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_4119315
_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 H29 F3 N P Ru, C3 H7'
_chemical_formula_sum            'C40 H36 F3 N P Ru'
_chemical_formula_weight         719.74
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_date             2012-07-26
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  Olex2 1.2
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_cell_angle_alpha                90.00
_cell_angle_beta                 96.724(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3602(11)
_cell_length_b                   15.4872(11)
_cell_length_c                   17.2133(10)
_cell_measurement_reflns_used    7576
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      30.5491
_cell_measurement_theta_min      3.2572
_cell_volume                     3272.4(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
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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 0.9962
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_details
;
  1 omega  -92.00   46.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.4240    0.0000  150.0000 138

  2 omega   -7.00   93.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6740   77.0000  120.0000 100
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0540061000
_diffrn_orient_matrix_UB_12      -0.0145298000
_diffrn_orient_matrix_UB_13      0.0110748000
_diffrn_orient_matrix_UB_21      -0.0177864000
_diffrn_orient_matrix_UB_22      -0.0227460000
_diffrn_orient_matrix_UB_23      0.0320712000
_diffrn_orient_matrix_UB_31      -0.0103132000
_diffrn_orient_matrix_UB_32      -0.0370860000
_diffrn_orient_matrix_UB_33      -0.0239233000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17427
_diffrn_reflns_theta_full        28.22
_diffrn_reflns_theta_max         30.59
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'SuperNova (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       block
_exptl_crystal_F_000             1476
_exptl_crystal_recrystallization_method 'Hexane at -15degC'
_exptl_crystal_size_max          0.1905
_exptl_crystal_size_mid          0.0984
_exptl_crystal_size_min          0.0429
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         8791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0343P)^2^+1.7017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0879
_reflns_number_gt                7264
_reflns_number_total             8791
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3097256_si_002_5.cif
_cod_data_source_block           '[10b].CH2Cl2'
_cod_database_code               4119315
_chemical_oxdiff_formula         'C37 H29 F9 N1 P2 Ru1'
_chemical_oxdiff_usercomment     'Neetisha's NM233'
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22