#------------------------------------------------------------------------------
#$Date: 2023-04-20 07:03:00 +0300 (Thu, 20 Apr 2023) $
#$Revision: 282758 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/20/2312086.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_2312086
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 H14 N2 O4 S'
_chemical_formula_moiety         'C11 H14 N2 O4 S'
_chemical_formula_sum            'C11 H14 N2 O4 S'
_chemical_formula_weight         270.30
_chemical_name_systematic
;
1-[(2-Nitrophenyl)sulfonyl]piperidine
;
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 106.526(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6881(9)
_cell_length_b                   15.0266(14)
_cell_length_c                   9.8337(10)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.55
_cell_volume                     1230.8(2)
_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      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0165
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25328
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_min         2.550
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9406
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.483
_exptl_crystal_size_mid          0.469
_exptl_crystal_size_min          0.453
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0363
_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)+(0.0546P)²+0.3577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                2662
_reflns_number_total             3059
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oj3005sup1.cif
_cod_data_source_block           ja198
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2312086
_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   0.880
_shelx_estimated_absorpt_t_max   0.887
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_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 0.50241(4) 0.66804(2) 0.66863(4) 0.04006(12) Uani d 1 . .
O O1 0.57946(15) 0.75271(8) 0.69071(16) 0.0609(3) Uani d 1 . .
O O2 0.46987(14) 0.62642(8) 0.53305(11) 0.0521(3) Uani d 1 . .
O O3 0.23990(17) 0.49620(9) 0.58739(17) 0.0705(4) Uani d 1 . .
O O4 0.08960(18) 0.57419(11) 0.41946(13) 0.0734(4) Uani d 1 . .
N N1 0.61016(14) 0.60117(8) 0.78644(13) 0.0416(3) Uani d 1 . .
N N2 0.17049(15) 0.56417(9) 0.54124(14) 0.0463(3) Uani d 1 . .
C C11 0.5872(2) 0.50422(11) 0.76898(19) 0.0517(4) Uani d 1 . .
H H11A 0.564441 0.488569 0.669528 0.062 Uiso calc 1 . .
H H11B 0.496745 0.485803 0.801683 0.062 Uiso calc 1 . .
C C12 0.7374(2) 0.45729(13) 0.8536(2) 0.0627(5) Uani d 1 . .
H H12A 0.720629 0.393457 0.845762 0.075 Uiso calc 1 . .
H H12B 0.825213 0.471853 0.814835 0.075 Uiso calc 1 . .
C C13 0.7814(2) 0.48376(14) 1.0071(2) 0.0606(5) Uani d 1 . .
H H13A 0.881221 0.455002 1.057712 0.073 Uiso calc 1 . .
H H13B 0.698481 0.463866 1.048463 0.073 Uiso calc 1 . .
C C14 0.8004(2) 0.58345(15) 1.0233(2) 0.0662(5) Uani d 1 . .
H H14A 0.819586 0.599222 1.122396 0.079 Uiso calc 1 . .
H H14B 0.892831 0.602183 0.993857 0.079 Uiso calc 1 . .
C C15 0.6533(2) 0.63160(13) 0.93604(18) 0.0582(4) Uani d 1 . .
H H15A 0.564368 0.620532 0.975063 0.070 Uiso calc 1 . .
H H15B 0.673748 0.695143 0.939930 0.070 Uiso calc 1 . .
C C21 0.31422(16) 0.68463(9) 0.70518(14) 0.0357(3) Uani d 1 . .
C C22 0.17424(16) 0.63776(9) 0.64082(14) 0.0372(3) Uani d 1 . .
C C23 0.02972(18) 0.65753(11) 0.66598(17) 0.0468(3) Uani d 1 . .
H H23 -0.062624 0.626220 0.619609 0.056 Uiso calc 1 . .
C C24 0.0237(2) 0.72436(12) 0.76084(19) 0.0530(4) Uani d 1 . .
H H24 -0.072622 0.737406 0.780184 0.064 Uiso calc 1 . .
C C25 0.1604(2) 0.77165(12) 0.82675(18) 0.0529(4) Uani d 1 . .
H H25 0.156178 0.816624 0.890548 0.063 Uiso calc 1 . .
C C26 0.30433(19) 0.75250(10) 0.79841(16) 0.0449(3) Uani d 1 . .
H H26 0.395471 0.785498 0.842346 0.054 Uiso calc 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
O1 S1 O2 . . 119.57(8) ?
O1 S1 N1 . . 107.14(7) ?
O2 S1 N1 . . 108.53(7) ?
O1 S1 C21 . . 105.16(7) ?
O2 S1 C21 . . 107.43(7) ?
N1 S1 C21 . . 108.59(6) ?
C11 N1 C15 . . 114.07(14) ?
C11 N1 S1 . . 119.97(10) ?
C15 N1 S1 . . 116.79(10) ?
O3 N2 O4 . . 124.29(15) ?
O3 N2 C22 . . 118.14(13) ?
O4 N2 C22 . . 117.42(14) ?
N1 C11 C12 . . 109.30(14) ?
N1 C11 H11A . . 109.8 ?
C12 C11 H11A . . 109.8 ?
N1 C11 H11B . . 109.8 ?
C12 C11 H11B . . 109.8 ?
H11A C11 H11B . . 108.3 ?
C13 C12 C11 . . 111.34(15) ?
C13 C12 H12A . . 109.4 ?
C11 C12 H12A . . 109.4 ?
C13 C12 H12B . . 109.4 ?
C11 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C12 C13 C14 . . 110.97(16) ?
C12 C13 H13A . . 109.4 ?
C14 C13 H13A . . 109.4 ?
C12 C13 H13B . . 109.4 ?
C14 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
C15 C14 C13 . . 111.53(16) ?
C15 C14 H14A . . 109.3 ?
C13 C14 H14A . . 109.3 ?
C15 C14 H14B . . 109.3 ?
C13 C14 H14B . . 109.3 ?
H14A C14 H14B . . 108.0 ?
N1 C15 C14 . . 110.56(14) ?
N1 C15 H15A . . 109.5 ?
C14 C15 H15A . . 109.5 ?
N1 C15 H15B . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 108.1 ?
C26 C21 C22 . . 117.46(13) ?
C26 C21 S1 . . 117.79(11) ?
C22 C21 S1 . . 124.65(11) ?
C23 C22 C21 . . 122.11(13) ?
C23 C22 N2 . . 115.62(13) ?
C21 C22 N2 . . 122.27(12) ?
C22 C23 C24 . . 119.28(15) ?
C22 C23 H23 . . 120.4 ?
C24 C23 H23 . . 120.4 ?
C25 C24 C23 . . 119.93(14) ?
C25 C24 H24 . . 120.0 ?
C23 C24 H24 . . 120.0 ?
C24 C25 C26 . . 120.31(15) ?
C24 C25 H25 . . 119.8 ?
C26 C25 H25 . . 119.8 ?
C25 C26 C21 . . 120.88(15) ?
C25 C26 H26 . . 119.6 ?
C21 C26 H26 . . 119.6 ?
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 O1 . 1.4252(12) ?
S1 O2 . 1.4263(12) ?
S1 N1 . 1.6160(13) ?
S1 C21 . 1.7885(14) ?
O3 N2 . 1.2070(19) ?
O4 N2 . 1.2132(18) ?
N1 C11 . 1.474(2) ?
N1 C15 . 1.4833(19) ?
N2 C22 . 1.4713(19) ?
C11 C12 . 1.508(2) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.501(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.511(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.506(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C21 C26 . 1.390(2) ?
C21 C22 . 1.3921(19) ?
C22 C23 . 1.379(2) ?
C23 C24 . 1.382(2) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.378(3) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.386(2) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
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
C11 H11A O2 . 0.97 2.48 2.907(2) 107 yes
C11 H11A O2 3_666 0.97 2.59 3.476(2) 152 yes
C15 H15B O1 . 0.97 2.51 2.943(2) 107 yes
C25 H25 O2 4_576 0.93 2.57 3.3337(19) 140 yes
C26 H26 O1 . 0.93 2.53 2.877(2) 103 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
O1 S1 N1 C11 . . . . -163.84(12) ?
O2 S1 N1 C11 . . . . -33.45(14) ?
C21 S1 N1 C11 . . . . 83.04(13) ?
O1 S1 N1 C15 . . . . 51.20(14) ?
O2 S1 N1 C15 . . . . -178.40(12) ?
C21 S1 N1 C15 . . . . -61.91(13) ?
C15 N1 C11 C12 . . . . -56.72(19) ?
S1 N1 C11 C12 . . . . 157.43(13) ?
N1 C11 C12 C13 . . . . 56.4(2) ?
C11 C12 C13 C14 . . . . -56.2(2) ?
C12 C13 C14 C15 . . . . 54.1(2) ?
C11 N1 C15 C14 . . . . 55.3(2) ?
S1 N1 C15 C14 . . . . -157.73(14) ?
C13 C14 C15 N1 . . . . -52.6(2) ?
O1 S1 C21 C26 . . . . -26.70(14) ?
O2 S1 C21 C26 . . . . -155.08(12) ?
N1 S1 C21 C26 . . . . 87.72(12) ?
O1 S1 C21 C22 . . . . 149.47(12) ?
O2 S1 C21 C22 . . . . 21.08(14) ?
N1 S1 C21 C22 . . . . -96.11(13) ?
C26 C21 C22 C23 . . . . 0.7(2) ?
S1 C21 C22 C23 . . . . -175.47(11) ?
C26 C21 C22 N2 . . . . -179.50(13) ?
S1 C21 C22 N2 . . . . 4.32(19) ?
O3 N2 C22 C23 . . . . -111.68(16) ?
O4 N2 C22 C23 . . . . 64.06(19) ?
O3 N2 C22 C21 . . . . 68.51(19) ?
O4 N2 C22 C21 . . . . -115.74(16) ?
C21 C22 C23 C24 . . . . -1.7(2) ?
N2 C22 C23 C24 . . . . 178.45(14) ?
C22 C23 C24 C25 . . . . 1.4(2) ?
C23 C24 C25 C26 . . . . 0.0(3) ?
C24 C25 C26 C21 . . . . -1.0(3) ?
C22 C21 C26 C25 . . . . 0.7(2) ?
S1 C21 C26 C25 . . . . 177.14(12) ?

_cod_database_fobs_code 2312086
