Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.
Johnston, Ryne C.; Cohen, Daniel T.; Eichman, Chad C.; Scheidt, Karl A.; Cheong, Paul Ha-Yeon; Chemical science (Royal Society of Chemistry : 2010) 5 (2014) 1974–1982; doi:10.1039/C4SC00317A

data_1514307
_publ_section_title
;
 Catalytic Kinetic Resolution of a Dynamic Racemate: Highly
 Stereoselective \b-Lactone Formation by N-Heterocyclic Carbene Catalysis.
;
_journal_issue                   5
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              1974
_journal_page_last               1982
_journal_paper_doi               10.1039/C4SC00317A
_journal_volume                  5
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H15 Br O4'
_chemical_formula_weight         339.18
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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_method           SHELXL-97
_audit_update_record
;
2012-01-09 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4193(3)
_cell_length_b                   9.4004(5)
_cell_length_c                   28.0840(14)
_cell_measurement_reflns_used    4940
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.93
_cell_measurement_theta_min      2.90
_cell_volume                     1430.70(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_sigmaI/netI    0.0744
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            12801
_diffrn_reflns_theta_full        30.21
_diffrn_reflns_theta_max         30.21
_diffrn_reflns_theta_min         1.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.883
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.584
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.584
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.7641P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                3204
_reflns_number_total             4174
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc00317a2.cif
_cod_data_source_block           n1209_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1514306--1514307.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1514307