# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_XBY-20220625
_database_code_depnum_ccdc_archive 'CCDC 2225438'
loop_
_audit_author_name
_audit_author_address
a
;a CCDC number
China
;
_audit_update_record             
;
2022-12-09 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_audit_creation_date             2022-07-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C27 H23 Br N2 O2'
_chemical_formula_sum            'C27 H23 Br N2 O2'
_chemical_formula_weight         487.40
_chemical_absolute_configuration ad
_chemical_oxdiff_formula         'Br1 C1 N1 O1 H1'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   9.5102(2)
_cell_length_b                   10.95350(10)
_cell_length_c                   22.7080(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2365.49(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16389
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.4950
_cell_measurement_theta_min      4.4530
_exptl_absorpt_coefficient_mu    2.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44329
_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_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3685
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             999.9146
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            35611
_diffrn_reflns_theta_full        71.5492
_diffrn_reflns_theta_max         71.55
_diffrn_reflns_theta_min         3.89
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9941
_diffrn_measured_fraction_theta_max 0.9941
_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  34.00   1.00    1.82    --  -35.62   6.00   8.00  138
  2  ω     27.00  92.00   1.00    1.82    --   35.62-130.00 129.00   65
  3  ω     94.00 176.00   1.00    7.50    --  107.12 125.00 113.00   82
  4  ω     37.00 176.00   1.00    7.50    --  107.12  -6.00-168.00  139
  5  ω     91.00 176.00   1.00    7.50    --  107.12 130.00-158.00   85
  6  ω     57.00 108.00   1.00    1.82    --   35.62 178.00  90.00   51
  7  ω     57.00 108.00   1.00    1.82    --   35.62 178.00 -30.00   51
  8  ω    -34.00  55.00   1.00    1.82    --   35.62 -38.00  90.00   89
  9  ω     37.00 129.00   1.00    7.50    --  107.12 -30.00 -30.00   92
 10  ω     37.00 113.00   1.00    7.50    --  107.12-111.00   0.00   76
 11  ω     89.00 174.00   1.00    7.50    --  107.12  61.00-120.00   85
 12  ω     40.00 134.00   1.00    7.50    --  107.12 -77.00   0.00   94
 13  ω     40.00 125.00   1.00    7.50    --  107.12 -61.00 -90.00   85
 14  ω     37.00 113.00   1.00    7.50    --  107.12-111.00-180.00   76
 15  ω     19.00 103.00   1.00    1.82    --   35.62  57.00   0.00   84
 16  ω      9.00 103.00   1.00    1.82    --   35.62  77.00 -90.00   94
 17  ω     19.00 103.00   1.00    1.82    --   35.62  57.00-120.00   84
 18  ω      9.00 103.00   1.00    1.82    --   35.62  77.00 120.00   94
 19  ω     80.00 175.00   1.00    7.50    --  107.12  77.00 -30.00   95
 20  ω     90.00 176.00   1.00    7.50    --  107.12  45.00 -60.00   86
 21  ω     40.00 125.00   1.00    7.50    --  107.12 -61.00 150.00   85
 22  ω     80.00 175.00   1.00    7.50    --  107.12  77.00 120.00   95
 23  ω     69.00 178.00   1.00    7.50    --  107.12  15.00  30.00  109
 24  ω     80.00 175.00   1.00    7.50    --  107.12  77.00  30.00   95
 25  ω     86.00 177.00   1.00    7.50    --  107.12  30.00-150.00   91
 26  ω     80.00 175.00   1.00    7.50    --  107.12  77.00  60.00   95
 27  ω    -65.00  36.00   1.00    1.82    --  -35.62  19.00  90.00  101
 28  ω     32.00  97.00   1.00    1.82    --   35.62-140.00 -44.00   65
 29  ω      9.00 103.00   1.00    1.82    --   35.62  77.00-180.00   94
 30  ω      9.00 103.00   1.00    1.82    --   35.62  77.00  30.00   94
 31  ω     80.00 175.00   1.00    7.50    --  107.12  77.00  90.00   95
 32  ω     80.00 175.00   1.00    7.50    --  107.12  77.00-150.00   95
 33  ω     90.00 176.00   1.00    7.50    --  107.12  45.00 -90.00   86
 34  ω     80.00 171.00   1.00    7.50    --  107.12  77.00 150.00   91
 35  ω     80.00 175.00   1.00    7.50    --  107.12  77.00   0.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0377585000
_diffrn_orient_matrix_UB_12      -0.1367760000
_diffrn_orient_matrix_UB_13      0.0006239000
_diffrn_orient_matrix_UB_21      -0.1571163000
_diffrn_orient_matrix_UB_22      0.0326107000
_diffrn_orient_matrix_UB_23      -0.0051850000
_diffrn_orient_matrix_UB_31      0.0116271000
_diffrn_orient_matrix_UB_32      -0.0037760000
_diffrn_orient_matrix_UB_33      -0.0676267000
_diffrn_oxdiff_digest_frames     
;
014094db4519d441cf971a03e887eec329000302847
;
_diffrn_oxdiff_digest_hkl        
;
01e0b79a8e4822e62a5b5aca804225ce553493
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.989
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              27
_reflns_limit_l_min              -27
_reflns_number_gt                4354
_reflns_number_total             4585
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.7218
_refine_diff_density_min         -0.7315
_refine_diff_density_rms         0.0574
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.017(19)
_refine_ls_d_res_high            0.8127
_refine_ls_d_res_low             11.3540
_refine_ls_goodness_of_fit_ref   1.0388
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4585
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.0388
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+1.1314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1020
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22a,H22b)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C14(H14), C17(H17), C2(H2), C16(H16), C20(H20), C24(H24),
 C28(H28), C27(H27), C3(H3), C4(H4), C26(H26), C25(H25)
2.d Idealised Me refined as rotating group:
 C31(H31a,H31b,H31c), C21(H21a,H21b,H21c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Br18 Br 0.80697(7) 0.72244(4) 0.537052(19) 0.1039(2) Uani 1.000000 .
O30 O 0.7248(2) 0.2075(2) 0.25135(9) 0.0610(5) Uani 1.000000 .
N11 N 0.4299(2) 0.0954(2) 0.33345(11) 0.0496(5) Uani 1.000000 .
O32 O 0.5431(3) 0.0990(3) 0.21884(10) 0.0778(7) Uani 1.000000 .
C12 C 0.5697(3) 0.4109(2) 0.43817(11) 0.0412(5) Uani 1.000000 .
C29 C 0.5992(3) 0.1572(3) 0.25714(12) 0.0483(6) Uani 1.000000 .
C9 C 0.5649(3) 0.2791(2) 0.34729(11) 0.0406(5) Uani 1.000000 .
H9 H 0.6312(3) 0.3333(2) 0.33233(11) 0.0487(6) Uiso 1.000000 R
C10 C 0.5345(3) 0.1799(2) 0.31606(12) 0.0414(5) Uani 1.000000 .
N19 N 0.1188(3) 0.3935(3) 0.39903(15) 0.0729(8) Uani 1.000000 .
C8 C 0.4974(3) 0.3082(2) 0.40584(11) 0.0416(5) Uani 1.000000 .
H8 H 0.5068(3) 0.2351(2) 0.43043(11) 0.0500(7) Uiso 1.000000 R
C13 C 0.5843(3) 0.5259(2) 0.41288(13) 0.0492(6) Uani 1.000000 .
H13 H 0.5478(3) 0.5401(2) 0.37550(13) 0.0591(8) Uiso 1.000000 R
C1 C 0.2885(3) 0.1368(3) 0.33406(12) 0.0495(6) Uani 1.000000 .
C6 C 0.2575(3) 0.2468(3) 0.36323(12) 0.0474(6) Uani 1.000000 .
C7 C 0.3425(3) 0.3284(3) 0.39642(12) 0.0466(6) Uani 1.000000 .
C14 C 0.6521(3) 0.6195(2) 0.44242(13) 0.0517(7) Uani 1.000000 .
H14 H 0.6616(3) 0.6961(2) 0.42521(13) 0.0621(8) Uiso 1.000000 R
C23 C 0.6044(4) -0.0703(2) 0.33985(15) 0.0583(8) Uani 1.000000 .
C17 C 0.6240(4) 0.3931(3) 0.49412(13) 0.0569(7) Uani 1.000000 .
H17 H 0.6148(4) 0.3171(3) 0.51194(13) 0.0682(9) Uiso 1.000000 R
C15 C 0.7051(4) 0.5970(3) 0.49750(12) 0.0554(7) Uani 1.000000 .
C2 C 0.1779(4) 0.0724(3) 0.30968(15) 0.0643(8) Uani 1.000000 .
H2 H 0.1949(4) -0.0009(3) 0.29035(15) 0.0771(10) Uiso 1.000000 R
C22 C 0.4565(4) -0.0347(3) 0.32342(16) 0.0613(8) Uani 1.000000 .
H22a H 0.3906(4) -0.0825(3) 0.34652(16) 0.0735(10) Uiso 1.000000 R
H22b H 0.4406(4) -0.0534(3) 0.28220(16) 0.0735(10) Uiso 1.000000 R
C16 C 0.6913(5) 0.4857(3) 0.52387(13) 0.0682(9) Uani 1.000000 .
H16 H 0.7270(5) 0.4725(3) 0.56147(13) 0.0818(11) Uiso 1.000000 R
C5 C 0.1171(3) 0.2894(4) 0.36629(15) 0.0627(8) Uani 1.000000 .
C20 C 0.2553(3) 0.4165(3) 0.41729(16) 0.0611(8) Uani 1.000000 .
H20 H 0.2829(3) 0.4823(3) 0.44039(16) 0.0733(9) Uiso 1.000000 R
C24 C 0.6840(4) -0.1419(3) 0.30274(18) 0.0759(10) Uani 1.000000 .
H24 H 0.6476(4) -0.1661(3) 0.26658(18) 0.0911(12) Uiso 1.000000 R
C28 C 0.6632(4) -0.0328(3) 0.39224(15) 0.0620(8) Uani 1.000000 .
H28 H 0.6113(4) 0.0162(3) 0.41769(15) 0.0744(10) Uiso 1.000000 R
C27 C 0.7988(4) -0.0672(3) 0.40759(17) 0.0714(9) Uani 1.000000 .
H27 H 0.8377(4) -0.0405(3) 0.44288(17) 0.0857(11) Uiso 1.000000 R
C3 C 0.0400(4) 0.1174(4) 0.31397(18) 0.0767(11) Uani 1.000000 .
H3 H -0.0323(4) 0.0721(4) 0.29715(18) 0.0921(14) Uiso 1.000000 R
C4 C 0.0070(4) 0.2237(5) 0.34149(19) 0.0805(11) Uani 1.000000 .
H4 H -0.0853(4) 0.2514(5) 0.34363(19) 0.0966(14) Uiso 1.000000 R
C26 C 0.8755(4) -0.1409(4) 0.3705(2) 0.0810(11) Uani 1.000000 .
H26 H 0.9660(4) -0.1651(4) 0.3807(2) 0.0972(13) Uiso 1.000000 R
C25 C 0.8176(5) -0.1779(4) 0.3190(2) 0.0917(13) Uani 1.000000 .
H25 H 0.8689(5) -0.2285(4) 0.2941(2) 0.1100(16) Uiso 1.000000 R
C31 C 0.7939(5) 0.1852(5) 0.19601(16) 0.0879(12) Uani 1.000000 .
H31a H 0.7370(19) 0.216(3) 0.1645(2) 0.1318(19) Uiso 1.000000 GR
H31b H 0.8836(18) 0.225(3) 0.1957(6) 0.1318(19) Uiso 1.000000 GR
H31c H 0.807(3) 0.0989(5) 0.1909(7) 0.1318(19) Uiso 1.000000 GR
C21 C -0.0028(5) 0.4676(5) 0.4133(3) 0.118(2) Uani 1.000000 .
H21a H -0.024(3) 0.520(3) 0.3807(8) 0.177(3) Uiso 1.000000 GR
H21b H -0.0818(13) 0.4156(5) 0.421(2) 0.177(3) Uiso 1.000000 GR
H21c H 0.0173(18) 0.516(3) 0.4475(13) 0.177(3) Uiso 1.000000 GR


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
Br18 C15 1.906(3) . ?
O30 C29 1.322(4) . ?
O30 C31 1.439(4) . ?
N11 C10 1.415(3) . ?
N11 C1 1.419(4) . ?
N11 C22 1.465(4) . ?
O32 C29 1.203(4) . ?
C12 C8 1.509(4) . ?
C12 C13 1.391(4) . ?
C12 C17 1.385(4) . ?
C29 C10 1.494(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.330(4) . ?
C9 C8 1.511(4) . ?
N19 C5 1.361(5) . ?
N19 C20 1.386(4) . ?
N19 C21 1.450(5) . ?
C8 H8 0.9800 . ?
C8 C7 1.505(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(4) . ?
C1 C6 1.407(4) . ?
C1 C2 1.381(4) . ?
C6 C7 1.422(4) . ?
C6 C5 1.416(4) . ?
C7 C20 1.357(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.370(4) . ?
C23 C22 1.507(5) . ?
C23 C24 1.378(5) . ?
C23 C28 1.377(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.376(4) . ?
C15 C16 1.365(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.405(5) . ?
C22 H22a 0.9700 . ?
C22 H22b 0.9700 . ?
C16 H16 0.9300 . ?
C5 C4 1.389(5) . ?
C20 H20 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.380(6) . ?
C28 H28 0.9300 . ?
C28 C27 1.388(5) . ?
C27 H27 0.9300 . ?
C27 C26 1.375(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(6) . ?
C4 H4 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.356(6) . ?
C25 H25 0.9300 . ?
C31 H31a 0.9600 . ?
C31 H31b 0.9600 . ?
C31 H31c 0.9600 . ?
C21 H21a 0.9600 . ?
C21 H21b 0.9600 . ?
C21 H21c 0.9600 . ?

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
C31 O30 C29 115.4(3) . . ?
C1 N11 C10 117.4(2) . . ?
C22 N11 C10 118.1(2) . . ?
C22 N11 C1 118.4(2) . . ?
C13 C12 C8 121.3(2) . . ?
C17 C12 C8 120.7(2) . . ?
C17 C12 C13 118.0(3) . . ?
O32 C29 O30 123.3(3) . . ?
C10 C29 O30 113.1(2) . . ?
C10 C29 O32 123.6(3) . . ?
C10 C9 H9 118.35(15) . . ?
C8 C9 H9 118.35(13) . . ?
C8 C9 C10 123.3(2) . . ?
C29 C10 N11 115.5(2) . . ?
C9 C10 N11 122.6(2) . . ?
C9 C10 C29 121.6(2) . . ?
C20 N19 C5 109.1(3) . . ?
C21 N19 C5 125.6(4) . . ?
C21 N19 C20 125.3(4) . . ?
C9 C8 C12 113.1(2) . . ?
H8 C8 C12 106.89(14) . . ?
H8 C8 C9 106.89(14) . . ?
C7 C8 C12 113.9(2) . . ?
C7 C8 C9 108.8(2) . . ?
C7 C8 H8 106.89(14) . . ?
H13 C13 C12 119.45(16) . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.45(16) . . ?
C6 C1 N11 118.5(2) . . ?
C2 C1 N11 123.7(3) . . ?
C2 C1 C6 117.8(3) . . ?
C7 C6 C1 132.0(2) . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 C7 107.7(3) . . ?
C6 C7 C8 122.6(2) . . ?
C20 C7 C8 130.8(3) . . ?
C20 C7 C6 106.5(3) . . ?
H14 C14 C13 120.64(16) . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14 120.64(17) . . ?
C24 C23 C22 120.6(3) . . ?
C28 C23 C22 121.1(3) . . ?
C28 C23 C24 118.3(3) . . ?
H17 C17 C12 119.35(16) . . ?
C16 C17 C12 121.3(3) . . ?
C16 C17 H17 119.35(17) . . ?
C14 C15 Br18 119.2(2) . . ?
C16 C15 Br18 119.1(2) . . ?
C16 C15 C14 121.7(3) . . ?
H2 C2 C1 119.9(2) . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.9(2) . . ?
C23 C22 N11 112.0(2) . . ?
H22a C22 N11 109.21(17) . . ?
H22a C22 C23 109.21(17) . . ?
H22b C22 N11 109.21(18) . . ?
H22b C22 C23 109.21(18) . . ?
H22b C22 H22a 107.9 . . ?
C15 C16 C17 119.2(3) . . ?
H16 C16 C17 120.41(17) . . ?
H16 C16 C15 120.41(18) . . ?
C6 C5 N19 106.9(3) . . ?
C4 C5 N19 131.6(4) . . ?
C4 C5 C6 121.3(4) . . ?
C7 C20 N19 109.8(3) . . ?
H20 C20 N19 125.1(2) . . ?
H20 C20 C7 125.09(19) . . ?
H24 C24 C23 119.8(2) . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8(2) . . ?
H28 C28 C23 119.6(2) . . ?
C27 C28 C23 120.9(3) . . ?
C27 C28 H28 119.6(2) . . ?
H27 C27 C28 120.0(2) . . ?
C26 C27 C28 119.9(4) . . ?
C26 C27 H27 120.0(3) . . ?
H3 C3 C2 118.4(2) . . ?
C4 C3 C2 123.2(3) . . ?
C4 C3 H3 118.4(2) . . ?
C3 C4 C5 117.2(3) . . ?
H4 C4 C5 121.4(3) . . ?
H4 C4 C3 121.4(2) . . ?
H26 C26 C27 120.4(3) . . ?
C25 C26 C27 119.3(4) . . ?
C25 C26 H26 120.4(3) . . ?
C26 C25 C24 121.2(4) . . ?
H25 C25 C24 119.4(2) . . ?
H25 C25 C26 119.4(3) . . ?
H31a C31 O30 109.5 . . ?
H31b C31 O30 109.5 . . ?
H31b C31 H31a 109.5 . . ?
H31c C31 O30 109.5 . . ?
H31c C31 H31a 109.5 . . ?
H31c C31 H31b 109.5 . . ?
H21a C21 N19 109.5 . . ?
H21b C21 N19 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 N19 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?

_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 2.341
_oxdiff_exptl_absorpt_empirical_full_min 0.446
####################################################################### 
# 
# 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_xby-2-20221012
_database_code_depnum_ccdc_archive 'CCDC 2225441'
loop_
_audit_author_name
_audit_author_address
c
;a CCDC number
China
;
_audit_update_record             
;
2022-12-09 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_audit_creation_date             2022-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 Cl N2'
_chemical_formula_sum            'C16 H15 Cl N2'
_chemical_formula_weight         270.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 Cl1'
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'

_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                   10.2358(3)
_cell_length_b                   5.6225(2)
_cell_length_c                   24.3001(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.373(3)
_cell_angle_gamma                90
_cell_volume                     1371.03(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2802
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0410
_cell_measurement_theta_min      3.7220
_shelx_estimated_absorpt_T_max   0.892
_shelx_estimated_absorpt_T_min   0.720
_exptl_absorpt_coefficient_mu    2.344
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81830
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5865
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.519
_diffrn_reflns_theta_min         3.711
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  36.00   1.00    1.00    --  -35.62  15.00 -81.00  100
  2  ω    -76.00 -51.00   1.00    1.00    --  -35.62 -15.00 108.00   25
  3  ω   -105.00 -79.00   1.00    1.00    --  -35.62 -15.00 108.00   26
  4  ω     28.00  53.00   1.00    1.00    --   35.62  15.00 -81.00   25
  5  ω     47.00 136.00   1.00    2.37    --  107.12 -15.00 108.00   89
  6  ω    124.00 174.00   1.00    2.37    --  107.12  15.00 -81.00   50
  7  ω   -104.00 -28.00   1.00    1.00    --  -35.62 -38.00  90.00   76
  8  ω     -5.00  20.00   1.00    1.00    --   35.62 -15.00 108.00   25
  9  ω     60.00 106.00   1.00    1.00    --   35.62 178.00 -90.00   46
 10  ω      5.00  75.00   1.00    1.00    --   35.62 -99.00  60.00   70
 11  ω     55.00  80.00   1.00    1.00    --   35.62-178.00  60.00   25
 12  ω     40.00 124.00   1.00    2.37    --  107.12 -61.00 150.00   84
 13  ω    118.00 170.00   1.00    2.37    --  107.12  61.00 -60.00   52
 14  ω     39.00  65.00   1.00    2.37    --  107.12 -95.00 -90.00   26
 15  ω     66.00  91.00   1.00    2.37    --  107.12 -95.00-120.00   25
 16  ω     38.00  63.00   1.00    2.37    --  107.12 -95.00-120.00   25
 17  ω     43.00  89.00   1.00    2.37    --  107.12 -30.00  30.00   46
 18  ω     51.00  96.00   1.00    2.37    --  107.12 -95.00  90.00   45
 19  ω     84.00 110.00   1.00    2.37    --  107.12 -95.00 -90.00   26
 20  ω     46.00  72.00   1.00    2.37    --  107.12-111.00 -90.00   26
 21  ω     40.00 109.00   1.00    2.37    --  107.12 -95.00 150.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0244854000
_diffrn_orient_matrix_UB_12      -0.0511862000
_diffrn_orient_matrix_UB_13      -0.0635168000
_diffrn_orient_matrix_UB_21      0.1514904000
_diffrn_orient_matrix_UB_22      -0.0132946000
_diffrn_orient_matrix_UB_23      0.0028694000
_diffrn_orient_matrix_UB_31      -0.0028549000
_diffrn_orient_matrix_UB_32      -0.2688190000
_diffrn_orient_matrix_UB_33      0.0119095000
_diffrn_oxdiff_digest_frames     
;
016c18c3661195182ee58b9c1eee30657b000297523
;
_diffrn_oxdiff_digest_hkl        
;
010ed0760cf062ffacdfa3b869b098c95e68f7
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2120
_reflns_number_total             2614
_reflns_odcompleteness_completeness 99.89
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0788
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1484P)²+0.2659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2180
_refine_ls_wR_factor_ref         0.2348
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C2(H2), C17(H17), C8(H8), C13(H13), C16(H16), C15(H15),
 C14(H14)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl18 Cl 0.89723(8) 0.4611(2) 0.43527(4) 0.0802(4) Uani 1 1 d . . . . .
N10 N 0.6414(3) 0.1990(5) 0.41024(10) 0.0653(7) Uani 1 1 d . . . . .
N9 N 0.4730(3) 0.5887(5) 0.23916(10) 0.0650(7) Uani 1 1 d . . . . .
C5 C 0.6575(3) 0.3610(5) 0.36978(11) 0.0509(6) Uani 1 1 d . . . . .
C6 C 0.5604(3) 0.4042(5) 0.32041(11) 0.0523(6) Uani 1 1 d . . . . .
C11 C 0.5595(3) -0.0121(5) 0.39988(12) 0.0573(7) Uani 1 1 d . . . . .
H11A H 0.608862 -0.143807 0.419759 0.069 Uiso 1 1 calc R . . . .
H11B H 0.545218 -0.048032 0.360100 0.069 Uiso 1 1 calc R . . . .
C1 C 0.5820(3) 0.5794(5) 0.28249(12) 0.0555(7) Uani 1 1 d . . . . .
C12 C 0.4260(3) 0.0004(5) 0.41662(12) 0.0556(7) Uani 1 1 d . . . . .
C7 C 0.4307(3) 0.3071(6) 0.29820(12) 0.0624(8) Uani 1 1 d . . . . .
H7 H 0.387536 0.187584 0.314173 0.075 Uiso 1 1 calc R . . . .
C4 C 0.7704(3) 0.5053(6) 0.37588(13) 0.0588(7) Uani 1 1 d . . . . .
C3 C 0.7899(3) 0.6779(6) 0.33790(15) 0.0682(8) Uani 1 1 d . . . . .
H3 H 0.868183 0.766463 0.344863 0.082 Uiso 1 1 calc R . . . .
C2 C 0.6967(3) 0.7221(6) 0.29015(14) 0.0685(8) Uani 1 1 d . . . . .
H2 H 0.708759 0.838937 0.264523 0.082 Uiso 1 1 calc R . . . .
C17 C 0.3889(4) 0.1864(6) 0.44693(13) 0.0712(9) Uani 1 1 d . . . . .
H17 H 0.445837 0.314930 0.456932 0.085 Uiso 1 1 calc R . . . .
C8 C 0.3837(3) 0.4231(6) 0.24964(13) 0.0678(8) Uani 1 1 d . . . . .
H8 H 0.301493 0.394004 0.226485 0.081 Uiso 1 1 calc R . . . .
C13 C 0.3383(4) -0.1884(6) 0.40276(16) 0.0744(9) Uani 1 1 d . . . . .
H13 H 0.362017 -0.314928 0.382103 0.089 Uiso 1 1 calc R . . . .
C16 C 0.2637(5) 0.1801(9) 0.46265(16) 0.0945(15) Uani 1 1 d . . . . .
H16 H 0.237685 0.306489 0.482708 0.113 Uiso 1 1 calc R . . . .
C19 C 0.4541(5) 0.7505(8) 0.19211(15) 0.0872(11) Uani 1 1 d . . . . .
H19A H 0.450133 0.910706 0.205363 0.131 Uiso 1 1 calc GR . . . .
H19B H 0.372420 0.712836 0.166721 0.131 Uiso 1 1 calc GR . . . .
H19C H 0.527292 0.735645 0.172965 0.131 Uiso 1 1 calc GR . . . .
C15 C 0.1799(5) -0.0094(11) 0.4488(2) 0.1040(17) Uani 1 1 d . . . . .
H15 H 0.097858 -0.012816 0.459826 0.125 Uiso 1 1 calc R . . . .
C14 C 0.2171(4) -0.1919(9) 0.4190(2) 0.0989(14) Uani 1 1 d . . . . .
H14 H 0.160221 -0.320766 0.409357 0.119 Uiso 1 1 calc R . . . .
H10 H 0.703(4) 0.178(7) 0.4402(17) 0.083(12) Uiso 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
Cl18 C4 1.758(3) . ?
N10 C5 1.374(4) . ?
N10 C11 1.446(4) . ?
N10 H10 0.87(4) . ?
N9 C1 1.375(4) . ?
N9 C8 1.363(4) . ?
N9 C19 1.444(4) . ?
C5 C6 1.420(4) . ?
C5 C4 1.396(4) . ?
C6 C1 1.396(4) . ?
C6 C7 1.439(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.502(4) . ?
C1 C2 1.404(5) . ?
C12 C17 1.375(4) . ?
C12 C13 1.389(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.351(4) . ?
C4 C3 1.380(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.372(5) . ?
C2 H2 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.408(6) . ?
C8 H8 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.373(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.368(8) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C14 1.355(7) . ?
C14 H14 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
C5 N10 C11 124.5(2) . . ?
C5 N10 H10 121(3) . . ?
C11 N10 H10 109(3) . . ?
C1 N9 C19 126.3(3) . . ?
C8 N9 C1 107.6(2) . . ?
C8 N9 C19 126.0(3) . . ?
N10 C5 C6 123.7(3) . . ?
N10 C5 C4 121.5(3) . . ?
C4 C5 C6 114.7(3) . . ?
C5 C6 C7 133.9(3) . . ?
C1 C6 C5 120.2(3) . . ?
C1 C6 C7 105.9(3) . . ?
N10 C11 H11A 108.2 . . ?
N10 C11 H11B 108.2 . . ?
N10 C11 C12 116.2(2) . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
N9 C1 C6 108.8(3) . . ?
N9 C1 C2 127.6(3) . . ?
C6 C1 C2 123.5(3) . . ?
C17 C12 C11 122.9(3) . . ?
C17 C12 C13 118.5(3) . . ?
C13 C12 C11 118.5(3) . . ?
C6 C7 H7 126.6 . . ?
C8 C7 C6 106.7(3) . . ?
C8 C7 H7 126.6 . . ?
C5 C4 Cl18 117.8(2) . . ?
C3 C4 Cl18 117.9(2) . . ?
C3 C4 C5 124.3(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.2 . . ?
C1 C2 H2 122.2 . . ?
C3 C2 C1 115.6(3) . . ?
C3 C2 H2 122.2 . . ?
C12 C17 H17 120.4 . . ?
C12 C17 C16 119.2(4) . . ?
C16 C17 H17 120.4 . . ?
N9 C8 H8 124.6 . . ?
C7 C8 N9 110.9(3) . . ?
C7 C8 H8 124.6 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.3(4) . . ?
C14 C13 H13 119.4 . . ?
C17 C16 H16 119.5 . . ?
C15 C16 C17 120.9(4) . . ?
C15 C16 H16 119.5 . . ?
N9 C19 H19A 109.5 . . ?
N9 C19 H19B 109.5 . . ?
N9 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C15 H15 120.3 . . ?
C14 C15 C16 119.5(4) . . ?
C14 C15 H15 120.3 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(5) . . ?
C15 C14 H14 119.7 . . ?

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
Cl18 C4 C3 C2 179.3(2) . . . . ?
N10 C5 C6 C1 177.2(3) . . . . ?
N10 C5 C6 C7 -0.6(5) . . . . ?
N10 C5 C4 Cl18 3.8(4) . . . . ?
N10 C5 C4 C3 -177.2(3) . . . . ?
N10 C11 C12 C17 -8.6(4) . . . . ?
N10 C11 C12 C13 173.9(3) . . . . ?
N9 C1 C2 C3 178.8(3) . . . . ?
C5 N10 C11 C12 -102.2(3) . . . . ?
C5 C6 C1 N9 -178.9(2) . . . . ?
C5 C6 C1 C2 -0.4(4) . . . . ?
C5 C6 C7 C8 178.6(3) . . . . ?
C5 C4 C3 C2 0.3(5) . . . . ?
C6 C5 C4 Cl18 -179.00(18) . . . . ?
C6 C5 C4 C3 -0.1(4) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C6 C7 C8 N9 -0.4(4) . . . . ?
C11 N10 C5 C6 27.7(4) . . . . ?
C11 N10 C5 C4 -155.4(3) . . . . ?
C11 C12 C17 C16 -177.7(3) . . . . ?
C11 C12 C13 C14 177.2(3) . . . . ?
C1 N9 C8 C7 0.1(4) . . . . ?
C1 C6 C7 C8 0.6(3) . . . . ?
C12 C17 C16 C15 0.9(5) . . . . ?
C12 C13 C14 C15 0.3(6) . . . . ?
C7 C6 C1 N9 -0.6(3) . . . . ?
C7 C6 C1 C2 177.9(3) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C5 C6 C7 -177.7(3) . . . . ?
C4 C3 C2 C1 -0.6(5) . . . . ?
C17 C12 C13 C14 -0.3(5) . . . . ?
C17 C16 C15 C14 -0.9(6) . . . . ?
C8 N9 C1 C6 0.3(3) . . . . ?
C8 N9 C1 C2 -178.1(3) . . . . ?
C13 C12 C17 C16 -0.3(4) . . . . ?
C16 C15 C14 C13 0.3(7) . . . . ?
C19 N9 C1 C6 178.2(3) . . . . ?
C19 N9 C1 C2 -0.2(5) . . . . ?
C19 N9 C8 C7 -177.8(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 1.802
_oxdiff_exptl_absorpt_empirical_full_min 0.584
####################################################################### 
# 
# 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_xby-20220506
_database_code_depnum_ccdc_archive 'CCDC 2225440'
loop_
_audit_author_name
_audit_author_address
b
;a CCDC number
China
;
_audit_update_record             
;
2022-12-09 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_audit_creation_date             2022-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 Br N2 O2'
_chemical_formula_sum            'C27 H23 Br N2 O2'
_chemical_formula_weight         487.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 Br1'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4265(4)
_cell_length_b                   10.3316(5)
_cell_length_c                   13.1925(5)
_cell_angle_alpha                81.151(4)
_cell_angle_beta                 78.346(3)
_cell_angle_gamma                64.360(4)
_cell_volume                     1131.22(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5577
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.4070
_cell_measurement_theta_min      4.7550
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.673
_exptl_absorpt_coefficient_mu    2.687
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63637
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9034
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.692
_diffrn_reflns_theta_min         3.430
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  31.00   1.00    1.00    --  -35.62  60.00   1.00   84
  2  ω   -103.00 -18.00   1.00    1.00    --  -35.62 -60.00-137.00   85
  3  ω     18.00 103.00   1.00    1.00    --   35.62  60.00   1.00   85
  4  ω    -31.00  53.00   1.00    1.00    --   35.62 -60.00-137.00   84
  5  ω     89.00 174.00   1.00    1.00    --  107.12  60.00   1.00   85
  6  ω     40.00 125.00   1.00    1.00    --  107.12 -60.00-137.00   85
  7  ω   -108.00 -34.00   1.00    1.00    --  -35.62 178.00   0.00   74
  8  ω   -104.00 -35.00   1.00    1.00    --  -35.62-178.00  30.00   69
  9  ω     18.00  45.00   1.00    1.00    --   35.62  38.00 150.00   27
 10  ω     34.00  73.00   1.00    1.00    --   35.62 -99.00-120.00   39
 11  ω     27.00  53.00   1.00    1.00    --   35.62 -99.00-180.00   26
 12  ω     57.00 100.00   1.00    1.00    --   35.62  38.00 150.00   43
 13  ω    -31.00  41.00   1.00    1.00    --   35.62 -57.00-120.00   72
 14  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00  60.00   74
 15  ω     17.00  98.00   1.00    1.00    --   35.62  38.00-120.00   81
 16  ω     48.00 118.00   1.00    1.00    --  107.12 -61.00 -60.00   70
 17  ω     69.00 110.00   1.00    1.00    --  107.12 -95.00 -30.00   41
 18  ω     79.00 125.00   1.00    1.00    --  107.12 -61.00  30.00   46
 19  ω     87.00 129.00   1.00    1.00    --  107.12 -30.00  30.00   42
 20  ω     39.00  92.00   1.00    1.00    --  107.12 -95.00 -60.00   53
 21  ω     45.00  76.00   1.00    1.00    --  107.12 -61.00  30.00   31
 22  ω     88.00 165.00   1.00    1.00    --  107.12  77.00 -30.00   77
 23  ω    101.00 175.00   1.00    1.00    --  107.12  45.00  60.00   74
 24  ω    133.00 162.00   1.00    1.00    --  107.12  61.00-180.00   29
 25  ω    145.00 177.00   1.00    1.00    --  107.12  30.00 -90.00   32
 26  ω     39.00  74.00   1.00    1.00    --  107.12 -95.00-120.00   35
 27  ω     79.00 113.00   1.00    1.00    --  107.12-111.00 150.00   34
 28  ω     94.00 131.00   1.00    1.00    --  107.12  30.00 -90.00   37
 29  ω     86.00 142.00   1.00    1.00    --  107.12  30.00 -30.00   56
 30  ω     46.00 113.00   1.00    1.00    --  107.12-111.00-150.00   67
 31  ω     39.00  77.00   1.00    1.00    --  107.12 -30.00  30.00   38
 32  ω     70.00  99.00   1.00    1.00    --  107.12 -95.00  60.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0565347000
_diffrn_orient_matrix_UB_12      -0.1048486000
_diffrn_orient_matrix_UB_13      -0.0323513000
_diffrn_orient_matrix_UB_21      0.0940427000
_diffrn_orient_matrix_UB_22      -0.1181213000
_diffrn_orient_matrix_UB_23      0.0777527000
_diffrn_orient_matrix_UB_31      -0.1469686000
_diffrn_orient_matrix_UB_32      0.0506591000
_diffrn_orient_matrix_UB_33      0.0848852000
_diffrn_oxdiff_digest_frames     
;
01cdaef18a6dddbaddadc5e261012cf29a00028ff0d
;
_diffrn_oxdiff_digest_hkl        
;
01e6ddb260605de0af2d83618c5bcbe3ac452e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3733
_reflns_number_total             4301
_reflns_odcompleteness_completeness 99.75
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0320P)²+0.8094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1010
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C27(H27), C15(H15), C12(H12), C19(H19), C7(H7), C8(H8), C18(H18),
 C11(H11), C16(H16), C23(H23), C26(H26), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Br20 Br 0.20382(5) 0.17078(4) 1.11314(3) 0.07331(15) Uani 1 1 d . . . . .
N4 N 0.6702(2) 0.5236(2) 0.64677(15) 0.0343(4) Uani 1 1 d . . . . .
O2 O 0.3913(2) 0.84600(19) 0.76857(17) 0.0577(5) Uani 1 1 d . . . . .
O1 O 0.6093(2) 0.8136(2) 0.65211(17) 0.0599(5) Uani 1 1 d . . . . .
N9 N 0.9302(3) 0.1512(2) 0.42001(16) 0.0434(5) Uani 1 1 d . . . . .
C5 C 0.6675(3) 0.4064(2) 0.60420(16) 0.0322(5) Uani 1 1 d . . . . .
C6 C 0.7991(3) 0.3242(2) 0.53316(17) 0.0346(5) Uani 1 1 d . . . . .
C14 C 0.3428(3) 0.3865(2) 0.79427(17) 0.0328(5) Uani 1 1 d . . . . .
C22 C 0.8050(2) 0.4010(2) 0.80179(18) 0.0331(5) Uani 1 1 d . . . . .
C13 C 0.5350(3) 0.3749(2) 0.62545(17) 0.0348(5) Uani 1 1 d . . . . .
C3 C 0.5227(3) 0.6233(2) 0.69336(18) 0.0352(5) Uani 1 1 d . . . . .
C10 C 0.7922(3) 0.2108(3) 0.48933(17) 0.0370(5) Uani 1 1 d . . . . .
C1 C 0.3841(3) 0.4656(3) 0.69310(18) 0.0364(5) Uani 1 1 d . . . . .
H1 H 0.296643 0.494346 0.653216 0.044 Uiso 1 1 calc R . . . .
C21 C 0.8065(3) 0.4915(3) 0.70080(19) 0.0370(5) Uani 1 1 d . . . . .
H21A H 0.805547 0.581526 0.714360 0.044 Uiso 1 1 calc R . . . .
H21B H 0.904657 0.441634 0.655255 0.044 Uiso 1 1 calc R . . . .
C2 C 0.3908(3) 0.6011(2) 0.71428(18) 0.0380(5) Uani 1 1 d . . . . .
H2 H 0.297523 0.673572 0.743628 0.046 Uiso 1 1 calc R . . . .
C17 C 0.2609(3) 0.2566(3) 0.98200(19) 0.0413(5) Uani 1 1 d . . . . .
C28 C 0.5172(3) 0.7682(3) 0.7015(2) 0.0426(6) Uani 1 1 d . . . . .
C27 C 0.7164(3) 0.4625(3) 0.8931(2) 0.0425(6) Uani 1 1 d . . . . .
H27 H 0.657800 0.561697 0.892456 0.051 Uiso 1 1 calc R . . . .
C15 C 0.1852(3) 0.4143(3) 0.8332(2) 0.0430(6) Uani 1 1 d . . . . .
H15 H 0.105927 0.477879 0.795294 0.052 Uiso 1 1 calc R . . . .
C12 C 0.5348(3) 0.2605(3) 0.57957(19) 0.0428(6) Uani 1 1 d . . . . .
H12 H 0.444448 0.241746 0.595065 0.051 Uiso 1 1 calc R . . . .
C19 C 0.4587(3) 0.2906(3) 0.85167(19) 0.0394(5) Uani 1 1 d . . . . .
H19 H 0.565223 0.269685 0.826502 0.047 Uiso 1 1 calc R . . . .
C7 C 0.9478(3) 0.3290(3) 0.4862(2) 0.0439(6) Uani 1 1 d . . . . .
H7 H 0.986501 0.392785 0.499286 0.053 Uiso 1 1 calc R . . . .
C8 C 1.0220(3) 0.2236(3) 0.4192(2) 0.0473(6) Uani 1 1 d . . . . .
H8 H 1.120908 0.203635 0.378571 0.057 Uiso 1 1 calc R . . . .
C18 C 0.4188(3) 0.2253(3) 0.9457(2) 0.0431(6) Uani 1 1 d . . . . .
H18 H 0.497458 0.161173 0.983900 0.052 Uiso 1 1 calc R . . . .
C11 C 0.6620(3) 0.1757(3) 0.51316(19) 0.0441(6) Uani 1 1 d . . . . .
H11 H 0.661298 0.098593 0.485410 0.053 Uiso 1 1 calc R . . . .
C16 C 0.1430(3) 0.3498(3) 0.9268(2) 0.0465(6) Uani 1 1 d . . . . .
H16 H 0.036780 0.369222 0.951857 0.056 Uiso 1 1 calc R . . . .
C23 C 0.8919(3) 0.2531(3) 0.8049(2) 0.0433(6) Uani 1 1 d . . . . .
H23 H 0.953042 0.210028 0.744531 0.052 Uiso 1 1 calc R . . . .
C32 C 0.9664(4) 0.0380(3) 0.3537(2) 0.0515(7) Uani 1 1 d . . . . .
H32A H 0.937832 -0.035791 0.392941 0.077 Uiso 1 1 calc GR . . . .
H32B H 1.078227 -0.002395 0.327514 0.077 Uiso 1 1 calc GR . . . .
H32C H 0.907085 0.077196 0.296733 0.077 Uiso 1 1 calc GR . . . .
C26 C 0.7141(3) 0.3782(3) 0.9850(2) 0.0532(7) Uani 1 1 d . . . . .
H26 H 0.654520 0.420951 1.045782 0.064 Uiso 1 1 calc R . . . .
C24 C 0.8886(4) 0.1686(3) 0.8969(2) 0.0559(7) Uani 1 1 d . . . . .
H24 H 0.946616 0.069353 0.897866 0.067 Uiso 1 1 calc R . . . .
C25 C 0.7997(3) 0.2312(3) 0.9870(2) 0.0576(7) Uani 1 1 d . . . . .
H25 H 0.797494 0.174412 1.048737 0.069 Uiso 1 1 calc R . . . .
C30 C 0.3701(4) 0.9921(3) 0.7743(3) 0.0774(11) Uani 1 1 d . . . . .
H30A H 0.346048 1.045967 0.709194 0.116 Uiso 1 1 calc GR . . . .
H30B H 0.466210 0.991132 0.789071 0.116 Uiso 1 1 calc GR . . . .
H30C H 0.284060 1.036051 0.828441 0.116 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br20 C17 1.906(2) . ?
N4 C5 1.422(3) . ?
N4 C3 1.408(3) . ?
N4 C21 1.482(3) . ?
O2 C28 1.344(3) . ?
O2 C30 1.446(3) . ?
O1 C28 1.196(3) . ?
N9 C10 1.381(3) . ?
N9 C8 1.364(3) . ?
N9 C32 1.448(3) . ?
C5 C6 1.415(3) . ?
C5 C13 1.388(3) . ?
C6 C10 1.414(3) . ?
C6 C7 1.432(3) . ?
C14 C1 1.526(3) . ?
C14 C15 1.386(3) . ?
C14 C19 1.384(3) . ?
C22 C21 1.507(3) . ?
C22 C27 1.386(3) . ?
C22 C23 1.385(3) . ?
C13 C1 1.513(3) . ?
C13 C12 1.410(3) . ?
C3 C2 1.328(3) . ?
C3 C28 1.495(3) . ?
C10 C11 1.389(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.499(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C2 H2 0.9300 . ?
C17 C18 1.376(3) . ?
C17 C16 1.370(4) . ?
C27 H27 0.9300 . ?
C27 C26 1.383(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.369(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.382(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.359(4) . ?
C8 H8 0.9300 . ?
C18 H18 0.9300 . ?
C11 H11 0.9300 . ?
C16 H16 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.385(4) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C26 H26 0.9300 . ?
C26 C25 1.376(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.378(4) . ?
C25 H25 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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
C5 N4 C21 116.89(18) . . ?
C3 N4 C5 116.35(18) . . ?
C3 N4 C21 114.86(18) . . ?
C28 O2 C30 115.4(2) . . ?
C10 N9 C32 125.8(2) . . ?
C8 N9 C10 108.5(2) . . ?
C8 N9 C32 125.5(2) . . ?
C6 C5 N4 119.66(19) . . ?
C13 C5 N4 121.8(2) . . ?
C13 C5 C6 118.4(2) . . ?
C5 C6 C7 135.3(2) . . ?
C10 C6 C5 118.8(2) . . ?
C10 C6 C7 105.8(2) . . ?
C15 C14 C1 120.1(2) . . ?
C19 C14 C1 121.8(2) . . ?
C19 C14 C15 118.1(2) . . ?
C27 C22 C21 121.3(2) . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 C27 118.5(2) . . ?
C5 C13 C1 121.8(2) . . ?
C5 C13 C12 120.3(2) . . ?
C12 C13 C1 117.8(2) . . ?
N4 C3 C28 114.6(2) . . ?
C2 C3 N4 123.7(2) . . ?
C2 C3 C28 120.9(2) . . ?
N9 C10 C6 108.0(2) . . ?
N9 C10 C11 129.0(2) . . ?
C11 C10 C6 123.0(2) . . ?
C14 C1 H1 106.9 . . ?
C13 C1 C14 114.34(19) . . ?
C13 C1 H1 106.9 . . ?
C2 C1 C14 110.63(19) . . ?
C2 C1 C13 110.64(19) . . ?
C2 C1 H1 106.9 . . ?
N4 C21 C22 113.68(18) . . ?
N4 C21 H21A 108.8 . . ?
N4 C21 H21B 108.8 . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C3 C2 C1 123.5(2) . . ?
C3 C2 H2 118.3 . . ?
C1 C2 H2 118.3 . . ?
C18 C17 Br20 119.4(2) . . ?
C16 C17 Br20 119.04(19) . . ?
C16 C17 C18 121.6(2) . . ?
O2 C28 C3 112.1(2) . . ?
O1 C28 O2 122.9(2) . . ?
O1 C28 C3 124.9(2) . . ?
C22 C27 H27 119.6 . . ?
C26 C27 C22 120.8(2) . . ?
C26 C27 H27 119.6 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.6(2) . . ?
C16 C15 H15 119.2 . . ?
C13 C12 H12 118.6 . . ?
C11 C12 C13 122.8(2) . . ?
C11 C12 H12 118.6 . . ?
C14 C19 H19 119.4 . . ?
C18 C19 C14 121.1(2) . . ?
C18 C19 H19 119.4 . . ?
C6 C7 H7 126.2 . . ?
C8 C7 C6 107.5(2) . . ?
C8 C7 H7 126.2 . . ?
N9 C8 H8 124.9 . . ?
C7 C8 N9 110.1(2) . . ?
C7 C8 H8 124.9 . . ?
C17 C18 C19 118.9(2) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C10 C11 H11 121.7 . . ?
C12 C11 C10 116.6(2) . . ?
C12 C11 H11 121.7 . . ?
C17 C16 C15 118.6(2) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
N9 C32 H32A 109.5 . . ?
N9 C32 H32B 109.5 . . ?
N9 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C27 C26 H26 119.9 . . ?
C25 C26 C27 120.2(3) . . ?
C25 C26 H26 119.9 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 119.6(3) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
O2 C30 H30A 109.5 . . ?
O2 C30 H30B 109.5 . . ?
O2 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

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
Br20 C17 C18 C19 -178.55(19) . . . . ?
Br20 C17 C16 C15 178.36(19) . . . . ?
N4 C5 C6 C10 -178.1(2) . . . . ?
N4 C5 C6 C7 -1.7(4) . . . . ?
N4 C5 C13 C1 1.5(3) . . . . ?
N4 C5 C13 C12 178.2(2) . . . . ?
N4 C3 C2 C1 1.6(4) . . . . ?
N4 C3 C28 O2 -164.2(2) . . . . ?
N4 C3 C28 O1 18.5(4) . . . . ?
N9 C10 C11 C12 -175.1(2) . . . . ?
C5 N4 C3 C2 11.5(3) . . . . ?
C5 N4 C3 C28 -158.5(2) . . . . ?
C5 N4 C21 C22 -69.3(3) . . . . ?
C5 C6 C10 N9 177.6(2) . . . . ?
C5 C6 C10 C11 -0.3(3) . . . . ?
C5 C6 C7 C8 -176.9(3) . . . . ?
C5 C13 C1 C14 -115.3(2) . . . . ?
C5 C13 C1 C2 10.4(3) . . . . ?
C5 C13 C12 C11 0.1(4) . . . . ?
C6 C5 C13 C1 -174.6(2) . . . . ?
C6 C5 C13 C12 2.0(3) . . . . ?
C6 C10 C11 C12 2.4(4) . . . . ?
C6 C7 C8 N9 0.0(3) . . . . ?
C14 C1 C2 C3 115.7(2) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C14 C19 C18 C17 0.2(4) . . . . ?
C22 C27 C26 C25 -0.3(4) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C13 C5 C6 C10 -1.9(3) . . . . ?
C13 C5 C6 C7 174.6(3) . . . . ?
C13 C1 C2 C3 -12.1(3) . . . . ?
C13 C12 C11 C10 -2.2(4) . . . . ?
C3 N4 C5 C6 163.3(2) . . . . ?
C3 N4 C5 C13 -12.8(3) . . . . ?
C3 N4 C21 C22 72.3(2) . . . . ?
C10 N9 C8 C7 0.1(3) . . . . ?
C10 C6 C7 C8 -0.1(3) . . . . ?
C1 C14 C15 C16 -177.0(2) . . . . ?
C1 C14 C19 C18 176.7(2) . . . . ?
C1 C13 C12 C11 176.9(2) . . . . ?
C21 N4 C5 C6 -55.7(3) . . . . ?
C21 N4 C5 C13 128.2(2) . . . . ?
C21 N4 C3 C2 -130.3(2) . . . . ?
C21 N4 C3 C28 59.7(3) . . . . ?
C21 C22 C27 C26 179.1(2) . . . . ?
C21 C22 C23 C24 -178.6(2) . . . . ?
C2 C3 C28 O2 25.6(3) . . . . ?
C2 C3 C28 O1 -151.8(3) . . . . ?
C28 C3 C2 C1 170.9(2) . . . . ?
C27 C22 C21 N4 -83.6(3) . . . . ?
C27 C22 C23 C24 0.8(4) . . . . ?
C27 C26 C25 C24 0.5(4) . . . . ?
C15 C14 C1 C13 -143.3(2) . . . . ?
C15 C14 C1 C2 91.0(3) . . . . ?
C15 C14 C19 C18 -0.7(4) . . . . ?
C12 C13 C1 C14 67.9(3) . . . . ?
C12 C13 C1 C2 -166.4(2) . . . . ?
C19 C14 C1 C13 39.3(3) . . . . ?
C19 C14 C1 C2 -86.4(3) . . . . ?
C19 C14 C15 C16 0.5(4) . . . . ?
C7 C6 C10 N9 0.1(3) . . . . ?
C7 C6 C10 C11 -177.7(2) . . . . ?
C8 N9 C10 C6 -0.1(3) . . . . ?
C8 N9 C10 C11 177.6(3) . . . . ?
C18 C17 C16 C15 -0.7(4) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
C23 C22 C21 N4 95.8(3) . . . . ?
C23 C22 C27 C26 -0.3(4) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C32 N9 C10 C6 -176.0(2) . . . . ?
C32 N9 C10 C11 1.7(4) . . . . ?
C32 N9 C8 C7 175.9(2) . . . . ?
C30 O2 C28 O1 2.4(4) . . . . ?
C30 O2 C28 C3 -175.0(2) . . . . ?

_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 1.421
_oxdiff_exptl_absorpt_empirical_full_min 0.660
####################################################################### 
# 
# 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_20221118-xby-2
_database_code_depnum_ccdc_archive 'CCDC 2225454'
loop_
_audit_author_name
_audit_author_address
e
;a CCDC number
China
;
_audit_update_record             
;
2022-12-09 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_audit_creation_date             2022-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 N2'
_chemical_formula_sum            'C17 H18 N2'
_chemical_formula_weight         250.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 N1'
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'

_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                   10.7952(4)
_cell_length_b                   5.4138(2)
_cell_length_c                   24.3400(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.872(4)
_cell_angle_gamma                90
_cell_volume                     1401.44(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2357
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2660
_cell_measurement_theta_min      3.6970
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74858
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5862
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.522
_diffrn_reflns_theta_min         3.687
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.968
_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 -70.00   1.00    1.00    --  -35.62 -42.00 133.00   34
  2  ω    -66.00 -19.00   1.00    1.00    --  -35.62 -42.00 133.00   47
  3  ω     19.00 103.00   1.00    1.00    --   35.62  42.00 -74.00   84
  4  ω     11.00  43.00   1.00    1.00    --   35.62 -42.00 133.00   32
  5  ω     89.00 175.00   1.00    3.90    --  107.12  42.00 -74.00   86
  6  ω     39.00 119.00   1.00    3.90    --  107.12 -42.00 133.00   80
  7  ω    -34.00  -9.00   1.00    1.00    --  -35.62  42.00 -74.00   25
  8  ω    -99.00 -34.00   1.00    1.00    --  -35.62 178.00  60.00   65
  9  ω    -78.00 -37.00   1.00    1.00    --  -35.62-178.00   0.00   41
 10  ω     69.00 103.00   1.00    1.00    --   35.62 178.00  90.00   34
 11  ω    -27.00  55.00   1.00    1.00    --   35.62 -38.00   0.00   82
 12  ω     58.00 121.00   1.00    3.90    --  107.12 -45.00-150.00   63
 13  ω    103.00 143.00   1.00    3.90    --  107.12  61.00 -30.00   40
 14  ω     62.00 110.00   1.00    3.90    --  107.12 -95.00 -60.00   48
 15  ω     46.00  73.00   1.00    3.90    --  107.12-111.00  60.00   27
 16  ω    108.00 133.00   1.00    3.90    --  107.12 -77.00 150.00   25
 17  ω     83.00 109.00   1.00    3.90    --  107.12-111.00-180.00   26
 18  ω     40.00  86.00   1.00    3.90    --  107.12 -77.00 150.00   46
 19  ω     62.00 110.00   1.00    3.90    --  107.12 -95.00-150.00   48
 20  ω     38.00  63.00   1.00    3.90    --  107.12-111.00-180.00   25
 21  ω     53.00 108.00   1.00    3.90    --  107.12-111.00 120.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0134032000
_diffrn_orient_matrix_UB_12      -0.1312167000
_diffrn_orient_matrix_UB_13      -0.0569194000
_diffrn_orient_matrix_UB_21      0.1395363000
_diffrn_orient_matrix_UB_22      -0.0749957000
_diffrn_orient_matrix_UB_23      0.0129141000
_diffrn_orient_matrix_UB_31      -0.0361202000
_diffrn_orient_matrix_UB_32      -0.2410974000
_diffrn_orient_matrix_UB_33      0.0269433000
_diffrn_oxdiff_digest_frames     
;
012c41004096ac540c9918d2929c2f263c00029bfa9
;
_diffrn_oxdiff_digest_hkl        
;
01a228a7f7e05b6f506713ae28bcfd7520b24b
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1832
_reflns_number_total             2654
_reflns_odcompleteness_completeness 99.39
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0672
_refine_ls_restrained_S_all      1.162
_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)+(0.0530P)²+1.1158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1921
_refine_ls_wR_factor_ref         0.2020
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C4(H4), C17(H17), C3(H3), C16(H16), C15(H15), C13(H13),
 C14(H14)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
N10 N 0.6485(3) 0.0725(6) 0.42071(11) 0.0587(7) Uani 1 1 d . . . . .
N6 N 0.5316(3) 0.4496(6) 0.24681(11) 0.0640(8) Uani 1 1 d . . . . .
C9 C 0.5929(3) 0.2773(6) 0.33118(11) 0.0468(7) Uani 1 1 d . . . . .
C1 C 0.6724(3) 0.2533(6) 0.38344(12) 0.0487(7) Uani 1 1 d . . . . .
C5 C 0.6194(3) 0.4638(6) 0.29417(12) 0.0529(8) Uani 1 1 d . . . . .
C8 C 0.4820(3) 0.1512(7) 0.30386(13) 0.0549(8) Uani 1 1 d . . . . .
C2 C 0.7704(3) 0.4213(7) 0.39628(13) 0.0585(9) Uani 1 1 d . . . . .
H2 H 0.823373 0.410681 0.430616 0.070 Uiso 1 1 calc R . . . .
C7 C 0.4491(3) 0.2640(7) 0.25335(14) 0.0656(10) Uani 1 1 d . . . . .
H7 H 0.379879 0.220559 0.226844 0.079 Uiso 1 1 calc R . . . .
C12 C 0.7430(3) 0.2034(7) 0.51667(12) 0.0591(9) Uani 1 1 d . . . . .
C4 C 0.7184(3) 0.6301(7) 0.30746(15) 0.0654(10) Uani 1 1 d . . . . .
H4 H 0.734020 0.751838 0.282586 0.078 Uiso 1 1 calc R . . . .
C17 C 0.6333(3) 0.3023(7) 0.52919(13) 0.0653(10) Uani 1 1 d . . . . .
H17 H 0.556186 0.254780 0.508752 0.078 Uiso 1 1 calc R . . . .
C3 C 0.7912(3) 0.6055(7) 0.35880(15) 0.0669(10) Uani 1 1 d . . . . .
H3 H 0.857117 0.715645 0.369220 0.080 Uiso 1 1 calc R . . . .
C11 C 0.7403(4) 0.0160(7) 0.47018(13) 0.0676(10) Uani 1 1 d . . . . .
H11A H 0.823076 0.007688 0.459871 0.081 Uiso 1 1 calc R . . . .
H11B H 0.721511 -0.145417 0.483975 0.081 Uiso 1 1 calc R . . . .
C19 C 0.4129(4) -0.0582(7) 0.32465(16) 0.0721(10) Uani 1 1 d . . . . .
H19A H 0.465251 -0.202634 0.328691 0.108 Uiso 1 1 calc GR . . . .
H19B H 0.337494 -0.091320 0.298505 0.108 Uiso 1 1 calc GR . . . .
H19C H 0.391397 -0.015398 0.360123 0.108 Uiso 1 1 calc GR . . . .
C16 C 0.6377(4) 0.4713(8) 0.57194(15) 0.0767(12) Uani 1 1 d . . . . .
H16 H 0.563131 0.537710 0.579716 0.092 Uiso 1 1 calc R . . . .
C15 C 0.7485(4) 0.5420(9) 0.60273(15) 0.0847(13) Uani 1 1 d . . . . .
H15 H 0.750208 0.655358 0.631566 0.102 Uiso 1 1 calc R . . . .
C18 C 0.5225(5) 0.6150(8) 0.19926(15) 0.0894(14) Uani 1 1 d . . . . .
H18A H 0.502873 0.778640 0.210307 0.134 Uiso 1 1 calc GR . . . .
H18B H 0.457441 0.558348 0.170064 0.134 Uiso 1 1 calc GR . . . .
H18C H 0.601301 0.617335 0.185990 0.134 Uiso 1 1 calc GR . . . .
C13 C 0.8543(4) 0.2766(9) 0.54792(16) 0.0911(15) Uani 1 1 d . . . . .
H13 H 0.929345 0.212249 0.540262 0.109 Uiso 1 1 calc R . . . .
C14 C 0.8568(4) 0.4458(11) 0.59102(18) 0.1049(18) Uani 1 1 d . . . . .
H14 H 0.933333 0.493266 0.611974 0.126 Uiso 1 1 calc R . . . .
H10 H 0.612(4) -0.060(8) 0.4064(16) 0.079(13) Uiso 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
N10 C1 1.389(4) . ?
N10 C11 1.455(4) . ?
N10 H10 0.86(4) . ?
N6 C5 1.363(4) . ?
N6 C7 1.370(5) . ?
N6 C18 1.453(4) . ?
C9 C1 1.413(4) . ?
C9 C5 1.415(4) . ?
C9 C8 1.438(4) . ?
C1 C2 1.390(4) . ?
C5 C4 1.392(5) . ?
C8 C7 1.364(5) . ?
C8 C19 1.492(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.395(5) . ?
C7 H7 0.9300 . ?
C12 C17 1.380(5) . ?
C12 C11 1.517(5) . ?
C12 C13 1.365(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.364(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.380(5) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C15 1.353(6) . ?
C15 H15 0.9300 . ?
C15 C14 1.354(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.390(6) . ?
C14 H14 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
C1 N10 C11 120.8(3) . . ?
C1 N10 H10 116(3) . . ?
C11 N10 H10 111(3) . . ?
C5 N6 C7 108.3(3) . . ?
C5 N6 C18 125.5(4) . . ?
C7 N6 C18 126.0(3) . . ?
C1 C9 C5 118.7(3) . . ?
C1 C9 C8 134.6(3) . . ?
C5 C9 C8 106.7(3) . . ?
N10 C1 C9 120.0(3) . . ?
N10 C1 C2 122.3(3) . . ?
C2 C1 C9 117.6(3) . . ?
N6 C5 C9 108.1(3) . . ?
N6 C5 C4 128.8(3) . . ?
C4 C5 C9 123.0(3) . . ?
C9 C8 C19 129.0(3) . . ?
C7 C8 C9 105.8(3) . . ?
C7 C8 C19 125.3(3) . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.5(3) . . ?
C3 C2 H2 119.3 . . ?
N6 C7 H7 124.5 . . ?
C8 C7 N6 111.1(3) . . ?
C8 C7 H7 124.5 . . ?
C17 C12 C11 121.1(3) . . ?
C13 C12 C17 118.1(3) . . ?
C13 C12 C11 120.8(3) . . ?
C5 C4 H4 121.7 . . ?
C3 C4 C5 116.6(3) . . ?
C3 C4 H4 121.7 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.2(4) . . ?
C16 C17 H17 119.9 . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.5(3) . . ?
C4 C3 H3 118.8 . . ?
N10 C11 C12 113.6(3) . . ?
N10 C11 H11A 108.8 . . ?
N10 C11 H11B 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C16 H16 119.4 . . ?
C15 C16 C17 121.2(4) . . ?
C15 C16 H16 119.4 . . ?
C16 C15 H15 120.4 . . ?
C16 C15 C14 119.2(4) . . ?
C14 C15 H15 120.4 . . ?
N6 C18 H18A 109.5 . . ?
N6 C18 H18B 109.5 . . ?
N6 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.9(4) . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 120.5(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?

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
N10 C1 C2 C3 -178.4(3) . . . . ?
N6 C5 C4 C3 178.6(3) . . . . ?
C9 C1 C2 C3 -0.8(5) . . . . ?
C9 C5 C4 C3 0.3(5) . . . . ?
C9 C8 C7 N6 0.5(4) . . . . ?
C1 N10 C11 C12 77.4(4) . . . . ?
C1 C9 C5 N6 179.4(3) . . . . ?
C1 C9 C5 C4 -1.9(5) . . . . ?
C1 C9 C8 C7 179.8(3) . . . . ?
C1 C9 C8 C19 0.3(6) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C5 N6 C7 C8 -1.2(4) . . . . ?
C5 C9 C1 N10 179.8(3) . . . . ?
C5 C9 C1 C2 2.1(4) . . . . ?
C5 C9 C8 C7 0.3(3) . . . . ?
C5 C9 C8 C19 -179.1(3) . . . . ?
C5 C4 C3 C2 1.2(5) . . . . ?
C8 C9 C1 N10 0.4(5) . . . . ?
C8 C9 C1 C2 -177.2(3) . . . . ?
C8 C9 C5 N6 -1.0(3) . . . . ?
C8 C9 C5 C4 177.6(3) . . . . ?
C7 N6 C5 C9 1.3(4) . . . . ?
C7 N6 C5 C4 -177.2(3) . . . . ?
C12 C17 C16 C15 -0.6(6) . . . . ?
C12 C13 C14 C15 -0.2(8) . . . . ?
C17 C12 C11 N10 40.8(5) . . . . ?
C17 C12 C13 C14 -0.1(7) . . . . ?
C17 C16 C15 C14 0.4(7) . . . . ?
C11 N10 C1 C9 169.2(3) . . . . ?
C11 N10 C1 C2 -13.3(5) . . . . ?
C11 C12 C17 C16 179.5(3) . . . . ?
C11 C12 C13 C14 -179.1(4) . . . . ?
C19 C8 C7 N6 180.0(3) . . . . ?
C16 C15 C14 C13 0.0(8) . . . . ?
C18 N6 C5 C9 177.4(3) . . . . ?
C18 N6 C5 C4 -1.1(5) . . . . ?
C18 N6 C7 C8 -177.2(3) . . . . ?
C13 C12 C17 C16 0.5(6) . . . . ?
C13 C12 C11 N10 -140.2(4) . . . . ?

_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 0.497
####################################################################### 
# 
# 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_2022.11.18-xby-1
_database_code_depnum_ccdc_archive 'CCDC 2225450'
loop_
_audit_author_name
_audit_author_address
d
;a CCDC number
China
;
_audit_update_record             
;
2022-12-09 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 Cl2 N2'
_chemical_formula_weight         304.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5101(4)
_cell_length_b                   5.3886(2)
_cell_length_c                   23.0853(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.195(3)
_cell_angle_gamma                90
_cell_volume                     1425.95(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    4.004
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5399
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.845
_diffrn_reflns_theta_max         71.337
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2718
_reflns_number_gt                2303
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0766P)²+0.4148P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2718
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
Cl18 Cl 0.08731(6) 0.22929(15) 0.47452(3) 0.0617(2) Uani 1 1 d . . . . .
Cl19 Cl 0.00398(7) 0.90745(15) 0.30757(4) 0.0722(3) Uani 1 1 d . . . . .
N10 N 0.30749(17) 0.1231(4) 0.42490(9) 0.0496(5) Uani 1 1 d . . . . .
N9 N 0.2534(2) 0.6960(5) 0.26904(9) 0.0547(5) Uani 1 1 d . . . . .
C5 C 0.24067(19) 0.2988(4) 0.39424(10) 0.0404(5) Uani 1 1 d . . . . .
C6 C 0.27267(19) 0.4214(4) 0.34350(10) 0.0409(5) Uani 1 1 d . . . . .
C1 C 0.1997(2) 0.6080(5) 0.31593(10) 0.0438(5) Uani 1 1 d . . . . .
C12 C 0.5195(2) 0.0518(5) 0.41224(11) 0.0453(5) Uani 1 1 d . . . . .
C4 C 0.13559(19) 0.3759(5) 0.41364(10) 0.0439(5) Uani 1 1 d . . . . .
C3 C 0.0651(2) 0.5600(5) 0.38734(11) 0.0478(6) Uani 1 1 d . . . . .
H3 H -0.003515 0.603922 0.403105 0.057 Uiso 1 1 calc R U . . .
C2 C 0.0956(2) 0.6777(5) 0.33848(11) 0.0471(5) Uani 1 1 d . . . . .
C11 C 0.3932(2) -0.0333(5) 0.40091(12) 0.0500(6) Uani 1 1 d . . . . .
H11A H 0.374180 -0.044305 0.359197 0.060 Uiso 1 1 calc R U . . .
H11B H 0.386927 -0.198966 0.416747 0.060 Uiso 1 1 calc R U . . .
C7 C 0.3725(2) 0.4066(6) 0.31132(11) 0.0537(6) Uani 1 1 d . . . . .
H7 H 0.436515 0.302502 0.318996 0.064 Uiso 1 1 calc R U . . .
C8 C 0.3564(3) 0.5720(6) 0.26776(11) 0.0611(7) Uani 1 1 d . . . . .
H8 H 0.409047 0.598715 0.240131 0.073 Uiso 1 1 calc R U . . .
C13 C 0.6052(3) -0.0810(6) 0.38811(14) 0.0648(7) Uani 1 1 d . . . . .
H13 H 0.585732 -0.219439 0.365210 0.078 Uiso 1 1 calc R U . . .
C17 C 0.5500(3) 0.2552(6) 0.44649(15) 0.0631(7) Uani 1 1 d . . . . .
H17 H 0.492918 0.345275 0.463348 0.076 Uiso 1 1 calc R U . . .
C20 C 0.2146(3) 0.8928(6) 0.22806(13) 0.0723(9) Uani 1 1 d . . . . .
H20A H 0.142894 0.844289 0.206603 0.108 Uiso 1 1 calc R U . . .
H20B H 0.273066 0.920386 0.201611 0.108 Uiso 1 1 calc R U . . .
H20C H 0.202550 1.042941 0.249094 0.108 Uiso 1 1 calc R U . . .
C15 C 0.7504(3) 0.1944(9) 0.43182(19) 0.0896(14) Uani 1 1 d . . . . .
H15 H 0.828184 0.241983 0.438336 0.107 Uiso 1 1 calc R U . . .
C16 C 0.6667(3) 0.3255(8) 0.45579(17) 0.0817(11) Uani 1 1 d . . . . .
H16 H 0.687207 0.463537 0.478640 0.098 Uiso 1 1 calc R U . . .
C14 C 0.7207(3) -0.0073(9) 0.39813(19) 0.0880(12) Uani 1 1 d . . . . .
H14 H 0.778477 -0.096624 0.381654 0.106 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
Cl18 C4 1.746(2) . ?
Cl19 C2 1.737(2) . ?
N10 C5 1.375(3) . ?
N10 C11 1.446(3) . ?
N9 C8 1.364(4) . ?
N9 C1 1.378(3) . ?
N9 C20 1.464(4) . ?
C5 C4 1.391(3) . ?
C5 C6 1.422(3) . ?
C6 C1 1.423(3) . ?
C6 C7 1.426(3) . ?
C1 C2 1.401(4) . ?
C12 C13 1.377(4) . ?
C12 C17 1.378(4) . ?
C12 C11 1.523(3) . ?
C4 C3 1.386(4) . ?
C3 C2 1.367(4) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C7 C8 1.344(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C13 C14 1.386(5) . ?
C13 H13 0.9300 . ?
C17 C16 1.393(4) . ?
C17 H17 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C15 C16 1.353(6) . ?
C15 C14 1.362(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C14 H14 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
C5 N10 C11 125.0(2) . . ?
C8 N9 C1 107.5(2) . . ?
C8 N9 C20 123.7(3) . . ?
C1 N9 C20 128.7(3) . . ?
N10 C5 C4 120.1(2) . . ?
N10 C5 C6 124.7(2) . . ?
C4 C5 C6 115.1(2) . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 C7 133.2(2) . . ?
C1 C6 C7 106.1(2) . . ?
N9 C1 C2 131.3(2) . . ?
N9 C1 C6 107.8(2) . . ?
C2 C1 C6 120.9(2) . . ?
C13 C12 C17 119.4(3) . . ?
C13 C12 C11 118.8(2) . . ?
C17 C12 C11 121.8(2) . . ?
C3 C4 C5 124.3(2) . . ?
C3 C4 Cl18 117.39(18) . . ?
C5 C4 Cl18 118.25(19) . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C2 C1 118.3(2) . . ?
C3 C2 Cl19 118.6(2) . . ?
C1 C2 Cl19 123.1(2) . . ?
N10 C11 C12 115.6(2) . . ?
N10 C11 H11A 108.4 . . ?
C12 C11 H11A 108.4 . . ?
N10 C11 H11B 108.4 . . ?
C12 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
C8 C7 C6 106.8(3) . . ?
C8 C7 H7 126.6 . . ?
C6 C7 H7 126.6 . . ?
C7 C8 N9 111.7(2) . . ?
C7 C8 H8 124.1 . . ?
N9 C8 H8 124.1 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C12 C17 C16 119.8(3) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
N9 C20 H20A 109.5 . . ?
N9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.5(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C15 C14 C13 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?

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
C11 N10 C5 C4 157.3(2) . . . . ?
C11 N10 C5 C6 -25.4(4) . . . . ?
N10 C5 C6 C1 -177.5(2) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
N10 C5 C6 C7 -0.3(4) . . . . ?
C4 C5 C6 C7 177.2(2) . . . . ?
C8 N9 C1 C2 177.0(3) . . . . ?
C20 N9 C1 C2 -0.4(4) . . . . ?
C8 N9 C1 C6 -0.8(3) . . . . ?
C20 N9 C1 C6 -178.2(3) . . . . ?
C5 C6 C1 N9 178.9(2) . . . . ?
C7 C6 C1 N9 1.0(3) . . . . ?
C5 C6 C1 C2 0.9(3) . . . . ?
C7 C6 C1 C2 -177.1(2) . . . . ?
N10 C5 C4 C3 176.7(2) . . . . ?
C6 C5 C4 C3 -0.8(3) . . . . ?
N10 C5 C4 Cl18 -4.2(3) . . . . ?
C6 C5 C4 Cl18 178.23(16) . . . . ?
C5 C4 C3 C2 1.0(4) . . . . ?
Cl18 C4 C3 C2 -178.03(19) . . . . ?
C4 C3 C2 C1 -0.2(4) . . . . ?
C4 C3 C2 Cl19 -179.85(19) . . . . ?
N9 C1 C2 C3 -178.2(2) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
N9 C1 C2 Cl19 1.4(4) . . . . ?
C6 C1 C2 Cl19 178.93(17) . . . . ?
C5 N10 C11 C12 98.8(3) . . . . ?
C13 C12 C11 N10 -176.7(2) . . . . ?
C17 C12 C11 N10 4.3(4) . . . . ?
C5 C6 C7 C8 -178.4(2) . . . . ?
C1 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 N9 0.3(3) . . . . ?
C1 N9 C8 C7 0.3(3) . . . . ?
C20 N9 C8 C7 177.9(3) . . . . ?
C17 C12 C13 C14 -0.6(5) . . . . ?
C11 C12 C13 C14 -179.7(3) . . . . ?
C13 C12 C17 C16 0.7(5) . . . . ?
C11 C12 C17 C16 179.8(3) . . . . ?
C14 C15 C16 C17 0.3(6) . . . . ?
C12 C17 C16 C15 -0.5(5) . . . . ?
C16 C15 C14 C13 -0.2(6) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?

_refine_diff_density_max         0.518
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.050

