Synthesis of six-membered silacycles by borane-catalyzed double sila-Friedel‒Crafts reaction
Dong, Yafang; Sakai, Masahiko; Fuji, Kazuto; Sekine, Kohei; Kuninobu, Yoichiro; Beilstein Journal of Organic Chemistry 16 (2020) 409–414; doi:10.3762/bjoc.16.39

data_4038068
_publ_section_title
;
 Synthesis of six-membered silacycles by borane-catalyzed double
 sila-Friedel--Crafts reaction
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              409
_journal_page_last               414
_journal_paper_doi               10.3762/bjoc.16.39
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         '0.8(C28 H28 N2 O Si)'
_chemical_formula_sum            'C28 H28 N2 O Si'
_chemical_formula_weight         436.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                83.723(3)
_cell_angle_beta                 73.112(3)
_cell_angle_gamma                86.634(3)
_cell_formula_units_Z            5
_cell_length_a                   12.4645(5)
_cell_length_b                   12.9987(5)
_cell_length_c                   16.7305(5)
_cell_measurement_reflns_used    28800
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.0640
_cell_measurement_theta_min      1.9060
_cell_volume                     2577.23(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      123(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn70 area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.898
_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  70.00   0.50    5.00    --  -20.00  45.00 180.00  360
  2  \w   -110.00  70.00   0.50    5.00    --  -20.00  45.00  90.00  360
  3  \w   -110.00  70.00   0.50    5.00    --  -20.00  45.00   0.00  360
  4  \w   -110.00  70.00   0.50    5.00    --  -20.00  45.00 270.00  360
;
_diffrn_measurement_device       AFC10
_diffrn_measurement_device_type  'Fixed Chi 2 circle'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0135958000
_diffrn_orient_matrix_UB_12      -0.0499952000
_diffrn_orient_matrix_UB_13      -0.0139890000
_diffrn_orient_matrix_UB_21      -0.0100057000
_diffrn_orient_matrix_UB_22      -0.0217861000
_diffrn_orient_matrix_UB_23      0.0421818000
_diffrn_orient_matrix_UB_31      -0.0570489000
_diffrn_orient_matrix_UB_32      -0.0064703000
_diffrn_orient_matrix_UB_33      0.0025580000
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            45536
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.010
_diffrn_reflns_theta_min         1.577
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_current           16.0000
_diffrn_source_power             0.8000
_diffrn_source_type              micromax007
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74440
_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    1.407
_exptl_crystal_description       prism
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.507
_refine_diff_density_min         -1.075
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     585
_refine_ls_number_reflns         14757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0870
_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^)+(0.1541P)^2^+1.3325P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2284
_refine_ls_wR_factor_ref         0.2555
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11159
_reflns_number_total             14757
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-39-S2.cif
_cod_data_source_block           3a
_cod_depositor_comments          'Adding full bibliography for 4038068.cif.'
_cod_database_code               4038068
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H28 N2 O1 Si1'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H00C), C28(H00D), C46(H00E), C52(H00G), C22(H00H), C19(H00I), C24(H00J),
 C26(H00L), C25(H00O), C31(H00P), C50(H00Q), C30(H00R), C27(H00U), C47(H00V),
 C53(H00X), C56(H00Z), C10(H010), C21(H011), C41(H012), C2(H013), C20(H014),
 C38(H015), C55(H017), C54(H019), C33(H01q), C49(H01r), C48(H01v), C11(H01G),
 C13(H01I), C5(H01J), C39(H01w), C3(H01L)
2.b Idealised Me refined as rotating group:
 C35(H01s,H01t,H01u), C36(H01x,H01y,H), C43(H01z,Ha,Hb), C44(H01,Hc,Hd),
 C15(H01a,H01b,H01c), C16(H01d,H01e,H01f), C7(H01h,H01k,H01m), C8(H01n,H01o,
 H01p)
;
_shelx_res_checksum              63073
_shelx_hkl_checksum              88643
_shelx_fab_checksum              31159
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.044
_oxdiff_exptl_absorpt_empirical_full_min 0.787