Ag(I)-Fesulphos-Catalyzed Enantioselective Synthesis of 3-Silylproline Derivatives.
Chowdhury, Raghunath; Dubey, Akhil K.; Ghosh, Sunil K.; The Journal of organic chemistry 84 (2019) 2404–2414; doi:10.1021/acs.joc.8b02412

data_4033731
_publ_section_title
;
 Ag(I)-Fesulphos-Catalyzed Enantioselective Synthesis of 3-Silylproline
 Derivatives.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2404
_journal_page_last               2414
_journal_paper_doi               10.1021/acs.joc.8b02412
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C26 H32 Cl N O6 Si'
_chemical_formula_sum            'C26 H32 Cl N O6 Si'
_chemical_formula_weight         518.57
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-11
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                80.839(4)
_cell_angle_beta                 85.378(4)
_cell_angle_gamma                67.764(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4745(3)
_cell_length_b                   9.6998(4)
_cell_length_c                   20.0096(10)
_cell_measurement_reflns_used    7091
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.4180
_cell_measurement_theta_min      2.0930
_cell_volume                     1325.38(11)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -110.00   1.50   0.50    8.00    --  -20.00   0.00-108.00  223
  2  \w    -93.50  19.00   0.50    8.00    --  -20.00 -72.00  36.00  225
  3  \w    -87.00  18.00   0.50    8.00    --  -20.00 -72.00-108.00  210
  4  \w    -75.50 -11.00   0.50    8.00    --  -20.00 -72.00-180.00  129
  5  \w    -39.00  -9.00   0.50    8.00    --  -20.00 -72.00 -36.00   60
  6  \w    -53.00 -23.00   0.50    8.00    --  -20.00  72.00-180.00   60
  7  \w    -59.00  60.50   0.50    8.00    --  -20.00  72.00 -36.00  239
  8  \w    -74.00  30.00   0.50    8.00    --  -20.00   0.00 -36.00  208
  9  \w    -81.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  200
 10  \w    -55.50  -7.00   0.50    8.00    --  -20.00  72.00  36.00   97
 11  \w    -43.00  -7.00   0.50    8.00    --  -20.00  72.00-108.00   72
 12  \w    -59.00 -28.50   0.50    8.00    --  -20.00  72.00 108.00   61
 13  \w   -110.00  37.00   0.50    8.00    --  -20.00   0.00  36.00  294
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0074405000
_diffrn_orient_matrix_UB_12      0.0748769000
_diffrn_orient_matrix_UB_13      0.0006582000
_diffrn_orient_matrix_UB_21      0.0051930000
_diffrn_orient_matrix_UB_22      -0.0142356000
_diffrn_orient_matrix_UB_23      0.0358170000
_diffrn_orient_matrix_UB_31      0.1021428000
_diffrn_orient_matrix_UB_32      -0.0235792000
_diffrn_orient_matrix_UB_33      -0.0025750000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1074
_diffrn_reflns_av_unetI/netI     0.1376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25688
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.062
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.299
_exptl_crystal_description       plate
_exptl_crystal_F_000             549
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.157
_refine_ls_abs_structure_details
;
 Flack x determined using 1789 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         9209
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.1364
_refine_ls_R_factor_gt           0.0947
_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^)+(0.1404P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2179
_refine_ls_wR_factor_ref         0.2732
_reflns_Friedel_coverage         0.972
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                6393
_reflns_number_total             9209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02412_si_003.cif
_cod_data_source_block           rc-1209-d_mo
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1325.39(11)
_cod_original_formula_moiety     '2(C26 H32 Cl N O6 Si)'
_cod_original_formula_sum        'C52 H65 Cl2 N2 O12 Si2'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     1037.14
_cod_database_code               4033731
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.955
_reflns_odcompleteness_completeness 92.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.07
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2)
2.b Ternary CH refined with riding coordinates:
 C40(H40), C20(H20), C35(H35), C46(H46), C10(H10), C9(H9)
2.c Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C42(H42A,H42B), C15(H15A,H15B), C18(H18A,H18B)
2.d Aromatic/amide H refined with riding coordinates:
 C32(H32), N1(H1), C25(H25), C28(H28), C2(H2A), C3(H3), C51(H51), C4(H4),
 C30(H30), C6(H6), C24(H24), C22(H22), C49(H49), C23(H23), C48(H48), C31(H31),
 C5(H5), C29(H29), C50(H50)
2.e Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C45(H45A,H45B,
 H45C), C33(H33A,H33B,H33C), C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C43(H43A,
 H43B,H43C), C34(H34A,H34B,H34C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              99711
_shelx_hkl_checksum              11839
_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 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.647