Ruthenium-Catalyzed Cross-Coupling of 7-Azabenzonorbornadienes with Alkynes. An Entry to 3a,9b-Dihydrobenzo[g]indoles
Alphonse Tenaglia; Sylvain Marc; Journal of Organic Chemistry 73 (2008) 1397–1402; doi:10.1021/jo702248r

data_4023271
_publ_section_title
;
 Ruthenium-Catalyzed Cross-Coupling of 7-Azabenzonorbornadienes
 with Alkynes. An Entry to 3a,9b-Dihydrobenzo[g]indoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1397
_journal_page_last               1402
_journal_paper_doi               10.1021/jo702248r
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C24 H25 N O4 S'
_chemical_formula_weight         423.51
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 123.9211(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.9080(3)
_cell_length_b                   6.08900(10)
_cell_length_c                   22.6160(4)
_cell_measurement_reflns_used    6241
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.76
_cell_measurement_theta_min      1.08
_cell_volume                     2274.92(6)
_computing_cell_refinement
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD (Bruker-Nonius, 1998)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.792
_diffrn_measured_fraction_theta_max 0.792
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.068
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5623
_diffrn_reflns_theta_full        30.76
_diffrn_reflns_theta_max         30.76
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.1421
_refine_ls_R_factor_gt           0.0959
_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^)+(0.0415P)^2^+2.4962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1714
_refine_ls_wR_factor_ref         0.1942
_reflns_number_gt                3930
_reflns_number_total             5623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702248r-File001.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023271