data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Norikazu Ueyama' 'Daisuke Kanamori' 'Taka-aki Okamura' 'Hitoshi Yamamoto' _publ_contact_author_name 'Mr Norikazu Ueyama' _publ_contact_author_address ; Science Osaka University Machikaneyamacho1-1 Toyonaka 560-0043 ; _publ_contact_author_email UEYAMA@CHEM.SCI.OSAKA-U.AC.JP _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Contribution of the Intramolecular Hydrogen Bond to the Shift of the pKa Value and the Oxidation Potential of Phenols and Phenolate Anions ; data_1OH _database_code_depnum_ccdc_archive 'CCDC 259697' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H31 N O2' _chemical_formula_sum 'C19 H31 N O2' _chemical_formula_weight 305.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6747(6) _cell_length_b 12.0073(3) _cell_length_c 15.3190(11) _cell_angle_alpha 101.634(3) _cell_angle_beta 99.209(4) _cell_angle_gamma 90.717(4) _cell_volume 1896.34(18) _cell_formula_units_Z 4 _cell_measurement_temperature 200 _cell_measurement_reflns_used 8123 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 27.4 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.600 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.070 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.960 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16337 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0868 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.48 _reflns_number_total 8344 _reflns_number_gt 4113 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'teXsan Ver. 1.11' _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^)+(0.1368P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8344 _refine_ls_number_parameters 459 _refine_ls_number_restraints 108 _refine_ls_R_factor_all 0.1544 _refine_ls_R_factor_gt 0.0775 _refine_ls_wR_factor_ref 0.2478 _refine_ls_wR_factor_gt 0.2110 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.988 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.08455(18) 0.29019(19) 0.09565(14) 0.0582(6) Uani 1 1 d . . . O3 O 0.58302(18) 0.2717(2) 0.09485(15) 0.0598(6) Uani 1 1 d . . . O11 O 0.03837(17) 0.46164(18) 0.20661(13) 0.0457(5) Uani 1 1 d . . . H11 H 0.034(3) 0.393(3) 0.161(2) 0.055 Uiso 1 1 d . . . O31 O 0.52866(18) 0.14395(19) 0.19609(14) 0.0489(5) Uani 1 1 d . . . H31 H 0.523(3) 0.180(3) 0.149(2) 0.059 Uiso 1 1 d . . . N1 N 0.2798(2) 0.25429(18) 0.06715(14) 0.0387(6) Uani 1 1 d . . . H1 H 0.3613 0.2729 0.0845 0.046 Uiso 1 1 calc R . . N3 N 0.7787(2) 0.28537(19) 0.06375(15) 0.0413(6) Uani 1 1 d . . . H3 H 0.8588 0.2698 0.0781 0.050 Uiso 1 1 calc R . . C1 C 0.2013(2) 0.3132(2) 0.11510(17) 0.0357(6) Uani 1 1 d . . . C3 C 0.6984(2) 0.2520(2) 0.11145(17) 0.0354(6) Uani 1 1 d . . . C11 C 0.1651(2) 0.4780(2) 0.23518(17) 0.0366(6) Uani 1 1 d . . . C12 C 0.2515(2) 0.4088(2) 0.19267(16) 0.0338(6) Uani 1 1 d . . . C13 C 0.3814(2) 0.4292(2) 0.22553(18) 0.0380(6) Uani 1 1 d . . . H13 H 0.4402 0.3819 0.1973 0.046 Uiso 1 1 calc R . . C14 C 0.4267(3) 0.5170(2) 0.29843(18) 0.0401(7) Uani 1 1 d . . . C15 C 0.3374(3) 0.5833(2) 0.33743(18) 0.0426(7) Uani 1 1 d . . . H15 H 0.3675 0.6438 0.3871 0.051 Uiso 1 1 calc R . . C16 C 0.2076(3) 0.5682(2) 0.30950(18) 0.0389(6) Uani 1 1 d . . . C17 C 0.2452(3) 0.1592(2) -0.01349(19) 0.0432(7) Uani 1 1 d . . . C18 C 0.1955(10) 0.2149(8) -0.0922(4) 0.071(2) Uani 0.712(18) 1 d PU . . H18A H 0.1185 0.2548 -0.0803 0.086 Uiso 0.712(18) 1 calc PR . . H18B H 0.1755 0.1563 -0.1477 0.086 Uiso 0.712(18) 1 calc PR . . H18C H 0.2603 0.2694 -0.0993 0.086 Uiso 0.712(18) 1 calc PR . . C19 C 0.1481(9) 0.0744(7) -0.0009(6) 0.069(2) Uani 0.712(18) 1 d PU . . H19A H 0.0692 0.1124 0.0084 0.083 Uiso 0.712(18) 1 calc PR . . H19B H 0.1806 0.0424 0.0519 0.083 Uiso 0.712(18) 1 calc PR . . H19C H 0.1314 0.0131 -0.0548 0.083 Uiso 0.712(18) 1 calc PR . . C20 C 0.3675(8) 0.0987(7) -0.0283(6) 0.062(2) Uani 0.712(18) 1 d PU . . H20A H 0.4318 0.1537 -0.0357 0.075 Uiso 0.712(18) 1 calc PR . . H20B H 0.3503 0.0383 -0.0828 0.075 Uiso 0.712(18) 1 calc PR . . H20C H 0.3990 0.0655 0.0240 0.075 Uiso 0.712(18) 1 calc PR . . C21 C 0.5706(3) 0.5371(3) 0.3334(2) 0.0490(8) Uani 1 1 d . . . C22 C 0.6265(4) 0.4329(4) 0.3565(4) 0.1059(18) Uani 1 1 d . . . H22A H 0.6067 0.3697 0.3042 0.127 Uiso 1 1 calc R . . H22B H 0.5910 0.4145 0.4074 0.127 Uiso 1 1 calc R . . H22C H 0.7189 0.4453 0.3734 0.127 Uiso 1 1 calc R . . C23 C 0.6340(4) 0.5691(6) 0.2581(3) 0.117(2) Uani 1 1 d . . . H23A H 0.5979 0.6385 0.2422 0.140 Uiso 1 1 calc R . . H23B H 0.6189 0.5069 0.2047 0.140 Uiso 1 1 calc R . . H23C H 0.7256 0.5824 0.2791 0.140 Uiso 1 1 calc R . . C24 C 0.5995(4) 0.6349(4) 0.4158(3) 0.115(2) Uani 1 1 d . . . H24A H 0.5654 0.7049 0.3999 0.138 Uiso 1 1 calc R . . H24B H 0.6916 0.6456 0.4353 0.138 Uiso 1 1 calc R . . H24C H 0.5600 0.6168 0.4650 0.138 Uiso 1 1 calc R . . C25 C 0.1129(3) 0.6438(3) 0.3569(2) 0.0516(8) Uani 1 1 d . . . C26 C 0.1810(4) 0.7368(3) 0.4328(2) 0.0725(11) Uani 1 1 d . . . H26A H 0.1183 0.7833 0.4616 0.087 Uiso 1 1 calc R . . H26B H 0.2351 0.7849 0.4081 0.087 Uiso 1 1 calc R . . H26C H 0.2336 0.7020 0.4777 0.087 Uiso 1 1 calc R . . C27 C 0.0305(3) 0.7020(3) 0.2896(2) 0.0659(10) Uani 1 1 d . . . H27A H -0.0296 0.7496 0.3206 0.079 Uiso 1 1 calc R . . H27B H -0.0165 0.6441 0.2405 0.079 Uiso 1 1 calc R . . H27C H 0.0848 0.7497 0.2646 0.079 Uiso 1 1 calc R . . C28 C 0.0300(4) 0.5709(3) 0.3981(2) 0.0696(10) Uani 1 1 d . . . H28A H -0.0307 0.6188 0.4282 0.084 Uiso 1 1 calc R . . H28B H 0.0838 0.5361 0.4423 0.084 Uiso 1 1 calc R . . H28C H -0.0163 0.5111 0.3503 0.084 Uiso 1 1 calc R . . C31 C 0.6552(2) 0.1393(2) 0.22476(17) 0.0348(6) Uani 1 1 d . . . C32 C 0.7445(2) 0.1909(2) 0.18552(17) 0.0339(6) Uani 1 1 d . . . C33 C 0.8735(2) 0.1845(2) 0.21771(17) 0.0359(6) Uani 1 1 d . . . H33 H 0.9342 0.2190 0.1912 0.043 Uiso 1 1 calc R . . C34 C 0.9155(2) 0.1293(2) 0.28722(17) 0.0368(6) Uani 1 1 d . . . C35 C 0.8240(3) 0.0789(2) 0.32360(17) 0.0396(7) Uani 1 1 d . . . H35 H 0.8518 0.0399 0.3708 0.048 Uiso 1 1 calc R . . C36 C 0.6941(3) 0.0823(2) 0.29522(17) 0.0369(6) Uani 1 1 d . . . C37 C 0.7483(3) 0.3466(3) -0.01181(18) 0.0436(7) Uani 1 1 d . . . C38 C 0.6578(13) 0.4415(10) 0.0078(8) 0.081(3) Uani 0.564(16) 1 d PU . . H38A H 0.5766 0.4092 0.0156 0.097 Uiso 0.564(16) 1 calc PR . . H38B H 0.6439 0.4810 -0.0428 0.097 Uiso 0.564(16) 1 calc PR . . H38C H 0.6945 0.4956 0.0632 0.097 Uiso 0.564(16) 1 calc PR . . C39 C 0.6919(15) 0.2544(12) -0.0928(7) 0.092(4) Uani 0.564(16) 1 d PU . . H39A H 0.6130 0.2218 -0.0813 0.111 Uiso 0.564(16) 1 calc PR . . H39B H 0.7527 0.1944 -0.1026 0.111 Uiso 0.564(16) 1 calc PR . . H39C H 0.6739 0.2876 -0.1467 0.111 Uiso 0.564(16) 1 calc PR . . C40 C 0.8696(10) 0.4002(12) -0.0236(9) 0.075(3) Uani 0.564(16) 1 d PU . . H40A H 0.9226 0.4268 0.0356 0.090 Uiso 0.564(16) 1 calc PR . . H40B H 0.8510 0.4649 -0.0529 0.090 Uiso 0.564(16) 1 calc PR . . H40C H 0.9148 0.3441 -0.0613 0.090 Uiso 0.564(16) 1 calc PR . . C41 C 1.0580(3) 0.1244(3) 0.32225(19) 0.0449(7) Uani 1 1 d . . . C42 C 1.1191(4) 0.0616(5) 0.2468(3) 0.122(2) Uani 1 1 d . . . H42A H 1.0812 -0.0160 0.2269 0.146 Uiso 1 1 calc R . . H42B H 1.2104 0.0585 0.2679 0.146 Uiso 1 1 calc R . . H42C H 1.1059 0.1010 0.1962 0.146 Uiso 1 1 calc R . . C43 C 1.1148(4) 0.2434(4) 0.3547(3) 0.0941(15) Uani 1 1 d . . . H43A H 1.0745 0.2827 0.4047 0.113 Uiso 1 1 calc R . . H43B H 1.1009 0.2844 0.3051 0.113 Uiso 1 1 calc R . . H43C H 1.2063 0.2407 0.3755 0.113 Uiso 1 1 calc R . . C44 C 1.0836(4) 0.0638(4) 0.4001(3) 0.0983(15) Uani 1 1 d . . . H44A H 1.0435 0.1033 0.4502 0.118 Uiso 1 1 calc R . . H44B H 1.1754 0.0633 0.4201 0.118 Uiso 1 1 calc R . . H44C H 1.0484 -0.0148 0.3805 0.118 Uiso 1 1 calc R . . C45 C 0.5954(3) 0.0271(3) 0.33848(19) 0.0486(8) Uani 1 1 d . . . C46 C 0.6603(4) -0.0305(3) 0.4133(2) 0.0637(10) Uani 1 1 d . . . H46A H 0.5956 -0.0651 0.4395 0.076 Uiso 1 1 calc R . . H46B H 0.7125 0.0264 0.4604 0.076 Uiso 1 1 calc R . . H46C H 0.7143 -0.0896 0.3877 0.076 Uiso 1 1 calc R . . C47 C 0.5121(3) 0.1184(3) 0.3817(2) 0.0608(9) Uani 1 1 d . . . H47A H 0.4493 0.0827 0.4089 0.073 Uiso 1 1 calc R . . H47B H 0.4681 0.1562 0.3353 0.073 Uiso 1 1 calc R . . H47C H 0.5655 0.1747 0.4285 0.073 Uiso 1 1 calc R . . C48 C 0.5123(3) -0.0647(3) 0.2678(2) 0.0643(10) Uani 1 1 d . . . H48A H 0.4502 -0.0986 0.2967 0.077 Uiso 1 1 calc R . . H48B H 0.5661 -0.1239 0.2421 0.077 Uiso 1 1 calc R . . H48C H 0.4676 -0.0301 0.2197 0.077 Uiso 1 1 calc R . . C51 C 0.134(3) 0.1794(17) -0.0826(13) 0.079(6) Uani 0.288(18) 1 d PU . . H51A H 0.0701 0.2207 -0.0515 0.094 Uiso 0.288(18) 1 calc PR . . H51B H 0.0970 0.1061 -0.1184 0.094 Uiso 0.288(18) 1 calc PR . . H51C H 0.1640 0.2244 -0.1226 0.094 Uiso 0.288(18) 1 calc PR . . C52 C 0.210(3) 0.0523(18) 0.0235(15) 0.079(6) Uani 0.288(18) 1 d PU . . H52A H 0.1269 0.0613 0.0429 0.095 Uiso 0.288(18) 1 calc PR . . H52B H 0.2745 0.0449 0.0750 0.095 Uiso 0.288(18) 1 calc PR . . H52C H 0.2066 -0.0161 -0.0243 0.095 Uiso 0.288(18) 1 calc PR . . C53 C 0.355(2) 0.136(2) -0.0607(16) 0.076(6) Uani 0.288(18) 1 d PU . . H53A H 0.3683 0.1977 -0.0922 0.091 Uiso 0.288(18) 1 calc PR . . H53B H 0.3397 0.0637 -0.1045 0.091 Uiso 0.288(18) 1 calc PR . . H53C H 0.4316 0.1318 -0.0165 0.091 Uiso 0.288(18) 1 calc PR . . C54 C 0.7360(17) 0.4684(9) 0.0302(8) 0.076(4) Uani 0.436(16) 1 d PU . . H54A H 0.6547 0.4773 0.0523 0.091 Uiso 0.436(16) 1 calc PR . . H54B H 0.7392 0.5153 -0.0150 0.091 Uiso 0.436(16) 1 calc PR . . H54C H 0.8058 0.4927 0.0808 0.091 Uiso 0.436(16) 1 calc PR . . C55 C 0.6352(15) 0.2993(14) -0.0815(10) 0.080(5) Uani 0.436(16) 1 d PU . . H55A H 0.5702 0.2705 -0.0522 0.096 Uiso 0.436(16) 1 calc PR . . H55B H 0.6609 0.2371 -0.1262 0.096 Uiso 0.436(16) 1 calc PR . . H55C H 0.6006 0.3595 -0.1118 0.096 Uiso 0.436(16) 1 calc PR . . C56 C 0.8637(14) 0.3401(16) -0.0605(10) 0.075(4) Uani 0.436(16) 1 d PU . . H56A H 0.8600 0.2668 -0.1030 0.090 Uiso 0.436(16) 1 calc PR . . H56B H 0.9418 0.3472 -0.0160 0.090 Uiso 0.436(16) 1 calc PR . . H56C H 0.8630 0.4020 -0.0935 0.090 Uiso 0.436(16) 1 calc PR . . 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 0.0351(11) 0.0671(14) 0.0590(13) -0.0166(11) 0.0062(10) -0.0039(10) O3 0.0375(11) 0.0948(17) 0.0623(14) 0.0496(13) 0.0101(10) 0.0118(11) O11 0.0332(10) 0.0516(12) 0.0469(11) -0.0023(9) 0.0064(9) 0.0037(9) O31 0.0378(11) 0.0687(14) 0.0457(12) 0.0262(10) 0.0051(9) 0.0007(10) N1 0.0336(12) 0.0406(13) 0.0376(12) -0.0002(10) 0.0038(10) -0.0013(10) N3 0.0321(12) 0.0518(14) 0.0444(13) 0.0234(11) 0.0024(10) 0.0014(11) C1 0.0348(14) 0.0411(15) 0.0309(13) 0.0065(11) 0.0058(11) 0.0015(12) C3 0.0332(14) 0.0361(14) 0.0363(14) 0.0104(11) 0.0005(11) 0.0002(11) C11 0.0373(14) 0.0395(15) 0.0340(14) 0.0111(11) 0.0050(11) 0.0004(12) C12 0.0367(14) 0.0350(14) 0.0296(13) 0.0063(11) 0.0059(11) -0.0010(11) C13 0.0377(14) 0.0386(15) 0.0370(14) 0.0055(12) 0.0066(12) 0.0031(12) C14 0.0397(15) 0.0368(14) 0.0415(15) 0.0062(12) 0.0024(12) -0.0033(12) C15 0.0502(17) 0.0342(14) 0.0385(15) 0.0026(12) -0.0010(13) -0.0029(13) C16 0.0438(15) 0.0374(15) 0.0351(14) 0.0052(11) 0.0077(12) 0.0022(12) C17 0.0414(15) 0.0438(16) 0.0393(15) -0.0060(12) 0.0102(12) -0.0024(13) C18 0.097(5) 0.075(5) 0.036(3) 0.004(3) 0.001(3) 0.007(4) C19 0.082(5) 0.050(4) 0.067(5) -0.018(3) 0.028(4) -0.017(4) C20 0.057(3) 0.057(4) 0.060(5) -0.014(3) 0.007(3) 0.012(3) C21 0.0392(16) 0.0492(17) 0.0519(18) 0.0033(14) -0.0025(13) -0.0053(14) C22 0.060(2) 0.081(3) 0.152(5) 0.012(3) -0.040(3) 0.004(2) C23 0.058(2) 0.193(6) 0.100(4) 0.037(4) 0.009(2) -0.043(3) C24 0.061(3) 0.126(4) 0.115(4) -0.050(3) -0.019(3) -0.012(3) C25 0.0515(17) 0.0506(18) 0.0474(17) -0.0041(14) 0.0098(14) 0.0079(15) C26 0.074(2) 0.064(2) 0.066(2) -0.0186(18) 0.0111(19) 0.0124(19) C27 0.064(2) 0.057(2) 0.070(2) 0.0017(17) 0.0069(18) 0.0218(17) C28 0.070(2) 0.081(3) 0.059(2) 0.0010(19) 0.0292(18) 0.0085(19) C31 0.0352(14) 0.0362(14) 0.0324(13) 0.0056(11) 0.0055(11) 0.0016(11) C32 0.0364(14) 0.0345(14) 0.0318(13) 0.0097(11) 0.0042(11) 0.0039(11) C33 0.0402(14) 0.0376(14) 0.0316(13) 0.0110(11) 0.0058(11) 0.0029(12) C34 0.0393(14) 0.0352(14) 0.0353(14) 0.0094(11) 0.0012(12) 0.0037(12) C35 0.0526(17) 0.0334(14) 0.0322(14) 0.0115(11) -0.0008(12) 0.0016(13) C36 0.0474(16) 0.0340(14) 0.0301(13) 0.0082(11) 0.0077(12) -0.0026(12) C37 0.0422(15) 0.0551(18) 0.0400(15) 0.0272(14) 0.0038(13) 0.0001(14) C38 0.095(7) 0.084(6) 0.091(7) 0.062(6) 0.039(6) 0.038(6) C39 0.127(10) 0.111(8) 0.037(4) 0.027(5) -0.004(5) -0.017(6) C40 0.063(4) 0.095(7) 0.086(7) 0.065(6) 0.011(5) -0.007(5) C41 0.0397(15) 0.0531(17) 0.0414(15) 0.0155(13) -0.0025(13) 0.0101(14) C42 0.057(2) 0.196(6) 0.090(3) -0.014(4) -0.005(2) 0.056(3) C43 0.061(2) 0.097(3) 0.112(4) 0.028(3) -0.029(2) -0.011(2) C44 0.065(2) 0.144(4) 0.095(3) 0.063(3) -0.010(2) 0.015(3) C45 0.0589(19) 0.0520(18) 0.0372(15) 0.0154(13) 0.0079(14) -0.0118(15) C46 0.085(2) 0.065(2) 0.0458(18) 0.0276(16) 0.0080(17) -0.0157(19) C47 0.061(2) 0.080(2) 0.0472(18) 0.0157(17) 0.0246(16) -0.0038(18) C48 0.079(2) 0.064(2) 0.0504(19) 0.0182(16) 0.0051(17) -0.0282(19) C51 0.108(13) 0.062(9) 0.048(8) -0.017(7) -0.004(9) -0.012(9) C52 0.108(15) 0.056(9) 0.070(10) 0.003(7) 0.021(10) -0.003(10) C53 0.067(10) 0.084(13) 0.061(11) -0.019(8) 0.012(9) 0.004(10) C54 0.099(9) 0.060(6) 0.076(6) 0.030(5) 0.014(6) 0.005(6) C55 0.094(9) 0.089(9) 0.055(7) 0.045(7) -0.029(6) -0.030(7) C56 0.064(6) 0.114(10) 0.070(8) 0.054(7) 0.035(6) 0.018(8) _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 1.248(3) . ? O3 C3 1.253(3) . ? O11 C11 1.353(3) . ? O11 H11 0.96(3) . ? O31 C31 1.357(3) . ? O31 H31 0.90(3) . ? N1 C1 1.321(3) . ? N1 C17 1.497(3) . ? N1 H1 0.8800 . ? N3 C3 1.319(3) . ? N3 C37 1.488(3) . ? N3 H3 0.8800 . ? C1 C12 1.499(3) . ? C3 C32 1.494(4) . ? C11 C12 1.400(4) . ? C11 C16 1.414(4) . ? C12 C13 1.398(4) . ? C13 C14 1.390(4) . ? C13 H13 0.9500 . ? C14 C15 1.381(4) . ? C14 C21 1.543(4) . ? C15 C16 1.382(4) . ? C15 H15 0.9500 . ? C16 C25 1.538(4) . ? C17 C53 1.48(2) . ? C17 C19 1.505(8) . ? C17 C51 1.513(19) . ? C17 C18 1.520(7) . ? C17 C20 1.529(8) . ? C17 C52 1.57(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.475(5) . ? C21 C24 1.528(5) . ? C21 C23 1.536(6) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.521(4) . ? C25 C28 1.526(5) . ? C25 C27 1.530(5) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C31 C36 1.403(4) . ? C31 C32 1.405(4) . ? C32 C33 1.395(3) . ? C33 C34 1.384(4) . ? C33 H33 0.9500 . ? C34 C35 1.388(4) . ? C34 C41 1.536(4) . ? C35 C36 1.388(4) . ? C35 H35 0.9500 . ? C36 C45 1.540(4) . ? C37 C54 1.490(12) . ? C37 C40 1.491(10) . ? C37 C55 1.498(12) . ? C37 C38 1.518(9) . ? C37 C39 1.523(11) . ? C37 C56 1.533(13) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 C42 1.494(5) . ? C41 C43 1.501(5) . ? C41 C44 1.509(5) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 C46 1.532(4) . ? C45 C47 1.534(5) . ? C45 C48 1.536(4) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 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 C11 O11 H11 101.4(18) . . ? C31 O31 H31 105(2) . . ? C1 N1 C17 127.0(2) . . ? C1 N1 H1 116.5 . . ? C17 N1 H1 116.5 . . ? C3 N3 C37 126.9(2) . . ? C3 N3 H3 116.5 . . ? C37 N3 H3 116.5 . . ? O1 C1 N1 120.2(2) . . ? O1 C1 C12 119.5(2) . . ? N1 C1 C12 120.3(2) . . ? O3 C3 N3 119.9(2) . . ? O3 C3 C32 119.8(2) . . ? N3 C3 C32 120.3(2) . . ? O11 C11 C12 121.4(2) . . ? O11 C11 C16 117.6(2) . . ? C12 C11 C16 121.0(2) . . ? C13 C12 C11 118.9(2) . . ? C13 C12 C1 122.3(2) . . ? C11 C12 C1 118.8(2) . . ? C14 C13 C12 121.8(3) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C15 C14 C13 117.0(2) . . ? C15 C14 C21 122.5(2) . . ? C13 C14 C21 120.6(3) . . ? C14 C15 C16 124.8(2) . . ? C14 C15 H15 117.6 . . ? C16 C15 H15 117.6 . . ? C15 C16 C11 116.6(3) . . ? C15 C16 C25 122.3(2) . . ? C11 C16 C25 121.1(2) . . ? C53 C17 N1 109.7(8) . . ? N1 C17 C19 113.1(3) . . ? C53 C17 C51 107.3(10) . . ? N1 C17 C51 115.5(7) . . ? N1 C17 C18 106.1(4) . . ? C19 C17 C18 111.0(4) . . ? N1 C17 C20 106.6(3) . . ? C19 C17 C20 108.9(4) . . ? C18 C17 C20 111.0(4) . . ? C53 C17 C52 109.8(11) . . ? N1 C17 C52 106.4(8) . . ? C51 C17 C52 108.2(9) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C24 109.3(3) . . ? C22 C21 C23 108.7(4) . . ? C24 C21 C23 107.7(4) . . ? C22 C21 C14 110.7(3) . . ? C24 C21 C14 112.0(3) . . ? C23 C21 C14 108.3(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C28 107.8(3) . . ? C26 C25 C27 107.5(3) . . ? C28 C25 C27 110.4(3) . . ? C26 C25 C16 111.4(3) . . ? C28 C25 C16 109.3(3) . . ? C27 C25 C16 110.3(3) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O31 C31 C36 118.1(2) . . ? O31 C31 C32 120.9(2) . . ? C36 C31 C32 121.0(2) . . ? C33 C32 C31 118.8(2) . . ? C33 C32 C3 122.1(2) . . ? C31 C32 C3 119.1(2) . . ? C34 C33 C32 121.8(2) . . ? C34 C33 H33 119.1 . . ? C32 C33 H33 119.1 . . ? C33 C34 C35 117.4(2) . . ? C33 C34 C41 120.9(2) . . ? C35 C34 C41 121.7(2) . . ? C34 C35 C36 124.0(2) . . ? C34 C35 H35 118.0 . . ? C36 C35 H35 118.0 . . ? C35 C36 C31 117.0(2) . . ? C35 C36 C45 122.4(2) . . ? C31 C36 C45 120.6(2) . . ? N3 C37 C54 106.7(5) . . ? N3 C37 C40 107.3(4) . . ? N3 C37 C55 115.7(5) . . ? C54 C37 C55 112.3(7) . . ? N3 C37 C38 112.8(4) . . ? C40 C37 C38 107.2(6) . . ? N3 C37 C39 104.5(6) . . ? C40 C37 C39 112.9(7) . . ? C38 C37 C39 112.1(6) . . ? N3 C37 C56 107.2(5) . . ? C54 C37 C56 107.6(7) . . ? C55 C37 C56 107.1(8) . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C37 C39 H39A 109.5 . . ? C37 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C37 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C42 C41 C43 110.7(4) . . ? C42 C41 C44 108.2(3) . . ? C43 C41 C44 107.7(3) . . ? C42 C41 C34 108.4(2) . . ? C43 C41 C34 109.2(3) . . ? C44 C41 C34 112.6(3) . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C41 C43 H43A 109.5 . . ? C41 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C41 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C41 C44 H44A 109.5 . . ? C41 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C41 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C46 C45 C47 107.4(3) . . ? C46 C45 C48 107.4(3) . . ? C47 C45 C48 110.1(3) . . ? C46 C45 C36 111.1(3) . . ? C47 C45 C36 109.9(2) . . ? C48 C45 C36 110.8(2) . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C45 C47 H47A 109.5 . . ? C45 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C45 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C45 C48 H48A 109.5 . . ? C45 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C45 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C17 C51 H51A 109.5 . . ? C17 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C17 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C17 C52 H52A 109.5 . . ? C17 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C17 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C17 C53 H53A 109.5 . . ? C17 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C17 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C37 C54 H54A 109.5 . . ? C37 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C37 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C37 C55 H55A 109.5 . . ? C37 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C37 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C37 C56 H56A 109.5 . . ? C37 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C37 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 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 C17 N1 C1 O1 1.4(4) . . . . ? C17 N1 C1 C12 -178.1(2) . . . . ? C37 N3 C3 O3 -0.3(4) . . . . ? C37 N3 C3 C32 179.9(2) . . . . ? O11 C11 C12 C13 -179.6(2) . . . . ? C16 C11 C12 C13 0.7(4) . . . . ? O11 C11 C12 C1 -1.3(4) . . . . ? C16 C11 C12 C1 179.1(2) . . . . ? O1 C1 C12 C13 171.3(3) . . . . ? N1 C1 C12 C13 -9.3(4) . . . . ? O1 C1 C12 C11 -7.0(4) . . . . ? N1 C1 C12 C11 172.5(2) . . . . ? C11 C12 C13 C14 -0.7(4) . . . . ? C1 C12 C13 C14 -179.0(3) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? C12 C13 C14 C21 179.7(3) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? C21 C14 C15 C16 -179.2(3) . . . . ? C14 C15 C16 C11 -0.3(4) . . . . ? C14 C15 C16 C25 178.9(3) . . . . ? O11 C11 C16 C15 -180.0(2) . . . . ? C12 C11 C16 C15 -0.3(4) . . . . ? O11 C11 C16 C25 0.8(4) . . . . ? C12 C11 C16 C25 -179.5(3) . . . . ? C1 N1 C17 C53 165.8(13) . . . . ? C1 N1 C17 C19 -45.1(6) . . . . ? C1 N1 C17 C51 44.5(14) . . . . ? C1 N1 C17 C18 76.7(5) . . . . ? C1 N1 C17 C20 -164.8(5) . . . . ? C1 N1 C17 C52 -75.6(12) . . . . ? C15 C14 C21 C22 123.9(4) . . . . ? C13 C14 C21 C22 -55.7(4) . . . . ? C15 C14 C21 C24 1.5(5) . . . . ? C13 C14 C21 C24 -178.0(3) . . . . ? C15 C14 C21 C23 -117.1(4) . . . . ? C13 C14 C21 C23 63.4(4) . . . . ? C15 C16 C25 C26 2.5(4) . . . . ? C11 C16 C25 C26 -178.3(3) . . . . ? C15 C16 C25 C28 -116.5(3) . . . . ? C11 C16 C25 C28 62.6(4) . . . . ? C15 C16 C25 C27 121.9(3) . . . . ? C11 C16 C25 C27 -59.0(4) . . . . ? O31 C31 C32 C33 179.6(2) . . . . ? C36 C31 C32 C33 0.1(4) . . . . ? O31 C31 C32 C3 0.2(4) . . . . ? C36 C31 C32 C3 -179.2(2) . . . . ? O3 C3 C32 C33 -168.3(3) . . . . ? N3 C3 C32 C33 11.5(4) . . . . ? O3 C3 C32 C31 11.1(4) . . . . ? N3 C3 C32 C31 -169.2(2) . . . . ? C31 C32 C33 C34 -0.3(4) . . . . ? C3 C32 C33 C34 179.0(2) . . . . ? C32 C33 C34 C35 0.6(4) . . . . ? C32 C33 C34 C41 -179.3(2) . . . . ? C33 C34 C35 C36 -0.9(4) . . . . ? C41 C34 C35 C36 179.1(2) . . . . ? C34 C35 C36 C31 0.7(4) . . . . ? C34 C35 C36 C45 -178.9(2) . . . . ? O31 C31 C36 C35 -179.8(2) . . . . ? C32 C31 C36 C35 -0.3(4) . . . . ? O31 C31 C36 C45 -0.1(4) . . . . ? C32 C31 C36 C45 179.3(2) . . . . ? C3 N3 C37 C54 78.9(8) . . . . ? C3 N3 C37 C40 161.1(7) . . . . ? C3 N3 C37 C55 -46.7(10) . . . . ? C3 N3 C37 C38 43.3(7) . . . . ? C3 N3 C37 C39 -78.7(7) . . . . ? C3 N3 C37 C56 -166.1(8) . . . . ? C33 C34 C41 C42 -62.2(4) . . . . ? C35 C34 C41 C42 117.8(4) . . . . ? C33 C34 C41 C43 58.5(4) . . . . ? C35 C34 C41 C43 -121.5(3) . . . . ? C33 C34 C41 C44 178.1(3) . . . . ? C35 C34 C41 C44 -1.9(4) . . . . ? C35 C36 C45 C46 -0.7(4) . . . . ? C31 C36 C45 C46 179.7(3) . . . . ? C35 C36 C45 C47 118.1(3) . . . . ? C31 C36 C45 C47 -61.6(3) . . . . ? C35 C36 C45 C48 -120.0(3) . . . . ? C31 C36 C45 C48 60.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.568 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.057 #===END data_1'OH _database_code_depnum_ccdc_archive 'CCDC 259698' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H15 N O2' _chemical_formula_sum 'C11 H15 N O2' _chemical_formula_weight 193.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.266(6) _cell_length_b 12.599(4) _cell_length_c 19.587(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.86(2) _cell_angle_gamma 90.00 _cell_volume 3457.3(18) _cell_formula_units_Z 12 _cell_measurement_temperature 298 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14.3 _cell_measurement_theta_max 15.0 _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.500 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.114 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.077 _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 298 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.31 _diffrn_reflns_number 7518 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7197 _reflns_number_gt 2741 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'teXsan Ver. 1.11' _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^)+(0.0649P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7197 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1816 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1588 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _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 -0.03799(13) 0.40434(13) 0.29590(10) 0.0784(5) Uani 1 1 d . . . O2 O 0.27407(13) 0.96144(14) 0.50872(11) 0.0955(6) Uani 1 1 d . . . O3 O 0.57364(13) 0.53949(14) 0.42353(10) 0.0899(6) Uani 1 1 d . . . O11 O 0.00809(14) 0.71444(13) 0.23944(10) 0.0810(5) Uani 1 1 d . . . H11 H 0.0245 0.7714 0.2252 0.097 Uiso 1 1 calc R . . O21 O 0.35058(13) 0.64918(12) 0.55956(11) 0.0863(6) Uani 1 1 d . . . H21 H 0.3770 0.5913 0.5665 0.104 Uiso 1 1 calc R . . O31 O 0.67190(15) 0.84955(12) 0.44465(11) 0.0880(6) Uani 1 1 d . . . H31 H 0.6879 0.9083 0.4607 0.106 Uiso 1 1 calc R . . N1 N -0.09132(14) 0.57169(15) 0.28985(11) 0.0658(6) Uani 1 1 d . . . H1 H -0.0800 0.6354 0.2778 0.079 Uiso 1 1 calc R . . N2 N 0.22853(14) 0.79243(16) 0.49564(10) 0.0697(6) Uani 1 1 d . . . H2 H 0.2451 0.7280 0.5063 0.084 Uiso 1 1 calc R . . N3 N 0.53827(14) 0.70719(16) 0.39572(11) 0.0743(6) Uani 1 1 d . . . H3 H 0.5544 0.7722 0.4048 0.089 Uiso 1 1 calc R . . C11 C 0.06879(18) 0.63681(19) 0.22650(12) 0.0585(6) Uani 1 1 d . . . C12 C 0.05153(16) 0.53296(18) 0.24521(12) 0.0565(6) Uani 1 1 d . . . C13 C 0.11424(19) 0.4549(2) 0.23152(13) 0.0740(7) Uani 1 1 d . . . H13 H 0.1045 0.3850 0.2438 0.089 Uiso 1 1 calc R . . C14 C 0.1903(2) 0.4783(2) 0.20022(16) 0.0888(9) Uani 1 1 d . . . H14 H 0.2312 0.4248 0.1912 0.107 Uiso 1 1 calc R . . C15 C 0.2054(2) 0.5819(3) 0.18228(15) 0.0858(8) Uani 1 1 d . . . H15 H 0.2570 0.5984 0.1614 0.103 Uiso 1 1 calc R . . C16 C 0.1449(2) 0.6603(2) 0.19503(14) 0.0750(8) Uani 1 1 d . . . H16 H 0.1551 0.7299 0.1824 0.090 Uiso 1 1 calc R . . C1 C -0.02974(18) 0.49816(19) 0.27892(12) 0.0598(6) Uani 1 1 d . . . C17 C -0.17732(18) 0.5566(2) 0.32040(15) 0.0739(7) Uani 1 1 d . . . C18 C -0.2475(2) 0.4851(2) 0.27451(19) 0.1128(12) Uani 1 1 d . . . H18A H -0.2638 0.5156 0.2289 0.135 Uiso 1 1 calc R . . H18B H -0.3041 0.4779 0.2940 0.135 Uiso 1 1 calc R . . H18C H -0.2192 0.4166 0.2715 0.135 Uiso 1 1 calc R . . C19 C -0.1498(2) 0.5107(2) 0.39342(17) 0.1027(10) Uani 1 1 d . . . H19A H -0.1052 0.5573 0.4216 0.123 Uiso 1 1 calc R . . H19B H -0.1209 0.4423 0.3911 0.123 Uiso 1 1 calc R . . H19C H -0.2058 0.5036 0.4135 0.123 Uiso 1 1 calc R . . C20 C -0.2195(2) 0.6678(2) 0.32303(19) 0.1031(11) Uani 1 1 d . . . H20A H -0.1744 0.7124 0.3523 0.124 Uiso 1 1 calc R . . H20B H -0.2772 0.6636 0.3414 0.124 Uiso 1 1 calc R . . H20C H -0.2334 0.6970 0.2770 0.124 Uiso 1 1 calc R . . C21 C 0.41698(17) 0.72771(18) 0.57298(12) 0.0609(6) Uani 1 1 d . . . C22 C 0.39036(17) 0.83151(18) 0.55443(12) 0.0576(6) Uani 1 1 d . . . C23 C 0.46003(19) 0.9090(2) 0.56840(15) 0.0773(8) Uani 1 1 d . . . H23 H 0.4436 0.9790 0.5568 0.093 Uiso 1 1 calc R . . C24 C 0.5524(2) 0.8862(2) 0.59866(16) 0.0879(9) Uani 1 1 d . . . H24 H 0.5981 0.9398 0.6068 0.105 Uiso 1 1 calc R . . C25 C 0.5765(2) 0.7832(2) 0.61670(14) 0.0823(8) Uani 1 1 d . . . H25 H 0.6388 0.7669 0.6379 0.099 Uiso 1 1 calc R . . C26 C 0.50984(19) 0.7044(2) 0.60378(13) 0.0726(7) Uani 1 1 d . . . H26 H 0.5271 0.6347 0.6158 0.087 Uiso 1 1 calc R . . C2 C 0.29246(19) 0.86611(19) 0.51838(13) 0.0637(7) Uani 1 1 d . . . C27 C 0.13255(19) 0.8073(2) 0.45429(15) 0.0790(8) Uani 1 1 d . . . C28 C 0.1378(3) 0.8645(3) 0.38718(18) 0.1245(13) Uani 1 1 d . . . H28A H 0.1770 0.8246 0.3616 0.149 Uiso 1 1 calc R . . H28B H 0.1649 0.9337 0.3975 0.149 Uiso 1 1 calc R . . H28C H 0.0747 0.8714 0.3598 0.149 Uiso 1 1 calc R . . C29 C 0.0713(2) 0.8675(3) 0.4955(2) 0.1395(15) Uani 1 1 d . . . H29A H 0.0976 0.9371 0.5060 0.167 Uiso 1 1 calc R . . H29B H 0.0694 0.8304 0.5379 0.167 Uiso 1 1 calc R . . H29C H 0.0078 0.8737 0.4688 0.167 Uiso 1 1 calc R . . C30 C 0.0932(2) 0.6969(3) 0.4363(2) 0.1420(16) Uani 1 1 d . . . H30A H 0.1338 0.6601 0.4103 0.170 Uiso 1 1 calc R . . H30B H 0.0301 0.7022 0.4090 0.170 Uiso 1 1 calc R . . H30C H 0.0910 0.6586 0.4784 0.170 Uiso 1 1 calc R . . C31 C 0.71539(18) 0.77310(19) 0.48880(13) 0.0678(7) Uani 1 1 d . . . C32 C 0.67738(17) 0.67040(18) 0.48388(12) 0.0591(6) Uani 1 1 d . . . C33 C 0.7235(2) 0.5950(2) 0.52999(14) 0.0762(8) Uani 1 1 d . . . H33 H 0.6993 0.5263 0.5279 0.091 Uiso 1 1 calc R . . C34 C 0.8036(2) 0.6182(3) 0.57850(16) 0.0989(10) Uani 1 1 d . . . H34 H 0.8330 0.5662 0.6088 0.119 Uiso 1 1 calc R . . C35 C 0.8393(2) 0.7188(3) 0.58149(17) 0.1036(11) Uani 1 1 d . . . H35 H 0.8938 0.7354 0.6139 0.124 Uiso 1 1 calc R . . C36 C 0.7958(2) 0.7954(2) 0.53738(16) 0.0920(9) Uani 1 1 d . . . H36 H 0.8209 0.8637 0.5402 0.110 Uiso 1 1 calc R . . C3 C 0.59228(18) 0.63473(19) 0.43235(13) 0.0617(6) Uani 1 1 d . . . C37 C 0.45358(19) 0.6902(2) 0.34109(16) 0.0797(8) Uani 1 1 d . . . C38 C 0.4802(2) 0.6246(3) 0.28235(17) 0.1261(14) Uani 1 1 d . . . H38A H 0.5017 0.5558 0.2996 0.151 Uiso 1 1 calc R . . H38B H 0.5303 0.6597 0.2646 0.151 Uiso 1 1 calc R . . H38C H 0.4254 0.6170 0.2458 0.151 Uiso 1 1 calc R . . C39 C 0.3766(2) 0.6339(3) 0.37086(18) 0.1130(12) Uani 1 1 d . . . H39A H 0.3988 0.5647 0.3870 0.136 Uiso 1 1 calc R . . H39B H 0.3204 0.6270 0.3355 0.136 Uiso 1 1 calc R . . H39C H 0.3618 0.6743 0.4090 0.136 Uiso 1 1 calc R . . C40 C 0.4199(3) 0.7978(3) 0.3153(3) 0.188(2) Uani 1 1 d . . . H40A H 0.4693 0.8328 0.2966 0.226 Uiso 1 1 calc R . . H40B H 0.4049 0.8389 0.3530 0.226 Uiso 1 1 calc R . . H40C H 0.3640 0.7909 0.2796 0.226 Uiso 1 1 calc R . . 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 0.0924(13) 0.0464(10) 0.1035(14) -0.0024(9) 0.0368(11) -0.0028(10) O2 0.0918(14) 0.0486(11) 0.1315(17) 0.0008(11) -0.0167(12) 0.0015(10) O3 0.0930(14) 0.0479(11) 0.1159(16) 0.0059(10) -0.0128(11) 0.0010(10) O11 0.0880(13) 0.0530(10) 0.1070(15) 0.0105(10) 0.0311(11) -0.0003(10) O21 0.0746(12) 0.0502(10) 0.1239(16) 0.0119(11) -0.0072(11) -0.0041(9) O31 0.0983(14) 0.0465(10) 0.1070(15) 0.0078(10) -0.0118(12) -0.0005(10) N1 0.0661(13) 0.0499(12) 0.0848(15) -0.0060(10) 0.0229(11) -0.0017(11) N2 0.0690(14) 0.0489(11) 0.0827(14) 0.0038(10) -0.0070(11) -0.0041(11) N3 0.0702(14) 0.0523(12) 0.0912(16) 0.0048(11) -0.0085(12) 0.0077(11) C11 0.0640(16) 0.0540(15) 0.0565(15) -0.0013(12) 0.0083(13) 0.0007(13) C12 0.0583(15) 0.0546(14) 0.0552(14) -0.0073(11) 0.0073(12) -0.0006(12) C13 0.0764(18) 0.0650(16) 0.0840(19) -0.0027(14) 0.0242(15) -0.0005(15) C14 0.083(2) 0.084(2) 0.107(2) -0.0035(18) 0.0365(19) 0.0128(17) C15 0.0766(19) 0.103(2) 0.084(2) 0.0067(18) 0.0289(16) -0.0059(19) C16 0.080(2) 0.0711(18) 0.0754(19) 0.0101(15) 0.0191(16) -0.0057(16) C1 0.0656(16) 0.0498(14) 0.0625(15) -0.0098(12) 0.0082(13) -0.0036(13) C17 0.0648(17) 0.0634(16) 0.098(2) -0.0147(15) 0.0269(16) -0.0073(14) C18 0.0677(19) 0.111(3) 0.158(3) -0.042(2) 0.016(2) -0.0196(18) C19 0.111(3) 0.100(2) 0.109(3) -0.0008(19) 0.051(2) -0.0111(19) C20 0.092(2) 0.082(2) 0.147(3) -0.0120(19) 0.052(2) 0.0080(18) C21 0.0633(17) 0.0541(15) 0.0637(16) -0.0023(12) 0.0083(13) -0.0031(13) C22 0.0617(15) 0.0504(14) 0.0594(15) -0.0040(11) 0.0081(12) -0.0015(12) C23 0.0694(18) 0.0558(15) 0.103(2) -0.0049(15) 0.0072(16) -0.0045(14) C24 0.071(2) 0.073(2) 0.116(3) -0.0161(17) 0.0089(18) -0.0127(16) C25 0.0632(18) 0.089(2) 0.090(2) -0.0143(17) 0.0034(15) 0.0035(17) C26 0.0692(18) 0.0660(16) 0.0804(18) -0.0022(14) 0.0087(15) 0.0051(15) C2 0.0727(18) 0.0484(15) 0.0675(16) -0.0024(12) 0.0068(13) -0.0036(13) C27 0.0699(19) 0.0712(18) 0.085(2) 0.0036(16) -0.0127(16) -0.0008(15) C28 0.130(3) 0.130(3) 0.096(2) 0.023(2) -0.022(2) 0.000(2) C29 0.073(2) 0.203(4) 0.134(3) -0.031(3) -0.001(2) 0.015(3) C30 0.111(3) 0.100(3) 0.183(4) 0.011(3) -0.057(3) -0.034(2) C31 0.0694(17) 0.0527(16) 0.0776(18) -0.0029(13) 0.0044(14) 0.0058(13) C32 0.0671(16) 0.0484(14) 0.0601(15) 0.0023(11) 0.0081(13) 0.0091(12) C33 0.092(2) 0.0614(16) 0.0707(17) 0.0047(14) 0.0039(16) 0.0131(15) C34 0.116(3) 0.081(2) 0.084(2) 0.0063(17) -0.021(2) 0.0233(19) C35 0.098(2) 0.092(2) 0.102(2) -0.013(2) -0.0301(19) 0.010(2) C36 0.089(2) 0.0696(18) 0.106(2) -0.0075(18) -0.0113(19) -0.0019(17) C3 0.0678(17) 0.0480(14) 0.0695(16) 0.0047(12) 0.0132(14) 0.0066(13) C37 0.0639(17) 0.0727(18) 0.095(2) 0.0079(16) -0.0047(16) 0.0045(14) C38 0.091(2) 0.206(4) 0.077(2) -0.004(2) 0.0054(18) 0.002(3) C39 0.068(2) 0.151(3) 0.118(3) -0.010(2) 0.013(2) -0.002(2) C40 0.152(4) 0.102(3) 0.257(6) 0.055(3) -0.099(4) 0.013(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 C1 1.239(3) . ? O2 C2 1.236(3) . ? O3 C3 1.234(3) . ? O11 C11 1.361(3) . ? O11 H11 0.8200 . ? O21 C21 1.361(3) . ? O21 H21 0.8200 . ? O31 C31 1.363(3) . ? O31 H31 0.8200 . ? N1 C1 1.322(3) . ? N1 C17 1.475(3) . ? N1 H1 0.8600 . ? N2 C2 1.319(3) . ? N2 C27 1.466(3) . ? N2 H2 0.8600 . ? N3 C3 1.317(3) . ? N3 C37 1.471(3) . ? N3 H3 0.8600 . ? C11 C16 1.378(3) . ? C11 C12 1.393(3) . ? C12 C13 1.389(3) . ? C12 C1 1.504(3) . ? C13 C14 1.375(4) . ? C13 H13 0.9300 . ? C14 C15 1.379(4) . ? C14 H14 0.9300 . ? C15 C16 1.366(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.511(4) . ? C17 C19 1.524(4) . ? C17 C20 1.529(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C26 1.380(3) . ? C21 C22 1.391(3) . ? C22 C23 1.383(3) . ? C22 C2 1.506(3) . ? C23 C24 1.370(4) . ? C23 H23 0.9300 . ? C24 C25 1.372(4) . ? C24 H24 0.9300 . ? C25 C26 1.366(4) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C29 1.501(4) . ? C27 C28 1.513(4) . ? C27 C30 1.516(4) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 C36 1.374(4) . ? C31 C32 1.399(3) . ? C32 C33 1.388(3) . ? C32 C3 1.494(3) . ? C33 C34 1.373(4) . ? C33 H33 0.9300 . ? C34 C35 1.363(4) . ? C34 H34 0.9300 . ? C35 C36 1.364(4) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 C40 1.495(4) . ? C37 C39 1.513(4) . ? C37 C38 1.521(4) . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O11 H11 109.5 . . ? C21 O21 H21 109.5 . . ? C31 O31 H31 109.5 . . ? C1 N1 C17 127.2(2) . . ? C1 N1 H1 116.4 . . ? C17 N1 H1 116.4 . . ? C2 N2 C27 127.7(2) . . ? C2 N2 H2 116.2 . . ? C27 N2 H2 116.2 . . ? C3 N3 C37 127.7(2) . . ? C3 N3 H3 116.2 . . ? C37 N3 H3 116.2 . . ? O11 C11 C16 120.8(2) . . ? O11 C11 C12 118.4(2) . . ? C16 C11 C12 120.8(2) . . ? C13 C12 C11 117.5(2) . . ? C13 C12 C1 117.1(2) . . ? C11 C12 C1 125.3(2) . . ? C14 C13 C12 121.6(3) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 119.4(3) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 120.2(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 120.3(3) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? O1 C1 N1 121.7(2) . . ? O1 C1 C12 121.1(2) . . ? N1 C1 C12 117.2(2) . . ? N1 C17 C18 110.1(2) . . ? N1 C17 C19 110.0(2) . . ? C18 C17 C19 110.9(3) . . ? N1 C17 C20 105.0(2) . . ? C18 C17 C20 110.2(2) . . ? C19 C17 C20 110.5(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O21 C21 C26 120.4(2) . . ? O21 C21 C22 119.2(2) . . ? C26 C21 C22 120.5(2) . . ? C23 C22 C21 117.5(2) . . ? C23 C22 C2 117.2(2) . . ? C21 C22 C2 125.3(2) . . ? C24 C23 C22 122.4(3) . . ? C24 C23 H23 118.8 . . ? C22 C23 H23 118.8 . . ? C23 C24 C25 118.9(3) . . ? C23 C24 H24 120.6 . . ? C25 C24 H24 120.6 . . ? C26 C25 C24 120.6(3) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C21 120.2(3) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? O2 C2 N2 121.3(2) . . ? O2 C2 C22 120.3(2) . . ? N2 C2 C22 118.4(2) . . ? N2 C27 C29 110.2(2) . . ? N2 C27 C28 110.3(3) . . ? C29 C27 C28 110.8(3) . . ? N2 C27 C30 106.1(2) . . ? C29 C27 C30 111.2(3) . . ? C28 C27 C30 108.2(3) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O31 C31 C36 121.0(2) . . ? O31 C31 C32 119.0(2) . . ? C36 C31 C32 119.9(2) . . ? C33 C32 C31 117.2(2) . . ? C33 C32 C3 117.3(2) . . ? C31 C32 C3 125.4(2) . . ? C34 C33 C32 122.4(3) . . ? C34 C33 H33 118.8 . . ? C32 C33 H33 118.8 . . ? C35 C34 C33 118.9(3) . . ? C35 C34 H34 120.6 . . ? C33 C34 H34 120.6 . . ? C34 C35 C36 120.6(3) . . ? C34 C35 H35 119.7 . . ? C36 C35 H35 119.7 . . ? C35 C36 C31 121.0(3) . . ? C35 C36 H36 119.5 . . ? C31 C36 H36 119.5 . . ? O3 C3 N3 120.6(2) . . ? O3 C3 C32 120.9(2) . . ? N3 C3 C32 118.5(2) . . ? N3 C37 C40 106.3(2) . . ? N3 C37 C39 110.1(2) . . ? C40 C37 C39 110.2(3) . . ? N3 C37 C38 110.0(2) . . ? C40 C37 C38 110.3(3) . . ? C39 C37 C38 109.9(3) . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C37 C39 H39A 109.5 . . ? C37 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C37 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 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 O11 C11 C12 C13 179.9(2) . . . . ? C16 C11 C12 C13 0.6(3) . . . . ? O11 C11 C12 C1 0.1(3) . . . . ? C16 C11 C12 C1 -179.2(2) . . . . ? C11 C12 C13 C14 -0.5(4) . . . . ? C1 C12 C13 C14 179.4(2) . . . . ? C12 C13 C14 C15 0.4(4) . . . . ? C13 C14 C15 C16 -0.5(4) . . . . ? C14 C15 C16 C11 0.6(4) . . . . ? O11 C11 C16 C15 180.0(2) . . . . ? C12 C11 C16 C15 -0.7(4) . . . . ? C17 N1 C1 O1 -1.8(4) . . . . ? C17 N1 C1 C12 178.5(2) . . . . ? C13 C12 C1 O1 2.5(3) . . . . ? C11 C12 C1 O1 -177.6(2) . . . . ? C13 C12 C1 N1 -177.8(2) . . . . ? C11 C12 C1 N1 2.1(3) . . . . ? C1 N1 C17 C18 -63.3(3) . . . . ? C1 N1 C17 C19 59.3(3) . . . . ? C1 N1 C17 C20 178.1(2) . . . . ? O21 C21 C22 C23 -179.5(2) . . . . ? C26 C21 C22 C23 -0.3(4) . . . . ? O21 C21 C22 C2 -1.4(4) . . . . ? C26 C21 C22 C2 177.7(2) . . . . ? C21 C22 C23 C24 0.7(4) . . . . ? C2 C22 C23 C24 -177.6(3) . . . . ? C22 C23 C24 C25 -1.0(5) . . . . ? C23 C24 C25 C26 1.0(4) . . . . ? C24 C25 C26 C21 -0.7(4) . . . . ? O21 C21 C26 C25 179.5(2) . . . . ? C22 C21 C26 C25 0.3(4) . . . . ? C27 N2 C2 O2 3.5(4) . . . . ? C27 N2 C2 C22 -174.3(2) . . . . ? C23 C22 C2 O2 -7.3(4) . . . . ? C21 C22 C2 O2 174.6(3) . . . . ? C23 C22 C2 N2 170.5(2) . . . . ? C21 C22 C2 N2 -7.5(4) . . . . ? C2 N2 C27 C29 -65.1(4) . . . . ? C2 N2 C27 C28 57.6(4) . . . . ? C2 N2 C27 C30 174.5(3) . . . . ? O31 C31 C32 C33 -179.7(2) . . . . ? C36 C31 C32 C33 0.7(4) . . . . ? O31 C31 C32 C3 1.4(4) . . . . ? C36 C31 C32 C3 -178.2(3) . . . . ? C31 C32 C33 C34 -0.5(4) . . . . ? C3 C32 C33 C34 178.5(3) . . . . ? C32 C33 C34 C35 -0.1(5) . . . . ? C33 C34 C35 C36 0.5(5) . . . . ? C34 C35 C36 C31 -0.3(5) . . . . ? O31 C31 C36 C35 -179.9(3) . . . . ? C32 C31 C36 C35 -0.3(5) . . . . ? C37 N3 C3 O3 -1.1(4) . . . . ? C37 N3 C3 C32 177.9(2) . . . . ? C33 C32 C3 O3 -11.8(4) . . . . ? C31 C32 C3 O3 167.1(3) . . . . ? C33 C32 C3 N3 169.2(2) . . . . ? C31 C32 C3 N3 -11.9(4) . . . . ? C3 N3 C37 C40 -179.0(3) . . . . ? C3 N3 C37 C39 61.7(4) . . . . ? C3 N3 C37 C38 -59.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.168 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.033 #===END data_1'ONEt4 _database_code_depnum_ccdc_archive 'CCDC 259699' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 N O2, C8 H20 N, H2 O' _chemical_formula_sum 'C19 H36 N2 O3' _chemical_formula_weight 340.50 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 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0678(16) _cell_length_b 12.211(3) _cell_length_c 9.0829(12) _cell_angle_alpha 97.147(15) _cell_angle_beta 92.285(15) _cell_angle_gamma 109.753(14) _cell_volume 1038.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298 _cell_measurement_reflns_used 9 _cell_measurement_theta_min 13.1 _cell_measurement_theta_max 13.7 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.500 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.089 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.073 _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 298 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.53 _diffrn_reflns_number 5729 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.2334 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4752 _reflns_number_gt 1179 _reflns_threshold_expression >2sigma(I) _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution MULTAN88 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'teXsan Ver. 1.11' _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^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4752 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3179 _refine_ls_R_factor_gt 0.0688 _refine_ls_wR_factor_ref 0.2319 _refine_ls_wR_factor_gt 0.1691 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 O11 O 0.3893(2) 0.3755(2) 0.7916(3) 0.0593(8) Uani 1 1 d . . . O1 O -0.0119(3) 0.1119(2) 0.7047(3) 0.0829(10) Uani 1 1 d . . . O100 O 0.3411(3) 0.5125(2) 1.0420(3) 0.0850(10) Uani 1 1 d . . . N1 N 0.1076(3) 0.3059(3) 0.7266(3) 0.0543(9) Uani 1 1 d . . . H1 H 0.1906 0.3583 0.7309 0.065 Uiso 1 1 calc R . . N21 N 0.3178(4) 0.2147(3) 0.2154(4) 0.0677(10) Uani 1 1 d . . . C11 C 0.3731(4) 0.2667(4) 0.7449(4) 0.0491(10) Uani 1 1 d . . . C12 C 0.2390(4) 0.1748(3) 0.7057(4) 0.0473(10) Uani 1 1 d . . . C13 C 0.2319(5) 0.0606(4) 0.6528(4) 0.0621(12) Uani 1 1 d . . . H13 H 0.1439 0.0019 0.6279 0.075 Uiso 1 1 calc R . . C14 C 0.3530(6) 0.0334(4) 0.6370(5) 0.0754(14) Uani 1 1 d . . . H14 H 0.3467 -0.0431 0.6010 0.091 Uiso 1 1 calc R . . C15 C 0.4836(5) 0.1199(5) 0.6747(5) 0.0795(14) Uani 1 1 d . . . H15 H 0.5655 0.1016 0.6639 0.095 Uiso 1 1 calc R . . C16 C 0.4937(5) 0.2321(4) 0.7277(4) 0.0667(12) Uani 1 1 d . . . H16 H 0.5832 0.2884 0.7538 0.080 Uiso 1 1 calc R . . C1 C 0.1018(4) 0.1940(4) 0.7141(4) 0.0510(10) Uani 1 1 d . . . C17 C -0.0118(4) 0.3497(3) 0.7339(5) 0.0607(11) Uani 1 1 d . . . C18 C -0.1115(5) 0.2982(4) 0.5929(5) 0.0901(16) Uani 1 1 d . . . H18A H -0.0603 0.3187 0.5076 0.108 Uiso 1 1 calc R . . H18B H -0.1873 0.3293 0.5956 0.108 Uiso 1 1 calc R . . H18C H -0.1498 0.2142 0.5865 0.108 Uiso 1 1 calc R . . C19 C 0.0525(5) 0.4822(4) 0.7431(6) 0.0943(16) Uani 1 1 d . . . H19A H 0.1015 0.5012 0.6561 0.113 Uiso 1 1 calc R . . H19B H 0.1180 0.5137 0.8303 0.113 Uiso 1 1 calc R . . H19C H -0.0212 0.5155 0.7487 0.113 Uiso 1 1 calc R . . C20 C -0.0893(5) 0.3193(4) 0.8694(5) 0.0913(16) Uani 1 1 d . . . H20A H -0.0248 0.3523 0.9572 0.110 Uiso 1 1 calc R . . H20B H -0.1280 0.2354 0.8643 0.110 Uiso 1 1 calc R . . H20C H -0.1647 0.3509 0.8733 0.110 Uiso 1 1 calc R . . C21 C 0.2033(5) 0.2215(4) 0.1130(6) 0.1031(17) Uani 1 1 d . . . H21A H 0.2070 0.1815 0.0149 0.124 Uiso 1 1 calc R . . H21B H 0.2199 0.3034 0.1045 0.124 Uiso 1 1 calc R . . C22 C 0.0530(5) 0.1662(5) 0.1647(7) 0.134(2) Uani 1 1 d . . . H22A H -0.0162 0.1733 0.0943 0.161 Uiso 1 1 calc R . . H22B H 0.0476 0.2065 0.2608 0.161 Uiso 1 1 calc R . . H22C H 0.0348 0.0846 0.1710 0.161 Uiso 1 1 calc R . . C23 C 0.3155(8) 0.2609(6) 0.3704(6) 0.138(3) Uani 1 1 d . . . H23A H 0.3967 0.2571 0.4280 0.165 Uiso 1 1 calc R . . H23B H 0.2307 0.2119 0.4089 0.165 Uiso 1 1 calc R . . C24 C 0.3189(7) 0.3965(6) 0.3917(6) 0.144(3) Uani 1 1 d . . . H24A H 0.3174 0.4232 0.4954 0.173 Uiso 1 1 calc R . . H24B H 0.2376 0.4005 0.3367 0.173 Uiso 1 1 calc R . . H24C H 0.4037 0.4457 0.3554 0.173 Uiso 1 1 calc R . . C25 C 0.4544(5) 0.2800(4) 0.1536(6) 0.1009(17) Uani 1 1 d . . . H25A H 0.4620 0.3616 0.1559 0.121 Uiso 1 1 calc R . . H25B H 0.4514 0.2467 0.0503 0.121 Uiso 1 1 calc R . . C26 C 0.5868(6) 0.2756(6) 0.2391(9) 0.162(3) Uani 1 1 d . . . H26A H 0.6698 0.3188 0.1947 0.194 Uiso 1 1 calc R . . H26B H 0.5814 0.1953 0.2352 0.194 Uiso 1 1 calc R . . H26C H 0.5918 0.3101 0.3411 0.194 Uiso 1 1 calc R . . C27 C 0.3081(6) 0.0835(5) 0.2142(7) 0.1074(19) Uani 1 1 d . . . H27A H 0.3840 0.0818 0.2821 0.129 Uiso 1 1 calc R . . H27B H 0.2191 0.0404 0.2509 0.129 Uiso 1 1 calc R . . C28 C 0.3177(7) 0.0234(5) 0.0647(7) 0.132(2) Uani 1 1 d . . . H28A H 0.3111 -0.0561 0.0715 0.159 Uiso 1 1 calc R . . H28B H 0.4067 0.0643 0.0285 0.159 Uiso 1 1 calc R . . H28C H 0.2416 0.0230 -0.0027 0.159 Uiso 1 1 calc R . . 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 O11 0.0438(16) 0.0593(19) 0.0654(19) -0.0070(15) -0.0024(13) 0.0123(14) O1 0.0539(19) 0.0589(19) 0.121(3) 0.0081(18) 0.0224(18) 0.0008(16) O100 0.066(2) 0.085(2) 0.099(2) -0.0077(17) 0.0010(16) 0.0282(17) N1 0.0352(19) 0.052(2) 0.073(2) 0.0088(17) 0.0062(16) 0.0105(16) N21 0.063(2) 0.071(2) 0.059(2) 0.032(2) 0.0017(19) 0.0019(19) C11 0.052(3) 0.067(3) 0.030(2) 0.001(2) 0.0004(18) 0.025(2) C12 0.054(3) 0.049(3) 0.039(2) 0.006(2) 0.0057(19) 0.019(2) C13 0.070(3) 0.056(3) 0.059(3) 0.007(2) 0.014(2) 0.019(2) C14 0.096(4) 0.068(3) 0.072(3) -0.003(3) 0.010(3) 0.045(3) C15 0.081(4) 0.099(4) 0.074(3) -0.004(3) 0.004(3) 0.058(4) C16 0.061(3) 0.086(4) 0.056(3) -0.009(2) -0.005(2) 0.037(3) C1 0.049(3) 0.051(3) 0.052(3) 0.008(2) 0.012(2) 0.014(2) C17 0.046(2) 0.061(3) 0.076(3) 0.008(2) 0.000(2) 0.021(2) C18 0.068(3) 0.114(4) 0.086(4) 0.004(3) -0.018(3) 0.036(3) C19 0.079(3) 0.076(4) 0.136(5) 0.018(3) 0.002(3) 0.038(3) C20 0.080(3) 0.120(4) 0.089(4) 0.012(3) 0.019(3) 0.053(3) C21 0.094(4) 0.104(4) 0.100(4) 0.043(3) -0.012(3) 0.012(3) C22 0.071(4) 0.130(5) 0.191(6) 0.074(5) 0.000(4) 0.005(3) C23 0.192(7) 0.140(6) 0.056(4) 0.027(4) 0.016(4) 0.019(5) C24 0.174(7) 0.153(6) 0.075(4) -0.013(4) 0.023(4) 0.028(5) C25 0.090(4) 0.101(4) 0.106(4) 0.040(3) 0.025(3) 0.016(3) C26 0.063(4) 0.147(6) 0.260(9) 0.076(5) -0.018(5) 0.005(4) C27 0.089(4) 0.106(4) 0.118(5) 0.059(4) -0.001(4) 0.008(3) C28 0.166(7) 0.101(5) 0.117(5) 0.012(4) 0.010(5) 0.031(4) _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 O11 C11 1.295(4) . ? O1 C1 1.232(4) . ? N1 C1 1.338(4) . ? N1 C17 1.472(5) . ? N1 H1 0.8600 . ? N21 C23 1.454(6) . ? N21 C21 1.484(5) . ? N21 C25 1.508(5) . ? N21 C27 1.570(6) . ? C11 C16 1.423(5) . ? C11 C12 1.431(5) . ? C12 C13 1.394(5) . ? C12 C1 1.481(5) . ? C13 C14 1.376(6) . ? C13 H13 0.9300 . ? C14 C15 1.377(6) . ? C14 H14 0.9300 . ? C15 C16 1.363(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C20 1.502(6) . ? C17 C19 1.515(5) . ? C17 C18 1.521(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.552(7) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.632(7) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.535(7) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.485(7) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C17 127.5(3) . . ? C1 N1 H1 116.2 . . ? C17 N1 H1 116.2 . . ? C23 N21 C21 114.7(5) . . ? C23 N21 C25 111.6(4) . . ? C21 N21 C25 105.6(3) . . ? C23 N21 C27 105.8(4) . . ? C21 N21 C27 110.7(3) . . ? C25 N21 C27 108.4(4) . . ? O11 C11 C16 120.0(4) . . ? O11 C11 C12 124.6(4) . . ? C16 C11 C12 115.4(4) . . ? C13 C12 C11 120.6(4) . . ? C13 C12 C1 116.2(4) . . ? C11 C12 C1 123.2(3) . . ? C14 C13 C12 121.1(4) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 119.7(4) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 120.5(4) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 122.8(4) . . ? C15 C16 H16 118.6 . . ? C11 C16 H16 118.6 . . ? O1 C1 N1 121.6(4) . . ? O1 C1 C12 122.2(4) . . ? N1 C1 C12 116.1(3) . . ? N1 C17 C20 111.0(3) . . ? N1 C17 C19 106.0(3) . . ? C20 C17 C19 109.7(4) . . ? N1 C17 C18 109.4(3) . . ? C20 C17 C18 110.6(4) . . ? C19 C17 C18 110.0(4) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N21 C21 C22 113.4(4) . . ? N21 C21 H21A 108.9 . . ? C22 C21 H21A 108.9 . . ? N21 C21 H21B 108.9 . . ? C22 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N21 C23 C24 112.4(4) . . ? N21 C23 H23A 109.1 . . ? C24 C23 H23A 109.1 . . ? N21 C23 H23B 109.1 . . ? C24 C23 H23B 109.1 . . ? H23A C23 H23B 107.8 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N21 C25 C26 113.6(4) . . ? N21 C25 H25A 108.9 . . ? C26 C25 H25A 108.9 . . ? N21 C25 H25B 108.9 . . ? C26 C25 H25B 108.9 . . ? H25A C25 H25B 107.7 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 N21 113.6(4) . . ? C28 C27 H27A 108.8 . . ? N21 C27 H27A 108.8 . . ? C28 C27 H27B 108.8 . . ? N21 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 O11 C11 C12 C13 178.4(3) . . . . ? C16 C11 C12 C13 -0.9(5) . . . . ? O11 C11 C12 C1 0.1(6) . . . . ? C16 C11 C12 C1 -179.1(3) . . . . ? C11 C12 C13 C14 0.0(6) . . . . ? C1 C12 C13 C14 178.4(4) . . . . ? C12 C13 C14 C15 0.4(6) . . . . ? C13 C14 C15 C16 0.1(7) . . . . ? C14 C15 C16 C11 -1.0(7) . . . . ? O11 C11 C16 C15 -177.9(4) . . . . ? C12 C11 C16 C15 1.4(6) . . . . ? C17 N1 C1 O1 1.2(6) . . . . ? C17 N1 C1 C12 178.6(3) . . . . ? C13 C12 C1 O1 14.3(5) . . . . ? C11 C12 C1 O1 -167.4(4) . . . . ? C13 C12 C1 N1 -163.2(3) . . . . ? C11 C12 C1 N1 15.2(5) . . . . ? C1 N1 C17 C20 62.5(5) . . . . ? C1 N1 C17 C19 -178.4(4) . . . . ? C1 N1 C17 C18 -59.9(5) . . . . ? C23 N21 C21 C22 -52.6(6) . . . . ? C25 N21 C21 C22 -175.9(5) . . . . ? C27 N21 C21 C22 67.0(6) . . . . ? C21 N21 C23 C24 -55.6(6) . . . . ? C25 N21 C23 C24 64.4(6) . . . . ? C27 N21 C23 C24 -177.8(5) . . . . ? C23 N21 C25 C26 58.8(6) . . . . ? C21 N21 C25 C26 -176.0(5) . . . . ? C27 N21 C25 C26 -57.4(6) . . . . ? C23 N21 C27 C28 -176.6(5) . . . . ? C21 N21 C27 C28 58.6(6) . . . . ? C25 N21 C27 C28 -56.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.429 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.047 #===END data_2'OH _database_code_depnum_ccdc_archive 'CCDC 259700' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H24 N2 O3' _chemical_formula_sum 'C16 H24 N2 O3' _chemical_formula_weight 292.37 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 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.233(4) _cell_length_b 13.207(4) _cell_length_c 11.841(4) _cell_angle_alpha 105.46(2) _cell_angle_beta 109.07(3) _cell_angle_gamma 90.81(3) _cell_volume 1732.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used 22 _cell_measurement_theta_min 11.0 _cell_measurement_theta_max 12.3 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.078 _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 293 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.01 _diffrn_reflns_number 5813 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0940 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5561 _reflns_number_gt 2337 _reflns_threshold_expression >2sigma(I) _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'teXsan Ver. 1.11' _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^)+(0.1190P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5561 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1885 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.2267 _refine_ls_wR_factor_gt 0.1706 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.9768(3) 0.4813(2) 0.3498(3) 0.0746(9) Uani 1 1 d . . . O2 O 0.6137(3) 0.7356(2) 0.0431(3) 0.0777(9) Uani 1 1 d . . . O3 O 0.5020(3) 0.1646(2) 0.3533(3) 0.0849(10) Uani 1 1 d . . . O4 O 0.0816(3) -0.2051(2) 0.0587(3) 0.0792(9) Uani 1 1 d . . . O11 O 0.8268(2) 0.6005(2) 0.3004(2) 0.0603(7) Uani 1 1 d . . . H11 H 0.8659 0.5631 0.3397 0.072 Uiso 1 1 calc R . . O31 O 0.3375(3) 0.0337(2) 0.3131(2) 0.0664(8) Uani 1 1 d . . . H31 H 0.3913 0.0810 0.3519 0.080 Uiso 1 1 calc R . . N1 N 1.0075(3) 0.3513(2) 0.2008(3) 0.0590(9) Uani 1 1 d . . . H1 H 0.9875 0.3210 0.1220 0.071 Uiso 1 1 calc R . . N2 N 0.6430(3) 0.7043(3) 0.2262(3) 0.0670(10) Uani 1 1 d . . . H2 H 0.6829 0.6709 0.2762 0.080 Uiso 1 1 calc R . . N3 N 0.5067(3) 0.2364(2) 0.2034(3) 0.0629(9) Uani 1 1 d . . . H3 H 0.4796 0.2307 0.1249 0.075 Uiso 1 1 calc R . . N4 N 0.1548(3) -0.1046(3) 0.2576(3) 0.0698(10) Uani 1 1 d . . . H4 H 0.2054 -0.0526 0.3082 0.084 Uiso 1 1 calc R . . C1 C 0.9588(3) 0.4378(3) 0.2382(4) 0.0569(10) Uani 1 1 d . . . C2 C 0.6620(3) 0.6892(3) 0.1199(4) 0.0555(10) Uani 1 1 d . . . C3 C 0.4685(4) 0.1614(3) 0.2408(4) 0.0587(10) Uani 1 1 d . . . C4 C 0.1507(4) -0.1321(3) 0.1404(4) 0.0610(11) Uani 1 1 d . . . C11 C 0.8170(3) 0.5640(3) 0.1801(3) 0.0470(9) Uani 1 1 d . . . C12 C 0.8824(3) 0.4835(3) 0.1415(3) 0.0489(9) Uani 1 1 d . . . C13 C 0.8753(4) 0.4525(3) 0.0189(4) 0.0650(11) Uani 1 1 d . . . H13 H 0.9184 0.3992 -0.0066 0.078 Uiso 1 1 calc R . . C14 C 0.8059(4) 0.4980(3) -0.0680(4) 0.0690(12) Uani 1 1 d . . . H14 H 0.8028 0.4769 -0.1505 0.083 Uiso 1 1 calc R . . C15 C 0.7410(4) 0.5762(3) -0.0277(4) 0.0649(12) Uani 1 1 d . . . H15 H 0.6945 0.6078 -0.0852 0.078 Uiso 1 1 calc R . . C16 C 0.7423(3) 0.6091(3) 0.0929(3) 0.0487(9) Uani 1 1 d . . . C17 C 1.0946(4) 0.3040(3) 0.2871(4) 0.0680(12) Uani 1 1 d . . . C18 C 1.0369(4) 0.2598(4) 0.3620(5) 0.0879(15) Uani 1 1 d . . . H18A H 0.9727 0.2083 0.3063 0.106 Uiso 1 1 calc R . . H18B H 1.0090 0.3161 0.4119 0.106 Uiso 1 1 calc R . . H18C H 1.0923 0.2270 0.4154 0.106 Uiso 1 1 calc R . . C19 C 1.1964(4) 0.3849(4) 0.3729(5) 0.0964(17) Uani 1 1 d . . . H19A H 1.1699 0.4409 0.4247 0.116 Uiso 1 1 calc R . . H19B H 1.2307 0.4135 0.3241 0.116 Uiso 1 1 calc R . . H19C H 1.2534 0.3519 0.4245 0.116 Uiso 1 1 calc R . . C20 C 1.1345(5) 0.2144(4) 0.2040(5) 0.112(2) Uani 1 1 d . . . H20A H 1.0690 0.1636 0.1503 0.135 Uiso 1 1 calc R . . H20B H 1.1914 0.1808 0.2550 0.135 Uiso 1 1 calc R . . H20C H 1.1683 0.2422 0.1544 0.135 Uiso 1 1 calc R . . C21 C 0.5613(4) 0.7719(4) 0.2693(4) 0.0771(13) Uani 1 1 d . . . C22 C 0.4415(5) 0.7437(5) 0.1779(6) 0.123(2) Uani 1 1 d . . . H22A H 0.4396 0.7561 0.1010 0.147 Uiso 1 1 calc R . . H22B H 0.3895 0.7863 0.2103 0.147 Uiso 1 1 calc R . . H22C H 0.4176 0.6704 0.1630 0.147 Uiso 1 1 calc R . . C23 C 0.5997(6) 0.8859(4) 0.2891(6) 0.132(2) Uani 1 1 d . . . H23A H 0.6769 0.9048 0.3493 0.159 Uiso 1 1 calc R . . H23B H 0.5473 0.9298 0.3190 0.159 Uiso 1 1 calc R . . H23C H 0.5993 0.8959 0.2116 0.159 Uiso 1 1 calc R . . C24 C 0.5643(6) 0.7537(6) 0.3894(6) 0.172(4) Uani 1 1 d . . . H24A H 0.6421 0.7720 0.4485 0.207 Uiso 1 1 calc R . . H24B H 0.5401 0.6806 0.3754 0.207 Uiso 1 1 calc R . . H24C H 0.5127 0.7969 0.4217 0.207 Uiso 1 1 calc R . . C31 C 0.3175(3) 0.0132(3) 0.1895(3) 0.0499(9) Uani 1 1 d . . . C32 C 0.3824(3) 0.0735(3) 0.1474(4) 0.0534(10) Uani 1 1 d . . . C33 C 0.3641(4) 0.0469(3) 0.0215(4) 0.0704(12) Uani 1 1 d . . . H33 H 0.4080 0.0851 -0.0074 0.085 Uiso 1 1 calc R . . C34 C 0.2827(5) -0.0344(3) -0.0627(4) 0.0826(15) Uani 1 1 d . . . H34 H 0.2716 -0.0514 -0.1474 0.099 Uiso 1 1 calc R . . C35 C 0.2176(4) -0.0904(3) -0.0184(4) 0.0730(13) Uani 1 1 d . . . H35 H 0.1631 -0.1459 -0.0750 0.088 Uiso 1 1 calc R . . C36 C 0.2303(3) -0.0672(3) 0.1059(4) 0.0548(10) Uani 1 1 d . . . C37 C 0.5919(4) 0.3295(3) 0.2847(4) 0.0679(12) Uani 1 1 d . . . C38 C 0.5415(5) 0.3981(4) 0.3730(5) 0.112(2) Uani 1 1 d . . . H38A H 0.4703 0.4200 0.3267 0.134 Uiso 1 1 calc R . . H38B H 0.5958 0.4592 0.4242 0.134 Uiso 1 1 calc R . . H38C H 0.5258 0.3591 0.4249 0.134 Uiso 1 1 calc R . . C39 C 0.7042(5) 0.2931(5) 0.3521(6) 0.125(2) Uani 1 1 d . . . H39A H 0.7346 0.2504 0.2924 0.150 Uiso 1 1 calc R . . H39B H 0.6903 0.2522 0.4030 0.150 Uiso 1 1 calc R . . H39C H 0.7595 0.3534 0.4039 0.150 Uiso 1 1 calc R . . C40 C 0.6125(6) 0.3886(5) 0.1996(5) 0.137(3) Uani 1 1 d . . . H40A H 0.6464 0.3446 0.1442 0.165 Uiso 1 1 calc R . . H40B H 0.6644 0.4517 0.2485 0.165 Uiso 1 1 calc R . . H40C H 0.5397 0.4070 0.1519 0.165 Uiso 1 1 calc R . . C41 C 0.0820(4) -0.1533(4) 0.3108(5) 0.0807(14) Uani 1 1 d . . . C42 C -0.0441(5) -0.1422(6) 0.2513(6) 0.129(2) Uani 1 1 d . . . H42A H -0.0544 -0.0687 0.2624 0.155 Uiso 1 1 calc R . . H42B H -0.0894 -0.1720 0.2895 0.155 Uiso 1 1 calc R . . H42C H -0.0692 -0.1787 0.1638 0.155 Uiso 1 1 calc R . . C43 C 0.1014(6) -0.2685(4) 0.2978(5) 0.1053(18) Uani 1 1 d . . . H43A H 0.1824 -0.2735 0.3374 0.126 Uiso 1 1 calc R . . H43B H 0.0776 -0.3070 0.2110 0.126 Uiso 1 1 calc R . . H43C H 0.0564 -0.2979 0.3368 0.126 Uiso 1 1 calc R . . C44 C 0.1249(5) -0.0922(4) 0.4498(5) 0.117(2) Uani 1 1 d . . . H44A H 0.2054 -0.1006 0.4870 0.141 Uiso 1 1 calc R . . H44B H 0.0797 -0.1191 0.4904 0.141 Uiso 1 1 calc R . . H44C H 0.1164 -0.0186 0.4590 0.141 Uiso 1 1 calc R . . 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 0.083(2) 0.0726(19) 0.0531(18) 0.0093(15) 0.0104(16) 0.0311(16) O2 0.095(2) 0.0670(19) 0.083(2) 0.0364(17) 0.0322(18) 0.0369(17) O3 0.096(2) 0.083(2) 0.062(2) 0.0156(16) 0.0149(18) -0.0276(18) O4 0.086(2) 0.0599(18) 0.072(2) 0.0020(15) 0.0154(17) -0.0196(17) O11 0.0627(19) 0.0576(17) 0.0526(17) 0.0088(13) 0.0145(14) 0.0167(13) O31 0.070(2) 0.0584(18) 0.0618(18) 0.0093(13) 0.0176(15) -0.0112(14) N1 0.053(2) 0.061(2) 0.057(2) 0.0136(16) 0.0126(16) 0.0185(17) N2 0.073(2) 0.073(2) 0.067(2) 0.0272(18) 0.032(2) 0.038(2) N3 0.067(2) 0.056(2) 0.060(2) 0.0147(17) 0.0172(18) -0.0095(17) N4 0.073(2) 0.055(2) 0.074(3) -0.0011(18) 0.033(2) -0.0117(18) C1 0.047(2) 0.052(2) 0.061(3) 0.009(2) 0.010(2) 0.0060(19) C2 0.054(2) 0.049(2) 0.064(3) 0.017(2) 0.020(2) 0.0125(19) C3 0.066(3) 0.051(2) 0.057(3) 0.012(2) 0.020(2) 0.003(2) C4 0.060(3) 0.041(2) 0.075(3) 0.007(2) 0.022(2) 0.003(2) C11 0.047(2) 0.038(2) 0.050(2) 0.0039(17) 0.0171(19) -0.0030(18) C12 0.047(2) 0.044(2) 0.054(2) 0.0100(17) 0.0182(19) 0.0043(17) C13 0.063(3) 0.062(3) 0.071(3) 0.018(2) 0.025(2) 0.022(2) C14 0.084(3) 0.072(3) 0.059(3) 0.021(2) 0.032(2) 0.026(3) C15 0.070(3) 0.064(3) 0.070(3) 0.030(2) 0.026(2) 0.023(2) C16 0.052(2) 0.040(2) 0.058(3) 0.0162(18) 0.021(2) 0.0082(18) C17 0.058(3) 0.066(3) 0.075(3) 0.027(2) 0.011(2) 0.023(2) C18 0.081(4) 0.084(3) 0.090(4) 0.037(3) 0.008(3) 0.014(3) C19 0.060(3) 0.105(4) 0.108(4) 0.043(3) -0.002(3) 0.011(3) C20 0.117(5) 0.119(5) 0.106(4) 0.037(4) 0.039(4) 0.073(4) C21 0.077(3) 0.085(3) 0.072(3) 0.020(2) 0.028(3) 0.040(3) C22 0.083(4) 0.146(6) 0.132(5) 0.017(4) 0.045(4) 0.039(4) C23 0.145(6) 0.089(4) 0.144(6) -0.010(4) 0.059(5) 0.037(4) C24 0.226(9) 0.247(9) 0.125(6) 0.099(6) 0.123(6) 0.175(8) C31 0.059(2) 0.038(2) 0.047(2) 0.0072(17) 0.015(2) 0.0110(19) C32 0.060(3) 0.037(2) 0.059(3) 0.0100(18) 0.018(2) 0.0045(19) C33 0.086(3) 0.052(2) 0.066(3) 0.007(2) 0.026(3) -0.004(2) C34 0.112(4) 0.071(3) 0.050(3) 0.005(2) 0.019(3) -0.017(3) C35 0.088(3) 0.052(3) 0.066(3) 0.002(2) 0.021(3) -0.009(2) C36 0.058(2) 0.039(2) 0.059(3) 0.0090(18) 0.014(2) 0.0070(19) C37 0.058(3) 0.062(3) 0.071(3) 0.009(2) 0.015(2) -0.015(2) C38 0.099(4) 0.076(3) 0.134(5) -0.021(3) 0.047(4) -0.017(3) C39 0.064(3) 0.106(5) 0.154(6) -0.004(4) 0.005(4) -0.009(3) C40 0.150(6) 0.125(5) 0.113(5) 0.028(4) 0.023(4) -0.085(5) C41 0.079(3) 0.073(3) 0.089(3) 0.002(3) 0.045(3) -0.018(3) C42 0.085(4) 0.153(6) 0.154(6) 0.028(5) 0.060(4) -0.001(4) C43 0.142(5) 0.078(4) 0.105(4) 0.024(3) 0.057(4) -0.010(3) C44 0.148(5) 0.100(4) 0.110(4) -0.003(3) 0.080(4) -0.030(4) _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 1.235(4) . ? O2 C2 1.228(4) . ? O3 C3 1.247(4) . ? O4 C4 1.234(4) . ? O11 C11 1.341(4) . ? O11 H11 0.8200 . ? O31 C31 1.352(4) . ? O31 H31 0.8200 . ? N1 C1 1.334(5) . ? N1 C17 1.489(5) . ? N1 H1 0.8600 . ? N2 C2 1.317(5) . ? N2 C21 1.474(5) . ? N2 H2 0.8600 . ? N3 C3 1.323(5) . ? N3 C37 1.484(5) . ? N3 H3 0.8600 . ? N4 C4 1.321(5) . ? N4 C41 1.473(5) . ? N4 H4 0.8600 . ? C1 C12 1.494(5) . ? C2 C16 1.497(5) . ? C3 C32 1.483(5) . ? C4 C36 1.508(5) . ? C11 C16 1.408(5) . ? C11 C12 1.408(5) . ? C12 C13 1.373(5) . ? C13 C14 1.383(6) . ? C13 H13 0.9300 . ? C14 C15 1.391(5) . ? C14 H14 0.9300 . ? C15 C16 1.372(5) . ? C15 H15 0.9300 . ? C17 C19 1.512(6) . ? C17 C18 1.516(6) . ? C17 C20 1.522(6) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.480(7) . ? C21 C24 1.494(7) . ? C21 C23 1.504(7) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C31 C36 1.401(5) . ? C31 C32 1.402(5) . ? C32 C33 1.377(5) . ? C33 C34 1.375(6) . ? C33 H33 0.9300 . ? C34 C35 1.385(6) . ? C34 H34 0.9300 . ? C35 C36 1.376(5) . ? C35 H35 0.9300 . ? C37 C38 1.491(6) . ? C37 C39 1.504(7) . ? C37 C40 1.505(6) . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C41 C42 1.500(7) . ? C41 C43 1.518(7) . ? C41 C44 1.533(7) . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O11 H11 109.5 . . ? C31 O31 H31 109.5 . . ? C1 N1 C17 124.0(3) . . ? C1 N1 H1 118.0 . . ? C17 N1 H1 118.0 . . ? C2 N2 C21 127.5(3) . . ? C2 N2 H2 116.2 . . ? C21 N2 H2 116.2 . . ? C3 N3 C37 125.8(4) . . ? C3 N3 H3 117.1 . . ? C37 N3 H3 117.1 . . ? C4 N4 C41 127.0(4) . . ? C4 N4 H4 116.5 . . ? C41 N4 H4 116.5 . . ? O1 C1 N1 121.7(4) . . ? O1 C1 C12 119.8(3) . . ? N1 C1 C12 118.5(4) . . ? O2 C2 N2 122.3(4) . . ? O2 C2 C16 120.3(4) . . ? N2 C2 C16 117.4(3) . . ? O3 C3 N3 121.1(4) . . ? O3 C3 C32 119.6(4) . . ? N3 C3 C32 119.2(4) . . ? O4 C4 N4 122.7(4) . . ? O4 C4 C36 119.6(4) . . ? N4 C4 C36 117.6(4) . . ? O11 C11 C16 119.0(3) . . ? O11 C11 C12 120.7(3) . . ? C16 C11 C12 120.3(3) . . ? C13 C12 C11 119.0(3) . . ? C13 C12 C1 123.2(3) . . ? C11 C12 C1 117.7(3) . . ? C12 C13 C14 122.0(4) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C13 C14 C15 117.8(4) . . ? C13 C14 H14 121.1 . . ? C15 C14 H14 121.1 . . ? C16 C15 C14 123.0(4) . . ? C16 C15 H15 118.5 . . ? C14 C15 H15 118.5 . . ? C15 C16 C11 117.8(3) . . ? C15 C16 C2 116.7(3) . . ? C11 C16 C2 125.5(3) . . ? N1 C17 C19 110.8(3) . . ? N1 C17 C18 109.6(3) . . ? C19 C17 C18 110.5(4) . . ? N1 C17 C20 105.7(4) . . ? C19 C17 C20 110.4(4) . . ? C18 C17 C20 109.7(4) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 C21 C22 111.3(4) . . ? N2 C21 C24 106.5(4) . . ? C22 C21 C24 109.7(5) . . ? N2 C21 C23 109.7(4) . . ? C22 C21 C23 109.2(5) . . ? C24 C21 C23 110.5(5) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O31 C31 C36 118.8(3) . . ? O31 C31 C32 119.8(3) . . ? C36 C31 C32 121.4(4) . . ? C33 C32 C31 118.2(4) . . ? C33 C32 C3 123.4(4) . . ? C31 C32 C3 118.4(3) . . ? C34 C33 C32 121.9(4) . . ? C34 C33 H33 119.0 . . ? C32 C33 H33 119.0 . . ? C33 C34 C35 118.4(4) . . ? C33 C34 H34 120.8 . . ? C35 C34 H34 120.8 . . ? C36 C35 C34 122.7(4) . . ? C36 C35 H35 118.6 . . ? C34 C35 H35 118.6 . . ? C35 C36 C31 117.2(4) . . ? C35 C36 C4 117.1(4) . . ? C31 C36 C4 125.7(4) . . ? N3 C37 C38 109.5(4) . . ? N3 C37 C39 109.6(4) . . ? C38 C37 C39 111.9(4) . . ? N3 C37 C40 106.3(4) . . ? C38 C37 C40 109.8(5) . . ? C39 C37 C40 109.5(5) . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C37 C39 H39A 109.5 . . ? C37 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C37 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? N4 C41 C42 111.0(5) . . ? N4 C41 C43 110.7(4) . . ? C42 C41 C43 111.0(5) . . ? N4 C41 C44 105.0(4) . . ? C42 C41 C44 110.3(5) . . ? C43 C41 C44 108.8(5) . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C41 C43 H43A 109.5 . . ? C41 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C41 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C41 C44 H44A 109.5 . . ? C41 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C41 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 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 C17 N1 C1 O1 -5.4(6) . . . . ? C17 N1 C1 C12 173.6(3) . . . . ? C21 N2 C2 O2 2.9(7) . . . . ? C21 N2 C2 C16 -174.8(4) . . . . ? C37 N3 C3 O3 1.1(6) . . . . ? C37 N3 C3 C32 179.7(4) . . . . ? C41 N4 C4 O4 0.3(7) . . . . ? C41 N4 C4 C36 177.2(4) . . . . ? O11 C11 C12 C13 -176.2(3) . . . . ? C16 C11 C12 C13 2.3(5) . . . . ? O11 C11 C12 C1 2.3(5) . . . . ? C16 C11 C12 C1 -179.2(3) . . . . ? O1 C1 C12 C13 167.4(4) . . . . ? N1 C1 C12 C13 -11.6(6) . . . . ? O1 C1 C12 C11 -11.0(5) . . . . ? N1 C1 C12 C11 170.0(3) . . . . ? C11 C12 C13 C14 0.0(6) . . . . ? C1 C12 C13 C14 -178.3(4) . . . . ? C12 C13 C14 C15 -1.0(6) . . . . ? C13 C14 C15 C16 -0.5(7) . . . . ? C14 C15 C16 C11 2.8(6) . . . . ? C14 C15 C16 C2 -176.2(4) . . . . ? O11 C11 C16 C15 174.9(3) . . . . ? C12 C11 C16 C15 -3.7(5) . . . . ? O11 C11 C16 C2 -6.2(5) . . . . ? C12 C11 C16 C2 175.3(3) . . . . ? O2 C2 C16 C15 -12.3(5) . . . . ? N2 C2 C16 C15 165.5(4) . . . . ? O2 C2 C16 C11 168.8(4) . . . . ? N2 C2 C16 C11 -13.5(5) . . . . ? C1 N1 C17 C19 -54.8(5) . . . . ? C1 N1 C17 C18 67.5(5) . . . . ? C1 N1 C17 C20 -174.4(4) . . . . ? C2 N2 C21 C22 55.3(6) . . . . ? C2 N2 C21 C24 174.7(5) . . . . ? C2 N2 C21 C23 -65.7(6) . . . . ? O31 C31 C32 C33 176.6(3) . . . . ? C36 C31 C32 C33 -4.4(6) . . . . ? O31 C31 C32 C3 -2.4(5) . . . . ? C36 C31 C32 C3 176.5(3) . . . . ? O3 C3 C32 C33 -161.7(4) . . . . ? N3 C3 C32 C33 19.7(6) . . . . ? O3 C3 C32 C31 17.3(6) . . . . ? N3 C3 C32 C31 -161.3(4) . . . . ? C31 C32 C33 C34 1.7(6) . . . . ? C3 C32 C33 C34 -179.3(4) . . . . ? C32 C33 C34 C35 0.2(7) . . . . ? C33 C34 C35 C36 0.7(7) . . . . ? C34 C35 C36 C31 -3.3(6) . . . . ? C34 C35 C36 C4 177.8(4) . . . . ? O31 C31 C36 C35 -175.9(3) . . . . ? C32 C31 C36 C35 5.2(5) . . . . ? O31 C31 C36 C4 2.9(6) . . . . ? C32 C31 C36 C4 -176.0(3) . . . . ? O4 C4 C36 C35 2.9(6) . . . . ? N4 C4 C36 C35 -174.1(4) . . . . ? O4 C4 C36 C31 -175.8(4) . . . . ? N4 C4 C36 C31 7.2(6) . . . . ? C3 N3 C37 C38 -64.3(6) . . . . ? C3 N3 C37 C39 58.8(6) . . . . ? C3 N3 C37 C40 177.1(4) . . . . ? C4 N4 C41 C42 -61.9(6) . . . . ? C4 N4 C41 C43 61.8(6) . . . . ? C4 N4 C41 C44 179.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.911 _refine_diff_density_max 0.559 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.051 #===END data_2'ONMe4 _database_code_depnum_ccdc_archive 'CCDC 259701' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H23 N2 O3, C4 H12 N' _chemical_formula_sum 'C20 H35 N3 O3' _chemical_formula_weight 365.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'C m c 21 ' _symmetry_space_group_name_Hall 'C 2c -2 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.2912(6) _cell_length_b 13.0775(5) _cell_length_c 12.1094(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2104.80(15) _cell_formula_units_Z 4 _cell_measurement_temperature 200 _cell_measurement_reflns_used 10935 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9436 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2451 _reflns_number_gt 2171 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'teXsan Ver. 1.11' _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^)+(0.0637P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 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 0.5(10) _refine_ls_number_reflns 2451 _refine_ls_number_parameters 127 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0928 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.72771(7) 0.66397(7) 0.85876(8) 0.0370(2) Uani 1 1 d . . . O11 O 1.0000 0.54281(10) 0.97458(12) 0.0334(3) Uani 1 2 d S . . N1 N 0.80465(8) 0.53963(8) 0.95973(9) 0.0281(3) Uani 1 1 d . . . H1 H 0.8637 0.5153 0.9794 0.034 Uiso 1 1 calc R . . N11 N 1.0000 0.30242(11) 0.77480(13) 0.0295(3) Uani 1 2 d S . . C1 C 0.80537(9) 0.62052(9) 0.89151(10) 0.0254(3) Uani 1 1 d . . . C11 C 1.0000 0.61349(12) 0.89826(15) 0.0246(4) Uani 1 2 d S . . C12 C 0.90796(9) 0.65401(9) 0.85382(11) 0.0252(3) Uani 1 1 d . . . C13 C 0.91059(9) 0.72639(10) 0.77009(11) 0.0284(3) Uani 1 1 d . . . H13 H 0.8489 0.7519 0.7415 0.034 Uiso 1 1 calc R . . C14 C 1.0000 0.76262(14) 0.72685(16) 0.0324(4) Uani 1 2 d S . . H14 H 1.0000 0.8114 0.6687 0.039 Uiso 1 2 calc SR . . C17 C 0.71609(9) 0.48729(10) 1.00523(11) 0.0292(3) Uani 1 1 d . . . C18 C 0.64712(14) 0.45046(15) 0.91402(16) 0.0569(5) Uani 1 1 d . . . H18A H 0.6844 0.4047 0.8647 0.068 Uiso 1 1 calc R . . H18B H 0.6223 0.5093 0.8720 0.068 Uiso 1 1 calc R . . H18C H 0.5901 0.4136 0.9464 0.068 Uiso 1 1 calc R . . C19 C 0.66019(13) 0.55816(13) 1.08305(14) 0.0494(4) Uani 1 1 d . . . H19A H 0.7059 0.5812 1.1415 0.059 Uiso 1 1 calc R . . H19B H 0.6033 0.5216 1.1161 0.059 Uiso 1 1 calc R . . H19C H 0.6353 0.6175 1.0419 0.059 Uiso 1 1 calc R . . C20 C 0.75680(14) 0.39590(13) 1.06882(19) 0.0589(5) Uani 1 1 d . . . H20A H 0.8014 0.4199 1.1279 0.071 Uiso 1 1 calc R . . H20B H 0.7946 0.3515 1.0185 0.071 Uiso 1 1 calc R . . H20C H 0.7007 0.3575 1.1010 0.071 Uiso 1 1 calc R . . C21 C 1.0000 0.19983(17) 0.7210(2) 0.0459(5) Uani 1 2 d S . . H21A H 1.0000 0.2082 0.6406 0.055 Uiso 1 2 calc SR . . H21B H 0.9398 0.1619 0.7435 0.055 Uiso 0.50 1 calc PR . . H21C H 1.0602 0.1619 0.7435 0.055 Uiso 0.50 1 calc PR . . C22 C 1.0000 0.28741(18) 0.89683(17) 0.0421(5) Uani 1 2 d S . . H22A H 1.0000 0.3542 0.9336 0.051 Uiso 1 2 calc SR . . H22B H 1.0602 0.2491 0.9185 0.051 Uiso 0.50 1 calc PR . . H22C H 0.9398 0.2491 0.9185 0.051 Uiso 0.50 1 calc PR . . C23 C 0.90792(11) 0.36003(14) 0.74125(15) 0.0465(4) Uani 1 1 d . . . H23A H 0.9080 0.4274 0.7768 0.056 Uiso 1 1 calc R . . H23B H 0.8479 0.3219 0.7641 0.056 Uiso 1 1 calc R . . H23C H 0.9074 0.3686 0.6609 0.056 Uiso 1 1 calc R . . 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 0.0213(4) 0.0439(5) 0.0459(5) 0.0086(5) 0.0007(4) 0.0057(4) O11 0.0190(6) 0.0431(7) 0.0380(7) 0.0174(6) 0.000 0.000 N1 0.0163(5) 0.0341(6) 0.0339(6) 0.0039(5) 0.0022(4) 0.0013(4) N11 0.0195(7) 0.0327(7) 0.0363(8) -0.0010(7) 0.000 0.000 C1 0.0212(6) 0.0254(5) 0.0295(7) -0.0024(5) 0.0010(5) 0.0012(5) C11 0.0211(8) 0.0247(8) 0.0280(9) -0.0016(7) 0.000 0.000 C12 0.0212(6) 0.0253(6) 0.0291(6) -0.0022(5) 0.0001(5) 0.0008(4) C13 0.0249(6) 0.0263(6) 0.0340(7) 0.0018(5) -0.0021(5) 0.0039(5) C14 0.0317(10) 0.0288(8) 0.0367(10) 0.0069(8) 0.000 0.000 C17 0.0187(5) 0.0349(6) 0.0339(6) 0.0015(6) 0.0053(5) -0.0014(5) C18 0.0479(10) 0.0717(11) 0.0510(10) -0.0099(9) 0.0000(8) -0.0289(9) C19 0.0446(9) 0.0562(9) 0.0475(9) -0.0055(8) 0.0219(8) 0.0031(8) C20 0.0353(8) 0.0572(9) 0.0842(14) 0.0337(10) 0.0190(9) 0.0053(8) C21 0.0384(12) 0.0453(11) 0.0538(13) -0.0192(11) 0.000 0.000 C22 0.0432(12) 0.0485(11) 0.0347(11) 0.0027(9) 0.000 0.000 C23 0.0344(9) 0.0550(9) 0.0502(10) 0.0073(8) -0.0043(7) 0.0137(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2433(15) . ? O11 C11 1.307(2) . ? N1 C1 1.3421(16) . ? N1 C17 1.4690(15) . ? N1 H1 0.8800 . ? N11 C22 1.491(3) . ? N11 C21 1.492(3) . ? N11 C23 1.4934(16) 2_755 ? N11 C23 1.4934(16) . ? C1 C12 1.5032(17) . ? C11 C12 1.4377(14) . ? C11 C12 1.4377(14) 2_755 ? C12 C13 1.3875(18) . ? C13 C14 1.3823(15) . ? C13 H13 0.9500 . ? C14 C13 1.3823(15) 2_755 ? C14 H14 0.9500 . ? C17 C18 1.514(2) . ? C17 C19 1.516(2) . ? C17 C20 1.521(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 N1 C17 127.14(11) . . ? C1 N1 H1 116.4 . . ? C17 N1 H1 116.4 . . ? C22 N11 C21 108.34(17) . . ? C22 N11 C23 109.64(11) . 2_755 ? C21 N11 C23 109.56(11) . 2_755 ? C22 N11 C23 109.64(11) . . ? C21 N11 C23 109.56(11) . . ? C23 N11 C23 110.07(17) 2_755 . ? O1 C1 N1 123.42(12) . . ? O1 C1 C12 121.53(11) . . ? N1 C1 C12 115.02(10) . . ? O11 C11 C12 121.69(7) . . ? O11 C11 C12 121.69(7) . 2_755 ? C12 C11 C12 116.62(15) . 2_755 ? C13 C12 C11 120.23(11) . . ? C13 C12 C1 116.33(10) . . ? C11 C12 C1 123.42(11) . . ? C14 C13 C12 122.16(11) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C13 118.56(16) . 2_755 ? C13 C14 H14 120.7 . . ? C13 C14 H14 120.7 2_755 . ? N1 C17 C18 111.09(12) . . ? N1 C17 C19 109.93(11) . . ? C18 C17 C19 110.56(13) . . ? N1 C17 C20 105.72(11) . . ? C18 C17 C20 109.55(15) . . ? C19 C17 C20 109.87(14) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N11 C21 H21A 109.5 . . ? N11 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N11 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N11 C22 H22A 109.5 . . ? N11 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N11 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N11 C23 H23A 109.5 . . ? N11 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N11 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C17 N1 C1 O1 1.4(2) . . . . ? C17 N1 C1 C12 -176.83(11) . . . . ? O11 C11 C12 C13 -177.71(14) . . . . ? C12 C11 C12 C13 1.8(2) 2_755 . . . ? O11 C11 C12 C1 0.9(2) . . . . ? C12 C11 C12 C1 -179.63(8) 2_755 . . . ? O1 C1 C12 C13 -8.22(18) . . . . ? N1 C1 C12 C13 170.07(11) . . . . ? O1 C1 C12 C11 173.12(13) . . . . ? N1 C1 C12 C11 -8.59(18) . . . . ? C11 C12 C13 C14 -0.4(2) . . . . ? C1 C12 C13 C14 -179.10(14) . . . . ? C12 C13 C14 C13 -1.0(3) . . . 2_755 ? C1 N1 C17 C18 56.43(17) . . . . ? C1 N1 C17 C19 -66.27(18) . . . . ? C1 N1 C17 C20 175.20(14) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.198 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.045 #===END