##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.3
_journal_date_recd_electronic     2011-01-03
_journal_date_accepted     2011-01-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      2
_journal_page_first     o369
_journal_page_last     o369
_journal_paper_category     QO
_journal_coeditor_code     JH2254
_publ_contact_author_name     'Prof. Sung Kwon Kang'
_publ_contact_author_address
;
Department of Chemistry
Chungnam National University
Daejeon 305-764
Korea
;
_publ_contact_author_email     skkang@cnu.ac.kr
_publ_contact_author_fax      8E307(4)
_publ_contact_author_phone      8E307(4)
_publ_section_title
;
2,5-Dichloro-N-(4-methoxyphenyl)benzensulfonamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Khan, Islam Ullah'
;
Materials Chemistry Laboratory,
Department of Chemistry,
Government College University,
Lahore 54000,
Pakistan
;
    'Bibi, Sajida'
;
Materials Chemistry Laboratory,
Department of Chemistry,
Government College University,
Lahore 54000,
Pakistan
;
    'Mariam, Irfana'
;
Materials Chemistry Laboratory,
Department of Chemistry,
Government College University,
Lahore 54000,
Pakistan
;
    'Sharif, Shahzad'
;
Materials Chemistry Laboratory,
Department of Chemistry,
Government College University,
Lahore 54000,
Pakistan
;
    'Kang, Sung Kwon'
;
Department of Chemistry,
Chungnam National University,
Daejeon 305-764,
Republic of Korea
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
2,5-Dichloro-N-(4-methoxyphenyl)benzensulfonamide
;
_chemical_formula_moiety     'C13 H11 Cl2 N O3 S'
_chemical_formula_sum     'C13 H11 Cl2 N O3 S'
_chemical_formula_iupac     'C13 H11 Cl2 N O3 S'
_chemical_formula_weight     332.19
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     13.1599(4)
_cell_length_b     7.8179(2)
_cell_length_c     14.4830(5)
_cell_angle_alpha     90
_cell_angle_beta     110.5660(10)
_cell_angle_gamma     90
_cell_volume     1395.09(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4792
_cell_measurement_theta_min     2.88
_cell_measurement_theta_max     27.97
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.17
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.582
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     680
_exptl_absorpt_coefficient_mu     0.62
_exptl_absorpt_correction_type     none
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_reflns_number     13132
_diffrn_reflns_av_R_equivalents     0.0295
_diffrn_reflns_theta_min     3.01
_diffrn_reflns_theta_max     28.31
_diffrn_reflns_theta_full     28.31
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     19
_reflns_number_total     3456
_reflns_number_gt     2690
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_gt     0.0394
_refine_ls_wR_factor_ref     0.1084
_refine_ls_goodness_of_fit_ref     1.061
_refine_ls_restrained_S_all     1.061
_refine_ls_number_reflns     3456
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0450P)²+0.6614P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     0.001
_refine_diff_density_max     0.458
_refine_diff_density_min     -0.31
_refine_ls_extinction_method     none
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 0 '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 0.006 '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'
    Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 0.72780(4) 0.85926(6) 0.82650(3) 0.03916(14) Uani d . 1 . .
    O O2 0.73299(14) 1.04147(19) 0.82443(12) 0.0552(4) Uani d . 1 . .
    O O3 0.69500(12) 0.7655(2) 0.73648(10) 0.0493(4) Uani d . 1 . .
    C C4 0.85981(16) 0.7804(2) 0.89567(14) 0.0369(4) Uani d . 1 . .
    C C5 0.91579(17) 0.8160(3) 0.99528(15) 0.0419(4) Uani d . 1 . .
    C C6 1.02137(18) 0.7615(3) 1.03996(17) 0.0509(5) Uani d . 1 . .
    H H6 1.0576 0.7843 1.1065 0.061 Uiso calc R 1 . .
    C C7 1.07387(19) 0.6737(3) 0.98749(18) 0.0539(6) Uani d . 1 . .
    H H7 1.1455 0.6385 1.0176 0.065 Uiso calc R 1 . .
    C C8 1.01785(18) 0.6389(3) 0.88887(17) 0.0485(5) Uani d . 1 . .
    C C9 0.91210(17) 0.6898(3) 0.84328(15) 0.0427(4) Uani d . 1 . .
    H H9 0.8756 0.6635 0.7772 0.051 Uiso calc R 1 . .
    Cl Cl10 0.85599(5) 0.93075(8) 1.06480(4) 0.05536(17) Uani d . 1 . .
    Cl Cl11 1.08144(6) 0.53037(11) 0.82003(6) 0.0786(2) Uani d . 1 . .
    N N12 0.64500(14) 0.8123(2) 0.88365(13) 0.0398(4) Uani d . 1 . .
    H H12 0.6441(19) 0.888(3) 0.9181(17) 0.046(7) Uiso d . 1 . .
    C C13 0.63424(15) 0.6413(2) 0.91467(13) 0.0350(4) Uani d . 1 . .
    C C14 0.65129(17) 0.6093(3) 1.01225(14) 0.0412(4) Uani d . 1 . .
    H H14 0.6706 0.6986 1.0575 0.049 Uiso calc R 1 . .
    C C15 0.64003(17) 0.4456(3) 1.04402(15) 0.0423(5) Uani d . 1 . .
    H H15 0.6504 0.4257 1.11 0.051 Uiso calc R 1 . .
    C C16 0.61338(16) 0.3123(3) 0.97760(15) 0.0405(4) Uani d . 1 . .
    C C17 0.59349(19) 0.3448(3) 0.87865(15) 0.0476(5) Uani d . 1 . .
    H H17 0.5737 0.2557 0.8333 0.057 Uiso calc R 1 . .
    C C18 0.60287(18) 0.5083(3) 0.84720(15) 0.0448(5) Uani d . 1 . .
    H H18 0.5881 0.5295 0.7806 0.054 Uiso calc R 1 . .
    O O19 0.60296(14) 0.1448(2) 1.00210(12) 0.0560(4) Uani d . 1 . .
    C C20 0.6237(2) 0.1095(3) 1.10353(19) 0.0610(6) Uani d . 1 . .
    H H20A 0.6977 0.138 1.1414 0.091 Uiso calc R 1 . .
    H H20B 0.6117 -0.0098 1.1116 0.091 Uiso calc R 1 . .
    H H20C 0.5759 0.1765 1.126 0.091 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0448(3) 0.0397(3) 0.0347(2) 0.0049(2) 0.0162(2) 0.00713(19)
    O2 0.0669(10) 0.0399(8) 0.0638(10) 0.0066(7) 0.0292(9) 0.0140(7)
    O3 0.0502(8) 0.0672(10) 0.0303(7) 0.0043(7) 0.0137(6) 0.0024(7)
    C4 0.0414(10) 0.0341(9) 0.0361(9) -0.0023(8) 0.0147(8) 0.0044(7)
    C5 0.0504(11) 0.0387(10) 0.0371(10) -0.0093(9) 0.0158(9) 0.0011(8)
    C6 0.0489(12) 0.0532(13) 0.0423(11) -0.0122(10) 0.0056(10) 0.0042(10)
    C7 0.0414(11) 0.0580(14) 0.0583(14) -0.0021(10) 0.0128(10) 0.0121(11)
    C8 0.0474(12) 0.0490(12) 0.0533(12) 0.0055(9) 0.0231(10) 0.0097(10)
    C9 0.0471(11) 0.0426(11) 0.0404(10) 0.0018(9) 0.0178(9) 0.0049(8)
    Cl10 0.0707(4) 0.0531(3) 0.0446(3) -0.0098(3) 0.0231(3) -0.0122(2)
    Cl11 0.0661(4) 0.1040(6) 0.0740(5) 0.0343(4) 0.0349(4) 0.0095(4)
    N12 0.0480(10) 0.0371(9) 0.0386(9) 0.0037(7) 0.0205(8) -0.0011(7)
    C13 0.0340(9) 0.0368(10) 0.0363(9) 0.0017(7) 0.0151(8) -0.0002(8)
    C14 0.0475(11) 0.0427(11) 0.0356(10) -0.0059(8) 0.0175(9) -0.0070(8)
    C15 0.0475(11) 0.0487(12) 0.0332(10) -0.0065(9) 0.0172(9) -0.0002(8)
    C16 0.0415(10) 0.0391(10) 0.0427(11) -0.0018(8) 0.0171(9) 0.0011(8)
    C17 0.0629(13) 0.0414(11) 0.0390(11) -0.0044(9) 0.0185(10) -0.0090(9)
    C18 0.0574(13) 0.0449(11) 0.0312(9) -0.0003(9) 0.0146(9) -0.0023(8)
    O19 0.0776(11) 0.0403(8) 0.0550(9) -0.0060(7) 0.0290(8) 0.0021(7)
    C20 0.0800(17) 0.0519(14) 0.0613(15) 0.0073(12) 0.0377(13) 0.0149(12)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 O3 . 1.4243(15) ?
    S1 O2 . 1.4269(16) ?
    S1 N12 . 1.6250(17) ?
    S1 C4 . 1.783(2) ?
    C4 C9 . 1.385(3) ?
    C4 C5 . 1.398(3) ?
    C5 C6 . 1.378(3) ?
    C5 Cl10 . 1.731(2) ?
    C6 C7 . 1.377(3) ?
    C6 H6 . 0.93 ?
    C7 C8 . 1.385(3) ?
    C7 H7 . 0.93 ?
    C8 C9 . 1.373(3) ?
    C8 Cl11 . 1.732(2) ?
    C9 H9 . 0.93 ?
    N12 C13 . 1.433(3) ?
    N12 H12 . 0.78(2) ?
    C13 C14 . 1.374(3) ?
    C13 C18 . 1.387(3) ?
    C14 C15 . 1.386(3) ?
    C14 H14 . 0.93 ?
    C15 C16 . 1.377(3) ?
    C15 H15 . 0.93 ?
    C16 O19 . 1.376(2) ?
    C16 C17 . 1.387(3) ?
    C17 C18 . 1.377(3) ?
    C17 H17 . 0.93 ?
    C18 H18 . 0.93 ?
    O19 C20 . 1.424(3) ?
    C20 H20A . 0.96 ?
    C20 H20B . 0.96 ?
    C20 H20C . 0.96 ?
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
    O3 S1 O2 . . 119.74(10) ?
    O3 S1 N12 . . 107.95(10) ?
    O2 S1 N12 . . 106.36(10) ?
    O3 S1 C4 . . 104.98(9) ?
    O2 S1 C4 . . 108.22(10) ?
    N12 S1 C4 . . 109.34(9) ?
    C9 C4 C5 . . 118.95(19) ?
    C9 C4 S1 . . 116.27(15) ?
    C5 C4 S1 . . 124.56(16) ?
    C6 C5 C4 . . 120.1(2) ?
    C6 C5 Cl10 . . 118.46(17) ?
    C4 C5 Cl10 . . 121.40(16) ?
    C7 C6 C5 . . 120.9(2) ?
    C7 C6 H6 . . 119.5 ?
    C5 C6 H6 . . 119.5 ?
    C6 C7 C8 . . 118.6(2) ?
    C6 C7 H7 . . 120.7 ?
    C8 C7 H7 . . 120.7 ?
    C9 C8 C7 . . 121.4(2) ?
    C9 C8 Cl11 . . 118.56(18) ?
    C7 C8 Cl11 . . 120.00(18) ?
    C8 C9 C4 . . 120.0(2) ?
    C8 C9 H9 . . 120 ?
    C4 C9 H9 . . 120 ?
    C13 N12 S1 . . 121.87(14) ?
    C13 N12 H12 . . 119.1(18) ?
    S1 N12 H12 . . 108.5(18) ?
    C14 C13 C18 . . 119.27(18) ?
    C14 C13 N12 . . 119.59(17) ?
    C18 C13 N12 . . 121.09(17) ?
    C13 C14 C15 . . 120.78(18) ?
    C13 C14 H14 . . 119.6 ?
    C15 C14 H14 . . 119.6 ?
    C16 C15 C14 . . 119.84(18) ?
    C16 C15 H15 . . 120.1 ?
    C14 C15 H15 . . 120.1 ?
    O19 C16 C15 . . 124.31(18) ?
    O19 C16 C17 . . 116.17(18) ?
    C15 C16 C17 . . 119.51(19) ?
    C18 C17 C16 . . 120.37(19) ?
    C18 C17 H17 . . 119.8 ?
    C16 C17 H17 . . 119.8 ?
    C17 C18 C13 . . 120.14(18) ?
    C17 C18 H18 . . 119.9 ?
    C13 C18 H18 . . 119.9 ?
    C16 O19 C20 . . 116.76(18) ?
    O19 C20 H20A . . 109.5 ?
    O19 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    O19 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
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
    N12 H12 O19 1_565 0.78(2) 2.50(3) 3.267(2) 168(2)
