Regioselective Formation of α-Vinylpyrroles from the Ruthenium-Catalyzed Coupling Reaction of Pyrroles and Terminal Alkynes Involving C-H Bond Activation
Ruili Gao; Chae S. Yi; Journal of Organic Chemistry 75 (2010) 3144–3146; doi:10.1021/jo100269y

data_4025396
_publ_section_title
;
 Regioselective Formation of \a-Vinylpyrroles from the Ruthenium-Catalyzed
 Coupling Reaction of Pyrroles and Terminal Alkynes Involving C-H Bond
 Activation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3144
_journal_page_last               3146
_journal_paper_doi               10.1021/jo100269y
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C19 H17 N O'
_chemical_formula_weight         275.34
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.4510(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.3228(3)
_cell_length_b                   17.3708(2)
_cell_length_c                   8.83840(10)
_cell_measurement_reflns_used    6910
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67
_cell_measurement_theta_min      3
_cell_volume                     2947.85(7)
_computing_cell_refinement       'SAINT v7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 v2.1-4 (Bruker, 2007)'
_computing_data_reduction        'SADABS-2004/1 (Bruker, 2005)'
_computing_molecular_graphics    'XP v5.1 (Bruker, 1998)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)'
_computing_structure_solution    'XS/SHELXTL v6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX2 CCD detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            24399
_diffrn_reflns_theta_full        67.84
_diffrn_reflns_theta_max         67.84
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  0.8901
_exptl_absorpt_correction_T_min  0.7548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS. Program for empirical absorption correction of
 area-detector data. University of Goetingen. Germany. 
 Sheldrick, G. M. 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.00105(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         5215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+1.0195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0787
_reflns_number_gt                4848
_reflns_number_total             5215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100269y_si_002.cif
_cod_data_source_block           yis
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4025396