# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jik Chin' _publ_contact_author_address ; Lash Miller Chemical Laboratories University of Toronto 80 St George Street Toronto Ontario M5S 3H6 CANADA ; _publ_contact_author_email JCHIN@CHEM.UTORONTO.CA _publ_section_title ; Diastereoselective Diaza-Cope Rearrangement Reaction ; loop_ _publ_author_name 'Jik Chin' 'Doo Choi' 'Hyunwoo Kim' 'Alan J. Lough' 'Choong Song' 'Cindy Pai-Hui Yen.' data_k0725 _database_code_depnum_ccdc_archive 'CCDC 665963' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H40 N2 O2' _chemical_formula_sum 'C34 H40 N2 O2' _chemical_formula_weight 508.68 _chemical_absolute_configuration rm 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 Trigonal _symmetry_space_group_name_H-M 'P 31' _symmetry_space_group_name_Hall 'P 31' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' _cell_length_a 24.194(3) _cell_length_b 24.194(3) _cell_length_c 13.040(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6610.2(19) _cell_formula_units_Z 9 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 32252 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colouless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.150 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2466 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32252 _diffrn_reflns_av_R_equivalents 0.1033 _diffrn_reflns_av_sigmaI/netI 0.1277 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.47 _reflns_number_total 10052 _reflns_number_gt 5785 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1(Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL V6.1' _computing_publication_material 'SHELXTL V6.1' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0546P)^2^] 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 0.0015(3) _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 0.8(13) _refine_ls_number_reflns 10052 _refine_ls_number_parameters 1064 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1345 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1299 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.003 _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 O1A O 0.04091(15) 0.81928(14) 0.5641(3) 0.0384(8) Uani 1 1 d . . . O2A O 0.22588(17) 0.70546(15) 0.5487(3) 0.0546(10) Uani 1 1 d . . . N1A N 0.07185(15) 0.75339(15) 0.4432(3) 0.0284(8) Uani 1 1 d . . . N2A N 0.20389(15) 0.78639(16) 0.4360(3) 0.0298(8) Uani 1 1 d . . . C1A C 0.10208(18) 0.74090(18) 0.5305(3) 0.0283(10) Uani 1 1 d . . . H1AA H 0.0980 0.6980 0.5218 0.034 Uiso 1 1 calc R . . C2A C 0.17528(18) 0.79373(19) 0.5298(3) 0.0291(10) Uani 1 1 d . . . H2AA H 0.1788 0.8367 0.5290 0.035 Uiso 1 1 calc R . . C3A C 0.06887(18) 0.74141(17) 0.6282(3) 0.0267(9) Uani 1 1 d . . . C4A C 0.03993(19) 0.78002(19) 0.6399(3) 0.0295(10) Uani 1 1 d . . . C5A C 0.00967(19) 0.77842(19) 0.7310(3) 0.0323(10) Uani 1 1 d . . . H5AA H -0.0110 0.8029 0.7373 0.039 Uiso 1 1 calc R . . C6A C 0.00909(19) 0.7421(2) 0.8122(4) 0.0344(11) Uani 1 1 d . . . H6AA H -0.0111 0.7422 0.8746 0.041 Uiso 1 1 calc R . . C7A C 0.0381(2) 0.7051(2) 0.8033(4) 0.0375(11) Uani 1 1 d . . . H7AA H 0.0381 0.6800 0.8594 0.045 Uiso 1 1 calc R . . C8A C 0.06684(19) 0.70518(18) 0.7118(4) 0.0306(10) Uani 1 1 d . . . H8AA H 0.0860 0.6793 0.7059 0.037 Uiso 1 1 calc R . . C9A C 0.21061(19) 0.78971(19) 0.6222(3) 0.0308(10) Uani 1 1 d . . . C10A C 0.2327(2) 0.7455(2) 0.6275(4) 0.0385(11) Uani 1 1 d . . . C11A C 0.2626(2) 0.7420(2) 0.7161(4) 0.0420(12) Uani 1 1 d . . . H11A H 0.2772 0.7122 0.7198 0.050 Uiso 1 1 calc R . . C12A C 0.2714(2) 0.7809(2) 0.7987(4) 0.0485(13) Uani 1 1 d . . . H12A H 0.2908 0.7770 0.8595 0.058 Uiso 1 1 calc R . . C13A C 0.2518(2) 0.8259(2) 0.7935(4) 0.0499(13) Uani 1 1 d . . . H13A H 0.2592 0.8539 0.8494 0.060 Uiso 1 1 calc R . . C14A C 0.22165(19) 0.8293(2) 0.7060(4) 0.0370(11) Uani 1 1 d . . . H14A H 0.2079 0.8598 0.7030 0.044 Uiso 1 1 calc R . . C15A C 0.06305(18) 0.72259(19) 0.3602(3) 0.0299(10) Uani 1 1 d . . . H15A H 0.0752 0.6909 0.3573 0.036 Uiso 1 1 calc R . . C16A C 0.03520(19) 0.73381(19) 0.2699(3) 0.0317(10) Uani 1 1 d . . . C17A C 0.00823(19) 0.7785(2) 0.2708(4) 0.0341(10) Uani 1 1 d . . . H17A H 0.0057 0.7959 0.3390 0.041 Uiso 1 1 calc R . . C18A C -0.05389(19) 0.7462(2) 0.2066(4) 0.0380(11) Uani 1 1 d . . . H18A H -0.0779 0.6990 0.2113 0.046 Uiso 1 1 calc R . . H18B H -0.0821 0.7644 0.2174 0.046 Uiso 1 1 calc R . . C19A C -0.0103(2) 0.7725(2) 0.1113(4) 0.0366(11) Uani 1 1 d . . . H19A H -0.0282 0.7853 0.0526 0.044 Uiso 1 1 calc R . . C20A C 0.0132(2) 0.7262(2) 0.0848(4) 0.0400(12) Uani 1 1 d . . . H20A H -0.0218 0.6875 0.0523 0.048 Uiso 1 1 calc R . . H20B H 0.0488 0.7465 0.0351 0.048 Uiso 1 1 calc R . . C21A C 0.03545(19) 0.70754(19) 0.1796(4) 0.0337(11) Uani 1 1 d . . . H21A H 0.0496 0.6774 0.1754 0.040 Uiso 1 1 calc R . . C22A C 0.03794(19) 0.82796(19) 0.1805(4) 0.0344(11) Uani 1 1 d . . . C23A C 0.0219(2) 0.8817(2) 0.1901(4) 0.0479(13) Uani 1 1 d . . . H23A H 0.0325 0.9058 0.1258 0.072 Uiso 1 1 calc R . . H23B H 0.0468 0.9104 0.2462 0.072 Uiso 1 1 calc R . . H23C H -0.0237 0.8633 0.2045 0.072 Uiso 1 1 calc R . . C24A C 0.10864(19) 0.8571(2) 0.1584(4) 0.0410(12) Uani 1 1 d . . . H24A H 0.1190 0.8812 0.0940 0.061 Uiso 1 1 calc R . . H24B H 0.1192 0.8230 0.1523 0.061 Uiso 1 1 calc R . . H24C H 0.1333 0.8858 0.2145 0.061 Uiso 1 1 calc R . . C25A C 0.21884(18) 0.82744(19) 0.3647(3) 0.0305(10) Uani 1 1 d . . . H25A H 0.2078 0.8597 0.3740 0.037 Uiso 1 1 calc R . . C26A C 0.25117(18) 0.82898(19) 0.2709(4) 0.0315(10) Uani 1 1 d . . . C27A C 0.27490(19) 0.7828(2) 0.2482(4) 0.0343(10) Uani 1 1 d . . . H27A H 0.2670 0.7502 0.3020 0.041 Uiso 1 1 calc R . . C28A C 0.3458(2) 0.8248(2) 0.2096(4) 0.0438(12) Uani 1 1 d . . . H28A H 0.3694 0.8675 0.2420 0.053 Uiso 1 1 calc R . . H28B H 0.3709 0.8028 0.2108 0.053 Uiso 1 1 calc R . . C29A C 0.3167(2) 0.8244(2) 0.1036(4) 0.0423(12) Uani 1 1 d . . . H29A H 0.3415 0.8239 0.0427 0.051 Uiso 1 1 calc R . . C30A C 0.2978(2) 0.8764(2) 0.1031(4) 0.0467(13) Uani 1 1 d . . . H30A H 0.3365 0.9188 0.0955 0.056 Uiso 1 1 calc R . . H30B H 0.2693 0.8696 0.0441 0.056 Uiso 1 1 calc R . . C31A C 0.26432(19) 0.8743(2) 0.2007(3) 0.0354(11) Uani 1 1 d . . . H31A H 0.2523 0.9055 0.2131 0.042 Uiso 1 1 calc R . . C32A C 0.2579(2) 0.7581(2) 0.1350(4) 0.0420(12) Uani 1 1 d . . . C33A C 0.1923(2) 0.7402(2) 0.0925(4) 0.0454(13) Uani 1 1 d . . . H33A H 0.1601 0.6994 0.1221 0.068 Uiso 1 1 calc R . . H33B H 0.1925 0.7362 0.0177 0.068 Uiso 1 1 calc R . . H33C H 0.1821 0.7735 0.1103 0.068 Uiso 1 1 calc R . . C34A C 0.2715(2) 0.7039(2) 0.1132(4) 0.0524(14) Uani 1 1 d . . . H34A H 0.2406 0.6655 0.1502 0.079 Uiso 1 1 calc R . . H34B H 0.3148 0.7164 0.1359 0.079 Uiso 1 1 calc R . . H34C H 0.2677 0.6950 0.0394 0.079 Uiso 1 1 calc R . . O1B O -0.19092(13) 0.40809(13) 0.4323(3) 0.0371(8) Uani 1 1 d . . . O2B O 0.09549(13) 0.60295(13) 0.4628(3) 0.0338(7) Uani 1 1 d . . . N1B N -0.10674(15) 0.49606(15) 0.5544(3) 0.0268(8) Uani 1 1 d . . . N2B N 0.01348(14) 0.49983(15) 0.5696(3) 0.0258(8) Uani 1 1 d . . . C1B C -0.06241(18) 0.51749(19) 0.4682(3) 0.0278(10) Uani 1 1 d . . . H1BA H -0.0327 0.5645 0.4744 0.033 Uiso 1 1 calc R . . C2B C -0.02249(17) 0.48234(17) 0.4727(3) 0.0230(9) Uani 1 1 d . . . H2BA H -0.0521 0.4351 0.4708 0.028 Uiso 1 1 calc R . . C3B C -0.09825(17) 0.50395(18) 0.3674(3) 0.0250(9) Uani 1 1 d . . . C4B C -0.15923(18) 0.45008(18) 0.3546(3) 0.0262(10) Uani 1 1 d . . . C5B C -0.18954(19) 0.4380(2) 0.2607(4) 0.0363(11) Uani 1 1 d . . . H5BA H -0.2304 0.4011 0.2524 0.044 Uiso 1 1 calc R . . C6B C -0.1613(2) 0.4786(2) 0.1786(4) 0.0421(12) Uani 1 1 d . . . H6BA H -0.1826 0.4699 0.1145 0.051 Uiso 1 1 calc R . . C7B C -0.1014(2) 0.5322(2) 0.1905(4) 0.0406(12) Uani 1 1 d . . . H7BA H -0.0815 0.5607 0.1348 0.049 Uiso 1 1 calc R . . C8B C -0.07122(19) 0.54358(19) 0.2841(3) 0.0304(10) Uani 1 1 d . . . H8BA H -0.0301 0.5802 0.2915 0.037 Uiso 1 1 calc R . . C9B C 0.02310(18) 0.50178(18) 0.3838(3) 0.0264(9) Uani 1 1 d . . . C10B C 0.07866(19) 0.56232(19) 0.3815(3) 0.0293(10) Uani 1 1 d . . . C11B C 0.1171(2) 0.5826(2) 0.2949(4) 0.0342(11) Uani 1 1 d . . . H11B H 0.1541 0.6238 0.2938 0.041 Uiso 1 1 calc R . . C12B C 0.1021(2) 0.5436(2) 0.2108(4) 0.0409(12) Uani 1 1 d . . . H12B H 0.1281 0.5584 0.1512 0.049 Uiso 1 1 calc R . . C13B C 0.0489(2) 0.4822(2) 0.2123(4) 0.0393(11) Uani 1 1 d . . . H13B H 0.0395 0.4543 0.1555 0.047 Uiso 1 1 calc R . . C14B C 0.00999(19) 0.4630(2) 0.2986(4) 0.0321(10) Uani 1 1 d . . . H14B H -0.0269 0.4217 0.2992 0.038 Uiso 1 1 calc R . . C15B C -0.09397(18) 0.53199(18) 0.6316(3) 0.0264(10) Uani 1 1 d . . . H15B H -0.0550 0.5715 0.6316 0.032 Uiso 1 1 calc R . . C16B C -0.13548(18) 0.51641(18) 0.7204(3) 0.0273(10) Uani 1 1 d . . . C17B C -0.20263(17) 0.45838(19) 0.7208(3) 0.0290(10) Uani 1 1 d . . . H17B H -0.2169 0.4318 0.6572 0.035 Uiso 1 1 calc R . . C18B C -0.24677(19) 0.4839(2) 0.7625(3) 0.0334(11) Uani 1 1 d . . . H18C H -0.2326 0.5287 0.7435 0.040 Uiso 1 1 calc R . . H18D H -0.2928 0.4556 0.7483 0.040 Uiso 1 1 calc R . . C19B C -0.2257(2) 0.4759(2) 0.8705(4) 0.0359(11) Uani 1 1 d . . . H19B H -0.2586 0.4623 0.9256 0.043 Uiso 1 1 calc R . . C20B C -0.1606(2) 0.53524(19) 0.8942(4) 0.0357(11) Uani 1 1 d . . . H20C H -0.1669 0.5713 0.9130 0.043 Uiso 1 1 calc R . . H20D H -0.1406 0.5262 0.9532 0.043 Uiso 1 1 calc R . . C21B C -0.11754(19) 0.5531(2) 0.8030(3) 0.0310(10) Uani 1 1 d . . . H21B H -0.0771 0.5910 0.8044 0.037 Uiso 1 1 calc R . . C22B C -0.2152(2) 0.42245(19) 0.8245(4) 0.0350(11) Uani 1 1 d . . . C23B C -0.2782(2) 0.3578(2) 0.8220(4) 0.0484(13) Uani 1 1 d . . . H23D H -0.2906 0.3419 0.8922 0.073 Uiso 1 1 calc R . . H23E H -0.2722 0.3271 0.7817 0.073 Uiso 1 1 calc R . . H23F H -0.3118 0.3636 0.7907 0.073 Uiso 1 1 calc R . . C24B C -0.1632(2) 0.4126(2) 0.8721(4) 0.0434(12) Uani 1 1 d . . . H24D H -0.1232 0.4536 0.8752 0.065 Uiso 1 1 calc R . . H24E H -0.1569 0.3826 0.8301 0.065 Uiso 1 1 calc R . . H24F H -0.1760 0.3954 0.9415 0.065 Uiso 1 1 calc R . . C25B C 0.00019(19) 0.45622(19) 0.6359(3) 0.0293(10) Uani 1 1 d . . . H25B H -0.0337 0.4145 0.6206 0.035 Uiso 1 1 calc R . . C26B C 0.03318(18) 0.46568(19) 0.7333(3) 0.0271(10) Uani 1 1 d . . . C27B C 0.08785(18) 0.52918(19) 0.7675(3) 0.0296(10) Uani 1 1 d . . . H27B H 0.1007 0.5658 0.7194 0.035 Uiso 1 1 calc R . . C28B C 0.1418(2) 0.5168(2) 0.8038(4) 0.0354(11) Uani 1 1 d . . . H28C H 0.1441 0.4827 0.7655 0.042 Uiso 1 1 calc R . . H28D H 0.1842 0.5557 0.8093 0.042 Uiso 1 1 calc R . . C29B C 0.10496(19) 0.49460(19) 0.9065(4) 0.0311(10) Uani 1 1 d . . . H29B H 0.1319 0.5047 0.9696 0.037 Uiso 1 1 calc R . . C30B C 0.0523(2) 0.4257(2) 0.8952(4) 0.0358(11) Uani 1 1 d . . . H30C H 0.0710 0.3974 0.8963 0.043 Uiso 1 1 calc R . . H30D H 0.0223 0.4138 0.9536 0.043 Uiso 1 1 calc R . . C31B C 0.0168(2) 0.4165(2) 0.7968(4) 0.0333(11) Uani 1 1 d . . . H31B H -0.0175 0.3754 0.7793 0.040 Uiso 1 1 calc R . . C32B C 0.07960(19) 0.54166(19) 0.8814(3) 0.0322(10) Uani 1 1 d . . . C33B C 0.0135(2) 0.5245(2) 0.9219(4) 0.0461(13) Uani 1 1 d . . . H33D H -0.0002 0.5524 0.8899 0.069 Uiso 1 1 calc R . . H33E H 0.0155 0.5303 0.9964 0.069 Uiso 1 1 calc R . . H33F H -0.0171 0.4800 0.9051 0.069 Uiso 1 1 calc R . . C34B C 0.1270(3) 0.6102(2) 0.9142(4) 0.0495(13) Uani 1 1 d . . . H34D H 0.1142 0.6393 0.8847 0.074 Uiso 1 1 calc R . . H34E H 0.1698 0.6219 0.8898 0.074 Uiso 1 1 calc R . . H34F H 0.1274 0.6132 0.9892 0.074 Uiso 1 1 calc R . . O1C O 0.42630(13) 1.10955(13) 0.1761(2) 0.0303(7) Uani 1 1 d . . . O2C O 0.14841(13) 1.05079(14) 0.2215(3) 0.0358(8) Uani 1 1 d . . . N1C N 0.34359(15) 1.12964(14) 0.0781(3) 0.0255(8) Uani 1 1 d . . . N2C N 0.21617(14) 1.02434(14) 0.0959(3) 0.0254(8) Uani 1 1 d . . . C1C C 0.30897(18) 1.11570(17) 0.1749(3) 0.0251(9) Uani 1 1 d . . . H1CA H 0.2841 1.1385 0.1773 0.030 Uiso 1 1 calc R . . C2C C 0.26185(17) 1.04153(17) 0.1801(3) 0.0247(9) Uani 1 1 d . . . H2CA H 0.2864 1.0187 0.1717 0.030 Uiso 1 1 calc R . . C3C C 0.35509(17) 1.13703(17) 0.2636(3) 0.0250(9) Uani 1 1 d . . . C4C C 0.41105(18) 1.13282(17) 0.2603(3) 0.0252(9) Uani 1 1 d . . . C5C C 0.45240(19) 1.15293(19) 0.3429(3) 0.0312(10) Uani 1 1 d . . . H5CA H 0.4905 1.1508 0.3396 0.037 Uiso 1 1 calc R . . C6C C 0.4387(2) 1.1759(2) 0.4292(4) 0.0355(11) Uani 1 1 d . . . H6CA H 0.4674 1.1893 0.4857 0.043 Uiso 1 1 calc R . . C7C C 0.3836(2) 1.1798(2) 0.4354(4) 0.0371(11) Uani 1 1 d . . . H7CA H 0.3742 1.1955 0.4957 0.044 Uiso 1 1 calc R . . C8C C 0.34228(19) 1.16028(19) 0.3524(3) 0.0305(10) Uani 1 1 d . . . H8CA H 0.3044 1.1629 0.3563 0.037 Uiso 1 1 calc R . . C9C C 0.22629(19) 1.02256(18) 0.2803(3) 0.0275(10) Uani 1 1 d . . . C10C C 0.17210(18) 1.02916(18) 0.2973(3) 0.0289(10) Uani 1 1 d . . . C11C C 0.14153(19) 1.0133(2) 0.3907(4) 0.0354(11) Uani 1 1 d . . . H11C H 0.1050 1.0177 0.4008 0.043 Uiso 1 1 calc R . . C12C C 0.1633(2) 0.9911(2) 0.4705(4) 0.0456(12) Uani 1 1 d . . . H12C H 0.1415 0.9799 0.5344 0.055 Uiso 1 1 calc R . . C13C C 0.2172(2) 0.9856(2) 0.4562(4) 0.0405(12) Uani 1 1 d . . . H13C H 0.2331 0.9713 0.5105 0.049 Uiso 1 1 calc R . . C14C C 0.2474(2) 1.00091(18) 0.3624(4) 0.0330(11) Uani 1 1 d . . . H14C H 0.2840 0.9966 0.3531 0.040 Uiso 1 1 calc R . . C15C C 0.33237(18) 1.15898(18) 0.0076(3) 0.0278(10) Uani 1 1 d . . . H15C H 0.3007 1.1704 0.0203 0.033 Uiso 1 1 calc R . . C16C C 0.36471(19) 1.17633(18) -0.0914(3) 0.0300(10) Uani 1 1 d . . . C17C C 0.41919(19) 1.16466(19) -0.1173(4) 0.0326(10) Uani 1 1 d . . . H17C H 0.4322 1.1443 -0.0628 0.039 Uiso 1 1 calc R . . C18C C 0.4730(2) 1.2283(2) -0.1637(4) 0.0385(11) Uani 1 1 d . . . H18E H 0.4755 1.2672 -0.1342 0.046 Uiso 1 1 calc R . . H18F H 0.5155 1.2317 -0.1654 0.046 Uiso 1 1 calc R . . C19C C 0.4360(2) 1.2063(2) -0.2648(4) 0.0393(11) Uani 1 1 d . . . H19C H 0.4626 1.2188 -0.3284 0.047 Uiso 1 1 calc R . . C20C C 0.3822(2) 1.2226(2) -0.2632(4) 0.0468(13) Uani 1 1 d . . . H20E H 0.4003 1.2688 -0.2758 0.056 Uiso 1 1 calc R . . H20F H 0.3513 1.1989 -0.3185 0.056 Uiso 1 1 calc R . . C21C C 0.3489(2) 1.2053(2) -0.1623(4) 0.0394(11) Uani 1 1 d . . . H21C H 0.3162 1.2151 -0.1486 0.047 Uiso 1 1 calc R . . C22C C 0.4104(2) 1.13660(19) -0.2274(4) 0.0396(12) Uani 1 1 d . . . C23C C 0.4576(2) 1.1134(2) -0.2496(4) 0.0529(14) Uani 1 1 d . . . H23G H 0.4591 1.1072 -0.3236 0.079 Uiso 1 1 calc R . . H23H H 0.4437 1.0729 -0.2141 0.079 Uiso 1 1 calc R . . H23I H 0.5001 1.1453 -0.2253 0.079 Uiso 1 1 calc R . . C24C C 0.3451(2) 1.0848(2) -0.2635(4) 0.0546(15) Uani 1 1 d . . . H24G H 0.3453 1.0809 -0.3383 0.082 Uiso 1 1 calc R . . H24H H 0.3129 1.0959 -0.2435 0.082 Uiso 1 1 calc R . . H24I H 0.3351 1.0440 -0.2319 0.082 Uiso 1 1 calc R . . C25C C 0.22288(18) 0.99849(17) 0.0151(3) 0.0258(9) Uani 1 1 d . . . H25C H 0.2582 0.9916 0.0120 0.031 Uiso 1 1 calc R . . C26C C 0.18049(17) 0.97901(18) -0.0718(3) 0.0282(10) Uani 1 1 d . . . C27C C 0.11903(19) 0.9818(2) -0.0684(4) 0.0347(11) Uani 1 1 d . . . H27C H 0.1095 0.9971 -0.0030 0.042 Uiso 1 1 calc R . . C28C C 0.0657(2) 0.9168(2) -0.1110(4) 0.0409(12) Uani 1 1 d . . . H28E H 0.0715 0.8801 -0.0941 0.049 Uiso 1 1 calc R . . H28F H 0.0218 0.9074 -0.0955 0.049 Uiso 1 1 calc R . . C29C C 0.0896(2) 0.9449(2) -0.2180(4) 0.0384(11) Uani 1 1 d . . . H29C H 0.0559 0.9311 -0.2721 0.046 Uiso 1 1 calc R . . C30C C 0.1475(2) 0.9376(2) -0.2461(4) 0.0401(11) Uani 1 1 d . . . H30E H 0.1329 0.8928 -0.2656 0.048 Uiso 1 1 calc R . . H30F H 0.1704 0.9653 -0.3052 0.048 Uiso 1 1 calc R . . C31C C 0.19147(19) 0.95590(18) -0.1557(4) 0.0309(10) Uani 1 1 d . . . H31C H 0.2279 0.9507 -0.1591 0.037 Uiso 1 1 calc R . . C32C C 0.1116(2) 1.0117(2) -0.1700(4) 0.0405(12) Uani 1 1 d . . . C33C C 0.1698(2) 1.0704(2) -0.2126(4) 0.0482(13) Uani 1 1 d . . . H33G H 0.1615 1.0773 -0.2836 0.072 Uiso 1 1 calc R . . H33H H 0.2066 1.0639 -0.2106 0.072 Uiso 1 1 calc R . . H33I H 0.1787 1.1077 -0.1711 0.072 Uiso 1 1 calc R . . C34C C 0.0561(2) 1.0260(3) -0.1644(5) 0.0585(15) Uani 1 1 d . . . H34G H 0.0464 1.0347 -0.2335 0.088 Uiso 1 1 calc R . . H34H H 0.0685 1.0633 -0.1206 0.088 Uiso 1 1 calc R . . H34I H 0.0182 0.9891 -0.1356 0.088 Uiso 1 1 calc R . . H1 H 0.050(2) 0.807(2) 0.501(4) 0.054(16) Uiso 1 1 d . . . H2 H 0.216(3) 0.720(3) 0.491(5) 0.08(2) Uiso 1 1 d . . . H3 H -0.169(2) 0.426(2) 0.504(4) 0.046(13) Uiso 1 1 d . . . H4 H 0.079(3) 0.580(3) 0.521(5) 0.07(2) Uiso 1 1 d . . . H5 H 0.403(3) 1.110(3) 0.113(4) 0.075(18) Uiso 1 1 d . . . H6 H 0.164(2) 1.045(2) 0.156(4) 0.048(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.0485(19) 0.0410(18) 0.034(2) 0.0036(16) 0.0011(16) 0.0288(16) O2A 0.071(2) 0.040(2) 0.062(3) -0.0147(19) -0.029(2) 0.0352(18) N1A 0.0247(18) 0.0255(18) 0.029(2) 0.0014(17) -0.0023(16) 0.0076(15) N2A 0.0255(18) 0.0295(19) 0.029(2) -0.0050(18) -0.0052(16) 0.0099(15) C1A 0.031(2) 0.023(2) 0.030(3) -0.0019(19) -0.006(2) 0.0125(19) C2A 0.029(2) 0.026(2) 0.027(3) -0.0024(19) -0.005(2) 0.0101(18) C3A 0.021(2) 0.018(2) 0.031(3) -0.0031(19) -0.0049(19) 0.0028(17) C4A 0.027(2) 0.024(2) 0.031(3) -0.004(2) -0.006(2) 0.0086(18) C5A 0.028(2) 0.030(2) 0.035(3) -0.003(2) -0.004(2) 0.0111(19) C6A 0.026(2) 0.033(2) 0.033(3) -0.005(2) 0.002(2) 0.0067(19) C7A 0.031(2) 0.030(2) 0.041(3) 0.005(2) -0.002(2) 0.007(2) C8A 0.027(2) 0.026(2) 0.034(3) 0.001(2) 0.001(2) 0.0100(19) C9A 0.025(2) 0.031(2) 0.027(3) 0.003(2) 0.0010(19) 0.0072(19) C10A 0.036(2) 0.029(2) 0.042(3) 0.003(2) -0.007(2) 0.010(2) C11A 0.035(3) 0.039(3) 0.047(4) 0.006(2) -0.008(2) 0.015(2) C12A 0.034(3) 0.060(3) 0.036(3) 0.009(3) -0.008(2) 0.012(2) C13A 0.035(3) 0.060(3) 0.040(3) -0.012(3) -0.005(2) 0.013(3) C14A 0.027(2) 0.042(3) 0.033(3) -0.004(2) -0.003(2) 0.010(2) C15A 0.027(2) 0.023(2) 0.032(3) 0.005(2) 0.000(2) 0.0066(18) C16A 0.027(2) 0.028(2) 0.029(3) 0.001(2) -0.001(2) 0.0054(19) C17A 0.033(2) 0.037(2) 0.030(3) 0.001(2) -0.003(2) 0.017(2) C18A 0.026(2) 0.039(2) 0.041(3) 0.008(2) -0.002(2) 0.009(2) C19A 0.029(2) 0.043(3) 0.031(3) 0.003(2) -0.004(2) 0.013(2) C20A 0.034(2) 0.041(3) 0.030(3) 0.000(2) 0.000(2) 0.008(2) C21A 0.026(2) 0.028(2) 0.036(3) -0.001(2) 0.000(2) 0.0056(18) C22A 0.029(2) 0.031(2) 0.039(3) 0.007(2) 0.000(2) 0.0115(19) C23A 0.042(3) 0.046(3) 0.054(4) 0.004(3) -0.006(3) 0.021(2) C24A 0.027(2) 0.032(2) 0.056(4) 0.007(2) -0.004(2) 0.009(2) C25A 0.025(2) 0.028(2) 0.032(3) -0.004(2) -0.002(2) 0.0086(19) C26A 0.022(2) 0.031(2) 0.032(3) -0.006(2) -0.002(2) 0.0059(18) C27A 0.032(2) 0.034(2) 0.030(3) -0.004(2) 0.007(2) 0.011(2) C28A 0.027(2) 0.046(3) 0.042(3) -0.009(2) 0.004(2) 0.005(2) C29A 0.029(2) 0.041(3) 0.039(3) -0.007(2) 0.004(2) 0.004(2) C30A 0.034(3) 0.043(3) 0.044(3) -0.002(2) 0.000(2) 0.005(2) C31A 0.025(2) 0.031(2) 0.033(3) -0.004(2) -0.004(2) 0.0010(19) C32A 0.030(2) 0.038(3) 0.043(3) -0.010(2) 0.003(2) 0.006(2) C33A 0.030(2) 0.045(3) 0.046(3) -0.011(2) 0.001(2) 0.007(2) C34A 0.039(3) 0.056(3) 0.057(4) -0.019(3) 0.007(3) 0.019(2) O1B 0.0307(16) 0.0276(16) 0.040(2) 0.0053(15) -0.0035(15) 0.0051(13) O2B 0.0309(16) 0.0258(16) 0.040(2) -0.0021(16) -0.0003(15) 0.0107(13) N1B 0.0221(17) 0.0253(18) 0.031(2) -0.0001(17) -0.0009(16) 0.0102(14) N2B 0.0221(17) 0.0268(18) 0.030(2) -0.0042(17) -0.0015(16) 0.0132(15) C1B 0.023(2) 0.024(2) 0.038(3) 0.0012(19) 0.001(2) 0.0129(18) C2B 0.0200(19) 0.0173(19) 0.028(2) -0.0030(18) -0.0073(18) 0.0063(16) C3B 0.0187(19) 0.024(2) 0.033(3) -0.0047(19) 0.0007(18) 0.0110(17) C4B 0.023(2) 0.026(2) 0.030(3) 0.000(2) 0.001(2) 0.0129(18) C5B 0.024(2) 0.037(2) 0.047(3) -0.002(2) -0.005(2) 0.014(2) C6B 0.033(3) 0.053(3) 0.040(3) 0.000(3) -0.014(2) 0.021(2) C7B 0.040(3) 0.048(3) 0.034(3) 0.008(2) -0.001(2) 0.022(2) C8B 0.023(2) 0.033(2) 0.034(3) 0.001(2) -0.001(2) 0.0126(19) C9B 0.025(2) 0.027(2) 0.032(3) -0.001(2) -0.0002(19) 0.0167(18) C10B 0.028(2) 0.028(2) 0.038(3) 0.002(2) -0.004(2) 0.0181(19) C11B 0.024(2) 0.035(2) 0.041(3) 0.005(2) 0.002(2) 0.0123(19) C12B 0.034(3) 0.057(3) 0.038(3) 0.012(3) 0.008(2) 0.028(2) C13B 0.040(3) 0.049(3) 0.032(3) -0.006(2) 0.001(2) 0.024(2) C14B 0.028(2) 0.034(2) 0.034(3) -0.004(2) -0.004(2) 0.0151(19) C15B 0.019(2) 0.026(2) 0.032(3) 0.000(2) -0.0017(19) 0.0093(17) C16B 0.025(2) 0.027(2) 0.031(3) 0.002(2) 0.0009(19) 0.0140(18) C17B 0.024(2) 0.028(2) 0.031(3) -0.0001(19) -0.0002(19) 0.0100(18) C18B 0.027(2) 0.032(2) 0.044(3) 0.007(2) 0.010(2) 0.0163(19) C19B 0.033(2) 0.039(3) 0.040(3) 0.004(2) 0.008(2) 0.021(2) C20B 0.046(3) 0.033(2) 0.035(3) -0.003(2) 0.001(2) 0.025(2) C21B 0.028(2) 0.031(2) 0.038(3) -0.003(2) -0.004(2) 0.0167(19) C22B 0.032(2) 0.029(2) 0.041(3) 0.004(2) 0.002(2) 0.0136(19) C23B 0.053(3) 0.029(2) 0.053(4) 0.004(2) 0.010(3) 0.013(2) C24B 0.057(3) 0.043(3) 0.044(3) 0.000(2) -0.003(2) 0.036(2) C25B 0.027(2) 0.024(2) 0.035(3) -0.002(2) 0.002(2) 0.0113(18) C26B 0.027(2) 0.029(2) 0.028(3) -0.007(2) -0.0054(19) 0.0165(19) C27B 0.028(2) 0.029(2) 0.033(3) -0.003(2) -0.002(2) 0.0159(19) C28B 0.031(2) 0.041(3) 0.037(3) -0.003(2) -0.007(2) 0.020(2) C29B 0.028(2) 0.035(2) 0.032(3) -0.006(2) -0.009(2) 0.0167(19) C30B 0.040(3) 0.034(2) 0.036(3) 0.005(2) -0.003(2) 0.020(2) C31B 0.033(2) 0.027(2) 0.037(3) -0.003(2) -0.005(2) 0.0125(19) C32B 0.036(2) 0.033(2) 0.033(3) -0.010(2) -0.008(2) 0.020(2) C33B 0.051(3) 0.063(3) 0.045(3) -0.002(3) 0.003(3) 0.044(3) C34B 0.067(3) 0.041(3) 0.045(3) -0.016(3) -0.019(3) 0.031(3) O1C 0.0325(16) 0.0349(16) 0.0311(19) -0.0008(14) 0.0017(14) 0.0225(14) O2C 0.0338(17) 0.0442(18) 0.037(2) 0.0011(16) 0.0050(15) 0.0252(15) N1C 0.0245(18) 0.0238(17) 0.028(2) 0.0002(16) -0.0007(16) 0.0123(15) N2C 0.0237(17) 0.0245(17) 0.026(2) 0.0030(16) 0.0030(15) 0.0109(15) C1C 0.026(2) 0.023(2) 0.030(3) 0.0027(18) 0.0024(19) 0.0142(17) C2C 0.022(2) 0.021(2) 0.032(3) 0.0007(18) -0.0025(19) 0.0107(17) C3C 0.022(2) 0.0182(19) 0.031(3) 0.0026(18) 0.0021(19) 0.0074(17) C4C 0.025(2) 0.022(2) 0.027(3) 0.0018(18) 0.0042(19) 0.0107(18) C5C 0.028(2) 0.034(2) 0.036(3) -0.001(2) -0.003(2) 0.018(2) C6C 0.029(2) 0.043(3) 0.036(3) -0.005(2) -0.002(2) 0.020(2) C7C 0.039(3) 0.040(3) 0.033(3) -0.004(2) 0.007(2) 0.020(2) C8C 0.023(2) 0.031(2) 0.036(3) -0.004(2) 0.000(2) 0.0129(19) C9C 0.031(2) 0.019(2) 0.029(3) 0.0003(18) 0.000(2) 0.0090(18) C10C 0.026(2) 0.025(2) 0.033(3) -0.003(2) 0.000(2) 0.0107(18) C11C 0.023(2) 0.041(3) 0.038(3) -0.004(2) 0.005(2) 0.013(2) C12C 0.041(3) 0.045(3) 0.042(3) 0.005(2) 0.011(2) 0.015(2) C13C 0.045(3) 0.035(3) 0.036(3) 0.008(2) 0.001(2) 0.016(2) C14C 0.029(2) 0.022(2) 0.043(3) 0.003(2) 0.000(2) 0.0093(18) C15C 0.026(2) 0.024(2) 0.035(3) -0.004(2) 0.000(2) 0.0138(18) C16C 0.033(2) 0.022(2) 0.030(3) -0.0009(19) -0.004(2) 0.0098(18) C17C 0.034(2) 0.030(2) 0.031(3) 0.005(2) 0.008(2) 0.015(2) C18C 0.034(2) 0.028(2) 0.040(3) -0.002(2) 0.002(2) 0.006(2) C19C 0.030(2) 0.035(2) 0.037(3) 0.006(2) 0.005(2) 0.004(2) C20C 0.050(3) 0.041(3) 0.043(3) 0.012(2) -0.005(2) 0.017(2) C21C 0.046(3) 0.036(3) 0.039(3) 0.008(2) 0.000(2) 0.022(2) C22C 0.038(3) 0.025(2) 0.044(3) 0.003(2) 0.011(2) 0.007(2) C23C 0.057(3) 0.044(3) 0.056(4) 0.005(3) 0.026(3) 0.025(3) C24C 0.041(3) 0.037(3) 0.060(4) -0.015(3) 0.009(3) 0.000(2) C25C 0.019(2) 0.021(2) 0.033(3) 0.0017(19) 0.0039(19) 0.0069(17) C26C 0.020(2) 0.026(2) 0.035(3) -0.003(2) -0.0027(19) 0.0088(18) C27C 0.027(2) 0.042(3) 0.038(3) -0.009(2) -0.001(2) 0.019(2) C28C 0.028(2) 0.044(3) 0.050(3) -0.003(2) -0.005(2) 0.017(2) C29C 0.031(2) 0.045(3) 0.038(3) -0.007(2) -0.010(2) 0.018(2) C30C 0.037(3) 0.047(3) 0.036(3) -0.006(2) -0.003(2) 0.020(2) C31C 0.025(2) 0.027(2) 0.039(3) -0.002(2) 0.000(2) 0.0122(19) C32C 0.037(3) 0.046(3) 0.041(3) 0.001(2) -0.004(2) 0.023(2) C33C 0.052(3) 0.042(3) 0.052(4) 0.008(2) -0.005(3) 0.024(2) C34C 0.053(3) 0.071(4) 0.071(4) -0.011(3) -0.019(3) 0.045(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 O1A C4A 1.363(5) . ? O2A C10A 1.364(6) . ? N1A C15A 1.270(5) . ? N1A C1A 1.464(5) . ? N2A C25A 1.274(5) . ? N2A C2A 1.459(5) . ? C1A C3A 1.510(6) . ? C1A C2A 1.583(5) . ? C2A C9A 1.508(6) . ? C3A C8A 1.384(6) . ? C3A C4A 1.428(6) . ? C4A C5A 1.386(6) . ? C5A C6A 1.372(6) . ? C6A C7A 1.392(6) . ? C7A C8A 1.380(6) . ? C9A C14A 1.388(6) . ? C9A C10A 1.415(6) . ? C10A C11A 1.389(6) . ? C11A C12A 1.376(7) . ? C12A C13A 1.388(7) . ? C13A C14A 1.380(7) . ? C15A C16A 1.448(6) . ? C16A C21A 1.340(6) . ? C16A C17A 1.516(6) . ? C17A C18A 1.548(6) . ? C17A C22A 1.573(6) . ? C18A C19A 1.546(6) . ? C19A C20A 1.527(6) . ? C19A C22A 1.554(6) . ? C20A C21A 1.504(6) . ? C22A C24A 1.517(6) . ? C22A C23A 1.536(6) . ? C25A C26A 1.442(6) . ? C26A C31A 1.338(6) . ? C26A C27A 1.519(6) . ? C27A C32A 1.568(6) . ? C27A C28A 1.576(6) . ? C28A C29A 1.550(7) . ? C29A C30A 1.536(7) . ? C29A C32A 1.575(6) . ? C30A C31A 1.496(6) . ? C32A C33A 1.527(6) . ? C32A C34A 1.529(7) . ? O1B C4B 1.366(5) . ? O2B C10B 1.363(5) . ? N1B C15B 1.264(5) . ? N1B C1B 1.458(5) . ? N2B C25B 1.275(5) . ? N2B C2B 1.471(5) . ? C1B C3B 1.517(6) . ? C1B C2B 1.575(5) . ? C2B C9B 1.504(6) . ? C3B C8B 1.378(6) . ? C3B C4B 1.407(5) . ? C4B C5B 1.382(6) . ? C5B C6B 1.381(6) . ? C6B C7B 1.387(6) . ? C7B C8B 1.378(6) . ? C9B C14B 1.386(6) . ? C9B C10B 1.409(6) . ? C10B C11B 1.387(6) . ? C11B C12B 1.372(6) . ? C12B C13B 1.396(6) . ? C13B C14B 1.390(6) . ? C15B C16B 1.453(6) . ? C16B C21B 1.324(6) . ? C16B C17B 1.526(5) . ? C17B C22B 1.552(6) . ? C17B C18B 1.575(6) . ? C18B C19B 1.542(6) . ? C19B C20B 1.541(6) . ? C19B C22B 1.556(6) . ? C20B C21B 1.495(6) . ? C22B C24B 1.524(6) . ? C22B C23B 1.544(6) . ? C25B C26B 1.457(6) . ? C26B C31B 1.337(6) . ? C26B C27B 1.509(6) . ? C27B C32B 1.547(6) . ? C27B C28B 1.551(6) . ? C28B C29B 1.548(6) . ? C29B C30B 1.517(6) . ? C29B C32B 1.574(6) . ? C30B C31B 1.498(6) . ? C32B C33B 1.531(6) . ? C32B C34B 1.532(6) . ? O1C C4C 1.366(5) . ? O2C C10C 1.370(5) . ? N1C C15C 1.271(5) . ? N1C C1C 1.458(5) . ? N2C C25C 1.276(5) . ? N2C C2C 1.463(5) . ? C1C C3C 1.508(6) . ? C1C C2C 1.574(5) . ? C2C C9C 1.504(6) . ? C3C C8C 1.388(6) . ? C3C C4C 1.408(5) . ? C4C C5C 1.382(6) . ? C5C C6C 1.367(6) . ? C6C C7C 1.387(6) . ? C7C C8C 1.386(6) . ? C9C C14C 1.395(6) . ? C9C C10C 1.415(6) . ? C10C C11C 1.377(6) . ? C11C C12C 1.390(7) . ? C12C C13C 1.389(7) . ? C13C C14C 1.376(6) . ? C15C C16C 1.459(6) . ? C16C C21C 1.326(6) . ? C16C C17C 1.517(6) . ? C17C C22C 1.557(7) . ? C17C C18C 1.559(6) . ? C18C C19C 1.532(6) . ? C19C C20C 1.537(7) . ? C19C C22C 1.556(6) . ? C20C C21C 1.490(7) . ? C22C C24C 1.520(6) . ? C22C C23C 1.529(7) . ? C25C C26C 1.440(6) . ? C26C C31C 1.315(6) . ? C26C C27C 1.523(6) . ? C27C C28C 1.556(6) . ? C27C C32C 1.562(6) . ? C28C C29C 1.533(7) . ? C29C C30C 1.542(6) . ? C29C C32C 1.558(6) . ? C30C C31C 1.498(6) . ? C32C C33C 1.519(6) . ? C32C C34C 1.548(6) . ? 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 C15A N1A C1A 119.7(4) . . ? C25A N2A C2A 119.0(3) . . ? N1A C1A C3A 109.4(3) . . ? N1A C1A C2A 107.6(3) . . ? C3A C1A C2A 112.5(3) . . ? N2A C2A C9A 110.0(3) . . ? N2A C2A C1A 108.3(3) . . ? C9A C2A C1A 112.7(3) . . ? C8A C3A C4A 117.1(4) . . ? C8A C3A C1A 120.7(4) . . ? C4A C3A C1A 122.2(4) . . ? O1A C4A C5A 117.8(4) . . ? O1A C4A C3A 122.3(4) . . ? C5A C4A C3A 119.9(4) . . ? C6A C5A C4A 121.0(4) . . ? C5A C6A C7A 120.0(4) . . ? C8A C7A C6A 119.1(4) . . ? C7A C8A C3A 122.7(4) . . ? C14A C9A C10A 117.9(4) . . ? C14A C9A C2A 120.3(4) . . ? C10A C9A C2A 121.9(4) . . ? O2A C10A C11A 117.7(4) . . ? O2A C10A C9A 122.9(4) . . ? C11A C10A C9A 119.5(4) . . ? C12A C11A C10A 121.1(5) . . ? C11A C12A C13A 120.1(5) . . ? C14A C13A C12A 119.0(5) . . ? C13A C14A C9A 122.4(5) . . ? N1A C15A C16A 122.7(4) . . ? C21A C16A C15A 120.9(4) . . ? C21A C16A C17A 116.8(4) . . ? C15A C16A C17A 122.3(4) . . ? C16A C17A C18A 107.0(3) . . ? C16A C17A C22A 109.9(4) . . ? C18A C17A C22A 86.5(3) . . ? C19A C18A C17A 86.4(3) . . ? C20A C19A C18A 107.9(4) . . ? C20A C19A C22A 111.7(4) . . ? C18A C19A C22A 87.2(3) . . ? C21A C20A C19A 110.8(4) . . ? C16A C21A C20A 119.5(4) . . ? C24A C22A C23A 109.0(3) . . ? C24A C22A C19A 118.4(4) . . ? C23A C22A C19A 112.4(4) . . ? C24A C22A C17A 118.4(4) . . ? C23A C22A C17A 111.8(4) . . ? C19A C22A C17A 85.2(3) . . ? N2A C25A C26A 125.3(4) . . ? C31A C26A C25A 120.3(4) . . ? C31A C26A C27A 116.5(4) . . ? C25A C26A C27A 123.1(4) . . ? C26A C27A C32A 109.9(4) . . ? C26A C27A C28A 106.1(3) . . ? C32A C27A C28A 86.5(3) . . ? C29A C28A C27A 86.3(3) . . ? C30A C29A C28A 108.6(4) . . ? C30A C29A C32A 110.4(4) . . ? C28A C29A C32A 87.1(3) . . ? C31A C30A C29A 110.3(4) . . ? C26A C31A C30A 120.8(4) . . ? C33A C32A C34A 109.1(4) . . ? C33A C32A C27A 119.1(4) . . ? C34A C32A C27A 112.0(4) . . ? C33A C32A C29A 118.4(4) . . ? C34A C32A C29A 110.8(4) . . ? C27A C32A C29A 85.7(3) . . ? C15B N1B C1B 119.1(3) . . ? C25B N2B C2B 118.5(3) . . ? N1B C1B C3B 110.6(3) . . ? N1B C1B C2B 108.6(3) . . ? C3B C1B C2B 110.8(3) . . ? N2B C2B C9B 109.6(3) . . ? N2B C2B C1B 108.1(3) . . ? C9B C2B C1B 110.7(3) . . ? C8B C3B C4B 117.6(4) . . ? C8B C3B C1B 120.7(3) . . ? C4B C3B C1B 121.6(4) . . ? O1B C4B C5B 117.3(4) . . ? O1B C4B C3B 122.7(4) . . ? C5B C4B C3B 120.1(4) . . ? C6B C5B C4B 121.0(4) . . ? C5B C6B C7B 119.5(4) . . ? C8B C7B C6B 119.1(4) . . ? C7B C8B C3B 122.6(4) . . ? C14B C9B C10B 117.6(4) . . ? C14B C9B C2B 121.5(4) . . ? C10B C9B C2B 120.8(4) . . ? O2B C10B C11B 118.2(4) . . ? O2B C10B C9B 121.2(4) . . ? C11B C10B C9B 120.5(4) . . ? C12B C11B C10B 120.5(4) . . ? C11B C12B C13B 120.4(4) . . ? C14B C13B C12B 118.6(4) . . ? C9B C14B C13B 122.3(4) . . ? N1B C15B C16B 123.8(4) . . ? C21B C16B C15B 121.5(4) . . ? C21B C16B C17B 117.1(4) . . ? C15B C16B C17B 121.4(4) . . ? C16B C17B C22B 109.8(3) . . ? C16B C17B C18B 105.0(3) . . ? C22B C17B C18B 86.4(3) . . ? C19B C18B C17B 86.1(3) . . ? C20B C19B C18B 108.3(4) . . ? C20B C19B C22B 109.7(3) . . ? C18B C19B C22B 87.4(3) . . ? C21B C20B C19B 110.5(4) . . ? C16B C21B C20B 120.4(4) . . ? C24B C22B C23B 108.9(4) . . ? C24B C22B C17B 119.7(4) . . ? C23B C22B C17B 111.5(4) . . ? C24B C22B C19B 117.5(4) . . ? C23B C22B C19B 111.1(4) . . ? C17B C22B C19B 86.4(3) . . ? N2B C25B C26B 124.8(4) . . ? C31B C26B C25B 120.3(4) . . ? C31B C26B C27B 116.3(4) . . ? C25B C26B C27B 123.4(4) . . ? C26B C27B C32B 110.4(3) . . ? C26B C27B C28B 106.7(3) . . ? C32B C27B C28B 87.0(3) . . ? C29B C28B C27B 86.4(3) . . ? C30B C29B C28B 108.6(4) . . ? C30B C29B C32B 111.0(3) . . ? C28B C29B C32B 86.2(3) . . ? C31B C30B C29B 110.5(4) . . ? C26B C31B C30B 120.4(4) . . ? C33B C32B C34B 108.2(4) . . ? C33B C32B C27B 119.8(4) . . ? C34B C32B C27B 112.3(4) . . ? C33B C32B C29B 117.7(4) . . ? C34B C32B C29B 111.9(3) . . ? C27B C32B C29B 85.6(3) . . ? C15C N1C C1C 119.8(3) . . ? C25C N2C C2C 119.7(3) . . ? N1C C1C C3C 110.1(3) . . ? N1C C1C C2C 107.8(3) . . ? C3C C1C C2C 110.3(3) . . ? N2C C2C C9C 109.3(3) . . ? N2C C2C C1C 107.8(3) . . ? C9C C2C C1C 111.3(3) . . ? C8C C3C C4C 118.2(4) . . ? C8C C3C C1C 120.1(3) . . ? C4C C3C C1C 121.7(4) . . ? O1C C4C C5C 118.3(3) . . ? O1C C4C C3C 121.5(4) . . ? C5C C4C C3C 120.2(4) . . ? C6C C5C C4C 120.3(4) . . ? C5C C6C C7C 120.8(4) . . ? C8C C7C C6C 119.1(4) . . ? C7C C8C C3C 121.3(4) . . ? C14C C9C C10C 117.1(4) . . ? C14C C9C C2C 121.3(4) . . ? C10C C9C C2C 121.4(4) . . ? O2C C10C C11C 118.3(4) . . ? O2C C10C C9C 121.3(4) . . ? C11C C10C C9C 120.4(4) . . ? C10C C11C C12C 121.0(4) . . ? C13C C12C C11C 119.5(5) . . ? C14C C13C C12C 119.3(4) . . ? C13C C14C C9C 122.6(4) . . ? N1C C15C C16C 124.6(4) . . ? C21C C16C C15C 120.9(4) . . ? C21C C16C C17C 116.8(4) . . ? C15C C16C C17C 122.3(4) . . ? C16C C17C C22C 110.2(4) . . ? C16C C17C C18C 106.1(3) . . ? C22C C17C C18C 86.4(3) . . ? C19C C18C C17C 86.3(3) . . ? C18C C19C C20C 108.8(4) . . ? C18C C19C C22C 87.4(3) . . ? C20C C19C C22C 110.1(4) . . ? C21C C20C C19C 110.4(4) . . ? C16C C21C C20C 120.3(4) . . ? C24C C22C C23C 107.3(4) . . ? C24C C22C C19C 118.9(4) . . ? C23C C22C C19C 111.9(4) . . ? C24C C22C C17C 120.3(4) . . ? C23C C22C C17C 111.8(4) . . ? C19C C22C C17C 85.5(3) . . ? N2C C25C C26C 124.4(4) . . ? C31C C26C C25C 122.1(4) . . ? C31C C26C C27C 116.9(4) . . ? C25C C26C C27C 120.9(4) . . ? C26C C27C C28C 106.2(3) . . ? C26C C27C C32C 109.7(4) . . ? C28C C27C C32C 86.3(3) . . ? C29C C28C C27C 86.5(3) . . ? C28C C29C C30C 109.1(4) . . ? C28C C29C C32C 87.2(3) . . ? C30C C29C C32C 110.8(4) . . ? C31C C30C C29C 109.3(4) . . ? C26C C31C C30C 121.1(4) . . ? C33C C32C C34C 108.1(4) . . ? C33C C32C C29C 119.9(4) . . ? C34C C32C C29C 111.5(4) . . ? C33C C32C C27C 118.4(4) . . ? C34C C32C C27C 112.2(4) . . ? C29C C32C C27C 85.4(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.219 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.048 # Attachment 'rr3a.txt' data_k06185 _database_code_depnum_ccdc_archive 'CCDC 665964' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H40 N2 O2' _chemical_formula_sum 'C34 H40 N2 O2' _chemical_formula_weight 508.68 _chemical_absolute_configuration rm 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 Hexagonal _symmetry_space_group_name_H-M 'P 65 2 2' _symmetry_space_group_name_Hall 'P 65 2 ( 0 0 1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' 'y, x, -z+2/3' 'x-y, -y, -z' '-x, -x+y, -z+1/3' '-y, -x, -z+1/6' '-x+y, y, -z+1/2' 'x, x-y, -z+5/6' _cell_length_a 14.1593(4) _cell_length_b 14.1593(4) _cell_length_c 25.3297(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4397.9(2) _cell_formula_units_Z 6 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 12503 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 25.0 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.152 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1644 _exptl_absorpt_coefficient_mu 0.071 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ?0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12503 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1589 _reflns_number_gt 1174 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1(Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL V6.1' _computing_publication_material 'SHELXTL V6.1' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0827P)^2^+0.3492P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? #_refine_ls_abs_structure_details # 'Flack H D (1983), Acta Cryst. A39, 876-881' #_refine_ls_abs_structure_Flack -2(4) _refine_ls_number_reflns 1589 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1353 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.66319(19) 0.8610(2) 0.07167(9) 0.0555(7) Uani 1 1 d . . . N1 N 0.7603(2) 1.0550(2) 0.10941(10) 0.0416(7) Uani 1 1 d . . . C1 C 0.8160(2) 1.0287(2) 0.13910(12) 0.0411(7) Uani 1 1 d . . . H1A H 0.8685 1.0820 0.1621 0.049 Uiso 1 1 calc R . . C2 C 0.8016(2) 0.9194(2) 0.13884(12) 0.0422(8) Uani 1 1 d . . . C3 C 0.7285(2) 0.8409(2) 0.10350(13) 0.0473(8) Uani 1 1 d . . . C4 C 0.7219(3) 0.7391(3) 0.10014(15) 0.0581(10) Uani 1 1 d . . . H4A H 0.6737 0.6862 0.0756 0.070 Uiso 1 1 calc R . . C5 C 0.7857(3) 0.7162(3) 0.13267(16) 0.0656(11) Uani 1 1 d . . . H5A H 0.7825 0.6478 0.1297 0.079 Uiso 1 1 calc R . . C6 C 0.8547(3) 0.7915(3) 0.16982(17) 0.0666(11) Uani 1 1 d . . . H6A H 0.8961 0.7738 0.1932 0.080 Uiso 1 1 calc R . . C7 C 0.8621(3) 0.8922(3) 0.17221(15) 0.0537(9) Uani 1 1 d . . . H7A H 0.9097 0.9442 0.1973 0.064 Uiso 1 1 calc R . . C8 C 0.7798(3) 1.1671(2) 0.10991(12) 0.0418(8) Uani 1 1 d . . . H8 H 0.8307 1.2087 0.1394 0.050 Uiso 1 1 calc R . . C9 C 0.6715(2) 1.1614(2) 0.11870(12) 0.0450(8) Uani 1 1 d . . . C10 C 0.5777(3) 1.0968(3) 0.08160(14) 0.0532(9) Uani 1 1 d . . . H10A H 0.5937 1.0647 0.0501 0.064 Uiso 1 1 calc R . . C11 C 0.5229(3) 1.1668(3) 0.07048(14) 0.0628(10) Uani 1 1 d . . . H11A H 0.5741 1.2465 0.0697 0.075 Uiso 1 1 calc R . . H11B H 0.4735 1.1427 0.0395 0.075 Uiso 1 1 calc R . . C12 C 0.6533(3) 1.2079(3) 0.15975(14) 0.0519(9) Uani 1 1 d . . . H12A H 0.7104 1.2506 0.1838 0.062 Uiso 1 1 calc R . . C13 C 0.5401(3) 1.1923(3) 0.16791(14) 0.0570(10) Uani 1 1 d . . . H13A H 0.5108 1.1563 0.2023 0.068 Uiso 1 1 calc R . . H13B H 0.5444 1.2642 0.1685 0.068 Uiso 1 1 calc R . . C14 C 0.4645(3) 1.1232(3) 0.12404(13) 0.0566(10) Uani 1 1 d . . . H14A H 0.3886 1.1107 0.1260 0.068 Uiso 1 1 calc R . . C15 C 0.4735(3) 1.0182(3) 0.11405(14) 0.0547(9) Uani 1 1 d . . . C16 C 0.3818(3) 0.9357(3) 0.07825(16) 0.0764(12) Uani 1 1 d . . . H16A H 0.3900 0.8715 0.0733 0.115 Uiso 1 1 calc R . . H16B H 0.3858 0.9694 0.0439 0.115 Uiso 1 1 calc R . . H16C H 0.3111 0.9136 0.0946 0.115 Uiso 1 1 calc R . . C17 C 0.4865(3) 0.9592(3) 0.16066(15) 0.0629(10) Uani 1 1 d . . . H17A H 0.4894 0.8951 0.1482 0.094 Uiso 1 1 calc R . . H17B H 0.4244 0.9359 0.1846 0.094 Uiso 1 1 calc R . . H17C H 0.5542 1.0082 0.1794 0.094 Uiso 1 1 calc R . . H1O H 0.687(3) 0.936(4) 0.0787(15) 0.084(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0582(15) 0.0535(15) 0.0549(15) -0.0046(12) -0.0060(12) 0.0280(12) N1 0.0436(15) 0.0461(15) 0.0418(14) 0.0043(12) 0.0054(12) 0.0275(13) C1 0.0412(17) 0.0439(18) 0.0414(17) 0.0036(14) 0.0067(15) 0.0238(15) C2 0.0387(17) 0.0462(19) 0.0488(18) 0.0066(15) 0.0106(15) 0.0267(16) C3 0.0462(18) 0.0470(19) 0.050(2) 0.0052(17) 0.0139(16) 0.0245(16) C4 0.058(2) 0.045(2) 0.069(2) 0.0020(18) 0.022(2) 0.0240(18) C5 0.068(3) 0.052(2) 0.090(3) 0.015(2) 0.032(2) 0.041(2) C6 0.065(2) 0.064(3) 0.089(3) 0.022(2) 0.013(2) 0.045(2) C7 0.0474(19) 0.055(2) 0.067(2) 0.0108(18) 0.0060(17) 0.0314(17) C8 0.0495(19) 0.0460(18) 0.0410(17) 0.0065(15) 0.0041(15) 0.0322(16) C9 0.0510(19) 0.0498(19) 0.0465(17) 0.0075(16) 0.0071(16) 0.0343(16) C10 0.057(2) 0.070(2) 0.0464(18) -0.0012(18) 0.0040(17) 0.0418(18) C11 0.063(2) 0.086(3) 0.062(2) 0.012(2) 0.0078(19) 0.055(2) C12 0.056(2) 0.053(2) 0.055(2) 0.0040(18) 0.0088(17) 0.0337(17) C13 0.060(2) 0.056(2) 0.067(2) 0.004(2) 0.0167(19) 0.0380(19) C14 0.052(2) 0.071(2) 0.061(2) 0.011(2) 0.0142(18) 0.042(2) C15 0.052(2) 0.061(2) 0.061(2) -0.0015(19) 0.0021(18) 0.0350(18) C16 0.056(2) 0.085(3) 0.084(3) -0.015(3) 0.003(2) 0.032(2) C17 0.059(2) 0.056(2) 0.081(3) 0.010(2) 0.014(2) 0.0347(19) _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 C3 1.360(4) . ? N1 C1 1.273(3) . ? N1 C8 1.469(4) . ? C1 C2 1.457(4) . ? C2 C7 1.388(4) . ? C2 C3 1.399(4) . ? C3 C4 1.399(4) . ? C4 C5 1.376(5) . ? C5 C6 1.391(5) . ? C6 C7 1.378(5) . ? C8 C9 1.511(4) . ? C8 C8 1.542(6) 10_775 ? C9 C12 1.323(4) . ? C9 C10 1.506(4) . ? C10 C11 1.560(4) . ? C10 C15 1.565(5) . ? C11 C14 1.547(5) . ? C12 C13 1.519(4) . ? C13 C14 1.513(5) . ? C14 C15 1.575(5) . ? C15 C17 1.510(5) . ? C15 C16 1.534(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 C1 N1 C8 120.1(3) . . ? N1 C1 C2 122.0(3) . . ? C7 C2 C3 118.9(3) . . ? C7 C2 C1 120.9(3) . . ? C3 C2 C1 120.1(3) . . ? O1 C3 C2 121.6(3) . . ? O1 C3 C4 118.5(3) . . ? C2 C3 C4 119.9(3) . . ? C5 C4 C3 119.6(3) . . ? C4 C5 C6 121.1(3) . . ? C7 C6 C5 118.9(4) . . ? C6 C7 C2 121.5(4) . . ? N1 C8 C9 107.8(3) . . ? N1 C8 C8 107.6(2) . 10_775 ? C9 C8 C8 112.9(2) . 10_775 ? C12 C9 C10 117.4(3) . . ? C12 C9 C8 122.2(3) . . ? C10 C9 C8 120.3(3) . . ? C9 C10 C11 107.2(3) . . ? C9 C10 C15 109.6(3) . . ? C11 C10 C15 87.4(2) . . ? C14 C11 C10 85.7(2) . . ? C9 C12 C13 119.2(3) . . ? C14 C13 C12 110.4(3) . . ? C13 C14 C11 108.8(3) . . ? C13 C14 C15 111.3(3) . . ? C11 C14 C15 87.5(3) . . ? C17 C15 C16 109.4(3) . . ? C17 C15 C10 118.1(3) . . ? C16 C15 C10 111.6(3) . . ? C17 C15 C14 119.1(3) . . ? C16 C15 C14 112.1(3) . . ? C10 C15 C14 84.5(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O N1 0.96(4) 1.66(4) 2.564(3) 154(3) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.137 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.032