Lewis Acid-Catalyzed Synthesis of Silafluorene Derivatives from Biphenyls and Dihydrosilanes via Double Sila-Friedel-Crafts Reaction
Dong, Yafang; Takata, Yuta; Yoshigoe, Yusuke; Sekine, Kohei; Kuninobu, Yoichiro; Chemical Communications  (2019) –; doi:10.1039/C9CC07692A

data_7124303
_publ_section_title
;
 Lewis Acid-Catalyzed Synthesis of Silafluorene Derivatives from Biphenyls
 and Dihydrosilanes via Double Sila-Friedel-Crafts Reaction
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07692A
_journal_year                    2019
_chemical_formula_moiety         'C28 H28 N2 Si'
_chemical_formula_sum            'C28 H28 N2 Si'
_chemical_formula_weight         420.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-29 deposited with the CCDC.    2019-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                113.798(3)
_cell_angle_beta                 91.992(4)
_cell_angle_gamma                112.004(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4768(4)
_cell_length_b                   10.9099(4)
_cell_length_c                   13.1313(5)
_cell_measurement_reflns_used    10732
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.9290
_cell_measurement_theta_min      2.3570
_cell_volume                     1123.73(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.847
_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     28.00  54.00   0.50    0.50    --    5.00  45.00  60.00   52
  2  \w    -72.00 -46.00   0.50    0.50    --    5.00  45.00  60.00   52
  3  \w    -27.00  -1.00   0.50    0.50    --    5.00  45.00 120.00   52
  4  \w    -98.00 -46.00   0.50    0.50    --  -10.00  45.00 150.00  104
  5  \w    -43.00  79.00   0.50    0.50    --  -10.00  45.00 150.00  244
  6  \w    -98.00  79.00   0.50    0.50    --  -10.00  45.00  90.00  354
  7  \w    -61.00  50.00   0.50    0.50    --  -10.00  45.00   0.00  222
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0043009000
_diffrn_orient_matrix_UB_12      0.0631982000
_diffrn_orient_matrix_UB_13      0.0482525000
_diffrn_orient_matrix_UB_21      -0.0305547000
_diffrn_orient_matrix_UB_22      -0.0441319000
_diffrn_orient_matrix_UB_23      0.0284283000
_diffrn_orient_matrix_UB_31      0.0767688000
_diffrn_orient_matrix_UB_32      0.0148571000
_diffrn_orient_matrix_UB_33      0.0229042000
_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  0.0303
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19804
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.026
_diffrn_reflns_theta_min         2.376
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.547
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.243
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         6081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0402
_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^+0.3420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5254
_reflns_number_total             6081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07692a2.cif
_cod_data_source_block           181116
_cod_original_cell_volume        1123.73(8)
_cod_database_code               7124303
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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:
 C8AA(H8AA), C0BA(H0BA), C1BA(H1BA), C2BA(H2BA), C4BA(H4BA), C5BA(H5BA),
 C6BA(H6BA), C7BA(H7BA), C8BA(H8BA), C9BA(H9BA), C0CA(H0CA), C1CA(H1CA),
 C3CA(H3CA), C5CA(H5CA), C6CA(H6CA), C7CA(H7CA)
2.b Idealised Me refined as rotating group:
 C(HA,HB,HC), C2CA(H2CA,H2CB,H2CC), C4CA(H4CA,H4CB,H4CC), C8CA(H8CA,H8CB,H8CC)
;
_shelx_res_checksum              22506
_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 1.073
_oxdiff_exptl_absorpt_empirical_full_min 0.904