#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/56/1505649.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1505649
loop_
_publ_author_name
'Harmata, Michael'
'Zheng, Pinguan'
_publ_section_title
;
 A stereospecific synthesis of chiral cyclic sulfinamides.
;
_journal_issue                   25
_journal_name_full               'Organic letters'
_journal_page_first              5251
_journal_page_last               5253
_journal_paper_doi               10.1021/ol7024394
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H12 N O S'
_chemical_formula_weight         194.27
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3752(4)
_cell_length_b                   8.4870(6)
_cell_length_c                   21.9878(16)
_cell_measurement_temperature    173(2)
_cell_volume                     1003.07(13)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7086
_diffrn_reflns_theta_full        27.11
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         1.85
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0303
_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)+(0.0498P)²+0.1578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                2144
_reflns_number_total             2196
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7024394-file001.cif
_cod_data_source_block           PZ-IX-38A1
_cod_database_code               1505649
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.23318(8) 0.58494(4) 0.231066(16) 0.03404(12) Uani 1 1 d .
O1 O 0.0530(3) 0.49502(14) 0.26922(6) 0.0569(4) Uani 1 1 d .
N1 N 0.0876(3) 0.70028(14) 0.18282(6) 0.0333(3) Uani 1 1 d .
C1 C 0.3408(3) 0.44712(19) 0.17480(7) 0.0337(3) Uani 1 1 d .
H1A H 0.4496 0.5025 0.1454 0.040 Uiso 1 1 calc R
H1B H 0.4410 0.3642 0.1949 0.040 Uiso 1 1 calc R
C2 C 0.1242(3) 0.37024(17) 0.14055(6) 0.0283(3) Uani 1 1 d .
H2 H 0.0179 0.3150 0.1712 0.034 Uiso 1 1 calc R
C3 C -0.0362(3) 0.49414(16) 0.10949(6) 0.0257(3) Uani 1 1 d .
C4 C -0.1808(3) 0.45843(18) 0.05844(7) 0.0306(3) Uani 1 1 d .
H4 H -0.1714 0.3555 0.0416 0.037 Uiso 1 1 calc R
C5 C -0.3372(3) 0.5677(2) 0.03163(7) 0.0366(3) Uani 1 1 d .
H5 H -0.4354 0.5390 -0.0026 0.044 Uiso 1 1 calc R
C6 C -0.3502(3) 0.7194(2) 0.05486(8) 0.0389(4) Uani 1 1 d .
H6 H -0.4555 0.7955 0.0364 0.047 Uiso 1 1 calc R
C7 C -0.2086(3) 0.75945(17) 0.10520(7) 0.0359(3) Uani 1 1 d .
H7 H -0.2179 0.8631 0.1213 0.043 Uiso 1 1 calc R
C8 C -0.0527(3) 0.64861(17) 0.13241(6) 0.0283(3) Uani 1 1 d .
C9 C 0.2218(3) 0.24484(18) 0.09553(7) 0.0383(4) Uani 1 1 d .
H9A H 0.0777 0.1886 0.0778 0.046 Uiso 1 1 calc R
H9B H 0.3092 0.2991 0.0619 0.046 Uiso 1 1 calc R
C10 C 0.3976(4) 0.1241(2) 0.12334(10) 0.0494(5) Uani 1 1 d .
H10A H 0.5580 0.1740 0.1321 0.074 Uiso 1 1 calc R
H10B H 0.4222 0.0370 0.0947 0.074 Uiso 1 1 calc R
H10C H 0.3257 0.0834 0.1612 0.074 Uiso 1 1 calc R
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
O1 S1 N1 111.04(8)
O1 S1 C1 105.26(8)
N1 S1 C1 95.55(7)
C8 N1 S1 125.25(10)
C2 C1 S1 111.74(11)
C2 C1 H1A 109.3
S1 C1 H1A 109.3
C2 C1 H1B 109.3
S1 C1 H1B 109.3
H1A C1 H1B 107.9
C3 C2 C1 110.91(12)
C3 C2 C9 112.38(12)
C1 C2 C9 110.50(13)
C3 C2 H2 107.6
C1 C2 H2 107.6
C9 C2 H2 107.6
C4 C3 C8 117.02(13)
C4 C3 C2 121.70(13)
C8 C3 C2 121.24(13)
C5 C4 C3 122.30(14)
C5 C4 H4 118.8
C3 C4 H4 118.8
C4 C5 C6 119.72(15)
C4 C5 H5 120.1
C6 C5 H5 120.1
C7 C6 C5 119.63(15)
C7 C6 H6 120.2
C5 C6 H6 120.2
C6 C7 C8 120.50(14)
C6 C7 H7 119.8
C8 C7 H7 119.8
C7 C8 C3 120.82(14)
C7 C8 N1 116.66(13)
C3 C8 N1 122.52(13)
C10 C9 C2 114.65(13)
C10 C9 H9A 108.6
C2 C9 H9A 108.6
C10 C9 H9B 108.6
C2 C9 H9B 108.6
H9A C9 H9B 107.6
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4912(13)
S1 N1 1.6420(14)
S1 C1 1.7983(15)
N1 C8 1.4103(19)
C1 C2 1.533(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.5217(19)
C2 C9 1.5453(19)
C2 H2 1.0000
C3 C4 1.399(2)
C3 C8 1.4073(19)
C4 C5 1.384(2)
C4 H4 0.9500
C5 C6 1.387(2)
C5 H5 0.9500
C6 C7 1.385(2)
C6 H6 0.9500
C7 C8 1.395(2)
C7 H7 0.9500
C9 C10 1.522(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
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
O1 S1 N1 C8 -69.15(14)
C1 S1 N1 C8 39.55(14)
O1 S1 C1 C2 53.55(13)
N1 S1 C1 C2 -60.05(12)
S1 C1 C2 C3 58.35(15)
S1 C1 C2 C9 -176.34(10)
C1 C2 C3 C4 155.18(14)
C9 C2 C3 C4 30.94(19)
C1 C2 C3 C8 -27.28(18)
C9 C2 C3 C8 -151.52(14)
C8 C3 C4 C5 -1.0(2)
C2 C3 C4 C5 176.62(14)
C3 C4 C5 C6 1.2(3)
C4 C5 C6 C7 -0.8(3)
C5 C6 C7 C8 0.3(3)
C6 C7 C8 C3 -0.2(2)
C6 C7 C8 N1 179.00(15)
C4 C3 C8 C7 0.5(2)
C2 C3 C8 C7 -177.16(14)
C4 C3 C8 N1 -178.62(13)
C2 C3 C8 N1 3.7(2)
S1 N1 C8 C7 165.53(12)
S1 N1 C8 C3 -15.3(2)
C3 C2 C9 C10 176.11(16)
C1 C2 C9 C10 51.64(19)
