#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2012475.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_2012475 loop_ _publ_author_name 'Masci, Bernardo' 'Nierlich, Martine' 'Thu\'ery, Pierre' _publ_section_title ; 2,3,6,7-Tetrahydroxy-9,10-dimethyl-9,10-dihydro-9,10-ethanoanthracene bis(1,4-dioxane) solvate ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o86 _journal_page_last o87 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C18 H18 O4, 2(C4 H8 O2)' _chemical_formula_sum 'C26 H34 O8' _chemical_formula_weight 474.53 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 111.630(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 25.6848(18) _cell_length_b 9.7131(10) _cell_length_c 10.5531(13) _cell_measurement_reflns_used 7056 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 25.67 _cell_measurement_theta_min 3.31 _cell_volume 2447.4(4) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa-CCD software (Nonius, 1998)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material 'SHELXTL (Bruker, 1999); PARST97 (Nardelli, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 18 _diffrn_measured_fraction_theta_full .991 _diffrn_measured_fraction_theta_max .991 _diffrn_measurement_device_type 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans' _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 .0628 _diffrn_reflns_av_sigmaI/netI .0564 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 7056 _diffrn_reflns_theta_full 25.67 _diffrn_reflns_theta_max 25.67 _diffrn_reflns_theta_min 3.31 _diffrn_standards_decay_% none _exptl_absorpt_coefficient_mu .095 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description parallelepiped _exptl_crystal_F_000 1016 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .15 _refine_diff_density_max .199 _refine_diff_density_min -.260 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 2312 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all .0686 _refine_ls_R_factor_gt .0463 _refine_ls_shift/su_max .000 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+1.9711P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .1020 _refine_ls_wR_factor_ref .1125 _reflns_number_gt 1723 _reflns_number_total 2312 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file av1094.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M C2/c _cod_database_code 2012475 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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_type_symbol O1 .18347(5) .02013(14) .25789(13) .0256(3) Uani d . 1 O H1 .2129 -.0150 .3439 .031 Uiso d R 1 H O2 .19407(5) .02895(14) .52017(13) .0258(3) Uani d . 1 O H2 .1903 .0182 .6194 .031 Uiso d R 1 H C1 .14009(7) .07344(18) .29069(18) .0207(4) Uani d . 1 C C2 .14481(7) .07759(18) .42595(18) .0211(4) Uani d . 1 C C3 .10113(7) .13098(18) .45892(18) .0206(4) Uani d . 1 C H3 .1041 .1339 .5494 .025 Uiso calc R 1 H C4 .05314(7) .17986(18) .35673(18) .0200(4) Uani d . 1 C C5 .04900(7) .17763(18) .22041(17) .0200(4) Uani d . 1 C C6 .09264(7) .12356(18) .18798(18) .0209(4) Uani d . 1 C H6 .0900 .1210 .0977 .025 Uiso calc R 1 H C7 -.00355(7) .24621(18) .12102(19) .0214(4) Uani d . 1 C C8 -.00171(8) .39700(19) .17547(19) .0253(4) Uani d . 1 C H8A .0306 .4445 .1699 .030 Uiso calc R 1 H H8B -.0351 .4461 .1189 .030 Uiso calc R 1 H C9 -.00750(8) .2455(2) -.02641(19) .0257(4) Uani d . 1 C H9A .0246 .2910 -.0327 .039 Uiso calc R 1 H H9B -.0409 .2928 -.0823 .039 Uiso calc R 1 H H9C -.0087 .1521 -.0573 .039 Uiso calc R 1 H O3 .28878(5) -.04911(13) .41065(14) .0295(3) Uani d . 1 O O4 .37317(6) -.07483(14) .67391(15) .0371(4) Uani d . 1 O C10 .32075(9) -.1723(2) .4532(2) .0385(5) Uani d . 1 C H10A .3528 -.1690 .4256 .046 Uiso calc R 1 H H10B .2980 -.2508 .4089 .046 Uiso calc R 1 H C11 .34054(10) -.1898(2) .6046(2) .0448(6) Uani d . 1 C H11A .3084 -.1998 .6314 .054 Uiso calc R 1 H H11B .3629 -.2729 .6309 .054 Uiso calc R 1 H C12 .34128(8) .0487(2) .6314(2) .0335(5) Uani d . 1 C H12A .3641 .1270 .6762 .040 Uiso calc R 1 H H12B .3091 .0455 .6587 .040 Uiso calc R 1 H C13 .32170(8) .0668(2) .4801(2) .0316(5) Uani d . 1 C H13A .2994 .1501 .4538 .038 Uiso calc R 1 H H13B .3539 .0767 .4535 .038 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 O1 .0198(7) .0351(7) .0223(7) .0050(5) .0080(5) .0007(6) O2 .0179(6) .0375(8) .0205(7) .0060(6) .0053(5) .0043(6) C1 .0192(9) .0206(9) .0249(9) -.0005(7) .0112(8) -.0003(7) C2 .0184(9) .0207(9) .0221(9) .0005(7) .0049(7) .0017(7) C3 .0201(9) .0216(9) .0202(9) -.0012(7) .0077(7) .0000(7) C4 .0190(9) .0170(8) .0235(9) -.0022(7) .0073(7) -.0022(7) C5 .0189(9) .0182(9) .0210(9) -.0029(7) .0053(7) .0009(7) C6 .0214(9) .0212(9) .0197(9) -.0020(7) .0073(8) .0005(7) C7 .0181(9) .0218(9) .0232(9) -.0011(7) .0064(8) .0025(8) C8 .0189(9) .0207(9) .0330(11) -.0010(7) .0057(8) .0023(8) C9 .0208(9) .0291(10) .0263(10) -.0004(8) .0076(8) .0063(8) O3 .0219(7) .0280(7) .0347(8) .0024(5) .0058(6) -.0056(6) O4 .0326(8) .0330(8) .0365(8) -.0052(6) .0021(7) .0036(6) C10 .0309(11) .0281(11) .0486(14) .0056(9) .0054(10) -.0080(10) C11 .0419(13) .0295(12) .0506(14) -.0070(10) .0023(11) .0036(10) C12 .0272(11) .0332(11) .0377(12) -.0044(9) .0092(9) -.0066(9) C13 .0258(10) .0256(11) .0390(12) -.0018(8) .0067(9) -.0023(9) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C1 O1 H1 . . 107.9 C2 O2 H2 . . 110.1 O1 C1 C6 . . 119.52(15) O1 C1 C2 . . 119.68(15) C6 C1 C2 . . 120.79(15) O2 C2 C1 . . 116.26(15) O2 C2 C3 . . 124.05(16) C1 C2 C3 . . 119.69(16) C4 C3 C2 . . 120.00(16) C4 C3 H3 . . 120.0 C2 C3 H3 . . 120.0 C3 C4 C5 . . 120.08(16) C3 C4 C7 . 2 125.39(16) C5 C4 C7 . 2 114.42(15) C6 C5 C4 . . 119.67(16) C6 C5 C7 . . 125.85(16) C4 C5 C7 . . 114.35(15) C1 C6 C5 . . 119.76(16) C1 C6 H6 . . 120.1 C5 C6 H6 . . 120.1 C4 C7 C9 2 . 114.32(15) C4 C7 C5 2 . 106.75(14) C9 C7 C5 . . 114.21(15) C4 C7 C8 2 . 104.66(14) C9 C7 C8 . . 111.16(15) C5 C7 C8 . . 104.88(14) C8 C8 C7 2 . 110.88(10) C8 C8 H8A 2 . 109.5 C7 C8 H8A . . 109.5 C8 C8 H8B 2 . 109.5 C7 C8 H8B . . 109.5 H8A C8 H8B . . 108.1 C7 C9 H9A . . 109.5 C7 C9 H9B . . 109.5 H9A C9 H9B . . 109.5 C7 C9 H9C . . 109.5 H9A C9 H9C . . 109.5 H9B C9 H9C . . 109.5 C10 O3 C13 . . 109.53(15) C11 O4 C12 . . 109.65(15) O3 C10 C11 . . 111.16(18) O3 C10 H10A . . 109.4 C11 C10 H10A . . 109.4 O3 C10 H10B . . 109.4 C11 C10 H10B . . 109.4 H10A C10 H10B . . 108.0 O4 C11 C10 . . 111.26(18) O4 C11 H11A . . 109.4 C10 C11 H11A . . 109.4 O4 C11 H11B . . 109.4 C10 C11 H11B . . 109.4 H11A C11 H11B . . 108.0 O4 C12 C13 . . 111.18(16) O4 C12 H12A . . 109.4 C13 C12 H12A . . 109.4 O4 C12 H12B . . 109.4 C13 C12 H12B . . 109.4 H12A C12 H12B . . 108.0 O3 C13 C12 . . 110.81(16) O3 C13 H13A . . 109.5 C12 C13 H13A . . 109.5 O3 C13 H13B . . 109.5 C12 C13 H13B . . 109.5 H13A C13 H13B . . 108.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C1 . 1.383(2) O1 H1 . 1.0025 O2 C2 . 1.373(2) O2 H2 . 1.0911 C1 C6 . 1.387(2) C1 C2 . 1.388(2) C2 C3 . 1.392(2) C3 C4 . 1.388(2) C3 H3 . .9300 C4 C5 . 1.403(2) C4 C7 2 1.521(2) C5 C6 . 1.390(2) C5 C7 . 1.524(2) C6 H6 . .9300 C7 C4 2 1.521(2) C7 C9 . 1.521(3) C7 C8 . 1.568(3) C8 C8 2 1.543(4) C8 H8A . .9700 C8 H8B . .9700 C9 H9A . .9600 C9 H9B . .9600 C9 H9C . .9600 O3 C10 . 1.426(2) O3 C13 . 1.436(2) O4 C11 . 1.425(2) O4 C12 . 1.429(2) C10 C11 . 1.497(3) C10 H10A . .9700 C10 H10B . .9700 C11 H11A . .9700 C11 H11B . .9700 C12 C13 . 1.498(3) C12 H12A . .9700 C12 H12B . .9700 C13 H13A . .9700 C13 H13B . .9700 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 O1 H1 O3 . 1.00 1.84 2.6745(18) 138.1 O2 H2 O1 6_556 1.09 1.58 2.6644(18) 171.8