#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:55:18 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178829 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/83/4108357.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_4108357
loop_
_publ_author_name
'Le Li'
'Eric G. Klauber'
'Daniel Seidel'
_publ_section_title
;
 Catalytic Enantioselective Aldol Additions of α-Isothiocyanato Imides to
 Aldehydes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12248
_journal_page_last               12249
_journal_paper_doi               10.1021/ja804838y
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C13 H15 N O4 S'
_chemical_formula_weight         281.32
_chemical_name_systematic
; 

 ? 

;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 100.446(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.9697(5)
_cell_length_b                   5.1144(3)
_cell_length_c                   11.8901(6)
_cell_measurement_reflns_used    7645
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.05
_cell_measurement_theta_min      2.33
_cell_volume                     656.02(6)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8677
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9044
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker SAINT'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       flat_rod
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4394
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0420P)²+0.1560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0711
_reflns_number_gt                4293
_reflns_number_total             4394
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja804838y_si_003.cif
_cod_data_source_block           le3meo
_cod_database_code               4108357
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
S1 S 0.88746(2) 1.03739(5) 0.71526(2) 0.01565(6) Uani 1 1 d
O1 O 0.20527(8) 1.37261(19) 0.69267(7) 0.02064(17) Uani 1 1 d
O2 O 0.67925(6) 1.03660(17) 0.79260(6) 0.01353(13) Uani 1 1 d
O3 O 0.57823(8) 0.37884(18) 0.97329(7) 0.01795(15) Uani 1 1 d
O4 O 0.77966(8) 0.47592(17) 0.97433(7) 0.01801(16) Uani 1 1 d
N1 N 0.74010(9) 0.63935(19) 0.75933(8) 0.01414(16) Uani 1 1 d
C1 C 0.46527(9) 0.9265(2) 0.72051(8) 0.01183(17) Uani 1 1 d
C2 C 0.38144(10) 1.1129(2) 0.74386(9) 0.01342(17) Uani 1 1 d
C3 C 0.28155(10) 1.1885(2) 0.65967(9) 0.01447(18) Uani 1 1 d
C4 C 0.26528(10) 1.0748(2) 0.55134(9) 0.01620(19) Uani 1 1 d
C5 C 0.34945(11) 0.8851(2) 0.52929(9) 0.01694(19) Uani 1 1 d
C6 C 0.44941(10) 0.8106(2) 0.61225(9) 0.01547(19) Uani 1 1 d
C7 C 0.10542(11) 1.4648(3) 0.60787(11) 0.0206(2) Uani 1 1 d
C8 C 0.76728(9) 0.8932(2) 0.75649(8) 0.01226(17) Uani 1 1 d
C9 C 0.57601(9) 0.8668(2) 0.81218(9) 0.01173(16) Uani 1 1 d
C10 C 0.63152(9) 0.58962(18) 0.81017(9) 0.01168(17) Uani 1 1 d
C11 C 0.65985(10) 0.4678(2) 0.92917(9) 0.01280(17) Uani 1 1 d
C12 C 0.82034(12) 0.3430(3) 1.08406(10) 0.0231(2) Uani 1 1 d
C13 C 0.89804(14) 0.1114(3) 1.06489(11) 0.0238(2) Uani 1 1 d
H1 H 0.3899(19) 1.196(5) 0.8132(18) 0.036(5) Uiso 1 1 d
H2 H 0.1962(15) 1.119(3) 0.4926(14) 0.016(4) Uiso 1 1 d
H3 H 0.3363(17) 0.803(4) 0.4520(16) 0.027(5) Uiso 1 1 d
H4 H 0.5034(16) 0.682(4) 0.5923(15) 0.020(4) Uiso 1 1 d
H5 H 0.0477(16) 1.327(4) 0.5835(16) 0.024(4) Uiso 1 1 d
H6 H 0.0641(19) 1.593(4) 0.6340(18) 0.034(5) Uiso 1 1 d
H7 H 0.1337(16) 1.532(4) 0.5452(15) 0.025(4) Uiso 1 1 d
H8 H 0.5592(12) 0.912(3) 0.8885(12) 0.007(3) Uiso 1 1 d
H9 H 0.5741(15) 0.478(3) 0.7666(13) 0.015(4) Uiso 1 1 d
H10 H 0.7903(15) 0.524(4) 0.7481(14) 0.022(4) Uiso 1 1 d
H11 H 0.8650(19) 0.480(5) 1.1302(18) 0.039(5) Uiso 1 1 d
H12 H 0.7499(16) 0.301(4) 1.1153(16) 0.026(4) Uiso 1 1 d
H13 H 0.970(3) 0.151(6) 1.040(2) 0.065(8) Uiso 1 1 d
H14 H 0.9287(16) 0.027(5) 1.1345(16) 0.031(4) Uiso 1 1 d
H15 H 0.8525(19) -0.006(5) 1.0186(18) 0.039(5) Uiso 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'
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
C3 O1 C7 117.20(9)
C8 O2 C9 110.19(8)
C11 O4 C12 117.68(9)
C8 N1 C10 112.63(9)
C8 N1 H10 122.0(14)
C10 N1 H10 123.7(14)
C2 C1 C6 119.93(9)
C2 C1 C9 118.07(9)
C6 C1 C9 121.90(9)
C1 C2 C3 120.58(10)
C1 C2 H1 122.4(14)
C3 C2 H1 117.0(14)
O1 C3 C4 124.82(10)
O1 C3 C2 115.28(10)
C4 C3 C2 119.89(10)
C3 C4 C5 118.99(9)
C3 C4 H2 121.7(10)
C5 C4 H2 119.3(10)
C6 C5 C4 121.40(10)
C6 C5 H3 120.2(11)
C4 C5 H3 118.4(11)
C5 C6 C1 119.20(10)
C5 C6 H4 117.6(11)
C1 C6 H4 123.2(11)
O1 C7 H5 110.7(11)
O1 C7 H6 111.9(13)
H5 C7 H6 107.4(16)
O1 C7 H7 111.4(11)
H5 C7 H7 109.2(16)
H6 C7 H7 106.0(19)
N1 C8 O2 110.26(9)
N1 C8 S1 129.25(8)
O2 C8 S1 120.48(8)
O2 C9 C1 107.86(8)
O2 C9 C10 102.78(8)
C1 C9 C10 116.27(9)
O2 C9 H8 106.4(9)
C1 C9 H8 110.9(8)
C10 C9 H8 111.8(9)
N1 C10 C11 114.39(9)
N1 C10 C9 101.60(8)
C11 C10 C9 112.03(8)
N1 C10 H9 113.4(9)
C11 C10 H9 105.6(10)
C9 C10 H9 109.9(10)
O3 C11 O4 126.49(10)
O3 C11 C10 121.01(10)
O4 C11 C10 112.50(9)
O4 C12 C13 108.68(10)
O4 C12 H11 102.0(13)
C13 C12 H11 114.6(13)
O4 C12 H12 108.6(11)
C13 C12 H12 114.0(13)
H11 C12 H12 108.1(17)
C12 C13 H13 115(2)
C12 C13 H14 110.5(13)
H13 C13 H14 101(2)
C12 C13 H15 110.5(14)
H13 C13 H15 112(2)
H14 C13 H15 108(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.6603(11)
O1 C3 1.3639(13)
O1 C7 1.4276(14)
O2 C8 1.3434(12)
O2 C9 1.4788(12)
O3 C11 1.2059(13)
O4 C11 1.3272(13)
O4 C12 1.4671(14)
N1 C8 1.3340(15)
N1 C10 1.4525(13)
N1 H10 0.84(2)
C1 C2 1.3872(14)
C1 C6 1.3989(14)
C1 C9 1.5089(14)
C2 C3 1.3980(14)
C2 H1 0.92(2)
C3 C4 1.3949(15)
C4 C5 1.3964(16)
C4 H2 0.959(16)
C5 C6 1.3886(15)
C5 H3 0.997(19)
C6 H4 0.943(18)
C7 H5 0.95(2)
C7 H6 0.89(2)
C7 H7 0.923(18)
C9 C10 1.5446(14)
C9 H8 0.986(14)
C10 C11 1.5256(14)
C10 H9 0.934(17)
C12 C13 1.5008(19)
C12 H11 0.97(2)
C12 H12 0.941(18)
C13 H13 0.91(3)
C13 H14 0.94(2)
C13 H15 0.90(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H10 S1 0.84(2) 2.76(2) 3.5599(10) 160.7(17) 1_545
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
C6 C1 C2 C3 -0.64(16)
C9 C1 C2 C3 175.83(10)
C7 O1 C3 C4 -3.49(17)
C7 O1 C3 C2 177.08(10)
C1 C2 C3 O1 179.84(10)
C1 C2 C3 C4 0.38(17)
O1 C3 C4 C5 -179.04(11)
C2 C3 C4 C5 0.37(16)
C3 C4 C5 C6 -0.88(17)
C4 C5 C6 C1 0.63(17)
C2 C1 C6 C5 0.14(16)
C9 C1 C6 C5 -176.19(10)
C10 N1 C8 O2 -5.53(12)
C10 N1 C8 S1 175.11(8)
C9 O2 C8 N1 -5.66(11)
C9 O2 C8 S1 173.77(7)
C8 O2 C9 C1 -109.95(9)
C8 O2 C9 C10 13.40(10)
C2 C1 C9 O2 -92.58(11)
C6 C1 C9 O2 83.81(11)
C2 C1 C9 C10 152.70(9)
C6 C1 C9 C10 -30.91(14)
C8 N1 C10 C11 -107.54(10)
C8 N1 C10 C9 13.37(11)
O2 C9 C10 N1 -15.17(9)
C1 C9 C10 N1 102.39(9)
O2 C9 C10 C11 107.37(9)
C1 C9 C10 C11 -135.07(9)
C12 O4 C11 O3 6.19(16)
C12 O4 C11 C10 -174.41(9)
N1 C10 C11 O3 -168.14(10)
C9 C10 C11 O3 76.92(12)
N1 C10 C11 O4 12.43(12)
C9 C10 C11 O4 -102.52(10)
C11 O4 C12 C13 111.91(12)
