#------------------------------------------------------------------------------
#$Date: 2023-04-20 07:03:00 +0300 (Thu, 20 Apr 2023) $
#$Revision: 282758 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/20/2312089.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_2312089
loop_
_publ_author_name
'Kolade, Sherif O.'
'Izunobi, Josephat U.'
'Gordon, Allen T.'
'Hosten, Eric C.'
'Olasupo, Idris A.'
'Ogunlaja, Adeniyi S.'
'Asekun, Olayinka T.'
'Familoni, Oluwole B.'
_publ_section_title
;
 N-Cycloamino substituent effects on the packing architecture of
 ortho-sulfanilamide molecular crystals and their in silico carbonic
 anhydrase II and IX inhibitory activities.
;
_journal_coeditor_code           OJ3005
_journal_issue                   'Pt 12'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              730
_journal_page_last               742
_journal_paper_doi               10.1107/S2053229622010130
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C11 H16 N2 O2 S'
_chemical_formula_moiety         'C11 H16 N2 O2 S'
_chemical_formula_sum            'C11 H16 N2 O2 S'
_chemical_formula_weight         240.32
_chemical_name_systematic
;
2-(Piperidine-1-sulfonyl)aniline
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.1747(4)
_cell_length_b                   10.4850(4)
_cell_length_c                   20.1368(8)
_cell_measurement_reflns_used    9577
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.85
_cell_volume                     2359.36(15)
_computing_cell_refinement
;
APEX2 (Bruker, 2011)
;
_computing_data_collection
;
APEX2 (Bruker, 2011)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020) and Mercury (Macrae et al.,  2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b) and
ShelXle (Hübschle et al.,  2011)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0197
_diffrn_reflns_av_unetI/netI     0.0084
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            57075
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.322
_diffrn_reflns_theta_min         2.023
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9435
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.246
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.357
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0456P)²+0.8126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                2583
_reflns_number_total             2935
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oj3005sup1.cif
_cod_data_source_block           ka115
_cod_database_code               2312089
_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   0.883
_shelx_estimated_absorpt_t_max   0.938
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.66247(2) 0.46255(3) 0.35628(2) 0.02489(10) Uani d 1 . .
O O1 0.78413(7) 0.45299(8) 0.37905(5) 0.0331(2) Uani d 1 . .
O O2 0.60807(8) 0.58657(8) 0.35302(5) 0.0344(2) Uani d 1 . .
N N1 0.48648(11) 0.51544(13) 0.23579(7) 0.0417(3) Uani d 1 . .
N N2 0.58073(8) 0.37768(9) 0.40733(5) 0.0257(2) Uani d 1 . .
C C11 0.65595(9) 0.38973(11) 0.27755(6) 0.0245(2) Uani d 1 . .
C C12 0.56770(10) 0.41892(11) 0.22957(6) 0.0281(2) Uani d 1 . .
C C13 0.56702(11) 0.34467(13) 0.17139(6) 0.0340(3) Uani d 1 . .
H H13 0.509126 0.361787 0.138016 0.041 Uiso calc 1 . .
C C14 0.64803(12) 0.24808(13) 0.16172(6) 0.0357(3) Uani d 1 . .
H H14 0.644395 0.199006 0.122112 0.043 Uiso calc 1 . .
C C15 0.73532(11) 0.22069(12) 0.20879(6) 0.0336(3) Uani d 1 . .
H H15 0.791553 0.154219 0.201449 0.040 Uiso calc 1 . .
C C16 0.73871(10) 0.29170(11) 0.26622(6) 0.0280(2) Uani d 1 . .
H H16 0.798089 0.273989 0.298703 0.034 Uiso calc 1 . .
C C21 0.61856(11) 0.24349(12) 0.41533(6) 0.0320(3) Uani d 1 . .
H H21A 0.706433 0.239499 0.421235 0.038 Uiso calc 1 . .
H H21B 0.597532 0.194456 0.374968 0.038 Uiso calc 1 . .
C C22 0.55700(14) 0.18533(15) 0.47531(7) 0.0429(3) Uani d 1 . .
H H22A 0.584669 0.229165 0.516052 0.051 Uiso calc 1 . .
H H22B 0.579347 0.094219 0.478891 0.051 Uiso calc 1 . .
C C23 0.42189(13) 0.19665(15) 0.47012(8) 0.0460(3) Uani d 1 . .
H H23A 0.392700 0.144432 0.432495 0.055 Uiso calc 1 . .
H H23B 0.384336 0.164250 0.511330 0.055 Uiso calc 1 . .
C C24 0.38708(12) 0.33508(15) 0.45955(8) 0.0448(3) Uani d 1 . .
H H24A 0.408917 0.385359 0.499357 0.054 Uiso calc 1 . .
H H24B 0.299337 0.341143 0.453508 0.054 Uiso calc 1 . .
C C25 0.44964(11) 0.39042(13) 0.39903(7) 0.0358(3) Uani d 1 . .
H H25A 0.423672 0.344456 0.358573 0.043 Uiso calc 1 . .
H H25B 0.428110 0.481486 0.393957 0.043 Uiso calc 1 . .
H H1A 0.4305(18) 0.5177(17) 0.2083(9) 0.050(5) Uiso d 1 . .
H H1B 0.4888(14) 0.5639(15) 0.2697(8) 0.037(4) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O1 . . 118.52(5) ?
O2 S1 N2 . . 106.51(5) ?
O1 S1 N2 . . 106.81(5) ?
O2 S1 C11 . . 109.50(5) ?
O1 S1 C11 . . 107.21(5) ?
N2 S1 C11 . . 107.84(5) ?
C12 N1 H1A . . 117.2(12) ?
C12 N1 H1B . . 119.7(10) ?
H1A N1 H1B . . 122.5(16) ?
C21 N2 C25 . . 112.41(10) ?
C21 N2 S1 . . 115.21(8) ?
C25 N2 S1 . . 115.59(8) ?
C16 C11 C12 . . 120.52(11) ?
C16 C11 S1 . . 115.92(8) ?
C12 C11 S1 . . 123.37(9) ?
N1 C12 C13 . . 118.89(11) ?
N1 C12 C11 . . 124.15(12) ?
C13 C12 C11 . . 116.94(11) ?
C14 C13 C12 . . 121.54(11) ?
C14 C13 H13 . . 119.2 ?
C12 C13 H13 . . 119.2 ?
C13 C14 C15 . . 121.24(12) ?
C13 C14 H14 . . 119.4 ?
C15 C14 H14 . . 119.4 ?
C16 C15 C14 . . 118.73(12) ?
C16 C15 H15 . . 120.6 ?
C14 C15 H15 . . 120.6 ?
C15 C16 C11 . . 121.03(11) ?
C15 C16 H16 . . 119.5 ?
C11 C16 H16 . . 119.5 ?
N2 C21 C22 . . 109.85(11) ?
N2 C21 H21A . . 109.7 ?
C22 C21 H21A . . 109.7 ?
N2 C21 H21B . . 109.7 ?
C22 C21 H21B . . 109.7 ?
H21A C21 H21B . . 108.2 ?
C21 C22 C23 . . 111.39(11) ?
C21 C22 H22A . . 109.4 ?
C23 C22 H22A . . 109.4 ?
C21 C22 H22B . . 109.4 ?
C23 C22 H22B . . 109.4 ?
H22A C22 H22B . . 108.0 ?
C24 C23 C22 . . 109.84(12) ?
C24 C23 H23A . . 109.7 ?
C22 C23 H23A . . 109.7 ?
C24 C23 H23B . . 109.7 ?
C22 C23 H23B . . 109.7 ?
H23A C23 H23B . . 108.2 ?
C23 C24 C25 . . 111.08(12) ?
C23 C24 H24A . . 109.4 ?
C25 C24 H24A . . 109.4 ?
C23 C24 H24B . . 109.4 ?
C25 C24 H24B . . 109.4 ?
H24A C24 H24B . . 108.0 ?
N2 C25 C24 . . 109.28(11) ?
N2 C25 H25A . . 109.8 ?
C24 C25 H25A . . 109.8 ?
N2 C25 H25B . . 109.8 ?
C24 C25 H25B . . 109.8 ?
H25A C25 H25B . . 108.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 . 1.4369(9) ?
S1 O1 . 1.4382(8) ?
S1 N2 . 1.6381(10) ?
S1 C11 . 1.7611(12) ?
N1 C12 . 1.3652(17) ?
N1 H1A . 0.836(19) ?
N1 H1B . 0.852(17) ?
N2 C21 . 1.4780(15) ?
N2 C25 . 1.4804(15) ?
C11 C16 . 1.4014(16) ?
C11 C12 . 1.4141(15) ?
C12 C13 . 1.4066(18) ?
C13 C14 . 1.3723(19) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.3901(18) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.3759(17) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 C22 . 1.5178(17) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 C23 . 1.518(2) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 C24 . 1.518(2) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 C25 . 1.5200(18) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 H25A . 0.9900 ?
C25 H25B . 0.9900 ?
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
_geom_hbond_publ_flag
N1 H1A O1 6_556 0.836(19) 2.496(19) 3.3000(16) 161.8(16) yes
N1 H1B O2 . 0.852(17) 2.156(17) 2.8240(17) 135.1(14) yes
C16 H16 O1 . 0.95 2.48 2.8774(15) 105 yes
C16 H16 O2 8_755 0.95 2.48 3.2576(14) 139 yes
C21 H21A O1 . 0.99 2.55 2.9635(15) 105 yes
C25 H25B O2 . 0.99 2.44 2.8675(15) 106 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 S1 N2 C21 . . . . 177.25(8) ?
O1 S1 N2 C21 . . . . -55.17(9) ?
C11 S1 N2 C21 . . . . 59.79(9) ?
O2 S1 N2 C25 . . . . 43.41(10) ?
O1 S1 N2 C25 . . . . 170.99(9) ?
C11 S1 N2 C25 . . . . -74.05(10) ?
O2 S1 C11 C16 . . . . 158.65(8) ?
O1 S1 C11 C16 . . . . 28.86(10) ?
N2 S1 C11 C16 . . . . -85.83(9) ?
O2 S1 C11 C12 . . . . -26.31(11) ?
O1 S1 C11 C12 . . . . -156.11(9) ?
N2 S1 C11 C12 . . . . 89.20(10) ?
C16 C11 C12 N1 . . . . -177.75(12) ?
S1 C11 C12 N1 . . . . 7.43(17) ?
C16 C11 C12 C13 . . . . 0.61(16) ?
S1 C11 C12 C13 . . . . -174.21(8) ?
N1 C12 C13 C14 . . . . 178.65(12) ?
C11 C12 C13 C14 . . . . 0.20(17) ?
C12 C13 C14 C15 . . . . -0.85(19) ?
C13 C14 C15 C16 . . . . 0.67(19) ?
C14 C15 C16 C11 . . . . 0.15(18) ?
C12 C11 C16 C15 . . . . -0.80(17) ?
S1 C11 C16 C15 . . . . 174.39(9) ?
C25 N2 C21 C22 . . . . -58.70(14) ?
S1 N2 C21 C22 . . . . 166.02(9) ?
N2 C21 C22 C23 . . . . 55.96(15) ?
C21 C22 C23 C24 . . . . -54.92(17) ?
C22 C23 C24 C25 . . . . 55.71(17) ?
C21 N2 C25 C24 . . . . 59.34(14) ?
S1 N2 C25 C24 . . . . -165.56(9) ?
C23 C24 C25 N2 . . . . -57.41(16) ?

_cod_database_fobs_code 2312089
