Intramolecular Bromonium Ion Assisted Epoxide Ring-Opening: Capture of the Oxonium Ion with an Added External Nucleophile
Karl J. Bonney; D. Christopher Braddock; Andrew J. P. White; Muhammad Yaqoob; Journal of Organic Chemistry 76 (2011) 97–104; doi:10.1021/jo101617h

data_4025937
_publ_section_title
;
 Intramolecular Bromonium Ion Assisted Epoxide Ring-Opening: Capture of
 the Oxonium Ion with an Added External Nucleophile
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              97
_journal_page_last               104
_journal_paper_doi               10.1021/jo101617h
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C8 H12 Br Cl O'
_chemical_formula_sum            'C8 H12 Br Cl O'
_chemical_formula_weight         239.54
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 93.620(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0338(5)
_cell_length_b                   9.1341(4)
_cell_length_c                   7.5874(3)
_cell_measurement_reflns_used    3924
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.2848
_cell_measurement_theta_min      3.7516
_cell_volume                     901.49(6)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_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      173(2)
_diffrn_detector_area_resol_mean 15.9863
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'OD Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
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_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6426
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         32.37
_diffrn_reflns_theta_min         3.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.796
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) 
(compiled May  8 2007,13:10:02) 
empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_description       blocks
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_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         1504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0547P)^2^+0.0298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                1124
_reflns_number_total             1504
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101617h_si_001_5.cif
_cod_data_source_block           7d
_cod_database_code               4025937