Synthesis of benzo[b]siloles via KH-promoted cyclization of (2-alkynylphenyl)silanes.
Ilies, Laurean; Tsuji, Hayato; Nakamura, Eiichi; Organic letters 11 (2009) 3966–3968; doi:10.1021/ol9015282

data_1504111
_publ_section_title
;
 Synthesis of benzo[b]siloles via KH-promoted cyclization of
 (2-alkynylphenyl)silanes.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3966
_journal_page_last               3968
_journal_paper_doi               10.1021/ol9015282
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C22 H20 Si'
_chemical_formula_sum            'C22 H20 Si'
_chemical_formula_weight         312.47
_chemical_melting_point          409.5(5)
_chemical_name_common            2-biphenylBS
_chemical_name_systematic
; 
2-(4-Biphenyl)-1,1-dimethylbenzo[b]silole
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.76(3)
_cell_angle_beta                 68.27(3)
_cell_angle_gamma                70.39(3)
_cell_formula_units_Z            2
_cell_length_a                   9.318(5)
_cell_length_b                   9.838(7)
_cell_length_c                   10.808(7)
_cell_measurement_reflns_used    2654
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      4.6642
_cell_volume                     862.6(10)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_molecular_graphics    'ORTEP III (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXL-97 and Yadokari-XG (Wakita, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 14.5666
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device
;
Mercury CCD (2x2 bin mode)
;
_diffrn_measurement_method       dtintegrate.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7686
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         4.67
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0428P)^2^+0.6085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                2734
_reflns_number_total             3027
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9015282_si_002.cif
_cod_data_source_block           li4m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '409-410' was changed to '409.5(5)' -
the average value was taken and precision was
estimated.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1504111