# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 # CCDC Number: 440/227 # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_compound[11](mbdw3z) _audit_creation_method 'maXus + CRYSTALS_ver_12-03-99' _publ_contact_author_name ' Alison Edwards' _publ_contact_author_email 'ajed@rsc.anu.edu.au' _publ_contact_author_fax ' australia + 2 6249 0750' _publ_contact_author_phone 'australia + 2 62494109' _publ_contact_author_address ; Research School of Chemistry, ANU, A.C.T., 0200 Australia ; _publ_section_title ; mbdw3z ; _publ_section_abstract ; We present the crystal and molecular structure of ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using maXus (Nonius, Delft & MacScience, Japan). ; _publ_section_synopsis ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'plate' _exptl_crystal_colour 'Colourless' _cell_measurement_temperature 200 _refine_ls_hydrogen_treatment 'noref' # Submission details _publ_requested_journal 'test ' _diffrn_measurement_device 'KappaCCD' _diffrn_measurement_method 'CCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) maxus(Mackay et al., 1999) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 272.297 _diffrn_radiation_type ' MoK\a' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X+ 1/2,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X,+Y+ 1/2,-Z+ 1/2' _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_cell_setting 'Orthorhombic' _chemical_formula_moiety 'C13 H20 O6 ' _chemical_formula_sum 'C13 H20 O6 ' _chemical_name_systematic ; ? ; _cell_length_a 8.4308(4) _cell_length_b 10.5457(5) _cell_length_c 15.6538(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1391.80(10) _diffrn_reflns_number 17901 _diffrn_reflns_theta_max 26.4 _cell_measurement_reflns_used 17814 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 25.485 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 1 0.120 1 0 -1 0.160 0 1 0 0.135 0 -1 0 0.220 0 0 -1 0.000 0 0 1 0.040 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_reflns_av_R_equivalents 0.060 _exptl_absorpt_coefficient_mu 0.103 _exptl_crystal_F_000 584 # Refinement statistics _reflns_d_resolution_low 1.58 _reflns_d_resolution_high 0.77 _reflns_number_total 1590 _reflns_number_gt 1331 _reflns_limit_h_min 0 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _refine_diff_density_min -0.22 _refine_diff_density_max 0.23 _reflns_threshold_expression >2.50\s(I) _refine_ls_number_reflns 1331 _refine_ls_number_parameters 172 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.0224 _refine_ls_goodness_of_fit_ref 0.9997 _refine_ls_shift/su_max 0.000148 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 1.29 1.49 0.971 ; _refine_ls_extinction_method 'None' _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Carruthers, J.R. and Watkin, D.J. (1979), Acta Cryst, A35, 698-699 Coppens, P. (1970). In Crystallographic Computing, edited by F.R. Ahmed, S.R.Hall & C.P.Huber, pp 255-270. Copenhagen: Munksgaard. Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W. (1996) CRYSTALS Issue 10. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 0.18992(11) 0.32319(11) 0.38780(6) 0.0389 1.0000 Uani O3 0.38986(11) 0.22011(11) 0.32153(6) 0.0396 1.0000 Uani O4 0.25617(18) 0.06334(11) 0.15279(7) 0.0522 1.0000 Uani O5 0.25863(13) 0.2716(1) 0.14977(6) 0.0399 1.0000 Uani O7 -0.04819(13) 0.3979(1) 0.14882(7) 0.0405 1.0000 Uani O9 -0.06892(13) 0.20963(9) 0.22013(6) 0.0386 1.0000 Uani C2 0.34957(17) 0.27980(18) 0.40074(9) 0.0410 1.0000 Uani C3 0.25067(19) 0.16135(14) 0.29033(8) 0.0358 1.0000 Uani C4 0.25229(19) 0.16115(15) 0.19265(9) 0.0371 1.0000 Uani C6 0.23029(18) 0.39250(15) 0.19289(8) 0.0369 1.0000 Uani C8 -0.13362(18) 0.27936(15) 0.14979(9) 0.0418 1.0000 Uani C9 -0.00590(15) 0.30074(13) 0.27851(9) 0.0336 1.0000 Uani C10 0.2789(2) 0.49339(17) 0.1295(1) 0.0519 1.0000 Uani C11 -0.1006(3) 0.2060(2) 0.06835(11) 0.0622 1.0000 Uani C12 -0.3083(2) 0.30504(18) 0.16406(13) 0.0556 1.0000 Uani C13 0.3569(2) 0.1854(2) 0.47396(11) 0.0544 1.0000 Uani C14 0.4559(2) 0.3935(2) 0.41295(12) 0.0552 1.0000 Uani C61 0.05694(17) 0.40448(12) 0.22055(8) 0.0334 1.0000 Uani C91 0.11248(14) 0.23150(14) 0.33544(7) 0.0339 1.0000 Uani H31 0.23968(19) 0.06911(14) 0.30389(8) 0.0600 1.0000 Uiso H61 0.29296(18) 0.40050(15) 0.24686(8) 0.0600 1.0000 Uiso H91 -0.08035(15) 0.34119(13) 0.32011(9) 0.0600 1.0000 Uiso H101 0.2622(2) 0.57904(17) 0.1554(1) 0.0612 1.0000 Uiso H102 0.3935(2) 0.48257(17) 0.1147(1) 0.0612 1.0000 Uiso H103 0.2131(2) 0.48541(17) 0.0766(1) 0.0612 1.0000 Uiso H111 -0.1602(3) 0.1240(2) 0.06954(11) 0.0741 1.0000 Uiso H112 -0.1355(3) 0.2572(2) 0.01797(11) 0.0741 1.0000 Uiso H113 0.0156(3) 0.1883(2) 0.06387(11) 0.0741 1.0000 Uiso H121 -0.3676(2) 0.22294(18) 0.16479(13) 0.0627 1.0000 Uiso H122 -0.3230(2) 0.34944(18) 0.21995(13) 0.0627 1.0000 Uiso H123 -0.3496(2) 0.35973(18) 0.11685(13) 0.0627 1.0000 Uiso H131 0.4689(2) 0.1564(2) 0.48203(11) 0.0617 1.0000 Uiso H132 0.3185(2) 0.2269(2) 0.52757(11) 0.0617 1.0000 Uiso H133 0.2881(2) 0.1108(2) 0.46045(11) 0.0617 1.0000 Uiso H141 0.5675(2) 0.3645(2) 0.42206(12) 0.0639 1.0000 Uiso H142 0.4197(2) 0.4430(2) 0.46385(12) 0.0639 1.0000 Uiso H143 0.4508(2) 0.4485(2) 0.36095(12) 0.0639 1.0000 Uiso H611 0.05848(17) 0.48758(12) 0.25131(8) 0.0600 1.0000 Uiso H911 0.04616(14) 0.16660(14) 0.36533(7) 0.0600 1.0000 Uiso 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 0.0288(5) 0.0491(6) 0.0387(5) -0.0091(4) 0.0006(4) 0.0020(4) O3 0.0282(5) 0.0527(6) 0.0379(5) 0.0015(4) 0.0028(3) 0.0048(4) O4 0.0544(7) 0.0471(6) 0.0552(5) -0.0132(5) 0.0027(6) 0.0136(5) O5 0.0361(5) 0.0463(6) 0.0373(4) -0.0007(4) 0.0069(5) 0.0066(5) O7 0.0367(5) 0.0402(5) 0.0447(5) 0.0041(4) -0.0047(4) 0.0031(4) O9 0.0361(5) 0.0325(5) 0.0473(5) -0.0026(4) -0.0054(4) -0.0011(4) C2 0.0255(6) 0.0576(9) 0.0399(7) -0.0019(7) 0.0005(5) 0.0023(6) C3 0.0293(6) 0.0357(7) 0.0425(6) 0.0041(5) 0.0009(7) 0.0036(6) C4 0.0322(7) 0.0362(7) 0.0428(6) -0.0044(6) 0.0044(7) 0.0075(6) C6 0.0327(7) 0.0375(7) 0.0406(6) 0.0011(5) 0.0052(6) -0.0015(5) C8 0.0371(7) 0.0384(7) 0.0499(8) 0.0001(7) -0.0091(6) 0.0005(6) C9 0.0284(6) 0.0338(8) 0.0385(6) -0.0040(5) 0.0002(5) -0.0028(5) C10 0.044(1) 0.052(1) 0.0600(8) 0.0187(8) 0.0068(6) -0.0013(6) C11 0.0634(12) 0.0715(13) 0.0517(9) -0.0120(9) -0.0159(8) 0.007(1) C12 0.0332(7) 0.0572(11) 0.0764(12) -0.0025(9) -0.0105(6) 0.0015(7) C13 0.0440(8) 0.0794(13) 0.0399(7) 0.0053(8) -0.0026(6) 0.0028(8) C14 0.0391(8) 0.0693(11) 0.057(1) -0.0097(8) -0.0057(7) -0.0110(8) C61 0.0292(6) 0.0327(7) 0.0382(6) 0.0003(5) -0.0029(5) 0.0007(5) C91 0.0272(6) 0.0364(7) 0.0381(6) -0.0005(5) 0.0010(4) -0.0038(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.4360(17) yes O1 . C91 . 1.4258(18) yes O3 . C2 . 1.4314(19) yes O3 . C3 . 1.414(2) yes O4 . C4 . 1.206(2) yes O5 . C4 . 1.346(2) yes O5 . C6 . 1.462(2) yes O7 . C8 . 1.443(2) yes O7 . C61 . 1.4322(18) yes O9 . C8 . 1.4321(18) yes O9 . C9 . 1.4284(16) yes C2 . C13 . 1.519(2) yes C2 . C14 . 1.509(3) yes C3 . C4 . 1.5291(18) yes C3 . C91 . 1.550(2) yes C3 . H31 . 1.000 no C6 . C10 . 1.511(2) yes C6 . C61 . 1.529(2) yes C6 . H61 . 1.000 no C8 . C11 . 1.517(3) yes C8 . C12 . 1.514(2) yes C9 . C61 . 1.5168(19) yes C9 . C91 . 1.5243(18) yes C9 . H91 . 1.000 no C10 . H101 . 1.000 no C10 . H102 . 1.000 no C10 . H103 . 1.000 no C11 . H111 . 1.000 no C11 . H112 . 1.000 no C11 . H113 . 1.000 no C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 1.000 no C61 . H611 . 1.000 no C91 . H911 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C91 . 107.11(11) yes C2 . O3 . C3 . 107.2(1) yes C4 . O5 . C6 . 121.2(1) yes C8 . O7 . C61 . 110.0(1) yes C8 . O9 . C9 . 106.7(1) yes O1 . C2 . O3 . 103.91(11) yes O1 . C2 . C13 . 110.69(13) yes O3 . C2 . C13 . 110.84(15) yes O1 . C2 . C14 . 108.73(15) yes O3 . C2 . C14 . 108.56(12) yes C13 . C2 . C14 . 113.62(14) yes O3 . C3 . C4 . 109.79(12) yes O3 . C3 . C91 . 104.91(11) yes C4 . C3 . C91 . 117.57(12) yes O3 . C3 . H31 . 115.46(8) no C4 . C3 . H31 . 102.22(8) no C91 . C3 . H31 . 107.33(8) no O4 . C4 . O5 . 118.77(12) yes O4 . C4 . C3 . 121.26(14) yes O5 . C4 . C3 . 119.86(13) yes O5 . C6 . C10 . 105.45(12) yes O5 . C6 . C61 . 111.03(12) yes C10 . C6 . C61 . 112.76(13) yes O5 . C6 . H61 . 112.16(7) no C10 . C6 . H61 . 110.60(9) no C61 . C6 . H61 . 105.00(7) no O7 . C8 . O9 . 105.2(1) yes O7 . C8 . C11 . 109.97(14) yes O9 . C8 . C11 . 108.31(13) yes O7 . C8 . C12 . 109.40(13) yes O9 . C8 . C12 . 110.43(14) yes C11 . C8 . C12 . 113.18(14) yes O9 . C9 . C61 . 103.44(11) yes O9 . C9 . C91 . 107.2(1) yes C61 . C9 . C91 . 117.81(11) yes O9 . C9 . H91 . 118.04(7) no C61 . C9 . H91 . 107.52(7) no C91 . C9 . H91 . 103.57(7) no C6 . C10 . H101 . 109.37(9) no C6 . C10 . H102 . 109.5(1) no H101 . C10 . H102 . 109.476 no C6 . C10 . H103 . 109.49(9) no H101 . C10 . H103 . 109.476 no H102 . C10 . H103 . 109.476 no C8 . C11 . H111 . 109.45(11) no C8 . C11 . H112 . 109.5(1) no H111 . C11 . H112 . 109.476 no C8 . C11 . H113 . 109.5(1) no H111 . C11 . H113 . 109.476 no H112 . C11 . H113 . 109.476 no C8 . C12 . H121 . 109.5(1) no C8 . C12 . H122 . 109.5(1) no H121 . C12 . H122 . 109.476 no C8 . C12 . H123 . 109.5(1) no H121 . C12 . H123 . 109.476 no H122 . C12 . H123 . 109.476 no C2 . C13 . H131 . 109.52(9) no C2 . C13 . H132 . 109.5(1) no H131 . C13 . H132 . 109.476 no C2 . C13 . H133 . 109.4(1) no H131 . C13 . H133 . 109.476 no H132 . C13 . H133 . 109.476 no C2 . C14 . H141 . 109.5(1) no C2 . C14 . H142 . 109.53(9) no H141 . C14 . H142 . 109.476 no C2 . C14 . H143 . 109.38(9) no H141 . C14 . H143 . 109.476 no H142 . C14 . H143 . 109.476 no O7 . C61 . C6 . 111.43(11) yes O7 . C61 . C9 . 102.59(11) yes C6 . C61 . C9 . 116.33(11) yes O7 . C61 . H611 . 115.33(6) no C6 . C61 . H611 . 101.32(7) no C9 . C61 . H611 . 110.40(7) no O1 . C91 . C3 . 104.0(1) yes O1 . C91 . C9 . 108.12(11) yes C3 . C91 . C9 . 117.0(1) yes O1 . C91 . H911 . 116.82(7) no C3 . C91 . H911 . 107.86(8) no C9 . C91 . H911 . 103.61(7) no # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_compound[13](mbdw1z) _vrf_REFNR_01_mbdw1z ; PROBLEM: Alert B Ratio of reflections to parameters is < 6 for a RESPONSE: Structure is included here primarily for identification of compound and has been independently determined by others referred to in manuscript. ; _vrf_THETM_01_mbdw1z ; PROBLEM: Alert A The value of sine(theta_max)/wavelength is less than 0.550 RESPONSE: The crystal did not diffract at higher resolution ; _audit_creation_method 'maXus + CRYSTALS_ver_12-03-99' _publ_contact_author_name ' Alison Edwards' _publ_contact_author_email 'ajed@rsc.anu.edu.au' _publ_contact_author_fax ' australia + 2 6249 0750' _publ_contact_author_phone 'australia + 2 62494109' _publ_contact_author_address ; Research School of Chemistry, ANU, A.C.T., 0200 Australia ; _publ_section_title ; Crystal and molecular structure of mbdw1z ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_synopsis ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'needle' _exptl_crystal_colour 'Colourless' _cell_measurement_temperature 200 _refine_ls_hydrogen_treatment 'noref' # Submission details _publ_requested_journal 'Acta Crystallographica Section C ' _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) maxus(Mackay et al., 1999) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 0.02584 _diffrn_orient_matrix_UB_12 0.04261 _diffrn_orient_matrix_UB_13 -0.04434 _diffrn_orient_matrix_UB_21 0.01197 _diffrn_orient_matrix_UB_22 -0.08458 _diffrn_orient_matrix_UB_23 -0.02241 _diffrn_orient_matrix_UB_31 -0.14127 _diffrn_orient_matrix_UB_32 0.00063 _diffrn_orient_matrix_UB_33 -0.01001 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 274.313 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X+ 1/2,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X,+Y+ 1/2,-Z+ 1/2' _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_cell_setting 'Orthorhombic' _chemical_formula_moiety 'C13 H22 O6 ' _chemical_formula_sum 'C13 H22 O6 ' _chemical_name_systematic ; ? ; _cell_length_a 6.9393(5) _cell_length_b 10.5584(8) _cell_length_c 19.7333(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1445.8(2) _diffrn_reflns_number 5379 _diffrn_reflns_theta_max 22.45 _diffrn_reflns_av_R_equivalents 0.045 _cell_measurement_reflns_used 3127 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 22.465 _diffrn_measurement_method 'CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_coefficient_mu 0.10 _exptl_crystal_F_000 592 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' # Refinement statistics _reflns_d_resolution_low 1.68 _reflns_d_resolution_high 0.68 _reflns_limit_h_max 7 _reflns_limit_h_min 0 _reflns_limit_k_max 11 _reflns_limit_k_min 0 _reflns_limit_l_max 20 _reflns_limit_l_min 0 _reflns_number_total 1113 _refine_diff_density_min -0.22 _refine_diff_density_max 0.31 _reflns_threshold_expression >2.50\s(I) _reflns_number_gt 985 _refine_ls_number_reflns 985 _refine_ls_number_parameters 173 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.0463 _refine_ls_goodness_of_fit_ref 0.9641 _refine_ls_shift/su_max 0.000494 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 0.819 0.494 0.556 ; _refine_ls_extinction_coef 401.2(1129) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Larson, A.C. (1970), Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294 Carruthers, J.R. and Watkin, D.J. (1979), Acta Cryst, A35, 698-699 Coppens, P. (1970). In Crystallographic Computing, edited by F.R. Ahmed, S.R.Hall & C.P.Huber, pp 255-270. Copenhagen: Munksgaard. Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W. (1996) CRYSTALS Issue 10. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 -0.2789(3) 0.3302(3) 0.07119(14) 0.0699 1.0000 Uani O2 0.0712(4) 0.5675(2) 0.04114(14) 0.0714 1.0000 Uani O3 0.3170(3) 0.4531(2) 0.08202(12) 0.0519 1.0000 Uani O4 -0.0486(3) 0.3781(2) 0.15335(11) 0.0489 1.0000 Uani O5 0.3986(3) 0.2031(2) 0.15439(12) 0.0572 1.0000 Uani O6 0.3555(3) 0.1336(2) 0.26260(12) 0.0575 1.0000 Uani C1 -0.1526(5) 0.4233(4) 0.09532(18) 0.0564 1.0000 Uani C2 0.0005(5) 0.4403(4) 0.04094(18) 0.0552 1.0000 Uani C3 0.1735(5) 0.3613(3) 0.06449(16) 0.0474 1.0000 Uani C4 0.0979(5) 0.2961(3) 0.12778(16) 0.0439 1.0000 Uani C5 0.2466(5) 0.2745(3) 0.18312(16) 0.0430 1.0000 Uani C6 0.1788(5) 0.1962(3) 0.24284(17) 0.0511 1.0000 Uani C7 0.1031(6) 0.2684(4) 0.30273(19) 0.0674 1.0000 Uani C8 0.2775(5) 0.5616(4) 0.04288(19) 0.0577 1.0000 Uani C9 0.3523(8) 0.6770(4) 0.0794(3) 0.0804 1.0000 Uani C10 0.3606(9) 0.5486(5) -0.0276(2) 0.0911 1.0000 Uani C11 0.4560(5) 0.1055(3) 0.20174(18) 0.0504 1.0000 Uani C12 0.6682(5) 0.1181(4) 0.2156(2) 0.0590 1.0000 Uani C13 0.4003(6) -0.0210(4) 0.1733(2) 0.0743 1.0000 Uani H1 -0.3918(3) 0.3352(3) 0.09596(14) 0.0500 1.0000 Uiso H11 -0.2274(5) 0.5015(4) 0.10662(17) 0.0659 1.0000 Uiso H21 -0.0517(5) 0.4149(4) -0.00428(18) 0.0674 1.0000 Uiso H31 0.2284(5) 0.2987(3) 0.03174(16) 0.0565 1.0000 Uiso H41 0.0526(5) 0.2095(3) 0.11485(16) 0.0549 1.0000 Uiso H51 0.2804(5) 0.3612(3) 0.19974(16) 0.0521 1.0000 Uiso H61 0.0665(5) 0.1422(3) 0.22959(17) 0.0589 1.0000 Uiso H71 -0.0195(6) 0.3128(4) 0.29065(19) 0.0834 1.0000 Uiso H72 0.2022(6) 0.3323(4) 0.31636(19) 0.0834 1.0000 Uiso H73 0.0791(6) 0.2090(4) 0.34127(19) 0.0834 1.0000 Uiso H91 0.4963(8) 0.6747(4) 0.0812(3) 0.0894 1.0000 Uiso H92 0.3096(8) 0.7554(4) 0.0552(3) 0.0894 1.0000 Uiso H93 0.2994(8) 0.6772(4) 0.1265(3) 0.0894 1.0000 Uiso H101 0.5047(9) 0.5461(5) -0.0263(2) 0.0954 1.0000 Uiso H102 0.3174(9) 0.6213(5) -0.0562(2) 0.0954 1.0000 Uiso H103 0.3107(9) 0.4676(5) -0.0472(2) 0.0954 1.0000 Uiso H121 0.7121(5) 0.0518(4) 0.2484(2) 0.0647 1.0000 Uiso H122 0.6915(5) 0.2039(4) 0.2354(2) 0.0647 1.0000 Uiso H123 0.7418(5) 0.1095(4) 0.1723(2) 0.0647 1.0000 Uiso H131 0.4373(6) -0.0901(4) 0.2054(2) 0.0813 1.0000 Uiso H132 0.4671(6) -0.0342(4) 0.1289(2) 0.0813 1.0000 Uiso H133 0.2576(6) -0.0223(4) 0.1661(2) 0.0813 1.0000 Uiso 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 0.0328(12) 0.112(2) 0.0646(16) -0.0204(16) -0.0006(12) -0.0011(14) O2 0.0589(16) 0.0622(16) 0.0930(19) 0.0168(15) -0.0106(15) 0.0101(15) O3 0.0414(13) 0.0595(14) 0.0548(13) 0.0106(12) -0.0022(12) -0.0022(12) O4 0.0374(11) 0.0626(13) 0.0465(12) -0.0062(11) 0.000(1) 0.0082(12) O5 0.0418(13) 0.0696(15) 0.0600(13) 0.0174(12) 0.0104(11) 0.0150(12) O6 0.0437(13) 0.0703(15) 0.0586(14) 0.0179(12) -0.0027(11) -0.0012(13) C1 0.0435(18) 0.075(2) 0.051(2) -0.0039(18) -0.0092(16) 0.0090(19) C2 0.052(2) 0.062(2) 0.0519(18) 0.0010(18) -0.0107(16) 0.0048(18) C3 0.0449(19) 0.0535(19) 0.0439(18) -0.0051(15) -0.0000(15) 0.0109(17) C4 0.0397(18) 0.0442(16) 0.0478(16) -0.0054(14) -0.0021(15) 0.0027(15) C5 0.0380(17) 0.0442(17) 0.0468(18) -0.0031(14) -0.0014(14) -0.0027(15) C6 0.0379(18) 0.059(2) 0.0565(19) 0.0035(17) -0.0013(16) -0.0015(18) C7 0.061(2) 0.084(2) 0.057(2) -0.000(2) 0.0089(18) -0.004(2) C8 0.057(2) 0.063(2) 0.054(2) 0.0093(19) -0.0035(17) 0.0009(19) C9 0.084(3) 0.069(2) 0.088(3) 0.002(2) 0.002(3) -0.014(2) C10 0.114(4) 0.106(3) 0.054(2) 0.019(2) 0.009(3) -0.009(3) C11 0.0424(17) 0.0481(19) 0.061(2) 0.0104(15) -0.0003(16) 0.0033(18) C12 0.0444(19) 0.058(2) 0.075(2) 0.0081(19) -0.0057(18) 0.004(2) C13 0.059(2) 0.064(2) 0.100(3) -0.001(2) -0.005(2) -0.008(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.400(5) yes O1 . H1 . 0.925 no O2 . C2 . 1.429(5) yes O2 . C8 . 1.434(5) yes O3 . C3 . 1.432(4) yes O3 . C8 . 1.409(4) yes O4 . C1 . 1.436(4) yes O4 . C4 . 1.427(4) yes O5 . C5 . 1.415(4) yes O5 . C11 . 1.447(4) yes O6 . C6 . 1.446(4) yes O6 . C11 . 1.420(4) yes C1 . C2 . 1.521(5) yes C1 . H11 . 1.0000 no C2 . C3 . 1.534(5) yes C2 . H21 . 1.000 no C3 . C4 . 1.520(5) yes C3 . H31 . 1.000 no C4 . C5 . 1.520(5) yes C4 . H41 . 1.000 no C5 . C6 . 1.515(5) yes C5 . H51 . 1.000 no C6 . C7 . 1.501(5) yes C6 . H61 . 1.000 no C7 . H71 . 1.000 no C7 . H72 . 1.000 no C7 . H73 . 1.000 no C8 . C9 . 1.508(6) yes C8 . C10 . 1.511(6) yes C9 . H91 . 1.000 no C9 . H92 . 1.000 no C9 . H93 . 1.000 no C10 . H101 . 1.000 no C10 . H102 . 1.000 no C10 . H103 . 1.000 no C11 . C12 . 1.504(5) yes C11 . C13 . 1.499(5) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . H1 . 108.05(18) no C2 . O2 . C8 . 107.6(3) yes C3 . O3 . C8 . 106.4(2) yes C1 . O4 . C4 . 106.1(2) yes C5 . O5 . C11 . 109.0(2) yes C6 . O6 . C11 . 106.5(2) yes O1 . C1 . O4 . 110.6(3) yes O1 . C1 . C2 . 106.3(3) yes O4 . C1 . C2 . 104.5(3) yes O1 . C1 . H11 . 110.61(17) no O4 . C1 . H11 . 110.95(17) no C2 . C1 . H11 . 114.98(17) no O2 . C2 . C1 . 110.4(3) yes O2 . C2 . C3 . 104.0(3) yes C1 . C2 . C3 . 105.6(3) yes O2 . C2 . H21 . 112.28(18) no C1 . C2 . H21 . 110.17(18) no C3 . C2 . H21 . 114.05(18) no O3 . C3 . C2 . 104.4(3) yes O3 . C3 . C4 . 110.4(3) yes C2 . C3 . C4 . 103.0(3) yes O3 . C3 . H31 . 109.76(16) no C2 . C3 . H31 . 117.54(18) no C4 . C3 . H31 . 111.32(17) no O4 . C4 . C3 . 105.2(2) yes O4 . C4 . C5 . 108.7(2) yes C3 . C4 . C5 . 115.1(3) yes O4 . C4 . H41 . 114.90(15) no C3 . C4 . H41 . 108.23(17) no C5 . C4 . H41 . 105.05(17) no O5 . C5 . C4 . 107.4(2) yes O5 . C5 . C6 . 104.6(3) yes C4 . C5 . C6 . 115.4(3) yes O5 . C5 . H51 . 116.39(16) no C4 . C5 . H51 . 104.93(17) no C6 . C5 . H51 . 108.51(18) no O6 . C6 . C5 . 101.3(3) yes O6 . C6 . C7 . 108.4(3) yes C5 . C6 . C7 . 116.3(3) yes O6 . C6 . H61 . 118.07(16) no C5 . C6 . H61 . 110.48(18) no C7 . C6 . H61 . 102.9(2) no C6 . C7 . H71 . 110.4(2) no C6 . C7 . H72 . 108.3(2) no H71 . C7 . H72 . 109.476 no C6 . C7 . H73 . 109.8(2) no H71 . C7 . H73 . 109.476 no H72 . C7 . H73 . 109.476 no O2 . C8 . O3 . 104.0(3) yes O2 . C8 . C9 . 108.7(4) yes O3 . C8 . C9 . 109.2(3) yes O2 . C8 . C10 . 111.3(4) yes O3 . C8 . C10 . 110.8(3) yes C9 . C8 . C10 . 112.4(4) yes C8 . C9 . H91 . 110.0(2) no C8 . C9 . H92 . 109.8(2) no H91 . C9 . H92 . 109.476 no C8 . C9 . H93 . 108.6(2) no H91 . C9 . H93 . 109.476 no H92 . C9 . H93 . 109.476 no C8 . C10 . H101 . 111.2(3) no C8 . C10 . H102 . 109.6(2) no H101 . C10 . H102 . 109.476 no C8 . C10 . H103 . 107.6(3) no H101 . C10 . H103 . 109.476 no H102 . C10 . H103 . 109.476 no O5 . C11 . O6 . 105.2(3) yes O5 . C11 . C12 . 108.9(3) yes O6 . C11 . C12 . 108.0(3) yes O5 . C11 . C13 . 108.7(3) yes O6 . C11 . C13 . 112.1(3) yes C12 . C11 . C13 . 113.6(3) yes C11 . C12 . H121 . 110.7(2) no C11 . C12 . H122 . 108.0(2) no H121 . C12 . H122 . 109.476 no C11 . C12 . H123 . 109.6(2) no H121 . C12 . H123 . 109.476 no H122 . C12 . H123 . 109.476 no C11 . C13 . H131 . 110.3(2) no C11 . C13 . H132 . 109.4(2) no H131 . C13 . H132 . 109.476 no C11 . C13 . H133 . 108.7(2) no H131 . C13 . H133 . 109.476 no H132 . C13 . H133 . 109.476 no # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_compound[14](mbdw2z) _audit_creation_method 'maXus + CRYSTALS_ver_12-03-99' _publ_contact_author_name ' Alison Edwards' _publ_contact_author_email 'ajed@rsc.anu.edu.au' _publ_contact_author_fax ' australia + 2 6249 0750' _publ_contact_author_phone 'australia + 2 62494109' _publ_contact_author_address ; Research School of Chemistry, ANU, A.C.T., 0200 Australia ; _publ_section_title ; mbdw2z ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_synopsis ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Plate ' _exptl_crystal_colour 'Colourless' _cell_measurement_temperature 200 _refine_ls_hydrogen_treatment 'noref' # Submission details _publ_requested_journal 'test ' _exptl_absorpt_correction_type none _exptl_absorpt_coefficient_mu 0.103 _exptl_crystal_F_000 584 _diffrn_measurement_device 'KappaCCD' _diffrn_measurement_method 'CCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) maxus(Mackay et al., 1999) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 272.297 _diffrn_radiation_type ' MoK\a' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X+ 1/2,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X,+Y+ 1/2,-Z+ 1/2' _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_cell_setting 'Orthorhombic' _chemical_formula_moiety 'C13 H20 O6 ' _chemical_formula_sum 'C13 H20 O6 ' _chemical_name_systematic ; ? ; _cell_length_a 6.5102(2) _cell_length_b 8.9104(4) _cell_length_c 23.7859(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1379.8(1) _diffrn_reflns_number 3169 _diffrn_reflns_theta_max 27.52 _cell_measurement_reflns_used 11243 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _reflns_number_total 1864 _reflns_number_gt 1358 _reflns_d_resolution_low 1.72 _reflns_d_resolution_high 0.62 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 30 _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.11 _refine_diff_density_max 0.11 _refine_ls_number_reflns 1358 _reflns_threshold_expression >2.50\s(I) _refine_ls_number_parameters 173 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0204 _refine_ls_goodness_of_fit_ref 1.0490 _refine_ls_shift/su_max 0.000465 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 4 parameters, Carruthers & Watkin , 1979, -.816E-01-.721 -.340 -.310 ; _refine_ls_extinction_coef 391.6(490) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Larson, A.C. (1970), Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294 Carruthers, J.R. and Watkin, D.J. (1979), Acta Cryst, A35, 698-699 Coppens, P. (1970). In Crystallographic Computing, edited by F.R. Ahmed, S.R.Hall & C.P.Huber, pp 255-270. Copenhagen: Munksgaard. Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W. (1996) CRYSTALS Issue 10. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 0.7927(2) 0.02086(14) 0.87935(5) 0.0467 1.0000 Uani O3 0.7672(2) 0.12120(16) 0.96585(5) 0.0502 1.0000 Uani O4 0.6915(3) 0.4124(2) 0.94977(7) 0.0717 1.0000 Uani O5 0.9832(2) 0.46391(15) 0.90863(6) 0.0498 1.0000 Uani O7 1.2985(2) 0.26329(16) 0.80745(6) 0.0492 1.0000 Uani O9 1.0198(3) 0.12324(17) 0.78230(5) 0.0539 1.0000 Uani C2 0.7301(3) -0.0136(2) 0.93489(7) 0.0440 1.0000 Uani C3 0.9226(3) 0.2045(2) 0.93888(7) 0.0383 1.0000 Uani C4 0.8521(3) 0.3657(2) 0.93263(8) 0.0451 1.0000 Uani C6 1.1737(3) 0.4118(2) 0.88355(8) 0.0445 1.0000 Uani C8 1.2280(4) 0.1583(2) 0.76629(8) 0.0471 1.0000 Uani C9 0.9623(3) 0.2142(2) 0.82907(7) 0.0391 1.0000 Uani C10 1.3073(4) 0.5490(2) 0.87595(9) 0.0637 1.0000 Uani C11 1.3611(4) 0.0209(3) 0.7702(1) 0.0718 1.0000 Uani C12 1.2250(4) 0.2271(3) 0.70832(8) 0.0605 1.0000 Uani C13 0.5049(4) -0.0438(3) 0.93454(11) 0.0713 1.0000 Uani C14 0.8559(5) -0.1410(3) 0.9585(1) 0.0737 1.0000 Uani C61 1.1211(3) 0.3387(2) 0.82766(7) 0.0416 1.0000 Uani C91 0.9615(3) 0.1204(2) 0.88260(7) 0.0370 1.0000 Uani H31 1.0548(3) 0.2113(2) 0.96012(7) 0.0447 1.0000 Uiso H61 1.2484(3) 0.3363(2) 0.90699(8) 0.0531 1.0000 Uiso H91 0.8203(3) 0.2568(2) 0.82768(7) 0.0455 1.0000 Uiso H101 1.4412(4) 0.5191(2) 0.85867(9) 0.0753 1.0000 Uiso H102 1.3330(4) 0.5965(2) 0.91339(9) 0.0753 1.0000 Uiso H103 1.2360(4) 0.6224(2) 0.85082(9) 0.0753 1.0000 Uiso H111 1.3150(4) -0.0544(3) 0.7417(1) 0.0838 1.0000 Uiso H112 1.3492(4) -0.0233(3) 0.8088(1) 0.0838 1.0000 Uiso H113 1.5074(4) 0.0488(3) 0.7628(1) 0.0838 1.0000 Uiso H121 1.1754(4) 0.1511(3) 0.68052(8) 0.0693 1.0000 Uiso H122 1.3669(4) 0.2600(3) 0.69792(8) 0.0693 1.0000 Uiso H123 1.1308(4) 0.3157(3) 0.70813(8) 0.0693 1.0000 Uiso H131 0.4583(4) -0.0684(3) 0.97353(11) 0.0854 1.0000 Uiso H132 0.4303(4) 0.0472(3) 0.92083(11) 0.0854 1.0000 Uiso H133 0.4750(4) -0.1304(3) 0.90907(11) 0.0854 1.0000 Uiso H141 0.8091(5) -0.1633(3) 0.9976(1) 0.0848 1.0000 Uiso H142 1.0043(5) -0.1119(3) 0.9590(1) 0.0848 1.0000 Uiso H143 0.8376(5) -0.2321(3) 0.9345(1) 0.0848 1.0000 Uiso H611 1.0672(3) 0.4239(2) 0.80465(7) 0.0493 1.0000 Uiso H911 1.1025(3) 0.0760(2) 0.88387(7) 0.0600 1.0000 Uiso 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 0.0620(9) 0.0463(7) 0.0319(6) -0.0013(5) 0.0003(6) -0.0144(7) O3 0.063(1) 0.0475(7) 0.0396(6) -0.0062(6) 0.0142(7) -0.0145(8) O4 0.0668(12) 0.064(1) 0.0841(11) 0.0012(9) 0.029(1) 0.017(1) O5 0.0632(9) 0.0361(7) 0.0501(7) -0.0020(6) 0.0144(7) 0.0019(7) O7 0.0476(8) 0.0542(8) 0.0459(7) -0.0116(6) 0.0073(6) -0.0031(8) O9 0.068(1) 0.0580(8) 0.0355(6) -0.0110(7) 0.0114(7) -0.0169(8) C2 0.0578(13) 0.039(1) 0.0351(9) -0.0012(8) 0.0022(9) -0.005(1) C3 0.042(1) 0.043(1) 0.0305(8) -0.0017(8) 0.0010(7) -0.0044(9) C4 0.0531(13) 0.0430(11) 0.0392(9) -0.0023(8) 0.0054(9) 0.002(1) C6 0.0500(11) 0.0430(11) 0.0404(9) -0.0035(8) 0.0061(9) -0.0052(9) C8 0.0579(13) 0.0476(11) 0.0359(9) -0.0065(8) 0.0094(9) -0.0043(11) C9 0.0467(11) 0.041(1) 0.0292(8) -0.0017(7) 0.0008(8) 0.0004(9) C10 0.0764(16) 0.0585(13) 0.0562(12) -0.008(1) 0.0103(13) -0.0265(13) C11 0.091(2) 0.0657(16) 0.0590(12) -0.0091(12) 0.0017(14) 0.0193(16) C12 0.0776(16) 0.0629(13) 0.041(1) -0.0009(9) 0.0119(11) -0.0109(14) C13 0.0672(16) 0.0794(18) 0.0673(14) -0.0014(14) 0.0068(13) -0.0282(15) C14 0.107(2) 0.0548(14) 0.0589(13) 0.0168(12) 0.0026(16) 0.0146(16) C61 0.0471(11) 0.041(1) 0.0368(9) -0.0001(8) 0.0047(8) -0.0024(9) C91 0.0402(9) 0.0372(9) 0.0337(8) -0.0021(7) 0.0007(7) 0.0002(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.416(2) yes O1 . C91 . 1.415(2) yes O3 . C2 . 1.429(2) yes O3 . C3 . 1.409(2) yes O4 . C4 . 1.197(2) yes O5 . C4 . 1.349(2) yes O5 . C6 . 1.452(2) yes O7 . C8 . 1.430(2) yes O7 . C61 . 1.420(2) yes O9 . C8 . 1.442(3) yes O9 . C9 . 1.426(2) yes C2 . C13 . 1.490(3) yes C2 . C14 . 1.508(3) yes C3 . C4 . 1.515(3) yes C3 . C91 . 1.554(2) yes C3 . H31 . 1.000 no C6 . C10 . 1.511(3) yes C6 . C61 . 1.520(2) yes C6 . H61 . 1.000 no C8 . C11 . 1.503(3) yes C8 . C12 . 1.509(3) yes C9 . C61 . 1.517(3) yes C9 . C91 . 1.523(2) yes C9 . H91 . 1.000 no C10 . H101 . 1.000 no C10 . H102 . 1.000 no C10 . H103 . 1.000 no C11 . H111 . 1.000 no C11 . H112 . 1.000 no C11 . H113 . 1.000 no C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 1.000 no C61 . H611 . 1.000 no C91 . H911 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C91 . 107.97(13) yes C2 . O3 . C3 . 109.22(14) yes C4 . O5 . C6 . 120.44(14) yes C8 . O7 . C61 . 106.30(15) yes C8 . O9 . C9 . 109.25(15) yes O1 . C2 . O3 . 104.47(14) yes O1 . C2 . C13 . 108.49(19) yes O3 . C2 . C13 . 108.72(19) yes O1 . C2 . C14 . 110.72(17) yes O3 . C2 . C14 . 110.43(17) yes C13 . C2 . C14 . 113.6(2) yes O3 . C3 . C4 . 109.04(16) yes O3 . C3 . C91 . 104.80(14) yes C4 . C3 . C91 . 114.92(15) yes O3 . C3 . H31 . 114.86(9) no C4 . C3 . H31 . 104.60(11) no C91 . C3 . H31 . 108.9(1) no O4 . C4 . O5 . 118.08(19) yes O4 . C4 . C3 . 124.1(2) yes O5 . C4 . C3 . 117.72(17) yes O5 . C6 . C10 . 106.39(16) yes O5 . C6 . C61 . 107.69(16) yes C10 . C6 . C61 . 111.84(16) yes O5 . C6 . H61 . 113.65(9) no C10 . C6 . H61 . 109.36(13) no C61 . C6 . H61 . 107.96(11) no O7 . C8 . O9 . 105.20(15) yes O7 . C8 . C11 . 107.78(18) yes O9 . C8 . C11 . 110.42(19) yes O7 . C8 . C12 . 111.36(17) yes O9 . C8 . C12 . 108.48(18) yes C11 . C8 . C12 . 113.31(18) yes O9 . C9 . C61 . 102.67(14) yes O9 . C9 . C91 . 109.98(14) yes C61 . C9 . C91 . 114.97(15) yes O9 . C9 . H91 . 115.6(1) no C61 . C9 . H91 . 110.6(1) no C91 . C9 . H91 . 103.5(1) no C6 . C10 . H101 . 109.57(12) no C6 . C10 . H102 . 109.37(11) no H101 . C10 . H102 . 109.476 no C6 . C10 . H103 . 109.45(13) no H101 . C10 . H103 . 109.476 no H102 . C10 . H103 . 109.476 no C8 . C11 . H111 . 109.33(13) no C8 . C11 . H112 . 109.47(12) no H111 . C11 . H112 . 109.476 no C8 . C11 . H113 . 109.60(14) no H111 . C11 . H113 . 109.476 no H112 . C11 . H113 . 109.476 no C8 . C12 . H121 . 109.48(12) no C8 . C12 . H122 . 109.46(13) no H121 . C12 . H122 . 109.476 no C8 . C12 . H123 . 109.45(13) no H121 . C12 . H123 . 109.476 no H122 . C12 . H123 . 109.476 no C2 . C13 . H131 . 109.44(14) no C2 . C13 . H132 . 109.44(14) no H131 . C13 . H132 . 109.476 no C2 . C13 . H133 . 109.52(14) no H131 . C13 . H133 . 109.476 no H132 . C13 . H133 . 109.476 no C2 . C14 . H141 . 109.32(12) no C2 . C14 . H142 . 109.55(14) no H141 . C14 . H142 . 109.476 no C2 . C14 . H143 . 109.52(12) no H141 . C14 . H143 . 109.476 no H142 . C14 . H143 . 109.475 no O7 . C61 . C6 . 108.42(16) yes O7 . C61 . C9 . 102.46(14) yes C6 . C61 . C9 . 116.61(15) yes O7 . C61 . H611 . 117.38(9) no C6 . C61 . H611 . 103.42(11) no C9 . C61 . H611 . 109.2(1) no O1 . C91 . C3 . 102.86(14) yes O1 . C91 . C9 . 107.53(14) yes C3 . C91 . C9 . 117.16(15) yes O1 . C91 . H911 . 117.81(9) no C3 . C91 . H911 . 108.3(1) no C9 . C91 . H911 . 103.8(1) no