Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'Dec 12 13:33:54 2004' _audit_creation_method 'PLATON option' _audit_update_record ; ? ; #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name 'Goverdhan Mehta' _publ_contact_author_address ; Department of Organic Chemistry Indian Institute of Science Bangalore 560 012 INDIA ; _publ_section_title ; Additive induced polymorphous behaviour of a conformationally locked hexol ; _publ_contact_author_email gm@orgchem.iisc.ernet.in _publ_contact_author_fax +91-80-23600936 _publ_contact_author_phone +91-80-22932850 # Insert blank lines between references _publ_section_references ; Allen, F.H. & Kennard, O. (1993). Chem. Des. Autom. News., 8, 31-37. 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., Garcia-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, 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, 276, 307-326. 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. ; loop_ _publ_author_name G.Mehta S.Sen #===END #=============================================================================== data_hexol_monohydrate _database_code_depnum_ccdc_archive 'CCDC 620926' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; all trans-perhydro-2,3,4a,6,7,8a-naphthalenehexaol monohydrate ; _chemical_name_common 'all trans-perhydro-2,3,4a,6,7,8a-naphthalenehexaol monohydrate' _chemical_melting_point ? _chemical_formula_moiety 'C10 H18 O6, H2 O' _chemical_formula_structural ? _chemical_formula_sum 'C10 H20 O7' _chemical_formula_iupac ? _chemical_formula_weight 252.26 _chemical_compound_source 'see text' 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 6.663(2) _cell_length_b 9.045(3) _cell_length_c 10.707(3) _cell_angle_alpha 72.385(5) _cell_angle_beta 81.655(5) _cell_angle_gamma 69.238(5) _cell_volume 574.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.24 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.124 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)' _exptl_absorpt_correction_T_min 0.9327 _exptl_absorpt_correction_T_max 0.9709 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoKa _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 4399 _diffrn_reflns_av_R_equivalents 0.0149 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.85 _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 2187 _reflns_number_gt 1923 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _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. ; _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^)+(0.0602P)^2^+0.1265P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2187 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.320 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.046 #=============================================================================== # 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 O1W O 0.8023(3) 0.95245(18) 0.23935(15) 0.0613(4) Uani 1 1 d . . . O1 O 0.72007(19) 0.21777(13) 0.33775(10) 0.0430(3) Uani 1 1 d . . . O2 O 0.76257(18) 0.14953(12) 0.68940(10) 0.0390(3) Uani 1 1 d . . . O3 O 0.50178(16) 0.46187(11) 0.67925(9) 0.0318(2) Uani 1 1 d . . . O4 O 0.66697(18) 0.79303(13) 1.11186(10) 0.0405(3) Uani 1 1 d . . . O5 O 0.77539(19) 0.83319(12) 0.76323(10) 0.0423(3) Uani 1 1 d . . . O6 O 1.06276(17) 0.52394(11) 0.82300(9) 0.0332(3) Uani 1 1 d . . . C1 C 0.6414(2) 0.19758(16) 0.47180(14) 0.0335(3) Uani 1 1 d . . . C2 C 0.8062(2) 0.20877(16) 0.55128(13) 0.0324(3) Uani 1 1 d . . . C3 C 0.8041(2) 0.38408(16) 0.52638(13) 0.0299(3) Uani 1 1 d . . . C4 C 0.5799(2) 0.50377(15) 0.54434(12) 0.0258(3) Uani 1 1 d . . . C5 C 0.5816(2) 0.67998(16) 0.51436(14) 0.0314(3) Uani 1 1 d . . . C6 C 0.7970(2) 0.81332(16) 0.99268(13) 0.0329(3) Uani 1 1 d . . . C7 C 0.6918(2) 0.77634(16) 0.89340(14) 0.0338(3) Uani 1 1 d . . . C8 C 0.7173(2) 0.59418(16) 0.92828(14) 0.0315(3) Uani 1 1 d . . . C9 C 0.9496(2) 0.48187(15) 0.94761(12) 0.0260(3) Uani 1 1 d . . . C10 C 1.0295(2) 0.69998(15) 1.01467(13) 0.0299(3) Uani 1 1 d . . . H2W H 0.757(3) 1.034(3) 0.265(2) 0.069(7) Uiso 1 1 d . . . H1W H 0.932(4) 0.920(3) 0.248(2) 0.070(7) Uiso 1 1 d . . . H1O H 0.6778 0.3154 0.2978 0.064 Uiso 1 1 calc R . . H2O H 0.7665 0.0538 0.7066 0.059 Uiso 1 1 calc R . . H3O H 0.5559 0.3629 0.7122 0.048 Uiso 1 1 calc R . . H5O H 0.8891 0.7641 0.7498 0.063 Uiso 1 1 calc R . . H4O H 0.6850 0.8455 1.1572 0.061 Uiso 1 1 calc R . . H6O H 1.1683 0.4448 0.8161 0.050 Uiso 1 1 calc R . . H1 H 0.6312 0.0868 0.5055 0.040 Uiso 1 1 calc R . . H2 H 0.9498 0.1411 0.5279 0.039 Uiso 1 1 calc R . . H3A H 0.8591 0.4206 0.4376 0.036 Uiso 1 1 calc R . . H3B H 0.8993 0.3858 0.5861 0.036 Uiso 1 1 calc R . . H5A H 0.6759 0.6836 0.5736 0.038 Uiso 1 1 calc R . . H5B H 0.6392 0.7122 0.4256 0.038 Uiso 1 1 calc R . . H6 H 0.7942 0.9277 0.9613 0.039 Uiso 1 1 calc R . . H7 H 0.5378 0.8379 0.8964 0.041 Uiso 1 1 calc R . . H8A H 0.6329 0.5669 1.0082 0.038 Uiso 1 1 calc R . . H8B H 0.6605 0.5740 0.8589 0.038 Uiso 1 1 calc R . . H10A H 1.1159 0.7245 0.9351 0.036 Uiso 1 1 calc R . . H10B H 1.0853 0.7216 1.0837 0.036 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 O1W 0.0565(9) 0.0522(8) 0.0825(11) -0.0393(7) -0.0220(7) -0.0016(7) O1 0.0583(7) 0.0319(5) 0.0361(6) -0.0159(4) 0.0044(5) -0.0086(5) O2 0.0483(6) 0.0262(5) 0.0338(6) -0.0018(4) -0.0014(5) -0.0072(5) O3 0.0386(6) 0.0269(5) 0.0256(5) -0.0062(4) 0.0019(4) -0.0075(4) O4 0.0473(6) 0.0356(6) 0.0385(6) -0.0167(4) 0.0094(5) -0.0123(5) O5 0.0556(7) 0.0292(5) 0.0313(6) -0.0002(4) -0.0048(5) -0.0067(5) O6 0.0409(6) 0.0284(5) 0.0249(5) -0.0051(4) 0.0050(4) -0.0092(4) C1 0.0422(8) 0.0229(6) 0.0345(7) -0.0088(5) 0.0019(6) -0.0101(6) C2 0.0309(7) 0.0254(7) 0.0331(7) -0.0064(5) 0.0012(6) -0.0024(5) C3 0.0267(7) 0.0297(7) 0.0309(7) -0.0066(5) 0.0005(5) -0.0085(5) C4 0.0266(7) 0.0241(6) 0.0259(7) -0.0063(5) 0.0012(5) -0.0085(5) C5 0.0351(7) 0.0267(7) 0.0349(7) -0.0086(5) -0.0005(6) -0.0135(6) C6 0.0409(8) 0.0226(6) 0.0326(7) -0.0068(5) 0.0025(6) -0.0096(6) C7 0.0329(7) 0.0273(7) 0.0343(8) -0.0043(6) -0.0042(6) -0.0040(5) C8 0.0305(7) 0.0304(7) 0.0331(7) -0.0062(5) -0.0051(6) -0.0102(6) C9 0.0304(7) 0.0239(6) 0.0230(6) -0.0045(5) 0.0006(5) -0.0104(5) C10 0.0357(7) 0.0261(7) 0.0306(7) -0.0080(5) 0.0006(6) -0.0138(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 O1W H2W 0.80(2) . ? O1W H1W 0.82(3) . ? O1 C1 1.4349(17) . ? O1 H1O 0.8200 . ? O2 C2 1.4369(17) . ? O2 H2O 0.8200 . ? O3 C4 1.4460(15) . ? O3 H3O 0.8200 . ? O4 C6 1.4363(17) . ? O4 H4O 0.8200 . ? O5 C7 1.4356(17) . ? O5 H5O 0.8200 . ? O6 C9 1.4483(15) . ? O6 H6O 0.8200 . ? C1 H1 0.9800 . ? C2 C1 1.530(2) . ? C2 H2 0.9800 . ? C3 C2 1.5215(19) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C3 1.5287(18) . ? C4 C5 1.5316(18) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.527(2) . ? C6 C10 1.529(2) . ? C6 H6 0.9800 . ? C7 H7 0.9800 . ? C8 C9 1.5234(19) . ? C8 C7 1.5266(19) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? 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 O1 C1 C2 108.54(12) . . ? O1 C1 H1 107.8 . . ? O2 C2 C1 110.58(11) . . ? O2 C2 C3 107.01(11) . . ? O2 C2 H2 108.9 . . ? O3 C4 C3 110.37(10) . . ? O3 C4 C5 105.97(10) . . ? O4 C6 C7 106.03(12) . . ? O4 C6 C10 111.10(11) . . ? O4 C6 H6 109.2 . . ? O5 C7 C6 110.20(12) . . ? O5 C7 C8 111.93(11) . . ? O5 C7 H7 107.7 . . ? O6 C9 C8 105.74(10) . . ? C1 O1 H1O 109.5 . . ? C1 C2 H2 108.9 . . ? C2 C3 C4 112.86(11) . . ? C2 O2 H2O 109.5 . . ? C2 C1 H1 107.8 . . ? C2 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C3 C2 C1 112.49(11) . . ? C3 C4 C5 111.65(11) . . ? C3 C2 H2 108.9 . . ? C4 O3 H3O 109.5 . . ? C4 C3 H3A 109.0 . . ? C4 C3 H3B 109.0 . . ? C4 C5 H5A 109.1 . . ? C4 C5 H5B 109.1 . . ? C6 O4 H4O 109.5 . . ? C6 C7 H7 107.7 . . ? C6 C10 H10A 109.1 . . ? C6 C10 H10B 109.1 . . ? C7 C6 C10 112.11(11) . . ? C7 O5 H5O 109.5 . . ? C7 C6 H6 109.2 . . ? C7 C8 H8A 108.9 . . ? C7 C8 H8B 108.9 . . ? C8 C7 C6 111.45(11) . . ? C8 C7 H7 107.7 . . ? C9 C8 C7 113.30(11) . . ? C9 O6 H6O 109.5 . . ? C9 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C10 C6 H6 109.2 . . ? H3A C3 H3B 107.8 . . ? H5A C5 H5B 107.8 . . ? H8A C8 H8B 107.7 . . ? H10A C10 H10B 107.8 . . ? H2W O1W H1W 105(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C2 C1 O1 -165.68(10) . . . . ? O3 C4 C3 C2 64.25(14) . . . . ? O4 C6 C7 O5 165.25(10) . . . . ? O4 C6 C7 C8 -69.85(14) . . . . ? C3 C2 C1 O1 74.74(13) . . . . ? C4 C3 C2 O2 -69.27(14) . . . . ? C4 C3 C2 C1 52.37(15) . . . . ? C5 C4 C3 C2 -178.17(11) . . . . ? C7 C8 C9 O6 -61.40(13) . . . . ? C9 C8 C7 O5 70.56(15) . . . . ? C9 C8 C7 C6 -53.36(16) . . . . ? C10 C6 C7 O5 -73.34(14) . . . . ? C10 C6 C7 C8 51.56(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # D H A D - H H...A D...A D - H...A symm(A) # - - - ----- ----- ----- --------- ------- O1 H1O O3 0.82 2.01 2.7086(17) 142 2_666 yes O2 H2O O5 0.82 1.88 2.7010(18) 174 1_545 yes O3 H3O O2 0.82 2.00 2.7205(17) 147 1_555 yes O4 H4O O1W 0.82 1.89 2.688(2) 164 1_556 yes O5 H5O O6 0.82 2.03 2.7157(17) 141 1_555 yes O6 H6O O4 0.82 2.00 2.7282(18) 148 2_767 yes O1W H1W O2 0.82(3) 2.05(3) 2.856(3) 167.15(2) 2_766 yes O1W H2W O1 0.81(3) 1.97(3) 2.757(2) 165.88(2) 1_565 yes #===END #=============================================================================== data_beta_polymorph _database_code_depnum_ccdc_archive 'CCDC 620927' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; all trans-perhydro-2,3,4a,6,7,8a-naphthalenehexaol ; _chemical_name_common 'all trans-perhydro-2,3,4a,6,7,8a-naphthalenehexaol' _chemical_melting_point ? _chemical_formula_moiety 'C10 H18 O6' _chemical_formula_structural ? _chemical_formula_sum 'C10 H18 O6' _chemical_formula_weight 234.24 _chemical_compound_source 'see text' 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 Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 6.5273(14) _cell_length_b 5.9589(12) _cell_length_c 13.166(3) _cell_angle_alpha 90 _cell_angle_beta 90.163(3) _cell_angle_gamma 90 _cell_volume 512.10(19) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ? ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.06 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 252 _exptl_absorpt_coefficient_mu 0.125 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)' _exptl_absorpt_correction_T_min 0.9593 _exptl_absorpt_correction_T_max 0.9925 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoKa _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 3602 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 953 _reflns_number_gt 839 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _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. ; _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^)+(0.0332P)^2^+0.1421P] 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 953 _refine_ls_number_parameters 76 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0796 _refine_ls_wR_factor_gt 0.0759 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.166 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.034 #=============================================================================== # 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 O1 O 0.19346(16) 0.64527(17) 0.88185(8) 0.0324(3) Uani 1 1 d . . . O2 O 0.59290(17) 0.98418(19) 0.75996(8) 0.0358(3) Uani 1 1 d . . . O3 O 0.68981(15) 1.18626(15) 0.93925(7) 0.0269(3) Uani 1 1 d . . . C1 C 0.2856(2) 0.8471(2) 0.84360(11) 0.0262(3) Uani 1 1 d . . . C2 C 0.5112(2) 0.8031(2) 0.81919(11) 0.0270(4) Uani 1 1 d . . . C3 C 0.6406(2) 0.7844(2) 0.91490(11) 0.0250(3) Uani 1 1 d . . . C4 C 0.6150(2) 0.9831(2) 0.98678(11) 0.0221(3) Uani 1 1 d . . . C5 C 0.7399(2) 0.9554(2) 1.08398(11) 0.0241(3) Uani 1 1 d . . . H1O H 0.1988 0.6453 0.9441 0.049 Uiso 1 1 calc R . . H2O H 0.5166 1.0095 0.7117 0.054 Uiso 1 1 calc R . . H3O H 0.6821 1.1736 0.8773 0.040 Uiso 1 1 calc R . . H1 H 0.2161 0.8857 0.7799 0.031 Uiso 1 1 calc R . . H2 H 0.5223 0.6632 0.7804 0.032 Uiso 1 1 calc R . . H3A H 0.7836 0.7725 0.8958 0.030 Uiso 1 1 calc R . . H3B H 0.6037 0.6478 0.9505 0.030 Uiso 1 1 calc R . . H5A H 0.6977 0.8187 1.1180 0.029 Uiso 1 1 calc R . . H5B H 0.8836 0.9402 1.0666 0.029 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 O1 0.0361(6) 0.0308(6) 0.0302(6) -0.0017(5) -0.0027(5) -0.0091(5) O2 0.0346(7) 0.0482(7) 0.0244(6) 0.0064(5) -0.0011(5) -0.0067(5) O3 0.0318(6) 0.0261(6) 0.0228(6) 0.0030(4) 0.0002(4) -0.0045(4) C1 0.0265(7) 0.0283(8) 0.0238(8) 0.0021(7) -0.0058(6) -0.0012(6) C2 0.0307(8) 0.0269(8) 0.0236(8) -0.0035(6) 0.0006(6) -0.0008(6) C3 0.0218(7) 0.0254(8) 0.0277(8) -0.0005(6) 0.0008(6) 0.0030(6) C4 0.0232(8) 0.0197(7) 0.0234(8) 0.0016(6) -0.0007(6) 0.0009(5) C5 0.0203(7) 0.0250(7) 0.0270(8) 0.0038(6) -0.0010(6) 0.0016(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 O1 C1 1.4366(17) . ? O1 H1O 0.8200 . ? O2 C2 1.4353(17) . ? O2 H2O 0.8200 . ? O3 C4 1.4481(16) . ? O3 H3O 0.8200 . ? C1 H1 0.9800 . ? C2 C1 1.530(2) . ? C2 H2 0.9800 . ? C3 C2 1.519(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.524(2) . ? C4 C3 1.5255(19) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? 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 O1 C1 C2 109.51(11) . . ? O1 C1 H1 107.7 . . ? O2 C2 C1 110.15(12) . . ? O2 C2 C3 107.41(12) . . ? O2 C2 H2 109.1 . . ? O3 C4 C3 110.07(11) . . ? O3 C4 C5 105.86(11) . . ? C1 O1 H1O 109.5 . . ? C1 C2 H2 109.1 . . ? C2 O2 H2O 109.5 . . ? C2 C3 C4 113.33(11) . . ? C2 C1 H1 107.7 . . ? C2 C3 H3A 108.9 . . ? C2 C3 H3B 108.9 . . ? C3 C2 C1 111.80(12) . . ? C3 C2 H2 109.1 . . ? C4 O3 H3O 109.5 . . ? C4 C3 H3A 108.9 . . ? C4 C3 H3B 108.9 . . ? C4 C5 H5A 109.1 . . ? C4 C5 H5B 109.1 . . ? C5 C4 C3 112.18(11) . . ? H3A C3 H3B 107.7 . . ? H5A C5 H5B 107.8 . . ? 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 O2 C2 C1 O1 166.84(11) . . . . ? O3 C4 C3 C2 -64.71(15) . . . . ? C3 C2 C1 O1 -73.82(14) . . . . ? C4 C3 C2 O2 68.32(15) . . . . ? C4 C3 C2 C1 -52.62(16) . . . . ? C5 C4 C3 C2 177.70(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # D H A D - H H...A D...A D - H...A symm(A) # - - - ----- ----- ----- --------- ------- O1 H1O O3 0.82 1.97 2.6695(15) 142 3_677 yes O2 H2O O1 0.82 2.01 2.8074(16) 164 2_556 yes O3 H3O O2 0.82 2.00 2.7228(15) 147 1_555 yes