Bromonium Ion Induced Transannular Oxonium Ion Formation-Fragmentation in Model Obtusallene Systems and Structural Reassignment of Obtusallenes V-VII
D. Christopher Braddock; David S. Millan; Yolanda Pérez-Fuertes; Rebecca H. Pouwer; Richard N. Sheppard; Savade Solanki; Andrew J. P. White; Journal of Organic Chemistry 74 (2009) 1835–1841; doi:10.1021/jo8026577

data_4024383
_publ_section_title
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Bromonium Ion Induced Transannular Oxonium Ion Formation-Fragmentation in
Model Obtusallene Systems and Structural Reassignment of Obtusallenes
V-VII
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1835
_journal_page_last               1841
_journal_paper_doi               10.1021/jo8026577
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H18 Br3 Cl O3'
_chemical_formula_sum            'C15 H18 Br3 Cl O3'
_chemical_formula_weight         521.47
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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
_cell_angle_beta                 112.271(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6506(3)
_cell_length_b                   5.65986(9)
_cell_length_c                   19.6269(3)
_cell_measurement_reflns_used    4927
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.2843
_cell_measurement_theta_min      2.4294
_cell_volume                     1814.46(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 8.2556
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12862
_diffrn_reflns_theta_full        71.42
_diffrn_reflns_theta_max         71.42
_diffrn_reflns_theta_min         2.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36386
_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    1.909
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1506 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.00009(2)
_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   0.901
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.901
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0306P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0604
_reflns_number_gt                2652
_reflns_number_total             3449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8026577_si_002_1.cif
_cod_data_source_block           Compound_3
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4024383