data_22019779_0m
_audit_creation_date               2019-07-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_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           'C18 H15 N O2'
_chemical_formula_sum              'C18 H15 N O2'
_chemical_formula_weight           277.31
_chemical_melting_point            ?
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                     3.999(2)
_cell_length_b                     18.448(10)
_cell_length_c                     18.493(11)
_cell_angle_alpha                  90
_cell_angle_beta                   90.662(19)
_cell_angle_gamma                  90
_cell_volume                       1364.3(13)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      2233
_cell_measurement_temperature      298
_cell_measurement_theta_max        26.735
_cell_measurement_theta_min        2.464
_shelx_estimated_absorpt_T_max     0.993
_shelx_estimated_absorpt_T_min     0.987
_exptl_absorpt_coefficient_mu      0.088
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.5062
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1377 before and 0.0779 after correction. The Ratio of minimum to maximum transmission is 0.6789. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.350
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               584
_exptl_crystal_size_max            0.15
_exptl_crystal_size_mid            0.12
_exptl_crystal_size_min            0.08
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.1037
_diffrn_reflns_av_unetI/netI       0.0776
_diffrn_reflns_Laue_measured_fraction_full  0.995
_diffrn_reflns_Laue_measured_fraction_max  0.995
_diffrn_reflns_limit_h_max         4
_diffrn_reflns_limit_h_min         -4
_diffrn_reflns_limit_k_max         21
_diffrn_reflns_limit_k_min         -21
_diffrn_reflns_limit_l_max         22
_diffrn_reflns_limit_l_min         -21
_diffrn_reflns_number              11590
_diffrn_reflns_point_group_measured_fraction_full  0.995
_diffrn_reflns_point_group_measured_fraction_max  0.995
_diffrn_reflns_theta_full          25.022
_diffrn_reflns_theta_max           25.022
_diffrn_reflns_theta_min           2.464
_diffrn_ambient_temperature        298
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.995
_diffrn_measured_fraction_theta_max  0.995
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1583
_reflns_number_total               2397
_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         'SAINT V8.38A (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (?, 2016)'
_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           0.164
_refine_diff_density_min           -0.181
_refine_diff_density_rms           0.044
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.074
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       191
_refine_ls_number_reflns           2397
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0986
_refine_ls_R_factor_gt             0.0590
_refine_ls_restrained_S_all        1.074
_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)+(0.0436P)²+0.4425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1253
_refine_ls_wR_factor_ref           0.1434
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C13(H13), C6(H6), C5(H5), C3(H3), C4(H4)
2.c 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
 O1 O 0.6444(5) 0.49816(10) 0.70006(9) 0.0473(5) Uani 1 1 d . . . . .
 O2 O 0.5769(5) 0.34817(10) 0.50550(9) 0.0481(5) Uani 1 1 d . . . . .
 N1 N 0.6024(5) 0.42332(12) 0.60436(11) 0.0420(6) Uani 1 1 d . . . . .
 C10 C 0.3308(6) 0.31219(14) 0.69045(14) 0.0371(6) Uani 1 1 d . . . . .
 C15 C 0.3584(6) 0.30380(14) 0.61453(14) 0.0381(6) Uani 1 1 d . . . . .
 C8 C 0.4582(6) 0.37698(14) 0.72334(13) 0.0367(6) Uani 1 1 d . . . . .
 C9 C 0.5590(6) 0.43057(14) 0.67623(14) 0.0382(6) Uani 1 1 d . . . . .
 C11 C 0.1662(6) 0.25642(14) 0.72839(15) 0.0437(7) Uani 1 1 d . . . . .
 H11 H 0.141606 0.260353 0.778179 0.052 Uiso 1 1 calc R . . . .
 C16 C 0.5194(6) 0.36111(15) 0.57604(14) 0.0397(6) Uani 1 1 d . . . . .
 C12 C 0.0433(7) 0.19725(16) 0.69361(17) 0.0516(8) Uani 1 1 d . . . . .
 H12 H -0.065620 0.161543 0.719902 0.062 Uiso 1 1 calc R . . . .
 C7 C 0.5203(6) 0.38977(15) 0.80120(14) 0.0401(7) Uani 1 1 d . . . . .
 C14 C 0.2325(7) 0.24164(15) 0.57986(15) 0.0457(7) Uani 1 1 d . . . . .
 H14 H 0.254815 0.236344 0.530139 0.055 Uiso 1 1 calc R . . . .
 C2 C 0.5496(7) 0.46196(16) 0.82314(15) 0.0453(7) Uani 1 1 d . . . . .
 C13 C 0.0775(7) 0.18902(16) 0.61898(17) 0.0520(8) Uani 1 1 d . . . . .
 H13 H -0.005213 0.147788 0.596032 0.062 Uiso 1 1 calc R . . . .
 C1 C 0.4813(7) 0.51749(16) 0.76644(15) 0.0512(8) Uani 1 1 d . . . . .
 H1A H 0.242126 0.521208 0.757955 0.061 Uiso 1 1 calc R . . . .
 H1B H 0.561876 0.564344 0.782853 0.061 Uiso 1 1 calc R . . . .
 C6 C 0.5903(7) 0.33542(17) 0.85207(14) 0.0490(7) Uani 1 1 d . . . . .
 H6 H 0.574905 0.286932 0.838688 0.059 Uiso 1 1 calc R . . . .
 C18 C 0.7449(8) 0.40427(16) 0.46453(14) 0.0515(8) Uani 1 1 d . . . . .
 H18A H 0.941828 0.421089 0.490641 0.062 Uiso 1 1 calc R . . . .
 H18B H 0.596427 0.445164 0.456679 0.062 Uiso 1 1 calc R . . . .
 C5 C 0.6825(8) 0.3536(2) 0.92229(16) 0.0606(9) Uani 1 1 d . . . . .
 H5 H 0.727237 0.317019 0.955661 0.073 Uiso 1 1 calc R . . . .
 C3 C 0.6445(8) 0.47886(19) 0.89328(17) 0.0623(9) Uani 1 1 d . . . . .
 H3 H 0.665450 0.527169 0.906991 0.075 Uiso 1 1 calc R . . . .
 C17 C 0.8421(9) 0.37166(18) 0.39372(15) 0.0616(9) Uani 1 1 d . . . . .
 H17A H 0.961867 0.406873 0.365899 0.092 Uiso 1 1 calc GR . . . .
 H17B H 0.644706 0.356990 0.367584 0.092 Uiso 1 1 calc GR . . . .
 H17C H 0.982252 0.330210 0.402258 0.092 Uiso 1 1 calc GR . . . .
 C4 C 0.7085(9) 0.4248(2) 0.94318(17) 0.0686(10) Uani 1 1 d . . . . .
 H4 H 0.768573 0.436472 0.990491 0.082 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 C9 1.364(3) . ?
 O1 C1 1.441(3) . ?
 O2 C16 1.349(3) . ?
 O2 C18 1.452(3) . ?
 N1 C9 1.349(3) . ?
 N1 C16 1.303(3) . ?
 C10 C15 1.418(4) . ?
 C10 C8 1.432(4) . ?
 C10 C11 1.412(4) . ?
 C15 C16 1.432(4) . ?
 C15 C14 1.404(4) . ?
 C8 C9 1.381(4) . ?
 C8 C7 1.477(4) . ?
 C11 H11 0.9300 . ?
 C11 C12 1.356(4) . ?
 C12 H12 0.9300 . ?
 C12 C13 1.397(4) . ?
 C7 C2 1.397(4) . ?
 C7 C6 1.401(4) . ?
 C14 H14 0.9300 . ?
 C14 C13 1.364(4) . ?
 C2 C1 1.489(4) . ?
 C2 C3 1.383(4) . ?
 C13 H13 0.9300 . ?
 C1 H1A 0.9700 . ?
 C1 H1B 0.9700 . ?
 C6 H6 0.9300 . ?
 C6 C5 1.387(4) . ?
 C18 H18A 0.9700 . ?
 C18 H18B 0.9700 . ?
 C18 C17 1.497(4) . ?
 C5 H5 0.9300 . ?
 C5 C4 1.373(5) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.381(5) . ?
 C17 H17A 0.9600 . ?
 C17 H17B 0.9600 . ?
 C17 H17C 0.9600 . ?
 C4 H4 0.9300 . ?

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
 C9 O1 C1 112.8(2) . . ?
 C16 O2 C18 117.6(2) . . ?
 C16 N1 C9 116.6(2) . . ?
 C15 C10 C8 118.7(2) . . ?
 C11 C10 C15 117.0(2) . . ?
 C11 C10 C8 124.2(2) . . ?
 C10 C15 C16 116.9(2) . . ?
 C14 C15 C10 120.6(2) . . ?
 C14 C15 C16 122.5(2) . . ?
 C10 C8 C7 127.0(2) . . ?
 C9 C8 C10 115.8(2) . . ?
 C9 C8 C7 117.0(2) . . ?
 O1 C9 C8 121.6(2) . . ?
 N1 C9 O1 112.0(2) . . ?
 N1 C9 C8 126.3(2) . . ?
 C10 C11 H11 119.4 . . ?
 C12 C11 C10 121.3(3) . . ?
 C12 C11 H11 119.4 . . ?
 O2 C16 C15 115.7(2) . . ?
 N1 C16 O2 120.0(2) . . ?
 N1 C16 C15 124.4(2) . . ?
 C11 C12 H12 119.4 . . ?
 C11 C12 C13 121.1(3) . . ?
 C13 C12 H12 119.4 . . ?
 C2 C7 C8 116.6(2) . . ?
 C2 C7 C6 118.2(3) . . ?
 C6 C7 C8 124.8(3) . . ?
 C15 C14 H14 119.9 . . ?
 C13 C14 C15 120.1(3) . . ?
 C13 C14 H14 119.9 . . ?
 C7 C2 C1 115.9(2) . . ?
 C3 C2 C7 120.6(3) . . ?
 C3 C2 C1 123.5(3) . . ?
 C12 C13 H13 120.1 . . ?
 C14 C13 C12 119.8(3) . . ?
 C14 C13 H13 120.1 . . ?
 O1 C1 C2 110.4(2) . . ?
 O1 C1 H1A 109.6 . . ?
 O1 C1 H1B 109.6 . . ?
 C2 C1 H1A 109.6 . . ?
 C2 C1 H1B 109.6 . . ?
 H1A C1 H1B 108.1 . . ?
 C7 C6 H6 119.8 . . ?
 C5 C6 C7 120.3(3) . . ?
 C5 C6 H6 119.8 . . ?
 O2 C18 H18A 110.3 . . ?
 O2 C18 H18B 110.3 . . ?
 O2 C18 C17 107.3(2) . . ?
 H18A C18 H18B 108.5 . . ?
 C17 C18 H18A 110.3 . . ?
 C17 C18 H18B 110.3 . . ?
 C6 C5 H5 119.6 . . ?
 C4 C5 C6 120.9(3) . . ?
 C4 C5 H5 119.6 . . ?
 C2 C3 H3 119.6 . . ?
 C4 C3 C2 120.7(3) . . ?
 C4 C3 H3 119.6 . . ?
 C18 C17 H17A 109.5 . . ?
 C18 C17 H17B 109.5 . . ?
 C18 C17 H17C 109.5 . . ?
 H17A C17 H17B 109.5 . . ?
 H17A C17 H17C 109.5 . . ?
 H17B C17 H17C 109.5 . . ?
 C5 C4 C3 119.4(3) . . ?
 C5 C4 H4 120.3 . . ?
 C3 C4 H4 120.3 . . ?


_olex2_submission_special_instructions  'No special instructions were received'
