data_2011573 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 1338 _journal_page_last 1342 _publ_section_title ; Diels-Alder adducts of maleic anhydride and dienes: new compounds by crystallization ; loop_ _publ_author_name 'Bolte, Michael' 'Degen, Alexander' 'Egert, Ernst' _chemical_formula_moiety 'C9 H4 Cl6 O4' _chemical_formula_sum 'C9 H4 Cl6 O4' _chemical_formula_weight 388.82 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.4430(10) _cell_length_b 24.8090(10) _cell_length_c 13.5940(10) _cell_angle_alpha 90 _cell_angle_beta 90.380(10) _cell_angle_gamma 90 _cell_volume 2847.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _exptl_crystal_density_diffrn 1.814 _diffrn_ambient_temperature 173(2) 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 .40303(17) .57589(6) .05060(10) .0152(3) Uani d . 1 . . C H1 .3967 .5592 -.0163 .018 Uiso calc R 1 . . H C11 .31014(19) .54093(6) .12113(11) .0183(3) Uani d . 1 . . C O11 .20251(15) .55721(5) .17186(10) .0281(3) Uani d . 1 . . O O12 .36090(16) .49070(5) .12002(9) .0266(3) Uani d . 1 . . O H12 .312(4) .4732(12) .158(2) .065(9) Uiso d . 1 . . H C2 .58295(18) .58333(6) .07849(11) .0164(3) Uani d . 1 . . C H2 .6469 .5730 .0198 .020 Uiso calc R 1 . . H C21 .64166(19) .55000(6) .16492(11) .0199(3) Uani d . 1 . . C O21 .60277(16) .55752(5) .25014(8) .0289(3) Uani d . 1 . . O O22 .73663(17) .51146(6) .13545(10) .0319(3) Uani d . 1 . . O H22 .761(3) .4947(12) .180(2) .062(9) Uiso d . 1 . . H C3 .59588(17) .64548(6) .09100(11) .0161(3) Uani d . 1 . . C Cl3 .79204(5) .668329(19) .09327(3) .02970(9) Uani d . 1 . . Cl C4 .49067(18) .66525(6) .17445(11) .0178(3) Uani d . 1 . . C Cl4 .56021(5) .692073(19) .28104(3) .03112(10) Uani d . 1 . . Cl C5 .34005(18) .66042(6) .14541(11) .0165(3) Uani d . 1 . . C Cl5 .17543(5) .681273(17) .20501(3) .02577(9) Uani d . 1 . . Cl C6 .34183(17) .63490(6) .04291(10) .0142(3) Uani d . 1 . . C Cl6 .16874(5) .641385(16) -.02796(3) .02392(8) Uani d . 1 . . Cl C7 .49143(18) .66422(6) .00175(11) .0154(3) Uani d . 1 . . C Cl71 .55830(5) .640423(15) -.11362(3) .02192(8) Uani d . 1 . . Cl Cl72 .46621(5) .734510(15) -.00749(3) .02487(9) Uani d . 1 . . Cl C1A .90607(17) .57664(6) .58458(11) .0158(3) Uani d . 1 . . C H1A .8400 .5626 .5289 .019 Uiso calc R 1 . . H C11A .85269(19) .54735(6) .67609(11) .0200(3) Uani d . 1 . . C O11A .78471(15) .56857(5) .74461(9) .0263(3) Uani d . 1 . . O O12A .88191(17) .49534(5) .66866(10) .0309(3) Uani d . 1 . . O H12A .854(3) .4793(12) .719(2) .063(9) Uiso d . 1 . . H C2A 1.08377(17) .56819(6) .55473(10) .0154(3) Uani d . 1 . . C H2A 1.0887 .5480 .4912 .019 Uiso calc R 1 . . H C21A 1.18283(19) .53924(6) .63230(11) .0187(3) Uani d . 1 . . C O21A 1.17476(17) .55117(5) .71922(9) .0306(3) Uani d . 1 . . O O22A 1.27283(15) .50093(5) .59729(9) .0262(3) Uani d . 1 . . O H22A 1.322(4) .4843(14) .648(3) .084(11) Uiso d . 1 . . H C3A 1.14044(17) .62763(6) .53850(11) .0157(3) Uani d . 1 . . C Cl3A 1.31328(5) .632293(17) .46804(3) .02498(8) Uani d . 1 . . Cl C4A 1.14115(18) .65700(6) .63701(11) .0172(3) Uani d . 1 . . C Cl4A 1.30844(5) .674789(18) .69863(3) .02864(9) Uani d . 1 . . Cl C5A .99106(18) .66355(6) .66446(11) .0173(3) Uani d . 1 . . C Cl5A .92267(5) .693265(17) .76826(3) .02881(9) Uani d . 1 . . Cl C6A .88620(17) .63890(6) .58465(11) .0162(3) Uani d . 1 . . C Cl6A .68949(5) .660605(19) .58116(3) .02991(9) Uani d . 1 . . Cl C7A .98846(18) .65370(6) .49272(11) .0172(3) Uani d . 1 . . C Cl73 .92290(5) .623165(17) .38217(3) .02441(8) Uani d . 1 . . Cl Cl74 1.00832(5) .723432(16) .47172(3) .02732(9) Uani d . 1 . . Cl 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 .0193(7) .0128(6) .0135(6) -.0003(5) .0014(5) .0017(5) C11 .0235(7) .0140(7) .0173(7) -.0020(5) .0010(6) .0021(5) O11 .0306(6) .0190(6) .0349(7) .0026(5) .0149(5) .0077(5) O12 .0400(7) .0136(5) .0263(6) .0008(5) .0127(5) .0044(5) C2 .0185(7) .0166(7) .0141(6) .0038(5) .0016(5) .0023(5) C21 .0215(7) .0206(7) .0176(7) .0038(6) -.0015(6) .0036(6) O21 .0384(7) .0317(7) .0167(5) .0122(5) .0007(5) .0049(5) O22 .0425(8) .0321(7) .0212(6) .0215(6) -.0010(5) .0060(5) C3 .0131(6) .0185(7) .0168(7) -.0007(5) .0011(5) .0005(5) Cl3 .01599(18) .0381(2) .0350(2) -.00718(16) .00140(15) -.00055(18) C4 .0212(7) .0175(7) .0148(7) -.0006(6) .0014(5) -.0018(5) Cl4 .0346(2) .0387(2) .02006(18) -.00542(18) -.00291(16) -.01031(16) C5 .0194(7) .0145(6) .0157(7) .0014(5) .0049(5) .0003(5) Cl5 .02282(19) .02711(19) .02753(19) .00383(15) .01106(15) -.00218(15) C6 .0145(6) .0138(6) .0143(6) -.0005(5) .0004(5) .0019(5) Cl6 .01877(17) .02762(19) .02530(19) .00227(14) -.00638(14) .00333(15) C7 .0186(7) .0128(6) .0150(6) .0007(5) .0031(5) .0027(5) Cl71 .02922(19) .02264(18) .01397(16) .00442(14) .00587(14) .00377(13) Cl72 .0339(2) .01278(16) .02804(19) -.00005(14) .00640(16) .00511(14) C1A .0174(7) .0151(7) .0150(6) -.0014(5) .0009(5) .0017(5) C11A .0234(8) .0167(7) .0200(7) -.0032(6) .0034(6) .0013(6) O11A .0370(7) .0181(5) .0241(6) -.0002(5) .0143(5) .0022(4) O12A .0508(8) .0144(5) .0277(6) -.0004(5) .0186(6) .0031(5) C2A .0180(7) .0144(6) .0139(6) .0013(5) .0008(5) .0020(5) C21A .0222(7) .0144(7) .0196(7) .0023(6) -.0009(6) .0022(5) O21A .0481(8) .0257(6) .0178(6) .0145(6) -.0061(5) .0014(5) O22A .0298(6) .0259(6) .0229(6) .0124(5) -.0014(5) .0008(5) C3A .0146(6) .0168(7) .0156(6) .0002(5) .0015(5) .0022(5) Cl3A .01929(18) .0307(2) .02506(19) -.00258(15) .00769(14) .00209(15) C4A .0184(7) .0160(7) .0171(7) -.0009(5) -.0028(5) .0016(5) Cl4A .02277(19) .0360(2) .0270(2) -.00537(16) -.00761(15) -.00312(17) C5A .0220(7) .0141(6) .0157(7) .0017(5) .0011(5) .0002(5) Cl5A .0350(2) .0279(2) .02368(19) .00196(17) .00765(16) -.00799(15) C6A .0135(6) .0171(7) .0180(7) .0018(5) .0000(5) .0032(5) Cl6A .01629(18) .0357(2) .0378(2) .00892(16) -.00020(15) .00513(18) C7A .0196(7) .0162(7) .0157(7) .0002(5) -.0015(5) .0043(5) Cl73 .0293(2) .02846(19) .01538(16) -.00220(15) -.00557(14) .00405(14) Cl74 .0368(2) .01635(17) .0288(2) .00087(15) -.00033(16) .00963(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 C11 . 1.515(2) ? C1 C6 . 1.5558(19) ? C1 C2 . 1.574(2) ? C1 H1 . 1.0000 ? C11 O11 . 1.214(2) ? C11 O12 . 1.3180(18) ? O12 H12 . .79(3) ? C2 C21 . 1.517(2) ? C2 C3 . 1.555(2) ? C2 H2 . 1.0000 ? C21 O21 . 1.2206(19) ? C21 O22 . 1.312(2) ? O22 H22 . .76(3) ? C3 C4 . 1.526(2) ? C3 C7 . 1.566(2) ? C3 Cl3 . 1.7506(15) ? C4 C5 . 1.334(2) ? C4 Cl4 . 1.6959(15) ? C5 C6 . 1.531(2) ? C5 Cl5 . 1.6944(15) ? C6 C7 . 1.564(2) ? C6 Cl6 . 1.7524(15) ? C7 Cl72 . 1.7612(15) ? C7 Cl71 . 1.7717(15) ? C1A C11A . 1.512(2) ? C1A C6A . 1.554(2) ? C1A C2A . 1.571(2) ? C1A H1A . 1.0000 ? C11A O11A . 1.2171(19) ? C11A O12A . 1.3178(19) ? O12A H12A . .83(3) ? C2A C21A . 1.522(2) ? C2A C3A . 1.567(2) ? C2A H2A . 1.0000 ? C21A O21A . 1.2205(19) ? C21A O22A . 1.3085(19) ? O22A H22A . .90(4) ? C3A C4A . 1.524(2) ? C3A C7A . 1.562(2) ? C3A Cl3A . 1.7547(15) ? C4A C5A . 1.333(2) ? C4A Cl4A . 1.6958(15) ? C5A C6A . 1.524(2) ? C5A Cl5A . 1.6967(15) ? C6A C7A . 1.567(2) ? C6A Cl6A . 1.7463(15) ? C7A Cl74 . 1.7615(15) ? C7A Cl73 . 1.7686(16) ?