#------------------------------------------------------------------------------
#$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/42/2104233.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_2104233
loop_
_publ_author_name
'Kalinowska-T\/lu\'scik, Justyna'
'Jarzembek, Krystyna'
'\'Sliwi\'nski, Jan'
'Oleksyn, Barbara J.'
'Kozik, Violetta'
'Pola\'nski, Jaros\/law'
_publ_section_title
;
 Bitter sweeteners: tetrazole derivatives of arylsulfonylalcanoids --
 synthesis, structure and comparative study
;
_journal_coeditor_code           BS5063
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              760
_journal_page_last               770
_journal_paper_doi               10.1107/S0108768108027481
_journal_volume                  64
_journal_year                    2008
_chemical_formula_moiety         'C9 H8 Cl N O2 S'
_chemical_formula_sum            'C9 H8 Cl N O2 S'
_chemical_formula_weight         229.67
_chemical_name_systematic
;
 1-(4-chlorphenylsulfonyl)-ethyl-1-cyanide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 98.114(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0770(6)
_cell_length_b                   15.5895(12)
_cell_length_c                   9.3409(7)
_cell_measurement_reflns_used    97
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1020.24(14)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Automatic single crystal diffractometer KM4'
_diffrn_measurement_method       'omega/2theta scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5005
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.55
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+0.3677P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1054
_reflns_number_gt                2057
_reflns_number_total             2354
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bs5063.cif
_cod_data_source_block           (2a)
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               2104233
loop_
_symmetry_equiv_pos_as_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_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_refinement_flags
_atom_site_occupancy
S S1 0.10494(6) 0.31823(3) 0.60158(5) 0.04569(15) Uani d . 1
O O1 0.0714(2) 0.23528(9) 0.65816(17) 0.0604(4) Uani d . 1
O O2 -0.0382(2) 0.35765(10) 0.49813(18) 0.0674(4) Uani d . 1
Cl Cl1 0.28760(7) 0.56883(4) 1.12078(6) 0.06189(18) Uani d . 1
C C4 0.2443(2) 0.49909(12) 0.9751(2) 0.0441(4) Uani d . 1
C C5 0.2643(3) 0.41193(12) 0.99914(19) 0.0458(4) Uani d . 1
H H5 0.303 0.3909 1.0918 0.055 Uiso calc R 1
C C6 0.2261(2) 0.35660(11) 0.88378(19) 0.0424(4) Uani d . 1
H H6 0.2401 0.2978 0.8977 0.051 Uiso calc R 1
C C1 0.1665(2) 0.38919(10) 0.74646(18) 0.0394(4) Uani d . 1
C C2 0.1495(3) 0.47719(11) 0.7235(2) 0.0486(4) Uani d . 1
H H2 0.1109 0.4985 0.631 0.058 Uiso calc R 1
C C3 0.1899(3) 0.53235(12) 0.8384(2) 0.0514(4) Uani d . 1
H H3 0.1808 0.5913 0.8243 0.062 Uiso calc R 1
C C7 0.3164(3) 0.30820(12) 0.51376(19) 0.0475(4) Uani d . 1
H H7 0.2877 0.2662 0.4357 0.057 Uiso calc R 1
C C9 0.3728(4) 0.39135(16) 0.4457(3) 0.0719(6) Uani d . 1
H H9A 0.2674 0.412 0.3785 0.086 Uiso calc R 1
H H9B 0.4801 0.3811 0.3957 0.086 Uiso calc R 1
H H9C 0.4064 0.4334 0.5199 0.086 Uiso calc R 1
C C8 0.4717(3) 0.27246(12) 0.61813(19) 0.0467(4) Uani d . 1
N N1 0.5880(3) 0.24667(15) 0.6977(2) 0.0715(5) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0442(2) 0.0395(2) 0.0495(3) -0.00198(18) -0.00676(18) -0.00082(17)
O1 0.0612(9) 0.0422(7) 0.0759(10) -0.0152(6) 0.0030(7) -0.0005(7)
O2 0.0597(9) 0.0687(10) 0.0650(9) 0.0091(7) -0.0219(7) -0.0006(8)
Cl1 0.0575(3) 0.0658(3) 0.0644(3) -0.0062(2) 0.0156(2) -0.0241(2)
C4 0.0378(8) 0.0454(9) 0.0506(9) -0.0010(7) 0.0117(7) -0.0080(8)
C5 0.0465(9) 0.0504(10) 0.0406(9) 0.0023(8) 0.0072(7) 0.0049(7)
C6 0.0455(9) 0.0348(8) 0.0470(9) 0.0034(7) 0.0070(7) 0.0069(7)
C1 0.0397(8) 0.0351(8) 0.0426(8) 0.0020(6) 0.0032(7) 0.0014(7)
C2 0.0581(11) 0.0386(9) 0.0472(10) 0.0065(8) 0.0011(8) 0.0072(7)
C3 0.0583(11) 0.0337(8) 0.0627(11) 0.0051(8) 0.0102(9) 0.0023(8)
C7 0.0589(11) 0.0454(9) 0.0360(8) 0.0010(8) -0.0014(7) -0.0038(7)
C9 0.0938(18) 0.0649(14) 0.0598(13) -0.0022(13) 0.0208(12) 0.0106(11)
C8 0.0537(10) 0.0471(10) 0.0395(9) 0.0034(8) 0.0072(8) -0.0067(7)
N1 0.0683(12) 0.0875(14) 0.0575(11) 0.0171(11) 0.0045(9) -0.0053(10)
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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
O1 S1 O2 119.87(9)
O1 S1 C1 108.74(9)
O2 S1 C1 108.90(9)
O1 S1 C7 106.27(9)
O2 S1 C7 106.34(10)
C1 S1 C7 105.82(8)
C5 C4 C3 121.86(17)
C5 C4 Cl1 119.12(15)
C3 C4 Cl1 119.01(15)
C6 C5 C4 119.01(16)
C6 C5 H5 120.5
C4 C5 H5 120.5
C5 C6 C1 119.61(16)
C5 C6 H6 120.2
C1 C6 H6 120.2
C6 C1 C2 120.76(16)
C6 C1 S1 119.45(13)
C2 C1 S1 119.76(13)
C3 C2 C1 119.55(17)
C3 C2 H2 120.2
C1 C2 H2 120.2
C2 C3 C4 119.17(17)
C2 C3 H3 120.4
C4 C3 H3 120.4
C8 C7 C9 112.58(18)
C8 C7 S1 108.66(13)
C9 C7 S1 113.44(15)
C8 C7 H7 107.3
C9 C7 H7 107.3
S1 C7 H7 107.3
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N1 C8 C7 179.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4293(15)
S1 O2 1.4356(14)
S1 C1 1.7546(17)
S1 C7 1.812(2)
Cl1 C4 1.7346(18)
C4 C5 1.381(3)
C4 C3 1.382(3)
C5 C6 1.377(2)
C5 H5 0.93
C6 C1 1.389(2)
C6 H6 0.93
C1 C2 1.391(2)
C2 C3 1.373(3)
C2 H2 0.93
C3 H3 0.93
C7 C8 1.472(3)
C7 C9 1.522(3)
C7 H7 0.98
C9 H9A 0.96
C9 H9B 0.96
C9 H9C 0.96
C8 N1 1.104(3)
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
C3 C4 C5 C6 -1.0(3)
Cl1 C4 C5 C6 178.68(13)
C4 C5 C6 C1 -0.7(3)
C5 C6 C1 C2 1.6(3)
C5 C6 C1 S1 -176.41(14)
O1 S1 C1 C6 17.65(17)
O2 S1 C1 C6 149.87(15)
C7 S1 C1 C6 -96.16(15)
O1 S1 C1 C2 -160.38(15)
O2 S1 C1 C2 -28.15(19)
C7 S1 C1 C2 85.81(16)
C6 C1 C2 C3 -0.8(3)
S1 C1 C2 C3 177.21(15)
C1 C2 C3 C4 -0.9(3)
C5 C4 C3 C2 1.8(3)
Cl1 C4 C3 C2 -177.88(15)
O1 S1 C7 C8 -54.38(15)
O2 S1 C7 C8 176.85(13)
C1 S1 C7 C8 61.12(14)
O1 S1 C7 C9 179.59(15)
O2 S1 C7 C9 50.83(17)
C1 S1 C7 C9 -64.90(16)
C9 C7 C8 N1 65(14)
S1 C7 C8 N1 -61(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139063873