Highly enantioselective α-chlorination of cyclic β-ketoesters catalyzed by N,N′-Dioxide using NCS as the chlorine source
Cai, Yunfei; Wang, Wentao; Shen, Ke; Wang, Jun; Hu, Xiaolei; Lin, Lili; Liu, Xiaohua; Feng, Xiaoming; Chemical Communications 46 (2010) 1250–; doi:10.1039/b922769e

data_7105265
_publ_section_title
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 Highly enantioselective \a-chlorination of cyclic \b-ketoesters
 catalyzed by N,N&#x2032;-Dioxide using NCS as the chlorine source
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_journal_issue                   8
_journal_name_full               'Chemical Communications'
_journal_page_first              1250
_journal_paper_doi               10.1039/b922769e
_journal_volume                  46
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H22 Br Cl O3'
_chemical_formula_weight         437.75
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9369(14)
_cell_length_b                   7.2436(14)
_cell_length_c                   36.835(7)
_cell_measurement_reflns_used    4022
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.80
_cell_volume                     1850.9(6)
_computing_cell_refinement       crystalClear
_computing_data_collection       'CrystalClear(Rigaku/MSC Inc.,2005)'
_computing_data_reduction        CrystalClear
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku Saturn CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            12953
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    2.384
_exptl_absorpt_correction_T_max  0.6736
_exptl_absorpt_correction_T_min  0.5985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.614
_refine_diff_density_min         -1.495
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.055(15)
_refine_ls_extinction_coef       0.035(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+1.2845P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1510
_reflns_number_gt                3497
_reflns_number_total             4334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b922769e.txt
_cod_data_source_block           cd4
_cod_depositor_comments
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The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               7105265