#------------------------------------------------------------------------------
#$Date: 2021-04-05 17:29:41 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263714 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/02/1560204.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_1560204
loop_
_publ_author_name
'Zhong, Xia'
'Zhong, Ziwei'
'Wu, Zhikun'
'Ye, Zhen'
'Feng, Yuxiang'
'Dong, Shunxi'
'Liu, Xiaohua'
'Peng, Qian'
'Feng, Xiaoming'
_publ_section_title
;
 Chiral Lewis acid-bonded picolinaldehyde enables enantiodivergent
 carbonyl catalysis in the Mannich/condensation reaction of glycine ester
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              4353
_journal_page_last               4360
_journal_paper_doi               10.1039/D0SC07052A
_journal_volume                  12
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H18 N2 O2 S2'
_chemical_formula_sum            'C19 H18 N2 O2 S2'
_chemical_formula_weight         370.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-02-11 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.2220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6009(2)
_cell_length_b                   10.3983(2)
_cell_length_c                   9.9867(2)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      74.75
_cell_measurement_theta_min      4.89
_cell_volume                     901.95(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16275
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.738
_diffrn_reflns_theta_min         4.895
_exptl_absorpt_coefficient_mu    2.797
_exptl_absorpt_correction_T_max  0.8321
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 1633 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.036(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0236
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0284P)²+0.1612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0607
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                3574
_reflns_number_total             3635
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc07052a2.cif
_cod_data_source_block           zhx002
_cod_depositor_comments
'Adding full bibliography for 1560204--1560206.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1560204
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.619
_shelx_estimated_absorpt_t_max   0.769
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42612(6) 0.44336(5) 0.36657(6) 0.03304(14) Uani 1 1 d . . . . .
S2 S 0.90102(6) 0.28901(5) 0.27189(6) 0.02792(13) Uani 1 1 d . . . . .
O1 O 0.8002(2) 0.82180(16) 0.2544(2) 0.0366(4) Uani 1 1 d . . . . .
O2 O 0.57662(18) 0.74357(15) 0.08509(16) 0.0280(3) Uani 1 1 d . . . . .
N1 N 0.75583(18) 0.52010(16) 0.51028(17) 0.0182(3) Uani 1 1 d . . . . .
N2 N 0.88038(19) 0.56533(16) 0.35800(18) 0.0192(3) Uani 1 1 d . . . . .
H2N H 0.933(3) 0.632(3) 0.401(3) 0.022(6) Uiso 1 1 d . . . . .
C1 C 0.7208(2) 0.60838(18) 0.2829(2) 0.0177(4) Uani 1 1 d . . . . .
H1 H 0.659002 0.542675 0.207997 0.021 Uiso 1 1 calc R U . . .
C2 C 0.7073(2) 0.7368(2) 0.2074(2) 0.0210(4) Uani 1 1 d . . . . .
C3 C 0.5437(3) 0.8657(3) 0.0074(3) 0.0416(6) Uani 1 1 d . . . . .
H3A H 0.450070 0.857678 -0.085099 0.062 Uiso 1 1 calc R U . . .
H3B H 0.630195 0.889888 -0.014842 0.062 Uiso 1 1 calc R U . . .
H3C H 0.528459 0.931927 0.069710 0.062 Uiso 1 1 calc R U . . .
C11 C 0.7795(2) 0.52276(19) 0.6586(2) 0.0188(4) Uani 1 1 d . . . . .
C12 C 0.8871(2) 0.4409(2) 0.7629(2) 0.0236(4) Uani 1 1 d . . . . .
H12 H 0.945735 0.383559 0.733270 0.028 Uiso 1 1 calc R U . . .
C13 C 0.9085(2) 0.4432(3) 0.9090(2) 0.0303(4) Uani 1 1 d . . . . .
H13 H 0.982979 0.388015 0.978843 0.036 Uiso 1 1 calc R U . . .
C14 C 0.8233(3) 0.5243(3) 0.9550(2) 0.0365(5) Uani 1 1 d . . . . .
H14 H 0.839233 0.525767 1.055623 0.044 Uiso 1 1 calc R U . . .
C15 C 0.7147(3) 0.6032(3) 0.8518(3) 0.0365(5) Uani 1 1 d . . . . .
H15 H 0.654597 0.658376 0.882073 0.044 Uiso 1 1 calc R U . . .
C16 C 0.6914(3) 0.6034(2) 0.7043(2) 0.0268(4) Uani 1 1 d . . . . .
H16 H 0.615861 0.658211 0.634868 0.032 Uiso 1 1 calc R U . . .
C21 C 0.6620(2) 0.61763(18) 0.4063(2) 0.0175(4) Uani 1 1 d . . . . .
H21 H 0.687170 0.704299 0.454069 0.021 Uiso 1 1 calc R U . . .
C22 C 0.4921(2) 0.5931(2) 0.3490(2) 0.0205(4) Uani 1 1 d . . . . .
C23 C 0.3717(2) 0.6762(2) 0.2711(3) 0.0289(5) Uani 1 1 d . . . . .
H23 H 0.384055 0.763399 0.249703 0.035 Uiso 1 1 calc R U . . .
C24 C 0.2260(3) 0.6133(3) 0.2270(3) 0.0375(5) Uani 1 1 d . . . . .
H24 H 0.130142 0.654594 0.171975 0.045 Uiso 1 1 calc R U . . .
C25 C 0.2382(3) 0.4898(3) 0.2713(3) 0.0383(6) Uani 1 1 d . . . . .
H25 H 0.152670 0.434877 0.251837 0.046 Uiso 1 1 calc R U . . .
C31 C 0.8760(2) 0.47326(18) 0.4663(2) 0.0179(4) Uani 1 1 d . . . . .
H31 H 0.978007 0.470753 0.554455 0.021 Uiso 1 1 calc R U . . .
C32 C 0.8348(2) 0.34086(19) 0.3982(2) 0.0192(4) Uani 1 1 d . . . . .
C33 C 0.7508(3) 0.2469(2) 0.4250(2) 0.0260(4) Uani 1 1 d . . . . .
H33 H 0.704757 0.256548 0.491837 0.031 Uiso 1 1 calc R U . . .
C34 C 0.7394(3) 0.1327(2) 0.3420(3) 0.0297(5) Uani 1 1 d . . . . .
H34 H 0.684666 0.058229 0.347384 0.036 Uiso 1 1 calc R U . . .
C35 C 0.8147(3) 0.1417(2) 0.2549(3) 0.0300(5) Uani 1 1 d . . . . .
H35 H 0.819245 0.074864 0.192122 0.036 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C25 S1 C22 92.00(11) . . ?
C35 S2 C32 92.18(11) . . ?
C2 O2 C3 116.31(18) . . ?
C11 N1 C21 120.87(15) . . ?
C11 N1 C31 121.62(15) . . ?
C21 N1 C31 109.93(14) . . ?
C31 N2 C1 103.10(14) . . ?
N2 C1 C2 112.06(16) . . ?
N2 C1 C21 105.45(15) . . ?
C2 C1 C21 110.85(15) . . ?
O1 C2 O2 125.03(19) . . ?
O1 C2 C1 124.33(18) . . ?
O2 C2 C1 110.60(17) . . ?
C16 C11 C12 118.61(18) . . ?
C16 C11 N1 120.58(18) . . ?
C12 C11 N1 120.75(17) . . ?
C13 C12 C11 120.3(2) . . ?
C14 C13 C12 121.2(2) . . ?
C15 C14 C13 118.7(2) . . ?
C14 C15 C16 121.4(2) . . ?
C15 C16 C11 119.8(2) . . ?
N1 C21 C22 113.24(16) . . ?
N1 C21 C1 101.43(14) . . ?
C22 C21 C1 112.81(15) . . ?
C23 C22 C21 128.19(19) . . ?
C23 C22 S1 111.50(15) . . ?
C21 C22 S1 120.18(14) . . ?
C22 C23 C24 111.0(2) . . ?
C25 C24 C23 113.4(2) . . ?
C24 C25 S1 112.04(18) . . ?
N2 C31 N1 106.05(14) . . ?
N2 C31 C32 110.38(15) . . ?
N1 C31 C32 110.22(15) . . ?
C33 C32 C31 128.83(18) . . ?
C33 C32 S2 110.67(15) . . ?
C31 C32 S2 120.47(14) . . ?
C32 C33 C34 112.83(19) . . ?
C35 C34 C33 112.8(2) . . ?
C34 C35 S2 111.56(17) . . ?
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 C25 1.712(3) . ?
S1 C22 1.718(2) . ?
S2 C35 1.715(2) . ?
S2 C32 1.7231(19) . ?
O1 C2 1.200(3) . ?
O2 C2 1.329(3) . ?
O2 C3 1.451(3) . ?
N1 C11 1.400(2) . ?
N1 C21 1.456(2) . ?
N1 C31 1.480(2) . ?
N2 C31 1.459(2) . ?
N2 C1 1.460(2) . ?
C1 C2 1.512(3) . ?
C1 C21 1.562(3) . ?
C11 C16 1.399(3) . ?
C11 C12 1.399(3) . ?
C12 C13 1.384(3) . ?
C13 C14 1.383(4) . ?
C14 C15 1.380(4) . ?
C15 C16 1.393(3) . ?
C21 C22 1.502(3) . ?
C22 C23 1.387(3) . ?
C23 C24 1.433(3) . ?
C24 C25 1.347(4) . ?
C31 C32 1.512(3) . ?
C32 C33 1.364(3) . ?
C33 C34 1.425(3) . ?
C34 C35 1.350(3) . ?
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
C31 N2 C1 C2 158.70(15) . . . . ?
C31 N2 C1 C21 38.01(18) . . . . ?
C3 O2 C2 O1 -2.4(3) . . . . ?
C3 O2 C2 C1 175.63(19) . . . . ?
N2 C1 C2 O1 -34.7(3) . . . . ?
C21 C1 C2 O1 82.8(2) . . . . ?
N2 C1 C2 O2 147.26(16) . . . . ?
C21 C1 C2 O2 -95.23(18) . . . . ?
C21 N1 C11 C16 12.2(3) . . . . ?
C31 N1 C11 C16 158.75(19) . . . . ?
C21 N1 C11 C12 -170.58(18) . . . . ?
C31 N1 C11 C12 -24.0(3) . . . . ?
C16 C11 C12 C13 -2.0(3) . . . . ?
N1 C11 C12 C13 -179.2(2) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C11 -0.2(4) . . . . ?
C12 C11 C16 C15 1.6(3) . . . . ?
N1 C11 C16 C15 178.9(2) . . . . ?
C11 N1 C21 C22 -80.1(2) . . . . ?
C31 N1 C21 C22 129.83(16) . . . . ?
C11 N1 C21 C1 158.74(16) . . . . ?
C31 N1 C21 C1 8.68(18) . . . . ?
N2 C1 C21 N1 -28.84(18) . . . . ?
C2 C1 C21 N1 -150.32(16) . . . . ?
N2 C1 C21 C22 -150.29(16) . . . . ?
C2 C1 C21 C22 88.23(19) . . . . ?
N1 C21 C22 C23 167.4(2) . . . . ?
C1 C21 C22 C23 -78.2(3) . . . . ?
N1 C21 C22 S1 -17.1(2) . . . . ?
C1 C21 C22 S1 97.43(17) . . . . ?
C25 S1 C22 C23 -0.16(18) . . . . ?
C25 S1 C22 C21 -176.44(17) . . . . ?
C21 C22 C23 C24 175.8(2) . . . . ?
S1 C22 C23 C24 -0.1(2) . . . . ?
C22 C23 C24 C25 0.5(3) . . . . ?
C23 C24 C25 S1 -0.6(3) . . . . ?
C22 S1 C25 C24 0.4(2) . . . . ?
C1 N2 C31 N1 -32.33(18) . . . . ?
C1 N2 C31 C32 87.05(17) . . . . ?
C11 N1 C31 N2 -135.53(17) . . . . ?
C21 N1 C31 N2 14.27(19) . . . . ?
C11 N1 C31 C32 104.98(19) . . . . ?
C21 N1 C31 C32 -105.22(17) . . . . ?
N2 C31 C32 C33 -145.8(2) . . . . ?
N1 C31 C32 C33 -28.9(3) . . . . ?
N2 C31 C32 S2 36.4(2) . . . . ?
N1 C31 C32 S2 153.18(13) . . . . ?
C35 S2 C32 C33 0.32(17) . . . . ?
C35 S2 C32 C31 178.56(16) . . . . ?
C31 C32 C33 C34 -178.41(19) . . . . ?
S2 C32 C33 C34 -0.4(2) . . . . ?
C32 C33 C34 C35 0.2(3) . . . . ?
C33 C34 C35 S2 0.0(3) . . . . ?
C32 S2 C35 C34 -0.19(18) . . . . ?
