Stereospecific Intramolecular Reductive Cross-Electrophile Coupling Reactions for Cyclopropane Synthesis.
Tollefson, Emily J.; Erickson, Lucas W.; Jarvo, Elizabeth R.; Journal of the American Chemical Society 137 (2015) 9760–9763; doi:10.1021/jacs.5b03870

data_4124344
_publ_section_title
;
 Stereospecific Intramolecular Reductive Cross-Electrophile Coupling
 Reactions for Cyclopropane Synthesis.
;
_journal_issue                   31
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9760
_journal_page_last               9763
_journal_paper_doi               10.1021/jacs.5b03870
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H21 Br F6 O2'
_chemical_formula_weight         595.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 97.0064(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4814(5)
_cell_length_b                   6.0033(4)
_cell_length_c                   27.9363(18)
_cell_measurement_reflns_used    7265
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.74
_cell_volume                     1245.34(14)
_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 2014/4'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.925
_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  0.0276
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            15060
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.803
_diffrn_reflns_theta_min         1.469
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.722
_exptl_absorpt_correction_T_max  0.8040
_exptl_absorpt_correction_T_min  0.5925
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.438
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
; 
 Flack x determined using 2037 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.005(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5777
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.6474P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.854
_reflns_number_gt                5215
_reflns_number_total             5777
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b03870_si_004.cif
_cod_data_source_block           erj25
_cod_depositor_comments
;
The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_database_code               4124344
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.519
_shelx_estimated_absorpt_t_max   0.825
_shelx_res_checksum              416
_shelx_hkl_checksum              9966