Nickel-Catalyzed Cross-Electrophile Coupling of Alkyl Fluorides: Stereospecific Synthesis of Vinylcyclopropanes.
Erickson, Lucas W.; Lucas, Erika L.; Tollefson, Emily J.; Jarvo, Elizabeth R.; Journal of the American Chemical Society 138 (2016) 14006–14011; doi:10.1021/jacs.6b07567

data_4130860
_publ_section_title
;
 Nickel-Catalyzed Cross-Electrophile Coupling of Alkyl Fluorides:
 Stereospecific Synthesis of Vinylcyclopropanes.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14006
_journal_page_last               14011
_journal_paper_doi               10.1021/jacs.6b07567
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H18 O4 S'
_chemical_formula_weight         282.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3550(3)
_cell_length_b                   8.9629(5)
_cell_length_c                   28.7336(16)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.69
_cell_measurement_theta_min      2.38
_cell_volume                     1379.11(13)
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_collection       'Bruker APEX2 2014.11-0, 2014'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2013/1'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker SMART 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  0.0206
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            16518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.820
_diffrn_reflns_theta_min         1.417
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
; 
 Flack x determined using 1282 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.035(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0394P)^2^+0.3522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0708
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                3237
_reflns_number_total             3352
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b07567_si_003.cif
_cod_data_source_block           erj30
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not_measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4130860
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.973
_shelx_res_checksum              6853
_shelx_hkl_checksum              15048