# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
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data_mo_szj55q_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2115491'
loop_
_audit_author_name
_audit_author_address
'Zhaojiang Shi'
;FuZhou University
China
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_audit_creation_date             2021-03-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 N O6 S'
_chemical_formula_sum            'C24 H19 N O6 S'
_chemical_formula_weight         449.46
_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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.649(3)
_cell_length_b                   14.265(3)
_cell_length_c                   11.970(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.46(3)
_cell_angle_gamma                90
_cell_volume                     2153.9(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.346
_cell_measurement_theta_min      2.157
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1099 before and 0.0659 after correction.
The Ratio of minimum to maximum transmission is 0.9572.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            99956
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.293
_diffrn_reflns_theta_min         2.155
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3334
_reflns_number_total             5762
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.280
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5762
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1274
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.028
_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)+(0.0408P)²+0.6115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.1075
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_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
S1 S 0.32168(4) 0.57871(3) 0.06664(4) 0.03087(13) Uani 1 1 d . . . . .
O1 O 0.33389(11) 0.65246(9) 0.30957(11) 0.0354(3) Uani 1 1 d . . . . .
O2 O 0.51668(10) 0.43631(9) 0.21243(11) 0.0355(3) Uani 1 1 d . . . . .
O3 O 0.25403(9) 0.37458(8) 0.11791(10) 0.0290(3) Uani 1 1 d . . . . .
O4 O 0.13771(10) 0.44237(10) 0.18604(12) 0.0431(4) Uani 1 1 d . . . . .
O5 O 0.22456(10) 0.62942(9) 0.03135(11) 0.0380(3) Uani 1 1 d . . . . .
O6 O 0.33445(10) 0.50821(9) -0.01137(11) 0.0364(3) Uani 1 1 d . . . . .
N1 N 0.33712(12) 0.52181(10) 0.19509(12) 0.0279(3) Uani 1 1 d . . . . .
C1 C 0.34084(14) 0.56849(13) 0.30026(15) 0.0289(4) Uani 1 1 d . . . . .
C2 C 0.35452(14) 0.49462(12) 0.39052(15) 0.0276(4) Uani 1 1 d . . . . .
C3 C 0.36374(15) 0.50463(13) 0.50925(16) 0.0332(4) Uani 1 1 d . . . . .
H3 H 0.364662 0.563543 0.542912 0.040 Uiso 1 1 calc R U . . .
C4 C 0.37154(16) 0.42358(14) 0.57601(16) 0.0372(5) Uani 1 1 d . . . . .
H4 H 0.377759 0.427855 0.655969 0.045 Uiso 1 1 calc R U . . .
C5 C 0.37016(15) 0.33649(14) 0.52484(16) 0.0357(5) Uani 1 1 d . . . . .
H5 H 0.376032 0.283065 0.571492 0.043 Uiso 1 1 calc R U . . .
C6 C 0.36021(14) 0.32668(13) 0.40526(16) 0.0318(4) Uani 1 1 d . . . . .
H6 H 0.359010 0.267841 0.371298 0.038 Uiso 1 1 calc R U . . .
C7 C 0.35217(14) 0.40760(12) 0.33898(15) 0.0266(4) Uani 1 1 d . . . . .
C8 C 0.34288(14) 0.41933(12) 0.20804(15) 0.0268(4) Uani 1 1 d . . . . .
C9 C 0.44503(15) 0.38071(12) 0.19601(14) 0.0272(4) Uani 1 1 d . . . . .
C10 C 0.45981(14) 0.27930(12) 0.17589(15) 0.0283(4) Uani 1 1 d . . . . .
C11 C 0.38701(15) 0.20851(13) 0.16616(16) 0.0326(4) Uani 1 1 d . . . . .
H11 H 0.321733 0.222998 0.169460 0.039 Uiso 1 1 calc R U . . .
C12 C 0.41184(17) 0.11630(14) 0.15155(19) 0.0426(5) Uani 1 1 d . . . . .
H12 H 0.363698 0.068896 0.147042 0.051 Uiso 1 1 calc R U . . .
C13 C 0.50694(18) 0.09438(15) 0.1437(2) 0.0494(6) Uani 1 1 d . . . . .
H13 H 0.522451 0.032379 0.132827 0.059 Uiso 1 1 calc R U . . .
C14 C 0.57949(18) 0.16383(15) 0.1517(2) 0.0489(6) Uani 1 1 d . . . . .
H14 H 0.643933 0.148885 0.146540 0.059 Uiso 1 1 calc R U . . .
C15 C 0.55584(16) 0.25589(14) 0.16764(17) 0.0379(5) Uani 1 1 d . . . . .
H15 H 0.604730 0.302796 0.172884 0.045 Uiso 1 1 calc R U . . .
C16 C 0.15363(15) 0.39410(13) 0.11360(17) 0.0331(4) Uani 1 1 d . . . . .
C17 C 0.07298(17) 0.34654(16) 0.00745(19) 0.0467(5) Uani 1 1 d . . . . .
H17A H 0.086866 0.360050 -0.063692 0.070 Uiso 1 1 calc R U . . .
H17B H 0.003594 0.368839 -0.003314 0.070 Uiso 1 1 calc R U . . .
H17C H 0.076499 0.280060 0.020932 0.070 Uiso 1 1 calc R U . . .
C18 C 0.42707(15) 0.65892(13) 0.10679(16) 0.0315(4) Uani 1 1 d . . . . .
C19 C 0.52198(16) 0.63201(14) 0.09870(16) 0.0340(5) Uani 1 1 d . . . . .
H19 H 0.530951 0.571421 0.075525 0.041 Uiso 1 1 calc R U . . .
C20 C 0.60286(16) 0.69714(14) 0.12580(17) 0.0378(5) Uani 1 1 d . . . . .
H20 H 0.666562 0.679777 0.120365 0.045 Uiso 1 1 calc R U . . .
C21 C 0.59110(16) 0.78819(14) 0.16107(17) 0.0392(5) Uani 1 1 d . . . . .
C22 C 0.49553(17) 0.81238(14) 0.16989(18) 0.0396(5) Uani 1 1 d . . . . .
H22 H 0.486925 0.872455 0.194920 0.048 Uiso 1 1 calc R U . . .
C23 C 0.41368(16) 0.74923(13) 0.14235(17) 0.0366(5) Uani 1 1 d . . . . .
H23 H 0.349881 0.766724 0.147433 0.044 Uiso 1 1 calc R U . . .
C24 C 0.67854(18) 0.85941(16) 0.1871(2) 0.0545(6) Uani 1 1 d . . . . .
H24A H 0.703917 0.876948 0.270847 0.082 Uiso 1 1 calc R U . . .
H24B H 0.651799 0.913856 0.137691 0.082 Uiso 1 1 calc R U . . .
H24C H 0.735620 0.832814 0.169465 0.082 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
S1 O5 1.4252(14) . ?
S1 O6 1.4277(13) . ?
S1 N1 1.6792(14) . ?
S1 C18 1.755(2) . ?
O1 C1 1.210(2) . ?
O2 C9 1.216(2) . ?
O3 C8 1.429(2) . ?
O3 C16 1.380(2) . ?
O4 C16 1.191(2) . ?
N1 C1 1.408(2) . ?
N1 C8 1.469(2) . ?
C1 C2 1.469(2) . ?
C2 C3 1.385(2) . ?
C2 C7 1.381(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(2) . ?
C7 C8 1.533(2) . ?
C8 C9 1.556(3) . ?
C9 C10 1.493(2) . ?
C10 C11 1.390(3) . ?
C10 C15 1.392(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.489(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.389(3) . ?
C18 C23 1.391(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.394(3) . ?
C21 C22 1.392(3) . ?
C21 C24 1.506(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(3) . ?
C23 H23 0.9300 . ?
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
O5 S1 O6 119.72(8) . . ?
O5 S1 N1 107.09(8) . . ?
O5 S1 C18 108.82(9) . . ?
O6 S1 N1 104.74(7) . . ?
O6 S1 C18 110.26(9) . . ?
N1 S1 C18 105.15(8) . . ?
C16 O3 C8 118.84(13) . . ?
C1 N1 S1 122.63(12) . . ?
C1 N1 C8 113.21(13) . . ?
C8 N1 S1 124.10(11) . . ?
O1 C1 N1 124.98(16) . . ?
O1 C1 C2 129.39(16) . . ?
N1 C1 C2 105.63(15) . . ?
C3 C2 C1 128.08(16) . . ?
C7 C2 C1 109.96(15) . . ?
C7 C2 C3 121.90(16) . . ?
C2 C3 H3 121.2 . . ?
C2 C3 C4 117.54(17) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.60(17) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.70(17) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 H6 121.2 . . ?
C7 C6 C5 117.50(17) . . ?
C7 C6 H6 121.2 . . ?
C2 C7 C6 120.75(16) . . ?
C2 C7 C8 109.72(14) . . ?
C6 C7 C8 129.51(16) . . ?
O3 C8 N1 111.65(14) . . ?
O3 C8 C7 115.98(14) . . ?
O3 C8 C9 107.69(13) . . ?
N1 C8 C7 101.35(13) . . ?
N1 C8 C9 110.88(14) . . ?
C7 C8 C9 109.20(14) . . ?
O2 C9 C8 116.62(15) . . ?
O2 C9 C10 120.56(17) . . ?
C10 C9 C8 122.62(15) . . ?
C11 C10 C9 125.53(17) . . ?
C11 C10 C15 118.82(17) . . ?
C15 C10 C9 115.65(16) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.90(18) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.53(19) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.88(19) . . ?
C14 C15 H15 119.6 . . ?
O3 C16 C17 109.87(17) . . ?
O4 C16 O3 122.99(17) . . ?
O4 C16 C17 127.14(19) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 S1 119.29(15) . . ?
C19 C18 C23 120.82(18) . . ?
C23 C18 S1 119.86(15) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.68(18) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 119.2 . . ?
C19 C20 C21 121.53(19) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 C24 121.15(19) . . ?
C22 C21 C20 118.28(19) . . ?
C22 C21 C24 120.56(19) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.28(19) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 H23 120.3 . . ?
C22 C23 C18 119.41(19) . . ?
C22 C23 H23 120.3 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 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
S1 N1 C1 O1 -0.3(3) . . . . ?
S1 N1 C1 C2 179.79(12) . . . . ?
S1 N1 C8 O3 -53.70(19) . . . . ?
S1 N1 C8 C7 -177.79(12) . . . . ?
S1 N1 C8 C9 66.39(18) . . . . ?
S1 C18 C19 C20 177.35(14) . . . . ?
S1 C18 C23 C22 -177.95(14) . . . . ?
O1 C1 C2 C3 -0.7(3) . . . . ?
O1 C1 C2 C7 176.37(19) . . . . ?
O2 C9 C10 C11 174.38(17) . . . . ?
O2 C9 C10 C15 -5.0(2) . . . . ?
O3 C8 C9 O2 142.50(15) . . . . ?
O3 C8 C9 C10 -42.62(19) . . . . ?
O5 S1 N1 C1 -58.41(16) . . . . ?
O5 S1 N1 C8 118.52(14) . . . . ?
O5 S1 C18 C19 -154.99(14) . . . . ?
O5 S1 C18 C23 22.90(17) . . . . ?
O6 S1 N1 C1 173.48(14) . . . . ?
O6 S1 N1 C8 -9.60(16) . . . . ?
O6 S1 C18 C19 -21.83(16) . . . . ?
O6 S1 C18 C23 156.06(14) . . . . ?
N1 S1 C18 C19 90.56(15) . . . . ?
N1 S1 C18 C23 -91.55(16) . . . . ?
N1 C1 C2 C3 179.26(18) . . . . ?
N1 C1 C2 C7 -3.7(2) . . . . ?
N1 C8 C9 O2 20.1(2) . . . . ?
N1 C8 C9 C10 -165.05(14) . . . . ?
C1 N1 C8 O3 123.48(15) . . . . ?
C1 N1 C8 C7 -0.60(18) . . . . ?
C1 N1 C8 C9 -116.43(16) . . . . ?
C1 C2 C3 C4 177.28(18) . . . . ?
C1 C2 C7 C6 -178.00(16) . . . . ?
C1 C2 C7 C8 3.4(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C7 C8 O3 -122.85(16) . . . . ?
C2 C7 C8 N1 -1.76(18) . . . . ?
C2 C7 C8 C9 115.30(16) . . . . ?
C3 C2 C7 C6 -0.7(3) . . . . ?
C3 C2 C7 C8 -179.31(17) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C5 C6 C7 C2 0.3(3) . . . . ?
C5 C6 C7 C8 178.57(17) . . . . ?
C6 C7 C8 O3 58.7(2) . . . . ?
C6 C7 C8 N1 179.82(18) . . . . ?
C6 C7 C8 C9 -63.1(2) . . . . ?
C7 C2 C3 C4 0.5(3) . . . . ?
C7 C8 C9 O2 -90.78(18) . . . . ?
C7 C8 C9 C10 84.11(18) . . . . ?
C8 O3 C16 O4 -4.6(3) . . . . ?
C8 O3 C16 C17 175.33(15) . . . . ?
C8 N1 C1 O1 -177.49(17) . . . . ?
C8 N1 C1 C2 2.56(19) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C8 C9 C10 C15 -179.71(15) . . . . ?
C9 C10 C11 C12 -177.81(17) . . . . ?
C9 C10 C15 C14 178.56(18) . . . . ?
C10 C11 C12 C13 -1.6(3) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C10 0.2(3) . . . . ?
C15 C10 C11 C12 1.6(3) . . . . ?
C16 O3 C8 N1 -60.97(18) . . . . ?
C16 O3 C8 C7 54.4(2) . . . . ?
C16 O3 C8 C9 177.09(13) . . . . ?
C18 S1 N1 C1 57.24(16) . . . . ?
C18 S1 N1 C8 -125.83(14) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C18 C23 C22 -0.1(3) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C19 C20 C21 C24 -178.32(18) . . . . ?
C20 C21 C22 C23 -1.3(3) . . . . ?
C21 C22 C23 C18 1.0(3) . . . . ?
C23 C18 C19 C20 -0.5(3) . . . . ?
C24 C21 C22 C23 177.70(19) . . . . ?

_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_ln-22n-1
_database_code_depnum_ccdc_archive 'CCDC 2115493'
loop_
_audit_author_name
_audit_author_address
'Zhaojiang Shi'
;FuZhou University
China
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_audit_creation_date             2021-09-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 Br O3'
_chemical_formula_sum            'C15 H11 Br O3'
_chemical_formula_weight         319.15
_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'
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                   6.8870(4)
_cell_length_b                   8.0452(6)
_cell_length_c                   12.4860(10)
_cell_angle_alpha                91.227(3)
_cell_angle_beta                 91.751(3)
_cell_angle_gamma                113.005(2)
_cell_volume                     636.08(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5433
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.006
_cell_measurement_theta_min      3.150
_shelx_estimated_absorpt_T_max   0.738
_shelx_estimated_absorpt_T_min   0.564
_exptl_absorpt_coefficient_mu    3.231
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.4517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1646 before and 0.0736 after correction.
The Ratio of minimum to maximum transmission is 0.6048.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.760
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17388
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.316
_diffrn_reflns_theta_min         2.752
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.760
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2508
_reflns_number_total             4043
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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         0.882
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         4043
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.026
_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)+(0.0464P)²+0.0815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1145
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H008), C8(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H00A), C12(H00C), C3(H00D), C14(H00F), C15(H00G), C11(H00H), C5(H00I),
 C4(H00J)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H003)
;
_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
Br1 Br -0.27934(5) 0.27340(4) 1.03248(2) 0.05324(14) Uani 1 1 d . . . . .
O2 O 0.3663(3) 0.1858(2) 0.50404(13) 0.0298(4) Uani 1 1 d . . . . .
O3 O 0.3089(3) 0.0077(2) 0.69427(14) 0.0318(4) Uani 1 1 d . . . . .
H003 H 0.317733 -0.066246 0.650530 0.048 Uiso 1 1 calc R U . . .
O1 O 0.6998(3) 0.2440(2) 0.45962(15) 0.0388(4) Uani 1 1 d . . . . .
C10 C 0.0496(3) 0.1134(3) 0.75039(18) 0.0223(5) Uani 1 1 d . . . . .
C2 C 0.6247(4) 0.4075(3) 0.60614(19) 0.0267(5) Uani 1 1 d . . . . .
C7 C 0.4349(4) 0.3921(3) 0.64760(19) 0.0258(5) Uani 1 1 d . . . . .
C9 C 0.1570(4) 0.0702(3) 0.65717(18) 0.0241(5) Uani 1 1 d . . . . .
H008 H 0.051128 -0.025000 0.611690 0.029 Uiso 1 1 calc R U . . .
C1 C 0.5779(4) 0.2747(3) 0.51658(19) 0.0286(5) Uani 1 1 d . . . . .
C6 C 0.4335(4) 0.5090(3) 0.7311(2) 0.0299(5) Uani 1 1 d . . . . .
H00A H 0.307474 0.503628 0.758821 0.036 Uiso 1 1 calc R U . . .
C13 C -0.1460(4) 0.2080(3) 0.9178(2) 0.0303(5) Uani 1 1 d . . . . .
C12 C 0.0464(4) 0.1952(4) 0.9368(2) 0.0346(6) Uani 1 1 d . . . . .
H00C H 0.110548 0.218848 1.005201 0.041 Uiso 1 1 calc R U . . .
C3 C 0.8177(4) 0.5310(3) 0.6460(2) 0.0321(6) Uani 1 1 d . . . . .
H00D H 0.943376 0.538387 0.616989 0.039 Uiso 1 1 calc R U . . .
C8 C 0.2612(4) 0.2386(3) 0.58989(18) 0.0263(5) Uani 1 1 d . . . . .
H00E H 0.154239 0.278855 0.560126 0.032 Uiso 1 1 calc R U . . .
C14 C -0.2432(4) 0.1724(3) 0.8179(2) 0.0336(6) Uani 1 1 d . . . . .
H00F H -0.373453 0.179977 0.806229 0.040 Uiso 1 1 calc R U . . .
C15 C -0.1451(4) 0.1250(3) 0.7345(2) 0.0289(5) Uani 1 1 d . . . . .
H00G H -0.210760 0.100449 0.666433 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1416(4) 0.1470(3) 0.8532(2) 0.0305(5) Uani 1 1 d . . . . .
H00H H 0.270100 0.136664 0.865920 0.037 Uiso 1 1 calc R U . . .
C5 C 0.6259(4) 0.6334(3) 0.7714(2) 0.0361(6) Uani 1 1 d . . . . .
H00I H 0.628296 0.712752 0.827183 0.043 Uiso 1 1 calc R U . . .
C4 C 0.8157(4) 0.6432(3) 0.7310(2) 0.0349(6) Uani 1 1 d . . . . .
H00J H 0.942557 0.726001 0.761466 0.042 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
Br1 C13 1.896(2) . ?
O2 C1 1.351(3) . ?
O2 C8 1.457(3) . ?
O3 H003 0.8200 . ?
O3 C9 1.397(3) . ?
O1 C1 1.210(3) . ?
C10 C9 1.503(3) . ?
C10 C15 1.388(3) . ?
C10 C11 1.387(3) . ?
C2 C7 1.381(3) . ?
C2 C1 1.468(3) . ?
C2 C3 1.381(4) . ?
C7 C6 1.392(3) . ?
C7 C8 1.493(3) . ?
C9 H008 0.9800 . ?
C9 C8 1.543(3) . ?
C6 H00A 0.9300 . ?
C6 C5 1.383(4) . ?
C13 C12 1.382(4) . ?
C13 C14 1.367(4) . ?
C12 H00C 0.9300 . ?
C12 C11 1.376(3) . ?
C3 H00D 0.9300 . ?
C3 C4 1.382(4) . ?
C8 H00E 0.9800 . ?
C14 H00F 0.9300 . ?
C14 C15 1.384(3) . ?
C15 H00G 0.9300 . ?
C11 H00H 0.9300 . ?
C5 H00I 0.9300 . ?
C5 C4 1.390(4) . ?
C4 H00J 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C8 110.36(18) . . ?
C9 O3 H003 109.5 . . ?
C15 C10 C9 120.0(2) . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 C15 118.1(2) . . ?
C7 C2 C1 107.7(2) . . ?
C3 C2 C7 123.1(2) . . ?
C3 C2 C1 129.2(2) . . ?
C2 C7 C6 119.6(2) . . ?
C2 C7 C8 108.6(2) . . ?
C6 C7 C8 131.8(2) . . ?
O3 C9 C10 109.89(18) . . ?
O3 C9 H008 108.8 . . ?
O3 C9 C8 110.03(19) . . ?
C10 C9 H008 108.8 . . ?
C10 C9 C8 110.59(18) . . ?
C8 C9 H008 108.8 . . ?
O2 C1 C2 108.78(19) . . ?
O1 C1 O2 122.6(2) . . ?
O1 C1 C2 128.6(2) . . ?
C7 C6 H00A 121.1 . . ?
C5 C6 C7 117.7(2) . . ?
C5 C6 H00A 121.1 . . ?
C12 C13 Br1 119.5(2) . . ?
C14 C13 Br1 119.31(18) . . ?
C14 C13 C12 121.2(2) . . ?
C13 C12 H00C 120.4 . . ?
C11 C12 C13 119.1(2) . . ?
C11 C12 H00C 120.4 . . ?
C2 C3 H00D 121.5 . . ?
C2 C3 C4 117.1(2) . . ?
C4 C3 H00D 121.5 . . ?
O2 C8 C7 103.92(18) . . ?
O2 C8 C9 106.70(17) . . ?
O2 C8 H00E 110.4 . . ?
C7 C8 C9 114.68(19) . . ?
C7 C8 H00E 110.4 . . ?
C9 C8 H00E 110.4 . . ?
C13 C14 H00F 120.5 . . ?
C13 C14 C15 119.1(2) . . ?
C15 C14 H00F 120.5 . . ?
C10 C15 H00G 119.4 . . ?
C14 C15 C10 121.3(2) . . ?
C14 C15 H00G 119.4 . . ?
C10 C11 H00H 119.4 . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H00H 119.4 . . ?
C6 C5 H00I 119.0 . . ?
C6 C5 C4 121.9(2) . . ?
C4 C5 H00I 119.0 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H00J 119.7 . . ?
C5 C4 H00J 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C13 C12 C11 179.7(2) . . . . ?
Br1 C13 C14 C15 179.92(18) . . . . ?
O3 C9 C8 O2 56.6(2) . . . . ?
O3 C9 C8 C7 -57.8(2) . . . . ?
C10 C9 C8 O2 178.23(18) . . . . ?
C10 C9 C8 C7 63.8(2) . . . . ?
C2 C7 C6 C5 -2.0(3) . . . . ?
C2 C7 C8 O2 -7.2(2) . . . . ?
C2 C7 C8 C9 108.8(2) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C7 C2 C1 O2 1.2(2) . . . . ?
C7 C2 C1 O1 -179.4(2) . . . . ?
C7 C2 C3 C4 -0.4(3) . . . . ?
C7 C6 C5 C4 0.0(4) . . . . ?
C9 C10 C15 C14 -177.1(2) . . . . ?
C9 C10 C11 C12 176.7(2) . . . . ?
C1 O2 C8 C7 8.1(2) . . . . ?
C1 O2 C8 C9 -113.44(19) . . . . ?
C1 C2 C7 C6 -177.2(2) . . . . ?
C1 C2 C7 C8 3.9(2) . . . . ?
C1 C2 C3 C4 179.0(2) . . . . ?
C6 C7 C8 O2 174.1(2) . . . . ?
C6 C7 C8 C9 -69.8(3) . . . . ?
C6 C5 C4 C3 2.0(4) . . . . ?
C13 C12 C11 C10 0.8(4) . . . . ?
C13 C14 C15 C10 -0.1(4) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C3 C2 C7 C6 2.3(3) . . . . ?
C3 C2 C7 C8 -176.6(2) . . . . ?
C3 C2 C1 O2 -178.2(2) . . . . ?
C3 C2 C1 O1 1.1(4) . . . . ?
C8 O2 C1 O1 174.6(2) . . . . ?
C8 O2 C1 C2 -6.0(2) . . . . ?
C8 C7 C6 C5 176.5(2) . . . . ?
C14 C13 C12 C11 0.5(4) . . . . ?
C15 C10 C9 O3 -160.6(2) . . . . ?
C15 C10 C9 C8 77.7(3) . . . . ?
C15 C10 C11 C12 -1.7(4) . . . . ?
C11 C10 C9 O3 21.0(3) . . . . ?
C11 C10 C9 C8 -100.7(2) . . . . ?
C11 C10 C15 C14 1.4(3) . . . . ?

_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_ln22u2_0m
_database_code_depnum_ccdc_archive 'CCDC 2115495'
loop_
_audit_author_name
_audit_author_address
'Zhaojiang Shi'
;FuZhou University
China
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_audit_creation_date             2021-10-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 Br O2'
_chemical_formula_sum            'C15 H9 Br O2'
_chemical_formula_weight         301.13
_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'
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                   7.106(10)
_cell_length_b                   7.215(11)
_cell_length_c                   13.194(19)
_cell_angle_alpha                104.92(6)
_cell_angle_beta                 94.22(7)
_cell_angle_gamma                111.29(6)
_cell_volume                     598.4(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4887
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.683
_cell_measurement_theta_min      3.099
_shelx_estimated_absorpt_T_max   0.726
_shelx_estimated_absorpt_T_min   0.548
_exptl_absorpt_coefficient_mu    3.423
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1361 before and 0.0726 after correction.
The Ratio of minimum to maximum transmission is 0.6516.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12879
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.109
_diffrn_reflns_theta_max         25.109
_diffrn_reflns_theta_min         3.100
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1749
_reflns_number_total             2123
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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         0.740
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.082
_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)+(0.0589P)²+0.1058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H008), C12(H009), C15(H00B), C14(H00C), C11(H00D), C6(H00E), C3(H00G),
 C5(H00H), C4(H00I)
;
_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
Br1 Br 0.68276(6) 0.35500(6) 0.93941(3) 0.0457(2) Uani 1 1 d . . . . .
O2 O 0.2426(3) 0.4558(3) 0.49367(19) 0.0271(5) Uani 1 1 d . . . . .
O1 O 0.1348(4) 0.6391(4) 0.4120(2) 0.0359(6) Uani 1 1 d . . . . .
C9 C 0.2548(5) 0.2709(5) 0.4992(3) 0.0245(7) Uani 1 1 d . . . . .
C10 C 0.3531(5) 0.2906(5) 0.6055(3) 0.0262(8) Uani 1 1 d . . . . .
C7 C 0.0851(5) 0.1045(5) 0.3151(3) 0.0257(8) Uani 1 1 d . . . . .
C2 C 0.0595(5) 0.2863(5) 0.3115(3) 0.0267(8) Uani 1 1 d . . . . .
C8 C 0.1816(5) 0.1012(5) 0.4135(3) 0.0258(7) Uani 1 1 d . . . . .
H008 H 0.193542 -0.020839 0.417785 0.031 Uiso 1 1 calc R U . . .
C12 C 0.5105(5) 0.4956(6) 0.7886(3) 0.0345(9) Uani 1 1 d . . . . .
H009 H 0.549618 0.619403 0.844112 0.041 Uiso 1 1 calc R U . . .
C13 C 0.5473(5) 0.3291(6) 0.8043(3) 0.0320(8) Uani 1 1 d . . . . .
C15 C 0.3898(5) 0.1234(5) 0.6243(3) 0.0289(8) Uani 1 1 d . . . . .
H00B H 0.348523 -0.001683 0.569439 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4861(5) 0.1418(6) 0.7229(3) 0.0312(8) Uani 1 1 d . . . . .
H00C H 0.509789 0.029977 0.734942 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4142(5) 0.4752(6) 0.6886(3) 0.0291(8) Uani 1 1 d . . . . .
H00D H 0.390149 0.587281 0.677065 0.035 Uiso 1 1 calc R U . . .
C6 C 0.0120(5) -0.0673(5) 0.2228(3) 0.0301(8) Uani 1 1 d . . . . .
H00E H 0.027766 -0.189341 0.223692 0.036 Uiso 1 1 calc R U . . .
C1 C 0.1430(5) 0.4723(6) 0.4050(3) 0.0274(8) Uani 1 1 d . . . . .
C3 C -0.0374(5) 0.2943(6) 0.2183(3) 0.0332(9) Uani 1 1 d . . . . .
H00G H -0.054104 0.415625 0.216715 0.040 Uiso 1 1 calc R U . . .
C5 C -0.0825(5) -0.0585(6) 0.1309(3) 0.0365(9) Uani 1 1 d . . . . .
H00H H -0.129303 -0.173975 0.069991 0.044 Uiso 1 1 calc R U . . .
C4 C -0.1089(5) 0.1222(6) 0.1280(3) 0.0396(9) Uani 1 1 d . . . . .
H00I H -0.174339 0.127112 0.065602 0.048 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
Br1 C13 1.894(5) . ?
O2 C9 1.388(4) . ?
O2 C1 1.377(5) . ?
O1 C1 1.205(4) . ?
C9 C10 1.468(5) . ?
C9 C8 1.336(5) . ?
C10 C15 1.399(5) . ?
C10 C11 1.386(5) . ?
C7 C2 1.400(5) . ?
C7 C8 1.433(5) . ?
C7 C6 1.397(5) . ?
C2 C1 1.462(6) . ?
C2 C3 1.389(5) . ?
C8 H008 0.9300 . ?
C12 H009 0.9300 . ?
C12 C13 1.379(6) . ?
C12 C11 1.388(5) . ?
C13 C14 1.387(6) . ?
C15 H00B 0.9300 . ?
C15 C14 1.376(5) . ?
C14 H00C 0.9300 . ?
C11 H00D 0.9300 . ?
C6 H00E 0.9300 . ?
C6 C5 1.370(5) . ?
C3 H00G 0.9300 . ?
C3 C4 1.382(6) . ?
C5 H00H 0.9300 . ?
C5 C4 1.393(6) . ?
C4 H00I 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C9 123.2(3) . . ?
O2 C9 C10 112.3(3) . . ?
C8 C9 O2 120.3(3) . . ?
C8 C9 C10 127.4(3) . . ?
C15 C10 C9 120.3(3) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 C15 118.7(3) . . ?
C2 C7 C8 118.8(3) . . ?
C6 C7 C2 118.3(3) . . ?
C6 C7 C8 122.9(3) . . ?
C7 C2 C1 119.8(3) . . ?
C3 C2 C7 120.6(3) . . ?
C3 C2 C1 119.5(3) . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H008 119.5 . . ?
C7 C8 H008 119.5 . . ?
C13 C12 H009 120.5 . . ?
C13 C12 C11 118.9(3) . . ?
C11 C12 H009 120.5 . . ?
C12 C13 Br1 119.6(3) . . ?
C12 C13 C14 121.3(4) . . ?
C14 C13 Br1 119.1(3) . . ?
C10 C15 H00B 119.6 . . ?
C14 C15 C10 120.8(3) . . ?
C14 C15 H00B 119.6 . . ?
C13 C14 H00C 120.4 . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H00C 120.4 . . ?
C10 C11 C12 121.0(4) . . ?
C10 C11 H00D 119.5 . . ?
C12 C11 H00D 119.5 . . ?
C7 C6 H00E 119.5 . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 H00E 119.5 . . ?
O2 C1 C2 116.6(3) . . ?
O1 C1 O2 116.7(3) . . ?
O1 C1 C2 126.6(3) . . ?
C2 C3 H00G 120.0 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H00G 120.0 . . ?
C6 C5 H00H 119.8 . . ?
C6 C5 C4 120.5(3) . . ?
C4 C5 H00H 119.8 . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H00I 120.2 . . ?
C5 C4 H00I 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C13 C14 C15 -179.2(2) . . . . ?
O2 C9 C10 C15 -176.2(3) . . . . ?
O2 C9 C10 C11 2.8(4) . . . . ?
O2 C9 C8 C7 -1.5(5) . . . . ?
C9 O2 C1 O1 176.5(3) . . . . ?
C9 O2 C1 C2 -4.0(4) . . . . ?
C9 C10 C15 C14 178.5(3) . . . . ?
C9 C10 C11 C12 -178.8(3) . . . . ?
C10 C9 C8 C7 178.6(3) . . . . ?
C10 C15 C14 C13 -0.1(5) . . . . ?
C7 C2 C1 O2 -0.7(4) . . . . ?
C7 C2 C1 O1 178.7(3) . . . . ?
C7 C2 C3 C4 -0.2(5) . . . . ?
C7 C6 C5 C4 -0.5(5) . . . . ?
C2 C7 C8 C9 -3.1(5) . . . . ?
C2 C7 C6 C5 0.0(5) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C8 C9 C10 C15 3.7(5) . . . . ?
C8 C9 C10 C11 -177.3(3) . . . . ?
C8 C7 C2 C1 4.1(4) . . . . ?
C8 C7 C2 C3 -178.6(3) . . . . ?
C8 C7 C6 C5 178.9(3) . . . . ?
C12 C13 C14 C15 1.1(5) . . . . ?
C13 C12 C11 C10 0.7(5) . . . . ?
C15 C10 C11 C12 0.2(5) . . . . ?
C11 C10 C15 C14 -0.5(5) . . . . ?
C11 C12 C13 Br1 178.9(2) . . . . ?
C11 C12 C13 C14 -1.4(5) . . . . ?
C6 C7 C2 C1 -177.0(3) . . . . ?
C6 C7 C2 C3 0.3(5) . . . . ?
C6 C7 C8 C9 178.1(3) . . . . ?
C6 C5 C4 C3 0.6(5) . . . . ?
C1 O2 C9 C10 -174.9(3) . . . . ?
C1 O2 C9 C8 5.2(4) . . . . ?
C1 C2 C3 C4 177.1(3) . . . . ?
C3 C2 C1 O2 -178.1(3) . . . . ?
C3 C2 C1 O1 1.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
