#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011570.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_2011570
loop_
_publ_author_name
'Bolte, Michael'
'Degen, Alexander'
'Egert, Ernst'
_publ_section_title
;
 Diels--Alder adducts of maleic anhydride and dienes: new compounds by
 crystallization
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1338
_journal_page_last               1342
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C9 H2 Cl6 O3 , 0.16C4 H10 O'
_chemical_formula_sum            'C9 H2 Cl6 O3 , 0.16C4 H10 O'
_chemical_formula_weight         383.16
_chemical_name_systematic
;
1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-endo-cis-5,6-dicarboxylic
anhydride diethyl ether solvate
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   29.639(4)
_cell_length_b                   29.639(4)
_cell_length_c                   8.119(2)
_cell_measurement_reflns_used    512
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      1
_cell_volume                     6176.8(19)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens CCD three-circle'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .045
_diffrn_reflns_av_sigmaI/netI    .022
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            31306
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  1800
_diffrn_standards_number         317
_exptl_absorpt_coefficient_mu    1.249
_exptl_absorpt_correction_T_max  .835
_exptl_absorpt_correction_T_min  .706
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3402
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .15
_refine_diff_density_max         .73
_refine_diff_density_min         -.38
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2811
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          .046
_refine_ls_R_factor_gt           .032
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0319P)^2^+19.3097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .078
_reflns_number_gt                2314
_reflns_number_total             2811
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    sk1412.cif
_[local]_cod_data_source_block   II
_[local]_cod_cif_authors_sg_H-M  R-3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
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               2011570
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 .32288(9) .40866(9) .3739(3) .0236(5) Uani d . 1 C
H1 .3598 .4163 .3724 .028 Uiso calc R 1 H
C2 .31361(9) .44191(9) .2488(3) .0251(5) Uani d . 1 C
H2 .3461 .4657 .1866 .030 Uiso calc R 1 H
C3 .29484(10) .47295(9) .3578(3) .0252(5) Uani d . 1 C
Cl3 .29797(3) .52706(3) .26211(10) .0464(2) Uani d . 1 Cl
C4 .24234(9) .43351(9) .4300(3) .0230(5) Uani d . 1 C
Cl4 .18418(3) .42570(3) .36819(8) .03901(18) Uani d . 1 Cl
C5 .25017(9) .40453(9) .5379(3) .0215(5) Uani d . 1 C
Cl5 .20471(2) .35140(3) .64147(8) .03192(16) Uani d . 1 Cl
C6 .30830(9) .42379(9) .5416(3) .0230(5) Uani d . 1 C
Cl6 .33108(3) .40670(3) .71498(8) .03710(17) Uani d . 1 Cl
C7 .32971(9) .48300(10) .5122(3) .0280(5) Uani d . 1 C
Cl71 .39703(3) .51862(3) .46847(10) .04236(19) Uani d . 1 Cl
Cl72 .31643(3) .51406(3) .67495(9) .03886(18) Uani d . 1 Cl
C8 .28509(9) .35302(10) .3245(3) .0242(5) Uani d . 1 C
O2 .27761(7) .31351(7) .3867(2) .0313(4) Uani d . 1 O
C9 .27141(10) .40316(10) .1365(3) .0260(5) Uani d . 1 C
O3 .25089(8) .40991(8) .0220(2) .0374(5) Uani d . 1 O
O1 .25653(7) .35263(6) .1891(2) .0270(4) Uani d . 1 O
C11 .3617(6) .6579(6) .4546(18) .092(4) Uiso d P .33 C
H11A .3643 .6786 .5488 .138 Uiso d PR .33 H
H11B .3435 .6217 .4846 .138 Uiso d PR .33 H
H11C .3960 .6674 .4163 .138 Uiso d PR .33 H
C12 .3333 .6667 .3124(14) .143(4) Uiso d SD 1 C
H12A .3514 .7031 .2861 .172 Uiso d PR .33 H
H12B .2996 .6580 .3536 .172 Uiso d PR .33 H
O13 .327(4) .6365(16) .1648(11) .117(8) Uiso d PD .17 O
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
C1 .0163(11) .0244(12) .0297(12) .0098(10) .0005(9) -.0036(10)
C2 .0226(12) .0254(12) .0252(12) .0105(10) .0069(10) .0026(10)
C3 .0274(13) .0212(12) .0276(12) .0126(11) .0023(10) .0013(10)
Cl3 .0623(5) .0302(4) .0521(4) .0272(4) .0087(4) .0121(3)
C4 .0201(12) .0278(13) .0247(12) .0148(10) -.0013(9) -.0045(10)
Cl4 .0288(3) .0604(5) .0383(4) .0301(3) -.0026(3) .0027(3)
C5 .0174(11) .0250(12) .0198(11) .0088(10) .0006(9) -.0037(9)
Cl5 .0289(3) .0317(3) .0282(3) .0100(3) .0069(2) .0046(3)
C6 .0214(12) .0258(12) .0238(12) .0132(10) -.0045(9) -.0043(10)
Cl6 .0406(4) .0486(4) .0313(3) .0292(3) -.0153(3) -.0080(3)
C7 .0205(12) .0257(13) .0345(13) .0091(11) .0004(10) -.0082(11)
Cl71 .0207(3) .0332(4) .0579(5) .0020(3) .0024(3) -.0138(3)
Cl72 .0386(4) .0346(4) .0427(4) .0177(3) -.0013(3) -.0169(3)
C8 .0220(12) .0288(13) .0241(12) .0143(10) .0011(9) -.0056(10)
O2 .0387(11) .0248(9) .0342(10) .0188(8) .0008(8) -.0013(8)
C9 .0278(13) .0302(13) .0221(12) .0162(11) .0069(10) .0004(10)
O3 .0455(12) .0462(12) .0254(9) .0265(10) -.0022(8) .0009(8)
O1 .0279(9) .0270(9) .0267(9) .0141(8) -.0042(7) -.0048(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C8 C1 C2 . . 104.60(19)
C8 C1 C6 . . 112.60(19)
C2 C1 C6 . . 103.24(18)
C8 C1 H1 . . 112.0
C2 C1 H1 . . 112.0
C6 C1 H1 . . 112.0
C9 C2 C1 . . 104.94(19)
C9 C2 C3 . . 112.7(2)
C1 C2 C3 . . 103.54(19)
C9 C2 H2 . . 111.7
C1 C2 H2 . . 111.7
C3 C2 H2 . . 111.7
C4 C3 C7 . . 99.37(18)
C4 C3 C2 . . 107.09(19)
C7 C3 C2 . . 99.84(19)
C4 C3 Cl3 . . 116.27(17)
C7 C3 Cl3 . . 117.28(17)
C2 C3 Cl3 . . 114.71(17)
C5 C4 C3 . . 108.0(2)
C5 C4 Cl4 . . 127.02(19)
C3 C4 Cl4 . . 124.75(18)
C4 C5 C6 . . 107.6(2)
C4 C5 Cl5 . . 127.83(19)
C6 C5 Cl5 . . 124.30(18)
C5 C6 C7 . . 99.60(18)
C5 C6 C1 . . 107.42(18)
C7 C6 C1 . . 100.04(19)
C5 C6 Cl6 . . 115.98(17)
C7 C6 Cl6 . . 116.93(17)
C1 C6 Cl6 . . 114.71(16)
C3 C7 C6 . . 92.89(18)
C3 C7 Cl72 . . 113.80(17)
C6 C7 Cl72 . . 113.67(18)
C3 C7 Cl71 . . 113.36(18)
C6 C7 Cl71 . . 113.99(17)
Cl72 C7 Cl71 . . 108.61(13)
O2 C8 O1 . . 121.1(2)
O2 C8 C1 . . 129.2(2)
O1 C8 C1 . . 109.7(2)
O3 C9 O1 . . 120.5(2)
O3 C9 C2 . . 130.3(2)
O1 C9 C2 . . 109.1(2)
C8 O1 C9 . . 111.65(18)
C12 C11 C11 . 3_565 55.5(5)
C12 C11 C11 . 2_665 55.5(5)
C11 C11 C11 3_565 2_665 60.002(4)
C12 C11 H11A . . 111.7
C12 C11 H11B . . 109.4
H11A C11 H11B . . 109.5
C12 C11 H11C . . 107.3
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
O13 C12 C11 . . 115(3)
O13 C12 H12A . . 109.7
C11 C12 H12A . . 108.4
O13 C12 H12B . . 109.3
C11 C12 H12B . . 106.3
H12A C12 H12B . . 107.5
C12 O13 C12 13_565 . 110.6(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C8 1.513(3)
C1 C2 1.532(3)
C1 C6 1.561(3)
C1 H1 1.0000
C2 C9 1.509(3)
C2 C3 1.565(3)
C2 H2 1.0000
C3 C4 1.521(3)
C3 C7 1.556(3)
C3 Cl3 1.742(2)
C4 C5 1.326(3)
C4 Cl4 1.697(2)
C5 C6 1.520(3)
C5 Cl5 1.697(2)
C6 C7 1.558(3)
C6 Cl6 1.742(2)
C7 Cl72 1.764(2)
C7 Cl71 1.765(2)
C8 O2 1.190(3)
C8 O1 1.384(3)
C9 O3 1.182(3)
C9 O1 1.400(3)
C11 C12 1.525(15)
C11 H11A .9601
C11 H11B .9599
C11 H11C .9599
C12 O13 1.451(9)
C12 H12A .9601
C12 H12B .9600
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C8 C1 C2 C9 . . -.2(2)
C6 C1 C2 C9 . . -118.14(19)
C8 C1 C2 C3 . . 118.2(2)
C6 C1 C2 C3 . . .2(2)
C9 C2 C3 C4 . . 46.6(3)
C1 C2 C3 C4 . . -66.2(2)
C9 C2 C3 C7 . . 149.7(2)
C1 C2 C3 C7 . . 36.9(2)
C9 C2 C3 Cl3 . . -84.0(2)
C1 C2 C3 Cl3 . . 163.17(16)
C7 C3 C4 C5 . . -34.5(2)
C2 C3 C4 C5 . . 68.9(2)
Cl3 C3 C4 C5 . . -161.34(17)
C7 C3 C4 Cl4 . . 150.29(18)
C2 C3 C4 Cl4 . . -106.3(2)
Cl3 C3 C4 Cl4 . . 23.5(3)
C3 C4 C5 C6 . . .2(2)
Cl4 C4 C5 C6 . . 175.22(18)
C3 C4 C5 Cl5 . . -174.04(18)
Cl4 C4 C5 Cl5 . . 1.0(3)
C4 C5 C6 C7 . . 34.2(2)
Cl5 C5 C6 C7 . . -151.32(18)
C4 C5 C6 C1 . . -69.6(2)
Cl5 C5 C6 C1 . . 104.9(2)
C4 C5 C6 Cl6 . . 160.62(17)
Cl5 C5 C6 Cl6 . . -24.9(3)
C8 C1 C6 C5 . . -46.0(3)
C2 C1 C6 C5 . . 66.2(2)
C8 C1 C6 C7 . . -149.5(2)
C2 C1 C6 C7 . . -37.2(2)
C8 C1 C6 Cl6 . . 84.5(2)
C2 C1 C6 Cl6 . . -163.23(16)
C4 C3 C7 C6 . . 51.21(19)
C2 C3 C7 C6 . . -58.12(19)
Cl3 C3 C7 C6 . . 177.35(17)
C4 C3 C7 Cl72 . . -66.3(2)
C2 C3 C7 Cl72 . . -175.61(16)
Cl3 C3 C7 Cl72 . . 59.9(2)
C4 C3 C7 Cl71 . . 168.94(16)
C2 C3 C7 Cl71 . . 59.6(2)
Cl3 C3 C7 Cl71 . . -64.9(2)
C5 C6 C7 C3 . . -51.29(19)
C1 C6 C7 C3 . . 58.49(19)
Cl6 C6 C7 C3 . . -177.04(16)
C5 C6 C7 Cl72 . . 66.3(2)
C1 C6 C7 Cl72 . . 176.08(16)
Cl6 C6 C7 Cl72 . . -59.4(2)
C5 C6 C7 Cl71 . . -168.49(16)
C1 C6 C7 Cl71 . . -58.7(2)
Cl6 C6 C7 Cl71 . . 65.8(2)
C2 C1 C8 O2 . . -179.0(2)
C6 C1 C8 O2 . . -67.6(3)
C2 C1 C8 O1 . . -.5(2)
C6 C1 C8 O1 . . 110.9(2)
C1 C2 C9 O3 . . 179.5(3)
C3 C2 C9 O3 . . 67.5(3)
C1 C2 C9 O1 . . .8(2)
C3 C2 C9 O1 . . -111.2(2)
O2 C8 O1 C9 . . 179.6(2)
C1 C8 O1 C9 . . 1.0(3)
O3 C9 O1 C8 . . 180.0(2)
C2 C9 O1 C8 . . -1.1(3)
C11 C12 O13 C12 . 13_565 -142(5)
C11 C12 O13 C12 3_565 13_565 140(5)