Ruthenium-catalyzed highly regioselective cyclization of ketoximes with alkynes by C-H bond activation: a practical route to synthesize substituted isoquinolines.
Chinnagolla, Ravi Kiran; Pimparkar, Sandeep; Jeganmohan, Masilamani; Organic letters 14 (2012) 3032–3035; doi:10.1021/ol301091z

data_1507821
_publ_section_title
;
 Ruthenium-catalyzed highly regioselective cyclization of ketoximes with
 alkynes by C-H bond activation: a practical route to synthesize
 substituted isoquinolines.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3032
_journal_page_last               3035
_journal_paper_doi               10.1021/ol301091z
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C19 H23 Br Cl N O Ru'
_chemical_formula_weight         497.81
_chemical_name_systematic
; 
 ? 
;
_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                 97.487(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9632(13)
_cell_length_b                   9.4235(10)
_cell_length_c                   17.273(2)
_cell_measurement_temperature    200(2)
_cell_volume                     1930.7(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14591
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    3.025
_exptl_absorpt_correction_T_max  0.785
_exptl_absorpt_correction_T_min  0.565
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         2.512
_refine_diff_density_min         -1.038
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.453
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3401
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.453
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.083
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0272P)^2^+6.1943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1336
_reflns_number_gt                2465
_reflns_number_total             3401
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301091z_si_002.cif
_cod_data_source_block           trail2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'Constr' changed to 'constr'
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_values 1891 2012-01-12 08:04:46Z andrius 

 Adding full bibliography for 1507821.cif.
;
_cod_original_sg_symbol_H-M      p2(1)/c
_cod_database_code               1507821