1,3-Chlorine Shift to a Vinyl Cation: A Combined Experimental and Theoretical Investigation of the E-Selective Gold(I)-Catalyzed Dimerization of Chloroacetylenes.
Kreuzahler, Mathis; Daniels, Alyssa; Wölper, Christoph; Haberhauer, Gebhard; Journal of the American Chemical Society 141 (2019) 1337–1348; doi:10.1021/jacs.8b11501

data_4133593
_publ_section_title
;
 1,3-Chlorine Shift to a Vinyl Cation: A Combined Experimental and
 Theoretical Investigation of the E-Selective Gold(I)-Catalyzed
 Dimerization of Chloroacetylenes.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1337
_journal_page_last               1348
_journal_paper_doi               10.1021/jacs.8b11501
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C18 H14 Cl2 O2'
_chemical_formula_weight         333.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 98.3549(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.1358(10)
_cell_length_b                   22.5942(13)
_cell_length_c                   7.6401(4)
_cell_measurement_reflns_used    9207
_cell_measurement_temperature    131(2)
_cell_measurement_theta_max      79.25
_cell_measurement_theta_min      3.15
_cell_volume                     3097.4(3)
_computing_cell_refinement       'Bruker APEX3(v2017.3-0)'
_computing_data_collection       'Bruker APEX3(v2017.3-0)'
_computing_data_reduction        'Bruker APEX3(v2017.3-0)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'Bruker APEX3(v2017.3-0)'
_diffrn_ambient_temperature      131(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture (Photon II detector)'
_diffrn_measurement_method       'Data collection strategy APEX 3/Queen'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            66924
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.684
_diffrn_reflns_theta_min         2.462
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'INCOATEC I\mS 3.0'
_exptl_absorpt_coefficient_mu    3.801
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;
_exptl_crystal_colour            'greenish yellow'
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         6684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0607P)^2^+1.3170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1033
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6146
_reflns_number_total             6684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b11501_si_002.cif
_cod_data_source_block           mjk_199_2m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_secondary' value 'diffmap' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4133593
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.385
_shelx_estimated_absorpt_t_max   0.771
_shelx_res_checksum              40156
_shelx_hkl_checksum              34463