# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full MedChemComm _journal_coden_cambridge 1476 _publ_contact_author_name B.Sridhar _publ_contact_author_address ;Laboratory of X-ray Crystallography Indian Institute of Chemical Technology Hyderabad 500 007 India ; _publ_contact_author_email sshiya@yahoo.com _publ_contact_author_phone 09104027193118 _publ_contact_author_fax 09104027193118 loop_ _publ_author_address ;Organic Chemistry Division Indian Institute of Chemical Technology Hyderabad 500 007 India ; ;Organic Chemistry Division Indian Institute of Chemical Technology Hyderabad 500 007 India ; ;Organic Chemistry Division Indian Institute of Chemical Technology Hyderabad 500 007 India ; ;Center for Chemical Biology Indian Institute of Chemical Technology Hyderabad 500 007 India ; ;Center for Nuclear Magnetic Resonance Indian Institute of Chemical Technology Hyderabad 500 007 India ; ;Center for Nuclear Magnetic Resonance Indian Institute of Chemical Technology Hyderabad 500 007 India ; ;Laboratory of X-ray Crystallography Indian Institute of Chemical Technology Hyderabad 500 007 India ; ;Center for Chemical Biology Indian Institute of Chemical Technology Hyderabad 500 007 India ; loop_ _publ_author_name K.Nagaiah A.Venkatesham R.S.Rao data_ae91 _database_code_depnum_ccdc_archive 'CCDC 839724' #TrackingRef '6762_web_deposit_cif_file_0_B.Sridhar_1313556540.ae91f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2,8,9,13,13-Hexamethyl-2a,3,10c,12,13,14-hexahydro-2H-1,4,10- trioxa-dibenzo[c,g]phenanthrene-7,11-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H28 O5' _chemical_formula_sum 'C25 H28 O5' _chemical_formula_weight 408.47 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 0.0016 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 11.7974(15) _cell_length_b 13.9420(18) _cell_length_c 13.4238(17) _cell_angle_alpha 90.00 _cell_angle_beta 101.254(2) _cell_angle_gamma 90.00 _cell_volume 2165.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 6526 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 25.62 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _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 'CCD Area Detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20554 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3806 _reflns_number_gt 3113 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0672P)^2^+0.3974P] 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 3806 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1279 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.61291(14) 0.15938(11) 0.56179(12) 0.0499(4) Uani 1 1 d . . . C2 C 0.61754(16) 0.13223(12) 0.66105(13) 0.0593(4) Uani 1 1 d . . . C3 C 0.52085(18) 0.09554(14) 0.69434(14) 0.0704(5) Uani 1 1 d . . . H3 H 0.5262 0.0782 0.7620 0.085 Uiso 1 1 calc R . . C4 C 0.41951(17) 0.08541(13) 0.62758(14) 0.0670(5) Uani 1 1 d . . . H4 H 0.3549 0.0627 0.6503 0.080 Uiso 1 1 calc R . . C5 C 0.41076(14) 0.10854(11) 0.52534(13) 0.0556(4) Uani 1 1 d . . . C6 C 0.30299(15) 0.09920(12) 0.45159(15) 0.0630(5) Uani 1 1 d . . . C7 C 0.30903(15) 0.12188(12) 0.34773(15) 0.0636(5) Uani 1 1 d . . . C8 C 0.41059(15) 0.14735(11) 0.32393(13) 0.0572(4) Uani 1 1 d . . . C9 C 0.50889(14) 0.14205(10) 0.49456(12) 0.0488(4) Uani 1 1 d . . . C10 C 0.81849(17) 0.17097(15) 0.70523(14) 0.0719(5) Uani 1 1 d . . . H10A H 0.8842 0.1409 0.7488 0.086 Uiso 1 1 calc R . . H10B H 0.8248 0.2396 0.7166 0.086 Uiso 1 1 calc R . . C11 C 0.82436(15) 0.15049(12) 0.59525(13) 0.0610(4) Uani 1 1 d . . . H11 H 0.8205 0.0809 0.5849 0.073 Uiso 1 1 calc R . . C12 C 0.93602(15) 0.18719(14) 0.56694(15) 0.0691(5) Uani 1 1 d . . . C13 C 0.84353(13) 0.34188(12) 0.55500(13) 0.0549(4) Uani 1 1 d . . . C14 C 0.87080(14) 0.44648(13) 0.56237(15) 0.0644(5) Uani 1 1 d . . . H14A H 0.9035 0.4649 0.5042 0.077 Uiso 1 1 calc R . . H14B H 0.9293 0.4575 0.6229 0.077 Uiso 1 1 calc R . . C15 C 0.76834(14) 0.51028(12) 0.56646(13) 0.0579(4) Uani 1 1 d . . . C16 C 0.67060(14) 0.47509(12) 0.48359(13) 0.0560(4) Uani 1 1 d . . . H16A H 0.6024 0.5135 0.4848 0.067 Uiso 1 1 calc R . . H16B H 0.6921 0.4847 0.4182 0.067 Uiso 1 1 calc R . . C17 C 0.64093(13) 0.37085(11) 0.49385(11) 0.0472(4) Uani 1 1 d . . . C18 C 0.73675(12) 0.30399(11) 0.52677(11) 0.0469(4) Uani 1 1 d . . . C19 C 0.71936(13) 0.19580(11) 0.52673(12) 0.0496(4) Uani 1 1 d . . . H19 H 0.7165 0.1725 0.4574 0.059 Uiso 1 1 calc R . . C20 C 0.20002(17) 0.11231(18) 0.26839(18) 0.0913(7) Uani 1 1 d . . . H20A H 0.1993 0.1602 0.2169 0.137 Uiso 1 1 calc R . . H20B H 0.1341 0.1209 0.2995 0.137 Uiso 1 1 calc R . . H20C H 0.1972 0.0497 0.2382 0.137 Uiso 1 1 calc R . . C21 C 1.04382(17) 0.14869(18) 0.63571(19) 0.0943(7) Uani 1 1 d . . . H21A H 1.1110 0.1712 0.6123 0.141 Uiso 1 1 calc R . . H21B H 1.0424 0.0799 0.6345 0.141 Uiso 1 1 calc R . . H21C H 1.0463 0.1707 0.7039 0.141 Uiso 1 1 calc R . . C22 C 0.93974(18) 0.16749(19) 0.45662(16) 0.0895(7) Uani 1 1 d . . . H22A H 0.8799 0.2033 0.4137 0.134 Uiso 1 1 calc R . . H22B H 0.9281 0.1002 0.4430 0.134 Uiso 1 1 calc R . . H22C H 1.0136 0.1864 0.4433 0.134 Uiso 1 1 calc R . . C23 C 0.79750(19) 0.61469(14) 0.54668(18) 0.0838(6) Uani 1 1 d . . . H23A H 0.8597 0.6361 0.5991 0.126 Uiso 1 1 calc R . . H23B H 0.7308 0.6541 0.5465 0.126 Uiso 1 1 calc R . . H23C H 0.8203 0.6193 0.4820 0.126 Uiso 1 1 calc R . . C24 C 0.43460(18) 0.16522(15) 0.22115(14) 0.0774(6) Uani 1 1 d . . . H24A H 0.4497 0.1054 0.1908 0.116 Uiso 1 1 calc R . . H24B H 0.5008 0.2063 0.2263 0.116 Uiso 1 1 calc R . . H24C H 0.3688 0.1956 0.1797 0.116 Uiso 1 1 calc R . . C25 C 0.7310(2) 0.50384(17) 0.66841(15) 0.0865(7) Uani 1 1 d . . . H25A H 0.7067 0.4395 0.6788 0.130 Uiso 1 1 calc R . . H25B H 0.6680 0.5472 0.6692 0.130 Uiso 1 1 calc R . . H25C H 0.7947 0.5207 0.7217 0.130 Uiso 1 1 calc R . . O1 O 0.71526(12) 0.13780(10) 0.73398(9) 0.0774(4) Uani 1 1 d . . . O2 O 0.50939(9) 0.15816(8) 0.39447(8) 0.0541(3) Uani 1 1 d . . . O3 O 0.21273(11) 0.07306(11) 0.47699(12) 0.0870(5) Uani 1 1 d . . . O4 O 0.54096(9) 0.34514(8) 0.47250(10) 0.0668(4) Uani 1 1 d . . . O5 O 0.94201(9) 0.29096(9) 0.58280(10) 0.0704(4) 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 0.0580(9) 0.0393(8) 0.0521(9) -0.0001(6) 0.0105(7) 0.0020(7) C2 0.0731(11) 0.0503(9) 0.0540(10) 0.0035(7) 0.0111(8) 0.0056(8) C3 0.0917(14) 0.0632(11) 0.0609(11) 0.0120(9) 0.0261(11) 0.0017(10) C4 0.0783(13) 0.0552(10) 0.0754(12) 0.0041(9) 0.0341(10) -0.0033(9) C5 0.0612(10) 0.0397(8) 0.0687(11) -0.0036(7) 0.0195(8) -0.0009(7) C6 0.0548(10) 0.0470(9) 0.0897(13) -0.0118(9) 0.0200(9) -0.0012(7) C7 0.0579(10) 0.0494(9) 0.0794(12) -0.0073(8) 0.0030(9) 0.0019(8) C8 0.0612(10) 0.0431(8) 0.0621(10) -0.0036(7) -0.0006(8) -0.0038(7) C9 0.0592(9) 0.0366(7) 0.0517(9) -0.0005(6) 0.0135(7) 0.0005(6) C10 0.0739(12) 0.0712(12) 0.0628(11) 0.0085(9) -0.0061(9) 0.0040(10) C11 0.0611(10) 0.0514(9) 0.0653(11) -0.0011(8) -0.0004(8) 0.0105(8) C12 0.0538(10) 0.0691(12) 0.0806(13) -0.0068(9) 0.0040(9) 0.0165(9) C13 0.0446(9) 0.0601(10) 0.0595(10) -0.0008(7) 0.0086(7) 0.0025(7) C14 0.0508(10) 0.0650(11) 0.0756(11) -0.0007(9) 0.0079(8) -0.0118(8) C15 0.0590(10) 0.0530(9) 0.0628(10) -0.0065(8) 0.0146(8) -0.0087(7) C16 0.0530(9) 0.0495(9) 0.0650(10) 0.0032(7) 0.0100(8) 0.0021(7) C17 0.0446(8) 0.0492(8) 0.0469(8) -0.0016(6) 0.0071(6) -0.0005(7) C18 0.0448(8) 0.0493(9) 0.0465(8) 0.0004(6) 0.0087(6) 0.0008(7) C19 0.0507(9) 0.0482(9) 0.0482(8) -0.0027(7) 0.0058(7) 0.0025(7) C20 0.0642(12) 0.0948(16) 0.1047(17) -0.0030(13) -0.0086(11) -0.0017(11) C21 0.0649(13) 0.0963(17) 0.1123(18) -0.0078(13) -0.0061(12) 0.0277(11) C22 0.0664(12) 0.1117(18) 0.0924(15) -0.0137(13) 0.0205(11) 0.0181(12) C23 0.0872(14) 0.0578(11) 0.1038(16) -0.0070(11) 0.0125(12) -0.0154(10) C24 0.0892(14) 0.0745(12) 0.0619(11) 0.0032(9) -0.0017(10) -0.0217(11) C25 0.1003(16) 0.0922(15) 0.0707(13) -0.0242(11) 0.0256(12) -0.0207(12) O1 0.0827(9) 0.0917(10) 0.0533(7) 0.0117(6) 0.0019(6) 0.0022(7) O2 0.0578(7) 0.0507(6) 0.0525(6) -0.0020(5) 0.0076(5) -0.0084(5) O3 0.0605(8) 0.0886(10) 0.1183(12) -0.0168(8) 0.0328(8) -0.0104(7) O4 0.0453(7) 0.0513(7) 0.0980(9) 0.0022(6) -0.0005(6) 0.0003(5) O5 0.0427(6) 0.0691(8) 0.0951(9) -0.0031(7) 0.0034(6) 0.0055(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.376(2) . ? C1 C9 1.395(2) . ? C1 C19 1.512(2) . ? C2 O1 1.361(2) . ? C2 C3 1.401(3) . ? C3 C4 1.354(3) . ? C3 H3 0.9300 . ? C4 C5 1.394(2) . ? C4 H4 0.9300 . ? C5 C9 1.384(2) . ? C5 C6 1.457(2) . ? C6 O3 1.235(2) . ? C6 C7 1.445(3) . ? C7 C8 1.347(3) . ? C7 C20 1.507(3) . ? C8 O2 1.3591(19) . ? C8 C24 1.483(3) . ? C9 O2 1.3634(18) . ? C10 O1 1.425(2) . ? C10 C11 1.519(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C19 1.528(2) . ? C11 C12 1.529(3) . ? C11 H11 0.9800 . ? C12 O5 1.462(2) . ? C12 C22 1.515(3) . ? C12 C21 1.516(2) . ? C13 C18 1.350(2) . ? C13 O5 1.3506(19) . ? C13 C14 1.493(2) . ? C14 C15 1.510(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.519(2) . ? C15 C25 1.520(2) . ? C15 C23 1.531(3) . ? C16 C17 1.508(2) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O4 1.2123(18) . ? C17 C18 1.465(2) . ? C18 C19 1.522(2) . ? C19 H19 0.9800 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? 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 C2 C1 C9 116.26(15) . . ? C2 C1 C19 121.01(15) . . ? C9 C1 C19 122.40(14) . . ? O1 C2 C1 123.28(16) . . ? O1 C2 C3 114.81(15) . . ? C1 C2 C3 121.91(17) . . ? C4 C3 C2 119.72(17) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.90(17) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C9 C5 C4 117.80(16) . . ? C9 C5 C6 119.81(16) . . ? C4 C5 C6 122.38(16) . . ? O3 C6 C7 122.59(18) . . ? O3 C6 C5 121.60(18) . . ? C7 C6 C5 115.81(15) . . ? C8 C7 C6 120.03(16) . . ? C8 C7 C20 122.12(19) . . ? C6 C7 C20 117.82(17) . . ? C7 C8 O2 123.07(16) . . ? C7 C8 C24 127.27(16) . . ? O2 C8 C24 109.64(15) . . ? O2 C9 C5 120.96(15) . . ? O2 C9 C1 115.88(13) . . ? C5 C9 C1 123.14(15) . . ? O1 C10 C11 113.96(15) . . ? O1 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? O1 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C10 C11 C19 108.79(14) . . ? C10 C11 C12 112.57(15) . . ? C19 C11 C12 110.41(14) . . ? C10 C11 H11 108.3 . . ? C19 C11 H11 108.3 . . ? C12 C11 H11 108.3 . . ? O5 C12 C22 108.17(17) . . ? O5 C12 C21 104.51(16) . . ? C22 C12 C21 110.48(16) . . ? O5 C12 C11 108.34(13) . . ? C22 C12 C11 111.90(16) . . ? C21 C12 C11 113.03(17) . . ? C18 C13 O5 125.25(15) . . ? C18 C13 C14 125.32(15) . . ? O5 C13 C14 109.42(14) . . ? C13 C14 C15 114.47(14) . . ? C13 C14 H14A 108.6 . . ? C15 C14 H14A 108.6 . . ? C13 C14 H14B 108.6 . . ? C15 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? C14 C15 C16 106.36(14) . . ? C14 C15 C25 111.87(16) . . ? C16 C15 C25 109.17(15) . . ? C14 C15 C23 110.19(15) . . ? C16 C15 C23 110.13(15) . . ? C25 C15 C23 109.08(16) . . ? C17 C16 C15 113.64(13) . . ? C17 C16 H16A 108.8 . . ? C15 C16 H16A 108.8 . . ? C17 C16 H16B 108.8 . . ? C15 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? O4 C17 C18 122.75(14) . . ? O4 C17 C16 119.73(14) . . ? C18 C17 C16 117.49(13) . . ? C13 C18 C17 117.28(14) . . ? C13 C18 C19 120.40(14) . . ? C17 C18 C19 122.29(13) . . ? C1 C19 C18 116.92(12) . . ? C1 C19 C11 107.38(13) . . ? C18 C19 C11 108.42(13) . . ? C1 C19 H19 107.9 . . ? C18 C19 H19 107.9 . . ? C11 C19 H19 107.9 . . ? C7 C20 H20A 109.5 . . ? C7 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C7 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C12 C21 H21A 109.5 . . ? C12 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C12 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C12 C22 H22A 109.5 . . ? C12 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C12 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C15 C23 H23A 109.5 . . ? C15 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C15 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C8 C24 H24A 109.5 . . ? C8 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C8 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C15 C25 H25A 109.5 . . ? C15 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C15 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C2 O1 C10 118.19(14) . . ? C8 O2 C9 120.02(13) . . ? C13 O5 C12 117.73(13) . . ? 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 C9 C1 C2 O1 175.00(14) . . . . ? C19 C1 C2 O1 1.4(2) . . . . ? C9 C1 C2 C3 -4.4(2) . . . . ? C19 C1 C2 C3 -177.99(15) . . . . ? O1 C2 C3 C4 -178.91(16) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C5 1.8(3) . . . . ? C3 C4 C5 C9 0.0(3) . . . . ? C3 C4 C5 C6 -179.54(16) . . . . ? C9 C5 C6 O3 -177.19(16) . . . . ? C4 C5 C6 O3 2.4(3) . . . . ? C9 C5 C6 C7 3.1(2) . . . . ? C4 C5 C6 C7 -177.32(15) . . . . ? O3 C6 C7 C8 -178.06(17) . . . . ? C5 C6 C7 C8 1.6(2) . . . . ? O3 C6 C7 C20 -0.3(3) . . . . ? C5 C6 C7 C20 179.37(16) . . . . ? C6 C7 C8 O2 -3.6(3) . . . . ? C20 C7 C8 O2 178.71(16) . . . . ? C6 C7 C8 C24 174.65(17) . . . . ? C20 C7 C8 C24 -3.0(3) . . . . ? C4 C5 C9 O2 174.27(14) . . . . ? C6 C5 C9 O2 -6.1(2) . . . . ? C4 C5 C9 C1 -4.3(2) . . . . ? C6 C5 C9 C1 175.32(14) . . . . ? C2 C1 C9 O2 -172.27(13) . . . . ? C19 C1 C9 O2 1.3(2) . . . . ? C2 C1 C9 C5 6.3(2) . . . . ? C19 C1 C9 C5 179.86(14) . . . . ? O1 C10 C11 C19 57.2(2) . . . . ? O1 C10 C11 C12 179.88(14) . . . . ? C10 C11 C12 O5 -60.00(19) . . . . ? C19 C11 C12 O5 61.78(18) . . . . ? C10 C11 C12 C22 -179.17(17) . . . . ? C19 C11 C12 C22 -57.4(2) . . . . ? C10 C11 C12 C21 55.3(2) . . . . ? C19 C11 C12 C21 177.11(15) . . . . ? C18 C13 C14 C15 17.5(3) . . . . ? O5 C13 C14 C15 -161.33(15) . . . . ? C13 C14 C15 C16 -46.3(2) . . . . ? C13 C14 C15 C25 72.9(2) . . . . ? C13 C14 C15 C23 -165.61(16) . . . . ? C14 C15 C16 C17 57.23(18) . . . . ? C25 C15 C16 C17 -63.64(19) . . . . ? C23 C15 C16 C17 176.63(15) . . . . ? C15 C16 C17 O4 142.88(15) . . . . ? C15 C16 C17 C18 -39.0(2) . . . . ? O5 C13 C18 C17 -176.77(15) . . . . ? C14 C13 C18 C17 4.6(2) . . . . ? O5 C13 C18 C19 1.4(3) . . . . ? C14 C13 C18 C19 -177.24(15) . . . . ? O4 C17 C18 C13 -175.67(15) . . . . ? C16 C17 C18 C13 6.3(2) . . . . ? O4 C17 C18 C19 6.2(2) . . . . ? C16 C17 C18 C19 -171.86(14) . . . . ? C2 C1 C19 C18 -94.44(18) . . . . ? C9 C1 C19 C18 92.34(18) . . . . ? C2 C1 C19 C11 27.59(19) . . . . ? C9 C1 C19 C11 -145.63(14) . . . . ? C13 C18 C19 C1 141.37(15) . . . . ? C17 C18 C19 C1 -40.5(2) . . . . ? C13 C18 C19 C11 19.9(2) . . . . ? C17 C18 C19 C11 -162.00(14) . . . . ? C10 C11 C19 C1 -53.78(18) . . . . ? C12 C11 C19 C1 -177.77(13) . . . . ? C10 C11 C19 C18 73.40(17) . . . . ? C12 C11 C19 C18 -50.60(17) . . . . ? C1 C2 O1 C10 -1.8(2) . . . . ? C3 C2 O1 C10 177.65(16) . . . . ? C11 C10 O1 C2 -28.3(2) . . . . ? C7 C8 O2 C9 0.7(2) . . . . ? C24 C8 O2 C9 -177.85(14) . . . . ? C5 C9 O2 C8 4.3(2) . . . . ? C1 C9 O2 C8 -177.05(13) . . . . ? C18 C13 O5 C12 9.7(3) . . . . ? C14 C13 O5 C12 -171.45(15) . . . . ? C22 C12 O5 C13 80.94(18) . . . . ? C21 C12 O5 C13 -161.32(16) . . . . ? C11 C12 O5 C13 -40.6(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.183 _refine_diff_density_min -0.119 _refine_diff_density_rms 0.030 data_af24m _database_code_depnum_ccdc_archive 'CCDC 848040' #TrackingRef '7564_web_deposit_cif_file_0_B.Sridhar_1318247199.af24mf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2,8,-Trimethyl-2a,3,10c,12,13,14-hexahydro-2H-1,4,10-trioxa-dibenzo[c.g] phenanthrene-7,11-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 O5' _chemical_formula_sum 'C22 H22 O5' _chemical_formula_weight 366.40 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 0.0016 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.4539(11) _cell_length_b 7.4613(5) _cell_length_c 16.2148(11) _cell_angle_alpha 90.00 _cell_angle_beta 106.214(1) _cell_angle_gamma 90.00 _cell_volume 1795.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 9849 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 27.92 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _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 'CCD Area Detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16576 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3161 _reflns_number_gt 2889 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0732P)^2^+0.7442P] 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 3161 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1329 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _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 1.09580(11) 0.5540(3) 0.13670(10) 0.0415(4) Uani 1 1 d . . . C2 C 1.00299(10) 0.4876(2) 0.11603(10) 0.0367(4) Uani 1 1 d . . . C3 C 0.98392(12) 0.3083(2) 0.13040(11) 0.0436(4) Uani 1 1 d . . . H3 H 1.0309 0.2306 0.1556 0.052 Uiso 1 1 calc R . . C4 C 0.89744(12) 0.2462(2) 0.10791(12) 0.0452(4) Uani 1 1 d . . . H4 H 0.8857 0.1264 0.1162 0.054 Uiso 1 1 calc R . . C5 C 0.82618(11) 0.3650(2) 0.07208(10) 0.0379(4) Uani 1 1 d . . . C6 C 0.66699(11) 0.3961(3) 0.00572(13) 0.0486(4) Uani 1 1 d . . . H6A H 0.6379 0.4408 0.0474 0.058 Uiso 1 1 calc R . . H6B H 0.6240 0.3206 -0.0344 0.058 Uiso 1 1 calc R . . C7 C 0.69058(10) 0.5540(2) -0.04295(10) 0.0400(4) Uani 1 1 d . . . H7 H 0.7160 0.5072 -0.0876 0.048 Uiso 1 1 calc R . . C8 C 0.60814(11) 0.6685(3) -0.08651(11) 0.0455(4) Uani 1 1 d . . . C9 C 0.62882(11) 0.8013(2) 0.05387(10) 0.0385(4) Uani 1 1 d . . . C10 C 0.57896(12) 0.9047(3) 0.10499(12) 0.0509(5) Uani 1 1 d . . . H10A H 0.5704 1.0268 0.0837 0.061 Uiso 1 1 calc R . . H10B H 0.5199 0.8515 0.0972 0.061 Uiso 1 1 calc R . . C11 C 0.62762(15) 0.9072(4) 0.19803(14) 0.0669(6) Uani 1 1 d . . . H11A H 0.6224 0.7907 0.2227 0.080 Uiso 1 1 calc R . . H11B H 0.5998 0.9949 0.2268 0.080 Uiso 1 1 calc R . . C12 C 0.72464(13) 0.9522(3) 0.21307(12) 0.0540(5) Uani 1 1 d . . . H12A H 0.7552 0.9353 0.2735 0.065 Uiso 1 1 calc R . . H12B H 0.7296 1.0779 0.1999 0.065 Uiso 1 1 calc R . . C13 C 0.77206(11) 0.8426(2) 0.16096(10) 0.0374(4) Uani 1 1 d . . . C14 C 0.71866(10) 0.7694(2) 0.07823(10) 0.0339(4) Uani 1 1 d . . . C15 C 0.76294(10) 0.6683(2) 0.01889(10) 0.0335(4) Uani 1 1 d . . . H15 H 0.7847 0.7569 -0.0153 0.040 Uiso 1 1 calc R . . C16 C 0.84046(10) 0.5445(2) 0.06034(9) 0.0335(4) Uani 1 1 d . . . C17 C 0.93081(10) 0.6006(2) 0.08040(10) 0.0336(3) Uani 1 1 d . . . C18 C 1.02968(11) 0.8387(2) 0.08660(11) 0.0419(4) Uani 1 1 d . . . H18 H 1.0372 0.9600 0.0775 0.050 Uiso 1 1 calc R . . C19 C 1.10411(11) 0.7447(3) 0.12253(11) 0.0432(4) Uani 1 1 d . . . C20 C 1.19491(13) 0.8335(3) 0.14564(14) 0.0616(6) Uani 1 1 d . . . H20A H 1.2288 0.7912 0.1081 0.092 Uiso 1 1 calc R . . H20B H 1.2267 0.8050 0.2040 0.092 Uiso 1 1 calc R . . H20C H 1.1874 0.9610 0.1396 0.092 Uiso 1 1 calc R . . C21 C 0.63265(14) 0.8251(3) -0.13555(13) 0.0630(6) Uani 1 1 d . . . H21A H 0.5787 0.8855 -0.1671 0.095 Uiso 1 1 calc R . . H21B H 0.6643 0.7815 -0.1747 0.095 Uiso 1 1 calc R . . H21C H 0.6705 0.9072 -0.0958 0.095 Uiso 1 1 calc R . . C22 C 0.53093(14) 0.5592(4) -0.14340(14) 0.0686(6) Uani 1 1 d . . . H22A H 0.5113 0.4717 -0.1091 0.103 Uiso 1 1 calc R . . H22B H 0.5511 0.4996 -0.1871 0.103 Uiso 1 1 calc R . . H22C H 0.4817 0.6375 -0.1698 0.103 Uiso 1 1 calc R . . O1 O 1.16145(8) 0.4556(2) 0.16401(9) 0.0606(4) Uani 1 1 d . . . O2 O 0.74280(8) 0.28880(17) 0.04950(9) 0.0506(3) Uani 1 1 d . . . O3 O 0.57085(7) 0.74392(18) -0.02035(7) 0.0458(3) Uani 1 1 d . . . O4 O 0.85302(8) 0.81992(19) 0.18741(8) 0.0512(3) Uani 1 1 d . . . O5 O 0.94426(7) 0.77504(15) 0.06207(7) 0.0402(3) 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 0.0338(8) 0.0574(11) 0.0326(8) -0.0003(7) 0.0080(7) 0.0063(8) C2 0.0345(8) 0.0421(9) 0.0339(8) -0.0005(7) 0.0101(6) 0.0051(7) C3 0.0436(9) 0.0417(9) 0.0456(9) 0.0054(7) 0.0125(8) 0.0129(7) C4 0.0507(10) 0.0341(9) 0.0524(10) 0.0054(7) 0.0169(8) 0.0028(7) C5 0.0373(9) 0.0390(9) 0.0395(9) -0.0008(7) 0.0143(7) -0.0028(7) C6 0.0346(9) 0.0467(10) 0.0629(11) -0.0068(8) 0.0110(8) -0.0070(7) C7 0.0327(8) 0.0493(10) 0.0372(8) -0.0078(7) 0.0084(7) -0.0003(7) C8 0.0345(9) 0.0642(12) 0.0353(8) -0.0062(8) 0.0056(7) 0.0027(8) C9 0.0350(8) 0.0424(9) 0.0369(8) 0.0019(7) 0.0081(7) 0.0029(7) C10 0.0432(10) 0.0587(12) 0.0524(10) -0.0047(9) 0.0156(8) 0.0108(8) C11 0.0628(13) 0.0858(16) 0.0557(12) -0.0103(11) 0.0226(10) 0.0142(12) C12 0.0569(11) 0.0571(11) 0.0462(10) -0.0136(9) 0.0114(9) 0.0031(9) C13 0.0397(9) 0.0351(8) 0.0362(8) 0.0019(6) 0.0088(7) -0.0024(7) C14 0.0340(8) 0.0336(8) 0.0339(8) 0.0021(6) 0.0089(6) 0.0012(6) C15 0.0296(8) 0.0366(8) 0.0340(8) 0.0020(6) 0.0081(6) -0.0003(6) C16 0.0321(8) 0.0371(8) 0.0320(7) -0.0003(6) 0.0100(6) 0.0018(6) C17 0.0340(8) 0.0352(8) 0.0323(7) 0.0003(6) 0.0106(6) 0.0015(6) C18 0.0397(9) 0.0440(9) 0.0432(9) -0.0021(7) 0.0135(7) -0.0084(7) C19 0.0361(9) 0.0570(11) 0.0363(8) -0.0063(8) 0.0100(7) -0.0057(8) C20 0.0420(11) 0.0767(15) 0.0647(13) -0.0120(11) 0.0126(9) -0.0148(10) C21 0.0510(11) 0.0885(16) 0.0479(11) 0.0197(11) 0.0110(9) 0.0134(11) C22 0.0449(11) 0.0924(17) 0.0571(12) -0.0196(12) -0.0045(9) 0.0032(11) O1 0.0361(7) 0.0753(10) 0.0657(8) 0.0107(7) 0.0064(6) 0.0137(7) O2 0.0407(7) 0.0426(7) 0.0676(8) 0.0052(6) 0.0134(6) -0.0075(5) O3 0.0305(6) 0.0637(8) 0.0404(6) -0.0053(6) 0.0054(5) 0.0062(5) O4 0.0381(7) 0.0651(9) 0.0452(7) -0.0107(6) 0.0029(5) -0.0030(6) O5 0.0337(6) 0.0372(6) 0.0485(7) 0.0055(5) 0.0096(5) -0.0013(5) _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 O1 1.230(2) . ? C1 C19 1.453(3) . ? C1 C2 1.465(2) . ? C2 C17 1.389(2) . ? C2 C3 1.403(2) . ? C3 C4 1.364(3) . ? C3 H3 0.9300 . ? C4 C5 1.406(2) . ? C4 H4 0.9300 . ? C5 O2 1.362(2) . ? C5 C16 1.379(2) . ? C6 O2 1.433(2) . ? C6 C7 1.518(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.533(2) . ? C7 C15 1.535(2) . ? C7 H7 0.9800 . ? C8 O3 1.465(2) . ? C8 C21 1.519(3) . ? C8 C22 1.525(3) . ? C9 O3 1.354(2) . ? C9 C14 1.354(2) . ? C9 C10 1.494(2) . ? C10 C11 1.486(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.489(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.505(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O4 1.216(2) . ? C13 C14 1.470(2) . ? C14 C15 1.527(2) . ? C15 C16 1.514(2) . ? C15 H15 0.9800 . ? C16 C17 1.406(2) . ? C17 O5 1.3641(19) . ? C18 C19 1.334(3) . ? C18 O5 1.3539(19) . ? C18 H18 0.9300 . ? C19 C20 1.502(2) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C19 122.74(16) . . ? O1 C1 C2 122.48(17) . . ? C19 C1 C2 114.78(15) . . ? C17 C2 C3 117.80(15) . . ? C17 C2 C1 120.73(15) . . ? C3 C2 C1 121.46(15) . . ? C4 C3 C2 120.97(16) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.49(16) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? O2 C5 C16 122.97(15) . . ? O2 C5 C4 114.90(15) . . ? C16 C5 C4 122.13(15) . . ? O2 C6 C7 114.17(14) . . ? O2 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? O2 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C6 C7 C8 112.51(14) . . ? C6 C7 C15 109.18(14) . . ? C8 C7 C15 110.57(14) . . ? C6 C7 H7 108.1 . . ? C8 C7 H7 108.1 . . ? C15 C7 H7 108.1 . . ? O3 C8 C21 107.13(16) . . ? O3 C8 C22 104.31(14) . . ? C21 C8 C22 111.22(17) . . ? O3 C8 C7 108.84(13) . . ? C21 C8 C7 111.91(15) . . ? C22 C8 C7 112.95(17) . . ? O3 C9 C14 125.04(15) . . ? O3 C9 C10 109.91(14) . . ? C14 C9 C10 125.05(15) . . ? C11 C10 C9 112.13(16) . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C10 C11 C12 111.73(18) . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C13 114.30(16) . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? O4 C13 C14 122.04(15) . . ? O4 C13 C12 119.47(15) . . ? C14 C13 C12 118.48(15) . . ? C9 C14 C13 118.02(15) . . ? C9 C14 C15 120.42(14) . . ? C13 C14 C15 121.50(13) . . ? C16 C15 C14 117.40(13) . . ? C16 C15 C7 107.01(13) . . ? C14 C15 C7 108.25(12) . . ? C16 C15 H15 107.9 . . ? C14 C15 H15 107.9 . . ? C7 C15 H15 107.9 . . ? C5 C16 C17 116.36(14) . . ? C5 C16 C15 121.12(14) . . ? C17 C16 C15 122.18(14) . . ? O5 C17 C2 121.10(14) . . ? O5 C17 C16 115.83(13) . . ? C2 C17 C16 123.07(15) . . ? C19 C18 O5 126.51(16) . . ? C19 C18 H18 116.7 . . ? O5 C18 H18 116.7 . . ? C18 C19 C1 118.72(16) . . ? C18 C19 C20 120.57(18) . . ? C1 C19 C20 120.69(17) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C8 C21 H21A 109.5 . . ? C8 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C8 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C8 C22 H22A 109.5 . . ? C8 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C8 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C5 O2 C6 118.78(13) . . ? C9 O3 C8 118.33(12) . . ? C18 O5 C17 117.78(13) . . ? 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 O1 C1 C2 C17 -176.04(16) . . . . ? C19 C1 C2 C17 4.0(2) . . . . ? O1 C1 C2 C3 3.2(3) . . . . ? C19 C1 C2 C3 -176.76(15) . . . . ? C17 C2 C3 C4 1.7(2) . . . . ? C1 C2 C3 C4 -177.50(16) . . . . ? C2 C3 C4 C5 -1.8(3) . . . . ? C3 C4 C5 O2 178.12(16) . . . . ? C3 C4 C5 C16 -1.4(3) . . . . ? O2 C6 C7 C8 -178.22(14) . . . . ? O2 C6 C7 C15 -55.07(19) . . . . ? C6 C7 C8 O3 62.26(19) . . . . ? C15 C7 C8 O3 -60.12(18) . . . . ? C6 C7 C8 C21 -179.52(16) . . . . ? C15 C7 C8 C21 58.10(19) . . . . ? C6 C7 C8 C22 -53.1(2) . . . . ? C15 C7 C8 C22 -175.46(15) . . . . ? O3 C9 C10 C11 156.74(18) . . . . ? C14 C9 C10 C11 -23.2(3) . . . . ? C9 C10 C11 C12 47.3(3) . . . . ? C10 C11 C12 C13 -50.2(3) . . . . ? C11 C12 C13 O4 -154.16(19) . . . . ? C11 C12 C13 C14 27.2(3) . . . . ? O3 C9 C14 C13 179.67(15) . . . . ? C10 C9 C14 C13 -0.4(3) . . . . ? O3 C9 C14 C15 2.6(3) . . . . ? C10 C9 C14 C15 -177.48(16) . . . . ? O4 C13 C14 C9 179.99(16) . . . . ? C12 C13 C14 C9 -1.4(2) . . . . ? O4 C13 C14 C15 -3.0(2) . . . . ? C12 C13 C14 C15 175.60(15) . . . . ? C9 C14 C15 C16 -144.52(15) . . . . ? C13 C14 C15 C16 38.5(2) . . . . ? C9 C14 C15 C7 -23.3(2) . . . . ? C13 C14 C15 C7 159.75(14) . . . . ? C6 C7 C15 C16 54.40(16) . . . . ? C8 C7 C15 C16 178.71(13) . . . . ? C6 C7 C15 C14 -73.02(16) . . . . ? C8 C7 C15 C14 51.28(17) . . . . ? O2 C5 C16 C17 -175.05(14) . . . . ? C4 C5 C16 C17 4.4(2) . . . . ? O2 C5 C16 C15 -1.5(2) . . . . ? C4 C5 C16 C15 177.93(15) . . . . ? C14 C15 C16 C5 92.85(18) . . . . ? C7 C15 C16 C5 -28.99(19) . . . . ? C14 C15 C16 C17 -94.03(18) . . . . ? C7 C15 C16 C17 144.13(14) . . . . ? C3 C2 C17 O5 -177.89(14) . . . . ? C1 C2 C17 O5 1.3(2) . . . . ? C3 C2 C17 C16 1.6(2) . . . . ? C1 C2 C17 C16 -179.18(14) . . . . ? C5 C16 C17 O5 174.94(13) . . . . ? C15 C16 C17 O5 1.5(2) . . . . ? C5 C16 C17 C2 -4.6(2) . . . . ? C15 C16 C17 C2 -177.99(14) . . . . ? O5 C18 C19 C1 1.0(3) . . . . ? O5 C18 C19 C20 179.37(16) . . . . ? O1 C1 C19 C18 174.94(17) . . . . ? C2 C1 C19 C18 -5.1(2) . . . . ? O1 C1 C19 C20 -3.4(3) . . . . ? C2 C1 C19 C20 176.49(15) . . . . ? C16 C5 O2 C6 4.8(2) . . . . ? C4 C5 O2 C6 -174.66(15) . . . . ? C7 C6 O2 C5 24.4(2) . . . . ? C14 C9 O3 C8 -11.1(3) . . . . ? C10 C9 O3 C8 169.02(15) . . . . ? C21 C8 O3 C9 -81.97(18) . . . . ? C22 C8 O3 C9 160.02(16) . . . . ? C7 C8 O3 C9 39.2(2) . . . . ? C19 C18 O5 C17 4.6(2) . . . . ? C2 C17 O5 C18 -5.7(2) . . . . ? C16 C17 O5 C18 174.83(13) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.778 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.047