# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Zachary Ball' _publ_contact_author_email ZB1@RICE.EDU _publ_section_title ; Synthesis and Isotopic Labeling of a Naturally Occurring Alkyl-thiadiamondoid ; loop_ _publ_author_name 'Zachary Ball' 'John Allen' 'Vincenzo Russo' # Attachment 'C18H22O10_VRUSSO.CIF' data_vrusm _database_code_depnum_ccdc_archive 'CCDC 703400' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ; tetramethyl 1-methyl-2-oxo-6-hydroxybicyclo(1.3.3)nonane- 1,3,5,7-tetracarboxylate ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 O10' _chemical_formula_sum 'C18 H22 O10' _chemical_formula_weight 398.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_int_tables_number 33 _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 16.400(3) _cell_length_b 11.699(2) _cell_length_c 19.703(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3780.2(13) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6531 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 21.30 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9144 _exptl_absorpt_correction_T_max 0.9660 _exptl_absorpt_process_details 'SADABS v2.10 (Bruker-AXS, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker SMART CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 38032 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.35 _reflns_number_total 4807 _reflns_number_gt 3320 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)' _computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)' _computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)' _computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)' _computing_structure_refinement 'SHELXTL v5.1' _computing_molecular_graphics 'SHELXTL v5.1' _computing_publication_material 'SHELXTL v5.1' _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^)+(0.0478P)^2^+1.4350P] 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 SHELXL _refine_ls_extinction_coef 0.0065(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4807 _refine_ls_number_parameters 507 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0807 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 -0.1895(2) 0.0447(3) -0.48211(19) 0.0391(8) Uani 1 1 d . . . C2 C -0.0971(2) 0.0332(3) -0.4943(2) 0.0404(8) Uani 1 1 d . . . H2A H -0.0861 0.0293 -0.5426 0.049 Uiso 1 1 calc R . . H2B H -0.0690 0.0995 -0.4760 0.049 Uiso 1 1 calc R . . C3 C -0.0661(2) -0.0760(3) -0.45914(18) 0.0360(7) Uani 1 1 d . . . C4 C -0.0883(2) -0.0733(3) -0.38502(18) 0.0364(7) Uani 1 1 d . . . C5 C -0.1528(2) -0.0144(3) -0.36104(19) 0.0390(8) Uani 1 1 d . . . C6 C -0.2046(2) 0.0607(3) -0.40578(18) 0.0409(8) Uani 1 1 d . . . H6A H -0.1943 0.1399 -0.3941 0.049 Uiso 1 1 calc R . . H6B H -0.2615 0.0450 -0.3963 0.049 Uiso 1 1 calc R . . C7 C -0.2325(2) -0.0617(3) -0.51124(18) 0.0384(8) Uani 1 1 d . . . C8 C -0.1995(2) -0.1804(3) -0.49251(19) 0.0378(7) Uani 1 1 d . . . C9 C -0.1051(2) -0.1814(3) -0.4928(2) 0.0380(8) Uani 1 1 d . . . H9A H -0.0864 -0.2495 -0.4694 0.046 Uiso 1 1 calc R . . H9B H -0.0864 -0.1861 -0.5394 0.046 Uiso 1 1 calc R . . C10 C -0.2305(3) -0.2702(4) -0.5435(3) 0.0505(11) Uani 1 1 d . . . H10A H -0.2890 -0.2700 -0.5439 0.076 Uiso 1 1 calc R . . H10B H -0.2112 -0.3444 -0.5304 0.076 Uiso 1 1 calc R . . H10C H -0.2105 -0.2520 -0.5880 0.076 Uiso 1 1 calc R . . C11 C -0.2326(2) -0.2198(3) -0.4235(2) 0.0403(8) Uani 1 1 d . . . C12 C -0.3451(3) -0.2065(5) -0.3479(3) 0.0717(14) Uani 1 1 d . . . H12A H -0.3950 -0.1643 -0.3430 0.108 Uiso 1 1 calc R . . H12B H -0.3109 -0.1931 -0.3092 0.108 Uiso 1 1 calc R . . H12C H -0.3572 -0.2866 -0.3512 0.108 Uiso 1 1 calc R . . C13 C -0.1719(3) -0.0211(3) -0.2891(2) 0.0471(9) Uani 1 1 d . . . C14 C -0.2621(4) 0.0413(4) -0.2018(3) 0.0743(14) Uani 1 1 d . . . H14A H -0.3083 0.0909 -0.1964 0.111 Uiso 1 1 calc R . . H14B H -0.2184 0.0671 -0.1731 0.111 Uiso 1 1 calc R . . H14C H -0.2770 -0.0352 -0.1894 0.111 Uiso 1 1 calc R . . C15 C 0.0261(2) -0.0834(3) -0.4683(2) 0.0423(8) Uani 1 1 d . . . C16 C 0.1501(3) 0.0161(4) -0.4541(4) 0.0775(16) Uani 1 1 d . . . H16A H 0.1701 0.0866 -0.4356 0.116 Uiso 1 1 calc R . . H16B H 0.1629 0.0125 -0.5016 0.116 Uiso 1 1 calc R . . H16C H 0.1754 -0.0470 -0.4311 0.116 Uiso 1 1 calc R . . C17 C -0.2246(2) 0.1492(3) -0.5189(2) 0.0468(9) Uani 1 1 d . . . C18 C -0.2131(4) 0.2652(4) -0.6159(3) 0.0780(16) Uani 1 1 d . . . H18A H -0.1828 0.2693 -0.6575 0.117 Uiso 1 1 calc R . . H18B H -0.2030 0.3327 -0.5895 0.117 Uiso 1 1 calc R . . H18C H -0.2702 0.2597 -0.6258 0.117 Uiso 1 1 calc R . . O1 O -0.04058(16) -0.1420(2) -0.34758(14) 0.0478(6) Uani 1 1 d . . . H1A H -0.0563 -0.1413 -0.3081 0.072 Uiso 1 1 calc R . . O2 O -0.28905(17) -0.0511(2) -0.54982(16) 0.0578(7) Uani 1 1 d . . . O3 O -0.30306(16) -0.1693(2) -0.40922(15) 0.0516(7) Uani 1 1 d . . . O4 O -0.20177(19) -0.2930(2) -0.38984(16) 0.0590(8) Uani 1 1 d . . . O5 O -0.23558(18) 0.0431(2) -0.27210(15) 0.0549(7) Uani 1 1 d . . . O6 O -0.1347(2) -0.0794(3) -0.24774(16) 0.0682(9) Uani 1 1 d . . . O7 O 0.06287(16) 0.0102(2) -0.44512(19) 0.0619(8) Uani 1 1 d . . . O8 O 0.06132(16) -0.1620(3) -0.4927(2) 0.0702(9) Uani 1 1 d . . . O9 O -0.18767(18) 0.1658(3) -0.57800(17) 0.0631(8) Uani 1 1 d . . . O10 O -0.2782(2) 0.2073(3) -0.49771(19) 0.0730(10) Uani 1 1 d . . . C19 C -0.0659(2) 0.5515(3) -0.22727(17) 0.0356(7) Uani 1 1 d . . . C20 C -0.1577(2) 0.5401(3) -0.21329(19) 0.0368(7) Uani 1 1 d . . . H20A H -0.1675 0.5392 -0.1647 0.044 Uiso 1 1 calc R . . H20B H -0.1866 0.6046 -0.2327 0.044 Uiso 1 1 calc R . . C21 C -0.18819(19) 0.4284(3) -0.24524(18) 0.0351(7) Uani 1 1 d . . . C22 C -0.1678(2) 0.4257(3) -0.31971(17) 0.0356(7) Uani 1 1 d . . . C23 C -0.1038(2) 0.4827(3) -0.34548(18) 0.0374(8) Uani 1 1 d . . . C24 C -0.0517(2) 0.5626(3) -0.30425(18) 0.0393(8) Uani 1 1 d . . . H24A H -0.0631 0.6406 -0.3180 0.047 Uiso 1 1 calc R . . H24B H 0.0052 0.5472 -0.3140 0.047 Uiso 1 1 calc R . . C25 C -0.0208(2) 0.4480(3) -0.19731(18) 0.0390(8) Uani 1 1 d . . . C26 C -0.0538(2) 0.3286(3) -0.21215(19) 0.0392(8) Uani 1 1 d . . . C27 C -0.14753(19) 0.3257(3) -0.20990(19) 0.0372(8) Uani 1 1 d . . . H27A H -0.1650 0.3237 -0.1629 0.045 Uiso 1 1 calc R . . H27B H -0.1663 0.2558 -0.2314 0.045 Uiso 1 1 calc R . . C28 C -0.0205(3) 0.2434(4) -0.1589(3) 0.0575(13) Uani 1 1 d . . . H28A H -0.0382 0.2661 -0.1145 0.086 Uiso 1 1 calc R . . H28B H 0.0380 0.2430 -0.1605 0.086 Uiso 1 1 calc R . . H28C H -0.0406 0.1681 -0.1687 0.086 Uiso 1 1 calc R . . C29 C -0.0219(2) 0.2826(3) -0.2802(2) 0.0426(8) Uani 1 1 d . . . C30 C 0.0884(3) 0.2878(5) -0.3573(3) 0.0734(14) Uani 1 1 d . . . H30A H 0.1382 0.3291 -0.3648 0.110 Uiso 1 1 calc R . . H30B H 0.0531 0.2973 -0.3958 0.110 Uiso 1 1 calc R . . H30C H 0.1003 0.2082 -0.3512 0.110 Uiso 1 1 calc R . . C31 C -0.0846(3) 0.4697(3) -0.4176(2) 0.0492(9) Uani 1 1 d . . . C32 C 0.0067(5) 0.5217(6) -0.5060(3) 0.0907(18) Uani 1 1 d . . . H32A H 0.0534 0.5697 -0.5127 0.136 Uiso 1 1 calc R . . H32B H -0.0365 0.5459 -0.5356 0.136 Uiso 1 1 calc R . . H32C H 0.0208 0.4439 -0.5161 0.136 Uiso 1 1 calc R . . C33 C -0.2807(2) 0.4194(3) -0.2346(2) 0.0414(8) Uani 1 1 d . . . C34 C -0.4058(2) 0.5159(4) -0.2486(3) 0.0729(15) Uani 1 1 d . . . H34A H -0.4267 0.5846 -0.2688 0.109 Uiso 1 1 calc R . . H34B H -0.4169 0.5164 -0.2008 0.109 Uiso 1 1 calc R . . H34C H -0.4315 0.4507 -0.2690 0.109 Uiso 1 1 calc R . . C35 C -0.0304(2) 0.6578(3) -0.1931(2) 0.0455(9) Uani 1 1 d . . . C36 C -0.0346(4) 0.7761(5) -0.0965(3) 0.0863(19) Uani 1 1 d . . . H36A H -0.0638 0.7838 -0.0545 0.129 Uiso 1 1 calc R . . H36B H -0.0418 0.8439 -0.1232 0.129 Uiso 1 1 calc R . . H36C H 0.0224 0.7653 -0.0872 0.129 Uiso 1 1 calc R . . O11 O -0.21592(16) 0.3540(2) -0.35522(14) 0.0490(6) Uani 1 1 d . . . H11A H -0.2005 0.3517 -0.3948 0.073 Uiso 1 1 calc R . . O12 O 0.03897(17) 0.4629(3) -0.16254(16) 0.0567(7) Uani 1 1 d . . . O13 O 0.04850(16) 0.3316(2) -0.29713(14) 0.0514(7) Uani 1 1 d . . . O14 O -0.05373(19) 0.2067(3) -0.31123(18) 0.0626(8) Uani 1 1 d . . . O15 O -0.02020(19) 0.5301(3) -0.43600(15) 0.0609(8) Uani 1 1 d . . . O16 O -0.1231(2) 0.4081(3) -0.45662(16) 0.0756(10) Uani 1 1 d . . . O17 O -0.31861(16) 0.5098(2) -0.25943(18) 0.0579(8) Uani 1 1 d . . . O18 O -0.31447(16) 0.3432(3) -0.2061(2) 0.0686(9) Uani 1 1 d . . . O19 O -0.06560(18) 0.6782(2) -0.13357(15) 0.0590(8) Uani 1 1 d . . . O20 O 0.0225(2) 0.7156(3) -0.21677(17) 0.0703(10) Uani 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 0.0395(18) 0.0364(17) 0.042(2) 0.0045(15) 0.0005(16) 0.0071(14) C2 0.0371(17) 0.0390(17) 0.045(2) 0.0052(16) 0.0040(16) -0.0023(14) C3 0.0341(17) 0.0344(16) 0.0396(19) -0.0012(15) 0.0010(14) 0.0018(14) C4 0.0382(18) 0.0322(16) 0.0388(19) -0.0016(14) -0.0041(15) -0.0005(14) C5 0.0421(19) 0.0337(17) 0.041(2) -0.0032(15) 0.0007(16) -0.0033(15) C6 0.0437(19) 0.0372(17) 0.042(2) -0.0016(15) 0.0017(16) 0.0056(15) C7 0.0346(17) 0.0443(18) 0.0362(19) 0.0061(15) 0.0024(15) -0.0006(14) C8 0.0370(17) 0.0352(16) 0.0410(19) 0.0004(15) 0.0005(16) -0.0002(13) C9 0.0370(17) 0.0370(17) 0.0400(19) -0.0022(15) 0.0030(16) 0.0009(14) C10 0.053(3) 0.049(2) 0.049(3) -0.0071(19) -0.003(2) -0.0107(18) C11 0.039(2) 0.0390(18) 0.043(2) -0.0003(18) 0.0016(16) -0.0061(16) C12 0.065(3) 0.080(3) 0.071(3) 0.012(3) 0.028(3) 0.001(3) C13 0.054(2) 0.0420(19) 0.046(2) -0.0013(17) 0.0027(18) -0.0027(17) C14 0.096(4) 0.067(3) 0.059(3) 0.002(2) 0.034(3) 0.004(3) C15 0.0356(18) 0.0446(19) 0.047(2) -0.0016(17) -0.0008(17) 0.0016(16) C16 0.035(2) 0.068(3) 0.129(5) -0.015(3) 0.000(3) -0.006(2) C17 0.045(2) 0.0431(19) 0.052(2) 0.0087(18) 0.0024(18) 0.0030(17) C18 0.082(4) 0.065(3) 0.086(4) 0.037(3) -0.004(3) 0.007(3) O1 0.0478(14) 0.0511(14) 0.0444(15) 0.0039(12) -0.0077(12) 0.0071(12) O2 0.0533(16) 0.0595(16) 0.0607(18) 0.0093(14) -0.0189(15) -0.0007(13) O3 0.0434(14) 0.0568(15) 0.0547(17) 0.0096(13) 0.0112(13) 0.0031(12) O4 0.0629(19) 0.0497(16) 0.065(2) 0.0207(15) 0.0033(16) 0.0055(14) O5 0.0632(18) 0.0531(15) 0.0483(16) 0.0003(13) 0.0158(14) 0.0050(13) O6 0.085(2) 0.076(2) 0.0432(17) 0.0067(16) 0.0020(16) 0.0191(18) O7 0.0363(14) 0.0539(16) 0.096(2) -0.0189(16) 0.0018(15) -0.0050(12) O8 0.0415(15) 0.0629(18) 0.106(3) -0.0291(18) 0.0054(17) 0.0044(13) O9 0.0628(18) 0.0624(18) 0.0642(19) 0.0299(15) 0.0093(16) 0.0137(15) O10 0.075(2) 0.0690(19) 0.075(2) 0.0186(18) 0.0123(19) 0.0369(19) C19 0.0361(17) 0.0390(17) 0.0316(17) -0.0024(14) 0.0015(14) -0.0054(14) C20 0.0374(17) 0.0350(16) 0.0378(19) -0.0025(14) 0.0048(15) -0.0031(13) C21 0.0309(16) 0.0327(16) 0.0418(19) 0.0015(15) 0.0007(15) -0.0016(13) C22 0.0403(18) 0.0319(16) 0.0344(18) -0.0009(14) -0.0065(15) 0.0022(14) C23 0.044(2) 0.0369(17) 0.0309(18) 0.0006(14) -0.0009(15) -0.0018(15) C24 0.0458(19) 0.0366(17) 0.0355(18) 0.0019(15) 0.0009(15) -0.0071(15) C25 0.0346(17) 0.054(2) 0.0284(17) -0.0018(16) 0.0043(15) -0.0017(15) C26 0.0355(17) 0.0427(18) 0.039(2) 0.0076(15) 0.0014(15) 0.0065(14) C27 0.0360(17) 0.0355(16) 0.040(2) 0.0065(15) 0.0008(15) -0.0015(14) C28 0.056(3) 0.062(3) 0.055(3) 0.019(2) -0.002(2) 0.010(2) C29 0.038(2) 0.0419(19) 0.048(2) 0.0017(19) 0.0034(17) 0.0041(17) C30 0.063(3) 0.085(3) 0.072(3) -0.010(3) 0.029(3) 0.011(3) C31 0.061(2) 0.052(2) 0.035(2) -0.0007(17) 0.0003(19) 0.0021(19) C32 0.117(4) 0.109(4) 0.046(3) 0.000(3) 0.033(3) -0.011(4) C33 0.0325(17) 0.0397(18) 0.052(2) 0.0000(17) -0.0021(17) 0.0014(15) C34 0.037(2) 0.067(3) 0.115(5) 0.009(3) 0.001(3) 0.010(2) C35 0.049(2) 0.0474(19) 0.040(2) -0.0061(17) 0.0020(17) -0.0084(17) C36 0.092(4) 0.083(3) 0.083(4) -0.052(3) 0.012(3) -0.030(3) O11 0.0494(14) 0.0499(14) 0.0476(15) -0.0084(12) -0.0057(13) -0.0079(12) O12 0.0468(16) 0.0701(19) 0.0533(17) -0.0081(14) -0.0145(13) -0.0004(13) O13 0.0453(14) 0.0580(16) 0.0511(16) -0.0058(13) 0.0119(13) 0.0019(13) O14 0.0600(18) 0.0534(17) 0.074(2) -0.0189(16) 0.0076(16) -0.0046(14) O15 0.0711(19) 0.074(2) 0.0375(15) 0.0019(14) 0.0139(15) -0.0113(16) O16 0.097(2) 0.088(2) 0.0414(17) -0.0173(17) 0.0007(17) -0.023(2) O17 0.0355(13) 0.0491(15) 0.089(2) 0.0159(15) 0.0014(14) 0.0053(11) O18 0.0382(14) 0.0636(18) 0.104(3) 0.0327(19) 0.0051(16) -0.0062(13) O19 0.0638(18) 0.0613(17) 0.0521(16) -0.0234(14) 0.0093(14) -0.0194(14) O20 0.079(2) 0.069(2) 0.063(2) -0.0117(17) 0.0121(17) -0.0400(18) _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 C17 1.534(5) . ? C1 C6 1.536(5) . ? C1 C2 1.540(5) . ? C1 C7 1.542(5) . ? C2 C3 1.539(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.506(5) . ? C3 C15 1.525(5) . ? C3 C9 1.540(5) . ? C4 O1 1.343(4) . ? C4 C5 1.348(5) . ? C5 C13 1.454(6) . ? C5 C6 1.506(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O2 1.205(4) . ? C7 C8 1.535(5) . ? C8 C11 1.535(5) . ? C8 C10 1.540(5) . ? C8 C9 1.548(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 O4 1.196(5) . ? C11 O3 1.327(4) . ? C12 O3 1.458(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O6 1.226(5) . ? C13 O5 1.329(5) . ? C14 O5 1.452(6) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O8 1.189(4) . ? C15 O7 1.330(4) . ? C16 O7 1.444(5) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O10 1.186(5) . ? C17 O9 1.327(5) . ? C18 O9 1.443(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O1 H1A 0.8200 . ? C19 C35 1.529(5) . ? C19 C20 1.535(5) . ? C19 C25 1.537(5) . ? C19 C24 1.540(5) . ? C20 C21 1.534(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.505(5) . ? C21 C33 1.535(5) . ? C21 C27 1.541(5) . ? C22 C23 1.344(5) . ? C22 O11 1.347(4) . ? C23 C31 1.464(5) . ? C23 C24 1.505(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 O12 1.208(4) . ? C25 C26 1.528(5) . ? C26 C29 1.537(5) . ? C26 C27 1.538(5) . ? C26 C28 1.546(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 O14 1.198(5) . ? C29 O13 1.331(4) . ? C30 O13 1.448(5) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 O16 1.228(5) . ? C31 O15 1.322(5) . ? C32 O15 1.452(6) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 O18 1.190(4) . ? C33 O17 1.321(4) . ? C34 O17 1.447(5) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 O20 1.195(5) . ? C35 O19 1.330(5) . ? C36 O19 1.451(5) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? O11 H11A 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 C17 C1 C6 107.8(3) . . ? C17 C1 C2 111.4(3) . . ? C6 C1 C2 108.8(3) . . ? C17 C1 C7 107.2(3) . . ? C6 C1 C7 112.9(3) . . ? C2 C1 C7 108.8(3) . . ? C3 C2 C1 109.1(3) . . ? C3 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? C3 C2 H2B 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C4 C3 C15 110.8(3) . . ? C4 C3 C2 109.8(3) . . ? C15 C3 C2 108.7(3) . . ? C4 C3 C9 109.5(3) . . ? C15 C3 C9 108.4(3) . . ? C2 C3 C9 109.5(3) . . ? O1 C4 C5 124.8(3) . . ? O1 C4 C3 112.3(3) . . ? C5 C4 C3 122.7(3) . . ? C4 C5 C13 118.9(3) . . ? C4 C5 C6 122.4(3) . . ? C13 C5 C6 118.7(3) . . ? C5 C6 C1 114.3(3) . . ? C5 C6 H6A 108.7 . . ? C1 C6 H6A 108.7 . . ? C5 C6 H6B 108.7 . . ? C1 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? O2 C7 C8 121.1(3) . . ? O2 C7 C1 120.2(3) . . ? C8 C7 C1 118.6(3) . . ? C7 C8 C11 111.1(3) . . ? C7 C8 C10 110.1(3) . . ? C11 C8 C10 104.9(3) . . ? C7 C8 C9 111.0(3) . . ? C11 C8 C9 110.8(3) . . ? C10 C8 C9 108.8(3) . . ? C3 C9 C8 114.1(3) . . ? C3 C9 H9A 108.7 . . ? C8 C9 H9A 108.7 . . ? C3 C9 H9B 108.7 . . ? C8 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O4 C11 O3 124.7(4) . . ? O4 C11 C8 123.8(3) . . ? O3 C11 C8 111.2(3) . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O6 C13 O5 122.6(4) . . ? O6 C13 C5 124.8(4) . . ? O5 C13 C5 112.6(4) . . ? O5 C14 H14A 109.5 . . ? O5 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O5 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O8 C15 O7 123.7(3) . . ? O8 C15 C3 125.0(3) . . ? O7 C15 C3 111.3(3) . . ? O7 C16 H16A 109.5 . . ? O7 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O7 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O10 C17 O9 124.2(4) . . ? O10 C17 C1 124.7(4) . . ? O9 C17 C1 111.1(3) . . ? O9 C18 H18A 109.5 . . ? O9 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O9 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C4 O1 H1A 109.5 . . ? C11 O3 C12 117.0(3) . . ? C13 O5 C14 117.9(4) . . ? C15 O7 C16 116.5(3) . . ? C17 O9 C18 116.1(4) . . ? C35 C19 C20 111.4(3) . . ? C35 C19 C25 106.7(3) . . ? C20 C19 C25 109.6(3) . . ? C35 C19 C24 107.9(3) . . ? C20 C19 C24 109.4(3) . . ? C25 C19 C24 111.8(3) . . ? C21 C20 C19 108.7(3) . . ? C21 C20 H20A 110.0 . . ? C19 C20 H20A 110.0 . . ? C21 C20 H20B 110.0 . . ? C19 C20 H20B 110.0 . . ? H20A C20 H20B 108.3 . . ? C22 C21 C20 110.2(3) . . ? C22 C21 C33 110.5(3) . . ? C20 C21 C33 109.0(3) . . ? C22 C21 C27 109.1(3) . . ? C20 C21 C27 109.7(3) . . ? C33 C21 C27 108.2(3) . . ? C23 C22 O11 124.8(3) . . ? C23 C22 C21 122.1(3) . . ? O11 C22 C21 112.9(3) . . ? C22 C23 C31 118.9(3) . . ? C22 C23 C24 123.2(3) . . ? C31 C23 C24 117.8(3) . . ? C23 C24 C19 113.1(3) . . ? C23 C24 H24A 108.9 . . ? C19 C24 H24A 108.9 . . ? C23 C24 H24B 108.9 . . ? C19 C24 H24B 108.9 . . ? H24A C24 H24B 107.8 . . ? O12 C25 C26 121.8(3) . . ? O12 C25 C19 119.7(3) . . ? C26 C25 C19 118.4(3) . . ? C25 C26 C29 111.5(3) . . ? C25 C26 C27 111.7(3) . . ? C29 C26 C27 111.0(3) . . ? C25 C26 C28 109.6(3) . . ? C29 C26 C28 104.2(3) . . ? C27 C26 C28 108.6(3) . . ? C26 C27 C21 113.7(3) . . ? C26 C27 H27A 108.8 . . ? C21 C27 H27A 108.8 . . ? C26 C27 H27B 108.8 . . ? C21 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O14 C29 O13 124.7(4) . . ? O14 C29 C26 123.8(3) . . ? O13 C29 C26 111.3(3) . . ? O13 C30 H30A 109.5 . . ? O13 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O13 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O16 C31 O15 123.6(4) . . ? O16 C31 C23 123.9(4) . . ? O15 C31 C23 112.4(4) . . ? O15 C32 H32A 109.5 . . ? O15 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O15 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O18 C33 O17 123.7(3) . . ? O18 C33 C21 125.2(3) . . ? O17 C33 C21 111.1(3) . . ? O17 C34 H34A 109.5 . . ? O17 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O17 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O20 C35 O19 123.9(4) . . ? O20 C35 C19 124.5(4) . . ? O19 C35 C19 111.6(3) . . ? O19 C36 H36A 109.5 . . ? O19 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O19 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C22 O11 H11A 109.5 . . ? C29 O13 C30 116.4(3) . . ? C31 O15 C32 117.8(4) . . ? C33 O17 C34 116.7(3) . . ? C35 O19 C36 115.7(3) . . ? 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 C17 C1 C2 C3 -177.3(3) . . . . ? C6 C1 C2 C3 64.1(4) . . . . ? C7 C1 C2 C3 -59.3(4) . . . . ? C1 C2 C3 C4 -55.7(4) . . . . ? C1 C2 C3 C15 -177.1(3) . . . . ? C1 C2 C3 C9 64.6(4) . . . . ? C15 C3 C4 O1 -37.9(4) . . . . ? C2 C3 C4 O1 -158.1(3) . . . . ? C9 C3 C4 O1 81.6(3) . . . . ? C15 C3 C4 C5 146.5(3) . . . . ? C2 C3 C4 C5 26.4(4) . . . . ? C9 C3 C4 C5 -93.9(4) . . . . ? O1 C4 C5 C13 2.1(5) . . . . ? C3 C4 C5 C13 177.1(3) . . . . ? O1 C4 C5 C6 -179.5(3) . . . . ? C3 C4 C5 C6 -4.5(5) . . . . ? C4 C5 C6 C1 12.3(5) . . . . ? C13 C5 C6 C1 -169.3(3) . . . . ? C17 C1 C6 C5 -162.4(3) . . . . ? C2 C1 C6 C5 -41.5(4) . . . . ? C7 C1 C6 C5 79.4(4) . . . . ? C17 C1 C7 O2 -7.5(5) . . . . ? C6 C1 C7 O2 111.0(4) . . . . ? C2 C1 C7 O2 -128.1(4) . . . . ? C17 C1 C7 C8 169.9(3) . . . . ? C6 C1 C7 C8 -71.6(4) . . . . ? C2 C1 C7 C8 49.2(4) . . . . ? O2 C7 C8 C11 -99.5(4) . . . . ? C1 C7 C8 C11 83.2(4) . . . . ? O2 C7 C8 C10 16.2(5) . . . . ? C1 C7 C8 C10 -161.1(3) . . . . ? O2 C7 C8 C9 136.7(4) . . . . ? C1 C7 C8 C9 -40.6(4) . . . . ? C4 C3 C9 C8 63.6(4) . . . . ? C15 C3 C9 C8 -175.3(3) . . . . ? C2 C3 C9 C8 -56.8(4) . . . . ? C7 C8 C9 C3 43.3(4) . . . . ? C11 C8 C9 C3 -80.7(4) . . . . ? C10 C8 C9 C3 164.6(3) . . . . ? C7 C8 C11 O4 -160.4(4) . . . . ? C10 C8 C11 O4 80.7(5) . . . . ? C9 C8 C11 O4 -36.5(5) . . . . ? C7 C8 C11 O3 24.9(4) . . . . ? C10 C8 C11 O3 -94.0(4) . . . . ? C9 C8 C11 O3 148.8(3) . . . . ? C4 C5 C13 O6 -1.9(6) . . . . ? C6 C5 C13 O6 179.6(4) . . . . ? C4 C5 C13 O5 178.5(3) . . . . ? C6 C5 C13 O5 0.0(5) . . . . ? C4 C3 C15 O8 115.0(5) . . . . ? C2 C3 C15 O8 -124.2(5) . . . . ? C9 C3 C15 O8 -5.2(6) . . . . ? C4 C3 C15 O7 -64.9(4) . . . . ? C2 C3 C15 O7 55.9(4) . . . . ? C9 C3 C15 O7 174.9(3) . . . . ? C6 C1 C17 O10 -25.5(5) . . . . ? C2 C1 C17 O10 -144.7(4) . . . . ? C7 C1 C17 O10 96.3(5) . . . . ? C6 C1 C17 O9 155.0(3) . . . . ? C2 C1 C17 O9 35.8(5) . . . . ? C7 C1 C17 O9 -83.2(4) . . . . ? O4 C11 O3 C12 0.1(6) . . . . ? C8 C11 O3 C12 174.7(4) . . . . ? O6 C13 O5 C14 -1.2(6) . . . . ? C5 C13 O5 C14 178.4(4) . . . . ? O8 C15 O7 C16 3.2(7) . . . . ? C3 C15 O7 C16 -176.9(4) . . . . ? O10 C17 O9 C18 3.3(7) . . . . ? C1 C17 O9 C18 -177.2(4) . . . . ? C35 C19 C20 C21 -176.6(3) . . . . ? C25 C19 C20 C21 -58.8(4) . . . . ? C24 C19 C20 C21 64.2(4) . . . . ? C19 C20 C21 C22 -55.7(4) . . . . ? C19 C20 C21 C33 -177.1(3) . . . . ? C19 C20 C21 C27 64.6(4) . . . . ? C20 C21 C22 C23 27.3(4) . . . . ? C33 C21 C22 C23 147.9(3) . . . . ? C27 C21 C22 C23 -93.3(4) . . . . ? C20 C21 C22 O11 -157.7(3) . . . . ? C33 C21 C22 O11 -37.1(4) . . . . ? C27 C21 C22 O11 81.7(3) . . . . ? O11 C22 C23 C31 1.5(5) . . . . ? C21 C22 C23 C31 175.9(3) . . . . ? O11 C22 C23 C24 179.6(3) . . . . ? C21 C22 C23 C24 -5.9(5) . . . . ? C22 C23 C24 C19 13.4(5) . . . . ? C31 C23 C24 C19 -168.5(3) . . . . ? C35 C19 C24 C23 -163.4(3) . . . . ? C20 C19 C24 C23 -42.0(4) . . . . ? C25 C19 C24 C23 79.6(4) . . . . ? C35 C19 C25 O12 -10.5(4) . . . . ? C20 C19 C25 O12 -131.2(3) . . . . ? C24 C19 C25 O12 107.2(4) . . . . ? C35 C19 C25 C26 169.0(3) . . . . ? C20 C19 C25 C26 48.2(4) . . . . ? C24 C19 C25 C26 -73.3(4) . . . . ? O12 C25 C26 C29 -95.5(4) . . . . ? C19 C25 C26 C29 85.1(4) . . . . ? O12 C25 C26 C27 139.8(3) . . . . ? C19 C25 C26 C27 -39.7(4) . . . . ? O12 C25 C26 C28 19.4(5) . . . . ? C19 C25 C26 C28 -160.0(3) . . . . ? C25 C26 C27 C21 43.0(4) . . . . ? C29 C26 C27 C21 -82.1(4) . . . . ? C28 C26 C27 C21 163.9(3) . . . . ? C22 C21 C27 C26 63.9(4) . . . . ? C20 C21 C27 C26 -57.0(4) . . . . ? C33 C21 C27 C26 -175.9(3) . . . . ? C25 C26 C29 O14 -160.1(4) . . . . ? C27 C26 C29 O14 -34.9(5) . . . . ? C28 C26 C29 O14 81.8(5) . . . . ? C25 C26 C29 O13 24.8(4) . . . . ? C27 C26 C29 O13 150.0(3) . . . . ? C28 C26 C29 O13 -93.3(4) . . . . ? C22 C23 C31 O16 -0.9(6) . . . . ? C24 C23 C31 O16 -179.2(4) . . . . ? C22 C23 C31 O15 -179.8(3) . . . . ? C24 C23 C31 O15 2.0(5) . . . . ? C22 C21 C33 O18 116.9(4) . . . . ? C20 C21 C33 O18 -121.8(4) . . . . ? C27 C21 C33 O18 -2.6(5) . . . . ? C22 C21 C33 O17 -65.3(4) . . . . ? C20 C21 C33 O17 56.0(4) . . . . ? C27 C21 C33 O17 175.3(3) . . . . ? C20 C19 C35 O20 -144.4(4) . . . . ? C25 C19 C35 O20 96.0(5) . . . . ? C24 C19 C35 O20 -24.3(5) . . . . ? C20 C19 C35 O19 35.7(4) . . . . ? C25 C19 C35 O19 -83.9(4) . . . . ? C24 C19 C35 O19 155.8(3) . . . . ? O14 C29 O13 C30 -0.4(6) . . . . ? C26 C29 O13 C30 174.6(3) . . . . ? O16 C31 O15 C32 -0.7(7) . . . . ? C23 C31 O15 C32 178.1(4) . . . . ? O18 C33 O17 C34 2.0(7) . . . . ? C21 C33 O17 C34 -175.8(4) . . . . ? O20 C35 O19 C36 -1.3(6) . . . . ? C19 C35 O19 C36 178.6(4) . . . . ? 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 O1 H1A O6 0.82 1.89 2.605(4) 144 . O11 H11A O16 0.82 1.88 2.590(4) 144 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.236 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.041 _diffrn_ambient_pressure 101.33 _exptl_crystal_recrystallization_method 'sat. soln in methylene chloride allowed to sit for several days'