#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:56:18 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178412 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/33/4023302.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_4023302
loop_
_publ_author_name
'Changqing Dong'
'Fanyang Mo'
'Jianbo Wang'
_publ_section_title
;
 Highly Diastereoselective Addition of the Lithium Enolate of
 α-Diazoacetoacetate to N-Sulfinyl Imines: Enantioselective Synthesis
 of 2-Oxo and 3-Oxo Pyrrolidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1971
_journal_page_last               1974
_journal_paper_doi               10.1021/jo702275a
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C22 H23 N3 O5 S'
_chemical_formula_weight         441.49
_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                 102.91(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.542(2)
_cell_length_b                   7.5962(15)
_cell_length_c                   13.125(3)
_cell_measurement_reflns_used    4314
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.13
_cell_volume                     1121.6(4)
_computing_cell_refinement       Rapid-AUTO
_computing_data_collection       'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics    'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material  SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement  SHELXL-97,(Sheldrick,1997)
_computing_structure_solution    SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Ω
_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  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0844
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4314
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
                                  HIGASHI, T. (1995). Abscor-Empirical
                                  Absorption Correction based on Fourier
                                  Series Approximation.
                                  Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.19(17)
_refine_ls_extinction_coef       0.48(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0580
_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)+(0.0750P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1562
_reflns_number_gt                1747
_reflns_number_total             3265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702275a-File004.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023302
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50311(15) 0.3631 0.13352(13) 0.0911(7) Uani 1 1 d . . .
O1 O 0.6277(3) -0.2248(7) 0.1174(3) 0.0844(13) Uani 1 1 d . . .
O2 O 0.5080(4) -0.1213(8) 0.3944(3) 0.1056(16) Uani 1 1 d . . .
O3 O 0.7044(3) -0.1360(8) 0.4673(3) 0.1062(17) Uani 1 1 d . . .
O4 O 0.4127(4) 0.4495(7) 0.1739(5) 0.128(2) Uani 1 1 d . . .
O5 O -0.0897(3) 0.0407(6) 0.0958(3) 0.0841(13) Uani 1 1 d . . .
N1 N 0.4728(4) 0.1489(7) 0.1020(3) 0.0718(14) Uani 1 1 d . . .
HN1 H 0.4252 0.1203 0.0388 0.100 Uiso 1 1 d . . .
N2 N 0.7586(4) -0.1983(7) 0.2971(3) 0.0690(15) Uani 1 1 d . . .
N3 N 0.8505(6) -0.2354(14) 0.2995(4) 0.135(3) Uani 1 1 d . . .
C1 C 0.6110(6) -0.1344(10) 0.3894(4) 0.0774(17) Uani 1 1 d . . .
C2 C 0.6497(5) -0.1588(10) 0.2882(4) 0.0747(17) Uani 1 1 d . . .
C3 C 0.5779(5) -0.1696(10) 0.1866(4) 0.0708(17) Uani 1 1 d . . .
C4 C 0.4445(4) -0.1500(8) 0.1616(4) 0.0631(15) Uani 1 1 d . . .
H4A H 0.4112 -0.1972 0.0926 0.076 Uiso 1 1 calc R . .
H4B H 0.4116 -0.2154 0.2120 0.076 Uiso 1 1 calc R . .
C5 C 0.4126(4) 0.0425(7) 0.1653(4) 0.0531(13) Uani 1 1 d . . .
H5 H 0.4442 0.0800 0.2376 0.064 Uiso 1 1 calc R . .
C6 C 0.2740(5) 0.0607(7) 0.1466(4) 0.0574(13) Uani 1 1 d . . .
C7 C 0.2190(5) -0.0112(9) 0.2152(5) 0.0723(17) Uani 1 1 d . . .
H7 H 0.2644 -0.0571 0.2770 0.087 Uiso 1 1 calc R . .
C8 C 0.0955(5) -0.0200(10) 0.1974(4) 0.0772(19) Uani 1 1 d . . .
H8 H 0.0594 -0.0748 0.2456 0.093 Uiso 1 1 calc R . .
C9 C 0.0246(5) 0.0557(9) 0.1043(4) 0.0675(16) Uani 1 1 d . . .
C10 C 0.0862(5) 0.1251(8) 0.0355(5) 0.0710(17) Uani 1 1 d . . .
H10 H 0.0436 0.1739 -0.0266 0.085 Uiso 1 1 calc R . .
C11 C 0.2069(4) 0.1255(9) 0.0543(4) 0.0679(16) Uani 1 1 d . . .
H11 H 0.2445 0.1701 0.0041 0.081 Uiso 1 1 calc R . .
C12 C -0.1625(5) 0.0941(14) -0.0030(4) 0.112(3) Uani 1 1 d . . .
H12A H -0.1504 0.2171 -0.0138 0.168 Uiso 1 1 calc R . .
H12B H -0.2446 0.0736 -0.0031 0.168 Uiso 1 1 calc R . .
H12C H -0.1411 0.0272 -0.0581 0.168 Uiso 1 1 calc R . .
C13 C 0.6215(3) 0.3260(5) 0.2447(2) 0.0653(15) Uani 1 1 d G . .
C14 C 0.7281(3) 0.2658(5) 0.23818(19) 0.092(2) Uani 1 1 d G . .
H14 H 0.7367 0.2207 0.1744 0.110 Uiso 1 1 calc R . .
C15 C 0.8306(3) 0.2665(6) 0.3235(2) 0.106(2) Uani 1 1 d G . .
H15 H 0.9032 0.2187 0.3182 0.128 Uiso 1 1 calc R . .
C16 C 0.8130(3) 0.3431(6) 0.4137(2) 0.125(3) Uani 1 1 d GD . .
C17 C 0.7039(4) 0.4015(5) 0.4255(2) 0.125(3) Uani 1 1 d G . .
H17 H 0.6930 0.4389 0.4902 0.150 Uiso 1 1 calc R . .
C18 C 0.6096(3) 0.4031(5) 0.3370(2) 0.113(3) Uani 1 1 d G . .
H18 H 0.5382 0.4567 0.3407 0.136 Uiso 1 1 calc R . .
C19 C 0.9197(3) 0.2986(8) 0.5025(3) 0.158(4) Uani 1 1 d GD . .
H19A H 0.9561 0.1918 0.4861 0.237 Uiso 1 1 calc R . .
H19B H 0.8933 0.2834 0.5663 0.237 Uiso 1 1 calc R . .
H19C H 0.9764 0.3929 0.5107 0.237 Uiso 1 1 calc R . .
C20 C 0.6817(4) -0.1098(7) 0.5690(3) 0.110(3) Uani 1 1 d GD . .
H20A H 0.6273 -0.1981 0.5843 0.132 Uiso 1 1 calc R . .
H20B H 0.6485 0.0061 0.5749 0.132 Uiso 1 1 calc R . .
C21 C 0.8003(5) -0.1275(8) 0.6396(3) 0.158(4) Uani 1 1 d GD . .
H21 H 0.8343 -0.2391 0.6471 0.189 Uiso 1 1 calc R . .
C22 C 0.8638(4) 0.0063(9) 0.6946(2) 0.178(5) Uani 1 1 d GD . .
H22A H 0.8329 0.1198 0.6892 0.213 Uiso 1 1 calc R . .
H22B H 0.9381 -0.0159 0.7375 0.213 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 N1 113.8(3) . . ?
O4 S1 C13 105.0(3) . . ?
N1 S1 C13 97.3(2) . . ?
C1 O3 C20 115.9(4) . . ?
C9 O5 C12 115.4(4) . . ?
C5 N1 S1 119.7(4) . . ?
C5 N1 HN1 96.9(4) . . ?
S1 N1 HN1 120.0(4) . . ?
N3 N2 C2 176.3(6) . . ?
O2 C1 O3 127.3(5) . . ?
O2 C1 C2 123.3(5) . . ?
O3 C1 C2 109.4(5) . . ?
N2 C2 C3 115.7(5) . . ?
N2 C2 C1 115.5(5) . . ?
C3 C2 C1 128.0(5) . . ?
O1 C3 C2 116.0(5) . . ?
O1 C3 C4 119.2(4) . . ?
C2 C3 C4 123.8(5) . . ?
C5 C4 C3 109.4(5) . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 C4 111.8(5) . . ?
N1 C5 C6 117.7(4) . . ?
C4 C5 C6 109.1(4) . . ?
N1 C5 H5 105.8 . . ?
C4 C5 H5 105.8 . . ?
C6 C5 H5 105.8 . . ?
C7 C6 C11 118.9(5) . . ?
C7 C6 C5 118.8(5) . . ?
C11 C6 C5 121.5(5) . . ?
C6 C7 C8 122.1(5) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C7 C8 C9 119.5(5) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
O5 C9 C10 129.8(5) . . ?
O5 C9 C8 114.4(5) . . ?
C10 C9 C8 115.7(5) . . ?
C11 C10 C9 122.8(5) . . ?
C11 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
C10 C11 C6 120.7(5) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 118.4 . . ?
C14 C13 S1 123.42(19) . . ?
C18 C13 S1 116.3(2) . . ?
C13 C14 C15 124.1 . . ?
C13 C14 H14 118.0 . . ?
C15 C14 H14 118.0 . . ?
C16 C15 C14 114.8 . . ?
C16 C15 H15 122.6 . . ?
C14 C15 H15 122.6 . . ?
C15 C16 C17 123.3 . . ?
C15 C16 C19 108.3 . . ?
C17 C16 C19 125.8 . . ?
C16 C17 C18 118.0 . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C13 C18 C17 120.8 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C21 103.6(3) . . ?
O3 C20 H20A 111.0 . . ?
C21 C20 H20A 111.0 . . ?
O3 C20 H20B 111.0 . . ?
C21 C20 H20B 111.0 . . ?
H20A C20 H20B 109.0 . . ?
C22 C21 C20 125.3 . . ?
C22 C21 H21 117.4 . . ?
C20 C21 H21 117.4 . . ?
C21 C22 H22A 120.0 . . ?
C21 C22 H22B 120.0 . . ?
H22A C22 H22B 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.431(6) . ?
S1 N1 1.696(6) . ?
S1 C13 1.785(3) . ?
O1 C3 1.250(6) . ?
O2 C1 1.210(6) . ?
O3 C1 1.311(6) . ?
O3 C20 1.431(5) . ?
O5 C9 1.303(6) . ?
O5 C12 1.437(7) . ?
N1 C5 1.444(6) . ?
N1 HN1 0.913(4) . ?
N2 N3 1.091(6) . ?
N2 C2 1.271(7) . ?
C1 C2 1.504(8) . ?
C2 C3 1.407(7) . ?
C3 C4 1.508(7) . ?
C4 C5 1.511(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.569(7) . ?
C5 H5 0.9800 . ?
C6 C7 1.329(7) . ?
C6 C11 1.376(7) . ?
C7 C8 1.394(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.430(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(7) . ?
C10 C11 1.359(7) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.3330 . ?
C13 C18 1.3806 . ?
C14 C15 1.4356 . ?
C14 H14 0.9300 . ?
C15 C16 1.3740 . ?
C15 H15 0.9300 . ?
C16 C17 1.3758 . ?
C16 C19 1.5325 . ?
C17 C18 1.4034 . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.4778 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.3617 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9300 . ?
C22 H22B 0.9300 . ?
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 HN1 O1 0.913(4) 2.324(4) 3.011(6) 131.9(4) 2_655
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 S1 N1 C5 -36.3(5) . . . . ?
C13 S1 N1 C5 73.6(4) . . . . ?
C20 O3 C1 O2 -3.6(12) . . . . ?
C20 O3 C1 C2 178.5(5) . . . . ?
N3 N2 C2 C3 -10(12) . . . . ?
N3 N2 C2 C1 161(11) . . . . ?
O2 C1 C2 N2 -169.2(8) . . . . ?
O3 C1 C2 N2 8.7(9) . . . . ?
O2 C1 C2 C3 0.3(12) . . . . ?
O3 C1 C2 C3 178.2(7) . . . . ?
N2 C2 C3 O1 3.3(9) . . . . ?
C1 C2 C3 O1 -166.1(6) . . . . ?
N2 C2 C3 C4 172.2(6) . . . . ?
C1 C2 C3 C4 2.8(11) . . . . ?
O1 C3 C4 C5 -114.4(6) . . . . ?
C2 C3 C4 C5 77.0(7) . . . . ?
S1 N1 C5 C4 -152.2(4) . . . . ?
S1 N1 C5 C6 80.3(5) . . . . ?
C3 C4 C5 N1 51.7(5) . . . . ?
C3 C4 C5 C6 -176.3(4) . . . . ?
N1 C5 C6 C7 -168.4(5) . . . . ?
C4 C5 C6 C7 62.9(7) . . . . ?
N1 C5 C6 C11 21.4(8) . . . . ?
C4 C5 C6 C11 -107.3(6) . . . . ?
C11 C6 C7 C8 -1.2(9) . . . . ?
C5 C6 C7 C8 -171.7(5) . . . . ?
C6 C7 C8 C9 -2.3(10) . . . . ?
C12 O5 C9 C10 4.5(10) . . . . ?
C12 O5 C9 C8 -171.9(6) . . . . ?
C7 C8 C9 O5 -179.7(6) . . . . ?
C7 C8 C9 C10 3.3(9) . . . . ?
O5 C9 C10 C11 -177.5(6) . . . . ?
C8 C9 C10 C11 -1.1(9) . . . . ?
C9 C10 C11 C6 -2.4(10) . . . . ?
C7 C6 C11 C10 3.6(9) . . . . ?
C5 C6 C11 C10 173.8(5) . . . . ?
O4 S1 C13 C14 -172.1(3) . . . . ?
N1 S1 C13 C14 70.9(2) . . . . ?
O4 S1 C13 C18 -7.9(3) . . . . ?
N1 S1 C13 C18 -125.0(2) . . . . ?
C18 C13 C14 C15 3.9 . . . . ?
S1 C13 C14 C15 167.7(2) . . . . ?
C13 C14 C15 C16 -3.2 . . . . ?
C14 C15 C16 C17 5.4 . . . . ?
C14 C15 C16 C19 168.0 . . . . ?
C15 C16 C17 C18 -8.3 . . . . ?
C19 C16 C17 C18 -167.8 . . . . ?
C14 C13 C18 C17 -6.7 . . . . ?
S1 C13 C18 C17 -171.67(18) . . . . ?
C16 C17 C18 C13 8.8 . . . . ?
C1 O3 C20 C21 177.1(5) . . . . ?
O3 C20 C21 C22 110.1(3) . . . . ?
