Double Dehydrogenation of Primary Amines to Nitriles by a Ruthenium Complex Featuring Pyrazole Functionality.
Dutta, Indranil; Yadav, Sudhir; Sarbajna, Abir; De, Subhabrata; Hölscher, Markus; Leitner, Walter; Bera, Jitendra K.; Journal of the American Chemical Society 140 (2018) 8662–8666; doi:10.1021/jacs.8b05009

data_4132581
_publ_section_title
;
 Double Dehydrogenation of Primary Amines to Nitriles by a Ruthenium
 Complex Featuring Pyrazole Functionality.
;
_journal_issue                   28
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8662
_journal_page_last               8666
_journal_paper_doi               10.1021/jacs.8b05009
_journal_volume                  140
_journal_year                    2018
_chemical_formula_sum            'C22 H29 Cl2 N3 Ru'
_chemical_formula_weight         507.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.270(2)
_cell_length_b                   9.9659(12)
_cell_length_c                   11.8072(14)
_cell_measurement_reflns_used    4622
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.30
_cell_volume                     2267.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    DIAMOND
_computing_publication_material  ciftab
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8672
_diffrn_reflns_point_group_measured_fraction_full 0.795
_diffrn_reflns_point_group_measured_fraction_max 0.795
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.114
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  0.841
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(Bera et al., 2017)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.934
_refine_diff_density_min         -1.071
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details
;
 Flack x determined using 799 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+2.5305P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.517
_reflns_Friedel_fraction_full    0.571
_reflns_Friedel_fraction_max     0.571
_reflns_number_gt                2721
_reflns_number_total             3194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05009_si_002.cif
_cod_data_source_block           compound4
_cod_original_cell_volume        2267.4(5)
_cod_database_code               4132581
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.827
_shelx_estimated_absorpt_t_max   0.849
_exptl_absorpt_special_details   SADABS
_shelx_res_checksum              61806
_shelx_hkl_checksum              87866