#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:40:12 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178910 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/39/4113957.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_4113957
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            'C17 H17 N O2 S2'
_chemical_formula_weight         331.44
_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                   9.0460(13)
_cell_length_b                   12.5033(18)
_cell_length_c                   14.244(2)
_cell_measurement_temperature    193(2)
_cell_volume                     1611.1(4)
_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      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11727
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       shard
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0405
_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)+(0.0761P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                3633
_reflns_number_total             3996
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja035509jsi20030407_021301.cif
_cod_data_source_block           cwd113t
_cod_database_code               4113957
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 -0.01939(7) -0.13905(4) -0.63357(3) 0.04412(16) Uani 1 1 d .
S2 S 0.01537(8) -0.24512(4) -0.44989(4) 0.05283(18) Uani 1 1 d .
N1 N 0.15153(16) -0.07190(12) -0.48799(10) 0.0280(3) Uani 1 1 d .
O2 O -0.08332(19) 0.23784(12) -0.53879(13) 0.0519(4) Uani 1 1 d .
H2A H -0.0926 0.2995 -0.5161 0.078 Uiso 1 1 calc R
O1 O 0.32330(15) 0.05585(12) -0.50694(11) 0.0405(3) Uani 1 1 d .
C5 C 0.0864(2) 0.09972(15) -0.57082(13) 0.0321(4) Uani 1 1 d .
H5A H -0.0028 0.0569 -0.5884 0.039 Uiso 1 1 calc R
C1 C 0.0519(2) -0.14163(15) -0.52763(13) 0.0325(4) Uani 1 1 d .
C8 C 0.0176(2) 0.14318(15) -0.39841(14) 0.0358(4) Uani 1 1 d .
C3 C 0.2313(2) -0.11439(15) -0.40550(13) 0.0337(4) Uani 1 1 d .
H3A H 0.2610 -0.0555 -0.3631 0.040 Uiso 1 1 calc R
H3B H 0.3211 -0.1535 -0.4255 0.040 Uiso 1 1 calc R
C4 C 0.19803(19) 0.02760(14) -0.52384(13) 0.0284(4) Uani 1 1 d .
C9 C -0.1028(2) 0.07594(17) -0.37393(15) 0.0389(4) Uani 1 1 d .
C15 C 0.0029(3) 0.0531(2) -0.21710(17) 0.0549(6) Uani 1 1 d .
H15A H -0.0009 0.0223 -0.1562 0.066 Uiso 1 1 calc R
C14 C -0.1128(3) 0.03012(18) -0.28422(17) 0.0470(5) Uani 1 1 d .
C6 C 0.1515(3) 0.15103(19) -0.65856(15) 0.0468(5) Uani 1 1 d .
H6A H 0.1787 0.0951 -0.7036 0.070 Uiso 1 1 calc R
H6B H 0.2396 0.1923 -0.6416 0.070 Uiso 1 1 calc R
H6C H 0.0781 0.1987 -0.6870 0.070 Uiso 1 1 calc R
C2 C 0.1250(2) -0.18899(16) -0.35645(14) 0.0359(4) Uani 1 1 d .
H2B H 0.0620 -0.1494 -0.3115 0.043 Uiso 1 1 calc R
H2C H 0.1790 -0.2458 -0.3222 0.043 Uiso 1 1 calc R
C10 C -0.2202(2) 0.04991(19) -0.4400(2) 0.0501(6) Uani 1 1 d .
H10A H -0.2188 0.0798 -0.5013 0.060 Uiso 1 1 calc R
C7 C 0.0416(2) 0.18679(15) -0.49787(15) 0.0369(4) Uani 1 1 d .
H7A H 0.1234 0.2404 -0.4949 0.044 Uiso 1 1 calc R
C17 C 0.1219(2) 0.16420(19) -0.33140(16) 0.0441(5) Uani 1 1 d .
H17A H 0.2010 0.2113 -0.3462 0.053 Uiso 1 1 calc R
C13 C -0.2279(4) -0.0404(2) -0.2610(2) 0.0657(8) Uani 1 1 d .
H13A H -0.2320 -0.0709 -0.1999 0.079 Uiso 1 1 calc R
C16 C 0.1158(3) 0.1177(2) -0.24031(16) 0.0525(6) Uani 1 1 d .
H16A H 0.1915 0.1324 -0.1959 0.063 Uiso 1 1 calc R
C11 C -0.3312(3) -0.0165(3) -0.4148(2) 0.0636(8) Uani 1 1 d .
H11A H -0.4089 -0.0307 -0.4579 0.076 Uiso 1 1 calc R
C12 C -0.3332(4) -0.0652(3) -0.3248(3) 0.0771(9) Uani 1 1 d .
H12A H -0.4084 -0.1152 -0.3095 0.093 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 S2 C2 94.36(9)
C1 N1 C4 127.35(16)
C1 N1 C3 114.74(15)
C4 N1 C3 117.37(15)
C4 C5 C6 110.89(17)
C4 C5 C7 107.19(15)
C6 C5 C7 110.69(16)
N1 C1 S1 128.50(14)
N1 C1 S2 109.62(13)
S1 C1 S2 121.77(11)
C17 C8 C9 118.1(2)
C17 C8 C7 118.58(19)
C9 C8 C7 123.13(18)
N1 C3 C2 106.18(16)
O1 C4 N1 117.70(17)
O1 C4 C5 122.65(18)
N1 C4 C5 119.22(15)
C14 C9 C8 121.0(2)
C14 C9 C10 116.8(2)
C8 C9 C10 122.2(2)
C16 C15 C14 120.5(2)
C9 C14 C13 121.2(3)
C9 C14 C15 118.3(2)
C13 C14 C15 120.4(2)
C3 C2 S2 104.43(13)
C11 C10 C9 120.5(3)
O2 C7 C8 115.18(18)
O2 C7 C5 104.28(16)
C8 C7 C5 113.86(15)
C8 C17 C16 122.1(2)
C12 C13 C14 120.5(3)
C15 C16 C17 120.0(2)
C10 C11 C12 120.9(3)
C13 C12 C11 120.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6415(19)
S2 C1 1.7348(19)
S2 C2 1.802(2)
N1 C1 1.375(2)
N1 C4 1.409(2)
N1 C3 1.478(2)
O2 C7 1.423(2)
O1 C4 1.211(2)
C5 C4 1.510(3)
C5 C6 1.523(3)
C5 C7 1.559(3)
C8 C17 1.368(3)
C8 C9 1.419(3)
C8 C7 1.533(3)
C3 C2 1.511(3)
C9 C14 1.403(3)
C9 C10 1.456(3)
C15 C16 1.343(4)
C15 C14 1.446(4)
C14 C13 1.405(4)
C10 C11 1.351(4)
C17 C16 1.423(3)
C13 C12 1.353(5)
C11 C12 1.419(5)
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
C4 N1 C1 S1 10.9(3)
C3 N1 C1 S1 -160.37(15)
C4 N1 C1 S2 -172.88(14)
C3 N1 C1 S2 15.82(19)
C2 S2 C1 N1 4.51(15)
C2 S2 C1 S1 -179.00(13)
C1 N1 C3 C2 -32.5(2)
C4 N1 C3 C2 155.24(15)
C1 N1 C4 O1 -148.12(19)
C3 N1 C4 O1 23.0(2)
C1 N1 C4 C5 39.2(3)
C3 N1 C4 C5 -149.69(16)
C6 C5 C4 O1 49.2(3)
C7 C5 C4 O1 -71.7(2)
C6 C5 C4 N1 -138.48(18)
C7 C5 C4 N1 100.59(19)
C17 C8 C9 C14 -1.5(3)
C7 C8 C9 C14 174.11(18)
C17 C8 C9 C10 179.27(18)
C7 C8 C9 C10 -5.1(3)
C8 C9 C14 C13 -177.0(2)
C10 C9 C14 C13 2.2(3)
C8 C9 C14 C15 0.0(3)
C10 C9 C14 C15 179.24(19)
C16 C15 C14 C9 0.7(3)
C16 C15 C14 C13 177.8(2)
N1 C3 C2 S2 32.38(17)
C1 S2 C2 C3 -21.93(14)
C14 C9 C10 C11 -0.8(3)
C8 C9 C10 C11 178.4(2)
C17 C8 C7 O2 -133.23(19)
C9 C8 C7 O2 51.2(2)
C17 C8 C7 C5 106.4(2)
C9 C8 C7 C5 -69.2(2)
C4 C5 C7 O2 -168.63(15)
C6 C5 C7 O2 70.3(2)
C4 C5 C7 C8 -42.3(2)
C6 C5 C7 C8 -163.34(18)
C9 C8 C17 C16 2.4(3)
C7 C8 C17 C16 -173.41(19)
C9 C14 C13 C12 -0.5(4)
C15 C14 C13 C12 -177.5(3)
C14 C15 C16 C17 0.1(3)
C8 C17 C16 C15 -1.8(3)
C9 C10 C11 C12 -2.2(4)
C14 C13 C12 C11 -2.6(5)
C10 C11 C12 C13 4.0(5)
