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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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.                                        #
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# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
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# 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 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2007-03-28
_journal_date_accepted     2007-03-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      5
_journal_page_first     o2337
_journal_page_last     o2337
_journal_paper_category     QO
_journal_coeditor_code     BT2328
_publ_contact_author_name     'Prof. B. Thimme Gowda'
_publ_contact_author_address
;
  Department of Chemistry
  Mangalore University
  Mangalagangotri-574 199
  Mangalore, INDIA
;
_publ_contact_author_email     gowdabt@yahoo.com
_publ_contact_author_fax     '91 824 2287262'
_publ_contact_author_phone     '91 824 2287367'
_publ_section_title
;
N-(3-Nitrophenyl)methanesulfonamide
;
loop_
    _publ_author_name
    _publ_author_address
    'B. Thimme Gowda'
; Department of Chemistry
  Mangalore University
  Mangalagangotri 574 199
  Mangalore, India
;
    'Sabine Foro'
; Institute of Materials Science
  Darmstadt University of Technology
  Petersenstrasse 23
  D-64287 Darmstadt,
  Germany
;
    'Hartmut Fuess '
; Institute of Materials Science
  Darmstadt University of Technology
  Petersenstrasse 23
  D-64287 Darmstadt,
  Germany
;
data_I
_chemical_name_systematic
;
N-(3-nitrophenyl)methanesulfonamide
;
_chemical_name_common     'N-(3-nitrophenyl)-methanesulfonamide'
_chemical_formula_moiety     'C7 H8 N2 O4 S'
_chemical_formula_sum     'C7 H8 N2 O4 S'
_chemical_formula_iupac     'C7 H8 N2 O4 S'
_chemical_formula_weight     216.21
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_HALL     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.9590(10)
_cell_length_b     8.2070(10)
_cell_length_c     8.7590(10)
_cell_angle_alpha     96.930(10)
_cell_angle_beta     111.050(10)
_cell_angle_gamma     99.780(10)
_cell_volume     451.02(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     5.51
_cell_measurement_theta_max     25.30
_cell_measurement_temperature     299(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.592
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     224
_exptl_absorpt_coefficient_mu     3.178
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     299(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2782
_diffrn_reflns_av_R_equivalents     0.0709
_diffrn_reflns_av_sigmaI/netI     0.0650
_diffrn_reflns_theta_min     5.52
_diffrn_reflns_theta_max     66.93
_diffrn_reflns_theta_full     66.93
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     5
_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 > 2sigma(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     1611
_reflns_number_gt     1427
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0539
_refine_ls_R_factor_gt     0.0419
_refine_ls_wR_factor_gt     0.1010
_refine_ls_wR_factor_ref     0.1050
_refine_ls_goodness_of_fit_ref     1.084
_refine_ls_restrained_S_all     1.084
_refine_ls_number_reflns     1611
_refine_ls_number_parameters     143
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0588P)²+0.0989P] 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     0.493
_refine_diff_density_min     -0.487
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.091(5)
_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' 0.0181 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'
_computing_data_collection
;
CAD-4-PC (Nonius, 1996)
;
_computing_cell_refinement
;
CAD-4-PC
;
_computing_data_reduction     'REDU4 (Stoe & Cie, 1987)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL97'
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
    C C1 0.0954(4) 0.8080(3) 0.6291(3) 0.0525(6) Uani d . 1 . .
    H H1A 0.1469 0.9231 0.6882 0.063 Uiso calc R 1 . .
    H H1B 0.1232 0.7341 0.7074 0.063 Uiso calc R 1 . .
    H H1C -0.0542 0.7869 0.5660 0.063 Uiso calc R 1 . .
    C C6 0.5674(3) 0.7198(2) 0.7373(2) 0.0362(4) Uani d . 1 . .
    C C7 0.5029(3) 0.5475(3) 0.7208(2) 0.0390(4) Uani d . 1 . .
    H H7 0.398(4) 0.479(3) 0.622(3) 0.047 Uiso d . 1 . .
    C C8 0.6099(3) 0.4749(2) 0.8503(2) 0.0386(4) Uani d . 1 . .
    C C9 0.7761(3) 0.5638(3) 0.9932(3) 0.0447(5) Uani d . 1 . .
    H H9 0.838(4) 0.505(4) 1.075(3) 0.054 Uiso d . 1 . .
    C C10 0.8369(3) 0.7366(3) 1.0067(3) 0.0501(5) Uani d . 1 . .
    H H10 0.947(4) 0.796(4) 1.100(4) 0.060 Uiso d . 1 . .
    C C11 0.7328(3) 0.8137(3) 0.8807(3) 0.0456(5) Uani d . 1 . .
    H H11 0.770(4) 0.938(4) 0.890(3) 0.055 Uiso d . 1 . .
    N N5 0.4746(3) 0.8055(2) 0.6095(2) 0.0478(5) Uani d D 1 . .
    H H5N 0.539(4) 0.9067(17) 0.621(3) 0.057 Uiso d D 1 . .
    N N12 0.5437(3) 0.2912(2) 0.8337(2) 0.0515(5) Uani d . 1 . .
    O O3 0.2113(2) 0.8999(2) 0.39469(18) 0.0530(4) Uani d . 1 . .
    O O4 0.1475(2) 0.59956(19) 0.41044(18) 0.0507(4) Uani d . 1 . .
    O O13 0.6464(3) 0.2257(2) 0.9437(3) 0.0758(6) Uani d . 1 . .
    O O14 0.3897(4) 0.2133(2) 0.7117(2) 0.0742(6) Uani d . 1 . .
    S S2 0.22342(7) 0.77189(6) 0.49366(5) 0.0378(2) Uani d . 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
    C1 0.0592(13) 0.0449(12) 0.0550(12) 0.0107(10) 0.0241(10) 0.0113(10)
    C6 0.0321(9) 0.0376(10) 0.0367(9) 0.0036(7) 0.0118(7) 0.0111(8)
    C7 0.0412(10) 0.0353(10) 0.0350(9) 0.0021(8) 0.0117(8) 0.0062(8)
    C8 0.0439(10) 0.0349(10) 0.0435(10) 0.0106(8) 0.0225(8) 0.0115(8)
    C9 0.0390(10) 0.0542(12) 0.0437(11) 0.0151(9) 0.0142(8) 0.0192(9)
    C10 0.0378(10) 0.0538(13) 0.0434(11) 0.0019(9) 0.0022(9) 0.0091(10)
    C11 0.0384(10) 0.0386(11) 0.0479(11) -0.0021(8) 0.0075(8) 0.0095(9)
    N5 0.0372(9) 0.0424(9) 0.0494(10) -0.0069(7) 0.0029(7) 0.0230(8)
    N12 0.0689(12) 0.0380(10) 0.0583(11) 0.0180(9) 0.0324(10) 0.0162(9)
    O3 0.0497(8) 0.0513(9) 0.0454(8) -0.0002(7) 0.0041(6) 0.0257(7)
    O4 0.0506(8) 0.0392(8) 0.0468(8) -0.0013(6) 0.0087(6) 0.0006(7)
    O13 0.0925(14) 0.0541(11) 0.0904(14) 0.0316(10) 0.0319(12) 0.0393(11)
    O14 0.1008(15) 0.0382(9) 0.0638(11) -0.0025(9) 0.0188(10) 0.0045(8)
    S2 0.0367(3) 0.0330(3) 0.0339(3) -0.00126(19) 0.0055(2) 0.00977(19)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    C1 S2 . 1.747(2) y
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C6 C7 . 1.382(3) ?
    C6 C11 . 1.387(3) ?
    C6 N5 . 1.411(2) y
    C7 C8 . 1.380(3) ?
    C7 H7 . 0.94(3) ?
    C8 C9 . 1.375(3) ?
    C8 N12 . 1.472(3) ?
    C9 C10 . 1.387(3) ?
    C9 H9 . 0.93(3) ?
    C10 C11 . 1.376(3) ?
    C10 H10 . 0.91(3) ?
    C11 H11 . 1.00(3) ?
    N5 S2 . 1.6293(17) y
    N5 H5N . 0.849(10) ?
    N12 O14 . 1.216(3) ?
    N12 O13 . 1.221(3) ?
    O3 S2 . 1.4351(15) y
    O4 S2 . 1.4254(15) y
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
    S2 C1 H1A . . 109.5 ?
    S2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    S2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    C7 C6 C11 . . 120.16(19) ?
    C7 C6 N5 . . 122.12(17) y
    C11 C6 N5 . . 117.69(18) y
    C8 C7 C6 . . 117.54(18) ?
    C8 C7 H7 . . 120.1(15) ?
    C6 C7 H7 . . 122.1(15) ?
    C9 C8 C7 . . 123.82(19) ?
    C9 C8 N12 . . 118.12(19) ?
    C7 C8 N12 . . 118.06(19) ?
    C8 C9 C10 . . 117.39(19) ?
    C8 C9 H9 . . 118.3(16) ?
    C10 C9 H9 . . 124.3(16) ?
    C11 C10 C9 . . 120.5(2) ?
    C11 C10 H10 . . 121.6(19) ?
    C9 C10 H10 . . 117.9(19) ?
    C10 C11 C6 . . 120.6(2) ?
    C10 C11 H11 . . 121.9(15) ?
    C6 C11 H11 . . 117.4(15) ?
    C6 N5 S2 . . 126.27(13) y
    C6 N5 H5N . . 116.1(19) ?
    S2 N5 H5N . . 111.8(19) ?
    O14 N12 O13 . . 123.6(2) ?
    O14 N12 C8 . . 118.38(19) ?
    O13 N12 C8 . . 118.0(2) ?
    O4 S2 O3 . . 118.55(9) y
    O4 S2 N5 . . 109.14(10) y
    O3 S2 N5 . . 104.09(9) y
    O4 S2 C1 . . 108.26(10) ?
    O3 S2 C1 . . 109.55(12) ?
    N5 S2 C1 . . 106.62(11) y
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
    C11 C6 C7 C8 . . . . -0.6(3) ?
    N5 C6 C7 C8 . . . . 177.35(18) ?
    C6 C7 C8 C9 . . . . -0.2(3) ?
    C6 C7 C8 N12 . . . . -179.54(17) ?
    C7 C8 C9 C10 . . . . 0.5(3) ?
    N12 C8 C9 C10 . . . . 179.83(19) ?
    C8 C9 C10 C11 . . . . 0.0(4) ?
    C9 C10 C11 C6 . . . . -0.8(4) ?
    C7 C6 C11 C10 . . . . 1.1(3) ?
    N5 C6 C11 C10 . . . . -176.9(2) ?
    C7 C6 N5 S2 . . . . 41.2(3) y
    C11 C6 N5 S2 . . . . -140.83(19) y
    C9 C8 N12 O14 . . . . 176.1(2) ?
    C7 C8 N12 O14 . . . . -4.6(3) ?
    C9 C8 N12 O13 . . . . -3.6(3) ?
    C7 C8 N12 O13 . . . . 175.7(2) ?
    C6 N5 S2 O4 . . . . -57.2(2) y
    C6 N5 S2 O3 . . . . 175.34(19) y
    C6 N5 S2 C1 . . . . 59.6(2) y
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
    N5 H5N O3 2_676 0.849(10) 2.203(16) 2.984(2) 153(3)
