##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-05-29
_journal_date_accepted     2012-05-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      7
_journal_page_first     o2090
_journal_page_last     o2090
_journal_paper_category     QO
_journal_paper_doi     10.1107/S160053681202483X
_journal_coeditor_code     IS5148
_publ_contact_author_name     'Yousuf, S. '
_publ_contact_author_address
;
      H.E.J. Research Institute of Chemistry,
      International Cenetr for Chemical and Biological Sciences,
      University of Karachi,
      Karachi 75270, Pakistan
;
_publ_contact_author_email     'dr.sammer.yousuf@gmail.com'
_publ_contact_author_fax     '+92-21 34819018-9'
_publ_contact_author_phone     '+92-21 34824924'
_publ_section_title
;
N-(4-Methoxy-2-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Sammer Yousuf' ?
;     H.E.J. Research Institute of Chemistry,
      International Center for Chemical and Biological Sciences,
      University of Karachi,
      Karachi 75270, Pakistan
;
    'Hina Siddiqui' ?
;     H.E.J. Research Institute of Chemistry,
      International Center for Chemical and Biological Sciences,
      University of Karachi,
      Karachi 75270, Pakistan
;
    'Rabia Farooq' ?
;     H.E.J. Research Institute of Chemistry,
      International Center for Chemical and Biological Sciences,
      University of Karachi,
      Karachi 75270, Pakistan
;
    'M. Iqbal Choudhary' ?
;
H.E.J. Research Institute of Chemistry,
International Center for Chemical and Biological Sciences,
University of Karachi,
Karachi 75270, Pakistan
Department of Biochemistry, Faculty of Sciences,
King Abdul Aziz University, Jeddah 21589, Saudi Arabia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-(4-Methoxy-2-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H12 N2 O7 S2'
_chemical_formula_sum     'C9 H12 N2 O7 S2'
_chemical_formula_iupac     'C9 H12 N2 O7 S2'
_chemical_formula_weight     324.33
_chemical_melting_point     ?
_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     9.4976(7)
_cell_length_b     7.5987(6)
_cell_length_c     19.2434(15)
_cell_angle_alpha     90.00
_cell_angle_beta     103.672(2)
_cell_angle_gamma     90.00
_cell_volume     1349.43(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3096
_cell_measurement_theta_min     2.18
_cell_measurement_theta_max     27.68
_cell_measurement_temperature     273(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.47
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.596
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     672
_exptl_absorpt_coefficient_mu     0.427
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.7989
_exptl_absorpt_correction_T_max     0.9545
_exptl_special_details     ?
_diffrn_ambient_temperature     273(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9504
_diffrn_reflns_av_R_equivalents     0.0234
_diffrn_reflns_av_sigmaI/netI     0.0253
_diffrn_reflns_theta_min     2.18
_diffrn_reflns_theta_max     28.33
_diffrn_reflns_theta_full     28.33
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     3362
_reflns_number_gt     2711
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0505
_refine_ls_R_factor_gt     0.0397
_refine_ls_wR_factor_gt     0.1057
_refine_ls_wR_factor_ref     0.1133
_refine_ls_goodness_of_fit_ref     1.046
_refine_ls_restrained_S_all     1.046
_refine_ls_number_reflns     3362
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0641P)²+0.2074P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.308
_refine_diff_density_min     -0.301
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0101(14)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.80706(5) 0.21065(6) -0.02024(2) 0.03866(15) Uani d . 1 1 . .
    S S2 0.67671(5) 0.31016(6) 0.09782(2) 0.03825(15) Uani d . 1 1 . .
    O O1 0.55361(15) 0.22596(19) 0.05410(8) 0.0529(4) Uani d . 1 1 . .
    O O2 0.71498(16) 0.2788(2) 0.17294(7) 0.0514(4) Uani d . 1 1 . .
    O O3 0.95185(15) 0.2109(2) -0.02879(7) 0.0522(4) Uani d . 1 1 . .
    O O4 0.70649(16) 0.3355(2) -0.05856(7) 0.0561(4) Uani d . 1 1 . .
    O O5 0.80101(17) -0.07491(19) 0.12618(9) 0.0608(4) Uani d . 1 1 . .
    O O6 0.99411(19) -0.20742(17) 0.18046(9) 0.0602(4) Uani d . 1 1 . .
    O O7 1.36416(14) 0.2232(2) 0.25913(8) 0.0503(4) Uani d . 1 1 . .
    N N1 0.92993(18) -0.07629(18) 0.15472(8) 0.0381(3) Uani d . 1 1 . .
    N N2 0.82155(15) 0.24662(18) 0.06736(7) 0.0329(3) Uani d . 1 1 . .
    C C1 1.14724(19) 0.0885(2) 0.20463(9) 0.0345(4) Uani d . 1 1 . .
    H H1B 1.1802 -0.0117 0.2313 0.041 Uiso calc R 1 1 . .
    C C2 1.01332(18) 0.0890(2) 0.15816(8) 0.0311(3) Uani d . 1 1 . .
    C C3 0.96028(17) 0.2371(2) 0.11724(8) 0.0315(3) Uani d . 1 1 . .
    C C4 1.04925(19) 0.3835(2) 0.12521(10) 0.0406(4) Uani d . 1 1 . .
    H H4B 1.0171 0.4833 0.0982 0.049 Uiso calc R 1 1 . .
    C C5 1.1838(2) 0.3863(2) 0.17185(10) 0.0428(4) Uani d . 1 1 . .
    H H5A 1.2407 0.4872 0.1764 0.051 Uiso calc R 1 1 . .
    C C6 1.23354(19) 0.2382(3) 0.21179(9) 0.0366(4) Uani d . 1 1 . .
    C C7 1.4561(2) 0.3748(3) 0.27101(13) 0.0630(6) Uani d . 1 1 . .
    H H7A 1.5458 0.3458 0.3040 0.095 Uiso calc R 1 1 . .
    H H7B 1.4090 0.4680 0.2905 0.095 Uiso calc R 1 1 . .
    H H7C 1.4752 0.4123 0.2265 0.095 Uiso calc R 1 1 . .
    C C8 0.6647(3) 0.5369(3) 0.08270(13) 0.0576(6) Uani d . 1 1 . .
    H H8A 0.5830 0.5830 0.0981 0.086 Uiso calc R 1 1 . .
    H H8B 0.6528 0.5598 0.0326 0.086 Uiso calc R 1 1 . .
    H H8C 0.7517 0.5927 0.1091 0.086 Uiso calc R 1 1 . .
    C C9 0.7335(2) -0.0003(3) -0.03754(11) 0.0507(5) Uani d . 1 1 . .
    H H9A 0.7196 -0.0262 -0.0875 0.076 Uiso calc R 1 1 . .
    H H9B 0.6421 -0.0054 -0.0246 0.076 Uiso calc R 1 1 . .
    H H9C 0.7986 -0.0849 -0.0100 0.076 Uiso calc R 1 1 . .
_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 O4 . 1.4223(15) ?
    S1 O3 . 1.4231(14) ?
    S1 N2 . 1.6809(14) ?
    S1 C9 . 1.748(2) ?
    S2 O1 . 1.4210(14) ?
    S2 O2 . 1.4247(14) ?
    S2 N2 . 1.6882(15) ?
    S2 C8 . 1.747(2) ?
    O5 N1 . 1.218(2) ?
    O6 N1 . 1.211(2) ?
    O7 C6 . 1.359(2) ?
    O7 C7 . 1.431(3) ?
    N1 C2 . 1.478(2) ?
    N2 C3 . 1.437(2) ?
    C1 C2 . 1.371(2) ?
    C1 C6 . 1.389(2) ?
    C1 H1B . 0.9300 ?
    C2 C3 . 1.397(2) ?
    C3 C4 . 1.383(2) ?
    C4 C5 . 1.377(2) ?
    C4 H4B . 0.9300 ?
    C5 C6 . 1.382(3) ?
    C5 H5A . 0.9300 ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
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
    O4 S1 O3 . . 119.21(9) ?
    O4 S1 N2 . . 107.30(8) ?
    O3 S1 N2 . . 105.27(8) ?
    O4 S1 C9 . . 108.87(10) ?
    O3 S1 C9 . . 109.43(10) ?
    N2 S1 C9 . . 105.93(9) ?
    O1 S2 O2 . . 120.15(9) ?
    O1 S2 N2 . . 106.83(8) ?
    O2 S2 N2 . . 105.73(8) ?
    O1 S2 C8 . . 109.48(11) ?
    O2 S2 C8 . . 108.96(10) ?
    N2 S2 C8 . . 104.52(10) ?
    C6 O7 C7 . . 117.75(16) ?
    O6 N1 O5 . . 123.14(15) ?
    O6 N1 C2 . . 117.92(15) ?
    O5 N1 C2 . . 118.94(14) ?
    C3 N2 S1 . . 120.43(11) ?
    C3 N2 S2 . . 118.43(11) ?
    S1 N2 S2 . . 120.96(8) ?
    C2 C1 C6 . . 119.80(16) ?
    C2 C1 H1B . . 120.1 ?
    C6 C1 H1B . . 120.1 ?
    C1 C2 C3 . . 121.66(15) ?
    C1 C2 N1 . . 115.57(14) ?
    C3 C2 N1 . . 122.77(15) ?
    C4 C3 C2 . . 117.11(15) ?
    C4 C3 N2 . . 118.25(15) ?
    C2 C3 N2 . . 124.63(15) ?
    C5 C4 C3 . . 122.23(16) ?
    C5 C4 H4B . . 118.9 ?
    C3 C4 H4B . . 118.9 ?
    C4 C5 C6 . . 119.50(17) ?
    C4 C5 H5A . . 120.3 ?
    C6 C5 H5A . . 120.3 ?
    O7 C6 C5 . . 125.38(17) ?
    O7 C6 C1 . . 114.93(17) ?
    C5 C6 C1 . . 119.70(16) ?
    O7 C7 H7A . . 109.5 ?
    O7 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    O7 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    S2 C8 H8A . . 109.5 ?
    S2 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    S2 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    S1 C9 H9A . . 109.5 ?
    S1 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    S1 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
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
    O4 S1 N2 C3 . . . . -139.57(14) ?
    O3 S1 N2 C3 . . . . -11.63(15) ?
    C9 S1 N2 C3 . . . . 104.25(14) ?
    O4 S1 N2 S2 . . . . 35.55(12) ?
    O3 S1 N2 S2 . . . . 163.50(10) ?
    C9 S1 N2 S2 . . . . -80.63(12) ?
    O1 S2 N2 C3 . . . . -150.32(13) ?
    O2 S2 N2 C3 . . . . -21.24(15) ?
    C8 S2 N2 C3 . . . . 93.69(15) ?
    O1 S2 N2 S1 . . . . 34.46(12) ?
    O2 S2 N2 S1 . . . . 163.53(10) ?
    C8 S2 N2 S1 . . . . -81.53(12) ?
    C6 C1 C2 C3 . . . . 0.0(3) ?
    C6 C1 C2 N1 . . . . -179.76(15) ?
    O6 N1 C2 C1 . . . . -14.8(2) ?
    O5 N1 C2 C1 . . . . 165.47(17) ?
    O6 N1 C2 C3 . . . . 165.42(17) ?
    O5 N1 C2 C3 . . . . -14.3(2) ?
    C1 C2 C3 C4 . . . . 0.4(2) ?
    N1 C2 C3 C4 . . . . -179.79(15) ?
    C1 C2 C3 N2 . . . . 179.70(15) ?
    N1 C2 C3 N2 . . . . -0.5(3) ?
    S1 N2 C3 C4 . . . . 82.83(19) ?
    S2 N2 C3 C4 . . . . -92.42(17) ?
    S1 N2 C3 C2 . . . . -96.42(17) ?
    S2 N2 C3 C2 . . . . 88.33(19) ?
    C2 C3 C4 C5 . . . . -0.8(3) ?
    N2 C3 C4 C5 . . . . 179.87(17) ?
    C3 C4 C5 C6 . . . . 0.7(3) ?
    C7 O7 C6 C5 . . . . 2.6(3) ?
    C7 O7 C6 C1 . . . . -177.73(17) ?
    C4 C5 C6 O7 . . . . 179.46(18) ?
    C4 C5 C6 C1 . . . . -0.2(3) ?
    C2 C1 C6 O7 . . . . -179.86(15) ?
    C2 C1 C6 C5 . . . . -0.2(3) ?
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
    C1 H1B O2 2_745 0.93 2.46 3.368(2) 165 yes
    C8 H8B O4 . 0.96 2.58 3.225(3) 125 yes
    C8 H8C O5 1_565 0.96 2.58 3.250(3) 127 yes
    C9 H9B O1 . 0.96 2.59 3.226(3) 124 yes
    C9 H9B O1 3_655 0.96 2.47 3.173(3) 130 yes
