#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/05/2230500.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_2230500
loop_
_publ_author_name
'Shakuntala, K.'
'Foro, Sabine'
'Gowda, B. Thimme'
_publ_section_title
;
 N-(2-Chlorophenylsulfonyl)-2,2-dimethylpropanamide
;
_journal_coeditor_code           TK2742
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1400
_journal_paper_doi               10.1107/S1600536811017429
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H14 Cl N O3 S'
_chemical_formula_moiety         'C11 H14 Cl N O3 S'
_chemical_formula_sum            'C11 H14 Cl N O3 S'
_chemical_formula_weight         275.74
_chemical_name_systematic
;
N-(2-Chlorophenylsulfonyl)-2,2-dimethylpropanamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.120(10)
_cell_angle_beta                 107.140(10)
_cell_angle_gamma                94.200(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7850(10)
_cell_length_b                   8.9140(10)
_cell_length_c                   9.3130(10)
_cell_measurement_reflns_used    2522
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.69
_cell_measurement_theta_min      3.14
_cell_volume                     670.98(14)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ
;
_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  0.0117
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4355
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.8519
_exptl_absorpt_correction_T_min  0.8314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.259
_refine_ls_extinction_coef       0.129(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0533P)²+0.2343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                2321
_reflns_number_total             2730
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            tk2742.cif
_cod_data_source_block           I
_cod_original_cell_volume        670.98(13)
_cod_database_code               2230500
_cod_database_fobs_code          2230500
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1873(2) 0.8220(2) 0.6448(2) 0.0421(4) Uani d . 1 1 . .
C C2 0.2567(2) 0.9285(2) 0.5857(2) 0.0506(5) Uani d . 1 1 . .
C C3 0.1853(3) 0.9346(3) 0.4339(3) 0.0635(6) Uani d . 1 1 . .
H H3 0.2316 1.0059 0.3940 0.076 Uiso calc R 1 1 . .
C C4 0.0468(3) 0.8358(3) 0.3420(3) 0.0666(6) Uani d . 1 1 . .
H H4 -0.0012 0.8417 0.2405 0.080 Uiso calc R 1 1 . .
C C5 -0.0218(2) 0.7287(3) 0.3977(3) 0.0603(5) Uani d . 1 1 . .
H H5 -0.1153 0.6614 0.3341 0.072 Uiso calc R 1 1 . .
C C6 0.0485(2) 0.7210(2) 0.5489(2) 0.0482(4) Uani d . 1 1 . .
H H6 0.0026 0.6476 0.5868 0.058 Uiso calc R 1 1 . .
C C7 0.4718(2) 0.6231(2) 0.7753(2) 0.0424(4) Uani d . 1 1 . .
C C8 0.6484(2) 0.6029(2) 0.8078(2) 0.0473(4) Uani d . 1 1 . .
C C9 0.7309(3) 0.7253(3) 0.7535(4) 0.0773(7) Uani d . 1 1 . .
H H9A 0.7220 0.8274 0.8089 0.093 Uiso calc R 1 1 . .
H H9B 0.6802 0.7112 0.6439 0.093 Uiso calc R 1 1 . .
H H9C 0.8427 0.7144 0.7735 0.093 Uiso calc R 1 1 . .
C C10 0.7287(3) 0.6256(4) 0.9819(3) 0.0817(8) Uani d . 1 1 . .
H H10A 0.6750 0.5503 1.0166 0.098 Uiso calc R 1 1 . .
H H10B 0.7221 0.7287 1.0368 0.098 Uiso calc R 1 1 . .
H H10C 0.8398 0.6122 1.0018 0.098 Uiso calc R 1 1 . .
C C11 0.6588(3) 0.4422(3) 0.7175(4) 0.0894(9) Uani d . 1 1 . .
H H11A 0.6088 0.4308 0.6082 0.107 Uiso calc R 1 1 . .
H H11B 0.6044 0.3650 0.7496 0.107 Uiso calc R 1 1 . .
H H11C 0.7699 0.4287 0.7373 0.107 Uiso calc R 1 1 . .
N N1 0.44486(18) 0.76248(19) 0.86001(19) 0.0483(4) Uani d D 1 1 . .
H H1N 0.515(2) 0.838(2) 0.912(2) 0.058 Uiso d D 1 1 . .
O O1 0.29358(17) 0.96456(19) 0.94151(18) 0.0656(4) Uani d . 1 1 . .
O O2 0.16258(17) 0.69277(19) 0.86012(18) 0.0635(4) Uani d . 1 1 . .
O O3 0.36032(17) 0.52985(17) 0.68368(18) 0.0614(4) Uani d . 1 1 . .
Cl Cl1 0.43167(8) 1.05545(7) 0.69656(9) 0.0820(2) Uani d . 1 1 . .
S S1 0.26460(5) 0.81187(6) 0.83971(5) 0.04740(17) Uani d . 1 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 . . 119.18(18) ?
C6 C1 S1 . . 117.88(15) ?
C2 C1 S1 . . 122.92(14) ?
C3 C2 C1 . . 119.74(18) ?
C3 C2 Cl1 . . 118.34(16) ?
C1 C2 Cl1 . . 121.92(16) ?
C4 C3 C2 . . 120.2(2) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C5 C4 C3 . . 120.8(2) ?
C5 C4 H4 . . 119.6 ?
C3 C4 H4 . . 119.6 ?
C4 C5 C6 . . 119.62(19) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C5 C6 C1 . . 120.45(19) ?
C5 C6 H6 . . 119.8 ?
C1 C6 H6 . . 119.8 ?
O3 C7 N1 . . 120.27(17) ?
O3 C7 C8 . . 124.89(17) ?
N1 C7 C8 . . 114.84(15) ?
C11 C8 C7 . . 109.01(18) ?
C11 C8 C9 . . 109.4(2) ?
C7 C8 C9 . . 108.39(16) ?
C11 C8 C10 . . 110.8(2) ?
C7 C8 C10 . . 109.76(17) ?
C9 C8 C10 . . 109.4(2) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C8 C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C8 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C7 N1 S1 . . 123.31(13) ?
C7 N1 H1N . . 125.0(16) ?
S1 N1 H1N . . 110.5(16) ?
O2 S1 O1 . . 118.83(10) ?
O2 S1 N1 . . 109.93(9) ?
O1 S1 N1 . . 104.49(9) ?
O2 S1 C1 . . 107.67(9) ?
O1 S1 C1 . . 109.39(9) ?
N1 S1 C1 . . 105.81(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 C6 . 1.389(2) ?
C1 C2 . 1.388(3) ?
C1 S1 . 1.7664(19) ?
C2 C3 . 1.383(3) ?
C2 Cl1 . 1.728(2) ?
C3 C4 . 1.370(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.368(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O3 . 1.202(2) ?
C7 N1 . 1.389(2) ?
C7 C8 . 1.523(2) ?
C8 C11 . 1.512(3) ?
C8 C9 . 1.524(3) ?
C8 C10 . 1.524(3) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
N1 S1 . 1.6434(15) ?
N1 H1N . 0.826(16) ?
O1 S1 . 1.4274(15) ?
O2 S1 . 1.4209(16) ?
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 H1N O1 2_677 0.826(16) 2.217(16) 3.042(2) 178(2)
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 . . . . 1.3(3) ?
S1 C1 C2 C3 . . . . -177.01(16) ?
C6 C1 C2 Cl1 . . . . -178.68(14) ?
S1 C1 C2 Cl1 . . . . 3.0(2) ?
C1 C2 C3 C4 . . . . -0.1(3) ?
Cl1 C2 C3 C4 . . . . 179.88(18) ?
C2 C3 C4 C5 . . . . -0.9(4) ?
C3 C4 C5 C6 . . . . 0.6(3) ?
C4 C5 C6 C1 . . . . 0.6(3) ?
C2 C1 C6 C5 . . . . -1.5(3) ?
S1 C1 C6 C5 . . . . 176.85(15) ?
O3 C7 C8 C11 . . . . -4.9(3) ?
N1 C7 C8 C11 . . . . 175.7(2) ?
O3 C7 C8 C9 . . . . 114.0(2) ?
N1 C7 C8 C9 . . . . -65.3(2) ?
O3 C7 C8 C10 . . . . -126.5(2) ?
N1 C7 C8 C10 . . . . 54.2(2) ?
O3 C7 N1 S1 . . . . -1.5(3) ?
C8 C7 N1 S1 . . . . 177.89(13) ?
C7 N1 S1 O2 . . . . 54.30(18) ?
C7 N1 S1 O1 . . . . -177.13(15) ?
C7 N1 S1 C1 . . . . -61.69(17) ?
C6 C1 S1 O2 . . . . 0.55(16) ?
C2 C1 S1 O2 . . . . 178.86(15) ?
C6 C1 S1 O1 . . . . -129.89(14) ?
C2 C1 S1 O1 . . . . 48.42(17) ?
C6 C1 S1 N1 . . . . 118.06(15) ?
C2 C1 S1 N1 . . . . -63.63(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656740
