# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

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

data_202106187
_audit_block_doi                 10.5517/ccdc.csd.cc28px30
_database_code_depnum_ccdc_archive 'CCDC 2106422'
loop_
_audit_author_name
_audit_author_address
yang
;Henan Agricultural University
China
;
_audit_update_record             
;
2021-08-28 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-07-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 Br N O6'
_chemical_formula_sum            'C24 H20 Br N O6'
_chemical_formula_weight         498.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O5N2S1
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.6396(8)
_cell_length_b                   11.0916(11)
_cell_length_c                   11.1581(9)
_cell_angle_alpha                115.315(9)
_cell_angle_beta                 103.598(7)
_cell_angle_gamma                101.463(7)
_cell_volume                     1087.78(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2405
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.1800
_cell_measurement_theta_min      4.5230
_shelx_estimated_absorpt_T_max   0.758
_shelx_estimated_absorpt_T_min   0.651
_exptl_absorpt_coefficient_mu    2.936
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7827
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         4.548
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00 -60.00   87
  2  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00 120.00   81
  3  ω     18.00 105.00   1.00    1.00    --   36.47  57.00  90.00   87
  4  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00 -30.00   81
  5  ω    -34.00  59.00   1.00    1.00    --   36.47 -37.00-180.00   93
  6  ω     57.00 110.00   1.00    1.00    --   36.47 178.00  30.00   53
  7  ω    -34.00  59.00   1.00    1.00    --   36.47 -37.00 -60.00   93
  8  ω    -33.00  65.00   1.00    1.00    --   36.47 -77.00-150.00   98
  9  ω     18.00 105.00   1.00    1.00    --   36.47  57.00-180.00   87
 10  ω     37.00 112.00   1.00    2.50    --  108.00-111.00-120.00   75
 11  ω     43.00 125.00   1.00    2.50    --  108.00 -61.00-150.00   82
 12  ω    145.00 174.00   1.00    2.50    --  108.00  61.00-150.00   29
 13  ω     57.00 118.00   1.00    2.50    --  108.00 -77.00 120.00   61
 14  ω    128.00 155.00   1.00    2.50    --  108.00  30.00  30.00   27
 15  ω     40.00 106.00   1.00    2.50    --  108.00-111.00 120.00   66
 16  ω     75.00 112.00   1.00    2.50    --  108.00-111.00 -30.00   37
 17  ω     52.00  96.00   1.00    2.50    --  108.00 -94.00  30.00   44
 18  ω     86.00 137.00   1.00    2.50    --  108.00  30.00 120.00   51
 19  ω     38.00 124.00   1.00    2.50    --  108.00 -30.00 120.00   86
 20  ω     39.00 106.00   1.00    2.50    --  108.00 -45.00  60.00   67
 21  ω     47.00 141.00   1.00    2.50    --  108.00 -15.00 -90.00   94
 22  ω     40.00  66.00   1.00    2.50    --  108.00-111.00 -30.00   26
 23  ω     41.00 127.00   1.00    2.50    --  108.00 -61.00 -60.00   86
 24  ω     63.00 168.00   1.00    2.50    --  108.00  15.00 -30.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0323910000
_diffrn_orient_matrix_UB_12      -0.1363764000
_diffrn_orient_matrix_UB_13      -0.0254505000
_diffrn_orient_matrix_UB_21      -0.0827271000
_diffrn_orient_matrix_UB_22      -0.0212342000
_diffrn_orient_matrix_UB_23      0.0899716000
_diffrn_orient_matrix_UB_31      -0.1311923000
_diffrn_orient_matrix_UB_32      -0.0875036000
_diffrn_orient_matrix_UB_33      -0.1344888000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2925
_reflns_number_total             3878
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3878
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.037
_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)+(0.0692P)²+0.2797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1411
_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:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C24(H24A,H24B,
 H24C)
;
_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 -0.13430(5) 0.56122(6) 0.82860(6) 0.0783(2) Uani 1 1 d . . . . .
O1 O 0.5249(3) 0.6646(3) 0.5778(3) 0.0583(6) Uani 1 1 d . . . . .
O2 O 0.3442(3) 0.5223(3) 1.0171(3) 0.0715(8) Uani 1 1 d . . . . .
O3 O 0.4985(3) 0.7301(3) 1.1870(3) 0.0766(9) Uani 1 1 d . . . . .
O4 O 0.3902(2) 0.8602(3) 0.6893(2) 0.0507(6) Uani 1 1 d . . . . .
O5 O -0.0941(4) 0.6750(6) 0.4479(4) 0.1086(15) Uani 1 1 d . . . . .
O6 O 0.0443(4) 0.7586(5) 0.3621(4) 0.1089(15) Uani 1 1 d . . . . .
N1 N 0.5175(3) 0.8196(3) 0.8539(3) 0.0451(6) Uani 1 1 d . . . . .
C1 C 0.1517(4) 0.6324(4) 0.8855(4) 0.0549(9) Uani 1 1 d . . . . .
H1 H 0.1530 0.6101 0.9571 0.066 Uiso 1 1 calc R . . . .
C2 C 0.0298(4) 0.6218(4) 0.7977(4) 0.0554(9) Uani 1 1 d . . . . .
C3 C 0.0216(4) 0.6566(4) 0.6920(4) 0.0550(9) Uani 1 1 d . . . . .
H3 H -0.0629 0.6482 0.6354 0.066 Uiso 1 1 calc R . . . .
C4 C 0.1407(4) 0.7042(4) 0.6709(4) 0.0488(8) Uani 1 1 d . . . . .
C5 C 0.2651(3) 0.7108(4) 0.7574(3) 0.0454(7) Uani 1 1 d . . . . .
C6 C 0.2729(4) 0.6772(4) 0.8653(4) 0.0479(8) Uani 1 1 d . . . . .
C7 C 0.4091(4) 0.7008(4) 0.9577(3) 0.0484(8) Uani 1 1 d . . . . .
C8 C 0.5248(4) 0.7714(4) 0.9520(3) 0.0472(8) Uani 1 1 d . . . . .
C9 C 0.3917(3) 0.7526(4) 0.7284(3) 0.0442(7) Uani 1 1 d . . . . .
C10 C 0.4056(3) 0.6250(4) 0.6098(3) 0.0477(8) Uani 1 1 d . . . . .
H10A H 0.4113 0.5546 0.6385 0.057 Uiso 1 1 calc R . . . .
H10B H 0.3242 0.5824 0.5247 0.057 Uiso 1 1 calc R . . . .
C11 C 0.6350(4) 0.7802(4) 0.6846(4) 0.0493(8) Uani 1 1 d . . . . .
C12 C 0.6352(4) 0.8622(4) 0.8208(3) 0.0473(8) Uani 1 1 d . . . . .
C13 C 0.7456(4) 0.9841(4) 0.9175(4) 0.0600(9) Uani 1 1 d . . . . .
H13 H 0.7436 1.0429 1.0060 0.072 Uiso 1 1 calc R . . . .
C14 C 0.8595(4) 1.0197(5) 0.8839(5) 0.0700(11) Uani 1 1 d . . . . .
H14 H 0.9351 1.1004 0.9506 0.084 Uiso 1 1 calc R . . . .
C15 C 0.8601(4) 0.9345(5) 0.7505(5) 0.0700(11) Uani 1 1 d . . . . .
H15 H 0.9369 0.9575 0.7280 0.084 Uiso 1 1 calc R . . . .
C16 C 0.7484(4) 0.8168(5) 0.6515(4) 0.0583(9) Uani 1 1 d . . . . .
H16 H 0.7490 0.7612 0.5614 0.070 Uiso 1 1 calc R . . . .
C17 C 0.6679(4) 0.8020(5) 1.0461(4) 0.0596(9) Uani 1 1 d . . . . .
H17A H 0.7265 0.7883 0.9914 0.089 Uiso 1 1 calc GR . . . .
H17B H 0.6650 0.7389 1.0840 0.089 Uiso 1 1 calc GR . . . .
H17C H 0.7033 0.8983 1.1227 0.089 Uiso 1 1 calc GR . . . .
C18 C 0.4130(4) 0.6402(4) 1.0534(4) 0.0573(9) Uani 1 1 d . . . . .
C19 C 0.5151(6) 0.6721(7) 1.2812(5) 0.104(2) Uani 1 1 d . . . . .
H19A H 0.5623 0.6054 1.2533 0.156 Uiso 1 1 calc GR . . . .
H19B H 0.4263 0.6249 1.2760 0.156 Uiso 1 1 calc GR . . . .
H19C H 0.5676 0.7473 1.3769 0.156 Uiso 1 1 calc GR . . . .
C20 C 0.3088(5) 0.9259(5) 0.5233(5) 0.0743(13) Uani 1 1 d . . . . .
H20A H 0.4016 0.9903 0.5776 0.112 Uiso 1 1 calc GR . . . .
H20B H 0.2475 0.9786 0.5226 0.112 Uiso 1 1 calc GR . . . .
H20C H 0.3008 0.8650 0.4276 0.112 Uiso 1 1 calc GR . . . .
C21 C 0.2721(4) 0.8379(4) 0.5891(4) 0.0515(8) Uani 1 1 d . . . . .
C22 C 0.1495(4) 0.7565(4) 0.5706(4) 0.0505(8) Uani 1 1 d . . . . .
C23 C 0.0203(4) 0.7299(5) 0.4595(4) 0.0581(9) Uani 1 1 d . . . . .
C24 C -0.0752(6) 0.7451(7) 0.2565(6) 0.115(2) Uani 1 1 d . . . . .
H24A H -0.0491 0.7555 0.1838 0.173 Uiso 1 1 calc GR . . . .
H24B H -0.1122 0.8174 0.3009 0.173 Uiso 1 1 calc GR . . . .
H24C H -0.1435 0.6534 0.2149 0.173 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.907(4) . ?
O1 C10 1.434(4) . ?
O1 C11 1.370(4) . ?
O2 C18 1.199(5) . ?
O3 C18 1.332(5) . ?
O3 C19 1.445(5) . ?
O4 C9 1.437(4) . ?
O4 C21 1.367(4) . ?
O5 C23 1.197(5) . ?
O6 C23 1.319(5) . ?
O6 C24 1.447(5) . ?
N1 C8 1.402(4) . ?
N1 C9 1.462(4) . ?
N1 C12 1.435(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.378(5) . ?
C1 C6 1.392(5) . ?
C2 C3 1.379(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(5) . ?
C4 C5 1.410(5) . ?
C4 C22 1.477(5) . ?
C5 C6 1.394(5) . ?
C5 C9 1.489(5) . ?
C6 C7 1.466(5) . ?
C7 C8 1.352(5) . ?
C7 C18 1.483(5) . ?
C8 C17 1.508(5) . ?
C9 C10 1.533(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.398(5) . ?
C11 C16 1.378(5) . ?
C12 C13 1.378(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(6) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 C21 1.497(5) . ?
C21 C22 1.344(5) . ?
C22 C23 1.495(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C10 117.7(3) . . ?
C18 O3 C19 115.9(4) . . ?
C21 O4 C9 117.3(3) . . ?
C23 O6 C24 115.8(4) . . ?
C8 N1 C9 118.3(3) . . ?
C8 N1 C12 121.7(3) . . ?
C12 N1 C9 110.6(3) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.9(3) . . ?
C6 C1 H1 120.6 . . ?
C1 C2 Br1 117.9(3) . . ?
C1 C2 C3 123.3(3) . . ?
C3 C2 Br1 118.7(3) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.3(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 117.6(3) . . ?
C3 C4 C22 125.3(3) . . ?
C5 C4 C22 117.0(3) . . ?
C4 C5 C9 117.7(3) . . ?
C6 C5 C4 122.7(3) . . ?
C6 C5 C9 119.5(3) . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 C7 123.5(3) . . ?
C5 C6 C7 118.2(3) . . ?
C6 C7 C18 116.8(3) . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 C18 122.3(3) . . ?
N1 C8 C17 115.5(3) . . ?
C7 C8 N1 120.8(3) . . ?
C7 C8 C17 123.6(3) . . ?
O4 C9 N1 103.6(3) . . ?
O4 C9 C5 110.3(3) . . ?
O4 C9 C10 109.4(3) . . ?
N1 C9 C5 113.1(3) . . ?
N1 C9 C10 108.7(3) . . ?
C5 C9 C10 111.4(3) . . ?
O1 C10 C9 112.0(3) . . ?
O1 C10 H10A 109.2 . . ?
O1 C10 H10B 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O1 C11 C12 123.3(3) . . ?
O1 C11 C16 116.8(3) . . ?
C16 C11 C12 119.9(3) . . ?
C11 C12 N1 118.8(3) . . ?
C13 C12 N1 121.9(3) . . ?
C13 C12 C11 119.2(4) . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.5(4) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.5(4) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.3(4) . . ?
C15 C16 H16 119.9 . . ?
C8 C17 H17A 109.5 . . ?
C8 C17 H17B 109.5 . . ?
C8 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 O3 121.9(3) . . ?
O2 C18 C7 124.1(4) . . ?
O3 C18 C7 114.0(3) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
O4 C21 C20 107.8(3) . . ?
C22 C21 O4 121.1(3) . . ?
C22 C21 C20 130.9(3) . . ?
C4 C22 C23 119.4(3) . . ?
C21 C22 C4 119.1(3) . . ?
C21 C22 C23 121.2(3) . . ?
O5 C23 O6 121.5(4) . . ?
O5 C23 C22 125.5(4) . . ?
O6 C23 C22 112.6(4) . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
Br1 C2 C3 C4 178.4(3) . . . . ?
O1 C11 C12 N1 3.5(5) . . . . ?
O1 C11 C12 C13 -174.1(3) . . . . ?
O1 C11 C16 C15 177.1(4) . . . . ?
O4 C9 C10 O1 56.0(4) . . . . ?
O4 C21 C22 C4 7.0(5) . . . . ?
O4 C21 C22 C23 -179.0(3) . . . . ?
N1 C9 C10 O1 -56.4(4) . . . . ?
N1 C12 C13 C14 177.8(4) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C1 C6 C7 C8 -166.2(4) . . . . ?
C1 C6 C7 C18 15.5(5) . . . . ?
C2 C1 C6 C5 0.7(6) . . . . ?
C2 C1 C6 C7 176.0(3) . . . . ?
C2 C3 C4 C5 1.8(6) . . . . ?
C2 C3 C4 C22 -174.6(4) . . . . ?
C3 C4 C5 C6 -2.7(5) . . . . ?
C3 C4 C5 C9 176.0(3) . . . . ?
C3 C4 C22 C21 160.1(4) . . . . ?
C3 C4 C22 C23 -14.0(6) . . . . ?
C4 C5 C6 C1 1.4(5) . . . . ?
C4 C5 C6 C7 -174.2(3) . . . . ?
C4 C5 C9 O4 37.5(4) . . . . ?
C4 C5 C9 N1 153.0(3) . . . . ?
C4 C5 C9 C10 -84.2(4) . . . . ?
C4 C22 C23 O5 4.3(7) . . . . ?
C4 C22 C23 O6 -168.3(4) . . . . ?
C5 C4 C22 C21 -16.3(5) . . . . ?
C5 C4 C22 C23 169.7(3) . . . . ?
C5 C6 C7 C8 9.2(5) . . . . ?
C5 C6 C7 C18 -169.1(3) . . . . ?
C5 C9 C10 O1 178.2(3) . . . . ?
C6 C1 C2 Br1 -179.7(3) . . . . ?
C6 C1 C2 C3 -1.6(6) . . . . ?
C6 C5 C9 O4 -143.9(3) . . . . ?
C6 C5 C9 N1 -28.3(4) . . . . ?
C6 C5 C9 C10 94.4(4) . . . . ?
C6 C7 C8 N1 -2.3(5) . . . . ?
C6 C7 C8 C17 178.7(3) . . . . ?
C6 C7 C18 O2 45.3(6) . . . . ?
C6 C7 C18 O3 -133.2(4) . . . . ?
C8 N1 C9 O4 154.7(3) . . . . ?
C8 N1 C9 C5 35.2(4) . . . . ?
C8 N1 C9 C10 -89.1(3) . . . . ?
C8 N1 C12 C11 112.6(4) . . . . ?
C8 N1 C12 C13 -69.9(5) . . . . ?
C8 C7 C18 O2 -133.0(5) . . . . ?
C8 C7 C18 O3 48.5(5) . . . . ?
C9 O4 C21 C20 -157.6(3) . . . . ?
C9 O4 C21 C22 26.7(5) . . . . ?
C9 N1 C8 C7 -21.0(5) . . . . ?
C9 N1 C8 C17 158.2(3) . . . . ?
C9 N1 C12 C11 -33.1(4) . . . . ?
C9 N1 C12 C13 144.4(3) . . . . ?
C9 C5 C6 C1 -177.2(3) . . . . ?
C9 C5 C6 C7 7.2(5) . . . . ?
C10 O1 C11 C12 -1.4(5) . . . . ?
C10 O1 C11 C16 -179.7(3) . . . . ?
C11 O1 C10 C9 27.9(4) . . . . ?
C11 C12 C13 C14 -4.6(6) . . . . ?
C12 N1 C8 C7 -164.2(3) . . . . ?
C12 N1 C8 C17 15.0(5) . . . . ?
C12 N1 C9 O4 -58.3(3) . . . . ?
C12 N1 C9 C5 -177.8(3) . . . . ?
C12 N1 C9 C10 57.9(3) . . . . ?
C12 C11 C16 C15 -1.3(6) . . . . ?
C12 C13 C14 C15 2.1(7) . . . . ?
C13 C14 C15 C16 0.9(7) . . . . ?
C14 C15 C16 C11 -1.3(7) . . . . ?
C16 C11 C12 N1 -178.2(3) . . . . ?
C16 C11 C12 C13 4.2(5) . . . . ?
C18 C7 C8 N1 175.9(3) . . . . ?
C18 C7 C8 C17 -3.1(6) . . . . ?
C19 O3 C18 O2 6.8(7) . . . . ?
C19 O3 C18 C7 -174.7(4) . . . . ?
C20 C21 C22 C4 -167.6(4) . . . . ?
C20 C21 C22 C23 6.3(7) . . . . ?
C21 O4 C9 N1 -169.1(3) . . . . ?
C21 O4 C9 C5 -47.7(4) . . . . ?
C21 O4 C9 C10 75.2(4) . . . . ?
C21 C22 C23 O5 -169.7(5) . . . . ?
C21 C22 C23 O6 17.8(6) . . . . ?
C22 C4 C5 C6 174.0(3) . . . . ?
C22 C4 C5 C9 -7.4(5) . . . . ?
C24 O6 C23 O5 11.3(8) . . . . ?
C24 O6 C23 C22 -175.8(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 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.873
####################################################################### 
# 
# 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_WH18
_audit_block_doi                 10.5517/ccdc.csd.cc29z7q8
_database_code_depnum_ccdc_archive 'CCDC 2144230'
loop_
_audit_author_name
_audit_author_address
yang
;Henan Agricultural University
China
;
_audit_update_record             
;
2022-01-25 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 Cl N O6'
_chemical_formula_weight         433.70

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'
Cl Cl 0.1484 0.1585 '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'

_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.4404(7)
_cell_length_b                   13.2210(11)
_cell_length_c                   18.9283(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2112.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9087
_cell_measurement_theta_min      2.6422
_cell_measurement_theta_max      24.9097

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.5698
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15926
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.879
_diffrn_reflns_theta_max         25.090
_diffrn_reflns_theta_full        25.090
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3748
_reflns_number_gt                2974
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1165P)²+0.6757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1042 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3748
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1862
_refine_ls_wR_factor_gt          0.1733
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3740(7) 0.3974(5) 0.7551(3) 0.0358(14) Uani 1 1 d . . . . .
C2 C 0.4277(6) 0.4165(4) 0.6868(3) 0.0275(13) Uani 1 1 d . . . . .
C3 C 0.4213(6) 0.3429(4) 0.6359(3) 0.0273(13) Uani 1 1 d . . . . .
C4 C 0.3696(7) 0.2454(5) 0.6533(3) 0.0375(15) Uani 1 1 d . . . . .
C5 C 0.3138(8) 0.2246(5) 0.7205(4) 0.0429(16) Uani 1 1 d . . . . .
C6 C 0.3138(7) 0.3025(5) 0.7700(3) 0.0377(15) Uani 1 1 d . . . . .
C7 C 0.5388(7) 0.5339(4) 0.6053(3) 0.0292(13) Uani 1 1 d . . . . .
C8 C 0.5991(6) 0.4413(4) 0.5666(3) 0.0245(12) Uani 1 1 d . . . . .
C9 C 0.6582(6) 0.4684(4) 0.4943(3) 0.0236(12) Uani 1 1 d . . . . .
C10 C 0.5678(6) 0.4528(4) 0.4347(3) 0.0268(12) Uani 1 1 d . . . . .
C11 C 0.4143(6) 0.4017(4) 0.4438(3) 0.0275(13) Uani 1 1 d . . . . .
C12 C 0.3707(7) 0.3625(4) 0.5070(3) 0.0287(13) Uani 1 1 d . . . . .
C13 C 0.8091(6) 0.5118(4) 0.4913(3) 0.0268(13) Uani 1 1 d . . . . .
C14 C 0.8674(7) 0.5441(4) 0.4261(3) 0.0328(14) Uani 1 1 d . . . . .
C15 C 0.7737(8) 0.5334(5) 0.3664(3) 0.0394(15) Uani 1 1 d . . . . .
C16 C 0.6250(7) 0.4881(5) 0.3705(3) 0.0367(15) Uani 1 1 d . . . . .
C17 C 0.8634(6) 0.4495(4) 0.6099(3) 0.0296(13) Uani 1 1 d . . . . .
C18 C 0.9038(6) 0.5124(4) 0.5573(3) 0.0291(13) Uani 1 1 d . . . . .
C19 C 0.9521(8) 0.4245(6) 0.6757(4) 0.0457(17) Uani 1 1 d . . . . .
C20 C 1.0432(7) 0.5772(5) 0.5644(4) 0.0364(15) Uani 1 1 d . . . . .
C21 C 1.1489(11) 0.7396(6) 0.5421(5) 0.068(2) Uani 1 1 d . . . . .
C22 C 0.2132(8) 0.3107(5) 0.5174(3) 0.0405(15) Uani 1 1 d . . . . .
C23 C 0.3088(8) 0.3889(5) 0.3815(3) 0.0344(14) Uani 1 1 d . . . . .
C24 C 0.2850(11) 0.3226(6) 0.2658(4) 0.062(2) Uani 1 1 d . . . . .
Cl1 Cl 0.2335(3) 0.27992(16) 0.85301(10) 0.0690(7) Uani 1 1 d . . . . .
N1 N 0.4730(5) 0.3666(3) 0.5651(2) 0.0271(11) Uani 1 1 d . . . . .
O1 O 0.4922(5) 0.5097(3) 0.6762(2) 0.0378(11) Uani 1 1 d . . . . .
O2 O 0.7247(4) 0.3950(3) 0.6065(2) 0.0289(9) Uani 1 1 d . . . . .
O3 O 1.1643(6) 0.5566(4) 0.5946(3) 0.0605(15) Uani 1 1 d . . . . .
O4 O 1.0198(5) 0.6682(3) 0.5349(3) 0.0458(12) Uani 1 1 d . . . . .
O5 O 0.1751(6) 0.4209(5) 0.3762(3) 0.0575(14) Uani 1 1 d . . . . .
O6 O 0.3775(6) 0.3372(3) 0.3296(2) 0.0455(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.383(9) . ?
C1 C2 1.392(9) . ?
C2 O1 1.362(7) . ?
C2 C3 1.371(8) . ?
C3 C4 1.401(8) . ?
C3 N1 1.444(7) . ?
C4 C5 1.383(9) . ?
C5 C6 1.393(9) . ?
C6 Cl1 1.738(6) . ?
C7 O1 1.435(7) . ?
C7 C8 1.515(8) . ?
C8 O2 1.439(7) . ?
C8 N1 1.452(7) . ?
C8 C9 1.500(8) . ?
C9 C10 1.378(8) . ?
C9 C13 1.398(8) . ?
C10 C16 1.388(9) . ?
C10 C11 1.471(8) . ?
C11 C12 1.355(8) . ?
C11 C23 1.488(9) . ?
C12 N1 1.399(7) . ?
C12 C22 1.508(8) . ?
C13 C14 1.395(9) . ?
C13 C18 1.482(8) . ?
C14 C15 1.387(9) . ?
C15 C16 1.393(9) . ?
C17 C18 1.343(8) . ?
C17 O2 1.376(7) . ?
C17 C19 1.490(9) . ?
C18 C20 1.461(8) . ?
C20 O3 1.204(8) . ?
C20 O4 1.341(8) . ?
C21 O4 1.448(8) . ?
C23 O5 1.210(8) . ?
C23 O6 1.329(8) . ?
C24 O6 1.450(8) . ?

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
C6 C1 C2 118.3(6) . . ?
O1 C2 C3 123.7(5) . . ?
O1 C2 C1 115.5(5) . . ?
C3 C2 C1 120.7(5) . . ?
C2 C3 C4 120.0(5) . . ?
C2 C3 N1 119.1(5) . . ?
C4 C3 N1 120.8(5) . . ?
C5 C4 C3 120.4(6) . . ?
C4 C5 C6 118.1(6) . . ?
C1 C6 C5 122.3(6) . . ?
C1 C6 Cl1 119.0(5) . . ?
C5 C6 Cl1 118.8(5) . . ?
O1 C7 C8 111.4(5) . . ?
O2 C8 N1 105.2(4) . . ?
O2 C8 C9 109.6(4) . . ?
N1 C8 C9 112.9(4) . . ?
O2 C8 C7 109.7(5) . . ?
N1 C8 C7 108.3(4) . . ?
C9 C8 C7 111.1(4) . . ?
C10 C9 C13 122.2(5) . . ?
C10 C9 C8 121.8(5) . . ?
C13 C9 C8 116.0(5) . . ?
C9 C10 C16 118.3(5) . . ?
C9 C10 C11 117.4(5) . . ?
C16 C10 C11 124.3(6) . . ?
C12 C11 C10 121.3(5) . . ?
C12 C11 C23 119.6(5) . . ?
C10 C11 C23 119.1(5) . . ?
C11 C12 N1 120.7(5) . . ?
C11 C12 C22 121.9(5) . . ?
N1 C12 C22 117.4(5) . . ?
C14 C13 C9 118.8(5) . . ?
C14 C13 C18 123.6(5) . . ?
C9 C13 C18 117.3(5) . . ?
C15 C14 C13 119.3(5) . . ?
C14 C15 C16 120.8(6) . . ?
C10 C16 C15 120.5(6) . . ?
C18 C17 O2 120.4(5) . . ?
C18 C17 C19 129.1(5) . . ?
O2 C17 C19 110.5(5) . . ?
C17 C18 C20 120.0(5) . . ?
C17 C18 C13 119.0(5) . . ?
C20 C18 C13 121.0(5) . . ?
O3 C20 O4 121.7(6) . . ?
O3 C20 C18 126.5(6) . . ?
O4 C20 C18 111.7(5) . . ?
O5 C23 O6 121.6(6) . . ?
O5 C23 C11 125.8(6) . . ?
O6 C23 C11 112.6(5) . . ?
C12 N1 C3 122.3(5) . . ?
C12 N1 C8 119.7(5) . . ?
C3 N1 C8 110.5(4) . . ?
C2 O1 C7 116.7(4) . . ?
C17 O2 C8 115.4(4) . . ?
C20 O4 C21 115.8(6) . . ?
C23 O6 C24 116.7(5) . . ?

_refine_diff_density_max         0.563
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.099



