Atom Efficient Synthesis of Selectively Difluorinated Carbocycles through a Gold(I)-Catalyzed Cyclization.
McCarter, Adam W.; Sommer, Magdalena; Percy, Jonathan M.; Jamieson, Craig; Kennedy, Alan R.; Hirst, David J.; The Journal of organic chemistry 83 (2018) 8888–8905; doi:10.1021/acs.joc.8b01121

data_4035342
_publ_section_title
;
 Atom Efficient Synthesis of Selectively Difluorinated Carbocycles through
 a Gold(I)-Catalyzed Cyclization.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8888
_journal_page_last               8905
_journal_paper_doi               10.1021/acs.joc.8b01121
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C11 H16 F2 O4'
_chemical_formula_weight         250.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.0944(13)
_cell_length_b                   6.5258(5)
_cell_length_c                   18.8242(14)
_cell_measurement_reflns_used    2177
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5940
_cell_measurement_theta_min      2.1690
_cell_volume                     2222.8(3)
_computing_cell_refinement       CrysalisPro
_computing_data_collection       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku FRE+'
_diffrn_measurement_method       'profiled \w scans'
_diffrn_radiation_monochromator  'confocal mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_av_unetI/netI     0.1110
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11704
_diffrn_reflns_point_group_measured_fraction_full 0.910
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.164
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9g (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Flack x determined using 1125 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4342
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0709
_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^)+(0.0627P)^2^+3.3209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1692
_refine_ls_wR_factor_ref         0.1822
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.824
_reflns_Friedel_fraction_max     0.789
_reflns_number_gt                3401
_reflns_number_total             4342
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01121_si_002.cif
_cod_data_source_block           2017ncs0420z
_cod_database_code               4035342
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              2929
_shelx_hkl_checksum              47941