#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225803.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_2225803
loop_
_publ_author_name
'Khan, Islam Ullah'
'Dong, Gui-Ying'
'Ali, Sharafat'
'Sharif, Shahzad'
'Haide, Zeeshan'
_publ_section_title
;
 N-Phenyl-N-(prop-2-en-1-yl)benzenesulfonamide
;
_journal_coeditor_code           CI5071
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1087
_journal_paper_doi               10.1107/S1600536810013152
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H15 N O2 S'
_chemical_formula_moiety         'C15 H15 N O2 S'
_chemical_formula_sum            'C15 H15 N O2 S'
_chemical_formula_weight         273.35
_chemical_name_systematic
;
N-Phenyl-N-(prop-2-en-1-yl)benzenesulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 103.535(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6302(8)
_cell_length_b                   5.7041(4)
_cell_length_c                   21.9408(14)
_cell_measurement_reflns_used    3368
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.3
_cell_measurement_theta_min      2.38
_cell_volume                     1415.12(17)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9448
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_correction_T_min  0.9584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.583
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1687P)²+2.1422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1922
_refine_ls_wR_factor_ref         0.2448
_reflns_number_gt                1803
_reflns_number_total             2467
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5071.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225803
_cod_database_fobs_code          2225803
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.69888(9) -0.0377(2) 0.71607(5) 0.0425(4) Uani d . 1 . .
N N1 0.6478(3) 0.1073(6) 0.65082(15) 0.0421(9) Uani d . 1 . .
C C9 0.7280(4) -0.0195(9) 0.5639(2) 0.0500(11) Uani d . 1 . .
H H9 0.6824 -0.1545 0.5615 0.060 Uiso calc R 1 . .
C C10 0.7692(3) 0.1656(8) 0.77270(17) 0.0398(10) Uani d . 1 . .
C C13 0.8729(5) 0.5034(11) 0.8566(2) 0.0683(15) Uani d . 1 . .
H H13 0.9082 0.6188 0.8848 0.082 Uiso calc R 1 . .
C C3 0.4412(6) 0.5309(14) 0.5687(3) 0.092(2) Uani d . 1 . .
H H3A 0.4626 0.6644 0.5930 0.111 Uiso calc R 1 . .
H H3B 0.3918 0.5436 0.5288 0.111 Uiso calc R 1 . .
C C4 0.7260(4) 0.1466(8) 0.60926(17) 0.0407(10) Uani d . 1 . .
C C1 0.5584(4) 0.2901(9) 0.6524(2) 0.0504(11) Uani d . 1 . .
H H1A 0.5114 0.2434 0.6815 0.060 Uiso calc R 1 . .
H H1B 0.5982 0.4356 0.6675 0.060 Uiso calc R 1 . .
C C11 0.8892(4) 0.2012(9) 0.7843(2) 0.0525(12) Uani d . 1 . .
H H11 0.9351 0.1128 0.7633 0.063 Uiso calc R 1 . .
C C5 0.7939(4) 0.3460(8) 0.6128(2) 0.0512(11) Uani d . 1 . .
H H5 0.7929 0.4574 0.6437 0.061 Uiso calc R 1 . .
C C2 0.4799(4) 0.3294(11) 0.5901(2) 0.0631(14) Uani d . 1 . .
H H2 0.4569 0.1994 0.5645 0.076 Uiso calc R 1 . .
C C15 0.7010(4) 0.2992(10) 0.80332(19) 0.0548(13) Uani d . 1 . .
H H15 0.6199 0.2745 0.7958 0.066 Uiso calc R 1 . .
C C7 0.8644(4) 0.2144(11) 0.5249(2) 0.0616(14) Uani d . 1 . .
H H7 0.9106 0.2384 0.4962 0.074 Uiso calc R 1 . .
C C6 0.8631(5) 0.3801(10) 0.5706(2) 0.0616(13) Uani d . 1 . .
H H6 0.9090 0.5148 0.5728 0.074 Uiso calc R 1 . .
C C14 0.7545(5) 0.4699(11) 0.8452(2) 0.0686(16) Uani d . 1 . .
H H14 0.7090 0.5619 0.8655 0.082 Uiso calc R 1 . .
O O2 0.7865(3) -0.1951(6) 0.70389(14) 0.0545(9) Uani d . 1 . .
O O1 0.5986(3) -0.1260(6) 0.73525(15) 0.0582(9) Uani d . 1 . .
C C8 0.7983(5) 0.0159(10) 0.5219(2) 0.0616(14) Uani d . 1 . .
H H8 0.8005 -0.0963 0.4914 0.074 Uiso calc R 1 . .
C C12 0.9411(4) 0.3693(11) 0.8272(2) 0.0641(15) Uani d . 1 . .
H H12 1.0226 0.3915 0.8361 0.077 Uiso calc R 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 . . 120.2(2) ?
O1 S1 N1 . . 106.41(19) ?
O2 S1 N1 . . 106.38(18) ?
O1 S1 C10 . . 107.66(19) ?
O2 S1 C10 . . 108.22(19) ?
N1 S1 C10 . . 107.3(2) ?
C4 N1 C1 . . 117.0(3) ?
C4 N1 S1 . . 118.4(3) ?
C1 N1 S1 . . 116.6(3) ?
C4 C9 C8 . . 119.6(5) ?
C4 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C11 C10 C15 . . 120.2(4) ?
C11 C10 S1 . . 120.9(3) ?
C15 C10 S1 . . 118.9(3) ?
C14 C13 C12 . . 120.7(5) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C2 C3 H3A . . 120.0 ?
C2 C3 H3B . . 120.0 ?
H3A C3 H3B . . 120.0 ?
C5 C4 C9 . . 120.2(4) ?
C5 C4 N1 . . 121.9(4) ?
C9 C4 N1 . . 117.9(4) ?
C2 C1 N1 . . 111.8(4) ?
C2 C1 H1A . . 109.3 ?
N1 C1 H1A . . 109.3 ?
C2 C1 H1B . . 109.3 ?
N1 C1 H1B . . 109.3 ?
H1A C1 H1B . . 107.9 ?
C10 C11 C12 . . 119.4(4) ?
C10 C11 H11 . . 120.3 ?
C12 C11 H11 . . 120.3 ?
C4 C5 C6 . . 119.8(5) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C3 C2 C1 . . 124.3(6) ?
C3 C2 H2 . . 117.8 ?
C1 C2 H2 . . 117.8 ?
C14 C15 C10 . . 119.4(4) ?
C14 C15 H15 . . 120.3 ?
C10 C15 H15 . . 120.3 ?
C8 C7 C6 . . 120.2(5) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C5 C6 C7 . . 120.0(5) ?
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C13 C14 C15 . . 120.1(5) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C7 C8 C9 . . 120.3(5) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
C13 C12 C11 . . 120.1(4) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
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 . 1.422(3) ?
S1 O2 . 1.429(3) ?
S1 N1 . 1.640(3) ?
S1 C10 . 1.756(4) ?
N1 C4 . 1.448(5) ?
N1 C1 . 1.479(5) ?
C9 C4 . 1.379(6) ?
C9 C8 . 1.382(7) ?
C9 H9 . 0.93 ?
C10 C11 . 1.374(6) ?
C10 C15 . 1.382(6) ?
C13 C14 . 1.354(8) ?
C13 C12 . 1.368(8) ?
C13 H13 . 0.93 ?
C3 C2 . 1.283(8) ?
C3 H3A . 0.93 ?
C3 H3B . 0.93 ?
C4 C5 . 1.376(6) ?
C1 C2 . 1.473(6) ?
C1 H1A . 0.97 ?
C1 H1B . 0.97 ?
C11 C12 . 1.380(7) ?
C11 H11 . 0.93 ?
C5 C6 . 1.377(7) ?
C5 H5 . 0.93 ?
C2 H2 . 0.93 ?
C15 C14 . 1.382(7) ?
C15 H15 . 0.93 ?
C7 C8 . 1.361(8) ?
C7 C6 . 1.379(7) ?
C7 H7 . 0.93 ?
C6 H6 . 0.93 ?
C14 H14 . 0.93 ?
C8 H8 . 0.93 ?
C12 H12 . 0.93 ?
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
C1 H1A O1 2_656 0.97 2.57 3.427(6) 147
C5 H5 O2 1_565 0.93 2.39 3.307(6) 167
C15 H15 O1 2_656 0.93 2.54 3.415(6) 158
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 C4 . . . . -158.8(3) ?
O2 S1 N1 C4 . . . . -29.5(4) ?
C10 S1 N1 C4 . . . . 86.2(3) ?
O1 S1 N1 C1 . . . . 53.2(4) ?
O2 S1 N1 C1 . . . . -177.5(3) ?
C10 S1 N1 C1 . . . . -61.9(3) ?
O1 S1 C10 C11 . . . . 150.3(4) ?
O2 S1 C10 C11 . . . . 19.0(4) ?
N1 S1 C10 C11 . . . . -95.5(4) ?
O1 S1 C10 C15 . . . . -33.1(4) ?
O2 S1 C10 C15 . . . . -164.5(4) ?
N1 S1 C10 C15 . . . . 81.1(4) ?
C8 C9 C4 C5 . . . . -0.2(7) ?
C8 C9 C4 N1 . . . . 177.7(4) ?
C1 N1 C4 C5 . . . . 55.6(5) ?
S1 N1 C4 C5 . . . . -92.3(4) ?
C1 N1 C4 C9 . . . . -122.2(4) ?
S1 N1 C4 C9 . . . . 89.8(4) ?
C4 N1 C1 C2 . . . . 58.4(5) ?
S1 N1 C1 C2 . . . . -153.1(4) ?
C15 C10 C11 C12 . . . . 0.8(7) ?
S1 C10 C11 C12 . . . . 177.3(4) ?
C9 C4 C5 C6 . . . . 0.5(7) ?
N1 C4 C5 C6 . . . . -177.3(4) ?
N1 C1 C2 C3 . . . . -141.8(6) ?
C11 C10 C15 C14 . . . . 0.5(7) ?
S1 C10 C15 C14 . . . . -176.1(4) ?
C4 C5 C6 C7 . . . . -0.1(7) ?
C8 C7 C6 C5 . . . . -0.7(8) ?
C12 C13 C14 C15 . . . . -0.1(9) ?
C10 C15 C14 C13 . . . . -0.9(8) ?
C6 C7 C8 C9 . . . . 1.0(8) ?
C4 C9 C8 C7 . . . . -0.6(7) ?
C14 C13 C12 C11 . . . . 1.5(9) ?
C10 C11 C12 C13 . . . . -1.8(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744866
2 PubChem 51413612
