Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global # SUBMISSION DETAILS _publ_contact_author ; Prof. Dr. Edwin Weber Institut f\"ur Organische Chemie TU Bergakademie Freiberg Leipziger Str. 29 D-09596 Freiberg/Sachsen Germany ; _publ_contact_author_email weber@tu-freiberg.de _publ_contact_author_fax '49(03731)393170' _publ_contact_author_phone '49(03731)392386' _publ-contact_letter ; Please consider this CIF submission for publication in J. Chem. Soc., Perkin Trans. 2. ; _publ_requested_journal 'J. Chem. Soc., Perkin Trans. 2' _journal_coden_Cambridge 188 # TITLE AND AUTHOR LIST _publ_section_title ; 4,4'-(Fluoren-9,9'-diyl)diphenol: A new versatile building block for clathrate type and macrocyclic host-guest inclusion ; loop_ _publ_author_name _publ_author_address 'Weber, Edwin' ;Institut f\"ur Organische Chemie TU Bergakademie Freiberg Leipziger Str. 29 D-09596 Freiberg/Sachsen Germany ; 'Apel, Sylke' ;Institut f\"ur Organische Chemie TU Bergakademie Freiberg Leipziger Str. 29 D-09596 Freiberg/Sachsen Germany ; 'Nitsche, Silke' ;Institut f\"ur Organische Chemie TU Bergakademie Freiberg Leipziger Str. 29 D-09596 Freiberg/Sachsen Germany ; 'Beketov, Kayrat' ;Institute of Bioorganic Chemistry of Uzbekistan Academy of Sciences H. Abdulleav Str. 83 700 143 Tashkent Uzbekistan ; 'Seichter, Wilhelm' ;Institut f\"ur Organische Chemie TU Bergakademie Freiberg Leipziger Str. 29 D-09596 Freiberg/Sachsen Germany ; # TEXT _publ_section_abstract ; 4,4'-(Fluoren-9,9'-diyl)diphenol (1) is demonstrated to be both an effective clathrate host by itself and a useful construction element to form a rigid macrocyclic host compound 2. The X-ray crystal structures of 1 and of its inclusion compounds with acetonitrile (1:1) and ethanol (1:2) as well as the inclusion compound of 2 with dimethyl sulphoxide (1:4) and the mixed-guest inclusion compounds of 2 with 2-picoline, 3-picoline or 4-picoline and acetone (2:2:1) are reported. Inclusion compounds of 1 with acetonitrile and ethanol are studied by thermal analysis. ; _audit_creation_method SHELXL ############################################################################ data_etoh2 _database_code_CSD 150561 # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C29 H25.50 O4' _chemical_formula_weight 437.99 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.281(3) _cell_length_b 17.888(3) _cell_length_c 23.950(3) _cell_angle_alpha 90.00(3) _cell_angle_beta 90.00(3) _cell_angle_gamma 90.00(3) _cell_volume 4833.0(16) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 22.403 _cell_measurement_theta_max 28.258 _exptl_crystal_description ? _exptl_crystal_colour colourless _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 1.204 _exptl_crystal_density_method ? _exptl_crystal_F_000 1852 _exptl_absorpt_coefficient_mu 0.636 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device CAD4 _diffrn_measurement_method 'omega-2theta scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 250 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% ? _diffrn_reflns_number 5510 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 75.11 _reflns_number_total 5510 _reflns_number_observed 3579 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Enraf-Nonius' _computing_cell_refinement 'Enraf-Nonius' _computing_data_reduction 'Helena' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON' _computing_publication_material 'PLATON' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 591 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1031P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(50) _refine_ls_number_reflns 4919 _refine_ls_number_parameters 604 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.1115 _refine_ls_R_factor_obs 0.0638 _refine_ls_wR_factor_all 0.1907 _refine_ls_wR_factor_obs 0.1612 _refine_ls_goodness_of_fit_all 1.048 _refine_ls_goodness_of_fit_obs 1.160 _refine_ls_restrained_S_all 1.075 _refine_ls_restrained_S_obs 1.161 _refine_ls_shift/esd_max 0.010 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.9834(3) -0.0601(2) -0.1561(2) 0.0708(11) Uani 1 d . . H1O H 0.9675(3) -0.0518(2) -0.1890(2) 0.106 Uiso 1 calc R . O2 O 0.4917(4) -0.0884(2) 0.18596(13) 0.0664(11) Uani 1 d . . H2O H 0.5070(4) -0.0442(2) 0.19155(13) 0.100 Uiso 1 calc R . C1 C 0.5950(4) -0.2565(2) -0.0474(2) 0.0370(10) Uani 1 d . . C2 C 0.6855(5) -0.3027(2) -0.0322(2) 0.0478(12) Uani 1 d . . H2 H 0.7517(5) -0.2835(2) -0.0140(2) 0.057 Uiso 1 calc R . C3 C 0.6782(6) -0.3795(3) -0.0440(2) 0.065(2) Uani 1 d . . H3 H 0.7397(6) -0.4115(3) -0.0339(2) 0.077 Uiso 1 calc R . C4 C 0.5782(6) -0.4073(3) -0.0710(2) 0.068(2) Uani 1 d . . H4 H 0.5732(6) -0.4582(3) -0.0784(2) 0.082 Uiso 1 calc R . C5 C 0.4876(5) -0.3617(3) -0.0867(2) 0.0536(13) Uani 1 d . . H5 H 0.4218(5) -0.3810(3) -0.1050(2) 0.064 Uiso 1 calc R . C6 C 0.4951(5) -0.2860(2) -0.0748(2) 0.0423(12) Uani 1 d . . C7 C 0.4133(4) -0.2247(3) -0.0864(2) 0.0420(11) Uani 1 d . . C8 C 0.2996(5) -0.2257(3) -0.1110(2) 0.0566(14) Uani 1 d . . H8 H 0.2661(5) -0.2703(3) -0.1234(2) 0.068 Uiso 1 calc R . C9 C 0.2399(5) -0.1593(3) -0.1162(2) 0.063(2) Uani 1 d . . H9 H 0.1650(5) -0.1591(3) -0.1324(2) 0.075 Uiso 1 calc R . C10 C 0.2880(5) -0.0925(4) -0.0980(2) 0.062(2) Uani 1 d . . H10 H 0.2463(5) -0.0481(4) -0.1026(2) 0.075 Uiso 1 calc R . C11 C 0.3998(5) -0.0920(3) -0.0725(2) 0.0499(13) Uani 1 d . . H11 H 0.4319(5) -0.0474(3) -0.0596(2) 0.060 Uiso 1 calc R . C12 C 0.4617(4) -0.1573(2) -0.0667(2) 0.0393(11) Uani 1 d . . C13 C 0.5827(4) -0.1722(2) -0.0392(2) 0.0353(10) Uani 1 d . . C14 C 0.6861(4) -0.1342(2) -0.0688(2) 0.0374(11) Uani 1 d . . C15 C 0.6776(5) -0.1141(3) -0.1249(2) 0.0467(12) Uani 1 d . . H15 H 0.6048(5) -0.1177(3) -0.1429(2) 0.056 Uiso 1 calc R . C16 C 0.7757(5) -0.0887(3) -0.1545(2) 0.0554(14) Uani 1 d . . H16 H 0.7683(5) -0.0761(3) -0.1920(2) 0.067 Uiso 1 calc R . C17 C 0.8828(5) -0.0824(3) -0.1286(2) 0.0494(12) Uani 1 d . . C18 C 0.8924(5) -0.0998(3) -0.0729(2) 0.0506(13) Uani 1 d . . H18 H 0.9646(5) -0.0934(3) -0.0547(2) 0.061 Uiso 1 calc R . C19 C 0.7967(4) -0.1266(3) -0.0436(2) 0.0439(11) Uani 1 d . . H19 H 0.8059(4) -0.1399(3) -0.0063(2) 0.053 Uiso 1 calc R . C20 C 0.5701(4) -0.1504(2) 0.0228(2) 0.0349(10) Uani 1 d . . C21 C 0.5223(5) -0.2004(3) 0.0610(2) 0.0453(12) Uani 1 d . . H21 H 0.5058(5) -0.2490(3) 0.0497(2) 0.054 Uiso 1 calc R . C22 C 0.4985(5) -0.1795(3) 0.1155(2) 0.0530(13) Uani 1 d . . H22 H 0.4675(5) -0.2139(3) 0.1406(2) 0.064 Uiso 1 calc R . C23 C 0.5213(5) -0.1068(3) 0.1322(2) 0.0472(12) Uani 1 d . . C24 C 0.5681(5) -0.0563(3) 0.0953(2) 0.0504(13) Uani 1 d . . H24 H 0.5830(5) -0.0074(3) 0.1065(2) 0.061 Uiso 1 calc R . C25 C 0.5929(5) -0.0786(2) 0.0415(2) 0.0443(12) Uani 1 d . . H25 H 0.6261(5) -0.0442(2) 0.0169(2) 0.053 Uiso 1 calc R . O1A O 0.7564(4) 0.0821(2) 0.17902(13) 0.0622(10) Uani 1 d . . H1AO H 0.7784(4) 0.0387(2) 0.18274(13) 0.093 Uiso 1 calc R . O2A O 1.2421(3) 0.0857(2) -0.16443(15) 0.0632(10) Uani 1 d . . H2AO H 1.2279(3) 0.0846(2) -0.19799(15) 0.095 Uiso 1 calc R . C1A C 0.8436(4) 0.2696(2) -0.0464(2) 0.0356(10) Uani 1 d . . C2A C 0.9344(5) 0.3153(3) -0.0282(2) 0.0485(12) Uani 1 d . . H2A H 1.0014(5) 0.2952(3) -0.0112(2) 0.058 Uiso 1 calc R . C3A C 0.9235(6) 0.3918(3) -0.0358(2) 0.0581(15) Uani 1 d . . H3A H 0.9838(6) 0.4232(3) -0.0235(2) 0.070 Uiso 1 calc R . C4A C 0.8259(6) 0.4219(3) -0.0610(2) 0.064(2) Uani 1 d . . H4A H 0.8206(6) 0.4734(3) -0.0657(2) 0.077 Uiso 1 calc R . C5A C 0.7353(5) 0.3765(3) -0.0794(2) 0.0558(14) Uani 1 d . . H5A H 0.6687(5) 0.3969(3) -0.0964(2) 0.067 Uiso 1 calc R . C6A C 0.7451(5) 0.2996(2) -0.0721(2) 0.0433(12) Uani 1 d . . C7A C 0.6651(5) 0.2390(3) -0.0875(2) 0.0451(12) Uani 1 d . . C8A C 0.5537(5) 0.2396(4) -0.1116(2) 0.0602(15) Uani 1 d . . H8A H 0.5171(5) 0.2844(4) -0.1209(2) 0.072 Uiso 1 calc R . C9A C 0.4979(6) 0.1724(4) -0.1215(2) 0.072(2) Uani 1 d . . H9A H 0.4228(6) 0.1722(4) -0.1375(2) 0.086 Uiso 1 calc R . C10A C 0.5508(5) 0.1056(4) -0.1081(2) 0.064(2) Uani 1 d . . H10A H 0.5114(5) 0.0610(4) -0.1155(2) 0.076 Uiso 1 calc R . C11A C 0.6610(5) 0.1039(3) -0.0842(2) 0.0506(13) Uani 1 d . . H11A H 0.6973(5) 0.0586(3) -0.0758(2) 0.061 Uiso 1 calc R . C12A C 0.7168(4) 0.1703(2) -0.0728(2) 0.0401(11) Uani 1 d . . C13A C 0.8368(4) 0.1840(2) -0.0435(2) 0.0352(10) Uani 1 d . . C14A C 0.8226(4) 0.1565(2) 0.0166(2) 0.0358(10) Uani 1 d . . C15A C 0.8508(5) 0.0837(3) 0.0324(2) 0.0486(12) Uani 1 d . . H15A H 0.8841(5) 0.0514(3) 0.0063(2) 0.058 Uiso 1 calc R . C16A C 0.8303(5) 0.0585(3) 0.0860(2) 0.0545(14) Uani 1 d . . H16A H 0.8511(5) 0.0100(3) 0.0959(2) 0.065 Uiso 1 calc R . C17A C 0.7786(5) 0.1055(3) 0.1251(2) 0.0466(12) Uani 1 d . . C18A C 0.7482(5) 0.1769(2) 0.1100(2) 0.0479(12) Uani 1 d . . H18A H 0.7122(5) 0.2085(2) 0.1357(2) 0.057 Uiso 1 calc R . C19A C 0.7711(5) 0.2016(2) 0.0569(2) 0.0441(12) Uani 1 d . . H19A H 0.7513(5) 0.2505(2) 0.0475(2) 0.053 Uiso 1 calc R . C20A C 0.9417(4) 0.1510(2) -0.0750(2) 0.0375(10) Uani 1 d . . C21A C 0.9384(5) 0.1445(3) -0.1326(2) 0.0487(13) Uani 1 d . . H21A H 0.8682(5) 0.1552(3) -0.1513(2) 0.058 Uiso 1 calc R . C22A C 1.0372(5) 0.1225(3) -0.1632(2) 0.0515(13) Uani 1 d . . H22A H 1.0320(5) 0.1176(3) -0.2018(2) 0.062 Uiso 1 calc R . C23A C 1.1434(4) 0.1079(3) -0.1362(2) 0.0432(11) Uani 1 d . . C24A C 1.1490(5) 0.1132(3) -0.0790(2) 0.0455(12) Uani 1 d . . H24A H 1.2191(5) 0.1021(3) -0.0603(2) 0.055 Uiso 1 calc R . C25A C 1.0494(5) 0.1353(2) -0.0495(2) 0.0433(12) Uani 1 d . . H25A H 1.0549(5) 0.1397(2) -0.0109(2) 0.052 Uiso 1 calc R . O1G1 O 0.5370(4) 0.0553(2) 0.2213(2) 0.0696(11) Uani 1 d D . C1G1 C 0.4427(10) 0.1041(7) 0.2024(5) 0.153(5) Uani 1 d D . H1G1 H 0.4449(10) 0.1069(7) 0.1620(5) 0.184 Uiso 1 calc R . H1G2 H 0.3671(10) 0.0824(7) 0.2130(5) 0.184 Uiso 1 calc R . C2G1 C 0.4496(12) 0.1761(6) 0.2241(6) 0.194(6) Uani 1 d D . H2G1 H 0.3850(12) 0.2055(6) 0.2100(6) 0.291 Uiso 1 calc R . H2G2 H 0.5234(12) 0.1985(6) 0.2131(6) 0.291 Uiso 1 calc R . H2G3 H 0.4452(12) 0.1740(6) 0.2641(6) 0.291 Uiso 1 calc R . O1G2 O 0.8609(5) -0.0438(3) 0.2040(2) 0.105(2) Uani 1 d D . C1G2 C 0.8124(13) -0.0878(5) 0.2497(3) 0.158(5) Uani 1 d D . H1G3 H 0.8588(13) -0.0771(5) 0.2828(3) 0.190 Uiso 1 calc R . H1G4 H 0.7325(13) -0.0701(5) 0.2567(3) 0.190 Uiso 1 calc R . C2G2 C 0.8077(13) -0.1614(5) 0.2437(4) 0.170(5) Uani 1 d D . H2G4 H 0.7747(13) -0.1833(5) 0.2768(4) 0.255 Uiso 1 calc R . H2G5 H 0.8862(13) -0.1805(5) 0.2378(4) 0.255 Uiso 1 calc R . H2G6 H 0.7587(13) -0.1736(5) 0.2122(4) 0.255 Uiso 1 calc R . O1G3 O 1.0883(7) -0.0017(4) 0.2095(3) 0.161(3) Uani 1 d D . C1G3 C 1.1057(12) 0.0470(7) 0.2583(5) 0.173(6) Uani 1 d D . H1G5 H 1.0592(12) 0.0284(7) 0.2894(5) 0.207 Uiso 1 calc R . H1G6 H 1.1885(12) 0.0464(7) 0.2691(5) 0.207 Uiso 1 calc R . C2G3 C 1.0727(11) 0.1176(6) 0.2464(5) 0.170(5) Uani 1 d D . H2G7 H 1.0839(11) 0.1485(6) 0.2787(5) 0.256 Uiso 1 calc R . H2G8 H 0.9906(11) 0.1182(6) 0.2358(5) 0.256 Uiso 1 calc R . H2G9 H 1.1200(11) 0.1363(6) 0.2162(5) 0.256 Uiso 1 calc R . O1G4 O 1.2413(4) 0.1131(3) -0.2802(2) 0.0831(13) Uani 1 d D . C1G4 C 1.2828(11) 0.1858(6) -0.2995(4) 0.128(4) Uani 1 d D . C2GA C 1.2683(33) 0.2374(11) -0.2624(8) 0.139(10) Uani 0.50 d PD . C2GB C 1.3688(20) 0.2207(13) -0.2726(10) 0.126(8) Uani 0.50 d PD . 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 0.041(2) 0.088(3) 0.084(3) 0.017(2) 0.013(2) -0.009(2) O2 0.077(3) 0.077(2) 0.045(2) -0.017(2) 0.013(2) -0.009(2) C1 0.041(3) 0.035(2) 0.035(2) -0.003(2) 0.000(2) -0.001(2) C2 0.051(3) 0.044(2) 0.049(2) -0.005(2) -0.008(3) 0.011(2) C3 0.087(5) 0.045(3) 0.061(3) -0.006(2) -0.009(4) 0.018(3) C4 0.103(5) 0.036(2) 0.066(3) -0.008(2) -0.004(4) 0.005(3) C5 0.052(4) 0.046(3) 0.063(3) -0.012(2) -0.001(3) -0.005(3) C6 0.052(3) 0.038(2) 0.037(2) -0.001(2) 0.004(2) -0.001(2) C7 0.036(3) 0.051(2) 0.039(2) -0.002(2) 0.001(2) -0.005(2) C8 0.042(3) 0.077(3) 0.051(3) -0.008(3) -0.008(3) -0.009(3) C9 0.036(3) 0.092(4) 0.060(3) 0.013(3) -0.002(3) 0.006(3) C10 0.044(3) 0.078(4) 0.065(3) 0.016(3) 0.003(3) 0.020(3) C11 0.047(3) 0.047(3) 0.056(3) 0.005(2) 0.003(3) 0.011(3) C12 0.032(3) 0.048(2) 0.038(2) 0.004(2) 0.003(2) 0.003(2) C13 0.032(3) 0.034(2) 0.039(2) -0.001(2) -0.001(2) 0.003(2) C14 0.038(3) 0.037(2) 0.037(2) -0.004(2) 0.000(2) -0.003(2) C15 0.040(3) 0.057(3) 0.043(2) 0.004(2) -0.005(2) -0.003(3) C16 0.046(3) 0.072(3) 0.048(3) 0.015(2) 0.000(3) -0.001(3) C17 0.037(3) 0.048(3) 0.064(3) 0.005(2) 0.011(3) -0.001(2) C18 0.035(3) 0.059(3) 0.058(3) -0.009(2) -0.002(3) 0.003(3) C19 0.033(3) 0.054(3) 0.044(2) 0.000(2) -0.008(2) -0.002(2) C20 0.033(3) 0.033(2) 0.039(2) -0.002(2) 0.000(2) 0.005(2) C21 0.045(3) 0.049(3) 0.041(2) 0.000(2) 0.004(2) 0.001(2) C22 0.058(4) 0.054(3) 0.047(3) 0.007(2) 0.016(3) -0.002(3) C23 0.047(3) 0.058(3) 0.036(2) -0.008(2) 0.004(2) 0.001(3) C24 0.053(3) 0.046(2) 0.052(3) -0.010(2) 0.000(3) -0.004(3) C25 0.051(3) 0.044(2) 0.038(2) -0.001(2) 0.007(2) -0.005(2) O1A 0.070(3) 0.067(2) 0.049(2) 0.018(2) 0.015(2) 0.012(2) O2A 0.044(2) 0.086(3) 0.060(2) -0.005(2) 0.008(2) 0.015(2) C1A 0.035(3) 0.036(2) 0.036(2) 0.003(2) 0.002(2) 0.004(2) C2A 0.055(3) 0.048(3) 0.043(2) 0.005(2) -0.004(3) -0.004(3) C3A 0.077(4) 0.046(3) 0.052(3) -0.001(2) 0.006(3) -0.015(3) C4A 0.084(5) 0.036(2) 0.072(3) 0.005(2) 0.019(4) 0.000(3) C5A 0.055(4) 0.055(3) 0.057(3) 0.014(2) 0.011(3) 0.018(3) C6A 0.042(3) 0.049(2) 0.039(2) 0.008(2) 0.010(2) 0.010(2) C7A 0.034(3) 0.062(3) 0.039(2) 0.004(2) 0.001(2) 0.005(3) C8A 0.042(3) 0.088(4) 0.050(3) 0.015(3) 0.002(3) 0.008(3) C9A 0.048(4) 0.114(5) 0.052(3) 0.009(3) -0.009(3) -0.020(4) C10A 0.056(4) 0.084(4) 0.050(3) -0.001(3) -0.010(3) -0.032(4) C11A 0.051(3) 0.057(3) 0.044(2) -0.005(2) 0.003(3) -0.010(3) C12A 0.039(3) 0.047(2) 0.034(2) -0.001(2) 0.003(2) -0.001(2) C13A 0.033(3) 0.034(2) 0.038(2) -0.001(2) -0.003(2) 0.003(2) C14A 0.032(3) 0.037(2) 0.039(2) 0.002(2) -0.001(2) -0.004(2) C15A 0.058(3) 0.040(2) 0.048(3) -0.001(2) 0.010(3) 0.009(3) C16A 0.064(4) 0.047(3) 0.052(3) 0.009(2) 0.013(3) 0.010(3) C17A 0.047(3) 0.051(3) 0.042(2) 0.011(2) 0.003(2) 0.001(3) C18A 0.052(3) 0.044(2) 0.048(2) -0.003(2) 0.009(3) 0.003(3) C19A 0.054(3) 0.034(2) 0.045(2) 0.001(2) 0.005(3) 0.005(2) C20A 0.036(3) 0.037(2) 0.039(2) -0.001(2) -0.001(2) -0.003(2) C21A 0.043(3) 0.062(3) 0.041(2) 0.001(2) -0.002(2) 0.008(3) C22A 0.046(3) 0.068(3) 0.041(2) -0.006(2) 0.000(3) 0.005(3) C23A 0.032(3) 0.046(2) 0.052(3) -0.008(2) 0.000(2) 0.001(2) C24A 0.033(3) 0.053(3) 0.050(3) -0.002(2) -0.004(2) 0.005(2) C25A 0.046(3) 0.045(2) 0.039(2) -0.003(2) -0.006(2) 0.006(2) O1G1 0.065(3) 0.084(3) 0.060(2) -0.022(2) -0.003(2) 0.001(2) C1G1 0.121(9) 0.187(12) 0.150(9) -0.026(8) -0.062(7) 0.066(9) C2G1 0.202(14) 0.111(7) 0.270(16) 0.056(9) 0.042(13) 0.064(10) O1G2 0.141(5) 0.098(3) 0.077(3) 0.029(3) -0.001(3) 0.034(4) C1G2 0.286(17) 0.109(7) 0.080(5) 0.030(5) 0.022(8) 0.060(9) C2G2 0.273(16) 0.122(8) 0.114(7) -0.013(6) 0.033(10) -0.030(10) O1G3 0.159(7) 0.179(7) 0.145(6) -0.035(5) -0.026(5) 0.066(6) C1G3 0.217(15) 0.164(10) 0.137(9) -0.013(8) -0.058(9) 0.092(11) C2G3 0.166(11) 0.157(10) 0.189(12) 0.008(9) -0.066(10) 0.011(10) O1G4 0.065(3) 0.112(3) 0.072(3) 0.004(2) -0.007(3) -0.009(3) C1G4 0.138(9) 0.146(8) 0.102(6) 0.018(6) -0.012(6) -0.070(8) C2GA 0.231(31) 0.091(12) 0.095(12) -0.015(10) 0.023(19) 0.020(18) C2GB 0.122(17) 0.129(17) 0.127(16) 0.052(13) -0.038(16) -0.057(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C17 1.372(6) . ? O2 C23 1.371(5) . ? C1 C2 1.363(6) . ? C1 C6 1.406(7) . ? C1 C13 1.527(6) . ? C2 C3 1.405(7) . ? C3 C4 1.392(9) . ? C4 C5 1.360(8) . ? C5 C6 1.387(6) . ? C6 C7 1.460(7) . ? C7 C12 1.404(6) . ? C7 C8 1.412(7) . ? C8 C9 1.372(8) . ? C9 C10 1.382(8) . ? C10 C11 1.400(7) . ? C11 C12 1.368(6) . ? C12 C13 1.540(6) . ? C13 C14 1.524(6) . ? C13 C20 1.541(5) . ? C14 C15 1.395(6) . ? C14 C19 1.393(7) . ? C15 C16 1.391(7) . ? C16 C17 1.363(7) . ? C17 C18 1.375(7) . ? C18 C19 1.374(7) . ? C20 C25 1.386(6) . ? C20 C21 1.388(6) . ? C21 C22 1.384(6) . ? C22 C23 1.384(7) . ? C23 C24 1.369(7) . ? C24 C25 1.378(6) . ? O1A C17A 1.379(5) . ? O2A C23A 1.362(6) . ? C1A C2A 1.382(7) . ? C1A C6A 1.379(7) . ? C1A C13A 1.534(5) . ? C2A C3A 1.385(7) . ? C3A C4A 1.366(8) . ? C4A C5A 1.378(8) . ? C5A C6A 1.391(6) . ? C6A C7A 1.457(7) . ? C7A C8A 1.383(8) . ? C7A C12A 1.405(6) . ? C8A C9A 1.377(8) . ? C9A C10A 1.373(9) . ? C10A C11A 1.369(8) . ? C11A C12A 1.373(7) . ? C12A C13A 1.544(7) . ? C13A C20A 1.524(6) . ? C13A C14A 1.530(6) . ? C14A C19A 1.386(6) . ? C14A C15A 1.393(6) . ? C15A C16A 1.381(6) . ? C16A C17A 1.386(7) . ? C17A C18A 1.372(6) . ? C18A C19A 1.371(6) . ? C20A C21A 1.384(6) . ? C20A C25A 1.389(7) . ? C21A C22A 1.391(7) . ? C22A C23A 1.387(7) . ? C23A C24A 1.374(6) . ? C24A C25A 1.385(7) . ? O1G1 C1G1 1.449(9) . ? C1G1 C2G1 1.390(12) . ? O1G2 C1G2 1.453(9) . ? C1G2 C2G2 1.325(10) . ? O1G3 C1G3 1.470(11) . ? C1G3 C2G3 1.346(12) . ? O1G4 C1G4 1.457(9) . ? C1G4 C2GA 1.29(2) . ? C1G4 C2GB 1.32(2) . ? C2GA C2GB 1.20(3) . ? 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 C6 119.8(4) . . ? C2 C1 C13 129.2(4) . . ? C6 C1 C13 111.0(4) . . ? C1 C2 C3 119.7(5) . . ? C4 C3 C2 119.3(6) . . ? C5 C4 C3 121.6(5) . . ? C4 C5 C6 118.9(5) . . ? C5 C6 C1 120.7(5) . . ? C5 C6 C7 131.0(5) . . ? C1 C6 C7 108.3(4) . . ? C12 C7 C8 120.3(5) . . ? C12 C7 C6 109.5(4) . . ? C8 C7 C6 130.1(5) . . ? C9 C8 C7 118.1(5) . . ? C8 C9 C10 121.8(5) . . ? C9 C10 C11 119.8(5) . . ? C12 C11 C10 119.9(5) . . ? C11 C12 C7 120.0(5) . . ? C11 C12 C13 130.1(4) . . ? C7 C12 C13 109.9(4) . . ? C14 C13 C1 108.1(4) . . ? C14 C13 C12 113.7(3) . . ? C1 C13 C12 101.2(4) . . ? C14 C13 C20 114.0(4) . . ? C1 C13 C20 112.5(3) . . ? C12 C13 C20 106.7(4) . . ? C15 C14 C19 117.0(4) . . ? C15 C14 C13 120.7(4) . . ? C19 C14 C13 121.8(4) . . ? C16 C15 C14 121.4(5) . . ? C17 C16 C15 120.0(4) . . ? C16 C17 O1 122.5(5) . . ? C16 C17 C18 119.6(5) . . ? O1 C17 C18 117.9(5) . . ? C17 C18 C19 120.9(5) . . ? C18 C19 C14 121.1(4) . . ? C25 C20 C21 117.2(4) . . ? C25 C20 C13 121.8(4) . . ? C21 C20 C13 120.6(4) . . ? C22 C21 C20 121.5(4) . . ? C23 C22 C21 119.3(5) . . ? C24 C23 O2 122.8(4) . . ? C24 C23 C22 120.3(4) . . ? O2 C23 C22 116.8(4) . . ? C23 C24 C25 119.4(4) . . ? C24 C25 C20 122.2(4) . . ? C2A C1A C6A 120.5(4) . . ? C2A C1A C13A 127.9(4) . . ? C6A C1A C13A 111.6(4) . . ? C1A C2A C3A 118.5(5) . . ? C4A C3A C2A 121.3(6) . . ? C3A C4A C5A 120.5(5) . . ? C4A C5A C6A 118.9(5) . . ? C1A C6A C5A 120.3(5) . . ? C1A C6A C7A 108.8(4) . . ? C5A C6A C7A 130.9(5) . . ? C8A C7A C12A 119.2(5) . . ? C8A C7A C6A 131.6(5) . . ? C12A C7A C6A 109.3(4) . . ? C9A C8A C7A 118.7(6) . . ? C10A C9A C8A 121.4(6) . . ? C11A C10A C9A 120.7(6) . . ? C12A C11A C10A 118.7(5) . . ? C11A C12A C7A 121.2(5) . . ? C11A C12A C13A 129.0(4) . . ? C7A C12A C13A 109.8(4) . . ? C20A C13A C14A 115.0(4) . . ? C20A C13A C1A 109.0(4) . . ? C14A C13A C1A 111.7(3) . . ? C20A C13A C12A 113.2(3) . . ? C14A C13A C12A 106.5(4) . . ? C1A C13A C12A 100.5(4) . . ? C19A C14A C15A 116.9(4) . . ? C19A C14A C13A 120.7(4) . . ? C15A C14A C13A 122.2(4) . . ? C16A C15A C14A 121.2(4) . . ? C15A C16A C17A 120.1(4) . . ? C18A C17A O1A 119.0(4) . . ? C18A C17A C16A 119.4(4) . . ? O1A C17A C16A 121.7(4) . . ? C17A C18A C19A 119.9(4) . . ? C18A C19A C14A 122.5(4) . . ? C21A C20A C25A 116.4(5) . . ? C21A C20A C13A 120.4(4) . . ? C25A C20A C13A 122.7(4) . . ? C20A C21A C22A 121.8(5) . . ? C23A C22A C21A 120.0(4) . . ? O2A C23A C24A 118.5(5) . . ? O2A C23A C22A 122.0(4) . . ? C24A C23A C22A 119.5(5) . . ? C23A C24A C25A 119.4(5) . . ? C24A C25A C20A 122.9(4) . . ? C2G1 C1G1 O1G1 113.6(9) . . ? C2G2 C1G2 O1G2 118.2(8) . . ? C2G3 C1G3 O1G3 110.5(10) . . ? C2GA C1G4 C2GB 54.5(15) . . ? C2GA C1G4 O1G4 112.3(13) . . ? C2GB C1G4 O1G4 120.2(11) . . ? C2GB C2GA C1G4 64.0(13) . . ? C2GA C2GB C1G4 61.5(12) . . ? _refine_diff_density_max 0.243 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.052 data_model7 _database_code_CSD 150562 # CHEMICAL DATA ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C25 H18 O2' _chemical_formula_weight 350.39 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P22121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, -z' '-x, y+1/2, -z+1/2' '-x, -y+1/2, z+1/2' _cell_length_a 9.054(3) _cell_length_b 10.761(3) _cell_length_c 18.539(3) _cell_angle_alpha 90.00(3) _cell_angle_beta 90.00(3) _cell_angle_gamma 90.00(3) _cell_volume 1806.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.540 _cell_measurement_theta_max 38.671 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method ? _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.635 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device CAD4 (Enraf-Nonius) _diffrn_measurement_method \w--2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 250 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% ? _diffrn_reflns_number 1971 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.75 _diffrn_reflns_theta_max 74.40 _reflns_number_total 1971 _reflns_number_observed 1687 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 Software' _computing_cell_refinement 'CAD4 Software' _computing_data_reduction 'Helena' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON' _computing_publication_material 'PLATON' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 78 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0837P)^2^+0.5652P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0039(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.38(57) _refine_ls_number_reflns 1893 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_obs 0.0494 _refine_ls_wR_factor_all 0.1376 _refine_ls_wR_factor_obs 0.1241 _refine_ls_goodness_of_fit_all 1.034 _refine_ls_goodness_of_fit_obs 1.064 _refine_ls_restrained_S_all 1.076 _refine_ls_restrained_S_obs 1.064 _refine_ls_shift/esd_max 0.006 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.8799(3) 0.1903(2) 0.45103(13) 0.0311(6) Uani 1 d . . H1A H 0.9657(3) 0.2060(2) 0.46577(13) 0.047 Uiso 1 calc R . O2 O 0.0612(3) 0.7559(3) 0.4321(2) 0.0386(7) Uani 1 d . . C1 C 0.6323(4) 0.5966(3) 0.2348(2) 0.0225(7) Uani 1 d . . C2 C 0.5723(4) 0.5046(4) 0.1913(2) 0.0259(8) Uani 1 d . . C3 C 0.6078(4) 0.5036(4) 0.1180(2) 0.0297(8) Uani 1 d . . C4 C 0.6996(5) 0.5941(4) 0.0888(2) 0.0343(9) Uani 1 d . . C5 C 0.7579(4) 0.6875(4) 0.1319(2) 0.0325(9) Uani 1 d . . C6 C 0.7226(4) 0.6882(3) 0.2052(2) 0.0250(7) Uani 1 d . . C7 C 0.7648(4) 0.7768(3) 0.2617(2) 0.0252(8) Uani 1 d . . C8 C 0.8437(4) 0.8881(4) 0.2576(2) 0.0335(9) Uani 1 d . . C9 C 0.8591(5) 0.9584(4) 0.3205(2) 0.0342(9) Uani 1 d . . C10 C 0.7970(5) 0.9184(4) 0.3847(2) 0.0322(9) Uani 1 d . . C11 C 0.7198(4) 0.8075(4) 0.3889(2) 0.0274(8) Uani 1 d . . C12 C 0.7040(4) 0.7364(3) 0.3268(2) 0.0224(7) Uani 1 d . . C13 C 0.6187(4) 0.6139(3) 0.3170(2) 0.0229(7) Uani 1 d . . C14 C 0.6909(3) 0.5026(3) 0.3552(2) 0.0210(7) Uani 1 d . . C15 C 0.8321(4) 0.5083(4) 0.3837(2) 0.0274(8) Uani 1 d . . C16 C 0.8975(4) 0.4066(4) 0.4162(2) 0.0285(8) Uani 1 d . . C17 C 0.8203(4) 0.2949(3) 0.4204(2) 0.0247(8) Uani 1 d . . C18 C 0.6787(4) 0.2867(4) 0.3929(2) 0.0276(8) Uani 1 d . . C19 C 0.6148(4) 0.3896(4) 0.3608(2) 0.0256(8) Uani 1 d . . C20 C 0.4602(4) 0.6361(3) 0.3442(2) 0.0230(7) Uani 1 d . . C21 C 0.3492(4) 0.6823(4) 0.2998(2) 0.0253(8) Uani 1 d . . C22 C 0.2153(4) 0.7200(4) 0.3273(2) 0.0301(8) Uani 1 d . . C23 C 0.1895(4) 0.7121(4) 0.4010(2) 0.0288(8) Uani 1 d . . C24 C 0.2944(4) 0.6604(4) 0.4461(2) 0.0310(8) Uani 1 d . . C25 C 0.4289(4) 0.6230(4) 0.4178(2) 0.0283(8) Uani 1 d . . H2 H 0.5019(40) 0.4427(37) 0.2111(19) 0.024(10) Uiso 1 d . . H16 H 0.9948(47) 0.4113(41) 0.4316(21) 0.035(11) Uiso 1 d . . H3 H 0.5693(50) 0.4381(42) 0.0881(23) 0.038(12) Uiso 1 d . . H19 H 0.5156(40) 0.3839(37) 0.3422(19) 0.021(9) Uiso 1 d . . H25 H 0.5080(43) 0.5918(40) 0.4479(21) 0.032(11) Uiso 1 d . . H8 H 0.8889(44) 0.9165(36) 0.2086(20) 0.027(10) Uiso 1 d . . H18 H 0.6222(49) 0.2030(44) 0.3957(21) 0.037(11) Uiso 1 d . . H22 H 0.1493(50) 0.7585(41) 0.2970(22) 0.037(11) Uiso 1 d . . H21 H 0.3709(57) 0.6947(47) 0.2482(26) 0.056(14) Uiso 1 d . . H9 H 0.9132(61) 1.0337(54) 0.3195(28) 0.066(16) Uiso 1 d . . H24 H 0.2764(46) 0.6578(43) 0.5010(27) 0.052(13) Uiso 1 d . . H15 H 0.8868(49) 0.5817(42) 0.3782(20) 0.031(11) Uiso 1 d . . H5 H 0.8174(52) 0.7573(45) 0.1103(23) 0.042(12) Uiso 1 d . . H10 H 0.8079(55) 0.9712(44) 0.4296(25) 0.054(14) Uiso 1 d . . H2A H 0.0109(84) 0.7977(76) 0.3999(41) 0.114(29) Uiso 1 d . . H11 H 0.6845(47) 0.7834(38) 0.4366(21) 0.033(11) Uiso 1 d . . H4 H 0.7255(53) 0.5882(46) 0.0398(27) 0.053(13) Uiso 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 O1 0.0372(13) 0.0258(14) 0.0304(12) 0.0040(10) -0.0058(11) 0.0030(12) O2 0.0301(13) 0.045(2) 0.0405(14) -0.0048(13) 0.0095(12) 0.0054(14) C1 0.0202(14) 0.027(2) 0.0208(14) 0.0029(13) 0.0014(13) 0.0020(15) C2 0.028(2) 0.025(2) 0.0246(15) -0.0023(14) 0.0012(14) 0.000(2) C3 0.036(2) 0.031(2) 0.0220(15) -0.004(2) -0.0018(15) 0.004(2) C4 0.046(2) 0.037(2) 0.0200(15) -0.0003(15) 0.006(2) -0.001(2) C5 0.039(2) 0.033(2) 0.026(2) 0.003(2) 0.0042(15) -0.004(2) C6 0.024(2) 0.027(2) 0.0242(15) -0.0008(14) 0.0006(14) 0.000(2) C7 0.026(2) 0.023(2) 0.0259(15) 0.0024(13) -0.0013(13) 0.001(2) C8 0.039(2) 0.028(2) 0.034(2) 0.001(2) 0.000(2) -0.003(2) C9 0.040(2) 0.020(2) 0.042(2) -0.001(2) -0.006(2) -0.005(2) C10 0.041(2) 0.023(2) 0.032(2) -0.004(2) -0.008(2) 0.002(2) C11 0.034(2) 0.022(2) 0.027(2) -0.0017(14) -0.0023(15) 0.007(2) C12 0.0227(15) 0.019(2) 0.0257(15) 0.0027(13) 0.0002(14) 0.0021(15) C13 0.0234(15) 0.025(2) 0.0201(14) -0.0015(13) -0.0001(13) 0.001(2) C14 0.0225(14) 0.021(2) 0.0193(14) -0.0019(13) 0.0029(12) 0.002(2) C15 0.026(2) 0.026(2) 0.030(2) 0.001(2) 0.0010(15) -0.002(2) C16 0.023(2) 0.033(2) 0.029(2) -0.002(2) -0.0051(14) 0.003(2) C17 0.034(2) 0.023(2) 0.0171(13) 0.0000(13) 0.0028(13) 0.002(2) C18 0.037(2) 0.024(2) 0.0217(14) 0.0004(14) -0.0035(14) -0.006(2) C19 0.026(2) 0.029(2) 0.0225(15) -0.0002(14) -0.0048(14) -0.001(2) C20 0.024(2) 0.026(2) 0.0191(14) -0.0008(13) 0.0018(13) 0.001(2) C21 0.028(2) 0.026(2) 0.0228(14) 0.0010(13) -0.0023(14) -0.002(2) C22 0.030(2) 0.032(2) 0.027(2) 0.000(2) -0.003(2) 0.002(2) C23 0.023(2) 0.031(2) 0.032(2) -0.0032(15) 0.0059(15) -0.001(2) C24 0.033(2) 0.036(2) 0.024(2) 0.0005(14) 0.007(2) 0.001(2) C25 0.032(2) 0.033(2) 0.020(2) 0.0020(15) 0.0014(14) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C17 1.371(4) . ? O2 C23 1.380(4) . ? C1 C2 1.388(5) . ? C1 C6 1.393(5) . ? C1 C13 1.540(4) . ? C2 C3 1.397(4) . ? C3 C4 1.390(6) . ? C4 C5 1.389(6) . ? C5 C6 1.396(5) . ? C6 C7 1.467(5) . ? C7 C12 1.396(4) . ? C7 C8 1.396(5) . ? C8 C9 1.397(5) . ? C9 C10 1.385(6) . ? C10 C11 1.385(6) . ? C11 C12 1.390(5) . ? C12 C13 1.538(5) . ? C13 C14 1.538(5) . ? C13 C20 1.540(5) . ? C14 C15 1.385(5) . ? C14 C19 1.402(5) . ? C15 C16 1.382(5) . ? C16 C17 1.393(5) . ? C17 C18 1.383(5) . ? C18 C19 1.384(5) . ? C20 C21 1.391(5) . ? C20 C25 1.402(4) . ? C21 C22 1.377(5) . ? C22 C23 1.388(5) . ? C23 C24 1.382(5) . ? C24 C25 1.386(5) . ? 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 C6 120.4(3) . . ? C2 C1 C13 129.1(3) . . ? C6 C1 C13 110.5(3) . . ? C1 C2 C3 118.8(3) . . ? C4 C3 C2 120.7(4) . . ? C5 C4 C3 120.7(3) . . ? C4 C5 C6 118.5(4) . . ? C1 C6 C5 120.9(3) . . ? C1 C6 C7 109.4(3) . . ? C5 C6 C7 129.7(3) . . ? C12 C7 C8 121.1(3) . . ? C12 C7 C6 108.2(3) . . ? C8 C7 C6 130.6(3) . . ? C7 C8 C9 118.1(3) . . ? C10 C9 C8 120.5(4) . . ? C9 C10 C11 121.4(3) . . ? C10 C11 C12 118.7(3) . . ? C11 C12 C7 120.3(3) . . ? C11 C12 C13 128.5(3) . . ? C7 C12 C13 111.2(3) . . ? C14 C13 C12 113.6(3) . . ? C14 C13 C1 109.2(3) . . ? C12 C13 C1 100.5(3) . . ? C14 C13 C20 111.4(3) . . ? C12 C13 C20 107.2(3) . . ? C1 C13 C20 114.6(3) . . ? C15 C14 C19 117.6(3) . . ? C15 C14 C13 122.3(3) . . ? C19 C14 C13 120.1(3) . . ? C16 C15 C14 121.8(4) . . ? C15 C16 C17 119.5(3) . . ? O1 C17 C18 117.7(3) . . ? O1 C17 C16 122.3(3) . . ? C18 C17 C16 120.0(3) . . ? C17 C18 C19 119.7(3) . . ? C18 C19 C14 121.3(3) . . ? C21 C20 C25 117.8(3) . . ? C21 C20 C13 122.4(3) . . ? C25 C20 C13 119.5(3) . . ? C22 C21 C20 121.4(3) . . ? C21 C22 C23 119.7(3) . . ? O2 C23 C24 117.6(3) . . ? O2 C23 C22 122.2(3) . . ? C24 C23 C22 120.2(3) . . ? C23 C24 C25 119.5(3) . . ? C24 C25 C20 121.1(3) . . ? _refine_diff_density_max 0.287 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.055 data_model8 _database_code_CSD 150563 # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C27 H18 N O2' _chemical_formula_weight 388.42 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 11.338(3) _cell_length_b 12.733(3) _cell_length_c 14.245(3) _cell_angle_alpha 90.00(3) _cell_angle_beta 94.45(3) _cell_angle_gamma 90.00(3) _cell_volume 2050.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.900 _cell_measurement_theta_max 46.428 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method ? _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 0.628 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device CAD4 (Enraf-Nonius' _diffrn_measurement_method \w--2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 250 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% ? _diffrn_reflns_number 4226 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0165 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.66 _diffrn_reflns_theta_max 74.75 _reflns_number_total 4014 _reflns_number_observed 3648 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 software' _computing_cell_refinement 'CAD4 software' _computing_data_reduction 'Helena' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON' _computing_publication_material 'PLATON' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 100 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0442P)^2^+0.8283P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0041(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3914 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_obs 0.0414 _refine_ls_wR_factor_all 0.1097 _refine_ls_wR_factor_obs 0.1066 _refine_ls_goodness_of_fit_all 1.198 _refine_ls_goodness_of_fit_obs 1.223 _refine_ls_restrained_S_all 1.195 _refine_ls_restrained_S_obs 1.223 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O -0.21940(11) 0.29862(9) 1.12189(8) 0.0332(3) Uani 1 d . . H1A H -0.2094(22) 0.2704(20) 1.1826(18) 0.065(7) Uiso 1 d . . O2 O 0.15643(10) 0.01759(9) 0.59222(8) 0.0310(3) Uani 1 d . . C1 C -0.19468(13) -0.13659(11) 0.88953(9) 0.0208(3) Uani 1 d . . C2 C -0.09924(14) -0.17934(12) 0.94317(10) 0.0239(3) Uani 1 d . . H2 H -0.0270(16) -0.1371(14) 0.9562(12) 0.030(5) Uiso 1 d . . C3 C -0.10971(15) -0.28047(12) 0.97904(11) 0.0284(3) Uani 1 d . . H3 H -0.0426(16) -0.3118(14) 1.0173(12) 0.027(4) Uiso 1 d . . C4 C -0.2132(2) -0.33801(12) 0.96044(11) 0.0310(4) Uani 1 d . . H4 H -0.2212(18) -0.4087(17) 0.9863(14) 0.042(5) Uiso 1 d . . C5 C -0.30772(15) -0.29674(12) 0.90480(11) 0.0282(3) Uani 1 d . . H5 H -0.3793(17) -0.3368(15) 0.8920(13) 0.034(5) Uiso 1 d . . C6 C -0.29799(13) -0.19537(11) 0.86949(10) 0.0230(3) Uani 1 d . . C7 C -0.38235(13) -0.13180(12) 0.80983(10) 0.0242(3) Uani 1 d . . C8 C -0.49567(14) -0.15527(13) 0.77066(11) 0.0303(3) Uani 1 d . . H8 H -0.5316(17) -0.2240(16) 0.7817(13) 0.037(5) Uiso 1 d . . C9 C -0.55576(15) -0.08041(14) 0.71395(11) 0.0329(4) Uani 1 d . . H9 H -0.6339(18) -0.0944(15) 0.6854(13) 0.037(5) Uiso 1 d . . C10 C -0.50321(15) 0.01560(14) 0.69678(11) 0.0312(4) Uani 1 d . . H10 H -0.5464(17) 0.0668(15) 0.6591(13) 0.034(5) Uiso 1 d . . C11 C -0.39036(14) 0.03977(13) 0.73682(10) 0.0266(3) Uani 1 d . . H11 H -0.3546(16) 0.1086(16) 0.7248(13) 0.033(5) Uiso 1 d . . C12 C -0.33018(13) -0.03424(11) 0.79365(9) 0.0222(3) Uani 1 d . . C13 C -0.20634(13) -0.02665(11) 0.84606(9) 0.0204(3) Uani 1 d . . C14 C -0.20855(12) 0.05939(11) 0.92175(9) 0.0202(3) Uani 1 d . . C15 C -0.22140(13) 0.03576(11) 1.01574(10) 0.0226(3) Uani 1 d . . H15 H -0.2250(15) -0.0378(14) 1.0352(12) 0.025(4) Uiso 1 d . . C16 C -0.22727(13) 0.11403(12) 1.08350(10) 0.0249(3) Uani 1 d . . H16 H -0.2351(16) 0.0963(15) 1.1493(13) 0.033(5) Uiso 1 d . . C17 C -0.21842(13) 0.21818(11) 1.05750(10) 0.0242(3) Uani 1 d . . C18 C -0.20674(13) 0.24438(12) 0.96402(10) 0.0244(3) Uani 1 d . . H18 H -0.1992(16) 0.3188(15) 0.9483(13) 0.031(5) Uiso 1 d . . C19 C -0.20291(13) 0.16582(11) 0.89675(10) 0.0229(3) Uani 1 d . . H19 H -0.1951(15) 0.1854(14) 0.8291(13) 0.027(4) Uiso 1 d . . C20 C -0.10814(13) -0.01017(11) 0.77912(9) 0.0202(3) Uani 1 d . . H2A H 0.2049(21) 0.0778(19) 0.6087(16) 0.056(6) Uiso 1 d . . C21 C -0.00550(13) 0.04595(11) 0.80458(10) 0.0224(3) Uani 1 d . . H21 H 0.0054(16) 0.0818(14) 0.8678(13) 0.030(4) Uiso 1 d . . C22 C 0.08412(13) 0.05574(11) 0.74371(10) 0.0235(3) Uani 1 d . . H22 H 0.1564(17) 0.0969(15) 0.7633(12) 0.030(4) Uiso 1 d . . C23 C 0.07197(13) 0.00860(11) 0.65552(10) 0.0229(3) Uani 1 d . . C24 C -0.02838(14) -0.05015(12) 0.62965(10) 0.0263(3) Uani 1 d . . H24 H -0.0380(16) -0.0799(15) 0.5666(13) 0.035(5) Uiso 1 d . . C25 C -0.11695(14) -0.05918(11) 0.69100(10) 0.0246(3) Uani 1 d . . H25 H -0.1894(17) -0.1023(16) 0.6719(13) 0.036(5) Uiso 1 d . . N N 0.1684(2) 0.72985(13) 0.68682(11) 0.0445(4) Uani 1 d . . C1G C 0.1036(2) 0.69469(15) 0.63071(12) 0.0350(4) Uani 1 d . . C2G C 0.0193(2) 0.6483(2) 0.55985(13) 0.0509(5) Uani 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 O1 0.0466(7) 0.0271(6) 0.0253(6) -0.0076(4) -0.0024(5) 0.0066(5) O2 0.0345(7) 0.0312(6) 0.0291(6) -0.0033(4) 0.0141(5) -0.0022(5) C1 0.0249(8) 0.0193(7) 0.0186(6) -0.0020(5) 0.0051(5) -0.0015(5) C2 0.0259(8) 0.0237(7) 0.0223(7) 0.0002(5) 0.0034(6) -0.0010(6) C3 0.0344(9) 0.0255(7) 0.0256(7) 0.0033(6) 0.0048(6) 0.0035(6) C4 0.0410(10) 0.0206(7) 0.0326(8) 0.0024(6) 0.0113(7) -0.0011(6) C5 0.0301(9) 0.0222(7) 0.0330(8) -0.0035(6) 0.0084(6) -0.0063(6) C6 0.0245(8) 0.0223(7) 0.0230(7) -0.0041(5) 0.0060(5) -0.0025(5) C7 0.0237(8) 0.0262(7) 0.0230(7) -0.0059(6) 0.0042(5) -0.0020(6) C8 0.0253(8) 0.0320(8) 0.0337(8) -0.0076(6) 0.0030(6) -0.0069(6) C9 0.0232(9) 0.0448(10) 0.0300(8) -0.0083(7) -0.0026(6) -0.0009(7) C10 0.0285(9) 0.0396(9) 0.0247(7) -0.0019(6) -0.0022(6) 0.0052(7) C11 0.0272(8) 0.0295(8) 0.0229(7) -0.0003(6) 0.0008(6) 0.0017(6) C12 0.0224(8) 0.0255(7) 0.0188(6) -0.0037(5) 0.0028(5) -0.0008(5) C13 0.0227(8) 0.0197(7) 0.0187(6) 0.0003(5) 0.0006(5) -0.0017(5) C14 0.0181(7) 0.0220(7) 0.0204(6) -0.0013(5) 0.0012(5) -0.0013(5) C15 0.0230(8) 0.0224(7) 0.0227(7) 0.0012(5) 0.0026(5) -0.0009(5) C16 0.0263(8) 0.0285(7) 0.0200(7) -0.0003(6) 0.0029(5) 0.0020(6) C17 0.0226(8) 0.0257(7) 0.0236(7) -0.0056(6) -0.0014(5) 0.0036(6) C18 0.0264(8) 0.0205(7) 0.0257(7) -0.0004(5) -0.0016(6) 0.0017(6) C19 0.0243(8) 0.0232(7) 0.0211(7) 0.0013(5) 0.0007(5) 0.0005(5) C20 0.0232(8) 0.0185(6) 0.0190(6) 0.0016(5) 0.0021(5) 0.0010(5) C21 0.0243(8) 0.0246(7) 0.0182(6) 0.0001(5) 0.0009(5) -0.0009(6) C22 0.0245(8) 0.0234(7) 0.0224(7) 0.0012(5) 0.0008(6) -0.0011(6) C23 0.0270(8) 0.0201(7) 0.0223(7) 0.0025(5) 0.0063(5) 0.0039(5) C24 0.0343(9) 0.0234(7) 0.0214(7) -0.0051(6) 0.0050(6) 0.0001(6) C25 0.0275(8) 0.0221(7) 0.0243(7) -0.0042(5) 0.0018(6) -0.0032(6) N 0.0536(10) 0.0448(9) 0.0338(8) 0.0009(7) -0.0053(7) 0.0058(7) C1G 0.0345(10) 0.0434(10) 0.0275(8) 0.0042(7) 0.0048(7) 0.0063(7) C2G 0.0338(11) 0.085(2) 0.0345(9) -0.0080(10) 0.0027(8) -0.0107(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C17 1.376(2) . ? O2 C23 1.370(2) . ? C1 C2 1.387(2) . ? C1 C6 1.401(2) . ? C1 C13 1.532(2) . ? C2 C3 1.394(2) . ? C3 C4 1.391(2) . ? C4 C5 1.386(2) . ? C5 C6 1.393(2) . ? C6 C7 1.472(2) . ? C7 C8 1.393(2) . ? C7 C12 1.403(2) . ? C8 C9 1.393(2) . ? C9 C10 1.390(3) . ? C10 C11 1.394(2) . ? C11 C12 1.387(2) . ? C12 C13 1.541(2) . ? C13 C20 1.535(2) . ? C13 C14 1.539(2) . ? C14 C15 1.391(2) . ? C14 C19 1.404(2) . ? C15 C16 1.393(2) . ? C16 C17 1.383(2) . ? C17 C18 1.389(2) . ? C18 C19 1.388(2) . ? C20 C21 1.390(2) . ? C20 C25 1.398(2) . ? C21 C22 1.392(2) . ? C22 C23 1.389(2) . ? C23 C24 1.387(2) . ? C24 C25 1.386(2) . ? N C1G 1.135(2) . ? C1G C2G 1.460(3) . ? 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 C6 120.47(13) . . ? C2 C1 C13 128.35(13) . . ? C6 C1 C13 111.18(13) . . ? C1 C2 C3 118.66(14) . . ? C4 C3 C2 120.75(15) . . ? C5 C4 C3 120.84(14) . . ? C4 C5 C6 118.58(15) . . ? C5 C6 C1 120.66(14) . . ? C5 C6 C7 130.70(14) . . ? C1 C6 C7 108.64(13) . . ? C8 C7 C12 120.79(15) . . ? C8 C7 C6 130.64(14) . . ? C12 C7 C6 108.57(13) . . ? C9 C8 C7 118.7(2) . . ? C10 C9 C8 120.5(2) . . ? C9 C10 C11 121.0(2) . . ? C12 C11 C10 118.9(2) . . ? C11 C12 C7 120.20(14) . . ? C11 C12 C13 128.95(13) . . ? C7 C12 C13 110.84(13) . . ? C1 C13 C20 109.38(11) . . ? C1 C13 C14 111.89(11) . . ? C20 C13 C14 112.95(11) . . ? C1 C13 C12 100.68(11) . . ? C20 C13 C12 112.64(11) . . ? C14 C13 C12 108.68(12) . . ? C15 C14 C19 117.59(13) . . ? C15 C14 C13 121.95(12) . . ? C19 C14 C13 120.39(12) . . ? C14 C15 C16 121.77(14) . . ? C17 C16 C15 119.50(13) . . ? O1 C17 C16 122.08(13) . . ? O1 C17 C18 117.82(13) . . ? C16 C17 C18 120.10(13) . . ? C19 C18 C17 119.93(14) . . ? C18 C19 C14 121.07(13) . . ? C21 C20 C25 117.64(13) . . ? C21 C20 C13 122.76(12) . . ? C25 C20 C13 119.45(13) . . ? C20 C21 C22 121.37(13) . . ? C23 C22 C21 119.92(14) . . ? O2 C23 C24 118.09(13) . . ? O2 C23 C22 122.25(14) . . ? C24 C23 C22 119.66(14) . . ? C25 C24 C23 119.77(13) . . ? C24 C25 C20 121.61(14) . . ? N C1G C2G 178.9(2) . . ? _refine_diff_density_max 0.512 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.049 data_2 _database_code_CSD 150564 # CHEMICAL DATA ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C77.50 H66 N O8.50' _chemical_formula_weight 1147.31 _chemical_melting_point ? _chemical_compound_source ? 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 12.802(7) _cell_length_b 10.930(2) _cell_length_c 21.704(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.39(3) _cell_angle_gamma 90.00 _cell_volume 3036.9(19) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.639 _cell_measurement_theta_max 10.280 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method ? _exptl_crystal_F_000 1212 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71140 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CAD4 (Enraf-Nonius)' _diffrn_measurement_method /w--2/q _diffrn_standards_number 3 _diffrn_standards_interval_count 250 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% none _diffrn_reflns_number 6703 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 26.99 _reflns_number_total 6407 _reflns_number_observed 4124 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 software' _computing_cell_refinement 'CAD4 software' _computing_data_reduction 'Helena' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON' _computing_publication_material 'PLATON' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 9 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1990P)^2^+0.8807P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6398 _refine_ls_number_parameters 390 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1361 _refine_ls_R_factor_obs 0.0832 _refine_ls_wR_factor_all 0.2983 _refine_ls_wR_factor_obs 0.2377 _refine_ls_goodness_of_fit_all 1.028 _refine_ls_goodness_of_fit_obs 1.059 _refine_ls_restrained_S_all 1.060 _refine_ls_restrained_S_obs 1.059 _refine_ls_shift/esd_max 0.017 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O2 O 0.1446(2) 0.2144(2) 0.23584(10) 0.0352(6) Uani 1 d . . O28 O -0.3103(2) 0.7130(2) 0.48499(11) 0.0429(7) Uani 1 d . . O32 O -0.3173(2) 0.6108(2) 0.62949(12) 0.0399(6) Uani 1 d . . O37 O -0.2920(3) 1.1144(2) 0.63064(13) 0.0585(9) Uani 1 d . . C1 C 0.2336(3) 0.2701(4) 0.2641(2) 0.0356(8) Uani 1 d . . H1A H 0.2152(3) 0.3543(4) 0.2768(2) 0.043 Uiso 1 calc R . H1B H 0.2903(3) 0.2758(4) 0.2335(2) 0.043 Uiso 1 calc R . C3 C 0.0492(3) 0.2407(3) 0.26008(15) 0.0287(7) Uani 1 d . . C4 C 0.0342(3) 0.2943(3) 0.3175(2) 0.0349(8) Uani 1 d . . H4A H 0.0932(3) 0.3156(3) 0.3428(2) 0.042 Uiso 1 d R . C5 C -0.0670(3) 0.3170(3) 0.3378(2) 0.0343(8) Uani 1 d . . H5A H -0.0772(3) 0.3534(3) 0.3776(2) 0.041 Uiso 1 d R . C6 C -0.1532(3) 0.2882(3) 0.30223(14) 0.0256(7) Uani 1 d . . C7 C -0.1366(3) 0.2350(3) 0.24478(14) 0.0276(7) Uani 1 d . . H7A H -0.1953(3) 0.2149(3) 0.21900(14) 0.033 Uiso 1 d R . C8 C -0.0362(3) 0.2103(3) 0.22462(14) 0.0291(7) Uani 1 d . . H8A H -0.0261(3) 0.1713(3) 0.18547(14) 0.035 Uiso 1 d R . C9 C -0.2653(3) 0.3013(3) 0.32618(14) 0.0255(7) Uani 1 d . . C10 C -0.3449(2) 0.3133(3) 0.27382(14) 0.0260(7) Uani 1 d . . C11 C -0.4100(3) 0.2107(3) 0.27109(15) 0.0281(7) Uani 1 d . . C12 C -0.4868(3) 0.2012(3) 0.2263(2) 0.0355(8) Uani 1 d . . H12A H -0.5304(3) 0.1298(3) 0.2241(2) 0.043 Uiso 1 d R . C13 C -0.4995(3) 0.2958(4) 0.1844(2) 0.0419(9) Uani 1 d . . H13A H -0.5532(3) 0.2908(4) 0.1534(2) 0.050 Uiso 1 d R . C14 C -0.4353(3) 0.3987(4) 0.1876(2) 0.0385(8) Uani 1 d . . H14A H -0.4448(3) 0.4639(4) 0.1585(2) 0.046 Uiso 1 d R . C15 C -0.3578(3) 0.4074(3) 0.23172(14) 0.0307(7) Uani 1 d . . H15A H -0.3135(3) 0.4782(3) 0.23372(14) 0.037 Uiso 1 d R . C16 C -0.2959(3) 0.1768(3) 0.35346(14) 0.0282(7) Uani 1 d . . C17 C -0.3793(3) 0.1254(3) 0.31971(15) 0.0285(7) Uani 1 d . . C18 C -0.4152(3) 0.0088(3) 0.3338(2) 0.0382(8) Uani 1 d . . H18A H -0.4716(3) -0.0269(3) 0.3107(2) 0.046 Uiso 1 d R . C19 C -0.3676(3) -0.0544(3) 0.3815(2) 0.0431(9) Uani 1 d . . H19A H -0.3923(3) -0.1347(3) 0.3918(2) 0.052 Uiso 1 d R . C20 C -0.2861(3) -0.0031(3) 0.4149(2) 0.0392(9) Uani 1 d . . H20A H -0.2543(3) -0.0490(3) 0.4477(2) 0.047 Uiso 1 d R . C21 C -0.2492(3) 0.1129(3) 0.4009(2) 0.0366(8) Uani 1 d . . H21A H -0.1921(3) 0.1480(3) 0.4236(2) 0.044 Uiso 1 d R . C22 C -0.2772(2) 0.4081(3) 0.37132(13) 0.0250(7) Uani 1 d . . C23 C -0.3373(3) 0.3988(3) 0.42403(15) 0.0308(7) Uani 1 d . . H23A H -0.3692(3) 0.3219(3) 0.43401(15) 0.037 Uiso 1 d R . C24 C -0.3531(3) 0.4986(3) 0.4623(2) 0.0357(8) Uani 1 d . . H24A H -0.3953(3) 0.4907(3) 0.4985(2) 0.043 Uiso 1 d R . C25 C -0.3072(3) 0.6100(3) 0.44871(14) 0.0310(7) Uani 1 d . . C26 C -0.2459(3) 0.6209(3) 0.39642(14) 0.0295(7) Uani 1 d . . H26A H -0.2131(3) 0.6975(3) 0.38685(14) 0.035 Uiso 1 d R . C27 C -0.2322(3) 0.5212(3) 0.35840(13) 0.0272(7) Uani 1 d . . H27A H -0.1908(3) 0.5299(3) 0.32192(13) 0.033 Uiso 1 d R . C29 C -0.3973(3) 0.7319(4) 0.5255(2) 0.0386(8) Uani 1 d . . H29A H -0.4268(3) 0.6524(4) 0.5387(2) 0.063(14) Uiso 1 calc R . H29B H -0.4528(3) 0.7794(4) 0.5044(2) 0.043(11) Uiso 1 calc R . C30 C -0.3565(3) 0.8010(3) 0.58000(15) 0.0325(8) Uani 1 d . . C31 C -0.3180(3) 0.7377(3) 0.6307(2) 0.0310(7) Uani 1 d . . C33 C -0.4024(3) 0.5556(4) 0.6622(2) 0.0446(9) Uani 1 d . . H33A H -0.3973(3) 0.4682(4) 0.6590(2) 0.067 Uiso 1 d R . H33B H -0.3986(3) 0.5791(4) 0.7048(2) 0.067 Uiso 1 d R . H33C H -0.4677(3) 0.5822(4) 0.6449(2) 0.067 Uiso 1 d R . C34 C -0.2733(3) 0.7994(3) 0.68027(15) 0.0308(7) Uani 1 d . . C35 C -0.2664(3) 0.9258(3) 0.6777(2) 0.0371(8) Uani 1 d . . H35A H -0.2347(3) 0.9692(3) 0.7114(2) 0.045 Uiso 1 d R . C36 C -0.3046(3) 0.9897(3) 0.6276(2) 0.0381(8) Uani 1 d . . C38 C -0.3347(5) 1.1858(4) 0.5827(2) 0.0621(13) Uani 1 d . . H38A H -0.3197(5) 1.2705(4) 0.5904(2) 0.093 Uiso 1 d R . H38B H -0.3046(5) 1.1619(4) 0.5441(2) 0.093 Uiso 1 d R . H38C H -0.4090(5) 1.1740(4) 0.5809(2) 0.093 Uiso 1 d R . C39 C -0.3503(3) 0.9279(3) 0.57898(15) 0.0348(8) Uani 1 d . . H39A H -0.3779(3) 0.9725(3) 0.54439(15) 0.042 Uiso 1 d R . C1G C 0.0020(15) -0.3241(16) 0.4872(8) 0.120(5) Uiso 0.50 d P . H1GA H -0.0502(15) -0.3691(16) 0.5093(8) 0.180 Uiso 0.50 d PR . H1GB H -0.0046(15) -0.3409(16) 0.4439(8) 0.180 Uiso 0.50 d PR . H1GC H 0.0701(15) -0.3483(16) 0.5013(8) 0.180 Uiso 0.50 d PR . C2G C -0.0054(14) -0.1911(17) 0.4980(8) 0.115(5) Uiso 0.50 d P . C3G C -0.0716(11) -0.1272(13) 0.5337(7) 0.092(4) Uiso 0.50 d P . H3GA H -0.1216(11) -0.1702(13) 0.5584(7) 0.110 Uiso 0.50 d PR . C4G C -0.0657(7) 0.0004(9) 0.5341(4) 0.119(3) Uiso 1 d . . H4GA H -0.1171(7) 0.0448(9) 0.5571(4) 0.143 Uiso 1 d R . C5G C 0.0073(14) 0.0631(16) 0.5031(8) 0.113(5) Uiso 0.50 d P . H5GA H 0.0168(14) 0.1496(16) 0.5086(8) 0.136 Uiso 0.50 d PR . N7G N 0.0721(10) -0.1214(12) 0.4636(6) 0.104(4) Uiso 0.50 d P . C1A C -0.0445(15) -0.5257(21) 0.5179(10) 0.070(5) Uiso 0.25 d PD . C2A C 0.0521(14) -0.5839(18) 0.4903(9) 0.127(6) Uiso 0.50 d PD . H2AA H 0.0903(14) -0.5256(18) 0.4663(9) 0.191 Uiso 0.50 d PR . H2AB H 0.0961(14) -0.6147(18) 0.5228(9) 0.191 Uiso 0.50 d PR . H2AC H 0.0300(14) -0.6503(18) 0.4644(9) 0.191 Uiso 0.50 d PR . O1A O -0.1051(26) -0.5646(32) 0.5467(15) 0.171(11) Uiso 0.25 d P . 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 O2 0.0269(13) 0.0475(15) 0.0313(12) -0.0001(10) 0.0019(10) 0.0057(10) O28 0.062(2) 0.0318(13) 0.0350(13) -0.0126(10) 0.0177(12) -0.0107(12) O32 0.0409(14) 0.0284(12) 0.0506(15) -0.0015(10) 0.0100(12) 0.0024(10) O37 0.101(3) 0.0274(14) 0.047(2) -0.0036(11) -0.021(2) 0.0016(15) C1 0.026(2) 0.045(2) 0.036(2) 0.0070(15) -0.0003(14) 0.0007(15) C3 0.026(2) 0.030(2) 0.029(2) 0.0038(13) 0.0021(13) 0.0026(13) C4 0.028(2) 0.044(2) 0.033(2) -0.0098(15) -0.0060(14) 0.0024(15) C5 0.033(2) 0.041(2) 0.029(2) -0.0086(14) -0.0003(13) 0.0053(15) C6 0.032(2) 0.0213(14) 0.0237(14) -0.0009(11) 0.0019(12) 0.0022(12) C7 0.026(2) 0.030(2) 0.0274(15) -0.0032(12) -0.0017(12) 0.0003(13) C8 0.033(2) 0.031(2) 0.0233(14) -0.0032(12) -0.0005(13) 0.0029(13) C9 0.030(2) 0.0217(14) 0.0248(14) -0.0018(11) 0.0024(12) 0.0008(12) C10 0.023(2) 0.028(2) 0.0266(15) -0.0049(12) 0.0005(12) 0.0043(12) C11 0.025(2) 0.028(2) 0.032(2) -0.0059(12) 0.0057(13) 0.0016(12) C12 0.030(2) 0.038(2) 0.038(2) -0.0082(15) -0.0008(14) -0.0024(15) C13 0.035(2) 0.057(2) 0.035(2) -0.004(2) -0.0064(15) 0.004(2) C14 0.036(2) 0.045(2) 0.035(2) 0.0052(15) 0.0005(15) 0.005(2) C15 0.031(2) 0.033(2) 0.028(2) 0.0010(13) -0.0008(13) 0.0027(14) C16 0.034(2) 0.0216(15) 0.029(2) -0.0025(12) 0.0061(13) -0.0006(13) C17 0.029(2) 0.025(2) 0.032(2) -0.0037(12) 0.0046(13) 0.0007(13) C18 0.036(2) 0.031(2) 0.047(2) -0.0036(15) 0.005(2) -0.0073(15) C19 0.052(2) 0.028(2) 0.049(2) 0.004(2) 0.013(2) -0.005(2) C20 0.054(2) 0.027(2) 0.036(2) 0.0080(14) 0.008(2) 0.005(2) C21 0.048(2) 0.031(2) 0.030(2) -0.0015(13) 0.0052(15) 0.000(2) C22 0.030(2) 0.0222(14) 0.0227(14) -0.0015(11) -0.0014(12) 0.0010(12) C23 0.034(2) 0.026(2) 0.032(2) 0.0013(13) 0.0052(14) -0.0043(13) C24 0.045(2) 0.033(2) 0.030(2) -0.0026(13) 0.0146(15) -0.0053(15) C25 0.044(2) 0.025(2) 0.0238(15) -0.0046(12) 0.0042(14) -0.0026(14) C26 0.038(2) 0.0234(15) 0.028(2) 0.0000(12) 0.0033(13) -0.0046(13) C27 0.032(2) 0.029(2) 0.0208(14) 0.0002(12) 0.0021(12) -0.0032(13) C29 0.042(2) 0.040(2) 0.033(2) -0.0108(15) 0.003(2) 0.005(2) C30 0.031(2) 0.038(2) 0.028(2) -0.0071(13) 0.0050(13) 0.0045(14) C31 0.029(2) 0.028(2) 0.036(2) -0.0019(13) 0.0090(14) 0.0030(13) C33 0.039(2) 0.041(2) 0.054(2) 0.007(2) 0.001(2) -0.005(2) C34 0.028(2) 0.036(2) 0.028(2) 0.0013(13) 0.0065(13) 0.0038(14) C35 0.045(2) 0.036(2) 0.030(2) -0.0069(14) -0.0033(15) 0.001(2) C36 0.053(2) 0.030(2) 0.032(2) -0.0045(14) 0.000(2) 0.005(2) C38 0.100(4) 0.035(2) 0.051(2) 0.004(2) -0.008(2) 0.008(2) C39 0.042(2) 0.035(2) 0.028(2) -0.0007(13) 0.0038(14) 0.009(2) _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 O2 C3 1.364(4) . ? O2 C1 1.427(4) . ? O28 C25 1.375(4) . ? O28 C29 1.439(4) . ? O32 C31 1.386(4) . ? O32 C33 1.438(4) . ? O37 C36 1.374(4) . ? O37 C38 1.409(5) . ? C1 C34 1.511(5) 3_566 ? C3 C8 1.373(5) . ? C3 C4 1.392(5) . ? C4 C5 1.393(5) . ? C5 C6 1.379(5) . ? C6 C7 1.393(4) . ? C6 C9 1.536(4) . ? C7 C8 1.387(5) . ? C9 C10 1.527(4) . ? C9 C22 1.533(4) . ? C9 C16 1.535(4) . ? C10 C15 1.386(5) . ? C10 C11 1.398(4) . ? C11 C12 1.381(5) . ? C11 C17 1.460(5) . ? C12 C13 1.386(5) . ? C13 C14 1.395(6) . ? C14 C15 1.377(5) . ? C16 C21 1.377(5) . ? C16 C17 1.408(5) . ? C17 C18 1.389(5) . ? C18 C19 1.382(6) . ? C19 C20 1.385(6) . ? C20 C21 1.387(5) . ? C22 C23 1.387(4) . ? C22 C27 1.393(4) . ? C23 C24 1.387(5) . ? C24 C25 1.385(5) . ? C25 C26 1.390(4) . ? C26 C27 1.379(4) . ? C29 C30 1.494(5) . ? C30 C31 1.388(5) . ? C30 C39 1.390(5) . ? C31 C34 1.390(5) . ? C34 C35 1.385(5) . ? C34 C1 1.511(5) 3_566 ? C35 C36 1.378(5) . ? C36 C39 1.380(5) . ? C1G C2A 1.32(2) 3_546 ? C1G C2G 1.48(2) . ? C1G C1A 1.73(3) 3_546 ? C2G C3G 1.35(2) . ? C2G C5G 1.40(2) 3_556 ? C2G N7G 1.46(2) . ? C3G C5G 1.35(2) 3_556 ? C3G C4G 1.40(2) . ? C4G C5G 1.30(2) 3_556 ? C4G N7G 1.326(14) 3_556 ? C4G C5G 1.34(2) . ? C5G C4G 1.30(2) 3_556 ? C5G C3G 1.35(2) 3_556 ? C5G C2G 1.40(2) 3_556 ? C5G C5G 1.40(4) 3_556 ? C5G N7G 1.40(2) 3_556 ? N7G C4G 1.326(14) 3_556 ? N7G C5G 1.40(2) 3_556 ? C1A O1A 1.09(3) . ? C1A C2A 1.21(3) 3_546 ? C1A C1A 1.49(4) 3_546 ? C1A C2A 1.517(10) . ? C1A C1G 1.73(3) 3_546 ? C2A C1A 1.21(3) 3_546 ? C2A C1G 1.32(2) 3_546 ? 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 C3 O2 C1 117.3(3) . . ? C25 O28 C29 119.6(3) . . ? C31 O32 C33 113.9(3) . . ? C36 O37 C38 118.0(3) . . ? O2 C1 C34 113.1(3) . 3_566 ? O2 C3 C8 116.4(3) . . ? O2 C3 C4 124.3(3) . . ? C8 C3 C4 119.3(3) . . ? C3 C4 C5 119.5(3) . . ? C6 C5 C4 121.7(3) . . ? C5 C6 C7 118.0(3) . . ? C5 C6 C9 122.4(3) . . ? C7 C6 C9 119.4(3) . . ? C8 C7 C6 120.7(3) . . ? C3 C8 C7 120.8(3) . . ? C10 C9 C22 110.0(2) . . ? C10 C9 C16 101.1(3) . . ? C22 C9 C16 113.7(2) . . ? C10 C9 C6 112.1(2) . . ? C22 C9 C6 112.6(3) . . ? C16 C9 C6 106.8(2) . . ? C15 C10 C11 119.9(3) . . ? C15 C10 C9 129.1(3) . . ? C11 C10 C9 110.9(3) . . ? C12 C11 C10 120.8(3) . . ? C12 C11 C17 130.3(3) . . ? C10 C11 C17 108.9(3) . . ? C11 C12 C13 119.0(3) . . ? C12 C13 C14 120.2(3) . . ? C15 C14 C13 120.8(3) . . ? C14 C15 C10 119.3(3) . . ? C21 C16 C17 120.6(3) . . ? C21 C16 C9 128.9(3) . . ? C17 C16 C9 110.3(3) . . ? C18 C17 C16 120.1(3) . . ? C18 C17 C11 131.1(3) . . ? C16 C17 C11 108.7(3) . . ? C19 C18 C17 118.6(3) . . ? C18 C19 C20 121.0(3) . . ? C19 C20 C21 120.8(3) . . ? C16 C21 C20 118.8(4) . . ? C23 C22 C27 117.6(3) . . ? C23 C22 C9 122.0(3) . . ? C27 C22 C9 120.3(3) . . ? C22 C23 C24 121.4(3) . . ? C25 C24 C23 120.0(3) . . ? O28 C25 C24 125.7(3) . . ? O28 C25 C26 114.6(3) . . ? C24 C25 C26 119.5(3) . . ? C27 C26 C25 119.7(3) . . ? C26 C27 C22 121.7(3) . . ? O28 C29 C30 106.8(3) . . ? C31 C30 C39 119.4(3) . . ? C31 C30 C29 119.7(3) . . ? C39 C30 C29 120.8(3) . . ? O32 C31 C30 119.1(3) . . ? O32 C31 C34 119.8(3) . . ? C30 C31 C34 120.9(3) . . ? C35 C34 C31 118.6(3) . . ? C35 C34 C1 120.8(3) . 3_566 ? C31 C34 C1 120.6(3) . 3_566 ? C36 C35 C34 121.0(3) . . ? O37 C36 C35 115.1(3) . . ? O37 C36 C39 124.8(3) . . ? C35 C36 C39 120.1(3) . . ? C36 C39 C30 120.0(3) . . ? C2A C1G C2G 131.3(18) 3_546 . ? C2A C1G C1A 57.8(9) 3_546 3_546 ? C2G C1G C1A 164.5(17) . 3_546 ? C3G C2G C5G 58.8(12) . 3_556 ? C3G C2G N7G 117.1(16) . . ? C5G C2G N7G 58.7(11) 3_556 . ? C3G C2G C1G 130.0(17) . . ? C5G C2G C1G 169.5(18) 3_556 . ? N7G C2G C1G 112.8(15) . . ? C2G C3G C5G 62.5(12) . 3_556 ? C2G C3G C4G 119.1(15) . . ? C5G C3G C4G 56.7(10) 3_556 . ? C5G C4G N7G 126.2(14) 3_556 3_556 ? C5G C4G C5G 63.8(15) 3_556 . ? N7G C4G C5G 63.5(10) 3_556 . ? C5G C4G C3G 59.7(10) 3_556 . ? N7G C4G C3G 173.1(12) 3_556 . ? C5G C4G C3G 123.0(14) . . ? C4G C5G C4G 116.2(15) 3_556 . ? C4G C5G C3G 63.5(11) 3_556 3_556 ? C4G C5G C3G 172.9(17) . 3_556 ? C4G C5G C2G 122.1(17) 3_556 3_556 ? C4G C5G C2G 120.5(17) . 3_556 ? C3G C5G C2G 58.7(12) 3_556 3_556 ? C4G C5G C5G 59.4(13) 3_556 3_556 ? C4G C5G C5G 56.8(13) . 3_556 ? C3G C5G C5G 122.5(21) 3_556 3_556 ? C2G C5G C5G 169.2(23) 3_556 3_556 ? C4G C5G N7G 168.6(17) 3_556 3_556 ? C4G C5G N7G 57.7(10) . 3_556 ? C3G C5G N7G 121.1(16) 3_556 3_556 ? C2G C5G N7G 62.8(12) 3_556 3_556 ? C5G C5G N7G 113.6(20) 3_556 3_556 ? C4G N7G C5G 58.9(10) 3_556 3_556 ? C4G N7G C2G 117.3(13) 3_556 . ? C5G N7G C2G 58.4(11) 3_556 . ? O1A C1A C2A 114.4(28) . 3_546 ? O1A C1A C1A 175.6(35) . 3_546 ? C2A C1A C1A 67.2(18) 3_546 3_546 ? O1A C1A C2A 130.6(29) . . ? C2A C1A C2A 114.8(21) 3_546 . ? C1A C1A C2A 47.6(11) 3_546 . ? O1A C1A C1G 83.8(25) . 3_546 ? C2A C1A C1G 161.7(22) 3_546 3_546 ? C1A C1A C1G 94.7(16) 3_546 3_546 ? C2A C1A C1G 47.2(11) . 3_546 ? C1A C2A C1G 140.0(23) 3_546 3_546 ? C1A C2A C1A 65.2(21) 3_546 . ? C1G C2A C1A 75.0(15) 3_546 . ? 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 C3 O2 C1 C34 84.0(4) . . . 3_566 ? C1 O2 C3 C8 165.5(3) . . . . ? C1 O2 C3 C4 -15.0(5) . . . . ? O2 C3 C4 C5 -179.9(3) . . . . ? C8 C3 C4 C5 -0.5(5) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? C4 C5 C6 C7 0.1(5) . . . . ? C4 C5 C6 C9 174.1(3) . . . . ? C5 C6 C7 C8 0.9(5) . . . . ? C9 C6 C7 C8 -173.3(3) . . . . ? O2 C3 C8 C7 -179.0(3) . . . . ? C4 C3 C8 C7 1.5(5) . . . . ? C6 C7 C8 C3 -1.7(5) . . . . ? C5 C6 C9 C10 157.5(3) . . . . ? C7 C6 C9 C10 -28.5(4) . . . . ? C5 C6 C9 C22 32.9(4) . . . . ? C7 C6 C9 C22 -153.2(3) . . . . ? C5 C6 C9 C16 -92.6(3) . . . . ? C7 C6 C9 C16 81.3(3) . . . . ? C22 C9 C10 C15 59.3(4) . . . . ? C16 C9 C10 C15 179.8(3) . . . . ? C6 C9 C10 C15 -66.8(4) . . . . ? C22 C9 C10 C11 -121.1(3) . . . . ? C16 C9 C10 C11 -0.7(3) . . . . ? C6 C9 C10 C11 112.8(3) . . . . ? C15 C10 C11 C12 0.8(5) . . . . ? C9 C10 C11 C12 -178.8(3) . . . . ? C15 C10 C11 C17 179.4(3) . . . . ? C9 C10 C11 C17 -0.2(3) . . . . ? C10 C11 C12 C13 -0.9(5) . . . . ? C17 C11 C12 C13 -179.1(3) . . . . ? C11 C12 C13 C14 0.2(5) . . . . ? C12 C13 C14 C15 0.8(6) . . . . ? C13 C14 C15 C10 -0.9(5) . . . . ? C11 C10 C15 C14 0.1(5) . . . . ? C9 C10 C15 C14 179.6(3) . . . . ? C10 C9 C16 C21 176.9(3) . . . . ? C22 C9 C16 C21 -65.3(4) . . . . ? C6 C9 C16 C21 59.6(4) . . . . ? C10 C9 C16 C17 1.4(3) . . . . ? C22 C9 C16 C17 119.2(3) . . . . ? C6 C9 C16 C17 -116.0(3) . . . . ? C21 C16 C17 C18 -0.3(5) . . . . ? C9 C16 C17 C18 175.7(3) . . . . ? C21 C16 C17 C11 -177.6(3) . . . . ? C9 C16 C17 C11 -1.6(3) . . . . ? C12 C11 C17 C18 2.6(6) . . . . ? C10 C11 C17 C18 -175.8(3) . . . . ? C12 C11 C17 C16 179.5(3) . . . . ? C10 C11 C17 C16 1.2(3) . . . . ? C16 C17 C18 C19 0.3(5) . . . . ? C11 C17 C18 C19 176.9(3) . . . . ? C17 C18 C19 C20 0.2(5) . . . . ? C18 C19 C20 C21 -0.7(6) . . . . ? C17 C16 C21 C20 -0.2(5) . . . . ? C9 C16 C21 C20 -175.3(3) . . . . ? C19 C20 C21 C16 0.7(5) . . . . ? C10 C9 C22 C23 94.9(4) . . . . ? C16 C9 C22 C23 -17.6(4) . . . . ? C6 C9 C22 C23 -139.3(3) . . . . ? C10 C9 C22 C27 -81.3(4) . . . . ? C16 C9 C22 C27 166.2(3) . . . . ? C6 C9 C22 C27 44.5(4) . . . . ? C27 C22 C23 C24 0.6(5) . . . . ? C9 C22 C23 C24 -175.7(3) . . . . ? C22 C23 C24 C25 -0.9(6) . . . . ? C29 O28 C25 C24 -28.0(5) . . . . ? C29 O28 C25 C26 156.6(3) . . . . ? C23 C24 C25 O28 -175.0(3) . . . . ? C23 C24 C25 C26 0.3(6) . . . . ? O28 C25 C26 C27 176.4(3) . . . . ? C24 C25 C26 C27 0.6(5) . . . . ? C25 C26 C27 C22 -0.9(5) . . . . ? C23 C22 C27 C26 0.3(5) . . . . ? C9 C22 C27 C26 176.6(3) . . . . ? C25 O28 C29 C30 148.9(3) . . . . ? O28 C29 C30 C31 -89.9(4) . . . . ? O28 C29 C30 C39 85.9(4) . . . . ? C33 O32 C31 C30 -99.9(4) . . . . ? C33 O32 C31 C34 84.9(4) . . . . ? C39 C30 C31 O32 -175.2(3) . . . . ? C29 C30 C31 O32 0.6(5) . . . . ? C39 C30 C31 C34 -0.1(5) . . . . ? C29 C30 C31 C34 175.8(3) . . . . ? O32 C31 C34 C35 174.1(3) . . . . ? C30 C31 C34 C35 -1.1(5) . . . . ? O32 C31 C34 C1 -6.2(5) . . . 3_566 ? C30 C31 C34 C1 178.7(3) . . . 3_566 ? C31 C34 C35 C36 1.2(5) . . . . ? C1 C34 C35 C36 -178.5(3) 3_566 . . . ? C38 O37 C36 C35 -176.4(4) . . . . ? C38 O37 C36 C39 4.4(6) . . . . ? C34 C35 C36 O37 -179.5(4) . . . . ? C34 C35 C36 C39 -0.3(6) . . . . ? O37 C36 C39 C30 178.2(4) . . . . ? C35 C36 C39 C30 -0.9(6) . . . . ? C31 C30 C39 C36 1.1(5) . . . . ? C29 C30 C39 C36 -174.7(3) . . . . ? C2A C1G C2G C3G -1.1(37) 3_546 . . . ? C1A C1G C2G C3G -121.5(61) 3_546 . . . ? C2A C1G C2G C5G -145.5(93) 3_546 . . 3_556 ? C1A C1G C2G C5G 94.0(119) 3_546 . . 3_556 ? C2A C1G C2G N7G 179.2(20) 3_546 . . . ? C1A C1G C2G N7G 58.8(70) 3_546 . . . ? C5G C2G C3G C5G 0.000(5) 3_556 . . 3_556 ? N7G C2G C3G C5G 6.8(15) . . . 3_556 ? C1G C2G C3G C5G -172.9(25) . . . 3_556 ? C5G C2G C3G C4G -4.3(14) 3_556 . . . ? N7G C2G C3G C4G 2.5(22) . . . . ? C1G C2G C3G C4G -177.2(17) . . . . ? C2G C3G C4G C5G 4.6(15) . . . 3_556 ? C5G C3G C4G C5G 0.000(4) 3_556 . . 3_556 ? C2G C3G C4G N7G 154.1(93) . . . 3_556 ? C5G C3G C4G N7G 149.5(99) 3_556 . . 3_556 ? C2G C3G C4G C5G -3.9(21) . . . . ? C5G C3G C4G C5G -8.5(20) 3_556 . . . ? C5G C4G C5G C4G 0.000(3) 3_556 . . 3_556 ? N7G C4G C5G C4G -168.9(18) 3_556 . . 3_556 ? C3G C4G C5G C4G 8.2(19) . . . 3_556 ? C5G C4G C5G C3G 86.4(145) 3_556 . . 3_556 ? N7G C4G C5G C3G -82.6(145) 3_556 . . 3_556 ? C3G C4G C5G C3G 94.5(145) . . . 3_556 ? C5G C4G C5G C2G 167.7(27) 3_556 . . 3_556 ? N7G C4G C5G C2G -1.2(15) 3_556 . . 3_556 ? C3G C4G C5G C2G 175.9(15) . . . 3_556 ? C5G C4G C5G C5G 0.000(1) 3_556 . . 3_556 ? N7G C4G C5G C5G -168.9(18) 3_556 . . 3_556 ? C3G C4G C5G C5G 8.2(19) . . . 3_556 ? C5G C4G C5G N7G 168.9(18) 3_556 . . 3_556 ? N7G C4G C5G N7G 0.000(4) 3_556 . . 3_556 ? C3G C4G C5G N7G 177.1(14) . . . 3_556 ? C3G C2G N7G C4G -5.7(22) . . . 3_556 ? C5G C2G N7G C4G 1.1(14) 3_556 . . 3_556 ? C1G C2G N7G C4G 174.1(14) . . . 3_556 ? C3G C2G N7G C5G -6.8(15) . . . 3_556 ? C5G C2G N7G C5G 0.000(4) 3_556 . . 3_556 ? C1G C2G N7G C5G 172.9(20) . . . 3_556 ? O1A C1A C2A C1A -174.7(47) . . . 3_546 ? C2A C1A C2A C1A 0.000(6) 3_546 . . 3_546 ? C1A C1A C2A C1A 0.000(2) 3_546 . . 3_546 ? C1G C1A C2A C1A 175.7(26) 3_546 . . 3_546 ? O1A C1A C2A C1G 9.6(35) . . . 3_546 ? C2A C1A C2A C1G -175.7(26) 3_546 . . 3_546 ? C1A C1A C2A C1G -175.7(26) 3_546 . . 3_546 ? C1G C1A C2A C1G 0.000(2) 3_546 . . 3_546 ? _refine_diff_density_max 0.733 _refine_diff_density_min -0.512 _refine_diff_density_rmmny 0.113 data_3 _database_code_CSD 150565 # CHEMICAL DATA _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C77.50 H66 N O8.50' _chemical_formula_weight 1147.31 _chemical_melting_point ? _chemical_compound_source ? 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' 'N' 'N' 0.0061 0.0033 '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 P21/n 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 12.815(3) _cell_length_b 10.963(3) _cell_length_c 21.673(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.14(2) _cell_angle_gamma 90.00 _cell_volume 3044.8(12) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.961 _cell_measurement_theta_max 10.502 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method ? _exptl_crystal_F_000 1212 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'CAD4 (Enraf-Nonius)' _diffrn_measurement_method /w--2/q _diffrn_standards_number 3 _diffrn_standards_interval_count 250 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% ? _diffrn_reflns_number 6797 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.1133 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.03 _reflns_number_total 6502 _reflns_number_observed 3200 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 software' _computing_cell_refinement 'CAD4 software' _computing_data_reduction 'Helena' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON' _computing_publication_material 'PLATON' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1356 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.2270P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0115(30) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5146 _refine_ls_number_parameters 395 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.2204 _refine_ls_R_factor_obs 0.1124 _refine_ls_wR_factor_all 0.3999 _refine_ls_wR_factor_obs 0.3045 _refine_ls_goodness_of_fit_all 1.071 _refine_ls_goodness_of_fit_obs 1.241 _refine_ls_restrained_S_all 1.137 _refine_ls_restrained_S_obs 1.238 _refine_ls_shift/esd_max 0.057 _refine_ls_shift/esd_mean 0.003 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O2 O 0.1450(3) 0.7143(4) 0.2351(2) 0.0350(9) Uani 1 d . . O28 O -0.3121(4) 1.2122(4) 0.4848(2) 0.0452(11) Uani 1 d . . O32 O -0.3175(3) 1.1104(3) 0.6306(2) 0.0368(9) Uani 1 d . . O37 O -0.2913(4) 1.6121(4) 0.6299(2) 0.0599(15) Uani 1 d . . C1 C 0.2329(4) 0.7706(6) 0.2636(2) 0.0356(13) Uani 1 d . . H1A H 0.2138(4) 0.8545(6) 0.2761(2) 0.055(20) Uiso 1 calc R . H1B H 0.2901(4) 0.7766(6) 0.2331(2) 0.031(15) Uiso 1 calc R . C3 C 0.0497(4) 0.7417(5) 0.2599(2) 0.0308(12) Uani 1 d . . C4 C -0.0367(4) 0.7112(5) 0.2237(2) 0.0290(12) Uani 1 d . . H4A H -0.0275(4) 0.6735(5) 0.1841(2) 0.035 Uiso 1 d R . C5 C -0.1361(4) 0.7351(4) 0.2456(2) 0.0260(11) Uani 1 d . . H5A H -0.1952(4) 0.7132(4) 0.2207(2) 0.031 Uiso 1 d R . C6 C -0.1527(4) 0.7879(4) 0.3023(2) 0.0260(11) Uani 1 d . . C7 C -0.0673(4) 0.8172(5) 0.3373(2) 0.0329(13) Uani 1 d . . H7A H -0.0781(4) 0.8554(5) 0.3766(2) 0.040 Uiso 1 d R . C8 C 0.0337(4) 0.7950(5) 0.3175(2) 0.0354(13) Uani 1 d . . H8A H 0.0921(4) 0.8151(5) 0.3433(2) 0.043 Uiso 1 d R . C9 C -0.2652(4) 0.8014(5) 0.3270(2) 0.0258(11) Uani 1 d . . C10 C -0.3449(4) 0.8121(5) 0.2738(2) 0.0263(11) Uani 1 d . . C11 C -0.4104(4) 0.7092(5) 0.2724(2) 0.0299(12) Uani 1 d . . C12 C -0.4855(5) 0.7003(6) 0.2261(3) 0.0384(14) Uani 1 d . . H12A H -0.5288(5) 0.6290(6) 0.2239(3) 0.046 Uiso 1 d R . C13 C -0.4990(5) 0.7938(6) 0.1851(3) 0.045(2) Uani 1 d . . H13A H -0.5520(5) 0.7876(6) 0.1539(3) 0.054 Uiso 1 d R . C14 C -0.4353(4) 0.8971(6) 0.1878(2) 0.0396(14) Uani 1 d . . H14A H -0.4450(4) 0.9624(6) 0.1588(2) 0.048 Uiso 1 d R . C15 C -0.3576(4) 0.9056(5) 0.2319(2) 0.0330(13) Uani 1 d . . H15A H -0.3128(4) 0.9756(5) 0.2337(2) 0.040 Uiso 1 d R . C16 C -0.2952(4) 0.6770(4) 0.3536(2) 0.0285(12) Uani 1 d . . C17 C -0.3773(4) 0.6244(5) 0.3205(2) 0.0303(12) Uani 1 d . . C18 C -0.4128(5) 0.5081(5) 0.3354(3) 0.0376(14) Uani 1 d . . H18A H -0.4688(5) 0.4718(5) 0.3123(3) 0.045 Uiso 1 d R . C19 C -0.3648(5) 0.4454(5) 0.3818(3) 0.0419(15) Uani 1 d . . H19A H -0.3889(5) 0.3649(5) 0.3917(3) 0.050 Uiso 1 d R . C20 C -0.2832(5) 0.4976(5) 0.4160(3) 0.0406(14) Uani 1 d . . H20A H -0.2524(5) 0.4530(5) 0.4496(3) 0.049 Uiso 1 d R . C21 C -0.2482(5) 0.6133(5) 0.4013(3) 0.0359(13) Uani 1 d . . H21A H -0.1908(5) 0.6491(5) 0.4234(3) 0.043 Uiso 1 d R . C22 C -0.2784(4) 0.9070(5) 0.3715(2) 0.0264(11) Uani 1 d . . C23 C -0.2323(4) 1.0207(5) 0.3581(2) 0.0281(11) Uani 1 d . . H23A H -0.1924(4) 1.0304(5) 0.3210(2) 0.034 Uiso 1 d R . C24 C -0.2460(4) 1.1189(5) 0.3967(2) 0.0304(12) Uani 1 d . . H24A H -0.2113(4) 1.1947(5) 0.3884(2) 0.036 Uiso 1 d R . C25 C -0.3080(4) 1.1086(5) 0.4481(2) 0.0298(12) Uani 1 d . . C26 C -0.3544(5) 0.9983(5) 0.4628(2) 0.0363(14) Uani 1 d . . H26A H -0.3975(5) 0.9906(5) 0.4988(2) 0.044 Uiso 1 d R . C27 C -0.3370(4) 0.8992(5) 0.4238(2) 0.0331(13) Uani 1 d . . H27A H -0.3676(4) 0.8220(5) 0.4342(2) 0.040 Uiso 1 d R . C29 C -0.3981(5) 1.2294(5) 0.5261(2) 0.0375(14) Uani 1 d . . H29A H -0.4263(5) 1.1523(5) 0.5387(2) 0.045 Uiso 1 d R . H29B H -0.4522(5) 1.2755(5) 0.5061(2) 0.045 Uiso 1 d R . C30 C -0.3565(4) 1.2991(5) 0.5810(2) 0.0314(12) Uani 1 d . . C31 C -0.3170(4) 1.2368(5) 0.6310(2) 0.0280(11) Uani 1 d . . C33 C -0.4019(5) 1.0556(6) 0.6630(3) 0.046(2) Uani 1 d . . H33A H -0.3956(5) 0.9685(6) 0.6602(3) 0.069 Uiso 1 d R . H33B H -0.4005(5) 1.0797(6) 0.7055(3) 0.069 Uiso 1 d R . H33C H -0.4665(5) 1.0809(6) 0.6446(3) 0.069 Uiso 1 d R . C34 C -0.2715(4) 1.2985(5) 0.6804(2) 0.0300(12) Uani 1 d . . C35 C -0.2647(4) 1.4240(5) 0.6773(2) 0.0336(13) Uani 1 d . . H35A H -0.2317(4) 1.4679(5) 0.7103(2) 0.040 Uiso 1 d R . C36 C -0.3036(5) 1.4880(5) 0.6273(3) 0.0350(13) Uani 1 d . . C38 C -0.3390(7) 1.6833(6) 0.5833(3) 0.065(2) Uani 1 d . . H38A H -0.3243(7) 1.7681(6) 0.5899(3) 0.098 Uiso 1 d R . H38B H -0.3130(7) 1.6592(6) 0.5436(3) 0.098 Uiso 1 d R . H38C H -0.4130(7) 1.6701(6) 0.5847(3) 0.098 Uiso 1 d R . C39 C -0.3505(4) 1.4253(5) 0.5793(2) 0.0343(13) Uani 1 d . . H39A H -0.3775(4) 1.4696(5) 0.5445(2) 0.041 Uiso 1 d R . C2G C 0.0555(13) 0.2967(14) 0.4661(8) 0.152(11) Uiso 0.50 d PD 1 C3G C 0.0869(16) 0.4149(17) 0.4521(12) 0.248(22) Uiso 0.50 d PD 1 H3GA H 0.1431(16) 0.4266(17) 0.4235(12) 0.297 Uiso 0.50 d PR 1 C5G C -0.0403(16) 0.4940(13) 0.5232(11) 0.153(11) Uiso 0.50 d PD 1 H5GA H -0.0714(16) 0.5637(13) 0.5428(11) 0.184 Uiso 0.50 d PR 1 N6G N -0.0732(11) 0.3760(15) 0.5361(6) 0.137(8) Uiso 0.50 d PD 1 C7G C -0.0257(13) 0.2773(11) 0.5073(7) 0.202(8) Uiso 1 d D 1 H7GA H -0.0482(13) 0.1957(11) 0.5162(7) 0.242 Uiso 1 d R 1 C1G C 0.1074(23) 0.1854(22) 0.4338(14) 0.371(38) Uiso 0.50 d PD 1 H1GA H 0.0763(23) 0.1113(22) 0.4486(14) 0.556 Uiso 0.50 d PR 1 H1GB H 0.0985(23) 0.1906(22) 0.3899(14) 0.556 Uiso 0.50 d PR 1 H1GC H 0.1805(23) 0.1855(22) 0.4436(14) 0.556 Uiso 0.50 d PR 1 C2A C 0.0587(28) 0.8737(27) 0.4833(16) 0.067(9) Uiso 0.25 d PD 2 H2AA H 0.1244(28) 0.8586(27) 0.4635(16) 0.101 Uiso 0.25 d PR 2 H2AB H 0.0582(28) 0.8353(27) 0.5231(16) 0.101 Uiso 0.25 d PR 2 H2AC H 0.0032(28) 0.8411(27) 0.4584(16) 0.101 Uiso 0.25 d PR 2 C1A C 0.0413(22) 1.0089(29) 0.4846(12) 0.077(11) Uiso 0.25 d PD 2 O1A O 0.1088(29) 1.0597(37) 0.4560(16) 0.149(13) Uiso 0.25 d PD 2 C3A C -0.0516(26) 1.0525(38) 0.5193(17) 0.067(8) Uiso 0.25 d PD 2 H3AA H -0.0611(26) 1.1392(38) 0.5218(17) 0.101 Uiso 0.25 d PR 2 H3AB H -0.1081(26) 1.0171(38) 0.4963(17) 0.101 Uiso 0.25 d PR 2 H3AC H -0.0503(26) 1.0186(38) 0.5601(17) 0.101 Uiso 0.25 d PR 2 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 O2 0.032(2) 0.046(2) 0.027(2) -0.002(2) -0.001(2) 0.007(2) O28 0.070(3) 0.026(2) 0.040(2) -0.010(2) 0.013(2) -0.011(2) O32 0.035(2) 0.027(2) 0.048(2) 0.000(2) 0.003(2) 0.002(2) O37 0.102(4) 0.025(2) 0.052(3) -0.005(2) -0.033(3) 0.003(2) C1 0.025(3) 0.048(4) 0.034(3) 0.005(3) 0.004(2) 0.000(3) C3 0.038(3) 0.026(3) 0.028(3) 0.002(2) -0.001(2) 0.007(2) C4 0.038(3) 0.026(3) 0.023(2) -0.004(2) -0.002(2) 0.009(2) C5 0.023(3) 0.025(3) 0.030(3) -0.003(2) -0.006(2) 0.000(2) C6 0.031(3) 0.022(2) 0.025(2) 0.002(2) -0.002(2) 0.004(2) C7 0.032(3) 0.039(3) 0.028(3) -0.009(2) -0.001(2) 0.006(2) C8 0.031(3) 0.041(3) 0.035(3) -0.007(2) -0.008(2) 0.005(3) C9 0.030(3) 0.025(3) 0.022(2) -0.003(2) -0.001(2) 0.002(2) C10 0.028(3) 0.025(3) 0.026(2) -0.001(2) 0.000(2) 0.005(2) C11 0.027(3) 0.025(3) 0.037(3) -0.003(2) 0.001(2) 0.003(2) C12 0.040(3) 0.043(3) 0.033(3) -0.006(3) 0.003(2) -0.002(3) C13 0.034(3) 0.061(4) 0.039(3) -0.003(3) -0.010(3) 0.004(3) C14 0.034(3) 0.055(4) 0.029(3) 0.005(3) -0.001(2) 0.007(3) C15 0.033(3) 0.035(3) 0.031(3) 0.000(2) 0.007(2) 0.005(2) C16 0.038(3) 0.021(2) 0.027(2) -0.004(2) 0.004(2) 0.002(2) C17 0.032(3) 0.030(3) 0.030(3) -0.006(2) 0.007(2) 0.004(2) C18 0.038(3) 0.029(3) 0.045(3) -0.004(2) 0.005(3) -0.004(3) C19 0.060(4) 0.025(3) 0.040(3) 0.006(2) 0.009(3) -0.004(3) C20 0.050(4) 0.034(3) 0.038(3) 0.004(2) 0.005(3) 0.008(3) C21 0.047(3) 0.027(3) 0.034(3) 0.000(2) -0.001(2) 0.001(3) C22 0.035(3) 0.023(2) 0.022(2) -0.002(2) -0.003(2) 0.000(2) C23 0.031(3) 0.033(3) 0.020(2) 0.000(2) -0.001(2) -0.001(2) C24 0.037(3) 0.020(3) 0.034(3) 0.000(2) -0.003(2) -0.004(2) C25 0.046(3) 0.022(3) 0.021(2) -0.002(2) -0.005(2) 0.004(2) C26 0.054(4) 0.029(3) 0.025(3) -0.002(2) 0.008(2) -0.005(3) C27 0.043(3) 0.024(3) 0.033(3) -0.002(2) 0.002(2) -0.004(2) C29 0.049(4) 0.032(3) 0.032(3) -0.007(2) -0.004(3) 0.007(3) C30 0.033(3) 0.029(3) 0.032(3) -0.009(2) 0.006(2) 0.004(2) C31 0.026(3) 0.024(3) 0.034(3) -0.002(2) 0.004(2) 0.005(2) C33 0.049(4) 0.035(3) 0.054(4) 0.008(3) -0.005(3) -0.003(3) C34 0.027(3) 0.031(3) 0.032(3) 0.002(2) 0.000(2) 0.003(2) C35 0.034(3) 0.033(3) 0.034(3) -0.004(2) -0.008(2) 0.001(2) C36 0.047(3) 0.024(3) 0.034(3) -0.004(2) -0.006(2) 0.002(3) C38 0.117(7) 0.029(3) 0.049(4) 0.006(3) -0.013(4) 0.007(4) C39 0.041(3) 0.029(3) 0.033(3) 0.001(2) -0.003(2) 0.004(2) _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 O2 C3 1.369(6) . ? O2 C1 1.424(7) . ? O28 C25 1.388(6) . ? O28 C29 1.434(7) . ? O32 C31 1.386(6) . ? O32 C33 1.423(7) . ? O37 C36 1.371(7) . ? O37 C38 1.414(8) . ? C1 C34 1.513(7) 3_576 ? C3 C8 1.394(7) . ? C3 C4 1.396(8) . ? C4 C5 1.385(7) . ? C5 C6 1.377(7) . ? C6 C7 1.367(7) . ? C6 C9 1.545(7) . ? C7 C8 1.385(8) . ? C9 C22 1.518(7) . ? C9 C16 1.531(7) . ? C9 C10 1.543(7) . ? C10 C15 1.377(7) . ? C10 C11 1.407(7) . ? C11 C12 1.391(8) . ? C11 C17 1.458(8) . ? C12 C13 1.367(9) . ? C13 C14 1.397(9) . ? C14 C15 1.382(8) . ? C16 C21 1.384(8) . ? C16 C17 1.397(8) . ? C17 C18 1.393(8) . ? C18 C19 1.364(8) . ? C19 C20 1.402(9) . ? C20 C21 1.383(8) . ? C22 C27 1.363(7) . ? C22 C23 1.410(7) . ? C23 C24 1.375(7) . ? C24 C25 1.374(7) . ? C25 C26 1.385(8) . ? C26 C27 1.396(7) . ? C29 C30 1.509(7) . ? C30 C31 1.378(7) . ? C30 C39 1.386(7) . ? C31 C34 1.393(7) . ? C34 C35 1.380(8) . ? C34 C1 1.513(7) 3_576 ? C35 C36 1.382(8) . ? C36 C39 1.384(8) . ? C2G C7G 1.3900(11) . ? C2G C3G 1.3901(11) . ? C2G C1G 1.557(8) . ? C3G C5G 1.28(3) 3_566 ? C5G C3G 1.28(3) 3_566 ? C5G N6G 1.3898(11) . ? C5G C5G 1.45(4) 3_566 ? N6G C7G 1.3898(11) . ? C2A C3A 0.82(4) 3_576 ? C2A C1A 1.50(2) . ? C2A C1A 1.95(5) 3_576 ? C1A C3A 0.69(4) 3_576 ? C1A O1A 1.20(2) . ? C1A C1A 1.27(6) 3_576 ? C1A C3A 1.49(2) . ? C1A C2A 1.95(5) 3_576 ? O1A C3A 1.53(5) 3_576 ? C3A C1A 0.69(4) 3_576 ? C3A C2A 0.82(4) 3_576 ? C3A O1A 1.53(5) 3_576 ? C3A C3A 1.94(6) 3_576 ? 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 C3 O2 C1 116.1(4) . . ? C25 O28 C29 119.7(4) . . ? C31 O32 C33 115.0(4) . . ? C36 O37 C38 118.1(5) . . ? O2 C1 C34 112.8(5) . 3_576 ? O2 C3 C8 125.3(5) . . ? O2 C3 C4 115.7(4) . . ? C8 C3 C4 119.0(5) . . ? C5 C4 C3 119.4(5) . . ? C6 C5 C4 122.0(5) . . ? C7 C6 C5 117.9(5) . . ? C7 C6 C9 122.2(4) . . ? C5 C6 C9 119.7(4) . . ? C6 C7 C8 122.3(5) . . ? C7 C8 C3 119.4(5) . . ? C22 C9 C16 114.3(4) . . ? C22 C9 C10 110.0(4) . . ? C16 C9 C10 100.6(4) . . ? C22 C9 C6 113.5(4) . . ? C16 C9 C6 106.3(4) . . ? C10 C9 C6 111.5(4) . . ? C15 C10 C11 120.9(5) . . ? C15 C10 C9 128.7(5) . . ? C11 C10 C9 110.4(4) . . ? C12 C11 C10 118.8(5) . . ? C12 C11 C17 132.1(5) . . ? C10 C11 C17 108.9(5) . . ? C13 C12 C11 120.2(6) . . ? C12 C13 C14 120.5(6) . . ? C15 C14 C13 120.2(6) . . ? C10 C15 C14 119.3(6) . . ? C21 C16 C17 120.2(5) . . ? C21 C16 C9 128.5(5) . . ? C17 C16 C9 111.2(5) . . ? C18 C17 C16 120.3(5) . . ? C18 C17 C11 130.9(5) . . ? C16 C17 C11 108.8(5) . . ? C19 C18 C17 119.0(6) . . ? C18 C19 C20 121.3(5) . . ? C21 C20 C19 119.6(6) . . ? C20 C21 C16 119.6(6) . . ? C27 C22 C23 117.3(4) . . ? C27 C22 C9 122.9(5) . . ? C23 C22 C9 119.7(4) . . ? C24 C23 C22 120.8(4) . . ? C23 C24 C25 120.3(5) . . ? C24 C25 C26 120.5(5) . . ? C24 C25 O28 114.8(5) . . ? C26 C25 O28 124.4(5) . . ? C25 C26 C27 118.1(5) . . ? C22 C27 C26 123.0(5) . . ? O28 C29 C30 106.7(5) . . ? C31 C30 C39 119.8(5) . . ? C31 C30 C29 119.8(5) . . ? C39 C30 C29 120.3(5) . . ? C30 C31 O32 119.3(5) . . ? C30 C31 C34 121.1(5) . . ? O32 C31 C34 119.5(5) . . ? C35 C34 C31 118.2(5) . . ? C35 C34 C1 121.2(5) . 3_576 ? C31 C34 C1 120.5(5) . 3_576 ? C34 C35 C36 121.5(5) . . ? O37 C36 C35 115.6(5) . . ? O37 C36 C39 124.9(5) . . ? C35 C36 C39 119.5(5) . . ? C30 C39 C36 119.9(5) . . ? C7G C2G C3G 120.01(14) . . ? C7G C2G C1G 119.3(6) . . ? C3G C2G C1G 120.6(6) . . ? C5G C3G C2G 120.0(14) 3_566 . ? C3G C5G N6G 120.0(14) 3_566 . ? C3G C5G C5G 123.6(20) 3_566 3_566 ? N6G C5G C5G 116.1(10) . 3_566 ? C7G N6G C5G 120.07(14) . . ? N6G C7G C2G 119.94(12) . . ? C3A C2A C1A 5.5(36) 3_576 . ? C3A C2A C1A 45.2(35) 3_576 3_576 ? C1A C2A C1A 40.6(24) . 3_576 ? C3A C1A O1A 104.5(56) 3_576 . ? C3A C1A C1A 94.3(52) 3_576 3_576 ? O1A C1A C1A 161.0(46) . 3_576 ? C3A C1A C3A 121.9(51) 3_576 . ? O1A C1A C3A 133.6(40) . . ? C1A C1A C3A 27.6(18) 3_576 . ? C3A C1A C2A 6.5(43) 3_576 . ? O1A C1A C2A 109.9(29) . . ? C1A C1A C2A 89.0(35) 3_576 . ? C3A C1A C2A 116.5(34) . . ? C3A C1A C2A 144.5(56) 3_576 3_576 ? O1A C1A C2A 110.7(33) . 3_576 ? C1A C1A C2A 50.4(20) 3_576 3_576 ? C3A C1A C2A 22.9(19) . 3_576 ? C2A C1A C2A 139.4(24) . 3_576 ? C1A O1A C3A 26.0(22) . 3_576 ? C1A C3A C2A 168.0(79) 3_576 3_576 ? C1A C3A C1A 58.1(51) 3_576 . ? C2A C3A C1A 111.9(51) 3_576 . ? C1A C3A O1A 49.6(39) 3_576 3_576 ? C2A C3A O1A 140.2(49) 3_576 3_576 ? C1A C3A O1A 107.6(38) . 3_576 ? C1A C3A C3A 40.6(39) 3_576 3_576 ? C2A C3A C3A 129.3(56) 3_576 3_576 ? C1A C3A C3A 17.6(14) . 3_576 ? O1A C3A C3A 90.1(34) 3_576 3_576 ? 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 C3 O2 C1 C34 84.1(6) . . . 3_576 ? C1 O2 C3 C8 -15.7(7) . . . . ? C1 O2 C3 C4 165.2(5) . . . . ? O2 C3 C4 C5 179.6(5) . . . . ? C8 C3 C4 C5 0.4(8) . . . . ? C3 C4 C5 C6 -0.3(8) . . . . ? C4 C5 C6 C7 0.2(8) . . . . ? C4 C5 C6 C9 -174.3(5) . . . . ? C5 C6 C7 C8 -0.3(8) . . . . ? C9 C6 C7 C8 174.0(5) . . . . ? C6 C7 C8 C3 0.4(9) . . . . ? O2 C3 C8 C7 -179.6(5) . . . . ? C4 C3 C8 C7 -0.5(8) . . . . ? C7 C6 C9 C22 32.8(7) . . . . ? C5 C6 C9 C22 -153.0(5) . . . . ? C7 C6 C9 C16 -93.6(6) . . . . ? C5 C6 C9 C16 80.6(5) . . . . ? C7 C6 C9 C10 157.7(5) . . . . ? C5 C6 C9 C10 -28.1(6) . . . . ? C22 C9 C10 C15 59.2(7) . . . . ? C16 C9 C10 C15 -180.0(5) . . . . ? C6 C9 C10 C15 -67.6(7) . . . . ? C22 C9 C10 C11 -119.9(5) . . . . ? C16 C9 C10 C11 1.0(5) . . . . ? C6 C9 C10 C11 113.4(5) . . . . ? C15 C10 C11 C12 3.0(7) . . . . ? C9 C10 C11 C12 -177.8(5) . . . . ? C15 C10 C11 C17 178.4(5) . . . . ? C9 C10 C11 C17 -2.5(6) . . . . ? C10 C11 C12 C13 -3.9(8) . . . . ? C17 C11 C12 C13 -178.0(6) . . . . ? C11 C12 C13 C14 2.4(9) . . . . ? C12 C13 C14 C15 0.1(9) . . . . ? C11 C10 C15 C14 -0.6(8) . . . . ? C9 C10 C15 C14 -179.5(5) . . . . ? C13 C14 C15 C10 -1.0(8) . . . . ? C22 C9 C16 C21 -65.4(7) . . . . ? C10 C9 C16 C21 176.8(5) . . . . ? C6 C9 C16 C21 60.6(6) . . . . ? C22 C9 C16 C17 118.7(5) . . . . ? C10 C9 C16 C17 0.9(5) . . . . ? C6 C9 C16 C17 -115.4(5) . . . . ? C21 C16 C17 C18 0.3(7) . . . . ? C9 C16 C17 C18 176.6(5) . . . . ? C21 C16 C17 C11 -178.7(5) . . . . ? C9 C16 C17 C11 -2.4(6) . . . . ? C12 C11 C17 C18 -1.3(10) . . . . ? C10 C11 C17 C18 -175.9(5) . . . . ? C12 C11 C17 C16 177.6(6) . . . . ? C10 C11 C17 C16 3.0(6) . . . . ? C16 C17 C18 C19 -1.4(8) . . . . ? C11 C17 C18 C19 177.4(5) . . . . ? C17 C18 C19 C20 2.2(8) . . . . ? C18 C19 C20 C21 -2.0(9) . . . . ? C19 C20 C21 C16 0.9(8) . . . . ? C17 C16 C21 C20 -0.1(8) . . . . ? C9 C16 C21 C20 -175.7(5) . . . . ? C16 C9 C22 C27 -16.9(7) . . . . ? C10 C9 C22 C27 95.4(6) . . . . ? C6 C9 C22 C27 -139.0(5) . . . . ? C16 C9 C22 C23 165.8(5) . . . . ? C10 C9 C22 C23 -82.0(6) . . . . ? C6 C9 C22 C23 43.7(6) . . . . ? C27 C22 C23 C24 0.3(8) . . . . ? C9 C22 C23 C24 177.8(5) . . . . ? C22 C23 C24 C25 -2.2(8) . . . . ? C23 C24 C25 C26 2.3(8) . . . . ? C23 C24 C25 O28 177.3(5) . . . . ? C29 O28 C25 C24 158.6(5) . . . . ? C29 O28 C25 C26 -26.6(8) . . . . ? C24 C25 C26 C27 -0.6(9) . . . . ? O28 C25 C26 C27 -175.1(5) . . . . ? C23 C22 C27 C26 1.4(9) . . . . ? C9 C22 C27 C26 -176.0(5) . . . . ? C25 C26 C27 C22 -1.3(9) . . . . ? C25 O28 C29 C30 148.5(5) . . . . ? O28 C29 C30 C31 -90.2(6) . . . . ? O28 C29 C30 C39 84.9(6) . . . . ? C39 C30 C31 O32 -176.0(5) . . . . ? C29 C30 C31 O32 -0.9(8) . . . . ? C39 C30 C31 C34 0.4(8) . . . . ? C29 C30 C31 C34 175.5(5) . . . . ? C33 O32 C31 C30 -98.2(6) . . . . ? C33 O32 C31 C34 85.3(6) . . . . ? C30 C31 C34 C35 -1.5(8) . . . . ? O32 C31 C34 C35 174.9(5) . . . . ? C30 C31 C34 C1 177.2(5) . . . 3_576 ? O32 C31 C34 C1 -6.4(7) . . . 3_576 ? C31 C34 C35 C36 1.3(8) . . . . ? C1 C34 C35 C36 -177.4(5) 3_576 . . . ? C38 O37 C36 C35 -173.6(6) . . . . ? C38 O37 C36 C39 6.8(10) . . . . ? C34 C35 C36 O37 -179.7(6) . . . . ? C34 C35 C36 C39 -0.1(9) . . . . ? C31 C30 C39 C36 0.9(8) . . . . ? C29 C30 C39 C36 -174.2(5) . . . . ? O37 C36 C39 C30 178.5(6) . . . . ? C35 C36 C39 C30 -1.1(9) . . . . ? C7G C2G C3G C5G -0.6(33) . . . 3_566 ? C1G C2G C3G C5G 176.7(30) . . . 3_566 ? C3G C5G N6G C7G 177.2(30) 3_566 . . . ? C5G C5G N6G C7G 3.1(26) 3_566 . . . ? C5G N6G C7G C2G 0.8(6) . . . . ? C3G C2G C7G N6G -2.3(13) . . . . ? C1G C2G C7G N6G -179.6(7) . . . . ? C3A C2A C1A C3A 0.0(5) 3_576 . . 3_576 ? C1A C2A C1A C3A -144.7(432) 3_576 . . 3_576 ? C3A C2A C1A O1A -33.3(410) 3_576 . . . ? C1A C2A C1A O1A -178.0(26) 3_576 . . . ? C3A C2A C1A C1A 144.7(432) 3_576 . . 3_576 ? C1A C2A C1A C1A 0.000(8) 3_576 . . 3_576 ? C3A C2A C1A C3A 146.7(409) 3_576 . . . ? C1A C2A C1A C3A 1.9(25) 3_576 . . . ? C3A C2A C1A C2A 144.7(432) 3_576 . . 3_576 ? C1A C2A C1A C2A 0.000(11) 3_576 . . 3_576 ? C3A C1A O1A C3A 0.00(4) 3_576 . . 3_576 ? C1A C1A O1A C3A -170.2(126) 3_576 . . 3_576 ? C3A C1A O1A C3A -176.3(48) . . . 3_576 ? C2A C1A O1A C3A 3.7(48) . . . 3_576 ? C2A C1A O1A C3A -174.9(66) 3_576 . . 3_576 ? C3A C1A C3A C1A 0.000(14) 3_576 . . 3_576 ? O1A C1A C3A C1A 175.7(55) . . . 3_576 ? C1A C1A C3A C1A 0.00(2) 3_576 . . 3_576 ? C2A C1A C3A C1A -4.2(55) . . . 3_576 ? C2A C1A C3A C1A 172.6(97) 3_576 . . 3_576 ? C3A C1A C3A C2A -172.6(97) 3_576 . . 3_576 ? O1A C1A C3A C2A 3.2(43) . . . 3_576 ? C1A C1A C3A C2A -172.6(97) 3_576 . . 3_576 ? C2A C1A C3A C2A -176.8(43) . . . 3_576 ? C2A C1A C3A C2A 0.00(2) 3_576 . . 3_576 ? C3A C1A C3A O1A 2.5(33) 3_576 . . 3_576 ? O1A C1A C3A O1A 178.3(22) . . . 3_576 ? C1A C1A C3A O1A 2.5(33) 3_576 . . 3_576 ? C2A C1A C3A O1A -1.6(22) . . . 3_576 ? C2A C1A C3A O1A 175.1(65) 3_576 . . 3_576 ? C3A C1A C3A C3A 0.000(14) 3_576 . . 3_576 ? O1A C1A C3A C3A 175.7(55) . . . 3_576 ? C1A C1A C3A C3A 0.00(3) 3_576 . . 3_576 ? C2A C1A C3A C3A -4.2(55) . . . 3_576 ? C2A C1A C3A C3A 172.6(97) 3_576 . . 3_576 ? _refine_diff_density_max 1.046 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.140 data_44 _database_code_CSD 150566 # CHEMICAL DATA _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C78.50 H66 O8.50' _chemical_formula_weight 1145.31 _chemical_melting_point ? _chemical_compound_source ? 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 P21/n 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 12.8040(10) _cell_length_b 10.892(6) _cell_length_c 21.865 _cell_angle_alpha 90.00(3) _cell_angle_beta 90.47 _cell_angle_gamma 90.00 _cell_volume 3049.2(17) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.616 _cell_measurement_theta_max 10.213 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method ? _exptl_crystal_F_000 1210 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71140 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CAD4 (Enraf-Nonius)' _diffrn_measurement_method /w--2/q _diffrn_standards_number 3 _diffrn_standards_interval_count 250 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% none _diffrn_reflns_number 6716 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 26.99 _reflns_number_total 6419 _reflns_number_observed 4835 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 software' _computing_cell_refinement 'CAD4 software' _computing_data_reduction 'Helena' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON' _computing_publication_material 'PLATON' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 9 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1695P)^2^+3.9291P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6410 _refine_ls_number_parameters 380 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1123 _refine_ls_R_factor_obs 0.0859 _refine_ls_wR_factor_all 0.2850 _refine_ls_wR_factor_obs 0.2505 _refine_ls_goodness_of_fit_all 1.042 _refine_ls_goodness_of_fit_obs 1.080 _refine_ls_restrained_S_all 1.064 _refine_ls_restrained_S_obs 1.081 _refine_ls_shift/esd_max 0.042 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O2 O -0.3087(2) 1.2123(2) 0.48573(11) 0.0417(6) Uani 1 d . . O28 O 0.1449(2) 0.7135(2) 0.23644(10) 0.0340(5) Uani 1 d . . O32 O 0.3172(2) 0.8890(2) 0.37042(11) 0.0377(6) Uani 1 d . . O37 O 0.2908(2) 0.3840(2) 0.37051(12) 0.0506(7) Uani 1 d . . C1 C -0.3958(3) 1.2317(3) 0.52539(15) 0.0378(8) Uani 1 d . . H1A H -0.4256(3) 1.1521(3) 0.53833(15) 0.045 Uiso 1 calc R . H1B H -0.4510(3) 1.2793(3) 0.50401(15) 0.045 Uiso 1 calc R . C3 C -0.3057(3) 1.1094(3) 0.44928(13) 0.0294(6) Uani 1 d . . C4 C -0.3516(3) 0.9978(3) 0.46291(14) 0.0350(7) Uani 1 d . . H4A H -0.3941(3) 0.9893(3) 0.49864(14) 0.042 Uiso 1 d R . C5 C -0.3356(2) 0.8978(3) 0.42446(14) 0.0304(7) Uani 1 d . . H5A H -0.3670(2) 0.8203(3) 0.43431(14) 0.036 Uiso 1 d R . C6 C -0.2762(2) 0.9067(3) 0.37210(12) 0.0243(6) Uani 1 d . . C7 C -0.2310(2) 1.0205(3) 0.35918(13) 0.0264(6) Uani 1 d . . H7A H -0.1888(2) 1.0290(3) 0.32333(13) 0.032 Uiso 1 d R . C8 C -0.2452(2) 1.1203(3) 0.39713(13) 0.0284(6) Uani 1 d . . H8A H -0.2139(2) 1.1979(3) 0.38733(13) 0.034 Uiso 1 d R . C9 C -0.2644(2) 0.7996(3) 0.32735(13) 0.0241(6) Uani 1 d . . C10 C -0.3449(2) 0.8109(3) 0.27567(13) 0.0261(6) Uani 1 d . . C11 C -0.4097(2) 0.7074(3) 0.27312(14) 0.0278(6) Uani 1 d . . C12 C -0.4874(3) 0.6972(3) 0.2290(2) 0.0366(7) Uani 1 d . . H12A H -0.5316(3) 0.6260(3) 0.2275(2) 0.044 Uiso 1 d R . C13 C -0.5002(3) 0.7916(4) 0.1869(2) 0.0406(8) Uani 1 d . . H13A H -0.5533(3) 0.7857(4) 0.1558(2) 0.049 Uiso 1 d R . C14 C -0.4368(3) 0.8949(3) 0.18968(15) 0.0372(7) Uani 1 d . . H14A H -0.4475(3) 0.9601(3) 0.16079(15) 0.045 Uiso 1 d R . C15 C -0.3584(2) 0.9050(3) 0.23325(13) 0.0296(6) Uani 1 d . . H15A H -0.3137(2) 0.9758(3) 0.23441(13) 0.035 Uiso 1 d R . C16 C -0.2943(2) 0.6750(3) 0.35423(13) 0.0271(6) Uani 1 d . . C17 C -0.3775(2) 0.6228(3) 0.32186(14) 0.0282(6) Uani 1 d . . C18 C -0.4134(3) 0.5057(3) 0.3363(2) 0.0361(7) Uani 1 d . . H18A H -0.4708(3) 0.4699(3) 0.3141(2) 0.043 Uiso 1 d R . C19 C -0.3648(3) 0.4427(3) 0.3833(2) 0.0408(8) Uani 1 d . . H19A H -0.3884(3) 0.3619(3) 0.3939(2) 0.049 Uiso 1 d R . C20 C -0.2814(3) 0.4944(3) 0.4158(2) 0.0386(8) Uani 1 d . . H20A H -0.2484(3) 0.4495(3) 0.4484(2) 0.046 Uiso 1 d R . C21 C -0.2459(3) 0.6105(3) 0.40149(14) 0.0327(7) Uani 1 d . . H21A H -0.1884(3) 0.6463(3) 0.42358(14) 0.039 Uiso 1 d R . C22 C -0.1525(2) 0.7871(3) 0.30294(13) 0.0245(6) Uani 1 d . . C23 C -0.0664(3) 0.8165(3) 0.33832(14) 0.0333(7) Uani 1 d . . H23A H -0.0766(3) 0.8525(3) 0.37791(14) 0.040 Uiso 1 d R . C24 C 0.0351(3) 0.7939(3) 0.3180(2) 0.0358(7) Uani 1 d . . H24A H 0.0941(3) 0.8158(3) 0.3430(2) 0.043 Uiso 1 d R . C25 C 0.0494(2) 0.7403(3) 0.26100(13) 0.0268(6) Uani 1 d . . C26 C -0.0367(2) 0.7101(3) 0.22513(13) 0.0281(6) Uani 1 d . . H26A H -0.0275(2) 0.6721(3) 0.18593(13) 0.034 Uiso 1 d R . C27 C -0.1357(2) 0.7344(3) 0.24572(13) 0.0261(6) Uani 1 d . . H27A H -0.1947(2) 0.7145(3) 0.22028(13) 0.031 Uiso 1 d R . C29 C 0.2339(2) 0.7689(3) 0.2647(2) 0.0356(7) Uani 1 d . . H29A H 0.2157(2) 0.8537(3) 0.2770(2) 0.043 Uiso 1 calc R . H29B H 0.2908(2) 0.7740(3) 0.2345(2) 0.043 Uiso 1 calc R . C30 C 0.2730(2) 0.6996(3) 0.32037(14) 0.0301(7) Uani 1 d . . C31 C 0.3174(2) 0.7619(3) 0.36946(14) 0.0300(6) Uani 1 d . . C33 C 0.4026(3) 0.9437(3) 0.3380(2) 0.0440(8) Uani 1 d . . H33A H 0.3975(3) 1.0315(3) 0.3406(2) 0.066 Uiso 1 d R . H33B H 0.4677(3) 0.9173(3) 0.3556(2) 0.066 Uiso 1 d R . H33C H 0.3992(3) 0.9190(3) 0.2959(2) 0.066 Uiso 1 d R . C34 C 0.3558(2) 0.6984(3) 0.42004(14) 0.0309(7) Uani 1 d . . C35 C 0.3502(3) 0.5710(3) 0.42150(14) 0.0328(7) Uani 1 d . . H35A H 0.3781(3) 0.5265(3) 0.45581(14) 0.039 Uiso 1 d R . C36 C 0.3041(3) 0.5086(3) 0.37302(15) 0.0357(7) Uani 1 d . . C38 C 0.3385(4) 0.3119(4) 0.4169(2) 0.0620(12) Uani 1 d . . H38A H 0.3229(4) 0.2268(4) 0.4097(2) 0.093 Uiso 1 d R . H38B H 0.4127(4) 0.3239(4) 0.4161(2) 0.093 Uiso 1 d R . H38C H 0.3122(4) 0.3357(4) 0.4561(2) 0.093 Uiso 1 d R . C39 C 0.2660(3) 0.5729(3) 0.32289(15) 0.0349(7) Uani 1 d . . H39A H 0.2343(3) 0.5290(3) 0.28949(15) 0.042 Uiso 1 d R . C3G C 0.0611(7) 0.5704(9) 0.4668(4) 0.127(3) Uiso 1 d . . H3GA H 0.1052(7) 0.6189(9) 0.4411(4) 0.152 Uiso 1 d R . C2G C -0.0080(9) 0.6393(9) 0.5098(6) 0.152(4) Uiso 1 d D . C4G C -0.0645(7) 0.5494(9) 0.5356(4) 0.119(3) Uiso 1 d . . H4GA H -0.1164(7) 0.5824(9) 0.5624(4) 0.143 Uiso 1 d R . C1G C -0.0115(11) 0.7792(10) 0.5157(6) 0.089(3) Uiso 0.50 d PD . H1GA H -0.0629(11) 0.7982(10) 0.5460(6) 0.133 Uiso 0.50 d PR . H1GB H 0.0553(11) 0.8099(10) 0.5288(6) 0.133 Uiso 0.50 d PR . H1GC H -0.0309(11) 0.8170(10) 0.4776(6) 0.133 Uiso 0.50 d PR . C1A C 0.0477(10) 0.9806(14) 0.4827(6) 0.092(4) Uiso 0.50 d P . C2A C 0.1023(15) 1.0970(17) 0.4480(9) 0.061(4) Uiso 0.25 d P . H2AA H 0.1631(15) 1.0695(17) 0.4265(9) 0.092 Uiso 0.50 d PR . H2AB H 0.0537(15) 1.1329(17) 0.4196(9) 0.092 Uiso 0.50 d PR . H2AC H 0.1224(15) 1.1571(17) 0.4780(9) 0.092 Uiso 0.50 d PR . O3A O 0.0522(12) 0.8817(14) 0.4903(7) 0.072(4) Uiso 0.25 d P . 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 O2 0.060(2) 0.0305(12) 0.0349(12) -0.0115(9) 0.0158(11) -0.0092(11) O28 0.0237(11) 0.0474(14) 0.0310(11) -0.0024(10) 0.0010(8) 0.0051(9) O32 0.0355(13) 0.0274(11) 0.0503(14) -0.0026(10) 0.0091(10) 0.0010(9) O37 0.081(2) 0.0268(12) 0.0433(14) -0.0055(10) -0.0140(13) 0.0028(12) C1 0.041(2) 0.039(2) 0.034(2) -0.0110(14) 0.0012(13) 0.0038(14) C3 0.038(2) 0.0248(14) 0.0254(14) -0.0038(11) -0.0002(12) -0.0007(12) C4 0.045(2) 0.032(2) 0.0288(15) -0.0032(12) 0.0113(13) -0.0049(13) C5 0.036(2) 0.0235(14) 0.0313(15) -0.0002(11) 0.0051(12) -0.0034(12) C6 0.0247(14) 0.0237(13) 0.0244(13) -0.0011(10) -0.0018(10) 0.0025(10) C7 0.0287(15) 0.0277(14) 0.0228(13) 0.0006(11) 0.0005(11) -0.0007(11) C8 0.035(2) 0.0226(14) 0.0275(14) 0.0009(11) 0.0006(12) -0.0031(11) C9 0.0250(15) 0.0225(13) 0.0248(13) -0.0020(10) -0.0001(10) 0.0014(10) C10 0.0232(14) 0.0272(14) 0.0279(14) -0.0068(11) 0.0012(11) 0.0037(11) C11 0.0243(15) 0.0284(14) 0.0307(14) -0.0066(11) 0.0027(11) 0.0024(11) C12 0.026(2) 0.041(2) 0.042(2) -0.0099(14) -0.0035(13) -0.0005(13) C13 0.029(2) 0.058(2) 0.035(2) -0.006(2) -0.0091(13) 0.0045(15) C14 0.035(2) 0.045(2) 0.032(2) 0.0030(14) -0.0012(13) 0.0057(14) C15 0.028(2) 0.031(2) 0.0292(14) 0.0011(12) -0.0011(11) 0.0022(12) C16 0.031(2) 0.0215(13) 0.0288(14) -0.0029(11) 0.0046(11) 0.0024(11) C17 0.0234(14) 0.0273(14) 0.0339(15) -0.0053(12) 0.0037(11) 0.0022(11) C18 0.032(2) 0.027(2) 0.050(2) -0.0047(13) 0.0024(14) -0.0034(12) C19 0.045(2) 0.0247(15) 0.053(2) 0.0024(14) 0.011(2) -0.0023(14) C20 0.046(2) 0.032(2) 0.037(2) 0.0049(13) 0.0052(14) 0.0065(14) C21 0.036(2) 0.030(2) 0.032(2) -0.0008(12) -0.0016(12) 0.0030(13) C22 0.0243(15) 0.0225(13) 0.0268(14) -0.0007(10) -0.0009(11) 0.0022(10) C23 0.031(2) 0.039(2) 0.0298(15) -0.0100(13) -0.0034(12) 0.0029(13) C24 0.027(2) 0.043(2) 0.037(2) -0.0110(14) -0.0067(13) 0.0029(13) C25 0.0227(15) 0.0280(14) 0.0298(14) 0.0023(11) 0.0015(11) 0.0033(11) C26 0.028(2) 0.0292(15) 0.0265(14) -0.0023(11) -0.0014(11) 0.0045(11) C27 0.0254(15) 0.0257(14) 0.0273(14) -0.0023(11) -0.0027(11) 0.0014(11) C29 0.023(2) 0.044(2) 0.040(2) 0.0083(14) -0.0039(12) -0.0004(13) C30 0.0233(15) 0.036(2) 0.0307(15) 0.0007(12) 0.0012(11) 0.0026(12) C31 0.0252(15) 0.0279(15) 0.037(2) -0.0034(12) 0.0061(12) 0.0022(12) C33 0.041(2) 0.037(2) 0.055(2) 0.004(2) 0.005(2) -0.0065(15) C34 0.029(2) 0.034(2) 0.0300(15) -0.0069(12) 0.0030(12) 0.0020(12) C35 0.039(2) 0.032(2) 0.0276(15) -0.0044(12) -0.0008(12) 0.0071(13) C36 0.047(2) 0.028(2) 0.032(2) -0.0039(12) 0.0004(13) 0.0028(13) C38 0.100(4) 0.032(2) 0.054(2) 0.002(2) -0.013(2) 0.010(2) C39 0.038(2) 0.034(2) 0.032(2) -0.0059(13) -0.0042(13) 0.0019(13) _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 O2 C3 1.376(4) . ? O2 C1 1.434(4) . ? O28 C25 1.371(4) . ? O28 C29 1.426(4) . ? O32 C31 1.384(4) . ? O32 C33 1.437(4) . ? O37 C36 1.369(4) . ? O37 C38 1.417(5) . ? C1 C34 1.502(4) 3_576 ? C3 C4 1.384(4) . ? C3 C8 1.389(4) . ? C4 C5 1.392(4) . ? C5 C6 1.383(4) . ? C6 C7 1.398(4) . ? C6 C9 1.531(4) . ? C7 C8 1.381(4) . ? C9 C16 1.529(4) . ? C9 C10 1.528(4) . ? C9 C22 1.539(4) . ? C10 C15 1.392(4) . ? C10 C11 1.401(4) . ? C11 C12 1.384(4) . ? C11 C17 1.466(4) . ? C12 C13 1.389(5) . ? C13 C14 1.388(5) . ? C14 C15 1.383(4) . ? C16 C21 1.391(4) . ? C16 C17 1.395(4) . ? C17 C18 1.393(4) . ? C18 C19 1.379(5) . ? C19 C20 1.396(5) . ? C20 C21 1.381(5) . ? C22 C23 1.380(4) . ? C22 C27 1.395(4) . ? C23 C24 1.399(5) . ? C24 C25 1.389(4) . ? C25 C26 1.387(4) . ? C26 C27 1.374(4) . ? C29 C30 1.514(4) . ? C30 C39 1.385(5) . ? C30 C31 1.388(4) . ? C31 C34 1.391(5) . ? C34 C35 1.389(5) . ? C34 C1 1.502(4) 3_576 ? C35 C36 1.387(4) . ? C36 C39 1.386(5) . ? C3G C4G 1.306(11) 3_566 ? C3G C2G 1.497(13) . ? C2G C4G 1.344(13) . ? C2G C1G 1.530(9) . ? C4G C3G 1.306(11) 3_566 ? C1G O3A 1.49(2) . ? C1G C2A 1.95(2) 3_576 ? C1A O3A 1.09(2) . ? C1A C1A 1.50(3) 3_576 ? C1A C2A 1.64(2) . ? C2A C1G 1.95(2) 3_576 ? 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 C3 O2 C1 119.7(3) . . ? C25 O28 C29 116.9(2) . . ? C31 O32 C33 113.9(3) . . ? C36 O37 C38 117.9(3) . . ? O2 C1 C34 107.1(3) . 3_576 ? O2 C3 C4 125.2(3) . . ? O2 C3 C8 115.1(3) . . ? C4 C3 C8 119.5(3) . . ? C3 C4 C5 119.5(3) . . ? C6 C5 C4 122.0(3) . . ? C5 C6 C7 117.4(3) . . ? C5 C6 C9 122.3(3) . . ? C7 C6 C9 120.2(2) . . ? C8 C7 C6 121.4(3) . . ? C7 C8 C3 120.2(3) . . ? C16 C9 C10 100.8(2) . . ? C16 C9 C6 113.8(2) . . ? C10 C9 C6 110.0(2) . . ? C16 C9 C22 107.0(2) . . ? C10 C9 C22 112.0(2) . . ? C6 C9 C22 112.7(2) . . ? C15 C10 C11 119.7(3) . . ? C15 C10 C9 129.1(3) . . ? C11 C10 C9 111.1(3) . . ? C12 C11 C10 121.0(3) . . ? C12 C11 C17 130.7(3) . . ? C10 C11 C17 108.3(3) . . ? C11 C12 C13 118.8(3) . . ? C14 C13 C12 120.4(3) . . ? C13 C14 C15 121.0(3) . . ? C14 C15 C10 119.0(3) . . ? C21 C16 C17 120.3(3) . . ? C21 C16 C9 128.5(3) . . ? C17 C16 C9 111.1(3) . . ? C16 C17 C18 120.7(3) . . ? C16 C17 C11 108.8(3) . . ? C18 C17 C11 130.5(3) . . ? C19 C18 C17 118.5(3) . . ? C18 C19 C20 121.1(3) . . ? C21 C20 C19 120.4(3) . . ? C20 C21 C16 119.0(3) . . ? C23 C22 C27 118.0(3) . . ? C23 C22 C9 121.8(3) . . ? C27 C22 C9 119.9(3) . . ? C22 C23 C24 121.4(3) . . ? C25 C24 C23 119.3(3) . . ? O28 C25 C26 115.8(3) . . ? O28 C25 C24 124.4(3) . . ? C26 C25 C24 119.8(3) . . ? C27 C26 C25 120.0(3) . . ? C26 C27 C22 121.5(3) . . ? O28 C29 C30 113.3(3) . . ? C39 C30 C31 118.9(3) . . ? C39 C30 C29 120.6(3) . . ? C31 C30 C29 120.6(3) . . ? O32 C31 C30 120.0(3) . . ? O32 C31 C34 119.1(3) . . ? C30 C31 C34 120.7(3) . . ? C35 C34 C31 119.8(3) . . ? C35 C34 C1 120.4(3) . 3_576 ? C31 C34 C1 119.7(3) . 3_576 ? C34 C35 C36 119.6(3) . . ? O37 C36 C39 115.2(3) . . ? O37 C36 C35 124.7(3) . . ? C39 C36 C35 120.1(3) . . ? C36 C39 C30 120.8(3) . . ? C4G C3G C2G 123.1(9) 3_566 . ? C4G C2G C3G 102.7(8) . . ? C4G C2G C1G 132.4(11) . . ? C3G C2G C1G 124.8(11) . . ? C3G C4G C2G 133.8(10) 3_566 . ? O3A C1G C2G 134.2(12) . . ? O3A C1G C2A 87.9(9) . 3_576 ? C2G C1G C2A 137.7(11) . 3_576 ? O3A C1A C1A 104.0(17) . 3_576 ? O3A C1A C2A 144.4(16) . . ? C1A C1A C2A 111.6(16) 3_576 . ? C1A C2A C1G 95.1(11) . 3_576 ? C1A O3A C1G 140.1(16) . . ? 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 C3 O2 C1 C34 149.7(3) . . . 3_576 ? C1 O2 C3 C4 -29.0(5) . . . . ? C1 O2 C3 C8 155.5(3) . . . . ? O2 C3 C4 C5 -174.7(3) . . . . ? C8 C3 C4 C5 0.6(5) . . . . ? C3 C4 C5 C6 -1.0(5) . . . . ? C4 C5 C6 C7 0.7(5) . . . . ? C4 C5 C6 C9 -175.7(3) . . . . ? C5 C6 C7 C8 -0.1(4) . . . . ? C9 C6 C7 C8 176.5(3) . . . . ? C6 C7 C8 C3 -0.3(5) . . . . ? O2 C3 C8 C7 175.8(3) . . . . ? C4 C3 C8 C7 0.0(5) . . . . ? C5 C6 C9 C16 -17.6(4) . . . . ? C7 C6 C9 C16 166.0(3) . . . . ? C5 C6 C9 C10 94.5(3) . . . . ? C7 C6 C9 C10 -81.8(3) . . . . ? C5 C6 C9 C22 -139.7(3) . . . . ? C7 C6 C9 C22 43.9(4) . . . . ? C16 C9 C10 C15 -179.4(3) . . . . ? C6 C9 C10 C15 60.2(4) . . . . ? C22 C9 C10 C15 -66.0(4) . . . . ? C16 C9 C10 C11 -0.8(3) . . . . ? C6 C9 C10 C11 -121.2(3) . . . . ? C22 C9 C10 C11 112.6(3) . . . . ? C15 C10 C11 C12 -0.2(4) . . . . ? C9 C10 C11 C12 -179.0(3) . . . . ? C15 C10 C11 C17 179.0(3) . . . . ? C9 C10 C11 C17 0.2(3) . . . . ? C10 C11 C12 C13 0.1(5) . . . . ? C17 C11 C12 C13 -178.8(3) . . . . ? C11 C12 C13 C14 -0.8(5) . . . . ? C12 C13 C14 C15 1.5(5) . . . . ? C13 C14 C15 C10 -1.5(5) . . . . ? C11 C10 C15 C14 0.8(4) . . . . ? C9 C10 C15 C14 179.3(3) . . . . ? C10 C9 C16 C21 176.8(3) . . . . ? C6 C9 C16 C21 -65.6(4) . . . . ? C22 C9 C16 C21 59.6(4) . . . . ? C10 C9 C16 C17 1.1(3) . . . . ? C6 C9 C16 C17 118.7(3) . . . . ? C22 C9 C16 C17 -116.1(3) . . . . ? C21 C16 C17 C18 0.0(4) . . . . ? C9 C16 C17 C18 176.1(3) . . . . ? C21 C16 C17 C11 -177.2(3) . . . . ? C9 C16 C17 C11 -1.1(3) . . . . ? C12 C11 C17 C16 179.6(3) . . . . ? C10 C11 C17 C16 0.6(3) . . . . ? C12 C11 C17 C18 2.8(5) . . . . ? C10 C11 C17 C18 -176.3(3) . . . . ? C16 C17 C18 C19 0.0(5) . . . . ? C11 C17 C18 C19 176.5(3) . . . . ? C17 C18 C19 C20 -0.1(5) . . . . ? C18 C19 C20 C21 0.2(5) . . . . ? C19 C20 C21 C16 -0.1(5) . . . . ? C17 C16 C21 C20 0.0(5) . . . . ? C9 C16 C21 C20 -175.3(3) . . . . ? C16 C9 C22 C23 -92.7(3) . . . . ? C10 C9 C22 C23 157.8(3) . . . . ? C6 C9 C22 C23 33.1(4) . . . . ? C16 C9 C22 C27 81.4(3) . . . . ? C10 C9 C22 C27 -28.1(4) . . . . ? C6 C9 C22 C27 -152.8(3) . . . . ? C27 C22 C23 C24 -0.4(5) . . . . ? C9 C22 C23 C24 173.8(3) . . . . ? C22 C23 C24 C25 -0.2(5) . . . . ? C29 O28 C25 C26 165.4(3) . . . . ? C29 O28 C25 C24 -14.8(4) . . . . ? C23 C24 C25 O28 -179.7(3) . . . . ? C23 C24 C25 C26 0.0(5) . . . . ? O28 C25 C26 C27 -179.5(3) . . . . ? C24 C25 C26 C27 0.7(5) . . . . ? C25 C26 C27 C22 -1.3(5) . . . . ? C23 C22 C27 C26 1.2(4) . . . . ? C9 C22 C27 C26 -173.1(3) . . . . ? C25 O28 C29 C30 83.2(3) . . . . ? O28 C29 C30 C39 33.8(4) . . . . ? O28 C29 C30 C31 -146.9(3) . . . . ? C33 O32 C31 C30 -84.7(4) . . . . ? C33 O32 C31 C34 99.8(3) . . . . ? C39 C30 C31 O32 -174.5(3) . . . . ? C29 C30 C31 O32 6.2(4) . . . . ? C39 C30 C31 C34 1.0(5) . . . . ? C29 C30 C31 C34 -178.4(3) . . . . ? O32 C31 C34 C35 175.7(3) . . . . ? C30 C31 C34 C35 0.2(5) . . . . ? O32 C31 C34 C1 0.3(4) . . . 3_576 ? C30 C31 C34 C1 -175.2(3) . . . 3_576 ? C31 C34 C35 C36 -1.4(5) . . . . ? C1 C34 C35 C36 174.0(3) 3_576 . . . ? C38 O37 C36 C39 172.9(4) . . . . ? C38 O37 C36 C35 -8.1(6) . . . . ? C34 C35 C36 O37 -177.5(3) . . . . ? C34 C35 C36 C39 1.4(5) . . . . ? O37 C36 C39 C30 178.9(3) . . . . ? C35 C36 C39 C30 -0.2(5) . . . . ? C31 C30 C39 C36 -1.0(5) . . . . ? C29 C30 C39 C36 178.3(3) . . . . ? C4G C3G C2G C4G -5.8(16) 3_566 . . . ? C4G C3G C2G C1G 177.7(11) 3_566 . . . ? C3G C2G C4G C3G 6.7(18) . . . 3_566 ? C1G C2G C4G C3G -177.2(12) . . . 3_566 ? C4G C2G C1G O3A 176.7(14) . . . . ? C3G C2G C1G O3A -7.9(22) . . . . ? C4G C2G C1G C2A -9.5(26) . . . 3_576 ? C3G C2G C1G C2A 165.8(13) . . . 3_576 ? O3A C1A C2A C1G -175.2(25) . . . 3_576 ? C1A C1A C2A C1G 6.5(17) 3_576 . . 3_576 ? C1A C1A O3A C1G 10.6(32) 3_576 . . . ? C2A C1A O3A C1G -167.7(19) . . . . ? C2G C1G O3A C1A 161.8(21) . . . . ? C2A C1G O3A C1A -14.0(26) 3_576 . . . ? _refine_diff_density_max 1.345 _refine_diff_density_min -0.643 _refine_diff_density_rms 0.097 data_dd _database_code_CSD 150567 # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C78 H80 O12 S4' _chemical_formula_weight 1337.66 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _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 9.475(2) _cell_length_b 13.591(2) _cell_length_c 26.899(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.000(10) _cell_angle_gamma 90.00 _cell_volume 3411.3(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 15 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method none _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 1.794 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'enraf nonius cad4 diffractometer' _diffrn_measurement_method 'omega 2theat-scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 250 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 2 _diffrn_reflns_number 7211 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 74.73 _reflns_number_total 6776 _reflns_number_observed 3737 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'nonius' _computing_cell_refinement 'nonius' _computing_data_reduction 'helena' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'platon' _computing_publication_material 'platon' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1098 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1884P)^2^+7.7581P] 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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0000(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5678 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1911 _refine_ls_R_factor_obs 0.1260 _refine_ls_wR_factor_all 0.3996 _refine_ls_wR_factor_obs 0.3329 _refine_ls_goodness_of_fit_all 1.023 _refine_ls_goodness_of_fit_obs 1.180 _refine_ls_restrained_S_all 1.046 _refine_ls_restrained_S_obs 1.180 _refine_ls_shift/esd_max -0.076 _refine_ls_shift/esd_mean 0.002 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O2' O 0.7468(5) 0.5080(3) 0.46216(15) 0.0631(12) Uani 1 d . . O28 O 0.4432(4) 0.9325(3) 0.3390(2) 0.0573(11) Uani 1 d . . O32 O 0.4119(5) 0.6794(3) 0.4226(2) 0.0599(11) Uani 1 d . . O37 O 0.8359(5) 0.7261(3) 0.3081(2) 0.0629(11) Uani 1 d . . C1' C 0.6180(7) 0.5216(4) 0.4270(2) 0.059(2) Uani 1 d . . H1'A H 0.5377(7) 0.5247(4) 0.4444(2) 0.071 Uiso 1 d R . H1'B H 0.6047(7) 0.4656(4) 0.4049(2) 0.071 Uiso 1 d R . C3' C 0.7646(7) 0.5603(4) 0.5069(2) 0.0532(14) Uani 1 d . . C4' C 0.6688(7) 0.6286(4) 0.5196(2) 0.0581(15) Uani 1 d . . H4'A H 0.5829(7) 0.6440(4) 0.4963(2) 0.070 Uiso 1 d R . C5 C 0.3013(7) 1.3256(4) 0.4331(2) 0.0556(14) Uani 1 d . . H5A H 0.3691(7) 1.2797(4) 0.4237(2) 0.067 Uiso 1 d R . C6 C 0.1793(6) 1.3435(4) 0.4002(2) 0.0451(12) Uani 1 d . . C7 C 0.0840(7) 1.4123(4) 0.4132(2) 0.0539(14) Uani 1 d . . H7A H -0.0025(7) 1.4265(4) 0.3900(2) 0.065 Uiso 1 d R . C8' C 0.8872(7) 0.5396(4) 0.5408(2) 0.0571(15) Uani 1 d . . H8'A H 0.9531(7) 0.4914(4) 0.5323(2) 0.068 Uiso 1 d R . C9 C 0.1535(6) 1.3001(4) 0.3465(2) 0.0507(13) Uani 1 d . . C10 C -0.0049(7) 1.2949(4) 0.3239(3) 0.063(2) Uani 1 d . . C11 C -0.0342(9) 1.3607(5) 0.2822(3) 0.077(2) Uani 1 d . . C12 C -0.1765(12) 1.3682(8) 0.2580(4) 0.117(4) Uani 1 d . . H12A H -0.1980(12) 1.4125(8) 0.2299(4) 0.141 Uiso 1 d R . C13 C -0.2836(12) 1.3163(9) 0.2731(6) 0.135(6) Uani 1 d . . H13A H -0.3806(12) 1.3235(9) 0.2558(6) 0.163 Uiso 1 d R . C14 C -0.2520(9) 1.2540(7) 0.3138(5) 0.122(4) Uani 1 d . . H14A H -0.3274(9) 1.2169(7) 0.3246(5) 0.146 Uiso 1 d R . C15 C -0.1128(8) 1.2414(5) 0.3398(4) 0.091(3) Uani 1 d . . H15A H -0.0913(8) 1.1970(5) 0.3678(4) 0.109 Uiso 1 d R . C16 C 0.2065(7) 1.3765(4) 0.3118(2) 0.0560(15) Uani 1 d . . C17 C 0.0947(9) 1.4093(5) 0.2756(3) 0.073(2) Uani 1 d . . C18 C 0.1228(14) 1.4831(7) 0.2405(3) 0.114(4) Uani 1 d . . H18A H 0.0472(14) 1.5075(7) 0.2150(3) 0.137 Uiso 1 d R . C19 C 0.2612(16) 1.5176(8) 0.2450(5) 0.135(5) Uani 1 d . . H19A H 0.2810(16) 1.5677(8) 0.2221(5) 0.161 Uiso 1 d R . C20 C 0.3715(12) 1.4848(6) 0.2815(4) 0.099(3) Uani 1 d . . H20A H 0.4668(12) 1.5105(6) 0.2839(4) 0.119 Uiso 1 d R . C21 C 0.3441(9) 1.4131(5) 0.3148(3) 0.072(2) Uani 1 d . . H21A H 0.4196(9) 1.3887(5) 0.3403(3) 0.087 Uiso 1 d R . C22 C 0.2282(6) 1.1988(4) 0.3441(2) 0.0484(13) Uani 1 d . . C23 C 0.2081(6) 1.1251(4) 0.3773(2) 0.0531(14) Uani 1 d . . H23A H 0.1453(6) 1.1366(4) 0.4011(2) 0.064 Uiso 1 d R . C24 C 0.2755(6) 1.0329(4) 0.3767(2) 0.0518(14) Uani 1 d . . H24A H 0.2624(6) 0.9822(4) 0.4003(2) 0.062 Uiso 1 d R . C25 C 0.3658(6) 1.0176(4) 0.3425(2) 0.0497(13) Uani 1 d . . C26 C 0.3841(7) 1.0899(4) 0.3086(2) 0.0548(14) Uani 1 d . . H26A H 0.4448(7) 1.0775(4) 0.2842(2) 0.066 Uiso 1 d R . C27 C 0.3165(6) 1.1797(4) 0.3095(2) 0.0517(13) Uani 1 d . . H27A H 0.3299(6) 1.2296(4) 0.2855(2) 0.062 Uiso 1 d R . C29 C 0.4209(7) 0.8535(4) 0.3710(3) 0.061(2) Uani 1 d . . H29A H 0.3250(7) 0.8294(4) 0.3610(3) 0.073 Uiso 1 d R . H29B H 0.4320(7) 0.8751(4) 0.4055(3) 0.073 Uiso 1 d R . C30 C 0.5267(6) 0.7729(4) 0.3659(2) 0.0518(14) Uani 1 d . . C31 C 0.5191(6) 0.6870(4) 0.3939(2) 0.0499(13) Uani 1 d . . C33 C 0.2831(8) 0.6353(6) 0.3962(3) 0.082(2) Uani 1 d . . H33A H 0.2131(8) 0.6322(6) 0.4180(3) 0.098 Uiso 1 d R . H33B H 0.2465(8) 0.6742(6) 0.3670(3) 0.098 Uiso 1 d R . H33C H 0.3036(8) 0.5701(6) 0.3858(3) 0.098 Uiso 1 d R . C34 C 0.6210(6) 0.6134(4) 0.3947(2) 0.0496(13) Uani 1 d . . C35 C 0.7272(6) 0.6242(4) 0.3657(2) 0.0525(14) Uani 1 d . . H35A H 0.7970(6) 0.5731(4) 0.3656(2) 0.063 Uiso 1 d R . C36 C 0.7338(7) 0.7070(4) 0.3368(2) 0.0521(14) Uani 1 d . . C39 C 0.6324(7) 0.7818(4) 0.3376(2) 0.0563(15) Uani 1 d . . H39A H 0.6362(7) 0.8399(4) 0.3175(2) 0.068 Uiso 1 d R . C38 C 0.9351(7) 0.6496(5) 0.3032(3) 0.071(2) Uani 1 d . . H38A H 1.0014(7) 0.6716(5) 0.2824(3) 0.086 Uiso 1 d R . H38B H 0.9866(7) 0.6327(5) 0.3361(3) 0.086 Uiso 1 d R . H38C H 0.8843(7) 0.5929(5) 0.2882(3) 0.086 Uiso 1 d R . S1 S -0.3649(5) 1.1718(4) 0.4248(2) 0.102(2) Uiso 0.542(7) d P 1 O1S1 O -0.2693(15) 1.0969(11) 0.4081(6) 0.134(5) Uiso 0.542(7) d P 1 C1S1 C -0.4313(21) 1.1242(14) 0.4701(8) 0.099(5) Uiso 0.542(7) d P 1 H1SB1 H -0.4985(21) 1.0744(14) 0.4561(8) 0.149 Uiso 0.542(7) d PR 1 H1SC1 H -0.3572(21) 1.0951(14) 0.4945(8) 0.149 Uiso 0.542(7) d PR 1 H1SD1 H -0.4800(21) 1.1738(14) 0.4861(8) 0.149 Uiso 0.542(7) d PR 1 C2S1 C -0.2558(29) 1.2584(21) 0.4526(11) 0.151(10) Uiso 0.542(7) d P 1 H2SA2 H -0.2105(29) 1.2905(21) 0.4277(11) 0.227 Uiso 0.542(7) d PR 1 H2SB2 H -0.3071(29) 1.3060(21) 0.4688(11) 0.227 Uiso 0.542(7) d PR 1 H2SC2 H -0.1843(29) 1.2274(21) 0.4773(11) 0.227 Uiso 0.542(7) d PR 1 S1' S -0.3720(8) 1.1436(5) 0.4954(3) 0.119(2) Uiso 0.458(7) d P 2 O1S' O -0.5249(23) 1.1462(16) 0.5029(8) 0.164(7) Uiso 0.458(7) d P 2 C1S' C -0.3247(46) 1.0335(36) 0.4591(18) 0.241(20) Uiso 0.458(7) d P 2 H1SB' H -0.3540(46) 0.9705(36) 0.4698(18) 0.361 Uiso 0.458(7) d PR 2 H1SC' H -0.3841(46) 1.0513(36) 0.4277(18) 0.361 Uiso 0.458(7) d PR 2 H1SD' H -0.2266(46) 1.0302(36) 0.4546(18) 0.361 Uiso 0.458(7) d PR 2 C2S' C -0.3120(27) 1.2609(19) 0.4677(10) 0.109(7) Uiso 0.458(7) d P 2 H2SA' H -0.3175(27) 1.3149(19) 0.4903(10) 0.164 Uiso 0.458(7) d PR 2 H2SB' H -0.2148(27) 1.2530(19) 0.4627(10) 0.164 Uiso 0.458(7) d PR 2 H2SC' H -0.3723(27) 1.2741(19) 0.4359(10) 0.164 Uiso 0.458(7) d PR 2 S2 S 0.0209(7) 1.1713(5) 0.5765(2) 0.109(2) Uiso 0.348(6) d P 3 S2' S 0.0288(27) 1.0610(19) 0.5621(10) 0.210(9) Uiso 0.232(4) d P 3 O1S2 O -0.1298(16) 1.1505(11) 0.5592(6) 0.148(5) Uiso 0.580(10) d P 3 C1S2 C 0.0901(22) 1.0700(15) 0.6090(9) 0.134(7) Uiso 0.580(10) d P 3 H1SB H 0.0565(22) 1.0666(15) 0.6406(9) 0.201 Uiso 0.580(10) d PR 3 H1SC H 0.0600(22) 1.0123(15) 0.5894(9) 0.201 Uiso 0.580(10) d PR 3 H1SD H 0.1929(22) 1.0738(15) 0.6151(9) 0.201 Uiso 0.580(10) d PR 3 C2S2 C 0.0864(10) 1.1688(7) 0.5224(3) 0.192(4) Uiso 0.580(10) d P 3 H2SA H 0.0509(10) 1.2249(7) 0.5024(3) 0.288 Uiso 0.580(10) d PR 3 H2SB H 0.1892(10) 1.1711(7) 0.5298(3) 0.288 Uiso 0.580(10) d PR 3 H2SC H 0.0563(10) 1.1097(7) 0.5041(3) 0.288 Uiso 0.580(10) d PR 3 S3 S 0.0864(10) 1.1688(7) 0.5224(3) 0.192(4) Uiso 0.420(10) d P 4 O1S3 O 0.1686(25) 1.0975(18) 0.5279(9) 0.164(9) Uiso 0.420(10) d P 4 C1S3 C -0.0169(19) 1.1257(13) 0.4738(7) 0.077(5) Uiso 0.420(10) d P 4 H1SA3 H 0.0302(19) 1.1284(13) 0.4450(7) 0.115 Uiso 0.420(10) d PR 4 H1SD3 H -0.0394(19) 1.0586(13) 0.4804(7) 0.115 Uiso 0.420(10) d PR 4 H1SB3 H -0.1037(19) 1.1636(13) 0.4672(7) 0.115 Uiso 0.420(10) d PR 4 C2S3 C 0.0209(7) 1.1713(5) 0.5765(2) 0.109(2) Uiso 0.420(10) d P 4 H2SC3 H 0.0937(2007) 1.2002(2007) 0.6038(50) 0.164(9) Uiso 0.420(10) d PR 4 H2SD3 H -0.0621(2007) 1.2113(2007) 0.5733(50) 0.164 Uiso 0.420(10) d PR 4 H2SA3 H 0.0022(2007) 1.1063(2007) 0.5864(50) 0.164 Uiso 0.420(10) d PR 4 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 O2' 0.100(3) 0.045(2) 0.046(2) 0.004(2) 0.019(2) 0.021(2) O28 0.072(3) 0.039(2) 0.062(2) 0.003(2) 0.016(2) 0.011(2) O32 0.072(3) 0.045(2) 0.063(3) -0.001(2) 0.014(2) -0.002(2) O37 0.077(3) 0.052(2) 0.064(3) 0.002(2) 0.024(2) 0.007(2) C1' 0.088(4) 0.036(3) 0.052(3) -0.001(2) 0.010(3) 0.001(3) C3' 0.075(4) 0.041(3) 0.047(3) 0.002(2) 0.019(3) 0.006(3) C4' 0.068(4) 0.054(3) 0.050(3) -0.007(3) 0.005(3) 0.011(3) C5 0.063(4) 0.049(3) 0.055(3) -0.009(3) 0.011(3) 0.011(3) C6 0.053(3) 0.037(2) 0.047(3) 0.003(2) 0.013(2) 0.003(2) C7 0.065(4) 0.050(3) 0.049(3) 0.008(3) 0.016(3) 0.011(3) C8' 0.068(4) 0.046(3) 0.060(4) 0.005(3) 0.022(3) 0.015(3) C9 0.065(4) 0.037(3) 0.051(3) 0.001(2) 0.011(3) 0.008(2) C10 0.065(4) 0.042(3) 0.075(4) -0.017(3) -0.008(3) 0.012(3) C11 0.093(5) 0.064(4) 0.062(4) -0.019(3) -0.017(4) 0.037(4) C12 0.118(8) 0.124(8) 0.088(6) -0.047(6) -0.046(6) 0.071(7) C13 0.076(6) 0.114(9) 0.188(12) -0.082(9) -0.056(7) 0.039(6) C14 0.057(5) 0.077(6) 0.217(13) -0.039(7) -0.014(6) 0.005(4) C15 0.063(4) 0.057(4) 0.148(8) -0.015(5) 0.005(5) 0.004(3) C16 0.088(4) 0.038(3) 0.043(3) -0.003(2) 0.014(3) 0.011(3) C17 0.101(6) 0.062(4) 0.055(4) 0.004(3) 0.014(4) 0.034(4) C18 0.166(10) 0.108(7) 0.075(5) 0.035(5) 0.038(6) 0.089(7) C19 0.188(12) 0.094(7) 0.150(10) 0.059(7) 0.109(10) 0.061(8) C20 0.144(8) 0.056(4) 0.116(7) 0.006(4) 0.075(7) 0.004(5) C21 0.107(6) 0.047(3) 0.071(4) -0.004(3) 0.036(4) -0.004(4) C22 0.058(3) 0.038(3) 0.047(3) -0.002(2) 0.004(3) 0.002(2) C23 0.064(4) 0.045(3) 0.052(3) 0.001(2) 0.014(3) 0.004(3) C24 0.061(3) 0.036(3) 0.058(3) 0.006(2) 0.011(3) 0.004(2) C25 0.056(3) 0.038(3) 0.053(3) 0.001(2) 0.005(3) 0.002(2) C26 0.065(4) 0.047(3) 0.052(3) -0.002(3) 0.010(3) 0.011(3) C27 0.064(4) 0.041(3) 0.050(3) 0.001(2) 0.009(3) 0.003(3) C29 0.072(4) 0.046(3) 0.068(4) 0.013(3) 0.018(3) 0.013(3) C30 0.061(3) 0.040(3) 0.053(3) 0.003(2) 0.005(3) 0.006(2) C31 0.063(3) 0.045(3) 0.042(3) -0.002(2) 0.010(3) -0.005(3) C33 0.074(5) 0.079(5) 0.093(6) -0.005(4) 0.018(4) -0.011(4) C34 0.069(4) 0.035(3) 0.042(3) -0.006(2) 0.003(3) -0.001(2) C35 0.066(4) 0.040(3) 0.048(3) -0.001(2) 0.000(3) 0.007(3) C36 0.068(4) 0.042(3) 0.044(3) -0.003(2) 0.004(3) 0.000(3) C39 0.073(4) 0.038(3) 0.057(3) 0.005(2) 0.009(3) 0.005(3) C38 0.066(4) 0.073(4) 0.078(5) 0.009(4) 0.020(4) 0.016(3) _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 O2' C3' 1.383(7) . ? O2' C1' 1.420(8) . ? O28 C25 1.382(6) . ? O28 C29 1.416(7) . ? O32 C31 1.382(7) . ? O32 C33 1.433(8) . ? O37 C36 1.364(7) . ? O37 C38 1.423(7) . ? C1' C34 1.523(7) . ? C3' C8' 1.375(9) . ? C3' C4' 1.381(8) . ? C4' C5 1.400(8) 3_676 ? C5 C6 1.351(8) . ? C5 C4' 1.400(8) 3_676 ? C6 C7 1.386(7) . ? C6 C9 1.541(8) . ? C7 C8' 1.385(8) 3_676 ? C8' C7 1.385(8) 3_676 ? C9 C10 1.519(9) . ? C9 C16 1.538(8) . ? C9 C22 1.555(7) . ? C10 C15 1.382(10) . ? C10 C11 1.423(10) . ? C11 C12 1.396(12) . ? C11 C17 1.426(11) . ? C12 C13 1.36(2) . ? C13 C14 1.37(2) . ? C14 C15 1.391(12) . ? C16 C17 1.381(9) . ? C16 C21 1.385(10) . ? C17 C18 1.435(12) . ? C18 C19 1.38(2) . ? C19 C20 1.38(2) . ? C20 C21 1.379(10) . ? C22 C27 1.379(8) . ? C22 C23 1.377(8) . ? C23 C24 1.408(7) . ? C24 C25 1.375(8) . ? C25 C26 1.372(8) . ? C26 C27 1.381(7) . ? C29 C30 1.507(8) . ? C30 C39 1.365(8) . ? C30 C31 1.398(7) . ? C31 C34 1.387(8) . ? C34 C35 1.384(8) . ? C35 C36 1.374(8) . ? C36 C39 1.402(8) . ? S1 O1S1 1.483(15) . ? S1 C1S1 1.60(2) . ? S1 C2S1 1.66(3) . ? S1' O1S' 1.50(2) . ? S1' C1S' 1.88(5) . ? S1' C2S' 1.89(3) . ? S2 O1S2 1.451(15) . ? S2 S2' 1.55(3) . ? S2 C2S2 1.677(10) . ? S2 C1S2 1.70(2) . ? S2' C1S2 1.30(3) . ? S2' O1S2 1.92(3) . ? S2' C2S2 1.95(3) . ? S3 O1S3 1.24(2) . ? S3 C1S3 1.60(2) . ? S3 C2S3 1.677(10) . ? 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 C3' O2' C1' 118.3(5) . . ? C25 O28 C29 117.1(4) . . ? C31 O32 C33 113.5(5) . . ? C36 O37 C38 117.2(5) . . ? O2' C1' C34 112.8(5) . . ? C8' C3' O2' 115.7(5) . . ? C8' C3' C4' 119.3(5) . . ? O2' C3' C4' 125.0(6) . . ? C3' C4' C5 119.0(6) . 3_676 ? C6 C5 C4' 122.0(5) . 3_676 ? C5 C6 C7 118.5(5) . . ? C5 C6 C9 121.7(5) . . ? C7 C6 C9 119.3(5) . . ? C8' C7 C6 120.5(5) 3_676 . ? C3' C8' C7 120.6(5) . 3_676 ? C10 C9 C16 101.1(5) . . ? C10 C9 C6 112.2(5) . . ? C16 C9 C6 107.2(4) . . ? C10 C9 C22 111.6(5) . . ? C16 C9 C22 112.0(5) . . ? C6 C9 C22 112.2(4) . . ? C15 C10 C11 121.3(7) . . ? C15 C10 C9 129.3(6) . . ? C11 C10 C9 109.3(6) . . ? C12 C11 C17 133.4(9) . . ? C12 C11 C10 117.0(9) . . ? C17 C11 C10 109.5(6) . . ? C13 C12 C11 122.3(11) . . ? C12 C13 C14 119.2(9) . . ? C13 C14 C15 122.2(11) . . ? C10 C15 C14 117.9(9) . . ? C17 C16 C21 121.6(6) . . ? C17 C16 C9 110.7(6) . . ? C21 C16 C9 127.6(6) . . ? C16 C17 C11 109.4(6) . . ? C16 C17 C18 118.8(8) . . ? C11 C17 C18 131.8(8) . . ? C19 C18 C17 117.5(9) . . ? C20 C19 C18 123.1(9) . . ? C19 C20 C21 119.1(10) . . ? C20 C21 C16 119.8(8) . . ? C27 C22 C23 118.0(5) . . ? C27 C22 C9 121.9(5) . . ? C23 C22 C9 120.2(5) . . ? C22 C23 C24 121.7(5) . . ? C25 C24 C23 118.6(5) . . ? C24 C25 C26 120.0(5) . . ? C24 C25 O28 124.9(5) . . ? C26 C25 O28 115.1(5) . . ? C25 C26 C27 120.6(6) . . ? C22 C27 C26 121.0(5) . . ? O28 C29 C30 108.9(5) . . ? C39 C30 C31 119.1(5) . . ? C39 C30 C29 123.4(5) . . ? C31 C30 C29 117.4(5) . . ? O32 C31 C34 121.0(5) . . ? O32 C31 C30 118.3(5) . . ? C34 C31 C30 120.6(5) . . ? C31 C34 C35 119.1(5) . . ? C31 C34 C1' 121.2(5) . . ? C35 C34 C1' 119.7(5) . . ? C36 C35 C34 121.0(5) . . ? O37 C36 C35 125.7(5) . . ? O37 C36 C39 115.1(5) . . ? C35 C36 C39 119.2(6) . . ? C30 C39 C36 121.0(5) . . ? O1S1 S1 C1S1 107.1(9) . . ? O1S1 S1 C2S1 104.9(12) . . ? C1S1 S1 C2S1 103.9(14) . . ? O1S' S1' C1S' 114.3(17) . . ? O1S' S1' C2S' 113.4(12) . . ? C1S' S1' C2S' 110.5(17) . . ? O1S2 S2 S2' 79.6(11) . . ? O1S2 S2 C2S2 102.2(8) . . ? S2' S2 C2S2 73.9(11) . . ? O1S2 S2 C1S2 106.1(10) . . ? S2' S2 C1S2 46.8(11) . . ? C2S2 S2 C1S2 105.2(9) . . ? C1S2 S2' S2 72.5(17) . . ? C1S2 S2' O1S2 101.1(19) . . ? S2 S2' O1S2 47.9(9) . . ? C1S2 S2' C2S2 109.9(20) . . ? S2 S2' C2S2 55.9(9) . . ? O1S2 S2' C2S2 78.1(11) . . ? S2 O1S2 S2' 52.6(9) . . ? S2' C1S2 S2 60.6(15) . . ? S2 C2S2 S2' 50.2(8) . . ? O1S3 S3 C1S3 95.4(14) . . ? O1S3 S3 C2S3 103.5(13) . . ? C1S3 S3 C2S3 116.7(9) . . ? 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 C3' O2' C1' C34 81.5(6) . . . . ? C1' O2' C3' C8' 176.1(5) . . . . ? C1' O2' C3' C4' -2.8(8) . . . . ? C8' C3' C4' C5 -0.5(9) . . . 3_676 ? O2' C3' C4' C5 178.4(6) . . . 3_676 ? C4' C5 C6 C7 2.5(9) 3_676 . . . ? C4' C5 C6 C9 174.4(5) 3_676 . . . ? C5 C6 C7 C8' -0.9(8) . . . 3_676 ? C9 C6 C7 C8' -172.9(5) . . . 3_676 ? O2' C3' C8' C7 180.0(5) . . . 3_676 ? C4' C3' C8' C7 -1.0(9) . . . 3_676 ? C5 C6 C9 C10 157.6(5) . . . . ? C7 C6 C9 C10 -30.6(7) . . . . ? C5 C6 C9 C16 -92.3(6) . . . . ? C7 C6 C9 C16 79.5(6) . . . . ? C5 C6 C9 C22 31.0(7) . . . . ? C7 C6 C9 C22 -157.2(5) . . . . ? C16 C9 C10 C15 -177.2(6) . . . . ? C6 C9 C10 C15 -63.3(8) . . . . ? C22 C9 C10 C15 63.6(8) . . . . ? C16 C9 C10 C11 -0.2(6) . . . . ? C6 C9 C10 C11 113.7(5) . . . . ? C22 C9 C10 C11 -119.4(5) . . . . ? C15 C10 C11 C12 -0.4(10) . . . . ? C9 C10 C11 C12 -177.7(6) . . . . ? C15 C10 C11 C17 177.3(6) . . . . ? C9 C10 C11 C17 0.0(7) . . . . ? C17 C11 C12 C13 -176.6(8) . . . . ? C10 C11 C12 C13 0.5(12) . . . . ? C11 C12 C13 C14 0.0(15) . . . . ? C12 C13 C14 C15 -0.7(15) . . . . ? C11 C10 C15 C14 -0.3(11) . . . . ? C9 C10 C15 C14 176.5(7) . . . . ? C13 C14 C15 C10 0.8(14) . . . . ? C10 C9 C16 C17 0.3(6) . . . . ? C6 C9 C16 C17 -117.3(5) . . . . ? C22 C9 C16 C17 119.2(5) . . . . ? C10 C9 C16 C21 178.6(6) . . . . ? C6 C9 C16 C21 60.9(7) . . . . ? C22 C9 C16 C21 -62.5(7) . . . . ? C21 C16 C17 C11 -178.7(6) . . . . ? C9 C16 C17 C11 -0.3(7) . . . . ? C21 C16 C17 C18 0.0(9) . . . . ? C9 C16 C17 C18 178.4(6) . . . . ? C12 C11 C17 C16 177.4(7) . . . . ? C10 C11 C17 C16 0.2(7) . . . . ? C12 C11 C17 C18 -1.1(14) . . . . ? C10 C11 C17 C18 -178.3(7) . . . . ? C16 C17 C18 C19 -0.3(12) . . . . ? C11 C17 C18 C19 178.1(8) . . . . ? C17 C18 C19 C20 -0.2(16) . . . . ? C18 C19 C20 C21 0.9(15) . . . . ? C19 C20 C21 C16 -1.1(11) . . . . ? C17 C16 C21 C20 0.7(9) . . . . ? C9 C16 C21 C20 -177.4(6) . . . . ? C10 C9 C22 C27 104.7(6) . . . . ? C16 C9 C22 C27 -7.8(8) . . . . ? C6 C9 C22 C27 -128.4(6) . . . . ? C10 C9 C22 C23 -75.8(7) . . . . ? C16 C9 C22 C23 171.7(5) . . . . ? C6 C9 C22 C23 51.1(7) . . . . ? C27 C22 C23 C24 0.3(9) . . . . ? C9 C22 C23 C24 -179.2(5) . . . . ? C22 C23 C24 C25 1.4(9) . . . . ? C23 C24 C25 C26 -2.7(9) . . . . ? C23 C24 C25 O28 177.4(5) . . . . ? C29 O28 C25 C24 3.8(8) . . . . ? C29 O28 C25 C26 -176.1(5) . . . . ? C24 C25 C26 C27 2.4(9) . . . . ? O28 C25 C26 C27 -177.7(5) . . . . ? C23 C22 C27 C26 -0.7(9) . . . . ? C9 C22 C27 C26 178.8(5) . . . . ? C25 C26 C27 C22 -0.6(9) . . . . ? C25 O28 C29 C30 -173.4(5) . . . . ? O28 C29 C30 C39 4.8(9) . . . . ? O28 C29 C30 C31 -178.4(5) . . . . ? C33 O32 C31 C34 -92.3(7) . . . . ? C33 O32 C31 C30 90.9(6) . . . . ? C39 C30 C31 O32 179.7(5) . . . . ? C29 C30 C31 O32 2.8(8) . . . . ? C39 C30 C31 C34 2.8(8) . . . . ? C29 C30 C31 C34 -174.1(5) . . . . ? O32 C31 C34 C35 -179.5(5) . . . . ? C30 C31 C34 C35 -2.7(8) . . . . ? O32 C31 C34 C1' 0.3(8) . . . . ? C30 C31 C34 C1' 177.1(5) . . . . ? O2' C1' C34 C31 -122.0(6) . . . . ? O2' C1' C34 C35 57.8(7) . . . . ? C31 C34 C35 C36 0.8(8) . . . . ? C1' C34 C35 C36 -179.0(5) . . . . ? C38 O37 C36 C35 7.2(8) . . . . ? C38 O37 C36 C39 -175.6(6) . . . . ? C34 C35 C36 O37 178.1(5) . . . . ? C34 C35 C36 C39 1.0(8) . . . . ? C31 C30 C39 C36 -1.0(9) . . . . ? C29 C30 C39 C36 175.7(6) . . . . ? O37 C36 C39 C30 -178.3(5) . . . . ? C35 C36 C39 C30 -0.9(9) . . . . ? O1S2 S2 S2' C1S2 -123.9(16) . . . . ? C2S2 S2 S2' C1S2 130.1(16) . . . . ? C1S2 S2 S2' C1S2 0.00(2) . . . . ? O1S2 S2 S2' O1S2 0.000(6) . . . . ? C2S2 S2 S2' O1S2 -106.0(8) . . . . ? C1S2 S2 S2' O1S2 123.9(16) . . . . ? O1S2 S2 S2' C2S2 106.0(8) . . . . ? C2S2 S2 S2' C2S2 0.000(13) . . . . ? C1S2 S2 S2' C2S2 -130.1(16) . . . . ? S2' S2 O1S2 S2' 0.000(5) . . . . ? C2S2 S2 O1S2 S2' 70.9(11) . . . . ? C1S2 S2 O1S2 S2' -39.0(12) . . . . ? C1S2 S2' O1S2 S2 53.8(17) . . . . ? S2 S2' O1S2 S2 0.000(8) . . . . ? C2S2 S2' O1S2 S2 -54.5(8) . . . . ? S2 S2' C1S2 S2 0.00(2) . . . . ? O1S2 S2' C1S2 S2 -38.8(10) . . . . ? C2S2 S2' C1S2 S2 42.4(12) . . . . ? O1S2 S2 C1S2 S2' 58.1(17) . . . . ? S2' S2 C1S2 S2' 0.00(3) . . . . ? C2S2 S2 C1S2 S2' -49.6(17) . . . . ? O1S2 S2 C2S2 S2' -75.2(12) . . . . ? S2' S2 C2S2 S2' 0.000(14) . . . . ? C1S2 S2 C2S2 S2' 35.3(12) . . . . ? C1S2 S2' C2S2 S2 -50.9(17) . . . . ? S2 S2' C2S2 S2 0.00(2) . . . . ? O1S2 S2' C2S2 S2 46.8(7) . . . . ? _refine_diff_density_max 0.718 _refine_diff_density_min -0.851 _refine_diff_density_rms 0.094