#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/15/2011572.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_2011572 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 H4 Cl6 O4' _chemical_formula_sum 'C9 H4 Cl6 O4' _chemical_formula_weight 388.82 _chemical_name_systematic ; 1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-endo-cis-5,6-dicarboxylic acid ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 101.650(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.4990(10) _cell_length_b 7.924(2) _cell_length_c 11.873(2) _cell_measurement_reflns_used 511 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 1 _cell_volume 691.0(2) _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 .025 _diffrn_reflns_av_sigmaI/netI .017 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _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 19175 _diffrn_reflns_theta_full 28.28 _diffrn_reflns_theta_max 28.28 _diffrn_reflns_theta_min 1.75 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 1200 _diffrn_standards_number 325 _exptl_absorpt_coefficient_mu 1.246 _exptl_absorpt_correction_T_max .835 _exptl_absorpt_correction_T_min .636 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.869 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 384 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .15 _refine_diff_density_max .28 _refine_diff_density_min -.21 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack .02(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 180 _refine_ls_number_reflns 3424 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all .020 _refine_ls_R_factor_gt .019 _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^)+(0.03P)^2^+0.0924P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .048 _reflns_number_gt 3293 _reflns_number_total 3424 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1412.cif _[local]_cod_data_source_block IVa _[local]_cod_cif_authors_sg_H-M 'P 21' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 'Monoclinic' changed to 'monoclinic' 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 2011572 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 .69443(18) .56656(19) .66518(12) .0136(3) Uani d . 1 . . C H1 .5763 .5043 .6443 .016 Uiso calc R 1 . . H C11 .8403(2) .45674(19) .62955(13) .0157(3) Uani d . 1 . . C O11 .99048(15) .42735(15) .68550(9) .0197(2) Uani d . 1 . . O O12 .77577(16) .39949(16) .52437(10) .0242(3) Uani d . 1 . . O H12 .854(3) .356(3) .500(2) .034(6) Uiso d . 1 . . H C2 .66776(19) .74293(18) .60301(12) .0147(3) Uani d . 1 . . C H2 .5418 .7502 .5554 .018 Uiso calc R 1 . . H C21 .8045(2) .78274(19) .52874(14) .0164(3) Uani d . 1 . . C O21 .96690(15) .75069(17) .55919(11) .0253(3) Uani d . 1 . . O O22 .73263(16) .85559(18) .43038(10) .0252(3) Uani d . 1 . . O H22 .815(4) .866(4) .394(2) .055(8) Uiso d . 1 . . H C3 .6853(2) .86596(19) .70806(13) .0169(3) Uani d . 1 . . C Cl3 .59753(6) 1.06861(5) .67095(4) .02737(9) Uani d . 1 . . Cl C4 .8791(2) .8599(2) .77924(13) .0179(3) Uani d . 1 . . C Cl4 1.03082(6) 1.02032(5) .78540(4) .02851(10) Uani d . 1 . . Cl C5 .90148(19) .7098(2) .83183(12) .0177(3) Uani d . 1 . . C Cl5 1.08377(5) .63452(6) .92641(3) .02633(9) Uani d . 1 . . Cl C6 .7233(2) .61224(19) .79471(13) .0163(3) Uani d . 1 . . C Cl6 .68870(6) .44331(5) .88242(4) .02736(9) Uani d . 1 . . Cl C7 .5867(2) .7625(2) .78891(13) .0181(3) Uani d . 1 . . C Cl71 .35827(5) .70969(5) .72692(3) .02249(9) Uani d . 1 . . Cl Cl72 .58781(6) .86019(6) .92252(4) .02939(10) 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 .0126(6) .0134(6) .0160(6) -.0002(5) .0055(5) -.0003(5) C11 .0181(7) .0121(6) .0189(7) -.0018(5) .0083(6) -.0005(6) O11 .0187(5) .0206(5) .0202(5) .0040(5) .0049(4) .0004(5) O12 .0159(5) .0322(7) .0244(6) .0045(5) .0039(5) -.0116(5) C2 .0140(6) .0144(7) .0166(7) .0002(5) .0048(5) .0006(5) C21 .0174(7) .0144(6) .0180(7) -.0009(5) .0052(5) .0022(5) O21 .0151(5) .0350(7) .0268(6) .0003(5) .0068(4) .0113(5) O22 .0192(5) .0369(7) .0204(6) .0022(5) .0059(5) .0131(5) C3 .0169(7) .0130(6) .0212(7) .0006(5) .0049(6) -.0010(6) Cl3 .0289(2) .01399(17) .0380(2) .00485(15) .00408(17) -.00003(16) C4 .0159(7) .0182(7) .0201(7) -.0022(6) .0046(5) -.0040(6) Cl4 .02409(19) .02241(18) .0388(2) -.00978(15) .00585(16) -.00508(17) C5 .0169(7) .0217(7) .0152(6) .0001(6) .0045(5) -.0015(6) Cl5 .02127(17) .0369(2) .01900(18) .00374(17) -.00037(14) .00260(16) C6 .0181(7) .0160(7) .0164(6) -.0005(6) .0075(5) .0015(5) Cl6 .0347(2) .02510(19) .0254(2) -.00138(17) .01352(16) .00918(17) C7 .0173(7) .0201(7) .0184(7) -.0006(6) .0073(6) -.0042(6) Cl71 .01438(15) .02752(19) .02752(19) -.00098(14) .00888(13) -.00406(16) Cl72 .0298(2) .0371(2) .0242(2) -.00039(18) .01248(16) -.01302(18) 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 . 1.523(2) ? C1 C6 . 1.552(2) ? C1 C2 . 1.574(2) ? C1 H1 . 1.0000 ? C11 O11 . 1.2087(19) ? C11 O12 . 1.3250(19) ? O12 H12 . .79(2) ? C2 C21 . 1.515(2) ? C2 C3 . 1.568(2) ? C2 H2 . 1.0000 ? C21 O21 . 1.2249(19) ? C21 O22 . 1.3165(19) ? O22 H22 . .83(3) ? C3 C4 . 1.527(2) ? C3 C7 . 1.558(2) ? C3 Cl3 . 1.7576(16) ? C4 C5 . 1.338(2) ? C4 Cl4 . 1.6978(16) ? C5 C6 . 1.530(2) ? C5 Cl5 . 1.6928(15) ? C6 C7 . 1.563(2) ? C6 Cl6 . 1.7471(16) ? C7 Cl72 . 1.7635(16) ? C7 Cl71 . 1.7725(16) ? 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 C11 C1 C6 116.37(12) C11 C1 C2 114.03(11) C6 C1 C2 103.69(11) C11 C1 H1 107.4 C6 C1 H1 107.4 C2 C1 H1 107.4 O11 C11 O12 125.07(14) O11 C11 C1 126.80(13) O12 C11 C1 108.12(12) C11 O12 H12 109.8(17) C21 C2 C3 112.07(12) C21 C2 C1 114.90(12) C3 C2 C1 101.35(11) C21 C2 H2 109.4 C3 C2 H2 109.4 C1 C2 H2 109.4 O21 C21 O22 123.87(14) O21 C21 C2 122.31(14) O22 C21 C2 113.81(13) C21 O22 H22 107(2) C4 C3 C7 99.17(12) C4 C3 C2 109.79(12) C7 C3 C2 100.90(12) C4 C3 Cl3 115.71(11) C7 C3 Cl3 115.77(11) C2 C3 Cl3 113.69(10) C5 C4 C3 107.57(13) C5 C4 Cl4 128.72(12) C3 C4 Cl4 123.71(12) C4 C5 C6 107.14(13) C4 C5 Cl5 129.14(12) C6 C5 Cl5 123.69(12) C5 C6 C1 110.01(12) C5 C6 C7 98.88(12) C1 C6 C7 100.08(12) C5 C6 Cl6 116.20(11) C1 C6 Cl6 113.84(11) C7 C6 Cl6 115.79(10) C3 C7 C6 92.27(11) C3 C7 Cl72 114.00(11) C6 C7 Cl72 114.25(11) C3 C7 Cl71 114.05(11) C6 C7 Cl71 114.08(11) Cl72 C7 Cl71 107.81(8) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O12 H12 O21 2_746 .79(2) 1.83(3) 2.6214(17) 179(3) O22 H22 O11 2_756 .83(3) 1.95(3) 2.7716(17) 171(3) 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 C6 C1 C11 O11 -14.7(2) C2 C1 C11 O11 105.94(17) C6 C1 C11 O12 166.21(12) C2 C1 C11 O12 -73.11(16) C11 C1 C2 C21 -6.57(18) C6 C1 C2 C21 120.97(13) C11 C1 C2 C3 -127.61(12) C6 C1 C2 C3 -.08(13) C3 C2 C21 O21 73.26(19) C1 C2 C21 O21 -41.7(2) C3 C2 C21 O22 -106.09(15) C1 C2 C21 O22 138.93(14) C21 C2 C3 C4 -56.69(16) C1 C2 C3 C4 66.32(14) C21 C2 C3 C7 -160.69(12) C1 C2 C3 C7 -37.68(13) C21 C2 C3 Cl3 74.70(14) C1 C2 C3 Cl3 -162.29(10) C7 C3 C4 C5 34.81(15) C2 C3 C4 C5 -70.36(16) Cl3 C3 C4 C5 159.32(12) C7 C3 C4 Cl4 -145.45(12) C2 C3 C4 Cl4 109.39(14) Cl3 C3 C4 Cl4 -20.94(18) C3 C4 C5 C6 .89(17) Cl4 C4 C5 C6 -178.83(12) C3 C4 C5 Cl5 -176.88(12) Cl4 C4 C5 Cl5 3.4(2) C4 C5 C6 C1 68.10(16) Cl5 C5 C6 C1 -113.98(13) C4 C5 C6 C7 -36.11(15) Cl5 C5 C6 C7 141.81(12) C4 C5 C6 Cl6 -160.70(11) Cl5 C5 C6 Cl6 17.22(17) C11 C1 C6 C5 60.22(17) C2 C1 C6 C5 -65.85(14) C11 C1 C6 C7 163.61(12) C2 C1 C6 C7 37.55(13) C11 C1 C6 Cl6 -72.21(14) C2 C1 C6 Cl6 161.72(9) C4 C3 C7 C6 -52.81(13) C2 C3 C7 C6 59.55(12) Cl3 C3 C7 C6 -177.27(10) C4 C3 C7 Cl72 65.07(13) C2 C3 C7 Cl72 177.42(10) Cl3 C3 C7 Cl72 -59.40(14) C4 C3 C7 Cl71 -170.51(10) C2 C3 C7 Cl71 -58.15(13) Cl3 C3 C7 Cl71 65.03(14) C5 C6 C7 C3 53.28(12) C1 C6 C7 C3 -59.02(12) Cl6 C6 C7 C3 178.16(10) C5 C6 C7 Cl72 -64.38(13) C1 C6 C7 Cl72 -176.68(10) Cl6 C6 C7 Cl72 60.50(14) C5 C6 C7 Cl71 170.95(10) C1 C6 C7 Cl71 58.65(13) Cl6 C6 C7 Cl71 -64.16(14)