#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/96/2239699.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2239699
loop_
_publ_author_name
'Rai, Kartik'
'Wu, Vincent'
'Gupta, Priya'
'Laviska, David A.'
'Chan, Benny C.'
_publ_section_title
;
 N-Methyl-N-nitroso-p-toluenesulfonamide
;
_journal_coeditor_code           FJ2674
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o782
_journal_paper_doi               10.1107/S1600536814013518
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C8 H10 N2 O3 S'
_chemical_formula_moiety         'C8 H10 N2 O3 S'
_chemical_formula_sum            'C8 H10 N2 O3 S'
_chemical_formula_weight         214.24
_chemical_name_common            Diazald
_chemical_name_systematic
;
N-Methyl-N-nitroso-p-toluenesulfonamide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                81.4580(10)
_cell_angle_beta                 85.8830(10)
_cell_angle_gamma                80.3100(10)
_cell_formula_units_Z            2
_cell_length_a                   6.8911(8)
_cell_length_b                   8.4435(10)
_cell_length_c                   8.6248(10)
_cell_measurement_reflns_used    3237
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.0886
_cell_measurement_theta_min      2.4710
_cell_volume                     488.62(10)
_computing_cell_refinement       'SAINT (Bruker, 2011)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_molecular_graphics    'CrystalMaker (CrystalMaker, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5753
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.443
_diffrn_reflns_theta_min         2.391
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6869
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(SADABS; Bruker, 2011)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.84
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.372
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0374
_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)+(0.0425P)²+0.2042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                1892
_reflns_number_total             2275
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2674sup1.cif
_cod_data_source_block           I
_cod_database_code               2239699
_cod_database_fobs_code          2239699
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
S S1 0.20728(6) 0.03322(5) 0.28268(5) 0.01794(13) Uani d 1
O O1 0.33666(19) -0.07228(14) 0.38895(14) 0.0234(3) Uani d 1
O O2 0.05198(18) -0.02289(15) 0.21663(15) 0.0239(3) Uani d 1
O O3 -0.1436(2) 0.37946(16) 0.40008(15) 0.0301(3) Uani d 1
N N1 0.0960(2) 0.18010(17) 0.38888(16) 0.0184(3) Uani d 1
N N2 -0.0760(2) 0.26414(19) 0.33146(18) 0.0246(3) Uani d 1
C C1 0.3438(2) 0.13715(19) 0.13431(19) 0.0167(3) Uani d 1
C C2 0.5359(3) 0.1532(2) 0.1589(2) 0.0200(4) Uani d 1
H H2 0.5971 0.1025 0.2528 0.024 Uiso calc 1
C C3 0.6369(3) 0.2450(2) 0.0434(2) 0.0219(4) Uani d 1
H H3 0.7691 0.2557 0.0584 0.026 Uiso calc 1
C C4 0.5484(3) 0.3215(2) -0.0938(2) 0.0204(4) Uani d 1
C C5 0.3552(3) 0.3032(2) -0.1148(2) 0.0220(4) Uani d 1
H H5 0.2932 0.3554 -0.2079 0.026 Uiso calc 1
C C6 0.2519(3) 0.2107(2) -0.0028(2) 0.0204(4) Uani d 1
H H6 0.1209 0.1976 -0.0190 0.024 Uiso calc 1
C C7 0.6590(3) 0.4220(2) -0.2174(2) 0.0282(4) Uani d 1
H H7A 0.7301 0.4901 -0.1669 0.042 Uiso calc 1
H H7B 0.5657 0.4911 -0.2891 0.042 Uiso calc 1
H H7C 0.7532 0.3502 -0.2764 0.042 Uiso calc 1
C C8 0.1981(3) 0.2380(2) 0.5075(2) 0.0219(4) Uani d 1
H H8A 0.194(3) 0.352(3) 0.480(2) 0.033 Uiso d 1
H H8B 0.329(3) 0.181(3) 0.512(2) 0.033 Uiso d 1
H H8C 0.137(3) 0.215(3) 0.609(3) 0.033 Uiso d 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O1 121.43(8)
O2 S1 N1 105.80(7)
O1 S1 N1 104.15(7)
O2 S1 C1 109.93(8)
O1 S1 C1 110.06(8)
N1 S1 C1 103.75(7)
N2 N1 C8 121.69(14)
N2 N1 S1 114.33(11)
C8 N1 S1 122.36(12)
O3 N2 N1 113.28(14)
C2 C1 C6 121.41(16)
C2 C1 S1 119.72(13)
C6 C1 S1 118.76(13)
C1 C2 C3 118.62(16)
C1 C2 H2 120.7
C3 C2 H2 120.7
C2 C3 C4 121.31(16)
C2 C3 H3 119.3
C4 C3 H3 119.3
C3 C4 C5 118.64(16)
C3 C4 C7 120.73(17)
C5 C4 C7 120.63(16)
C6 C5 C4 121.35(16)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 C1 118.66(16)
C5 C6 H6 120.7
C1 C6 H6 120.7
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N1 C8 H8A 108.3(13)
N1 C8 H8B 108.9(13)
H8A C8 H8B 112.2(19)
N1 C8 H8C 110.6(13)
H8A C8 H8C 110.3(18)
H8B C8 H8C 106.5(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4258(13)
S1 O1 1.4268(13)
S1 N1 1.6975(14)
S1 C1 1.7504(17)
O3 N2 1.2224(19)
N1 N2 1.360(2)
N1 C8 1.466(2)
C1 C2 1.388(2)
C1 C6 1.394(2)
C2 C3 1.390(2)
C2 H2 0.9500
C3 C4 1.391(2)
C3 H3 0.9500
C4 C5 1.393(3)
C4 C7 1.506(2)
C5 C6 1.384(2)
C5 H5 0.9500
C6 H6 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.96(2)
C8 H8B 0.95(2)
C8 H8C 0.96(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C8 H8b O1 2_656 0.95(2) 2.49(2) 3.401(2) 160
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
O2 S1 N1 N2 -30.84(14)
O1 S1 N1 N2 -159.92(12)
C1 S1 N1 N2 84.88(13)
O2 S1 N1 C8 163.44(13)
O1 S1 N1 C8 34.37(15)
C1 S1 N1 C8 -80.84(15)
C8 N1 N2 O3 -7.3(2)
S1 N1 N2 O3 -173.13(12)
O2 S1 C1 C2 -157.71(13)
O1 S1 C1 C2 -21.41(16)
N1 S1 C1 C2 89.53(14)
O2 S1 C1 C6 26.22(15)
O1 S1 C1 C6 162.52(13)
N1 S1 C1 C6 -86.55(14)
C6 C1 C2 C3 0.0(2)
S1 C1 C2 C3 -175.94(13)
C1 C2 C3 C4 0.8(3)
C2 C3 C4 C5 -0.6(3)
C2 C3 C4 C7 179.38(16)
C3 C4 C5 C6 -0.3(3)
C7 C4 C5 C6 179.71(16)
C4 C5 C6 C1 1.0(3)
C2 C1 C6 C5 -0.9(3)
S1 C1 C6 C5 175.10(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 6628
