# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name 'Qiang Liu' _publ_contact_author_address ;College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072 P. R. China ; _publ_contact_author_email qiangliu@whu.edu.cn loop_ _publ_author_name 'Qiang Liu' 'Qingyong Zhao' 'Jie Liu' 'Pan Wu' 'Hong Yi' 'Aiwen Lei' data_101015cm _database_code_depnum_ccdc_archive 'CCDC 822881' #TrackingRef '- 3b(CCDC 822881).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H46 N2 O12' _chemical_formula_weight 698.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1850(7) _cell_length_b 13.9246(11) _cell_length_c 16.2335(13) _cell_angle_alpha 75.704(2) _cell_angle_beta 87.418(2) _cell_angle_gamma 72.161(2) _cell_volume 1914.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1602 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 18.97 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.091 _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(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13934 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0909 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7448 _reflns_number_gt 3393 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0501P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7448 _refine_ls_number_parameters 463 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1454 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1515 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_restrained_S_all 0.901 _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 0.7216(2) 0.71559(14) 0.21332(12) 0.0563(5) Uani 1 1 d . . . O2 O 0.8615(3) 0.5927(2) 0.31995(15) 0.1084(10) Uani 1 1 d . . . O3 O 0.7774(2) 0.63653(14) 0.01639(12) 0.0566(5) Uani 1 1 d . . . O4 O 0.5982(4) 0.5675(2) 0.07337(19) 0.1323(12) Uani 1 1 d . . . O5 O 0.7549(3) 0.94128(17) -0.08573(14) 0.0867(8) Uani 1 1 d . . . O6 O 0.5885(3) 0.84665(16) -0.06866(13) 0.0705(6) Uani 1 1 d . . . N1 N 0.7802(3) 0.79996(18) 0.02463(15) 0.0548(7) Uani 1 1 d . . . C1 C 0.9224(4) 0.7916(2) 0.0620(2) 0.0571(8) Uani 1 1 d . . . C2 C 0.9537(3) 0.7120(2) 0.13497(19) 0.0535(8) Uani 1 1 d . . . C3 C 1.0893(4) 0.6855(3) 0.1803(2) 0.0692(10) Uani 1 1 d . . . H3 H 1.1115 0.6307 0.2287 0.083 Uiso 1 1 calc R . . C4 C 1.1929(4) 0.7405(3) 0.1538(3) 0.0804(11) Uani 1 1 d . . . C5 C 1.1550(4) 0.8220(3) 0.0829(3) 0.0863(12) Uani 1 1 d . . . H5 H 1.2228 0.8604 0.0664 0.104 Uiso 1 1 calc R . . C6 C 1.0205(4) 0.8503(3) 0.0342(2) 0.0730(10) Uani 1 1 d . . . H6 H 0.9981 0.9053 -0.0141 0.088 Uiso 1 1 calc R . . C7 C 1.3441(4) 0.7117(4) 0.2024(2) 0.1235(17) Uani 1 1 d . . . H7A H 1.3796 0.7716 0.1926 0.185 Uiso 1 1 calc R . . H7B H 1.4184 0.6571 0.1831 0.185 Uiso 1 1 calc R . . H7C H 1.3298 0.6883 0.2621 0.185 Uiso 1 1 calc R . . C8 C 0.7316(3) 0.7114(2) 0.06765(17) 0.0505(8) Uani 1 1 d . . . H8 H 0.6210 0.7314 0.0760 0.061 Uiso 1 1 calc R . . C9 C 0.8216(3) 0.6696(2) 0.15175(18) 0.0518(8) Uani 1 1 d . . . H9 H 0.8548 0.5933 0.1690 0.062 Uiso 1 1 calc R . . C10 C 0.7100(4) 0.8709(2) -0.0479(2) 0.0605(9) Uani 1 1 d . . . C11 C 0.4914(4) 0.9065(3) -0.1450(2) 0.0696(10) Uani 1 1 d . . . C12 C 0.3779(4) 0.8483(3) -0.1435(2) 0.1062(14) Uani 1 1 d . . . H12A H 0.4314 0.7760 -0.1389 0.159 Uiso 1 1 calc R . . H12B H 0.3161 0.8763 -0.1951 0.159 Uiso 1 1 calc R . . H12C H 0.3136 0.8551 -0.0957 0.159 Uiso 1 1 calc R . . C13 C 0.4159(6) 1.0153(3) -0.1375(3) 0.158(2) Uani 1 1 d . . . H13A H 0.3686 1.0139 -0.0834 0.236 Uiso 1 1 calc R . . H13B H 0.3394 1.0508 -0.1822 0.236 Uiso 1 1 calc R . . H13C H 0.4910 1.0513 -0.1420 0.236 Uiso 1 1 calc R . . C14 C 0.5866(5) 0.9004(4) -0.2226(2) 0.1233(16) Uani 1 1 d . . . H14A H 0.6613 0.9359 -0.2227 0.185 Uiso 1 1 calc R . . H14B H 0.5216 0.9327 -0.2728 0.185 Uiso 1 1 calc R . . H14C H 0.6377 0.8288 -0.2218 0.185 Uiso 1 1 calc R . . C15 C 0.6953(4) 0.5705(3) 0.0231(2) 0.0741(10) Uani 1 1 d . . . C16 C 0.7433(5) 0.5033(3) -0.0373(2) 0.0959(13) Uani 1 1 d . . . H16A H 0.7004 0.4468 -0.0216 0.144 Uiso 1 1 calc R . . H16B H 0.8529 0.4761 -0.0357 0.144 Uiso 1 1 calc R . . H16C H 0.7077 0.5434 -0.0938 0.144 Uiso 1 1 calc R . . C17 C 0.7538(4) 0.6682(3) 0.2956(2) 0.0656(9) Uani 1 1 d . . . C18 C 0.6438(4) 0.7229(3) 0.3515(2) 0.0894(12) Uani 1 1 d . . . H18A H 0.5803 0.6810 0.3774 0.134 Uiso 1 1 calc R . . H18B H 0.5809 0.7885 0.3183 0.134 Uiso 1 1 calc R . . H18C H 0.6992 0.7344 0.3950 0.134 Uiso 1 1 calc R . . O7 O 0.2631(3) 0.07630(18) 0.57286(15) 0.0901(8) Uani 1 1 d . . . O8 O 0.0035(3) 0.13296(16) 0.55675(13) 0.0710(6) Uani 1 1 d . . . O9 O -0.0410(2) 0.35931(15) 0.47960(12) 0.0577(6) Uani 1 1 d . . . O10 O -0.2867(3) 0.3830(3) 0.4604(2) 0.1530(15) Uani 1 1 d . . . O11 O 0.0080(2) 0.28623(14) 0.28056(12) 0.0581(6) Uani 1 1 d . . . O12 O -0.0020(3) 0.42208(18) 0.17266(14) 0.0968(9) Uani 1 1 d . . . N2 N 0.1387(3) 0.20856(18) 0.46228(16) 0.0570(7) Uani 1 1 d . . . C19 C 0.2651(4) 0.2367(2) 0.42074(19) 0.0559(8) Uani 1 1 d . . . C20 C 0.2110(3) 0.3179(2) 0.34999(19) 0.0526(8) Uani 1 1 d . . . C21 C 0.3112(4) 0.3623(3) 0.3015(2) 0.0649(9) Uani 1 1 d . . . H21 H 0.2743 0.4175 0.2543 0.078 Uiso 1 1 calc R . . C22 C 0.4665(5) 0.3256(3) 0.3222(2) 0.0786(11) Uani 1 1 d . . . C23 C 0.5154(4) 0.2434(3) 0.3917(3) 0.0864(12) Uani 1 1 d . . . H23 H 0.6197 0.2176 0.4055 0.104 Uiso 1 1 calc R . . C24 C 0.4190(4) 0.1964(3) 0.4429(2) 0.0752(10) Uani 1 1 d . . . H24 H 0.4561 0.1407 0.4897 0.090 Uiso 1 1 calc R . . C25 C 0.5777(4) 0.3769(4) 0.2709(2) 0.1202(16) Uani 1 1 d . . . H25A H 0.6009 0.4226 0.3003 0.180 Uiso 1 1 calc R . . H25B H 0.5320 0.4161 0.2160 0.180 Uiso 1 1 calc R . . H25C H 0.6702 0.3242 0.2641 0.180 Uiso 1 1 calc R . . C26 C -0.0018(3) 0.2867(2) 0.42650(18) 0.0514(8) Uani 1 1 d . . . H26 H -0.0838 0.2566 0.4223 0.062 Uiso 1 1 calc R . . C27 C 0.0420(3) 0.3405(2) 0.33939(17) 0.0515(8) Uani 1 1 d . . . H27 H -0.0123 0.4153 0.3236 0.062 Uiso 1 1 calc R . . C28 C 0.1458(5) 0.1326(3) 0.5354(2) 0.0637(9) Uani 1 1 d . . . C29 C -0.0282(5) 0.0657(3) 0.6364(2) 0.0810(11) Uani 1 1 d . . . C30 C -0.2009(5) 0.0927(4) 0.6287(3) 0.161(2) Uani 1 1 d . . . H30A H -0.2466 0.1659 0.6237 0.241 Uiso 1 1 calc R . . H30B H -0.2372 0.0542 0.6785 0.241 Uiso 1 1 calc R . . H30C H -0.2281 0.0751 0.5792 0.241 Uiso 1 1 calc R . . C31 C 0.0518(6) -0.0471(3) 0.6385(3) 0.1335(18) Uani 1 1 d . . . H31A H 0.0264 -0.0619 0.5873 0.200 Uiso 1 1 calc R . . H31B H 0.0196 -0.0905 0.6867 0.200 Uiso 1 1 calc R . . H31C H 0.1605 -0.0605 0.6429 0.200 Uiso 1 1 calc R . . C32 C 0.0228(5) 0.0963(3) 0.7101(2) 0.1244(16) Uani 1 1 d . . . H32A H 0.1321 0.0808 0.7107 0.187 Uiso 1 1 calc R . . H32B H -0.0072 0.0581 0.7623 0.187 Uiso 1 1 calc R . . H32C H -0.0240 0.1695 0.7045 0.187 Uiso 1 1 calc R . . C33 C -0.1894(5) 0.4015(3) 0.4920(2) 0.0721(10) Uani 1 1 d . . . C34 C -0.2134(4) 0.4732(3) 0.5486(2) 0.0894(12) Uani 1 1 d . . . H34A H -0.3199 0.4956 0.5612 0.134 Uiso 1 1 calc R . . H34B H -0.1820 0.5326 0.5208 0.134 Uiso 1 1 calc R . . H34C H -0.1540 0.4379 0.6004 0.134 Uiso 1 1 calc R . . C35 C -0.0117(4) 0.3361(3) 0.1987(2) 0.0599(8) Uani 1 1 d . . . C36 C -0.0447(4) 0.2723(3) 0.1448(2) 0.0849(11) Uani 1 1 d . . . H36A H -0.1502 0.2743 0.1495 0.127 Uiso 1 1 calc R . . H36B H 0.0195 0.2016 0.1636 0.127 Uiso 1 1 calc R . . H36C H -0.0249 0.2998 0.0865 0.127 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 0.0584(14) 0.0625(13) 0.0464(13) -0.0154(11) 0.0058(11) -0.0151(11) O2 0.134(3) 0.0871(19) 0.0658(17) -0.0142(15) -0.0121(17) 0.0196(18) O3 0.0685(14) 0.0586(12) 0.0557(13) -0.0223(11) 0.0097(11) -0.0328(12) O4 0.165(3) 0.175(3) 0.137(3) -0.092(2) 0.084(2) -0.134(3) O5 0.121(2) 0.0649(15) 0.0801(17) 0.0007(13) -0.0083(15) -0.0503(16) O6 0.0770(16) 0.0703(15) 0.0630(15) -0.0025(12) -0.0108(13) -0.0296(13) N1 0.0649(18) 0.0510(15) 0.0539(16) -0.0135(13) 0.0015(14) -0.0247(14) C1 0.060(2) 0.065(2) 0.060(2) -0.0308(18) 0.0078(17) -0.0278(18) C2 0.052(2) 0.061(2) 0.054(2) -0.0267(17) 0.0053(17) -0.0168(17) C3 0.054(2) 0.093(3) 0.065(2) -0.036(2) 0.0027(19) -0.015(2) C4 0.056(2) 0.124(3) 0.080(3) -0.052(3) 0.013(2) -0.034(3) C5 0.076(3) 0.128(4) 0.092(3) -0.057(3) 0.028(2) -0.064(3) C6 0.080(3) 0.088(3) 0.074(2) -0.036(2) 0.015(2) -0.047(2) C7 0.061(3) 0.217(5) 0.120(4) -0.079(4) 0.005(3) -0.051(3) C8 0.0506(19) 0.0536(18) 0.0518(19) -0.0182(16) 0.0033(15) -0.0184(16) C9 0.0499(19) 0.0526(18) 0.0535(19) -0.0211(16) 0.0001(16) -0.0102(16) C10 0.079(3) 0.050(2) 0.056(2) -0.0165(18) 0.0060(19) -0.0229(19) C11 0.087(3) 0.062(2) 0.053(2) -0.0073(18) -0.014(2) -0.017(2) C12 0.102(3) 0.127(3) 0.092(3) -0.009(3) -0.021(3) -0.047(3) C13 0.171(5) 0.082(3) 0.190(5) -0.052(3) -0.084(4) 0.032(3) C14 0.153(4) 0.177(5) 0.064(3) -0.031(3) 0.011(3) -0.086(4) C15 0.098(3) 0.088(3) 0.061(2) -0.027(2) 0.018(2) -0.059(2) C16 0.148(4) 0.097(3) 0.077(3) -0.047(2) 0.021(2) -0.068(3) C17 0.081(3) 0.064(2) 0.049(2) -0.0179(19) 0.001(2) -0.015(2) C18 0.096(3) 0.114(3) 0.058(2) -0.033(2) 0.015(2) -0.025(3) O7 0.0814(19) 0.0814(17) 0.0822(18) 0.0039(14) -0.0124(15) -0.0055(15) O8 0.0757(17) 0.0671(14) 0.0656(15) 0.0002(12) 0.0017(13) -0.0280(13) O9 0.0609(15) 0.0622(13) 0.0580(13) -0.0247(11) 0.0062(11) -0.0228(12) O10 0.0596(18) 0.219(4) 0.235(4) -0.173(3) 0.013(2) -0.029(2) O11 0.0759(15) 0.0546(12) 0.0482(13) -0.0136(11) -0.0027(11) -0.0245(11) O12 0.163(3) 0.0604(15) 0.0593(16) -0.0090(13) 0.0166(16) -0.0287(17) N2 0.0573(18) 0.0532(15) 0.0562(17) -0.0057(14) -0.0007(14) -0.0165(14) C19 0.057(2) 0.062(2) 0.057(2) -0.0250(17) 0.0054(17) -0.0220(18) C20 0.058(2) 0.0548(19) 0.055(2) -0.0259(17) 0.0086(17) -0.0226(17) C21 0.078(3) 0.078(2) 0.056(2) -0.0324(18) 0.0154(19) -0.038(2) C22 0.080(3) 0.111(3) 0.070(3) -0.043(2) 0.020(2) -0.051(3) C23 0.056(2) 0.128(3) 0.086(3) -0.047(3) 0.011(2) -0.028(3) C24 0.061(2) 0.096(3) 0.069(2) -0.026(2) -0.001(2) -0.020(2) C25 0.104(3) 0.192(5) 0.110(3) -0.060(3) 0.045(3) -0.097(3) C26 0.055(2) 0.0531(18) 0.0499(19) -0.0178(16) 0.0018(16) -0.0185(17) C27 0.065(2) 0.0448(17) 0.0491(18) -0.0153(15) 0.0045(16) -0.0213(16) C28 0.070(3) 0.062(2) 0.061(2) -0.0185(19) 0.000(2) -0.018(2) C29 0.115(3) 0.072(3) 0.053(2) 0.0022(19) 0.008(2) -0.038(2) C30 0.116(4) 0.201(5) 0.136(4) 0.052(4) 0.014(3) -0.082(4) C31 0.234(6) 0.071(3) 0.099(3) 0.001(2) -0.001(3) -0.067(3) C32 0.170(5) 0.129(4) 0.071(3) -0.038(3) 0.012(3) -0.032(3) C33 0.064(3) 0.084(3) 0.078(3) -0.042(2) 0.009(2) -0.021(2) C34 0.100(3) 0.097(3) 0.081(3) -0.052(2) 0.022(2) -0.023(2) C35 0.067(2) 0.057(2) 0.048(2) -0.0136(18) 0.0068(17) -0.0096(18) C36 0.101(3) 0.107(3) 0.057(2) -0.035(2) 0.006(2) -0.036(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C17 1.338(3) . ? O1 C9 1.459(3) . ? O2 C17 1.197(4) . ? O3 C15 1.340(3) . ? O3 C8 1.444(3) . ? O4 C15 1.185(4) . ? O5 C10 1.199(3) . ? O6 C10 1.339(3) . ? O6 C11 1.469(3) . ? N1 C10 1.372(3) . ? N1 C1 1.425(3) . ? N1 C8 1.447(3) . ? C1 C2 1.378(4) . ? C1 C6 1.385(4) . ? C2 C3 1.377(4) . ? C2 C9 1.492(4) . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C4 C5 1.371(5) . ? C4 C7 1.521(4) . ? C5 C6 1.393(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.517(3) . ? C8 H8 0.9800 . ? C9 H9 0.9800 . ? C11 C13 1.494(5) . ? C11 C12 1.501(4) . ? C11 C14 1.506(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.481(4) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.487(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O7 C28 1.204(4) . ? O8 C28 1.335(4) . ? O8 C29 1.473(3) . ? O9 C33 1.337(4) . ? O9 C26 1.440(3) . ? O10 C33 1.173(4) . ? O11 C35 1.331(3) . ? O11 C27 1.452(3) . ? O12 C35 1.197(3) . ? N2 C28 1.370(4) . ? N2 C19 1.426(4) . ? N2 C26 1.443(3) . ? C19 C24 1.379(4) . ? C19 C20 1.382(4) . ? C20 C21 1.375(4) . ? C20 C27 1.496(4) . ? C21 C22 1.386(4) . ? C21 H21 0.9300 . ? C22 C23 1.371(5) . ? C22 C25 1.524(4) . ? C23 C24 1.387(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.527(4) . ? C26 H26 0.9800 . ? C27 H27 0.9800 . ? C29 C32 1.503(5) . ? C29 C31 1.508(5) . ? C29 C30 1.517(5) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.480(4) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C36 1.490(4) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 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 C17 O1 C9 117.2(2) . . ? C15 O3 C8 116.5(2) . . ? C10 O6 C11 122.2(2) . . ? C10 N1 C1 126.4(3) . . ? C10 N1 C8 124.0(2) . . ? C1 N1 C8 109.0(2) . . ? C2 C1 C6 122.0(3) . . ? C2 C1 N1 109.2(3) . . ? C6 C1 N1 128.8(3) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 C9 130.6(3) . . ? C1 C2 C9 109.3(3) . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 118.3(3) . . ? C5 C4 C7 120.9(4) . . ? C3 C4 C7 120.8(4) . . ? C4 C5 C6 123.7(3) . . ? C4 C5 H5 118.2 . . ? C6 C5 H5 118.2 . . ? C1 C6 C5 116.0(3) . . ? C1 C6 H6 122.0 . . ? C5 C6 H6 122.0 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O3 C8 N1 106.8(2) . . ? O3 C8 C9 110.2(2) . . ? N1 C8 C9 104.6(2) . . ? O3 C8 H8 111.6 . . ? N1 C8 H8 111.6 . . ? C9 C8 H8 111.6 . . ? O1 C9 C2 110.6(2) . . ? O1 C9 C8 106.0(2) . . ? C2 C9 C8 103.4(2) . . ? O1 C9 H9 112.1 . . ? C2 C9 H9 112.1 . . ? C8 C9 H9 112.1 . . ? O5 C10 O6 127.1(3) . . ? O5 C10 N1 123.9(3) . . ? O6 C10 N1 109.0(3) . . ? O6 C11 C13 109.6(3) . . ? O6 C11 C12 102.8(3) . . ? C13 C11 C12 111.9(4) . . ? O6 C11 C14 109.1(3) . . ? C13 C11 C14 113.4(4) . . ? C12 C11 C14 109.4(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O4 C15 O3 122.0(3) . . ? O4 C15 C16 125.9(3) . . ? O3 C15 C16 112.1(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 O1 123.0(3) . . ? O2 C17 C18 125.1(3) . . ? O1 C17 C18 111.8(3) . . ? 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 . . ? C28 O8 C29 121.9(3) . . ? C33 O9 C26 117.5(2) . . ? C35 O11 C27 117.4(2) . . ? C28 N2 C19 126.3(3) . . ? C28 N2 C26 123.3(3) . . ? C19 N2 C26 109.2(2) . . ? C24 C19 C20 121.5(3) . . ? C24 C19 N2 129.6(3) . . ? C20 C19 N2 108.9(3) . . ? C21 C20 C19 119.9(3) . . ? C21 C20 C27 130.8(3) . . ? C19 C20 C27 109.4(3) . . ? C20 C21 C22 120.7(3) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C23 C22 C21 117.5(3) . . ? C23 C22 C25 121.4(4) . . ? C21 C22 C25 121.1(4) . . ? C22 C23 C24 124.0(4) . . ? C22 C23 H23 118.0 . . ? C24 C23 H23 118.0 . . ? C19 C24 C23 116.5(3) . . ? C19 C24 H24 121.8 . . ? C23 C24 H24 121.8 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O9 C26 N2 106.5(2) . . ? O9 C26 C27 109.1(2) . . ? N2 C26 C27 104.2(2) . . ? O9 C26 H26 112.2 . . ? N2 C26 H26 112.2 . . ? C27 C26 H26 112.2 . . ? O11 C27 C20 110.7(2) . . ? O11 C27 C26 105.3(2) . . ? C20 C27 C26 102.9(2) . . ? O11 C27 H27 112.4 . . ? C20 C27 H27 112.4 . . ? C26 C27 H27 112.4 . . ? O7 C28 O8 127.1(3) . . ? O7 C28 N2 124.2(3) . . ? O8 C28 N2 108.7(3) . . ? O8 C29 C32 108.7(3) . . ? O8 C29 C31 110.1(3) . . ? C32 C29 C31 111.5(3) . . ? O8 C29 C30 101.1(3) . . ? C32 C29 C30 112.5(4) . . ? C31 C29 C30 112.3(4) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O10 C33 O9 122.7(3) . . ? O10 C33 C34 125.3(4) . . ? O9 C33 C34 111.9(3) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O12 C35 O11 122.7(3) . . ? O12 C35 C36 124.9(3) . . ? O11 C35 C36 112.3(3) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.291 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.034 data_t _database_code_depnum_ccdc_archive 'CCDC 822882' #TrackingRef '- 3a(CCDC 822882).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 N O5' _chemical_formula_weight 277.27 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8633(10) _cell_length_b 18.912(2) _cell_length_c 8.4229(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.108(2) _cell_angle_gamma 90.00 _cell_volume 1408.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2274 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 27.87 _exptl_crystal_description block _exptl_crystal_colour colouress _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.100 _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(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5348 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2529 _reflns_number_gt 2132 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0628P)^2^+0.2675P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2529 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1555 _refine_ls_wR_factor_gt 0.1481 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0.150 _refine_ls_shift/su_mean 0.004 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2466(3) 0.66894(11) 0.7012(2) 0.0485(6) Uani 1 1 d . . . C2 C 0.2136(3) 0.73129(12) 0.7773(3) 0.0604(7) Uani 1 1 d . . . H2 H 0.2853 0.7670 0.7923 0.073 Uiso 1 1 calc R . . C3 C 0.0712(4) 0.73862(14) 0.8299(3) 0.0695(7) Uani 1 1 d . . . H3 H 0.0467 0.7802 0.8812 0.083 Uiso 1 1 calc R . . C4 C -0.0359(3) 0.68621(15) 0.8088(3) 0.0698(7) Uani 1 1 d . . . H4 H -0.1321 0.6932 0.8433 0.084 Uiso 1 1 calc R . . C5 C -0.0012(3) 0.62317(14) 0.7366(3) 0.0603(6) Uani 1 1 d . . . H5 H -0.0728 0.5873 0.7238 0.072 Uiso 1 1 calc R . . C6 C 0.1408(3) 0.61446(11) 0.6841(2) 0.0475(6) Uani 1 1 d . . . C7 C 0.2102(3) 0.55326(10) 0.6041(2) 0.0472(5) Uani 1 1 d . . . H7 H 0.1409 0.5326 0.5208 0.057 Uiso 1 1 calc R . . C8 C 0.3493(3) 0.58524(10) 0.5364(2) 0.0451(5) Uani 1 1 d . . . H8 H 0.4357 0.5528 0.5455 0.054 Uiso 1 1 calc R . . C9 C 0.1703(4) 0.44988(13) 0.7576(3) 0.0630(7) Uani 1 1 d . . . C10 C 0.2423(4) 0.39972(15) 0.8768(3) 0.0855(9) Uani 1 1 d . . . H10A H 0.2156 0.4127 0.9814 0.128 Uiso 1 1 calc R . . H10B H 0.3502 0.4016 0.8730 0.128 Uiso 1 1 calc R . . H10C H 0.2075 0.3526 0.8529 0.128 Uiso 1 1 calc R . . C11 C 0.3145(3) 0.55680(12) 0.2608(2) 0.0547(6) Uani 1 1 d . . . C12 C 0.2788(4) 0.58745(16) 0.0995(3) 0.0826(9) Uani 1 1 d . . . H12A H 0.2996 0.5531 0.0201 0.124 Uiso 1 1 calc R . . H12B H 0.3400 0.6287 0.0867 0.124 Uiso 1 1 calc R . . H12C H 0.1738 0.6003 0.0878 0.124 Uiso 1 1 calc R . . C13 C 0.5083(3) 0.68959(13) 0.6217(3) 0.0591(6) Uani 1 1 d . . . C14 C 0.6273(3) 0.66338(14) 0.5196(3) 0.0666(7) Uani 1 1 d . . . H14A H 0.7168 0.6917 0.5377 0.100 Uiso 1 1 calc R . . H14B H 0.5910 0.6666 0.4097 0.100 Uiso 1 1 calc R . . H14C H 0.6506 0.6150 0.5457 0.100 Uiso 1 1 calc R . . N1 N 0.3791(2) 0.64957(9) 0.62680(19) 0.0480(5) Uani 1 1 d . . . O1 O 0.26771(19) 0.50044(8) 0.71903(16) 0.0552(4) Uani 1 1 d . . . O2 O 0.0431(3) 0.44725(12) 0.7023(3) 0.1015(8) Uani 1 1 d . . . O3 O 0.31356(18) 0.60737(7) 0.37345(15) 0.0505(4) Uani 1 1 d . . . O4 O 0.3394(2) 0.49612(9) 0.29147(19) 0.0719(6) Uani 1 1 d . . . O5 O 0.5237(3) 0.74419(12) 0.6960(3) 0.0982(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0710(15) 0.0403(11) 0.0328(10) 0.0009(8) -0.0054(10) -0.0051(10) C2 0.0893(19) 0.0440(12) 0.0472(12) -0.0069(10) 0.0000(12) -0.0068(12) C3 0.102(2) 0.0540(15) 0.0532(14) -0.0067(11) 0.0089(14) 0.0078(15) C4 0.0796(19) 0.0729(18) 0.0579(15) 0.0037(13) 0.0129(13) 0.0105(15) C5 0.0704(17) 0.0568(14) 0.0530(13) 0.0063(11) 0.0005(12) -0.0053(12) C6 0.0654(15) 0.0415(11) 0.0345(10) 0.0032(8) -0.0043(9) -0.0039(10) C7 0.0683(14) 0.0363(10) 0.0353(10) 0.0025(8) -0.0090(9) -0.0061(10) C8 0.0679(14) 0.0332(10) 0.0330(10) 0.0027(8) -0.0061(9) -0.0022(10) C9 0.096(2) 0.0446(13) 0.0490(13) 0.0070(10) 0.0063(13) -0.0116(13) C10 0.131(3) 0.0601(16) 0.0668(17) 0.0255(13) 0.0162(17) 0.0004(17) C11 0.0792(16) 0.0431(12) 0.0405(11) -0.0036(9) -0.0047(10) 0.0013(11) C12 0.138(3) 0.0722(18) 0.0355(12) -0.0046(11) -0.0065(14) 0.0058(18) C13 0.0738(17) 0.0510(13) 0.0508(12) -0.0022(10) -0.0068(11) -0.0162(12) C14 0.0684(17) 0.0634(16) 0.0669(15) 0.0078(12) -0.0029(13) -0.0083(13) N1 0.0648(12) 0.0387(9) 0.0397(9) -0.0028(7) -0.0018(8) -0.0073(9) O1 0.0810(11) 0.0392(8) 0.0442(8) 0.0095(6) -0.0039(7) -0.0061(8) O2 0.1017(18) 0.0926(16) 0.1072(17) 0.0392(13) -0.0141(14) -0.0402(14) O3 0.0828(11) 0.0333(7) 0.0343(7) 0.0016(5) -0.0046(7) -0.0001(7) O4 0.1147(16) 0.0423(9) 0.0564(10) -0.0081(7) -0.0093(9) 0.0098(9) O5 0.1054(16) 0.0826(14) 0.1079(16) -0.0439(12) 0.0169(13) -0.0435(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.383(3) . ? C1 C6 1.394(3) . ? C1 N1 1.418(3) . ? C2 C3 1.374(4) . ? C2 H2 0.9300 . ? C3 C4 1.375(4) . ? C3 H3 0.9300 . ? C4 C5 1.383(4) . ? C4 H4 0.9300 . ? C5 C6 1.374(3) . ? C5 H5 0.9300 . ? C6 C7 1.494(3) . ? C7 O1 1.457(2) . ? C7 C8 1.520(3) . ? C7 H7 0.9800 . ? C8 O3 1.448(2) . ? C8 N1 1.450(2) . ? C8 H8 0.9800 . ? C9 O2 1.189(3) . ? C9 O1 1.344(3) . ? C9 C10 1.492(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 O4 1.193(3) . ? C11 O3 1.348(2) . ? C11 C12 1.490(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O5 1.210(3) . ? C13 N1 1.376(3) . ? C13 C14 1.493(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.0(2) . . ? C2 C1 N1 129.4(2) . . ? C6 C1 N1 109.61(18) . . ? C3 C2 C1 117.7(2) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 121.8(2) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C3 C4 C5 120.3(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 118.9(2) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C6 C1 120.2(2) . . ? C5 C6 C7 130.9(2) . . ? C1 C6 C7 108.9(2) . . ? O1 C7 C6 111.53(16) . . ? O1 C7 C8 105.53(17) . . ? C6 C7 C8 103.41(17) . . ? O1 C7 H7 112.0 . . ? C6 C7 H7 112.0 . . ? C8 C7 H7 112.0 . . ? O3 C8 N1 105.94(15) . . ? O3 C8 C7 110.04(17) . . ? N1 C8 C7 105.03(16) . . ? O3 C8 H8 111.8 . . ? N1 C8 H8 111.8 . . ? C7 C8 H8 111.8 . . ? O2 C9 O1 122.9(2) . . ? O2 C9 C10 125.8(3) . . ? O1 C9 C10 111.3(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O4 C11 O3 122.71(19) . . ? O4 C11 C12 126.5(2) . . ? O3 C11 C12 110.74(19) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O5 C13 N1 121.1(2) . . ? O5 C13 C14 121.6(2) . . ? N1 C13 C14 117.3(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 N1 C1 126.08(18) . . ? C13 N1 C8 124.50(19) . . ? C1 N1 C8 108.86(17) . . ? C9 O1 C7 116.62(19) . . ? C11 O3 C8 116.76(15) . . ? 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 C6 C1 C2 C3 -2.4(3) . . . . ? N1 C1 C2 C3 175.4(2) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C2 C3 C4 C5 1.7(4) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? C4 C5 C6 C1 -1.1(3) . . . . ? C4 C5 C6 C7 179.5(2) . . . . ? C2 C1 C6 C5 2.9(3) . . . . ? N1 C1 C6 C5 -175.25(18) . . . . ? C2 C1 C6 C7 -177.59(18) . . . . ? N1 C1 C6 C7 4.2(2) . . . . ? C5 C6 C7 O1 -82.9(3) . . . . ? C1 C6 C7 O1 97.74(19) . . . . ? C5 C6 C7 C8 164.2(2) . . . . ? C1 C6 C7 C8 -15.2(2) . . . . ? O1 C7 C8 O3 149.30(15) . . . . ? C6 C7 C8 O3 -93.45(18) . . . . ? O1 C7 C8 N1 -97.08(17) . . . . ? C6 C7 C8 N1 20.17(19) . . . . ? O5 C13 N1 C1 6.9(4) . . . . ? C14 C13 N1 C1 -172.4(2) . . . . ? O5 C13 N1 C8 177.3(2) . . . . ? C14 C13 N1 C8 -1.9(3) . . . . ? C2 C1 N1 C13 3.1(3) . . . . ? C6 C1 N1 C13 -178.91(18) . . . . ? C2 C1 N1 C8 -168.6(2) . . . . ? C6 C1 N1 C8 9.4(2) . . . . ? O3 C8 N1 C13 -74.0(2) . . . . ? C7 C8 N1 C13 169.51(19) . . . . ? O3 C8 N1 C1 97.81(18) . . . . ? C7 C8 N1 C1 -18.7(2) . . . . ? O2 C9 O1 C7 0.0(4) . . . . ? C10 C9 O1 C7 -179.5(2) . . . . ? C6 C7 O1 C9 89.0(2) . . . . ? C8 C7 O1 C9 -159.38(18) . . . . ? O4 C11 O3 C8 1.9(4) . . . . ? C12 C11 O3 C8 -178.9(2) . . . . ? N1 C8 O3 C11 165.63(19) . . . . ? C7 C8 O3 C11 -81.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.194 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.039