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#$Date: 2023-05-05 04:14:17 +0300 (Fri, 05 May 2023) $
#$Revision: 283192 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/81/1568131.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_1568131
loop_
_publ_author_name
'Lasso, Juan D.'
'Castillo-Pazos, Durbis J'
'Sim, Malcolm'
'Barroso-Flores, Joaquín'
'Li, Chao-Jun'
_publ_section_title
;
 EDA mediated S-N bond coupling of nitroarenes and sodium sulfinate salts.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              525
_journal_page_last               532
_journal_paper_doi               10.1039/d2sc06087f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C8 H8 N2 O3 S'
_chemical_formula_weight         212.22
_chemical_name_systematic        N-(4-cyanophenyl)-N-hydroxymethanesulfonamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2022-09-21 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.606(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2861(15)
_cell_length_b                   5.4731(10)
_cell_length_c                   20.821(4)
_cell_measurement_reflns_used    1764
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.214
_cell_measurement_theta_min      5.882
_cell_volume                     942.4(3)
_computing_cell_refinement       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13264
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.214
_diffrn_reflns_theta_min         5.882
_exptl_absorpt_coefficient_mu    2.951
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.203
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0338
_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)+(0.0495P)²+0.2907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1764
_reflns_number_total             1809
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc06087f1.cif
_cod_data_source_block           DC5
_cod_depositor_comments          'Adding full bibliography for 1568131.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1568131
_shelx_shelxl_version_number     2017/1
_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.
;
_shelx_estimated_absorpt_t_min   0.422
_shelx_estimated_absorpt_t_max   0.586
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'
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 0.47316(17) 0.5915(3) 0.58373(7) 0.0361(3) Uani 1 1 d . . . . .
C2 C 0.32327(19) 0.6715(3) 0.55826(7) 0.0405(3) Uani 1 1 d . . . . .
H2 H 0.316274 0.810096 0.532401 0.049 Uiso 1 1 calc R U . . .
C3 C 0.18473(17) 0.5453(3) 0.57129(7) 0.0382(3) Uani 1 1 d . . . . .
H3 H 0.084119 0.597987 0.554398 0.046 Uiso 1 1 calc R U . . .
C4 C 0.19788(16) 0.3382(3) 0.61008(6) 0.0310(3) Uani 1 1 d . . . . .
C5 C 0.34738(19) 0.2544(3) 0.63436(8) 0.0359(3) Uani 1 1 d . . . . .
H5 H 0.354263 0.113118 0.659212 0.043 Uiso 1 1 calc R U . . .
N8 N 0.72613(18) 0.8449(3) 0.56171(8) 0.0551(4) Uani 1 1 d . . . . .
C7 C 0.6152(2) 0.7300(3) 0.57132(8) 0.0427(4) Uani 1 1 d . . . . .
C6 C 0.48609(17) 0.3807(3) 0.62162(7) 0.0393(3) Uani 1 1 d . . . . .
H6 H 0.586720 0.326186 0.638018 0.047 Uiso 1 1 calc R U . . .
O10 O -0.07552(14) 0.2632(2) 0.58127(6) 0.0470(3) Uani 1 1 d . . . . .
H10 H -0.123(2) 0.145(4) 0.5718(10) 0.071 Uiso 1 1 calc R U . . .
S11 S -0.00423(4) 0.26527(6) 0.70155(2) 0.03512(16) Uani 1 1 d . . . . .
C12 C -0.0369(2) 0.5814(3) 0.70397(8) 0.0454(4) Uani 1 1 d . . . . .
H12A H 0.065296 0.664621 0.707347 0.068 Uiso 1 1 calc R U . . .
H12B H -0.096854 0.620880 0.740559 0.068 Uiso 1 1 calc R U . . .
H12C H -0.096976 0.631979 0.665319 0.068 Uiso 1 1 calc R U . . .
O13 O -0.15511(14) 0.1401(2) 0.70359(7) 0.0536(3) Uani 1 1 d . . . . .
O14 O 0.12774(15) 0.2000(3) 0.74531(6) 0.0513(3) Uani 1 1 d . . . . .
N9 N 0.05703(14) 0.2039(2) 0.62633(6) 0.0343(3) Uani 1 1 d . . . . .
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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'
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
C2 C1 C6 120.66(13) . . ?
C2 C1 C7 119.18(14) . . ?
C6 C1 C7 120.15(14) . . ?
C3 C2 C1 120.10(14) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.04(13) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.11(13) . . ?
C5 C4 N9 117.70(13) . . ?
C3 C4 N9 121.19(12) . . ?
C6 C5 C4 119.97(13) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
N8 C7 C1 178.41(19) . . ?
C5 C6 C1 119.10(13) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N9 O10 H10 109.5 . . ?
O14 S11 O13 119.93(8) . . ?
O14 S11 N9 106.04(7) . . ?
O13 S11 N9 104.11(7) . . ?
O14 S11 C12 110.06(8) . . ?
O13 S11 C12 109.62(8) . . ?
N9 S11 C12 105.99(7) . . ?
S11 C12 H12A 109.5 . . ?
S11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O10 N9 C4 109.23(11) . . ?
O10 N9 S11 107.16(9) . . ?
C4 N9 S11 114.04(9) . . ?
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 C2 1.390(2) . ?
C1 C6 1.398(2) . ?
C1 C7 1.436(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(2) . ?
C4 N9 1.4376(17) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9300 . ?
N8 C7 1.142(2) . ?
C6 H6 0.9300 . ?
O10 N9 1.4362(16) . ?
O10 H10 0.78(3) . ?
S11 O14 1.4241(12) . ?
S11 O13 1.4286(12) . ?
S11 N9 1.7098(13) . ?
S11 C12 1.7526(17) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
