Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'April 16 15:33:05 2005' _audit_creation_method 'PLATON option' _audit_update_record ; ? ; _publ_contact_author_name 'Prof. Goverdhan Mehta' _publ_contact_author_address ; Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012 ; _publ_contact_author_email gm@orgchem.iisc.ernet.in _publ_contact_author_fax +91-80-23600936 _publ_contact_author_phone +91-80-22932850 _publ_section_title ; Concomitant dimorphism and helical self- assembly in a C2h-symmetric locked cyclitol ; loop_ _publ_author_name _publ_author_address 'Goverdhan Mehta' ; Department of Organic Chemistry Indian Institute of Science Bangalore 560 012, Karnataka India ; 'Saikat Sen' ; Department of Organic Chemistry Indian Institute of Science Bangalore 560 012, Karnataka India ; 'Kailasam Venkatesan' ; Department of Organic Chemistry Indian Institute of Science Bangalore 560 012, Karnataka India ; # 4. TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; # Insert blank lines between paragraphs _publ_section_comment ; ? ; _publ_section_exptl_prep ; All the hydrogens in the molecule were located from a difference Fourier map and refined isotropically. ; _publ_section_exptl_refinement ; ? ; # Insert blank lines between references _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C. Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R. (1999) J. Appl. Cryst. 32, 115-119. Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W.P., Garc\'ia-Granda, S., Gould, R.O., Smits, J.M.M. & Smykalla, C. (1999) The DIRDIF99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410. Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320. Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358. Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft, The Netherlands. Flack, H.D. (1983). Acta Cryst. A39, 876-881. LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. Mackay, A.L. (1984). Acta Cryst. A40, 165-166. Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018. Nonius (1998). Collect Software, Nonius B.V., Delft, The Netherlands. North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968). Acta Cryst. A24, 351-359. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C.W. Carter & R.M. Sweet, pp. 307-326. London: Academic Press. Sheldrick, G.M. SHELXL93. Program for crystal structure refinement. University of Gottingen, Germany, 1993. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of Gottingen, Germany, 1997. Sheldrick, G.M. SHELXS86. Program for Crystal Structure solution. University of Gottingen, Germany, 1986. Sheldrick, G.M. SHELXS97. Program for Crystal Structure solution. University of Gottingen, Germany, 1997. Spek, A.L. (1987). Acta Cryst. C43, 1233-1235. Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579. Spek, A.L. (1990). Acta Cryst. A46, C-34. Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht University, The Netherlands. Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66. Wilson, A.J.C. (1992) Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_acknowledgements ; ? ; _publ_section_figure_captions ; View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. ; #=============================================================================== data_alphapolymorph _database_code_depnum_ccdc_archive 'CCDC 250223' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (4aR*,8aS*,9aR*,10aS*)-1,4,4a,5,8,8a,9,9a,10,10a-decahydro-4a,8a,9a,10a- anthracenetetraol ; _chemical_name_common ; (4aR*,8aS*,9aR*,10aS*)-1,4,4a,5,8,8a,9,9a,10,10a-decahydro- 4a,8a,9a,10a-anthracenetetraol ; _chemical_melting_point 253-256 _chemical_formula_moiety 'C14 H20 O4' _chemical_formula_structural 'C14 H20 O4' _chemical_formula_sum 'C14 H20 O4' _chemical_absolute_configuration unk _chemical_formula_iupac 'C14 H20 O4' _chemical_formula_weight 252.30 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Tetragonal _symmetry_space_group_name_Hall 'P 4w' _symmetry_space_group_name_H-M 'P 41' _symmetry_Int_Tables_number 76 loop_ _symmetry_equiv_pos_as_xyz x,y,z -y,x,1/4+z -x,-y,1/2+z y,-x,3/4+z _cell_length_a 6.7802(9) _cell_length_b 6.7802(9) _cell_length_c 27.425(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1260.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ? ; _exptl_crystal_description 'square pyramidal' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.24 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.096 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9411 _exptl_absorpt_correction_T_max 0.9773 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 12972 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.29 _diffrn_reflns_theta_full 27.29 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 1450 _reflns_number_gt 1415 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. 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.Due to the absence of any significant anomalous scatterers (Z>Si) in (1), attempts to confirm the absolute structure by refinement of the Flack parameter led to an inconclusive value of -0.4 (10). Therefore the intensities of the Friedel pairs (1243) were averaged prior to merging of data in P4~1~ and the absolute configuration was assigned arbitarily. The reported value of R~int~ corresponds to subsequent merging of equivalent reflections in this space group. All hydrogen atoms were located in the difference Fourier map, and their positions refined freely along with an isotropic displacement parameter. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0614P)^2^+0.1763P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_abs_structure_details 'see text' _refine_ls_abs_structure_Flack ? _refine_ls_extinction_coef ? _refine_ls_number_reflns 1450 _refine_ls_number_parameters 243 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.0993 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.224 _refine_ls_restrained_S_all 1.224 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.249 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.044 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1461(3) 0.1360(3) 0.33370(7) 0.0137(4) Uani 1 1 d . . . C2 C 0.3172(3) 0.0706(3) 0.36609(7) 0.0177(4) Uani 1 1 d . . . C3 C 0.4466(3) 0.2370(3) 0.38237(7) 0.0210(5) Uani 1 1 d . . . C4 C 0.4406(3) 0.4161(3) 0.36329(7) 0.0210(5) Uani 1 1 d . . . C5 C 0.2996(3) 0.4722(3) 0.32340(7) 0.0180(4) Uani 1 1 d . . . C6 C 0.2179(3) 0.2936(3) 0.29689(8) 0.0155(4) Uani 1 1 d . . . C7 C 0.0502(3) 0.3502(3) 0.26217(7) 0.0153(4) Uani 1 1 d . . . C8 C -0.0406(3) 0.1750(3) 0.23508(6) 0.0147(4) Uani 1 1 d . . . C9 C -0.2092(3) 0.2416(3) 0.20175(7) 0.0191(4) Uani 1 1 d . . . C10 C -0.3327(3) 0.0746(3) 0.18379(7) 0.0212(5) Uani 1 1 d . . . C11 C -0.3308(3) -0.1034(3) 0.20351(8) 0.0230(5) Uani 1 1 d . . . C12 C -0.1982(3) -0.1582(3) 0.24541(8) 0.0206(5) Uani 1 1 d . . . C13 C -0.1145(3) 0.0190(3) 0.27219(7) 0.0155(4) Uani 1 1 d . . . C14 C 0.0522(3) -0.0383(3) 0.30697(7) 0.0157(4) Uani 1 1 d . . . O1 O -0.0012(2) 0.2364(2) 0.36248(5) 0.0158(3) Uani 1 1 d . . . O2 O 0.3658(2) 0.2086(2) 0.26579(5) 0.0179(3) Uani 1 1 d . . . O3 O 0.1039(2) 0.0809(2) 0.20408(5) 0.0194(3) Uani 1 1 d . . . O4 O -0.27494(19) 0.1032(2) 0.29959(5) 0.0167(3) Uani 1 1 d . . . H1O H -0.024(4) 0.173(4) 0.3914(11) 0.041(7) Uiso 1 1 d . . . H2O H 0.484(4) 0.193(3) 0.2780(8) 0.019(6) Uiso 1 1 d . . . H3O H 0.210(4) 0.104(3) 0.2151(9) 0.019(6) Uiso 1 1 d . . . H4O H -0.225(4) 0.166(3) 0.3216(10) 0.022(6) Uiso 1 1 d . . . H2A H 0.264(3) 0.001(3) 0.3940(9) 0.018(5) Uiso 1 1 d . . . H2B H 0.391(3) -0.020(3) 0.3497(8) 0.009(5) Uiso 1 1 d . . . H3 H 0.542(3) 0.208(3) 0.4083(9) 0.014(5) Uiso 1 1 d . . . H4 H 0.527(3) 0.506(3) 0.3751(8) 0.013(5) Uiso 1 1 d . . . H5A H 0.194(3) 0.550(3) 0.3352(8) 0.013(5) Uiso 1 1 d . . . H5B H 0.368(3) 0.563(3) 0.2988(9) 0.025(6) Uiso 1 1 d . . . H7A H -0.046(3) 0.413(3) 0.2818(8) 0.013(5) Uiso 1 1 d . . . H7B H 0.107(3) 0.440(3) 0.2371(8) 0.010(5) Uiso 1 1 d . . . H9A H -0.294(3) 0.330(3) 0.2175(8) 0.015(5) Uiso 1 1 d . . . H9B H -0.149(3) 0.311(4) 0.1740(9) 0.022(6) Uiso 1 1 d . . . H10 H -0.423(3) 0.097(3) 0.1582(10) 0.022(6) Uiso 1 1 d . . . H11 H -0.411(4) -0.205(3) 0.1919(9) 0.021(6) Uiso 1 1 d . . . H12A H -0.271(4) -0.237(4) 0.2682(11) 0.037(7) Uiso 1 1 d . . . H12B H -0.091(4) -0.238(3) 0.2334(9) 0.017(5) Uiso 1 1 d . . . H14B H 0.151(3) -0.106(3) 0.2889(9) 0.019(6) Uiso 1 1 d . . . H14A H -0.004(3) -0.129(3) 0.3302(8) 0.015(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0161(9) 0.0178(9) 0.0073(8) 0.0025(7) 0.0013(7) 0.0037(8) C2 0.0181(10) 0.0242(10) 0.0109(9) 0.0046(9) 0.0018(8) 0.0062(8) C3 0.0164(10) 0.0363(12) 0.0104(9) -0.0022(8) -0.0032(8) 0.0050(8) C4 0.0180(10) 0.0289(11) 0.0162(10) -0.0079(9) -0.0023(8) 0.0009(9) C5 0.0171(10) 0.0199(10) 0.0172(10) 0.0005(8) 0.0004(8) 0.0018(8) C6 0.0138(9) 0.0217(10) 0.0110(8) 0.0001(8) 0.0023(7) 0.0018(8) C7 0.0176(10) 0.0178(10) 0.0106(9) 0.0029(8) 0.0021(8) 0.0023(8) C8 0.0103(9) 0.0235(10) 0.0104(9) -0.0017(8) 0.0012(7) 0.0035(8) C9 0.0187(10) 0.0278(11) 0.0109(9) 0.0009(9) -0.0006(8) 0.0051(9) C10 0.0158(9) 0.0358(12) 0.0119(10) -0.0047(9) -0.0044(9) 0.0042(8) C11 0.0198(11) 0.0292(12) 0.0199(10) -0.0131(9) -0.0024(8) -0.0006(9) C12 0.0191(11) 0.0212(10) 0.0214(11) -0.0032(9) 0.0020(8) -0.0017(8) C13 0.0171(10) 0.0190(9) 0.0105(9) -0.0022(8) 0.0002(7) 0.0040(8) C14 0.0172(10) 0.0157(9) 0.0143(10) 0.0043(8) 0.0031(8) 0.0016(8) O1 0.0171(7) 0.0217(7) 0.0085(6) 0.0009(6) 0.0031(5) 0.0034(5) O2 0.0110(7) 0.0317(8) 0.0111(7) -0.0003(6) -0.0003(5) 0.0043(6) O3 0.0145(8) 0.0317(8) 0.0120(7) -0.0051(6) 0.0007(6) 0.0016(6) O4 0.0123(7) 0.0242(8) 0.0135(8) -0.0031(6) 0.0005(6) 0.0018(6) #=============================================================================== # 10. MOLECULAR GEOMETRY _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.527(3) . ? C1 C6 1.549(2) . ? C1 C14 1.529(3) . ? C2 H2B 0.91(2) . ? C2 H2A 0.97(2) . ? C3 C2 1.498(3) . ? C3 H3 0.98(2) . ? C4 C3 1.323(3) . ? C4 H4 0.91(2) . ? C5 C4 1.502(3) . ? C5 H5B 1.02(2) . ? C5 H5A 0.94(2) . ? C6 C5 1.517(3) . ? C6 C7 1.532(3) . ? C7 C8 1.531(3) . ? C7 H7A 0.95(2) . ? C7 H7B 0.99(2) . ? C9 C8 1.532(3) . ? C9 C10 1.492(3) . ? C9 H9A 0.93(2) . ? C9 H9B 0.98(2) . ? C10 H10 0.94(3) . ? C11 C10 1.323(3) . ? C11 H11 0.93(3) . ? C12 C11 1.505(3) . ? C12 H12A 0.96(3) . ? C12 H12B 0.97(3) . ? C13 C8 1.551(3) . ? C13 C12 1.518(3) . ? C14 C13 1.530(3) . ? C14 H14B 0.95(2) . ? C14 H14A 0.97(2) . ? O1 C1 1.443(2) . ? O1 H1O 0.92(3) . ? O2 C6 1.437(3) . ? O2 H2O 0.87(2) . ? O3 C8 1.445(2) . ? O3 H3O 0.80(3) . ? O4 C13 1.440(2) . ? O4 H4O 0.81(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1O 111.6(17) . . ? C1 C14 C13 114.20(15) . . ? C1 C14 H14A 110.1(13) . . ? C1 C14 H14B 109.1(14) . . ? C1 C2 H2A 108.4(13) . . ? C1 C2 H2B 109.2(13) . . ? C2 C1 C6 109.91(15) . . ? C2 C1 C14 111.74(15) . . ? C2 C3 H3 116.6(12) . . ? C3 C2 C1 113.56(17) . . ? C3 C2 H2A 110.4(13) . . ? C3 C2 H2B 109.3(12) . . ? C3 C4 C5 122.7(2) . . ? C3 C4 H4 117.4(14) . . ? C4 C3 C2 123.8(2) . . ? C4 C3 H3 119.6(12) . . ? C4 C5 C6 112.32(17) . . ? C4 C5 H5A 111.9(13) . . ? C4 C5 H5B 110.0(13) . . ? C5 C4 H4 120.0(14) . . ? C5 C6 C1 110.69(16) . . ? C5 C6 C7 111.65(16) . . ? C6 C7 H7A 105.8(13) . . ? C6 C7 H7B 107.3(12) . . ? C6 C5 H5A 109.5(13) . . ? C6 C5 H5B 109.2(13) . . ? C6 O2 H2O 117.5(15) . . ? C7 C6 C1 110.16(15) . . ? C7 C8 C9 111.15(16) . . ? C7 C8 C13 109.93(14) . . ? C8 C7 C6 113.93(15) . . ? C8 C7 H7A 110.2(12) . . ? C8 C7 H7B 107.1(12) . . ? C8 O3 H3O 107.6(18) . . ? C8 C9 H9A 111.8(13) . . ? C8 C9 H9B 107.2(13) . . ? C9 C8 C13 110.56(16) . . ? C9 C10 H10 119.3(14) . . ? C10 C11 C12 122.89(19) . . ? C10 C11 H11 122.0(14) . . ? C10 C9 H9A 107.1(14) . . ? C10 C9 H9B 109.7(14) . . ? C10 C9 C8 113.10(17) . . ? C11 C10 C9 123.50(18) . . ? C11 C10 H10 117.1(14) . . ? C11 C12 C13 113.40(17) . . ? C11 C12 H12A 109.0(17) . . ? C11 C12 H12B 109.2(14) . . ? C12 C13 C14 112.13(16) . . ? C12 C11 H11 115.1(15) . . ? C12 C13 C8 110.06(16) . . ? C13 C12 H12A 108.4(18) . . ? C13 C12 H12B 109.0(14) . . ? C13 O4 H4O 106.4(17) . . ? C13 C14 H14A 106.2(13) . . ? C13 C14 H14B 108.6(14) . . ? C14 C1 C6 110.59(15) . . ? C14 C13 C8 110.09(15) . . ? O1 C1 C2 110.16(15) . . ? O1 C1 C14 109.80(15) . . ? O1 C1 C6 104.39(15) . . ? O2 C6 C5 110.45(15) . . ? O2 C6 C7 104.45(16) . . ? O2 C6 C1 109.24(15) . . ? O3 C8 C13 107.73(15) . . ? O3 C8 C7 110.82(15) . . ? O3 C8 C9 106.56(15) . . ? O4 C13 C12 106.48(16) . . ? O4 C13 C14 109.49(16) . . ? O4 C13 C8 108.46(14) . . ? H2B C2 H2A 105.6(19) . . ? H5B C5 H5A 103.5(17) . . ? H7A C7 H7B 112.6(17) . . ? H9A C9 H9B 107.8(19) . . ? H12A C12 H12B 108(2) . . ? H14B C14 H14A 108.6(18) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C6 C7 C8 -55.5(2) . . . . ? C1 C14 C13 O4 -63.9(2) . . . . ? C1 C14 C13 C12 178.19(17) . . . . ? C1 C14 C13 C8 55.3(2) . . . . ? C1 C6 C5 C4 47.6(2) . . . . ? C2 C1 C6 C5 -59.6(2) . . . . ? C2 C1 C14 C13 -177.47(16) . . . . ? C2 C1 C6 C7 176.40(16) . . . . ? C2 C1 C6 O2 62.2(2) . . . . ? C4 C3 C2 C1 -13.1(3) . . . . ? C5 C4 C3 C2 0.9(3) . . . . ? C6 C5 C4 C3 -18.9(3) . . . . ? C6 C1 C2 C3 41.4(2) . . . . ? C5 C6 C7 C8 -178.94(16) . . . . ? C6 C7 C8 O3 -62.7(2) . . . . ? C6 C7 C8 C9 179.02(16) . . . . ? C6 C7 C8 C13 56.3(2) . . . . ? C6 C1 C14 C13 -54.7(2) . . . . ? C7 C6 C5 C4 170.74(17) . . . . ? C8 C13 C12 C11 -44.8(2) . . . . ? C8 C9 C10 C11 16.1(3) . . . . ? C10 C9 C8 O3 72.8(2) . . . . ? C10 C9 C8 C7 -166.32(17) . . . . ? C10 C9 C8 C13 -44.0(2) . . . . ? C12 C13 C8 C7 -178.05(15) . . . . ? C12 C13 C8 O3 -57.19(19) . . . . ? C12 C13 C8 C9 58.9(2) . . . . ? C12 C11 C10 C9 -2.0(3) . . . . ? C13 C12 C11 C10 17.1(3) . . . . ? C14 C13 C8 C9 -177.03(16) . . . . ? C14 C13 C8 O3 66.90(19) . . . . ? C14 C1 C6 O2 -61.63(19) . . . . ? C14 C1 C6 C5 176.53(15) . . . . ? C14 C1 C6 C7 52.6(2) . . . . ? C14 C13 C12 C11 -167.66(17) . . . . ? C14 C1 C2 C3 164.61(17) . . . . ? C14 C13 C8 C7 -53.95(19) . . . . ? O1 C1 C6 O2 -179.66(15) . . . . ? O1 C1 C2 C3 -73.1(2) . . . . ? O1 C1 C6 C5 58.51(19) . . . . ? O1 C1 C6 C7 -65.47(18) . . . . ? O1 C1 C14 C13 60.0(2) . . . . ? O2 C6 C7 C8 61.68(19) . . . . ? O2 C6 C5 C4 -73.5(2) . . . . ? O4 C13 C12 C11 72.6(2) . . . . ? O4 C13 C8 O3 -173.32(15) . . . . ? O4 C13 C8 C7 65.83(18) . . . . ? O4 C13 C8 C9 -57.3(2) . . . . ? #===END #=============================================================================== data_betapolymorph _database_code_depnum_ccdc_archive 'CCDC 250224' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (4aR*,8aS*,9aR*,10aS*)-1,4,4a,5,8,8a,9,9a,10,10a-decahydro-4a,8a,9a,10a- anthracenetetraol ; _chemical_name_common ; (4aR*,8aS*,9aR*,10aS*)-1,4,4a,5,8,8a,9,9a,10,10a-decahydro- 4a,8a,9a,10a-anthracenetetraol ; _chemical_melting_point 292.0-292.5 _chemical_formula_moiety 'C14 H20 O4' _chemical_formula_structural ? _chemical_formula_sum 'C14 H20 O4' _chemical_formula_iupac 'C14 H20 O4' _chemical_formula_weight 252.30 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 9.2811(19) _cell_length_b 9.926(2) _cell_length_c 13.927(3) _cell_angle_alpha 92.912(3) _cell_angle_beta 101.065(3) _cell_angle_gamma 91.848(4) _cell_volume 1256.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ? ; _exptl_crystal_description 'rectangular block-type' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.097 _exptl_crystal_density_meas_temp 100(2) _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9540 _exptl_absorpt_correction_T_max 0.9828 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12479 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 4580 _reflns_number_gt 3422 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. 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. All hydrogen atoms were located in the difference Fourier map, and their positions refined freely along with an isotropic displacement parameter. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0761P)^2^+0.4454P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4580 _refine_ls_number_parameters 485 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1458 _refine_ls_wR_factor_gt 0.1322 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.373 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.053 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1834(3) 0.8427(2) 0.30572(15) 0.0396(6) Uani 1 1 d . . . C2 C 0.3437(2) 0.8216(2) 0.33635(14) 0.0319(5) Uani 1 1 d . . . C3 C 0.4270(2) 0.93892(18) 0.40139(12) 0.0241(4) Uani 1 1 d . . . C4 C 0.5779(2) 0.89866(19) 0.45333(14) 0.0252(4) Uani 1 1 d . . . C5 C 0.6647(2) 1.01000(18) 0.52305(13) 0.0243(4) Uani 1 1 d . . . C6 C 0.8110(2) 0.9622(2) 0.57519(16) 0.0337(5) Uani 1 1 d . . . C7 C 0.8867(3) 1.0621(2) 0.65460(16) 0.0410(6) Uani 1 1 d . . . C8 C 0.6691(2) 0.3552(2) 0.31044(14) 0.0311(5) Uani 1 1 d . . . C9 C 0.6038(2) 0.4456(2) 0.35830(14) 0.0324(5) Uani 1 1 d . . . C10 C 0.6863(2) 0.5385(2) 0.44002(14) 0.0269(4) Uani 1 1 d . . . C11 C 0.8363(2) 0.48898(17) 0.48390(12) 0.0199(4) Uani 1 1 d . . . C12 C 0.9273(2) 0.59661(18) 0.55474(13) 0.0200(4) Uani 1 1 d . . . C13 C 1.08140(19) 0.55461(17) 0.59858(12) 0.0193(4) Uani 1 1 d . . . C14 C 1.1693(2) 0.66764(19) 0.66555(13) 0.0246(4) Uani 1 1 d . . . C15 C 0.3666(3) 0.2808(3) -0.16950(17) 0.0399(6) Uani 1 1 d . . . C16 C 0.4765(3) 0.2684(2) -0.07663(16) 0.0330(5) Uani 1 1 d . . . C17 C 0.4556(2) 0.1374(2) -0.02752(14) 0.0263(4) Uani 1 1 d . . . C18 C 0.5839(2) 0.1139(2) 0.05474(14) 0.0256(4) Uani 1 1 d . . . C19 C 0.5685(2) -0.0185(2) 0.10444(13) 0.0248(4) Uani 1 1 d . . . C20 C 0.7030(2) -0.0386(3) 0.18426(16) 0.0366(6) Uani 1 1 d . . . C21 C 0.7128(2) -0.1780(3) 0.21739(16) 0.0391(6) Uani 1 1 d . . . C22 C 0.7807(2) 0.6876(3) 0.79017(16) 0.0380(6) Uani 1 1 d . . . C23 C 0.7783(2) 0.5498(3) 0.82690(18) 0.0418(6) Uani 1 1 d . . . C24 C 0.9178(2) 0.5186(2) 0.89826(13) 0.0259(4) Uani 1 1 d . . . C25 C 0.8941(2) 0.3937(2) 0.95486(14) 0.0277(5) Uani 1 1 d . . . C26 C 1.0292(2) 0.3606(2) 1.02956(13) 0.0269(5) Uani 1 1 d . . . C27 C 1.0005(3) 0.2371(2) 1.08436(14) 0.0325(5) Uani 1 1 d . . . C28 C 1.1218(3) 0.2169(2) 1.17012(15) 0.0377(6) Uani 1 1 d . . . O1 O 0.44124(16) 1.04767(13) 0.33730(9) 0.0273(3) Uani 1 1 d . . . O2 O 0.68699(16) 1.11718(14) 0.46104(9) 0.0261(3) Uani 1 1 d . . . O3 O 0.81150(15) 0.37098(12) 0.53566(9) 0.0220(3) Uani 1 1 d . . . O4 O 1.07182(14) 0.43498(12) 0.65306(9) 0.0216(3) Uani 1 1 d . . . O5 O 0.32009(18) 0.14445(18) 0.00968(12) 0.0503(5) Uani 1 1 d . . . O6 O 0.43435(14) -0.02101(14) 0.14384(10) 0.0251(3) Uani 1 1 d . . . O7 O 1.02931(16) 0.49538(14) 0.84005(9) 0.0298(4) Uani 1 1 d . . . O8 O 1.1443(2) 0.3394(2) 0.97568(12) 0.0626(6) Uani 1 1 d . . . H1 H 0.133(3) 0.781(2) 0.2569(17) 0.045(7) Uiso 1 1 d . . . H2A H 0.390(2) 0.809(2) 0.2770(17) 0.039(6) Uiso 1 1 d . . . H2B H 0.360(2) 0.738(2) 0.3712(15) 0.032(6) Uiso 1 1 d . . . H4A H 0.634(2) 0.873(2) 0.4035(16) 0.029(5) Uiso 1 1 d . . . H4B H 0.567(2) 0.822(2) 0.4899(15) 0.030(5) Uiso 1 1 d . . . H6A H 0.871(3) 0.949(2) 0.5280(17) 0.042(6) Uiso 1 1 d . . . H6B H 0.795(2) 0.876(2) 0.6026(15) 0.033(6) Uiso 1 1 d . . . H7 H 0.991(3) 1.053(2) 0.6784(17) 0.043(6) Uiso 1 1 d . . . H8 H 0.614(2) 0.298(2) 0.2570(16) 0.034(6) Uiso 1 1 d . . . H9 H 0.500(3) 0.459(2) 0.3375(16) 0.039(6) Uiso 1 1 d . . . H10A H 0.699(2) 0.625(2) 0.4166(15) 0.029(5) Uiso 1 1 d . . . H10B H 0.631(2) 0.549(2) 0.4920(16) 0.035(6) Uiso 1 1 d . . . H12B H 0.877(2) 0.6177(19) 0.6104(14) 0.022(5) Uiso 1 1 d . . . H12A H 0.936(2) 0.676(2) 0.5218(15) 0.026(5) Uiso 1 1 d . . . H14A H 1.152(2) 0.750(2) 0.6356(14) 0.021(5) Uiso 1 1 d . . . H14B H 1.130(2) 0.6763(19) 0.7275(15) 0.025(5) Uiso 1 1 d . . . H15 H 0.355(3) 0.363(3) -0.1919(18) 0.051(7) Uiso 1 1 d . . . H16A H 0.577(3) 0.277(2) -0.0842(16) 0.035(6) Uiso 1 1 d . . . H16B H 0.473(2) 0.343(2) -0.0293(18) 0.046(7) Uiso 1 1 d . . . H18A H 0.670(2) 0.114(2) 0.0326(15) 0.032(6) Uiso 1 1 d . . . H18B H 0.587(2) 0.191(2) 0.1006(17) 0.039(6) Uiso 1 1 d . . . H20A H 0.791(3) -0.012(3) 0.1608(18) 0.057(7) Uiso 1 1 d . . . H20B H 0.700(3) 0.025(3) 0.237(2) 0.059(8) Uiso 1 1 d . . . H21 H 0.782(3) -0.199(2) 0.2770(18) 0.047(7) Uiso 1 1 d . . . H22 H 0.705(3) 0.710(2) 0.7375(18) 0.049(7) Uiso 1 1 d . . . H23A H 0.699(3) 0.538(3) 0.8570(18) 0.056(8) Uiso 1 1 d . . . H23B H 0.769(3) 0.483(3) 0.773(2) 0.069(9) Uiso 1 1 d . . . H25A H 0.870(3) 0.315(2) 0.9103(18) 0.047(7) Uiso 1 1 d . . . H25B H 0.811(3) 0.409(2) 0.9883(18) 0.051(7) Uiso 1 1 d . . . H27A H 0.908(3) 0.246(2) 1.1070(16) 0.042(6) Uiso 1 1 d . . . H27B H 0.990(2) 0.158(2) 1.0379(16) 0.038(6) Uiso 1 1 d . . . H28 H 1.126(3) 0.136(2) 1.1928(17) 0.045(7) Uiso 1 1 d . . . H1O H 0.516(3) 1.095(2) 0.3674(18) 0.045(7) Uiso 1 1 d . . . H2O H 0.719(3) 1.179(3) 0.4888(17) 0.040(7) Uiso 1 1 d . . . H3O H 0.884(3) 0.364(2) 0.5791(18) 0.042(7) Uiso 1 1 d . . . H4O H 1.048(2) 0.460(2) 0.7101(18) 0.045(7) Uiso 1 1 d . . . H5O H 0.330(3) 0.097(3) 0.0585(19) 0.056(8) Uiso 1 1 d . . . H6O H 0.449(3) 0.004(2) 0.2043(19) 0.048(7) Uiso 1 1 d . . . H7O H 1.094(3) 0.447(3) 0.875(2) 0.071(9) Uiso 1 1 d . . . H8O H 1.195(3) 0.276(3) 0.9924(18) 0.058(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0551(15) 0.0421(13) 0.0168(10) 0.0045(9) -0.0005(10) -0.0302(12) C2 0.0543(14) 0.0279(11) 0.0135(9) -0.0045(8) 0.0119(9) -0.0210(10) C3 0.0401(12) 0.0199(9) 0.0133(9) 0.0004(7) 0.0098(8) -0.0117(8) C4 0.0433(12) 0.0178(10) 0.0170(9) -0.0003(8) 0.0138(9) -0.0093(8) C5 0.0380(11) 0.0210(9) 0.0152(9) 0.0033(7) 0.0095(8) -0.0092(8) C6 0.0390(13) 0.0340(12) 0.0298(12) 0.0110(9) 0.0103(10) -0.0076(9) C7 0.0419(14) 0.0495(15) 0.0278(12) 0.0179(11) -0.0036(10) -0.0184(11) C8 0.0364(12) 0.0389(12) 0.0144(9) 0.0023(9) -0.0010(8) -0.0173(10) C9 0.0271(11) 0.0448(13) 0.0235(10) 0.0097(9) -0.0005(9) -0.0072(9) C10 0.0271(11) 0.0321(11) 0.0230(10) 0.0038(9) 0.0088(8) -0.0028(8) C11 0.0276(10) 0.0188(9) 0.0141(9) 0.0012(7) 0.0076(7) -0.0059(7) C12 0.0305(10) 0.0165(9) 0.0149(9) -0.0015(7) 0.0106(8) -0.0043(7) C13 0.0289(10) 0.0171(9) 0.0125(8) 0.0018(7) 0.0067(7) -0.0073(7) C14 0.0381(12) 0.0218(10) 0.0139(9) -0.0016(8) 0.0079(8) -0.0106(8) C15 0.0448(14) 0.0503(15) 0.0380(13) 0.0329(12) 0.0291(11) 0.0325(12) C16 0.0465(14) 0.0277(11) 0.0307(11) 0.0089(9) 0.0187(10) 0.0108(10) C17 0.0284(10) 0.0307(10) 0.0235(10) 0.0088(8) 0.0108(8) 0.0096(8) C18 0.0312(11) 0.0292(11) 0.0154(9) -0.0001(8) 0.0032(8) -0.0039(8) C19 0.0211(10) 0.0358(11) 0.0177(9) 0.0076(8) 0.0031(7) 0.0010(8) C20 0.0198(11) 0.0667(16) 0.0223(11) 0.0190(11) -0.0014(8) -0.0053(10) C21 0.0209(11) 0.0726(17) 0.0296(12) 0.0308(12) 0.0100(9) 0.0154(11) C22 0.0251(11) 0.0670(16) 0.0268(11) 0.0262(11) 0.0084(9) 0.0183(11) C23 0.0231(12) 0.0723(18) 0.0295(12) 0.0267(12) -0.0021(9) -0.0025(11) C24 0.0242(10) 0.0368(11) 0.0169(9) 0.0082(8) 0.0025(7) 0.0040(8) C25 0.0320(11) 0.0336(11) 0.0159(10) 0.0036(8) 0.0014(8) -0.0050(9) C26 0.0323(11) 0.0333(11) 0.0186(10) 0.0089(8) 0.0103(8) 0.0111(8) C27 0.0545(15) 0.0273(11) 0.0179(10) 0.0045(9) 0.0110(9) 0.0076(10) C28 0.0566(15) 0.0412(13) 0.0257(11) 0.0201(10) 0.0245(11) 0.0303(12) O1 0.0415(9) 0.0263(7) 0.0141(7) 0.0034(5) 0.0074(6) -0.0160(6) O2 0.0408(8) 0.0222(7) 0.0153(7) 0.0010(6) 0.0088(6) -0.0165(6) O3 0.0282(7) 0.0238(7) 0.0134(6) 0.0034(5) 0.0045(6) -0.0117(6) O4 0.0323(7) 0.0211(7) 0.0125(6) 0.0038(5) 0.0075(5) -0.0067(5) O5 0.0540(10) 0.0703(12) 0.0454(10) 0.0410(9) 0.0396(8) 0.0475(9) O6 0.0263(7) 0.0386(8) 0.0143(7) 0.0074(6) 0.0109(5) 0.0107(6) O7 0.0401(9) 0.0392(8) 0.0148(7) 0.0092(6) 0.0128(6) 0.0152(7) O8 0.0894(14) 0.0763(13) 0.0463(10) 0.0432(10) 0.0532(10) 0.0676(12) #=============================================================================== # 10. MOLECULAR GEOMETRY _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C7 1.321(4) 2_676 ? C1 H1 0.93(2) . ? C2 C1 1.492(3) . ? C2 C3 1.530(2) . ? C2 H2A 1.01(2) . ? C2 H2B 0.98(2) . ? C3 C5 1.551(3) 2_676 ? C4 C3 1.524(3) . ? C4 C5 1.532(2) . ? C4 H4A 0.97(2) . ? C4 H4B 0.95(2) . ? C6 C7 1.499(3) . ? C6 C5 1.515(3) . ? C6 H6A 0.95(2) . ? C6 H6B 0.97(2) . ? C7 H7 0.97(2) . ? C8 C9 1.322(3) . ? C8 C14 1.500(3) 2_766 ? C8 H8 0.96(2) . ? C9 H9 0.97(2) . ? C10 C9 1.498(3) . ? C10 C11 1.517(3) . ? C10 H10A 0.94(2) . ? C10 H10B 0.96(2) . ? C12 C13 1.523(3) . ? C12 C11 1.531(2) . ? C12 H12B 1.00(2) . ? C12 H12A 0.94(2) . ? C13 C14 1.529(2) . ? C13 C11 1.548(2) 2_766 ? C14 H14A 0.94(2) . ? C14 H14B 1.00(2) . ? C15 C21 1.312(4) 2_655 ? C15 H15 0.89(3) . ? C16 C15 1.499(3) . ? C16 H16A 0.96(2) . ? C16 H16B 0.97(2) . ? C17 C16 1.524(3) . ? C17 C19 1.534(3) 2_655 ? C18 C17 1.519(3) . ? C18 C19 1.531(3) . ? C18 H18A 0.91(2) . ? C18 H18B 0.97(2) . ? C19 C20 1.530(3) . ? C20 H20A 0.97(3) . ? C20 H20B 0.95(3) . ? C21 C20 1.481(3) . ? C21 H21 0.98(2) . ? C22 C28 1.313(3) 2_767 ? C22 C23 1.485(3) . ? C22 H22 0.96(2) . ? C23 H23A 0.92(3) . ? C23 H23B 0.97(3) . ? C24 C23 1.524(3) . ? C24 C26 1.530(3) 2_767 ? C25 C26 1.524(3) . ? C25 C24 1.535(3) . ? C25 H25A 0.96(2) . ? C25 H25B 0.99(2) . ? C26 C24 1.530(3) 2_767 ? C27 C28 1.502(3) . ? C27 C26 1.519(3) . ? C27 H27A 0.97(2) . ? C27 H27B 0.98(2) . ? C28 H28 0.88(2) . ? O1 C3 1.454(2) . ? O1 H1O 0.85(2) . ? O2 C5 1.438(2) . ? O2 H2O 0.73(3) . ? O3 C11 1.441(2) . ? O3 H3O 0.82(2) . ? O4 C13 1.451(2) . ? O4 H4O 0.89(2) . ? O5 C17 1.451(2) . ? O5 H5O 0.84(3) . ? O6 C19 1.454(2) . ? O6 H6O 0.85(3) . ? O7 C24 1.449(2) . ? O7 H7O 0.87(3) . ? O8 C26 1.433(2) . ? O8 H8O 0.82(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 C3 113.34(19) . . ? C1 C2 H2B 110.6(12) . . ? C1 C2 H2A 110.1(12) . . ? C1 C7 C6 122.8(2) 2_676 . ? C1 C7 H7 120.0(14) 2_676 . ? C2 C3 C5 110.01(16) . 2_676 ? C2 C1 H1 115.2(14) . . ? C3 O1 H1O 104.0(16) . . ? C3 C2 H2A 108.0(12) . . ? C3 C2 H2B 108.8(12) . . ? C3 C4 C5 114.17(16) . . ? C3 C4 H4B 109.4(12) . . ? C3 C4 H4A 107.9(12) . . ? C4 C3 C2 111.51(16) . . ? C4 C5 C3 110.34(15) . 2_676 ? C4 C3 C5 110.53(15) . 2_676 ? C5 C4 H4B 108.3(12) . . ? C5 C4 H4A 109.1(12) . . ? C5 O2 H2O 112.8(19) . . ? C5 C6 H6A 107.9(14) . . ? C5 C6 H6B 108.7(12) . . ? C6 C5 C4 111.63(17) . . ? C6 C7 H7 117.2(14) . . ? C6 C5 C3 110.33(16) . 2_676 ? C7 C6 C5 112.19(19) . . ? C7 C6 H6B 110.0(12) . . ? C7 C6 H6A 109.2(14) . . ? C7 C1 C2 123.9(2) 2_676 . ? C7 C1 H1 120.9(14) 2_676 . ? C8 C9 C10 122.65(19) . . ? C8 C9 H9 120.1(13) . . ? C8 C14 C13 113.20(16) 2_766 . ? C8 C14 H14B 109.6(11) 2_766 . ? C8 C14 H14A 110.6(12) 2_766 . ? C9 C8 C14 123.67(18) . 2_766 ? C9 C8 H8 121.2(13) . . ? C9 C10 C11 112.92(17) . . ? C9 C10 H10A 109.4(12) . . ? C9 C10 H10B 110.5(12) . . ? C10 C11 C12 111.43(15) . . ? C10 C9 H9 117.0(13) . . ? C10 C11 C13 110.12(15) . 2_766 ? C11 O3 H3O 107.8(17) . . ? C11 C12 H12B 109.6(11) . . ? C11 C12 H12A 109.2(12) . . ? C11 C10 H10A 108.6(13) . . ? C11 C10 H10B 107.9(13) . . ? C12 C13 C14 111.70(15) . . ? C12 C13 C11 110.25(14) . 2_766 ? C12 C11 C13 110.73(14) . 2_766 ? C13 C14 H14A 108.6(11) . . ? C13 C14 H14B 108.7(11) . . ? C13 O4 H4O 107.9(15) . . ? C13 C12 C11 113.91(15) . . ? C13 C12 H12B 107.2(11) . . ? C13 C12 H12A 108.4(12) . . ? C14 C13 C11 110.29(14) . 2_766 ? C14 C8 H8 115.2(12) 2_766 . ? C15 C21 C20 123.1(2) 2_655 . ? C15 C21 H21 116.0(14) 2_655 . ? C15 C16 C17 113.0(2) . . ? C15 C16 H16A 114.1(13) . . ? C15 C16 H16B 111.7(14) . . ? C16 C17 C19 109.71(16) . 2_655 ? C16 C15 H15 117.0(16) . . ? C17 C16 H16B 108.0(14) . . ? C17 C16 H16A 108.2(13) . . ? C17 O5 H5O 106.5(17) . . ? C17 C18 C19 113.73(16) . . ? C17 C18 H18A 111.1(13) . . ? C17 C18 H18B 104.7(13) . . ? C18 C19 C17 109.81(15) . 2_655 ? C18 C17 C16 112.19(17) . . ? C18 C17 C19 110.71(16) . 2_655 ? C19 O6 H6O 112.8(16) . . ? C19 C18 H18A 107.8(14) . . ? C19 C18 H18B 111.1(13) . . ? C19 C20 H20B 107.3(16) . . ? C19 C20 H20A 109.1(15) . . ? C20 C19 C17 110.63(17) . 2_655 ? C20 C21 H21 121.0(14) . . ? C20 C19 C18 111.30(16) . . ? C21 C20 C19 113.75(19) . . ? C21 C20 H20A 110.4(15) . . ? C21 C20 H20B 111.2(16) . . ? C21 C15 C16 123.4(2) 2_655 . ? C21 C15 H15 119.6(16) 2_655 . ? C22 C28 C27 123.2(2) 2_767 . ? C22 C28 H28 120.3(16) 2_767 . ? C22 C23 H23A 109.8(16) . . ? C22 C23 C24 113.8(2) . . ? C22 C23 H23B 109.8(17) . . ? C23 C22 H22 119.0(15) . . ? C23 C24 C26 110.87(18) . 2_767 ? C23 C24 C25 111.41(17) . . ? C24 C23 H23B 106.1(17) . . ? C24 C23 H23A 108.8(16) . . ? C24 C25 H25B 108.2(14) . . ? C24 C25 H25A 110.2(14) . . ? C24 O7 H7O 105.5(19) . . ? C25 C26 C24 111.08(16) . 2_767 ? C26 O8 H8O 114.4(18) . . ? C26 C25 C24 113.48(16) . . ? C26 C25 H25B 109.8(14) . . ? C26 C27 H27B 107.9(13) . . ? C26 C25 H25A 106.3(14) . . ? C26 C27 H27A 109.0(13) . . ? C26 C24 C25 109.69(15) 2_767 . ? C27 C26 C25 111.69(17) . . ? C27 C26 C24 110.37(15) . 2_767 ? C27 C28 H28 116.5(16) . . ? C28 C27 C26 112.65(19) . . ? C28 C27 H27B 109.5(13) . . ? C28 C27 H27A 109.5(13) . . ? C28 C22 C23 123.2(2) 2_767 . ? C28 C22 H22 117.7(15) 2_767 . ? O1 C3 C5 107.66(14) . 2_676 ? O1 C3 C4 110.48(15) . . ? O1 C3 C2 106.50(14) . . ? O2 C5 C6 110.36(15) . . ? O2 C5 C4 104.73(14) . . ? O2 C5 C3 109.30(15) . 2_676 ? O3 C11 C10 106.84(14) . . ? O3 C11 C12 109.83(14) . . ? O3 C11 C13 107.75(13) . 2_766 ? O4 C13 C12 109.56(14) . . ? O4 C13 C14 109.83(14) . . ? O4 C13 C11 104.99(13) . 2_766 ? O5 C17 C18 110.53(16) . . ? O5 C17 C16 107.65(15) . . ? O5 C17 C19 105.81(16) . 2_655 ? O6 C19 C20 111.23(15) . . ? O6 C19 C18 109.89(15) . . ? O6 C19 C17 103.72(14) . 2_655 ? O7 C24 C23 106.54(16) . . ? O7 C24 C26 107.87(15) . 2_767 ? O7 C24 C25 110.37(16) . . ? O8 C26 C27 111.35(16) . . ? O8 C26 C25 106.30(16) . . ? O8 C26 C24 105.83(17) . 2_767 ? H2B C2 H2A 105.6(17) . . ? H4B C4 H4A 107.8(17) . . ? H6B C6 H6A 108.8(18) . . ? H10A C10 H10B 107.4(17) . . ? H12B C12 H12A 108.3(16) . . ? H14B C14 H14A 105.8(16) . . ? H16A C16 H16B 101.0(18) . . ? H18A C18 H18B 108.4(18) . . ? H20A C20 H20B 104(2) . . ? H23B C23 H23A 108(2) . . ? H25B C25 H25A 109(2) . . ? H27B C27 H27A 108.1(19) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 O1 -75.02(19) . . . . ? C1 C2 C3 C4 164.39(16) . . . . ? C1 C2 C3 C5 41.4(2) . . . 2_676 ? C3 C4 C5 O2 -62.71(19) . . . . ? C3 C4 C5 C6 177.86(15) . . . . ? C3 C4 C5 C3 54.8(2) . . . 2_676 ? C3 C2 C1 C7 -13.1(3) . . . 2_676 ? C5 C4 C3 O1 64.16(19) . . . . ? C5 C4 C3 C2 -177.61(15) . . . . ? C5 C4 C3 C5 -54.9(2) . . . 2_676 ? C5 C6 C7 C1 19.6(3) . . . 2_676 ? C7 C6 C5 O2 72.8(2) . . . . ? C7 C6 C5 C4 -171.20(16) . . . . ? C7 C6 C5 C3 -48.1(2) . . . 2_676 ? C9 C10 C11 O3 -69.55(19) . . . . ? C9 C10 C11 C12 170.48(15) . . . . ? C9 C10 C11 C13 47.2(2) . . . 2_766 ? C11 C12 C13 O4 -60.26(18) . . . . ? C11 C12 C13 C14 177.80(14) . . . . ? C11 C12 C13 C11 54.8(2) . . . 2_766 ? C11 C13 C14 C8 -42.4(2) 2_766 . . 2_766 ? C11 C10 C9 C8 -19.3(3) . . . . ? C12 C13 C14 C8 -165.35(15) . . . 2_766 ? C13 C12 C11 O3 63.82(18) . . . . ? C13 C12 C11 C10 -177.99(15) . . . . ? C13 C12 C11 C13 -55.1(2) . . . 2_766 ? C14 C8 C9 C10 2.1(3) 2_766 . . . ? C15 C21 C20 C19 13.9(3) 2_655 . . . ? C17 C16 C15 C21 -17.1(3) . . . 2_655 ? C17 C19 C20 C21 -42.9(2) 2_655 . . . ? C17 C18 C19 O6 -58.2(2) . . . . ? C17 C18 C19 C20 178.17(17) . . . . ? C17 C18 C19 C17 55.3(2) . . . 2_655 ? C18 C19 C20 C21 -165.29(18) . . . . ? C18 C17 C16 C15 168.95(17) . . . . ? C19 C17 C16 C15 45.5(2) 2_655 . . . ? C19 C18 C17 O5 61.1(2) . . . . ? C19 C18 C17 C16 -178.74(16) . . . . ? C19 C18 C17 C19 -55.8(2) . . . 2_655 ? C24 C25 C26 O8 -58.8(2) . . . . ? C24 C25 C26 C27 179.55(16) . . . . ? C24 C25 C26 C24 55.9(2) . . . 2_767 ? C25 C24 C23 C22 164.32(19) . . . . ? C26 C27 C28 C22 17.8(3) . . . 2_767 ? C26 C25 C24 O7 63.6(2) . . . . ? C26 C24 C23 C22 41.9(3) 2_767 . . . ? C26 C25 C24 C23 -178.25(18) . . . . ? C26 C25 C24 C26 -55.1(2) . . . 2_767 ? C28 C27 C26 O8 71.5(2) . . . . ? C28 C27 C26 C25 -169.81(17) . . . . ? C28 C27 C26 C24 -45.7(2) . . . 2_767 ? C28 C22 C23 C24 -13.6(3) 2_767 . . . ? O4 C13 C14 C8 72.87(19) . . . 2_766 ? O5 C17 C16 C15 -69.2(2) . . . . ? O6 C19 C20 C21 71.8(2) . . . . ? O7 C24 C23 C22 -75.3(2) . . . . ? #===END #=============================================================================== data_tetrol2 _database_code_depnum_ccdc_archive 'CCDC 250461' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (4aR,8aS,9aR,10aS)perhydro-4a,8a,9a,10a-anthracenetetraol ; _chemical_name_common (4aR,8aS,9aR,10aS)perhydro-4a,8a,9a,10a-anthracenetetraol _chemical_melting_point ? _chemical_formula_moiety 'C14 H24 O4' _chemical_formula_structural 'C14 H24 O4' _chemical_formula_sum 'C14 H24 O4' _chemical_formula_iupac 'C14 H24 O4' _chemical_formula_weight 256.33 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 5.958(5) _cell_length_b 5.994(5) _cell_length_c 9.867(8) _cell_angle_alpha 86.177(13) _cell_angle_beta 82.547(13) _cell_angle_gamma 73.200(12) _cell_volume 334.3(5) _cell_formula_units_Z 1 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ? ; _exptl_crystal_description 'rectangular block' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 140 _exptl_absorpt_coefficient_mu 0.092 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9620 _exptl_absorpt_correction_T_max 0.9918 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2431 _diffrn_reflns_av_R_equivalents 0.0129 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 1213 _reflns_number_gt 1038 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. 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. All CH~2~ and OH hydrogen atoms of the tetrol assymetric unit were placed in geometrically idealised positions and constrained to ride on their parent atoms with C---H distances fixed at 0.97 \%A and U~iso~(H) = 1.2U~eq~(C), and O---H distances fixed at 0.82 \%A and U~iso~(H) = 1.5U~eq~(O). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0789P)^2^+0.0974P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1213 _refine_ls_number_parameters 84 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1471 _refine_ls_wR_factor_gt 0.1405 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.315 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.044 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3898(4) 0.2968(4) 0.1427(2) 0.0597(6) Uani 1 1 d . . . C2 C 0.3106(3) 0.3558(3) 0.2922(2) 0.0468(5) Uani 1 1 d . . . C3 C 0.3722(3) 0.1405(3) 0.38721(17) 0.0359(4) Uani 1 1 d . . . C4 C 0.2954(3) 0.1971(3) 0.53806(17) 0.0366(4) Uani 1 1 d . . . C5 C 0.3580(3) -0.0150(3) 0.63657(18) 0.0367(4) Uani 1 1 d . . . C6 C 0.2834(3) 0.0466(3) 0.78608(19) 0.0483(5) Uani 1 1 d . . . C7 C 0.3460(4) -0.1689(4) 0.8811(2) 0.0591(6) Uani 1 1 d . . . O1 O 0.25339(19) -0.0214(2) 0.34856(13) 0.0427(4) Uani 1 1 d . . . O2 O 0.2379(2) -0.1823(2) 0.60746(13) 0.0429(4) Uani 1 1 d . . . H1 H 0.1122 0.0450 0.3483 0.064 Uiso 1 1 calc R . . H2 H 0.2346 -0.1839 0.5247 0.064 Uiso 1 1 calc R . . H1A H 0.3571 0.4394 0.0869 0.072 Uiso 1 1 calc R . . H1B H 0.3003 0.1995 0.1147 0.072 Uiso 1 1 calc R . . H2A H 0.1412 0.4268 0.3042 0.056 Uiso 1 1 calc R . . H2B H 0.3856 0.4686 0.3170 0.056 Uiso 1 1 calc R . . H4A H 0.1259 0.2671 0.5506 0.044 Uiso 1 1 calc R . . H4B H 0.3691 0.3116 0.5617 0.044 Uiso 1 1 calc R . . H6A H 0.1143 0.1192 0.7996 0.058 Uiso 1 1 calc R . . H6B H 0.3610 0.1583 0.8092 0.058 Uiso 1 1 calc R . . H7A H 0.2554 -0.2735 0.8649 0.071 Uiso 1 1 calc R . . H7B H 0.3044 -0.1222 0.9754 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0583(12) 0.0587(13) 0.0593(12) 0.0117(9) -0.0114(10) -0.0134(10) C2 0.0367(9) 0.0386(10) 0.0629(12) 0.0041(8) -0.0078(8) -0.0077(7) C3 0.0249(8) 0.0306(8) 0.0534(10) -0.0036(7) -0.0055(7) -0.0091(6) C4 0.0235(8) 0.0299(8) 0.0551(10) -0.0069(7) -0.0020(7) -0.0054(6) C5 0.0257(8) 0.0336(9) 0.0518(10) -0.0042(7) -0.0020(7) -0.0102(7) C6 0.0375(9) 0.0500(11) 0.0542(11) -0.0068(8) 0.0018(8) -0.0092(8) C7 0.0570(12) 0.0654(13) 0.0514(11) 0.0026(9) 0.0015(9) -0.0163(10) O1 0.0286(6) 0.0415(7) 0.0622(8) -0.0074(6) -0.0093(5) -0.0133(5) O2 0.0345(7) 0.0415(7) 0.0579(8) 0.0000(6) -0.0050(5) -0.0195(5) #=============================================================================== # 10. MOLECULAR GEOMETRY _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C7 1.534(3) 2_656 ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C1 1.521(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C2 1.528(2) . ? C3 C5 1.559(2) 2_656 ? C4 C3 1.530(3) . ? C4 C5 1.535(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.523(3) . ? C6 C7 1.529(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? O1 C3 1.451(2) . ? O1 H1 0.8200 . ? O2 C5 1.451(2) . ? O2 H2 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C7 H7A 109.4 2_656 . ? C1 C7 H7B 109.4 2_656 . ? C1 C2 C3 112.09(15) . . ? C1 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C2 C3 C5 110.10(14) . 2_656 ? C2 C1 C7 111.66(16) . 2_656 ? C2 C1 H1A 109.3 . . ? C2 C1 H1B 109.3 . . ? C3 C2 H2B 109.2 . . ? C3 C2 H2A 109.2 . . ? C3 C4 C5 114.12(13) . . ? C3 C4 H4A 108.7 . . ? C3 C4 H4B 108.7 . . ? C3 O1 H1 109.5 . . ? C4 C3 C5 110.58(13) . 2_656 ? C4 C5 C3 109.99(14) . 2_656 ? C5 O2 H2 109.5 . . ? C5 C4 H4A 108.7 . . ? C5 C4 H4B 108.7 . . ? C5 C6 C7 111.68(16) . . ? C5 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? C6 C5 C4 113.08(14) . . ? C6 C5 C3 110.44(14) . 2_656 ? C6 C7 C1 110.95(16) . 2_656 ? C6 C7 H7A 109.4 . . ? C6 C7 H7B 109.4 . . ? C7 C6 H6A 109.3 . . ? C7 C6 H6B 109.3 . . ? C7 C1 H1A 109.3 2_656 . ? C7 C1 H1B 109.3 2_656 . ? O1 C3 C2 107.44(14) . . ? O1 C3 C4 109.28(13) . . ? O1 C3 C5 106.41(13) . 2_656 ? O2 C5 C6 107.09(14) . . ? O2 C5 C4 109.37(14) . . ? O2 C5 C3 106.62(13) . 2_656 ? H1A C1 H1B 108.0 . . ? H2A C2 H2B 107.9 . . ? H4A C4 H4B 107.6 . . ? H6A C6 H6B 107.9 . . ? H7A C7 H7B 108.0 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C4 C5 O2 -61.72(17) . . . . ? C3 C4 C5 C6 179.04(12) . . . . ? C3 C4 C5 C3 55.06(19) . . . 2_656 ? C3 C5 C6 C7 -56.9(2) 2_656 . . . ? C3 C2 C1 C7 -55.1(2) . . . 2_656 ? C4 C5 C6 C7 179.39(14) . . . . ? C4 C3 C2 C1 179.57(14) . . . . ? C5 C3 C2 C1 55.5(2) 2_656 . . . ? C5 C4 C3 O1 61.44(17) . . . . ? C5 C4 C3 C2 -179.14(12) . . . . ? C5 C4 C3 C5 -55.37(19) . . . 2_656 ? C5 C6 C7 C1 55.8(2) . . . 2_656 ? O1 C3 C2 C1 -59.94(19) . . . . ? O2 C5 C6 C7 58.84(19) . . . . ? #===END