#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:08:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178422 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/43/4024384.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_4024384
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_formula_moiety         'C11 H16 Br Cl O2'
_chemical_formula_sum            'C11 H16 Br Cl O2'
_chemical_formula_weight         295.60
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.0480(13)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   10.08901(12)
_cell_length_b                   14.1397(2)
_cell_length_c                   26.0378(4)
_cell_measurement_reflns_used    20098
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.3250
_cell_measurement_theta_min      3.7760
_cell_volume                     3700.03(9)
_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 0.993
_diffrn_measured_fraction_theta_max 0.914
_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
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            51476
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.33
_diffrn_reflns_theta_min         3.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.528
_exptl_absorpt_correction_T_max  0.789
_exptl_absorpt_correction_T_min  0.331
_exptl_absorpt_correction_type   analytical
_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) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         12075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0583
_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/[σ²(Fo²)+(0.0184P)²+5.3793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                7802
_reflns_number_total             12075
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8026577_si_002_2.cif
_cod_data_source_block           Compound_15
_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      P2(1)/n
_cod_database_code               4024384
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.5785(2) 0.68065(15) 0.44721(9) 0.0339(5) Uani 1 1 d . . .
O2 O 0.30230(17) 0.54136(14) 0.38573(7) 0.0217(4) Uani 1 1 d . . .
C4 C 0.5632(3) 0.6330(2) 0.39834(12) 0.0288(7) Uani 1 1 d . . .
H4A H 0.6448 0.6417 0.3804 0.035 Uiso 1 1 calc R . .
H4B H 0.4879 0.6615 0.3767 0.035 Uiso 1 1 calc R . .
C5 C 0.5375(3) 0.5278(2) 0.40497(13) 0.0287(7) Uani 1 1 d . . .
H5A H 0.5433 0.4954 0.3715 0.034 Uiso 1 1 calc R . .
H5B H 0.6073 0.5011 0.4299 0.034 Uiso 1 1 calc R . .
C6 C 0.4028(3) 0.50909(19) 0.42379(11) 0.0214(6) Uani 1 1 d . . .
H6A H 0.3960 0.5483 0.4554 0.026 Uiso 1 1 calc R . .
C7 C 0.3587(3) 0.4100(2) 0.43600(12) 0.0261(6) Uani 1 1 d . . .
H7A H 0.4012 0.3882 0.4701 0.031 Uiso 1 1 calc R . .
Cl Cl 0.39251(9) 0.32886(6) 0.38529(4) 0.0492(2) Uani 1 1 d . . .
C8 C 0.2099(3) 0.4250(2) 0.43792(12) 0.0260(6) Uani 1 1 d . . .
H8A H 0.1894 0.4489 0.4721 0.031 Uiso 1 1 calc R . .
H8B H 0.1600 0.3656 0.4303 0.031 Uiso 1 1 calc R . .
C9 C 0.1769(3) 0.4991(2) 0.39570(11) 0.0230(6) Uani 1 1 d . . .
H9A H 0.1397 0.4658 0.3637 0.028 Uiso 1 1 calc R . .
C10 C 0.0825(3) 0.5797(2) 0.40703(12) 0.0272(6) Uani 1 1 d . . .
H10A H 0.0677 0.6183 0.3749 0.033 Uiso 1 1 calc R . .
Br Br -0.08851(3) 0.52107(3) 0.419119(13) 0.03903(9) Uani 1 1 d . . .
C11 C 0.1263(3) 0.6476(2) 0.45097(12) 0.0308(7) Uani 1 1 d . . .
H11A H 0.0526 0.6916 0.4565 0.037 Uiso 1 1 calc R . .
H11B H 0.1472 0.6112 0.4831 0.037 Uiso 1 1 calc R . .
C12 C 0.2467(3) 0.7033(2) 0.43903(13) 0.0311(7) Uani 1 1 d . . .
H12A H 0.2431 0.7342 0.4065 0.037 Uiso 1 1 calc R . .
C13 C 0.3567(3) 0.7131(2) 0.46965(14) 0.0334(7) Uani 1 1 d . . .
H13A H 0.3554 0.6926 0.5043 0.040 Uiso 1 1 calc R . .
C14 C 0.4842(3) 0.7544(2) 0.45377(15) 0.0387(8) Uani 1 1 d . . .
H14A H 0.4662 0.7896 0.4210 0.046 Uiso 1 1 calc R . .
H14B H 0.5213 0.7993 0.4805 0.046 Uiso 1 1 calc R . .
O1' O -0.1966(2) 0.40326(16) 0.22792(9) 0.0368(5) Uani 1 1 d . . .
O2' O 0.06964(17) 0.56003(15) 0.28171(7) 0.0239(4) Uani 1 1 d . . .
C4' C -0.1861(3) 0.4604(2) 0.27306(13) 0.0338(7) Uani 1 1 d . . .
H4'A H -0.1103 0.4382 0.2967 0.041 Uiso 1 1 calc R . .
H4'B H -0.2681 0.4537 0.2910 0.041 Uiso 1 1 calc R . .
C5' C -0.1658(3) 0.5636(2) 0.26031(13) 0.0303(7) Uani 1 1 d . . .
H5'A H -0.2361 0.5839 0.2337 0.036 Uiso 1 1 calc R . .
H5'B H -0.1738 0.6024 0.2915 0.036 Uiso 1 1 calc R . .
C6' C -0.0309(2) 0.5800(2) 0.24084(11) 0.0215(6) Uani 1 1 d . . .
H6'A H -0.0205 0.5328 0.2128 0.026 Uiso 1 1 calc R . .
C7' C 0.0083(3) 0.6756(2) 0.22091(13) 0.0278(6) Uani 1 1 d . . .
H7'A H -0.0338 0.6871 0.1852 0.033 Uiso 1 1 calc R . .
Cl' Cl -0.03188(9) 0.76847(7) 0.26388(5) 0.0620(3) Uani 1 1 d . . .
C8' C 0.1581(3) 0.6628(2) 0.22090(12) 0.0274(6) Uani 1 1 d . . .
H8'A H 0.2047 0.7244 0.2241 0.033 Uiso 1 1 calc R . .
H8'B H 0.1810 0.6310 0.1890 0.033 Uiso 1 1 calc R . .
C9' C 0.1939(3) 0.6006(2) 0.26838(11) 0.0228(6) Uani 1 1 d . . .
H9'A H 0.2302 0.6421 0.2974 0.027 Uiso 1 1 calc R . .
C10' C 0.2903(3) 0.5182(2) 0.26329(12) 0.0263(6) Uani 1 1 d . . .
H10B H 0.3059 0.4878 0.2980 0.032 Uiso 1 1 calc R . .
Br' Br 0.46034(3) 0.57383(3) 0.246545(13) 0.03582(9) Uani 1 1 d . . .
C11' C 0.2488(3) 0.4402(2) 0.22435(12) 0.0301(7) Uani 1 1 d . . .
H11C H 0.2250 0.4690 0.1901 0.036 Uiso 1 1 calc R . .
H11D H 0.3249 0.3970 0.2212 0.036 Uiso 1 1 calc R . .
C12' C 0.1327(3) 0.3847(2) 0.24022(13) 0.0283(7) Uani 1 1 d . . .
H12B H 0.1368 0.3620 0.2747 0.034 Uiso 1 1 calc R . .
C13' C 0.0252(3) 0.3651(2) 0.20949(13) 0.0342(7) Uani 1 1 d . . .
H13B H 0.0287 0.3756 0.1736 0.041 Uiso 1 1 calc R . .
C14' C -0.1026(3) 0.3274(2) 0.22712(14) 0.0377(8) Uani 1 1 d . . .
H14C H -0.1385 0.2772 0.2034 0.045 Uiso 1 1 calc R . .
H14D H -0.0860 0.2998 0.2620 0.045 Uiso 1 1 calc R . .
O1" O 0.8051(2) 0.68889(16) 0.11799(9) 0.0382(6) Uani 1 1 d . . .
O2" O 0.57218(18) 0.51577(14) 0.05687(7) 0.0218(4) Uani 1 1 d . . .
C4" C 0.8192(3) 0.6234(2) 0.07716(14) 0.0339(7) Uani 1 1 d . . .
H4"A H 0.9096 0.6291 0.0654 0.041 Uiso 1 1 calc R . .
H4"B H 0.7541 0.6390 0.0477 0.041 Uiso 1 1 calc R . .
C5" C 0.7970(3) 0.5222(2) 0.09414(13) 0.0293(7) Uani 1 1 d . . .
H5"A H 0.8217 0.4783 0.0669 0.035 Uiso 1 1 calc R . .
H5"B H 0.8555 0.5089 0.1258 0.035 Uiso 1 1 calc R . .
C6" C 0.6543(3) 0.5047(2) 0.10447(11) 0.0224(6) Uani 1 1 d . . .
H6"A H 0.6285 0.5553 0.1285 0.027 Uiso 1 1 calc R . .
C7" C 0.6097(3) 0.4115(2) 0.12533(12) 0.0273(6) Uani 1 1 d . . .
H7"A H 0.6356 0.4060 0.1632 0.033 Uiso 1 1 calc R . .
Cl" Cl 0.67221(9) 0.31292(6) 0.09056(4) 0.0424(2) Uani 1 1 d . . .
C8" C 0.4594(3) 0.4212(2) 0.11431(11) 0.0267(6) Uani 1 1 d . . .
H8"A H 0.4209 0.4586 0.1415 0.032 Uiso 1 1 calc R . .
H8"B H 0.4159 0.3584 0.1118 0.032 Uiso 1 1 calc R . .
C9" C 0.4441(3) 0.4730(2) 0.06231(11) 0.0216(6) Uani 1 1 d . . .
H9"A H 0.4258 0.4252 0.0343 0.026 Uiso 1 1 calc R . .
C10" C 0.3413(3) 0.5517(2) 0.05485(12) 0.0259(6) Uani 1 1 d . . .
H10C H 0.3413 0.5743 0.0184 0.031 Uiso 1 1 calc R . .
Br" Br 0.16530(3) 0.49462(3) 0.062198(15) 0.04136(10) Uani 1 1 d . . .
C11" C 0.3572(3) 0.6384(2) 0.08962(13) 0.0320(7) Uani 1 1 d . . .
H11E H 0.2782 0.6797 0.0831 0.038 Uiso 1 1 calc R . .
H11F H 0.3621 0.6181 0.1261 0.038 Uiso 1 1 calc R . .
C12" C 0.4804(3) 0.6938(2) 0.08050(13) 0.0297(7) Uani 1 1 d . . .
H12C H 0.4938 0.7105 0.0460 0.036 Uiso 1 1 calc R . .
C13" C 0.5709(3) 0.7205(2) 0.11721(13) 0.0322(7) Uani 1 1 d . . .
H13C H 0.5497 0.7143 0.1519 0.039 Uiso 1 1 calc R . .
C14" C 0.7042(3) 0.7598(2) 0.10827(15) 0.0385(8) Uani 1 1 d . . .
H14E H 0.7035 0.7821 0.0722 0.046 Uiso 1 1 calc R . .
H14F H 0.7242 0.8146 0.1314 0.046 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 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C14 O1 C4 115.2(2) . . ?
C6 O2 C9 108.8(2) . . ?
O1 C4 C5 111.3(3) . . ?
C6 C5 C4 112.0(2) . . ?
O2 C6 C5 108.9(2) . . ?
O2 C6 C7 103.8(2) . . ?
C5 C6 C7 121.4(2) . . ?
C6 C7 C8 100.8(2) . . ?
C6 C7 Cl 110.9(2) . . ?
C8 C7 Cl 111.3(2) . . ?
C7 C8 C9 102.9(2) . . ?
O2 C9 C10 107.2(2) . . ?
O2 C9 C8 105.9(2) . . ?
C10 C9 C8 118.0(2) . . ?
C11 C10 C9 117.9(2) . . ?
C11 C10 Br 110.2(2) . . ?
C9 C10 Br 106.7(2) . . ?
C12 C11 C10 111.1(3) . . ?
C13 C12 C11 125.7(3) . . ?
C12 C13 C14 124.8(3) . . ?
O1 C14 C13 110.1(3) . . ?
C4' O1' C14' 115.8(2) . . ?
C6' O2' C9' 108.4(2) . . ?
O1' C4' C5' 111.6(3) . . ?
C6' C5' C4' 111.4(2) . . ?
O2' C6' C5' 108.7(2) . . ?
O2' C6' C7' 104.0(2) . . ?
C5' C6' C7' 121.5(2) . . ?
C6' C7' C8' 100.5(2) . . ?
C6' C7' Cl' 111.1(2) . . ?
C8' C7' Cl' 111.5(2) . . ?
C7' C8' C9' 103.4(2) . . ?
O2' C9' C10' 106.8(2) . . ?
O2' C9' C8' 105.8(2) . . ?
C10' C9' C8' 118.2(2) . . ?
C9' C10' C11' 117.9(2) . . ?
C9' C10' Br' 106.71(19) . . ?
C11' C10' Br' 109.48(19) . . ?
C12' C11' C10' 111.7(2) . . ?
C13' C12' C11' 124.3(3) . . ?
C12' C13' C14' 124.8(3) . . ?
O1' C14' C13' 109.0(3) . . ?
C4" O1" C14" 116.0(3) . . ?
C6" O2" C9" 108.8(2) . . ?
O1" C4" C5" 111.6(3) . . ?
C6" C5" C4" 112.0(2) . . ?
O2" C6" C5" 108.4(2) . . ?
O2" C6" C7" 103.8(2) . . ?
C5" C6" C7" 121.9(2) . . ?
C6" C7" C8" 100.2(2) . . ?
C6" C7" Cl" 111.4(2) . . ?
C8" C7" Cl" 111.1(2) . . ?
C7" C8" C9" 103.3(2) . . ?
O2" C9" C10" 106.6(2) . . ?
O2" C9" C8" 105.4(2) . . ?
C10" C9" C8" 118.4(2) . . ?
C9" C10" C11" 118.5(2) . . ?
C9" C10" Br" 107.3(2) . . ?
C11" C10" Br" 108.65(19) . . ?
C12" C11" C10" 111.7(3) . . ?
C13" C12" C11" 124.3(3) . . ?
C12" C13" C14" 124.8(3) . . ?
O1" C14" C13" 110.3(3) . . ?
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 C14 1.432(4) . ?
O1 C4 1.436(4) . ?
O2 C6 1.429(3) . ?
O2 C9 1.443(3) . ?
C4 C5 1.523(4) . ?
C5 C6 1.508(4) . ?
C6 C7 1.512(4) . ?
C7 C8 1.522(4) . ?
C7 Cl 1.804(3) . ?
C8 C9 1.534(4) . ?
C9 C10 1.531(4) . ?
C10 C11 1.529(4) . ?
C10 Br 1.964(3) . ?
C11 C12 1.503(4) . ?
C12 C13 1.315(4) . ?
C13 C14 1.503(5) . ?
O1' C4' 1.423(4) . ?
O1' C14' 1.433(4) . ?
O2' C6' 1.432(3) . ?
O2' C9' 1.449(3) . ?
C4' C5' 1.514(5) . ?
C5' C6' 1.511(4) . ?
C6' C7' 1.514(4) . ?
C7' C8' 1.522(4) . ?
C7' Cl' 1.794(3) . ?
C8' C9' 1.534(4) . ?
C9' C10' 1.530(4) . ?
C10' C11' 1.532(4) . ?
C10' Br' 1.971(3) . ?
C11' C12' 1.497(4) . ?
C12' C13' 1.320(4) . ?
C13' C14' 1.503(5) . ?
O1" C4" 1.427(4) . ?
O1" C14" 1.436(4) . ?
O2" C6" 1.438(3) . ?
O2" C9" 1.445(3) . ?
C4" C5" 1.519(4) . ?
C5" C6" 1.508(4) . ?
C6" C7" 1.508(4) . ?
C7" C8" 1.524(4) . ?
C7" Cl" 1.806(3) . ?
C8" C9" 1.535(4) . ?
C9" C10" 1.523(4) . ?
C10" C11" 1.524(4) . ?
C10" Br" 1.975(3) . ?
C11" C12" 1.505(4) . ?
C12" C13" 1.318(4) . ?
C13" C14" 1.492(5) . ?
