Ionic liquid media resulted in the first asymmetric aminohalogenation reaction of alkenes.
Xu, Xin; Kotti, S. R. S. Saibabu; Liu, Junying; Cannon, John F.; Headley, Allan D.; Li, Guigen; Organic letters 6 (2004) 4881–4884; doi:10.1021/ol048045i

data_1506933
_publ_section_title
;
 Ionic liquid media resulted in the first asymmetric aminohalogenation
 reaction of alkenes.
;
_journal_issue                   26
_journal_name_full               'Organic letters'
_journal_page_first              4881
_journal_page_last               4884
_journal_paper_doi               10.1021/ol048045i
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C25 H22 Cl2 N2 O5 S'
_chemical_formula_weight         533.41
_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                 97.890(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.3777(10)
_cell_length_b                   14.0810(18)
_cell_length_c                   14.2429(15)
_cell_measurement_reflns_used    86
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      11.33
_cell_measurement_theta_min      5.92
_cell_volume                     1267.0(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '2\q/\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  0.0689
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3248
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.89
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         2537
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0443P)^2^+0.7979P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                1975
_reflns_number_total             2537
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048045isi20041024_032257.cif
_cod_data_source_block           li2
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1506933