#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/43/4024383.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024383
loop_
_publ_author_name
'D. Christopher Braddock'
'David S. Millan'
'Yolanda Pérez-Fuertes'
'Rebecca H. Pouwer'
'Richard N. Sheppard'
'Savade Solanki'
'Andrew J. P. White'
_publ_section_title
;
Bromonium Ion Induced Transannular Oxonium Ion Formation-Fragmentation in
Model Obtusallene Systems and Structural Reassignment of Obtusallenes
V-VII
;
_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
_chemical_name_systematic
; 
 ? 
;
_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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0306P)²+0.0000P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.71798(18) 0.0692(5) 0.36768(15) 0.0358(7) Uani 1 1 d . . .
O2 O 0.62050(15) 0.3026(6) 0.27997(13) 0.0363(6) Uani 1 1 d . . .
O3 O 0.68174(16) -0.1261(4) 0.22064(15) 0.0357(7) Uani 1 1 d . . .
C1 C 0.7210(3) 0.3209(11) 0.0503(2) 0.0516(12) Uani 1 1 d . . .
H1A H 0.7567 0.4469 0.0508 0.062 Uiso 1 1 calc R . .
Br1 Br 0.61771(4) 0.29529(15) -0.02780(3) 0.0727(2) Uani 1 1 d . . .
C2 C 0.7433(3) 0.1663(8) 0.1035(2) 0.0398(11) Uani 1 1 d . . .
C3 C 0.7645(2) 0.0186(9) 0.1578(2) 0.0385(10) Uani 1 1 d . . .
H3A H 0.7967 -0.1147 0.1567 0.046 Uiso 1 1 calc R . .
C4 C 0.7398(2) 0.0507(8) 0.2224(2) 0.0324(10) Uani 1 1 d . . .
H4A H 0.7142 0.2099 0.2193 0.039 Uiso 1 1 calc R . .
C5 C 0.8098(2) 0.0257(8) 0.2970(2) 0.0342(9) Uani 1 1 d . . .
H5A H 0.8224 -0.1445 0.3065 0.041 Uiso 1 1 calc R . .
H5B H 0.8589 0.1024 0.2941 0.041 Uiso 1 1 calc R . .
C6 C 0.7953(3) 0.1286(8) 0.3626(3) 0.0359(11) Uani 1 1 d . . .
H6A H 0.8401 0.0711 0.4084 0.043 Uiso 1 1 calc R . .
C7 C 0.7980(3) 0.3998(8) 0.3631(3) 0.0381(11) Uani 1 1 d . . .
H7A H 0.7875 0.4568 0.3121 0.046 Uiso 1 1 calc R . .
Cl Cl 0.89494(7) 0.5102(2) 0.42376(6) 0.0469(3) Uani 1 1 d . . .
C8 C 0.7282(3) 0.4752(9) 0.3841(3) 0.0450(12) Uani 1 1 d . . .
H8A H 0.7043 0.6262 0.3601 0.054 Uiso 1 1 calc R . .
H8B H 0.7461 0.4932 0.4382 0.054 Uiso 1 1 calc R . .
C9 C 0.6675(2) 0.2738(8) 0.3561(2) 0.0356(9) Uani 1 1 d . . .
C10 C 0.6042(3) 0.2272(8) 0.3910(3) 0.0468(13) Uani 1 1 d . . .
H10A H 0.6253 0.1059 0.4308 0.056 Uiso 1 1 calc R . .
Br2 Br 0.57636(4) 0.51984(11) 0.42992(3) 0.06497(19) Uani 1 1 d . . .
C11 C 0.5289(3) 0.1373(10) 0.3293(3) 0.0713(19) Uani 1 1 d . . .
H11A H 0.4804 0.2332 0.3252 0.086 Uiso 1 1 calc R . .
H11B H 0.5182 -0.0295 0.3379 0.086 Uiso 1 1 calc R . .
C12 C 0.5476(3) 0.1602(8) 0.2595(3) 0.0418(11) Uani 1 1 d . . .
H12A H 0.5017 0.2485 0.2218 0.050 Uiso 1 1 calc R . .
C13 C 0.5551(2) -0.0802(7) 0.2276(2) 0.0329(10) Uani 1 1 d . . .
H13A H 0.5865 -0.1860 0.2696 0.039 Uiso 1 1 calc R . .
Br3 Br 0.44127(2) -0.19718(9) 0.18561(2) 0.04627(14) Uani 1 1 d . . .
C14 C 0.5980(2) -0.0833(8) 0.1733(2) 0.0375(10) Uani 1 1 d . . .
H14A H 0.5930 0.0752 0.1495 0.045 Uiso 1 1 calc R . .
C15 C 0.5714(3) -0.2742(9) 0.1150(2) 0.0562(15) Uani 1 1 d . . .
H15A H 0.6018 -0.2576 0.0826 0.084 Uiso 1 1 calc R . .
H15B H 0.5126 -0.2589 0.0859 0.084 Uiso 1 1 calc R . .
H15C H 0.5825 -0.4298 0.1387 0.084 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C6 110.5(3) . . ?
C9 O2 C12 109.5(3) . . ?
C4 O3 C14 116.9(3) . . ?
C2 C1 Br1 120.3(4) . . ?
C3 C2 C1 177.7(5) . . ?
C2 C3 C4 122.2(5) . . ?
O3 C4 C3 109.4(3) . . ?
O3 C4 C5 105.8(3) . . ?
C3 C4 C5 114.4(3) . . ?
C6 C5 C4 116.3(3) . . ?
O1 C6 C5 115.9(4) . . ?
O1 C6 C7 105.1(4) . . ?
C5 C6 C7 111.9(4) . . ?
C8 C7 C6 105.0(4) . . ?
C8 C7 Cl 113.3(3) . . ?
C6 C7 Cl 111.9(4) . . ?
C7 C8 C9 103.1(4) . . ?
O2 C9 O1 110.0(3) . . ?
O2 C9 C8 110.3(4) . . ?
O1 C9 C8 103.9(3) . . ?
O2 C9 C10 104.8(3) . . ?
O1 C9 C10 107.8(3) . . ?
C8 C9 C10 120.0(4) . . ?
C11 C10 C9 105.6(4) . . ?
C11 C10 Br2 108.8(4) . . ?
C9 C10 Br2 111.1(3) . . ?
C10 C11 C12 105.4(4) . . ?
O2 C12 C13 114.0(3) . . ?
O2 C12 C11 105.7(4) . . ?
C13 C12 C11 111.9(4) . . ?
C14 C13 C12 116.1(3) . . ?
C14 C13 Br3 113.6(3) . . ?
C12 C13 Br3 103.8(3) . . ?
O3 C14 C15 108.4(3) . . ?
O3 C14 C13 102.3(3) . . ?
C15 C14 C13 116.3(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.426(5) . ?
O1 C6 1.445(5) . ?
O2 C9 1.417(4) . ?
O2 C12 1.440(5) . ?
O3 C4 1.424(5) . ?
O3 C14 1.438(5) . ?
C1 C2 1.302(7) . ?
C1 Br1 1.891(4) . ?
C2 C3 1.293(6) . ?
C3 C4 1.500(5) . ?
C4 C5 1.524(5) . ?
C5 C6 1.520(6) . ?
C6 C7 1.536(6) . ?
C7 C8 1.503(6) . ?
C7 Cl 1.786(5) . ?
C8 C9 1.518(6) . ?
C9 C10 1.538(6) . ?
C10 C11 1.508(7) . ?
C10 Br2 1.963(4) . ?
C11 C12 1.532(7) . ?
C12 C13 1.524(6) . ?
C13 C14 1.523(6) . ?
C13 Br3 1.974(4) . ?
C14 C15 1.514(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658910
