#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/15/2011570.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_paper_doi               10.1107/S0108270100010131
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C9 H2 Cl6 O3 , 0.16(C4 H10 O)'
_chemical_formula_sum            'C9.64 H3.6 Cl6 O3.16'
_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       ω
_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/[σ²(Fo²)+(0.0319P)²+19.3097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .078
_reflns_number_gt                2314
_reflns_number_total             2811
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1412.cif
_cod_data_source_block           II
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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_original_sg_symbol_H-M      'R -3'
_cod_original_formula_sum        'C9 H2 Cl6 O3 , 0.16(C4 H10 O)'
_cod_database_code               2011570
_cod_database_fobs_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_disorder_assembly
_atom_site_disorder_group
_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_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
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)
