#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:01:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180165 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/61/7106163.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_7106163
loop_
_publ_author_name
'Yan Zhang'
'Choon Wee Kee'
'Richmond Lee'
'Xiao Fu'
'Julian Ying-Teck Soh'
'Esther Mun Foong Loh'
'Kuo-Wei Huang'
'Choon-Hong Tan'
_publ_section_title
;
 Guanidine-Catalyzed Enantioselective Desymmetrization of meso-Aziridines
;
_journal_name_full               Chem.Commun.
_journal_page_first              3897
_journal_paper_doi               10.1039/c0cc05840h
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C25 H31 Cl2 N O6 S2'
_chemical_formula_weight         576.53
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.126(2)
_cell_angle_beta                 101.706(2)
_cell_angle_gamma                99.829(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3366(10)
_cell_length_b                   10.2792(11)
_cell_length_c                   16.2940(17)
_cell_measurement_reflns_used    5126
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.30
_cell_measurement_theta_min      2.29
_cell_volume                     1436.2(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      273(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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18790
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_T_max  0.9680
_exptl_absorpt_correction_T_min  0.8031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         6589
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0660
_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)+(0.0851P)²+1.3339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1672
_refine_ls_wR_factor_ref         0.1800
_reflns_number_gt                5680
_reflns_number_total             6589
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc05840h.txt
_cod_data_source_block           a106
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7106163
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C10 C 0.3437(9) -0.0628(8) 0.2254(10) 0.096(3) Uani 0.59(2) 1 d PD A 1
H10A H 0.3651 -0.1300 0.1791 0.144 Uiso 0.59(2) 1 calc PR A 1
H10B H 0.2376 -0.0677 0.2121 0.144 Uiso 0.59(2) 1 calc PR A 1
H10C H 0.3746 -0.0819 0.2801 0.144 Uiso 0.59(2) 1 calc PR A 1
C11 C 0.3869(11) 0.1032(13) 0.1419(5) 0.096(3) Uani 0.59(2) 1 d PD A 1
H11A H 0.4401 0.1934 0.1445 0.144 Uiso 0.59(2) 1 calc PR A 1
H11B H 0.2805 0.0957 0.1246 0.144 Uiso 0.59(2) 1 calc PR A 1
H11C H 0.4135 0.0335 0.0997 0.144 Uiso 0.59(2) 1 calc PR A 1
C12 C 0.4160(11) 0.1977(11) 0.3055(5) 0.096(3) Uani 0.59(2) 1 d PDU A 1
H12A H 0.4612 0.1871 0.3611 0.144 Uiso 0.59(2) 1 calc PR A 1
H12B H 0.3116 0.1963 0.3010 0.144 Uiso 0.59(2) 1 calc PR A 1
H12C H 0.4665 0.2844 0.3015 0.144 Uiso 0.59(2) 1 calc PR A 1
C10A C 0.3444(11) -0.0182(13) 0.2702(10) 0.066(3) Uani 0.41(2) 1 d PD A 2
H10D H 0.3557 -0.1100 0.2446 0.099 Uiso 0.41(2) 1 calc PR A 2
H10E H 0.2396 -0.0175 0.2566 0.099 Uiso 0.41(2) 1 calc PR A 2
H10F H 0.3841 0.0092 0.3330 0.099 Uiso 0.41(2) 1 calc PR A 2
C11A C 0.3519(12) 0.0740(13) 0.1410(4) 0.066(3) Uani 0.41(2) 1 d PD A 2
H11D H 0.4245 0.1098 0.1134 0.099 Uiso 0.41(2) 1 calc PR A 2
H11E H 0.2773 0.1277 0.1427 0.099 Uiso 0.41(2) 1 calc PR A 2
H11F H 0.3042 -0.0210 0.1079 0.099 Uiso 0.41(2) 1 calc PR A 2
C12A C 0.4498(14) 0.2321(8) 0.2953(7) 0.066(3) Uani 0.41(2) 1 d PD A 2
H12D H 0.4972 0.2375 0.3546 0.099 Uiso 0.41(2) 1 calc PR A 2
H12E H 0.3530 0.2533 0.2930 0.099 Uiso 0.41(2) 1 calc PR A 2
H12F H 0.5115 0.2975 0.2767 0.099 Uiso 0.41(2) 1 calc PR A 2
S1 S 0.86361(9) -0.02522(7) 0.16261(5) 0.03402(19) Uani 1 1 d . . .
S2 S 0.98223(8) 0.27286(7) 0.47425(4) 0.02903(18) Uani 1 1 d . . .
Cl1 Cl 1.00952(11) -0.14342(11) 0.31682(6) 0.0551(3) Uani 1 1 d . . .
Cl2 Cl 0.55171(13) -0.21435(12) 0.03181(7) 0.0707(3) Uani 1 1 d . . .
O1 O 1.0039(2) 0.2477(2) 0.16502(13) 0.0341(5) Uani 1 1 d . . .
O2 O 1.0326(3) 0.4431(2) 0.27497(16) 0.0523(7) Uani 1 1 d . . .
O3 O 0.5835(2) 0.0599(3) 0.24628(18) 0.0497(6) Uani 1 1 d . A .
O4 O 0.6879(3) 0.2479(3) 0.21477(19) 0.0521(6) Uani 1 1 d . . .
O5 O 0.8970(2) 0.1345(2) 0.45631(14) 0.0353(5) Uani 1 1 d . . .
O6 O 0.9521(3) 0.3840(2) 0.53697(14) 0.0372(5) Uani 1 1 d . . .
N1 N 0.9530(3) 0.3121(2) 0.38273(15) 0.0302(5) Uani 1 1 d . . .
H1N H 0.974(4) 0.396(4) 0.392(2) 0.036 Uiso 1 1 d . . .
C1 C 0.9759(3) 0.2242(3) 0.30213(18) 0.0278(5) Uani 1 1 d . . .
H1 H 1.0659 0.1896 0.3178 0.033 Uiso 1 1 calc R . .
C2 C 1.0059(3) 0.3203(3) 0.24620(19) 0.0320(6) Uani 1 1 d . . .
C3 C 1.0207(4) 0.3198(3) 0.0979(2) 0.0385(7) Uani 1 1 d . . .
C4 C 1.0027(6) 0.1986(5) 0.0169(3) 0.0648(11) Uani 1 1 d . . .
H4A H 1.0784 0.1486 0.0286 0.097 Uiso 1 1 calc R . .
H4B H 1.0135 0.2326 -0.0316 0.097 Uiso 1 1 calc R . .
H4C H 0.9047 0.1380 0.0024 0.097 Uiso 1 1 calc R . .
C5 C 0.8969(5) 0.3954(5) 0.0851(3) 0.0637(11) Uani 1 1 d . . .
H5A H 0.8026 0.3364 0.0811 0.096 Uiso 1 1 calc R . .
H5B H 0.8911 0.4202 0.0318 0.096 Uiso 1 1 calc R . .
H5C H 0.9182 0.4779 0.1341 0.096 Uiso 1 1 calc R . .
C6 C 1.1766(5) 0.4135(5) 0.1250(3) 0.0632(11) Uani 1 1 d . . .
H6A H 1.1838 0.4924 0.1739 0.095 Uiso 1 1 calc R . .
H6B H 1.1954 0.4441 0.0765 0.095 Uiso 1 1 calc R . .
H6C H 1.2497 0.3635 0.1417 0.095 Uiso 1 1 calc R . .
C7 C 0.8394(3) 0.0997(3) 0.25956(18) 0.0279(5) Uani 1 1 d . . .
H7 H 0.8300 0.0512 0.3033 0.034 Uiso 1 1 calc R . .
C8 C 0.6954(3) 0.1466(3) 0.23723(19) 0.0324(6) Uani 1 1 d . . .
C9 C 0.4295(4) 0.0825(4) 0.2331(3) 0.0694(13) Uani 1 1 d D . .
C13 C 0.7748(3) -0.1818(3) 0.17658(19) 0.0326(6) Uani 1 1 d . . .
C14 C 0.8393(4) -0.2340(3) 0.2427(2) 0.0394(7) Uani 1 1 d . . .
C15 C 0.7710(5) -0.3587(4) 0.2516(3) 0.0552(10) Uani 1 1 d . . .
H15 H 0.8157 -0.3901 0.2968 0.066 Uiso 1 1 calc R . .
C16 C 0.6372(6) -0.4353(4) 0.1934(3) 0.0650(12) Uani 1 1 d . . .
H16 H 0.5912 -0.5190 0.1990 0.078 Uiso 1 1 calc R . .
C17 C 0.5709(5) -0.3897(4) 0.1271(3) 0.0612(11) Uani 1 1 d . . .
H17 H 0.4800 -0.4422 0.0877 0.073 Uiso 1 1 calc R . .
C18 C 0.6395(4) -0.2648(3) 0.1187(2) 0.0447(8) Uani 1 1 d . . .
C19 C 1.1739(3) 0.2741(3) 0.50768(18) 0.0320(6) Uani 1 1 d . . .
C20 C 1.2152(4) 0.1538(3) 0.5139(2) 0.0411(7) Uani 1 1 d . . .
H20 H 1.1426 0.0712 0.4975 0.049 Uiso 1 1 calc R . .
C21 C 1.3648(4) 0.1569(4) 0.5444(3) 0.0503(8) Uani 1 1 d . . .
H21 H 1.3920 0.0755 0.5487 0.060 Uiso 1 1 calc R . .
C22 C 1.4762(4) 0.2783(4) 0.5688(2) 0.0492(8) Uani 1 1 d . . .
C23 C 1.4317(4) 0.3972(4) 0.5624(2) 0.0493(8) Uani 1 1 d . . .
H23 H 1.5044 0.4800 0.5790 0.059 Uiso 1 1 calc R . .
C24 C 1.2825(4) 0.3971(3) 0.5320(2) 0.0431(7) Uani 1 1 d . . .
H24 H 1.2552 0.4786 0.5280 0.052 Uiso 1 1 calc R . .
C25 C 1.6400(5) 0.2817(6) 0.6032(4) 0.0788(15) Uani 1 1 d . . .
H25A H 1.7018 0.3565 0.5920 0.118 Uiso 1 1 calc R . .
H25B H 1.6604 0.1955 0.5740 0.118 Uiso 1 1 calc R . .
H25C H 1.6622 0.2952 0.6654 0.118 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'
Cl Cl 0.1484 0.1585 '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
C13 S1 C7 99.48(12) . . ?
O5 S2 O6 119.20(13) . . ?
O5 S2 N1 107.82(13) . . ?
O6 S2 N1 105.10(12) . . ?
O5 S2 C19 107.80(13) . . ?
O6 S2 C19 108.21(14) . . ?
N1 S2 C19 108.30(13) . . ?
C2 O1 C3 120.0(2) . . ?
C8 O3 C9 121.9(3) . . ?
C1 N1 S2 121.84(19) . . ?
N1 C1 C2 105.7(2) . . ?
N1 C1 C7 109.0(2) . . ?
C2 C1 C7 115.9(2) . . ?
O2 C2 O1 126.2(3) . . ?
O2 C2 C1 122.7(3) . . ?
O1 C2 C1 111.1(2) . . ?
O1 C3 C5 109.8(3) . . ?
O1 C3 C6 109.4(3) . . ?
C5 C3 C6 113.3(3) . . ?
O1 C3 C4 101.6(3) . . ?
C5 C3 C4 111.5(3) . . ?
C6 C3 C4 110.7(3) . . ?
C8 C7 C1 111.2(2) . . ?
C8 C7 S1 111.07(19) . . ?
C1 C7 S1 112.54(18) . . ?
O4 C8 O3 126.5(3) . . ?
O4 C8 C7 124.0(3) . . ?
O3 C8 C7 109.5(2) . . ?
O3 C9 C12 112.4(5) . . ?
O3 C9 C11A 115.8(5) . . ?
C12 C9 C11A 117.1(8) . . ?
O3 C9 C10A 105.4(5) . . ?
C12 C9 C10A 88.4(5) . . ?
C11A C9 C10A 114.0(5) . . ?
O3 C9 C10 98.9(4) . . ?
C12 C9 C10 116.2(4) . . ?
C11A C9 C10 93.7(6) . . ?
C10A C9 C10 28.6(5) . . ?
O3 C9 C11 106.9(4) . . ?
C12 C9 C11 113.7(5) . . ?
C11A C9 C11 15.0(5) . . ?
C10A C9 C11 129.0(6) . . ?
C10 C9 C11 107.5(4) . . ?
O3 C9 C12A 104.2(5) . . ?
C12 C9 C12A 19.3(4) . . ?
C11A C9 C12A 109.1(5) . . ?
C10A C9 C12A 107.6(4) . . ?
C10 C9 C12A 135.5(5) . . ?
C11 C9 C12A 101.5(7) . . ?
C18 C13 C14 115.8(3) . . ?
C18 C13 S1 121.5(2) . . ?
C14 C13 S1 122.6(2) . . ?
C15 C14 C13 122.2(3) . . ?
C15 C14 Cl1 117.5(3) . . ?
C13 C14 Cl1 120.3(2) . . ?
C16 C15 C14 119.5(4) . . ?
C17 C16 C15 120.5(3) . . ?
C16 C17 C18 119.7(4) . . ?
C17 C18 C13 122.3(4) . . ?
C17 C18 Cl2 117.5(3) . . ?
C13 C18 Cl2 120.2(3) . . ?
C20 C19 C24 120.1(3) . . ?
C20 C19 S2 119.7(2) . . ?
C24 C19 S2 120.1(2) . . ?
C21 C20 C19 119.5(3) . . ?
C20 C21 C22 121.7(3) . . ?
C23 C22 C21 117.6(3) . . ?
C23 C22 C25 120.8(4) . . ?
C21 C22 C25 121.6(4) . . ?
C22 C23 C24 121.9(3) . . ?
C23 C24 C19 119.1(3) . . ?
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
C10 C9 1.530(5) . ?
C11 C9 1.538(5) . ?
C12 C9 1.481(5) . ?
C10A C9 1.520(5) . ?
C11A C9 1.502(5) . ?
C12A C9 1.561(5) . ?
S1 C13 1.773(3) . ?
S1 C7 1.839(3) . ?
S2 O5 1.430(2) . ?
S2 O6 1.430(2) . ?
S2 N1 1.627(2) . ?
S2 C19 1.759(3) . ?
Cl1 C14 1.726(4) . ?
Cl2 C18 1.732(4) . ?
O1 C2 1.333(3) . ?
O1 C3 1.491(3) . ?
O2 C2 1.188(4) . ?
O3 C8 1.312(3) . ?
O3 C9 1.478(4) . ?
O4 C8 1.198(4) . ?
N1 C1 1.465(3) . ?
C1 C2 1.537(4) . ?
C1 C7 1.538(4) . ?
C3 C5 1.510(5) . ?
C3 C6 1.510(5) . ?
C3 C4 1.517(5) . ?
C7 C8 1.512(4) . ?
C13 C18 1.393(4) . ?
C13 C14 1.400(4) . ?
C14 C15 1.388(5) . ?
C15 C16 1.369(6) . ?
C16 C17 1.364(7) . ?
C17 C18 1.388(5) . ?
C19 C20 1.378(4) . ?
C19 C24 1.387(4) . ?
C20 C21 1.376(5) . ?
C21 C22 1.388(5) . ?
C22 C23 1.379(5) . ?
C22 C25 1.509(5) . ?
C23 C24 1.380(5) . ?
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 H1N O6 0.81(4) 2.17(4) 2.951(3) 160(3) 2_766
