#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:37:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178434 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/55/4025591.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_4025591
loop_
_publ_author_name
'Devarajulu Sureshkumar'
'Srinivasamurthy Koutha'
'Venkataraman Ganesh'
'Srinivasan Chandrasekaran'
_publ_contact_author_address
; 
Department of Organic Chemistry
Indian Institute of Science
Bangaloe 560012, Karnataka
India
;
_publ_contact_author_email       scn@orgchem.iisc.ernet.in
_publ_contact_author_fax         '+91 80 23602423'
_publ_contact_author_name        'Prof. Srinivasan Chandrasekaran'
_publ_contact_author_phone       '+91 80 22932404'
_publ_section_title
;
 Tetrathiomolybdate Mediated Rearrangement of Aziridinemethanol Tosylates:
 A Thia-Aza-Payne Rearrangement
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5533
_journal_page_last               5541
_journal_paper_doi               10.1021/jo100640w
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C12 H17 N O2 S3'
_chemical_formula_sum            'C12 H17 N O2 S3'
_chemical_formula_weight         303.45
_chemical_melting_point          415.15
_chemical_name_common            cyclic-disulfide
_chemical_name_systematic
;
 (S*)-N-(3,3-dimethyl-1,2-dithiolan-4-yl)-4-methylbenzenesulfonamide
;
_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
_cell_angle_alpha                109.161(8)
_cell_angle_beta                 102.369(8)
_cell_angle_gamma                94.459(9)
_cell_formula_units_Z            2
_cell_length_a                   7.238(4)
_cell_length_b                   10.304(5)
_cell_length_c                   10.950(6)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.04
_cell_volume                     743.7(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_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  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7746
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.492
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.8238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0491
_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)+(0.0874P)²+0.2843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1505
_reflns_number_gt                2567
_reflns_number_total             2959
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo100640w_si_001_5.cif
_cod_data_source_block           compound4j
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '142 deg' was changed to '415.15' -
it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        743.8(7)
_cod_database_code               4025591
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0842(3) 0.2575(2) 0.0982(2) 0.0540(5) Uani 1 1 d . . .
C2 C 0.1685(4) 0.1638(3) 0.1485(2) 0.0621(6) Uani 1 1 d . . .
H2 H 0.2982 0.1596 0.1566 0.075 Uiso 1 1 calc R . .
C3 C 0.0581(5) 0.0770(3) 0.1863(3) 0.0719(7) Uani 1 1 d . . .
H3 H 0.1147 0.0134 0.2197 0.086 Uiso 1 1 calc R . .
C4 C -0.1349(5) 0.0814(3) 0.1763(3) 0.0706(7) Uani 1 1 d . . .
C5 C -0.2173(4) 0.1756(3) 0.1239(3) 0.0784(8) Uani 1 1 d . . .
H5 H -0.3473 0.1791 0.1149 0.094 Uiso 1 1 calc R . .
C6 C -0.1099(4) 0.2633(3) 0.0854(3) 0.0706(7) Uani 1 1 d . . .
H6 H -0.1666 0.3261 0.0510 0.085 Uiso 1 1 calc R . .
C7 C -0.2540(6) -0.0135(3) 0.2184(4) 0.0999(11) Uani 1 1 d . . .
H7A H -0.3098 0.0410 0.2864 0.150 Uiso 1 1 calc R . .
H7B H -0.1746 -0.0702 0.2532 0.150 Uiso 1 1 calc R . .
H7C H -0.3540 -0.0721 0.1428 0.150 Uiso 1 1 calc R . .
N1 N 0.2363(3) 0.52647(19) 0.15869(18) 0.0571(5) Uani 1 1 d . . .
H1 H 0.2045 0.5927 0.1312 0.069 Uiso 1 1 calc R A 1
O1 O 0.4120(3) 0.33650(19) 0.06581(19) 0.0692(5) Uani 1 1 d . . .
O2 O 0.1191(3) 0.37450(19) -0.07326(16) 0.0651(5) Uani 1 1 d . . .
S1 S 0.22390(8) 0.37222(6) 0.05294(5) 0.0541(2) Uani 1 1 d . B .
C8A C 0.3019(8) 0.5524(6) 0.3013(6) 0.0487(13) Uani 0.529(3) 1 d P B 1
H8A H 0.3835 0.4832 0.3114 0.058 Uiso 0.529(3) 1 calc PR B 1
S1A S 0.4916(8) 0.7218(6) 0.5393(5) 0.133(2) Uani 0.529(3) 1 d P B 1
S2A S 0.2204(4) 0.6545(2) 0.54343(19) 0.1294(11) Uani 0.529(3) 1 d P B 1
C9A C 0.4301(8) 0.6953(5) 0.3632(5) 0.0636(13) Uani 0.529(3) 1 d P B 1
C12A C 0.1448(13) 0.5415(8) 0.3731(8) 0.082(2) Uani 0.529(3) 1 d P B 1
H12A H 0.1159 0.4463 0.3686 0.098 Uiso 0.529(3) 1 calc PR B 1
H12B H 0.0291 0.5662 0.3289 0.098 Uiso 0.529(3) 1 calc PR B 1
C11A C 0.328(2) 0.8109(14) 0.3347(14) 0.091(4) Uani 0.529(3) 1 d P B 1
H11A H 0.2972 0.7933 0.2404 0.136 Uiso 0.529(3) 1 calc PR B 1
H11B H 0.4109 0.8989 0.3813 0.136 Uiso 0.529(3) 1 calc PR B 1
H11C H 0.2127 0.8131 0.3645 0.136 Uiso 0.529(3) 1 calc PR B 1
C13A C 0.5973(19) 0.6393(14) 0.2890(14) 0.111(5) Uani 0.529(3) 1 d P B 1
H13A H 0.5937 0.5417 0.2731 0.166 Uiso 0.529(3) 1 calc PR B 1
H13B H 0.7203 0.6891 0.3450 0.166 Uiso 0.529(3) 1 calc PR B 1
H13C H 0.5758 0.6542 0.2053 0.166 Uiso 0.529(3) 1 calc PR B 1
C8B C 0.3821(9) 0.5766(7) 0.2931(7) 0.0500(14) Uani 0.471(3) 1 d P B 2
H8B H 0.4099 0.4972 0.3203 0.060 Uiso 0.471(3) 1 calc PR B 2
S1B S 0.4965(4) 0.7246(3) 0.5475(3) 0.0575(6) Uani 0.471(3) 1 d P B 2
S2B S 0.7122(3) 0.7501(3) 0.4555(2) 0.1211(11) Uani 0.471(3) 1 d P B 2
C9B C 0.3053(8) 0.6787(6) 0.3964(5) 0.0606(13) Uani 0.471(3) 1 d P B 2
C11B C 0.257(2) 0.8076(17) 0.3667(14) 0.113(6) Uani 0.471(3) 1 d P B 2
H11D H 0.1562 0.7810 0.2860 0.169 Uiso 0.471(3) 1 calc PR B 2
H11E H 0.3684 0.8549 0.3557 0.169 Uiso 0.471(3) 1 calc PR B 2
H11F H 0.2157 0.8686 0.4395 0.169 Uiso 0.471(3) 1 calc PR B 2
C12B C 0.604(2) 0.6917(15) 0.3242(15) 0.111(5) Uani 0.471(3) 1 d P B 2
H12C H 0.6838 0.6397 0.2711 0.133 Uiso 0.471(3) 1 calc PR B 2
H12D H 0.5738 0.7666 0.2921 0.133 Uiso 0.471(3) 1 calc PR B 2
C13B C 0.1362(15) 0.6105(14) 0.4212(11) 0.120(4) Uani 0.471(3) 1 d P B 2
H13D H 0.0392 0.5684 0.3386 0.179 Uiso 0.471(3) 1 calc PR B 2
H13E H 0.0866 0.6788 0.4838 0.179 Uiso 0.471(3) 1 calc PR B 2
H13F H 0.1732 0.5403 0.4571 0.179 Uiso 0.471(3) 1 calc PR 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.4(2) . . ?
C2 C1 S1 119.7(2) . . ?
C6 C1 S1 119.82(18) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 118.1(3) . . ?
C3 C4 C7 121.5(3) . . ?
C5 C4 C7 120.5(3) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8A N1 C8B 25.1(2) . . ?
C8A N1 S1 119.3(3) . . ?
C8B N1 S1 120.3(3) . . ?
C8A N1 H1 120.3 . . ?
C8B N1 H1 113.4 . . ?
S1 N1 H1 120.3 . . ?
O1 S1 O2 119.29(11) . . ?
O1 S1 N1 108.73(11) . . ?
O2 S1 N1 105.30(10) . . ?
O1 S1 C1 108.03(11) . . ?
O2 S1 C1 107.85(12) . . ?
N1 S1 C1 107.05(11) . . ?
N1 C8A C12A 115.9(5) . . ?
N1 C8A C9A 106.3(4) . . ?
C12A C8A C9A 112.4(5) . . ?
N1 C8A H8A 107.3 . . ?
C12A C8A H8A 107.3 . . ?
C9A C8A H8A 107.3 . . ?
C9A S1A S2A 95.1(3) . . ?
C12A S2A S1A 96.3(3) . . ?
C11A C9A C8A 112.8(7) . . ?
C11A C9A C13A 120.2(9) . . ?
C8A C9A C13A 93.0(6) . . ?
C11A C9A S1A 111.7(6) . . ?
C8A C9A S1A 102.8(4) . . ?
C13A C9A S1A 113.4(7) . . ?
C8A C12A S2A 110.4(5) . . ?
C8A C12A H12A 109.6 . . ?
S2A C12A H12A 109.6 . . ?
C8A C12A H12B 109.6 . . ?
S2A C12A H12B 109.6 . . ?
H12A C12A H12B 108.1 . . ?
C9B C8B N1 109.9(5) . . ?
C9B C8B C12B 95.2(6) . . ?
N1 C8B C12B 121.4(7) . . ?
C9B C8B H8B 109.7 . . ?
N1 C8B H8B 109.7 . . ?
C12B C8B H8B 109.7 . . ?
C9B S1B S2B 94.5(3) . . ?
C12B S2B S1B 98.0(6) . . ?
C13B C9B C8B 111.4(6) . . ?
C13B C9B C11B 109.3(9) . . ?
C8B C9B C11B 115.2(7) . . ?
C13B C9B S1B 106.6(6) . . ?
C8B C9B S1B 103.2(4) . . ?
C11B C9B S1B 110.8(7) . . ?
C9B C11B H11D 109.5 . . ?
C9B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C9B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
S2B C12B C8B 116.7(10) . . ?
S2B C12B H12C 108.1 . . ?
C8B C12B H12C 108.1 . . ?
S2B C12B H12D 108.1 . . ?
C8B C12B H12D 108.1 . . ?
H12C C12B H12D 107.3 . . ?
C9B C13B H13D 109.5 . . ?
C9B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C9B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.380(3) . ?
C1 C6 1.390(4) . ?
C1 S1 1.755(3) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 C7 1.500(4) . ?
C5 C6 1.370(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
N1 C8A 1.457(6) . ?
N1 C8B 1.516(7) . ?
N1 S1 1.612(2) . ?
N1 H1 0.8600 . ?
O1 S1 1.4275(19) . ?
O2 S1 1.4356(18) . ?
C8A C12A 1.531(9) . ?
C8A C9A 1.533(7) . ?
C8A H8A 0.9800 . ?
S1A C9A 1.805(7) . ?
S1A S2A 2.046(6) . ?
S2A C12A 1.781(7) . ?
C9A C11A 1.530(15) . ?
C9A C13A 1.637(13) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C8B C9B 1.508(9) . ?
C8B C12B 1.821(16) . ?
C8B H8B 0.9800 . ?
S1B C9B 1.811(6) . ?
S1B S2B 2.074(4) . ?
S2B C12B 1.384(16) . ?
C9B C13B 1.483(12) . ?
C9B C11B 1.517(17) . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(4) . . . . ?
S1 C1 C2 C3 178.52(19) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C2 C3 C4 C7 -179.7(3) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C7 C4 C5 C6 179.7(3) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
S1 C1 C6 C5 -178.5(2) . . . . ?
C8A N1 S1 O1 -62.7(3) . . . . ?
C8B N1 S1 O1 -33.7(3) . . . . ?
C8A N1 S1 O2 168.4(3) . . . . ?
C8B N1 S1 O2 -162.6(3) . . . . ?
C8A N1 S1 C1 53.8(3) . . . . ?
C8B N1 S1 C1 82.8(3) . . . . ?
C2 C1 S1 O1 5.7(2) . . . . ?
C6 C1 S1 O1 -175.4(2) . . . . ?
C2 C1 S1 O2 135.87(19) . . . . ?
C6 C1 S1 O2 -45.2(2) . . . . ?
C2 C1 S1 N1 -111.3(2) . . . . ?
C6 C1 S1 N1 67.6(2) . . . . ?
C8B N1 C8A C12A 166.4(14) . . . . ?
S1 N1 C8A C12A -94.2(6) . . . . ?
C8B N1 C8A C9A 40.7(9) . . . . ?
S1 N1 C8A C9A 140.1(3) . . . . ?
C9A S1A S2A C12A 27.3(4) . . . . ?
N1 C8A C9A C11A 56.3(7) . . . . ?
C12A C8A C9A C11A -71.5(8) . . . . ?
N1 C8A C9A C13A -68.4(8) . . . . ?
C12A C8A C9A C13A 163.8(9) . . . . ?
N1 C8A C9A S1A 176.8(4) . . . . ?
C12A C8A C9A S1A 49.0(7) . . . . ?
S2A S1A C9A C11A 77.2(7) . . . . ?
S2A S1A C9A C8A -44.1(4) . . . . ?
S2A S1A C9A C13A -143.1(6) . . . . ?
N1 C8A C12A S2A -150.3(5) . . . . ?
C9A C8A C12A S2A -27.8(8) . . . . ?
S1A S2A C12A C8A -3.9(7) . . . . ?
C8A N1 C8B C9B -54.3(9) . . . . ?
S1 N1 C8B C9B -149.5(4) . . . . ?
C8A N1 C8B C12B -163.8(15) . . . . ?
S1 N1 C8B C12B 100.9(7) . . . . ?
C9B S1B S2B C12B -11.7(7) . . . . ?
N1 C8B C9B C13B 65.7(8) . . . . ?
C12B C8B C9B C13B -168.2(9) . . . . ?
N1 C8B C9B C11B -59.5(9) . . . . ?
C12B C8B C9B C11B 66.6(10) . . . . ?
N1 C8B C9B S1B 179.6(4) . . . . ?
C12B C8B C9B S1B -54.3(7) . . . . ?
S2B S1B C9B C13B 162.3(6) . . . . ?
S2B S1B C9B C8B 44.9(4) . . . . ?
S2B S1B C9B C11B -78.9(7) . . . . ?
S1B S2B C12B C8B -20.2(11) . . . . ?
C9B C8B C12B S2B 52.2(12) . . . . ?
N1 C8B C12B S2B 169.4(8) . . . . ?
