Nickel-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Alkynes with Formic Acid through Catalytic CO Recycling
Fu, Ming-Chen; Shang, Rui; Cheng, Wan-Min; Fu, Yao; ACS Catalysis 6 (2016) 2501–; doi:10.1021/acscatal.6b00276

data_4513841
_publ_section_title
;
 Nickel-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Alkynes
 with Formic Acid through Catalytic CO Recycling
;
_journal_issue                   4
_journal_name_full               'ACS Catalysis'
_journal_page_first              2501
_journal_paper_doi               10.1021/acscatal.6b00276
_journal_volume                  6
_journal_year                    2016
_chemical_formula_sum            'C12 H12 O4'
_chemical_formula_weight         220.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 94.374(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.5824(2)
_cell_length_b                   19.9078(8)
_cell_length_c                   12.0067(4)
_cell_measurement_reflns_used    2202
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      69.7560
_cell_measurement_theta_min      4.2900
_cell_volume                     1092.13(7)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3945
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.885
_diffrn_reflns_theta_min         4.309
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.310
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0700P)^2^+0.1484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1255
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1785
_reflns_number_total             1961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b00276_si_003.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4513840--4513841.cif.'
_cod_database_code               4513841
_shelx_estimated_absorpt_t_min   0.703
_shelx_estimated_absorpt_t_max   0.780
_shelxl_version_number           2013-4
_shelx_res_checksum              86550
_shelx_hkl_checksum              78035