data_9827-11378_ca203ii
_audit_creation_date               2018-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_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           'C16 H14 N2 O'
_chemical_formula_sum              'C16 H14 N2 O'
_chemical_formula_weight           250.29
_chemical_melting_point            ?
_chemical_oxdiff_formula           'O N2 C16'
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 '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                     12.8072(7)
_cell_length_b                     6.0525(4)
_cell_length_c                     16.8346(9)
_cell_angle_alpha                  90
_cell_angle_beta                   91.053(5)
_cell_angle_gamma                  90
_cell_volume                       1304.72(13)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      2935
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        75.1690
_cell_measurement_theta_min        6.1980
_shelx_estimated_absorpt_T_max     0.743
_shelx_estimated_absorpt_T_min     0.703
_exptl_absorpt_coefficient_mu      0.643
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.58862
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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      1.274
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         ?
_exptl_crystal_F_000               528
_exptl_crystal_preparation         ?
_exptl_crystal_size_max            0.59
_exptl_crystal_size_mid            0.5
_exptl_crystal_size_min            0.49
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0230
_diffrn_reflns_av_unetI/netI       0.0242
_diffrn_reflns_Laue_measured_fraction_full  0.956
_diffrn_reflns_Laue_measured_fraction_max  0.921
_diffrn_reflns_limit_h_max         15
_diffrn_reflns_limit_h_min         -15
_diffrn_reflns_limit_k_max         6
_diffrn_reflns_limit_k_min         -7
_diffrn_reflns_limit_l_max         19
_diffrn_reflns_limit_l_min         -20
_diffrn_reflns_number              4425
_diffrn_reflns_point_group_measured_fraction_full  0.956
_diffrn_reflns_point_group_measured_fraction_max  0.921
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           76.141
_diffrn_reflns_theta_min           3.452
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100(2)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   10.3829
_diffrn_detector_type              Atlas
_diffrn_measured_fraction_theta_full  0.956
_diffrn_measured_fraction_theta_max  0.921
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -114.00 -25.00   1.00    1.00    --  -40.38 -57.00 -60.00   89
  2  ω   -119.00 -13.00   1.00    1.00    --  -40.38 -77.00-150.00  106
  3  ω     33.00 108.00   1.00    1.00    --  113.00 -95.00  60.00   75
  4  ω     92.00 131.00   1.00    1.00    --  113.00 -45.00 150.00   39
  5  ω     42.00  74.00   1.00    1.00    --  113.00 -45.00 150.00   32
  6  ω    117.00 175.00   1.00    1.00    --  113.00 112.00   0.00   58
  7  ω    144.00 170.00   1.00    1.00    --  113.00 112.00 -90.00   26
  8  ω    112.00 147.00   1.00    1.00    --  113.00  77.00-120.00   35
  9  ω    101.00 165.00   1.00    1.00    --  113.00 112.00-120.00   64
 10  ω     58.00 107.00   1.00    1.00    --   40.38 178.00-150.00   49
 11  ω     57.00 134.00   1.00    1.00    --  113.00 178.00  60.00   77
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        0.0622609000
_diffrn_orient_matrix_UB_12        -0.2130258000
_diffrn_orient_matrix_UB_13        0.0166679000
_diffrn_orient_matrix_UB_21        -0.0745202000
_diffrn_orient_matrix_UB_22        -0.0582762000
_diffrn_orient_matrix_UB_23        0.0676154000
_diffrn_orient_matrix_UB_31        -0.0708525000
_diffrn_orient_matrix_UB_32        -0.1271105000
_diffrn_orient_matrix_UB_33        -0.0593540000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Cu) X-ray Source'
_diffrn_special_details            ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2261
_reflns_number_total               2516
_reflns_odcompleteness_completeness  94.76
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       72.42
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection         'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction          'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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           0.234
_refine_diff_density_min           -0.252
_refine_diff_density_rms           0.054
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.032
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       173
_refine_ls_number_reflns           2516
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0466
_refine_ls_R_factor_gt             0.0428
_refine_ls_restrained_S_all        1.032
_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)+(0.0679P)²+0.3686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1110
_refine_ls_wR_factor_ref           0.1147
_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 Ternary CH refined with riding coordinates:
 C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C16(H16), C10(H10), C12(H12), C7(H7), C8(H8), C15(H15), C9(H9),
 C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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 0.49658(7) 0.80090(17) 0.85226(6) 0.0247(2) Uani 1 1 d . . . . .
 N1 N 0.65673(8) 0.90814(19) 0.82483(6) 0.0197(2) Uani 1 1 d . . . . .
 N2 N 0.54034(8) 0.63297(19) 0.80388(7) 0.0227(3) Uani 1 1 d . . . . .
 C5 C 0.81403(8) 0.5533(2) 0.79046(7) 0.0178(3) Uani 1 1 d . . . . .
 C2 C 0.63406(9) 0.7066(2) 0.79072(7) 0.0170(3) Uani 1 1 d . . . . .
 C11 C 0.72565(8) 0.6562(2) 0.65989(7) 0.0180(3) Uani 1 1 d . . . . .
 C1 C 0.57117(9) 0.9556(2) 0.86112(7) 0.0207(3) Uani 1 1 d . . . . .
 C6 C 0.88334(9) 0.7304(2) 0.79268(8) 0.0212(3) Uani 1 1 d . . . . .
 H6 H 0.8673 0.8616 0.7640 0.025 Uiso 1 1 calc R . . . .
 C16 C 0.69833(9) 0.8672(2) 0.63517(8) 0.0226(3) Uani 1 1 d . . . . .
 H16 H 0.6688 0.9682 0.6717 0.027 Uiso 1 1 calc R . . . .
 C10 C 0.83896(9) 0.3607(2) 0.83166(8) 0.0218(3) Uani 1 1 d . . . . .
 H10 H 0.7926 0.2383 0.8298 0.026 Uiso 1 1 calc R . . . .
 C3 C 0.71041(9) 0.5717(2) 0.74435(7) 0.0174(3) Uani 1 1 d . . . . .
 H3 H 0.6810 0.4190 0.7398 0.021 Uiso 1 1 calc R . . . .
 C12 C 0.76960(10) 0.5107(3) 0.60552(8) 0.0249(3) Uani 1 1 d . . . . .
 H12 H 0.7887 0.3659 0.6219 0.030 Uiso 1 1 calc R . . . .
 C7 C 0.97611(9) 0.7159(3) 0.83674(8) 0.0265(3) Uani 1 1 d . . . . .
 H7 H 1.0232 0.8372 0.8381 0.032 Uiso 1 1 calc R . . . .
 C8 C 0.99984(10) 0.5248(3) 0.87862(8) 0.0285(3) Uani 1 1 d . . . . .
 H8 H 1.0627 0.5159 0.9093 0.034 Uiso 1 1 calc R . . . .
 C15 C 0.71420(10) 0.9314(3) 0.55657(8) 0.0279(3) Uani 1 1 d . . . . .
 H15 H 0.6946 1.0757 0.5398 0.033 Uiso 1 1 calc R . . . .
 C9 C 0.93206(10) 0.3470(3) 0.87582(8) 0.0273(3) Uani 1 1 d . . . . .
 H9 H 0.9489 0.2153 0.9040 0.033 Uiso 1 1 calc R . . . .
 C13 C 0.78554(11) 0.5761(3) 0.52768(8) 0.0322(4) Uani 1 1 d . . . . .
 H13 H 0.8154 0.4759 0.4911 0.039 Uiso 1 1 calc R . . . .
 C4 C 0.54794(11) 1.1494(3) 0.91091(9) 0.0293(3) Uani 1 1 d . . . . .
 H4A H 0.5504 1.2836 0.8784 0.044 Uiso 1 1 calc GR . . . .
 H4B H 0.5999 1.1599 0.9542 0.044 Uiso 1 1 calc GR . . . .
 H4C H 0.4782 1.1334 0.9331 0.044 Uiso 1 1 calc GR . . . .
 C14 C 0.75801(11) 0.7873(3) 0.50301(8) 0.0316(4) Uani 1 1 d . . . . .
 H14 H 0.7692 0.8323 0.4498 0.038 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 N2 1.4238(14) . ?
 O1 C1 1.3441(16) . ?
 N1 C2 1.3770(17) . ?
 N1 C1 1.2966(16) . ?
 N2 C2 1.3030(16) . ?
 C5 C6 1.3919(18) . ?
 C5 C10 1.3904(18) . ?
 C5 C3 1.5292(15) . ?
 C2 C3 1.5035(16) . ?
 C11 C16 1.3863(18) . ?
 C11 C3 1.5269(17) . ?
 C11 C12 1.3960(18) . ?
 C1 C4 1.4749(19) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.3918(18) . ?
 C16 H16 0.9500 . ?
 C16 C15 1.3974(18) . ?
 C10 H10 0.9500 . ?
 C10 C9 1.3960(18) . ?
 C3 H3 1.0000 . ?
 C12 H12 0.9500 . ?
 C12 C13 1.387(2) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.385(2) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.383(2) . ?
 C15 H15 0.9500 . ?
 C15 C14 1.381(2) . ?
 C9 H9 0.9500 . ?
 C13 H13 0.9500 . ?
 C13 C14 1.387(2) . ?
 C4 H4A 0.9800 . ?
 C4 H4B 0.9800 . ?
 C4 H4C 0.9800 . ?
 C14 H14 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
 C1 O1 N2 105.93(9) . . ?
 C1 N1 C2 102.66(11) . . ?
 C2 N2 O1 103.10(10) . . ?
 C6 C5 C3 120.31(11) . . ?
 C10 C5 C6 119.45(11) . . ?
 C10 C5 C3 120.23(11) . . ?
 N1 C2 C3 124.29(10) . . ?
 N2 C2 N1 114.83(11) . . ?
 N2 C2 C3 120.83(12) . . ?
 C16 C11 C3 123.53(11) . . ?
 C16 C11 C12 119.12(12) . . ?
 C12 C11 C3 117.34(12) . . ?
 O1 C1 C4 117.82(11) . . ?
 N1 C1 O1 113.48(12) . . ?
 N1 C1 C4 128.69(13) . . ?
 C5 C6 H6 119.9 . . ?
 C7 C6 C5 120.24(12) . . ?
 C7 C6 H6 119.9 . . ?
 C11 C16 H16 120.0 . . ?
 C11 C16 C15 120.00(13) . . ?
 C15 C16 H16 120.0 . . ?
 C5 C10 H10 119.9 . . ?
 C5 C10 C9 120.11(12) . . ?
 C9 C10 H10 119.9 . . ?
 C5 C3 H3 107.1 . . ?
 C2 C3 C5 110.04(10) . . ?
 C2 C3 C11 113.39(10) . . ?
 C2 C3 H3 107.1 . . ?
 C11 C3 C5 111.87(9) . . ?
 C11 C3 H3 107.1 . . ?
 C11 C12 H12 119.7 . . ?
 C13 C12 C11 120.50(14) . . ?
 C13 C12 H12 119.7 . . ?
 C6 C7 H7 120.0 . . ?
 C8 C7 C6 120.06(13) . . ?
 C8 C7 H7 120.0 . . ?
 C7 C8 H8 120.0 . . ?
 C9 C8 C7 120.05(12) . . ?
 C9 C8 H8 120.0 . . ?
 C16 C15 H15 119.7 . . ?
 C14 C15 C16 120.70(14) . . ?
 C14 C15 H15 119.7 . . ?
 C10 C9 H9 120.0 . . ?
 C8 C9 C10 120.07(13) . . ?
 C8 C9 H9 120.0 . . ?
 C12 C13 H13 119.9 . . ?
 C14 C13 C12 120.30(14) . . ?
 C14 C13 H13 119.9 . . ?
 C1 C4 H4A 109.5 . . ?
 C1 C4 H4B 109.5 . . ?
 C1 C4 H4C 109.5 . . ?
 H4A C4 H4B 109.5 . . ?
 H4A C4 H4C 109.5 . . ?
 H4B C4 H4C 109.5 . . ?
 C15 C14 C13 119.37(13) . . ?
 C15 C14 H14 120.3 . . ?
 C13 C14 H14 120.3 . . ?

_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  3.957
_oxdiff_exptl_absorpt_empirical_full_min  0.331
