#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/47/2224715.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_2224715
loop_
_publ_author_name
'Datta, Mrityunjoy'
'Buglass, Alan J.'
'Elsegood, Mark R. J.'
_publ_section_title
;
 N-(3-Methoxyphenyl)-tert-butanesulfinamide
;
_journal_coeditor_code           NG2698
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o109
_journal_paper_doi               10.1107/S1600536809052507
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H17 N O2 S'
_chemical_formula_moiety         'C11 H17 N O2 S'
_chemical_formula_sum            'C11 H17 N O2 S'
_chemical_formula_weight         227.32
_chemical_name_systematic
;
N-(3-Methoxyphenyl)-tert-butanesulfinamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.2992(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4068(13)
_cell_length_b                   7.3076(8)
_cell_length_c                   12.9230(13)
_cell_measurement_reflns_used    4390
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      2.22
_cell_volume                     1169.7(2)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10627
_diffrn_reflns_theta_full        27.33
_diffrn_reflns_theta_max         27.33
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.403
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     149
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0560P)²+0.7085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1165
_reflns_number_gt                2237
_reflns_number_total             2633
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2698.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224715
_cod_database_fobs_code          2224715
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
O O1 0.54940(10) -0.05258(18) 0.36978(10) 0.0229(3) Uani d PDU 0.900(2) A 1
S S1 0.50816(3) 0.13248(6) 0.33748(3) 0.01938(15) Uani d PDU 0.900(2) A 1
N N1 0.42312(12) 0.2035(3) 0.42415(12) 0.0236(4) Uani d PDU 0.900(2) A 1
H H1 0.4482 0.2281 0.4877 0.028 Uiso calc PR 0.900(2) A 1
C C1 0.31128(13) 0.2253(2) 0.39789(13) 0.0253(4) Uani d . 1 . .
C C2 0.24035(14) 0.2103(3) 0.47687(14) 0.0277(4) Uani d . 1 A .
H H2 0.2669 0.1811 0.5453 0.033 Uiso calc R 1 . .
C C3 0.13034(14) 0.2383(3) 0.45550(14) 0.0289(4) Uani d . 1 . .
O O2 0.06872(11) 0.2258(3) 0.54029(11) 0.0462(4) Uani d . 1 A .
C C11 -0.04594(16) 0.2441(4) 0.52212(19) 0.0487(6) Uani d . 1 . .
H H11A -0.0626 0.3643 0.4916 0.073 Uiso calc R 1 A .
H H11B -0.0808 0.2325 0.5879 0.073 Uiso calc R 1 . .
H H11C -0.0727 0.1480 0.4744 0.073 Uiso calc R 1 . .
C C4 0.08935(14) 0.2716(3) 0.35566(15) 0.0300(4) Uani d . 1 A .
H H4 0.0140 0.2867 0.3407 0.036 Uiso calc R 1 . .
C C5 0.16122(16) 0.2821(3) 0.27816(15) 0.0384(5) Uani d . 1 . .
H H5 0.1340 0.3040 0.2090 0.046 Uiso calc R 1 A .
C C6 0.27117(15) 0.2620(3) 0.29758(14) 0.0328(4) Uani d . 1 A .
H H6 0.3188 0.2731 0.2429 0.039 Uiso calc R 1 . .
C C7 0.62017(14) 0.2928(3) 0.36663(14) 0.0212(4) Uani d PDU 0.900(2) A 1
C C8 0.57870(17) 0.4793(3) 0.32914(18) 0.0314(5) Uani d PDU 0.900(2) A 1
H H8A 0.5209 0.5198 0.3724 0.047 Uiso calc PR 0.900(2) A 1
H H8B 0.5507 0.4698 0.2569 0.047 Uiso calc PR 0.900(2) A 1
H H8C 0.6379 0.5682 0.3341 0.047 Uiso calc PR 0.900(2) A 1
C C9 0.65533(15) 0.2918(3) 0.48138(15) 0.0262(4) Uani d PDU 0.900(2) A 1
H H9A 0.6810 0.1694 0.5015 0.039 Uiso calc PR 0.900(2) A 1
H H9B 0.5939 0.3248 0.5220 0.039 Uiso calc PR 0.900(2) A 1
H H9C 0.7137 0.3807 0.4945 0.039 Uiso calc PR 0.900(2) A 1
C C10 0.7108(2) 0.2247(6) 0.3005(2) 0.0282(7) Uani d PDU 0.900(2) A 1
H H10A 0.7359 0.1048 0.3258 0.042 Uiso calc PR 0.900(2) A 1
H H10B 0.7710 0.3118 0.3054 0.042 Uiso calc PR 0.900(2) A 1
H H10C 0.6835 0.2141 0.2281 0.042 Uiso calc PR 0.900(2) A 1
O O1X 0.5509(11) 0.5520(16) 0.3695(10) 0.032(3) Uiso d PDU 0.100(2) A 2
S S1X 0.5084(4) 0.3681(6) 0.3374(3) 0.0303(15) Uiso d PDU 0.100(2) A 2
N N1X 0.4214(12) 0.288(2) 0.4216(13) 0.026(4) Uiso d PDU 0.100(2) A 2
H H1X 0.4450 0.2833 0.4871 0.032 Uiso calc PR 0.100(2) A 2
C C7X 0.6173(12) 0.204(2) 0.3663(12) 0.029(4) Uiso d PDU 0.100(2) A 2
C C8X 0.5762(16) 0.016(2) 0.3308(16) 0.034(4) Uiso d PDU 0.100(2) A 2
H H8D 0.5135 -0.0179 0.3694 0.052 Uiso calc PR 0.100(2) A 2
H H8E 0.6335 -0.0751 0.3436 0.052 Uiso calc PR 0.100(2) A 2
H H8F 0.5553 0.0197 0.2565 0.052 Uiso calc PR 0.100(2) A 2
C C9X 0.6514(16) 0.199(3) 0.4840(12) 0.032(5) Uiso d PDU 0.100(2) A 2
H H9D 0.6766 0.3204 0.5065 0.048 Uiso calc PR 0.100(2) A 2
H H9E 0.7096 0.1097 0.4964 0.048 Uiso calc PR 0.100(2) A 2
H H9F 0.5893 0.1635 0.5231 0.048 Uiso calc PR 0.100(2) A 2
C C10X 0.7138(19) 0.269(4) 0.308(2) 0.025(8) Uiso d PDU 0.100(2) A 2
H H10D 0.7374 0.3893 0.3344 0.038 Uiso calc PR 0.100(2) A 2
H H10E 0.6927 0.2793 0.2338 0.038 Uiso calc PR 0.100(2) A 2
H H10F 0.7731 0.1813 0.3179 0.038 Uiso calc PR 0.100(2) A 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
O1 S1 N1 . . 108.28(9) ?
O1 S1 C7 . . 106.04(8) ?
N1 S1 C7 . . 99.44(9) ?
C1 N1 S1 . . 121.54(13) ?
C1 N1 H1 . . 119.2 ?
S1 N1 H1 . . 119.2 ?
C6 C1 C2 . . 119.54(16) ?
C6 C1 N1 . . 122.58(16) ?
C2 C1 N1 . . 117.88(15) ?
C6 C1 N1X . . 114.7(6) ?
C2 C1 N1X . . 119.7(6) ?
C1 C2 C3 . . 119.86(16) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
O2 C3 C4 . . 124.38(16) ?
O2 C3 C2 . . 114.58(16) ?
C4 C3 C2 . . 121.03(17) ?
C3 O2 C11 . . 117.06(16) ?
O2 C11 H11A . . 109.5 ?
O2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C5 C4 C3 . . 117.97(16) ?
C5 C4 H4 . . 121.0 ?
C3 C4 H4 . . 121.0 ?
C6 C5 C4 . . 122.33(17) ?
C6 C5 H5 . . 118.8 ?
C4 C5 H5 . . 118.8 ?
C5 C6 C1 . . 119.20(17) ?
C5 C6 H6 . . 120.4 ?
C1 C6 H6 . . 120.4 ?
C9 C7 C8 . . 112.73(17) ?
C9 C7 C10 . . 111.27(18) ?
C8 C7 C10 . . 110.95(19) ?
C9 C7 S1 . . 111.54(13) ?
C8 C7 S1 . . 105.49(13) ?
C10 C7 S1 . . 104.40(18) ?
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 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O1X S1X N1X . . 111.3(8) ?
O1X S1X C7X . . 106.8(8) ?
N1X S1X C7X . . 97.7(8) ?
C1 N1X S1X . . 127.0(11) ?
C1 N1X H1X . . 116.5 ?
S1X N1X H1X . . 116.5 ?
C8X C7X C10X . . 112.9(15) ?
C8X C7X C9X . . 109.8(14) ?
C10X C7X C9X . . 108.3(16) ?
C8X C7X S1X . . 107.4(11) ?
C10X C7X S1X . . 106.6(14) ?
C9X C7X S1X . . 111.8(11) ?
C7X C8X H8D . . 109.5 ?
C7X C8X H8E . . 109.5 ?
H8D C8X H8E . . 109.5 ?
C7X C8X H8F . . 109.5 ?
H8D C8X H8F . . 109.5 ?
H8E C8X H8F . . 109.5 ?
C7X C9X H9D . . 109.5 ?
C7X C9X H9E . . 109.5 ?
H9D C9X H9E . . 109.5 ?
C7X C9X H9F . . 109.5 ?
H9D C9X H9F . . 109.5 ?
H9E C9X H9F . . 109.5 ?
C7X C10X H10D . . 109.5 ?
C7X C10X H10E . . 109.5 ?
H10D C10X H10E . . 109.5 ?
C7X C10X H10F . . 109.5 ?
H10D C10X H10F . . 109.5 ?
H10E C10X H10F . . 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
O1 S1 . 1.4967(14) ?
S1 N1 . 1.6652(16) ?
S1 C7 . 1.8401(19) ?
N1 C1 . 1.418(2) ?
N1 H1 . 0.8800 ?
C1 C6 . 1.388(3) ?
C1 C2 . 1.390(2) ?
C1 N1X . 1.457(16) ?
C2 C3 . 1.392(2) ?
C2 H2 . 0.9500 ?
C3 O2 . 1.375(2) ?
C3 C4 . 1.381(3) ?
O2 C11 . 1.435(2) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C4 C5 . 1.381(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C9 . 1.522(3) ?
C7 C8 . 1.526(3) ?
C7 C10 . 1.534(3) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
O1X S1X . 1.493(12) ?
S1X N1X . 1.681(13) ?
S1X C7X . 1.828(13) ?
N1X H1X . 0.8800 ?
C7X C8X . 1.528(16) ?
C7X C10X . 1.528(16) ?
C7X C9X . 1.555(15) ?
C8X H8D . 0.9800 ?
C8X H8E . 0.9800 ?
C8X H8F . 0.9800 ?
C9X H9D . 0.9800 ?
C9X H9E . 0.9800 ?
C9X H9F . 0.9800 ?
C10X H10D . 0.9800 ?
C10X H10E . 0.9800 ?
C10X H10F . 0.9800 ?
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 H1 O1 3_656 0.88 2.24 2.884(2) 129.6
N1X H1X O1X 3_666 0.88 2.21 2.94(2) 141.0
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 N1 C1 . . . . -113.14(17) ?
C7 S1 N1 C1 . . . . 136.38(17) ?
S1 N1 C1 C6 . . . . -26.5(3) ?
S1 N1 C1 C2 . . . . 154.05(16) ?
S1 N1 C1 N1X . . . . -104.9(15) ?
C6 C1 C2 C3 . . . . -2.1(3) ?
N1 C1 C2 C3 . . . . 177.31(18) ?
N1X C1 C2 C3 . . . . 149.0(8) ?
C1 C2 C3 O2 . . . . -177.99(17) ?
C1 C2 C3 C4 . . . . 3.4(3) ?
C4 C3 O2 C11 . . . . 1.7(3) ?
C2 C3 O2 C11 . . . . -176.92(19) ?
O2 C3 C4 C5 . . . . 179.45(19) ?
C2 C3 C4 C5 . . . . -2.1(3) ?
C3 C4 C5 C6 . . . . -0.5(3) ?
C4 C5 C6 C1 . . . . 1.6(3) ?
C2 C1 C6 C5 . . . . -0.3(3) ?
N1 C1 C6 C5 . . . . -179.7(2) ?
N1X C1 C6 C5 . . . . -152.9(8) ?
O1 S1 C7 C9 . . . . -59.63(15) ?
N1 S1 C7 C9 . . . . 52.62(15) ?
O1 S1 C7 C8 . . . . 177.66(12) ?
N1 S1 C7 C8 . . . . -70.09(14) ?
O1 S1 C7 C10 . . . . 60.64(17) ?
N1 S1 C7 C10 . . . . 172.89(16) ?
C6 C1 N1X S1X . . . . -10.0(16) ?
C2 C1 N1X S1X . . . . -162.5(9) ?
N1 C1 N1X S1X . . . . 105(2) ?
O1X S1X N1X C1 . . . . 125.7(13) ?
C7X S1X N1X C1 . . . . -122.9(14) ?
O1X S1X C7X C8X . . . . -178.2(12) ?
N1X S1X C7X C8X . . . . 66.7(13) ?
O1X S1X C7X C10X . . . . -57.0(15) ?
N1X S1X C7X C10X . . . . -172.0(15) ?
O1X S1X C7X C9X . . . . 61.2(14) ?
N1X S1X C7X C9X . . . . -53.9(14) ?
