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#$Date: 2020-03-25 02:28:51 +0200 (Wed, 25 Mar 2020) $
#$Revision: 249678 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038100.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_4038100
loop_
_publ_author_name
'Blahun, Oleksandr P.'
'Rozhenko, Alexander B.'
'Rusanov, Eduard'
'Zhersh, Serhii'
'Tolmachev, Andrey A.'
'Volochnyuk, Dmitriy M.'
'Grygorenko, Oleksandr O.'
_publ_section_title
;
 Twisting and turning the sulfonamide bond: synthetic, quantum chemical
 and crystallographic study.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03394
_journal_year                    2020
_chemical_formula_moiety         'C5 H9 N O2 S'
_chemical_formula_sum            'C5 H9 N O2 S'
_chemical_formula_weight         147.19
_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
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 96.211(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4204(11)
_cell_length_b                   11.0682(19)
_cell_length_c                   8.9552(11)
_cell_measurement_reflns_used    860
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.94
_cell_volume                     632.64(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5573
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.936
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       prizm
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0536P)²+0.3483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1121
_reflns_number_total             1242
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03394_si_006.cif
_cod_data_source_block           xr35
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038100
_shelx_shelxl_version_number     2016/4
_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.
;
_shelx_estimated_absorpt_t_min   0.843
_shelx_estimated_absorpt_t_max   0.931
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
S1 S 0.05338(6) 0.27880(3) 0.19394(4) 0.01897(17) Uani 1 1 d . . . . .
O1 O -0.1389(2) 0.31908(12) 0.24417(15) 0.0314(3) Uani 1 1 d . . . . .
O2 O 0.1642(2) 0.36083(11) 0.10714(14) 0.0293(3) Uani 1 1 d . . . . .
N1 N 0.2146(2) 0.22593(12) 0.34026(16) 0.0217(3) Uani 1 1 d . . . . .
C1 C 0.3825(3) 0.16720(17) 0.2617(2) 0.0261(4) Uani 1 1 d . . . . .
H1A H 0.457491 0.108171 0.327085 0.031 Uiso 1 1 calc R U . . .
H1B H 0.481740 0.227403 0.234795 0.031 Uiso 1 1 calc R U . . .
C2 C 0.2754(3) 0.10396(15) 0.11703(19) 0.0253(4) Uani 1 1 d . . . . .
H2A H 0.324311 0.138408 0.027513 0.030 Uiso 1 1 calc R U . . .
H2B H 0.304533 0.017943 0.119240 0.030 Uiso 1 1 calc R U . . .
C3 C 0.0421(3) 0.12765(14) 0.12055(18) 0.0221(4) Uani 1 1 d . . . . .
H3 H -0.045369 0.116657 0.024868 0.027 Uiso 1 1 calc R U . . .
C4 C -0.0321(3) 0.06146(16) 0.2555(2) 0.0271(4) Uani 1 1 d . . . . .
H4A H 0.004459 -0.023536 0.253963 0.033 Uiso 1 1 calc R U . . .
H4B H -0.182622 0.068819 0.255688 0.033 Uiso 1 1 calc R U . . .
C5 C 0.0855(3) 0.12570(16) 0.3949(2) 0.0265(4) Uani 1 1 d . . . . .
H5A H -0.014479 0.157986 0.458241 0.032 Uiso 1 1 calc R U . . .
H5B H 0.175111 0.068519 0.453384 0.032 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 117.97(8) . . ?
O1 S1 N1 110.02(8) . . ?
O2 S1 N1 110.04(8) . . ?
O1 S1 C3 113.80(8) . . ?
O2 S1 C3 113.22(8) . . ?
N1 S1 C3 87.60(7) . . ?
C5 N1 C1 106.48(13) . . ?
C5 N1 S1 101.30(11) . . ?
C1 N1 S1 101.43(10) . . ?
N1 C1 C2 108.00(13) . . ?
C3 C2 C1 104.52(13) . . ?
C2 C3 C4 108.92(13) . . ?
C2 C3 S1 99.62(11) . . ?
C4 C3 S1 99.24(11) . . ?
C3 C4 C5 104.37(13) . . ?
N1 C5 C4 108.28(13) . . ?
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
S1 O1 1.4299(13) . ?
S1 O2 1.4331(12) . ?
S1 N1 1.6845(14) . ?
S1 C3 1.7960(16) . ?
N1 C5 1.498(2) . ?
N1 C1 1.498(2) . ?
C1 C2 1.564(2) . ?
C2 C3 1.524(3) . ?
C3 C4 1.532(2) . ?
C4 C5 1.559(3) . ?
