#------------------------------------------------------------------------------
#$Date: 2024-08-05 22:36:44 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293878 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/89/7248943.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7248943
loop_
_publ_author_name
'Huang, Cheng'
'Kang, Chen'
'Liu, Hong-Jun'
'Wang, Chen-Lu'
'Tang, Sheng'
'Qin, Yu-Shu'
'Wei, Zhenhong'
'Cai, Hu'
_publ_section_title
;
 N-Sulfonylation of azoles with sulfonyl hydrazides enabled by
 electrocatalysis
;
_journal_issue                   15
_journal_name_full               'Green Chemistry'
_journal_page_first              8706
_journal_page_last               8710
_journal_paper_doi               10.1039/D4GC02474E
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '0.27(C10 H9 Br N2 O2 S)'
_chemical_formula_sum            'C H Br0.07 Cl N O S0.07'
_chemical_formula_weight         85.94
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-01-27 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                101.928(6)
_cell_angle_beta                 102.068(6)
_cell_angle_gamma                105.796(6)
_cell_formula_units_Z            15
_cell_length_a                   7.976(3)
_cell_length_b                   12.668(4)
_cell_length_c                   12.714(4)
_cell_measurement_reflns_used    2037
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      2.74
_cell_volume                     1160.4(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.926
_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_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.1244
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7022
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.855
_diffrn_reflns_theta_min         2.740
_exptl_absorpt_coefficient_mu    1.867
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2825
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1487 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.3789.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_F_000             636
_refine_diff_density_max         1.132
_refine_diff_density_min         -0.987
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1530
_refine_ls_R_factor_gt           0.0635
_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)+(0.0705P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2603
_reflns_number_total             5121
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4gc02474e2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 7248943--7248944.cif.'
_cod_original_cell_volume        1160.5(7)
_cod_database_code               7248943
_shelx_shelxl_version_number     2018/3
_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.
;
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.94271(12) 0.06778(6) 0.87231(6) 0.0650(3) Uani 1 1 d . . . . .
O1 O 1.1862(6) 0.3492(4) 0.5322(4) 0.0600(13) Uani 1 1 d . . . . .
S1 S 1.0575(2) 0.24254(14) 0.51936(13) 0.0426(4) Uani 1 1 d . . . . .
N1 N 1.0642(7) 0.2297(4) 0.6482(4) 0.0373(12) Uani 1 1 d . . . . .
C1 C 0.8382(8) 0.2460(5) 0.4682(5) 0.0374(15) Uani 1 1 d . . . . .
N2 N 1.0765(7) 0.3225(4) 0.7313(4) 0.0385(12) Uani 1 1 d . . . . .
C2 C 0.8077(11) 0.3484(6) 0.4818(6) 0.0559(19) Uani 1 1 d . . . . .
H2 H 0.903750 0.416602 0.514814 0.067 Uiso 1 1 calc R . . . .
O2 O 1.0737(6) 0.1394(4) 0.4604(4) 0.0555(12) Uani 1 1 d . . . . .
C3 C 0.6347(14) 0.3493(8) 0.4463(7) 0.071(2) Uani 1 1 d . . . . .
H3 H 0.612325 0.418468 0.456544 0.086 Uiso 1 1 calc R . . . .
C4 C 0.4941(12) 0.2494(11) 0.3959(6) 0.076(3) Uani 1 1 d . . . . .
H4 H 0.376370 0.250502 0.371690 0.091 Uiso 1 1 calc R . . . .
C5 C 0.5265(11) 0.1484(9) 0.3813(6) 0.075(3) Uani 1 1 d . . . . .
H5 H 0.430722 0.080476 0.345636 0.090 Uiso 1 1 calc R . . . .
C6 C 0.7007(10) 0.1452(6) 0.4190(6) 0.0548(19) Uani 1 1 d . . . . .
H6 H 0.722819 0.075945 0.410740 0.066 Uiso 1 1 calc R . . . .
C7 C 1.0167(8) 0.1318(5) 0.6786(5) 0.0370(15) Uani 1 1 d . . . . .
H7 H 0.995895 0.058203 0.635311 0.044 Uiso 1 1 calc R . . . .
C8 C 1.0059(8) 0.1629(5) 0.7845(5) 0.0378(15) Uani 1 1 d . . . . .
C9 C 1.0428(8) 0.2818(5) 0.8152(5) 0.0342(14) Uani 1 1 d . . . . .
C10 C 1.0493(10) 0.3569(5) 0.9244(5) 0.0540(19) Uani 1 1 d . . . . .
H10A H 1.094925 0.435528 0.925155 0.081 Uiso 1 1 calc GR . . . .
H10B H 1.127913 0.343197 0.984565 0.081 Uiso 1 1 calc GR . . . .
H10C H 0.929378 0.340314 0.933717 0.081 Uiso 1 1 calc GR . . . .
S2 S 0.4852(2) 0.20639(13) 0.08902(13) 0.0367(4) Uani 1 1 d . . . . .
Br2 Br 0.53468(11) 0.17607(7) -0.34381(6) 0.0650(3) Uani 1 1 d . . . . .
N3 N 0.4679(7) 0.2272(4) -0.0380(4) 0.0374(12) Uani 1 1 d . . . . .
O3 O 0.3980(6) 0.2753(4) 0.1427(3) 0.0499(12) Uani 1 1 d . . . . .
N4 N 0.4945(7) 0.3347(4) -0.0454(4) 0.0426(13) Uani 1 1 d . . . . .
O4 O 0.4206(6) 0.0862(4) 0.0679(4) 0.0528(12) Uani 1 1 d . . . . .
C11 C 0.7183(7) 0.2605(5) 0.1530(5) 0.0301(13) Uani 1 1 d . . . . .
C12 C 0.8020(9) 0.3760(5) 0.2023(5) 0.0390(16) Uani 1 1 d . . . . .
H12 H 0.734138 0.425119 0.205372 0.047 Uiso 1 1 calc R . . . .
C13 C 0.9878(9) 0.4178(5) 0.2469(5) 0.0428(16) Uani 1 1 d . . . . .
H13 H 1.045682 0.495782 0.279743 0.051 Uiso 1 1 calc R . . . .
C14 C 1.0878(9) 0.3463(5) 0.2435(5) 0.0438(16) Uani 1 1 d . . . . .
H14 H 1.213061 0.375180 0.274596 0.053 Uiso 1 1 calc R . . . .
C15 C 1.0032(9) 0.2317(5) 0.1942(6) 0.0475(18) Uani 1 1 d . . . . .
H15 H 1.071507 0.182729 0.192267 0.057 Uiso 1 1 calc R . . . .
C16 C 0.8205(9) 0.1886(5) 0.1482(5) 0.0418(16) Uani 1 1 d . . . . .
H16 H 0.764354 0.110742 0.113471 0.050 Uiso 1 1 calc R . . . .
C17 C 0.4853(8) 0.1567(5) -0.1301(5) 0.0371(15) Uani 1 1 d . . . . .
H17 H 0.477868 0.080459 -0.141776 0.045 Uiso 1 1 calc R . . . .
C18 C 0.5148(8) 0.2210(5) -0.1986(5) 0.0407(15) Uani 1 1 d . . . . .
C19 C 0.5176(8) 0.3307(5) -0.1465(5) 0.0355(15) Uani 1 1 d . . . . .
C20 C 0.5483(10) 0.4333(6) -0.1874(6) 0.060(2) Uani 1 1 d . . . . .
H20A H 0.526988 0.492724 -0.137030 0.091 Uiso 1 1 calc GR . . . .
H20B H 0.466504 0.414987 -0.260659 0.091 Uiso 1 1 calc GR . . . .
H20C H 0.671247 0.458798 -0.191029 0.091 Uiso 1 1 calc GR . . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
O1 S1 N1 106.7(3) . . ?
O1 S1 C1 109.7(3) . . ?
O1 S1 O2 120.9(3) . . ?
N1 S1 C1 103.3(3) . . ?
O2 S1 N1 104.7(3) . . ?
O2 S1 C1 109.9(3) . . ?
N2 N1 S1 119.3(4) . . ?
C7 N1 S1 127.4(4) . . ?
C7 N1 N2 111.4(5) . . ?
C2 C1 S1 119.9(5) . . ?
C6 C1 S1 118.4(5) . . ?
C6 C1 C2 121.6(7) . . ?
C9 N2 N1 105.5(5) . . ?
C3 C2 C1 119.2(7) . . ?
C2 C3 C4 120.5(8) . . ?
C5 C4 C3 119.8(8) . . ?
C4 C5 C6 120.8(8) . . ?
C1 C6 C5 118.1(8) . . ?
C8 C7 N1 105.9(5) . . ?
C7 C8 Br1 127.1(4) . . ?
C7 C8 C9 107.5(5) . . ?
C9 C8 Br1 125.4(5) . . ?
N2 C9 C8 109.6(5) . . ?
N2 C9 C10 122.4(5) . . ?
C8 C9 C10 128.1(6) . . ?
N3 S2 C11 103.1(3) . . ?
O3 S2 N3 106.1(3) . . ?
O3 S2 O4 120.8(3) . . ?
O3 S2 C11 110.0(3) . . ?
O4 S2 N3 104.5(3) . . ?
O4 S2 C11 110.6(3) . . ?
N4 N3 S2 117.7(4) . . ?
N4 N3 C17 112.5(4) . . ?
C17 N3 S2 126.6(4) . . ?
C19 N4 N3 104.5(5) . . ?
C12 C11 S2 120.0(4) . . ?
C12 C11 C16 120.0(6) . . ?
C16 C11 S2 119.9(4) . . ?
C11 C12 C13 119.1(5) . . ?
C14 C13 C12 120.8(6) . . ?
C13 C14 C15 119.7(6) . . ?
C16 C15 C14 120.6(6) . . ?
C15 C16 C11 119.8(5) . . ?
C18 C17 N3 105.0(5) . . ?
C17 C18 Br2 127.7(5) . . ?
C17 C18 C19 108.1(6) . . ?
C19 C18 Br2 124.2(5) . . ?
N4 C19 C18 109.8(5) . . ?
N4 C19 C20 121.0(6) . . ?
C18 C19 C20 129.1(6) . . ?
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 C8 1.848(6) . ?
O1 S1 1.410(4) . ?
S1 N1 1.670(5) . ?
S1 C1 1.749(7) . ?
S1 O2 1.420(4) . ?
N1 N2 1.374(6) . ?
N1 C7 1.354(7) . ?
C1 C2 1.367(9) . ?
C1 C6 1.359(8) . ?
N2 C9 1.322(7) . ?
C2 C3 1.363(11) . ?
C3 C4 1.365(12) . ?
C4 C5 1.357(12) . ?
C5 C6 1.387(10) . ?
C7 C8 1.351(8) . ?
C8 C9 1.405(8) . ?
C9 C10 1.494(8) . ?
S2 N3 1.673(5) . ?
S2 O3 1.412(4) . ?
S2 O4 1.415(4) . ?
S2 C11 1.741(6) . ?
Br2 C18 1.869(6) . ?
N3 N4 1.346(6) . ?
N3 C17 1.375(7) . ?
N4 C19 1.329(7) . ?
C11 C12 1.375(7) . ?
C11 C16 1.379(8) . ?
C12 C13 1.377(8) . ?
C13 C14 1.359(8) . ?
C14 C15 1.367(8) . ?
C15 C16 1.357(9) . ?
C17 C18 1.323(8) . ?
C18 C19 1.403(8) . ?
C19 C20 1.476(8) . ?
