Nickel-Catalyzed Direct Alkylation of Terminal Alkynes at Room Temperature: A Hemilabile Pincer Ligand Enhances Catalytic Activity
Pérez García, Pablo M.; Ren, Peng; Scopelliti, Rosario; Hu, Xile; ACS Catalysis 5 (2015) 1164–; doi:10.1021/cs501502u

data_4512585
_publ_section_title
;
 Nickel-Catalyzed Direct Alkylation of Terminal Alkynes at Room
 Temperature: A Hemilabile Pincer Ligand Enhances Catalytic Activity
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              1164
_journal_paper_doi               10.1021/cs501502u
_journal_volume                  5
_journal_year                    2015
_chemical_formula_moiety         'C20 H25 N3 Ni'
_chemical_formula_sum            'C20 H25 N3 Ni'
_chemical_formula_weight         366.14
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_audit_update_record
;
2014-06-13 # Formatted by publCIF

;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.806(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7694(8)
_cell_length_b                   14.6639(17)
_cell_length_c                   12.8939(12)
_cell_measurement_reflns_used    117
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      3
_cell_volume                     1814.4(3)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs, 1990-2000)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19221
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    1.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008, Bruker AXS, 2008'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.267
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4143
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.280
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+3.9215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1242
_reflns_number_gt                3109
_reflns_number_total             4143
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs501502u_si_003.cif
_cod_data_source_block           ppe153
_cod_depositor_comments
'Adding full bibliography for 4512584--4512585.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4512585