#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/45/1504541.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_1504541
loop_
_publ_author_name
'Osorio-Lozada, Antonio'
'Olivo, Horacio F.'
_publ_section_title
;
 Indene-based thiazolidinethione chiral auxiliary for propionate and
 acetate aldol additions.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              617
_journal_page_last               620
_journal_paper_doi               10.1021/ol702980p
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H19 N O2 S2, H2 O'
_chemical_formula_sum            'C16 H21 N O3 S2'
_chemical_formula_weight         339.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                   4.7392(6)
_cell_length_b                   11.8411(13)
_cell_length_c                   29.781(4)
_cell_measurement_reflns_used    3221
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.0
_cell_volume                     1671.2(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL v6.1 (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL v6.1 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXTL v6.1 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL v6.1 (Sheldrick, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega 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  0.0651
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10258
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.5
_diffrn_reflns_theta_min         3.2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.8766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2124
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0569
_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)+(0.0203P)²+2.9042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                1767
_reflns_number_total             2124
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol702980p-file005.cif
_cod_data_source_block           oli72
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1504541
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+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 0.1300(4) 0.66809(12) 0.77589(5) 0.0447(4) Uani 1 1 d .
C2' C 0.1591(13) 0.5356(5) 0.80083(16) 0.0377(14) Uani 1 1 d .
S2' S 0.3717(4) 0.44058(13) 0.77787(5) 0.0489(4) Uani 1 1 d .
N3' N -0.0069(9) 0.5288(4) 0.83868(14) 0.0358(12) Uani 1 1 d .
C3A' C -0.1123(13) 0.6394(4) 0.85515(16) 0.0387(13) Uani 1 1 d .
H3A' H -0.3036 0.6303 0.8689 0.046 Uiso 1 1 calc R
C3B' C 0.0870(12) 0.6953(5) 0.88833(16) 0.0373(14) Uani 1 1 d .
C4' C 0.2116(13) 0.6498(5) 0.92584(18) 0.0430(16) Uani 1 1 d .
H4' H 0.1743 0.5739 0.9343 0.052 Uiso 1 1 calc R
C5' C 0.3952(15) 0.7170(6) 0.95163(18) 0.0515(16) Uani 1 1 d .
H5' H 0.4854 0.6863 0.9774 0.062 Uiso 1 1 calc R
C6' C 0.4437(13) 0.8280(6) 0.93928(19) 0.0523(18) Uani 1 1 d .
H6' H 0.5653 0.8734 0.9571 0.063 Uiso 1 1 calc R
C7' C 0.3200(13) 0.8737(5) 0.90195(19) 0.0480(17) Uani 1 1 d .
H7' H 0.3578 0.9496 0.8936 0.058 Uiso 1 1 calc R
C7A' C 0.1372(13) 0.8073(5) 0.87623(17) 0.0403(14) Uani 1 1 d .
C7B' C -0.0301(12) 0.8381(5) 0.83483(18) 0.0458(16) Uani 1 1 d .
H7A' H 0.0888 0.8791 0.8129 0.055 Uiso 1 1 calc R
H7B' H -0.1947 0.8856 0.8427 0.055 Uiso 1 1 calc R
C8A' C -0.1249(13) 0.7234(4) 0.81595(17) 0.0426(14) Uani 1 1 d .
H8A' H -0.3185 0.7277 0.8027 0.051 Uiso 1 1 calc R
C1 C -0.0888(14) 0.4318(5) 0.86379(17) 0.0408(15) Uani 1 1 d .
O1 O -0.2327(9) 0.4468(3) 0.89691(13) 0.0568(13) Uani 1 1 d .
C2 C 0.0005(12) 0.3166(4) 0.84863(17) 0.0382(14) Uani 1 1 d .
H2A H 0.2091 0.3122 0.8493 0.046 Uiso 1 1 calc R
H2B H -0.0602 0.3056 0.8171 0.046 Uiso 1 1 calc R
C3 C -0.1204(13) 0.2209(4) 0.87733(16) 0.0363(13) Uani 1 1 d .
H3A H -0.3245 0.2368 0.8830 0.044 Uiso 1 1 calc R
O3 O -0.0983(9) 0.1169(3) 0.85273(11) 0.0437(10) Uani 1 1 d .
H3B H -0.250(12) 0.1042(10) 0.8395(10) 0.065 Uiso 1 1 calc R
C4 C 0.0254(12) 0.2055(5) 0.92189(17) 0.0413(15) Uani 1 1 d .
H4A H 0.0260 0.2786 0.9380 0.050 Uiso 1 1 calc R
H4B H 0.2242 0.1839 0.9164 0.050 Uiso 1 1 calc R
C5 C -0.1098(14) 0.1168(5) 0.95187(17) 0.0488(15) Uani 1 1 d .
H5A H -0.1156 0.0442 0.9355 0.059 Uiso 1 1 calc R
H5B H -0.3069 0.1395 0.9582 0.059 Uiso 1 1 calc R
C6 C 0.0428(14) 0.0990(5) 0.99624(19) 0.059(2) Uani 1 1 d .
H6A H -0.0579 0.0423 1.0140 0.089 Uiso 1 1 calc R
H6B H 0.0490 0.1704 1.0129 0.089 Uiso 1 1 calc R
H6C H 0.2356 0.0729 0.9904 0.089 Uiso 1 1 calc R
O10 O 0.5885(9) 0.5901(5) 0.68914(16) 0.0723(14) Uani 1 1 d D
H10A H 0.588(13) 0.573(6) 0.7167(7) 0.108 Uiso 1 1 d D
H10B H 0.761(4) 0.596(7) 0.682(2) 0.108 Uiso 1 1 d 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'
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_publ_flag
C2' S1' C8A' 95.6(3) yes
N3' C2' S2' 130.2(4) yes
N3' C2' S1' 110.9(4) yes
S2' C2' S1' 118.9(3) yes
C2' N3' C1 129.3(5) yes
C2' N3' C3A' 114.3(4) yes
C1 N3' C3A' 116.5(4) yes
N3' C3A' C3B' 113.0(5) yes
N3' C3A' C8A' 109.5(4) yes
C3B' C3A' C8A' 103.7(4) yes
N3' C3A' H3A' 110.2 ?
C3B' C3A' H3A' 110.2 ?
C8A' C3A' H3A' 110.2 ?
C4' C3B' C7A' 120.6(5) yes
C4' C3B' C3A' 128.7(5) yes
C7A' C3B' C3A' 110.6(5) yes
C3B' C4' C5' 119.2(5) yes
C3B' C4' H4' 120.4 ?
C5' C4' H4' 120.4 ?
C6' C5' C4' 119.6(6) yes
C6' C5' H5' 120.2 ?
C4' C5' H5' 120.2 ?
C7' C6' C5' 121.3(6) yes
C7' C6' H6' 119.3 ?
C5' C6' H6' 119.3 ?
C6' C7' C7A' 119.2(5) yes
C6' C7' H7' 120.4 ?
C7A' C7' H7' 120.4 ?
C3B' C7A' C7' 119.9(5) yes
C3B' C7A' C7B' 110.6(5) yes
C7' C7A' C7B' 129.5(5) yes
C7A' C7B' C8A' 103.8(4) yes
C7A' C7B' H7A' 111.0 ?
C8A' C7B' H7A' 111.0 ?
C7A' C7B' H7B' 111.0 ?
C8A' C7B' H7B' 111.0 ?
H7A' C7B' H7B' 109.0 ?
C3A' C8A' C7B' 106.5(4) yes
C3A' C8A' S1' 103.8(4) yes
C7B' C8A' S1' 111.4(4) yes
C3A' C8A' H8A' 111.6 ?
C7B' C8A' H8A' 111.6 ?
S1' C8A' H8A' 111.6 ?
O1 C1 N3' 117.5(5) yes
O1 C1 C2 122.5(5) yes
N3' C1 C2 119.9(5) yes
C1 C2 C3 113.6(4) yes
C1 C2 H2A 108.9 ?
C3 C2 H2A 108.9 ?
C1 C2 H2B 108.9 ?
C3 C2 H2B 108.9 ?
H2A C2 H2B 107.7 ?
O3 C3 C4 108.1(4) yes
O3 C3 C2 108.8(4) yes
C4 C3 C2 114.2(5) yes
O3 C3 H3A 108.5 ?
C4 C3 H3A 108.5 ?
C2 C3 H3A 108.5 ?
C3 O3 H3B 109.5 ?
C3 C4 C5 114.1(5) yes
C3 C4 H4A 108.7 ?
C5 C4 H4A 108.7 ?
C3 C4 H4B 108.7 ?
C5 C4 H4B 108.7 ?
H4A C4 H4B 107.6 ?
C4 C5 C6 113.9(5) yes
C4 C5 H5A 108.8 ?
C6 C5 H5A 108.8 ?
C4 C5 H5B 108.8 ?
C6 C5 H5B 108.8 ?
H5A C5 H5B 107.7 ?
C5 C6 H6A 109.5 ?
C5 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C5 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
H10A O10 H10B 105.0(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1' C2' 1.742(5) yes
S1' C8A' 1.820(6) yes
C2' N3' 1.377(6) yes
C2' S2' 1.658(6) yes
N3' C1 1.424(7) yes
N3' C3A' 1.485(6) yes
C3A' C3B' 1.519(7) yes
C3A' C8A' 1.536(7) yes
C3A' H3A' 1.0000 ?
C3B' C4' 1.373(7) yes
C3B' C7A' 1.394(7) yes
C4' C5' 1.407(8) yes
C4' H4' 0.9500 ?
C5' C6' 1.384(8) yes
C5' H5' 0.9500 ?
C6' C7' 1.368(8) yes
C6' H6' 0.9500 ?
C7' C7A' 1.399(8) yes
C7' H7' 0.9500 ?
C7A' C7B' 1.510(8) yes
C7B' C8A' 1.536(7) yes
C7B' H7A' 0.9900 ?
C7B' H7B' 0.9900 ?
C8A' H8A' 1.0000 ?
C1 O1 1.212(6) yes
C1 C2 1.498(7) yes
C2 C3 1.530(7) yes
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C3 O3 1.437(6) yes
C3 C4 1.507(7) yes
C3 H3A 1.0000 ?
O3 H3B 0.8345 ?
C4 C5 1.520(7) yes
C4 H4A 0.9900 ?
C4 H4B 0.9900 ?
C5 C6 1.521(8) yes
C5 H5A 0.9900 ?
C5 H5B 0.9900 ?
C6 H6A 0.9800 ?
C6 H6B 0.9800 ?
C6 H6C 0.9800 ?
O10 H10A 0.847(10) ?
O10 H10B 0.846(11) ?
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
_geom_hbond_publ_flag
O3 H3B O10 3_546 0.83 1.82 2.656(6) 175 yes
O10 H10A S1' . 0.85(1) 3.01(6) 3.500(5) 119(5) yes
O10 H10A S2' . 0.85(1) 2.61(4) 3.343(5) 145(6) yes
O10 H10B O3 3_656 0.85(1) 1.92(2) 2.737(6) 161(6) yes
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
C8A' S1' C2' N3' -1.3(4)
C8A' S1' C2' S2' 179.4(4)
S2' C2' N3' C1 -14.4(9)
S1' C2' N3' C1 166.4(5)
S2' C2' N3' C3A' 165.4(5)
S1' C2' N3' C3A' -13.9(6)
C2' N3' C3A' C3B' -89.4(5)
C1 N3' C3A' C3B' 90.4(6)
C2' N3' C3A' C8A' 25.5(7)
C1 N3' C3A' C8A' -154.7(5)
N3' C3A' C3B' C4' -49.6(8)
C8A' C3A' C3B' C4' -168.0(6)
N3' C3A' C3B' C7A' 130.4(5)
C8A' C3A' C3B' C7A' 12.0(6)
C7A' C3B' C4' C5' -1.1(8)
C3A' C3B' C4' C5' 178.8(5)
C3B' C4' C5' C6' 1.0(9)
C4' C5' C6' C7' -1.1(10)
C5' C6' C7' C7A' 1.1(9)
C4' C3B' C7A' C7' 1.2(9)
C3A' C3B' C7A' C7' -178.8(5)
C4' C3B' C7A' C7B' -178.2(5)
C3A' C3B' C7A' C7B' 1.8(7)
C6' C7' C7A' C3B' -1.1(9)
C6' C7' C7A' C7B' 178.1(6)
C3B' C7A' C7B' C8A' -14.8(6)
C7' C7A' C7B' C8A' 165.9(6)
N3' C3A' C8A' C7B' -141.5(5)
C3B' C3A' C8A' C7B' -20.7(6)
N3' C3A' C8A' S1' -23.8(6)
C3B' C3A' C8A' S1' 97.0(4)
C7A' C7B' C8A' C3A' 21.7(6)
C7A' C7B' C8A' S1' -90.8(5)
C2' S1' C8A' C3A' 14.7(4)
C2' S1' C8A' C7B' 128.8(4)
C2' N3' C1 O1 178.4(5)
C3A' N3' C1 O1 -1.4(8)
C2' N3' C1 C2 -2.2(9)
C3A' N3' C1 C2 178.0(5)
O1 C1 C2 C3 3.2(8)
N3' C1 C2 C3 -176.2(5)
C1 C2 C3 O3 162.2(5)
C1 C2 C3 C4 -76.9(6)
O3 C3 C4 C5 -63.4(6)
C2 C3 C4 C5 175.3(5)
C3 C4 C5 C6 178.3(5)
