Ruthenium-Mediated C-H Functionalization of Pyridine: The Role of Vinylidene and Pyridylidene Ligands
David G. Johnson; Jason M. Lynam; Neetisha S. Mistry; John M. Slattery; Robert J. Thatcher; Adrian C. Whitwood; Journal of the American Chemical Society 135 (2013) 2222–2234; doi:10.1021/ja3097256

data_4119317
_publ_contact_author_address
;Department of Chemistry
University of York
Heslington
York
YO10 5DD
UK
;
_publ_contact_author_email       jason.lynam@york.ac.uk
_publ_contact_author_fax         +44(0)1904322516
_publ_contact_author_name        'Jason M Lynam'
_publ_contact_author_phone       +44(0)1904322534
_publ_section_title
;
 Ruthenium-Mediated C-H Functionalization of Pyridine: The Role of
 Vinylidene and Pyridylidene Ligands
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2222
_journal_page_last               2234
_journal_paper_doi               10.1021/ja3097256
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C37 H30 F3 N P Ru, C H2 Cl2, F6 P'
_chemical_formula_sum            'C38 H32 Cl2 F9 N P2 Ru'
_chemical_formula_weight         907.56
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-07-26
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.298(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7064(4)
_cell_length_b                   18.5122(7)
_cell_length_c                   18.6411(7)
_cell_measurement_reflns_used    5137
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      27.8301
_cell_measurement_theta_min      2.8843
_cell_volume                     3694.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.9959
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_details
;
  1 omega  -34.00   23.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8267   19.0000  120.0000 57

  2 omega  -82.00   26.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8267  -19.0000   90.0000 108

  3 omega   57.00   92.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       16.3892  178.0000   90.0000 35
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0458923000
_diffrn_orient_matrix_UB_12      0.0232218000
_diffrn_orient_matrix_UB_13      -0.0147868000
_diffrn_orient_matrix_UB_21      -0.0019760000
_diffrn_orient_matrix_UB_22      0.0217091000
_diffrn_orient_matrix_UB_23      0.0313471000
_diffrn_orient_matrix_UB_31      0.0477645000
_diffrn_orient_matrix_UB_32      -0.0213519000
_diffrn_orient_matrix_UB_33      0.0157290000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14218
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.91
_diffrn_source                   'SuperNova (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_description       needle
_exptl_crystal_F_000             1824
_exptl_crystal_recrystallization_method 'CH2Cl2, pentane'
_exptl_crystal_size_max          0.2257
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.0362
_refine_diff_density_max         0.736
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         7322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0126P)^2^+4.6696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0802
_reflns_number_gt                5917
_reflns_number_total             7322
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3097256_si_002_7.cif
_cod_data_source_block           '[11b]PF6.CH2Cl2'
_cod_database_code               4119317
_chemical_oxdiff_formula         C37H30F9N1P2Ru1
_chemical_oxdiff_usercomment     NM249d
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.01