Catalytic enantioselective synthesis of perfluoroalkyl-substituted β-lactones via a concerted asynchronous [2+2] cycloaddition: A synthetic and computational study
Barrios Antunez, Diego; Greenhalgh, Mark; Brueckner, Alexander C.; Walden, Daniel M.; Elías-Rodríguez, Pilar; Roberts, Patrick; Young, Benjamin; West, Thomas; Slawin, Alexandra; Ha Yeon Cheong, Paul; Smith, Andrew D.; Chemical Science  (2019) –; doi:10.1039/C9SC00390H

data_1550959
_publ_section_title
;
 Catalytic enantioselective synthesis of perfluoroalkyl-substituted
 \b-lactones via a concerted asynchronous [2+2] cycloaddition: A synthetic
 and computational study
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00390H
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H15 Br F3 N O2'
_chemical_formula_sum            'C18 H15 Br F3 N O2'
_chemical_formula_weight         414.22
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-21
_audit_creation_method           'by CrystalStructure 4.2'
_audit_update_record
;
2018-12-19 deposited with the CCDC.    2019-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   9.2685(13)
_cell_length_b                   17.886(3)
_cell_length_c                   21.589(3)
_cell_measurement_reflns_used    7745
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      1.90
_cell_volume                     3578.9(9)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20510
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.406
_diffrn_reflns_theta_min         1.478
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.344
_exptl_absorpt_correction_T_max  0.791
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1664.00
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.39
_refine_ls_abs_structure_details
;
 Flack x determined using 1531 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6593
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0243P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0704
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4683
_reflns_number_total             6593
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c9sc00390h2.cif
_cod_data_source_block           53
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'ad ' changed to 'ad'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1550959
_shelx_res_checksum              12215