##############################################################################
###                                                                        ###
###        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     ?
_journal_date_recd_electronic     2010-08-19
_journal_date_accepted     2010-08-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      9
_journal_page_first     o2436
_journal_page_last     o2436
_journal_paper_category     QO
_journal_coeditor_code     HB5617
_publ_contact_author
;
Muhammad Nawaz Tahir
University of Sargodha
Department of Physics
Sargodha
Pakistan
;
_publ_contact_author_email     'dmntahir_uos@yahoo.com'
_publ_contact_author_fax     '0092 48 32 22 121'
_publ_contact_author_phone     '0092 48 92 30 914'
_publ_section_title
;
4-{2-[(Z)-(5-Methyl-2-furyl)methylideneamino]ethyl}benzenesulfonamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Khalid Mahmood'
;
Department of Chemistry
Bahauddin Zakariya University
Multan 60800
Pakistan
;
    'Muhammad Yaqub'
;
Department of Chemistry
Bahauddin Zakariya University
Multan 60800
Pakistan
;
    'Tahir, M. Nawaz'
;
Department of Physics
University of Sargodha
Sargodha
Pakistan
;
    'Zahid Shafiq'
;
Department of Chemistry
Bahauddin Zakariya University
Multan 60800
Pakistan
;
    'Ashfaq Mahmood Qureshi'
;
Department of Chemistry
Bahauddin Zakariya University
Multan 60800
Pakistan
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-{2-[(Z)-(5-Methyl-2-furyl)methylideneamino]ethyl}benzenesulfonamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H16 N2 O3 S'
_chemical_formula_sum     'C14 H16 N2 O3 S'
_chemical_formula_iupac     'C14 H16 N2 O3 S'
_chemical_formula_weight     292.35
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,-y,-z
_cell_length_a     9.1947(14)
_cell_length_b     9.7592(14)
_cell_length_c     9.8493(15)
_cell_angle_alpha     61.027(6)
_cell_angle_beta     70.650(6)
_cell_angle_gamma     81.574(7)
_cell_volume     729.4(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1461
_cell_measurement_theta_min     2.39
_cell_measurement_theta_max     25.25
_cell_measurement_temperature     296(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     'dark yellow'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.331
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     308
_exptl_absorpt_coefficient_mu     0.230
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.956
_exptl_absorpt_correction_T_max     0.977
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(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 Kappa APEXII CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.20
_diffrn_reflns_number     10058
_diffrn_reflns_av_R_equivalents     0.0677
_diffrn_reflns_av_sigmaI/netI     0.0788
_diffrn_reflns_theta_min     2.35
_diffrn_reflns_theta_max     25.50
_diffrn_reflns_theta_full     25.50
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_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     2638
_reflns_number_gt     1461
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1171
_refine_ls_R_factor_gt     0.0577
_refine_ls_wR_factor_gt     0.1249
_refine_ls_wR_factor_ref     0.1526
_refine_ls_goodness_of_fit_ref     0.971
_refine_ls_restrained_S_all     0.971
_refine_ls_number_reflns     2638
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0756P)²] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.219
_refine_diff_density_min     -0.326
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     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                  'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
                                'WinGX (Farrugia, 1999) 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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    S S1 0.74690(11) 0.53303(11) 0.83986(11) 0.0552(4) Uani . . 1.000
    O O1 0.6857(3) 0.4598(3) 1.0147(3) 0.0670(10) Uani . . 1.000
    O O2 0.8947(3) 0.6089(3) 0.7640(3) 0.0748(11) Uani . . 1.000
    O O3 0.7176(3) -0.2510(3) 0.3423(3) 0.0507(8) Uani . . 1.000
    N N1 0.6254(4) 0.6587(4) 0.7715(4) 0.0646(12) Uani . . 1.000
    N N2 0.7059(3) -0.0369(3) 0.4601(4) 0.0574(11) Uani . . 1.000
    C C1 0.7622(4) 0.1521(4) 0.6961(4) 0.0461(11) Uani . . 1.000
    C C2 0.8939(4) 0.2404(4) 0.6471(4) 0.0510(12) Uani . . 1.000
    C C3 0.8887(4) 0.3549(4) 0.6906(4) 0.0474(11) Uani . . 1.000
    C C4 0.7533(4) 0.3868(4) 0.7848(4) 0.0413(11) Uani . . 1.000
    C C5 0.6216(4) 0.2987(4) 0.8352(4) 0.0486(12) Uani . . 1.000
    C C6 0.6275(4) 0.1842(4) 0.7922(4) 0.0510(12) Uani . . 1.000
    C C7 0.7667(4) 0.0281(4) 0.6470(5) 0.0635(14) Uani . . 1.000
    C C8 0.7022(5) 0.0834(4) 0.5068(5) 0.0725(18) Uani . . 1.000
    C C9 0.7504(4) 0.0059(4) 0.3090(5) 0.0568(14) Uani . . 1.000
    C C10 0.7612(4) -0.0949(4) 0.2409(4) 0.0496(12) Uani . . 1.000
    C C11 0.8112(4) -0.0715(5) 0.0851(4) 0.0594(16) Uani . . 1.000
    C C12 0.8012(4) -0.2149(5) 0.0879(4) 0.0615(16) Uani . . 1.000
    C C13 0.7442(4) -0.3207(4) 0.2452(4) 0.0504(12) Uani . . 1.000
    C C14 0.7067(5) -0.4902(4) 0.3273(5) 0.0703(16) Uani . . 1.000
    H H1A 0.535(4) 0.638(5) 0.802(5) 0.0777 Uiso . . 1.000
    H H1B 0.643(4) 0.724(5) 0.676(5) 0.0777 Uiso . . 1.000
    H H2 0.98644 0.22087 0.58379 0.0612 Uiso . . 1.000
    H H3 0.97774 0.41220 0.65631 0.0567 Uiso . . 1.000
    H H5 0.52913 0.31836 0.89844 0.0585 Uiso . . 1.000
    H H6 0.53869 0.12590 0.82844 0.0611 Uiso . . 1.000
    H H7A 0.70791 -0.06283 0.73939 0.0768 Uiso . . 1.000
    H H7B 0.87257 -0.00344 0.61620 0.0768 Uiso . . 1.000
    H H8A 0.59655 0.11552 0.53728 0.0866 Uiso . . 1.000
    H H8B 0.76142 0.17392 0.41410 0.0866 Uiso . . 1.000
    H H9 0.77791 0.11076 0.23804 0.0682 Uiso . . 1.000
    H H11 0.84604 0.02315 -0.00750 0.0717 Uiso . . 1.000
    H H12 0.82872 -0.23341 -0.00147 0.0735 Uiso . . 1.000
    H H14A 0.74691 -0.53007 0.25033 0.1053 Uiso . . 1.000
    H H14B 0.59683 -0.50553 0.37049 0.1053 Uiso . . 1.000
    H H14C 0.75202 -0.54468 0.41435 0.1053 Uiso . . 1.000
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 0.0661(7) 0.0559(6) 0.0413(6) -0.0178(5) -0.0026(4) -0.0246(5)
    O1 0.0882(19) 0.0783(18) 0.0346(14) -0.0201(14) -0.0061(13) -0.0285(13)
    O2 0.0692(17) 0.0801(19) 0.0763(19) -0.0301(14) -0.0002(14) -0.0428(16)
    O3 0.0698(16) 0.0453(14) 0.0336(13) -0.0044(11) -0.0145(11) -0.0152(11)
    N1 0.073(2) 0.050(2) 0.052(2) -0.0051(18) -0.004(2) -0.0174(16)
    N2 0.081(2) 0.0476(18) 0.046(2) 0.0008(15) -0.0207(16) -0.0225(16)
    C1 0.064(2) 0.0387(19) 0.038(2) 0.0061(17) -0.0210(18) -0.0175(16)
    C2 0.058(2) 0.053(2) 0.034(2) 0.0076(18) -0.0114(17) -0.0176(18)
    C3 0.053(2) 0.047(2) 0.0345(19) -0.0092(16) -0.0091(16) -0.0132(17)
    C4 0.044(2) 0.0443(19) 0.0272(17) -0.0032(15) -0.0060(15) -0.0124(15)
    C5 0.048(2) 0.050(2) 0.046(2) -0.0018(16) -0.0060(16) -0.0255(18)
    C6 0.052(2) 0.049(2) 0.050(2) -0.0070(16) -0.0112(18) -0.0221(19)
    C7 0.089(3) 0.052(2) 0.060(2) 0.009(2) -0.032(2) -0.030(2)
    C8 0.118(4) 0.049(2) 0.064(3) 0.008(2) -0.042(2) -0.029(2)
    C9 0.073(3) 0.042(2) 0.052(2) -0.0064(18) -0.025(2) -0.0135(19)
    C10 0.060(2) 0.043(2) 0.037(2) -0.0075(16) -0.0156(16) -0.0092(17)
    C11 0.069(3) 0.062(3) 0.031(2) -0.0100(19) -0.0118(17) -0.0085(18)
    C12 0.070(3) 0.078(3) 0.038(2) 0.000(2) -0.0145(18) -0.029(2)
    C13 0.061(2) 0.055(2) 0.046(2) 0.0056(17) -0.0223(18) -0.029(2)
    C14 0.105(3) 0.054(2) 0.062(3) 0.004(2) -0.040(2) -0.026(2)
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O1 . . 1.441(3) no
    S1 O2 . . 1.428(3) no
    S1 N1 . . 1.582(4) no
    S1 C4 . . 1.743(4) no
    O3 C10 . . 1.385(5) no
    O3 C13 . . 1.365(5) no
    N2 C8 . . 1.446(6) no
    N2 C9 . . 1.265(5) no
    N1 H1B . . 0.82(4) no
    N1 H1A . . 0.80(4) no
    C1 C6 . . 1.387(5) no
    C1 C7 . . 1.496(6) no
    C1 C2 . . 1.399(6) no
    C2 C3 . . 1.367(6) no
    C3 C4 . . 1.382(5) no
    C4 C5 . . 1.395(6) no
    C5 C6 . . 1.363(6) no
    C7 C8 . . 1.509(6) no
    C9 C10 . . 1.412(6) no
    C10 C11 . . 1.357(5) no
    C11 C12 . . 1.402(7) no
    C12 C13 . . 1.346(5) no
    C13 C14 . . 1.482(6) no
    C2 H2 . . 0.9300 no
    C3 H3 . . 0.9300 no
    C5 H5 . . 0.9300 no
    C6 H6 . . 0.9300 no
    C7 H7A . . 0.9700 no
    C7 H7B . . 0.9700 no
    C8 H8A . . 0.9700 no
    C8 H8B . . 0.9700 no
    C9 H9 . . 0.9300 no
    C11 H11 . . 0.9300 no
    C12 H12 . . 0.9300 no
    C14 H14A . . 0.9600 no
    C14 H14B . . 0.9600 no
    C14 H14C . . 0.9600 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 S1 O2 . . . 118.85(17) no
    O1 S1 N1 . . . 106.50(18) no
    O1 S1 C4 . . . 106.27(18) no
    O2 S1 N1 . . . 107.94(19) no
    O2 S1 C4 . . . 108.41(19) no
    N1 S1 C4 . . . 108.5(2) no
    C10 O3 C13 . . . 107.0(3) no
    C8 N2 C9 . . . 116.4(4) no
    S1 N1 H1B . . . 123(3) no
    H1A N1 H1B . . . 105(4) no
    S1 N1 H1A . . . 122(3) no
    C6 C1 C7 . . . 121.5(4) no
    C2 C1 C6 . . . 117.2(4) no
    C2 C1 C7 . . . 121.3(3) no
    C1 C2 C3 . . . 121.1(4) no
    C2 C3 C4 . . . 121.1(4) no
    S1 C4 C3 . . . 121.0(3) no
    C3 C4 C5 . . . 118.3(4) no
    S1 C4 C5 . . . 120.7(3) no
    C4 C5 C6 . . . 120.4(4) no
    C1 C6 C5 . . . 121.9(4) no
    C1 C7 C8 . . . 112.3(4) no
    N2 C8 C7 . . . 112.2(4) no
    N2 C9 C10 . . . 124.4(4) no
    O3 C10 C9 . . . 119.6(3) no
    O3 C10 C11 . . . 108.0(4) no
    C9 C10 C11 . . . 132.4(4) no
    C10 C11 C12 . . . 108.2(3) no
    C11 C12 C13 . . . 106.7(4) no
    O3 C13 C12 . . . 110.1(4) no
    O3 C13 C14 . . . 117.0(3) no
    C12 C13 C14 . . . 132.9(4) no
    C1 C2 H2 . . . 119.00 no
    C3 C2 H2 . . . 120.00 no
    C2 C3 H3 . . . 119.00 no
    C4 C3 H3 . . . 119.00 no
    C4 C5 H5 . . . 120.00 no
    C6 C5 H5 . . . 120.00 no
    C1 C6 H6 . . . 119.00 no
    C5 C6 H6 . . . 119.00 no
    C1 C7 H7A . . . 109.00 no
    C1 C7 H7B . . . 109.00 no
    C8 C7 H7A . . . 109.00 no
    C8 C7 H7B . . . 109.00 no
    H7A C7 H7B . . . 108.00 no
    N2 C8 H8A . . . 109.00 no
    N2 C8 H8B . . . 109.00 no
    C7 C8 H8A . . . 109.00 no
    C7 C8 H8B . . . 109.00 no
    H8A C8 H8B . . . 108.00 no
    N2 C9 H9 . . . 118.00 no
    C10 C9 H9 . . . 118.00 no
    C10 C11 H11 . . . 126.00 no
    C12 C11 H11 . . . 126.00 no
    C11 C12 H12 . . . 127.00 no
    C13 C12 H12 . . . 127.00 no
    C13 C14 H14A . . . 109.00 no
    C13 C14 H14B . . . 109.00 no
    C13 C14 H14C . . . 109.00 no
    H14A C14 H14B . . . 110.00 no
    H14A C14 H14C . . . 110.00 no
    H14B C14 H14C . . . 109.00 no
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 C4 C3 . . . . -125.4(3) no
    O1 S1 C4 C5 . . . . 54.5(3) no
    O2 S1 C4 C3 . . . . 3.4(4) no
    O2 S1 C4 C5 . . . . -176.7(3) no
    N1 S1 C4 C3 . . . . 120.4(3) no
    N1 S1 C4 C5 . . . . -59.7(3) no
    C13 O3 C10 C9 . . . . -178.2(4) no
    C13 O3 C10 C11 . . . . 0.8(4) no
    C10 O3 C13 C12 . . . . -0.5(4) no
    C10 O3 C13 C14 . . . . 179.7(4) no
    C9 N2 C8 C7 . . . . -136.6(4) no
    C8 N2 C9 C10 . . . . -179.9(4) no
    C6 C1 C2 C3 . . . . -0.9(5) no
    C7 C1 C2 C3 . . . . 179.2(3) no
    C2 C1 C6 C5 . . . . 1.3(5) no
    C7 C1 C6 C5 . . . . -178.8(3) no
    C2 C1 C7 C8 . . . . -100.7(4) no
    C6 C1 C7 C8 . . . . 79.4(5) no
    C1 C2 C3 C4 . . . . 0.2(5) no
    C2 C3 C4 S1 . . . . -179.9(3) no
    C2 C3 C4 C5 . . . . 0.2(5) no
    S1 C4 C5 C6 . . . . -179.8(3) no
    C3 C4 C5 C6 . . . . 0.1(5) no
    C4 C5 C6 C1 . . . . -0.9(6) no
    C1 C7 C8 N2 . . . . -179.7(3) no
    N2 C9 C10 O3 . . . . 1.7(6) no
    N2 C9 C10 C11 . . . . -177.1(4) no
    O3 C10 C11 C12 . . . . -0.8(5) no
    C9 C10 C11 C12 . . . . 178.0(4) no
    C10 C11 C12 C13 . . . . 0.5(5) no
    C11 C12 C13 O3 . . . . 0.0(5) no
    C11 C12 C13 C14 . . . . 179.8(4) no
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
    N1 H1A O1 2_667 0.80(4) 2.18(4) 2.928(5) 155(4) yes
    N1 H1B N2 1_565 0.82(4) 2.25(5) 3.015(5) 156(5) yes
    C6 H6 Cg1 2_656 0.93 2.87 3.596(4) 136 yes
    C11 H11 Cg2 1_554 0.93 2.75 3.535(4) 143 yes
    C14 H14C Cg2 1_545 0.96 2.84 3.743(5) 157 yes
