Bifunctional squaramide catalyzed asymmetric synthesis of chiral α-mercaptosilanes.
Zhang, Ye; Guo, Jingcheng; Han, Jinna; Zhou, Xiangui; Cao, Wei; Fu, Zhenqian; Organic & biomolecular chemistry 19 (2021) 6412–6416; doi:10.1039/d1ob00981h

data_7158154
_publ_section_title
;
 Bifunctional squaramide catalyzed asymmetric synthesis of chiral
 \a-mercaptosilanes.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6412
_journal_page_last               6416
_journal_paper_doi               10.1039/d1ob00981h
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C20 H26 O4 S Si'
_chemical_formula_sum            'C20 H26 O4 S Si'
_chemical_formula_weight         390.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc26ml1h
_audit_creation_date             2020-11-07
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-06-03 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.067(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9277(3)
_cell_length_b                   10.9677(3)
_cell_length_c                   15.6981(5)
_cell_measurement_reflns_used    3817
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      73.6900
_cell_measurement_theta_min      4.9350
_cell_volume                     2038.02(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -31.00  58.00   1.00    1.00    --   41.11 -37.00 -30.00   89
  2  \w     81.00 168.00   1.00    2.00    --  107.58  30.00-120.00   87
  3  \w     52.00 107.00   1.00    2.00    --  107.58 -94.00-180.00   55
  4  \w     37.00 132.00   1.00    2.00    --  107.58 -45.00-180.00   95
  5  \w     35.00 103.00   1.00    2.00    --  107.58 -94.00 -30.00   68
  6  \w     35.00 130.00   1.00    2.00    --  107.58 -45.00  60.00   95
  7  \w     22.00 111.00   1.00    1.00    --   41.11  57.00 120.00   89
  8  \w     17.00  79.00   1.00    1.00    --   41.11  57.00 -30.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0881702000
_diffrn_orient_matrix_UB_12      0.0349877000
_diffrn_orient_matrix_UB_13      0.0762585000
_diffrn_orient_matrix_UB_21      0.0959793000
_diffrn_orient_matrix_UB_22      -0.0308323000
_diffrn_orient_matrix_UB_23      -0.0538314000
_diffrn_orient_matrix_UB_31      -0.0005949000
_diffrn_orient_matrix_UB_32      0.1323504000
_diffrn_orient_matrix_UB_33      -0.0324907000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7543
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.172
_diffrn_reflns_theta_min         4.404
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.153
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0459
_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/[\s^2^(Fo^2^)+(0.0492P)^2^+1.3762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1279
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3314
_reflns_number_total             4008
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00981h2.cif
_cod_data_source_block           f1107
_cod_depositor_comments          'Adding full bibliography for 7158154.cif.'
_cod_original_cell_volume        2038.01(10)
_cod_database_code               7158154
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.798
_shelx_estimated_absorpt_t_min   0.753
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              6897
_shelx_hkl_checksum              63785
_olex2_date_sample_data_collection 2020-11-07
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.295