Stereoselective cis-Vinylcyclopropanation via a Gold(I)-Catalyzed Retro-Buchner Reaction under Mild Conditions.
Herlé, Bart; Holstein, Philipp M.; Echavarren, Antonio M.; ACS catalysis 7 (2017) 3668–3675; doi:10.1021/acscatal.7b00737

data_4514141
_publ_section_title
;
 Stereoselective cis-Vinylcyclopropanation via a Gold(I)-Catalyzed
 Retro-Buchner Reaction under Mild Conditions.
;
_journal_issue                   5
_journal_name_full               'ACS catalysis'
_journal_page_first              3668
_journal_page_last               3675
_journal_paper_doi               10.1021/acscatal.7b00737
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H18'
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_space_group_name_Hall           'P 2yb'
_symmetry_cell_setting           monoclinic
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_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.891(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
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_cell_length_b                   5.7594(15)
_cell_length_c                   13.277(3)
_cell_measurement_reflns_used    3354
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.12
_cell_measurement_theta_min      3.01
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_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_k_max       5
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_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_point_group_measured_fraction_full 0.883
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_diffrn_reflns_theta_full        25.242
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_diffrn_source                   'Microfocus source E025 IuS'
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_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    0.064
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_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       block
_exptl_crystal_F_000             252
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_exptl_crystal_size_mid          0.15
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_refine_diff_density_max         0.251
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 913 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
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_refine_ls_number_reflns         3680
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_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0436P)^2^+0.1551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1056
_reflns_Friedel_coverage         0.483
_reflns_Friedel_fraction_full    0.742
_reflns_Friedel_fraction_max     0.531
_reflns_number_gt                3149
_reflns_number_total             3680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b00737_si_003.cif
_cod_data_source_block           mo_BHE_X252_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        678.5(3)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4514141
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              66805
_shelx_hkl_checksum              17010