# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

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

data_2101225864_0m
_database_code_depnum_ccdc_archive 'CCDC 2088807'
loop_
_audit_author_name
_audit_author_address
'Ma Tao'
;NJtech
China
;
_audit_update_record             
;
2021-06-08 deposited with the CCDC.	2021-09-24 downloaded from the CCDC.
;
_audit_creation_date             2021-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 Br N O4 S'
_chemical_formula_sum            'C14 H10 Br N O4 S'
_chemical_formula_weight         368.20
_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 0.0148 0.0070 '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 -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 '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                   8.6786(3)
_cell_length_b                   10.8331(4)
_cell_length_c                   14.7625(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.0010(10)
_cell_angle_gamma                90
_cell_volume                     1374.40(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.989
_cell_measurement_theta_min      4.869
_shelx_estimated_absorpt_T_max   0.832
_shelx_estimated_absorpt_T_min   0.725
_exptl_absorpt_coefficient_mu    3.823
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1623 before and 0.0815 after correction. The Ratio of minimum to maximum transmission is 0.6606. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13547
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.963
_diffrn_reflns_theta_min         4.419
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2523
_reflns_number_total             2612
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.277
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.050
_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)+(0.0671P)²+0.7184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1016
_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:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.49122(3) 0.77492(2) 0.20465(2) 0.03442(14) Uani 1 1 d . . . . .
S1 S 0.29716(6) 0.50067(5) 0.15868(3) 0.02598(16) Uani 1 1 d . . . . .
O1 O 0.46375(19) 0.32613(15) 0.29856(10) 0.0298(3) Uani 1 1 d . . . . .
O2 O 0.05946(19) 0.59268(18) 0.29422(12) 0.0374(4) Uani 1 1 d . . . . .
H2 H 0.041406 0.650960 0.256714 0.056 Uiso 1 1 calc GR . . . .
O3 O 0.20763(18) 0.60680(16) 0.12862(10) 0.0319(4) Uani 1 1 d . . . . .
O4 O 0.2485(2) 0.38215(17) 0.12349(11) 0.0373(4) Uani 1 1 d . . . . .
N1 N 0.3024(2) 0.49689(17) 0.27140(12) 0.0264(4) Uani 1 1 d . . . . .
C1 C 0.2186(3) 0.5869(2) 0.32483(15) 0.0278(5) Uani 1 1 d . . . . .
H1 H 0.266877 0.670673 0.324882 0.033 Uiso 1 1 calc R . . . .
C2 C 0.2492(3) 0.5293(2) 0.41831(15) 0.0272(5) Uani 1 1 d . . . . .
C3 C 0.1911(3) 0.5670(2) 0.49682(16) 0.0335(5) Uani 1 1 d . . . . .
H3 H 0.125843 0.637420 0.496800 0.040 Uiso 1 1 calc R . . . .
C4 C 0.2329(3) 0.4970(3) 0.57577(16) 0.0367(6) Uani 1 1 d . . . . .
H4 H 0.193756 0.519490 0.630426 0.044 Uiso 1 1 calc R . . . .
C5 C 0.3301(3) 0.3955(2) 0.57642(15) 0.0359(5) Uani 1 1 d . . . . .
H5 H 0.357663 0.350780 0.631666 0.043 Uiso 1 1 calc R . . . .
C6 C 0.3884(3) 0.3577(2) 0.49743(15) 0.0295(5) Uani 1 1 d . . . . .
H6 H 0.454893 0.288026 0.497416 0.035 Uiso 1 1 calc R . . . .
C7 C 0.3447(2) 0.4265(2) 0.41912(14) 0.0244(4) Uani 1 1 d . . . . .
C8 C 0.3817(2) 0.4044(2) 0.32584(14) 0.0242(4) Uani 1 1 d . . . . .
C9 C 0.4933(3) 0.5212(2) 0.14109(14) 0.0261(4) Uani 1 1 d . . . . .
C10 C 0.5745(2) 0.6315(2) 0.15706(14) 0.0272(4) Uani 1 1 d . . . . .
C11 C 0.7269(3) 0.6405(3) 0.13786(16) 0.0361(5) Uani 1 1 d . . . . .
H11 H 0.782612 0.715721 0.148676 0.043 Uiso 1 1 calc R . . . .
C12 C 0.7967(3) 0.5397(3) 0.10306(18) 0.0438(7) Uani 1 1 d . . . . .
H12 H 0.900271 0.546348 0.089543 0.053 Uiso 1 1 calc R . . . .
C13 C 0.7180(3) 0.4299(3) 0.08780(18) 0.0436(6) Uani 1 1 d . . . . .
H13 H 0.767063 0.361071 0.064064 0.052 Uiso 1 1 calc R . . . .
C14 C 0.5661(3) 0.4199(2) 0.10722(16) 0.0361(5) Uani 1 1 d . . . . .
H14 H 0.511912 0.343852 0.097357 0.043 Uiso 1 1 calc R . . . .


_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 C10 1.890(2) . ?
S1 O3 1.4235(17) . ?
S1 O4 1.4269(18) . ?
S1 N1 1.6587(18) . ?
S1 C9 1.772(2) . ?
O1 C8 1.211(3) . ?
O2 H2 0.8400 . ?
O2 C1 1.393(3) . ?
N1 C1 1.504(3) . ?
N1 C8 1.404(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.504(3) . ?
C2 C3 1.388(3) . ?
C2 C7 1.386(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C7 C8 1.477(3) . ?
C9 C10 1.390(3) . ?
C9 C14 1.393(3) . ?
C10 C11 1.394(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.374(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(4) . ?
C14 H14 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
O3 S1 O4 119.48(11) . . ?
O3 S1 N1 105.69(10) . . ?
O3 S1 C9 110.30(10) . . ?
O4 S1 N1 107.97(10) . . ?
O4 S1 C9 107.54(11) . . ?
N1 S1 C9 104.91(10) . . ?
C1 O2 H2 109.5 . . ?
C1 N1 S1 124.22(15) . . ?
C8 N1 S1 122.34(15) . . ?
C8 N1 C1 113.38(17) . . ?
O2 C1 N1 112.91(19) . . ?
O2 C1 H1 110.8 . . ?
O2 C1 C2 110.92(18) . . ?
N1 C1 H1 110.8 . . ?
N1 C1 C2 100.12(18) . . ?
C2 C1 H1 110.8 . . ?
C3 C2 C1 127.2(2) . . ?
C7 C2 C1 111.72(19) . . ?
C7 C2 C3 121.0(2) . . ?
C2 C3 H3 121.5 . . ?
C2 C3 C4 117.0(2) . . ?
C4 C3 H3 121.5 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 121.6 . . ?
C7 C6 C5 116.8(2) . . ?
C7 C6 H6 121.6 . . ?
C2 C7 C8 109.26(18) . . ?
C6 C7 C2 122.3(2) . . ?
C6 C7 C8 128.4(2) . . ?
O1 C8 N1 124.98(19) . . ?
O1 C8 C7 129.7(2) . . ?
N1 C8 C7 105.36(18) . . ?
C10 C9 S1 123.87(17) . . ?
C10 C9 C14 119.6(2) . . ?
C14 C9 S1 116.53(19) . . ?
C9 C10 Br1 123.99(16) . . ?
C9 C10 C11 119.9(2) . . ?
C11 C10 Br1 116.16(19) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.2(2) . . ?
C13 C14 H14 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
