data_2019acc0015_k1_100k
#Deposition Number 1967876

_audit_creation_date               2019-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2016/6'
loop_
  _audit_author_name
  _audit_author_email
  _audit_author_address
 'Light, M.E.' light@soton.ac.uk
;

University of Southampton
Chemistry
University Road Highfield
Southampton
;
 'McGlacken, G.' 'g.mcglacken@ucc.ie '
;

University College Cork 
Department of Chemistry 
Kane Building, College Road 
Cork
Ireland
;

_audit_contact_author_address
;
University of Southampton
Chemistry
University Road Highfield
Southampton
;
_audit_contact_author_email        light@soton.ac.uk
_audit_contact_author_name         'Light, M.E.'
_audit_contact_author_phone        02380599429
_publ_contact_author_id_orcid      0000-0002-0585-0843
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C21 H13 N O'
_chemical_formula_sum              'C21 H13 N O'
_chemical_formula_weight           295.32
_chemical_absolute_configuration   unk
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C22 H22 N1 O1'
_chemical_oxdiff_usercomment       RMS-269
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     11.4470(2)
_cell_length_b                     6.2048(2)
_cell_length_c                     20.0037(5)
_cell_angle_alpha                  90
_cell_angle_beta                   94.868(2)
_cell_angle_gamma                  90
_cell_volume                       1415.66(6)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      5920
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        30.6440
_cell_measurement_theta_min        3.0630
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.085
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.63299
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.386
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         prism
_exptl_crystal_F_000               616
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 0 0 1 0.0238
 0 0 -1 0.0238
 -5 0 -1 0.0224
 5 0 1 0.0224
 1 -5 2 0.1316
 -5 5 -3 0.1379

_exptl_crystal_preparation         ?
_exptl_crystal_recrystallization_method 
 'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max            0.314
_exptl_crystal_size_mid            0.057
_exptl_crystal_size_min            0.045
loop_
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 -0.0002 -0.0001 0.9960 0.0349 0.0027 -0.0057
 0.0002 0.0001 -0.9960 -0.0349 -0.0027 0.0057
 -4.9788 0.0004 -0.9990 -0.0320 -0.3108 0.0371
 4.9788 -0.0004 0.9990 0.0320 0.3108 -0.0371
 0.9963 -4.9812 1.9919 -0.0176 0.0093 -0.5772
 -4.9792 4.9815 -2.9902 -0.0150 -0.2585 0.6080

_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0461
_diffrn_reflns_av_unetI/netI       0.0644
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.998
_diffrn_reflns_limit_h_max         15
_diffrn_reflns_limit_h_min         -15
_diffrn_reflns_limit_k_max         8
_diffrn_reflns_limit_k_min         -8
_diffrn_reflns_limit_l_max         26
_diffrn_reflns_limit_l_min         -26
_diffrn_reflns_number              19713
_diffrn_reflns_point_group_measured_fraction_full  0.988
_diffrn_reflns_point_group_measured_fraction_max  0.971
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.495
_diffrn_reflns_theta_min           3.066
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100(2)
_diffrn_detector                   'CCD area detector'
_diffrn_detector_area_resol_mean   28.5714
_diffrn_detector_type              'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -108.00  16.00   1.00   22.50    --  -19.00 -60.00 -90.00  124
  2  ω    -54.00  70.00   1.00   22.50    --  -19.00  60.00  60.00  124
  3  ω   -108.00  16.00   1.00   22.50    --  -19.00 -57.00 150.00  124
  4  ω   -108.00 -45.00   1.00   22.50    --  -19.00 -60.00  30.00   63
  5  ω    -54.00  70.00   1.00   22.50    --  -19.00  60.00-120.00  124
;
_diffrn_measurement_device         'four-circle κ diffractometer'
_diffrn_measurement_device_type    'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2   'Rigaku AFC12 (Right)'
_diffrn_measurement_method         'profile data from ω-scans'
_diffrn_measurement_specimen_support  'MiTeGen MicroMesh'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0005978000
_diffrn_orient_matrix_UB_12        0.0174237000
_diffrn_orient_matrix_UB_13        0.0350323000
_diffrn_orient_matrix_UB_21        0.0618629000
_diffrn_orient_matrix_UB_22        0.0116055000
_diffrn_orient_matrix_UB_23        0.0027728000
_diffrn_orient_matrix_UB_31        -0.0062856000
_diffrn_orient_matrix_UB_32        0.1123241000
_diffrn_orient_matrix_UB_33        -0.0057224000
_diffrn_radiation_collimation      0.3
_diffrn_radiation_monochromator    'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'Rotating-anode X-ray tube'
_diffrn_source_current             55.0
_diffrn_source_power               2.475
_diffrn_source_target              Mo
_diffrn_source_type                'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage             45.0
_diffrn_special_details            ?
_reflns_Friedel_coverage           0.785
_reflns_Friedel_fraction_full      0.977
_reflns_Friedel_fraction_max       0.938
_reflns_number_gt                  5764
_reflns_number_total               6982
_reflns_odcompleteness_completeness  94.83
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       30.44
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection         'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction          'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.250
_refine_diff_density_min           -0.272
_refine_diff_density_rms           0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1846 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.7(9)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.067
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       415
_refine_ls_number_reflns           6982
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0718
_refine_ls_R_factor_gt             0.0547
_refine_ls_restrained_S_all        1.067
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0427P)²+0.0040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0991
_refine_ls_wR_factor_ref           0.1052
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B), C8B(H8B), C12B(H12B), C13B(H13B),
 C15B(H15B), C17B(H17B), C18B(H18B), C19B(H19B), C20B(H20B), C21B(H21B),
 C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C8A(H8A), C12A(H12A), C13A(H13A),
 C15A(H15A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1B O 0.79963(15) 0.0214(3) 0.82501(8) 0.0215(4) Uani 1 1 d . . . . .
 N1B N 0.83803(18) 0.3630(4) 0.65136(10) 0.0214(5) Uani 1 1 d . . . . .
 C1B C 0.7278(2) -0.1455(4) 0.79986(13) 0.0201(6) Uani 1 1 d . . . . .
 C2B C 0.6898(2) -0.3098(5) 0.83795(13) 0.0223(6) Uani 1 1 d . . . . .
 H2B H 0.709531 -0.317280 0.884989 0.027 Uiso 1 1 calc R . . . .
 C3B C 0.6208(2) -0.4649(5) 0.80405(13) 0.0243(6) Uani 1 1 d . . . . .
 H3B H 0.593076 -0.583620 0.828199 0.029 Uiso 1 1 calc R . . . .
 C4B C 0.5912(2) -0.4500(5) 0.73522(14) 0.0233(6) Uani 1 1 d . . . . .
 H4B H 0.543259 -0.558392 0.713474 0.028 Uiso 1 1 calc R . . . .
 C5B C 0.6299(2) -0.2815(5) 0.69787(13) 0.0230(6) Uani 1 1 d . . . . .
 H5B H 0.608516 -0.272221 0.651028 0.028 Uiso 1 1 calc R . . . .
 C6B C 0.7011(2) -0.1255(5) 0.73048(13) 0.0198(6) Uani 1 1 d . . . . .
 C7B C 0.7619(2) 0.0677(4) 0.71193(12) 0.0191(6) Uani 1 1 d . . . . .
 C8B C 0.7764(2) 0.1840(5) 0.65268(13) 0.0221(6) Uani 1 1 d . . . . .
 H8B H 0.739785 0.130595 0.611587 0.027 Uiso 1 1 calc R . . . .
 C9B C 0.8923(2) 0.4379(5) 0.71097(13) 0.0197(6) Uani 1 1 d . . . . .
 C10B C 0.8872(2) 0.3323(4) 0.77330(13) 0.0182(6) Uani 1 1 d . . . . .
 C11B C 0.8183(2) 0.1452(5) 0.77024(12) 0.0189(6) Uani 1 1 d . . . . .
 C12B C 0.9592(2) 0.6278(5) 0.71076(13) 0.0213(6) Uani 1 1 d . . . . .
 H12B H 0.964078 0.703993 0.669896 0.026 Uiso 1 1 calc R . . . .
 C13B C 1.0176(2) 0.7051(5) 0.76855(13) 0.0213(6) Uani 1 1 d . . . . .
 H13B H 1.062746 0.833067 0.766666 0.026 Uiso 1 1 calc R . . . .
 C14B C 1.0124(2) 0.5989(4) 0.83111(13) 0.0196(6) Uani 1 1 d . . . . .
 C15B C 0.9465(2) 0.4140(5) 0.83196(13) 0.0200(6) Uani 1 1 d . . . . .
 H15B H 0.941069 0.340158 0.873186 0.024 Uiso 1 1 calc R . . . .
 C16B C 1.0779(2) 0.6808(5) 0.89352(13) 0.0204(6) Uani 1 1 d . . . . .
 C17B C 1.1290(2) 0.8848(5) 0.89689(14) 0.0282(7) Uani 1 1 d . . . . .
 H17B H 1.119132 0.977736 0.859100 0.034 Uiso 1 1 calc R . . . .
 C18B C 1.1941(3) 0.9543(5) 0.95453(15) 0.0317(7) Uani 1 1 d . . . . .
 H18B H 1.228693 1.093534 0.955624 0.038 Uiso 1 1 calc R . . . .
 C19B C 1.2088(2) 0.8236(5) 1.01004(14) 0.0295(7) Uani 1 1 d . . . . .
 H19B H 1.254141 0.871193 1.049265 0.035 Uiso 1 1 calc R . . . .
 C20B C 1.1571(3) 0.6222(5) 1.00821(14) 0.0299(7) Uani 1 1 d . . . . .
 H20B H 1.165529 0.531817 1.046644 0.036 Uiso 1 1 calc R . . . .
 C21B C 1.0935(2) 0.5523(5) 0.95094(13) 0.0259(6) Uani 1 1 d . . . . .
 H21B H 1.059144 0.412885 0.950391 0.031 Uiso 1 1 calc R . . . .
 O1A O 0.63001(15) 0.0194(3) 0.36657(8) 0.0214(4) Uani 1 1 d . . . . .
 N1A N 0.92098(19) 0.3789(4) 0.43141(11) 0.0225(5) Uani 1 1 d . . . . .
 C1A C 0.6359(2) -0.1419(4) 0.41490(12) 0.0198(6) Uani 1 1 d . . . . .
 C2A C 0.5574(2) -0.3091(5) 0.41580(13) 0.0232(6) Uani 1 1 d . . . . .
 H2A H 0.493418 -0.323705 0.382651 0.028 Uiso 1 1 calc R . . . .
 C3A C 0.5773(2) -0.4559(5) 0.46812(13) 0.0260(6) Uani 1 1 d . . . . .
 H3A H 0.525594 -0.574647 0.471181 0.031 Uiso 1 1 calc R . . . .
 C4A C 0.6720(3) -0.4310(5) 0.51617(13) 0.0268(7) Uani 1 1 d . . . . .
 H4A H 0.683019 -0.532382 0.551734 0.032 Uiso 1 1 calc R . . . .
 C5A C 0.7504(3) -0.2622(5) 0.51323(13) 0.0253(7) Uani 1 1 d . . . . .
 H5A H 0.815145 -0.248741 0.545937 0.030 Uiso 1 1 calc R . . . .
 C6A C 0.7328(2) -0.1128(5) 0.46171(13) 0.0213(6) Uani 1 1 d . . . . .
 C7A C 0.7903(2) 0.0801(4) 0.44020(12) 0.0199(6) Uani 1 1 d . . . . .
 C8A C 0.8905(2) 0.2020(5) 0.46208(13) 0.0227(6) Uani 1 1 d . . . . .
 H8A H 0.937920 0.154524 0.500531 0.027 Uiso 1 1 calc R . . . .
 C9A C 0.8512(2) 0.4468(5) 0.37550(12) 0.0192(6) Uani 1 1 d . . . . .
 C10A C 0.7512(2) 0.3348(4) 0.34774(13) 0.0187(6) Uani 1 1 d . . . . .
 C11A C 0.7245(2) 0.1500(5) 0.38365(12) 0.0191(6) Uani 1 1 d . . . . .
 C12A C 0.8822(2) 0.6357(5) 0.34307(13) 0.0223(6) Uani 1 1 d . . . . .
 H12A H 0.948273 0.716043 0.360938 0.027 Uiso 1 1 calc R . . . .
 C13A C 0.8191(2) 0.7071(5) 0.28610(13) 0.0208(6) Uani 1 1 d . . . . .
 H13A H 0.842748 0.835735 0.265283 0.025 Uiso 1 1 calc R . . . .
 C14A C 0.7193(2) 0.5938(4) 0.25731(12) 0.0183(6) Uani 1 1 d . . . . .
 C15A C 0.6865(2) 0.4095(4) 0.28944(12) 0.0189(6) Uani 1 1 d . . . . .
 H15A H 0.619138 0.331926 0.271928 0.023 Uiso 1 1 calc R . . . .
 C16A C 0.6544(2) 0.6693(5) 0.19383(12) 0.0197(6) Uani 1 1 d . . . . .
 C17A C 0.6780(2) 0.8692(5) 0.16508(14) 0.0241(6) Uani 1 1 d . . . . .
 H17A H 0.733951 0.962661 0.187729 0.029 Uiso 1 1 calc R . . . .
 C18A C 0.6212(2) 0.9334(5) 0.10416(14) 0.0290(7) Uani 1 1 d . . . . .
 H18A H 0.639822 1.068352 0.085298 0.035 Uiso 1 1 calc R . . . .
 C19A C 0.5379(3) 0.8022(5) 0.07085(14) 0.0279(7) Uani 1 1 d . . . . .
 H19A H 0.499320 0.845550 0.029079 0.034 Uiso 1 1 calc R . . . .
 C20A C 0.5112(3) 0.6059(5) 0.09937(13) 0.0263(7) Uani 1 1 d . . . . .
 H20A H 0.452870 0.515655 0.077437 0.032 Uiso 1 1 calc R . . . .
 C21A C 0.5691(2) 0.5412(5) 0.15932(12) 0.0231(6) Uani 1 1 d . . . . .
 H21A H 0.550233 0.405563 0.177649 0.028 Uiso 1 1 calc R . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1B C1B 1.390(3) . ?
 O1B C11B 1.369(3) . ?
 N1B C8B 1.317(4) . ?
 N1B C9B 1.378(3) . ?
 C1B C2B 1.366(4) . ?
 C1B C6B 1.401(3) . ?
 C2B H2B 0.9500 . ?
 C2B C3B 1.385(4) . ?
 C3B H3B 0.9500 . ?
 C3B C4B 1.393(4) . ?
 C4B H4B 0.9500 . ?
 C4B C5B 1.380(4) . ?
 C5B H5B 0.9500 . ?
 C5B C6B 1.392(4) . ?
 C6B C7B 1.450(4) . ?
 C7B C8B 1.409(4) . ?
 C7B C11B 1.372(3) . ?
 C8B H8B 0.9500 . ?
 C9B C10B 1.414(4) . ?
 C9B C12B 1.406(4) . ?
 C10B C11B 1.402(4) . ?
 C10B C15B 1.400(4) . ?
 C12B H12B 0.9500 . ?
 C12B C13B 1.372(3) . ?
 C13B H13B 0.9500 . ?
 C13B C14B 1.420(4) . ?
 C14B C15B 1.374(4) . ?
 C14B C16B 1.490(3) . ?
 C15B H15B 0.9500 . ?
 C16B C17B 1.394(4) . ?
 C16B C21B 1.397(4) . ?
 C17B H17B 0.9500 . ?
 C17B C18B 1.387(4) . ?
 C18B H18B 0.9500 . ?
 C18B C19B 1.374(4) . ?
 C19B H19B 0.9500 . ?
 C19B C20B 1.382(4) . ?
 C20B H20B 0.9500 . ?
 C20B C21B 1.375(4) . ?
 C21B H21B 0.9500 . ?
 O1A C1A 1.390(3) . ?
 O1A C11A 1.371(3) . ?
 N1A C8A 1.319(4) . ?
 N1A C9A 1.384(3) . ?
 C1A C2A 1.373(4) . ?
 C1A C6A 1.401(3) . ?
 C2A H2A 0.9500 . ?
 C2A C3A 1.392(4) . ?
 C3A H3A 0.9500 . ?
 C3A C4A 1.396(4) . ?
 C4A H4A 0.9500 . ?
 C4A C5A 1.383(4) . ?
 C5A H5A 0.9500 . ?
 C5A C6A 1.388(4) . ?
 C6A C7A 1.449(4) . ?
 C7A C8A 1.412(4) . ?
 C7A C11A 1.375(3) . ?
 C8A H8A 0.9500 . ?
 C9A C10A 1.412(3) . ?
 C9A C12A 1.400(4) . ?
 C10A C11A 1.401(4) . ?
 C10A C15A 1.406(3) . ?
 C12A H12A 0.9500 . ?
 C12A C13A 1.370(3) . ?
 C13A H13A 0.9500 . ?
 C13A C14A 1.422(3) . ?
 C14A C15A 1.379(4) . ?
 C14A C16A 1.491(3) . ?
 C15A H15A 0.9500 . ?
 C16A C17A 1.403(4) . ?
 C16A C21A 1.396(4) . ?
 C17A H17A 0.9500 . ?
 C17A C18A 1.390(4) . ?
 C18A H18A 0.9500 . ?
 C18A C19A 1.382(4) . ?
 C19A H19A 0.9500 . ?
 C19A C20A 1.390(4) . ?
 C20A H20A 0.9500 . ?
 C20A C21A 1.379(4) . ?
 C21A H21A 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C11B O1B C1B 104.83(19) . . ?
 C8B N1B C9B 118.0(2) . . ?
 O1B C1B C6B 111.4(2) . . ?
 C2B C1B O1B 124.1(2) . . ?
 C2B C1B C6B 124.4(3) . . ?
 C1B C2B H2B 121.9 . . ?
 C1B C2B C3B 116.2(2) . . ?
 C3B C2B H2B 121.9 . . ?
 C2B C3B H3B 119.4 . . ?
 C2B C3B C4B 121.2(3) . . ?
 C4B C3B H3B 119.4 . . ?
 C3B C4B H4B 119.2 . . ?
 C5B C4B C3B 121.6(3) . . ?
 C5B C4B H4B 119.2 . . ?
 C4B C5B H5B 120.8 . . ?
 C4B C5B C6B 118.4(2) . . ?
 C6B C5B H5B 120.8 . . ?
 C1B C6B C7B 104.9(2) . . ?
 C5B C6B C1B 118.2(3) . . ?
 C5B C6B C7B 136.9(2) . . ?
 C8B C7B C6B 137.0(2) . . ?
 C11B C7B C6B 105.9(2) . . ?
 C11B C7B C8B 117.1(3) . . ?
 N1B C8B C7B 123.4(2) . . ?
 N1B C8B H8B 118.3 . . ?
 C7B C8B H8B 118.3 . . ?
 N1B C9B C10B 123.9(3) . . ?
 N1B C9B C12B 119.1(2) . . ?
 C12B C9B C10B 117.0(2) . . ?
 C11B C10B C9B 114.2(2) . . ?
 C15B C10B C9B 121.2(2) . . ?
 C15B C10B C11B 124.6(2) . . ?
 O1B C11B C7B 112.9(2) . . ?
 O1B C11B C10B 123.7(2) . . ?
 C7B C11B C10B 123.4(2) . . ?
 C9B C12B H12B 119.4 . . ?
 C13B C12B C9B 121.1(3) . . ?
 C13B C12B H12B 119.4 . . ?
 C12B C13B H13B 119.1 . . ?
 C12B C13B C14B 121.8(3) . . ?
 C14B C13B H13B 119.1 . . ?
 C13B C14B C16B 121.6(2) . . ?
 C15B C14B C13B 117.6(2) . . ?
 C15B C14B C16B 120.8(2) . . ?
 C10B C15B H15B 119.3 . . ?
 C14B C15B C10B 121.3(2) . . ?
 C14B C15B H15B 119.3 . . ?
 C17B C16B C14B 122.0(2) . . ?
 C17B C16B C21B 117.0(2) . . ?
 C21B C16B C14B 121.0(3) . . ?
 C16B C17B H17B 119.5 . . ?
 C18B C17B C16B 121.1(3) . . ?
 C18B C17B H17B 119.5 . . ?
 C17B C18B H18B 119.7 . . ?
 C19B C18B C17B 120.6(3) . . ?
 C19B C18B H18B 119.7 . . ?
 C18B C19B H19B 120.4 . . ?
 C18B C19B C20B 119.3(3) . . ?
 C20B C19B H19B 120.4 . . ?
 C19B C20B H20B 119.9 . . ?
 C21B C20B C19B 120.2(3) . . ?
 C21B C20B H20B 119.9 . . ?
 C16B C21B H21B 119.1 . . ?
 C20B C21B C16B 121.8(3) . . ?
 C20B C21B H21B 119.1 . . ?
 C11A O1A C1A 105.16(19) . . ?
 C8A N1A C9A 118.2(2) . . ?
 O1A C1A C6A 111.2(2) . . ?
 C2A C1A O1A 124.1(2) . . ?
 C2A C1A C6A 124.8(3) . . ?
 C1A C2A H2A 122.0 . . ?
 C1A C2A C3A 116.1(2) . . ?
 C3A C2A H2A 122.0 . . ?
 C2A C3A H3A 119.6 . . ?
 C2A C3A C4A 120.9(3) . . ?
 C4A C3A H3A 119.6 . . ?
 C3A C4A H4A 119.2 . . ?
 C5A C4A C3A 121.6(3) . . ?
 C5A C4A H4A 119.2 . . ?
 C4A C5A H5A 120.5 . . ?
 C4A C5A C6A 118.9(3) . . ?
 C6A C5A H5A 120.5 . . ?
 C1A C6A C7A 105.2(2) . . ?
 C5A C6A C1A 117.8(3) . . ?
 C5A C6A C7A 137.0(3) . . ?
 C8A C7A C6A 136.7(2) . . ?
 C11A C7A C6A 105.9(2) . . ?
 C11A C7A C8A 117.4(3) . . ?
 N1A C8A C7A 122.8(2) . . ?
 N1A C8A H8A 118.6 . . ?
 C7A C8A H8A 118.6 . . ?
 N1A C9A C10A 124.1(2) . . ?
 N1A C9A C12A 118.5(2) . . ?
 C12A C9A C10A 117.3(2) . . ?
 C11A C10A C9A 114.0(2) . . ?
 C11A C10A C15A 124.9(2) . . ?
 C15A C10A C9A 121.1(2) . . ?
 O1A C11A C7A 112.6(2) . . ?
 O1A C11A C10A 123.9(2) . . ?
 C7A C11A C10A 123.5(2) . . ?
 C9A C12A H12A 119.3 . . ?
 C13A C12A C9A 121.3(3) . . ?
 C13A C12A H12A 119.3 . . ?
 C12A C13A H13A 119.1 . . ?
 C12A C13A C14A 121.7(3) . . ?
 C14A C13A H13A 119.1 . . ?
 C13A C14A C16A 121.0(2) . . ?
 C15A C14A C13A 117.6(2) . . ?
 C15A C14A C16A 121.4(2) . . ?
 C10A C15A H15A 119.5 . . ?
 C14A C15A C10A 121.0(2) . . ?
 C14A C15A H15A 119.5 . . ?
 C17A C16A C14A 121.9(2) . . ?
 C21A C16A C14A 121.3(2) . . ?
 C21A C16A C17A 116.8(2) . . ?
 C16A C17A H17A 119.3 . . ?
 C18A C17A C16A 121.4(3) . . ?
 C18A C17A H17A 119.3 . . ?
 C17A C18A H18A 119.8 . . ?
 C19A C18A C17A 120.4(3) . . ?
 C19A C18A H18A 119.8 . . ?
 C18A C19A H19A 120.5 . . ?
 C18A C19A C20A 119.0(3) . . ?
 C20A C19A H19A 120.5 . . ?
 C19A C20A H20A 119.8 . . ?
 C21A C20A C19A 120.4(3) . . ?
 C21A C20A H20A 119.8 . . ?
 C16A C21A H21A 119.0 . . ?
 C20A C21A C16A 121.9(3) . . ?
 C20A C21A H21A 119.0 . . ?

_olex2_diffrn_ambient_temperature_device  'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
 'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id  RMS-269
_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  2.604
_oxdiff_exptl_absorpt_empirical_full_min  0.527
data_2019acc0016_k1_100k
# CCDC Deposition Number 1967484

_audit_creation_date               2019-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2016/6'
loop_
  _audit_author_name
  _audit_author_email
  _audit_author_address
 'Light, M.E.' light@soton.ac.uk
;

University of Southampton
Chemistry
University Road Highfield
Southampton
;
 'McGlacken, G.' 'g.mcglacken@ucc.ie '
;

University College Cork 
Department of Chemistry 
Kane Building, College Road 
Cork
Ireland
;

_audit_contact_author_address
;
University of Southampton
Chemistry
University Road Highfield
Southampton
;
_audit_contact_author_email        light@soton.ac.uk
_audit_contact_author_name         'Light, M.E.'
_audit_contact_author_phone        02380599429
_publ_contact_author_id_orcid      0000-0002-0585-0843
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C21 H13 N O'
_chemical_formula_sum              'C21 H13 N O'
_chemical_formula_weight           295.32
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C12 H12 N1 O1'
_chemical_oxdiff_usercomment       RMS-347
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                     10.7953(4)
_cell_length_b                     5.0922(2)
_cell_length_c                     25.8426(9)
_cell_angle_alpha                  90
_cell_angle_beta                   94.918(3)
_cell_angle_gamma                  90
_cell_volume                       1415.38(9)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      5616
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        30.7230
_cell_measurement_theta_min        3.7770
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.085
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.31290
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.386
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         rod
_exptl_crystal_F_000               616
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 1 0 -5 0.0224
 -1 0 5 0.0224
 1 5 2 0.2758
 -1 -5 -2 0.2758
 -5 0 -4 0.0254
 5 0 4 0.0254

_exptl_crystal_recrystallization_method 
 'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max            0.564
_exptl_crystal_size_mid            0.051
_exptl_crystal_size_min            0.045
loop_
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 0.9978 -0.0002 -4.9939 0.1464 -0.0153 0.0047
 -0.9978 0.0002 4.9939 -0.1464 0.0153 -0.0047
 0.9893 4.9929 2.0277 -0.0028 0.0028 -0.7013
 -0.9893 -4.9929 -2.0277 0.0028 -0.0028 0.7013
 -4.9932 0.0006 -3.9843 -0.0606 -0.3483 0.0415
 4.9932 -0.0006 3.9843 0.0606 0.3483 -0.0415

_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0725
_diffrn_reflns_av_unetI/netI       0.0619
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.913
_diffrn_reflns_limit_h_max         12
_diffrn_reflns_limit_h_min         -15
_diffrn_reflns_limit_k_max         7
_diffrn_reflns_limit_k_min         -7
_diffrn_reflns_limit_l_max         37
_diffrn_reflns_limit_l_min         -37
_diffrn_reflns_number              15415
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.913
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           30.959
_diffrn_reflns_theta_min           3.165
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100(2)
_diffrn_detector                   'CCD area detector'
_diffrn_detector_area_resol_mean   28.5714
_diffrn_detector_type              'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.913
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -105.00  13.00   1.00   10.00    --  -15.60 -38.00  90.00  118
  2  ω    -48.00  74.00   1.00   10.00    --  -15.60  60.00 120.00  122
  3  ω   -102.00  17.00   1.00   10.00    --  -15.60 -60.00  60.00  119
  4  ω    -45.00   5.00   1.00   10.00    --  -15.60  60.00-180.00   50
  5  ω     30.00  67.00   1.00   10.00    --  -15.60  60.00-180.00   37
;
_diffrn_measurement_device         'four-circle κ diffractometer'
_diffrn_measurement_device_type    'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2   'Rigaku AFC12 (Right)'
_diffrn_measurement_method         'profile data from ω-scans'
_diffrn_measurement_specimen_support  'MiTeGen MicroMesh'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        0.0306418000
_diffrn_orient_matrix_UB_12        0.0027957000
_diffrn_orient_matrix_UB_13        -0.0231935000
_diffrn_orient_matrix_UB_21        0.0580585000
_diffrn_orient_matrix_UB_22        -0.0169078000
_diffrn_orient_matrix_UB_23        0.0146648000
_diffrn_orient_matrix_UB_31        -0.0065311000
_diffrn_orient_matrix_UB_32        -0.1382569000
_diffrn_orient_matrix_UB_33        -0.0022503000
_diffrn_radiation_collimation      0.3
_diffrn_radiation_monochromator    'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'Rotating-anode X-ray tube'
_diffrn_source_current             55.0
_diffrn_source_power               2.475
_diffrn_source_target              Mo
_diffrn_source_type                'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage             45.0
_diffrn_special_details            ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3437
_reflns_number_total               4114
_reflns_odcompleteness_completeness  99.78
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       27.42
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection         'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction          'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.351
_refine_diff_density_min           -0.266
_refine_diff_density_rms           0.059
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.098
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       208
_refine_ls_number_reflns           4114
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0808
_refine_ls_R_factor_gt             0.0634
_refine_ls_restrained_S_all        1.098
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0596P)²+0.4838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1404
_refine_ls_wR_factor_ref           0.1508
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1 O 0.33687(9) 0.9168(2) 0.28625(4) 0.0177(2) Uani 1 1 d . . . . .
 N1 N 0.37259(12) 0.6587(3) 0.43839(5) 0.0196(3) Uani 1 1 d . . . . .
 C1 C 0.24890(13) 1.1129(3) 0.28972(6) 0.0172(3) Uani 1 1 d . . . . .
 C2 C 0.20471(14) 1.2713(3) 0.24877(6) 0.0196(3) Uani 1 1 d . . . . .
 H2 H 0.231779 1.251786 0.214957 0.024 Uiso 1 1 calc R . . . .
 C3 C 0.11841(14) 1.4608(3) 0.25999(6) 0.0219(3) Uani 1 1 d . . . . .
 H3 H 0.085008 1.574324 0.233142 0.026 Uiso 1 1 calc R . . . .
 C4 C 0.07971(14) 1.4880(3) 0.30990(6) 0.0214(3) Uani 1 1 d . . . . .
 H4 H 0.020117 1.618860 0.316215 0.026 Uiso 1 1 calc R . . . .
 C5 C 0.12638(14) 1.3280(3) 0.35051(6) 0.0195(3) Uani 1 1 d . . . . .
 H5 H 0.100192 1.349214 0.384436 0.023 Uiso 1 1 calc R . . . .
 C6 C 0.21272(13) 1.1354(3) 0.34017(6) 0.0171(3) Uani 1 1 d . . . . .
 C7 C 0.28399(13) 0.9366(3) 0.36993(6) 0.0169(3) Uani 1 1 d . . . . .
 C8 C 0.29536(14) 0.8472(3) 0.42180(6) 0.0190(3) Uani 1 1 d . . . . .
 H8 H 0.245069 0.926410 0.445879 0.023 Uiso 1 1 calc R . . . .
 C9 C 0.44585(13) 0.5438(3) 0.40333(6) 0.0171(3) Uani 1 1 d . . . . .
 C10 C 0.44081(13) 0.6149(3) 0.35005(6) 0.0164(3) Uani 1 1 d . . . . .
 C11 C 0.35585(13) 0.8154(3) 0.33549(5) 0.0164(3) Uani 1 1 d . . . . .
 C12 C 0.53424(14) 0.3545(3) 0.42221(6) 0.0183(3) Uani 1 1 d . . . . .
 H12 H 0.538573 0.304681 0.457748 0.022 Uiso 1 1 calc R . . . .
 C13 C 0.61443(14) 0.2406(3) 0.38986(6) 0.0173(3) Uani 1 1 d . . . . .
 C14 C 0.60389(14) 0.3072(3) 0.33625(6) 0.0190(3) Uani 1 1 d . . . . .
 H14 H 0.656336 0.223352 0.313603 0.023 Uiso 1 1 calc R . . . .
 C15 C 0.51954(14) 0.4901(3) 0.31668(6) 0.0189(3) Uani 1 1 d . . . . .
 H15 H 0.513952 0.532964 0.280782 0.023 Uiso 1 1 calc R . . . .
 C16 C 0.71437(14) 0.0575(3) 0.41028(6) 0.0173(3) Uani 1 1 d . . . . .
 C17 C 0.69660(15) -0.1163(3) 0.45081(6) 0.0203(3) Uani 1 1 d . . . . .
 H17 H 0.619563 -0.116728 0.466027 0.024 Uiso 1 1 calc R . . . .
 C18 C 0.79005(15) -0.2884(3) 0.46915(6) 0.0237(4) Uani 1 1 d . . . . .
 H18 H 0.776198 -0.407386 0.496372 0.028 Uiso 1 1 calc R . . . .
 C19 C 0.90366(15) -0.2868(3) 0.44775(6) 0.0251(4) Uani 1 1 d . . . . .
 H19 H 0.967457 -0.405100 0.460194 0.030 Uiso 1 1 calc R . . . .
 C20 C 0.92381(15) -0.1124(3) 0.40821(6) 0.0237(4) Uani 1 1 d . . . . .
 H20 H 1.001963 -0.109344 0.393887 0.028 Uiso 1 1 calc R . . . .
 C21 C 0.83014(15) 0.0579(3) 0.38946(6) 0.0215(3) Uani 1 1 d . . . . .
 H21 H 0.844606 0.176204 0.362195 0.026 Uiso 1 1 calc R . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1 C1 1.3860(18) . ?
 O1 C11 1.3725(17) . ?
 N1 C8 1.319(2) . ?
 N1 C9 1.383(2) . ?
 C1 C2 1.383(2) . ?
 C1 C6 1.398(2) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.389(2) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.396(2) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.389(2) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.395(2) . ?
 C6 C7 1.451(2) . ?
 C7 C8 1.411(2) . ?
 C7 C11 1.376(2) . ?
 C8 H8 0.9500 . ?
 C9 C10 1.420(2) . ?
 C9 C12 1.414(2) . ?
 C10 C11 1.402(2) . ?
 C10 C15 1.412(2) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.382(2) . ?
 C13 C14 1.421(2) . ?
 C13 C16 1.488(2) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.369(2) . ?
 C15 H15 0.9500 . ?
 C16 C17 1.397(2) . ?
 C16 C21 1.402(2) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.389(2) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.388(2) . ?
 C19 H19 0.9500 . ?
 C19 C20 1.385(2) . ?
 C20 H20 0.9500 . ?
 C20 C21 1.388(2) . ?
 C21 H21 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C11 O1 C1 105.07(11) . . ?
 C8 N1 C9 118.45(13) . . ?
 O1 C1 C6 111.54(13) . . ?
 C2 C1 O1 124.35(14) . . ?
 C2 C1 C6 124.09(15) . . ?
 C1 C2 H2 122.0 . . ?
 C1 C2 C3 116.05(15) . . ?
 C3 C2 H2 122.0 . . ?
 C2 C3 H3 119.3 . . ?
 C2 C3 C4 121.39(15) . . ?
 C4 C3 H3 119.3 . . ?
 C3 C4 H4 119.3 . . ?
 C5 C4 C3 121.48(15) . . ?
 C5 C4 H4 119.3 . . ?
 C4 C5 H5 120.9 . . ?
 C4 C5 C6 118.22(15) . . ?
 C6 C5 H5 120.9 . . ?
 C1 C6 C7 105.03(13) . . ?
 C5 C6 C1 118.78(14) . . ?
 C5 C6 C7 136.18(15) . . ?
 C8 C7 C6 136.68(14) . . ?
 C11 C7 C6 105.84(13) . . ?
 C11 C7 C8 117.49(14) . . ?
 N1 C8 C7 123.01(14) . . ?
 N1 C8 H8 118.5 . . ?
 C7 C8 H8 118.5 . . ?
 N1 C9 C10 123.42(13) . . ?
 N1 C9 C12 118.02(13) . . ?
 C12 C9 C10 118.49(14) . . ?
 C11 C10 C9 114.55(13) . . ?
 C11 C10 C15 125.29(13) . . ?
 C15 C10 C9 120.15(14) . . ?
 O1 C11 C7 112.52(13) . . ?
 O1 C11 C10 124.42(13) . . ?
 C7 C11 C10 123.05(13) . . ?
 C9 C12 H12 119.4 . . ?
 C13 C12 C9 121.12(14) . . ?
 C13 C12 H12 119.4 . . ?
 C12 C13 C14 119.18(13) . . ?
 C12 C13 C16 121.42(13) . . ?
 C14 C13 C16 119.36(14) . . ?
 C13 C14 H14 119.4 . . ?
 C15 C14 C13 121.19(14) . . ?
 C15 C14 H14 119.4 . . ?
 C10 C15 H15 120.1 . . ?
 C14 C15 C10 119.77(14) . . ?
 C14 C15 H15 120.1 . . ?
 C17 C16 C13 121.38(14) . . ?
 C17 C16 C21 118.21(14) . . ?
 C21 C16 C13 120.40(14) . . ?
 C16 C17 H17 119.6 . . ?
 C18 C17 C16 120.89(15) . . ?
 C18 C17 H17 119.6 . . ?
 C17 C18 H18 120.0 . . ?
 C19 C18 C17 120.08(15) . . ?
 C19 C18 H18 120.0 . . ?
 C18 C19 H19 120.1 . . ?
 C20 C19 C18 119.85(15) . . ?
 C20 C19 H19 120.1 . . ?
 C19 C20 H20 119.9 . . ?
 C19 C20 C21 120.17(15) . . ?
 C21 C20 H20 119.9 . . ?
 C16 C21 H21 119.6 . . ?
 C20 C21 C16 120.79(15) . . ?
 C20 C21 H21 119.6 . . ?

_olex2_diffrn_ambient_temperature_device  'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
 'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id  RMS-347
_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  6.018
_oxdiff_exptl_absorpt_empirical_full_min  0.418
data_2019acc0017_k1_100k
_audit_creation_date               2019-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2016/6'
loop_
  _audit_author_name
  _audit_author_email
  _audit_author_address
 'Light, M.E.' light@soton.ac.uk
;

University of Southampton
Chemistry
University Road Highfield
Southampton
;
 'McGlacken, G.' 'g.mcglacken@ucc.ie '
;

University College Cork 
Department of Chemistry 
Kane Building, College Road 
Cork
Ireland
;

_audit_contact_author_address
;
University of Southampton
Chemistry
University Road Highfield
Southampton
;
_audit_contact_author_email        light@soton.ac.uk
_audit_contact_author_name         'Light, M.E.'
_audit_contact_author_phone        02380599429
_publ_contact_author_id_orcid      0000-0002-0585-0843
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C22 H19 N O3'
_chemical_formula_sum              'C22 H19 N O3'
_chemical_formula_weight           345.38
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C22 H22 N1 O1'
_chemical_oxdiff_usercomment       RMS-576
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     5.6018(2)
_cell_length_b                     10.0673(5)
_cell_length_c                     16.0613(8)
_cell_angle_alpha                  106.886(4)
_cell_angle_beta                   91.313(4)
_cell_angle_gamma                  99.947(4)
_cell_volume                       851.12(7)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      3747
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        30.3810
_cell_measurement_theta_min        3.6810
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.090
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.65097
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.348
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         prism
_exptl_crystal_F_000               364
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 -5 2 1 0.0535
 5 -2 -1 0.0535
 0 0 1 0.0606
 0 0 -1 0.0606
 0 -4 5 0.0133
 0 4 -5 0.0133

_exptl_crystal_recrystallization_method 
 'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max            0.158
_exptl_crystal_size_mid            0.107
_exptl_crystal_size_min            0.027
loop_
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 -4.9796 1.9937 1.0034 -0.1371 -0.6124 0.0807
 4.9796 -1.9937 -1.0034 0.1371 0.6124 -0.0807
 0.0001 -0.0003 0.9965 -0.0064 -0.0076 -0.0450
 -0.0001 0.0003 -0.9965 0.0064 0.0076 0.0450
 0.0011 -3.9874 4.9792 -0.2924 0.0562 -0.1123
 -0.0011 3.9874 -4.9792 0.2924 -0.0562 0.1123

_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0397
_diffrn_reflns_av_unetI/netI       0.0484
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -7
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -13
_diffrn_reflns_limit_l_max         21
_diffrn_reflns_limit_l_min         -21
_diffrn_reflns_number              13102
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.997
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.500
_diffrn_reflns_theta_min           2.848
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100(2)
_diffrn_detector                   'CCD area detector'
_diffrn_detector_area_resol_mean   28.5714
_diffrn_detector_type              'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -108.00  16.00   1.00   12.00    --  -19.10 -60.00 150.00  124
  2  ω   -108.00  13.00   1.00   12.00    --  -19.10 -38.00  30.00  121
  3  ω   -108.00  16.00   1.00   12.00    --  -19.10 -60.00-150.00  124
  4  ω   -104.00  -4.00   1.00   12.00    --  -19.10 -60.00  60.00  100
  5  ω    -33.00   7.00   1.00   12.00    --  -19.10  38.00  30.00   40
  6  ω   -107.00  15.00   1.00   12.00    --  -19.10 -60.00 -37.73  122
;
_diffrn_measurement_device         'four-circle κ diffractometer'
_diffrn_measurement_device_type    'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2   'Rigaku AFC12 (Right)'
_diffrn_measurement_method         'profile data from ω-scans'
_diffrn_measurement_specimen_support  'MiTeGen MicroMesh'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        0.0523640000
_diffrn_orient_matrix_UB_12        0.0652845000
_diffrn_orient_matrix_UB_13        -0.0064528000
_diffrn_orient_matrix_UB_21        0.1119895000
_diffrn_orient_matrix_UB_22        -0.0235948000
_diffrn_orient_matrix_UB_23        -0.0076357000
_diffrn_orient_matrix_UB_31        -0.0366367000
_diffrn_orient_matrix_UB_32        -0.0282898000
_diffrn_orient_matrix_UB_33        -0.0451991000
_diffrn_radiation_collimation      0.3
_diffrn_radiation_monochromator    'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'Rotating-anode X-ray tube'
_diffrn_source_current             55.0
_diffrn_source_power               2.475
_diffrn_source_target              Mo
_diffrn_source_type                'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage             45.0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3942
_reflns_number_total               4317
_reflns_odcompleteness_completeness  92.60
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       30.44
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection         'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction          'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.402
_refine_diff_density_min           -0.290
_refine_diff_density_rms           0.062
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.314
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       238
_refine_ls_number_reflns           4317
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.1071
_refine_ls_R_factor_gt             0.0953
_refine_ls_restrained_S_all        1.314
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0376P)²+0.8016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1650
_refine_ls_wR_factor_ref           0.1697
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1 O -0.2591(3) 0.85380(18) 0.47348(10) 0.0201(4) Uani 1 1 d . . . . .
 O2 O 0.8818(3) 0.6498(2) 0.83976(11) 0.0287(4) Uani 1 1 d . . . . .
 O3 O 0.7649(3) 0.81574(18) 0.95143(10) 0.0192(4) Uani 1 1 d . . . . .
 N1 N 0.2088(4) 0.5691(2) 0.43081(13) 0.0194(4) Uani 1 1 d . . . . .
 C1 C -0.3802(4) 0.8137(2) 0.39100(15) 0.0187(5) Uani 1 1 d . . . . .
 C2 C -0.5580(4) 0.8771(3) 0.36776(17) 0.0232(5) Uani 1 1 d . . . . .
 H2 H -0.607213 0.956011 0.407440 0.028 Uiso 1 1 calc R . . . .
 C3 C -0.6615(5) 0.8191(3) 0.28277(17) 0.0248(6) Uani 1 1 d . . . . .
 H3 H -0.785107 0.859491 0.263365 0.030 Uiso 1 1 calc R . . . .
 C4 C -0.5885(5) 0.7027(3) 0.22501(16) 0.0251(6) Uani 1 1 d . . . . .
 H4 H -0.665526 0.664487 0.167606 0.030 Uiso 1 1 calc R . . . .
 C5 C -0.4068(4) 0.6421(3) 0.24972(16) 0.0216(5) Uani 1 1 d . . . . .
 H5 H -0.355984 0.563911 0.209923 0.026 Uiso 1 1 calc R . . . .
 C6 C -0.3000(4) 0.6988(3) 0.33469(15) 0.0187(5) Uani 1 1 d . . . . .
 C7 C -0.1125(4) 0.6675(2) 0.38617(15) 0.0173(5) Uani 1 1 d . . . . .
 C8 C 0.0501(4) 0.5717(3) 0.37046(15) 0.0190(5) Uani 1 1 d . . . . .
 H8 H 0.043876 0.506461 0.313862 0.023 Uiso 1 1 calc R . . . .
 C9 C 0.2143(4) 0.6624(2) 0.51322(15) 0.0177(5) Uani 1 1 d . . . . .
 C10 C 0.0583(4) 0.7632(2) 0.53708(15) 0.0172(5) Uani 1 1 d . . . . .
 C11 C -0.0996(4) 0.7624(2) 0.46795(15) 0.0175(5) Uani 1 1 d . . . . .
 C12 C 0.3793(4) 0.6555(3) 0.57826(15) 0.0190(5) Uani 1 1 d . . . . .
 H12 H 0.488100 0.591095 0.563002 0.023 Uiso 1 1 calc R . . . .
 C13 C 0.3887(4) 0.7390(3) 0.66337(15) 0.0185(5) Uani 1 1 d . . . . .
 C14 C 0.2283(5) 0.8374(3) 0.68583(16) 0.0224(5) Uani 1 1 d . . . . .
 H14 H 0.232353 0.895283 0.744470 0.027 Uiso 1 1 calc R . . . .
 C15 C 0.0700(4) 0.8493(3) 0.62443(16) 0.0218(5) Uani 1 1 d . . . . .
 H15 H -0.034115 0.916317 0.640347 0.026 Uiso 1 1 calc R . . . .
 C16 C 0.5577(4) 0.7187(3) 0.72712(16) 0.0201(5) Uani 1 1 d . . . . .
 H16 H 0.656027 0.650395 0.704609 0.024 Uiso 1 1 calc R . . . .
 C17 C 0.5923(4) 0.7833(3) 0.81262(16) 0.0219(5) Uani 1 1 d . . . . .
 H17 H 0.507035 0.856788 0.838712 0.026 Uiso 1 1 calc R . . . .
 C18 C 0.7631(4) 0.7408(3) 0.86693(15) 0.0195(5) Uani 1 1 d . . . . .
 C19 C 0.8997(4) 0.7810(3) 1.02015(15) 0.0188(5) Uani 1 1 d . . . . .
 C20 C 1.1699(4) 0.7991(3) 1.00729(17) 0.0269(6) Uani 1 1 d . . . . .
 H20A H 1.198012 0.726039 0.954885 0.040 Uiso 1 1 calc GR . . . .
 H20B H 1.258138 0.790206 1.058207 0.040 Uiso 1 1 calc GR . . . .
 H20C H 1.227804 0.892634 1.000467 0.040 Uiso 1 1 calc GR . . . .
 C21 C 0.7899(5) 0.6335(3) 1.02146(17) 0.0261(6) Uani 1 1 d . . . . .
 H21A H 0.614101 0.625777 1.025860 0.039 Uiso 1 1 calc GR . . . .
 H21B H 0.863267 0.614508 1.071776 0.039 Uiso 1 1 calc GR . . . .
 H21C H 0.821079 0.564613 0.967586 0.039 Uiso 1 1 calc GR . . . .
 C22 C 0.8527(5) 0.8908(3) 1.10276(16) 0.0230(5) Uani 1 1 d . . . . .
 H22A H 0.922222 0.985546 1.100033 0.034 Uiso 1 1 calc GR . . . .
 H22B H 0.928532 0.874631 1.153664 0.034 Uiso 1 1 calc GR . . . .
 H22C H 0.677150 0.882874 1.107792 0.034 Uiso 1 1 calc GR . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1 C1 1.390(3) . ?
 O1 C11 1.376(3) . ?
 O2 C18 1.210(3) . ?
 O3 C18 1.347(3) . ?
 O3 C19 1.479(3) . ?
 N1 C8 1.309(3) . ?
 N1 C9 1.379(3) . ?
 C1 C2 1.371(3) . ?
 C1 C6 1.395(3) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.387(4) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.398(4) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.379(4) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.392(3) . ?
 C6 C7 1.453(3) . ?
 C7 C8 1.413(3) . ?
 C7 C11 1.373(3) . ?
 C8 H8 0.9500 . ?
 C9 C10 1.427(3) . ?
 C9 C12 1.404(3) . ?
 C10 C11 1.401(3) . ?
 C10 C15 1.412(3) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.376(3) . ?
 C13 C14 1.426(3) . ?
 C13 C16 1.460(3) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.356(4) . ?
 C15 H15 0.9500 . ?
 C16 H16 0.9500 . ?
 C16 C17 1.331(3) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.476(3) . ?
 C19 C20 1.519(3) . ?
 C19 C21 1.512(4) . ?
 C19 C22 1.522(3) . ?
 C20 H20A 0.9800 . ?
 C20 H20B 0.9800 . ?
 C20 H20C 0.9800 . ?
 C21 H21A 0.9800 . ?
 C21 H21B 0.9800 . ?
 C21 H21C 0.9800 . ?
 C22 H22A 0.9800 . ?
 C22 H22B 0.9800 . ?
 C22 H22C 0.9800 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C11 O1 C1 105.19(17) . . ?
 C18 O3 C19 120.69(18) . . ?
 C8 N1 C9 118.4(2) . . ?
 O1 C1 C6 111.3(2) . . ?
 C2 C1 O1 124.6(2) . . ?
 C2 C1 C6 124.0(2) . . ?
 C1 C2 H2 122.0 . . ?
 C1 C2 C3 115.9(2) . . ?
 C3 C2 H2 122.0 . . ?
 C2 C3 H3 119.2 . . ?
 C2 C3 C4 121.6(2) . . ?
 C4 C3 H3 119.2 . . ?
 C3 C4 H4 119.4 . . ?
 C5 C4 C3 121.3(2) . . ?
 C5 C4 H4 119.4 . . ?
 C4 C5 H5 121.0 . . ?
 C4 C5 C6 118.1(2) . . ?
 C6 C5 H5 121.0 . . ?
 C1 C6 C7 105.2(2) . . ?
 C5 C6 C1 119.1(2) . . ?
 C5 C6 C7 135.7(2) . . ?
 C8 C7 C6 135.9(2) . . ?
 C11 C7 C6 106.0(2) . . ?
 C11 C7 C8 118.1(2) . . ?
 N1 C8 C7 122.6(2) . . ?
 N1 C8 H8 118.7 . . ?
 C7 C8 H8 118.7 . . ?
 N1 C9 C10 124.0(2) . . ?
 N1 C9 C12 118.0(2) . . ?
 C12 C9 C10 117.9(2) . . ?
 C11 C10 C9 113.8(2) . . ?
 C11 C10 C15 126.5(2) . . ?
 C15 C10 C9 119.7(2) . . ?
 O1 C11 C10 124.8(2) . . ?
 C7 C11 O1 112.3(2) . . ?
 C7 C11 C10 122.9(2) . . ?
 C9 C12 H12 118.9 . . ?
 C13 C12 C9 122.1(2) . . ?
 C13 C12 H12 118.9 . . ?
 C12 C13 C14 118.9(2) . . ?
 C12 C13 C16 118.0(2) . . ?
 C14 C13 C16 123.1(2) . . ?
 C13 C14 H14 119.6 . . ?
 C15 C14 C13 120.7(2) . . ?
 C15 C14 H14 119.6 . . ?
 C10 C15 H15 119.7 . . ?
 C14 C15 C10 120.7(2) . . ?
 C14 C15 H15 119.7 . . ?
 C13 C16 H16 115.7 . . ?
 C17 C16 C13 128.6(2) . . ?
 C17 C16 H16 115.7 . . ?
 C16 C17 H17 120.0 . . ?
 C16 C17 C18 120.1(2) . . ?
 C18 C17 H17 120.0 . . ?
 O2 C18 O3 124.6(2) . . ?
 O2 C18 C17 124.9(2) . . ?
 O3 C18 C17 110.45(19) . . ?
 O3 C19 C20 110.98(19) . . ?
 O3 C19 C21 109.0(2) . . ?
 O3 C19 C22 102.41(18) . . ?
 C20 C19 C22 110.3(2) . . ?
 C21 C19 C20 112.8(2) . . ?
 C21 C19 C22 110.8(2) . . ?
 C19 C20 H20A 109.5 . . ?
 C19 C20 H20B 109.5 . . ?
 C19 C20 H20C 109.5 . . ?
 H20A C20 H20B 109.5 . . ?
 H20A C20 H20C 109.5 . . ?
 H20B C20 H20C 109.5 . . ?
 C19 C21 H21A 109.5 . . ?
 C19 C21 H21B 109.5 . . ?
 C19 C21 H21C 109.5 . . ?
 H21A C21 H21B 109.5 . . ?
 H21A C21 H21C 109.5 . . ?
 H21B C21 H21C 109.5 . . ?
 C19 C22 H22A 109.5 . . ?
 C19 C22 H22B 109.5 . . ?
 C19 C22 H22C 109.5 . . ?
 H22A C22 H22B 109.5 . . ?
 H22A C22 H22C 109.5 . . ?
 H22B C22 H22C 109.5 . . ?

_olex2_diffrn_ambient_temperature_device  'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
 'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id  RMS-576
_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  2.030
_oxdiff_exptl_absorpt_empirical_full_min  0.676
data_2019acc0020_k1_100k
# CCDC: 1970630
_audit_creation_date               2019-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2016/6'
loop_
  _audit_author_name
  _audit_author_email
  _audit_author_address
 'McGlacken, G.' 'g.mcglacken@ucc.ie '
;

University College Cork 
Department of Chemistry 
Kane Building, College Road 
Cork
Ireland
;
 'Light, M.E.' light@soton.ac.uk
;

University of Southampton
Chemistry
University Road Highfield
Southampton
;

_audit_contact_author_address
;
University of Southampton
Chemistry
University Road Highfield
Southampton
;
_audit_contact_author_email        light@soton.ac.uk
_audit_contact_author_name         'Light, M.E.'
_audit_contact_author_phone        02380599429
_publ_contact_author_id_orcid      0000-0002-0585-0843
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C34 H26 Br2 N2 O6 Pd, 1.33(H2 O)'
_chemical_formula_sum              'C34 H28.67 Br2 N2 O7.33 Pd'
_chemical_formula_weight           848.80
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C12 H12 N2 O2 Pd1 Br1'
_chemical_oxdiff_usercomment       AH_05_410_Br
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br' 'Br' -0.2901 2.4595
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Pd' 'Pd' -0.9988 1.0072
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             15
_space_group_name_H-M_alt          'C 1 2/c 1'
_space_group_name_Hall             '-C 2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                     19.9231(3)
_cell_length_b                     10.1765(2)
_cell_length_c                     15.8477(4)
_cell_angle_alpha                  90
_cell_angle_beta                   93.433(2)
_cell_angle_gamma                  90
_cell_volume                       3207.31(11)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      8815
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        30.3870
_cell_measurement_theta_min        3.4500
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      3.124
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.70439
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear yellow'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      yellow
_exptl_crystal_density_diffrn      1.758
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1685
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 -5 -1 -1 0.0280
 5 1 1 0.0280
 2 -5 2 0.0420
 -2 5 -2 0.0420
 2 -1 -5 0.0490
 -2 1 5 0.0490

_exptl_crystal_recrystallization_method 
 'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max            0.111
_exptl_crystal_size_mid            0.084
_exptl_crystal_size_min            0.056
loop_
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 -4.9910 -0.9993 -0.9987 0.1327 0.1460 -0.0237
 4.9910 0.9993 0.9987 -0.1327 -0.1460 0.0237
 2.0070 -4.9917 2.0039 0.0032 -0.0191 -0.3670
 -2.0070 4.9917 -2.0039 -0.0032 0.0191 0.3670
 2.0035 -0.9995 -4.9943 0.1914 -0.1461 -0.0142
 -2.0035 0.9995 4.9943 -0.1914 0.1461 0.0142

_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0463
_diffrn_reflns_av_unetI/netI       0.0358
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         26
_diffrn_reflns_limit_h_min         -26
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -13
_diffrn_reflns_limit_l_max         21
_diffrn_reflns_limit_l_min         -21
_diffrn_reflns_number              20357
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.999
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.498
_diffrn_reflns_theta_min           3.194
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100(2)
_diffrn_detector                   'CCD area detector'
_diffrn_detector_area_resol_mean   28.5714
_diffrn_detector_type              'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -51.00  70.00   1.00   15.27    --  -19.00  38.00 -60.00  121
  2  ω   -108.00  16.00   1.00   15.27    --  -19.00 -57.00  30.00  124
  3  ω    -54.00  70.00   1.00   15.27    --  -19.00  60.00-180.00  124
  4  ω    -51.00   2.00   1.00   15.27    --  -19.00  38.00 120.00   53
  5  ω   -108.00  13.00   1.00   15.27    --  -19.00 -38.00-180.00  121
;
_diffrn_measurement_device         'four-circle κ diffractometer'
_diffrn_measurement_device_type    'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2   'Rigaku AFC12 (Right)'
_diffrn_measurement_method         'profile data from ω-scans'
_diffrn_measurement_specimen_support  'MiTeGen MicroMesh'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0142154000
_diffrn_orient_matrix_UB_12        -0.0222457000
_diffrn_orient_matrix_UB_13        -0.0395646000
_diffrn_orient_matrix_UB_21        -0.0321590000
_diffrn_orient_matrix_UB_22        -0.0023413000
_diffrn_orient_matrix_UB_23        0.0168295000
_diffrn_orient_matrix_UB_31        -0.0059129000
_diffrn_orient_matrix_UB_32        0.0660259000
_diffrn_orient_matrix_UB_33        -0.0127490000
_diffrn_radiation_collimation      0.3
_diffrn_radiation_monochromator    'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'Rotating-anode X-ray tube'
_diffrn_source_current             55.0
_diffrn_source_power               2.475
_diffrn_source_target              Mo
_diffrn_source_type                'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage             45.0
_diffrn_special_details            ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3566
_reflns_number_total               4057
_reflns_odcompleteness_completeness  94.65
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       30.44
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection         'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction          'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.791
_refine_diff_density_min           -0.556
_refine_diff_density_rms           0.102
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.127
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       223
_refine_ls_number_reflns           4057
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0512
_refine_ls_R_factor_gt             0.0413
_refine_ls_restrained_S_all        1.127
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0405P)²+6.7651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0924
_refine_ls_wR_factor_ref           0.0963
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H4A_$1-H4A
 1.4 with sigma of 0.02
3. Others
 Fixed Sof: O5(0.16667) H5A(0.33333)
4.a Free rotating group:
 O5(H5A)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Pd1 Pd 0.500000 0.500000 0.500000 0.02307(10) Uani 1 2 d S T P . .
 Br1 Br 0.20634(2) 0.18189(4) 0.41282(2) 0.03991(12) Uani 1 1 d . . . . .
 O1 O 0.33073(11) 0.0310(2) 0.36066(15) 0.0294(5) Uani 1 1 d . . . . .
 O2 O 0.58904(10) 0.4106(2) 0.48694(15) 0.0290(5) Uani 1 1 d . . . . .
 O3 O 0.57832(12) 0.4127(3) 0.34640(16) 0.0421(6) Uani 1 1 d . . . . .
 N1 N 0.44916(11) 0.3398(2) 0.45507(17) 0.0244(5) Uani 1 1 d . . . . .
 C1 C 0.44511(13) 0.2254(3) 0.4998(2) 0.0236(6) Uani 1 1 d . . . . .
 C2 C 0.48025(15) 0.2131(3) 0.5798(2) 0.0290(7) Uani 1 1 d . . . . .
 H2 H 0.505441 0.284914 0.603317 0.035 Uiso 1 1 calc R . . . .
 C3 C 0.47763(16) 0.0966(4) 0.6231(2) 0.0359(8) Uani 1 1 d . . . . .
 H3 H 0.501907 0.088025 0.676251 0.043 Uiso 1 1 calc R . . . .
 C4 C 0.43969(17) -0.0105(4) 0.5903(2) 0.0360(8) Uani 1 1 d . . . . .
 H4 H 0.439027 -0.090616 0.621049 0.043 Uiso 1 1 calc R . . . .
 C5 C 0.40391(16) 0.0003(3) 0.5146(2) 0.0295(7) Uani 1 1 d . . . . .
 H5 H 0.377648 -0.071693 0.493309 0.035 Uiso 1 1 calc R . . . .
 C6 C 0.40571(14) 0.1182(3) 0.4674(2) 0.0233(6) Uani 1 1 d . . . . .
 C7 C 0.36968(14) 0.1353(3) 0.3876(2) 0.0256(6) Uani 1 1 d . . . . .
 C8 C 0.37643(16) 0.2483(3) 0.3437(2) 0.0326(8) Uani 1 1 d . . . . .
 H8 H 0.353764 0.259429 0.289723 0.039 Uiso 1 1 calc R . . . .
 C9 C 0.41728(15) 0.3484(3) 0.3791(2) 0.0317(7) Uani 1 1 d . . . . .
 H9 H 0.422497 0.426381 0.347202 0.038 Uiso 1 1 calc R . . . .
 C10 C 0.28406(15) 0.0543(3) 0.2927(2) 0.0272(7) Uani 1 1 d . . . . .
 C11 C 0.29649(19) 0.0032(3) 0.2142(2) 0.0362(8) Uani 1 1 d . . . . .
 H11 H 0.336519 -0.044902 0.206347 0.043 Uiso 1 1 calc R . . . .
 C12 C 0.2498(2) 0.0232(4) 0.1472(2) 0.0452(10) Uani 1 1 d . . . . .
 H12 H 0.257800 -0.011682 0.093094 0.054 Uiso 1 1 calc R . . . .
 C13 C 0.1923(2) 0.0926(4) 0.1582(2) 0.0448(10) Uani 1 1 d . . . . .
 H13 H 0.161448 0.108062 0.111187 0.054 Uiso 1 1 calc R . . . .
 C14 C 0.17844(16) 0.1405(4) 0.2369(2) 0.0386(8) Uani 1 1 d . . . . .
 H14 H 0.137727 0.186326 0.244685 0.046 Uiso 1 1 calc R . . . .
 C15 C 0.22481(15) 0.1207(3) 0.3042(2) 0.0274(7) Uani 1 1 d . . . . .
 C16 C 0.60712(13) 0.3902(3) 0.41578(19) 0.0204(6) Uani 1 1 d . . . . .
 C17 C 0.67774(16) 0.3224(3) 0.4144(2) 0.0341(8) Uani 1 1 d . . . . .
 H17A H 0.706410 0.352505 0.463034 0.051 Uiso 1 1 calc GR . . . .
 H17B H 0.698666 0.345614 0.362035 0.051 Uiso 1 1 calc GR . . . .
 H17C H 0.672276 0.226885 0.417389 0.051 Uiso 1 1 calc GR . . . .
 O4 O 0.500000 0.5958(4) 0.250000 0.0442(9) Uani 1 2 d S T P . .
 H4A H 0.5242(16) 0.550(4) 0.2831(19) 0.048(12) Uiso 1 1 d D . . . .
 O5 O 0.500000 0.2103(11) 0.250000 0.041(3) Uani 0.3333 2 d S T P . .
 H5A H 0.524482 0.264339 0.278891 0.061 Uiso 0.3333 1 d G . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Pd1 O2 2.015(2) . ?
 Pd1 O2 2.015(2) 5_666 ?
 Pd1 N1 2.026(2) 5_666 ?
 Pd1 N1 2.026(2) . ?
 Br1 C15 1.888(3) . ?
 O1 C7 1.368(3) . ?
 O1 C10 1.400(4) . ?
 O2 C16 1.222(4) . ?
 O3 C16 1.231(4) . ?
 N1 C1 1.368(4) . ?
 N1 C9 1.330(4) . ?
 C1 C2 1.416(4) . ?
 C1 C6 1.422(4) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.372(5) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.408(5) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.363(5) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.415(4) . ?
 C6 C7 1.428(4) . ?
 C7 C8 1.354(5) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.400(4) . ?
 C9 H9 0.9500 . ?
 C10 C11 1.386(5) . ?
 C10 C15 1.381(4) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.384(6) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.366(6) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.383(6) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.383(4) . ?
 C16 C17 1.568(4) . ?
 C17 H17A 0.9800 . ?
 C17 H17B 0.9800 . ?
 C17 H17C 0.9800 . ?
 O4 H4A 0.83(3) . ?
 O4 H4A 0.83(3) 2_655 ?
 O5 H5A 0.8503 . ?
 O5 H5A 0.85(14) 2_655 ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O2 Pd1 O2 180.00(5) . 5_666 ?
 O2 Pd1 N1 91.44(9) . . ?
 O2 Pd1 N1 88.56(9) . 5_666 ?
 O2 Pd1 N1 88.56(9) 5_666 . ?
 O2 Pd1 N1 91.44(9) 5_666 5_666 ?
 N1 Pd1 N1 180.0 5_666 . ?
 C7 O1 C10 116.6(2) . . ?
 C16 O2 Pd1 118.78(18) . . ?
 C1 N1 Pd1 123.10(19) . . ?
 C9 N1 Pd1 117.8(2) . . ?
 C9 N1 C1 119.0(3) . . ?
 N1 C1 C2 119.9(3) . . ?
 N1 C1 C6 120.9(3) . . ?
 C2 C1 C6 119.2(3) . . ?
 C1 C2 H2 120.3 . . ?
 C3 C2 C1 119.5(3) . . ?
 C3 C2 H2 120.3 . . ?
 C2 C3 H3 119.3 . . ?
 C2 C3 C4 121.3(3) . . ?
 C4 C3 H3 119.3 . . ?
 C3 C4 H4 119.9 . . ?
 C5 C4 C3 120.2(3) . . ?
 C5 C4 H4 119.9 . . ?
 C4 C5 H5 119.8 . . ?
 C4 C5 C6 120.3(3) . . ?
 C6 C5 H5 119.8 . . ?
 C1 C6 C7 117.7(3) . . ?
 C5 C6 C1 119.4(3) . . ?
 C5 C6 C7 122.9(3) . . ?
 O1 C7 C6 115.3(3) . . ?
 C8 C7 O1 124.8(3) . . ?
 C8 C7 C6 119.9(3) . . ?
 C7 C8 H8 120.5 . . ?
 C7 C8 C9 119.0(3) . . ?
 C9 C8 H8 120.5 . . ?
 N1 C9 C8 123.3(3) . . ?
 N1 C9 H9 118.3 . . ?
 C8 C9 H9 118.3 . . ?
 C11 C10 O1 118.8(3) . . ?
 C15 C10 O1 121.0(3) . . ?
 C15 C10 C11 120.1(3) . . ?
 C10 C11 H11 120.5 . . ?
 C12 C11 C10 119.1(4) . . ?
 C12 C11 H11 120.5 . . ?
 C11 C12 H12 119.7 . . ?
 C13 C12 C11 120.6(4) . . ?
 C13 C12 H12 119.7 . . ?
 C12 C13 H13 119.6 . . ?
 C12 C13 C14 120.8(3) . . ?
 C14 C13 H13 119.6 . . ?
 C13 C14 H14 120.5 . . ?
 C15 C14 C13 118.9(3) . . ?
 C15 C14 H14 120.5 . . ?
 C10 C15 Br1 119.7(2) . . ?
 C10 C15 C14 120.4(3) . . ?
 C14 C15 Br1 119.8(3) . . ?
 O2 C16 O3 130.2(3) . . ?
 O2 C16 C17 113.7(3) . . ?
 O3 C16 C17 116.1(3) . . ?
 C16 C17 H17A 109.5 . . ?
 C16 C17 H17B 109.5 . . ?
 C16 C17 H17C 109.5 . . ?
 H17A C17 H17B 109.5 . . ?
 H17A C17 H17C 109.5 . . ?
 H17B C17 H17C 109.5 . . ?
 H4A O4 H4A 112(5) . 2_655 ?
 H5A O5 H5A 99.4 . 2_655 ?

_olex2_diffrn_ambient_temperature_device  'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
 'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id  AH_05_408_Br
_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  2.924
_oxdiff_exptl_absorpt_empirical_full_min  0.550
data_2019acc0018_k1_100k
_audit_creation_date               2019-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2016/6'
loop_
  _audit_author_name
  _audit_author_email
  _audit_author_address
 'Light, M.E.' light@soton.ac.uk
;

University of Southampton
Chemistry
University Road Highfield
Southampton
;
 'McGlacken, G.' 'g.mcglacken@ucc.ie '
;

University College Cork 
Department of Chemistry 
Kane Building, College Road 
Cork
Ireland
;

_audit_contact_author_address
;
University of Southampton
Chemistry
University Road Highfield
Southampton
;
_audit_contact_author_email        light@soton.ac.uk
_audit_contact_author_name         'Light, M.E.'
_audit_contact_author_phone        02380599429
_publ_contact_author_id_orcid      0000-0002-0585-0843
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C34 H28 N2 O6 Pd'
_chemical_formula_sum              'C34 H28 N2 O6 Pd'
_chemical_formula_weight           666.98
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C12 H12 N2 O2 Pd1'
_chemical_oxdiff_usercomment       AH_05_410
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Pd' 'Pd' -0.9988 1.0072
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             60
_space_group_name_H-M_alt          'P b c n'
_space_group_name_Hall             '-P 2n 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y+1/2, z+1/2'
 '-x, y, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y-1/2, -z-1/2'
 'x, -y, z-1/2'
 '-x-1/2, y-1/2, z'

_cell_length_a                     18.3076(3)
_cell_length_b                     7.82700(10)
_cell_length_c                     22.6989(4)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       3252.61(9)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      11042
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        30.9870
_cell_measurement_theta_min        3.7450
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.615
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.53034
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear dark yellow'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     dark
_exptl_crystal_colour_primary      yellow
_exptl_crystal_density_diffrn      1.362
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1360
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 0 0 1 0.0603
 0 0 -1 0.0603
 -1 0 0 0.2605
 1 0 0 0.2605
 -1 -1 0 0.2175
 1 -1 0 0.1509
 -2 5 0 0.1813
 5 3 0 0.1534

_exptl_crystal_recrystallization_method 
 'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max            0.535
_exptl_crystal_size_mid            0.364
_exptl_crystal_size_min            0.121
loop_
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 0.0001 -0.0007 0.9991 -0.0113 -0.0291 -0.0002
 -0.0001 0.0007 -0.9991 0.0113 0.0291 0.0002
 -0.9988 -0.0001 0.0010 0.0079 -0.0028 -0.0378
 0.9988 0.0001 -0.0010 -0.0079 0.0028 0.0378
 -0.9978 -0.9989 -0.0042 0.0901 -0.0351 -0.0183
 0.9998 -0.9987 -0.0061 0.0744 -0.0294 0.0573
 -2.0026 4.9938 0.0277 -0.3955 0.1557 -0.1732
 4.9909 2.9967 0.0105 -0.2861 0.1110 0.1304

_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0299
_diffrn_reflns_av_unetI/netI       0.0193
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         23
_diffrn_reflns_limit_h_min         -24
_diffrn_reflns_limit_k_max         10
_diffrn_reflns_limit_k_min         -10
_diffrn_reflns_limit_l_max         29
_diffrn_reflns_limit_l_min         -30
_diffrn_reflns_number              25683
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.999
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.495
_diffrn_reflns_theta_min           2.969
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100(2)
_diffrn_detector                   'CCD area detector'
_diffrn_detector_area_resol_mean   28.5714
_diffrn_detector_type              'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -7.00  18.00   1.00    2.00    --    5.00  38.00-120.00   25
  2  ω    -81.00  16.00   1.00    2.00    --  -12.00 -57.00 150.00   97
  3  ω    -22.00  40.00   1.00    2.00    --  -12.00  38.00 120.00   62
  4  ω    -19.00  60.00   1.00    2.00    --  -12.00  57.00-180.00   79
;
_diffrn_measurement_device         'four-circle κ diffractometer'
_diffrn_measurement_device_type    'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2   'Rigaku AFC12 (Right)'
_diffrn_measurement_method         'profile data from ω-scans'
_diffrn_measurement_specimen_support  'MiTeGen MicroMesh'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0078940000
_diffrn_orient_matrix_UB_12        -0.0822996000
_diffrn_orient_matrix_UB_13        -0.0114034000
_diffrn_orient_matrix_UB_21        0.0028105000
_diffrn_orient_matrix_UB_22        0.0324571000
_diffrn_orient_matrix_UB_23        -0.0290973000
_diffrn_orient_matrix_UB_31        0.0378340000
_diffrn_orient_matrix_UB_32        -0.0194998000
_diffrn_orient_matrix_UB_33        -0.0002181000
_diffrn_radiation_collimation      0.3
_diffrn_radiation_monochromator    'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'Rotating-anode X-ray tube'
_diffrn_source_current             55.0
_diffrn_source_power               2.475
_diffrn_source_target              Mo
_diffrn_source_type                'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage             45.0
_diffrn_special_details            ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3937
_reflns_number_total               4132
_reflns_odcompleteness_completeness  99.68
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       28.64
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection         'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction          'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.423
_refine_diff_density_min           -0.367
_refine_diff_density_rms           0.073
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.251
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       197
_refine_ls_number_reflns           4132
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0586
_refine_ls_R_factor_gt             0.0561
_refine_ls_restrained_S_all        1.251
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0173P)²+7.3479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0984
_refine_ls_wR_factor_ref           0.0996
_refine_special_details           
 'Solvent masking was used for a suspected disordered methanol'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Pd1 Pd 0.500000 0.500000 0.500000 0.02236(9) Uani 1 2 d S T P . .
 O1 O 0.19221(11) 0.5036(3) 0.38978(9) 0.0337(5) Uani 1 1 d . . . . .
 O2 O 0.49058(12) 0.7476(3) 0.52158(10) 0.0304(5) Uani 1 1 d . . . . .
 O3 O 0.46185(15) 0.6757(3) 0.61309(11) 0.0450(6) Uani 1 1 d . . . . .
 N1 N 0.39799(12) 0.5046(3) 0.46593(10) 0.0231(5) Uani 1 1 d . . . . .
 C1 C 0.33911(14) 0.4331(4) 0.49475(12) 0.0206(5) Uani 1 1 d . . . . .
 C2 C 0.34888(16) 0.3596(4) 0.55089(12) 0.0257(6) Uani 1 1 d . . . . .
 H2 H 0.396148 0.355732 0.568107 0.031 Uiso 1 1 calc R . . . .
 C3 C 0.29008(18) 0.2936(4) 0.58062(13) 0.0304(7) Uani 1 1 d . . . . .
 H3 H 0.297156 0.242911 0.618205 0.036 Uiso 1 1 calc R . . . .
 C4 C 0.21952(17) 0.3000(4) 0.55635(14) 0.0313(7) Uani 1 1 d . . . . .
 H4 H 0.179252 0.255904 0.577935 0.038 Uiso 1 1 calc R . . . .
 C5 C 0.20862(16) 0.3693(4) 0.50173(12) 0.0271(6) Uani 1 1 d . . . . .
 H5 H 0.160847 0.372598 0.485414 0.033 Uiso 1 1 calc R . . . .
 C6 C 0.26832(15) 0.4364(4) 0.46938(12) 0.0220(5) Uani 1 1 d . . . . .
 C7 C 0.26084(15) 0.5101(4) 0.41234(12) 0.0253(6) Uani 1 1 d . . . . .
 C8 C 0.32003(16) 0.5824(4) 0.38529(12) 0.0246(6) Uani 1 1 d . . . . .
 H8 H 0.315439 0.635146 0.347776 0.029 Uiso 1 1 calc R . . . .
 C9 C 0.38747(15) 0.5770(4) 0.41418(12) 0.0245(6) Uani 1 1 d . . . . .
 H9 H 0.428217 0.628554 0.395338 0.029 Uiso 1 1 calc R . . . .
 C10 C 0.17928(16) 0.5598(4) 0.33211(14) 0.0290(6) Uani 1 1 d . . . . .
 C11 C 0.2142(2) 0.4881(5) 0.28437(15) 0.0392(8) Uani 1 1 d . . . . .
 H11 H 0.249740 0.400981 0.289429 0.047 Uiso 1 1 calc R . . . .
 C12 C 0.1958(3) 0.5472(6) 0.22857(17) 0.0555(11) Uani 1 1 d . . . . .
 H12 H 0.220052 0.502120 0.195008 0.067 Uiso 1 1 calc R . . . .
 C13 C 0.1426(3) 0.6708(6) 0.2213(2) 0.0673(15) Uani 1 1 d . . . . .
 H13 H 0.130163 0.709526 0.182928 0.081 Uiso 1 1 calc R . . . .
 C14 C 0.1079(2) 0.7373(6) 0.2696(2) 0.0644(14) Uani 1 1 d . . . . .
 H14 H 0.070779 0.820850 0.264359 0.077 Uiso 1 1 calc R . . . .
 C15 C 0.12612(18) 0.6843(5) 0.32581(19) 0.0430(9) Uani 1 1 d . . . . .
 H15 H 0.102722 0.732128 0.359327 0.052 Uiso 1 1 calc R . . . .
 C16 C 0.47443(15) 0.7822(4) 0.57464(14) 0.0285(6) Uani 1 1 d . . . . .
 C17 C 0.4709(2) 0.9718(4) 0.58860(17) 0.0437(9) Uani 1 1 d . . . . .
 H17A H 0.503495 1.034353 0.561987 0.066 Uiso 1 1 calc GR . . . .
 H17B H 0.486212 0.990825 0.629449 0.066 Uiso 1 1 calc GR . . . .
 H17C H 0.420715 1.012689 0.583370 0.066 Uiso 1 1 calc GR . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Pd1 O2 2.006(2) 5_666 ?
 Pd1 O2 2.006(2) . ?
 Pd1 N1 2.022(2) . ?
 Pd1 N1 2.022(2) 5_666 ?
 O1 C7 1.358(3) . ?
 O1 C10 1.401(4) . ?
 O2 C16 1.270(4) . ?
 O3 C16 1.229(4) . ?
 N1 C1 1.380(3) . ?
 N1 C9 1.318(4) . ?
 C1 C2 1.409(4) . ?
 C1 C6 1.418(4) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.371(4) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.405(4) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.368(4) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.417(4) . ?
 C6 C7 1.424(4) . ?
 C7 C8 1.368(4) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.399(4) . ?
 C9 H9 0.9500 . ?
 C10 C11 1.377(5) . ?
 C10 C15 1.384(5) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.390(5) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.382(7) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.369(7) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.384(6) . ?
 C15 H15 0.9500 . ?
 C16 C17 1.519(5) . ?
 C17 H17A 0.9800 . ?
 C17 H17B 0.9800 . ?
 C17 H17C 0.9800 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O2 Pd1 O2 180.0 5_666 . ?
 O2 Pd1 N1 90.19(9) . 5_666 ?
 O2 Pd1 N1 89.81(9) . . ?
 O2 Pd1 N1 89.81(9) 5_666 5_666 ?
 O2 Pd1 N1 90.19(9) 5_666 . ?
 N1 Pd1 N1 180.0 . 5_666 ?
 C7 O1 C10 119.8(2) . . ?
 C16 O2 Pd1 117.3(2) . . ?
 C1 N1 Pd1 122.22(19) . . ?
 C9 N1 Pd1 118.92(19) . . ?
 C9 N1 C1 118.9(2) . . ?
 N1 C1 C2 119.7(2) . . ?
 N1 C1 C6 120.9(2) . . ?
 C2 C1 C6 119.4(3) . . ?
 C1 C2 H2 120.0 . . ?
 C3 C2 C1 119.9(3) . . ?
 C3 C2 H2 120.0 . . ?
 C2 C3 H3 119.5 . . ?
 C2 C3 C4 121.0(3) . . ?
 C4 C3 H3 119.5 . . ?
 C3 C4 H4 119.9 . . ?
 C5 C4 C3 120.2(3) . . ?
 C5 C4 H4 119.9 . . ?
 C4 C5 H5 119.9 . . ?
 C4 C5 C6 120.3(3) . . ?
 C6 C5 H5 119.9 . . ?
 C1 C6 C7 117.7(2) . . ?
 C5 C6 C1 119.2(3) . . ?
 C5 C6 C7 123.1(3) . . ?
 O1 C7 C6 114.6(3) . . ?
 O1 C7 C8 125.4(3) . . ?
 C8 C7 C6 120.0(3) . . ?
 C7 C8 H8 120.8 . . ?
 C7 C8 C9 118.4(3) . . ?
 C9 C8 H8 120.8 . . ?
 N1 C9 C8 124.1(3) . . ?
 N1 C9 H9 118.0 . . ?
 C8 C9 H9 118.0 . . ?
 C11 C10 O1 121.9(3) . . ?
 C11 C10 C15 122.1(3) . . ?
 C15 C10 O1 115.9(3) . . ?
 C10 C11 H11 121.0 . . ?
 C10 C11 C12 118.0(4) . . ?
 C12 C11 H11 121.0 . . ?
 C11 C12 H12 119.6 . . ?
 C13 C12 C11 120.8(4) . . ?
 C13 C12 H12 119.6 . . ?
 C12 C13 H13 120.1 . . ?
 C14 C13 C12 119.8(4) . . ?
 C14 C13 H13 120.1 . . ?
 C13 C14 H14 119.6 . . ?
 C13 C14 C15 120.8(4) . . ?
 C15 C14 H14 119.6 . . ?
 C10 C15 H15 120.8 . . ?
 C14 C15 C10 118.4(4) . . ?
 C14 C15 H15 120.8 . . ?
 O2 C16 C17 114.6(3) . . ?
 O3 C16 O2 124.9(3) . . ?
 O3 C16 C17 120.5(3) . . ?
 C16 C17 H17A 109.5 . . ?
 C16 C17 H17B 109.5 . . ?
 C16 C17 H17C 109.5 . . ?
 H17A C17 H17B 109.5 . . ?
 H17A C17 H17C 109.5 . . ?
 H17B C17 H17C 109.5 . . ?

_smtbx_masks_special_details       ?
loop_
  _smtbx_masks_void_nr
  _smtbx_masks_void_average_x
  _smtbx_masks_void_average_y
  _smtbx_masks_void_average_z
  _smtbx_masks_void_volume
  _smtbx_masks_void_count_electrons
  _smtbx_masks_void_content
 1 0.000 0.198 0.250 138.0 30.3 methanol
 2 0.000 -0.198 0.750 138.0 30.1 methanol
 3 0.500 0.302 0.750 138.0 30.3 methanol
 4 0.500 0.698 0.250 138.0 30.1 methanol

_olex2_diffrn_ambient_temperature_device  'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
 'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id  AH_05_410
_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  1.475
_oxdiff_exptl_absorpt_empirical_full_min  0.583
