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_4124345
_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            'C22 H19 Br O2'
_chemical_formula_weight         395.28
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.8906(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6894(8)
_cell_length_b                   5.9472(3)
_cell_length_c                   20.3256(11)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.73
_cell_measurement_theta_min      2.28
_cell_volume                     1754.33(16)
_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 1.000
_diffrn_measured_fraction_theta_max 0.941
_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  0.0181
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21151
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.748
_diffrn_reflns_theta_min         1.403
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.355
_exptl_absorpt_correction_T_max  0.5922
_exptl_absorpt_correction_T_min  0.3438
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
; 
 Flack x determined using 3366 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.012(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         8341
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0230
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0276P)^2^+0.2481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0507
_refine_ls_wR_factor_ref         0.0514
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                7989
_reflns_number_total             8341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b03870_si_003.cif
_cod_data_source_block           erj27
_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               4124345
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.369
_shelx_estimated_absorpt_t_max   0.756
_shelx_res_checksum              40492
_shelx_hkl_checksum              75776