Rhodium-catalyzed asymmetric ring-opening alkynylation of azabenzonorbornadienes.
Nishimura, Takahiro; Tsurumaki, Eiji; Kawamoto, Takahiro; Guo, Xun-Xiang; Hayashi, Tamio; Organic letters 10 (2008) 4057–4060; doi:10.1021/ol801549t

data_1504852
_publ_section_title
;
 Rhodium-catalyzed asymmetric ring-opening alkynylation of
 azabenzonorbornadienes.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4057
_journal_page_last               4060
_journal_paper_doi               10.1021/ol801549t
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_formula_sum            'C27 H42 Br N O3 Si'
_chemical_formula_weight         536.62
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.548(9)
_cell_length_b                   25.63(3)
_cell_length_c                   27.70(3)
_cell_measurement_reflns_used    27529
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     6069(12)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1459
_diffrn_reflns_av_sigmaI/netI    0.2163
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            53127
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    1.419
_exptl_absorpt_correction_T_max  0.6755
_exptl_absorpt_correction_T_min  0.5373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         13772
_refine_ls_number_restraints     557
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.1895
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0923P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1937
_reflns_number_gt                5091
_reflns_number_total             13772
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801549t_si_001.cif
_cod_data_source_block           80108yuk_2
_cod_original_cell_volume        6069(11)
_cod_database_code               1504852