#------------------------------------------------------------------------------
#$Date: 2017-03-02 08:10:16 +0200 (Thu, 02 Mar 2017) $
#$Revision: 192769 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/53/1545384.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_1545384
loop_
_publ_author_name
'Shakuntala, K.'
'Kumari, Vijaya'
'Lokanath, N. K.'
'Naveen, S.'
'Suchetan, P. A.'
_publ_section_title
;
 2,5-Dimethoxy-N-phenylbenzenesulfonamide
;
_journal_coeditor_code           HB4126
_journal_issue                   2
_journal_name_full               IUCrData
_journal_page_first              x170311
_journal_paper_doi               10.1107/S241431461700311X
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C14 H15 N O4 S'
_chemical_formula_moiety         'C14 H15 N O4 S'
_chemical_formula_sum            'C14 H15 N O4 S'
_chemical_formula_weight         293.33
_chemical_melting_point          439
_chemical_name_systematic
;
2,5-Dimethoxy-N-phenylbenzenesulfonamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 117.064(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4328(12)
_cell_length_b                   14.3157(15)
_cell_length_c                   10.4869(12)
_cell_measurement_reflns_used    143
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      64.5
_cell_measurement_theta_min      7.8
_cell_volume                     1394.7(3)
_computing_cell_refinement
;
APEX2 and SAINT-Plus (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT-Plus and XPREP (Bruker, 2009)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2016 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10083
_diffrn_reflns_theta_full        64.537
_diffrn_reflns_theta_max         64.537
_diffrn_reflns_theta_min         7.799
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_count 1
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    2.187
_exptl_absorpt_correction_T_max  0.689
_exptl_absorpt_correction_T_min  0.589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       Prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.332
_refine_ls_extinction_coef       0.0106(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2016 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0666
_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)+(0.1364P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.1857
_reflns_number_gt                1943
_reflns_number_total             2305
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4126sup1.cif
_cod_data_source_block           I
_cod_database_code               1545384
_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   0.579
_shelx_estimated_absorpt_t_max   0.707
loop_
_space_group_symop_operation_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_occupancy
C C1 0.3763(3) 0.95415(17) 0.1449(3) 0.0446(6) Uani d 1
C C2 0.4926(3) 0.8928(2) 0.2056(3) 0.0554(7) Uani d 1
C C3 0.5215(4) 0.8363(2) 0.1138(4) 0.0729(9) Uani d 1
H H3 0.598056 0.794521 0.151637 0.087 Uiso calc 1
C C4 0.4387(4) 0.8413(3) -0.0311(4) 0.0770(10) Uani d 1
H H4 0.460099 0.803009 -0.090500 0.092 Uiso calc 1
C C5 0.3243(3) 0.9021(2) -0.0908(3) 0.0629(8) Uani d 1
C C6 0.2922(3) 0.95933(18) -0.0021(3) 0.0517(7) Uani d 1
H H6 0.215095 1.000645 -0.040936 0.062 Uiso calc 1
C C7 0.1886(3) 0.89741(16) 0.3259(3) 0.0408(6) Uani d 1
C C8 0.1959(3) 0.8411(2) 0.4360(3) 0.0560(7) Uani d 1
H H8 0.272972 0.846112 0.527111 0.067 Uiso calc 1
C C9 0.0868(4) 0.7771(2) 0.4089(4) 0.0691(9) Uani d 1
H H9 0.090240 0.739609 0.482882 0.083 Uiso calc 1
C C10 -0.0254(3) 0.7683(2) 0.2754(3) 0.0642(8) Uani d 1
H H10 -0.097532 0.724621 0.258041 0.077 Uiso calc 1
C C11 -0.0312(3) 0.8241(2) 0.1673(3) 0.0592(7) Uani d 1
H H11 -0.108127 0.818391 0.076232 0.071 Uiso calc 1
C C12 0.0749(3) 0.88843(18) 0.1910(3) 0.0490(7) Uani d 1
H H12 0.070090 0.925756 0.116314 0.059 Uiso calc 1
C C13 0.6919(3) 0.8361(3) 0.4161(4) 0.0818(10) Uani d 1
H H13A 0.666377 0.771490 0.394795 0.123 Uiso calc 1
H H13B 0.736012 0.845323 0.517872 0.123 Uiso calc 1
H H13C 0.758229 0.853612 0.380173 0.123 Uiso calc 1
C C14 0.1182(5) 0.9532(3) -0.3002(4) 0.0897(12) Uani d 1
H H14A 0.056384 0.935813 -0.258691 0.135 Uiso calc 1
H H14B 0.070058 0.941372 -0.401306 0.135 Uiso calc 1
H H14C 0.140914 1.018497 -0.283666 0.135 Uiso calc 1
N N1 0.3015(3) 0.96370(15) 0.3628(2) 0.0477(6) Uani d 1
O O1 0.2068(2) 1.07776(12) 0.16321(19) 0.0545(6) Uani d 1
O O2 0.4588(2) 1.08222(13) 0.3458(2) 0.0583(6) Uani d 1
O O3 0.5672(2) 0.89154(16) 0.3507(2) 0.0716(7) Uani d 1
O O4 0.2466(3) 0.90022(19) -0.2364(2) 0.0871(8) Uani d 1
S S1 0.33445(6) 1.02855(4) 0.25483(6) 0.0437(3) Uani d 1
H H1 0.375(2) 0.9564(18) 0.443(2) 0.050(8) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C6 C1 C2 121.3(2)
C6 C1 S1 118.3(2)
C2 C1 S1 120.3(2)
O3 C2 C3 125.0(3)
O3 C2 C1 117.1(2)
C3 C2 C1 117.9(3)
C4 C3 C2 120.8(3)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 121.2(3)
C3 C4 H4 119.4
C5 C4 H4 119.4
O4 C5 C4 116.5(3)
O4 C5 C6 124.0(3)
C4 C5 C6 119.4(3)
C1 C6 C5 119.3(3)
C1 C6 H6 120.3
C5 C6 H6 120.3
C12 C7 C8 119.9(2)
C12 C7 N1 124.1(2)
C8 C7 N1 116.0(2)
C7 C8 C9 119.1(3)
C7 C8 H8 120.4
C9 C8 H8 120.4
C10 C9 C8 120.9(3)
C10 C9 H9 119.6
C8 C9 H9 119.6
C9 C10 C11 119.5(3)
C9 C10 H10 120.3
C11 C10 H10 120.3
C10 C11 C12 121.0(3)
C10 C11 H11 119.5
C12 C11 H11 119.5
C11 C12 C7 119.7(2)
C11 C12 H12 120.2
C7 C12 H12 120.2
O3 C13 H13A 109.5
O3 C13 H13B 109.5
H13A C13 H13B 109.5
O3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O4 C14 H14A 109.5
O4 C14 H14B 109.5
H14A C14 H14B 109.5
O4 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C7 N1 S1 127.30(18)
C7 N1 H1 116.7(19)
S1 N1 H1 113(2)
C2 O3 C13 119.0(2)
C5 O4 C14 118.0(2)
O1 S1 O2 117.96(12)
O1 S1 N1 108.95(12)
O2 S1 N1 104.93(11)
O1 S1 C1 106.93(11)
O2 S1 C1 109.90(12)
N1 S1 C1 107.79(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.386(4)
C1 C2 1.395(4)
C1 S1 1.764(3)
C2 O3 1.359(3)
C2 C3 1.391(4)
C3 C4 1.366(5)
C3 H3 0.9300
C4 C5 1.376(4)
C4 H4 0.9300
C5 O4 1.365(4)
C5 C6 1.390(4)
C6 H6 0.9300
C7 C12 1.378(4)
C7 C8 1.382(4)
C7 N1 1.422(3)
C8 C9 1.387(4)
C8 H8 0.9300
C9 C10 1.362(4)
C9 H9 0.9300
C10 C11 1.366(4)
C10 H10 0.9300
C11 C12 1.373(4)
C11 H11 0.9300
C12 H12 0.9300
C13 O3 1.407(4)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 O4 1.416(4)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
N1 S1 1.618(2)
N1 H1 0.849(18)
O1 S1 1.4240(19)
O2 S1 1.4345(19)
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
C12 H12 O1 5_555 0.93 2.52 3.1128 121 yes
N1 H1 O2 3_676 0.85 2.17 3.0116(10) 170 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
C6 C1 C2 O3 -178.9(3)
S1 C1 C2 O3 2.0(3)
C6 C1 C2 C3 -0.4(4)
S1 C1 C2 C3 -179.5(2)
O3 C2 C3 C4 178.8(3)
C1 C2 C3 C4 0.4(5)
C2 C3 C4 C5 -0.2(6)
C3 C4 C5 O4 -178.6(3)
C3 C4 C5 C6 -0.1(5)
C2 C1 C6 C5 0.1(4)
S1 C1 C6 C5 179.2(2)
O4 C5 C6 C1 178.5(3)
C4 C5 C6 C1 0.1(4)
C12 C7 C8 C9 -0.9(4)
N1 C7 C8 C9 177.8(2)
C7 C8 C9 C10 1.0(5)
C8 C9 C10 C11 -0.7(5)
C9 C10 C11 C12 0.4(5)
C10 C11 C12 C7 -0.4(4)
C8 C7 C12 C11 0.6(4)
N1 C7 C12 C11 -177.9(2)
C12 C7 N1 S1 -10.5(4)
C8 C7 N1 S1 170.9(2)
C3 C2 O3 C13 6.4(5)
C1 C2 O3 C13 -175.2(3)
C4 C5 O4 C14 172.4(3)
C6 C5 O4 C14 -6.0(5)
C7 N1 S1 O1 52.9(2)
C7 N1 S1 O2 -179.9(2)
C7 N1 S1 C1 -62.9(2)
C6 C1 S1 O1 4.3(2)
C2 C1 S1 O1 -176.6(2)
C6 C1 S1 O2 -124.9(2)
C2 C1 S1 O2 54.3(2)
C6 C1 S1 N1 121.3(2)
C2 C1 S1 N1 -59.5(2)

_cod_database_fobs_code 1545384
