Boron-Catalyzed Silylative Reduction of Quinolines: Selective sp(3) C-Si Bond Formation.
Gandhamsetty, Narasimhulu; Joung, Seewon; Park, Sung-Woo; Park, Sehoon; Chang, Sukbok; Journal of the American Chemical Society  (2014) 141120154130001–; doi:10.1021/ja510674u

data_4122991
_publ_section_title
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 Boron-Catalyzed Silylative Reduction of Quinolines: Selective sp(3) C-Si
 Bond Formation.
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_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141120154130001
_journal_paper_doi               10.1021/ja510674u
_journal_year                    2014
_chemical_formula_moiety         'C22 H26 N2 O2 S Si'
_chemical_formula_sum            'C22 H26 N2 O2 S Si'
_chemical_formula_weight         410.60
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 119.34(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.662(15)
_cell_length_b                   10.727(9)
_cell_length_c                   11.793(10)
_cell_measurement_reflns_used    9147
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.58
_cell_volume                     2058(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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Photon 100 CMOS 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  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
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_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9147
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.9543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platy
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.394
_refine_diff_density_min         -1.375
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(15)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4102
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0743
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+10.3681P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1717
_reflns_number_gt                3263
_reflns_number_total             4102
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja510674u_si_006.cif
_cod_data_source_block           n0106b-1
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

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 
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_cod_original_sg_symbol_H-M      Cc
_cod_database_code               4122991