#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/68/2006896.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, Robert W.'
'Lowe, David A.'
'Tsanaktsidis, John'
_publ_section_title
;endo-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_paper_doi               10.1107/S0108270197012286
_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       ω/2θ
_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      ?
_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          .0447
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0563P)²+1.0706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1188
_refine_ls_wR_factor_obs         .1052
_reflns_number_observed          2462
_reflns_number_total             3332
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ta1187.cif
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0563P)^2^+1.0706P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0563P)^2^+1.0706P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2006896
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_group
_atom_site_type_symbol
Br1 .38882(12) .16399(7) .10813(5) .0685(2) Uani d . 1 . Br
Br2 .19077(11) -.42733(7) .25926(5) .0625(2) Uani d . 1 . Br
Br3 -.28927(10) -.42905(7) .13982(6) .0674(2) Uani d . 1 . Br
O1 -.0794(7) -.2238(4) .3821(3) .0637(11) Uani d . 1 . O
O2 .4063(6) .3349(4) .3589(3) .0538(9) Uani d . 1 . O
O3 .6093(5) .1824(3) .3890(3) .0439(7) Uani d . 1 . O
C1 .2709(8) .0921(5) .2216(4) .0398(10) Uani d . 1 . C
C2 .2857(7) -.0622(5) .2341(3) .0338(9) Uani d . 1 . C
C3 .1054(8) -.1981(5) .1466(4) .0378(10) Uani d . 1 . C
C4 .0133(8) -.3024(5) .2154(4) .0397(10) Uani d . 1 . C
C5 .0418(8) -.2010(5) .3265(4) .0422(10) Uani d . 1 . C
C6 .2492(8) -.0667(5) .3501(4) .0377(10) Uani d . 1 . C
C7 .2250(8) .0853(5) .3897(4) .0433(11) Uani d . 1 . C
C8 .0156(9) .0876(6) .3109(6) .0552(14) Uani d . 1 . C
C9 .0417(9) .0908(6) .2124(5) .0518(13) Uani d . 1 . C
C10 .3952(8) .1858(5) .3442(4) .0385(10) Uani d . 1 . C
C11 .6324(10) .4270(6) .4103(5) .0587(14) Uani d . 1 . C
H11A .6587(16) .469(2) .486(4) .11(3) Uiso calc R 1 . H
H11B .670(2) .504(4) .3739(18) .062(17) Uiso calc R 1 . H
C12 .7626(10) .3275(5) .3995(6) .0588(15) Uani d . 1 . C
H12A .809(3) .3312(6) .337(3) .07(2) Uiso calc R 1 . H
H12B .885(6) .3528(14) .462(3) .072(19) Uiso calc R 1 . H
C13 .1783(11) -.2641(6) .0538(4) .0580(15) Uani d . 1 . C
H13A .302(6) -.296(4) .0857(12) .054(16) Uiso calc R 1 . H
H13B .224(6) -.190(3) .013(2) .053(15) Uiso calc R 1 . H
H13C .056(4) -.349(4) .003(2) .09(2) Uiso calc R 1 . H
H2 .433(8) -.064(5) .240(4) .029(11) Uiso d . 1 . H
H3 -.017(7) -.169(5) .116(3) .023(10) Uiso d . 1 . H
H6 .368(9) -.077(6) .402(4) .042(13) Uiso d . 1 . H
H7 .245(8) .107(6) .466(4) .043(13) Uiso d . 1 . H
H8 -.109(11) .066(7) .328(5) .063(18) Uiso d . 1 . H
H9 -.054(8) .092(5) .145(4) .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_site_symmetry_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 . .96(5) ?
C3 C13 . 1.509(7) ?
C3 C4 . 1.522(6) y
C3 H3 . .94(4) ?
C4 C5 . 1.529(6) y
C5 C6 . 1.516(6) ?
C6 C7 . 1.544(6) ?
C6 H6 . .92(5) ?
C7 C8 . 1.495(8) ?
C7 C10 . 1.551(7) y
C7 H7 . .93(5) ?
C8 C9 . 1.308(9) y
C8 H8 . .88(6) ?
C9 H9 . .92(5) ?
C11 C12 . 1.476(8) ?
C11 H11A . .93(5) ?
C11 H11B . .93(5) ?
C12 H12A . .92(4) ?
C12 H12B . .92(4) ?
C13 H13A . .97(3) ?
C13 H13B . .97(3) ?
C13 H13C . .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)
