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_1514988
_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 rmad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C29 H37 N1 O8 Si1'
_chemical_formula_sum            'C29 H37 N O8 Si'
_chemical_formula_weight         555.69
_chemical_name_common            'RajanBabu 1842'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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             2011-06-06T13:28:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1179(1)
_cell_length_b                   13.7992(1)
_cell_length_c                   21.5342(2)
_cell_measurement_reflns_used    3880
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     3006.58(5)
_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      210(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'omega scans'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.352192E-1
_diffrn_orient_matrix_UB_12      -0.284759E-1
_diffrn_orient_matrix_UB_13      0.393658E-1
_diffrn_orient_matrix_UB_21      0.776594E-1
_diffrn_orient_matrix_UB_22      -0.264436E-1
_diffrn_orient_matrix_UB_23      -0.23193E-1
_diffrn_orient_matrix_UB_31      0.499692E-1
_diffrn_orient_matrix_UB_32      0.611675E-1
_diffrn_orient_matrix_UB_33      0.82997E-2
_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       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            44069
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.22
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.19
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         6874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
' w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.2347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                5373
_reflns_number_total             6874
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c2sc00920j.txt
_cod_data_source_block           RajanBabu1842
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1514988