data_01_a
_audit_creation_date               2023-09-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_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
;
Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2015). Acta Cryst. A71, 59-75.

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. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C19 H14 Cl N O'
_chemical_formula_sum              'C19 H14 Cl N O'
_chemical_formula_weight           307.76
_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' 0.0148 0.0070 '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'
 'Cl' 'Cl' 0.3294 0.5404 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0412 0.0250 '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/n 1'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                     7.4040(6)
_cell_length_b                     14.9600(13)
_cell_length_c                     13.7178(12)
_cell_angle_alpha                  90
_cell_angle_beta                   92.581(4)
_cell_angle_gamma                  90
_cell_volume                       1517.9(2)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      7134
_cell_measurement_temperature      260.0
_cell_measurement_theta_max        57.143
_cell_measurement_theta_min        3.805
_shelx_estimated_absorpt_T_max     0.845
_shelx_estimated_absorpt_T_min     0.760
_exptl_absorpt_coefficient_mu      1.448
_exptl_absorpt_correction_T_max    0.7512
_exptl_absorpt_correction_T_min    0.4088
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1694 before and 0.0880 after correction.
The Ratio of minimum to maximum transmission is 0.5442.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear yellowish yellow'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     yellowish
_exptl_crystal_colour_primary      yellow
_exptl_crystal_density_diffrn      1.347
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               640
_exptl_crystal_size_max            0.2
_exptl_crystal_size_mid            0.15
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0802
_diffrn_reflns_av_unetI/netI       0.0633
_diffrn_reflns_Laue_measured_fraction_full  0.991
_diffrn_reflns_Laue_measured_fraction_max  0.986
_diffrn_reflns_limit_h_max         9
_diffrn_reflns_limit_h_min         -9
_diffrn_reflns_limit_k_max         18
_diffrn_reflns_limit_k_min         -18
_diffrn_reflns_limit_l_max         17
_diffrn_reflns_limit_l_min         -16
_diffrn_reflns_number              12632
_diffrn_reflns_point_group_measured_fraction_full  0.991
_diffrn_reflns_point_group_measured_fraction_max  0.986
_diffrn_reflns_theta_full          53.594
_diffrn_reflns_theta_max           57.270
_diffrn_reflns_theta_min           3.806
_diffrn_ambient_temperature        260.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.991
_diffrn_measured_fraction_theta_max  0.986
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             GaK\a
_diffrn_radiation_wavelength       1.34139
_diffrn_source                     ?
_diffrn_source_current             2.86
_diffrn_source_power               0.1998568
_diffrn_source_voltage             69.88
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2501
_reflns_number_total               3089
_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 V8.40B (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max           0.385
_refine_diff_density_min           -0.281
_refine_diff_density_rms           0.082
_refine_ls_extinction_coef         0.021(3)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.139
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       200
_refine_ls_number_reflns           3089
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0690
_refine_ls_R_factor_gt             0.0579
_refine_ls_restrained_S_all        1.139
_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)+(0.0754P)²+0.2469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1406
_refine_ls_wR_factor_ref           0.1531
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C11(H11), C12(H12),
 C13(H13), C15(H15), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       iterative
_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
 Cl1 Cl -0.25427(8) 0.26888(4) 0.72483(5) 0.0696(3) Uani 1 1 d . . . . .
 O1 O 0.67063(19) 0.65013(9) 0.44065(12) 0.0576(4) Uani 1 1 d . . . . .
 N1 N 0.1354(2) 0.52203(9) 0.60615(13) 0.0461(4) Uani 1 1 d . . . . .
 H1 H 0.193895 0.479598 0.579354 0.055 Uiso 1 1 calc R U . . .
 C1 C 0.5364(3) 0.87530(12) 0.42459(15) 0.0507(5) Uani 1 1 d . . . . .
 H1A H 0.412729 0.865444 0.427612 0.061 Uiso 1 1 calc R U . . .
 C2 C 0.5989(4) 0.95827(15) 0.39646(17) 0.0676(7) Uani 1 1 d . . . . .
 H2 H 0.517210 1.003320 0.378821 0.081 Uiso 1 1 calc R U . . .
 C3 C 0.7804(5) 0.97386(17) 0.3946(2) 0.0875(10) Uani 1 1 d . . . . .
 H3 H 0.822169 1.029985 0.377168 0.105 Uiso 1 1 calc R U . . .
 C4 C 0.9015(4) 0.9070(2) 0.4185(2) 0.0871(10) Uani 1 1 d . . . . .
 H4 H 1.024929 0.918209 0.417386 0.105 Uiso 1 1 calc R U . . .
 C5 C 0.8408(3) 0.82246(17) 0.44446(19) 0.0643(6) Uani 1 1 d . . . . .
 H5 H 0.923172 0.776920 0.459063 0.077 Uiso 1 1 calc R U . . .
 C6 C 0.6568(3) 0.80682(12) 0.44830(14) 0.0452(5) Uani 1 1 d . . . . .
 C7 C 0.5935(3) 0.71509(12) 0.47270(15) 0.0424(4) Uani 1 1 d . . . . .
 C8 C 0.4395(2) 0.70390(11) 0.53844(13) 0.0384(4) Uani 1 1 d . . . . .
 C9 C 0.3494(2) 0.62219(11) 0.53916(13) 0.0379(4) Uani 1 1 d . . . . .
 H9 H 0.378696 0.577955 0.494922 0.046 Uiso 1 1 calc R U . . .
 C10 C 0.2160(2) 0.60595(11) 0.60537(13) 0.0374(4) Uani 1 1 d . . . . .
 C11 C 0.1775(3) 0.67280(12) 0.67266(14) 0.0429(4) Uani 1 1 d . . . . .
 H11 H 0.092334 0.662350 0.719130 0.051 Uiso 1 1 calc R U . . .
 C12 C 0.2648(3) 0.75382(12) 0.67055(15) 0.0471(5) Uani 1 1 d . . . . .
 H12 H 0.235579 0.798022 0.714833 0.057 Uiso 1 1 calc R U . . .
 C13 C 0.3954(3) 0.77097(12) 0.60370(15) 0.0447(5) Uani 1 1 d . . . . .
 H13 H 0.452672 0.826271 0.602456 0.054 Uiso 1 1 calc R U . . .
 C14 C -0.0286(2) 0.49823(11) 0.64507(13) 0.0380(4) Uani 1 1 d . . . . .
 C15 C -0.0563(3) 0.40813(11) 0.66670(14) 0.0413(4) Uani 1 1 d . . . . .
 H15 H 0.033634 0.366196 0.656474 0.050 Uiso 1 1 calc R U . . .
 C16 C -0.2188(3) 0.38205(14) 0.70347(15) 0.0470(5) Uani 1 1 d . . . . .
 C17 C -0.3542(3) 0.44199(16) 0.72261(17) 0.0553(6) Uani 1 1 d . . . . .
 H17 H -0.460441 0.423371 0.750060 0.066 Uiso 1 1 calc R U . . .
 C18 C -0.3263(3) 0.53082(15) 0.69954(17) 0.0533(5) Uani 1 1 d . . . . .
 H18 H -0.416015 0.572480 0.711298 0.064 Uiso 1 1 calc R U . . .
 C19 C -0.1683(3) 0.55898(13) 0.65945(15) 0.0453(5) Uani 1 1 d . . . . .
 H19 H -0.154859 0.618585 0.641938 0.054 Uiso 1 1 calc R U . . .


_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
 Cl1 C16 1.740(2) . ?
 O1 C7 1.219(2) . ?
 N1 H1 0.8600 . ?
 N1 C10 1.390(2) . ?
 N1 C14 1.395(2) . ?
 C1 H1A 0.9300 . ?
 C1 C2 1.386(3) . ?
 C1 C6 1.387(3) . ?
 C2 H2 0.9300 . ?
 C2 C3 1.365(5) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.373(5) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.394(4) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.386(3) . ?
 C6 C7 1.493(2) . ?
 C7 C8 1.495(2) . ?
 C8 C9 1.393(2) . ?
 C8 C13 1.393(3) . ?
 C9 H9 0.9300 . ?
 C9 C10 1.393(2) . ?
 C10 C11 1.399(3) . ?
 C11 H11 0.9300 . ?
 C11 C12 1.374(3) . ?
 C12 H12 0.9300 . ?
 C12 C13 1.387(3) . ?
 C13 H13 0.9300 . ?
 C14 C15 1.397(2) . ?
 C14 C19 1.398(3) . ?
 C15 H15 0.9300 . ?
 C15 C16 1.382(3) . ?
 C16 C17 1.379(3) . ?
 C17 H17 0.9300 . ?
 C17 C18 1.384(3) . ?
 C18 H18 0.9300 . ?
 C18 C19 1.381(3) . ?
 C19 H19 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
 C10 N1 H1 116.0 . . ?
 C10 N1 C14 127.94(15) . . ?
 C14 N1 H1 116.0 . . ?
 C2 C1 H1A 119.7 . . ?
 C2 C1 C6 120.5(2) . . ?
 C6 C1 H1A 119.7 . . ?
 C1 C2 H2 120.0 . . ?
 C3 C2 C1 120.0(3) . . ?
 C3 C2 H2 120.0 . . ?
 C2 C3 H3 119.9 . . ?
 C2 C3 C4 120.3(2) . . ?
 C4 C3 H3 119.9 . . ?
 C3 C4 H4 119.8 . . ?
 C3 C4 C5 120.5(3) . . ?
 C5 C4 H4 119.8 . . ?
 C4 C5 H5 120.3 . . ?
 C6 C5 C4 119.4(3) . . ?
 C6 C5 H5 120.3 . . ?
 C1 C6 C7 121.75(18) . . ?
 C5 C6 C1 119.29(19) . . ?
 C5 C6 C7 118.9(2) . . ?
 O1 C7 C6 119.65(17) . . ?
 O1 C7 C8 120.72(16) . . ?
 C6 C7 C8 119.60(15) . . ?
 C9 C8 C7 118.75(15) . . ?
 C9 C8 C13 120.11(16) . . ?
 C13 C8 C7 120.93(16) . . ?
 C8 C9 H9 119.6 . . ?
 C8 C9 C10 120.76(16) . . ?
 C10 C9 H9 119.6 . . ?
 N1 C10 C9 118.67(15) . . ?
 N1 C10 C11 122.70(16) . . ?
 C9 C10 C11 118.49(16) . . ?
 C10 C11 H11 119.8 . . ?
 C12 C11 C10 120.44(17) . . ?
 C12 C11 H11 119.8 . . ?
 C11 C12 H12 119.3 . . ?
 C11 C12 C13 121.32(17) . . ?
 C13 C12 H12 119.3 . . ?
 C8 C13 H13 120.6 . . ?
 C12 C13 C8 118.82(16) . . ?
 C12 C13 H13 120.6 . . ?
 N1 C14 C15 117.80(16) . . ?
 N1 C14 C19 123.43(16) . . ?
 C15 C14 C19 118.71(16) . . ?
 C14 C15 H15 120.4 . . ?
 C16 C15 C14 119.25(17) . . ?
 C16 C15 H15 120.4 . . ?
 C15 C16 Cl1 118.46(16) . . ?
 C17 C16 Cl1 118.96(15) . . ?
 C17 C16 C15 122.57(19) . . ?
 C16 C17 H17 121.2 . . ?
 C16 C17 C18 117.64(18) . . ?
 C18 C17 H17 121.2 . . ?
 C17 C18 H18 119.3 . . ?
 C19 C18 C17 121.45(18) . . ?
 C19 C18 H18 119.3 . . ?
 C14 C19 H19 119.9 . . ?
 C18 C19 C14 120.25(18) . . ?
 C18 C19 H19 119.9 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 Cl1 C16 C17 C18 -176.28(17) . . . . ?
 O1 C7 C8 C9 -19.5(3) . . . . ?
 O1 C7 C8 C13 155.4(2) . . . . ?
 N1 C10 C11 C12 178.11(19) . . . . ?
 N1 C14 C15 C16 -178.68(18) . . . . ?
 N1 C14 C19 C18 -179.18(19) . . . . ?
 C1 C2 C3 C4 1.4(4) . . . . ?
 C1 C6 C7 O1 138.1(2) . . . . ?
 C1 C6 C7 C8 -43.6(3) . . . . ?
 C2 C1 C6 C5 0.6(3) . . . . ?
 C2 C1 C6 C7 -176.03(18) . . . . ?
 C2 C3 C4 C5 0.3(5) . . . . ?
 C3 C4 C5 C6 -1.6(4) . . . . ?
 C4 C5 C6 C1 1.1(3) . . . . ?
 C4 C5 C6 C7 177.8(2) . . . . ?
 C5 C6 C7 O1 -38.5(3) . . . . ?
 C5 C6 C7 C8 139.8(2) . . . . ?
 C6 C1 C2 C3 -1.9(3) . . . . ?
 C6 C7 C8 C9 162.26(18) . . . . ?
 C6 C7 C8 C13 -22.9(3) . . . . ?
 C7 C8 C9 C10 174.20(17) . . . . ?
 C7 C8 C13 C12 -173.0(2) . . . . ?
 C8 C9 C10 N1 -177.23(17) . . . . ?
 C8 C9 C10 C11 -1.5(3) . . . . ?
 C9 C8 C13 C12 1.8(3) . . . . ?
 C9 C10 C11 C12 2.5(3) . . . . ?
 C10 N1 C14 C15 -159.44(19) . . . . ?
 C10 N1 C14 C19 23.4(3) . . . . ?
 C10 C11 C12 C13 -1.5(3) . . . . ?
 C11 C12 C13 C8 -0.7(3) . . . . ?
 C13 C8 C9 C10 -0.7(3) . . . . ?
 C14 N1 C10 C9 -161.04(19) . . . . ?
 C14 N1 C10 C11 23.4(3) . . . . ?
 C14 C15 C16 Cl1 177.21(15) . . . . ?
 C14 C15 C16 C17 -2.0(3) . . . . ?
 C15 C14 C19 C18 3.7(3) . . . . ?
 C15 C16 C17 C18 2.9(3) . . . . ?
 C16 C17 C18 C19 -0.5(3) . . . . ?
 C17 C18 C19 C14 -2.8(3) . . . . ?
 C19 C14 C15 C16 -1.4(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
