#------------------------------------------------------------------------------
#$Date: 2024-05-06 07:18:53 +0300 (Mon, 06 May 2024) $
#$Revision: 291714 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023076.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_2023076
loop_
_publ_author_name
'Kolade, Sherif O.'
'Aina, Oluwafemi S.'
'Gordon, Allen T.'
'Hosten, Eric C.'
'Olasupo, Idris A.'
'Ogunlaja, Adeniyi S.'
'Asekun, Olayinka T.'
'Familoni, Oluwole B.'
_publ_section_title
;
 Synthesis, crystal structure and in-silico evaluation of arylsulfonamide
 Schiff bases for potential activity against colon cancer.
;
_journal_coeditor_code           EF3052
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              129
_journal_page_last               142
_journal_paper_doi               10.1107/S205322962400233X
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C18 H19 Br N2 O3 S'
_chemical_formula_moiety         'C18 H19 Br N2 O3 S'
_chemical_formula_sum            'C18 H19 Br N2 O3 S'
_chemical_formula_weight         423.32
_chemical_melting_point          427.45
_chemical_name_systematic
;
4-Bromo-2-{N-[2-(piperidine-1-sulfonyl)phenyl]carboximidoyl}phenol
;
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.4070(9)
_cell_length_b                   17.4250(14)
_cell_length_c                   17.5276(12)
_cell_measurement_reflns_used    9105
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.51
_cell_measurement_theta_min      2.32
_cell_volume                     3789.3(5)
_computing_cell_refinement
;
APEX2 (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0600
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27860
_diffrn_reflns_theta_full        25.104
_diffrn_reflns_theta_max         25.104
_diffrn_reflns_theta_min         2.324
_exptl_absorpt_coefficient_mu    2.299
_exptl_absorpt_correction_T_max  0.2407
_exptl_absorpt_correction_T_min  0.1328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.837
_exptl_crystal_size_mid          0.426
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.375
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0624
_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)+(0.0610P)²+7.1303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1724
_reflns_number_gt                2255
_reflns_number_total             3356
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ef3052.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023076.cif.'
_cod_database_code               2023076
_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   0.249
_shelx_estimated_absorpt_t_max   0.764
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
Br Br1 0.85040(8) 0.46864(5) 0.55005(4) 0.1140(4) Uani d 1 . .
S S1 0.56327(10) 0.22940(8) 0.14642(7) 0.0607(4) Uani d 1 . .
O O1 0.5496(3) 0.4349(3) 0.2834(3) 0.0907(13) Uani d 1 . .
H H1A 0.579549 0.413541 0.247549 0.136 Uiso calc 1 . .
O O2 0.4882(3) 0.2902(2) 0.1591(2) 0.0777(11) Uani d 1 . .
O O3 0.5316(3) 0.1682(2) 0.0968(2) 0.0883(12) Uani d 1 . .
N N1 0.6996(3) 0.3585(2) 0.2148(2) 0.0555(10) Uani d 1 . .
N N2 0.5983(3) 0.1974(2) 0.2293(2) 0.0565(10) Uani d 1 . .
C C1 0.7606(4) 0.3689(3) 0.2721(3) 0.0533(11) Uani d 1 . .
H H1 0.830912 0.350473 0.270688 0.064 Uiso calc 1 . .
C C11 0.7232(4) 0.4088(3) 0.3396(3) 0.0543(12) Uani d 1 . .
C C12 0.6188(5) 0.4412(3) 0.3421(3) 0.0688(15) Uani d 1 . .
C C13 0.5885(5) 0.4815(3) 0.4058(4) 0.091(2) Uani d 1 . .
H H13 0.520618 0.504049 0.407731 0.109 Uiso calc 1 . .
C C14 0.6568(6) 0.4888(4) 0.4667(4) 0.092(2) Uani d 1 . .
H H14 0.634378 0.515785 0.509646 0.111 Uiso calc 1 . .
C C15 0.7582(5) 0.4568(3) 0.4652(3) 0.0752(16) Uani d 1 . .
C C16 0.7913(4) 0.4171(3) 0.4014(3) 0.0629(13) Uani d 1 . .
H H16 0.859904 0.395629 0.400021 0.075 Uiso calc 1 . .
C C21 0.7416(4) 0.3243(3) 0.1480(2) 0.0518(11) Uani d 1 . .
C C22 0.6852(4) 0.2672(3) 0.1103(2) 0.0521(11) Uani d 1 . .
C C23 0.7250(4) 0.2370(3) 0.0428(3) 0.0665(14) Uani d 1 . .
H H23 0.687000 0.198557 0.017620 0.080 Uiso calc 1 . .
C C24 0.8208(5) 0.2636(3) 0.0126(3) 0.0719(15) Uani d 1 . .
H H24 0.846894 0.243698 -0.033050 0.086 Uiso calc 1 . .
C C25 0.8771(5) 0.3193(3) 0.0503(3) 0.0678(14) Uani d 1 . .
H H25 0.942106 0.336688 0.030261 0.081 Uiso calc 1 . .
C C26 0.8389(4) 0.3502(3) 0.1175(3) 0.0589(12) Uani d 1 . .
H H26 0.877962 0.388227 0.142523 0.071 Uiso calc 1 . .
C C31 0.6682(5) 0.1288(3) 0.2294(3) 0.0813(17) Uani d 1 . .
H H31A 0.719512 0.132034 0.187760 0.098 Uiso calc 1 . .
H H31B 0.624822 0.083122 0.222158 0.098 Uiso calc 1 . .
C C32 0.7269(6) 0.1238(4) 0.3034(4) 0.106(2) Uani d 1 . .
H H32A 0.775409 0.167263 0.308142 0.127 Uiso calc 1 . .
H H32B 0.769888 0.077342 0.304347 0.127 Uiso calc 1 . .
C C33 0.6496(6) 0.1234(4) 0.3696(4) 0.105(2) Uani d 1 . .
H H33A 0.689478 0.122977 0.417148 0.126 Uiso calc 1 . .
H H33B 0.605394 0.077539 0.367612 0.126 Uiso calc 1 . .
C C34 0.5783(7) 0.1938(4) 0.3663(3) 0.108(2) Uani d 1 . .
H H34A 0.525103 0.191096 0.406797 0.130 Uiso calc 1 . .
H H34B 0.621880 0.239270 0.374740 0.130 Uiso calc 1 . .
C C35 0.5233(5) 0.2003(4) 0.2927(3) 0.0880(19) Uani d 1 . .
H H35A 0.471669 0.158796 0.287800 0.106 Uiso calc 1 . .
H H35B 0.483889 0.248338 0.291006 0.106 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'
Br Br -0.2901 2.4595 '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 O3 . . 117.9(2) ?
O2 S1 N2 . . 107.0(2) ?
O3 S1 N2 . . 111.3(2) ?
O2 S1 C22 . . 109.7(2) ?
O3 S1 C22 . . 107.2(2) ?
N2 S1 C22 . . 102.8(2) ?
C12 O1 H1A . . 109.5 ?
C1 N1 C21 . . 119.7(4) ?
C35 N2 C31 . . 113.8(4) ?
C35 N2 S1 . . 120.3(3) ?
C31 N2 S1 . . 116.0(3) ?
N1 C1 C11 . . 121.5(4) ?
N1 C1 H1 . . 119.2 ?
C11 C1 H1 . . 119.2 ?
C16 C11 C12 . . 119.6(4) ?
C16 C11 C1 . . 119.6(4) ?
C12 C11 C1 . . 120.7(5) ?
O1 C12 C13 . . 119.3(6) ?
O1 C12 C11 . . 122.0(5) ?
C13 C12 C11 . . 118.7(6) ?
C14 C13 C12 . . 120.9(6) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C13 C14 C15 . . 120.9(5) ?
C13 C14 H14 . . 119.6 ?
C15 C14 H14 . . 119.6 ?
C16 C15 C14 . . 119.5(6) ?
C16 C15 Br1 . . 120.9(5) ?
C14 C15 Br1 . . 119.6(4) ?
C15 C16 C11 . . 120.4(5) ?
C15 C16 H16 . . 119.8 ?
C11 C16 H16 . . 119.8 ?
C22 C21 C26 . . 119.2(4) ?
C22 C21 N1 . . 120.8(4) ?
C26 C21 N1 . . 120.0(4) ?
C21 C22 C23 . . 120.0(4) ?
C21 C22 S1 . . 121.9(3) ?
C23 C22 S1 . . 118.0(4) ?
C24 C23 C22 . . 120.4(5) ?
C24 C23 H23 . . 119.8 ?
C22 C23 H23 . . 119.8 ?
C25 C24 C23 . . 119.6(5) ?
C25 C24 H24 . . 120.2 ?
C23 C24 H24 . . 120.2 ?
C24 C25 C26 . . 121.0(5) ?
C24 C25 H25 . . 119.5 ?
C26 C25 H25 . . 119.5 ?
C25 C26 C21 . . 119.8(5) ?
C25 C26 H26 . . 120.1 ?
C21 C26 H26 . . 120.1 ?
N2 C31 C32 . . 109.6(5) ?
N2 C31 H31A . . 109.7 ?
C32 C31 H31A . . 109.7 ?
N2 C31 H31B . . 109.7 ?
C32 C31 H31B . . 109.7 ?
H31A C31 H31B . . 108.2 ?
C31 C32 C33 . . 111.0(6) ?
C31 C32 H32A . . 109.4 ?
C33 C32 H32A . . 109.4 ?
C31 C32 H32B . . 109.4 ?
C33 C32 H32B . . 109.4 ?
H32A C32 H32B . . 108.0 ?
C32 C33 C34 . . 109.9(5) ?
C32 C33 H33A . . 109.7 ?
C34 C33 H33A . . 109.7 ?
C32 C33 H33B . . 109.7 ?
C34 C33 H33B . . 109.7 ?
H33A C33 H33B . . 108.2 ?
C35 C34 C33 . . 111.6(6) ?
C35 C34 H34A . . 109.3 ?
C33 C34 H34A . . 109.3 ?
C35 C34 H34B . . 109.3 ?
C33 C34 H34B . . 109.3 ?
H34A C34 H34B . . 108.0 ?
N2 C35 C34 . . 111.9(5) ?
N2 C35 H35A . . 109.2 ?
C34 C35 H35A . . 109.2 ?
N2 C35 H35B . . 109.2 ?
C34 C35 H35B . . 109.2 ?
H35A C35 H35B . . 107.9 ?
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
Br1 C15 . 1.888(6) ?
S1 O2 . 1.428(4) ?
S1 O3 . 1.431(4) ?
S1 N2 . 1.616(4) ?
S1 C22 . 1.767(5) ?
O1 C12 . 1.344(7) ?
O1 H1A . 0.8200 ?
N1 C1 . 1.270(6) ?
N1 C21 . 1.413(6) ?
N2 C35 . 1.451(6) ?
N2 C31 . 1.477(6) ?
C1 C11 . 1.449(6) ?
C1 H1 . 0.9300 ?
C11 C16 . 1.382(7) ?
C11 C12 . 1.413(7) ?
C12 C13 . 1.372(8) ?
C13 C14 . 1.368(10) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.377(9) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.376(7) ?
C16 H16 . 0.9300 ?
C21 C22 . 1.384(7) ?
C21 C26 . 1.395(7) ?
C22 C23 . 1.386(6) ?
C23 C24 . 1.381(7) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.366(8) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.380(7) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
C31 C32 . 1.489(8) ?
C31 H31A . 0.9700 ?
C31 H31B . 0.9700 ?
C32 C33 . 1.506(9) ?
C32 H32A . 0.9700 ?
C32 H32B . 0.9700 ?
C33 C34 . 1.513(9) ?
C33 H33A . 0.9700 ?
C33 H33B . 0.9700 ?
C34 C35 . 1.464(8) ?
C34 H34A . 0.9700 ?
C34 H34B . 0.9700 ?
C35 H35A . 0.9700 ?
C35 H35B . 0.9700 ?
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
O1 H1A N1 . 0.82 1.86 2.586(5) 146 yes
C1 H1 O2 6_656 0.93 2.54 3.363(6) 149 yes
C16 H16 O2 6_656 0.93 2.64 3.461(6) 147 yes
C23 H23 O3 . 0.93 2.43 2.846(7) 107 yes
C25 H25 O3 4 0.93 2.49 3.220(6) 135 yes
C26 H26 O1 6_656 0.93 2.62 3.467(7) 151 yes
C35 H35B O2 . 0.97 2.43 2.852(7) 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 C35 . . . . 30.7(5) ?
O3 S1 N2 C35 . . . . -99.4(5) ?
C22 S1 N2 C35 . . . . 146.2(5) ?
O2 S1 N2 C31 . . . . 174.4(4) ?
O3 S1 N2 C31 . . . . 44.3(5) ?
C22 S1 N2 C31 . . . . -70.2(4) ?
C21 N1 C1 C11 . . . . 175.3(4) ?
N1 C1 C11 C16 . . . . 178.2(4) ?
N1 C1 C11 C12 . . . . -3.5(7) ?
C16 C11 C12 O1 . . . . 180.0(5) ?
C1 C11 C12 O1 . . . . 1.6(7) ?
C16 C11 C12 C13 . . . . 1.2(7) ?
C1 C11 C12 C13 . . . . -177.1(5) ?
O1 C12 C13 C14 . . . . 179.7(6) ?
C11 C12 C13 C14 . . . . -1.4(9) ?
C12 C13 C14 C15 . . . . 0.8(10) ?
C13 C14 C15 C16 . . . . 0.2(9) ?
C13 C14 C15 Br1 . . . . 179.7(5) ?
C14 C15 C16 C11 . . . . -0.4(8) ?
Br1 C15 C16 C11 . . . . -179.9(4) ?
C12 C11 C16 C15 . . . . -0.2(7) ?
C1 C11 C16 C15 . . . . 178.1(4) ?
C1 N1 C21 C22 . . . . 135.0(5) ?
C1 N1 C21 C26 . . . . -47.6(6) ?
C26 C21 C22 C23 . . . . -0.6(7) ?
N1 C21 C22 C23 . . . . 176.8(4) ?
C26 C21 C22 S1 . . . . 178.2(3) ?
N1 C21 C22 S1 . . . . -4.4(6) ?
O2 S1 C22 C21 . . . . 55.2(4) ?
O3 S1 C22 C21 . . . . -175.7(4) ?
N2 S1 C22 C21 . . . . -58.3(4) ?
O2 S1 C22 C23 . . . . -126.0(4) ?
O3 S1 C22 C23 . . . . 3.2(4) ?
N2 S1 C22 C23 . . . . 120.5(4) ?
C21 C22 C23 C24 . . . . -0.1(7) ?
S1 C22 C23 C24 . . . . -179.0(4) ?
C22 C23 C24 C25 . . . . 0.9(8) ?
C23 C24 C25 C26 . . . . -0.9(8) ?
C24 C25 C26 C21 . . . . 0.2(8) ?
C22 C21 C26 C25 . . . . 0.6(7) ?
N1 C21 C26 C25 . . . . -176.9(4) ?
C35 N2 C31 C32 . . . . -55.6(7) ?
S1 N2 C31 C32 . . . . 158.4(5) ?
N2 C31 C32 C33 . . . . 56.1(8) ?
C31 C32 C33 C34 . . . . -56.3(9) ?
C32 C33 C34 C35 . . . . 54.6(9) ?
C31 N2 C35 C34 . . . . 54.9(7) ?
S1 N2 C35 C34 . . . . -160.7(5) ?
C33 C34 C35 N2 . . . . -53.6(9) ?
