#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:40:12 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178910 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/39/4113959.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_4113959
loop_
_publ_author_name
'David A. Evans'
'C. Wade Downey'
'Jed L. Hubbs'
_publ_section_title
;
 Ni(II) Bis(oxazoline)-Catalyzed Enantioselective Syn Aldol Reactions of
 N-Propionylthiazolidinethiones in the Presence of Silyl Triflates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8706
_journal_page_last               8707
_journal_paper_doi               10.1021/ja035509j
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C10 H15 N O2 S2'
_chemical_formula_weight         245.35
_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                   5.2860(8)
_cell_length_b                   7.6575(11)
_cell_length_c                   29.617(4)
_cell_measurement_temperature    213(2)
_cell_volume                     1198.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            7941
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0375
_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)+(0.0638P)²+0.3100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1054
_reflns_number_gt                2840
_reflns_number_total             2902
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja035509jsi20030407_021427.cif
_cod_data_source_block           cwd116t
_cod_database_code               4113959
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 0.83254(10) 0.52231(8) 0.230809(17) 0.03182(14) Uani 1 1 d .
S2 S 0.67977(13) 0.84920(7) 0.186871(18) 0.03747(15) Uani 1 1 d .
O1 O 0.1421(3) 0.4759(2) 0.12875(5) 0.0345(3) Uani 1 1 d .
O2 O 0.4986(3) 0.7168(2) 0.01659(5) 0.0301(3) Uani 1 1 d .
H2A H 0.6540 0.7133 0.0127 0.045 Uiso 1 1 calc R
C4 C 0.3321(4) 0.5637(3) 0.13209(6) 0.0245(4) Uani 1 1 d .
N1 N 0.5029(3) 0.5226(2) 0.16711(5) 0.0235(3) Uani 1 1 d .
C8 C 0.6252(3) 0.4575(3) 0.05615(7) 0.0261(4) Uani 1 1 d .
H8A H 0.7946 0.4922 0.0596 0.031 Uiso 1 1 calc R
C7 C 0.4292(3) 0.5977(3) 0.05172(6) 0.0227(4) Uani 1 1 d .
H7A H 0.2645 0.5435 0.0441 0.027 Uiso 1 1 calc R
C5 C 0.4034(4) 0.6986(3) 0.09710(6) 0.0227(4) Uani 1 1 d .
H5A H 0.5691 0.7503 0.1051 0.027 Uiso 1 1 calc R
C1 C 0.6582(4) 0.6348(3) 0.19051(6) 0.0243(3) Uani 1 1 d .
C6 C 0.2048(4) 0.8433(3) 0.09476(8) 0.0356(5) Uani 1 1 d .
H6A H 0.1965 0.9031 0.1236 0.053 Uiso 1 1 calc R
H6B H 0.0410 0.7928 0.0879 0.053 Uiso 1 1 calc R
H6C H 0.2508 0.9260 0.0713 0.053 Uiso 1 1 calc R
C9 C 0.5765(4) 0.2886(3) 0.05554(8) 0.0337(5) Uani 1 1 d .
H9A H 0.4095 0.2538 0.0494 0.040 Uiso 1 1 calc R
C2 C 0.7335(4) 0.3120(3) 0.20982(8) 0.0312(4) Uani 1 1 d .
H2B H 0.8559 0.2662 0.1880 0.037 Uiso 1 1 calc R
H2C H 0.7155 0.2281 0.2346 0.037 Uiso 1 1 calc R
C3 C 0.4815(4) 0.3462(3) 0.18751(7) 0.0282(4) Uani 1 1 d .
H3A H 0.4471 0.2584 0.1642 0.034 Uiso 1 1 calc R
H3B H 0.3446 0.3432 0.2098 0.034 Uiso 1 1 calc R
C10 C 0.7674(5) 0.1489(3) 0.06393(10) 0.0455(6) Uani 1 1 d .
H10A H 0.6867 0.0355 0.0616 0.068 Uiso 1 1 calc R
H10B H 0.8381 0.1630 0.0939 0.068 Uiso 1 1 calc R
H10C H 0.9014 0.1573 0.0417 0.068 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
C1 S1 C2 92.99(10)
O1 C4 N1 117.79(17)
O1 C4 C5 121.99(17)
N1 C4 C5 119.81(17)
C1 N1 C4 127.77(17)
C1 N1 C3 114.16(16)
C4 N1 C3 116.98(16)
C9 C8 C7 124.52(18)
O2 C7 C8 110.08(15)
O2 C7 C5 109.51(15)
C8 C7 C5 109.92(15)
C4 C5 C6 110.80(16)
C4 C5 C7 105.95(15)
C6 C5 C7 112.39(16)
N1 C1 S2 129.07(15)
N1 C1 S1 110.65(14)
S2 C1 S1 120.15(11)
C8 C9 C10 124.7(2)
C3 C2 S1 104.59(15)
N1 C3 C2 105.58(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.737(2)
S1 C2 1.804(2)
S2 C1 1.649(2)
O1 C4 1.213(2)
O2 C7 1.431(2)
C4 N1 1.411(2)
C4 C5 1.511(3)
N1 C1 1.376(2)
N1 C3 1.484(2)
C8 C9 1.318(3)
C8 C7 1.498(3)
C7 C5 1.556(3)
C5 C6 1.528(3)
C9 C10 1.492(3)
C2 C3 1.510(3)
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 C4 N1 C1 -148.5(2)
C5 C4 N1 C1 38.7(3)
O1 C4 N1 C3 18.8(3)
C5 C4 N1 C3 -154.00(18)
C9 C8 C7 O2 -127.4(2)
C9 C8 C7 C5 111.9(2)
O1 C4 C5 C6 63.1(3)
N1 C4 C5 C6 -124.43(19)
O1 C4 C5 C7 -59.1(2)
N1 C4 C5 C7 113.40(18)
O2 C7 C5 C4 -179.63(15)
C8 C7 C5 C4 -58.58(19)
O2 C7 C5 C6 59.2(2)
C8 C7 C5 C6 -179.73(17)
C4 N1 C1 S2 3.9(3)
C3 N1 C1 S2 -163.72(16)
C4 N1 C1 S1 179.58(15)
C3 N1 C1 S1 12.0(2)
C2 S1 C1 N1 9.03(15)
C2 S1 C1 S2 -174.82(14)
C7 C8 C9 C10 -174.4(2)
C1 S1 C2 C3 -26.08(15)
C1 N1 C3 C2 -31.6(2)
C4 N1 C3 C2 159.36(17)
S1 C2 C3 N1 35.17(19)
