#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:13:47 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178890 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/19/4111925.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_4111925
loop_
_publ_author_name
'Devarajulu Sureshkumar'
'Srinivasa Murthy Koutha'
'Srinivasan Chandrasekaran'
_publ_section_title
;
 Chemistry of Tetrathiomolybdate: Aziridine Ring Opening Reactions and
 Facile Synthesis of Interesting Sulfur Heterocycles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12760
_journal_page_last               12761
_journal_paper_doi               10.1021/ja052969z
_journal_volume                  127
_journal_year                    2005
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C11 H15 N O2 S3'
_chemical_formula_sum            'C11 H15 N O2 S3'
_chemical_formula_weight         289.45
_chemical_melting_point          367
_chemical_name_common            'cyclic aminodisulfide'
_chemical_name_systematic
;
N1-[(3R*,4S*)-3-methyl-1,2-dithiolan-4-yl]
methyl-4-methyl-1-benzenesulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90
_cell_angle_beta                 112.404(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.470(7)
_cell_length_b                   7.347(4)
_cell_length_c                   15.965(9)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.78
_cell_volume                     1352.3(13)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9165
_diffrn_reflns_reduction_process ' ?'
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.8384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0812P)²+0.8733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                1983
_reflns_number_total             2370
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ja052969zsi20050506_083554_03.cif
_cod_data_source_block           compound8
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4111925
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+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
S1 S 0.74724(7) 0.80366(11) 0.16034(6) 0.0385(3) Uani 1 1 d .
S2 S 0.77996(9) 1.33950(16) -0.05618(7) 0.0633(4) Uani 1 1 d .
S3 S 0.94374(9) 1.23561(16) 0.01163(8) 0.0631(4) Uani 1 1 d .
O1 O 0.6987(2) 0.7967(3) 0.22855(18) 0.0543(7) Uani 1 1 d .
O2 O 0.6974(2) 0.6969(3) 0.08043(17) 0.0507(6) Uani 1 1 d .
C5 C 0.8950(3) 0.7447(4) 0.2114(2) 0.0362(7) Uani 1 1 d .
N1 N 0.7400(2) 1.0157(4) 0.13158(18) 0.0404(7) Uani 1 1 d .
H1 H 0.7122 1.0936 0.1581 0.048 Uiso 1 1 calc R
C2 C 0.7801(3) 1.0781(4) 0.0608(2) 0.0416(8) Uani 1 1 d .
H2 H 0.7640 0.9835 0.0143 0.050 Uiso 1 1 calc R
C10 C 0.9447(3) 0.6399(4) 0.1647(2) 0.0422(8) Uani 1 1 d .
H10 H 0.8999 0.5934 0.1079 0.051 Uiso 1 1 calc R
C8 C 1.1307(3) 0.6757(5) 0.2868(3) 0.0490(9) Uani 1 1 d .
C1 C 0.7140(3) 1.2495(5) 0.0182(3) 0.0478(8) Uani 1 1 d .
H1A H 0.7228 1.3386 0.0660 0.057 Uiso 1 1 calc R
C3 C 0.9111(3) 1.1235(5) 0.0985(3) 0.0525(9) Uani 1 1 d .
H3A H 0.9563 1.0127 0.1168 0.063 Uiso 1 1 calc R
H3B H 0.9304 1.2021 0.1511 0.063 Uiso 1 1 calc R
C9 C 1.0617(3) 0.6049(5) 0.2031(3) 0.0495(9) Uani 1 1 d .
H9 H 1.0954 0.5320 0.1722 0.059 Uiso 1 1 calc R
C6 C 0.9605(3) 0.8132(5) 0.2958(2) 0.0499(9) Uani 1 1 d .
H6 H 0.9260 0.8826 0.3274 0.060 Uiso 1 1 calc R
C7 C 1.0777(3) 0.7775(5) 0.3328(3) 0.0571(10) Uani 1 1 d .
H7 H 1.1220 0.8230 0.3899 0.069 Uiso 1 1 calc R
C11 C 1.2593(3) 0.6419(7) 0.3245(3) 0.0731(13) Uani 1 1 d .
H11A H 1.2951 0.7098 0.3796 0.088 Uiso 1 1 calc R
H11B H 1.2910 0.6799 0.2812 0.088 Uiso 1 1 calc R
H11C H 1.2739 0.5145 0.3368 0.088 Uiso 1 1 calc R
C4 C 0.5864(4) 1.2158(7) -0.0344(4) 0.0861(15) Uani 1 1 d .
H4A H 0.5770 1.1219 -0.0785 0.103 Uiso 1 1 calc R
H4B H 0.5503 1.3257 -0.0646 0.103 Uiso 1 1 calc R
H4C H 0.5506 1.1783 0.0064 0.103 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
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 '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
O2 S1 O1 119.62(16)
O2 S1 N1 108.58(15)
O1 S1 N1 104.82(14)
O2 S1 C5 107.57(15)
O1 S1 C5 108.03(16)
N1 S1 C5 107.69(14)
C1 S2 S3 97.33(13)
C3 S3 S2 96.03(13)
C10 C5 C6 120.9(3)
C10 C5 S1 119.7(3)
C6 C5 S1 119.2(3)
C2 N1 S1 121.3(2)
C2 N1 H1 119.4
S1 N1 H1 119.4
N1 C2 C1 108.5(3)
N1 C2 C3 112.7(3)
C1 C2 C3 107.9(3)
N1 C2 H2 109.2
C1 C2 H2 109.2
C3 C2 H2 109.2
C5 C10 C9 119.0(3)
C5 C10 H10 120.5
C9 C10 H10 120.5
C7 C8 C9 118.0(3)
C7 C8 C11 122.1(4)
C9 C8 C11 120.0(4)
C4 C1 C2 113.0(3)
C4 C1 S2 110.0(3)
C2 C1 S2 107.0(2)
C4 C1 H1A 108.9
C2 C1 H1A 108.9
S2 C1 H1A 108.9
C2 C3 S3 108.4(2)
C2 C3 H3A 110.0
S3 C3 H3A 110.0
C2 C3 H3B 110.0
S3 C3 H3B 110.0
H3A C3 H3B 108.4
C10 C9 C8 121.5(3)
C10 C9 H9 119.2
C8 C9 H9 119.2
C7 C6 C5 119.1(3)
C7 C6 H6 120.5
C5 C6 H6 120.5
C6 C7 C8 121.4(3)
C6 C7 H7 119.3
C8 C7 H7 119.3
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
C1 C4 H4A 109.5
C1 C4 H4B 109.5
H4A C4 H4B 109.5
C1 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.423(3)
S1 O1 1.434(3)
S1 N1 1.617(3)
S1 C5 1.761(3)
S2 C1 1.807(4)
S2 S3 2.0591(17)
S3 C3 1.789(4)
C5 C10 1.373(5)
C5 C6 1.378(5)
N1 C2 1.472(4)
N1 H1 0.8600
C2 C1 1.517(5)
C2 C3 1.547(5)
C2 H2 0.9800
C10 C9 1.374(5)
C10 H10 0.9300
C8 C7 1.380(6)
C8 C9 1.386(5)
C8 C11 1.503(5)
C1 C4 1.510(6)
C1 H1A 0.9800
C3 H3A 0.9700
C3 H3B 0.9700
C9 H9 0.9300
C6 C7 1.377(5)
C6 H6 0.9300
C7 H7 0.9300
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 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
C1 S2 S3 C3 0.5(2)
O2 S1 C5 C10 11.2(3)
O1 S1 C5 C10 141.7(3)
N1 S1 C5 C10 -105.6(3)
O2 S1 C5 C6 -172.4(3)
O1 S1 C5 C6 -42.0(3)
N1 S1 C5 C6 70.7(3)
O2 S1 N1 C2 -49.9(3)
O1 S1 N1 C2 -178.8(2)
C5 S1 N1 C2 66.3(3)
S1 N1 C2 C1 153.4(2)
S1 N1 C2 C3 -87.2(3)
C6 C5 C10 C9 -0.4(5)
S1 C5 C10 C9 175.8(2)
N1 C2 C1 C4 -66.9(4)
C3 C2 C1 C4 170.7(4)
N1 C2 C1 S2 171.9(2)
C3 C2 C1 S2 49.5(3)
S3 S2 C1 C4 -150.6(3)
S3 S2 C1 C2 -27.5(3)
N1 C2 C3 S3 -169.6(2)
C1 C2 C3 S3 -49.8(3)
S2 S3 C3 C2 26.2(3)
C5 C10 C9 C8 -1.3(5)
C7 C8 C9 C10 2.5(5)
C11 C8 C9 C10 -177.0(3)
C10 C5 C6 C7 0.9(5)
S1 C5 C6 C7 -175.4(3)
C5 C6 C7 C8 0.4(6)
C9 C8 C7 C6 -2.0(5)
C11 C8 C7 C6 177.5(4)
