# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_202111324
_database_code_depnum_ccdc_archive 'CCDC 2132356'
loop_
_audit_author_name
_audit_author_address
'Wen-Bo Shen'
;Henan Agricultural University
China
;
_audit_update_record             
;
2022-01-04 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_audit_creation_date             2021-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H11 Br2 N O'
_chemical_formula_sum            'C18 H11 Br2 N O'
_chemical_formula_weight         417.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2S1
_chemical_oxdiff_usercomment     r
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'
Br Br -0.6763 1.2805 '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           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                   14.2057(2)
_cell_length_b                   10.32140(14)
_cell_length_c                   21.0985(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.5952(14)
_cell_angle_gamma                90
_cell_volume                     3078.78(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3205
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5770
_cell_measurement_theta_min      5.2850
_shelx_estimated_absorpt_T_max   0.585
_shelx_estimated_absorpt_T_min   0.455
_exptl_absorpt_coefficient_mu    6.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5665
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.211
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_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   -108.00 -32.00   1.00    3.50    --  -33.50 178.00  90.00   76
  2  ω    -58.00  35.00   1.00    3.50    --  -33.50  77.00  30.00   93
  3  ω     61.00  91.00   1.00    3.50    --   36.47 178.00 -90.00   30
  4  ω     46.00 108.00   1.00    3.50    --   36.47-158.00 160.00   62
  5  ω     59.00  90.00   1.00    3.50    --   36.47 178.00-150.00   31
  6  ω     41.00 103.00   1.00    3.50    --   36.47  57.00   0.00   62
  7  ω     71.00 109.00   1.00    3.50    --   36.47 178.00  60.00   38
  8  ω     57.00  82.00   1.00    3.50    --   36.47 178.00 150.00   25
  9  ω     48.00  80.00   1.00    9.00    --  108.00 -45.00 -90.00   32
 10  ω    114.00 161.00   1.00    9.00    --  108.00  61.00 150.00   47
 11  ω    101.00 128.00   1.00    9.00    --  108.00 -45.00 -90.00   27
 12  ω     48.00 109.00   1.00    9.00    --  108.00-111.00-150.00   61
 13  ω     44.00 103.00   1.00    9.00    --  108.00 -94.00 -60.00   59
 14  ω     38.00  64.00   1.00    9.00    --  108.00 -94.00-120.00   26
 15  ω     79.00 123.00   1.00    9.00    --  108.00 -30.00  30.00   44
 16  ω     42.00 119.00   1.00    9.00    --  108.00 -45.00   0.00   77
 17  ω     37.00 152.00   1.00    9.00    --  108.00 -15.00 150.00  115
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0016856000
_diffrn_orient_matrix_UB_12      -0.0142230000
_diffrn_orient_matrix_UB_13      -0.0725673000
_diffrn_orient_matrix_UB_21      0.0949939000
_diffrn_orient_matrix_UB_22      0.0729753000
_diffrn_orient_matrix_UB_23      0.0038250000
_diffrn_orient_matrix_UB_31      0.0533617000
_diffrn_orient_matrix_UB_32      -0.1294250000
_diffrn_orient_matrix_UB_33      0.0100888000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2472
_reflns_number_total             2753
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.00080(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2753
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.073
_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)+(0.0555P)²+2.9487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1009
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br1 Br 0.33807(3) -0.25865(4) 0.44159(2) 0.06044(19) Uani 1 1 d . . . . .
Br2 Br 0.08139(2) 0.08852(4) 0.45368(2) 0.05083(17) Uani 1 1 d . . . . .
O1 O 0.2501(2) 0.0941(3) 0.56452(12) 0.0653(8) Uani 1 1 d . . . . .
N1 N 0.46439(18) -0.1262(3) 0.37390(12) 0.0373(6) Uani 1 1 d . . . . .
C1 C 0.4499(3) 0.2256(3) 0.37878(17) 0.0465(8) Uani 1 1 d . . . . .
H1 H 0.4121 0.2870 0.3963 0.056 Uiso 1 1 calc R . . . .
C2 C 0.5246(3) 0.2630(4) 0.3443(2) 0.0571(10) Uani 1 1 d . . . . .
H2 H 0.5367 0.3504 0.3383 0.068 Uiso 1 1 calc R . . . .
C3 C 0.5810(3) 0.1698(4) 0.3189(2) 0.0596(10) Uani 1 1 d . . . . .
H3 H 0.6313 0.1965 0.2969 0.072 Uiso 1 1 calc R . . . .
C4 C 0.5644(2) 0.0386(4) 0.32552(17) 0.0481(8) Uani 1 1 d . . . . .
H4 H 0.6017 -0.0232 0.3079 0.058 Uiso 1 1 calc R . . . .
C5 C 0.4902(2) 0.0034(3) 0.35932(13) 0.0348(6) Uani 1 1 d . . . . .
C6 C 0.4339(2) 0.0952(3) 0.38602(14) 0.0348(6) Uani 1 1 d . . . . .
C7 C 0.3963(2) -0.1151(3) 0.40760(14) 0.0345(6) Uani 1 1 d . . . . .
C8 C 0.3644(2) 0.0224(3) 0.42278(13) 0.0327(6) Uani 1 1 d . . . . .
C9 C 0.3725(2) 0.0490(4) 0.49515(15) 0.0434(7) Uani 1 1 d . . . . .
H9A H 0.4005 -0.0248 0.5185 0.052 Uiso 1 1 calc R . . . .
H9B H 0.4117 0.1245 0.5054 0.052 Uiso 1 1 calc R . . . .
C10 C 0.2732(2) 0.0720(3) 0.51204(15) 0.0413(7) Uani 1 1 d . . . . .
C11 C 0.2120(2) 0.0673(3) 0.45233(15) 0.0355(6) Uani 1 1 d . . . . .
C12 C 0.2591(2) 0.0464(3) 0.40105(14) 0.0317(6) Uani 1 1 d . . . . .
C13 C 0.2210(2) 0.0468(3) 0.33388(14) 0.0358(6) Uani 1 1 d . . . . .
C14 C 0.2414(2) -0.0497(4) 0.29183(16) 0.0450(8) Uani 1 1 d . . . . .
H14 H 0.2825 -0.1160 0.3060 0.054 Uiso 1 1 calc R . . . .
C15 C 0.2021(3) -0.0499(5) 0.22921(18) 0.0600(10) Uani 1 1 d . . . . .
H15 H 0.2148 -0.1173 0.2021 0.072 Uiso 1 1 calc R . . . .
C16 C 0.1443(3) 0.0500(5) 0.20749(19) 0.0672(13) Uani 1 1 d . . . . .
H16 H 0.1182 0.0510 0.1653 0.081 Uiso 1 1 calc R . . . .
C17 C 0.1246(3) 0.1491(5) 0.2479(2) 0.0674(12) Uani 1 1 d . . . . .
H17 H 0.0860 0.2172 0.2327 0.081 Uiso 1 1 calc R . . . .
C18 C 0.1619(3) 0.1484(4) 0.31119(18) 0.0523(9) Uani 1 1 d . . . . .
H18 H 0.1477 0.2151 0.3383 0.063 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
Br1 C7 1.873(3) . ?
Br2 C11 1.871(3) . ?
O1 C10 1.207(4) . ?
N1 C5 1.428(4) . ?
N1 C7 1.261(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.399(5) . ?
C1 C6 1.376(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(4) . ?
C5 C6 1.393(4) . ?
C6 C8 1.513(4) . ?
C7 C8 1.533(4) . ?
C8 C9 1.544(4) . ?
C8 C12 1.541(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.507(4) . ?
C10 C11 1.461(5) . ?
C11 C12 1.344(4) . ?
C12 C13 1.467(4) . ?
C13 C14 1.384(5) . ?
C13 C18 1.398(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(6) . ?
C18 H18 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
C7 N1 C5 105.3(3) . . ?
C2 C1 H1 121.0 . . ?
C6 C1 H1 121.0 . . ?
C6 C1 C2 118.0(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.2(3) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 N1 125.7(3) . . ?
C4 C5 C6 121.9(3) . . ?
C6 C5 N1 112.3(3) . . ?
C1 C6 C5 120.9(3) . . ?
C1 C6 C8 131.7(3) . . ?
C5 C6 C8 107.4(3) . . ?
N1 C7 Br1 122.4(2) . . ?
N1 C7 C8 117.4(3) . . ?
C8 C7 Br1 120.1(2) . . ?
C6 C8 C7 97.6(2) . . ?
C6 C8 C9 115.4(3) . . ?
C6 C8 C12 115.5(2) . . ?
C7 C8 C9 112.0(3) . . ?
C7 C8 C12 112.6(2) . . ?
C12 C8 C9 104.0(2) . . ?
C8 C9 H9A 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C10 C9 C8 106.3(3) . . ?
C10 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
O1 C10 C9 126.2(3) . . ?
O1 C10 C11 127.3(3) . . ?
C11 C10 C9 106.5(3) . . ?
C10 C11 Br2 119.4(2) . . ?
C12 C11 Br2 127.2(2) . . ?
C12 C11 C10 113.4(3) . . ?
C11 C12 C8 109.4(3) . . ?
C11 C12 C13 127.7(3) . . ?
C13 C12 C8 123.0(2) . . ?
C14 C13 C12 122.5(3) . . ?
C14 C13 C18 118.5(3) . . ?
C18 C13 C12 119.1(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.5(4) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.5(4) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(4) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.7(4) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 120.2 . . ?
C17 C18 C13 119.6(4) . . ?
C17 C18 H18 120.2 . . ?

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
Br1 C7 C8 C6 178.6(2) . . . . ?
Br1 C7 C8 C9 57.3(3) . . . . ?
Br1 C7 C8 C12 -59.6(3) . . . . ?
Br2 C11 C12 C8 -174.9(2) . . . . ?
Br2 C11 C12 C13 5.9(5) . . . . ?
O1 C10 C11 Br2 -3.4(5) . . . . ?
O1 C10 C11 C12 177.0(4) . . . . ?
N1 C5 C6 C1 178.1(3) . . . . ?
N1 C5 C6 C8 0.8(3) . . . . ?
N1 C7 C8 C6 1.2(3) . . . . ?
N1 C7 C8 C9 -120.2(3) . . . . ?
N1 C7 C8 C12 123.0(3) . . . . ?
C1 C2 C3 C4 1.4(6) . . . . ?
C1 C6 C8 C7 -178.0(3) . . . . ?
C1 C6 C8 C9 -59.1(5) . . . . ?
C1 C6 C8 C12 62.5(4) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
C2 C1 C6 C8 176.0(3) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C3 C4 C5 N1 -176.9(3) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C1 0.9(5) . . . . ?
C4 C5 C6 C8 -176.4(3) . . . . ?
C5 N1 C7 Br1 -178.2(2) . . . . ?
C5 N1 C7 C8 -0.8(3) . . . . ?
C5 C6 C8 C7 -1.1(3) . . . . ?
C5 C6 C8 C9 117.8(3) . . . . ?
C5 C6 C8 C12 -120.6(3) . . . . ?
C6 C1 C2 C3 -0.6(6) . . . . ?
C6 C8 C9 C10 133.4(3) . . . . ?
C6 C8 C12 C11 -134.0(3) . . . . ?
C6 C8 C12 C13 45.2(4) . . . . ?
C7 N1 C5 C4 177.1(3) . . . . ?
C7 N1 C5 C6 0.0(3) . . . . ?
C7 C8 C9 C10 -116.2(3) . . . . ?
C7 C8 C12 C11 115.1(3) . . . . ?
C7 C8 C12 C13 -65.6(4) . . . . ?
C8 C9 C10 O1 178.8(4) . . . . ?
C8 C9 C10 C11 -3.3(4) . . . . ?
C8 C12 C13 C14 47.9(4) . . . . ?
C8 C12 C13 C18 -132.0(3) . . . . ?
C9 C8 C12 C11 -6.5(3) . . . . ?
C9 C8 C12 C13 172.8(3) . . . . ?
C9 C10 C11 Br2 178.8(2) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C10 C11 C12 C8 4.7(4) . . . . ?
C10 C11 C12 C13 -174.5(3) . . . . ?
C11 C12 C13 C14 -133.0(4) . . . . ?
C11 C12 C13 C18 47.1(5) . . . . ?
C12 C8 C9 C10 5.7(3) . . . . ?
C12 C13 C14 C15 177.7(3) . . . . ?
C12 C13 C18 C17 -179.3(3) . . . . ?
C13 C14 C15 C16 2.4(6) . . . . ?
C14 C13 C18 C17 0.8(5) . . . . ?
C14 C15 C16 C17 -0.7(6) . . . . ?
C15 C16 C17 C18 -0.9(7) . . . . ?
C16 C17 C18 C13 0.8(6) . . . . ?
C18 C13 C14 C15 -2.4(5) . . . . ?

_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 1.391
_oxdiff_exptl_absorpt_empirical_full_min 0.811
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_202110281
_database_code_depnum_ccdc_archive 'CCDC 2132359'
loop_
_audit_author_name
_audit_author_address
'Wen-Bo Shen'
;Henan Agricultural University
China
;
_audit_update_record             
;
2022-01-04 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_audit_creation_date             2021-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 Cl N O2'
_chemical_formula_sum            'C19 H14 Cl N O2'
_chemical_formula_weight         323.76
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3N1O4
_chemical_oxdiff_usercomment     r
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'
Cl Cl 0.3639 0.7018 '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/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                   15.4499(5)
_cell_length_b                   6.48001(16)
_cell_length_c                   16.3247(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.667(3)
_cell_angle_gamma                90
_cell_volume                     1606.11(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2269
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0720
_cell_measurement_theta_min      4.3680
_shelx_estimated_absorpt_T_max   0.812
_shelx_estimated_absorpt_T_min   0.709
_exptl_absorpt_coefficient_mu    2.176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5928
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.054
_diffrn_reflns_theta_max         67.054
_diffrn_reflns_theta_min         3.619
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_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   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00 -30.00   93
  2  ω    -52.00  35.00   1.00    1.00    --  -33.50  57.00 120.00   87
  3  ω     18.00 105.00   1.00    1.00    --   36.47  57.00  60.00   87
  4  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00 -30.00   81
  5  ω    -20.00  41.00   1.00    1.00    --   36.47 -37.00-120.00   61
  6  ω     81.00 109.00   1.00    1.00    --   36.47 178.00  90.00   28
  7  ω     -4.00  60.00   1.00    1.00    --   36.47 -99.00-120.00   64
  8  ω     37.00 102.00   1.00    3.50    --  108.00-111.00 -90.00   65
  9  ω     48.00 124.00   1.00    3.50    --  108.00 -45.00 -90.00   76
 10  ω     50.00  90.00   1.00    3.50    --  108.00 -94.00-180.00   40
 11  ω     43.00 103.00   1.00    3.50    --  108.00 -94.00 -60.00   60
 12  ω    100.00 126.00   1.00    3.50    --  108.00 -30.00  60.00   26
 13  ω     62.00 173.00   1.00    3.50    --  108.00   0.00 -60.00  111
 14  ω     40.00 122.00   1.00    3.50    --  108.00 -45.00 150.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0806076000
_diffrn_orient_matrix_UB_12      -0.0749146000
_diffrn_orient_matrix_UB_13      -0.0350000000
_diffrn_orient_matrix_UB_21      -0.0533129000
_diffrn_orient_matrix_UB_22      0.0175244000
_diffrn_orient_matrix_UB_23      -0.0892982000
_diffrn_orient_matrix_UB_31      0.0309999000
_diffrn_orient_matrix_UB_32      0.2248351000
_diffrn_orient_matrix_UB_33      -0.0047068000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2220
_reflns_number_total             2867
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.052
_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)+(0.0628P)²+0.3332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1333
_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. Restrained distances
 C14-C4
 1.55 with sigma of 0.02
 C14A-C4
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C15A) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C17)
\\sim Ueq, Uanis(C17A) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C18A) \\sim Ueq,
Uanis(C19A) \\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
Uanis(C17) = Uanis(C17A)
Uanis(C18) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(C14) = Uanis(C14A)
4. Others
 Sof(C14A)=Sof(C19A)=Sof(H19A)=Sof(C18A)=Sof(H18A)=Sof(C17A)=Sof(H17A)=
 Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=1-FVAR(1)
 Sof(C17)=Sof(H17)=Sof(C16)=Sof(H16)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(C19)=
 Sof(H19)=Sof(C18)=Sof(H18)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C12(H12), C19A(H19A), C18A(H18A), C17A(H17A),
 C16A(H16A), C15A(H15A), C17(H17), C16(H16), C15(H15), C19(H19), C18(H18)
5.c Fitted hexagon refined as free rotating group:
 C14A(C19A,C18A,C17A,C16A,C15A), C17(C16,C15,C14,C19,C18)
5.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.80535(16) 0.3225(4) 0.38277(13) 0.0474(5) Uani 1 1 d . . . . .
H1A H 0.8588 0.4040 0.3953 0.057 Uiso 1 1 calc R . . . .
H1B H 0.8095 0.2310 0.3366 0.057 Uiso 1 1 calc R . . . .
C2 C 0.72589(15) 0.4601(3) 0.36154(13) 0.0453(5) Uani 1 1 d . . . . .
C3 C 0.67446(15) 0.4327(3) 0.42741(14) 0.0461(5) Uani 1 1 d . . . . .
C4 C 0.70953(14) 0.2936(3) 0.48374(13) 0.0419(5) Uani 1 1 d D . . . .
C5 C 0.79176(14) 0.1974(3) 0.46008(12) 0.0405(5) Uani 1 1 d . . . . .
C6 C 0.78232(16) -0.0338(4) 0.44366(15) 0.0533(6) Uani 1 1 d . . . . .
H6 H 0.7391 -0.0877 0.4018 0.064 Uiso 1 1 calc R . . . .
C7 C 0.86952(13) 0.1911(3) 0.53163(12) 0.0373(4) Uani 1 1 d . . . . .
C8 C 0.89272(15) -0.0142(3) 0.54688(14) 0.0459(5) Uani 1 1 d . . . . .
C9 C 0.96168(16) -0.0657(4) 0.60978(16) 0.0548(6) Uani 1 1 d . . . . .
H9 H 0.9779 -0.2030 0.6197 0.066 Uiso 1 1 calc R . . . .
C10 C 1.00640(15) 0.0892(4) 0.65790(14) 0.0501(6) Uani 1 1 d . . . . .
H10 H 1.0525 0.0562 0.7011 0.060 Uiso 1 1 calc R . . . .
C11 C 0.98286(14) 0.2941(3) 0.64204(13) 0.0423(5) Uani 1 1 d . . . . .
C12 C 0.91355(14) 0.3471(3) 0.57793(12) 0.0403(5) Uani 1 1 d . . . . .
H12 H 0.8978 0.4843 0.5670 0.048 Uiso 1 1 calc R . . . .
C13 C 1.08594(19) 0.4166(5) 0.76014(16) 0.0683(8) Uani 1 1 d . . . . .
H13A H 1.1360 0.3475 0.7458 0.102 Uiso 1 1 calc GR . . . .
H13B H 1.0597 0.3308 0.7968 0.102 Uiso 1 1 calc GR . . . .
H13C H 1.1044 0.5446 0.7875 0.102 Uiso 1 1 calc GR . . . .
C14A C 0.6798(3) 0.2457(7) 0.5641(2) 0.0530(7) Uani 0.709(10) 1 d D U P A 2
C19A C 0.6778(4) 0.4075(7) 0.6196(3) 0.0690(14) Uani 0.709(10) 1 d G U P A 2
H19A H 0.6925 0.5403 0.6055 0.083 Uiso 0.709(10) 1 calc R . P A 2
C18A C 0.6537(3) 0.3708(9) 0.6963(3) 0.0850(16) Uani 0.709(10) 1 d G U P A 2
H18A H 0.6523 0.4791 0.7334 0.102 Uiso 0.709(10) 1 calc R . P A 2
C17A C 0.6317(3) 0.1723(9) 0.7174(3) 0.0939(18) Uani 0.709(10) 1 d G U P A 2
H17A H 0.6156 0.1478 0.7686 0.113 Uiso 0.709(10) 1 calc R . P A 2
C16A C 0.6338(4) 0.0106(6) 0.6618(4) 0.097(2) Uani 0.709(10) 1 d G U P A 2
H16A H 0.6190 -0.1222 0.6760 0.117 Uiso 0.709(10) 1 calc R . P A 2
C15A C 0.6578(4) 0.0473(6) 0.5852(3) 0.0786(15) Uani 0.709(10) 1 d G U P A 2
H15A H 0.6592 -0.0610 0.5481 0.094 Uiso 0.709(10) 1 calc R . P A 2
C17 C 0.6155(9) 0.104(2) 0.6988(6) 0.0939(18) Uani 0.291(10) 1 d . U P A 1
H17 H 0.5943 0.0618 0.7458 0.113 Uiso 0.291(10) 1 calc R . P A 1
C16 C 0.5981(10) -0.0122(17) 0.6262(9) 0.097(2) Uani 0.291(10) 1 d G U P A 1
H16 H 0.5652 -0.1329 0.6245 0.117 Uiso 0.291(10) 1 calc R . P A 1
C15 C 0.6298(9) 0.0514(19) 0.5559(7) 0.0786(15) Uani 0.291(10) 1 d G U P A 1
H15 H 0.6181 -0.0266 0.5073 0.094 Uiso 0.291(10) 1 calc R . P A 1
C14 C 0.6789(8) 0.232(2) 0.5584(6) 0.0530(7) Uani 0.291(10) 1 d DG U P A 1
C19 C 0.6964(8) 0.3483(19) 0.6310(8) 0.0690(14) Uani 0.291(10) 1 d G . P A 1
H19 H 0.7293 0.4689 0.6326 0.083 Uiso 0.291(10) 1 calc R . P A 1
C18 C 0.6647(9) 0.285(2) 0.7012(6) 0.0850(16) Uani 0.291(10) 1 d G U P A 1
H18 H 0.6764 0.3627 0.7498 0.102 Uiso 0.291(10) 1 calc R . P A 1
Cl1 Cl 0.57936(4) 0.57102(12) 0.42529(5) 0.0731(3) Uani 1 1 d . . . . .
N1 N 0.83719(15) -0.1487(3) 0.49077(13) 0.0571(5) Uani 1 1 d . . . . .
O1 O 0.70805(13) 0.5731(3) 0.30175(10) 0.0632(5) Uani 1 1 d . . . . .
O2 O 1.02324(11) 0.4568(2) 0.68655(10) 0.0549(4) Uani 1 1 d . . . . .


_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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.505(3) . ?
C1 C5 1.546(3) . ?
C2 C3 1.461(3) . ?
C2 O1 1.210(3) . ?
C3 C4 1.330(3) . ?
C3 Cl1 1.716(2) . ?
C4 C5 1.527(3) . ?
C4 C14A 1.500(4) . ?
C4 C14 1.443(8) . ?
C5 C6 1.524(3) . ?
C5 C7 1.513(3) . ?
C6 H6 0.9300 . ?
C6 N1 1.274(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.366(3) . ?
C8 C9 1.377(3) . ?
C8 N1 1.429(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(3) . ?
C11 C12 1.395(3) . ?
C11 O2 1.364(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 O2 1.421(3) . ?
C14A C19A 1.3900 . ?
C14A C15A 1.3900 . ?
C19A H19A 0.9300 . ?
C19A C18A 1.3900 . ?
C18A H18A 0.9300 . ?
C18A C17A 1.3900 . ?
C17A H17A 0.9300 . ?
C17A C16A 1.3900 . ?
C16A H16A 0.9300 . ?
C16A C15A 1.3900 . ?
C15A H15A 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.3900 . ?
C17 C18 1.3900 . ?
C16 H16 0.9300 . ?
C16 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C14 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C18 1.3900 . ?
C18 H18 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
H1A C1 H1B 108.7 . . ?
C2 C1 H1A 110.6 . . ?
C2 C1 H1B 110.6 . . ?
C2 C1 C5 105.68(19) . . ?
C5 C1 H1A 110.6 . . ?
C5 C1 H1B 110.6 . . ?
C3 C2 C1 106.85(18) . . ?
O1 C2 C1 126.8(2) . . ?
O1 C2 C3 126.4(2) . . ?
C2 C3 Cl1 120.13(16) . . ?
C4 C3 C2 112.6(2) . . ?
C4 C3 Cl1 127.3(2) . . ?
C3 C4 C5 110.7(2) . . ?
C3 C4 C14A 126.4(3) . . ?
C3 C4 C14 128.1(6) . . ?
C14A C4 C5 122.7(2) . . ?
C14 C4 C5 121.2(5) . . ?
C4 C5 C1 103.75(17) . . ?
C6 C5 C1 113.24(18) . . ?
C6 C5 C4 112.86(19) . . ?
C7 C5 C1 115.83(18) . . ?
C7 C5 C4 113.23(17) . . ?
C7 C5 C6 98.38(17) . . ?
C5 C6 H6 122.1 . . ?
N1 C6 C5 115.9(2) . . ?
N1 C6 H6 122.1 . . ?
C8 C7 C5 107.81(18) . . ?
C12 C7 C5 130.55(18) . . ?
C12 C7 C8 121.64(19) . . ?
C7 C8 N1 111.40(19) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 N1 128.3(2) . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.1(2) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 120.9(2) . . ?
O2 C11 C10 124.17(19) . . ?
O2 C11 C12 114.90(19) . . ?
C7 C12 C11 117.86(19) . . ?
C7 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
C19A C14A C4 117.5(3) . . ?
C19A C14A C15A 120.0 . . ?
C15A C14A C4 122.4(3) . . ?
C14A C19A H19A 120.0 . . ?
C18A C19A C14A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C19A C18A C17A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C16A C17A C18A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C17A C16A C15A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C14 C4 118.2(8) . . ?
C19 C14 C4 121.8(9) . . ?
C19 C14 C15 120.0 . . ?
C14 C19 H19 120.0 . . ?
C14 C19 C18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C6 N1 C8 106.52(19) . . ?
C11 O2 C13 118.82(19) . . ?

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
C1 C2 C3 C4 -2.2(3) . . . . ?
C1 C2 C3 Cl1 178.58(16) . . . . ?
C1 C5 C6 N1 123.0(2) . . . . ?
C1 C5 C7 C8 -121.3(2) . . . . ?
C1 C5 C7 C12 59.4(3) . . . . ?
C2 C1 C5 C4 -6.7(2) . . . . ?
C2 C1 C5 C6 116.0(2) . . . . ?
C2 C1 C5 C7 -131.40(19) . . . . ?
C2 C3 C4 C5 -2.4(3) . . . . ?
C2 C3 C4 C14A 172.5(3) . . . . ?
C2 C3 C4 C14 177.7(7) . . . . ?
C3 C4 C5 C1 5.7(2) . . . . ?
C3 C4 C5 C6 -117.2(2) . . . . ?
C3 C4 C5 C7 132.1(2) . . . . ?
C3 C4 C14A C19A -56.8(4) . . . . ?
C3 C4 C14A C15A 125.4(4) . . . . ?
C3 C4 C14 C15 99.0(9) . . . . ?
C3 C4 C14 C19 -80.2(10) . . . . ?
C4 C5 C6 N1 -119.5(2) . . . . ?
C4 C5 C7 C8 119.0(2) . . . . ?
C4 C5 C7 C12 -60.3(3) . . . . ?
C4 C14A C19A C18A -177.8(4) . . . . ?
C4 C14A C15A C16A 177.7(4) . . . . ?
C4 C14 C19 C18 179.1(11) . . . . ?
C5 C1 C2 C3 5.6(2) . . . . ?
C5 C1 C2 O1 -174.8(2) . . . . ?
C5 C4 C14A C19A 117.4(3) . . . . ?
C5 C4 C14A C15A -60.4(4) . . . . ?
C5 C4 C14 C15 -80.9(8) . . . . ?
C5 C4 C14 C19 99.9(8) . . . . ?
C5 C6 N1 C8 0.1(3) . . . . ?
C5 C7 C8 C9 -179.5(2) . . . . ?
C5 C7 C8 N1 0.5(3) . . . . ?
C5 C7 C12 C11 178.8(2) . . . . ?
C6 C5 C7 C8 -0.4(2) . . . . ?
C6 C5 C7 C12 -179.7(2) . . . . ?
C7 C5 C6 N1 0.2(3) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C7 C8 N1 C6 -0.3(3) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C9 C8 N1 C6 179.6(3) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C9 C10 C11 O2 179.8(2) . . . . ?
C10 C11 C12 C7 0.3(3) . . . . ?
C10 C11 O2 C13 -8.2(4) . . . . ?
C12 C7 C8 C9 -0.1(4) . . . . ?
C12 C7 C8 N1 179.8(2) . . . . ?
C12 C11 O2 C13 171.2(2) . . . . ?
C14A C4 C5 C1 -169.3(3) . . . . ?
C14A C4 C5 C6 67.7(3) . . . . ?
C14A C4 C5 C7 -42.9(3) . . . . ?
C14A C19A C18A C17A 0.0 . . . . ?
C19A C14A C15A C16A 0.0 . . . . ?
C19A C18A C17A C16A 0.0 . . . . ?
C18A C17A C16A C15A 0.0 . . . . ?
C17A C16A C15A C14A 0.0 . . . . ?
C15A C14A C19A C18A 0.0 . . . . ?
C17 C16 C15 C14 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C16 C15 C14 C4 -179.2(10) . . . . ?
C16 C15 C14 C19 0.0 . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C14 C4 C5 C1 -174.4(7) . . . . ?
C14 C4 C5 C6 62.7(7) . . . . ?
C14 C4 C5 C7 -48.0(7) . . . . ?
C14 C19 C18 C17 0.0 . . . . ?
C18 C17 C16 C15 0.0 . . . . ?
Cl1 C3 C4 C5 176.80(16) . . . . ?
Cl1 C3 C4 C14A -8.4(4) . . . . ?
Cl1 C3 C4 C14 -3.1(8) . . . . ?
N1 C8 C9 C10 -179.1(2) . . . . ?
O1 C2 C3 C4 178.2(2) . . . . ?
O1 C2 C3 Cl1 -1.0(3) . . . . ?
O2 C11 C12 C7 -179.14(19) . . . . ?

_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 1.084
_oxdiff_exptl_absorpt_empirical_full_min 0.919
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_202012291
_database_code_depnum_ccdc_archive 'CCDC 2132360'
loop_
_audit_author_name
_audit_author_address
'Wen-Bo Shen' 'Henan Agricultural University'
_audit_update_record             
;
2022-01-04 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_audit_creation_date             2020-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C18 H13 N O), C H2 Cl2'
_chemical_formula_sum            'C37 H28 Cl2 N2 O2'
_chemical_formula_weight         603.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2
_chemical_oxdiff_usercomment     r
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'
Cl Cl 0.3639 0.7018 '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           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                   30.272(3)
_cell_length_b                   7.2755(2)
_cell_length_c                   19.6366(18)
_cell_angle_alpha                90
_cell_angle_beta                 136.530(17)
_cell_angle_gamma                90
_cell_volume                     2975.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2046
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.5800
_cell_measurement_theta_min      4.2470
_shelx_estimated_absorpt_T_max   0.840
_shelx_estimated_absorpt_T_min   0.661
_exptl_absorpt_coefficient_mu    2.256
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9509
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         4.246
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_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   -108.00 -32.00   0.50    3.00    --  -33.50 178.00-180.00  152
  2  ω   -102.00 -15.00   0.50    3.00    --  -33.50 -57.00 150.00  174
  3  ω    -52.00  35.00   0.50    3.00    --  -33.50  57.00 -60.00  174
  4  ω     57.00 110.00   0.50    3.00    --   36.47 178.00  60.00  106
  5  ω     -4.00  77.00   0.50    3.00    --   36.47 -99.00 -90.00  162
  6  ω     14.00 107.00   0.50    3.00    --   36.47  37.00  60.00  186
  7  ω    -32.00  55.00   0.50    3.00    --   36.47 -57.00  60.00  174
  8  ω     64.00 105.00   0.50    3.00    --   36.47 178.00 150.00   82
  9  ω     35.00  73.00   0.50    3.00    --   36.47 -99.00 -30.00   76
 10  ω      0.00  77.00   0.50    3.00    --   36.47 -99.00 120.00  154
 11  ω    -24.00  71.00   0.50    3.00    --   36.47 -19.00  90.00  190
 12  ω     45.00 110.00   0.50   10.00    --  108.00 -94.00   0.00  130
 13  ω     77.00 112.00   0.50   10.00    --  108.00-111.00-120.00   70
 14  ω    138.00 163.00   0.50   10.00    --  108.00  61.00  30.00   50
 15  ω    112.00 139.00   0.50   10.00    --  108.00  61.00 -60.00   54
 16  ω     51.00  98.00   0.50   10.00    --  108.00 -94.00  90.00   94
 17  ω     84.00 109.00   0.50   10.00    --  108.00 -94.00 120.00   50
 18  ω     37.00 134.00   0.50   10.00    --  108.00 -30.00-150.00  194
 19  ω     38.00  66.00   0.50   10.00    --  108.00 -94.00 120.00   56
 20  ω    115.00 153.00   0.50   10.00    --  108.00 -15.00 -60.00   76
 21  ω     69.00 108.00   0.50   10.00    --  108.00 -15.00 -60.00   78
 22  ω     40.00 126.00   0.50   10.00    --  108.00 -61.00 120.00  172
 23  ω     36.00  68.00   0.50   10.00    --  108.00 -15.00 -60.00   64
 24  ω     38.00 127.00   0.50   10.00    --  108.00 -45.00 -30.00  178
 25  ω    127.00 174.00   0.50   10.00    --  108.00  61.00 -90.00   94
 26  ω     36.00 153.00   0.50   10.00    --  108.00 -15.00  90.00  234
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0532426500
_diffrn_orient_matrix_UB_12      0.0869228500
_diffrn_orient_matrix_UB_13      0.0156466000
_diffrn_orient_matrix_UB_21      -0.0508648000
_diffrn_orient_matrix_UB_22      0.0653567000
_diffrn_orient_matrix_UB_23      -0.1084850000
_diffrn_orient_matrix_UB_31      -0.0071649500
_diffrn_orient_matrix_UB_32      0.1816519500
_diffrn_orient_matrix_UB_33      0.0315520000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1929
_reflns_number_total             2665
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2665
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0774
_refine_ls_restrained_S_all      1.049
_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)+(0.1400P)²+1.4269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2127
_refine_ls_wR_factor_ref         0.2391
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: H19A(0.5) H19B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.19218(17) 1.0662(4) 0.4757(3) 0.0625(8) Uani 1 1 d . . . . .
H1 H 0.1487 1.0787 0.4175 0.075 Uiso 1 1 calc R . . . .
C2 C 0.2149(2) 1.1105(5) 0.5644(3) 0.0701(10) Uani 1 1 d . . . . .
H2 H 0.1868 1.1515 0.5665 0.084 Uiso 1 1 calc R . . . .
C3 C 0.2807(2) 1.0938(5) 0.6523(3) 0.0694(9) Uani 1 1 d . . . . .
H3 H 0.2960 1.1258 0.7123 0.083 Uiso 1 1 calc R . . . .
C4 C 0.32242(18) 1.0315(5) 0.6510(3) 0.0634(8) Uani 1 1 d . . . . .
H4 H 0.3658 1.0207 0.7101 0.076 Uiso 1 1 calc R . . . .
C5 C 0.30077(15) 0.9833(4) 0.5613(2) 0.0550(7) Uani 1 1 d . . . . .
C6 C 0.23454(15) 1.0016(4) 0.4723(2) 0.0547(7) Uani 1 1 d . . . . .
C7 C 0.21539(14) 0.9522(4) 0.3842(2) 0.0540(7) Uani 1 1 d . . . . .
C8 C 0.25976(14) 0.8923(4) 0.3876(2) 0.0519(7) Uani 1 1 d . . . . .
C9 C 0.32631(14) 0.8837(4) 0.4808(2) 0.0510(7) Uani 1 1 d . . . . .
C10 C 0.37696(14) 0.8337(4) 0.4872(2) 0.0536(7) Uani 1 1 d . . . . .
C11 C 0.42499(16) 0.7093(5) 0.5586(3) 0.0670(9) Uani 1 1 d . . . . .
H11 H 0.4255 0.6564 0.6022 0.080 Uiso 1 1 calc R . . . .
C12 C 0.47215(17) 0.6650(5) 0.5641(3) 0.0787(11) Uani 1 1 d . . . . .
H12 H 0.5038 0.5803 0.6109 0.094 Uiso 1 1 calc R . . . .
C13 C 0.47268(17) 0.7448(5) 0.5012(3) 0.0746(10) Uani 1 1 d . . . . .
H13 H 0.5043 0.7141 0.5051 0.089 Uiso 1 1 calc R . . . .
C14 C 0.42563(16) 0.8712(5) 0.4320(3) 0.0706(9) Uani 1 1 d . . . . .
H14 H 0.4261 0.9278 0.3901 0.085 Uiso 1 1 calc R . . . .
C15 C 0.37813(15) 0.9135(5) 0.4249(2) 0.0592(8) Uani 1 1 d . . . . .
H15 H 0.3463 0.9972 0.3773 0.071 Uiso 1 1 calc R . . . .
C16 C 0.22637(15) 0.8304(4) 0.2876(2) 0.0558(7) Uani 1 1 d . . . . .
C17 C 0.15709(17) 0.8903(5) 0.2170(3) 0.0715(10) Uani 1 1 d . . . . .
H17A H 0.1284 0.7895 0.1740 0.086 Uiso 1 1 calc R . . . .
H17B H 0.1480 0.9918 0.1763 0.086 Uiso 1 1 calc R . . . .
C18 C 0.14829(15) 0.9497(5) 0.2810(2) 0.0648(9) Uani 1 1 d . . . . .
H18A H 0.1289 1.0706 0.2618 0.078 Uiso 1 1 calc R . . . .
H18B H 0.1216 0.8629 0.2757 0.078 Uiso 1 1 calc R . . . .
N1 N 0.34520(12) 0.9254(4) 0.56380(18) 0.0556(6) Uani 1 1 d . . . . .
O1 O 0.24757(11) 0.7415(3) 0.26422(17) 0.0654(6) Uani 1 1 d . . . . .
C19 C 0.5000 0.9178(8) 0.2500 0.0832(15) Uani 1 2 d S T P . .
H19A H 0.5376 0.9965 0.2903 0.100 Uiso 0.5 1 calc R . . . .
H19B H 0.4624 0.9965 0.2097 0.100 Uiso 0.5 1 calc R . . . .
Cl1 Cl 0.50309(9) 0.7868(3) 0.32774(14) 0.1531(8) Uani 1 1 d . . . . .


_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
C1 H1 0.9300 . ?
C1 C2 1.368(5) . ?
C1 C6 1.413(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.405(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.358(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.406(4) . ?
C5 C6 1.416(5) . ?
C5 N1 1.376(4) . ?
C6 C7 1.415(4) . ?
C7 C8 1.366(4) . ?
C7 C18 1.503(4) . ?
C8 C9 1.436(4) . ?
C8 C16 1.483(4) . ?
C9 C10 1.490(4) . ?
C9 N1 1.312(4) . ?
C10 C11 1.392(5) . ?
C10 C15 1.378(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.513(5) . ?
C16 O1 1.212(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.524(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 Cl1 1.744(4) . ?
C19 Cl1 1.744(4) 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
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.3(4) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 118.5(3) . . ?
N1 C5 C4 118.4(3) . . ?
N1 C5 C6 123.0(3) . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 C7 124.2(3) . . ?
C7 C6 C5 116.2(3) . . ?
C6 C7 C18 127.3(3) . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 C18 112.4(3) . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 C16 109.3(3) . . ?
C9 C8 C16 130.7(3) . . ?
C8 C9 C10 121.6(3) . . ?
N1 C9 C8 121.1(3) . . ?
N1 C9 C10 117.2(3) . . ?
C11 C10 C9 120.1(3) . . ?
C15 C10 C9 120.7(3) . . ?
C15 C10 C11 119.1(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 120.9(3) . . ?
C14 C15 H15 119.5 . . ?
C8 C16 C17 106.6(3) . . ?
O1 C16 C8 128.6(3) . . ?
O1 C16 C17 124.7(3) . . ?
C16 C17 H17A 110.5 . . ?
C16 C17 H17B 110.5 . . ?
C16 C17 C18 106.3(3) . . ?
H17A C17 H17B 108.7 . . ?
C18 C17 H17A 110.5 . . ?
C18 C17 H17B 110.5 . . ?
C7 C18 C17 104.0(3) . . ?
C7 C18 H18A 111.0 . . ?
C7 C18 H18B 111.0 . . ?
C17 C18 H18A 111.0 . . ?
C17 C18 H18B 111.0 . . ?
H18A C18 H18B 109.0 . . ?
C9 N1 C5 119.5(3) . . ?
H19A C19 H19B 107.7 . . ?
Cl1 C19 H19A 108.8 . . ?
Cl1 C19 H19A 108.8 2_655 . ?
Cl1 C19 H19B 108.8 . . ?
Cl1 C19 H19B 108.8 2_655 . ?
Cl1 C19 Cl1 113.7(4) . 2_655 ?

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
C1 C2 C3 C4 -1.0(5) . . . . ?
C1 C6 C7 C8 179.4(3) . . . . ?
C1 C6 C7 C18 -3.1(5) . . . . ?
C2 C1 C6 C5 -0.1(5) . . . . ?
C2 C1 C6 C7 179.8(3) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C3 C4 C5 N1 178.4(3) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C4 C5 C6 C7 179.7(3) . . . . ?
C4 C5 N1 C9 -178.4(3) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C5 C6 C7 C18 176.9(3) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
C6 C5 N1 C9 -0.3(4) . . . . ?
C6 C7 C8 C9 -1.4(4) . . . . ?
C6 C7 C8 C16 173.7(3) . . . . ?
C6 C7 C18 C17 178.7(3) . . . . ?
C7 C8 C9 C10 -175.1(3) . . . . ?
C7 C8 C9 N1 2.8(4) . . . . ?
C7 C8 C16 C17 10.2(4) . . . . ?
C7 C8 C16 O1 -166.5(3) . . . . ?
C8 C7 C18 C17 -3.6(4) . . . . ?
C8 C9 C10 C11 -135.2(3) . . . . ?
C8 C9 C10 C15 46.8(4) . . . . ?
C8 C9 N1 C5 -1.8(4) . . . . ?
C8 C16 C17 C18 -12.2(4) . . . . ?
C9 C8 C16 C17 -175.3(3) . . . . ?
C9 C8 C16 O1 8.0(6) . . . . ?
C9 C10 C11 C12 -179.5(3) . . . . ?
C9 C10 C15 C14 178.4(3) . . . . ?
C10 C9 N1 C5 176.1(3) . . . . ?
C10 C11 C12 C13 1.2(6) . . . . ?
C11 C10 C15 C14 0.4(5) . . . . ?
C11 C12 C13 C14 0.3(6) . . . . ?
C12 C13 C14 C15 -1.4(6) . . . . ?
C13 C14 C15 C10 1.1(5) . . . . ?
C15 C10 C11 C12 -1.5(5) . . . . ?
C16 C8 C9 C10 10.9(5) . . . . ?
C16 C8 C9 N1 -171.2(3) . . . . ?
C16 C17 C18 C7 9.6(4) . . . . ?
C18 C7 C8 C9 -179.3(3) . . . . ?
C18 C7 C8 C16 -4.1(4) . . . . ?
N1 C5 C6 C1 -178.4(3) . . . . ?
N1 C5 C6 C7 1.6(4) . . . . ?
N1 C9 C10 C11 46.9(4) . . . . ?
N1 C9 C10 C15 -131.1(3) . . . . ?
O1 C16 C17 C18 164.7(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 1.665
_oxdiff_exptl_absorpt_empirical_full_min 0.617
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_202110266
_database_code_depnum_ccdc_archive 'CCDC 2132361'
loop_
_audit_author_name
_audit_author_address
'Wen-Bo Shen' 'Henan Agricultural University'
_audit_update_record             
;
2022-01-04 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_audit_creation_date             2021-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N O3'
_chemical_formula_sum            'C19 H15 N O3'
_chemical_formula_weight         305.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     r
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.0229(4)
_cell_length_b                   10.3734(4)
_cell_length_c                   15.9971(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1497.31(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2308
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3360
_cell_measurement_theta_min      5.0640
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.902
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5895
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.068
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         5.082
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.001
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  34.00   1.00    1.00    --  -33.50  57.00  30.00   26
  2  ω    -83.00 -56.00   1.00    1.00    --  -33.50 -77.00  90.00   27
  3  ω    -52.00  -5.00   1.00    1.00    --  -33.50 -77.00  90.00   47
  4  ω    -69.00 -33.00   1.00    1.00    --  -33.50 178.00 150.00   36
  5  ω     60.00 103.00   1.00    1.00    --   36.47 178.00  60.00   43
  6  ω     61.00 108.00   1.00    1.00    --   36.47 178.00 -60.00   47
  7  ω    107.00 149.00   1.00    5.00    --  108.00 111.00-150.00   42
  8  ω    106.00 132.00   1.00    5.00    --  108.00 111.00 -60.00   26
  9  ω     39.00  84.00   1.00    5.00    --  108.00 -94.00-180.00   45
 10  ω     39.00  94.00   1.00    5.00    --  108.00 -94.00-120.00   55
 11  ω     40.00 121.00   1.00    5.00    --  108.00 -61.00 -90.00   81
 12  ω     43.00 102.00   1.00    5.00    --  108.00 -77.00  90.00   59
 13  ω      2.00  28.00   1.00    2.00    --   36.47 -99.00 150.00   26
 14  ω     59.00  96.00   1.00    2.00    --   36.47  57.00-120.00   37
 15  ω     24.00  50.00   1.00    2.00    --   36.47  57.00-120.00   26
 16  ω     46.00  77.00   1.00    2.00    --   36.47 -99.00 150.00   31
 17  ω      0.00  50.00   1.00    2.00    --   36.47 -77.00   0.00   50
 18  ω     37.00  71.00   1.00    5.00    --  108.00 -30.00-120.00   34
 19  ω     87.00 112.00   1.00    5.00    --  108.00-111.00-180.00   25
 20  ω     47.00 103.00   1.00    5.00    --  108.00-111.00  90.00   56
 21  ω     56.00 125.00   1.00    5.00    --  108.00 -30.00  30.00   69
 22  ω     88.00 118.00   1.00    5.00    --  108.00  45.00 -90.00   30
 23  ω    -26.00   0.00   1.00    2.00    --   36.47 -37.00   0.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0643933000
_diffrn_orient_matrix_UB_12      -0.1308397000
_diffrn_orient_matrix_UB_13      -0.0277690000
_diffrn_orient_matrix_UB_21      -0.1300942000
_diffrn_orient_matrix_UB_22      0.0173636000
_diffrn_orient_matrix_UB_23      0.0613614000
_diffrn_orient_matrix_UB_31      -0.0901907000
_diffrn_orient_matrix_UB_32      0.0682792000
_diffrn_orient_matrix_UB_33      -0.0688185000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2389
_reflns_number_total             2676
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 869 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.052
_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)+(0.0617P)²+0.0077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1192
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 H1-O1
 0.9 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.6774(3) 0.5241(2) 0.48482(13) 0.0432(5) Uani 1 1 d D . . . .
H1 H 0.621(4) 0.584(3) 0.463(3) 0.056(12) Uiso 1 1 d D . . . .
O2 O 0.4913(3) 0.3204(2) 0.6110(2) 0.0752(10) Uani 1 1 d . . . . .
O3 O 0.9900(3) 0.7837(2) 0.57419(16) 0.0525(6) Uani 1 1 d . . . . .
N1 N 0.7630(3) 0.6832(2) 0.58133(15) 0.0376(6) Uani 1 1 d . . . . .
C1 C 0.4471(4) 0.8883(3) 0.6501(2) 0.0498(8) Uani 1 1 d . . . . .
H1A H 0.3540 0.8778 0.6742 0.060 Uiso 1 1 calc R . . . .
C2 C 0.4982(5) 1.0103(3) 0.6327(3) 0.0587(10) Uani 1 1 d . . . . .
H2 H 0.4415 1.0822 0.6463 0.070 Uiso 1 1 calc R . . . .
C3 C 0.6340(5) 1.0249(3) 0.5951(3) 0.0621(10) Uani 1 1 d . . . . .
H3 H 0.6667 1.1071 0.5811 0.074 Uiso 1 1 calc R . . . .
C4 C 0.7237(4) 0.9193(3) 0.5775(2) 0.0525(9) Uani 1 1 d . . . . .
H4 H 0.8160 0.9312 0.5527 0.063 Uiso 1 1 calc R . . . .
C5 C 0.6748(4) 0.7952(3) 0.59712(17) 0.0381(6) Uani 1 1 d . . . . .
C6 C 0.5335(4) 0.7797(3) 0.63199(18) 0.0381(7) Uani 1 1 d . . . . .
C7 C 0.4742(3) 0.6509(3) 0.64156(18) 0.0377(6) Uani 1 1 d . . . . .
C8 C 0.3244(4) 0.6191(3) 0.6772(3) 0.0519(8) Uani 1 1 d . . . . .
H8A H 0.2463 0.6621 0.6463 0.062 Uiso 1 1 calc R . . . .
H8B H 0.3182 0.6442 0.7355 0.062 Uiso 1 1 calc R . . . .
C9 C 0.3134(4) 0.4730(3) 0.6677(3) 0.0558(9) Uani 1 1 d . . . . .
H9A H 0.3003 0.4323 0.7218 0.067 Uiso 1 1 calc R . . . .
H9B H 0.2303 0.4502 0.6323 0.067 Uiso 1 1 calc R . . . .
C10 C 0.4589(4) 0.4302(3) 0.6279(2) 0.0482(8) Uani 1 1 d . . . . .
C11 C 0.5480(3) 0.5472(3) 0.61471(19) 0.0365(6) Uani 1 1 d . . . . .
C12 C 0.6951(3) 0.5507(3) 0.57058(18) 0.0357(6) Uani 1 1 d . . . . .
C13 C 0.7994(3) 0.4500(3) 0.6080(2) 0.0403(7) Uani 1 1 d . . . . .
C14 C 0.8544(4) 0.3485(3) 0.5614(3) 0.0526(8) Uani 1 1 d . . . . .
H14 H 0.8280 0.3393 0.5055 0.063 Uiso 1 1 calc R . . . .
C15 C 0.9494(5) 0.2604(4) 0.5988(4) 0.0733(14) Uani 1 1 d . . . . .
H15 H 0.9878 0.1929 0.5673 0.088 Uiso 1 1 calc R . . . .
C16 C 0.9872(5) 0.2711(5) 0.6808(4) 0.0824(17) Uani 1 1 d . . . . .
H16 H 1.0501 0.2107 0.7051 0.099 Uiso 1 1 calc R . . . .
C17 C 0.9319(5) 0.3717(5) 0.7280(3) 0.0752(14) Uani 1 1 d . . . . .
H17 H 0.9572 0.3791 0.7841 0.090 Uiso 1 1 calc R . . . .
C18 C 0.8390(4) 0.4614(4) 0.6916(2) 0.0538(9) Uani 1 1 d . . . . .
H18 H 0.8028 0.5297 0.7232 0.065 Uiso 1 1 calc R . . . .
C19 C 0.9118(4) 0.6896(3) 0.5654(2) 0.0409(7) Uani 1 1 d . . . . .
H19 H 0.9572 0.6148 0.5461 0.049 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 H1 0.87(2) . ?
O1 C12 1.408(4) . ?
O2 C10 1.206(4) . ?
O3 C19 1.212(4) . ?
N1 C5 1.431(4) . ?
N1 C12 1.515(4) . ?
N1 C19 1.368(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.376(5) . ?
C1 C6 1.400(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(4) . ?
C5 C6 1.400(5) . ?
C6 C7 1.447(4) . ?
C7 C8 1.503(5) . ?
C7 C11 1.336(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.527(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.525(5) . ?
C10 C11 1.471(4) . ?
C11 C12 1.504(4) . ?
C12 C13 1.528(4) . ?
C13 C14 1.382(5) . ?
C13 C18 1.390(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.360(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(6) . ?
C18 H18 0.9300 . ?
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
C12 O1 H1 109(3) . . ?
C5 N1 C12 122.1(2) . . ?
C19 N1 C5 122.7(3) . . ?
C19 N1 C12 114.8(2) . . ?
C2 C1 H1A 119.6 . . ?
C2 C1 C6 120.7(4) . . ?
C6 C1 H1A 119.6 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 N1 122.2(3) . . ?
C4 C5 C6 118.9(3) . . ?
C6 C5 N1 118.9(3) . . ?
C1 C6 C7 121.0(3) . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 C7 119.0(3) . . ?
C6 C7 C8 125.1(3) . . ?
C11 C7 C6 121.7(3) . . ?
C11 C7 C8 113.2(3) . . ?
C7 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C7 C8 C9 103.8(3) . . ?
H8A C8 H8B 109.0 . . ?
C9 C8 H8A 111.0 . . ?
C9 C8 H8B 111.0 . . ?
C8 C9 H9A 110.6 . . ?
C8 C9 H9B 110.6 . . ?
H9A C9 H9B 108.7 . . ?
C10 C9 C8 105.9(3) . . ?
C10 C9 H9A 110.6 . . ?
C10 C9 H9B 110.6 . . ?
O2 C10 C9 125.2(3) . . ?
O2 C10 C11 127.9(3) . . ?
C11 C10 C9 106.9(3) . . ?
C7 C11 C10 110.2(3) . . ?
C7 C11 C12 124.9(3) . . ?
C10 C11 C12 124.7(3) . . ?
O1 C12 N1 109.5(2) . . ?
O1 C12 C11 110.6(2) . . ?
O1 C12 C13 108.5(2) . . ?
N1 C12 C13 109.1(2) . . ?
C11 C12 N1 109.0(2) . . ?
C11 C12 C13 110.1(2) . . ?
C14 C13 C12 122.0(3) . . ?
C14 C13 C18 119.5(3) . . ?
C18 C13 C12 118.5(3) . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.3(4) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(5) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.9(4) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.3(4) . . ?
C17 C18 H18 119.8 . . ?
O3 C19 N1 126.1(3) . . ?
O3 C19 H19 117.0 . . ?
N1 C19 H19 117.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.87(2) 1.91(2) 2.779(3) 174(4) 3_466

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
O1 C12 C13 C14 -3.6(4) . . . . ?
O1 C12 C13 C18 176.7(3) . . . . ?
O2 C10 C11 C7 179.9(4) . . . . ?
O2 C10 C11 C12 4.8(6) . . . . ?
N1 C5 C6 C1 178.2(3) . . . . ?
N1 C5 C6 C7 -7.4(4) . . . . ?
N1 C12 C13 C14 -122.8(3) . . . . ?
N1 C12 C13 C18 57.5(3) . . . . ?
C1 C2 C3 C4 -2.8(6) . . . . ?
C1 C6 C7 C8 -5.2(5) . . . . ?
C1 C6 C7 C11 171.4(3) . . . . ?
C2 C1 C6 C5 1.2(5) . . . . ?
C2 C1 C6 C7 -173.2(3) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C3 C4 C5 N1 -179.3(3) . . . . ?
C3 C4 C5 C6 1.9(5) . . . . ?
C4 C5 C6 C1 -3.0(4) . . . . ?
C4 C5 C6 C7 171.4(3) . . . . ?
C5 N1 C12 O1 96.5(3) . . . . ?
C5 N1 C12 C11 -24.7(3) . . . . ?
C5 N1 C12 C13 -144.9(3) . . . . ?
C5 N1 C19 O3 11.2(5) . . . . ?
C5 C6 C7 C8 -179.6(3) . . . . ?
C5 C6 C7 C11 -2.9(4) . . . . ?
C6 C1 C2 C3 1.7(6) . . . . ?
C6 C7 C8 C9 176.3(3) . . . . ?
C6 C7 C11 C10 -176.8(3) . . . . ?
C6 C7 C11 C12 -1.7(5) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C7 C11 C12 O1 -106.1(3) . . . . ?
C7 C11 C12 N1 14.4(4) . . . . ?
C7 C11 C12 C13 134.0(3) . . . . ?
C8 C7 C11 C10 0.2(4) . . . . ?
C8 C7 C11 C12 175.3(3) . . . . ?
C8 C9 C10 O2 179.7(4) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C7 0.2(4) . . . . ?
C9 C10 C11 C12 -174.9(3) . . . . ?
C10 C11 C12 O1 68.3(4) . . . . ?
C10 C11 C12 N1 -171.2(3) . . . . ?
C10 C11 C12 C13 -51.6(4) . . . . ?
C11 C7 C8 C9 -0.5(4) . . . . ?
C11 C12 C13 C14 117.7(3) . . . . ?
C11 C12 C13 C18 -62.0(3) . . . . ?
C12 N1 C5 C4 -156.1(3) . . . . ?
C12 N1 C5 C6 22.6(4) . . . . ?
C12 N1 C19 O3 -176.0(3) . . . . ?
C12 C13 C14 C15 179.7(3) . . . . ?
C12 C13 C18 C17 179.4(3) . . . . ?
C13 C14 C15 C16 1.1(6) . . . . ?
C14 C13 C18 C17 -0.3(5) . . . . ?
C14 C15 C16 C17 -0.6(7) . . . . ?
C15 C16 C17 C18 -0.3(6) . . . . ?
C16 C17 C18 C13 0.7(6) . . . . ?
C18 C13 C14 C15 -0.6(5) . . . . ?
C19 N1 C5 C4 16.2(5) . . . . ?
C19 N1 C5 C6 -165.0(3) . . . . ?
C19 N1 C12 O1 -76.4(3) . . . . ?
C19 N1 C12 C11 162.4(3) . . . . ?
C19 N1 C12 C13 42.2(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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.924
