Stereoselective Cyclization of Functionalized 1,n-Diynes Mediated by [X-Y] Reagents [X-Y = R3Si-SnR'3 or (R2N)2B-SnR'3]: Synthesis and Properties of Atropisomeric 1,3-Dienes
Ramakrishna Reddy Singidi; Amanda M. Kutney; Judith C. Gallucci; T. V. RajanBabu; Journal of the American Chemical Society 132 (2010) 13078–13087; doi:10.1021/ja105939v

data_4103069
_publ_section_title
;
 Stereoselective Cyclization of Functionalized 1,n-Diynes Mediated by
 [X-Y] Reagents [X-Y = R3Si-SnR'3 or (R2N)2B-SnR'3]: Synthesis and
 Properties of Atropisomeric 1,3-Dienes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13078
_journal_page_last               13087
_journal_paper_doi               10.1021/ja105939v
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C24 H46 B1 N3 O2 Si1 Sn1'
_chemical_formula_sum            'C24 H46 B N3 O2 Si Sn'
_chemical_formula_weight         566.23
_chemical_name_common            RajanBabu1733
_chemical_name_systematic
;
 ?
;
_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             2010-03-08T17:52:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.936(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.8572(2)
_cell_length_b                   7.2490(1)
_cell_length_c                   15.4928(3)
_cell_measurement_reflns_used    3722
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     1503.69(4)
_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    'SIR-2004, J.Appl.Cryst., (2005), 38, 381.'
_diffrn_ambient_temperature      150(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       'phi and omega scans'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.174812E-1
_diffrn_orient_matrix_UB_12      0.310889E-1
_diffrn_orient_matrix_UB_13      0.650741E-1
_diffrn_orient_matrix_UB_21      -0.722029E-1
_diffrn_orient_matrix_UB_22      0.216942E-1
_diffrn_orient_matrix_UB_23      -0.36218E-2
_diffrn_orient_matrix_UB_31      -0.77121E-2
_diffrn_orient_matrix_UB_32      -0.132639
_diffrn_orient_matrix_UB_33      0.146602E-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  0.044
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29279
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.29
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular rod'
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.041(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         6777
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0255P)^2^+0.0970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0591
_reflns_number_gt                5796
_reflns_number_total             6777
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja105939v_si_001.cif
_cod_data_source_block           RajanBabu1733
_cod_original_cell_volume        1503.68(4)
_cod_database_code               4103069