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_4133432
_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 ad
_chemical_formula_moiety         'C22 H17 Br5 O2'
_chemical_formula_sum            'C22 H17 Br5 O2'
_chemical_formula_weight         712.91
_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
_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                   6.3241(4)
_cell_length_b                   8.6365(5)
_cell_length_c                   41.542(2)
_cell_measurement_reflns_used    6568
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.45
_cell_measurement_theta_min      2.78
_cell_volume                     2268.9(2)
_computing_cell_refinement       'APEX II v2014.11-0 (Bruker, 2018)'
_computing_data_collection       'APEX II v2014.11-0 (Bruker, 2018)'
_computing_data_reduction        'APEX II v2014.11-0 (Bruker, 2018)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2018)'
_computing_publication_material  'SHELXTL (Bruker, 2018)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2018)'
_computing_structure_solution    'SHELX (Bruker, 2018)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
'0.50 degree frames measured for 20 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  0.0335
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            13895
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.058
_diffrn_reflns_theta_min         1.961
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    8.873
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.3264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2018'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.087
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.817
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details
;
 Flack x determined using 1880 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         6351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0338
_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^)+(0.0157P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0643
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                5326
_reflns_number_total             6351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b10008_si_002.cif
_cod_data_source_block           18086
_cod_database_code               4133432
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.147
_shelx_estimated_absorpt_t_max   0.442
_shelx_res_checksum              14155
_shelx_hkl_checksum              87280