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_4119316
_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         'C36 H31 N P Ru, C H2 Cl2, F6 P'
_chemical_formula_sum            'C37 H33 Cl2 F6 N P2 Ru'
_chemical_formula_weight         839.55
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                85.101(4)
_cell_angle_beta                 65.774(5)
_cell_angle_gamma                70.153(5)
_cell_formula_units_Z            2
_cell_length_a                   11.4116(7)
_cell_length_b                   12.9092(6)
_cell_length_c                   13.8078(6)
_cell_measurement_reflns_used    11594
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      29.5087
_cell_measurement_theta_min      3.0508
_cell_volume                     1741.33(18)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_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      110.0
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -51.00   23.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672   77.0000  -60.0000 74

  2 omega  -42.00    2.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  -77.0000 -180.0000 44

  3 omega  -43.00   51.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -77.0000   30.0000 94

  4 omega   -4.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172   77.0000  150.0000 93

  5 omega  -21.00   56.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172    0.0000    0.0000 77
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0530075000
_diffrn_orient_matrix_UB_12      0.0137934000
_diffrn_orient_matrix_UB_13      0.0040235000
_diffrn_orient_matrix_UB_21      -0.0462594000
_diffrn_orient_matrix_UB_22      0.0535046000
_diffrn_orient_matrix_UB_23      0.0216056000
_diffrn_orient_matrix_UB_31      -0.0168355000
_diffrn_orient_matrix_UB_32      -0.0193091000
_diffrn_orient_matrix_UB_33      0.0519875000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15370
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'SuperNova (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.2745
_exptl_crystal_size_mid          0.1787
_exptl_crystal_size_min          0.1579
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         9706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0270
_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^)+(0.0213P)^2^+1.0315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0653
_reflns_number_gt                8844
_reflns_number_total             9706
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3097256_si_002_6.cif
_cod_data_source_block           '[11a]PF6.CH2Cl2'
_cod_original_cell_volume        1741.34(18)
_cod_database_code               4119316
_chemical_oxdiff_formula         'C36 H31 F6 N P2 Ru'
_chemical_oxdiff_usercomment     'Neetisha's NM205'
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97