#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$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_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 \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' _[local]_cod_chemical_formula_sum_orig 'C9 H2 Cl6 O3 , 0.16(C4 H10 O)' _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_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_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_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_ _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_ _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_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)