Competitive Carbon-Sulfur vs Carbon-Carbon Bond Activation of 2-Cyanothiophene with [Ni(dippe)H]2
Matthew R. Grochowski; Ting Li; William W. Brennessel; William D. Jones; Journal of the American Chemical Society 132 (2010) 12412–12421; doi:10.1021/ja104158h

data_4103004
_publ_contact_author_address
'Department of Chemistry, University of Rochester, Rochester, New York 14627'
_publ_contact_author_email       jones@chem.rochester.edu
_publ_contact_author_name        'William D. Jones'
_publ_section_title
;
 Competitive Carbon-Sulfur vs Carbon-Carbon Bond Activation of
 2-Cyanothiophene with [Ni(dippe)H]2
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12412
_journal_page_last               12421
_journal_paper_doi               10.1021/ja104158h
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C20 H34 N2 Ni P2 S'
_chemical_formula_sum            'C20 H34 N2 Ni P2 S'
_chemical_formula_weight         455.20
_chemical_name_common            jonmg19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 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                 110.245(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4435(14)
_cell_length_b                   15.405(2)
_cell_length_c                   14.9862(19)
_cell_measurement_reflns_used    4062
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      29.17
_cell_measurement_theta_min      2.46
_cell_volume                     2262.1(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, \w scans per \f'
_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  0.0974
_diffrn_reflns_av_sigmaI/netI    0.1439
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25932
_diffrn_reflns_theta_full        29.57
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         1.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.099
_exptl_absorpt_correction_T_max  0.9173
_exptl_absorpt_correction_T_min  0.7632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.069
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details
'Flack H D (1983), Friedel pairs, Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         12179
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0639
_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^)+(0.0428P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1374
_reflns_number_gt                8239
_reflns_number_total             12179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja104158h_si_001_1.cif
_cod_data_source_block           jonmg19_2c
_cod_database_code               4103004