#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006896.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006896
loop_
_publ_author_name
'Gable, R. W.'
'Lowe, D. A.'
'Tsanaktsidis, J.'
_publ_section_title
;
 <i>endo</i>-1,4,4-Tribromo-3-methyltricyclo[5.2.1.0^2,6^]dec-8-ene-5,10-dione
 10-Ethylene Acetal
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1916
_journal_page_last               1917
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C13 H13 Br3 O3'
_chemical_formula_weight         456.96
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                98.27(2)
_cell_angle_beta                 104.84(2)
_cell_angle_gamma                106.74(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6161(13)
_cell_length_b                   9.633(2)
_cell_length_c                   12.692(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293.0(10)
_cell_measurement_theta_max      21.2
_cell_measurement_theta_min      11.3
_cell_volume                     727.8(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293.0(10)
_diffrn_measurement_device       'Enraf Nonius CAD4-MachS diffractometer'
_diffrn_measurement_method       \w/2\q
_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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4197
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        18
_diffrn_standards_interval_time  160
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    8.314
_exptl_absorpt_correction_T_max  0.1655
_exptl_absorpt_correction_T_min  0.0410
_exptl_absorpt_correction_type   'Gaussian integration (Sheldrick, 1976)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.085
_exptl_crystal_density_meas      'Not measured'
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.667
_refine_ls_extinction_coef       0.0116(15)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.055
_refine_ls_goodness_of_fit_obs   1.097
_refine_ls_hydrogen_treatment    'Methine H atoms refined, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_restrained_S_obs      1.097
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_obs          0.0447
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0563P)^2^+1.0706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1188
_refine_ls_wR_factor_obs         0.1052
_reflns_number_observed          2462
_reflns_number_total             3332
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ta1187.cif
_[local]_cod_data_source_block   jt_7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               2006896
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0947(5) 0.0521(3) 0.0488(3) 0.0012(3) 0.0276(3) 0.0214(2)
Br2 0.0818(4) 0.0523(3) 0.0659(4) 0.0360(3) 0.0250(3) 0.0215(3)
Br3 0.0513(3) 0.0516(3) 0.0774(4) -0.0032(2) 0.0168(3) -0.0024(3)
O1 0.078(3) 0.049(2) 0.064(2) 0.003(2) 0.046(2) 0.008(2)
O2 0.051(2) 0.030(2) 0.073(2) 0.0130(15) 0.011(2) 0.003(2)
O3 0.038(2) 0.033(2) 0.053(2) 0.0065(13) 0.0096(14) 0.0081(14)
C1 0.049(3) 0.030(2) 0.041(2) 0.011(2) 0.015(2) 0.011(2)
C2 0.035(2) 0.031(2) 0.034(2) 0.008(2) 0.013(2) 0.006(2)
C3 0.045(3) 0.033(2) 0.032(2) 0.011(2) 0.012(2) 0.005(2)
C4 0.040(2) 0.030(2) 0.046(2) 0.010(2) 0.012(2) 0.006(2)
C5 0.051(3) 0.032(2) 0.045(2) 0.009(2) 0.022(2) 0.010(2)
C6 0.045(3) 0.035(2) 0.032(2) 0.012(2) 0.013(2) 0.005(2)
C7 0.052(3) 0.035(2) 0.043(3) 0.011(2) 0.024(2) 0.000(2)
C8 0.043(3) 0.035(3) 0.087(4) 0.014(2) 0.025(3) 0.004(3)
C9 0.044(3) 0.034(2) 0.066(4) 0.012(2) 0.001(3) 0.009(2)
C10 0.042(2) 0.026(2) 0.044(2) 0.010(2) 0.014(2) 0.002(2)
C11 0.059(3) 0.035(3) 0.070(4) 0.004(2) 0.020(3) 0.001(2)
C12 0.053(3) 0.031(3) 0.077(4) 0.001(2) 0.013(3) 0.006(2)
C13 0.084(4) 0.045(3) 0.041(3) 0.011(3) 0.031(3) 0.000(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Br1 0.38882(12) 0.16399(7) 0.10813(5) 0.0685(2) Uani d . 1 Br
Br2 0.19077(11) -0.42733(7) 0.25926(5) 0.0625(2) Uani d . 1 Br
Br3 -0.28927(10) -0.42905(7) 0.13982(6) 0.0674(2) Uani d . 1 Br
O1 -0.0794(7) -0.2238(4) 0.3821(3) 0.0637(11) Uani d . 1 O
O2 0.4063(6) 0.3349(4) 0.3589(3) 0.0538(9) Uani d . 1 O
O3 0.6093(5) 0.1824(3) 0.3890(3) 0.0439(7) Uani d . 1 O
C1 0.2709(8) 0.0921(5) 0.2216(4) 0.0398(10) Uani d . 1 C
C2 0.2857(7) -0.0622(5) 0.2341(3) 0.0338(9) Uani d . 1 C
C3 0.1054(8) -0.1981(5) 0.1466(4) 0.0378(10) Uani d . 1 C
C4 0.0133(8) -0.3024(5) 0.2154(4) 0.0397(10) Uani d . 1 C
C5 0.0418(8) -0.2010(5) 0.3265(4) 0.0422(10) Uani d . 1 C
C6 0.2492(8) -0.0667(5) 0.3501(4) 0.0377(10) Uani d . 1 C
C7 0.2250(8) 0.0853(5) 0.3897(4) 0.0433(11) Uani d . 1 C
C8 0.0156(9) 0.0876(6) 0.3109(6) 0.0552(14) Uani d . 1 C
C9 0.0417(9) 0.0908(6) 0.2124(5) 0.0518(13) Uani d . 1 C
C10 0.3952(8) 0.1858(5) 0.3442(4) 0.0385(10) Uani d . 1 C
C11 0.6324(10) 0.4270(6) 0.4103(5) 0.0587(14) Uani d . 1 C
H11A 0.6587(16) 0.469(2) 0.486(4) 0.11(3) Uiso calc R 1 H
H11B 0.670(2) 0.504(4) 0.3739(18) 0.062(17) Uiso calc R 1 H
C12 0.7626(10) 0.3275(5) 0.3995(6) 0.0588(15) Uani d . 1 C
H12A 0.809(3) 0.3312(6) 0.337(3) 0.07(2) Uiso calc R 1 H
H12B 0.885(6) 0.3528(14) 0.462(3) 0.072(19) Uiso calc R 1 H
C13 0.1783(11) -0.2641(6) 0.0538(4) 0.0580(15) Uani d . 1 C
H13A 0.302(6) -0.296(4) 0.0857(12) 0.054(16) Uiso calc R 1 H
H13B 0.224(6) -0.190(3) 0.013(2) 0.053(15) Uiso calc R 1 H
H13C 0.056(4) -0.349(4) 0.003(2) 0.09(2) Uiso calc R 1 H
H2 0.433(8) -0.064(5) 0.240(4) 0.029(11) Uiso d . 1 H
H3 -0.017(7) -0.169(5) 0.116(3) 0.023(10) Uiso d . 1 H
H6 0.368(9) -0.077(6) 0.402(4) 0.042(13) Uiso d . 1 H
H7 0.245(8) 0.107(6) 0.466(4) 0.043(13) Uiso d . 1 H
H8 -0.109(11) 0.066(7) 0.328(5) 0.063(18) Uiso d . 1 H
H9 -0.054(8) 0.092(5) 0.145(4) 0.040(13) Uiso d . 1 H
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'
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_publ_flag
C10 O2 C11 108.4(4) ?
C10 O3 C12 107.3(4) ?
C9 C1 C2 109.2(4) y
C9 C1 C10 99.8(4) y
C2 C1 C10 100.7(3) y
C9 C1 Br1 115.8(4) y
C2 C1 Br1 113.5(3) y
C10 C1 Br1 116.0(3) y
C3 C2 C1 116.1(4) ?
C3 C2 C6 108.1(3) ?
C1 C2 C6 101.1(3) ?
C3 C2 H2 112.(3) ?
C1 C2 H2 111.(3) ?
C6 C2 H2 108.(3) ?
C13 C3 C4 116.8(4) y
C13 C3 C2 115.0(4) y
C4 C3 C2 104.7(3) ?
C13 C3 H3 110.(3) ?
C4 C3 H3 102.(3) ?
C2 C3 H3 108.(3) ?
C3 C4 C5 105.4(3) y
C3 C4 Br3 112.7(3) y
C5 C4 Br3 112.9(3) y
C3 C4 Br2 113.1(3) y
C5 C4 Br2 104.0(3) y
Br3 C4 Br2 108.5(2) y
O1 C5 C6 127.3(4) ?
O1 C5 C4 125.8(4) ?
C6 C5 C4 106.9(4) ?
C5 C6 C7 114.9(4) ?
C5 C6 C2 105.0(3) ?
C7 C6 C2 104.4(4) ?
C5 C6 H6 110.(3) ?
C7 C6 H6 110.(3) ?
C2 C6 H6 112.(3) ?
C8 C7 C6 107.2(4) ?
C8 C7 C10 98.8(4) ?
C6 C7 C10 99.6(4) ?
C8 C7 H7 119.(3) ?
C6 C7 H7 112.(3) ?
C10 C7 H7 119.(3) ?
C9 C8 C7 108.8(5) ?
C9 C8 H8 129.(4) ?
C7 C8 H8 121.(4) ?
C8 C9 C1 107.5(5) ?
C8 C9 H9 131.(3) ?
C1 C9 H9 121.(3) ?
O3 C10 O2 108.4(3) ?
O3 C10 C7 112.1(4) ?
O2 C10 C7 115.4(4) ?
O3 C10 C1 114.7(4) ?
O2 C10 C1 113.6(4) ?
C7 C10 C1 92.1(3) y
O2 C11 C12 105.4(4) ?
O2 C11 H11A 110.7(3) ?
C12 C11 H11A 110.7(4) ?
O2 C11 H11B 110.7(3) ?
C12 C11 H11B 110.7(3) ?
H11A C11 H11B 108.8 ?
O3 C12 C11 103.6(5) ?
O3 C12 H12A 111.0(3) ?
C11 C12 H12A 111.0(4) ?
O3 C12 H12B 111.0(3) ?
C11 C12 H12B 111.0(3) ?
H12A C12 H12B 109.0 ?
C3 C13 H13A 109.5(3) ?
C3 C13 H13B 109.5(3) ?
H13A C13 H13B 109.5 ?
C3 C13 H13C 109.5(3) ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 1.927(5) y
Br2 C4 1.952(5) y
Br3 C4 1.921(5) y
O1 C5 1.193(6) ?
O2 C10 1.399(5) ?
O2 C11 1.422(6) ?
O3 C10 1.397(6) ?
O3 C12 1.435(6) ?
C1 C9 1.487(7) ?
C1 C2 1.545(6) y
C1 C10 1.557(6) y
C2 C3 1.541(6) y
C2 C6 1.556(6) ?
C2 H2 0.96(5) ?
C3 C13 1.509(7) ?
C3 C4 1.522(6) y
C3 H3 0.94(4) ?
C4 C5 1.529(6) y
C5 C6 1.516(6) ?
C6 C7 1.544(6) ?
C6 H6 0.92(5) ?
C7 C8 1.495(8) ?
C7 C10 1.551(7) y
C7 H7 0.93(5) ?
C8 C9 1.308(9) y
C8 H8 0.88(6) ?
C9 H9 0.92(5) ?
C11 C12 1.476(8) ?
C11 H11A 0.93(5) ?
C11 H11B 0.93(5) ?
C12 H12A 0.92(4) ?
C12 H12B 0.92(4) ?
C13 H13A 0.97(3) ?
C13 H13B 0.97(3) ?
C13 H13C 0.97(3) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C9 C1 C2 C3 51.1(5)
C10 C1 C2 C3 155.6(4)
Br1 C1 C2 C3 -79.7(4)
C9 C1 C2 C6 -65.5(5)
C10 C1 C2 C6 39.0(4)
Br1 C1 C2 C6 163.6(3)
C1 C2 C3 C13 101.2(5)
C6 C2 C3 C13 -146.1(4)
C1 C2 C3 C4 -129.2(4)
C6 C2 C3 C4 -16.6(5)
C13 C3 C4 C5 157.8(5)
C2 C3 C4 C5 29.3(5)
C13 C3 C4 Br3 -78.7(5)
C2 C3 C4 Br3 152.8(3)
C13 C3 C4 Br2 44.8(5)
C2 C3 C4 Br2 -83.6(4)
C3 C4 C5 O1 147.1(5)
Br3 C4 C5 O1 23.8(7)
Br2 C4 C5 O1 -93.6(6)
C3 C4 C5 C6 -31.9(5)
Br3 C4 C5 C6 -155.3(3)
Br2 C4 C5 C6 87.3(4)
O1 C5 C6 C7 -44.0(7)
C4 C5 C6 C7 135.1(4)
O1 C5 C6 C2 -158.1(5)
C4 C5 C6 C2 21.0(5)
C3 C2 C6 C5 -2.6(5)
C1 C2 C6 C5 119.7(4)
C3 C2 C6 C7 -123.8(4)
C1 C2 C6 C7 -1.5(5)
C5 C6 C7 C8 -48.4(6)
C2 C6 C7 C8 66.0(5)
C5 C6 C7 C10 -150.9(4)
C2 C6 C7 C10 -36.5(4)
C6 C7 C8 C9 -67.9(5)
C10 C7 C8 C9 35.1(5)
C7 C8 C9 C1 -0.5(6)
C2 C1 C9 C8 70.8(5)
C10 C1 C9 C8 -34.3(5)
Br1 C1 C9 C8 -159.6(4)
C12 O3 C10 O2 -18.0(5)
C12 O3 C10 C7 -146.5(4)
C12 O3 C10 C1 110.1(5)
C11 O2 C10 O3 2.1(5)
C11 O2 C10 C7 128.6(5)
C11 O2 C10 C1 -126.7(5)
C8 C7 C10 O3 -168.8(4)
C6 C7 C10 O3 -59.6(4)
C8 C7 C10 O2 66.5(5)
C6 C7 C10 O2 175.8(4)
C8 C7 C10 C1 -51.0(4)
C6 C7 C10 C1 58.3(4)
C9 C1 C10 O3 167.0(4)
C2 C1 C10 O3 55.1(5)
Br1 C1 C10 O3 -67.9(4)
C9 C1 C10 O2 -67.5(5)
C2 C1 C10 O2 -179.4(4)
Br1 C1 C10 O2 57.6(5)
C9 C1 C10 C7 51.4(4)
C2 C1 C10 C7 -60.5(4)
Br1 C1 C10 C7 176.6(3)
C10 O2 C11 C12 14.1(6)
C10 O3 C12 C11 26.0(6)
O2 C11 C12 O3 -24.3(6)