Highly Stereoselective Ruthenium(II)-Catalyzed Direct C2-syn-Alkenylation of Indoles with Alkynes.
Zhang, Wei; Wei, Jun; Fu, Shaomin; Lin, Dongen; Jiang, Huanfeng; Zeng, Wei; Organic letters 17 (2015) 1349–1352; doi:10.1021/ol503618m

data_1518783
_publ_section_title
;
 Highly Stereoselective Ruthenium(II)-Catalyzed Direct C2-syn-Alkenylation
 of Indoles with Alkynes.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1349
_journal_page_last               1352
_journal_paper_doi               10.1021/ol503618m
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C23 H16 N2'
_chemical_formula_weight         320.38
_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                 96.518(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.9264(6)
_cell_length_b                   8.5389(3)
_cell_length_c                   13.3223(6)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.66
_cell_measurement_theta_min      5.97
_cell_volume                     1687.02(12)
_computing_cell_refinement       'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7039
_diffrn_reflns_theta_full        62.66
_diffrn_reflns_theta_max         62.66
_diffrn_reflns_theta_min         5.97
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  0.8937
_exptl_absorpt_correction_T_min  0.8696
_exptl_crystal_colour            'light green'
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plane
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0535P)^2^+0.1198P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1126
_reflns_number_gt                2079
_reflns_number_total             2692
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503618m_si_003.cif
_cod_data_source_block           sad
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 

 Adding full bibliography for 1518783.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/C
_cod_database_code               1518783