############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # ############################################################################## data_I _audit_creation_method SHELXL97 _chemical_name_systematic ; 1,3-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde ; _chemical_name_common nordamnacanthal _chemical_formula_moiety 'C15 H8 O5' _chemical_formula_sum 'C15 H8 O5' _chemical_formula_iupac 'C15 H8 O5' _chemical_formula_weight 268.21 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.547(2) _cell_length_b 5.6690(10) _cell_length_c 20.231(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.62(4) _cell_angle_gamma 90.00 _cell_volume 1132.1(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 10451 _cell_measurement_theta_min 0.4 _cell_measurement_theta_max 26.4 _cell_measurement_temperature 293(2) _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.12 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14030 _diffrn_reflns_av_R_equivalents 0.029 _diffrn_reflns_av_sigmaI/netI 0.037 _diffrn_reflns_theta_min 2.1 _diffrn_reflns_theta_max 26.4 _diffrn_reflns_theta_full 26.4 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 22 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _refine_special_details ; Refinement of F^2^ against ALL reflections (2298) except two reflections with Delta(F^2^)/esd greater than 9 (2296). The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2298 _reflns_number_gt 1554 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.081 _refine_ls_R_factor_gt 0.051 _refine_ls_wR_factor_gt 0.132 _refine_ls_wR_factor_ref 0.150 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _refine_ls_number_reflns 2296 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0705P)^2^+0.3487P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.27 _refine_diff_density_min -0.20 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1999)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2008)' loop_ _atom_site_type_symbol _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 O O4 0.32777(16) 1.4401(3) -0.05914(8) 0.0669(5) Uani d . 1 . . O O5 0.02849(14) 0.7077(2) -0.03142(7) 0.0531(4) Uani d . 1 . . O O1 0.22406(15) 0.5649(2) 0.07880(7) 0.0525(4) Uani d . 1 . . H H1 0.1487 0.5610 0.0479 0.063 Uiso calc R 1 . . O O3 0.62014(15) 1.0321(3) 0.15870(9) 0.0746(5) Uani d . 1 . . H H3 0.6408 0.9283 0.1889 0.090 Uiso calc R 1 . . O O2 0.58762(18) 0.6610(3) 0.22568(9) 0.0811(6) Uani d . 1 . . C C6 0.2604(2) 1.2727(3) -0.05264(10) 0.0437(5) Uani d . 1 . . C C7 0.12238(19) 1.2323(3) -0.10446(9) 0.0388(5) Uani d . 1 . . C C12 0.04523(18) 1.0390(3) -0.09796(9) 0.0364(4) Uani d . 1 . . C C13 0.09986(19) 0.8728(3) -0.03790(10) 0.0388(5) Uani d . 1 . . C C14 0.23549(18) 0.9106(3) 0.01290(10) 0.0377(4) Uani d . 1 . . C C5 0.31419(18) 1.1053(3) 0.00715(10) 0.0396(5) Uani d . 1 . . C C4 0.4429(2) 1.1451(4) 0.05601(11) 0.0493(5) Uani d . 1 . . H H4 0.4935 1.2742 0.0513 0.059 Uiso calc R 1 . . C C3 0.4949(2) 0.9898(4) 0.11180(11) 0.0521(6) Uani d . 1 . . C C2 0.4211(2) 0.7925(4) 0.11979(10) 0.0461(5) Uani d . 1 . . C C1 0.2905(2) 0.7533(3) 0.06963(10) 0.0425(5) Uani d . 1 . . C C15 0.4762(3) 0.6333(4) 0.17886(13) 0.0652(7) Uani d . 1 . . H H15 0.4247 0.5031 0.1817 0.078 Uiso calc R 1 . . C C11 -0.0846(2) 1.0056(4) -0.14710(10) 0.0446(5) Uani d . 1 . . H H11 -0.1359 0.8766 -0.1430 0.054 Uiso calc R 1 . . C C10 -0.1371(2) 1.1638(4) -0.20178(10) 0.0509(5) Uani d . 1 . . H H10 -0.2239 1.1414 -0.2346 0.061 Uiso calc R 1 . . C C9 -0.0613(2) 1.3547(4) -0.20791(11) 0.0539(6) Uani d . 1 . . H H9 -0.0975 1.4613 -0.2447 0.065 Uiso calc R 1 . . C C8 0.0679(2) 1.3894(4) -0.15996(10) 0.0486(5) Uani d . 1 . . H H8 0.1185 1.5183 -0.1648 0.058 Uiso calc R 1 . . 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 O4 0.0621(10) 0.0626(10) 0.0708(11) -0.0288(8) 0.0169(8) 0.0066(8) O5 0.0512(9) 0.0466(8) 0.0591(9) -0.0150(7) 0.0163(7) 0.0068(7) O1 0.0511(9) 0.0471(8) 0.0565(9) -0.0020(7) 0.0155(7) 0.0087(7) O3 0.0437(9) 0.0866(12) 0.0726(11) -0.0075(8) -0.0056(8) -0.0060(9) O2 0.0657(11) 0.0934(13) 0.0606(11) 0.0183(10) -0.0071(9) 0.0054(9) C6 0.0458(11) 0.0411(11) 0.0474(11) -0.0107(9) 0.0201(9) -0.0052(9) C7 0.0434(11) 0.0367(10) 0.0381(10) -0.0049(8) 0.0167(9) -0.0044(8) C12 0.0367(10) 0.0360(10) 0.0374(10) -0.0028(8) 0.0142(8) -0.0048(8) C13 0.0419(11) 0.0355(10) 0.0421(11) -0.0054(8) 0.0187(9) -0.0036(8) C14 0.0370(10) 0.0388(10) 0.0378(10) 0.0018(8) 0.0138(8) -0.0027(8) C5 0.0359(10) 0.0413(10) 0.0426(11) -0.0048(8) 0.0152(8) -0.0075(8) C4 0.0450(12) 0.0496(12) 0.0536(13) -0.0085(9) 0.0176(10) -0.0075(10) C3 0.0386(11) 0.0605(13) 0.0511(13) 0.0012(10) 0.0081(10) -0.0113(11) C2 0.0427(11) 0.0504(12) 0.0423(11) 0.0075(9) 0.0112(9) -0.0026(9) C1 0.0432(11) 0.0404(11) 0.0474(11) 0.0016(8) 0.0202(9) -0.0033(8) C15 0.0664(15) 0.0655(15) 0.0561(14) 0.0136(12) 0.0122(12) 0.0028(12) C11 0.0413(11) 0.0467(11) 0.0457(11) -0.0068(9) 0.0149(9) -0.0065(9) C10 0.0433(11) 0.0603(13) 0.0430(11) 0.0026(10) 0.0075(9) -0.0059(10) C9 0.0634(14) 0.0528(13) 0.0422(12) 0.0073(11) 0.0146(11) 0.0072(9) C8 0.0578(13) 0.0430(11) 0.0471(12) -0.0066(9) 0.0209(11) 0.0014(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O4 C6 . 1.220(2) ? O5 C13 . 1.237(2) ? O1 C1 . 1.326(2) ? O1 H1 . 0.8200 ? O3 C3 . 1.349(3) ? O3 H3 . 0.8200 ? O2 C15 . 1.233(3) ? C6 C7 . 1.482(3) ? C6 C5 . 1.484(3) ? C7 C8 . 1.389(3) ? C7 C12 . 1.399(2) ? C12 C11 . 1.393(3) ? C12 C13 . 1.484(3) ? C13 C14 . 1.454(3) ? C14 C1 . 1.407(3) ? C14 C5 . 1.410(3) ? C5 C4 . 1.388(3) ? C4 C3 . 1.383(3) ? C4 H4 . 0.9300 ? C3 C2 . 1.404(3) ? C2 C1 . 1.411(3) ? C2 C15 . 1.446(3) ? C15 H15 . 0.9300 ? C11 C10 . 1.380(3) ? C11 H11 . 0.9300 ? C10 C9 . 1.377(3) ? C10 H10 . 0.9300 ? C9 C8 . 1.380(3) ? C9 H9 . 0.9300 ? C8 H8 . 0.9300 ? 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 _geom_angle_publ_flag C1 O1 H1 . . 109.5 ? C3 O3 H3 . . 109.5 ? O4 C6 C7 . . 120.56(18) ? O4 C6 C5 . . 121.01(18) ? C7 C6 C5 . . 118.43(16) ? C8 C7 C12 . . 119.32(18) ? C8 C7 C6 . . 119.77(17) ? C12 C7 C6 . . 120.91(17) ? C11 C12 C7 . . 119.84(17) ? C11 C12 C13 . . 119.92(16) ? C7 C12 C13 . . 120.23(16) ? O5 C13 C14 . . 121.38(17) ? O5 C13 C12 . . 119.46(17) ? C14 C13 C12 . . 119.15(16) ? C1 C14 C5 . . 118.53(17) ? C1 C14 C13 . . 120.26(17) ? C5 C14 C13 . . 121.21(17) ? C4 C5 C14 . . 121.66(18) ? C4 C5 C6 . . 118.30(17) ? C14 C5 C6 . . 120.04(17) ? C3 C4 C5 . . 119.03(19) ? C3 C4 H4 . . 120.5 ? C5 C4 H4 . . 120.5 ? O3 C3 C4 . . 118.0(2) ? O3 C3 C2 . . 120.4(2) ? C4 C3 C2 . . 121.61(18) ? C3 C2 C1 . . 118.88(18) ? C3 C2 C15 . . 121.0(2) ? C1 C2 C15 . . 120.1(2) ? O1 C1 C14 . . 122.54(18) ? O1 C1 C2 . . 117.17(18) ? C14 C1 C2 . . 120.29(18) ? O2 C15 C2 . . 123.5(3) ? O2 C15 H15 . . 118.2 ? C2 C15 H15 . . 118.2 ? C10 C11 C12 . . 120.01(19) ? C10 C11 H11 . . 120.0 ? C12 C11 H11 . . 120.0 ? C9 C10 C11 . . 120.08(19) ? C9 C10 H10 . . 120.0 ? C11 C10 H10 . . 120.0 ? C10 C9 C8 . . 120.6(2) ? C10 C9 H9 . . 119.7 ? C8 C9 H9 . . 119.7 ? C9 C8 C7 . . 120.12(19) ? C9 C8 H8 . . 119.9 ? C7 C8 H8 . . 119.9 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O4 C6 C7 C8 . . . . -1.6(3) ? C5 C6 C7 C8 . . . . 178.31(17) ? O4 C6 C7 C12 . . . . 179.08(18) ? C5 C6 C7 C12 . . . . -1.0(3) ? C8 C7 C12 C11 . . . . 0.3(3) ? C6 C7 C12 C11 . . . . 179.58(17) ? C8 C7 C12 C13 . . . . -178.19(17) ? C6 C7 C12 C13 . . . . 1.1(3) ? C11 C12 C13 O5 . . . . -1.1(3) ? C7 C12 C13 O5 . . . . 177.34(17) ? C11 C12 C13 C14 . . . . -179.93(16) ? C7 C12 C13 C14 . . . . -1.5(3) ? O5 C13 C14 C1 . . . . 2.3(3) ? C12 C13 C14 C1 . . . . -178.89(16) ? O5 C13 C14 C5 . . . . -177.04(18) ? C12 C13 C14 C5 . . . . 1.8(3) ? C1 C14 C5 C4 . . . . -0.4(3) ? C13 C14 C5 C4 . . . . 178.95(17) ? C1 C14 C5 C6 . . . . 178.98(16) ? C13 C14 C5 C6 . . . . -1.7(3) ? O4 C6 C5 C4 . . . . 0.6(3) ? C7 C6 C5 C4 . . . . -179.34(17) ? O4 C6 C5 C14 . . . . -178.84(19) ? C7 C6 C5 C14 . . . . 1.3(3) ? C14 C5 C4 C3 . . . . -0.2(3) ? C6 C5 C4 C3 . . . . -179.58(18) ? C5 C4 C3 O3 . . . . -179.91(17) ? C5 C4 C3 C2 . . . . 0.5(3) ? O3 C3 C2 C1 . . . . -179.82(18) ? C4 C3 C2 C1 . . . . -0.3(3) ? O3 C3 C2 C15 . . . . 1.2(3) ? C4 C3 C2 C15 . . . . -179.25(19) ? C5 C14 C1 O1 . . . . -179.51(17) ? C13 C14 C1 O1 . . . . 1.1(3) ? C5 C14 C1 C2 . . . . 0.7(3) ? C13 C14 C1 C2 . . . . -178.70(17) ? C3 C2 C1 O1 . . . . 179.83(17) ? C15 C2 C1 O1 . . . . -1.2(3) ? C3 C2 C1 C14 . . . . -0.3(3) ? C15 C2 C1 C14 . . . . 178.65(18) ? C3 C2 C15 O2 . . . . 1.2(4) ? C1 C2 C15 O2 . . . . -177.7(2) ? C7 C12 C11 C10 . . . . -0.4(3) ? C13 C12 C11 C10 . . . . 178.07(17) ? C12 C11 C10 C9 . . . . 0.0(3) ? C11 C10 C9 C8 . . . . 0.4(3) ? C10 C9 C8 C7 . . . . -0.5(3) ? C12 C7 C8 C9 . . . . 0.2(3) ? C6 C7 C8 C9 . . . . -179.14(18) ? 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 O3 H3 O2 . 0.82 1.86 2.590(3) 147.6 O1 H1 O5 . 0.82 1.86 2.577(2) 146.2 O1 H1 O5 3_565 0.82 2.34 2.933(2) 129.5 C4 H4 O4 3_685 0.93 2.45 3.358(2) 166.0 C10 H10 O2 4_475 0.93 2.53 3.312(3) 141.6 data_global _journal_date_recd_electronic 2008-01-28 _journal_date_accepted 2008-02-11 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2008 _journal_volume 64 _journal_issue 3 _journal_page_first o597 _journal_page_last o597 _journal_paper_category QO _journal_coeditor_code BG2162 _publ_contact_author_name 'Retailleau, Pascal' _publ_contact_author_address ; ICSN-CNRS 1 avenue de la Terrasse 91198 Gif sur Yvette France ; _publ_contact_author_email pascal.retailleau@icsn.cnrs-gif.fr _publ_contact_author_fax '33 1 69 07 72 47' _publ_contact_author_phone '33 1 69 82 45 83' _publ_section_title ; 1,3-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde ; loop_ _publ_author_name _publ_author_address 'Awang, Khalijah' ; Chemistry Department Faculty of Science University of Malaya 50603 Kuala Lumpur Malaysia ; 'Ismail, Nor Hadiani' ; Faculty of Applied Sciences Universiti Teknologi MARA Malaysia 40450 Shah Alam, Selangor Malaysia ; 'Ahmad, Rohaya' ; Faculty of Applied Sciences Universiti Teknologi MARA Malaysia 40450 Shah Alam, Selangor Malaysia ; 'Saidan, Nor Hafizoh' ; Faculty of Applied Sciences Universiti Teknologi MARA Malaysia 40450 Shah Alam, Selangor Malaysia ; 'Retailleau, Pascal' ; ICSN-CNRS 1 avenue de la Terrasse 91198 Gif sur Yvette France ; _publ_section_synopsis .