# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_202104102
_database_code_depnum_ccdc_archive 'CCDC 2079852'
loop_
_audit_author_name
_audit_author_address
'Mei guangjian'
;JiangSu normal universtiy
China
;
_audit_update_record             
;
2021-04-25 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_audit_creation_date             2021-04-21
_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         'C22 H19 N O3'
_chemical_formula_sum            'C22 H19 N O3'
_chemical_formula_weight         345.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O5N2
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.34646(16)
_cell_length_b                   28.3786(5)
_cell_length_c                   8.67019(14)
_cell_angle_alpha                90
_cell_angle_beta                 94.7923(18)
_cell_angle_gamma                90
_cell_volume                     2046.45(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3721
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.1510
_cell_measurement_theta_min      5.3110
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88389
_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    1.121
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14602
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.024
_diffrn_reflns_theta_max         67.024
_diffrn_reflns_theta_min         5.318
_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 1.000
_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   -102.00 -25.00   1.00    3.50    --  -33.50 -57.00 120.00   77
  2  ω    -50.00 -24.00   1.00    3.50    --  -33.50  57.00 -30.00   26
  3  ω   -104.00 -79.00   1.00    3.50    --  -33.50 -37.00 -30.00   25
  4  ω    -69.00 -15.00   1.00    3.50    --  -33.50 -57.00-150.00   54
  5  ω    -15.00  11.00   1.00    3.50    --  -33.50  57.00 -30.00   26
  6  ω    -64.00 -37.00   1.00    3.50    --  -33.50 -19.00-120.00   27
  7  ω     34.00  77.00   1.00    3.50    --   36.47 -99.00-180.00   43
  8  ω     58.00 110.00   1.00    3.50    --   36.47 178.00  60.00   52
  9  ω    -34.00  51.00   1.00    3.50    --   36.47 -37.00-150.00   85
 10  ω     66.00 106.00   1.00    3.50    --   36.47 178.00-120.00   40
 11  ω     47.00  73.00   1.00    3.50    --   36.47  19.00-120.00   26
 12  ω    -22.00  55.00   1.00    3.50    --   36.47 -57.00 150.00   77
 13  ω     -1.00  26.00   1.00    3.50    --   36.47  19.00-120.00   27
 14  ω     66.00 104.00   1.00    3.50    --   36.47  57.00-120.00   38
 15  ω      9.00  78.00   1.00    3.50    --   36.47-106.00  60.00   69
 16  ω     16.00  74.00   1.00    3.50    --   36.47 -19.00   0.00   58
 17  ω    -36.00   5.00   1.00    3.50    --   36.47 -19.00   0.00   41
 18  ω     39.00 117.00   1.00   10.00    --  108.00 -45.00  90.00   78
 19  ω     79.00 178.00   1.00   10.00    --  108.00  15.00-120.00   99
 20  ω     41.00 106.00   1.00   10.00    --  108.00-111.00 120.00   65
 21  ω     37.00 131.00   1.00   10.00    --  108.00 -30.00 -60.00   94
 22  ω     90.00 168.00   1.00   10.00    --  108.00  61.00 -60.00   78
 23  ω    153.00 178.00   1.00   10.00    --  108.00 111.00-120.00   25
 24  ω    153.00 178.00   1.00   10.00    --  108.00 111.00 -60.00   25
 25  ω     87.00 112.00   1.00   10.00    --  108.00-111.00   0.00   25
 26  ω    140.00 175.00   1.00   10.00    --  108.00  61.00  60.00   35
 27  ω    103.00 129.00   1.00   10.00    --  108.00  61.00  60.00   26
 28  ω     53.00 116.00   1.00   10.00    --  108.00 -45.00 150.00   63
 29  ω     39.00 136.00   1.00   10.00    --  108.00 -77.00 -60.00   97
 30  ω     45.00  80.00   1.00   10.00    --  108.00 -94.00 -60.00   35
 31  ω    121.00 157.00   1.00   10.00    --  108.00  30.00 -90.00   36
 32  ω     61.00 109.00   1.00   10.00    --  108.00 -94.00-150.00   48
 33  ω    101.00 147.00   1.00   10.00    --  108.00 111.00-120.00   46
 34  ω     42.00  93.00   1.00   10.00    --  108.00 -15.00-120.00   51
;
_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      -0.0406308000
_diffrn_orient_matrix_UB_12      0.0181667000
_diffrn_orient_matrix_UB_13      0.1596301000
_diffrn_orient_matrix_UB_21      0.0345528000
_diffrn_orient_matrix_UB_22      -0.0492757000
_diffrn_orient_matrix_UB_23      0.0695743000
_diffrn_orient_matrix_UB_31      0.1773359000
_diffrn_orient_matrix_UB_32      0.0137509000
_diffrn_orient_matrix_UB_33      0.0384706000
_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                2743
_reflns_number_total             3649
_reflns_odcompleteness_completeness 99.95
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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         0.146
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3649
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.034
_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)+(0.0977P)²+0.0140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1591
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_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
C1 C 0.5219(3) 0.58381(8) 0.7505(2) 0.0719(6) Uani 1 1 d . . . . .
H1A H 0.4703 0.6089 0.6982 0.086 Uiso 1 1 calc R . . . .
C2 C 0.5154(4) 0.53945(9) 0.6841(3) 0.0982(9) Uani 1 1 d . . . . .
H2 H 0.4600 0.5349 0.5877 0.118 Uiso 1 1 calc R . . . .
C3 C 0.5897(5) 0.50269(10) 0.7598(4) 0.1211(13) Uani 1 1 d . . . . .
H3 H 0.5839 0.4728 0.7159 0.145 Uiso 1 1 calc R . . . .
C4 C 0.6726(5) 0.50939(9) 0.8995(4) 0.1326(14) Uani 1 1 d . . . . .
H4 H 0.7244 0.4840 0.9499 0.159 Uiso 1 1 calc R . . . .
C5 C 0.6811(4) 0.55415(8) 0.9690(3) 0.0942(9) Uani 1 1 d . . . . .
H5 H 0.7380 0.5585 1.0648 0.113 Uiso 1 1 calc R . . . .
C6 C 0.6040(2) 0.59143(6) 0.8932(2) 0.0567(5) Uani 1 1 d . . . . .
C7 C 0.6062(2) 0.64112(6) 0.96086(19) 0.0487(4) Uani 1 1 d . . . . .
C8 C 0.4374(2) 0.65421(6) 1.0106(2) 0.0521(4) Uani 1 1 d . . . . .
H8 H 0.3513 0.6375 0.9492 0.063 Uiso 1 1 calc R . . . .
C9 C 0.4507(2) 0.63895(6) 1.1768(2) 0.0533(4) Uani 1 1 d . . . . .
C10 C 0.6082(2) 0.63534(6) 1.2232(2) 0.0539(4) Uani 1 1 d . . . . .
C11 C 0.6934(3) 0.62730(9) 1.3786(2) 0.0774(6) Uani 1 1 d . . . . .
H11A H 0.7757 0.6507 1.3980 0.116 Uiso 1 1 calc GR . . . .
H11B H 0.7414 0.5965 1.3819 0.116 Uiso 1 1 calc GR . . . .
H11C H 0.6181 0.6295 1.4562 0.116 Uiso 1 1 calc GR . . . .
C12 C 0.3179(3) 0.63522(8) 1.2742(3) 0.0691(5) Uani 1 1 d . . . . .
C13 C 0.1512(3) 0.64222(12) 1.1987(3) 0.1013(9) Uani 1 1 d . . . . .
H13A H 0.1248 0.6167 1.1283 0.152 Uiso 1 1 calc GR . . . .
H13B H 0.1464 0.6715 1.1429 0.152 Uiso 1 1 calc GR . . . .
H13C H 0.0760 0.6429 1.2765 0.152 Uiso 1 1 calc GR . . . .
C14 C 0.4185(3) 0.72702(7) 0.8664(3) 0.0677(5) Uani 1 1 d . . . . .
H14A H 0.4083 0.7609 0.8775 0.081 Uiso 1 1 calc R . . . .
H14B H 0.3317 0.7161 0.7937 0.081 Uiso 1 1 calc R . . . .
C15 C 0.5747(2) 0.71542(6) 0.8087(2) 0.0584(5) Uani 1 1 d . . . . .
C16 C 0.6654(2) 0.67701(6) 0.8538(2) 0.0512(4) Uani 1 1 d . . . . .
C17 C 0.8079(2) 0.67869(6) 0.7726(2) 0.0549(4) Uani 1 1 d . . . . .
C18 C 0.7958(3) 0.71950(7) 0.6809(2) 0.0626(5) Uani 1 1 d . . . . .
C19 C 0.9134(3) 0.73265(9) 0.5845(3) 0.0786(6) Uani 1 1 d . . . . .
H19 H 0.9040 0.7600 0.5255 0.094 Uiso 1 1 calc R . . . .
C20 C 1.0431(3) 0.70361(10) 0.5803(3) 0.0859(7) Uani 1 1 d . . . . .
H20 H 1.1238 0.7115 0.5172 0.103 Uiso 1 1 calc R . . . .
C21 C 1.0583(3) 0.66203(10) 0.6685(3) 0.0822(7) Uani 1 1 d . . . . .
H21 H 1.1476 0.6428 0.6616 0.099 Uiso 1 1 calc R . . . .
C22 C 0.9420(3) 0.64957(8) 0.7653(2) 0.0667(5) Uani 1 1 d . . . . .
H22 H 0.9527 0.6223 0.8246 0.080 Uiso 1 1 calc R . . . .
N1 N 0.6532(2) 0.74130(6) 0.7056(2) 0.0687(5) Uani 1 1 d . . . . .
H1 H 0.605(3) 0.7638(9) 0.646(3) 0.099(9) Uiso 1 1 d . . . . .
O1 O 0.70740(15) 0.64097(4) 1.10869(14) 0.0545(3) Uani 1 1 d . . . . .
O2 O 0.40946(16) 0.70443(4) 1.01345(15) 0.0600(4) Uani 1 1 d . . . . .
O3 O 0.3376(2) 0.62698(9) 1.4117(2) 0.1076(7) 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 0.9300 . ?
C1 C2 1.383(3) . ?
C1 C6 1.380(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.355(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.357(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.405(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(3) . ?
C6 C7 1.527(2) . ?
C7 C8 1.553(2) . ?
C7 C16 1.490(2) . ?
C7 O1 1.475(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.499(2) . ?
C8 O2 1.445(2) . ?
C9 C10 1.346(3) . ?
C9 C12 1.453(3) . ?
C10 C11 1.488(3) . ?
C10 O1 1.354(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.500(3) . ?
C12 O3 1.212(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.472(3) . ?
C14 O2 1.435(2) . ?
C15 C16 1.365(3) . ?
C15 N1 1.366(3) . ?
C16 C17 1.433(3) . ?
C17 C18 1.403(3) . ?
C17 C22 1.397(3) . ?
C18 C19 1.393(3) . ?
C18 N1 1.374(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.363(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.406(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(3) . ?
C22 H22 0.9300 . ?
N1 H1 0.89(3) . ?

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 H1A 119.5 . . ?
C6 C1 H1A 119.5 . . ?
C6 C1 C2 121.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 118.57(17) . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 122.44(19) . . ?
C6 C7 C8 110.22(14) . . ?
C16 C7 C6 112.72(14) . . ?
C16 C7 C8 111.44(14) . . ?
O1 C7 C6 108.59(13) . . ?
O1 C7 C8 103.07(13) . . ?
O1 C7 C16 110.34(14) . . ?
C7 C8 H8 112.0 . . ?
C9 C8 C7 101.66(14) . . ?
C9 C8 H8 112.0 . . ?
O2 C8 C7 113.09(14) . . ?
O2 C8 H8 112.0 . . ?
O2 C8 C9 105.53(14) . . ?
C10 C9 C8 107.53(16) . . ?
C10 C9 C12 126.44(19) . . ?
C12 C9 C8 125.53(18) . . ?
C9 C10 C11 131.57(18) . . ?
C9 C10 O1 114.44(16) . . ?
O1 C10 C11 113.98(17) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 C13 117.4(2) . . ?
O3 C12 C9 122.6(2) . . ?
O3 C12 C13 119.9(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
O2 C14 H14A 110.0 . . ?
O2 C14 H14B 110.0 . . ?
O2 C14 C15 108.38(15) . . ?
C16 C15 C14 124.53(17) . . ?
C16 C15 N1 109.39(18) . . ?
N1 C15 C14 126.06(18) . . ?
C15 C16 C7 121.30(17) . . ?
C15 C16 C17 107.21(16) . . ?
C17 C16 C7 131.37(16) . . ?
C18 C17 C16 106.37(17) . . ?
C22 C17 C16 134.72(18) . . ?
C22 C17 C18 118.89(19) . . ?
C19 C18 C17 122.7(2) . . ?
N1 C18 C17 107.82(17) . . ?
N1 C18 C19 129.5(2) . . ?
C18 C19 H19 121.5 . . ?
C20 C19 C18 117.1(2) . . ?
C20 C19 H19 121.5 . . ?
C19 C20 H20 119.0 . . ?
C19 C20 C21 121.9(2) . . ?
C21 C20 H20 119.0 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 120.6 . . ?
C21 C22 C17 118.8(2) . . ?
C21 C22 H22 120.6 . . ?
C15 N1 C18 109.20(16) . . ?
C15 N1 H1 122.8(18) . . ?
C18 N1 H1 125.9(18) . . ?
C10 O1 C7 107.23(13) . . ?
C14 O2 C8 113.90(14) . . ?

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
N1 H1 O1 0.89(3) 2.86(3) 3.484(2) 128(2) 4_575
N1 H1 O2 0.89(3) 2.12(3) 2.953(2) 155(2) 4_575

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(6) . . . . ?
C1 C6 C7 C8 70.7(2) . . . . ?
C1 C6 C7 C16 -54.5(2) . . . . ?
C1 C6 C7 O1 -177.06(16) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C2 C1 C6 C7 -179.7(2) . . . . ?
C2 C3 C4 C5 0.9(6) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 C7 179.6(3) . . . . ?
C5 C6 C7 C8 -109.5(2) . . . . ?
C5 C6 C7 C16 125.3(2) . . . . ?
C5 C6 C7 O1 2.7(3) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C6 C7 C8 C9 91.88(16) . . . . ?
C6 C7 C8 O2 -155.47(14) . . . . ?
C6 C7 C16 C15 123.77(18) . . . . ?
C6 C7 C16 C17 -51.7(3) . . . . ?
C6 C7 O1 C10 -95.68(16) . . . . ?
C7 C8 C9 C10 19.19(18) . . . . ?
C7 C8 C9 C12 -168.49(18) . . . . ?
C7 C8 O2 C14 60.41(19) . . . . ?
C7 C16 C17 C18 176.38(18) . . . . ?
C7 C16 C17 C22 -1.9(4) . . . . ?
C8 C7 C16 C15 -0.8(2) . . . . ?
C8 C7 C16 C17 -176.20(17) . . . . ?
C8 C7 O1 C10 21.22(16) . . . . ?
C8 C9 C10 C11 171.7(2) . . . . ?
C8 C9 C10 O1 -6.8(2) . . . . ?
C8 C9 C12 C13 6.9(3) . . . . ?
C8 C9 C12 O3 -172.9(2) . . . . ?
C9 C8 O2 C14 170.68(16) . . . . ?
C9 C10 O1 C7 -9.9(2) . . . . ?
C10 C9 C12 C13 177.7(2) . . . . ?
C10 C9 C12 O3 -2.0(4) . . . . ?
C11 C10 O1 C7 171.38(16) . . . . ?
C12 C9 C10 C11 -0.5(3) . . . . ?
C12 C9 C10 O1 -179.00(17) . . . . ?
C14 C15 C16 C7 4.0(3) . . . . ?
C14 C15 C16 C17 -179.56(18) . . . . ?
C14 C15 N1 C18 179.54(19) . . . . ?
C15 C14 O2 C8 -54.6(2) . . . . ?
C15 C16 C17 C18 0.5(2) . . . . ?
C15 C16 C17 C22 -177.8(2) . . . . ?
C16 C7 C8 C9 -142.20(15) . . . . ?
C16 C7 C8 O2 -29.5(2) . . . . ?
C16 C7 O1 C10 140.31(15) . . . . ?
C16 C15 N1 C18 0.7(2) . . . . ?
C16 C17 C18 C19 -179.66(18) . . . . ?
C16 C17 C18 N1 0.0(2) . . . . ?
C16 C17 C22 C21 178.3(2) . . . . ?
C17 C18 C19 C20 0.8(3) . . . . ?
C17 C18 N1 C15 -0.4(2) . . . . ?
C18 C17 C22 C21 0.2(3) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C19 C18 N1 C15 179.2(2) . . . . ?
C19 C20 C21 C22 -1.0(4) . . . . ?
C20 C21 C22 C17 0.8(3) . . . . ?
C22 C17 C18 C19 -1.1(3) . . . . ?
C22 C17 C18 N1 178.59(17) . . . . ?
N1 C15 C16 C7 -177.16(16) . . . . ?
N1 C15 C16 C17 -0.7(2) . . . . ?
N1 C18 C19 C20 -178.7(2) . . . . ?
O1 C7 C8 C9 -23.87(16) . . . . ?
O1 C7 C8 O2 88.78(15) . . . . ?
O1 C7 C16 C15 -114.63(18) . . . . ?
O1 C7 C16 C17 69.9(2) . . . . ?
O2 C8 C9 C10 -99.04(16) . . . . ?
O2 C8 C9 C12 73.3(2) . . . . ?
O2 C14 C15 C16 22.8(3) . . . . ?
O2 C14 C15 N1 -155.85(18) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.792 190.6 53.2 ?
2 0.000 0.500 0.271 190.6 53.2 ?

_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 2.352
_oxdiff_exptl_absorpt_empirical_full_min 0.808
####################################################################### 
# 
# 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_202104106
_database_code_depnum_ccdc_archive 'CCDC 2079855'
loop_
_audit_author_name
_audit_author_address
'Mei guangjian'
;JiangSu normal universtiy
China
;
_audit_update_record             
;
2021-04-25 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_audit_creation_date             2021-04-23
_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         'C22 H18 Br N O3'
_chemical_formula_sum            'C22 H18 Br N O3'
_chemical_formula_weight         424.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O5N2Br1
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1529(6)
_cell_length_b                   30.7743(11)
_cell_length_c                   8.7822(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.200(5)
_cell_angle_gamma                90
_cell_volume                     2194.41(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2025
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9910
_cell_measurement_theta_min      5.4260
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.703
_exptl_absorpt_coefficient_mu    2.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78709
_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    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8408
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         5.258
_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   -102.00 -11.00   1.00    1.75    --  -33.50 -77.00-180.00   91
  2  ω    -44.00 -16.00   1.00    1.75    --  -33.50 -57.00-150.00   28
  3  ω    -91.00 -65.00   1.00    1.75    --  -33.50 -57.00 120.00   26
  4  ω   -107.00 -81.00   1.00    1.75    --  -33.50 178.00   0.00   26
  5  ω     39.00  98.00   1.00    1.75    --   36.47  57.00  30.00   59
  6  ω     -3.00  74.00   1.00    1.75    --   36.47 -99.00  60.00   77
  7  ω     59.00 104.00   1.00    1.75    --   36.47  57.00  90.00   45
  8  ω     70.00  97.00   1.00   10.50    --  108.00 -94.00-150.00   27
  9  ω     79.00 177.00   1.00   10.50    --  108.00  77.00 -90.00   98
 10  ω    101.00 155.00   1.00   10.50    --  108.00 111.00 150.00   54
 11  ω    133.00 174.00   1.00   10.50    --  108.00  61.00-180.00   41
 12  ω     89.00 130.00   1.00   10.50    --  108.00  61.00-180.00   41
 13  ω    116.00 142.00   1.00   10.50    --  108.00  61.00-120.00   26
 14  ω     41.00 112.00   1.00   10.50    --  108.00-111.00 -30.00   71
 15  ω     38.00 110.00   1.00   10.50    --  108.00 -94.00-180.00   72
 16  ω    139.00 167.00   1.00   10.50    --  108.00  61.00 -60.00   28
 17  ω     41.00  67.00   1.00   10.50    --  108.00 -94.00   0.00   26
 18  ω     66.00 129.00   1.00   10.50    --  108.00 178.00   0.00   63
;
_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      -0.1864409000
_diffrn_orient_matrix_UB_12      -0.0009990000
_diffrn_orient_matrix_UB_13      -0.0479855000
_diffrn_orient_matrix_UB_21      0.0042915000
_diffrn_orient_matrix_UB_22      -0.0500479000
_diffrn_orient_matrix_UB_23      -0.0023492000
_diffrn_orient_matrix_UB_31      -0.0346879000
_diffrn_orient_matrix_UB_32      -0.0009694000
_diffrn_orient_matrix_UB_33      0.1695000000
_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                2805
_reflns_number_total             3918
_reflns_odcompleteness_completeness 99.85
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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         0.206
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.038
_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)+(0.0810P)²+0.2436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1675
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Br1) = Uanis(Br1A)
3. Others
 Sof(Br1A)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C18(H18), C19(H19), C21(H21), C22(H22), N1(H1A)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_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 0.3971(2) 0.46832(3) 0.7913(2) 0.1310(6) Uani 0.887(5) 1 d . . P A 1
Br1A Br 0.3414(19) 0.4625(2) 0.7217(17) 0.1310(6) Uani 0.113(5) 1 d . . P A 2
C1 C 0.0053(4) 0.65563(12) 0.6825(4) 0.0608(8) Uani 1 1 d . . . . .
H1 H -0.0066 0.6306 0.6234 0.073 Uiso 1 1 calc R . . . .
C2 C -0.1104(5) 0.66623(15) 0.7816(4) 0.0720(10) Uani 1 1 d . . . . .
H2 H -0.1990 0.6477 0.7913 0.086 Uiso 1 1 calc R . . . .
C3 C -0.0964(5) 0.70416(15) 0.8672(4) 0.0766(11) Uani 1 1 d . . . . .
H3 H -0.1776 0.7108 0.9313 0.092 Uiso 1 1 calc R . . . .
C4 C 0.0331(5) 0.73206(13) 0.8602(4) 0.0711(10) Uani 1 1 d . . . . .
H4 H 0.0415 0.7573 0.9186 0.085 Uiso 1 1 calc R . . . .
C5 C 0.1518(5) 0.72134(11) 0.7624(3) 0.0588(8) Uani 1 1 d . . . . .
C6 C 0.1410(4) 0.68310(10) 0.6721(3) 0.0520(7) Uani 1 1 d . . . . .
C7 C 0.2841(4) 0.68274(9) 0.5895(3) 0.0504(6) Uani 1 1 d . . . . .
C8 C 0.3751(4) 0.71875(10) 0.6326(3) 0.0571(7) Uani 1 1 d . . . . .
C9 C 0.5336(5) 0.73018(11) 0.5739(4) 0.0652(8) Uani 1 1 d . . . . .
H9A H 0.5414 0.7614 0.5617 0.078 Uiso 1 1 calc R . . . .
H9B H 0.6243 0.7207 0.6453 0.078 Uiso 1 1 calc R . . . .
C10 C 0.3465(4) 0.64967(9) 0.4852(3) 0.0469(6) Uani 1 1 d . . . . .
C11 C 0.5161(4) 0.66280(10) 0.4343(3) 0.0511(6) Uani 1 1 d . . . . .
H11 H 0.6064 0.6481 0.4951 0.061 Uiso 1 1 calc R . . . .
C12 C 0.5014(4) 0.64766(10) 0.2701(3) 0.0518(6) Uani 1 1 d . . . . .
C13 C 0.3393(4) 0.64265(10) 0.2262(3) 0.0525(7) Uani 1 1 d . . . . .
C14 C 0.2508(5) 0.63328(15) 0.0756(4) 0.0722(10) Uani 1 1 d . . . . .
H14A H 0.3278 0.6325 -0.0008 0.108 Uiso 1 1 calc GR . . . .
H14B H 0.1705 0.6556 0.0506 0.108 Uiso 1 1 calc GR . . . .
H14C H 0.1965 0.6057 0.0792 0.108 Uiso 1 1 calc GR . . . .
C15 C 0.6363(5) 0.64397(12) 0.1729(4) 0.0649(8) Uani 1 1 d . . . . .
C16 C 0.8085(5) 0.6511(2) 0.2465(5) 0.0946(15) Uani 1 1 d . . . . .
H16A H 0.8116 0.6772 0.3064 0.142 Uiso 1 1 calc GR . . . .
H16B H 0.8832 0.6537 0.1685 0.142 Uiso 1 1 calc GR . . . .
H16C H 0.8404 0.6268 0.3113 0.142 Uiso 1 1 calc GR . . . .
C17 C 0.3549(4) 0.60441(9) 0.5556(3) 0.0534(7) Uani 1 1 d . . . . .
C18 C 0.4310(5) 0.59934(12) 0.7021(4) 0.0638(8) Uani 1 1 d . . . . .
H18 H 0.4742 0.6236 0.7547 0.077 Uiso 1 1 calc R . . . .
C19 C 0.4442(6) 0.55919(14) 0.7717(5) 0.0794(11) Uani 1 1 d . . . . .
H19 H 0.4969 0.5562 0.8695 0.095 Uiso 1 1 calc R . . . .
C20 C 0.3779(7) 0.52374(12) 0.6931(5) 0.0910(14) Uani 1 1 d . . . . .
C21 C 0.3036(9) 0.52782(14) 0.5493(6) 0.1077(18) Uani 1 1 d . . . . .
H21 H 0.2622 0.5033 0.4969 0.129 Uiso 1 1 calc R . . . .
C22 C 0.2892(6) 0.56817(12) 0.4801(5) 0.0820(12) Uani 1 1 d . . . . .
H22 H 0.2353 0.5709 0.3827 0.098 Uiso 1 1 calc R . . . .
N1 N 0.2949(4) 0.74224(9) 0.7359(3) 0.0651(7) Uani 1 1 d . . . . .
H1A H 0.3291 0.7663 0.7775 0.078 Uiso 1 1 calc R . . . .
O1 O 0.2401(3) 0.64810(7) 0.3399(2) 0.0524(5) Uani 1 1 d . . . . .
O2 O 0.5417(3) 0.70903(7) 0.4292(2) 0.0576(5) Uani 1 1 d . . . . .
O3 O 0.6156(4) 0.63526(12) 0.0387(3) 0.0906(9) 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
Br1 C20 1.911(4) . ?
Br1A C20 1.926(9) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(5) . ?
C1 C6 1.402(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(5) . ?
C5 C6 1.418(4) . ?
C5 N1 1.371(5) . ?
C6 C7 1.428(5) . ?
C7 C8 1.368(5) . ?
C7 C10 1.489(4) . ?
C8 C9 1.477(5) . ?
C8 N1 1.371(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 O2 1.435(4) . ?
C10 C11 1.545(4) . ?
C10 C17 1.523(4) . ?
C10 O1 1.477(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.509(4) . ?
C11 O2 1.439(4) . ?
C12 C13 1.352(5) . ?
C12 C15 1.456(5) . ?
C13 C14 1.476(4) . ?
C13 O1 1.351(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.507(6) . ?
C15 O3 1.206(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.385(5) . ?
C17 C22 1.380(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.375(7) . ?
C20 C21 1.356(8) . ?
C21 H21 0.9300 . ?
C21 C22 1.383(6) . ?
C22 H22 0.9300 . ?
N1 H1A 0.8600 . ?

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 120.4 . . ?
C2 C1 C6 119.2(3) . . ?
C6 C1 H1 120.4 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.9(4) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.6(3) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 122.1(4) . . ?
N1 C5 C4 130.1(3) . . ?
N1 C5 C6 107.8(3) . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 135.6(3) . . ?
C5 C6 C7 106.2(3) . . ?
C6 C7 C10 131.2(3) . . ?
C8 C7 C6 107.5(3) . . ?
C8 C7 C10 121.1(3) . . ?
C7 C8 C9 124.5(3) . . ?
C7 C8 N1 109.4(3) . . ?
N1 C8 C9 126.2(3) . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
O2 C9 C8 108.2(3) . . ?
O2 C9 H9A 110.0 . . ?
O2 C9 H9B 110.0 . . ?
C7 C10 C11 111.4(2) . . ?
C7 C10 C17 112.4(2) . . ?
C17 C10 C11 110.4(2) . . ?
O1 C10 C7 110.3(2) . . ?
O1 C10 C11 103.3(2) . . ?
O1 C10 C17 108.8(2) . . ?
C10 C11 H11 111.7 . . ?
C12 C11 C10 101.5(2) . . ?
C12 C11 H11 111.7 . . ?
O2 C11 C10 113.8(2) . . ?
O2 C11 H11 111.7 . . ?
O2 C11 C12 105.9(2) . . ?
C13 C12 C11 107.4(3) . . ?
C13 C12 C15 126.5(3) . . ?
C15 C12 C11 125.8(3) . . ?
C12 C13 C14 131.6(3) . . ?
O1 C13 C12 114.2(3) . . ?
O1 C13 C14 114.2(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 C16 117.5(3) . . ?
O3 C15 C12 123.0(4) . . ?
O3 C15 C16 119.6(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C10 118.7(3) . . ?
C22 C17 C10 122.9(3) . . ?
C22 C17 C18 118.4(3) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.6(4) . . ?
C19 C18 H18 119.2 . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.5(4) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 Br1 118.0(4) . . ?
C19 C20 Br1A 140.2(6) . . ?
C21 C20 Br1 121.0(4) . . ?
C21 C20 Br1A 98.7(6) . . ?
C21 C20 C19 121.0(4) . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 120.1(4) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C5 N1 C8 109.2(3) . . ?
C5 N1 H1A 125.4 . . ?
C8 N1 H1A 125.4 . . ?
C13 O1 C10 107.4(2) . . ?
C9 O2 C11 113.7(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 C20 C21 C22 179.4(4) . . . . ?
Br1A C20 C21 C22 176.0(6) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
C1 C6 C7 C8 -178.0(3) . . . . ?
C1 C6 C7 C10 -3.9(6) . . . . ?
C2 C1 C6 C5 -1.2(5) . . . . ?
C2 C1 C6 C7 177.9(3) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C3 C4 C5 N1 -177.9(3) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C4 C5 C6 C7 -179.1(3) . . . . ?
C4 C5 N1 C8 178.2(3) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C5 C6 C7 C10 175.3(3) . . . . ?
C6 C1 C2 C3 1.9(6) . . . . ?
C6 C5 N1 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 179.5(3) . . . . ?
C6 C7 C8 N1 -1.3(4) . . . . ?
C6 C7 C10 C11 -175.1(3) . . . . ?
C6 C7 C10 C17 -50.7(4) . . . . ?
C6 C7 C10 O1 70.8(4) . . . . ?
C7 C8 C9 O2 22.6(4) . . . . ?
C7 C8 N1 C5 0.8(4) . . . . ?
C7 C10 C11 C12 -142.4(2) . . . . ?
C7 C10 C11 O2 -29.1(3) . . . . ?
C7 C10 C17 C18 -49.5(4) . . . . ?
C7 C10 C17 C22 130.2(4) . . . . ?
C7 C10 O1 C13 141.1(2) . . . . ?
C8 C7 C10 C11 -1.7(4) . . . . ?
C8 C7 C10 C17 122.7(3) . . . . ?
C8 C7 C10 O1 -115.7(3) . . . . ?
C8 C9 O2 C11 -54.4(4) . . . . ?
C9 C8 N1 C5 -180.0(3) . . . . ?
C10 C7 C8 C9 4.7(5) . . . . ?
C10 C7 C8 N1 -176.1(3) . . . . ?
C10 C11 C12 C13 18.9(3) . . . . ?
C10 C11 C12 C15 -167.3(3) . . . . ?
C10 C11 O2 C9 60.4(3) . . . . ?
C10 C17 C18 C19 -179.3(3) . . . . ?
C10 C17 C22 C21 178.8(4) . . . . ?
C11 C10 C17 C18 75.5(3) . . . . ?
C11 C10 C17 C22 -104.9(4) . . . . ?
C11 C10 O1 C13 22.0(3) . . . . ?
C11 C12 C13 C14 172.4(4) . . . . ?
C11 C12 C13 O1 -5.9(4) . . . . ?
C11 C12 C15 C16 7.2(5) . . . . ?
C11 C12 C15 O3 -173.4(4) . . . . ?
C12 C11 O2 C9 171.0(3) . . . . ?
C12 C13 O1 C10 -10.8(3) . . . . ?
C13 C12 C15 C16 179.8(4) . . . . ?
C13 C12 C15 O3 -0.9(6) . . . . ?
C14 C13 O1 C10 170.6(3) . . . . ?
C15 C12 C13 C14 -1.3(6) . . . . ?
C15 C12 C13 O1 -179.6(3) . . . . ?
C17 C10 C11 C12 92.0(3) . . . . ?
C17 C10 C11 O2 -154.6(2) . . . . ?
C17 C10 O1 C13 -95.2(3) . . . . ?
C17 C18 C19 C20 -0.9(6) . . . . ?
C18 C17 C22 C21 -1.5(7) . . . . ?
C18 C19 C20 Br1 -180.0(3) . . . . ?
C18 C19 C20 Br1A -175.4(7) . . . . ?
C18 C19 C20 C21 1.2(8) . . . . ?
C19 C20 C21 C22 -1.8(9) . . . . ?
C20 C21 C22 C17 2.0(9) . . . . ?
C22 C17 C18 C19 1.0(6) . . . . ?
N1 C5 C6 C1 178.7(3) . . . . ?
N1 C5 C6 C7 -0.7(3) . . . . ?
N1 C8 C9 O2 -156.5(3) . . . . ?
O1 C10 C11 C12 -24.1(3) . . . . ?
O1 C10 C11 O2 89.2(3) . . . . ?
O1 C10 C17 C18 -171.9(3) . . . . ?
O1 C10 C17 C22 7.8(4) . . . . ?
O2 C11 C12 C13 -100.2(3) . . . . ?
O2 C11 C12 C15 73.6(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.671 206.1 47.7 ?
2 0.000 0.500 -0.148 206.1 47.7 ?


_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 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.807
