# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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. 
# 
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data_20220719co2_auto
_database_code_depnum_ccdc_archive 'CCDC 2309598'
loop_
_audit_author_name
_audit_author_address
'Zhuoer Wang'
;Shandong University
China
;
_audit_update_record             
;
2023-11-22 deposited with the CCDC.	2024-04-05 downloaded from the CCDC.
;
_audit_creation_date             2023-11-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 Br0.975 N O3'
_chemical_formula_sum            'C15 H11 Br0.97 N O3'
_chemical_formula_weight         330.76
_chemical_melting_point          ?
_chemical_oxdiff_formula         CONBr
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.4015(4)
_cell_length_b                   8.5478(6)
_cell_length_c                   11.0934(5)
_cell_angle_alpha                96.710(4)
_cell_angle_beta                 92.275(4)
_cell_angle_gamma                111.131(6)
_cell_volume                     647.62(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3665
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      29.9660
_cell_measurement_theta_min      2.9530
_shelx_estimated_absorpt_T_max   0.913
_shelx_estimated_absorpt_T_min   0.836
_exptl_absorpt_coefficient_mu    3.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
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    1.696
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9238
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.855
_diffrn_reflns_theta_min         2.580
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.808
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  -4.00   1.00    3.82    --    5.67 -19.00 -30.00   65
  2  ω    -60.00 -15.00   1.00    3.82    --    5.67 -38.00  30.00   45
  3  ω    -65.00  15.00   1.00    3.82    --    5.67 -43.00  84.00   80
  4  ω     -8.00  18.00   1.00    3.82    --    5.67 -99.00  90.00   26
  5  ω     -7.00  78.00   1.00    3.82    --    5.67  43.00-123.00   85
  6  ω    -23.00  29.00   1.00    3.82    --   -4.50 -99.00  60.00   52
  7  ω    -15.00  11.00   1.00    3.82    --   -4.50 -99.00 -30.00   26
  8  ω    -23.00  14.00   1.00    3.82    --   -4.50 -99.00-150.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0517099000
_diffrn_orient_matrix_UB_12      -0.0817380000
_diffrn_orient_matrix_UB_13      -0.0326895000
_diffrn_orient_matrix_UB_21      -0.0892391000
_diffrn_orient_matrix_UB_22      0.0095587000
_diffrn_orient_matrix_UB_23      0.0117240000
_diffrn_orient_matrix_UB_31      0.0010149000
_diffrn_orient_matrix_UB_32      0.0360811000
_diffrn_orient_matrix_UB_33      -0.0545100000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2576
_reflns_number_total             3286
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.199
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+0.9002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1404
_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:
 C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C15(H15), C10(H10)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br13 Br -0.03629(7) 0.23583(6) 0.70518(4) 0.02848(19) Uani 0.885(4) 1 d . . . A
1
O20 O 0.6304(4) 0.8938(4) 0.3425(2) 0.0282(7) Uani 1 1 d . . . . .
O18 O 0.3401(5) 0.8754(4) 0.0970(3) 0.0378(8) Uani 1 1 d . . . . .
O21 O 0.2631(5) 0.3791(4) 0.1346(3) 0.0367(8) Uani 1 1 d . . . . .
N6 N 0.4408(5) 0.6386(4) 0.2369(3) 0.0228(7) Uani 1 1 d . . . . .
C8 C 0.4300(5) 0.6962(5) 0.4587(3) 0.0202(8) Uani 1 1 d . . . . .
C3 C 0.2896(5) 0.5310(5) 0.4565(3) 0.0204(8) Uani 1 1 d . . . . .
C2 C 0.2150(6) 0.4783(5) 0.5678(4) 0.0251(9) Uani 1 1 d . . . . .
C7 C 0.5090(5) 0.7542(5) 0.3441(3) 0.0198(8) Uani 1 1 d . . . . .
C4 C 0.2272(5) 0.4191(5) 0.3457(4) 0.0225(8) Uani 1 1 d . . . . .
C9 C 0.4923(6) 0.8053(5) 0.5658(3) 0.0240(8) Uani 1 1 d . . . . .
H9 H 0.585795 0.916030 0.565867 0.029 Uiso 1 1 calc R U . . .
C1 C 0.0743(6) 0.3115(6) 0.5604(4) 0.0275(9) Uani 1 1 d . . . . .
C5 C 0.3073(6) 0.4731(5) 0.2312(4) 0.0251(9) Uani 1 1 d . . . . .
C14 C 0.0131(6) 0.2053(6) 0.4537(4) 0.0306(10) Uani 1 1 d . . . . .
H14 H -0.081582 0.094826 0.452494 0.037 Uiso 1 1 calc R U . . .
C15 C 0.0892(6) 0.2582(5) 0.3449(4) 0.0280(9) Uani 1 1 d . . . . .
H15 H 0.045685 0.183233 0.270476 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2846(6) 0.5958(6) 0.6774(4) 0.0289(9) Uani 1 1 d . . . . .
C10 C 0.4183(6) 0.7540(6) 0.6756(4) 0.0296(9) Uani 1 1 d . . . . .
H10 H 0.462278 0.830596 0.749266 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5185(7) 0.6954(6) 0.1232(4) 0.0313(10) Uani 1 1 d . . . . .
H16A H 0.556979 0.606818 0.078386 0.038 Uiso 1 1 calc R U . . .
H16B H 0.636686 0.799117 0.143234 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3747(7) 0.7322(6) 0.0415(4) 0.0359(11) Uani 1 1 d . . . . .
H17A H 0.427097 0.754186 -0.038212 0.043 Uiso 1 1 calc R U . . .
H17B H 0.251146 0.632831 0.027057 0.043 Uiso 1 1 calc R U . . .
C19 C 0.2037(8) 0.9132(8) 0.0238(5) 0.0533(15) Uani 1 1 d . . . . .
H19A H 0.251231 0.932196 -0.056430 0.080 Uiso 1 1 calc R U . . .
H19B H 0.187359 1.015495 0.063118 0.080 Uiso 1 1 calc R U . . .
H19C H 0.078483 0.818100 0.014302 0.080 Uiso 1 1 calc R U . . .
Br1 Br 0.1332(8) 0.4601(8) 0.7944(4) 0.039(2) Uani 0.090(2) 1 d . . . B 2


_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
Br13 C1 1.906(4) . ?
O20 C7 1.210(5) . ?
O18 C17 1.417(6) . ?
O18 C19 1.419(6) . ?
O21 C5 1.217(5) . ?
N6 C7 1.401(5) . ?
N6 C5 1.396(5) . ?
N6 C16 1.469(5) . ?
C8 C3 1.417(5) . ?
C8 C7 1.484(5) . ?
C8 C9 1.372(5) . ?
C3 C2 1.427(5) . ?
C3 C4 1.414(5) . ?
C2 C1 1.421(6) . ?
C2 C11 1.430(6) . ?
C4 C5 1.476(6) . ?
C4 C15 1.385(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.407(6) . ?
C1 C14 1.356(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.406(6) . ?
C15 H15 0.9500 . ?
C11 C10 1.360(7) . ?
C11 Br1 1.953(7) . ?
C10 H10 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.511(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C17 O18 C19 111.6(4) . . ?
C7 N6 C16 117.4(3) . . ?
C5 N6 C7 124.6(3) . . ?
C5 N6 C16 118.0(3) . . ?
C3 C8 C7 120.1(3) . . ?
C9 C8 C3 120.7(3) . . ?
C9 C8 C7 119.2(4) . . ?
C8 C3 C2 119.1(3) . . ?
C4 C3 C8 120.3(3) . . ?
C4 C3 C2 120.6(4) . . ?
C3 C2 C11 118.3(4) . . ?
C1 C2 C3 116.7(4) . . ?
C1 C2 C11 124.9(4) . . ?
O20 C7 N6 120.8(3) . . ?
O20 C7 C8 122.0(3) . . ?
N6 C7 C8 117.2(3) . . ?
C3 C4 C5 120.4(3) . . ?
C15 C4 C3 119.6(4) . . ?
C15 C4 C5 120.0(4) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C2 C1 Br13 118.8(3) . . ?
C14 C1 Br13 118.8(3) . . ?
C14 C1 C2 122.4(4) . . ?
O21 C5 N6 120.0(4) . . ?
O21 C5 C4 122.6(4) . . ?
N6 C5 C4 117.4(3) . . ?
C1 C14 H14 119.9 . . ?
C1 C14 C15 120.3(4) . . ?
C15 C14 H14 119.9 . . ?
C4 C15 C14 120.3(4) . . ?
C4 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C2 C11 Br1 100.3(3) . . ?
C10 C11 C2 120.8(4) . . ?
C10 C11 Br1 138.9(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10 119.6 . . ?
N6 C16 H16A 109.0 . . ?
N6 C16 H16B 109.0 . . ?
N6 C16 C17 113.1(4) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
O18 C17 C16 109.7(4) . . ?
O18 C17 H17A 109.7 . . ?
O18 C17 H17B 109.7 . . ?
C16 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Br13 C1 C14 C15 178.9(3) . . . . ?
N6 C16 C17 O18 67.3(5) . . . . ?
C8 C3 C2 C1 179.9(3) . . . . ?
C8 C3 C2 C11 0.5(5) . . . . ?
C8 C3 C4 C5 -0.2(5) . . . . ?
C8 C3 C4 C15 -179.7(4) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
C3 C8 C7 O20 -179.3(4) . . . . ?
C3 C8 C7 N6 -0.9(5) . . . . ?
C3 C8 C9 C10 0.5(6) . . . . ?
C3 C2 C1 Br13 -178.2(3) . . . . ?
C3 C2 C1 C14 0.5(6) . . . . ?
C3 C2 C11 C10 0.0(6) . . . . ?
C3 C2 C11 Br1 178.9(3) . . . . ?
C3 C4 C5 O21 177.3(4) . . . . ?
C3 C4 C5 N6 -1.7(5) . . . . ?
C3 C4 C15 C14 -0.8(6) . . . . ?
C2 C3 C4 C5 -178.9(3) . . . . ?
C2 C3 C4 C15 1.5(6) . . . . ?
C2 C1 C14 C15 0.2(6) . . . . ?
C2 C11 C10 C9 -0.4(6) . . . . ?
C7 N6 C5 O21 -176.6(4) . . . . ?
C7 N6 C5 C4 2.4(6) . . . . ?
C7 N6 C16 C17 -105.8(4) . . . . ?
C7 C8 C3 C2 -179.7(3) . . . . ?
C7 C8 C3 C4 1.5(5) . . . . ?
C7 C8 C9 C10 179.4(3) . . . . ?
C4 C3 C2 C1 -1.3(5) . . . . ?
C4 C3 C2 C11 179.3(3) . . . . ?
C9 C8 C3 C2 -0.8(5) . . . . ?
C9 C8 C3 C4 -179.6(3) . . . . ?
C9 C8 C7 O20 1.8(6) . . . . ?
C9 C8 C7 N6 -179.8(3) . . . . ?
C1 C2 C11 C10 -179.3(4) . . . . ?
C1 C2 C11 Br1 -0.4(5) . . . . ?
C1 C14 C15 C4 0.0(6) . . . . ?
C5 N6 C7 O20 177.3(4) . . . . ?
C5 N6 C7 C8 -1.1(5) . . . . ?
C5 N6 C16 C17 75.2(5) . . . . ?
C5 C4 C15 C14 179.6(4) . . . . ?
C15 C4 C5 O21 -3.2(6) . . . . ?
C15 C4 C5 N6 177.8(4) . . . . ?
C11 C2 C1 Br13 1.1(5) . . . . ?
C11 C2 C1 C14 179.8(4) . . . . ?
C16 N6 C7 O20 -1.6(5) . . . . ?
C16 N6 C7 C8 180.0(3) . . . . ?
C16 N6 C5 O21 2.3(6) . . . . ?
C16 N6 C5 C4 -178.7(3) . . . . ?
C19 O18 C17 C16 -179.3(4) . . . . ?
Br1 C11 C10 C9 -178.7(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 1.242
_oxdiff_exptl_absorpt_empirical_full_min 0.762
####################################################################### 
# 
# 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_20220525wzeb_auto
_database_code_depnum_ccdc_archive 'CCDC 2309599'
loop_
_audit_author_name
_audit_author_address
'Zhuoer Wang'
;Shandong University
China
;
_audit_update_record             
;
2023-11-22 deposited with the CCDC.	2024-04-05 downloaded from the CCDC.
;
_audit_creation_date             2022-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Br N O3'
_chemical_formula_sum            'C21 H16 Br N O3'
_chemical_formula_weight         410.26
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         CONBr
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5671(2)
_cell_length_b                   6.22015(11)
_cell_length_c                   14.7354(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.310(2)
_cell_angle_gamma                90
_cell_volume                     849.68(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5653
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      75.4750
_cell_measurement_theta_min      4.7470
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    3.480
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
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    1.604
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7846
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.087
_diffrn_reflns_theta_min         3.095
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     92.00 169.00   1.00    0.10    --  105.98  15.00  90.00   77
  2  ω     89.00 169.00   1.00    0.10    --  105.98  65.00 151.00   80
  3  ω     81.00 113.00   1.00    0.10    --   48.21  65.00 151.00   32
  4  ω     41.00  66.00   1.00    0.10    --   48.21 -65.00  15.00   25
  5  ω    -19.00  37.00   1.00    0.10    --   48.21 -65.00  15.00   56
  6  ω     38.00  69.00   1.00    0.10    --  105.98 -61.00 120.00   31
  7  ω     34.00  70.00   1.00    0.10    --  105.98 -61.00  60.00   36
  8  ω     33.00  78.00   1.00    0.10    --  105.98 -65.00  15.00   45
  9  ω     39.00 108.00   1.00    0.10    --  105.98-125.00 -30.00   69
 10  ω    -40.00  24.00   1.00    0.10    --  -48.21  65.00 151.00   64
 11  ω    -27.00  26.00   1.00    0.10    --  -48.21  19.00 150.00   53
 12  ω    -51.00 -26.00   1.00    0.10    --  -91.75  45.00 150.00   25
 13  ω    -47.00 -19.00   1.00    0.10    --  -91.75  65.00 151.00   28
 14  ω    -78.00 -52.00   1.00    0.10    --  -91.75  65.00 151.00   26
 15  ω    -46.00 -20.00   1.00    0.10    --  -91.75  45.00   0.00   26
 16  ω    -71.00 -19.00   1.00    0.10    --  -91.75  61.00 -30.00   52
 17  ω    -48.00 -20.00   1.00    0.10    --  -91.75  45.00-150.00   28
 18  ω    -65.00 -34.00   1.00    0.10    --  -48.21 -65.00  15.00   31
 19  ω   -112.00 -80.00   1.00    0.10    --  -48.21 -65.00  15.00   32
 20  ω   -124.00 -99.00   1.00    0.10    --  -91.75 -65.00  15.00   25
 21  ω   -163.00 -80.00   1.00    0.10    --  -91.75 -45.00  60.00   83
 22  ω   -166.00 -81.00   1.00    0.10    --  -91.75 -30.00 -60.00   85
 23  ω   -131.00 -82.00   1.00    0.10    --  -91.75 -30.00 -90.00   49
 24  ω   -165.00-138.00   1.00    0.10    --  -91.75 -30.00 -90.00   27
 25  ω   -157.00 -88.00   1.00    0.10    --  -91.75 -45.00-120.00   69
 26  ω   -116.00 -80.00   1.00    0.10    --  -91.75 -61.00 -90.00   36
 27  ω   -160.00-123.00   1.00    0.10    --  -91.75 -61.00 -90.00   37
 28  ω   -161.00-135.00   1.00    0.10    --  -91.75 -94.00 150.00   26
 29  ω   -124.00 -91.00   1.00    0.10    --  -91.75 -94.00 150.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1458682000
_diffrn_orient_matrix_UB_12      -0.0223871000
_diffrn_orient_matrix_UB_13      0.0258340000
_diffrn_orient_matrix_UB_21      0.0622327000
_diffrn_orient_matrix_UB_22      -0.1839197000
_diffrn_orient_matrix_UB_23      0.0680934000
_diffrn_orient_matrix_UB_31      0.0497659000
_diffrn_orient_matrix_UB_32      0.1641826000
_diffrn_orient_matrix_UB_33      0.0796483000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                3066
_reflns_number_total             3212
_reflns_odcompleteness_completeness 99.82
_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 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.037(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.046
_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)+(0.0650P)²+0.0088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.0999
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C20(H20), C19(H19), C21(H21), C5(H5), C4(H4), C3(H3A),
 C18(H18), C17(H17)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.33811(6) 0.33187(9) 0.36113(3) 0.0458(2) Uani 1 1 d . . . . .
O2 O 0.1147(4) 1.0688(6) 0.7187(2) 0.0405(8) Uani 1 1 d . . . . .
N1 N 0.2424(4) 0.7673(5) 0.7758(2) 0.0234(7) Uani 1 1 d . . . . .
O1 O 0.3749(4) 0.4693(5) 0.8292(2) 0.0314(7) Uani 1 1 d . . . . .
C10 C 0.1793(4) 0.8460(8) 0.6060(3) 0.0249(7) Uani 1 1 d . . . . .
C13 C 0.2530(4) 0.8430(9) 0.8727(3) 0.0279(8) Uani 1 1 d . . . . .
H13 H 0.194323 0.977608 0.867091 0.034 Uiso 1 1 calc R U . . .
O3 O 0.4732(4) 1.0386(5) 0.8652(2) 0.0363(7) Uani 1 1 d . . . . .
H3 H 0.427087 1.154305 0.853237 0.054 Uiso 1 1 calc R U . . .
C14 C 0.4068(5) 0.9055(7) 0.9207(3) 0.0321(10) Uani 1 1 d . . . . .
H14A H 0.406878 0.981884 0.979680 0.038 Uiso 1 1 calc R U . . .
H14B H 0.464917 0.773121 0.937300 0.038 Uiso 1 1 calc R U . . .
C6 C 0.3890(4) 0.3403(9) 0.6486(3) 0.0302(8) Uani 1 1 d . . . . .
H6 H 0.434696 0.250608 0.699464 0.036 Uiso 1 1 calc R U . . .
C16 C 0.0327(5) 0.6367(7) 0.8947(3) 0.0276(9) Uani 1 1 d . . . . .
C7 C 0.3175(4) 0.5232(6) 0.6649(3) 0.0233(8) Uani 1 1 d . . . . .
C1 C 0.3313(5) 0.4156(8) 0.4837(3) 0.0335(10) Uani 1 1 d . . . . .
C9 C 0.1146(5) 0.9798(8) 0.5328(3) 0.0307(9) Uani 1 1 d . . . . .
H9 H 0.065257 1.105302 0.544521 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2514(4) 0.6579(7) 0.5896(3) 0.0241(8) Uani 1 1 d . . . . .
C20 C -0.2596(6) 0.5309(11) 0.8375(4) 0.0481(14) Uani 1 1 d . . . . .
H20 H -0.358891 0.493627 0.819448 0.058 Uiso 1 1 calc R U . . .
C19 C -0.1570(6) 0.3844(9) 0.8269(3) 0.0461(14) Uani 1 1 d . . . . .
H19 H -0.185714 0.247296 0.800460 0.055 Uiso 1 1 calc R U . . .
C21 C -0.2181(6) 0.7338(10) 0.8747(4) 0.0438(12) Uani 1 1 d . . . . .
H21 H -0.288843 0.836393 0.880674 0.053 Uiso 1 1 calc R U . . .
C5 C 0.3943(5) 0.2861(7) 0.5567(3) 0.0347(11) Uani 1 1 d . . . . .
H5 H 0.442153 0.158528 0.545634 0.042 Uiso 1 1 calc R U . . .
C4 C 0.1218(5) 0.9308(8) 0.4414(3) 0.0345(10) Uani 1 1 d . . . . .
H4 H 0.078202 1.024294 0.391391 0.041 Uiso 1 1 calc R U . . .
C3 C 0.1908(5) 0.7501(8) 0.4235(3) 0.0326(10) Uani 1 1 d . . . . .
H3A H 0.193879 0.718829 0.360937 0.039 Uiso 1 1 calc R U . . .
C2 C 0.2581(5) 0.6076(7) 0.4963(3) 0.0281(9) Uani 1 1 d . . . . .
C18 C -0.0722(5) 0.7848(8) 0.9030(3) 0.0341(10) Uani 1 1 d . . . . .
H18 H -0.043879 0.923092 0.928290 0.041 Uiso 1 1 calc R U . . .
C15 C 0.1900(5) 0.6874(8) 0.9331(3) 0.0342(10) Uani 1 1 d . . . . .
H15A H 0.245425 0.551463 0.939920 0.041 Uiso 1 1 calc R U . . .
H15B H 0.203189 0.750387 0.996386 0.041 Uiso 1 1 calc R U . . .
C17 C -0.0110(6) 0.4369(8) 0.8550(3) 0.0372(11) Uani 1 1 d . . . . .
H17 H 0.059279 0.335648 0.846960 0.045 Uiso 1 1 calc R U . . .
C12 C 0.3142(4) 0.5796(7) 0.7621(3) 0.0246(8) Uani 1 1 d . . . . .
C11 C 0.1740(5) 0.9058(7) 0.7025(3) 0.0269(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 C1 1.896(5) . ?
O2 C11 1.214(5) . ?
N1 C13 1.483(5) . ?
N1 C12 1.394(5) . ?
N1 C11 1.410(5) . ?
O1 C12 1.225(5) . ?
C10 C9 1.382(6) . ?
C10 C8 1.409(6) . ?
C10 C11 1.484(6) . ?
C13 H13 1.0000 . ?
C13 C14 1.518(6) . ?
C13 C15 1.535(6) . ?
O3 H3 0.8400 . ?
O3 C14 1.420(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C7 1.378(6) . ?
C6 C5 1.409(6) . ?
C16 C18 1.390(6) . ?
C16 C15 1.505(7) . ?
C16 C17 1.393(7) . ?
C7 C8 1.410(6) . ?
C7 C12 1.483(6) . ?
C1 C5 1.360(7) . ?
C1 C2 1.420(7) . ?
C9 H9 0.9500 . ?
C9 C4 1.399(7) . ?
C8 C2 1.427(6) . ?
C20 H20 0.9500 . ?
C20 C19 1.376(9) . ?
C20 C21 1.394(9) . ?
C19 H19 0.9500 . ?
C19 C17 1.394(8) . ?
C21 H21 0.9500 . ?
C21 C18 1.391(7) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.362(7) . ?
C3 H3A 0.9500 . ?
C3 C2 1.417(7) . ?
C18 H18 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C13 119.1(3) . . ?
C12 N1 C11 123.6(3) . . ?
C11 N1 C13 116.8(3) . . ?
C9 C10 C8 120.7(4) . . ?
C9 C10 C11 118.9(4) . . ?
C8 C10 C11 120.4(4) . . ?
N1 C13 H13 106.5 . . ?
N1 C13 C14 110.9(3) . . ?
N1 C13 C15 114.5(4) . . ?
C14 C13 H13 106.5 . . ?
C14 C13 C15 111.4(3) . . ?
C15 C13 H13 106.5 . . ?
C14 O3 H3 109.5 . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
O3 C14 C13 113.7(4) . . ?
O3 C14 H14A 108.8 . . ?
O3 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C7 C6 H6 119.9 . . ?
C7 C6 C5 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
C18 C16 C15 120.3(4) . . ?
C18 C16 C17 118.7(5) . . ?
C17 C16 C15 120.9(4) . . ?
C6 C7 C8 119.9(4) . . ?
C6 C7 C12 119.6(4) . . ?
C8 C7 C12 120.5(4) . . ?
C5 C1 Br1 118.5(4) . . ?
C5 C1 C2 122.1(4) . . ?
C2 C1 Br1 119.3(4) . . ?
C10 C9 H9 120.0 . . ?
C10 C9 C4 120.1(4) . . ?
C4 C9 H9 120.0 . . ?
C10 C8 C7 120.2(4) . . ?
C10 C8 C2 119.2(4) . . ?
C7 C8 C2 120.7(4) . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(5) . . ?
C21 C20 H20 119.9 . . ?
C20 C19 H19 119.9 . . ?
C20 C19 C17 120.1(5) . . ?
C17 C19 H19 119.9 . . ?
C20 C21 H21 120.3 . . ?
C18 C21 C20 119.4(5) . . ?
C18 C21 H21 120.3 . . ?
C6 C5 H5 119.9 . . ?
C1 C5 C6 120.3(4) . . ?
C1 C5 H5 119.9 . . ?
C9 C4 H4 119.8 . . ?
C3 C4 C9 120.5(4) . . ?
C3 C4 H4 119.8 . . ?
C4 C3 H3A 119.3 . . ?
C4 C3 C2 121.4(4) . . ?
C2 C3 H3A 119.3 . . ?
C1 C2 C8 116.8(4) . . ?
C3 C2 C1 125.0(4) . . ?
C3 C2 C8 118.1(4) . . ?
C16 C18 C21 121.0(5) . . ?
C16 C18 H18 119.5 . . ?
C21 C18 H18 119.5 . . ?
C13 C15 H15A 108.7 . . ?
C13 C15 H15B 108.7 . . ?
C16 C15 C13 114.4(4) . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C16 C17 C19 120.5(5) . . ?
C16 C17 H17 119.7 . . ?
C19 C17 H17 119.7 . . ?
N1 C12 C7 117.8(3) . . ?
O1 C12 N1 120.3(4) . . ?
O1 C12 C7 121.9(4) . . ?
O2 C11 N1 120.8(4) . . ?
O2 C11 C10 121.7(4) . . ?
N1 C11 C10 117.5(4) . . ?

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 C1 C5 C6 -178.7(3) . . . . ?
Br1 C1 C2 C8 177.5(3) . . . . ?
Br1 C1 C2 C3 -1.9(6) . . . . ?
N1 C13 C14 O3 47.3(5) . . . . ?
N1 C13 C15 C16 -59.2(5) . . . . ?
C10 C9 C4 C3 0.8(7) . . . . ?
C10 C8 C2 C1 -179.6(4) . . . . ?
C10 C8 C2 C3 -0.2(6) . . . . ?
C13 N1 C12 O1 6.1(6) . . . . ?
C13 N1 C12 C7 -172.2(3) . . . . ?
C13 N1 C11 O2 -7.0(6) . . . . ?
C13 N1 C11 C10 172.2(4) . . . . ?
C14 C13 C15 C16 173.8(4) . . . . ?
C6 C7 C8 C10 -179.5(4) . . . . ?
C6 C7 C8 C2 -0.3(6) . . . . ?
C6 C7 C12 N1 179.2(4) . . . . ?
C6 C7 C12 O1 0.9(6) . . . . ?
C7 C6 C5 C1 1.1(7) . . . . ?
C7 C8 C2 C1 1.2(6) . . . . ?
C7 C8 C2 C3 -179.4(4) . . . . ?
C9 C10 C8 C7 179.7(4) . . . . ?
C9 C10 C8 C2 0.5(6) . . . . ?
C9 C10 C11 O2 -0.1(7) . . . . ?
C9 C10 C11 N1 -179.3(4) . . . . ?
C9 C4 C3 C2 -0.5(7) . . . . ?
C8 C10 C9 C4 -0.8(6) . . . . ?
C8 C10 C11 O2 178.7(4) . . . . ?
C8 C10 C11 N1 -0.5(6) . . . . ?
C8 C7 C12 N1 0.8(5) . . . . ?
C8 C7 C12 O1 -177.6(4) . . . . ?
C20 C19 C17 C16 0.6(7) . . . . ?
C20 C21 C18 C16 0.0(7) . . . . ?
C19 C20 C21 C18 -1.5(7) . . . . ?
C21 C20 C19 C17 1.2(7) . . . . ?
C5 C6 C7 C8 -0.9(6) . . . . ?
C5 C6 C7 C12 -179.3(4) . . . . ?
C5 C1 C2 C8 -1.0(6) . . . . ?
C5 C1 C2 C3 179.7(4) . . . . ?
C4 C3 C2 C1 179.6(4) . . . . ?
C4 C3 C2 C8 0.2(6) . . . . ?
C2 C1 C5 C6 -0.2(7) . . . . ?
C18 C16 C15 C13 -76.7(5) . . . . ?
C18 C16 C17 C19 -2.1(7) . . . . ?
C15 C13 C14 O3 176.2(4) . . . . ?
C15 C16 C18 C21 -174.8(4) . . . . ?
C15 C16 C17 C19 174.4(4) . . . . ?
C17 C16 C18 C21 1.8(7) . . . . ?
C17 C16 C15 C13 106.8(5) . . . . ?
C12 N1 C13 C14 64.8(5) . . . . ?
C12 N1 C13 C15 -62.4(5) . . . . ?
C12 N1 C11 O2 -179.0(4) . . . . ?
C12 N1 C11 C10 0.2(6) . . . . ?
C12 C7 C8 C10 -1.1(6) . . . . ?
C12 C7 C8 C2 178.1(4) . . . . ?
C11 N1 C13 C14 -107.6(5) . . . . ?
C11 N1 C13 C15 125.2(4) . . . . ?
C11 N1 C12 O1 178.0(4) . . . . ?
C11 N1 C12 C7 -0.4(6) . . . . ?
C11 C10 C9 C4 178.0(4) . . . . ?
C11 C10 C8 C7 0.9(6) . . . . ?
C11 C10 C8 C2 -178.3(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 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.520
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2309600'
loop_
_audit_author_name
_audit_author_address
'Zhuoer Wang'
;Shandong University
China
;
_audit_update_record             
;
2023-11-22 deposited with the CCDC.	2024-04-05 downloaded from the CCDC.
;
_audit_creation_date             2023-05-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C11 H10 Br N O3)'
_chemical_formula_sum            'C22 H20 Br2 N2 O6'
_chemical_formula_weight         568.22
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.6432(6)
_cell_length_b                   5.5418(3)
_cell_length_c                   22.9285(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.000(6)
_cell_angle_gamma                90
_cell_volume                     1084.73(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4203
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      30.1450
_cell_measurement_theta_min      2.6620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.780
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16523
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.407
_diffrn_reflns_theta_min         2.678
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.781
_reflns_number_gt                3859
_reflns_number_total             5412
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 1373 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5412
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.009
_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)+(0.0126P)²+0.3131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0827
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00G), C00T(H00T)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00D,H00E), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00F), C00L(H00L), C00N(H00N), C00S(H00S), C00U(H00U)
2.d Idealised Me refined as rotating group:
 C006(H00A,H00B,H00C), C00R(H00I,H00J,H00K)
2.e Idealised tetrahedral OH refined as rotating group:
 O00E(H00H), O00Q(H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.61915(8) 0.67911(10) 0.85740(3) 0.0360(2) Uani 1 1 d . . . . .
Br02 Br 0.38049(8) 0.31025(9) 0.63929(3) 0.0372(2) Uani 1 1 d . . . . .
O003 O 0.9390(5) 1.4077(10) 0.6550(2) 0.0340(13) Uani 1 1 d . . . . .
O004 O 0.3760(5) 0.2823(10) 0.89454(18) 0.0339(11) Uani 1 1 d . . . . .
N005 N 0.2142(6) -0.0522(10) 0.8868(2) 0.0197(11) Uani 1 1 d . . . . .
C006 C 0.8773(8) 0.9013(13) 0.5246(3) 0.0359(17) Uani 1 1 d . . . . .
H00A H 0.804022 0.766574 0.525054 0.054 Uiso 1 1 calc R U . . .
H00B H 0.979086 0.857328 0.547291 0.054 Uiso 1 1 calc R U . . .
H00C H 0.889787 0.937504 0.483796 0.054 Uiso 1 1 calc R U . . .
C007 C 0.8598(7) 1.2333(12) 0.6604(3) 0.0243(16) Uani 1 1 d . . . . .
C008 C 0.6631(7) 0.7868(15) 0.7402(2) 0.0280(15) Uani 1 1 d . . . . .
H008 H 0.599974 0.648998 0.728985 0.034 Uiso 1 1 calc R U . . .
O009 O 0.6259(5) 0.7503(8) 0.60349(18) 0.0272(10) Uani 1 1 d . . . . .
O00A O 0.0757(5) -0.3922(8) 0.84975(19) 0.0301(12) Uani 1 1 d . . . . .
C00B C 0.2219(7) -0.0775(13) 0.6858(3) 0.0273(16) Uani 1 1 d . . . . .
H00F H 0.200704 -0.130528 0.645932 0.033 Uiso 1 1 calc R U . . .
C00C C 0.1892(8) -0.0780(12) 0.9487(3) 0.0222(14) Uani 1 1 d . . . . .
H00G H 0.099045 -0.190924 0.948973 0.027 Uiso 1 1 calc R U . . .
C00D C 0.6984(7) 0.8599(12) 0.7988(3) 0.0251(17) Uani 1 1 d . . . . .
O00E O 0.0104(4) 0.2644(7) 0.93854(17) 0.0337(9) Uani 1 1 d . . . . .
H00H H 0.039415 0.360150 0.913981 0.051 Uiso 1 1 calc R U . . .
C00F C 0.2878(7) 0.0815(11) 0.8007(3) 0.0195(14) Uani 1 1 d . . . . .
C00G C 0.1990(7) -0.1230(12) 0.7866(3) 0.0219(15) Uani 1 1 d . . . . .
C00H C 0.7053(7) 0.8979(12) 0.6339(3) 0.0221(15) Uani 1 1 d . . . . .
C00I C 0.3032(7) 0.1259(13) 0.8656(3) 0.0236(15) Uani 1 1 d . . . . .
C00J C 0.8151(7) 1.1289(12) 0.7151(3) 0.0224(14) Uani 1 1 d . . . . .
C00K C 0.6596(7) 1.2119(14) 0.5184(3) 0.0298(16) Uani 1 1 d . . . . .
H00D H 0.581119 1.080434 0.514022 0.036 Uiso 1 1 calc R U . . .
H00E H 0.618830 1.347565 0.539594 0.036 Uiso 1 1 calc R U . . .
C00L C 0.1643(7) -0.2091(15) 0.7300(2) 0.0261(14) Uani 1 1 d . . . . .
H00L H 0.104026 -0.351497 0.721082 0.031 Uiso 1 1 calc R U . . .
N00M N 0.7946(6) 1.0803(9) 0.6144(2) 0.0219(12) Uani 1 1 d . . . . .
C00N C 0.8477(7) 1.2025(15) 0.7734(3) 0.0277(15) Uani 1 1 d . . . . .
H00N H 0.908611 1.342838 0.784204 0.033 Uiso 1 1 calc R U . . .
C00O C 0.7239(7) 0.9238(13) 0.6993(3) 0.0242(15) Uani 1 1 d . . . . .
C00P C 0.3086(7) 0.1270(13) 0.6998(3) 0.0250(16) Uani 1 1 d . . . . .
O00Q O 0.6883(4) 1.2891(9) 0.46203(16) 0.0392(10) Uani 1 1 d . . . . .
H00Q H 0.602964 1.299226 0.438918 0.059 Uiso 1 1 calc R U . . .
C00R C 0.3317(7) -0.1919(16) 0.9868(3) 0.0347(16) Uani 1 1 d . . . . .
H00I H 0.356272 -0.345940 0.969339 0.052 Uiso 1 1 calc R U . . .
H00J H 0.308436 -0.219717 1.026714 0.052 Uiso 1 1 calc R U . . .
H00K H 0.421645 -0.082950 0.988644 0.052 Uiso 1 1 calc R U . . .
C00S C 0.7892(7) 1.0661(13) 0.8154(3) 0.0280(16) Uani 1 1 d . . . . .
H00S H 0.810506 1.112123 0.855731 0.034 Uiso 1 1 calc R U . . .
C00T C 0.8134(7) 1.1232(12) 0.5523(2) 0.0231(14) Uani 1 1 d . . . . .
H00T H 0.891789 1.255738 0.552070 0.028 Uiso 1 1 calc R U . . .
C00U C 0.3445(7) 0.2151(12) 0.7577(2) 0.0246(15) Uani 1 1 d . . . . .
H00U H 0.404171 0.357914 0.766828 0.029 Uiso 1 1 calc R U . . .
C00V C 0.1512(7) -0.2116(15) 0.8425(3) 0.0229(14) Uani 1 1 d . . . . .
C5 C 0.1442(7) 0.1599(13) 0.9736(2) 0.0289(14) Uani 1 1 d . . . . .
H5A H 0.121993 0.134286 1.014174 0.035 Uiso 1 1 calc R U . . .
H5B H 0.233491 0.273238 0.975774 0.035 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
Br01 C00D 1.888(6) . ?
Br02 C00P 1.900(6) . ?
O003 C007 1.202(8) . ?
O004 C00I 1.208(7) . ?
N005 C00C 1.477(7) . ?
N005 C00I 1.385(8) . ?
N005 C00V 1.390(8) . ?
C006 H00A 0.9800 . ?
C006 H00B 0.9800 . ?
C006 H00C 0.9800 . ?
C006 C00T 1.526(9) . ?
C007 C00J 1.487(9) . ?
C007 N00M 1.400(8) . ?
C008 H008 0.9500 . ?
C008 C00D 1.392(8) . ?
C008 C00O 1.373(9) . ?
O009 C00H 1.215(7) . ?
O00A C00V 1.220(9) . ?
C00B H00F 0.9500 . ?
C00B C00L 1.401(9) . ?
C00B C00P 1.369(9) . ?
C00C H00G 1.0000 . ?
C00C C00R 1.530(8) . ?
C00C C5 1.511(9) . ?
C00D C00S 1.404(9) . ?
O00E H00H 0.8400 . ?
O00E C5 1.424(7) . ?
C00F C00G 1.378(8) . ?
C00F C00I 1.493(8) . ?
C00F C00U 1.383(8) . ?
C00G C00L 1.373(8) . ?
C00G C00V 1.490(8) . ?
C00H N00M 1.388(8) . ?
C00H C00O 1.490(8) . ?
C00J C00N 1.383(8) . ?
C00J C00O 1.398(9) . ?
C00K H00D 0.9900 . ?
C00K H00E 0.9900 . ?
C00K O00Q 1.418(7) . ?
C00K C00T 1.513(8) . ?
C00L H00L 0.9500 . ?
N00M C00T 1.478(7) . ?
C00N H00N 0.9500 . ?
C00N C00S 1.380(9) . ?
C00P C00U 1.404(8) . ?
O00Q H00Q 0.8400 . ?
C00R H00I 0.9800 . ?
C00R H00J 0.9800 . ?
C00R H00K 0.9800 . ?
C00S H00S 0.9500 . ?
C00T H00T 1.0000 . ?
C00U H00U 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

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
C00I N005 C00C 125.4(5) . . ?
C00I N005 C00V 111.8(5) . . ?
C00V N005 C00C 122.8(5) . . ?
H00A C006 H00B 109.5 . . ?
H00A C006 H00C 109.5 . . ?
H00B C006 H00C 109.5 . . ?
C00T C006 H00A 109.5 . . ?
C00T C006 H00B 109.5 . . ?
C00T C006 H00C 109.5 . . ?
O003 C007 C00J 128.8(6) . . ?
O003 C007 N00M 125.4(7) . . ?
N00M C007 C00J 105.8(6) . . ?
C00D C008 H008 121.7 . . ?
C00O C008 H008 121.7 . . ?
C00O C008 C00D 116.6(7) . . ?
C00L C00B H00F 119.8 . . ?
C00P C00B H00F 119.8 . . ?
C00P C00B C00L 120.3(6) . . ?
N005 C00C H00G 107.3 . . ?
N005 C00C C00R 111.3(5) . . ?
N005 C00C C5 111.3(5) . . ?
C00R C00C H00G 107.3 . . ?
C5 C00C H00G 107.3 . . ?
C5 C00C C00R 112.1(5) . . ?
C008 C00D Br01 118.9(5) . . ?
C008 C00D C00S 121.8(6) . . ?
C00S C00D Br01 119.3(5) . . ?
C5 O00E H00H 109.5 . . ?
C00G C00F C00I 109.2(6) . . ?
C00G C00F C00U 121.3(6) . . ?
C00U C00F C00I 129.5(6) . . ?
C00F C00G C00V 106.8(6) . . ?
C00L C00G C00F 122.6(7) . . ?
C00L C00G C00V 130.6(7) . . ?
O009 C00H N00M 126.7(6) . . ?
O009 C00H C00O 127.3(6) . . ?
N00M C00H C00O 106.0(5) . . ?
O004 C00I N005 126.1(6) . . ?
O004 C00I C00F 128.6(6) . . ?
N005 C00I C00F 105.3(5) . . ?
C00N C00J C007 131.3(6) . . ?
C00N C00J C00O 120.8(6) . . ?
C00O C00J C007 107.9(5) . . ?
H00D C00K H00E 108.5 . . ?
O00Q C00K H00D 110.2 . . ?
O00Q C00K H00E 110.2 . . ?
O00Q C00K C00T 107.6(5) . . ?
C00T C00K H00D 110.2 . . ?
C00T C00K H00E 110.2 . . ?
C00B C00L H00L 121.5 . . ?
C00G C00L C00B 117.0(7) . . ?
C00G C00L H00L 121.5 . . ?
C007 N00M C00T 122.4(6) . . ?
C00H N00M C007 112.2(5) . . ?
C00H N00M C00T 125.3(5) . . ?
C00J C00N H00N 121.0 . . ?
C00S C00N C00J 118.1(7) . . ?
C00S C00N H00N 121.0 . . ?
C008 C00O C00H 129.8(6) . . ?
C008 C00O C00J 122.2(6) . . ?
C00J C00O C00H 107.9(6) . . ?
C00B C00P Br02 120.1(5) . . ?
C00B C00P C00U 122.8(6) . . ?
C00U C00P Br02 117.1(5) . . ?
C00K O00Q H00Q 109.5 . . ?
C00C C00R H00I 109.5 . . ?
C00C C00R H00J 109.5 . . ?
C00C C00R H00K 109.5 . . ?
H00I C00R H00J 109.5 . . ?
H00I C00R H00K 109.5 . . ?
H00J C00R H00K 109.5 . . ?
C00D C00S H00S 119.7 . . ?
C00N C00S C00D 120.5(6) . . ?
C00N C00S H00S 119.7 . . ?
C006 C00T H00T 107.5 . . ?
C00K C00T C006 113.2(5) . . ?
C00K C00T H00T 107.5 . . ?
N00M C00T C006 111.9(5) . . ?
N00M C00T C00K 109.1(5) . . ?
N00M C00T H00T 107.5 . . ?
C00F C00U C00P 116.0(6) . . ?
C00F C00U H00U 122.0 . . ?
C00P C00U H00U 122.0 . . ?
N005 C00V C00G 106.8(6) . . ?
O00A C00V N005 125.4(6) . . ?
O00A C00V C00G 127.8(6) . . ?
C00C C5 H5A 109.2 . . ?
C00C C5 H5B 109.2 . . ?
O00E C5 C00C 112.1(5) . . ?
O00E C5 H5A 109.2 . . ?
O00E C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br01 C00D C00S C00N -179.5(5) . . . . ?
Br02 C00P C00U C00F 178.5(4) . . . . ?
O003 C007 C00J C00N 1.5(12) . . . . ?
O003 C007 C00J C00O -179.1(7) . . . . ?
O003 C007 N00M C00H -178.3(6) . . . . ?
O003 C007 N00M C00T -1.8(10) . . . . ?
N005 C00C C5 O00E 55.4(7) . . . . ?
C007 C00J C00N C00S -179.9(6) . . . . ?
C007 C00J C00O C008 -179.5(6) . . . . ?
C007 C00J C00O C00H -1.5(7) . . . . ?
C007 N00M C00T C006 127.0(6) . . . . ?
C007 N00M C00T C00K -106.9(7) . . . . ?
C008 C00D C00S C00N -0.6(10) . . . . ?
O009 C00H N00M C007 174.2(6) . . . . ?
O009 C00H N00M C00T -2.2(10) . . . . ?
O009 C00H C00O C008 2.7(12) . . . . ?
O009 C00H C00O C00J -175.1(6) . . . . ?
C00B C00P C00U C00F 0.4(9) . . . . ?
C00C N005 C00I O004 1.8(10) . . . . ?
C00C N005 C00I C00F -177.9(6) . . . . ?
C00C N005 C00V O00A -3.3(10) . . . . ?
C00C N005 C00V C00G 178.8(5) . . . . ?
C00D C008 C00O C00H -178.4(6) . . . . ?
C00D C008 C00O C00J -0.9(10) . . . . ?
C00F C00G C00L C00B -0.8(10) . . . . ?
C00F C00G C00V N005 0.3(7) . . . . ?
C00F C00G C00V O00A -177.6(6) . . . . ?
C00G C00F C00I O004 177.4(6) . . . . ?
C00G C00F C00I N005 -2.9(7) . . . . ?
C00G C00F C00U C00P -1.2(9) . . . . ?
C00H N00M C00T C006 -57.0(8) . . . . ?
C00H N00M C00T C00K 69.1(8) . . . . ?
C00I N005 C00C C00R -78.0(8) . . . . ?
C00I N005 C00C C5 47.8(8) . . . . ?
C00I N005 C00V O00A 175.7(6) . . . . ?
C00I N005 C00V C00G -2.3(7) . . . . ?
C00I C00F C00G C00L 179.8(6) . . . . ?
C00I C00F C00G C00V 1.6(7) . . . . ?
C00I C00F C00U C00P -179.3(6) . . . . ?
C00J C007 N00M C00H 3.6(7) . . . . ?
C00J C007 N00M C00T -179.9(5) . . . . ?
C00J C00N C00S C00D -0.4(10) . . . . ?
C00L C00B C00P Br02 -177.9(5) . . . . ?
C00L C00B C00P C00U 0.1(10) . . . . ?
C00L C00G C00V N005 -177.8(6) . . . . ?
C00L C00G C00V O00A 4.4(12) . . . . ?
N00M C007 C00J C00N 179.5(7) . . . . ?
N00M C007 C00J C00O -1.1(7) . . . . ?
N00M C00H C00O C008 -178.6(7) . . . . ?
N00M C00H C00O C00J 3.7(7) . . . . ?
C00N C00J C00O C008 0.0(10) . . . . ?
C00N C00J C00O C00H 177.9(6) . . . . ?
C00O C008 C00D Br01 -179.8(5) . . . . ?
C00O C008 C00D C00S 1.2(10) . . . . ?
C00O C00H N00M C007 -4.5(7) . . . . ?
C00O C00H N00M C00T 179.1(6) . . . . ?
C00O C00J C00N C00S 0.7(10) . . . . ?
C00P C00B C00L C00G 0.0(10) . . . . ?
O00Q C00K C00T C006 -64.3(7) . . . . ?
O00Q C00K C00T N00M 170.4(5) . . . . ?
C00R C00C C5 O00E -179.3(5) . . . . ?
C00U C00F C00G C00L 1.4(9) . . . . ?
C00U C00F C00G C00V -176.9(6) . . . . ?
C00U C00F C00I O004 -4.3(11) . . . . ?
C00U C00F C00I N005 175.4(6) . . . . ?
C00V N005 C00C C00R 100.8(7) . . . . ?
C00V N005 C00C C5 -133.4(6) . . . . ?
C00V N005 C00I O004 -177.1(6) . . . . ?
C00V N005 C00I C00F 3.2(7) . . . . ?
C00V C00G C00L C00B 177.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_c32_auto
_database_code_depnum_ccdc_archive 'CCDC 2309602'
loop_
_audit_author_name
_audit_author_address
'Zhuoer Wang'
;Shandong University
China
;
_audit_update_record             
;
2023-11-22 deposited with the CCDC.	2024-04-05 downloaded from the CCDC.
;
_audit_creation_date             2023-11-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 Br0.969 N O3'
_chemical_formula_sum            'C15 H11 Br0.97 N O3'
_chemical_formula_weight         330.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3573(4)
_cell_length_b                   8.0361(6)
_cell_length_c                   21.7154(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.798(6)
_cell_angle_gamma                90
_cell_volume                     1281.08(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2923
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      29.8790
_cell_measurement_theta_min      2.8010
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    3.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
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    1.715
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9663
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.325
_diffrn_reflns_theta_min         2.775
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  30.00   1.00    2.80    --   -7.76 -99.00 -30.00   53
  2  ω    -11.00  14.00   1.00    2.80    --   -7.76-102.00-130.00   25
  3  ω     -7.00  18.00   1.00    2.80    --    8.78-102.00-130.00   25
  4  ω    -22.00  46.00   1.00    2.80    --    8.78 -99.00-180.00   68
  5  ω    -26.00  66.00   1.00    2.80    --   -7.76  57.00 -90.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0090307000
_diffrn_orient_matrix_UB_12      -0.0161129000
_diffrn_orient_matrix_UB_13      -0.0321675000
_diffrn_orient_matrix_UB_21      -0.0306926000
_diffrn_orient_matrix_UB_22      0.0826755000
_diffrn_orient_matrix_UB_23      -0.0054228000
_diffrn_orient_matrix_UB_31      0.0912102000
_diffrn_orient_matrix_UB_32      0.0262188000
_diffrn_orient_matrix_UB_33      -0.0027475000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2358
_reflns_number_total             3148
_reflns_odcompleteness_completeness 98.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.171
_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)+2.8422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1114
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C15(H15), C8(H8), C14(H14)
2.c Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br5 Br 0.88613(6) 0.82330(6) 0.40054(2) 0.02664(16) Uani 0.861(3) 1 d . . . A 2
O21 O 0.5833(4) 0.0836(4) 0.59275(13) 0.0323(7) Uani 1 1 d . . . . .
O20 O 0.6837(4) 0.5753(4) 0.69099(13) 0.0349(7) Uani 1 1 d . . . . .
O19 O 0.8458(5) 0.4094(4) 0.79506(13) 0.0432(9) Uani 1 1 d . . . . .
H19 H 0.777438 0.476118 0.774727 0.065 Uiso 1 1 calc R U . . .
N12 N 0.6317(4) 0.3286(4) 0.64233(14) 0.0239(7) Uani 1 1 d . . . . .
C10 C 0.6712(5) 0.3079(5) 0.53082(17) 0.0218(8) Uani 1 1 d . . . . .
C1 C 0.7368(5) 0.5704(5) 0.58506(18) 0.0223(8) Uani 1 1 d . . . . .
C13 C 0.6831(5) 0.4962(5) 0.64356(18) 0.0252(9) Uani 1 1 d . . . . .
C3 C 0.7741(5) 0.5465(5) 0.47301(19) 0.0261(9) Uani 1 1 d . . . . .
C2 C 0.7279(5) 0.4746(5) 0.53017(18) 0.0241(9) Uani 1 1 d . . . . .
C11 C 0.6268(5) 0.2287(5) 0.58943(18) 0.0246(9) Uani 1 1 d . . . . .
C9 C 0.6585(5) 0.2163(5) 0.47707(18) 0.0282(9) Uani 1 1 d . . . . .
H9 H 0.618712 0.103907 0.477994 0.034 Uiso 1 1 calc R U . . .
C4 C 0.8291(5) 0.7166(5) 0.47520(19) 0.0280(9) Uani 1 1 d . . . . .
C15 C 0.7921(5) 0.7332(5) 0.5842(2) 0.0305(10) Uani 1 1 d . . . . .
H15 H 0.798976 0.796984 0.621142 0.037 Uiso 1 1 calc R U . . .
C8 C 0.7033(5) 0.2863(6) 0.42141(19) 0.0333(10) Uani 1 1 d . . . . .
H8 H 0.693504 0.221385 0.384779 0.040 Uiso 1 1 calc R U . . .
C7 C 0.7612(5) 0.4478(6) 0.41905(18) 0.0294(10) Uani 1 1 d . . . . .
C14 C 0.8387(5) 0.8052(6) 0.5283(2) 0.0320(10) Uani 1 1 d . . . . .
H14 H 0.877549 0.917859 0.527830 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5805(5) 0.2512(5) 0.70012(18) 0.0280(9) Uani 1 1 d . . . . .
H16A H 0.482829 0.168705 0.690436 0.034 Uiso 1 1 calc R U . . .
H16B H 0.530972 0.337893 0.726737 0.034 Uiso 1 1 calc R U . . .
C17 C 0.7398(6) 0.1648(6) 0.73562(19) 0.0361(10) Uani 1 1 d . . . . .
H17A H 0.694150 0.111320 0.772647 0.043 Uiso 1 1 calc R U . . .
H17B H 0.785629 0.075604 0.709305 0.043 Uiso 1 1 calc R U . . .
C18 C 0.8965(6) 0.2766(6) 0.7558(2) 0.0378(11) Uani 1 1 d . . . . .
H18A H 0.992601 0.209248 0.777988 0.045 Uiso 1 1 calc R U . . .
H18B H 0.948414 0.324360 0.718806 0.045 Uiso 1 1 calc R U . . .
Br1 Br 0.8423(5) 0.6097(7) 0.36132(18) 0.0420(17) Uani 0.1079(19) 1 d . . . B 1


_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
Br5 C4 1.905(4) . ?
O21 C11 1.213(5) . ?
O20 C13 1.210(5) . ?
O19 H19 0.8400 . ?
O19 C18 1.431(5) . ?
N12 C13 1.399(5) . ?
N12 C11 1.400(5) . ?
N12 C16 1.472(5) . ?
C10 C2 1.403(6) . ?
C10 C11 1.479(5) . ?
C10 C9 1.378(5) . ?
C1 C13 1.481(5) . ?
C1 C2 1.417(5) . ?
C1 C15 1.370(6) . ?
C3 C2 1.431(5) . ?
C3 C4 1.425(6) . ?
C3 C7 1.413(6) . ?
C9 H9 0.9500 . ?
C9 C8 1.392(6) . ?
C4 C14 1.352(6) . ?
C15 H15 0.9500 . ?
C15 C14 1.408(6) . ?
C8 H8 0.9500 . ?
C8 C7 1.368(6) . ?
C7 Br1 1.929(6) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.526(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.504(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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
C18 O19 H19 109.5 . . ?
C13 N12 C11 124.1(3) . . ?
C13 N12 C16 118.4(3) . . ?
C11 N12 C16 117.6(3) . . ?
C2 C10 C11 120.1(4) . . ?
C9 C10 C2 120.3(4) . . ?
C9 C10 C11 119.5(4) . . ?
C2 C1 C13 120.2(4) . . ?
C15 C1 C13 119.5(4) . . ?
C15 C1 C2 120.4(4) . . ?
O20 C13 N12 120.5(4) . . ?
O20 C13 C1 122.2(4) . . ?
N12 C13 C1 117.3(3) . . ?
C4 C3 C2 116.2(4) . . ?
C7 C3 C2 119.0(4) . . ?
C7 C3 C4 124.7(4) . . ?
C10 C2 C1 120.5(4) . . ?
C10 C2 C3 118.9(4) . . ?
C1 C2 C3 120.6(4) . . ?
O21 C11 N12 119.7(4) . . ?
O21 C11 C10 122.6(4) . . ?
N12 C11 C10 117.7(4) . . ?
C10 C9 H9 119.6 . . ?
C10 C9 C8 120.9(4) . . ?
C8 C9 H9 119.6 . . ?
C3 C4 Br5 118.8(3) . . ?
C14 C4 Br5 119.1(3) . . ?
C14 C4 C3 122.1(4) . . ?
C1 C15 H15 120.2 . . ?
C1 C15 C14 119.5(4) . . ?
C14 C15 H15 120.2 . . ?
C9 C8 H8 119.7 . . ?
C7 C8 C9 120.5(4) . . ?
C7 C8 H8 119.7 . . ?
C3 C7 Br1 98.8(3) . . ?
C8 C7 C3 120.4(4) . . ?
C8 C7 Br1 140.8(4) . . ?
C4 C14 C15 121.2(4) . . ?
C4 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
N12 C16 H16A 109.0 . . ?
N12 C16 H16B 109.0 . . ?
N12 C16 C17 113.1(3) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C16 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C18 C17 C16 115.1(4) . . ?
C18 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
O19 C18 C17 113.2(4) . . ?
O19 C18 H18A 108.9 . . ?
O19 C18 H18B 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?

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
Br5 C4 C14 C15 177.9(3) . . . . ?
N12 C16 C17 C18 61.0(5) . . . . ?
C10 C9 C8 C7 0.1(6) . . . . ?
C1 C15 C14 C4 0.3(6) . . . . ?
C13 N12 C11 O21 178.8(3) . . . . ?
C13 N12 C11 C10 -2.8(5) . . . . ?
C13 N12 C16 C17 -93.1(4) . . . . ?
C13 C1 C2 C10 -1.1(5) . . . . ?
C13 C1 C2 C3 178.1(3) . . . . ?
C13 C1 C15 C14 -178.3(3) . . . . ?
C3 C4 C14 C15 -0.8(6) . . . . ?
C2 C10 C11 O21 -177.4(4) . . . . ?
C2 C10 C11 N12 4.2(5) . . . . ?
C2 C10 C9 C8 0.7(6) . . . . ?
C2 C1 C13 O20 -177.8(4) . . . . ?
C2 C1 C13 N12 2.5(5) . . . . ?
C2 C1 C15 C14 0.5(6) . . . . ?
C2 C3 C4 Br5 -178.2(3) . . . . ?
C2 C3 C4 C14 0.5(5) . . . . ?
C2 C3 C7 C8 0.7(6) . . . . ?
C2 C3 C7 Br1 -179.1(3) . . . . ?
C11 N12 C13 O20 179.8(3) . . . . ?
C11 N12 C13 C1 -0.5(5) . . . . ?
C11 N12 C16 C17 86.4(4) . . . . ?
C11 C10 C2 C1 -2.3(5) . . . . ?
C11 C10 C2 C3 178.5(3) . . . . ?
C11 C10 C9 C8 -178.6(3) . . . . ?
C9 C10 C2 C1 178.4(3) . . . . ?
C9 C10 C2 C3 -0.8(5) . . . . ?
C9 C10 C11 O21 1.9(6) . . . . ?
C9 C10 C11 N12 -176.5(3) . . . . ?
C9 C8 C7 C3 -0.8(6) . . . . ?
C9 C8 C7 Br1 179.0(4) . . . . ?
C4 C3 C2 C10 179.5(3) . . . . ?
C4 C3 C2 C1 0.3(5) . . . . ?
C4 C3 C7 C8 -178.6(4) . . . . ?
C4 C3 C7 Br1 1.5(4) . . . . ?
C15 C1 C13 O20 1.1(6) . . . . ?
C15 C1 C13 N12 -178.6(3) . . . . ?
C15 C1 C2 C10 -180.0(3) . . . . ?
C15 C1 C2 C3 -0.8(5) . . . . ?
C7 C3 C2 C10 0.0(5) . . . . ?
C7 C3 C2 C1 -179.1(3) . . . . ?
C7 C3 C4 Br5 1.1(5) . . . . ?
C7 C3 C4 C14 179.9(4) . . . . ?
C16 N12 C13 O20 -0.7(5) . . . . ?
C16 N12 C13 C1 179.0(3) . . . . ?
C16 N12 C11 O21 -0.8(5) . . . . ?
C16 N12 C11 C10 177.7(3) . . . . ?
C16 C17 C18 O19 59.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.566
####################################################################### 
# 
# 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_20220525wzec_auto
_database_code_depnum_ccdc_archive 'CCDC 2309601'
loop_
_audit_author_name
_audit_author_address
'Zhuoer Wang'
;Shandong University
China
;
_audit_update_record             
;
2023-11-22 deposited with the CCDC.	2024-04-05 downloaded from the CCDC.
;
_audit_creation_date             2022-07-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H14 Br N O3)'
_chemical_formula_sum            'C34 H28 Br2 N3 O6'
_chemical_formula_weight         734.41
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         CONBr
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.3065(3)
_cell_length_b                   13.7236(4)
_cell_length_c                   34.6883(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3002.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4826
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      71.9230
_cell_measurement_theta_min      3.4350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1484
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            14764
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.629
_diffrn_reflns_theta_min         3.463
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    107.00 172.00   1.00    1.69    --  105.98 100.00  -7.00   65
  2  ω     33.00  68.00   1.00    1.69    --  105.98 -61.00 150.00   35
  3  ω     38.00 128.00   1.00    1.69    --  105.98 -88.00 143.00   90
  4  ω     34.00  95.00   1.00    1.69    --  105.98 -77.00  60.00   61
  5  ω    -20.00  76.00   1.00    0.18    --   48.21 -88.00 143.00   96
  6  ω    -24.00  29.00   1.00    0.18    --   48.21 -42.00 -14.00   53
  7  ω   -120.00 -90.00   1.00    0.18    --  -48.21-125.00  60.00   30
  8  ω   -159.00 -89.00   1.00    1.69    --  -91.75 -94.00 -90.00   70
  9  ω   -154.00-117.00   1.00    1.69    --  -91.75 -42.00 -14.00   37
 10  ω   -109.00 -82.00   1.00    1.69    --  -91.75 -42.00 -14.00   27
 11  ω    -68.00 -20.00   1.00    1.69    --  -91.75  61.00 -90.00   48
 12  ω    -46.00 -20.00   1.00    1.69    --  -91.75  42.00 137.00   26
 13  ω   -120.00 -85.00   1.00    1.69    --  -91.75 -30.00 150.00   35
 14  ω   -166.00-135.00   1.00    1.69    --  -91.75 -30.00 150.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2049275000
_diffrn_orient_matrix_UB_12      0.0541201000
_diffrn_orient_matrix_UB_13      0.0112649000
_diffrn_orient_matrix_UB_21      0.0806035000
_diffrn_orient_matrix_UB_22      -0.0921661000
_diffrn_orient_matrix_UB_23      0.0206292000
_diffrn_orient_matrix_UB_31      0.1057577000
_diffrn_orient_matrix_UB_32      -0.0343029000
_diffrn_orient_matrix_UB_33      -0.0376831000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.881
_reflns_number_gt                4878
_reflns_number_total             5795
_reflns_odcompleteness_completeness 99.33
_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 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         3.088
_refine_diff_density_min         -1.268
_refine_diff_density_rms         0.202
_refine_ls_abs_structure_details 
;
 Flack x determined using 1562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       0.0047(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.546
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1362
_refine_ls_R_factor_gt           0.1254
_refine_ls_restrained_S_all      1.546
_refine_ls_shift/su_max          0.082
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3595
_refine_ls_wR_factor_ref         0.3757
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C32(H32), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C33(H33A,H33B), C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C45(H45), C26(H26), C4(H4), C6(H6), C7(H7), C20(H20), C44(H44),
 C28(H28), C41(H41), C43(H43), C22(H22), C42(H42), C18(H18), C21(H21), C19(H19)
2.d Idealised tetrahedral OH refined as rotating group:
 O34(H34), O12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br14 Br -0.3478(4) 0.22548(13) 0.27253(6) 0.0827(8) Uani 1 1 d . . . . .
Br36 Br 1.2990(5) 1.16225(18) 0.47569(7) 0.0953(9) Uani 1 1 d . . . . .
N23 N 0.7978(19) 0.9392(7) 0.3404(3) 0.046(2) Uani 1 1 d . . . . .
O15 O 0.462(2) 0.3423(9) 0.4043(4) 0.079(4) Uani 1 1 d . . . . .
O37 O 0.5053(19) 1.0405(9) 0.3419(3) 0.061(3) Uani 1 1 d . . . . .
O38 O 1.111(2) 0.8637(8) 0.3563(4) 0.075(3) Uani 1 1 d . . . . .
N1 N 0.168(3) 0.4431(9) 0.4082(5) 0.078(5) Uani 1 1 d . . . . .
O16 O -0.1528(18) 0.5159(8) 0.3921(7) 0.115(7) Uani 1 1 d . . . . .
C46 C 0.990(3) 1.0128(10) 0.3887(4) 0.055(3) Uani 1 1 d . . . . .
C31 C 0.678(3) 1.0196(9) 0.3539(4) 0.061(4) Uani 1 1 d . . . . .
C9 C 0.280(3) 0.3648(11) 0.3926(6) 0.078(6) Uani 1 1 d . . . . .
C40 C 0.910(3) 0.9235(9) 0.2545(4) 0.057(4) Uani 1 1 d . . . . .
C24 C 0.981(2) 0.9299(10) 0.3614(4) 0.051(3) Uani 1 1 d . . . . .
C32 C 0.708(3) 0.8668(10) 0.3145(3) 0.054(3) Uani 1 1 d . . . . .
H32 H 0.577706 0.896548 0.302852 0.065 Uiso 1 1 calc R U . . .
C29 C 0.777(3) 1.1508(10) 0.4074(4) 0.065(4) Uani 1 1 d . . . . .
H29 H 0.654504 1.190294 0.404109 0.078 Uiso 1 1 calc R U . . .
C45 C 0.765(3) 0.9541(10) 0.2284(4) 0.060(4) Uani 1 1 d . . . . .
H45 H 0.630828 0.922468 0.227511 0.072 Uiso 1 1 calc R U . . .
C26 C 1.154(3) 1.0399(11) 0.4159(5) 0.061(3) Uani 1 1 d . . . . .
H26 H 1.281618 1.004514 0.419713 0.073 Uiso 1 1 calc R U . . .
C8 C 0.143(3) 0.3175(11) 0.3646(4) 0.064(5) Uani 1 1 d . . . . .
C30 C 0.803(3) 1.0671(8) 0.3840(4) 0.053(3) Uani 1 1 d . . . . .
C4 C -0.200(3) 0.3436(10) 0.3333(7) 0.088(8) Uani 1 1 d . . . . .
H4 H -0.331020 0.376923 0.330823 0.106 Uiso 1 1 calc R U . . .
C10 C 0.237(2) 0.5212(9) 0.4322(7) 0.075(5) Uani 1 1 d . . . . .
H10 H 0.107650 0.548391 0.444781 0.090 Uiso 1 1 calc R U . . .
C3 C -0.034(3) 0.3695(10) 0.3606(6) 0.069(5) Uani 1 1 d . . . . .
C6 C 0.039(4) 0.2097(12) 0.3150(6) 0.073(5) Uani 1 1 d . . . . .
H6 H 0.059185 0.153740 0.299227 0.087 Uiso 1 1 calc R U . . .
C35 C 0.853(3) 0.8373(10) 0.2810(5) 0.068(4) Uani 1 1 d . . . . .
H35A H 0.781539 0.786268 0.265506 0.081 Uiso 1 1 calc R U . . .
H35B H 0.985048 0.809025 0.291524 0.081 Uiso 1 1 calc R U . . .
O34 O 0.511(3) 0.8038(13) 0.3703(5) 0.098(5) Uani 1 1 d . . . . .
H34 H 0.401915 0.834213 0.363158 0.147 Uiso 1 1 calc R U . . .
C5 C -0.142(3) 0.2655(10) 0.3121(5) 0.081(6) Uani 1 1 d . . . . .
C7 C 0.182(4) 0.2363(11) 0.3401(6) 0.079(7) Uani 1 1 d . . . . .
H7 H 0.312232 0.201478 0.341986 0.095 Uiso 1 1 calc R U . . .
C2 C -0.028(3) 0.4512(11) 0.3878(7) 0.075(5) Uani 1 1 d . . . . .
C27 C 1.101(4) 1.1240(12) 0.4355(5) 0.075(5) Uani 1 1 d . . . . .
C33 C 0.635(3) 0.7792(14) 0.3376(5) 0.073(5) Uani 1 1 d . . . . .
H33A H 0.551275 0.735825 0.320635 0.088 Uiso 1 1 calc R U . . .
H33B H 0.761391 0.742394 0.346292 0.088 Uiso 1 1 calc R U . . .
C20 C 0.434(4) 0.7104(13) 0.5528(8) 0.091(6) Uani 1 1 d . . . . .
H20 H 0.449450 0.763677 0.570074 0.109 Uiso 1 1 calc R U . . .
C44 C 0.803(4) 1.0283(12) 0.2035(5) 0.083(6) Uani 1 1 d . . . . .
H44 H 0.698296 1.049595 0.185686 0.099 Uiso 1 1 calc R U . . .
O12 O 0.470(3) 0.563(2) 0.3737(5) 0.122(7) Uani 1 1 d . . . . .
H12 H 0.591284 0.586883 0.376407 0.183 Uiso 1 1 calc R U . . .
C11 C 0.325(4) 0.6095(16) 0.3998(9) 0.136(14) Uani 1 1 d . . . . .
H11A H 0.203739 0.637326 0.385432 0.163 Uiso 1 1 calc R U . . .
H11B H 0.397641 0.662917 0.413735 0.163 Uiso 1 1 calc R U . . .
C28 C 0.923(3) 1.1759(12) 0.4342(4) 0.066(4) Uani 1 1 d . . . . .
H28 H 0.898720 1.228555 0.451466 0.079 Uiso 1 1 calc R U . . .
C41 C 1.103(3) 0.9702(13) 0.2562(7) 0.080(5) Uani 1 1 d . . . . .
H41 H 1.203116 0.951118 0.275166 0.096 Uiso 1 1 calc R U . . .
C43 C 0.995(6) 1.0702(15) 0.2052(7) 0.097(9) Uani 1 1 d . . . . .
H43 H 1.025160 1.121241 0.187524 0.117 Uiso 1 1 calc R U . . .
C17 C 0.394(3) 0.5585(12) 0.4952(8) 0.087(6) Uani 1 1 d . . . . .
C22 C 0.588(4) 0.6144(15) 0.5013(12) 0.120(12) Uani 1 1 d . . . . .
H22 H 0.710863 0.603017 0.486066 0.144 Uiso 1 1 calc R U . . .
C42 C 1.153(5) 1.0436(16) 0.2310(9) 0.105(10) Uani 1 1 d . . . . .
H42 H 1.287810 1.074556 0.231286 0.126 Uiso 1 1 calc R U . . .
C18 C 0.229(3) 0.5791(14) 0.5208(8) 0.094(7) Uani 1 1 d . . . . .
H18 H 0.103289 0.541614 0.518178 0.113 Uiso 1 1 calc R U . . .
C13 C 0.374(3) 0.4818(12) 0.4638(9) 0.100(8) Uani 1 1 d . . . . .
H13A H 0.515526 0.465038 0.453590 0.120 Uiso 1 1 calc R U . . .
H13B H 0.308988 0.421948 0.474565 0.120 Uiso 1 1 calc R U . . .
C21 C 0.587(4) 0.6854(15) 0.5301(10) 0.103(9) Uani 1 1 d . . . . .
H21 H 0.715869 0.719997 0.533447 0.124 Uiso 1 1 calc R U . . .
C19 C 0.231(5) 0.6530(16) 0.5514(7) 0.106(9) Uani 1 1 d . . . . .
H19 H 0.116077 0.663564 0.568507 0.127 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
Br14 C5 1.97(3) . ?
Br36 C27 1.95(2) . ?
N23 C31 1.416(15) . ?
N23 C24 1.37(2) . ?
N23 C32 1.45(2) . ?
O15 C9 1.25(2) . ?
O37 C31 1.20(2) . ?
O38 C24 1.238(17) . ?
N1 C9 1.396(19) . ?
N1 C10 1.43(3) . ?
N1 C2 1.43(3) . ?
O16 C2 1.20(2) . ?
C46 C24 1.48(2) . ?
C46 C26 1.45(3) . ?
C46 C30 1.40(2) . ?
C31 C30 1.46(3) . ?
C9 C8 1.45(3) . ?
C40 C45 1.35(3) . ?
C40 C35 1.54(2) . ?
C40 C41 1.38(3) . ?
C32 H32 1.0000 . ?
C32 C35 1.535(19) . ?
C32 C33 1.52(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.42(2) . ?
C29 C28 1.35(3) . ?
C45 H45 0.9500 . ?
C45 C44 1.36(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.38(2) . ?
C8 C3 1.33(2) . ?
C8 C7 1.42(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.45(3) . ?
C4 C5 1.35(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.74(3) . ?
C10 C13 1.50(3) . ?
C3 C2 1.47(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.38(3) . ?
C6 C7 1.31(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
O34 H34 0.8401 . ?
O34 C33 1.42(2) . ?
C7 H7 0.9500 . ?
C27 C28 1.33(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C20 H20 0.9500 . ?
C20 C21 1.29(4) . ?
C20 C19 1.50(4) . ?
C44 H44 0.9500 . ?
C44 C43 1.34(4) . ?
O12 H12 0.8400 . ?
O12 C11 1.44(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C28 H28 0.9500 . ?
C41 H41 0.9500 . ?
C41 C42 1.37(4) . ?
C43 H43 0.9500 . ?
C43 C42 1.39(4) . ?
C17 C22 1.46(3) . ?
C17 C18 1.40(4) . ?
C17 C13 1.52(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.40(4) . ?
C42 H42 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.47(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C21 H21 0.9500 . ?
C19 H19 0.9500 . ?

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 N23 C32 121.9(13) . . ?
C24 N23 C31 110.2(12) . . ?
C24 N23 C32 126.5(11) . . ?
C9 N1 C10 130.4(18) . . ?
C9 N1 C2 107.8(19) . . ?
C2 N1 C10 119.8(12) . . ?
C26 C46 C24 129.7(14) . . ?
C30 C46 C24 107.5(14) . . ?
C30 C46 C26 122.7(13) . . ?
N23 C31 C30 107.4(14) . . ?
O37 C31 N23 123.7(16) . . ?
O37 C31 C30 128.9(12) . . ?
O15 C9 N1 122(2) . . ?
O15 C9 C8 130.4(16) . . ?
N1 C9 C8 107.6(17) . . ?
C45 C40 C35 118.7(15) . . ?
C45 C40 C41 118.7(16) . . ?
C41 C40 C35 122.5(19) . . ?
N23 C24 C46 107.4(11) . . ?
O38 C24 N23 123.5(14) . . ?
O38 C24 C46 129.1(16) . . ?
N23 C32 H32 106.9 . . ?
N23 C32 C35 114.4(14) . . ?
N23 C32 C33 109.5(11) . . ?
C35 C32 H32 106.9 . . ?
C33 C32 H32 106.9 . . ?
C33 C32 C35 111.8(11) . . ?
C30 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C28 C29 C30 121.6(16) . . ?
C40 C45 H45 118.7 . . ?
C44 C45 C40 122.6(19) . . ?
C44 C45 H45 118.7 . . ?
C46 C26 H26 124.4 . . ?
C27 C26 C46 111.1(17) . . ?
C27 C26 H26 124.5 . . ?
C3 C8 C9 109.1(15) . . ?
C3 C8 C7 120(2) . . ?
C7 C8 C9 130.3(18) . . ?
C46 C30 C31 107.4(11) . . ?
C46 C30 C29 117.3(16) . . ?
C29 C30 C31 135.3(15) . . ?
C3 C4 H4 124.6 . . ?
C5 C4 H4 124.6 . . ?
C5 C4 C3 110.7(19) . . ?
N1 C10 H10 106.5 . . ?
N1 C10 C11 104.2(16) . . ?
N1 C10 C13 109.5(12) . . ?
C11 C10 H10 106.4 . . ?
C13 C10 H10 106.5 . . ?
C13 C10 C11 122.8(17) . . ?
C8 C3 C4 122.6(17) . . ?
C8 C3 C2 109(2) . . ?
C4 C3 C2 128.7(14) . . ?
C5 C6 H6 121.1 . . ?
C7 C6 H6 121.2 . . ?
C7 C6 C5 117.7(19) . . ?
C40 C35 H35A 109.0 . . ?
C40 C35 H35B 109.0 . . ?
C32 C35 C40 112.8(11) . . ?
C32 C35 H35A 109.0 . . ?
C32 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C33 O34 H34 109.5 . . ?
C4 C5 Br14 115.0(18) . . ?
C4 C5 C6 129(3) . . ?
C6 C5 Br14 116.2(15) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 C8 119.8(18) . . ?
C6 C7 H7 120.1 . . ?
N1 C2 C3 106.4(14) . . ?
O16 C2 N1 124(2) . . ?
O16 C2 C3 129(2) . . ?
C26 C27 Br36 114.9(17) . . ?
C28 C27 Br36 115.0(12) . . ?
C28 C27 C26 129.6(19) . . ?
C32 C33 H33A 108.8 . . ?
C32 C33 H33B 108.8 . . ?
O34 C33 C32 113.6(15) . . ?
O34 C33 H33A 108.8 . . ?
O34 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C21 C20 H20 120.8 . . ?
C21 C20 C19 118(2) . . ?
C19 C20 H20 120.8 . . ?
C45 C44 H44 121.5 . . ?
C43 C44 C45 117(2) . . ?
C43 C44 H44 121.5 . . ?
C11 O12 H12 109.5 . . ?
C10 C11 H11A 110.2 . . ?
C10 C11 H11B 110.2 . . ?
O12 C11 C10 107(2) . . ?
O12 C11 H11A 110.3 . . ?
O12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C29 C28 H28 121.3 . . ?
C27 C28 C29 117.3(14) . . ?
C27 C28 H28 121.3 . . ?
C40 C41 H41 119.4 . . ?
C42 C41 C40 121(2) . . ?
C42 C41 H41 119.3 . . ?
C44 C43 H43 117.8 . . ?
C44 C43 C42 124(2) . . ?
C42 C43 H43 117.9 . . ?
C22 C17 C13 123(2) . . ?
C18 C17 C22 115(2) . . ?
C18 C17 C13 122.0(19) . . ?
C17 C22 H22 121.2 . . ?
C21 C22 C17 118(3) . . ?
C21 C22 H22 121.1 . . ?
C41 C42 C43 116(2) . . ?
C41 C42 H42 122.0 . . ?
C43 C42 H42 122.0 . . ?
C17 C18 H18 116.9 . . ?
C17 C18 C19 126(2) . . ?
C19 C18 H18 116.9 . . ?
C10 C13 C17 109.0(15) . . ?
C10 C13 H13A 109.9 . . ?
C10 C13 H13B 109.9 . . ?
C17 C13 H13A 109.9 . . ?
C17 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C20 C21 C22 129(2) . . ?
C20 C21 H21 115.6 . . ?
C22 C21 H21 115.6 . . ?
C20 C19 H19 123.3 . . ?
C18 C19 C20 113(3) . . ?
C18 C19 H19 123.4 . . ?

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
Br36 C27 C28 C29 -178.5(11) . . . . ?
N23 C31 C30 C46 -1.8(13) . . . . ?
N23 C31 C30 C29 177.4(14) . . . . ?
N23 C32 C35 C40 -60.9(19) . . . . ?
N23 C32 C33 O34 49(2) . . . . ?
O15 C9 C8 C3 -178.1(15) . . . . ?
O15 C9 C8 C7 -5(3) . . . . ?
O37 C31 C30 C46 177.2(13) . . . . ?
O37 C31 C30 C29 -4(2) . . . . ?
N1 C9 C8 C3 5.6(16) . . . . ?
N1 C9 C8 C7 178.3(13) . . . . ?
N1 C10 C11 O12 -51(2) . . . . ?
N1 C10 C13 C17 -163.8(16) . . . . ?
C46 C26 C27 Br36 175.4(10) . . . . ?
C46 C26 C27 C28 4(2) . . . . ?
C31 N23 C24 O38 177.8(14) . . . . ?
C31 N23 C24 C46 -3.8(14) . . . . ?
C31 N23 C32 C35 135.9(12) . . . . ?
C31 N23 C32 C33 -97.7(14) . . . . ?
C9 N1 C10 C11 87(2) . . . . ?
C9 N1 C10 C13 -46(2) . . . . ?
C9 N1 C2 O16 -174(2) . . . . ?
C9 N1 C2 C3 3.6(17) . . . . ?
C9 C8 C3 C4 177.4(13) . . . . ?
C9 C8 C3 C2 -3.3(16) . . . . ?
C9 C8 C7 C6 -175.5(14) . . . . ?
C40 C45 C44 C43 1(2) . . . . ?
C40 C41 C42 C43 3(2) . . . . ?
C24 N23 C31 O37 -175.6(13) . . . . ?
C24 N23 C31 C30 3.6(14) . . . . ?
C24 N23 C32 C35 -59.6(16) . . . . ?
C24 N23 C32 C33 66.8(18) . . . . ?
C24 C46 C26 C27 178.8(14) . . . . ?
C24 C46 C30 C31 -0.4(14) . . . . ?
C24 C46 C30 C29 -179.8(12) . . . . ?
C32 N23 C31 O37 -8.8(18) . . . . ?
C32 N23 C31 C30 170.3(10) . . . . ?
C32 N23 C24 O38 12(2) . . . . ?
C32 N23 C24 C46 -169.7(11) . . . . ?
C45 C40 C35 C32 -78.2(18) . . . . ?
C45 C40 C41 C42 -3(2) . . . . ?
C45 C44 C43 C42 -1(3) . . . . ?
C26 C46 C24 N23 -176.5(13) . . . . ?
C26 C46 C24 O38 2(3) . . . . ?
C26 C46 C30 C31 178.7(12) . . . . ?
C26 C46 C30 C29 -0.7(19) . . . . ?
C26 C27 C28 C29 -8(3) . . . . ?
C8 C3 C2 N1 -0.1(17) . . . . ?
C8 C3 C2 O16 177(2) . . . . ?
C30 C46 C24 N23 2.6(14) . . . . ?
C30 C46 C24 O38 -179.2(15) . . . . ?
C30 C46 C26 C27 -0.1(19) . . . . ?
C30 C29 C28 C27 6(2) . . . . ?
C4 C3 C2 N1 179.1(14) . . . . ?
C4 C3 C2 O16 -4(3) . . . . ?
C10 N1 C9 O15 14(2) . . . . ?
C10 N1 C9 C8 -169.2(16) . . . . ?
C10 N1 C2 O16 -8(3) . . . . ?
C10 N1 C2 C3 169.3(14) . . . . ?
C3 C8 C7 C6 -3(2) . . . . ?
C3 C4 C5 Br14 -177.8(10) . . . . ?
C3 C4 C5 C6 4(2) . . . . ?
C35 C40 C45 C44 -178.8(13) . . . . ?
C35 C40 C41 C42 176.8(13) . . . . ?
C35 C32 C33 O34 176.4(17) . . . . ?
C5 C4 C3 C8 -4(2) . . . . ?
C5 C4 C3 C2 177.2(14) . . . . ?
C5 C6 C7 C8 3(2) . . . . ?
C7 C8 C3 C4 4(2) . . . . ?
C7 C8 C3 C2 -176.9(13) . . . . ?
C7 C6 C5 Br14 177.8(11) . . . . ?
C7 C6 C5 C4 -4(2) . . . . ?
C2 N1 C9 O15 177.8(14) . . . . ?
C2 N1 C9 C8 -5.5(16) . . . . ?
C2 N1 C10 C11 -74.7(19) . . . . ?
C2 N1 C10 C13 152.2(18) . . . . ?
C33 C32 C35 C40 173.9(16) . . . . ?
C44 C43 C42 C41 0(3) . . . . ?
C11 C10 C13 C17 74(3) . . . . ?
C28 C29 C30 C46 -2(2) . . . . ?
C28 C29 C30 C31 178.5(14) . . . . ?
C41 C40 C45 C44 1(2) . . . . ?
C41 C40 C35 C32 102.2(18) . . . . ?
C17 C22 C21 C20 -1(4) . . . . ?
C17 C18 C19 C20 1(3) . . . . ?
C22 C17 C18 C19 3(3) . . . . ?
C22 C17 C13 C10 -106(3) . . . . ?
C18 C17 C22 C21 -3(4) . . . . ?
C18 C17 C13 C10 75(3) . . . . ?
C13 C10 C11 O12 74(3) . . . . ?
C13 C17 C22 C21 178(2) . . . . ?
C13 C17 C18 C19 -178.4(18) . . . . ?
C21 C20 C19 C18 -5(3) . . . . ?
C19 C20 C21 C22 5(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 1.877
_oxdiff_exptl_absorpt_empirical_full_min 0.600
