##############################################################################
###                                                                        ###
###        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                                                              #
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# 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.                                        #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-(Phenylsulfonyl)-L-asparagine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H12 N2 O5 S'
_chemical_formula_sum     'C10 H12 N2 O5 S'
_chemical_formula_iupac     'C10 H12 N2 O5 S'
_chemical_formula_weight     272.28
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     10.5479(6)
_cell_length_b     5.1587(3)
_cell_length_c     11.0157(7)
_cell_angle_alpha     90.00
_cell_angle_beta     92.011(3)
_cell_angle_gamma     90.00
_cell_volume     599.03(6)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3825
_cell_measurement_theta_min     2.63
_cell_measurement_theta_max     27.41
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.13
_exptl_crystal_density_diffrn     1.510
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     284
_exptl_absorpt_coefficient_mu     0.286
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9320
_exptl_absorpt_correction_T_max     0.9638
_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 APEXII'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6832
_diffrn_reflns_av_R_equivalents     0.0232
_diffrn_reflns_av_sigmaI/netI     0.0278
_diffrn_reflns_theta_min     2.63
_diffrn_reflns_theta_max     27.57
_diffrn_reflns_theta_full     27.57
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_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     2732
_reflns_number_gt     2518
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0325
_refine_ls_R_factor_gt     0.0289
_refine_ls_wR_factor_gt     0.0739
_refine_ls_wR_factor_ref     0.0760
_refine_ls_goodness_of_fit_ref     1.058
_refine_ls_restrained_S_all     1.058
_refine_ls_number_reflns     2732
_refine_ls_number_parameters     176
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0464P)²+0.0133P] 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     0.334
_refine_diff_density_min     -0.164
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1187 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.01(6)
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, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 0.91282(16) 0.8736(3) 0.28950(15) 0.0323(4) Uani d . 1 . .
    C C2 0.93349(19) 0.7209(4) 0.18909(17) 0.0411(4) Uani d . 1 . .
    H H2 0.8795 0.5838 0.1688 0.049 Uiso calc R 1 . .
    C C3 1.03713(19) 0.7776(5) 0.11920(19) 0.0503(5) Uani d . 1 . .
    H H3 1.0534 0.6766 0.0516 0.060 Uiso calc R 1 . .
    C C4 1.11535(19) 0.9813(5) 0.1493(2) 0.0499(5) Uani d . 1 . .
    H H4 1.1837 1.0187 0.1012 0.060 Uiso calc R 1 . .
    C C5 1.09413(19) 1.1314(5) 0.2501(2) 0.0517(5) Uani d . 1 . .
    H H5 1.1483 1.2683 0.2700 0.062 Uiso calc R 1 . .
    C C6 0.99250(18) 1.0783(4) 0.32109(19) 0.0439(4) Uani d . 1 . .
    H H6 0.9775 1.1783 0.3893 0.053 Uiso calc R 1 . .
    C C7 0.59899(15) 0.9058(3) 0.19546(14) 0.0279(3) Uani d . 1 . .
    H H7 0.6111 0.7183 0.1873 0.034 Uiso calc R 1 . .
    C C8 0.64948(16) 1.0412(3) 0.08415(14) 0.0311(3) Uani d . 1 . .
    C C9 0.45593(16) 0.9649(3) 0.20037(16) 0.0333(4) Uani d . 1 . .
    H H9A 0.4444 1.1370 0.2336 0.040 Uiso calc R 1 . .
    H H9B 0.4187 0.9630 0.1186 0.040 Uiso calc R 1 . .
    C C10 0.38860(15) 0.7715(3) 0.27662(15) 0.0315(4) Uani d . 1 . .
    H H1A 0.379(3) 1.000(7) 0.406(3) 0.073(9) Uiso d . 1 . .
    H H2A 0.312(3) 0.722(7) 0.433(3) 0.090(10) Uiso d . 1 . .
    N N1 0.66143(14) 0.9939(3) 0.30846(13) 0.0300(3) Uani d . 1 . .
    H H1B 0.6757(17) 1.141(5) 0.3130(17) 0.027(5) Uiso d . 1 . .
    N N2 0.3616(2) 0.8376(5) 0.38858(16) 0.0575(5) Uani d . 1 . .
    O O1 0.73791(14) 0.5586(3) 0.36312(13) 0.0448(3) Uani d . 1 . .
    O O2 0.79671(14) 0.9371(3) 0.49048(11) 0.0458(3) Uani d . 1 . .
    O O3 0.70376(15) 1.2446(3) 0.08654(13) 0.0492(4) Uani d . 1 . .
    O O4 0.61999(16) 0.9065(3) -0.01409(11) 0.0485(4) Uani d . 1 . .
    H H4A 0.6403 0.9880 -0.0743 0.073 Uiso calc R 1 . .
    O O6 0.35901(14) 0.5579(3) 0.23573(12) 0.0430(3) Uani d . 1 . .
    S S1 0.77553(4) 0.82468(8) 0.37280(3) 0.03153(11) 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 0.0338(7) 0.0321(10) 0.0308(8) 0.0042(6) -0.0010(6) 0.0009(6)
    C2 0.0425(9) 0.0410(10) 0.0399(10) 0.0005(8) 0.0027(8) -0.0079(8)
    C3 0.0454(10) 0.0652(15) 0.0407(10) 0.0089(10) 0.0084(8) -0.0096(10)
    C4 0.0310(9) 0.0658(14) 0.0532(12) 0.0041(9) 0.0049(8) 0.0057(10)
    C5 0.0355(10) 0.0530(13) 0.0662(14) -0.0071(9) -0.0025(9) -0.0011(11)
    C6 0.0412(9) 0.0438(11) 0.0466(11) -0.0015(8) -0.0012(8) -0.0101(9)
    C7 0.0340(8) 0.0237(7) 0.0263(8) -0.0001(6) 0.0039(6) 0.0008(6)
    C8 0.0357(8) 0.0312(9) 0.0268(8) -0.0011(7) 0.0059(7) 0.0014(6)
    C9 0.0340(8) 0.0315(9) 0.0346(9) 0.0006(7) 0.0041(7) 0.0053(7)
    C10 0.0326(8) 0.0314(10) 0.0306(8) 0.0005(6) 0.0049(6) 0.0018(6)
    N1 0.0365(7) 0.0248(7) 0.0287(7) 0.0013(6) 0.0026(6) -0.0003(6)
    N2 0.0810(13) 0.0565(11) 0.0363(9) -0.0212(12) 0.0216(8) -0.0110(10)
    O1 0.0570(8) 0.0306(7) 0.0472(8) 0.0007(6) 0.0059(6) 0.0108(6)
    O2 0.0567(8) 0.0564(8) 0.0244(6) 0.0107(7) 0.0006(6) -0.0009(6)
    O3 0.0665(9) 0.0457(9) 0.0357(7) -0.0255(7) 0.0061(6) 0.0041(6)
    O4 0.0820(10) 0.0388(7) 0.0255(6) -0.0119(7) 0.0105(6) -0.0018(5)
    O6 0.0593(8) 0.0361(7) 0.0345(6) -0.0074(6) 0.0152(6) -0.0019(5)
    S1 0.0406(2) 0.0300(2) 0.02406(18) 0.00257(18) 0.00257(14) 0.00307(17)
_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
    C1 C2 . 1.382(3) ?
    C1 C6 . 1.386(3) ?
    C1 S1 . 1.7596(18) ?
    C2 C3 . 1.390(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.370(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.378(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.377(3) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 N1 . 1.460(2) ?
    C7 C8 . 1.523(2) ?
    C7 C9 . 1.542(2) ?
    C7 H7 . 0.9800 ?
    C8 O3 . 1.195(2) ?
    C8 O4 . 1.314(2) ?
    C9 C10 . 1.499(2) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 O6 . 1.226(2) ?
    C10 N2 . 1.320(2) ?
    N1 S1 . 1.6289(15) ?
    N1 H1B . 0.77(2) ?
    N2 H1A . 0.88(4) ?
    N2 H2A . 0.95(3) ?
    O1 S1 . 1.4319(14) ?
    O2 S1 . 1.4304(14) ?
    O4 H4A . 0.8200 ?
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
    C2 C1 C6 . . 121.60(18) ?
    C2 C1 S1 . . 119.45(14) ?
    C6 C1 S1 . . 118.76(14) ?
    C1 C2 C3 . . 118.21(19) ?
    C1 C2 H2 . . 120.9 ?
    C3 C2 H2 . . 120.9 ?
    C4 C3 C2 . . 120.39(19) ?
    C4 C3 H3 . . 119.8 ?
    C2 C3 H3 . . 119.8 ?
    C3 C4 C5 . . 120.86(19) ?
    C3 C4 H4 . . 119.6 ?
    C5 C4 H4 . . 119.6 ?
    C6 C5 C4 . . 119.82(19) ?
    C6 C5 H5 . . 120.1 ?
    C4 C5 H5 . . 120.1 ?
    C5 C6 C1 . . 119.11(18) ?
    C5 C6 H6 . . 120.4 ?
    C1 C6 H6 . . 120.4 ?
    N1 C7 C8 . . 112.54(13) ?
    N1 C7 C9 . . 108.73(13) ?
    C8 C7 C9 . . 107.92(13) ?
    N1 C7 H7 . . 109.2 ?
    C8 C7 H7 . . 109.2 ?
    C9 C7 H7 . . 109.2 ?
    O3 C8 O4 . . 125.58(16) ?
    O3 C8 C7 . . 124.44(15) ?
    O4 C8 C7 . . 109.93(14) ?
    C10 C9 C7 . . 111.80(14) ?
    C10 C9 H9A . . 109.3 ?
    C7 C9 H9A . . 109.3 ?
    C10 C9 H9B . . 109.3 ?
    C7 C9 H9B . . 109.3 ?
    H9A C9 H9B . . 107.9 ?
    O6 C10 N2 . . 120.99(18) ?
    O6 C10 C9 . . 120.76(16) ?
    N2 C10 C9 . . 118.24(18) ?
    C7 N1 S1 . . 120.55(12) ?
    C7 N1 H1B . . 116.2(14) ?
    S1 N1 H1B . . 110.9(14) ?
    C10 N2 H1A . . 113.9(19) ?
    C10 N2 H2A . . 117.8(19) ?
    H1A N2 H2A . . 127(3) ?
    C8 O4 H4A . . 109.5 ?
    O2 S1 O1 . . 119.35(9) ?
    O2 S1 N1 . . 105.46(8) ?
    O1 S1 N1 . . 106.44(8) ?
    O2 S1 C1 . . 108.01(9) ?
    O1 S1 C1 . . 109.25(8) ?
    N1 S1 C1 . . 107.77(8) ?
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
    C6 C1 C2 C3 . . . . -0.1(3) ?
    S1 C1 C2 C3 . . . . 174.80(16) ?
    C1 C2 C3 C4 . . . . -0.6(3) ?
    C2 C3 C4 C5 . . . . 0.9(3) ?
    C3 C4 C5 C6 . . . . -0.6(3) ?
    C4 C5 C6 C1 . . . . -0.1(3) ?
    C2 C1 C6 C5 . . . . 0.5(3) ?
    S1 C1 C6 C5 . . . . -174.49(16) ?
    N1 C7 C8 O3 . . . . -21.2(2) ?
    C9 C7 C8 O3 . . . . 98.8(2) ?
    N1 C7 C8 O4 . . . . 161.31(14) ?
    C9 C7 C8 O4 . . . . -78.71(17) ?
    N1 C7 C9 C10 . . . . -78.10(18) ?
    C8 C7 C9 C10 . . . . 159.55(14) ?
    C7 C9 C10 O6 . . . . -79.6(2) ?
    C7 C9 C10 N2 . . . . 100.7(2) ?
    C8 C7 N1 S1 . . . . -99.21(15) ?
    C9 C7 N1 S1 . . . . 141.28(13) ?
    C7 N1 S1 O2 . . . . -168.94(12) ?
    C7 N1 S1 O1 . . . . -41.22(15) ?
    C7 N1 S1 C1 . . . . 75.87(14) ?
    C2 C1 S1 O2 . . . . 160.50(14) ?
    C6 C1 S1 O2 . . . . -24.43(17) ?
    C2 C1 S1 O1 . . . . 29.25(17) ?
    C6 C1 S1 O1 . . . . -155.68(14) ?
    C2 C1 S1 N1 . . . . -86.01(16) ?
    C6 C1 S1 N1 . . . . 89.06(15) ?
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
    N1 H1B O1 1_565 0.77(2) 2.31(2) 3.076(2) 168.6(19)
    N2 H2A O2 2_646 0.95(3) 2.06(3) 2.998(3) 172(3)
    O4 H4A O6 2_655 0.82 1.82 2.5804(18) 155
data_global
_journal_date_recd_electronic     2009-10-28
_journal_date_accepted     2009-11-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     12
_journal_page_first     o3229
_journal_page_last     o3229
_journal_paper_category     QO
_journal_coeditor_code     OM2295
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Khan Islam Ullah'
;
Materials Chemistry Laboratory
Department of Chemistry
GC Universirty, lahore-54000,
Pakistan
;
 'iukhan.gcu@gmail.com'
    'Lo, Kong Mun'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
 'kmlo@um.edu.my'
_publ_contact_author_fax     '?'
_publ_contact_author_phone     '0333 4046740'
_publ_section_title
;
N-(Phenylsulfonyl)-L-asparagine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Muhammad Nadeem Arshad' .
;
Materials Chemistry Laboratory
Department of Chemistry
GC University,
Lahore 54000
Pakistan
;
    'Hafiz Mubashar-ur-Rehman' .
;
Materials Chemistry Laboratory
Department of Chemistry
GC University,
Lahore 54000
Pakistan
;
    'Islam Ullah Khan' .
;
Materials Chemistry Laboratory
Department of Chemistry
GC University,
Lahore 54000
Pakistan
;
    'Muhammad Shafiq' .
;
Materials Chemistry Laboratory
Department of Chemistry
GC University,
Lahore 54000
Pakistan
;
    'Lo, Kong Mun' .
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
