On the stereochemistry of acetylide additions to highly functionalized biphenylcarbaldehydes and multi-component cyclization of 1,n-diynes. Syntheses of dibenzocyclooctadiene lignans
Gong, Wei; Singidi, Ramakrishna Reddy; Gallucci, Judith C.; RajanBabu, T. V.; Chemical Science 3 (2012) 1221–; doi:10.1039/c2sc00920j

data_1514985
_publ_section_title
;
 On the stereochemistry of acetylide additions to highly functionalized
 biphenylcarbaldehydes and multi-component cyclization of 1,n-diynes.
 Syntheses of dibenzocyclooctadiene lignans
;
_journal_issue                   4
_journal_name_full               'Chemical Science'
_journal_page_first              1221
_journal_paper_doi               10.1039/c2sc00920j
_journal_volume                  3
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C28 H35 N1 O7 Si1'
_chemical_formula_sum            'C28 H35 N O7 Si'
_chemical_formula_weight         525.66
_chemical_name_common            'RajanBabu 1762'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2011-05-05T16:13:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.877(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4194(1)
_cell_length_b                   10.9563(1)
_cell_length_c                   12.2162(1)
_cell_measurement_reflns_used    3563
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     1477.19(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.684225E-1
_diffrn_orient_matrix_UB_12      0.561054E-1
_diffrn_orient_matrix_UB_13      0.22236E-2
_diffrn_orient_matrix_UB_21      0.10018E-2
_diffrn_orient_matrix_UB_22      0.327975E-1
_diffrn_orient_matrix_UB_23      -0.761451E-1
_diffrn_orient_matrix_UB_31      -0.593891E-1
_diffrn_orient_matrix_UB_32      -0.640861E-1
_diffrn_orient_matrix_UB_33      -0.370223E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            43607
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.18
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6764
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+0.1577P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                5446
_reflns_number_total             6764
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c2sc00920j.txt
_cod_data_source_block           RajanBabu1762
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1514985