#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024557.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_4024557
loop_
_publ_author_name
'Yolanda Arroyo'
'Ángela Meana'
'J. Félix Rodríguez'
'M. Ascensión Sanz-Tejedor'
'Inés Alonso'
'José L. García Ruano'
_publ_section_title
;
Stereoselective Control of Planar α-Dimethylsulfonium Benzyl Carbanions.
Synthesis of Optically Pure trans-Aziridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4217
_journal_page_last               4224
_journal_paper_doi               10.1021/jo900381b
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C28 H25 N O2 S2'
_chemical_formula_weight         471.61
_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                 103.209(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.761(4)
_cell_length_b                   9.713(3)
_cell_length_c                   12.308(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1252.4(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7929
_diffrn_reflns_theta_full        23.29
_diffrn_reflns_theta_max         23.29
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.768257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       0.0077(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3583
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0298
_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)+(0.0491P)²+0.1023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                3309
_reflns_number_total             3583
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900381b_si_002.cif
_cod_data_source_block           amr72am
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4024557
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 1.06817(5) 0.30197(6) 0.78689(5) 0.06055(19) Uani 1 1 d . . .
S2 S 0.84991(6) -0.21582(6) 0.83170(6) 0.0677(2) Uani 1 1 d . . .
O1 O 1.14047(15) 0.1699(2) 0.80391(15) 0.0719(5) Uani 1 1 d . . .
O2 O 0.8873(2) -0.2542(2) 0.7285(2) 0.0971(7) Uani 1 1 d . . .
N1 N 0.78464(17) -0.05307(19) 0.82081(16) 0.0541(5) Uani 1 1 d . . .
C1 C 0.8665(2) 0.0607(2) 0.79900(18) 0.0510(5) Uani 1 1 d . . .
H1 H 0.9506 0.0339 0.7882 0.061 Uiso 1 1 calc R . .
C2 C 0.7536(2) 0.0115(2) 0.7106(2) 0.0560(6) Uani 1 1 d . . .
H2 H 0.7767 -0.0439 0.6516 0.067 Uiso 1 1 calc R . .
C4 C 0.8633(2) 0.1884(2) 0.86559(17) 0.0465(5) Uani 1 1 d . . .
C5 C 0.7781(2) 0.2007(3) 0.93383(19) 0.0599(6) Uani 1 1 d . . .
H5 H 0.7233 0.1281 0.9387 0.072 Uiso 1 1 calc R . .
C6 C 0.7731(3) 0.3197(3) 0.9952(2) 0.0690(7) Uani 1 1 d . . .
H6 H 0.7144 0.3261 1.0399 0.083 Uiso 1 1 calc R . .
C7 C 0.8532(3) 0.4272(3) 0.9908(2) 0.0685(7) Uani 1 1 d . . .
H7 H 0.8492 0.5067 1.0320 0.082 Uiso 1 1 calc R . .
C8 C 0.9395(3) 0.4171(2) 0.9251(2) 0.0632(7) Uani 1 1 d . . .
H8 H 0.9951 0.4896 0.9225 0.076 Uiso 1 1 calc R . .
C9 C 0.94473(19) 0.2990(2) 0.86208(16) 0.0488(5) Uani 1 1 d . . .
C11 C 0.6304(2) 0.0857(3) 0.6749(2) 0.0589(6) Uani 1 1 d . . .
C12 C 0.5327(3) 0.0739(3) 0.7291(2) 0.0697(7) Uani 1 1 d . . .
H12 H 0.5427 0.0179 0.7918 0.084 Uiso 1 1 calc R . .
C13 C 0.4181(3) 0.1455(4) 0.6908(3) 0.0900(10) Uani 1 1 d . . .
H13 H 0.3522 0.1370 0.7278 0.108 Uiso 1 1 calc R . .
C14 C 0.4039(4) 0.2276(4) 0.5990(4) 0.1022(11) Uani 1 1 d . . .
H14 H 0.3279 0.2754 0.5735 0.123 Uiso 1 1 calc R . .
C15 C 0.4996(4) 0.2403(4) 0.5445(3) 0.1014(11) Uani 1 1 d . . .
H15 H 0.4892 0.2967 0.4820 0.122 Uiso 1 1 calc R . .
C16 C 0.6115(3) 0.1699(3) 0.5817(3) 0.0818(8) Uani 1 1 d . . .
H16 H 0.6764 0.1788 0.5436 0.098 Uiso 1 1 calc R . .
C21 C 0.9736(2) 0.3009(3) 0.64694(18) 0.0520(5) Uani 1 1 d . . .
C22 C 0.9965(3) 0.2026(3) 0.5738(2) 0.0742(7) Uani 1 1 d . . .
H22 H 1.0530 0.1308 0.5987 0.089 Uiso 1 1 calc R . .
C23 C 0.9348(3) 0.2120(3) 0.4630(2) 0.0841(9) Uani 1 1 d . . .
H23 H 0.9506 0.1457 0.4134 0.101 Uiso 1 1 calc R . .
C24 C 0.8509(3) 0.3157(3) 0.4237(2) 0.0705(7) Uani 1 1 d . . .
C25 C 0.8280(3) 0.4118(3) 0.4986(2) 0.0702(7) Uani 1 1 d . . .
H25 H 0.7695 0.4819 0.4739 0.084 Uiso 1 1 calc R . .
C26 C 0.8898(3) 0.4065(3) 0.6097(2) 0.0631(6) Uani 1 1 d . . .
H26 H 0.8749 0.4738 0.6590 0.076 Uiso 1 1 calc R . .
C27 C 0.7862(4) 0.3253(4) 0.3007(2) 0.1056(12) Uani 1 1 d . . .
H27A H 0.8256 0.2616 0.2592 0.158 Uiso 1 1 calc R . .
H27B H 0.7948 0.4172 0.2746 0.158 Uiso 1 1 calc R . .
H27C H 0.6973 0.3032 0.2905 0.158 Uiso 1 1 calc R . .
C31 C 0.7018(2) -0.2983(2) 0.82899(19) 0.0508(5) Uani 1 1 d . . .
C32 C 0.6527(3) -0.2939(3) 0.9222(2) 0.0698(7) Uani 1 1 d . . .
H32 H 0.6942 -0.2433 0.9840 0.084 Uiso 1 1 calc R . .
C33 C 0.5430(3) -0.3634(3) 0.9248(3) 0.0788(8) Uani 1 1 d . . .
H33 H 0.5095 -0.3577 0.9879 0.095 Uiso 1 1 calc R . .
C34 C 0.4820(3) -0.4409(3) 0.8364(3) 0.0827(9) Uani 1 1 d . . .
C35 C 0.5323(3) -0.4450(4) 0.7440(3) 0.0945(11) Uani 1 1 d . . .
H35 H 0.4909 -0.4962 0.6824 0.113 Uiso 1 1 calc R . .
C36 C 0.6434(3) -0.3750(3) 0.7392(2) 0.0701(7) Uani 1 1 d . . .
H36 H 0.6772 -0.3804 0.6762 0.084 Uiso 1 1 calc R . .
C37 C 0.3603(4) -0.5186(5) 0.8369(5) 0.146(2) Uani 1 1 d . . .
H37A H 0.3807 -0.6029 0.8777 0.218 Uiso 1 1 calc R . .
H37B H 0.3165 -0.5390 0.7615 0.218 Uiso 1 1 calc R . .
H37C H 0.3065 -0.4632 0.8717 0.218 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
O1 S1 C9 109.85(10) . . ?
O1 S1 C21 107.09(11) . . ?
C9 S1 C21 99.92(9) . . ?
O2 S2 N1 110.72(12) . . ?
O2 S2 C31 106.97(11) . . ?
N1 S2 C31 93.68(10) . . ?
C2 N1 C1 61.94(15) . . ?
C2 N1 S2 117.93(15) . . ?
C1 N1 S2 116.86(14) . . ?
N1 C1 C4 115.69(17) . . ?
N1 C1 C2 58.60(14) . . ?
C4 C1 C2 122.9(2) . . ?
N1 C2 C11 118.8(2) . . ?
N1 C2 C1 59.46(15) . . ?
C11 C2 C1 125.2(2) . . ?
C5 C4 C9 117.5(2) . . ?
C5 C4 C1 120.5(2) . . ?
C9 C4 C1 122.05(18) . . ?
C4 C5 C6 121.1(2) . . ?
C7 C6 C5 120.8(2) . . ?
C6 C7 C8 119.3(2) . . ?
C7 C8 C9 120.5(2) . . ?
C4 C9 C8 120.8(2) . . ?
C4 C9 S1 125.23(17) . . ?
C8 C9 S1 113.88(18) . . ?
C12 C11 C16 117.9(3) . . ?
C12 C11 C2 123.2(3) . . ?
C16 C11 C2 118.9(2) . . ?
C11 C12 C13 120.6(3) . . ?
C14 C13 C12 119.5(3) . . ?
C15 C14 C13 120.6(3) . . ?
C14 C15 C16 119.9(3) . . ?
C15 C16 C11 121.5(3) . . ?
C22 C21 C26 120.2(2) . . ?
C22 C21 S1 119.21(19) . . ?
C26 C21 S1 120.14(19) . . ?
C21 C22 C23 119.0(3) . . ?
C24 C23 C22 122.0(3) . . ?
C23 C24 C25 118.0(2) . . ?
C23 C24 C27 120.9(3) . . ?
C25 C24 C27 121.0(3) . . ?
C24 C25 C26 121.3(3) . . ?
C21 C26 C25 119.3(2) . . ?
C36 C31 C32 120.2(2) . . ?
C36 C31 S2 120.49(18) . . ?
C32 C31 S2 119.10(19) . . ?
C33 C32 C31 120.4(3) . . ?
C34 C33 C32 121.0(3) . . ?
C33 C34 C35 118.0(3) . . ?
C33 C34 C37 122.1(3) . . ?
C35 C34 C37 119.8(3) . . ?
C34 C35 C36 122.0(3) . . ?
C31 C36 C35 118.4(2) . . ?
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 O1 1.490(2) . ?
S1 C9 1.784(2) . ?
S1 C21 1.789(2) . ?
S2 O2 1.466(2) . ?
S2 N1 1.723(2) . ?
S2 C31 1.777(2) . ?
N1 C2 1.462(3) . ?
N1 C1 1.476(3) . ?
C1 C4 1.491(3) . ?
C1 C2 1.512(3) . ?
C2 C11 1.484(4) . ?
C4 C5 1.383(3) . ?
C4 C9 1.393(3) . ?
C5 C6 1.389(4) . ?
C6 C7 1.364(4) . ?
C7 C8 1.367(4) . ?
C8 C9 1.393(3) . ?
C11 C12 1.372(3) . ?
C11 C16 1.385(4) . ?
C12 C13 1.400(5) . ?
C13 C14 1.363(5) . ?
C14 C15 1.357(5) . ?
C15 C16 1.370(5) . ?
C21 C22 1.372(4) . ?
C21 C26 1.374(3) . ?
C22 C23 1.377(4) . ?
C23 C24 1.364(4) . ?
C24 C25 1.373(4) . ?
C24 C27 1.518(4) . ?
C25 C26 1.378(4) . ?
C31 C36 1.362(3) . ?
C31 C32 1.369(3) . ?
C32 C33 1.367(4) . ?
C33 C34 1.363(4) . ?
C34 C35 1.368(4) . ?
C34 C37 1.512(4) . ?
C35 C36 1.388(4) . ?
