#------------------------------------------------------------------------------
#$Date: 2023-04-20 07:03:00 +0300 (Thu, 20 Apr 2023) $
#$Revision: 282758 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/20/2312085.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_2312085
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          'C10 H12 N2 O4 S'
_chemical_formula_moiety         'C10 H12 N2 O4 S'
_chemical_formula_sum            'C10 H12 N2 O4 S'
_chemical_formula_weight         256.28
_chemical_name_systematic
;
1-[(2-Nitrophenyl)sulfonyl]pyrrolidine
;
_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                 108.075(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6173(5)
_cell_length_b                   14.6662(9)
_cell_length_c                   9.4885(6)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.65
_cell_volume                     1140.01(12)
_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 0.995
_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  0.0180
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24329
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.384
_diffrn_reflns_theta_min         2.651
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9337
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.674
_exptl_crystal_size_mid          0.665
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.467
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2849
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0412
_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)+(0.0517P)²+0.7926P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                2508
_reflns_number_total             2849
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oj3005sup1.cif
_cod_data_source_block           ka097
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2312085
_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   0.829
_shelx_estimated_absorpt_t_max   0.966
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 0.49089(5) 0.66797(3) 0.32216(4) 0.02954(13) Uani d 1 . .
O O1 0.52737(15) 0.62543(9) 0.46416(13) 0.0360(3) Uani d 1 . .
O O2 0.41164(17) 0.75483(10) 0.29726(18) 0.0481(4) Uani d 1 . .
O O3 0.91161(16) 0.56570(9) 0.57998(13) 0.0374(3) Uani d 1 . .
O O4 0.74333(16) 0.49165(8) 0.40041(15) 0.0387(3) Uani d 1 . .
N N1 0.3849(2) 0.59886(12) 0.20100(17) 0.0424(4) Uani d 1 . .
N N2 0.82322(16) 0.55892(9) 0.45200(15) 0.0261(3) Uani d 1 . .
C C21 0.67960(18) 0.68563(10) 0.28603(17) 0.0243(3) Uani d 1 . .
C C22 0.82125(18) 0.63575(9) 0.35184(16) 0.0233(3) Uani d 1 . .
C C23 0.9678(2) 0.65569(11) 0.32834(19) 0.0300(3) Uani d 1 . .
H H23 1.063007 0.621352 0.376473 0.036 Uiso calc 1 . .
C C24 0.9742(2) 0.72656(12) 0.2335(2) 0.0347(4) Uani d 1 . .
H H24 1.073735 0.740356 0.214723 0.042 Uiso calc 1 . .
C C25 0.8355(2) 0.77707(12) 0.1663(2) 0.0348(4) Uani d 1 . .
H H25 0.839913 0.825347 0.100842 0.042 Uiso calc 1 . .
C C26 0.6899(2) 0.75768(11) 0.19374(18) 0.0304(3) Uani d 1 . .
H H26 0.596179 0.793966 0.149089 0.036 Uiso calc 1 . .
C C11 0.3771(10) 0.4994(5) 0.2187(8) 0.0525(5) Uani d 0.579(7) A 1
H H11A 0.365697 0.483433 0.316363 0.063 Uiso calc 0.579(7) A 1
H H11B 0.475419 0.469108 0.207784 0.063 Uiso calc 0.579(7) A 1
C C12 0.2269(6) 0.4739(3) 0.0945(5) 0.0525(5) Uani d 0.579(7) A 1
H H12A 0.126167 0.490743 0.117592 0.063 Uiso calc 0.579(7) A 1
H H12B 0.224619 0.407828 0.072438 0.063 Uiso calc 0.579(7) A 1
C C13 0.2474(6) 0.5302(4) -0.0321(5) 0.0525(5) Uani d 0.579(7) A 1
H H13A 0.142720 0.536536 -0.112750 0.063 Uiso calc 0.579(7) A 1
H H13B 0.329694 0.502920 -0.072615 0.063 Uiso calc 0.579(7) A 1
C C14 0.3052(11) 0.6216(4) 0.0416(7) 0.0525(5) Uani d 0.579(7) A 1
H H14A 0.384050 0.650475 -0.001515 0.063 Uiso calc 0.579(7) A 1
H H14B 0.211994 0.663509 0.029701 0.063 Uiso calc 0.579(7) A 1
C C15 0.3620(14) 0.5024(7) 0.2240(11) 0.0525(5) Uani d 0.421(7) A 2
H H15A 0.289652 0.492782 0.285820 0.063 Uiso calc 0.421(7) A 2
H H15B 0.467484 0.471263 0.270293 0.063 Uiso calc 0.421(7) A 2
C C16 0.2804(9) 0.4696(4) 0.0620(7) 0.0525(5) Uani d 0.421(7) A 2
H H16A 0.362038 0.441474 0.021428 0.063 Uiso calc 0.421(7) A 2
H H16B 0.193459 0.424491 0.057238 0.063 Uiso calc 0.421(7) A 2
C C17 0.2083(8) 0.5567(5) -0.0247(7) 0.0525(5) Uani d 0.421(7) A 2
H H17A 0.207484 0.551559 -0.128998 0.063 Uiso calc 0.421(7) A 2
H H17B 0.094759 0.566045 -0.023970 0.063 Uiso calc 0.421(7) A 2
C C18 0.3140(15) 0.6354(6) 0.0501(10) 0.0525(5) Uani d 0.421(7) A 2
H H18A 0.399357 0.649069 0.003320 0.063 Uiso calc 0.421(7) A 2
H H18B 0.248645 0.691003 0.049588 0.063 Uiso calc 0.421(7) A 2
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 . . 119.93(9) ?
O1 S1 N1 . . 108.19(8) ?
O2 S1 N1 . . 108.08(9) ?
O1 S1 C21 . . 107.34(7) ?
O2 S1 C21 . . 104.85(8) ?
N1 S1 C21 . . 107.90(8) ?
C15 N1 C18 . . 117.8(5) ?
C11 N1 C14 . . 108.3(4) ?
C15 N1 S1 . . 125.8(4) ?
C11 N1 S1 . . 125.8(3) ?
C18 N1 S1 . . 116.2(3) ?
C14 N1 S1 . . 124.8(2) ?
O4 N2 O3 . . 124.55(14) ?
O4 N2 C22 . . 118.04(13) ?
O3 N2 C22 . . 117.32(13) ?
C26 C21 C22 . . 117.54(14) ?
C26 C21 S1 . . 118.12(12) ?
C22 C21 S1 . . 124.21(11) ?
C23 C22 C21 . . 122.31(14) ?
C23 C22 N2 . . 116.04(13) ?
C21 C22 N2 . . 121.64(13) ?
C22 C23 C24 . . 119.09(15) ?
C22 C23 H23 . . 120.5 ?
C24 C23 H23 . . 120.5 ?
C25 C24 C23 . . 119.87(15) ?
C25 C24 H24 . . 120.1 ?
C23 C24 H24 . . 120.1 ?
C24 C25 C26 . . 120.41(15) ?
C24 C25 H25 . . 119.8 ?
C26 C25 H25 . . 119.8 ?
C25 C26 C21 . . 120.75(15) ?
C25 C26 H26 . . 119.6 ?
C21 C26 H26 . . 119.6 ?
N1 C11 C12 . . 102.5(5) ?
N1 C11 H11A . . 111.3 ?
C12 C11 H11A . . 111.3 ?
N1 C11 H11B . . 111.3 ?
C12 C11 H11B . . 111.3 ?
H11A C11 H11B . . 109.2 ?
C11 C12 C13 . . 101.6(5) ?
C11 C12 H12A . . 111.4 ?
C13 C12 H12A . . 111.4 ?
C11 C12 H12B . . 111.4 ?
C13 C12 H12B . . 111.4 ?
H12A C12 H12B . . 109.3 ?
C12 C13 C14 . . 102.6(4) ?
C12 C13 H13A . . 111.2 ?
C14 C13 H13A . . 111.2 ?
C12 C13 H13B . . 111.2 ?
C14 C13 H13B . . 111.2 ?
H13A C13 H13B . . 109.2 ?
N1 C14 C13 . . 104.5(4) ?
N1 C14 H14A . . 110.8 ?
C13 C14 H14A . . 110.8 ?
N1 C14 H14B . . 110.8 ?
C13 C14 H14B . . 110.8 ?
H14A C14 H14B . . 108.9 ?
N1 C15 C16 . . 101.2(6) ?
N1 C15 H15A . . 111.5 ?
C16 C15 H15A . . 111.5 ?
N1 C15 H15B . . 111.5 ?
C16 C15 H15B . . 111.5 ?
H15A C15 H15B . . 109.4 ?
C17 C16 C15 . . 104.7(6) ?
C17 C16 H16A . . 110.8 ?
C15 C16 H16A . . 110.8 ?
C17 C16 H16B . . 110.8 ?
C15 C16 H16B . . 110.8 ?
H16A C16 H16B . . 108.9 ?
C18 C17 C16 . . 107.4(6) ?
C18 C17 H17A . . 110.2 ?
C16 C17 H17A . . 110.2 ?
C18 C17 H17B . . 110.2 ?
C16 C17 H17B . . 110.2 ?
H17A C17 H17B . . 108.5 ?
N1 C18 C17 . . 100.8(5) ?
N1 C18 H18A . . 111.6 ?
C17 C18 H18A . . 111.6 ?
N1 C18 H18B . . 111.6 ?
C17 C18 H18B . . 111.6 ?
H18A C18 H18B . . 109.4 ?
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 . 1.4285(12) ?
S1 O2 . 1.4300(13) ?
S1 N1 . 1.5913(17) ?
S1 C21 . 1.7818(15) ?
O3 N2 . 1.2209(18) ?
O4 N2 . 1.2157(18) ?
N1 C15 . 1.454(10) ?
N1 C11 . 1.472(8) ?
N1 C18 . 1.472(8) ?
N1 C14 . 1.492(6) ?
N2 C22 . 1.4706(18) ?
C21 C26 . 1.393(2) ?
C21 C22 . 1.394(2) ?
C22 C23 . 1.380(2) ?
C23 C24 . 1.387(2) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.382(2) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.388(2) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C11 C12 . 1.503(8) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.513(6) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.522(6) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.555(10) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 C17 . 1.543(8) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.505(8) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 H18A . 0.9900 ?
C18 H18B . 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
C11 H11A O1 3_666 0.99 2.56 3.398(7) 143 yes
C11 H11B O4 . 0.99 2.48 3.093(8) 120 yes
C25 H25 O4 2_655 0.95 2.54 3.240(2) 131 yes
C25 H25 O1 4_675 0.95 2.47 3.228(2) 137 yes
C26 H26 O2 . 0.95 2.49 2.860(2) 103 yes
C26 H26 O3 4_575 0.95 2.56 3.467(2) 160 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 C15 . . . . -13.5(6) ?
O2 S1 N1 C15 . . . . -144.8(6) ?
C21 S1 N1 C15 . . . . 102.3(6) ?
O1 S1 N1 C11 . . . . -21.2(5) ?
O2 S1 N1 C11 . . . . -152.5(5) ?
C21 S1 N1 C11 . . . . 94.6(5) ?
O1 S1 N1 C18 . . . . 171.1(7) ?
O2 S1 N1 C18 . . . . 39.8(7) ?
C21 S1 N1 C18 . . . . -73.1(7) ?
O1 S1 N1 C14 . . . . 172.3(5) ?
O2 S1 N1 C14 . . . . 41.0(5) ?
C21 S1 N1 C14 . . . . -71.9(5) ?
O1 S1 C21 C26 . . . . -152.34(13) ?
O2 S1 C21 C26 . . . . -23.76(15) ?
N1 S1 C21 C26 . . . . 91.26(14) ?
O1 S1 C21 C22 . . . . 23.24(15) ?
O2 S1 C21 C22 . . . . 151.82(14) ?
N1 S1 C21 C22 . . . . -93.15(15) ?
C26 C21 C22 C23 . . . . 0.1(2) ?
S1 C21 C22 C23 . . . . -175.54(12) ?
C26 C21 C22 N2 . . . . 179.49(14) ?
S1 C21 C22 N2 . . . . 3.9(2) ?
O4 N2 C22 C23 . . . . -114.81(16) ?
O3 N2 C22 C23 . . . . 61.75(19) ?
O4 N2 C22 C21 . . . . 65.74(19) ?
O3 N2 C22 C21 . . . . -117.70(16) ?
C21 C22 C23 C24 . . . . -1.4(2) ?
N2 C22 C23 C24 . . . . 179.13(15) ?
C22 C23 C24 C25 . . . . 1.2(3) ?
C23 C24 C25 C26 . . . . 0.4(3) ?
C24 C25 C26 C21 . . . . -1.8(3) ?
C22 C21 C26 C25 . . . . 1.5(2) ?
S1 C21 C26 C25 . . . . 177.41(13) ?
C14 N1 C11 C12 . . . . -27.8(8) ?
S1 N1 C11 C12 . . . . 163.9(4) ?
N1 C11 C12 C13 . . . . 43.3(8) ?
C11 C12 C13 C14 . . . . -42.6(7) ?
C11 N1 C14 C13 . . . . 1.2(8) ?
S1 N1 C14 C13 . . . . 169.7(3) ?
C12 C13 C14 N1 . . . . 25.6(7) ?
C18 N1 C15 C16 . . . . 6.6(11) ?
S1 N1 C15 C16 . . . . -168.8(4) ?
N1 C15 C16 C17 . . . . -21.2(10) ?
C15 C16 C17 C18 . . . . 29.7(11) ?
C15 N1 C18 C17 . . . . 11.2(12) ?
S1 N1 C18 C17 . . . . -173.0(5) ?
C16 C17 C18 N1 . . . . -24.5(11) ?

_cod_database_fobs_code 2312085
