Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.
Wiest, Johannes M.; Conner, Michael L.; Brown, M. Kevin; Journal of the American Chemical Society 140 (2018) 15943–15949; doi:10.1021/jacs.8b10008

data_4133431
_publ_section_title
;
 Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic
 Curiosity to a Stereospecific Transformation.
;
_journal_issue                   46
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15943
_journal_page_last               15949
_journal_paper_doi               10.1021/jacs.8b10008
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration
;
Absolute configuration was established from a 85% complete Cu
data set. 
;
_chemical_formula_moiety         'C20 H17 F3 O3'
_chemical_formula_sum            'C20 H17 F3 O3'
_chemical_formula_weight         362.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 126.339(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.392(3)
_cell_length_b                   8.3185(7)
_cell_length_c                   18.8264(19)
_cell_measurement_reflns_used    3239
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.64
_cell_measurement_theta_min      2.86
_cell_volume                     3455.5(6)
_computing_cell_refinement       'APEX II v2014.11-0 (Bruker, 2014)'
_computing_data_collection       'APEX II v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'APEX II v2014.11-0 (Bruker, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2016)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2016)'
_computing_structure_solution    'SHELX (Bruker, 2016)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 83.33
_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
'0.50 degree frames measured for 40 seconds each'
_diffrn_measurement_device       'APEX Kappa Duo'
_diffrn_measurement_device_type  Kappa
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13939
_diffrn_reflns_point_group_measured_fraction_full 0.828
_diffrn_reflns_point_group_measured_fraction_max 0.807
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.430
_diffrn_reflns_theta_min         1.343
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
; 
 Flack x determined using 1165 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         5742
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0601
_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^)+(0.1108P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_ref         0.1744
_reflns_Friedel_coverage         0.518
_reflns_Friedel_fraction_full    0.629
_reflns_Friedel_fraction_max     0.594
_reflns_number_gt                4138
_reflns_number_total             5742
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b10008_si_004.cif
_cod_data_source_block           17121
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4133431
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              61860
_shelx_hkl_checksum              87378