# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_k09sel3 _database_code_depnum_ccdc_archive 'CCDC 900347' #TrackingRef 'bigcif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 O2' _chemical_formula_weight 224.33 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2640(2) _cell_length_b 10.7540(2) _cell_length_c 13.3660(3) _cell_angle_alpha 67.311(1) _cell_angle_beta 70.995(1) _cell_angle_gamma 82.495(1) _cell_volume 1286.94(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 17301 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.953 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25723 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 27.59 _reflns_number_total 5889 _reflns_number_gt 4178 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97/2 (Sheldrick 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The asymmetric unit in this structure consists of 2 independent molecules. The alcoholic hydrogens (H2 and H2c) were located in the electron density map, and refine at a distance of 0.98 \%A from the parent oxygen atoms. As the OH functionalites in each molecule are proximate to different crystallographic inversion centres, the gross structure features discrete hydrogen-bonded dimers, each based on only one of the molecules in the asymmetric unit. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.4607P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5889 _refine_ls_number_parameters 300 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1193 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.10050(10) -0.04858(11) 0.87224(8) 0.0291(3) Uani 1 1 d . . . O2 O 0.16802(11) 0.03263(11) 0.98708(9) 0.0325(3) Uani 1 1 d D . . O1A O 0.48420(11) 0.44622(11) 0.38364(9) 0.0322(3) Uani 1 1 d . . . O2A O 0.63203(12) 0.60183(11) 0.37432(10) 0.0367(3) Uani 1 1 d D . . C1 C 0.18578(15) -0.07278(15) 0.94548(13) 0.0277(3) Uani 1 1 d . . . C2 C 0.33158(15) -0.06531(16) 0.86596(13) 0.0279(3) Uani 1 1 d . . . H2B H 0.3525 -0.1524 0.8531 0.033 Uiso 1 1 calc R . . C3 C 0.44841(15) -0.03669(17) 0.90007(14) 0.0325(4) Uani 1 1 d . . . H3A H 0.4563 -0.1107 0.9704 0.039 Uiso 1 1 calc R . . H3B H 0.4296 0.0481 0.9151 0.039 Uiso 1 1 calc R . . C4 C 0.58268(16) -0.02435(18) 0.80379(14) 0.0369(4) Uani 1 1 d . . . H4A H 0.6574 0.0031 0.8226 0.044 Uiso 1 1 calc R . . H4B H 0.6076 -0.1135 0.7970 0.044 Uiso 1 1 calc R . . C5 C 0.57124(16) 0.07810(18) 0.69003(15) 0.0370(4) Uani 1 1 d . . . H5A H 0.6579 0.0767 0.6297 0.044 Uiso 1 1 calc R . . H5B H 0.5605 0.1693 0.6935 0.044 Uiso 1 1 calc R . . C6 C 0.44964(15) 0.05091(17) 0.65800(13) 0.0314(4) Uani 1 1 d . . . H6A H 0.4416 0.1241 0.5873 0.038 Uiso 1 1 calc R . . H6B H 0.4642 -0.0353 0.6452 0.038 Uiso 1 1 calc R . . C7 C 0.31898(14) 0.04401(15) 0.75602(12) 0.0268(3) Uani 1 1 d . . . H7 H 0.3095 0.1321 0.7668 0.032 Uiso 1 1 calc R . . C8 C 0.17911(14) 0.01366(15) 0.75143(12) 0.0257(3) Uani 1 1 d . . . C9 C 0.18633(16) -0.08733(17) 0.69520(14) 0.0331(4) Uani 1 1 d . . . H9A H 0.2281 -0.1724 0.7357 0.040 Uiso 1 1 calc R . . H9B H 0.2467 -0.0512 0.6157 0.040 Uiso 1 1 calc R . . C10 C 0.04458(17) -0.11711(18) 0.69573(16) 0.0398(4) Uani 1 1 d . . . H10A H 0.0546 -0.1799 0.6556 0.048 Uiso 1 1 calc R . . H10B H -0.0136 -0.1611 0.7751 0.048 Uiso 1 1 calc R . . C11 C -0.02507(16) 0.01247(19) 0.63772(15) 0.0391(4) Uani 1 1 d . . . H11A H 0.0292 0.0525 0.5566 0.047 Uiso 1 1 calc R . . H11B H -0.1181 -0.0083 0.6414 0.047 Uiso 1 1 calc R . . C12 C -0.03723(16) 0.11339(18) 0.69478(14) 0.0343(4) Uani 1 1 d . . . H12A H -0.1000 0.0774 0.7734 0.041 Uiso 1 1 calc R . . H12B H -0.0774 0.1987 0.6528 0.041 Uiso 1 1 calc R . . C13 C 0.10364(15) 0.14143(16) 0.69749(13) 0.0295(3) Uani 1 1 d . . . H13A H 0.1613 0.1897 0.6188 0.035 Uiso 1 1 calc R . . H13B H 0.0911 0.2013 0.7407 0.035 Uiso 1 1 calc R . . C14 C 0.14487(17) -0.20733(17) 1.04093(14) 0.0363(4) Uani 1 1 d . . . H14A H 0.1990 -0.2252 1.0934 0.054 Uiso 1 1 calc R . . H14B H 0.1624 -0.2786 1.0094 0.054 Uiso 1 1 calc R . . H14C H 0.0466 -0.2056 1.0819 0.054 Uiso 1 1 calc R . . C1A C 0.62682(15) 0.48125(16) 0.35562(13) 0.0313(3) Uani 1 1 d . . . C2A C 0.68367(16) 0.50943(17) 0.22966(13) 0.0324(4) Uani 1 1 d . . . H2A H 0.7010 0.4202 0.2205 0.039 Uiso 1 1 calc R . . C3A C 0.81421(16) 0.59143(17) 0.15973(13) 0.0337(4) Uani 1 1 d . . . H3A1 H 0.8926 0.5438 0.1869 0.040 Uiso 1 1 calc R . . H3A2 H 0.8028 0.6801 0.1681 0.040 Uiso 1 1 calc R . . C4A C 0.84320(17) 0.61125(18) 0.03462(14) 0.0381(4) Uani 1 1 d . . . H4A1 H 0.9234 0.6715 -0.0121 0.046 Uiso 1 1 calc R . . H4A2 H 0.8673 0.5232 0.0257 0.046 Uiso 1 1 calc R . . C5A C 0.71989(17) 0.67167(18) -0.00892(14) 0.0392(4) Uani 1 1 d . . . H5A1 H 0.7417 0.6772 -0.0883 0.047 Uiso 1 1 calc R . . H5A2 H 0.7028 0.7644 -0.0088 0.047 Uiso 1 1 calc R . . C6A C 0.58934(17) 0.58789(18) 0.06387(13) 0.0360(4) Uani 1 1 d . . . H6A1 H 0.5103 0.6330 0.0366 0.043 Uiso 1 1 calc R . . H6A2 H 0.6019 0.4978 0.0580 0.043 Uiso 1 1 calc R . . C7A C 0.56096(16) 0.57317(16) 0.18739(13) 0.0314(3) Uani 1 1 d . . . H7A H 0.5484 0.6659 0.1897 0.038 Uiso 1 1 calc R . . C8A C 0.43989(16) 0.48787(16) 0.28091(13) 0.0296(3) Uani 1 1 d . . . C9A C 0.41451(17) 0.35987(17) 0.26587(14) 0.0370(4) Uani 1 1 d . . . H9A1 H 0.3958 0.3850 0.1923 0.044 Uiso 1 1 calc R . . H9A2 H 0.4986 0.3030 0.2636 0.044 Uiso 1 1 calc R . . C10A C 0.29324(18) 0.27857(18) 0.36188(15) 0.0411(4) Uani 1 1 d . . . H10C H 0.2785 0.1987 0.3474 0.049 Uiso 1 1 calc R . . H10D H 0.3150 0.2465 0.4348 0.049 Uiso 1 1 calc R . . C11A C 0.16235(18) 0.36347(19) 0.37088(16) 0.0437(4) Uani 1 1 d . . . H11C H 0.0858 0.3094 0.4344 0.052 Uiso 1 1 calc R . . H11D H 0.1372 0.3911 0.2998 0.052 Uiso 1 1 calc R . . C12A C 0.18368(17) 0.48802(18) 0.39130(16) 0.0412(4) Uani 1 1 d . . . H12C H 0.1996 0.4604 0.4662 0.049 Uiso 1 1 calc R . . H12D H 0.0996 0.5450 0.3927 0.049 Uiso 1 1 calc R . . C13A C 0.30641(16) 0.56932(17) 0.29842(15) 0.0361(4) Uani 1 1 d . . . H13C H 0.3220 0.6451 0.3177 0.043 Uiso 1 1 calc R . . H13D H 0.2834 0.6082 0.2259 0.043 Uiso 1 1 calc R . . C14A C 0.69300(18) 0.36662(17) 0.43134(14) 0.0370(4) Uani 1 1 d . . . H14D H 0.6480 0.3569 0.5108 0.055 Uiso 1 1 calc R . . H14E H 0.7911 0.3855 0.4108 0.055 Uiso 1 1 calc R . . H14F H 0.6829 0.2829 0.4216 0.055 Uiso 1 1 calc R . . H2 H 0.0784(13) 0.025(2) 1.0425(15) 0.068(7) Uiso 1 1 d D . . H2C H 0.599(2) 0.583(3) 0.4570(9) 0.090(8) Uiso 1 1 d 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 0.0232(5) 0.0395(6) 0.0242(5) -0.0103(5) -0.0074(4) -0.0023(4) O2 0.0298(6) 0.0387(6) 0.0328(6) -0.0190(5) -0.0069(5) -0.0006(5) O1A 0.0301(6) 0.0385(6) 0.0279(6) -0.0116(5) -0.0084(5) -0.0018(5) O2A 0.0432(7) 0.0348(6) 0.0351(6) -0.0154(5) -0.0115(5) -0.0024(5) C1 0.0281(7) 0.0319(8) 0.0272(8) -0.0128(7) -0.0120(6) 0.0023(6) C2 0.0257(7) 0.0324(8) 0.0288(8) -0.0139(7) -0.0098(6) 0.0014(6) C3 0.0287(8) 0.0383(9) 0.0360(9) -0.0160(8) -0.0143(7) 0.0004(7) C4 0.0253(8) 0.0461(10) 0.0432(10) -0.0183(8) -0.0136(7) 0.0014(7) C5 0.0240(8) 0.0415(10) 0.0422(10) -0.0132(8) -0.0071(7) -0.0029(7) C6 0.0253(7) 0.0363(9) 0.0295(8) -0.0101(7) -0.0069(6) 0.0001(6) C7 0.0239(7) 0.0300(8) 0.0277(8) -0.0119(7) -0.0077(6) -0.0003(6) C8 0.0221(7) 0.0324(8) 0.0225(7) -0.0107(6) -0.0057(6) -0.0005(6) C9 0.0321(8) 0.0370(9) 0.0362(9) -0.0190(8) -0.0117(7) 0.0018(7) C10 0.0372(9) 0.0457(10) 0.0466(10) -0.0262(9) -0.0128(8) -0.0036(8) C11 0.0283(8) 0.0603(12) 0.0392(9) -0.0263(9) -0.0135(7) -0.0012(8) C12 0.0278(8) 0.0468(10) 0.0323(8) -0.0180(8) -0.0124(7) 0.0061(7) C13 0.0285(8) 0.0338(8) 0.0278(8) -0.0123(7) -0.0099(6) 0.0016(6) C14 0.0378(9) 0.0370(9) 0.0316(9) -0.0089(8) -0.0116(7) -0.0004(7) C1A 0.0295(8) 0.0311(8) 0.0328(8) -0.0116(7) -0.0091(7) 0.0006(6) C2A 0.0324(8) 0.0358(9) 0.0308(8) -0.0131(7) -0.0100(7) -0.0018(7) C3A 0.0319(8) 0.0368(9) 0.0322(9) -0.0121(7) -0.0091(7) -0.0023(7) C4A 0.0341(9) 0.0449(10) 0.0324(9) -0.0147(8) -0.0048(7) -0.0024(7) C5A 0.0425(9) 0.0450(10) 0.0277(8) -0.0095(8) -0.0092(7) -0.0078(8) C6A 0.0386(9) 0.0419(10) 0.0300(8) -0.0129(8) -0.0120(7) -0.0052(7) C7A 0.0341(8) 0.0309(8) 0.0303(8) -0.0115(7) -0.0097(7) -0.0031(6) C8A 0.0333(8) 0.0303(8) 0.0268(8) -0.0102(7) -0.0108(6) -0.0024(6) C9A 0.0408(9) 0.0376(9) 0.0343(9) -0.0172(8) -0.0058(7) -0.0077(7) C10A 0.0440(10) 0.0377(10) 0.0399(10) -0.0169(8) -0.0032(8) -0.0114(8) C11A 0.0377(9) 0.0528(11) 0.0420(10) -0.0162(9) -0.0102(8) -0.0140(8) C12A 0.0310(8) 0.0456(10) 0.0489(11) -0.0201(9) -0.0113(8) 0.0006(7) C13A 0.0346(9) 0.0339(9) 0.0410(9) -0.0121(8) -0.0149(7) 0.0002(7) C14A 0.0402(9) 0.0399(9) 0.0337(9) -0.0155(8) -0.0146(7) 0.0060(7) _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 C1 1.4473(17) . ? O1 C8 1.4715(17) . ? O2 C1 1.4119(18) . ? O2 H2 0.965(9) . ? O1A C1A 1.4502(18) . ? O1A C8A 1.4736(18) . ? O2A C1A 1.4225(18) . ? O2A H2C 0.989(10) . ? C1 C14 1.511(2) . ? C1 C2 1.518(2) . ? C2 C3 1.517(2) . ? C2 C7 1.520(2) . ? C2 H2B 1.0000 . ? C3 C4 1.528(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.526(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.538(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.526(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.538(2) . ? C7 H7 1.0000 . ? C8 C9 1.524(2) . ? C8 C13 1.526(2) . ? C9 C10 1.527(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.524(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.522(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.529(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C1A C14A 1.507(2) . ? C1A C2A 1.510(2) . ? C2A C3A 1.518(2) . ? C2A C7A 1.521(2) . ? C2A H2A 1.0000 . ? C3A C4A 1.532(2) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A C5A 1.528(2) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C5A C6A 1.531(2) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C6A C7A 1.527(2) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A C8A 1.533(2) . ? C7A H7A 1.0000 . ? C8A C13A 1.528(2) . ? C8A C9A 1.531(2) . ? C9A C10A 1.529(2) . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C10A C11A 1.521(3) . ? C10A H10C 0.9900 . ? C10A H10D 0.9900 . ? C11A C12A 1.521(2) . ? C11A H11C 0.9900 . ? C11A H11D 0.9900 . ? C12A C13A 1.525(2) . ? C12A H12C 0.9900 . ? C12A H12D 0.9900 . ? C13A H13C 0.9900 . ? C13A H13D 0.9900 . ? C14A H14D 0.9800 . ? C14A H14E 0.9800 . ? C14A H14F 0.9800 . ? 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 C1 O1 C8 111.71(10) . . ? C1 O2 H2 109.0(13) . . ? C1A O1A C8A 111.49(11) . . ? C1A O2A H2C 109.3(15) . . ? O2 C1 O1 109.98(12) . . ? O2 C1 C14 111.63(12) . . ? O1 C1 C14 107.62(12) . . ? O2 C1 C2 108.12(12) . . ? O1 C1 C2 103.63(11) . . ? C14 C1 C2 115.50(13) . . ? C3 C2 C1 118.59(12) . . ? C3 C2 C7 111.50(13) . . ? C1 C2 C7 102.32(12) . . ? C3 C2 H2B 108.0 . . ? C1 C2 H2B 108.0 . . ? C7 C2 H2B 108.0 . . ? C2 C3 C4 109.03(13) . . ? C2 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? C2 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C5 C4 C3 112.16(13) . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C4 C5 C6 113.17(13) . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C5 107.78(13) . . ? C7 C6 H6A 110.1 . . ? C5 C6 H6A 110.1 . . ? C7 C6 H6B 110.1 . . ? C5 C6 H6B 110.1 . . ? H6A C6 H6B 108.5 . . ? C2 C7 C6 110.74(12) . . ? C2 C7 C8 102.95(12) . . ? C6 C7 C8 120.50(12) . . ? C2 C7 H7 107.3 . . ? C6 C7 H7 107.3 . . ? C8 C7 H7 107.3 . . ? O1 C8 C9 107.77(12) . . ? O1 C8 C13 108.48(11) . . ? C9 C8 C13 110.35(12) . . ? O1 C8 C7 103.06(11) . . ? C9 C8 C7 114.31(12) . . ? C13 C8 C7 112.38(12) . . ? C8 C9 C10 112.33(13) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 110.60(14) . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 110.85(13) . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C13 111.05(13) . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C8 C13 C12 113.11(13) . . ? C8 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? C8 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C1 C14 H14A 109.5 . . ? C1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O2A C1A O1A 109.40(12) . . ? O2A C1A C14A 110.26(13) . . ? O1A C1A C14A 107.94(13) . . ? O2A C1A C2A 108.75(13) . . ? O1A C1A C2A 103.82(12) . . ? C14A C1A C2A 116.33(13) . . ? C1A C2A C3A 120.08(13) . . ? C1A C2A C7A 102.54(12) . . ? C3A C2A C7A 112.47(14) . . ? C1A C2A H2A 107.0 . . ? C3A C2A H2A 107.0 . . ? C7A C2A H2A 107.0 . . ? C2A C3A C4A 108.95(13) . . ? C2A C3A H3A1 109.9 . . ? C4A C3A H3A1 109.9 . . ? C2A C3A H3A2 109.9 . . ? C4A C3A H3A2 109.9 . . ? H3A1 C3A H3A2 108.3 . . ? C5A C4A C3A 112.36(13) . . ? C5A C4A H4A1 109.1 . . ? C3A C4A H4A1 109.1 . . ? C5A C4A H4A2 109.1 . . ? C3A C4A H4A2 109.1 . . ? H4A1 C4A H4A2 107.9 . . ? C4A C5A C6A 112.05(14) . . ? C4A C5A H5A1 109.2 . . ? C6A C5A H5A1 109.2 . . ? C4A C5A H5A2 109.2 . . ? C6A C5A H5A2 109.2 . . ? H5A1 C5A H5A2 107.9 . . ? C7A C6A C5A 108.85(13) . . ? C7A C6A H6A1 109.9 . . ? C5A C6A H6A1 109.9 . . ? C7A C6A H6A2 109.9 . . ? C5A C6A H6A2 109.9 . . ? H6A1 C6A H6A2 108.3 . . ? C2A C7A C6A 110.85(13) . . ? C2A C7A C8A 102.78(13) . . ? C6A C7A C8A 120.39(13) . . ? C2A C7A H7A 107.4 . . ? C6A C7A H7A 107.4 . . ? C8A C7A H7A 107.4 . . ? O1A C8A C13A 108.55(12) . . ? O1A C8A C9A 107.67(12) . . ? C13A C8A C9A 110.03(13) . . ? O1A C8A C7A 103.00(11) . . ? C13A C8A C7A 112.61(13) . . ? C9A C8A C7A 114.48(12) . . ? C10A C9A C8A 112.14(13) . . ? C10A C9A H9A1 109.2 . . ? C8A C9A H9A1 109.2 . . ? C10A C9A H9A2 109.2 . . ? C8A C9A H9A2 109.2 . . ? H9A1 C9A H9A2 107.9 . . ? C11A C10A C9A 111.03(15) . . ? C11A C10A H10C 109.4 . . ? C9A C10A H10C 109.4 . . ? C11A C10A H10D 109.4 . . ? C9A C10A H10D 109.4 . . ? H10C C10A H10D 108.0 . . ? C10A C11A C12A 110.24(14) . . ? C10A C11A H11C 109.6 . . ? C12A C11A H11C 109.6 . . ? C10A C11A H11D 109.6 . . ? C12A C11A H11D 109.6 . . ? H11C C11A H11D 108.1 . . ? C11A C12A C13A 110.90(14) . . ? C11A C12A H12C 109.5 . . ? C13A C12A H12C 109.5 . . ? C11A C12A H12D 109.5 . . ? C13A C12A H12D 109.5 . . ? H12C C12A H12D 108.0 . . ? C12A C13A C8A 114.16(14) . . ? C12A C13A H13C 108.7 . . ? C8A C13A H13C 108.7 . . ? C12A C13A H13D 108.7 . . ? C8A C13A H13D 108.7 . . ? H13C C13A H13D 107.6 . . ? C1A C14A H14D 109.5 . . ? C1A C14A H14E 109.5 . . ? H14D C14A H14E 109.5 . . ? C1A C14A H14F 109.5 . . ? H14D C14A H14F 109.5 . . ? H14E C14A H14F 109.5 . . ? 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 C8 O1 C1 O2 97.62(13) . . . . ? C8 O1 C1 C14 -140.58(12) . . . . ? C8 O1 C1 C2 -17.76(15) . . . . ? O2 C1 C2 C3 42.01(18) . . . . ? O1 C1 C2 C3 158.70(13) . . . . ? C14 C1 C2 C3 -83.86(17) . . . . ? O2 C1 C2 C7 -81.11(13) . . . . ? O1 C1 C2 C7 35.59(14) . . . . ? C14 C1 C2 C7 153.03(13) . . . . ? C1 C2 C3 C4 -176.11(14) . . . . ? C7 C2 C3 C4 -57.69(17) . . . . ? C2 C3 C4 C5 53.37(18) . . . . ? C3 C4 C5 C6 -53.97(19) . . . . ? C4 C5 C6 C7 54.83(18) . . . . ? C3 C2 C7 C6 62.03(16) . . . . ? C1 C2 C7 C6 -170.20(12) . . . . ? C3 C2 C7 C8 -167.88(12) . . . . ? C1 C2 C7 C8 -40.11(14) . . . . ? C5 C6 C7 C2 -58.11(16) . . . . ? C5 C6 C7 C8 -178.19(13) . . . . ? C1 O1 C8 C9 113.93(12) . . . . ? C1 O1 C8 C13 -126.59(12) . . . . ? C1 O1 C8 C7 -7.28(15) . . . . ? C2 C7 C8 O1 29.30(13) . . . . ? C6 C7 C8 O1 153.16(13) . . . . ? C2 C7 C8 C9 -87.35(15) . . . . ? C6 C7 C8 C9 36.5(2) . . . . ? C2 C7 C8 C13 145.87(12) . . . . ? C6 C7 C8 C13 -90.26(16) . . . . ? O1 C8 C9 C10 64.47(17) . . . . ? C13 C8 C9 C10 -53.81(18) . . . . ? C7 C8 C9 C10 178.37(14) . . . . ? C8 C9 C10 C11 56.77(18) . . . . ? C9 C10 C11 C12 -57.06(18) . . . . ? C10 C11 C12 C13 55.58(19) . . . . ? O1 C8 C13 C12 -65.35(15) . . . . ? C9 C8 C13 C12 52.50(16) . . . . ? C7 C8 C13 C12 -178.63(12) . . . . ? C11 C12 C13 C8 -53.98(18) . . . . ? C8A O1A C1A O2A 99.70(13) . . . . ? C8A O1A C1A C14A -140.30(12) . . . . ? C8A O1A C1A C2A -16.25(15) . . . . ? O2A C1A C2A C3A 43.99(19) . . . . ? O1A C1A C2A C3A 160.40(14) . . . . ? C14A C1A C2A C3A -81.19(19) . . . . ? O2A C1A C2A C7A -81.55(14) . . . . ? O1A C1A C2A C7A 34.86(15) . . . . ? C14A C1A C2A C7A 153.27(14) . . . . ? C1A C2A C3A C4A -176.72(14) . . . . ? C7A C2A C3A C4A -55.99(18) . . . . ? C2A C3A C4A C5A 53.79(19) . . . . ? C3A C4A C5A C6A -55.46(19) . . . . ? C4A C5A C6A C7A 55.74(19) . . . . ? C1A C2A C7A C6A -170.33(13) . . . . ? C3A C2A C7A C6A 59.30(17) . . . . ? C1A C2A C7A C8A -40.42(15) . . . . ? C3A C2A C7A C8A -170.79(13) . . . . ? C5A C6A C7A C2A -57.15(18) . . . . ? C5A C6A C7A C8A -177.01(14) . . . . ? C1A O1A C8A C13A -128.57(13) . . . . ? C1A O1A C8A C9A 112.34(13) . . . . ? C1A O1A C8A C7A -8.99(15) . . . . ? C2A C7A C8A O1A 30.32(14) . . . . ? C6A C7A C8A O1A 154.11(14) . . . . ? C2A C7A C8A C13A 147.06(13) . . . . ? C6A C7A C8A C13A -89.15(18) . . . . ? C2A C7A C8A C9A -86.26(15) . . . . ? C6A C7A C8A C9A 37.5(2) . . . . ? O1A C8A C9A C10A 65.81(17) . . . . ? C13A C8A C9A C10A -52.33(19) . . . . ? C7A C8A C9A C10A 179.67(14) . . . . ? C8A C9A C10A C11A 57.14(19) . . . . ? C9A C10A C11A C12A -58.22(19) . . . . ? C10A C11A C12A C13A 56.0(2) . . . . ? C11A C12A C13A C8A -53.8(2) . . . . ? O1A C8A C13A C12A -66.31(17) . . . . ? C9A C8A C13A C12A 51.29(18) . . . . ? C7A C8A C13A C12A -179.69(13) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.265 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.041 data_k11sel1 _database_code_depnum_ccdc_archive 'CCDC 900348' #TrackingRef 'bigcif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 N4 O4' _chemical_formula_weight 386.45 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5080(6) _cell_length_b 11.6860(6) _cell_length_c 16.6470(10) _cell_angle_alpha 81.989(2) _cell_angle_beta 90.159(3) _cell_angle_gamma 78.388(3) _cell_volume 1981.81(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 97540 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25927 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1718 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_theta_max 25.03 _reflns_number_total 25927 _reflns_number_gt 14454 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97/2 (Sheldrick 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 2 molecules in the asymmetric unit. Model takes account of 50% twinning about the 0 0 1 reciprocal axis. The model is unambiguous - but despite modelling for twinning the residuals remain much higher than desirable. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+22.1385P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 25927 _refine_ls_number_parameters 516 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2588 _refine_ls_R_factor_gt 0.1792 _refine_ls_wR_factor_ref 0.4211 _refine_ls_wR_factor_gt 0.3768 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6724(5) 1.2273(4) 0.3727(3) 0.0477(13) Uani 1 1 d . . . O2 O 0.6591(5) 1.1050(4) 0.2875(3) 0.0511(14) Uani 1 1 d . . . O3 O 0.8445(6) 0.7025(4) 0.3496(3) 0.0545(16) Uani 1 1 d . . . O4 O 0.9404(5) 0.6221(4) 0.4651(3) 0.0385(12) Uani 1 1 d . . . N1 N 0.6927(6) 1.1274(4) 0.3533(4) 0.0352(14) Uani 1 1 d . . . N2 N 0.8813(5) 0.7098(5) 0.4187(4) 0.0351(14) Uani 1 1 d . . . N3 N 0.9473(6) 0.7499(5) 0.5820(3) 0.0359(14) Uani 1 1 d . . . H3 H 0.9753 0.6787 0.5693 0.043 Uiso 1 1 calc R . . N4 N 0.9598(5) 0.7745(5) 0.6620(3) 0.0344(13) Uani 1 1 d . . . C1 C 0.7622(6) 1.0300(5) 0.4118(4) 0.0324(16) Uani 1 1 d . . . C2 C 0.7927(6) 0.9183(5) 0.3900(4) 0.0297(15) Uani 1 1 d . . . H2 H 0.7700 0.9060 0.3371 0.036 Uiso 1 1 calc R . . C3 C 0.8563(7) 0.8242(5) 0.4449(4) 0.0336(16) Uani 1 1 d . . . C4 C 0.8902(6) 0.8411(5) 0.5256(4) 0.0295(15) Uani 1 1 d . . . C5 C 0.8585(7) 0.9579(5) 0.5433(4) 0.0359(17) Uani 1 1 d . . . H5 H 0.8802 0.9725 0.5958 0.043 Uiso 1 1 calc R . . C6 C 0.7980(7) 1.0505(5) 0.4884(4) 0.0358(17) Uani 1 1 d . . . H6 H 0.7805 1.1283 0.5021 0.043 Uiso 1 1 calc R . . C7 C 1.0134(6) 0.6816(6) 0.7134(4) 0.0331(16) Uani 1 1 d . . . C8 C 1.0610(8) 0.5583(6) 0.6943(5) 0.0453(19) Uani 1 1 d . . . H8A H 0.9865 0.5224 0.6855 0.068 Uiso 1 1 calc R . . H8B H 1.1155 0.5110 0.7398 0.068 Uiso 1 1 calc R . . H8C H 1.1122 0.5612 0.6452 0.068 Uiso 1 1 calc R . . C9 C 1.0324(7) 0.7079(6) 0.7985(4) 0.0379(17) Uani 1 1 d . . . H9 H 0.9840 0.7903 0.8008 0.045 Uiso 1 1 calc R . . C10 C 1.1759(8) 0.7046(7) 0.8167(5) 0.055(2) Uani 1 1 d . . . H10A H 1.2075 0.7602 0.7748 0.066 Uiso 1 1 calc R . . H10B H 1.2265 0.6243 0.8133 0.066 Uiso 1 1 calc R . . C11 C 1.2009(9) 0.7371(8) 0.9006(5) 0.059(2) Uani 1 1 d . . . H11A H 1.2956 0.7263 0.9113 0.071 Uiso 1 1 calc R . . H11B H 1.1610 0.8211 0.9021 0.071 Uiso 1 1 calc R . . C12 C 1.1436(7) 0.6599(7) 0.9651(5) 0.0463(19) Uani 1 1 d . . . H12A H 1.1529 0.6869 1.0182 0.056 Uiso 1 1 calc R . . H12B H 1.1936 0.5778 0.9689 0.056 Uiso 1 1 calc R . . C13 C 0.9990(6) 0.6610(6) 0.9483(4) 0.0377(17) Uani 1 1 d . . . H13A H 0.9687 0.6051 0.9905 0.045 Uiso 1 1 calc R . . H13B H 0.9470 0.7409 0.9510 0.045 Uiso 1 1 calc R . . C14 C 0.9779(7) 0.6261(5) 0.8641(4) 0.0359(17) Uani 1 1 d . . . H14 H 1.0304 0.5446 0.8641 0.043 Uiso 1 1 calc R . . C15 C 0.8341(6) 0.6204(5) 0.8490(4) 0.0286(14) Uani 1 1 d . . . C16 C 0.8028(7) 0.5184(6) 0.8406(4) 0.0390(17) Uani 1 1 d . . . H16 H 0.8713 0.4518 0.8397 0.047 Uiso 1 1 calc R . . C17 C 0.6669(7) 0.5017(6) 0.8325(5) 0.0444(19) Uani 1 1 d . . . H17A H 0.6451 0.4553 0.8831 0.053 Uiso 1 1 calc R . . H17B H 0.6614 0.4553 0.7876 0.053 Uiso 1 1 calc R . . C18 C 0.5685(9) 0.6148(7) 0.8163(7) 0.072(3) Uani 1 1 d . . . H18A H 0.5641 0.6436 0.7573 0.086 Uiso 1 1 calc R . . H18B H 0.4820 0.5992 0.8317 0.086 Uiso 1 1 calc R . . C19 C 0.5973(7) 0.7090(6) 0.8608(5) 0.052(2) Uani 1 1 d . . . H19A H 0.5856 0.6872 0.9195 0.062 Uiso 1 1 calc R . . H19B H 0.5350 0.7838 0.8422 0.062 Uiso 1 1 calc R . . C20 C 0.7350(7) 0.7279(5) 0.8475(5) 0.0400(18) Uani 1 1 d . . . H20A H 0.7365 0.7775 0.7943 0.048 Uiso 1 1 calc R . . H20B H 0.7582 0.7724 0.8898 0.048 Uiso 1 1 calc R . . C19A C 0.2887(14) 0.3208(13) 0.8622(19) 0.124(12) Uani 0.70 1 d PD A 1 H19C H 0.2646 0.3646 0.9085 0.149 Uiso 0.70 1 calc PR A 1 H19D H 0.2772 0.3809 0.8132 0.149 Uiso 0.70 1 calc PR A 1 O1A O 0.1731(4) 0.7328(3) 0.4244(3) 0.0413(13) Uani 1 1 d . . . O2A O 0.1632(5) 0.6277(4) 0.3274(3) 0.0447(13) Uani 1 1 d . . . O3A O 0.3497(5) 0.2243(4) 0.3603(3) 0.0494(15) Uani 1 1 d . . . O4A O 0.4546(5) 0.1289(4) 0.4689(3) 0.0389(12) Uani 1 1 d . . . N1A N 0.2013(5) 0.6393(4) 0.3962(4) 0.0321(13) Uani 1 1 d . . . N2A N 0.3937(5) 0.2220(4) 0.4292(3) 0.0348(14) Uani 1 1 d . . . N3A N 0.4889(5) 0.2400(4) 0.5907(3) 0.0296(13) Uani 1 1 d . . . H3A H 0.4955 0.1696 0.5760 0.036 Uiso 1 1 calc R . . N4A N 0.5499(5) 0.2530(4) 0.6629(3) 0.0275(12) Uani 1 1 d . . . C1A C 0.2768(6) 0.5355(5) 0.4459(4) 0.0285(15) Uani 1 1 d . . . C2A C 0.3030(6) 0.4301(5) 0.4170(4) 0.0308(15) Uani 1 1 d . . . H2A H 0.2733 0.4246 0.3641 0.037 Uiso 1 1 calc R . . C3A C 0.3725(6) 0.3320(5) 0.4646(4) 0.0288(15) Uani 1 1 d . . . C4A C 0.4191(6) 0.3373(5) 0.5432(4) 0.0269(14) Uani 1 1 d . . . C5A C 0.3922(6) 0.4460(5) 0.5726(4) 0.0311(16) Uani 1 1 d . . . H5A H 0.4234 0.4519 0.6252 0.037 Uiso 1 1 calc R . . C6A C 0.3183(6) 0.5475(6) 0.5241(4) 0.0364(17) Uani 1 1 d . . . H6A H 0.2976 0.6212 0.5439 0.044 Uiso 1 1 calc R . . C7A C 0.6004(6) 0.1522(5) 0.7051(4) 0.0296(15) Uani 1 1 d . . . C8A C 0.5895(7) 0.0347(5) 0.6843(4) 0.0346(16) Uani 1 1 d . . . H8A1 H 0.4981 0.0342 0.6729 0.052 Uiso 1 1 calc R . . H8A2 H 0.6229 -0.0264 0.7301 0.052 Uiso 1 1 calc R . . H8A3 H 0.6402 0.0190 0.6364 0.052 Uiso 1 1 calc R . . C9A C 0.6776(6) 0.1555(5) 0.7826(4) 0.0253(14) Uani 1 1 d . . . H9A H 0.6746 0.2401 0.7879 0.030 Uiso 1 1 calc R . . C10A C 0.8181(7) 0.0960(6) 0.7779(5) 0.0407(17) Uani 1 1 d . . . H10C H 0.8559 0.1339 0.7294 0.049 Uiso 1 1 calc R . . H10D H 0.8235 0.0120 0.7721 0.049 Uiso 1 1 calc R . . C11A C 0.8971(7) 0.1038(6) 0.8535(5) 0.048(2) Uani 1 1 d . . . H11C H 0.9874 0.0597 0.8502 0.057 Uiso 1 1 calc R . . H11D H 0.8998 0.1873 0.8564 0.057 Uiso 1 1 calc R . . C12A C 0.8368(7) 0.0527(6) 0.9290(5) 0.0421(18) Uani 1 1 d . . . H12C H 0.8854 0.0635 0.9775 0.051 Uiso 1 1 calc R . . H12D H 0.8442 -0.0331 0.9290 0.051 Uiso 1 1 calc R . . C13A C 0.6939(7) 0.1108(6) 0.9343(5) 0.0418(18) Uani 1 1 d . . . H13C H 0.6867 0.1953 0.9392 0.050 Uiso 1 1 calc R . . H13D H 0.6575 0.0729 0.9834 0.050 Uiso 1 1 calc R . . C14A C 0.6150(6) 0.0995(5) 0.8586(4) 0.0335(16) Uani 1 1 d . . . H14A H 0.6256 0.0134 0.8552 0.040 Uiso 1 1 calc R . . C15A C 0.4705(7) 0.1488(6) 0.8634(4) 0.0341(16) Uani 1 1 d . A . C16A C 0.3851(6) 0.0826(6) 0.8568(4) 0.0421(18) Uani 1 1 d . A . H16A H 0.4167 0.0024 0.8503 0.051 Uiso 1 1 calc R . . C17A C 0.2399(7) 0.1253(7) 0.8589(5) 0.051(2) Uani 1 1 d . . . H17C H 0.2074 0.0863 0.9091 0.062 Uiso 1 1 calc R B 1 H17D H 0.1982 0.1019 0.8121 0.062 Uiso 1 1 calc R B 1 C18A C 0.1998(12) 0.2619(12) 0.8560(10) 0.068(4) Uani 0.70 1 d PD A 1 H18C H 0.1509 0.2942 0.8042 0.082 Uiso 0.70 1 calc PR A 1 H18D H 0.1386 0.2775 0.9002 0.082 Uiso 0.70 1 calc PR A 1 C20A C 0.4297(7) 0.2751(6) 0.8722(5) 0.0452(19) Uani 1 1 d . . . H20C H 0.4586 0.2867 0.9267 0.054 Uiso 1 1 calc R A 1 H20D H 0.4743 0.3220 0.8315 0.054 Uiso 1 1 calc R A 1 C18B C 0.209(2) 0.2233(19) 0.8933(14) 0.021(5) Uiso 0.30 1 d PD A 2 H18E H 0.1270 0.2677 0.8657 0.025 Uiso 0.30 1 calc PR A 2 H18F H 0.1869 0.1965 0.9496 0.025 Uiso 0.30 1 calc PR A 2 C19B C 0.279(4) 0.301(4) 0.900(3) 0.059(12) Uiso 0.30 1 d PD A 2 H19E H 0.2785 0.3149 0.9570 0.070 Uiso 0.30 1 calc PR A 2 H19F H 0.2339 0.3763 0.8671 0.070 Uiso 0.30 1 calc PR A 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 O1 0.058(3) 0.036(3) 0.047(3) 0.003(2) -0.002(3) -0.009(2) O2 0.067(4) 0.047(3) 0.040(3) 0.007(2) -0.012(3) -0.024(3) O3 0.086(4) 0.035(3) 0.041(3) -0.015(2) -0.014(3) -0.001(3) O4 0.051(3) 0.023(2) 0.041(3) -0.007(2) 0.002(2) -0.006(2) N1 0.046(4) 0.023(3) 0.039(4) -0.006(2) 0.002(3) -0.011(2) N2 0.033(3) 0.036(3) 0.042(4) -0.014(3) 0.002(3) -0.014(3) N3 0.050(4) 0.030(3) 0.028(3) -0.008(2) 0.001(3) -0.006(3) N4 0.038(3) 0.038(3) 0.028(3) -0.002(3) -0.006(3) -0.010(2) C1 0.032(4) 0.026(3) 0.037(4) -0.002(3) -0.004(3) -0.001(3) C2 0.023(3) 0.029(4) 0.036(4) 0.001(3) -0.004(3) -0.006(3) C3 0.044(4) 0.023(3) 0.032(4) -0.005(3) 0.010(3) -0.003(3) C4 0.026(4) 0.031(3) 0.031(4) -0.003(3) 0.001(3) -0.006(3) C5 0.040(4) 0.030(4) 0.042(4) -0.017(3) 0.003(3) -0.008(3) C6 0.033(4) 0.025(3) 0.050(5) -0.008(3) 0.003(3) -0.007(3) C7 0.035(4) 0.035(4) 0.033(4) -0.011(3) 0.005(3) -0.014(3) C8 0.053(5) 0.045(4) 0.037(4) -0.011(3) -0.005(4) -0.005(3) C9 0.036(4) 0.049(4) 0.030(4) 0.002(3) 0.005(3) -0.019(3) C10 0.054(5) 0.073(6) 0.053(5) -0.026(4) 0.006(4) -0.036(4) C11 0.073(6) 0.074(6) 0.041(5) -0.012(4) -0.004(4) -0.042(5) C12 0.051(5) 0.056(5) 0.037(4) -0.008(3) -0.007(4) -0.021(4) C13 0.032(4) 0.045(4) 0.033(4) -0.007(3) -0.007(3) -0.002(3) C14 0.045(4) 0.026(3) 0.037(4) -0.007(3) -0.003(3) -0.004(3) C15 0.034(4) 0.022(3) 0.029(4) -0.001(3) 0.005(3) -0.006(3) C16 0.050(5) 0.027(4) 0.042(4) -0.007(3) 0.002(4) -0.011(3) C17 0.049(5) 0.032(4) 0.058(5) -0.013(3) -0.004(4) -0.017(3) C18 0.050(5) 0.052(5) 0.124(9) -0.025(5) 0.013(5) -0.025(4) C19 0.040(4) 0.045(4) 0.068(6) -0.017(4) -0.004(4) 0.001(3) C20 0.042(4) 0.022(3) 0.058(5) -0.007(3) -0.007(4) -0.009(3) C19A 0.019(7) 0.029(8) 0.32(4) -0.018(15) 0.009(14) 0.010(6) O1A 0.042(3) 0.018(2) 0.061(3) -0.007(2) -0.009(2) 0.0042(19) O2A 0.055(3) 0.035(3) 0.043(3) 0.004(2) -0.015(3) -0.013(2) O3A 0.077(4) 0.029(3) 0.041(3) -0.017(2) -0.011(3) 0.001(2) O4A 0.049(3) 0.023(2) 0.042(3) -0.001(2) -0.007(2) -0.003(2) N1A 0.034(3) 0.018(3) 0.047(4) -0.007(2) 0.007(3) -0.009(2) N2A 0.040(3) 0.025(3) 0.038(4) -0.002(3) -0.001(3) -0.006(2) N3A 0.039(3) 0.016(3) 0.034(3) -0.008(2) -0.007(3) -0.003(2) N4A 0.020(3) 0.028(3) 0.031(3) 0.000(2) -0.003(2) -0.001(2) C1A 0.031(4) 0.016(3) 0.036(4) 0.001(3) 0.001(3) -0.002(3) C2A 0.021(3) 0.038(4) 0.035(4) -0.006(3) -0.002(3) -0.008(3) C3A 0.037(4) 0.013(3) 0.038(4) -0.004(3) 0.005(3) -0.007(3) C4A 0.034(4) 0.022(3) 0.027(4) -0.006(3) 0.008(3) -0.009(3) C5A 0.046(4) 0.016(3) 0.036(4) -0.013(3) -0.008(3) -0.009(3) C6A 0.030(4) 0.033(4) 0.051(5) -0.008(3) 0.005(3) -0.015(3) C7A 0.022(3) 0.037(4) 0.033(4) -0.010(3) 0.002(3) -0.011(3) C8A 0.042(4) 0.026(3) 0.037(4) 0.000(3) -0.005(3) -0.011(3) C9A 0.022(3) 0.021(3) 0.034(4) -0.007(3) -0.007(3) -0.006(2) C10A 0.036(4) 0.038(4) 0.046(5) -0.001(3) -0.003(4) -0.007(3) C11A 0.032(4) 0.049(5) 0.063(6) -0.009(4) -0.014(4) -0.008(3) C12A 0.027(4) 0.050(4) 0.045(5) 0.001(3) -0.019(3) -0.002(3) C13A 0.036(4) 0.039(4) 0.048(5) -0.011(3) -0.009(4) 0.000(3) C14A 0.037(4) 0.023(3) 0.042(4) -0.002(3) -0.013(3) -0.013(3) C15A 0.037(4) 0.042(4) 0.023(4) -0.005(3) 0.004(3) -0.006(3) C16A 0.029(4) 0.048(4) 0.047(5) 0.008(3) -0.004(4) -0.013(3) C17A 0.043(5) 0.069(5) 0.045(5) -0.006(4) 0.011(4) -0.018(4) C18A 0.035(7) 0.073(9) 0.079(11) 0.014(9) 0.004(7) 0.013(7) C20A 0.029(4) 0.052(5) 0.056(5) -0.011(4) 0.004(4) -0.008(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 O1 N1 1.231(6) . ? O2 N1 1.228(7) . ? O3 N2 1.233(7) . ? O4 N2 1.247(7) . ? N1 C1 1.459(8) . ? N2 C3 1.438(8) . ? N3 C4 1.356(8) . ? N3 N4 1.411(7) . ? N3 H3 0.8800 . ? N4 C7 1.312(8) . ? C1 C2 1.379(8) . ? C1 C6 1.394(9) . ? C2 C3 1.382(9) . ? C2 H2 0.9500 . ? C3 C4 1.439(9) . ? C4 C5 1.410(8) . ? C5 C6 1.362(9) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.505(9) . ? C7 C9 1.511(9) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.530(10) . ? C9 C14 1.539(10) . ? C9 H9 1.0000 . ? C10 C11 1.532(10) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.511(11) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.542(10) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.540(9) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.547(9) . ? C14 H14 1.0000 . ? C15 C16 1.323(8) . ? C15 C20 1.459(8) . ? C16 C17 1.488(10) . ? C16 H16 0.9500 . ? C17 C18 1.496(11) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.488(11) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.519(10) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C19A C18A 1.279(14) . ? C19A C20A 1.472(16) . ? C19A H19C 0.9900 . ? C19A H19D 0.9900 . ? O1A N1A 1.232(6) . ? O2A N1A 1.246(7) . ? O3A N2A 1.230(7) . ? O4A N2A 1.244(6) . ? N1A C1A 1.454(8) . ? N2A C3A 1.465(7) . ? N3A C4A 1.366(8) . ? N3A N4A 1.402(7) . ? N3A H3A 0.8800 . ? N4A C7A 1.296(8) . ? C1A C2A 1.361(8) . ? C1A C6A 1.405(9) . ? C2A C3A 1.372(9) . ? C2A H2A 0.9500 . ? C3A C4A 1.409(9) . ? C4A C5A 1.402(8) . ? C5A C6A 1.422(9) . ? C5A H5A 0.9500 . ? C6A H6A 0.9500 . ? C7A C8A 1.487(8) . ? C7A C9A 1.531(8) . ? C8A H8A1 0.9800 . ? C8A H8A2 0.9800 . ? C8A H8A3 0.9800 . ? C9A C10A 1.508(9) . ? C9A C14A 1.552(9) . ? C9A H9A 1.0000 . ? C10A C11A 1.529(9) . ? C10A H10C 0.9900 . ? C10A H10D 0.9900 . ? C11A C12A 1.511(11) . ? C11A H11C 0.9900 . ? C11A H11D 0.9900 . ? C12A C13A 1.526(10) . ? C12A H12C 0.9900 . ? C12A H12D 0.9900 . ? C13A C14A 1.541(9) . ? C13A H13C 0.9900 . ? C13A H13D 0.9900 . ? C14A C15A 1.519(9) . ? C14A H14A 1.0000 . ? C15A C16A 1.311(9) . ? C15A C20A 1.480(9) . ? C16A C17A 1.509(10) . ? C16A H16A 0.9500 . ? C17A C18B 1.33(2) . ? C17A C18A 1.561(15) . ? C17A H17C 0.9900 . ? C17A H17D 0.9900 . ? C18A H18C 0.9900 . ? C18A H18D 0.9900 . ? C20A C19B 1.63(5) . ? C20A H20C 0.9900 . ? C20A H20D 0.9900 . ? C18B C19B 1.29(2) . ? C18B H18E 0.9900 . ? C18B H18F 0.9900 . ? C19B H19E 0.9900 . ? C19B H19F 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 N1 O1 124.0(6) . . ? O2 N1 C1 118.0(5) . . ? O1 N1 C1 118.0(5) . . ? O3 N2 O4 122.0(5) . . ? O3 N2 C3 118.1(5) . . ? O4 N2 C3 119.9(5) . . ? C4 N3 N4 116.9(5) . . ? C4 N3 H3 121.5 . . ? N4 N3 H3 121.5 . . ? C7 N4 N3 113.5(5) . . ? C2 C1 C6 120.7(6) . . ? C2 C1 N1 119.2(6) . . ? C6 C1 N1 120.0(5) . . ? C1 C2 C3 120.3(6) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 N2 117.1(6) . . ? C2 C3 C4 120.6(6) . . ? N2 C3 C4 122.3(5) . . ? N3 C4 C5 121.8(6) . . ? N3 C4 C3 122.1(6) . . ? C5 C4 C3 116.1(6) . . ? C6 C5 C4 122.9(6) . . ? C6 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C5 C6 C1 119.2(6) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? N4 C7 C8 126.5(6) . . ? N4 C7 C9 113.9(6) . . ? C8 C7 C9 119.5(6) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 C10 110.5(6) . . ? C7 C9 C14 113.5(5) . . ? C10 C9 C14 110.7(6) . . ? C7 C9 H9 107.3 . . ? C10 C9 H9 107.3 . . ? C14 C9 H9 107.3 . . ? C9 C10 C11 113.1(7) . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 109.9(6) . . ? C12 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? C12 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C11 C12 C13 113.2(6) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 111.2(6) . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C9 C14 C13 109.7(5) . . ? C9 C14 C15 114.3(5) . . ? C13 C14 C15 111.3(6) . . ? C9 C14 H14 107.0 . . ? C13 C14 H14 107.0 . . ? C15 C14 H14 107.0 . . ? C16 C15 C20 121.3(6) . . ? C16 C15 C14 119.9(6) . . ? C20 C15 C14 118.7(5) . . ? C15 C16 C17 124.1(6) . . ? C15 C16 H16 118.0 . . ? C17 C16 H16 118.0 . . ? C16 C17 C18 113.7(6) . . ? C16 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? C16 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C19 C18 C17 113.6(7) . . ? C19 C18 H18A 108.8 . . ? C17 C18 H18A 108.8 . . ? C19 C18 H18B 108.8 . . ? C17 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C18 C19 C20 111.7(7) . . ? C18 C19 H19A 109.3 . . ? C20 C19 H19A 109.3 . . ? C18 C19 H19B 109.3 . . ? C20 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? C15 C20 C19 115.3(5) . . ? C15 C20 H20A 108.5 . . ? C19 C20 H20A 108.5 . . ? C15 C20 H20B 108.5 . . ? C19 C20 H20B 108.5 . . ? H20A C20 H20B 107.5 . . ? C18A C19A C20A 127.6(13) . . ? C18A C19A H19C 105.4 . . ? C20A C19A H19C 105.4 . . ? C18A C19A H19D 105.4 . . ? C20A C19A H19D 105.4 . . ? H19C C19A H19D 106.0 . . ? O1A N1A O2A 122.8(5) . . ? O1A N1A C1A 119.4(5) . . ? O2A N1A C1A 117.8(5) . . ? O3A N2A O4A 121.5(5) . . ? O3A N2A C3A 118.6(5) . . ? O4A N2A C3A 119.9(5) . . ? C4A N3A N4A 119.6(5) . . ? C4A N3A H3A 120.2 . . ? N4A N3A H3A 120.2 . . ? C7A N4A N3A 112.1(5) . . ? C2A C1A C6A 121.9(6) . . ? C2A C1A N1A 120.0(6) . . ? C6A C1A N1A 118.1(5) . . ? C1A C2A C3A 119.8(6) . . ? C1A C2A H2A 120.1 . . ? C3A C2A H2A 120.1 . . ? C2A C3A C4A 121.6(5) . . ? C2A C3A N2A 116.1(6) . . ? C4A C3A N2A 122.3(5) . . ? N3A C4A C5A 119.8(6) . . ? N3A C4A C3A 121.8(5) . . ? C5A C4A C3A 118.4(5) . . ? C4A C5A C6A 120.2(6) . . ? C4A C5A H5A 119.9 . . ? C6A C5A H5A 119.9 . . ? C1A C6A C5A 118.0(6) . . ? C1A C6A H6A 121.0 . . ? C5A C6A H6A 121.0 . . ? N4A C7A C8A 125.5(6) . . ? N4A C7A C9A 116.7(5) . . ? C8A C7A C9A 117.9(5) . . ? C7A C8A H8A1 109.5 . . ? C7A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C7A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C10A C9A C7A 111.3(5) . . ? C10A C9A C14A 111.0(5) . . ? C7A C9A C14A 111.0(5) . . ? C10A C9A H9A 107.8 . . ? C7A C9A H9A 107.8 . . ? C14A C9A H9A 107.8 . . ? C9A C10A C11A 111.6(6) . . ? C9A C10A H10C 109.3 . . ? C11A C10A H10C 109.3 . . ? C9A C10A H10D 109.3 . . ? C11A C10A H10D 109.3 . . ? H10C C10A H10D 108.0 . . ? C12A C11A C10A 110.3(6) . . ? C12A C11A H11C 109.6 . . ? C10A C11A H11C 109.6 . . ? C12A C11A H11D 109.6 . . ? C10A C11A H11D 109.6 . . ? H11C C11A H11D 108.1 . . ? C11A C12A C13A 112.1(6) . . ? C11A C12A H12C 109.2 . . ? C13A C12A H12C 109.2 . . ? C11A C12A H12D 109.2 . . ? C13A C12A H12D 109.2 . . ? H12C C12A H12D 107.9 . . ? C12A C13A C14A 111.1(6) . . ? C12A C13A H13C 109.4 . . ? C14A C13A H13C 109.4 . . ? C12A C13A H13D 109.4 . . ? C14A C13A H13D 109.4 . . ? H13C C13A H13D 108.0 . . ? C15A C14A C13A 113.1(6) . . ? C15A C14A C9A 113.7(5) . . ? C13A C14A C9A 108.2(5) . . ? C15A C14A H14A 107.2 . . ? C13A C14A H14A 107.2 . . ? C9A C14A H14A 107.2 . . ? C16A C15A C20A 121.5(6) . . ? C16A C15A C14A 120.9(6) . . ? C20A C15A C14A 117.6(6) . . ? C15A C16A C17A 124.3(7) . . ? C15A C16A H16A 117.9 . . ? C17A C16A H16A 117.9 . . ? C18B C17A C16A 111.7(11) . . ? C18B C17A C18A 26.9(10) . . ? C16A C17A C18A 112.7(7) . . ? C18B C17A H17C 85.0 . . ? C16A C17A H17C 109.0 . . ? C18A C17A H17C 109.0 . . ? C18B C17A H17D 130.0 . . ? C16A C17A H17D 109.0 . . ? C18A C17A H17D 109.0 . . ? H17C C17A H17D 107.8 . . ? C19A C18A C17A 118.7(11) . . ? C19A C18A H18C 107.6 . . ? C17A C18A H18C 107.6 . . ? C19A C18A H18D 107.6 . . ? C17A C18A H18D 107.6 . . ? H18C C18A H18D 107.1 . . ? C19A C20A C15A 114.1(8) . . ? C19A C20A C19B 23(2) . . ? C15A C20A C19B 109.4(14) . . ? C19A C20A H20C 108.7 . . ? C15A C20A H20C 108.7 . . ? C19B C20A H20C 90.0 . . ? C19A C20A H20D 108.7 . . ? C15A C20A H20D 108.7 . . ? C19B C20A H20D 129.5 . . ? H20C C20A H20D 107.6 . . ? C19B C18B C17A 128(3) . . ? C19B C18B H18E 105.2 . . ? C17A C18B H18E 105.2 . . ? C19B C18B H18F 105.2 . . ? C17A C18B H18F 105.2 . . ? H18E C18B H18F 105.9 . . ? C18B C19B C20A 119(3) . . ? C18B C19B H19E 107.7 . . ? C20A C19B H19E 107.7 . . ? C18B C19B H19F 107.7 . . ? C20A C19B H19F 107.7 . . ? H19E C19B H19F 107.1 . . ? 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 C4 N3 N4 C7 178.6(6) . . . . ? O2 N1 C1 C2 3.0(10) . . . . ? O1 N1 C1 C2 -176.3(6) . . . . ? O2 N1 C1 C6 -177.6(7) . . . . ? O1 N1 C1 C6 3.0(10) . . . . ? C6 C1 C2 C3 1.9(10) . . . . ? N1 C1 C2 C3 -178.8(6) . . . . ? C1 C2 C3 N2 178.1(6) . . . . ? C1 C2 C3 C4 0.6(10) . . . . ? O3 N2 C3 C2 -0.2(9) . . . . ? O4 N2 C3 C2 178.6(6) . . . . ? O3 N2 C3 C4 177.2(7) . . . . ? O4 N2 C3 C4 -3.9(10) . . . . ? N4 N3 C4 C5 7.3(10) . . . . ? N4 N3 C4 C3 -171.5(6) . . . . ? C2 C3 C4 N3 177.0(7) . . . . ? N2 C3 C4 N3 -0.3(10) . . . . ? C2 C3 C4 C5 -1.9(10) . . . . ? N2 C3 C4 C5 -179.2(6) . . . . ? N3 C4 C5 C6 -178.3(7) . . . . ? C3 C4 C5 C6 0.7(10) . . . . ? C4 C5 C6 C1 1.8(11) . . . . ? C2 C1 C6 C5 -3.1(11) . . . . ? N1 C1 C6 C5 177.6(7) . . . . ? N3 N4 C7 C8 0.7(10) . . . . ? N3 N4 C7 C9 177.6(6) . . . . ? N4 C7 C9 C10 -106.2(7) . . . . ? C8 C7 C9 C10 71.0(8) . . . . ? N4 C7 C9 C14 128.9(6) . . . . ? C8 C7 C9 C14 -54.0(9) . . . . ? C7 C9 C10 C11 176.9(6) . . . . ? C14 C9 C10 C11 -56.5(8) . . . . ? C9 C10 C11 C12 54.0(10) . . . . ? C10 C11 C12 C13 -53.2(9) . . . . ? C11 C12 C13 C14 55.5(8) . . . . ? C7 C9 C14 C13 -178.9(6) . . . . ? C10 C9 C14 C13 56.3(7) . . . . ? C7 C9 C14 C15 -53.1(8) . . . . ? C10 C9 C14 C15 -177.9(6) . . . . ? C12 C13 C14 C9 -55.7(7) . . . . ? C12 C13 C14 C15 176.8(5) . . . . ? C9 C14 C15 C16 119.6(7) . . . . ? C13 C14 C15 C16 -115.4(7) . . . . ? C9 C14 C15 C20 -62.7(8) . . . . ? C13 C14 C15 C20 62.3(8) . . . . ? C20 C15 C16 C17 -2.7(11) . . . . ? C14 C15 C16 C17 174.9(7) . . . . ? C15 C16 C17 C18 12.8(11) . . . . ? C16 C17 C18 C19 -37.6(11) . . . . ? C17 C18 C19 C20 52.0(11) . . . . ? C16 C15 C20 C19 17.4(10) . . . . ? C14 C15 C20 C19 -160.3(6) . . . . ? C18 C19 C20 C15 -41.6(10) . . . . ? C4A N3A N4A C7A 173.2(6) . . . . ? O1A N1A C1A C2A 176.7(6) . . . . ? O2A N1A C1A C2A -0.4(9) . . . . ? O1A N1A C1A C6A -2.0(9) . . . . ? O2A N1A C1A C6A -179.0(6) . . . . ? C6A C1A C2A C3A -0.4(10) . . . . ? N1A C1A C2A C3A -178.9(6) . . . . ? C1A C2A C3A C4A -0.6(10) . . . . ? C1A C2A C3A N2A 178.7(6) . . . . ? O3A N2A C3A C2A 0.5(9) . . . . ? O4A N2A C3A C2A -179.2(6) . . . . ? O3A N2A C3A C4A 179.9(7) . . . . ? O4A N2A C3A C4A 0.1(10) . . . . ? N4A N3A C4A C5A -9.8(9) . . . . ? N4A N3A C4A C3A 170.3(6) . . . . ? C2A C3A C4A N3A -179.7(6) . . . . ? N2A C3A C4A N3A 1.0(10) . . . . ? C2A C3A C4A C5A 0.4(10) . . . . ? N2A C3A C4A C5A -178.9(6) . . . . ? N3A C4A C5A C6A -179.2(6) . . . . ? C3A C4A C5A C6A 0.7(10) . . . . ? C2A C1A C6A C5A 1.4(10) . . . . ? N1A C1A C6A C5A -180.0(6) . . . . ? C4A C5A C6A C1A -1.6(10) . . . . ? N3A N4A C7A C8A -3.9(9) . . . . ? N3A N4A C7A C9A 176.0(5) . . . . ? N4A C7A C9A C10A -117.3(6) . . . . ? C8A C7A C9A C10A 62.6(8) . . . . ? N4A C7A C9A C14A 118.5(6) . . . . ? C8A C7A C9A C14A -61.6(7) . . . . ? C7A C9A C10A C11A 177.5(6) . . . . ? C14A C9A C10A C11A -58.3(7) . . . . ? C9A C10A C11A C12A 55.7(8) . . . . ? C10A C11A C12A C13A -54.9(8) . . . . ? C11A C12A C13A C14A 57.1(8) . . . . ? C12A C13A C14A C15A 176.2(6) . . . . ? C12A C13A C14A C9A -57.0(7) . . . . ? C10A C9A C14A C15A -175.4(5) . . . . ? C7A C9A C14A C15A -51.1(6) . . . . ? C10A C9A C14A C13A 58.1(6) . . . . ? C7A C9A C14A C13A -177.6(5) . . . . ? C13A C14A C15A C16A -122.8(7) . . . . ? C9A C14A C15A C16A 113.3(7) . . . . ? C13A C14A C15A C20A 59.8(8) . . . . ? C9A C14A C15A C20A -64.1(7) . . . . ? C20A C15A C16A C17A -1.2(11) . . . . ? C14A C15A C16A C17A -178.5(7) . . . . ? C15A C16A C17A C18B -20.0(15) . . . . ? C15A C16A C17A C18A 9.1(12) . . . . ? C20A C19A C18A C17A 0(4) . . . . ? C18B C17A C18A C19A 85(3) . . . . ? C16A C17A C18A C19A -8(2) . . . . ? C18A C19A C20A C15A 8(4) . . . . ? C18A C19A C20A C19B -75(4) . . . . ? C16A C15A C20A C19A -7.5(17) . . . . ? C14A C15A C20A C19A 169.9(14) . . . . ? C16A C15A C20A C19B 17.2(18) . . . . ? C14A C15A C20A C19B -165.4(16) . . . . ? C16A C17A C18B C19B 24(4) . . . . ? C18A C17A C18B C19B -73(4) . . . . ? C17A C18B C19B C20A -8(5) . . . . ? C19A C20A C19B C18B 92(5) . . . . ? C15A C20A C19B C18B -14(4) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.618 _refine_diff_density_min -0.606 _refine_diff_density_rms 0.148 #=== end