Synthesis of Ene-yne-enes by Nickel-Catalyzed Double SN2’ substitution of 1,6-Dichlorohexa-2,4-diyne
Wang, Gongbao; Lindeboom, Erik-Jan; Heerewaarden, Chris van; Minnaard, Adriaan J.; Catal. Sci. Technol.  (2017) –; doi:10.1039/C7CY00429J

data_1545881
_publ_section_title
;
 Synthesis of Ene-yne-enes by Nickel-Catalyzed Double SN2&#x2019;
 substitution of 1,6-Dichlorohexa-2,4-diyne
;
_journal_name_full               'Catal. Sci. Technol.'
_journal_paper_doi               10.1039/C7CY00429J
_journal_year                    2017
_chemical_formula_sum            'C24 H14 Co2 O6'
_chemical_formula_weight         516.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-11-24 deposited with the CCDC.
2017-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                98.593(4)
_cell_angle_beta                 92.973(4)
_cell_angle_gamma                100.142(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4376(11)
_cell_length_b                   10.1022(12)
_cell_length_c                   13.0614(15)
_cell_measurement_reflns_used    9770
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      3.25
_cell_volume                     1080.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0193
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            44480
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.925
_diffrn_reflns_theta_min         3.245
_exptl_absorpt_coefficient_mu    1.574
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0190
_refine_ls_R_factor_gt           0.0178
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0228P)^2^+0.5470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0469
_refine_ls_wR_factor_ref         0.0478
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4915
_reflns_number_total             5140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cy00429j2.cif
_cod_data_source_block           mo_molan401_0m_a
_cod_database_code               1545881
_shelxl_version_number           2014/6
_shelx_res_checksum              88886