# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1719 data_global #=============================================================================== _audit_creation_date 22-02-99 # 1. SUBMISSION DETAILS _publ_contact_author ; Louis Ricard, Labo DCPH, Ecole Polytechnique Route de Saclay 91128 Palaiseau France ; _publ_contact_author_phone '01-69-33-45-72' _publ_contact_author_fax '01-69-33-39-90' _publ_contact_author_email ricard@neptune.polytechnique.fr _publ_requested_journal 'Chemical Communications' _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for publication as a new structure paper in Chem. Comm.. The figures, chemical structure diagram (scheme), Transfert of Copyright Agreement form and structure factors will be sent on receipt of your acknowledgement letter ; #=============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Short-cuts in forskolin synthesis: a pentacyclic approach. ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name ; M. Leclaire, R. Levet, F. Ferrera, PH. Ducrot, L. Ricard(b), J. Y. Lallemand(a) ; _publ_author_address ; DCSO Ecole Polytechnique, F-91128 Palaiseau Cedex France Laboratoire Heteroelements et Coordination, CNRS UMR 7653, DCPH Ecole Polytechnique, F-91128 Palaiseau Cedex France ; #=============================================================================== # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; All structures were solved using SIR97 (Altomare et al.) and refined with SHELXL97 (Sheldrick). Figures were drawn with Platon (Spek, 1990). ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993) J. Appl. Cryst. 26, 343-350. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of G\\"ottingen, Germany, 1997. Sluis, P. v.d., Spek, A.L. (1990). Acta Cryst. A46, 194-201. Spek, A.L. (1990). Acta Cryst. A46, C-34. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; #=============================================================================== # If more than one structure is reported, sections 5-10 should be filled in # per structure. For each data set, replace the ? in the data_? line below # by a unique identifier. #=============================================================================== data_pentac _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H23 O5' _chemical_formula_weight 319.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinique' _symmetry_space_group_name_H-M 'P21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.894(1) _cell_length_b 9.577(1) _cell_length_c 23.025(1) _cell_angle_alpha 90.00 _cell_angle_beta 92.43(1) _cell_angle_gamma 90.06 _cell_volume 3281.2 _cell_formula_units_Z 8 _cell_measurement_temperature 125.0(5) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 18.0 _exptl_crystal_description 'cube' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125.0(5) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CAD4 _diffrn_measurement_method q/2q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5097 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 30.00 _reflns_number_total 5097 _reflns_number_gt 5097 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^2^+0.0000P] 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 5097 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1568 _refine_ls_wR_factor_gt 0.1568 _refine_ls_goodness_of_fit_ref 1.236 _refine_ls_restrained_S_all 1.236 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 0.85513(18) -0.2319(3) 0.28702(12) 0.0233(6) Uani 1 1 d . . . C2 C 0.85569(19) -0.3867(3) 0.30048(13) 0.0280(7) Uani 1 1 d . . . C3 C 0.8252(2) -0.4140(3) 0.36135(15) 0.0301(7) Uani 1 1 d . . . C4 C 0.8796(2) -0.3347(3) 0.40975(13) 0.0244(6) Uani 1 1 d . . . C5 C 0.87997(17) -0.1771(3) 0.39282(11) 0.0165(5) Uani 1 1 d . . . C6 C 0.92578(16) -0.0792(3) 0.43867(11) 0.0157(5) Uani 1 1 d . . . C7 C 0.94717(17) 0.0705(3) 0.41683(11) 0.0168(5) Uani 1 1 d . . . C8 C 0.88819(17) 0.1175(3) 0.36393(11) 0.0177(5) Uani 1 1 d . . . C9 C 0.86475(17) -0.0026(3) 0.32163(11) 0.0166(5) Uani 1 1 d . . . C10 C 0.91243(17) -0.1440(3) 0.33068(11) 0.0175(5) Uani 1 1 d . . . C11 C 0.77379(17) -0.0662(3) 0.33206(11) 0.0175(5) Uani 1 1 d . . . C12 C 0.69558(18) 0.0322(3) 0.33319(12) 0.0223(6) Uani 1 1 d . . . C13 C 0.72924(18) 0.1767(3) 0.35177(11) 0.0203(6) Uani 1 1 d . . . C14 C 0.8305(2) -0.3617(3) 0.46602(14) 0.0355(8) Uani 1 1 d . . . C15 C 0.9748(2) -0.3948(3) 0.41725(14) 0.0310(7) Uani 1 1 d . . . C16 C 1.01186(18) -0.1526(3) 0.31787(12) 0.0236(6) Uani 1 1 d . . . C17 C 0.93243(19) 0.2373(3) 0.33250(12) 0.0242(6) Uani 1 1 d . . . C18 C 0.6599(2) 0.2578(3) 0.38409(13) 0.0289(7) Uani 1 1 d . . . O1 O 0.78630(11) -0.1297(2) 0.38810(7) 0.0171(4) Uani 1 1 d . . . O2 O 0.76480(12) -0.1740(2) 0.28999(8) 0.0233(4) Uani 1 1 d . . . O3 O 0.80697(12) 0.1667(2) 0.39057(7) 0.0183(4) Uani 1 1 d . . . O4 O 0.87227(12) -0.0679(2) 0.48872(8) 0.0190(4) Uani 1 1 d . . . O5 O 1.03905(12) 0.0822(2) 0.40330(8) 0.0237(4) Uani 1 1 d . . . C19 C 0.74593(18) 0.2807(3) 0.66001(11) 0.0191(5) Uani 1 1 d . . . C20 C 0.7179(2) 0.4326(3) 0.65382(13) 0.0258(6) Uani 1 1 d . . . C21 C 0.6168(2) 0.4472(3) 0.64316(12) 0.0254(6) Uani 1 1 d . . . C22 C 0.57758(19) 0.3596(3) 0.59201(12) 0.0207(6) Uani 1 1 d . . . C23 C 0.60999(16) 0.2062(3) 0.60026(10) 0.0145(5) Uani 1 1 d . . . C24 C 0.56689(16) 0.0985(3) 0.55676(11) 0.0170(5) Uani 1 1 d . . . C25 C 0.61684(16) -0.0414(3) 0.55316(11) 0.0155(5) Uani 1 1 d . . . C26 C 0.66863(16) -0.0817(3) 0.61010(10) 0.0142(5) Uani 1 1 d . . . C27 C 0.71395(16) 0.0447(3) 0.64051(10) 0.0139(5) Uani 1 1 d . . . C28 C 0.71385(16) 0.1865(3) 0.60846(11) 0.0142(5) Uani 1 1 d . . . C29 C 0.65746(17) 0.1034(3) 0.68856(10) 0.0157(5) Uani 1 1 d . . . C30 C 0.62614(18) 0.0042(3) 0.73354(11) 0.0188(5) Uani 1 1 d . . . C31 C 0.62190(17) -0.1428(3) 0.70671(11) 0.0167(5) Uani 1 1 d . . . C32 C 0.4747(2) 0.3713(3) 0.59278(13) 0.0294(7) Uani 1 1 d . . . C33 C 0.6073(2) 0.4212(3) 0.53450(12) 0.0263(6) Uani 1 1 d . . . C34 C 0.77471(17) 0.2037(3) 0.55736(11) 0.0191(5) Uani 1 1 d . . . C35 C 0.73541(18) -0.1982(3) 0.59975(11) 0.0189(5) Uani 1 1 d . . . C36 C 0.5543(2) -0.2358(3) 0.73463(12) 0.0251(6) Uani 1 1 d . . . O6 O 0.58038(12) 0.15945(19) 0.65714(7) 0.0156(4) Uani 1 1 d . . . O7 O 0.70828(13) 0.2175(2) 0.71124(8) 0.0203(4) Uani 1 1 d . . . O8 O 0.59734(12) -0.13457(19) 0.64571(7) 0.0164(4) Uani 1 1 d . . . O9 O 0.47650(12) 0.0697(2) 0.57270(8) 0.0228(4) Uani 1 1 d . . . O10 O 0.67585(12) -0.0429(2) 0.50563(8) 0.0201(4) Uani 1 1 d . . . H01 H 0.8784 -0.2271 0.2494 0.030 Uiso 1 1 d . . . H02 H 0.9149 -0.4216 0.2973 0.036 Uiso 1 1 d . . . H03 H 0.8162 -0.4332 0.2735 0.036 Uiso 1 1 d . . . H04 H 0.8309 -0.5115 0.3688 0.039 Uiso 1 1 d . . . H05 H 0.7641 -0.3875 0.3629 0.039 Uiso 1 1 d . . . H06 H 0.9820 -0.1224 0.4479 0.020 Uiso 1 1 d . . . H07 H 0.9339 0.1306 0.4481 0.022 Uiso 1 1 d . . . H08 H 0.8768 0.0456 0.2867 0.021 Uiso 1 1 d . . . H09 H 0.6538 -0.0007 0.3600 0.029 Uiso 1 1 d . . . H010 H 0.6674 0.0378 0.2955 0.029 Uiso 1 1 d . . . H011 H 0.7425 0.2233 0.3168 0.026 Uiso 1 1 d . . . H012 H 0.8611 -0.3152 0.4974 0.046 Uiso 1 1 d . . . H013 H 0.7707 -0.3278 0.4617 0.046 Uiso 1 1 d . . . H014 H 0.8293 -0.4593 0.4735 0.046 Uiso 1 1 d . . . H015 H 1.0062 -0.3793 0.3829 0.040 Uiso 1 1 d . . . H016 H 1.0056 -0.3505 0.4492 0.040 Uiso 1 1 d . . . H017 H 0.9713 -0.4925 0.4245 0.040 Uiso 1 1 d . . . H018 H 1.0198 -0.1296 0.2783 0.031 Uiso 1 1 d . . . H019 H 1.0449 -0.0893 0.3422 0.031 Uiso 1 1 d . . . H020 H 1.0328 -0.2451 0.3251 0.031 Uiso 1 1 d . . . H021 H 0.6473 0.2101 0.4190 0.038 Uiso 1 1 d . . . H022 H 0.6826 0.3482 0.3931 0.038 Uiso 1 1 d . . . H023 H 0.6064 0.2657 0.3604 0.038 Uiso 1 1 d . . . H024 H 0.9464 0.3103 0.3593 0.031 Uiso 1 1 d . . . H025 H 0.9861 0.2050 0.3161 0.031 Uiso 1 1 d . . . H026 H 0.8925 0.2711 0.3025 0.031 Uiso 1 1 d . . . H027 H 0.1279 0.1398 0.5094 0.024 Uiso 1 1 d . . . H028 H 0.0684 0.1128 0.4442 0.024 Uiso 1 1 d . . . H029 H 0.8097 0.2847 0.6621 0.024 Uiso 1 1 d . . . H030 H 0.7473 0.4726 0.6220 0.033 Uiso 1 1 d . . . H031 H 0.7354 0.4809 0.6885 0.033 Uiso 1 1 d . . . H032 H 0.6039 0.5427 0.6355 0.033 Uiso 1 1 d . . . H033 H 0.5885 0.4191 0.6775 0.033 Uiso 1 1 d . . . H034 H 0.4485 0.3186 0.5616 0.038 Uiso 1 1 d . . . H035 H 0.4549 0.3368 0.6286 0.038 Uiso 1 1 d . . . H036 H 0.4579 0.4667 0.5885 0.038 Uiso 1 1 d . . . H037 H 0.6708 0.4150 0.5329 0.034 Uiso 1 1 d . . . H038 H 0.5800 0.3704 0.5030 0.034 Uiso 1 1 d . . . H039 H 0.5895 0.5163 0.5319 0.034 Uiso 1 1 d . . . H040 H 0.8353 0.1884 0.5702 0.025 Uiso 1 1 d . . . H041 H 0.7579 0.1378 0.5280 0.025 Uiso 1 1 d . . . H042 H 0.7685 0.2955 0.5422 0.025 Uiso 1 1 d . . . H043 H 0.7710 0.0031 0.6483 0.018 Uiso 1 1 d . . . H044 H 0.5682 0.0307 0.7451 0.024 Uiso 1 1 d . . . H045 H 0.6670 0.0045 0.7663 0.024 Uiso 1 1 d . . . H046 H 0.6800 -0.1815 0.7131 0.022 Uiso 1 1 d . . . H047 H 0.5544 -0.3249 0.7166 0.033 Uiso 1 1 d . . . H048 H 0.5701 -0.2455 0.7748 0.033 Uiso 1 1 d . . . H049 H 0.4963 -0.1954 0.7300 0.033 Uiso 1 1 d . . . H050 H 0.7663 -0.2212 0.6353 0.024 Uiso 1 1 d . . . H051 H 0.7040 -0.2779 0.5850 0.024 Uiso 1 1 d . . . H052 H 0.7772 -0.1679 0.5724 0.024 Uiso 1 1 d . . . H053 H 0.5715 -0.1099 0.5466 0.020 Uiso 1 1 d . . . H054 H 0.5695 0.1408 0.5196 0.022 Uiso 1 1 d . . . H055 H 0.3333 0.1135 0.4991 0.024 Uiso 1 1 d . . . H056 H 0.4812 0.1118 0.6058 0.024 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 0.0158(12) 0.0333(16) 0.0208(14) -0.0117(12) 0.0013(10) 0.0013(11) C2 0.0228(14) 0.0292(16) 0.0319(16) -0.0150(13) -0.0015(12) -0.0010(12) C3 0.0254(15) 0.0212(15) 0.0440(19) -0.0078(14) 0.0045(13) -0.0023(12) C4 0.0245(14) 0.0216(14) 0.0273(15) -0.0009(12) 0.0023(11) -0.0003(12) C5 0.0129(11) 0.0207(13) 0.0160(12) -0.0014(10) 0.0019(9) 0.0018(10) C6 0.0131(11) 0.0212(13) 0.0130(11) -0.0005(10) 0.0011(9) 0.0014(10) C7 0.0150(11) 0.0222(13) 0.0131(11) -0.0022(10) 0.0004(9) -0.0022(10) C8 0.0143(12) 0.0240(14) 0.0149(12) 0.0017(10) 0.0020(9) 0.0001(10) C9 0.0151(12) 0.0237(14) 0.0111(11) 0.0006(10) 0.0015(9) 0.0001(10) C10 0.0159(12) 0.0237(14) 0.0129(11) -0.0052(10) 0.0010(9) -0.0005(10) C11 0.0146(11) 0.0241(14) 0.0134(11) -0.0038(10) -0.0023(9) 0.0018(10) C12 0.0139(12) 0.0322(16) 0.0208(13) -0.0011(12) -0.0014(10) 0.0032(11) C13 0.0175(12) 0.0298(15) 0.0136(12) 0.0018(11) -0.0006(9) 0.0047(11) C14 0.047(2) 0.0243(16) 0.0358(18) 0.0054(14) 0.0113(15) -0.0005(15) C15 0.0330(16) 0.0249(16) 0.0349(17) -0.0019(13) -0.0005(13) 0.0056(13) C16 0.0171(13) 0.0340(16) 0.0200(13) -0.0044(12) 0.0045(10) 0.0014(12) C17 0.0241(14) 0.0255(15) 0.0232(14) 0.0051(12) 0.0040(11) -0.0021(12) C18 0.0225(14) 0.0342(17) 0.0301(16) -0.0046(13) 0.0013(12) 0.0068(13) O1 0.0107(8) 0.0247(10) 0.0161(9) -0.0015(8) 0.0009(6) -0.0005(7) O2 0.0152(9) 0.0322(11) 0.0220(10) -0.0105(8) -0.0034(7) 0.0004(8) O3 0.0164(9) 0.0253(10) 0.0133(8) -0.0012(7) 0.0013(7) 0.0032(8) O4 0.0189(9) 0.0242(10) 0.0140(9) -0.0008(8) 0.0024(7) -0.0003(8) O5 0.0145(9) 0.0365(12) 0.0200(10) 0.0002(9) 0.0000(7) -0.0065(8) C19 0.0212(13) 0.0207(14) 0.0154(12) -0.0005(10) -0.0006(10) -0.0032(11) C20 0.0382(17) 0.0150(13) 0.0243(14) -0.0020(11) 0.0021(12) -0.0009(12) C21 0.0391(17) 0.0178(14) 0.0198(13) 0.0019(11) 0.0069(12) 0.0093(13) C22 0.0243(14) 0.0201(14) 0.0179(13) 0.0038(11) 0.0033(10) 0.0085(11) C23 0.0160(12) 0.0171(12) 0.0105(11) 0.0038(9) 0.0026(9) 0.0032(10) C24 0.0120(11) 0.0270(14) 0.0118(11) 0.0016(10) 0.0004(9) 0.0002(10) C25 0.0122(11) 0.0224(13) 0.0118(11) -0.0025(10) 0.0009(9) -0.0039(10) C26 0.0143(11) 0.0168(12) 0.0116(11) -0.0006(9) 0.0024(8) 0.0009(10) C27 0.0134(11) 0.0147(12) 0.0135(11) 0.0001(9) -0.0016(9) 0.0016(10) C28 0.0142(11) 0.0126(12) 0.0155(11) 0.0008(9) -0.0015(9) 0.0007(9) C29 0.0167(12) 0.0174(13) 0.0126(11) -0.0009(10) -0.0025(9) 0.0018(10) C30 0.0226(13) 0.0217(14) 0.0121(12) 0.0008(10) 0.0001(9) 0.0066(11) C31 0.0181(12) 0.0190(13) 0.0132(11) 0.0012(10) 0.0021(9) 0.0020(10) C32 0.0260(15) 0.0359(18) 0.0268(15) 0.0116(13) 0.0077(12) 0.0166(13) C33 0.0312(15) 0.0272(15) 0.0207(13) 0.0089(12) 0.0048(11) 0.0100(13) C34 0.0168(12) 0.0206(13) 0.0200(13) 0.0003(11) 0.0030(10) -0.0018(11) C35 0.0192(12) 0.0174(13) 0.0206(13) -0.0002(10) 0.0049(10) 0.0029(11) C36 0.0332(15) 0.0227(15) 0.0201(13) -0.0002(11) 0.0104(11) -0.0041(12) O6 0.0164(9) 0.0204(10) 0.0101(8) 0.0020(7) 0.0020(6) 0.0048(7) O7 0.0272(10) 0.0200(10) 0.0136(9) -0.0037(7) -0.0018(7) -0.0012(8) O8 0.0158(8) 0.0209(10) 0.0128(8) 0.0004(7) 0.0037(6) -0.0038(7) O9 0.0110(8) 0.0403(13) 0.0171(9) -0.0026(9) 0.0010(7) -0.0007(8) O10 0.0200(9) 0.0250(10) 0.0157(9) -0.0047(8) 0.0048(7) -0.0022(8) _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 O2 1.460(3) . ? C1 C2 1.515(4) . ? C1 C10 1.541(4) . ? C2 C3 1.514(4) . ? C3 C4 1.548(4) . ? C4 C15 1.533(4) . ? C4 C14 1.536(4) . ? C4 C5 1.560(4) . ? C5 O1 1.467(3) . ? C5 C6 1.547(4) . ? C5 C10 1.562(3) . ? C6 O4 1.433(3) . ? C6 C7 1.556(4) . ? C7 O5 1.421(3) . ? C7 C8 1.539(3) . ? C8 O3 1.458(3) . ? C8 C17 1.521(4) . ? C8 C9 1.538(4) . ? C9 C11 1.513(4) . ? C9 C10 1.539(4) . ? C10 C16 1.524(4) . ? C11 O2 1.418(3) . ? C11 O1 1.432(3) . ? C11 C12 1.500(4) . ? C12 C13 1.526(4) . ? C13 O3 1.435(3) . ? C13 C18 1.513(4) . ? C19 O7 1.459(3) . ? C19 C20 1.519(4) . ? C19 C28 1.550(4) . ? C20 C21 1.521(4) . ? C21 C22 1.540(4) . ? C22 C33 1.532(4) . ? C22 C32 1.537(4) . ? C22 C23 1.556(4) . ? C23 O6 1.469(3) . ? C23 C24 1.556(4) . ? C23 C28 1.562(3) . ? C24 O9 1.437(3) . ? C24 C25 1.538(4) . ? C25 O10 1.432(3) . ? C25 C26 1.542(3) . ? C26 O8 1.459(3) . ? C26 C35 1.521(4) . ? C26 C27 1.539(3) . ? C27 C29 1.526(3) . ? C27 C28 1.546(3) . ? C28 C34 1.524(3) . ? C29 O7 1.416(3) . ? C29 O6 1.435(3) . ? C29 C30 1.495(4) . ? C30 C31 1.537(4) . ? C31 O8 1.439(3) . ? C31 C36 1.507(4) . ? 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 O2 C1 C2 111.1(2) . . ? O2 C1 C10 104.3(2) . . ? C2 C1 C10 113.8(2) . . ? C3 C2 C1 111.0(2) . . ? C2 C3 C4 114.4(2) . . ? C15 C4 C14 108.2(3) . . ? C15 C4 C3 110.5(2) . . ? C14 C4 C3 105.8(2) . . ? C15 C4 C5 112.3(2) . . ? C14 C4 C5 112.3(2) . . ? C3 C4 C5 107.6(2) . . ? O1 C5 C6 104.7(2) . . ? O1 C5 C4 107.8(2) . . ? C6 C5 C4 114.9(2) . . ? O1 C5 C10 101.52(19) . . ? C6 C5 C10 111.0(2) . . ? C4 C5 C10 115.4(2) . . ? O4 C6 C5 110.5(2) . . ? O4 C6 C7 108.5(2) . . ? C5 C6 C7 115.3(2) . . ? O5 C7 C8 109.0(2) . . ? O5 C7 C6 110.8(2) . . ? C8 C7 C6 114.1(2) . . ? O3 C8 C17 109.9(2) . . ? O3 C8 C9 109.8(2) . . ? C17 C8 C9 110.7(2) . . ? O3 C8 C7 102.60(19) . . ? C17 C8 C7 110.7(2) . . ? C9 C8 C7 112.9(2) . . ? C11 C9 C8 112.4(2) . . ? C11 C9 C10 92.1(2) . . ? C8 C9 C10 118.8(2) . . ? C16 C10 C9 118.0(2) . . ? C16 C10 C1 111.1(2) . . ? C9 C10 C1 98.8(2) . . ? C16 C10 C5 120.5(2) . . ? C9 C10 C5 98.24(19) . . ? C1 C10 C5 107.6(2) . . ? O2 C11 O1 108.1(2) . . ? O2 C11 C12 114.8(2) . . ? O1 C11 C12 108.9(2) . . ? O2 C11 C9 104.1(2) . . ? O1 C11 C9 103.33(19) . . ? C12 C11 C9 116.8(2) . . ? C11 C12 C13 109.2(2) . . ? O3 C13 C18 106.1(2) . . ? O3 C13 C12 111.1(2) . . ? C18 C13 C12 112.4(2) . . ? C11 O1 C5 106.58(18) . . ? C11 O2 C1 104.39(19) . . ? C13 O3 C8 114.94(19) . . ? O7 C19 C20 111.1(2) . . ? O7 C19 C28 105.2(2) . . ? C20 C19 C28 114.3(2) . . ? C19 C20 C21 111.7(2) . . ? C20 C21 C22 114.4(2) . . ? C33 C22 C32 107.9(2) . . ? C33 C22 C21 109.7(2) . . ? C32 C22 C21 107.3(2) . . ? C33 C22 C23 111.7(2) . . ? C32 C22 C23 111.9(2) . . ? C21 C22 C23 108.4(2) . . ? O6 C23 C24 103.93(19) . . ? O6 C23 C22 107.05(19) . . ? C24 C23 C22 115.4(2) . . ? O6 C23 C28 100.86(18) . . ? C24 C23 C28 112.1(2) . . ? C22 C23 C28 115.5(2) . . ? O9 C24 C25 107.9(2) . . ? O9 C24 C23 109.1(2) . . ? C25 C24 C23 115.1(2) . . ? O10 C25 C24 111.4(2) . . ? O10 C25 C26 110.24(19) . . ? C24 C25 C26 113.5(2) . . ? O8 C26 C35 109.2(2) . . ? O8 C26 C27 109.39(19) . . ? C35 C26 C27 111.8(2) . . ? O8 C26 C25 102.41(18) . . ? C35 C26 C25 111.0(2) . . ? C27 C26 C25 112.6(2) . . ? C29 C27 C26 112.1(2) . . ? C29 C27 C28 91.86(19) . . ? C26 C27 C28 118.81(19) . . ? C34 C28 C19 110.8(2) . . ? C34 C28 C27 118.3(2) . . ? C19 C28 C27 98.72(19) . . ? C34 C28 C23 120.8(2) . . ? C19 C28 C23 107.1(2) . . ? C27 C28 C23 98.36(19) . . ? O7 C29 O6 107.5(2) . . ? O7 C29 C30 114.4(2) . . ? O6 C29 C30 108.7(2) . . ? O7 C29 C27 104.5(2) . . ? O6 C29 C27 103.10(18) . . ? C30 C29 C27 117.8(2) . . ? C29 C30 C31 108.2(2) . . ? O8 C31 C36 107.6(2) . . ? O8 C31 C30 110.3(2) . . ? C36 C31 C30 112.7(2) . . ? C29 O6 C23 107.43(17) . . ? C29 O7 C19 103.85(18) . . ? C31 O8 C26 114.01(18) . . ? _diffrn_measured_fraction_theta_max .992 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full .992 _refine_diff_density_max .693 _refine_diff_density_min -.478 _refine_diff_density_rms .075