#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224387.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224387
loop_
_publ_author_name
'Arshad, Muhammad Nadeem'
'Mubashar-ur-Rehman, Hafiz'
'Khan, Islam Ullah'
'Shafiq, Muhammad'
'Lo, Kong Mun'
_publ_section_title
;
 N-(Phenylsulfonyl)-<small>L</small>-asparagine
;
_journal_coeditor_code           OM2295
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3229
_journal_paper_doi               10.1107/S1600536809050247
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H12 N2 O5 S'
_chemical_formula_moiety         'C10 H12 N2 O5 S'
_chemical_formula_sum            'C10 H12 N2 O5 S'
_chemical_formula_weight         272.28
_chemical_name_systematic
;
N-(Phenylsulfonyl)-L-asparagine
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.011(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.5479(6)
_cell_length_b                   5.1587(3)
_cell_length_c                   11.0157(7)
_cell_measurement_reflns_used    3825
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.63
_cell_volume                     599.03(6)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6832
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.9638
_exptl_absorpt_correction_T_min  0.9320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.164
_refine_ls_abs_structure_details 'Flack (1983), 1187 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2732
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0464P)²+0.0133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0760
_reflns_number_gt                2518
_reflns_number_total             2732
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2295.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2224387
_cod_database_fobs_code          2224387
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_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'
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_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_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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8929957
