Ni(ii)-catalyzed dehydrative alkynylation of unactivated (hetero)aryl C-H bonds using oxygen: a user-friendly approach.
Liu, Yan-Hua; Liu, Yue-Jin; Yan, Sheng-Yi; Shi, Bing-Feng; Chemical communications (Cambridge, England) 51 (2015) 11650–11653; doi:10.1039/c5cc03729h

data_7117448
_publ_section_title
;
 Ni(ii)-catalyzed dehydrative alkynylation of unactivated (hetero)aryl C-H
 bonds using oxygen: a user-friendly approach.
;
_journal_issue                   58
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11650
_journal_page_last               11653
_journal_paper_doi               10.1039/c5cc03729h
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C30 H49 N O Si2'
_chemical_formula_weight         495.88
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_block_doi                 10.5517/cc14p2c8
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-05-04 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                74.497(2)
_cell_angle_beta                 75.4870(10)
_cell_angle_gamma                76.750(2)
_cell_formula_units_Z            4
_cell_length_a                   12.5020(8)
_cell_length_b                   15.8137(9)
_cell_length_c                   17.4136(10)
_cell_measurement_reflns_used    14144
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     3162.7(3)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0815
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24862
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.9638
_exptl_absorpt_correction_T_min  0.9428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.041
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       0.048(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         11075
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.2309
_refine_ls_R_factor_gt           0.1479
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+3.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3813
_refine_ls_wR_factor_ref         0.4410
_reflns_number_gt                5124
_reflns_number_total             11075
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc03729h2.cif
_cod_data_source_block           1186bp
_cod_database_code               7117448