# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_okano_okm_514_autored
_database_code_depnum_ccdc_archive 'CCDC 2184814'
loop_
_audit_author_name
_audit_author_address
'Kentaro Okano'
;Kobe University
Japan
;
_audit_update_record             
;
2022-07-08 deposited with the CCDC.	2022-12-22 downloaded from the CCDC.
;
_audit_creation_date             2022-07-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
okano@harbor.kobe-u.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        
2,4-dibromo-N,N-dimethyl-1H-pyrrole-1-sulfonamide
_chemical_formula_moiety         'C6 H8 Br2 N2 O2 S'
_chemical_formula_sum            'C6 H8 Br2 N2 O2 S'
_chemical_formula_weight         332.02
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.6616(4)
_cell_length_b                   10.2608(3)
_cell_length_c                   7.9533(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.120(3)
_cell_angle_gamma                90
_cell_volume                     1022.92(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14132
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30.8310
_cell_measurement_theta_min      1.8540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.814
_diffrn_reflns_theta_min         1.625
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2564
_reflns_number_total             3030
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.027
_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)+(0.0237P)²+0.9167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0576
_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:
 C4(H4), C2(H2)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C5(H5A,H5B,H5C)
;
_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
Br2 Br 0.84953(2) 0.29865(2) 0.36072(3) 0.01780(7) Uani 1 1 d . . . . .
Br1 Br 0.90311(2) 0.67634(3) 0.90684(3) 0.02854(8) Uani 1 1 d . . . . .
S1 S 0.62815(4) 0.61480(5) 0.75864(7) 0.01309(11) Uani 1 1 d . . . . .
O2 O 0.54210(13) 0.60893(16) 0.6231(2) 0.0183(3) Uani 1 1 d . . . . .
O1 O 0.66073(13) 0.73421(15) 0.8396(2) 0.0201(3) Uani 1 1 d . . . . .
N1 N 0.73443(14) 0.55952(18) 0.6702(2) 0.0134(4) Uani 1 1 d . . . . .
N2 N 0.60562(15) 0.51027(18) 0.8997(2) 0.0150(4) Uani 1 1 d . . . . .
C3 C 0.81970(17) 0.4226(2) 0.5216(3) 0.0130(4) Uani 1 1 d . . . . .
C1 C 0.84301(17) 0.5658(2) 0.7331(3) 0.0160(4) Uani 1 1 d . . . . .
C4 C 0.72145(17) 0.4679(2) 0.5389(3) 0.0135(4) Uani 1 1 d . . . . .
H4 H 0.655960 0.442304 0.473995 0.016 Uiso 1 1 calc R U . . .
C2 C 0.89738(17) 0.4833(2) 0.6427(3) 0.0163(4) Uani 1 1 d . . . . .
H2 H 0.972267 0.469113 0.657500 0.020 Uiso 1 1 calc R U . . .
C6 C 0.56645(19) 0.3811(2) 0.8380(3) 0.0207(5) Uani 1 1 d . . . . .
H6A H 0.513100 0.391703 0.736933 0.031 Uiso 1 1 calc R U . . .
H6B H 0.533997 0.336650 0.926993 0.031 Uiso 1 1 calc R U . . .
H6C H 0.626226 0.329059 0.808939 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6806(2) 0.5058(2) 1.0586(3) 0.0218(5) Uani 1 1 d . . . . .
H5A H 0.745333 0.459026 1.039334 0.033 Uiso 1 1 calc R U . . .
H5B H 0.647221 0.460597 1.146012 0.033 Uiso 1 1 calc R U . . .
H5C H 0.699337 0.594809 1.096412 0.033 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
Br2 C3 1.880(2) . ?
Br1 C1 1.865(2) . ?
S1 O2 1.4215(16) . ?
S1 O1 1.4180(16) . ?
S1 N1 1.7013(19) . ?
S1 N2 1.6063(19) . ?
N1 C1 1.396(3) . ?
N1 C4 1.397(3) . ?
N2 C6 1.475(3) . ?
N2 C5 1.471(3) . ?
C3 C4 1.353(3) . ?
C3 C2 1.419(3) . ?
C1 C2 1.359(3) . ?
C4 H4 0.9500 . ?
C2 H2 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N1 103.81(9) . . ?
O2 S1 N2 107.96(10) . . ?
O1 S1 O2 121.57(10) . . ?
O1 S1 N1 106.22(10) . . ?
O1 S1 N2 109.21(10) . . ?
N2 S1 N1 107.15(9) . . ?
C1 N1 S1 129.26(15) . . ?
C1 N1 C4 107.73(18) . . ?
C4 N1 S1 121.12(15) . . ?
C6 N2 S1 116.90(15) . . ?
C5 N2 S1 117.66(16) . . ?
C5 N2 C6 113.83(18) . . ?
C4 C3 Br2 125.29(16) . . ?
C4 C3 C2 109.82(19) . . ?
C2 C3 Br2 124.88(16) . . ?
N1 C1 Br1 124.84(17) . . ?
C2 C1 Br1 125.92(17) . . ?
C2 C1 N1 109.18(19) . . ?
N1 C4 H4 126.4 . . ?
C3 C4 N1 107.13(19) . . ?
C3 C4 H4 126.4 . . ?
C3 C2 H2 126.9 . . ?
C1 C2 C3 106.13(19) . . ?
C1 C2 H2 126.9 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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
Br2 C3 C4 N1 -179.04(15) . . . . ?
Br2 C3 C2 C1 179.80(16) . . . . ?
Br1 C1 C2 C3 -178.18(16) . . . . ?
S1 N1 C1 Br1 -17.2(3) . . . . ?
S1 N1 C1 C2 165.41(17) . . . . ?
S1 N1 C4 C3 -166.84(15) . . . . ?
O2 S1 N1 C1 167.0(2) . . . . ?
O2 S1 N1 C4 -30.65(19) . . . . ?
O2 S1 N2 C6 43.48(18) . . . . ?
O2 S1 N2 C5 -175.52(16) . . . . ?
O1 S1 N1 C1 37.8(2) . . . . ?
O1 S1 N1 C4 -159.92(16) . . . . ?
O1 S1 N2 C6 177.56(16) . . . . ?
O1 S1 N2 C5 -41.43(19) . . . . ?
N1 S1 N2 C6 -67.79(17) . . . . ?
N1 S1 N2 C5 73.22(18) . . . . ?
N1 C1 C2 C3 -0.9(3) . . . . ?
N2 S1 N1 C1 -78.9(2) . . . . ?
N2 S1 N1 C4 83.45(18) . . . . ?
C1 N1 C4 C3 -1.1(2) . . . . ?
C4 N1 C1 Br1 178.60(16) . . . . ?
C4 N1 C1 C2 1.2(3) . . . . ?
C4 C3 C2 C1 0.2(3) . . . . ?
C2 C3 C4 N1 0.6(2) . . . . ?

_olex2_submission_original_sample_id OKANO_OKM_514
_olex2_submission_special_instructions 'No special instructions were received'
