#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:26:56 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278993 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/56/7245622.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_7245622
loop_
_publ_author_name
'Wang, Hai-Xia'
'Li, Zhi-Hao'
'Li, Wan-Wan'
'Qu, Gui-Rong'
'Yang, Qi-Liang'
'Guo, Hai-Ming'
_publ_section_title
;
 Electrochemically driven oxidative C--H/N--H cross-coupling reactions of
 cyclic sulfamidate imines with primary anilines and secondary amines
;
_journal_issue                   21
_journal_name_full               'Green Chemistry'
_journal_page_first              8377
_journal_page_last               8385
_journal_paper_doi               10.1039/D2GC03218J
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C11 H12 N2 O3 S'
_chemical_formula_sum            'C11 H12 N2 O3 S'
_chemical_formula_weight         252.29
_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             2022-06-22
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2022-07-19 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                92.357(4)
_cell_angle_beta                 103.812(4)
_cell_angle_gamma                111.690(4)
_cell_formula_units_Z            2
_cell_length_a                   7.9773(4)
_cell_length_b                   8.6323(4)
_cell_length_c                   8.8553(4)
_cell_measurement_reflns_used    2921
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3400
_cell_measurement_theta_min      5.1910
_cell_volume                     544.55(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00 -10.00   1.00    1.00    --  -35.62  86.00 -41.00   27
  2  ω    -12.00  67.00   1.00    1.00    --   35.62 -86.00-160.00   79
  3  ω     99.00 159.00   1.00    1.00    --  107.12  86.00 -41.00   60
  4  ω     88.00 131.00   1.00    1.00    --  107.12 -86.00-160.00   43
  5  ω    -62.00  -3.00   1.00    1.00    --  -35.62  77.00 120.00   59
  6  ω      5.00  32.00   1.00    1.00    --  -35.62  77.00 120.00   27
  7  ω   -102.00 -18.00   1.00    1.00    --  -35.62 -38.00 -30.00   84
  8  ω    -83.00 -41.00   1.00    1.00    --  -35.62-178.00 150.00   42
  9  ω    -41.00  34.00   1.00    1.00    --  -35.62  38.00 120.00   75
 10  ω      1.00  49.00   1.00    1.00    --   35.62 -99.00 -30.00   48
 11  ω     42.00  71.00   1.00    1.00    --   35.62 -99.00   0.00   29
 12  ω     94.00 172.00   1.00    1.00    --  107.12  61.00   0.00   78
 13  ω     84.00 110.00   1.00    1.00    --  107.12 -95.00  30.00   26
 14  ω     81.00 175.00   1.00    1.00    --  107.12  77.00 120.00   94
 15  ω    125.00 153.00   1.00    1.00    --  107.12 111.00 -90.00   28
 16  ω     41.00 112.00   1.00    1.00    --  107.12-111.00   0.00   71
 17  ω     51.00 123.00   1.00    1.00    --  107.12 -61.00 150.00   72
 18  ω    100.00 130.00   1.00    1.00    --  107.12 111.00-150.00   30
 19  ω     40.00  71.00   1.00    1.00    --  107.12 -95.00  30.00   31
 20  ω    117.00 169.00   1.00    1.00    --  107.12  45.00-180.00   52
 21  ω     40.00 108.00   1.00    1.00    --  107.12 -95.00 150.00   68
 22  ω     85.00 129.00   1.00    1.00    --  107.12 -30.00-180.00   44
 23  ω    138.00 169.00   1.00    1.00    --  107.12 111.00-150.00   31
 24  ω    100.00 135.00   1.00    1.00    --  107.12 111.00  60.00   35
 25  ω    102.00 171.00   1.00    1.00    --  107.12 111.00-180.00   69
 26  ω     82.00 174.00   1.00    1.00    --  107.12  77.00-120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0062231000
_diffrn_orient_matrix_UB_12      -0.1791346000
_diffrn_orient_matrix_UB_13      -0.0316945000
_diffrn_orient_matrix_UB_21      -0.1438541000
_diffrn_orient_matrix_UB_22      -0.0293738000
_diffrn_orient_matrix_UB_23      -0.1602813000
_diffrn_orient_matrix_UB_31      0.1611052000
_diffrn_orient_matrix_UB_32      0.0686333000
_diffrn_orient_matrix_UB_33      -0.0779374000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3648
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.162
_diffrn_reflns_theta_min         5.197
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.047(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0421
_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)+(0.0659P)²+0.2422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1969
_reflns_number_total             2064
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc03218j2.cif
_cod_data_source_block           lzh-20211209
_cod_depositor_comments
'Adding full bibliography for 7245620--7245625.cif.'
_cod_database_code               7245622
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'S1 N1 C1 H1'
_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_max   0.503
_shelx_estimated_absorpt_t_min   0.503
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C6(H6), C7(H7)
;
_olex2_date_sample_data_collection 2021-12-09
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.268
_oxdiff_exptl_absorpt_empirical_full_min 0.540
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
S3 S 0.15343(6) 0.25190(5) 0.71015(5) 0.0310(2) Uani 1 1 d . . . . .
O4 O -0.00034(18) 0.25106(17) 0.55365(16) 0.0347(3) Uani 1 1 d . . . . .
O16 O 0.2539(2) 0.15950(19) 0.6652(2) 0.0464(4) Uani 1 1 d . . . . .
O17 O 0.0479(2) 0.1879(2) 0.81750(19) 0.0478(4) Uani 1 1 d . . . . .
N11 N 0.4488(2) 0.70204(19) 0.71721(18) 0.0290(4) Uani 1 1 d . . . . .
N2 N 0.2823(2) 0.4449(2) 0.76578(19) 0.0333(4) Uani 1 1 d . . . . .
C1 C 0.3275(2) 0.5457(2) 0.6595(2) 0.0264(4) Uani 1 1 d . . . . .
C5 C 0.0783(3) 0.3381(2) 0.4424(2) 0.0293(4) Uani 1 1 d . . . . .
C10 C 0.2422(3) 0.4858(2) 0.4887(2) 0.0267(4) Uani 1 1 d . . . . .
C9 C 0.3144(3) 0.5608(3) 0.3682(2) 0.0337(4) Uani 1 1 d . . . . .
H9 H 0.425924 0.655777 0.393620 0.040 Uiso 1 1 calc R U . . .
C14 C 0.5875(3) 0.9987(2) 0.7670(3) 0.0377(5) Uani 1 1 d . . . . .
H14A H 0.682945 1.094668 0.742399 0.045 Uiso 1 1 calc R U . . .
H14B H 0.490400 1.032357 0.786722 0.045 Uiso 1 1 calc R U . . .
C15 C 0.5060(3) 0.8509(2) 0.6351(2) 0.0338(4) Uani 1 1 d . . . . .
H15A H 0.399024 0.855290 0.558218 0.041 Uiso 1 1 calc R U . . .
H15B H 0.599371 0.849756 0.582639 0.041 Uiso 1 1 calc R U . . .
C12 C 0.5288(3) 0.7501(2) 0.8891(2) 0.0353(5) Uani 1 1 d . . . . .
H12A H 0.588688 0.676549 0.933381 0.042 Uiso 1 1 calc R U . . .
H12B H 0.432694 0.745968 0.940164 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2223(3) 0.4957(3) 0.2124(3) 0.0424(5) Uani 1 1 d . . . . .
H8 H 0.271425 0.548405 0.134059 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6713(3) 0.9289(3) 0.9064(2) 0.0389(5) Uani 1 1 d . . . . .
H13A H 0.792158 0.930035 0.902423 0.047 Uiso 1 1 calc R U . . .
H13B H 0.686366 0.993344 1.004621 0.047 Uiso 1 1 calc R U . . .
C6 C -0.0137(3) 0.2719(3) 0.2869(3) 0.0399(5) Uani 1 1 d . . . . .
H6 H -0.122306 0.174012 0.260327 0.048 Uiso 1 1 calc R U . . .
C7 C 0.0576(4) 0.3528(3) 0.1716(3) 0.0464(6) Uani 1 1 d . . . . .
H7 H -0.004885 0.311448 0.066295 0.056 Uiso 1 1 calc R U . . .
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'
N N 0.0311 0.0180 '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'
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
O16 S3 O4 107.22(9) . . ?
O16 S3 N2 111.99(9) . . ?
O17 S3 O4 104.33(9) . . ?
O17 S3 O16 117.65(10) . . ?
O17 S3 N2 110.36(10) . . ?
N2 S3 O4 104.02(8) . . ?
C5 O4 S3 113.48(11) . . ?
C1 N11 C15 129.24(16) . . ?
C1 N11 C12 119.52(15) . . ?
C12 N11 C15 110.85(15) . . ?
C1 N2 S3 119.60(14) . . ?
N11 C1 N2 115.43(16) . . ?
N11 C1 C10 123.17(16) . . ?
N2 C1 C10 121.38(16) . . ?
O4 C5 C10 120.79(16) . . ?
C6 C5 O4 116.49(17) . . ?
C6 C5 C10 122.72(18) . . ?
C5 C10 C1 117.78(16) . . ?
C9 C10 C1 125.68(17) . . ?
C9 C10 C5 116.51(17) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 C10 121.00(19) . . ?
C8 C9 H9 119.5 . . ?
H14A C14 H14B 109.1 . . ?
C15 C14 H14A 111.1 . . ?
C15 C14 H14B 111.1 . . ?
C13 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
C13 C14 C15 103.11(16) . . ?
N11 C15 C14 103.47(16) . . ?
N11 C15 H15A 111.1 . . ?
N11 C15 H15B 111.1 . . ?
C14 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
H15A C15 H15B 109.0 . . ?
N11 C12 H12A 111.0 . . ?
N11 C12 H12B 111.0 . . ?
N11 C12 C13 103.58(15) . . ?
H12A C12 H12B 109.0 . . ?
C13 C12 H12A 111.0 . . ?
C13 C12 H12B 111.0 . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C7 120.60(19) . . ?
C7 C8 H8 119.7 . . ?
C14 C13 H13A 111.0 . . ?
C14 C13 H13B 111.0 . . ?
C12 C13 C14 103.67(17) . . ?
C12 C13 H13A 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 H6 120.5 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
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
S3 O4 1.6144(14) . ?
S3 O16 1.4265(16) . ?
S3 O17 1.4141(15) . ?
S3 N2 1.5808(17) . ?
O4 C5 1.392(2) . ?
N11 C1 1.327(2) . ?
N11 C15 1.480(2) . ?
N11 C12 1.478(2) . ?
N2 C1 1.331(2) . ?
C1 C10 1.484(3) . ?
C5 C10 1.405(3) . ?
C5 C6 1.380(3) . ?
C10 C9 1.401(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.381(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.522(3) . ?
C14 C13 1.517(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.516(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.385(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C7 1.377(3) . ?
C7 H7 0.9300 . ?
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
S3 O4 C5 C10 -36.4(2) . . . . ?
S3 O4 C5 C6 143.84(16) . . . . ?
S3 N2 C1 N11 -174.46(13) . . . . ?
S3 N2 C1 C10 7.1(2) . . . . ?
O4 S3 N2 C1 -39.33(17) . . . . ?
O4 C5 C10 C1 -0.3(2) . . . . ?
O4 C5 C10 C9 177.68(16) . . . . ?
O4 C5 C6 C7 179.95(18) . . . . ?
O16 S3 O4 C5 -65.55(14) . . . . ?
O16 S3 N2 C1 76.14(17) . . . . ?
O17 S3 O4 C5 168.95(13) . . . . ?
O17 S3 N2 C1 -150.73(16) . . . . ?
N11 C1 C10 C5 -161.44(16) . . . . ?
N11 C1 C10 C9 20.8(3) . . . . ?
N11 C12 C13 C14 31.5(2) . . . . ?
N2 S3 O4 C5 53.23(14) . . . . ?
N2 C1 C10 C5 16.9(3) . . . . ?
N2 C1 C10 C9 -160.91(18) . . . . ?
C1 N11 C15 C14 159.94(18) . . . . ?
C1 N11 C12 C13 174.86(16) . . . . ?
C1 C10 C9 C8 -179.21(18) . . . . ?
C5 C10 C9 C8 3.0(3) . . . . ?
C5 C6 C7 C8 1.9(3) . . . . ?
C10 C5 C6 C7 0.2(3) . . . . ?
C10 C9 C8 C7 -1.0(3) . . . . ?
C9 C8 C7 C6 -1.5(3) . . . . ?
C15 N11 C1 N2 -169.67(18) . . . . ?
C15 N11 C1 C10 8.7(3) . . . . ?
C15 N11 C12 C13 -11.7(2) . . . . ?
C15 C14 C13 C12 -39.6(2) . . . . ?
C12 N11 C1 N2 2.5(2) . . . . ?
C12 N11 C1 C10 -179.14(17) . . . . ?
C12 N11 C15 C14 -12.7(2) . . . . ?
C13 C14 C15 N11 31.9(2) . . . . ?
C6 C5 C10 C1 179.40(18) . . . . ?
C6 C5 C10 C9 -2.6(3) . . . . ?
