Regioselective synthesis of multisubstituted benzenes by palladium-catalyzed intermolecular reaction of β-iodo-β-silylstyrenes with alkynes.
Kinoshita, Hidenori; Takahashi, Hirotoshi; Miura, Katsukiyo; Organic letters 15 (2013) 2962–2965; doi:10.1021/ol4010883

data_1556165
_publ_section_title
;
 Regioselective synthesis of multisubstituted benzenes by
 palladium-catalyzed intermolecular reaction of \b-iodo-\b-silylstyrenes
 with alkynes.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2962
_journal_page_last               2965
_journal_paper_doi               10.1021/ol4010883
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C37 H30 Si, 0.5(C6 H14)'
_chemical_formula_sum            'C37 H30 Si'
_chemical_formula_weight         502.70
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-03-07 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.3720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.6578(7)
_cell_length_b                   14.5155(10)
_cell_length_c                   39.626(3)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.45
_cell_measurement_theta_min      2.42
_cell_volume                     6128.5(7)
_computing_cell_refinement       'Bruker SAINT (Bruker 2008)'
_computing_data_collection       'Bruker APEX2 (Bruker 2008)'
_computing_data_reduction        'Bruker SAINT and XPREP (Bruker 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'XCIF (Bruker, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_sigmaI/netI    0.0654
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            34332
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.03
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2328
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_platon_squeeze_details
;
The hexane solvent molecule could not be resolved due to extensive
disorder and their assumed presence was removed from the overall 
scattering by the PLATON SQUEEZE procedure [Spek (2009). Acta Cryst. 
D65, 148-155]. A total of 102 e was found in each cavity (estimated 
volume 361 \%A^3^),corresponding to approximately two hexane molecules 
per cavity.
;
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.781
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.492
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     697
_refine_ls_number_reflns         13820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.492
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0000P)^2^+0.4946P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1039
_reflns_number_gt                10057
_reflns_number_total             13820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4010883_si_003.cif
_cod_data_source_block           triphenylbenzeneSi
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               1556165