#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2006979.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_2006979
loop_
_publ_author_name
'Gable, R. W.'
'Lowe, D. A.'
'Tsanaktsidis, J.'
_publ_section_title
;
 <i>endo</i>-2,4-Dibromo-3a,4,7,7a-tetrahydro-4,7-methanoindene-1,8-dione
 8-Ethylene Acetal
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              151
_journal_page_last               152
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C12 H10 Br2 O3'
_chemical_formula_sum            'C12 H10 Br2 O3'
_chemical_formula_weight         362.02
_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                91.43(2)
_cell_angle_beta                 94.74(2)
_cell_angle_gamma                90.56(2)
_cell_formula_units_Z            2
_cell_length_a                   6.2510(11)
_cell_length_b                   8.187(2)
_cell_length_c                   11.784(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293.0(10)
_cell_measurement_theta_max      18.4
_cell_measurement_theta_min      10.6
_cell_volume                     600.8(2)
_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  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3518
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        8
_diffrn_standards_interval_time  160
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    6.739
_exptl_absorpt_correction_T_max  0.299
_exptl_absorpt_correction_T_min  0.139
_exptl_absorpt_correction_type   'Gaussian integration (Sheldrick, 1976)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.001
_exptl_crystal_density_meas      'Not measured'
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.446
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.073
_refine_ls_goodness_of_fit_obs   1.115
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_restrained_S_obs      1.115
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_obs          0.0345
_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^)+(0.0504P)^2^+0.1744P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.0875
_refine_ls_wR_factor_obs         0.0808
_reflns_number_observed          2232
_reflns_number_total             2761
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ta1186.cif
_[local]_cod_data_source_block   jt_6
_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               2006979
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 0.0547(2) 0.0606(2) 0.0373(2) -0.0202(2) 0.01565(14) 0.00292(14)
Br2 0.0646(3) 0.0407(2) 0.0744(3) -0.0143(2) -0.0010(2) -0.0164(2)
O1 0.0466(13) 0.0414(12) 0.0538(13) -0.0092(10) 0.0104(11) 0.0084(10)
O2 0.0320(11) 0.0345(11) 0.0523(13) -0.0064(8) -0.0043(9) -0.0058(9)
O3 0.0368(11) 0.0258(10) 0.0529(12) 0.0024(8) 0.0064(10) -0.0046(8)
C1 0.0290(14) 0.0315(13) 0.0284(13) -0.0045(11) 0.0088(11) 0.0004(10)
C2 0.0272(14) 0.0322(14) 0.0322(14) 0.0002(11) 0.0013(11) 0.0018(11)
C3 0.0301(15) 0.045(2) 0.037(2) -0.0048(12) -0.0002(12) -0.0043(13)
C4 0.0266(14) 0.0343(14) 0.047(2) -0.0047(11) -0.0005(12) -0.0061(12)
C5 0.0231(13) 0.0314(14) 0.045(2) -0.0002(11) 0.0058(12) 0.0000(12)
C6 0.0263(13) 0.0290(13) 0.0363(14) 0.0016(11) 0.0101(11) 0.0004(11)
C7 0.035(2) 0.0317(13) 0.0279(14) -0.0032(11) 0.0035(12) 0.0010(11)
C8 0.0304(15) 0.0283(13) 0.050(2) -0.0006(11) -0.0077(13) 0.0041(12)
C9 0.0244(14) 0.0339(15) 0.051(2) 0.0009(11) 0.0053(13) -0.0111(13)
C10 0.0271(13) 0.0279(13) 0.0338(14) -0.0002(10) 0.0025(11) -0.0014(11)
C11 0.054(2) 0.035(2) 0.052(2) -0.0160(15) 0.001(2) -0.0043(14)
C12 0.057(2) 0.0275(15) 0.054(2) -0.0035(14) 0.007(2) 0.0024(14)
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_occupancy
_atom_site_type_symbol
Br1 0.20167(6) 0.01455(4) 0.41014(3) 0.05030(13) Uani d 1 Br
Br2 0.79857(7) 0.63623(4) 0.36816(4) 0.06066(14) Uani d 1 Br
O1 0.7366(4) 0.4695(3) 0.1153(2) 0.0468(5) Uani d 1 O
O2 0.0933(3) -0.0159(2) 0.1352(2) 0.0402(5) Uani d 1 O
O3 0.4368(3) -0.1007(2) 0.1667(2) 0.0384(5) Uani d 1 O
C1 0.3178(4) 0.1284(3) 0.2877(2) 0.0293(5) Uani d 1 C
C2 0.5621(4) 0.1635(3) 0.3043(2) 0.0306(6) Uani d 1 C
C3 0.6312(5) 0.3096(4) 0.3757(3) 0.0376(6) Uani d 1 C
C4 0.6992(4) 0.4297(3) 0.3146(3) 0.0363(6) Uani d 1 C
C5 0.6907(4) 0.3841(3) 0.1912(3) 0.0329(6) Uani d 1 C
C6 0.6108(5) 0.2076(3) 0.1810(2) 0.0301(6) Uani d 1 C
C7 0.3898(5) 0.1829(3) 0.1101(2) 0.0316(6) Uani d 1 C
C8 0.2452(5) 0.3124(4) 0.1490(3) 0.0369(6) Uani d 1 C
C9 0.2047(5) 0.2827(4) 0.2541(3) 0.0365(7) Uani d 1 C
C10 0.3034(4) 0.0348(3) 0.1712(2) 0.0296(6) Uani d 1 C
C11 0.0960(6) -0.1850(4) 0.1032(3) 0.0474(8) Uani d 1 C
C12 0.3035(6) -0.2446(4) 0.1603(3) 0.0460(8) Uani d 1 C
H2 0.637(5) 0.064(4) 0.329(3) 0.032(8) Uiso d 1 H
H3 0.613(6) 0.318(5) 0.460(3) 0.058(11) Uiso d 1 H
H6 0.717(6) 0.136(4) 0.158(3) 0.043(9) Uiso d 1 H
H7 0.393(6) 0.172(4) 0.037(3) 0.044(9) Uiso d 1 H
H8 0.200(5) 0.394(4) 0.107(3) 0.042(9) Uiso d 1 H
H9 0.139(6) 0.344(5) 0.300(3) 0.050(10) Uiso d 1 H
H11A 0.100(6) -0.199(5) 0.012(4) 0.064(12) Uiso d 1 H
H11B -0.028(6) -0.233(5) 0.129(3) 0.049(10) Uiso d 1 H
H12A 0.289(5) -0.285(4) 0.234(3) 0.032(8) Uiso d 1 H
H12B 0.378(7) -0.330(5) 0.115(4) 0.066(12) 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 108.5(2) ?
C10 O3 C12 107.9(2) ?
C9 C1 C2 108.9(2) y
C9 C1 C10 100.2(2) y
C2 C1 C10 100.2(2) y
C9 C1 Br1 115.2(2) y
C2 C1 Br1 114.9(2) y
C10 C1 Br1 115.5(2) y
C3 C2 C1 116.5(2) ?
C3 C2 C6 105.0(2) ?
C1 C2 C6 101.1(2) ?
C3 C2 H2 112.9(18) ?
C1 C2 H2 109.4(18) ?
C6 C2 H2 111.2(18) ?
C4 C3 C2 112.2(3) y
C4 C3 H3 125.(2) ?
C2 C3 H3 123.(2) ?
C3 C4 C5 112.0(3) y
C3 C4 Br2 127.0(2) y
C5 C4 Br2 121.0(2) y
O1 C5 C4 126.9(3) ?
O1 C5 C6 127.1(3) ?
C4 C5 C6 106.0(2) ?
C5 C6 C2 104.7(2) ?
C5 C6 C7 114.4(2) ?
C2 C6 C7 103.8(2) ?
C5 C6 H6 112.(2) ?
C2 C6 H6 108.(2) ?
C7 C6 H6 113.(2) ?
C8 C7 C10 100.1(2) y
C8 C7 C6 106.9(2) y
C10 C7 C6 99.5(2) y
C8 C7 H7 115.(2) ?
C10 C7 H7 116.(2) ?
C6 C7 H7 117.(2) ?
C9 C8 C7 108.2(3) ?
C9 C8 H8 128.(2) ?
C7 C8 H8 124.(2) ?
C8 C9 C1 107.6(3) ?
C8 C9 H9 128.(3) ?
C1 C9 H9 124.(3) ?
O3 C10 O2 108.2(2) ?
O3 C10 C7 112.6(2) ?
O2 C10 C7 115.9(2) ?
O3 C10 C1 114.8(2) ?
O2 C10 C1 112.5(2) ?
C7 C10 C1 92.4(2) y
O2 C11 C12 104.0(3) ?
O2 C11 H11A 110.(2) ?
C12 C11 H11A 109.(2) ?
O2 C11 H11B 107.(2) ?
C12 C11 H11B 115.(2) ?
H11A C11 H11B 112.(3) ?
O3 C12 C11 102.7(2) ?
O3 C12 H12A 110.7(19) ?
C11 C12 H12A 113.(2) ?
O3 C12 H12B 107.(3) ?
C11 C12 H12B 115.(2) ?
H12A C12 H12B 108.(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 1.925(3) y
Br2 C4 1.872(3) y
O1 C5 1.200(4) ?
O2 C10 1.401(3) ?
O2 C11 1.427(4) ?
O3 C10 1.397(3) ?
O3 C12 1.433(4) ?
C1 C9 1.499(4) y
C1 C2 1.547(4) y
C1 C10 1.552(4) y
C2 C3 1.485(4) ?
C2 C6 1.559(4) ?
C2 H2 0.98(3) ?
C3 C4 1.320(4) y
C3 H3 1.00(4) ?
C4 C5 1.488(4) ?
C5 C6 1.523(4) ?
C6 C7 1.563(4) y
C6 H6 0.94(4) ?
C7 C8 1.489(4) y
C7 C10 1.541(4) y
C7 H7 0.86(3) ?
C8 C9 1.313(4) y
C8 H8 0.88(3) ?
C9 H9 0.86(4) ?
C11 C12 1.503(5) ?
C11 H11A 1.07(4) ?
C11 H11B 0.94(4) ?
C12 H12A 0.94(3) ?
C12 H12B 1.01(4) ?
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 48.6(3)
C10 C1 C2 C3 153.2(2)
Br1 C1 C2 C3 -82.3(3)
C9 C1 C2 C6 -64.5(3)
C10 C1 C2 C6 40.2(2)
Br1 C1 C2 C6 164.6(2)
C1 C2 C3 C4 -107.7(3)
C6 C2 C3 C4 3.2(3)
C2 C3 C4 C5 -0.9(4)
C2 C3 C4 Br2 179.4(2)
C3 C4 C5 O1 177.8(3)
Br2 C4 C5 O1 -2.4(4)
C3 C4 C5 C6 -1.8(3)
Br2 C4 C5 C6 177.9(2)
O1 C5 C6 C2 -176.1(3)
C4 C5 C6 C2 3.6(3)
O1 C5 C6 C7 -63.1(4)
C4 C5 C6 C7 116.5(3)
C3 C2 C6 C5 -4.0(3)
C1 C2 C6 C5 117.5(2)
C3 C2 C6 C7 -124.3(2)
C1 C2 C6 C7 -2.8(3)
C5 C6 C7 C8 -45.4(3)
C2 C6 C7 C8 68.1(3)
C5 C6 C7 C10 -149.1(2)
C2 C6 C7 C10 -35.7(3)
C10 C7 C8 C9 35.4(3)
C6 C7 C8 C9 -67.9(3)
C7 C8 C9 C1 -1.5(3)
C2 C1 C9 C8 71.9(3)
C10 C1 C9 C8 -32.7(3)
Br1 C1 C9 C8 -157.3(2)
C12 O3 C10 O2 -16.8(3)
C12 O3 C10 C7 -146.2(3)
C12 O3 C10 C1 109.8(3)
C11 O2 C10 O3 -2.4(3)
C11 O2 C10 C7 125.2(3)
C11 O2 C10 C1 -130.2(3)
C8 C7 C10 O3 -168.8(2)
C6 C7 C10 O3 -59.6(3)
C8 C7 C10 O2 65.8(3)
C6 C7 C10 O2 175.0(2)
C8 C7 C10 C1 -50.7(2)
C6 C7 C10 C1 58.5(2)
C9 C1 C10 O3 166.2(2)
C2 C1 C10 O3 54.6(3)
Br1 C1 C10 O3 -69.4(3)
C9 C1 C10 O2 -69.5(3)
C2 C1 C10 O2 179.0(2)
Br1 C1 C10 O2 54.9(3)
C9 C1 C10 C7 49.9(2)
C2 C1 C10 C7 -61.7(2)
Br1 C1 C10 C7 174.3(2)
C10 O2 C11 C12 19.3(3)
C10 O3 C12 C11 27.8(3)
O2 C11 C12 O3 -28.3(3)