#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/61/2226133.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_2226133
loop_
_publ_author_name
'Sharif, Shahzad'
'Iqbal, Haffsah'
'Khan, Islam Ullah'
'John, Peter'
'Tiekink, Edward R. T.'
_publ_section_title
;
 2-(4-Acetamidobenzenesulfonamido)-3-methylbutanoic acid
;
_journal_coeditor_code           HB5434
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1288
_journal_paper_doi               10.1107/S1600536810016119
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H18 N2 O5 S'
_chemical_formula_moiety         'C13 H18 N2 O5 S'
_chemical_formula_sum            'C13 H18 N2 O5 S'
_chemical_formula_weight         314.35
_chemical_name_systematic
;
2-(4-Acetamidobenzenesulfonamido)-3-methylbutanoic acid
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1649(13)
_cell_length_b                   14.724(5)
_cell_length_c                   20.688(7)
_cell_measurement_reflns_used    815
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.5
_cell_measurement_theta_min      3.0
_cell_volume                     1573.3(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.075
_diffrn_reflns_av_sigmaI/netI    0.073
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7356
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.7
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.52
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.16
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         1647
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.16
_refine_ls_R_factor_all          0.110
_refine_ls_R_factor_gt           0.053
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1138P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.132
_refine_ls_wR_factor_ref         0.209
_reflns_number_gt                1083
_reflns_number_total             1647
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5434.cif
_cod_data_source_block           I
_cod_original_cell_volume        1573.2(8)
_cod_database_code               2226133
_cod_database_fobs_code          2226133
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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
S S1 0.6472(3) 0.98522(14) 0.24127(8) 0.0374(6) Uani d . 1 . .
O O1 0.7761(10) 0.9900(4) 0.3028(2) 0.0474(15) Uani d . 1 . .
O O2 0.3793(9) 1.0094(4) 0.2371(3) 0.0484(14) Uani d . 1 . .
O O3 0.4852(13) 0.6006(4) 0.0597(3) 0.0627(19) Uani d . 1 . .
O O4 1.0931(11) 0.9940(5) 0.0904(3) 0.068(2) Uani d . 1 . .
O O5 0.7406(11) 0.9868(5) 0.0302(3) 0.0618(19) Uani d . 1 . .
H H5O 0.8216 0.9540 -0.0023 0.093 Uiso d . 1 . .
N N1 0.8024(12) 0.6160(5) 0.1338(3) 0.0423(17) Uani d D 1 . .
H H1N 0.947(8) 0.593(5) 0.146(4) 0.051 Uiso d D 1 . .
N N2 0.8017(12) 1.0547(4) 0.1940(3) 0.0347(15) Uani d D 1 B .
H H2N 0.963(4) 1.041(5) 0.194(3) 0.042 Uiso d D 1 . .
C C1 0.6850(14) 0.8749(5) 0.2107(4) 0.0341(17) Uani d . 1 . .
C C2 0.5207(16) 0.8443(6) 0.1626(4) 0.044(2) Uani d . 1 . .
H H2 0.3858 0.8810 0.1483 0.053 Uiso calc R 1 . .
C C3 0.5570(17) 0.7596(6) 0.1360(4) 0.051(2) Uani d . 1 . .
H H3 0.4462 0.7395 0.1036 0.061 Uiso calc R 1 . .
C C4 0.7560(14) 0.7038(5) 0.1568(4) 0.0381(19) Uani d . 1 . .
C C5 0.9198(15) 0.7362(6) 0.2053(4) 0.045(2) Uani d . 1 . .
H H5 1.0537 0.6994 0.2201 0.054 Uiso calc R 1 . .
C C6 0.8875(16) 0.8207(6) 0.2314(4) 0.047(2) Uani d . 1 . .
H H6 1.0011 0.8417 0.2629 0.056 Uiso calc R 1 . .
C C7 0.6686(18) 0.5689(6) 0.0892(4) 0.045(2) Uani d . 1 . .
C C8 0.7567(19) 0.4720(5) 0.0793(4) 0.057(2) Uani d . 1 . .
H H8A 0.6125 0.4316 0.0850 0.086 Uiso calc R 1 . .
H H8B 0.8891 0.4575 0.1102 0.086 Uiso calc R 1 . .
H H8C 0.8245 0.4652 0.0364 0.086 Uiso calc R 1 . .
C C9 0.7105(16) 1.0683(6) 0.1282(3) 0.0403(19) Uani d . 1 . .
H H9 0.5295 1.0486 0.1256 0.048 Uiso calc R 1 A 1
C C10 0.8709(15) 1.0112(6) 0.0812(3) 0.0429(19) Uani d . 1 B .
C C11 0.724(2) 1.1699(7) 0.1107(5) 0.071(3) Uani d P 0.747(16) B 1
H H11 0.9013 1.1893 0.1209 0.086 Uiso calc PR 0.747(16) B 1
C C12 0.550(3) 1.2240(7) 0.1542(6) 0.103(5) Uani d P 0.747(16) B 1
H H12A 0.5831 1.2876 0.1483 0.154 Uiso calc PR 0.747(16) B 1
H H12B 0.5821 1.2077 0.1984 0.154 Uiso calc PR 0.747(16) B 1
H H12C 0.3724 1.2113 0.1437 0.154 Uiso calc PR 0.747(16) B 1
C C13 0.683(4) 1.1929(11) 0.0441(7) 0.109(7) Uani d P 0.747(16) B 1
H H13A 0.5309 1.1626 0.0286 0.164 Uiso calc PR 0.747(16) B 1
H H13B 0.8302 1.1742 0.0190 0.164 Uiso calc PR 0.747(16) B 1
H H13C 0.6608 1.2574 0.0402 0.164 Uiso calc PR 0.747(16) B 1
C C11A 0.724(2) 1.1699(7) 0.1107(5) 0.071(3) Uani d P 0.253(16) B 2
H H11A 0.6178 1.1695 0.0715 0.086 Uiso calc PR 0.253(16) B 2
C C12A 0.550(3) 1.2240(7) 0.1542(6) 0.103(5) Uani d P 0.253(16) B 2
H H12D 0.6523 1.2566 0.1851 0.154 Uiso calc PR 0.253(16) B 2
H H12E 0.4339 1.1837 0.1764 0.154 Uiso calc PR 0.253(16) B 2
H H12F 0.4513 1.2663 0.1288 0.154 Uiso calc PR 0.253(16) B 2
C C13A 0.928(14) 1.213(3) 0.088(2) 0.109(7) Uani d P 0.253(16) B 2
H H13D 0.9508 1.1990 0.0433 0.164 Uiso calc PR 0.253(16) B 2
H H13E 1.0795 1.1945 0.1118 0.164 Uiso calc PR 0.253(16) B 2
H H13F 0.9041 1.2774 0.0933 0.164 Uiso calc PR 0.253(16) B 2
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
O2 S1 O1 . . 119.3(3) ?
O2 S1 N2 . . 106.4(4) ?
O1 S1 N2 . . 105.9(3) ?
O2 S1 C1 . . 108.4(3) ?
O1 S1 C1 . . 108.2(4) ?
N2 S1 C1 . . 108.1(3) ?
C10 O5 H5O . . 119.8 ?
C7 N1 C4 . . 128.6(7) ?
C7 N1 H1N . . 116(6) ?
C4 N1 H1N . . 114(6) ?
C9 N2 S1 . . 119.4(5) ?
C9 N2 H2N . . 110(5) ?
S1 N2 H2N . . 109(5) ?
C6 C1 C2 . . 119.9(7) ?
C6 C1 S1 . . 120.4(6) ?
C2 C1 S1 . . 119.5(6) ?
C1 C2 C3 . . 119.9(8) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C4 C3 C2 . . 120.9(8) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 118.1(7) ?
C3 C4 N1 . . 124.7(7) ?
C5 C4 N1 . . 117.2(7) ?
C6 C5 C4 . . 121.4(7) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C1 . . 119.7(7) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
O3 C7 N1 . . 122.9(8) ?
O3 C7 C8 . . 121.8(8) ?
N1 C7 C8 . . 115.2(8) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N2 C9 C10 . . 110.1(6) ?
N2 C9 C11A . . 109.8(7) ?
C10 C9 C11A . . 111.0(7) ?
N2 C9 C11 . . 109.8(7) ?
C10 C9 C11 . . 111.0(7) ?
N2 C9 H9 . . 108.6 ?
C10 C9 H9 . . 108.6 ?
C11A C9 H9 . . 108.6 ?
C11 C9 H9 . . 108.6 ?
O4 C10 O5 . . 124.8(7) ?
O4 C10 C9 . . 122.4(8) ?
O5 C10 C9 . . 112.8(7) ?
C13 C11 C12 . . 111.1(12) ?
C13 C11 C9 . . 116.7(10) ?
C12 C11 C9 . . 110.2(9) ?
C13 C11 H11 . . 106.0 ?
C12 C11 H11 . . 106.0 ?
C9 C11 H11 . . 106.0 ?
C13A C11A C12A . . 116(2) ?
C13A C11A C9 . . 126(3) ?
C12A C11A C9 . . 110.2(9) ?
C13A C11A H11A . . 99.3 ?
C12A C11A H11A . . 99.3 ?
C9 C11A H11A . . 99.3 ?
C11A C12A H12D . . 109.5 ?
C11A C12A H12E . . 109.5 ?
H12D C12A H12E . . 109.5 ?
C11A C12A H12F . . 109.5 ?
H12D C12A H12F . . 109.5 ?
H12E C12A H12F . . 109.5 ?
C11A C13A H13D . . 109.5 ?
C11A C13A H13E . . 109.5 ?
H13D C13A H13E . . 109.5 ?
C11A C13A H13F . . 109.5 ?
H13D C13A H13F . . 109.5 ?
H13E C13A H13F . . 109.5 ?
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 O2 . 1.431(5) ?
S1 O1 . 1.438(5) ?
S1 N2 . 1.625(6) ?
S1 C1 . 1.754(8) ?
O3 C7 . 1.220(10) ?
O4 C10 . 1.191(9) ?
O5 C10 . 1.301(9) ?
O5 H5O . 0.9275 ?
N1 C7 . 1.345(10) ?
N1 C4 . 1.398(10) ?
N1 H1N . 0.86(5) ?
N2 C9 . 1.454(9) ?
N2 H2N . 0.86(3) ?
C1 C6 . 1.383(10) ?
C1 C2 . 1.383(10) ?
C2 C3 . 1.377(11) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.385(11) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.395(10) ?
C5 C6 . 1.368(11) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.512(12) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.530(10) ?
C9 C11A . 1.541(12) ?
C9 C11 . 1.541(12) ?
C9 H9 . 0.9800 ?
C11 C13 . 1.434(17) ?
C11 C12 . 1.503(14) ?
C11 H11 . 0.9800 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C11A C13A . 1.32(7) ?
C11A C12A . 1.503(14) ?
C11A H11A . 0.9800 ?
C12A H12D . 0.9600 ?
C12A H12E . 0.9600 ?
C12A H12F . 0.9600 ?
C13A H13D . 0.9600 ?
C13A H13E . 0.9600 ?
C13A H13F . 0.9600 ?
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
C3 H3 O3 1_555 0.93 2.25 2.848(11) 122
O5 H5o O3 2_565 0.93 1.66 2.591(9) 176
N1 H1n O1 3_745 0.86(5) 2.34(7) 3.147(9) 157(6)
N2 H2n O2 1_655 0.86(3) 2.37(3) 3.184(8) 158(6)
N2 H2n O4 1_555 0.86(3) 2.35(6) 2.767(9) 110(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
O2 S1 N2 C9 . . . . -49.5(6) ?
O1 S1 N2 C9 . . . . -177.4(6) ?
C1 S1 N2 C9 . . . . 66.8(6) ?
O2 S1 C1 C6 . . . . -153.6(6) ?
O1 S1 C1 C6 . . . . -22.9(7) ?
N2 S1 C1 C6 . . . . 91.4(7) ?
O2 S1 C1 C2 . . . . 30.5(7) ?
O1 S1 C1 C2 . . . . 161.2(6) ?
N2 S1 C1 C2 . . . . -84.5(7) ?
C6 C1 C2 C3 . . . . 0.8(12) ?
S1 C1 C2 C3 . . . . 176.7(7) ?
C1 C2 C3 C4 . . . . 0.2(13) ?
C2 C3 C4 C5 . . . . -0.4(13) ?
C2 C3 C4 N1 . . . . 178.2(8) ?
C7 N1 C4 C3 . . . . -0.9(13) ?
C7 N1 C4 C5 . . . . 177.7(8) ?
C3 C4 C5 C6 . . . . -0.5(12) ?
N1 C4 C5 C6 . . . . -179.2(7) ?
C4 C5 C6 C1 . . . . 1.5(12) ?
C2 C1 C6 C5 . . . . -1.7(12) ?
S1 C1 C6 C5 . . . . -177.6(6) ?
C4 N1 C7 O3 . . . . 3.5(13) ?
C4 N1 C7 C8 . . . . -174.9(8) ?
S1 N2 C9 C10 . . . . -99.4(7) ?
S1 N2 C9 C11A . . . . 138.0(7) ?
S1 N2 C9 C11 . . . . 138.0(7) ?
N2 C9 C10 O4 . . . . -31.3(11) ?
C11A C9 C10 O4 . . . . 90.5(11) ?
C11 C9 C10 O4 . . . . 90.5(11) ?
N2 C9 C10 O5 . . . . 150.7(7) ?
C11A C9 C10 O5 . . . . -87.5(9) ?
C11 C9 C10 O5 . . . . -87.5(9) ?
N2 C9 C11 C13 . . . . 169.7(13) ?
C10 C9 C11 C13 . . . . 47.7(16) ?
C11A C9 C11 C13 . . . . 0E1(10) ?
N2 C9 C11 C12 . . . . -62.3(12) ?
C10 C9 C11 C12 . . . . 175.7(9) ?
C11A C9 C11 C12 . . . . 0E1(10) ?
N2 C9 C11A C13A . . . . 85(3) ?
C10 C9 C11A C13A . . . . -37(3) ?
C11 C9 C11A C13A . . . . 0E1(10) ?
N2 C9 C11A C12A . . . . -62.3(12) ?
C10 C9 C11A C12A . . . . 175.7(9) ?
C11 C9 C11A C12A . . . . 0E1(10) ?
