#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:40:35 +0200 (Sun 07 de Aug de 2016) $
#$Revision: 185648 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/51/7155171.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_7155171
loop_
_publ_author_name
'Diebler, J.'
'Spannenberg, A.'
'Werner, T.'
_publ_section_title
;
 Atom economical synthesis of di- and trithiocarbonates by the lithium
 tert-butoxide catalyzed addition of carbon disulfide to epoxides and
 thiiranes.
;
_journal_issue                   31
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7480
_journal_page_last               7489
_journal_paper_doi               10.1039/c6ob01081d
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H16 O S2'
_chemical_formula_weight         228.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-05-09 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4952(2)
_cell_length_b                   9.1213(2)
_cell_length_c                   14.9630(3)
_cell_measurement_reflns_used    7630
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.83
_cell_measurement_theta_min      2.62
_cell_volume                     1159.44(4)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9562
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.498
_diffrn_reflns_theta_min         2.757
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.452
_exptl_crystal_size_mid          0.396
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1197 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0235
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0397P)²+0.1376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0635
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2861
_reflns_number_total             2938
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ob01081d2.cif
_cod_data_source_block           AX0806
_cod_depositor_comments          'Adding full bibliography for 7155171.cif.'
_cod_database_code               7155171
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 1.0300(2) 1.08513(16) 0.67370(10) 0.0238(3) Uani 1 1 d . .
C2 C 0.77181(18) 0.95993(17) 0.64869(9) 0.0208(3) Uani 1 1 d . .
H2 H 0.8121 0.8923 0.6013 0.025 Uiso 1 1 calc R U
C3 C 0.78036(19) 1.11439(17) 0.61040(11) 0.0244(3) Uani 1 1 d . .
C4 C 0.7130(2) 1.2367(2) 0.66839(14) 0.0353(4) Uani 1 1 d . .
H4A H 0.7548 1.2281 0.7292 0.053 Uiso 1 1 calc R U
H4B H 0.5980 1.2288 0.6700 0.053 Uiso 1 1 calc R U
H4C H 0.7429 1.3320 0.6433 0.053 Uiso 1 1 calc R U
C5 C 0.7074(2) 1.1106(2) 0.51793(11) 0.0298(3) Uani 1 1 d . .
H5A H 0.7702 1.0461 0.4784 0.036 Uiso 1 1 calc R U
H5B H 0.7068 1.2104 0.4919 0.036 Uiso 1 1 calc R U
C6 C 0.5376(2) 1.0522(2) 0.52487(12) 0.0302(3) Uani 1 1 d . .
H6A H 0.4724 1.1270 0.5553 0.036 Uiso 1 1 calc R U
H6B H 0.4952 1.0399 0.4637 0.036 Uiso 1 1 calc R U
C7 C 0.5199(2) 0.90593(18) 0.57512(11) 0.0264(3) Uani 1 1 d . .
H7 H 0.4050 0.8939 0.5877 0.032 Uiso 1 1 calc R U
C8 C 0.60314(19) 0.91520(18) 0.66733(10) 0.0253(3) Uani 1 1 d . .
H8A H 0.5508 0.9887 0.7058 0.030 Uiso 1 1 calc R U
H8B H 0.6000 0.8190 0.6979 0.030 Uiso 1 1 calc R U
C9 C 0.5704(2) 0.77097(19) 0.52319(12) 0.0309(4) Uani 1 1 d . .
C10 C 0.6081(2) 0.7738(2) 0.43675(14) 0.0393(4) Uani 1 1 d . .
H10A H 0.6344 0.6855 0.4067 0.047 Uiso 1 1 calc R U
H10B H 0.6085 0.8643 0.4052 0.047 Uiso 1 1 calc R U
C11 C 0.5695(3) 0.6283(2) 0.57311(15) 0.0502(6) Uani 1 1 d . .
H11A H 0.5761 0.5469 0.5305 0.075 Uiso 1 1 calc R U
H11B H 0.4719 0.6201 0.6077 0.075 Uiso 1 1 calc R U
H11C H 0.6600 0.6248 0.6137 0.075 Uiso 1 1 calc R U
O1 O 0.95213(14) 1.14327(13) 0.60441(8) 0.0261(2) Uani 1 1 d . .
S1 S 1.21504(5) 1.12257(5) 0.69392(3) 0.03124(12) Uani 1 1 d . .
S2 S 0.91887(5) 0.96258(4) 0.73695(2) 0.02535(10) Uani 1 1 d . .
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'
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 C1 S1 122.33(12)
O1 C1 S2 114.00(12)
S1 C1 S2 123.63(10)
C8 C2 C3 111.31(13)
C8 C2 S2 121.30(10)
C3 C2 S2 103.20(11)
C8 C2 H2 106.7
C3 C2 H2 106.7
S2 C2 H2 106.7
O1 C3 C5 110.51(13)
O1 C3 C2 103.51(12)
C5 C3 C2 107.61(13)
O1 C3 C4 105.85(14)
C5 C3 C4 112.50(14)
C2 C3 C4 116.43(14)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C3 C5 C6 109.20(14)
C3 C5 H5A 109.8
C6 C5 H5A 109.8
C3 C5 H5B 109.8
C6 C5 H5B 109.8
H5A C5 H5B 108.3
C7 C6 C5 115.07(14)
C7 C6 H6A 108.5
C5 C6 H6A 108.5
C7 C6 H6B 108.5
C5 C6 H6B 108.5
H6A C6 H6B 107.5
C9 C7 C6 115.18(14)
C9 C7 C8 111.74(14)
C6 C7 C8 110.02(13)
C9 C7 H7 106.4
C6 C7 H7 106.4
C8 C7 H7 106.4
C2 C8 C7 106.37(13)
C2 C8 H8A 110.5
C7 C8 H8A 110.5
C2 C8 H8B 110.5
C7 C8 H8B 110.5
H8A C8 H8B 108.6
C10 C9 C11 120.10(19)
C10 C9 C7 123.29(18)
C11 C9 C7 116.56(17)
C9 C10 H10A 120.0
C9 C10 H10B 120.0
H10A C10 H10B 120.0
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C1 O1 C3 111.61(12)
C1 S2 C2 89.22(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.339(2)
C1 S1 1.6368(18)
C1 S2 1.7425(16)
C2 C8 1.516(2)
C2 C3 1.523(2)
C2 S2 1.8180(15)
C2 H2 1.0000
C3 O1 1.4855(19)
C3 C5 1.516(2)
C3 C4 1.525(2)
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 C6 1.541(2)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.539(2)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C9 1.518(2)
C7 C8 1.553(2)
C7 H7 1.0000
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.333(3)
C9 C11 1.500(3)
C10 H10A 0.9500
C10 H10B 0.9500
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 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
C8 C2 C3 O1 175.11(12)
S2 C2 C3 O1 43.48(12)
C8 C2 C3 C5 -67.87(16)
S2 C2 C3 C5 160.51(11)
C8 C2 C3 C4 59.44(19)
S2 C2 C3 C4 -72.18(16)
O1 C3 C5 C6 169.46(13)
C2 C3 C5 C6 57.09(17)
C4 C3 C5 C6 -72.47(18)
C3 C5 C6 C7 -52.1(2)
C5 C6 C7 C9 -75.93(19)
C5 C6 C7 C8 51.4(2)
C3 C2 C8 C7 65.92(16)
S2 C2 C8 C7 -172.48(11)
C9 C7 C8 C2 73.89(17)
C6 C7 C8 C2 -55.38(17)
C6 C7 C9 C10 -8.4(3)
C8 C7 C9 C10 -134.94(18)
C6 C7 C9 C11 174.25(17)
C8 C7 C9 C11 47.7(2)
S1 C1 O1 C3 -169.43(11)
S2 C1 O1 C3 12.70(16)
C5 C3 O1 C1 -152.16(13)
C2 C3 O1 C1 -37.19(16)
C4 C3 O1 C1 85.77(15)
O1 C1 S2 C2 12.75(12)
S1 C1 S2 C2 -165.09(11)
C8 C2 S2 C1 -157.96(13)
C3 C2 S2 C1 -32.55(11)
