Asymmetric β-boration of α,β-unsaturated N-acyloxazolidinones by [2.2]paracyclophane-based bifunctional catalyst.
Zhao, Lei; Ma, Yudao; Duan, Wenzeng; He, Fuyan; Chen, Jianqiang; Song, Chun; Organic letters 14 (2012) 5780–5783; doi:10.1021/ol302839d

data_1508767
_publ_section_title
;
 Asymmetric \b-boration of \a,\b-unsaturated N-acyloxazolidinones by
 [2.2]paracyclophane-based bifunctional catalyst.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5780
_journal_page_last               5783
_journal_paper_doi               10.1021/ol302839d
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration S
_chemical_formula_sum            'C18 H23 B Br N O5'
_chemical_formula_weight         424.09
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.602(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.256(5)
_cell_length_b                   24.002(10)
_cell_length_c                   13.896(6)
_cell_measurement_reflns_used    4045
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.29
_cell_measurement_theta_min      2.33
_cell_volume                     4084(3)
_computing_cell_refinement       'APEX2 Software Suite'
_computing_data_collection       'APEX2 Software Suite (Bruker,2005)'
_computing_data_reduction        'APEX2 Software Suite'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2008)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX2 CCD area-detector diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20340
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    2.040
_exptl_absorpt_correction_T_max  0.8220
_exptl_absorpt_correction_T_min  0.6858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker,2005)'
_exptl_crystal_colour            stick
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       colorless
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.475
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.017(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     953
_refine_ls_number_reflns         11983
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_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                7470
_reflns_number_total             11983
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302839d_si_001.cif
_cod_data_source_block           test
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        4083(3)
_cod_original_sg_symbol_H-M      'P2(1)   '
_cod_database_code               1508767