#------------------------------------------------------------------------------ #$Date: 2016-02-19 22:18:51 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176760 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/15/2011569.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_2011569 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 H8 O3' _chemical_formula_sum 'C9 H8 O3' _chemical_formula_weight 164.15 _chemical_name_systematic ; bicyclo[2.2.1]hept-2-ene-endo-cis-5,6-dicarboxylic anhydride ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.926(2) _cell_length_b 9.489(3) _cell_length_c 13.452(5) _cell_measurement_reflns_used 7065 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 1 _cell_volume 756.4(4) _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 .037 _diffrn_reflns_av_sigmaI/netI .012 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 20569 _diffrn_reflns_theta_full 28.69 _diffrn_reflns_theta_max 28.69 _diffrn_reflns_theta_min 2.63 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 1440 _diffrn_standards_number 260 _exptl_absorpt_coefficient_mu .109 _exptl_absorpt_correction_T_max .981 _exptl_absorpt_correction_T_min .948 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 344 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .40 _exptl_crystal_size_min .18 _refine_diff_density_max .35 _refine_diff_density_min -.24 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 1155 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.138 _refine_ls_R_factor_all .043 _refine_ls_R_factor_gt .041 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0826P)^2^+0.0338P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .110 _reflns_number_gt 1082 _reflns_number_total 1155 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk1412.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 'Orthorhombic' changed to 'orthorhombic' 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 2011569 _cod_database_fobs_code 2011569 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' 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 .4506(3) .38619(15) .38354(11) .0212(3) Uani d . 1 . . C H1 .5270 .2939 .3711 .025 Uiso calc R 1 . . H C2 .5923(3) .48059(15) .45206(11) .0208(3) Uani d . 1 . . C H2 .7326 .4316 .4748 .025 Uiso calc R 1 . . H C3 .6486(3) .61180(17) .38476(12) .0253(3) Uani d . 1 . . C H3 .7792 .6711 .4063 .030 Uiso calc R 1 . . H C4 .4273(4) .68864(17) .36767(13) .0296(4) Uani d . 1 . . C H4 .3874 .7782 .3939 .036 Uiso calc R 1 . . H C5 .2991(3) .60833(18) .30933(13) .0288(4) Uani d . 1 . . C H5 .1512 .6301 .2869 .035 Uiso calc R 1 . . H C6 .4315(3) .47574(16) .28505(12) .0249(3) Uani d . 1 . . C H6 .3831 .4233 .2242 .030 Uiso calc R 1 . . H C7 .6743(3) .53521(18) .28384(12) .0265(3) Uani d . 1 . . C H7A .7016 .6007 .2278 .032 Uiso calc R 1 . . H H7B .7910 .4606 .2851 .032 Uiso calc R 1 . . H C8 .2314(3) .36648(16) .43786(13) .0246(3) Uani d . 1 . . C C9 .4384(3) .51363(17) .53771(12) .0240(3) Uani d . 1 . . C O1 .2306(2) .44609(13) .52451(9) .0276(3) Uani d . 1 . . O O2 .0700(2) .29646(14) .41689(11) .0351(3) Uani d . 1 . . O O3 .4683(3) .58680(15) .60864(9) .0352(4) Uani d . 1 . . 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 .0238(7) .0111(6) .0286(7) .0008(5) .0015(6) -.0004(5) C2 .0217(7) .0156(6) .0251(7) .0004(6) .0012(6) .0006(5) C3 .0279(8) .0194(7) .0288(7) -.0065(6) .0042(6) .0000(6) C4 .0385(10) .0154(7) .0351(8) .0044(7) .0124(8) .0065(6) C5 .0270(8) .0252(8) .0342(8) .0058(7) .0039(7) .0109(6) C6 .0269(8) .0225(7) .0253(7) .0011(7) -.0010(6) .0003(6) C7 .0272(8) .0258(8) .0266(7) .0007(7) .0068(6) .0017(6) C8 .0251(8) .0142(6) .0345(8) .0009(6) .0010(6) .0050(6) C9 .0278(8) .0184(7) .0258(7) .0022(6) .0023(6) .0044(5) O1 .0265(6) .0230(6) .0332(6) .0026(5) .0080(5) .0030(5) O2 .0273(6) .0241(6) .0540(8) -.0065(6) -.0022(6) .0069(6) O3 .0490(9) .0299(7) .0267(6) .0018(6) .0042(5) -.0042(5) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C8 C1 C2 104.69(13) C8 C1 C6 114.41(14) C2 C1 C6 103.24(12) C8 C1 H1 111.3 C2 C1 H1 111.3 C6 C1 H1 111.3 C9 C2 C1 104.48(13) C9 C2 C3 113.84(13) C1 C2 C3 103.41(12) C9 C2 H2 111.5 C1 C2 H2 111.5 C3 C2 H2 111.5 C4 C3 C7 100.25(14) C4 C3 C2 106.51(13) C7 C3 C2 98.85(12) C4 C3 H3 116.2 C7 C3 H3 116.2 C2 C3 H3 116.2 C5 C4 C3 107.89(14) C5 C4 H4 126.1 C3 C4 H4 126.1 C4 C5 C6 107.82(16) C4 C5 H5 126.1 C6 C5 H5 126.1 C5 C6 C7 100.42(13) C5 C6 C1 107.62(13) C7 C6 C1 97.96(13) C5 C6 H6 116.1 C7 C6 H6 116.1 C1 C6 H6 116.1 C6 C7 C3 94.05(13) C6 C7 H7A 112.9 C3 C7 H7A 112.9 C6 C7 H7B 112.9 C3 C7 H7B 112.9 H7A C7 H7B 110.3 O2 C8 O1 119.75(16) O2 C8 C1 130.15(16) O1 C8 C1 110.09(14) O3 C9 O1 119.88(16) O3 C9 C2 130.14(16) O1 C9 C2 109.96(13) C8 O1 C9 110.63(13) 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 . 1.502(2) ? C1 C2 . 1.535(2) ? C1 C6 . 1.578(2) ? C1 H1 . 1.0000 ? C2 C9 . 1.503(2) ? C2 C3 . 1.575(2) ? C2 H2 . 1.0000 ? C3 C4 . 1.518(3) ? C3 C7 . 1.547(2) ? C3 H3 . 1.0000 ? C4 C5 . 1.332(3) ? C4 H4 . .9500 ? C5 C6 . 1.518(2) ? C5 H5 . .9500 ? C6 C7 . 1.545(2) ? C6 H6 . 1.0000 ? C7 H7A . .9900 ? C7 H7B . .9900 ? C8 O2 . 1.198(2) ? C8 O1 . 1.389(2) ? C9 O3 . 1.193(2) ? C9 O1 . 1.400(2) ? 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 C8 C1 C2 C9 -2.86(15) C6 C1 C2 C9 117.18(13) C8 C1 C2 C3 -122.25(13) C6 C1 C2 C3 -2.21(15) C9 C2 C3 C4 -44.70(18) C1 C2 C3 C4 68.03(15) C9 C2 C3 C7 -148.22(14) C1 C2 C3 C7 -35.49(15) C7 C3 C4 C5 33.14(17) C2 C3 C4 C5 -69.37(16) C3 C4 C5 C6 -.39(18) C4 C5 C6 C7 -32.57(17) C4 C5 C6 C1 69.33(18) C8 C1 C6 C5 48.63(18) C2 C1 C6 C5 -64.50(17) C8 C1 C6 C7 152.28(13) C2 C1 C6 C7 39.15(14) C5 C6 C7 C3 49.16(15) C1 C6 C7 C3 -60.50(13) C4 C3 C7 C6 -49.33(14) C2 C3 C7 C6 59.35(14) C2 C1 C8 O2 -176.41(17) C6 C1 C8 O2 71.3(2) C2 C1 C8 O1 3.91(16) C6 C1 C8 O1 -108.37(15) C1 C2 C9 O3 -177.39(17) C3 C2 C9 O3 -65.3(2) C1 C2 C9 O1 1.01(16) C3 C2 C9 O1 113.10(14) O2 C8 O1 C9 176.83(14) C1 C8 O1 C9 -3.45(17) O3 C9 O1 C8 -179.94(15) C2 C9 O1 C8 1.47(17)