#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/10/2011049.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_2011049 loop_ _publ_author_name 'Winicker, Dominik' 'Bolte, Michael' _publ_section_title ; Diethyl 9,10-dihydro-9,10-ethanoanthracene-11,12-trans-dicarboxylate ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e271 _journal_page_last e272 _journal_paper_doi 10.1107/S0108270100006867 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C22 H22 O4' _chemical_formula_sum 'C22 H22 O4' _chemical_formula_weight 350.40 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 96.971(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.8786(7) _cell_length_b 18.4170(10) _cell_length_c 12.7580(10) _cell_measurement_reflns_used 510 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 20 _cell_measurement_theta_min 1 _cell_volume 1837.5(2) _computing_cell_refinement SMART _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full .901 _diffrn_measured_fraction_theta_max .901 _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 .023 _diffrn_reflns_av_sigmaI/netI .0128 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 34998 _diffrn_reflns_theta_full 29.62 _diffrn_reflns_theta_max 29.62 _diffrn_reflns_theta_min 1.95 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 1200 _diffrn_standards_number 123 _exptl_absorpt_coefficient_mu .086 _exptl_absorpt_correction_T_max .958 _exptl_absorpt_correction_T_min .942 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 744 _exptl_crystal_size_max .70 _exptl_crystal_size_mid .50 _exptl_crystal_size_min .50 _refine_diff_density_max .546 _refine_diff_density_min -.357 _refine_ls_extinction_coef .0147(16) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 4656 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all .059 _refine_ls_R_factor_gt .050 _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^)+(0.0648P)^2^+0.9045P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .138 _reflns_number_gt 4052 _reflns_number_total 4656 _reflns_threshold_expression I>2\s(I) _cod_data_source_file qa0300.cif _cod_data_source_block I _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_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2011049 _cod_database_fobs_code 2011049 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, 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 .38111(16) .59519(7) .13420(9) .0240(3) Uani d . 1 . . C H1 .3211 .5675 .0732 .029 Uiso calc R 1 . . H C2 .43939(16) .66933(7) .10161(9) .0242(2) Uani d . 1 . . C C3 .41512(17) .69909(8) .00107(10) .0297(3) Uani d . 1 . . C H3 .3542 .6729 -.0557 .036 Uiso calc R 1 . . H C4 .48097(19) .76782(8) -.01596(12) .0357(3) Uani d . 1 . . C H4 .4668 .7881 -.0849 .043 Uiso calc R 1 . . H C5 .56684(19) .80667(8) .06711(12) .0361(3) Uani d . 1 . . C H5 .6092 .8539 .0551 .043 Uiso calc R 1 . . H C6 .59141(18) .77681(7) .16847(11) .0313(3) Uani d . 1 . . C H6 .6508 .8034 .2254 .038 Uiso calc R 1 . . H C7 .52841(16) .70808(7) .18522(10) .0250(3) Uani d . 1 . . C C8 .54884(16) .66680(7) .28887(9) .0245(3) Uani d . 1 . . C H8 .6175 .6946 .3466 .029 Uiso calc R 1 . . H C9 .63006(16) .59444(7) .26816(10) .0249(3) Uani d . 1 . . C C10 .78081(17) .56647(8) .32041(11) .0314(3) Uani d . 1 . . C H10 .8405 .5918 .3784 .038 Uiso calc R 1 . . H C11 .84345(19) .50087(8) .28677(13) .0370(3) Uani d . 1 . . C H11 .9475 .4817 .3212 .044 Uiso calc R 1 . . H C12 .75461(19) .46345(8) .20331(12) .0363(3) Uani d . 1 . . C H12 .7992 .4191 .1803 .044 Uiso calc R 1 . . H C13 .60059(18) .49010(7) .15270(11) .0306(3) Uani d . 1 . . C H13 .5384 .4635 .0969 .037 Uiso calc R 1 . . H C14 .53918(16) .55603(7) .18489(10) .0248(3) Uani d . 1 . . C C15 .26295(16) .60938(7) .22189(9) .0250(3) Uani d . 1 . . C H15 .2269 .5614 .2484 .030 Uiso calc R 1 . . H C16 .36417(16) .65043(7) .31507(9) .0242(3) Uani d . 1 . . C H16 .3058 .6980 .3228 .029 Uiso calc R 1 . . H C51 .10326(17) .65088(8) .17813(10) .0305(3) Uani d . 1 . . C O51 .04149(14) .70085(7) .22068(9) .0466(3) Uani d . 1 . . O O52 .03809(13) .62427(7) .08508(8) .0409(3) Uani d . 1 . . O C53 -.1162(2) .65981(13) .03503(13) .0552(5) Uani d . 1 . . C H53A -.2131 .6497 .0756 .066 Uiso calc R 1 . . H H53B -.0986 .7130 .0335 .066 Uiso calc R 1 . . H C54 -.1541(3) .63215(17) -.07192(17) .0811(9) Uani d . 1 . . C H54A -.2564 .6563 -.1070 .122 Uiso calc R 1 . . H H54B -.1743 .5797 -.0696 .122 Uiso calc R 1 . . H H54C -.0571 .6418 -.1113 .122 Uiso calc R 1 . . H C61 .36465(17) .60932(7) .41834(10) .0269(3) Uani d . 1 . . C O61 .26785(15) .56111(6) .43353(8) .0416(3) Uani d . 1 . . O O62 .48275(14) .63583(6) .49145(8) .0386(3) Uani d . 1 . . O C63 .4992(2) .60234(11) .59578(12) .0467(4) Uani d . 1 . . C H63A .4739 .5498 .5894 .056 Uiso calc R 1 . . H H63B .4176 .6248 .6394 .056 Uiso calc R 1 . . H C64 .6758(3) .61366(12) .64529(14) .0547(5) Uani d . 1 . . C H64A .6902 .5917 .7158 .082 Uiso calc R 1 . . H H64B .6995 .6658 .6513 .082 Uiso calc R 1 . . H H64C .7554 .5910 .6018 .082 Uiso calc R 1 . . H 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 .0256(6) .0248(6) .0215(5) .0004(4) .0027(4) -.0013(4) C2 .0233(6) .0259(6) .0241(5) .0034(4) .0061(4) .0006(4) C3 .0305(7) .0346(7) .0247(6) .0072(5) .0061(5) .0034(5) C4 .0380(7) .0381(7) .0330(7) .0095(6) .0126(6) .0129(6) C5 .0383(8) .0280(7) .0447(8) .0021(5) .0159(6) .0089(6) C6 .0327(7) .0265(6) .0362(7) -.0014(5) .0099(5) -.0003(5) C7 .0247(6) .0256(6) .0255(6) .0013(5) .0066(4) .0008(4) C8 .0257(6) .0261(6) .0217(5) -.0034(5) .0027(4) -.0010(4) C9 .0254(6) .0261(6) .0239(5) -.0013(5) .0055(5) .0032(4) C10 .0268(6) .0354(7) .0312(6) -.0031(5) .0007(5) .0067(5) C11 .0284(7) .0377(8) .0448(8) .0056(6) .0039(6) .0130(6) C12 .0382(8) .0288(7) .0435(8) .0088(6) .0111(6) .0054(6) C13 .0355(7) .0264(6) .0306(6) .0018(5) .0070(5) .0010(5) C14 .0258(6) .0249(6) .0242(5) .0004(5) .0055(5) .0023(4) C15 .0251(6) .0281(6) .0221(5) -.0022(5) .0037(4) -.0008(4) C16 .0260(6) .0263(6) .0207(5) .0004(5) .0041(4) -.0005(4) C51 .0243(6) .0435(8) .0242(6) -.0007(5) .0056(5) -.0006(5) O51 .0389(6) .0605(8) .0391(6) .0175(5) -.0004(5) -.0109(5) O52 .0257(5) .0651(7) .0304(5) .0070(5) -.0023(4) -.0115(5) C53 .0289(8) .0993(15) .0356(8) .0193(9) -.0038(6) -.0097(9) C54 .0559(12) .137(2) .0459(11) .0379(14) -.0131(9) -.0235(13) C61 .0279(6) .0314(6) .0223(5) .0022(5) .0064(5) -.0002(5) O61 .0510(7) .0448(6) .0294(5) -.0144(5) .0061(4) .0047(4) O62 .0374(6) .0547(7) .0225(5) -.0114(5) -.0009(4) .0068(4) C63 .0413(8) .0735(12) .0247(7) -.0029(8) .0010(6) .0151(7) C64 .0564(11) .0637(12) .0396(9) -.0084(9) -.0120(8) .0080(8) 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 C14 C1 C2 106.59(10) C14 C1 C15 107.73(10) C2 C1 C15 105.82(10) C14 C1 H1 112.1 C2 C1 H1 112.1 C15 C1 H1 112.1 C3 C2 C7 120.25(12) C3 C2 C1 126.71(12) C7 C2 C1 113.02(10) C2 C3 C4 119.38(13) C2 C3 H3 120.3 C4 C3 H3 120.3 C5 C4 C3 120.38(13) C5 C4 H4 119.8 C3 C4 H4 119.8 C4 C5 C6 120.32(13) C4 C5 H5 119.8 C6 C5 H5 119.8 C7 C6 C5 119.37(13) C7 C6 H6 120.3 C5 C6 H6 120.3 C6 C7 C2 120.27(12) C6 C7 C8 126.18(12) C2 C7 C8 113.54(11) C9 C8 C7 106.93(10) C9 C8 C16 106.96(10) C7 C8 C16 106.28(10) C9 C8 H8 112.1 C7 C8 H8 112.1 C16 C8 H8 112.1 C10 C9 C14 120.40(12) C10 C9 C8 126.67(12) C14 C9 C8 112.90(11) C9 C10 C11 119.24(13) C9 C10 H10 120.4 C11 C10 H10 120.4 C12 C11 C10 120.26(13) C12 C11 H11 119.9 C10 C11 H11 119.9 C11 C12 C13 120.76(13) C11 C12 H12 119.6 C13 C12 H12 119.6 C14 C13 C12 119.13(13) C14 C13 H13 120.4 C12 C13 H13 120.4 C13 C14 C9 120.17(12) C13 C14 C1 126.05(12) C9 C14 C1 113.70(11) C51 C15 C16 111.31(11) C51 C15 C1 111.10(10) C16 C15 C1 109.63(10) C51 C15 H15 108.2 C16 C15 H15 108.2 C1 C15 H15 108.2 C61 C16 C15 111.71(10) C61 C16 C8 112.18(10) C15 C16 C8 109.69(10) C61 C16 H16 107.7 C15 C16 H16 107.7 C8 C16 H16 107.7 O51 C51 O52 123.55(13) O51 C51 C15 125.61(12) O52 C51 C15 110.84(12) C51 O52 C53 115.91(12) C54 C53 O52 108.61(15) C54 C53 H53A 110.0 O52 C53 H53A 110.0 C54 C53 H53B 110.0 O52 C53 H53B 110.0 H53A C53 H53B 108.3 C53 C54 H54A 109.5 C53 C54 H54B 109.5 H54A C54 H54B 109.5 C53 C54 H54C 109.5 H54A C54 H54C 109.5 H54B C54 H54C 109.5 O61 C61 O62 124.25(12) O61 C61 C16 124.99(12) O62 C61 C16 110.71(11) C61 O62 C63 117.56(12) O62 C63 C64 107.85(14) O62 C63 H63A 110.1 C64 C63 H63A 110.1 O62 C63 H63B 110.1 C64 C63 H63B 110.1 H63A C63 H63B 108.4 C63 C64 H64A 109.5 C63 C64 H64B 109.5 H64A C64 H64B 109.5 C63 C64 H64C 109.5 H64A C64 H64C 109.5 H64B C64 H64C 109.5 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 C14 . 1.5145(17) ? C1 C2 . 1.5149(17) ? C1 C15 . 1.5619(17) ? C1 H1 . 1.0000 ? C2 C3 . 1.3866(17) ? C2 C7 . 1.3991(17) ? C3 C4 . 1.395(2) ? C3 H3 . .9500 ? C4 C5 . 1.385(2) ? C4 H4 . .9500 ? C5 C6 . 1.397(2) ? C5 H5 . .9500 ? C6 C7 . 1.3857(18) ? C6 H6 . .9500 ? C7 C8 . 1.5169(17) ? C8 C9 . 1.5153(17) ? C8 C16 . 1.5613(17) ? C8 H8 . 1.0000 ? C9 C10 . 1.3885(18) ? C9 C14 . 1.3991(17) ? C10 C11 . 1.392(2) ? C10 H10 . .9500 ? C11 C12 . 1.385(2) ? C11 H11 . .9500 ? C12 C13 . 1.393(2) ? C12 H12 . .9500 ? C13 C14 . 1.3874(18) ? C13 H13 . .9500 ? C15 C51 . 1.5193(18) ? C15 C16 . 1.5461(17) ? C15 H15 . 1.0000 ? C16 C61 . 1.5191(17) ? C16 H16 . 1.0000 ? C51 O51 . 1.2012(18) ? C51 O52 . 1.3286(16) ? O52 C53 . 1.4580(19) ? C53 C54 . 1.453(3) ? C53 H53A . .9900 ? C53 H53B . .9900 ? C54 H54A . .9800 ? C54 H54B . .9800 ? C54 H54C . .9800 ? C61 O61 . 1.2013(17) ? C61 O62 . 1.3280(16) ? O62 C63 . 1.4584(17) ? C63 C64 . 1.472(2) ? C63 H63A . .9900 ? C63 H63B . .9900 ? C64 H64A . .9800 ? C64 H64B . .9800 ? C64 H64C . .9800 ? 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 C14 C1 C2 C3 123.71(13) C15 C1 C2 C3 -121.78(13) C14 C1 C2 C7 -55.12(13) C15 C1 C2 C7 59.39(13) C7 C2 C3 C4 .30(19) C1 C2 C3 C4 -178.45(12) C2 C3 C4 C5 -1.3(2) C3 C4 C5 C6 1.3(2) C4 C5 C6 C7 -.3(2) C5 C6 C7 C2 -.7(2) C5 C6 C7 C8 177.83(12) C3 C2 C7 C6 .70(19) C1 C2 C7 C6 179.61(11) C3 C2 C7 C8 -178.01(11) C1 C2 C7 C8 .91(15) C6 C7 C8 C9 -124.54(13) C2 C7 C8 C9 54.08(14) C6 C7 C8 C16 121.47(13) C2 C7 C8 C16 -59.91(13) C7 C8 C9 C10 123.60(13) C16 C8 C9 C10 -122.87(13) C7 C8 C9 C14 -54.46(13) C16 C8 C9 C14 59.06(13) C14 C9 C10 C11 2.06(19) C8 C9 C10 C11 -175.87(12) C9 C10 C11 C12 -1.1(2) C10 C11 C12 C13 -.9(2) C11 C12 C13 C14 1.9(2) C12 C13 C14 C9 -.94(19) C12 C13 C14 C1 175.69(12) C10 C9 C14 C13 -1.05(19) C8 C9 C14 C13 177.15(11) C10 C9 C14 C1 -178.07(11) C8 C9 C14 C1 .13(15) C2 C1 C14 C13 -122.06(13) C15 C1 C14 C13 124.74(13) C2 C1 C14 C9 54.75(13) C15 C1 C14 C9 -58.45(13) C14 C1 C15 C51 178.15(10) C2 C1 C15 C51 64.43(13) C14 C1 C15 C16 54.70(13) C2 C1 C15 C16 -59.02(12) C51 C15 C16 C61 113.84(12) C1 C15 C16 C61 -122.84(11) C51 C15 C16 C8 -121.13(11) C1 C15 C16 C8 2.20(14) C9 C8 C16 C61 66.45(12) C7 C8 C16 C61 -179.59(10) C9 C8 C16 C15 -58.32(12) C7 C8 C16 C15 55.65(13) C16 C15 C51 O51 -14.2(2) C1 C15 C51 O51 -136.67(15) C16 C15 C51 O52 166.16(11) C1 C15 C51 O52 43.68(15) O51 C51 O52 C53 .3(2) C15 C51 O52 C53 179.97(14) C51 O52 C53 C54 171.00(19) C15 C16 C61 O61 -17.07(19) C8 C16 C61 O61 -140.71(14) C15 C16 C61 O62 165.42(11) C8 C16 C61 O62 41.78(15) O61 C61 O62 C63 2.2(2) C16 C61 O62 C63 179.73(13) C61 O62 C63 C64 153.80(15) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 242704 2 PubChem 6958659