# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Nathan Schultheiss' 'Sarah Bethune' 'Jan-Olav Henck' _publ_contact_author_name 'Nathan Schultheiss' _publ_contact_author_email NATHAN.SCHULTHEISS@APTUIT.COM _publ_section_title ; Nutraceutical cocrystals: utilizing pterostilbene as a cocrystal former ; # Attachment '1.cif' data_215077 _database_code_depnum_ccdc_archive 'CCDC 764871' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 215077 (3694-81-02) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C8 H10 N4 O2) (C16 H16 O3) ; _chemical_formula_sum 'C24 H26 N4 O5' _chemical_formula_weight 450.49 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.4139(11) _cell_length_b 13.3693(8) _cell_length_c 18.4844(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.492(2) _cell_angle_gamma 90.00 _cell_volume 4303.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9953 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 30.50 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1904 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48373 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 33.14 _reflns_number_total 14776 _reflns_number_gt 9338 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.1000P)^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 14776 _refine_ls_number_parameters 611 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0935 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1833 _refine_ls_wR_factor_gt 0.1606 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 N11_1 N 0.02689(6) 0.15946(8) 0.78240(6) 0.0233(2) Uani 1 1 d . . . C11_1 C 0.11056(8) 0.15055(11) 0.78672(9) 0.0306(3) Uani 1 1 d . . . H11A_1 H 0.1310 0.1376 0.7384 0.046 Uiso 1 1 calc R . . H11B_1 H 0.1243 0.0951 0.8190 0.046 Uiso 1 1 calc R . . H11C_1 H 0.1324 0.2129 0.8057 0.046 Uiso 1 1 calc R . . C12_1 C -0.01050(8) 0.16531(9) 0.84897(7) 0.0233(3) Uani 1 1 d . . . O12_1 O 0.02490(6) 0.16469(8) 0.90574(6) 0.0316(2) Uani 1 1 d . . . N13_1 N -0.08897(6) 0.17154(8) 0.84733(6) 0.0232(2) Uani 1 1 d . . . C13_1 C -0.13020(9) 0.17572(11) 0.91567(7) 0.0304(3) Uani 1 1 d . . . H13A_1 H -0.1839 0.1939 0.9064 0.046 Uiso 1 1 calc R . . H13B_1 H -0.1064 0.2259 0.9473 0.046 Uiso 1 1 calc R . . H13C_1 H -0.1280 0.1101 0.9392 0.046 Uiso 1 1 calc R . . C14_1 C -0.12673(8) 0.17374(10) 0.78216(7) 0.0228(3) Uani 1 1 d . . . C15_1 C -0.08808(7) 0.16958(10) 0.71800(7) 0.0223(3) Uani 1 1 d . . . C16_1 C -0.00710(8) 0.16134(9) 0.71412(7) 0.0232(3) Uani 1 1 d . . . O16_1 O 0.03269(6) 0.15613(8) 0.65929(6) 0.0308(2) Uani 1 1 d . . . N17_1 N -0.14434(6) 0.17845(9) 0.66504(6) 0.0243(2) Uani 1 1 d . . . C17_1 C -0.13457(9) 0.18079(12) 0.58752(7) 0.0327(3) Uani 1 1 d . . . H17A_1 H -0.1843 0.1928 0.5639 0.049 Uiso 1 1 calc R . . H17B_1 H -0.1139 0.1166 0.5712 0.049 Uiso 1 1 calc R . . H17C_1 H -0.0989 0.2346 0.5748 0.049 Uiso 1 1 calc R . . C18_1 C -0.21101(8) 0.18555(11) 0.70101(8) 0.0297(3) Uani 1 1 d . . . H18_1 H -0.2593 0.1920 0.6772 0.036 Uiso 1 1 calc R . . N19_1 N -0.20350(6) 0.18284(9) 0.77254(7) 0.0282(3) Uani 1 1 d . . . C21_1 C 0.49813(8) 0.08630(10) 0.22076(7) 0.0233(3) Uani 1 1 d . . . O21_1 O 0.48680(6) 0.08496(8) 0.14754(5) 0.0325(2) Uani 1 1 d . . . C22_1 C 0.56983(8) 0.09478(9) 0.25324(7) 0.0228(3) Uani 1 1 d . . . H22_1 H 0.6149 0.0995 0.2249 0.027 Uiso 1 1 calc R . . C23_1 C 0.57404(7) 0.09627(9) 0.32830(7) 0.0219(3) Uani 1 1 d . . . O23_1 O 0.64661(5) 0.10664(7) 0.35644(5) 0.0267(2) Uani 1 1 d . . . C24_1 C 0.50860(7) 0.08916(9) 0.36991(7) 0.0220(3) Uani 1 1 d . . . H24_1 H 0.5126 0.0903 0.4212 0.026 Uiso 1 1 calc R . . C25_1 C 0.43646(7) 0.08024(9) 0.33656(7) 0.0209(2) Uani 1 1 d . . . C26_1 C 0.43174(8) 0.07912(10) 0.26145(7) 0.0232(3) Uani 1 1 d . . . H26_1 H 0.3832 0.0735 0.2380 0.028 Uiso 1 1 calc R . . C27_1 C 0.55090(9) 0.10548(12) 0.10279(8) 0.0323(3) Uani 1 1 d . . . H27A_1 H 0.5346 0.1047 0.0519 0.049 Uiso 1 1 calc R . . H27B_1 H 0.5905 0.0544 0.1107 0.049 Uiso 1 1 calc R . . H27C_1 H 0.5718 0.1715 0.1149 0.049 Uiso 1 1 calc R . . C28_1 C 0.65213(8) 0.11796(12) 0.43280(8) 0.0315(3) Uani 1 1 d . . . H28A_1 H 0.7055 0.1324 0.4465 0.047 Uiso 1 1 calc R . . H28B_1 H 0.6356 0.0560 0.4563 0.047 Uiso 1 1 calc R . . H28C_1 H 0.6191 0.1732 0.4482 0.047 Uiso 1 1 calc R . . C29_1 C 0.36865(7) 0.07757(10) 0.38259(7) 0.0224(3) Uani 1 1 d . . . H29_1 H 0.3771 0.0806 0.4334 0.027 Uiso 1 1 calc R . . C31_1 C 0.08938(8) 0.10293(10) 0.48020(7) 0.0244(3) Uani 1 1 d . . . O31_1 O 0.02155(6) 0.11775(9) 0.51434(6) 0.0335(2) Uani 1 1 d . . . H31_1 H 0.0322(11) 0.1295(13) 0.5639(11) 0.040 Uiso 1 1 d . . . C32_1 C 0.08720(8) 0.08291(11) 0.40705(8) 0.0294(3) Uani 1 1 d . . . H32_1 H 0.0392 0.0767 0.3826 0.035 Uiso 1 1 calc R . . C33_1 C 0.15473(8) 0.07183(11) 0.36941(7) 0.0274(3) Uani 1 1 d . . . H33_1 H 0.1523 0.0589 0.3189 0.033 Uiso 1 1 calc R . . C34_1 C 0.22661(7) 0.07900(10) 0.40328(7) 0.0221(3) Uani 1 1 d . . . C35_1 C 0.22728(8) 0.09717(10) 0.47774(7) 0.0245(3) Uani 1 1 d . . . H35_1 H 0.2750 0.1014 0.5028 0.029 Uiso 1 1 calc R . . C36_1 C 0.15984(8) 0.10914(10) 0.51562(7) 0.0242(3) Uani 1 1 d . . . H36_1 H 0.1617 0.1217 0.5662 0.029 Uiso 1 1 calc R . . C37_1 C 0.29583(8) 0.07125(10) 0.35973(7) 0.0245(3) Uani 1 1 d . . . H37_1 H 0.2883 0.0605 0.3094 0.029 Uiso 1 1 calc R . . N11_2 N 0.12308(6) 0.64318(8) 0.79312(6) 0.0231(2) Uani 1 1 d . . . C11_2 C 0.20598(8) 0.62580(11) 0.79703(9) 0.0301(3) Uani 1 1 d . . . H11A_2 H 0.2236 0.5976 0.7511 0.045 Uiso 1 1 calc R . . H11B_2 H 0.2175 0.5788 0.8364 0.045 Uiso 1 1 calc R . . H11C_2 H 0.2325 0.6893 0.8062 0.045 Uiso 1 1 calc R . . C12_2 C 0.08526(8) 0.64882(9) 0.85935(8) 0.0236(3) Uani 1 1 d . . . O12_2 O 0.11957(6) 0.63975(8) 0.91670(5) 0.0307(2) Uani 1 1 d . . . N13_2 N 0.00766(6) 0.66452(8) 0.85720(6) 0.0223(2) Uani 1 1 d . . . C13_2 C -0.03443(9) 0.66591(11) 0.92528(7) 0.0282(3) Uani 1 1 d . . . H13A_2 H -0.0869 0.6897 0.9164 0.042 Uiso 1 1 calc R . . H13B_2 H -0.0085 0.7108 0.9596 0.042 Uiso 1 1 calc R . . H13C_2 H -0.0361 0.5982 0.9455 0.042 Uiso 1 1 calc R . . C14_2 C -0.02950(8) 0.67022(9) 0.79242(7) 0.0220(3) Uani 1 1 d . . . C15_2 C 0.00903(7) 0.66285(10) 0.72807(7) 0.0220(3) Uani 1 1 d . . . C16_2 C 0.08949(8) 0.64881(9) 0.72475(7) 0.0225(3) Uani 1 1 d . . . O16_2 O 0.12967(6) 0.64145(8) 0.67018(5) 0.0300(2) Uani 1 1 d . . . N17_2 N -0.04682(6) 0.67185(9) 0.67512(6) 0.0245(2) Uani 1 1 d . . . C17_2 C -0.03728(9) 0.66663(12) 0.59735(7) 0.0323(3) Uani 1 1 d . . . H17A_2 H -0.0865 0.6805 0.5733 0.048 Uiso 1 1 calc R . . H17B_2 H -0.0196 0.5996 0.5840 0.048 Uiso 1 1 calc R . . H17C_2 H 0.0007 0.7163 0.5822 0.048 Uiso 1 1 calc R . . C18_2 C -0.11298(8) 0.68391(11) 0.71085(8) 0.0280(3) Uani 1 1 d . . . H18_2 H -0.1610 0.6919 0.6868 0.034 Uiso 1 1 calc R . . N19_2 N -0.10590(6) 0.68378(9) 0.78251(6) 0.0256(2) Uani 1 1 d . . . C21_2 C 0.60014(8) 0.60326(10) 0.23278(7) 0.0235(3) Uani 1 1 d . . . O21_2 O 0.58734(6) 0.60575(8) 0.16021(5) 0.0322(2) Uani 1 1 d . . . C22_2 C 0.67206(8) 0.61271(10) 0.26489(7) 0.0244(3) Uani 1 1 d . . . H22_2 H 0.7168 0.6193 0.2363 0.029 Uiso 1 1 calc R . . C23_2 C 0.67692(7) 0.61228(10) 0.33992(7) 0.0230(3) Uani 1 1 d . . . O23_2 O 0.74957(6) 0.62574(8) 0.36743(5) 0.0293(2) Uani 1 1 d . . . C24_2 C 0.61231(8) 0.60133(10) 0.38201(8) 0.0237(3) Uani 1 1 d . . . H24_2 H 0.6170 0.6001 0.4332 0.028 Uiso 1 1 calc R . . C25_2 C 0.53973(7) 0.59201(9) 0.34924(7) 0.0215(2) Uani 1 1 d . . . C26_2 C 0.53445(8) 0.59302(10) 0.27452(7) 0.0240(3) Uani 1 1 d . . . H26_2 H 0.4857 0.5867 0.2515 0.029 Uiso 1 1 calc R . . C27_2 C 0.65157(9) 0.61813(12) 0.11458(8) 0.0319(3) Uani 1 1 d . . . H27A_2 H 0.6345 0.6174 0.0639 0.048 Uiso 1 1 calc R . . H27B_2 H 0.6881 0.5634 0.1229 0.048 Uiso 1 1 calc R . . H27C_2 H 0.6766 0.6822 0.1253 0.048 Uiso 1 1 calc R . . C28_2 C 0.75473(8) 0.64858(12) 0.44232(8) 0.0301(3) Uani 1 1 d . . . H28A_2 H 0.8075 0.6682 0.4545 0.045 Uiso 1 1 calc R . . H28B_2 H 0.7405 0.5895 0.4706 0.045 Uiso 1 1 calc R . . H28C_2 H 0.7197 0.7038 0.4535 0.045 Uiso 1 1 calc R . . C29_2 C 0.47213(8) 0.58627(9) 0.39570(7) 0.0230(3) Uani 1 1 d . . . H29_2 H 0.4807 0.5849 0.4465 0.028 Uiso 1 1 calc R . . C31_2 C 0.19170(8) 0.59779(10) 0.49238(7) 0.0250(3) Uani 1 1 d . . . O31_2 O 0.12285(6) 0.60550(9) 0.52592(6) 0.0337(2) Uani 1 1 d . . . H31_2 H 0.1315(11) 0.6213(13) 0.5759(11) 0.040 Uiso 1 1 d . . . C32_2 C 0.19118(8) 0.56909(12) 0.42056(8) 0.0294(3) Uani 1 1 d . . . H32_2 H 0.1441 0.5527 0.3972 0.035 Uiso 1 1 calc R . . C33_2 C 0.25913(8) 0.56431(11) 0.38282(8) 0.0283(3) Uani 1 1 d . . . H33_2 H 0.2579 0.5455 0.3333 0.034 Uiso 1 1 calc R . . C34_2 C 0.32977(8) 0.58637(10) 0.41564(7) 0.0233(3) Uani 1 1 d . . . C35_2 C 0.32910(8) 0.61264(10) 0.48880(7) 0.0243(3) Uani 1 1 d . . . H35_2 H 0.3762 0.6265 0.5130 0.029 Uiso 1 1 calc R . . C36_2 C 0.26101(8) 0.61882(10) 0.52658(7) 0.0256(3) Uani 1 1 d . . . H36_2 H 0.2618 0.6376 0.5762 0.031 Uiso 1 1 calc R . . C37_2 C 0.39944(8) 0.58279(10) 0.37225(7) 0.0244(3) Uani 1 1 d . . . H37_2 H 0.3922 0.5773 0.3214 0.029 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 N11_1 0.0162(5) 0.0263(5) 0.0273(6) 0.0001(4) -0.0028(4) 0.0004(4) C11_1 0.0164(6) 0.0359(8) 0.0395(8) -0.0003(6) -0.0037(6) 0.0016(5) C12_1 0.0209(6) 0.0226(6) 0.0262(6) 0.0008(5) -0.0016(5) -0.0006(4) O12_1 0.0324(6) 0.0347(5) 0.0275(5) 0.0019(4) -0.0097(4) 0.0013(4) N13_1 0.0209(6) 0.0292(6) 0.0194(5) 0.0019(4) 0.0003(4) -0.0004(4) C13_1 0.0350(8) 0.0352(7) 0.0209(6) -0.0004(6) 0.0041(6) -0.0012(6) C14_1 0.0198(6) 0.0247(6) 0.0239(6) 0.0012(5) 0.0001(5) -0.0014(5) C15_1 0.0201(6) 0.0257(6) 0.0212(6) 0.0011(5) -0.0025(5) 0.0005(5) C16_1 0.0226(6) 0.0225(6) 0.0244(6) 0.0008(5) -0.0004(5) -0.0001(5) O16_1 0.0227(5) 0.0417(6) 0.0281(5) 0.0006(4) 0.0054(4) 0.0018(4) N17_1 0.0189(5) 0.0357(6) 0.0183(5) 0.0006(4) -0.0001(4) 0.0023(4) C17_1 0.0309(8) 0.0472(9) 0.0200(6) 0.0032(6) 0.0010(6) 0.0062(6) C18_1 0.0172(6) 0.0433(8) 0.0288(7) -0.0005(6) 0.0016(5) 0.0023(5) N19_1 0.0176(6) 0.0383(7) 0.0285(6) -0.0006(5) -0.0007(5) -0.0008(4) C21_1 0.0222(6) 0.0279(6) 0.0197(6) -0.0011(5) 0.0013(5) 0.0005(5) O21_1 0.0247(5) 0.0548(7) 0.0180(5) -0.0002(4) 0.0025(4) -0.0037(4) C22_1 0.0188(6) 0.0259(6) 0.0238(6) -0.0006(5) 0.0034(5) 0.0007(5) C23_1 0.0168(6) 0.0232(6) 0.0258(6) -0.0004(5) 0.0005(5) 0.0005(4) O23_1 0.0168(5) 0.0403(5) 0.0231(5) -0.0002(4) 0.0002(4) -0.0009(4) C24_1 0.0194(6) 0.0253(6) 0.0213(6) 0.0016(5) 0.0008(5) 0.0010(4) C25_1 0.0189(6) 0.0221(6) 0.0217(6) 0.0008(5) 0.0020(5) 0.0005(4) C26_1 0.0191(6) 0.0286(6) 0.0221(6) -0.0001(5) 0.0005(5) -0.0003(5) C27_1 0.0285(8) 0.0453(9) 0.0234(7) -0.0015(6) 0.0078(6) -0.0009(6) C28_1 0.0214(7) 0.0484(9) 0.0249(7) -0.0053(6) -0.0007(5) -0.0008(6) C29_1 0.0195(6) 0.0257(6) 0.0220(6) 0.0016(5) 0.0028(5) 0.0009(5) C31_1 0.0198(6) 0.0297(7) 0.0239(6) 0.0015(5) 0.0038(5) 0.0010(5) O31_1 0.0205(5) 0.0516(7) 0.0285(5) -0.0039(5) 0.0051(4) 0.0030(4) C32_1 0.0184(6) 0.0455(8) 0.0243(7) -0.0016(6) -0.0012(5) -0.0007(5) C33_1 0.0198(6) 0.0421(8) 0.0202(6) -0.0028(6) -0.0011(5) -0.0001(5) C34_1 0.0183(6) 0.0267(6) 0.0212(6) 0.0008(5) 0.0008(5) -0.0010(4) C35_1 0.0200(6) 0.0313(7) 0.0222(6) 0.0002(5) -0.0020(5) 0.0002(5) C36_1 0.0214(6) 0.0308(7) 0.0205(6) -0.0006(5) 0.0007(5) 0.0008(5) C37_1 0.0198(6) 0.0316(7) 0.0220(6) -0.0022(5) 0.0014(5) -0.0013(5) N11_2 0.0166(5) 0.0268(6) 0.0259(6) 0.0022(4) -0.0010(4) -0.0005(4) C11_2 0.0160(6) 0.0389(8) 0.0354(8) 0.0011(6) -0.0025(5) 0.0037(5) C12_2 0.0204(6) 0.0227(6) 0.0277(7) 0.0023(5) -0.0002(5) -0.0013(5) O12_2 0.0296(5) 0.0367(5) 0.0258(5) 0.0026(4) -0.0071(4) 0.0007(4) N13_2 0.0199(5) 0.0284(6) 0.0186(5) 0.0008(4) 0.0012(4) -0.0008(4) C13_2 0.0326(8) 0.0325(7) 0.0195(6) 0.0007(5) 0.0037(5) 0.0004(5) C14_2 0.0187(6) 0.0239(6) 0.0234(6) 0.0001(5) 0.0012(5) -0.0010(4) C15_2 0.0195(6) 0.0262(6) 0.0203(6) 0.0007(5) -0.0030(5) -0.0008(4) C16_2 0.0208(6) 0.0231(6) 0.0237(6) 0.0020(5) 0.0005(5) -0.0017(5) O16_2 0.0231(5) 0.0400(6) 0.0271(5) 0.0007(4) 0.0045(4) 0.0019(4) N17_2 0.0185(5) 0.0356(6) 0.0193(5) 0.0013(5) 0.0006(4) 0.0013(4) C17_2 0.0302(8) 0.0483(9) 0.0184(6) 0.0012(6) 0.0005(6) 0.0050(6) C18_2 0.0169(6) 0.0393(8) 0.0278(7) 0.0002(6) 0.0002(5) 0.0019(5) N19_2 0.0172(5) 0.0328(6) 0.0269(6) 0.0004(5) 0.0008(4) 0.0008(4) C21_2 0.0209(6) 0.0278(6) 0.0218(6) -0.0010(5) 0.0000(5) 0.0016(5) O21_2 0.0220(5) 0.0553(7) 0.0193(5) -0.0001(4) 0.0014(4) -0.0009(4) C22_2 0.0201(6) 0.0275(6) 0.0257(6) -0.0006(5) 0.0025(5) 0.0004(5) C23_2 0.0183(6) 0.0248(6) 0.0258(6) -0.0017(5) -0.0013(5) 0.0015(4) O23_2 0.0185(5) 0.0439(6) 0.0257(5) -0.0037(4) -0.0013(4) -0.0001(4) C24_2 0.0198(6) 0.0272(6) 0.0240(6) -0.0004(5) -0.0002(5) 0.0015(5) C25_2 0.0189(6) 0.0223(6) 0.0233(6) -0.0003(5) 0.0011(5) 0.0019(4) C26_2 0.0183(6) 0.0291(7) 0.0245(6) 0.0003(5) -0.0005(5) 0.0014(5) C27_2 0.0264(7) 0.0452(9) 0.0243(7) -0.0028(6) 0.0081(6) 0.0019(6) C28_2 0.0212(7) 0.0409(8) 0.0282(7) -0.0054(6) -0.0031(5) 0.0010(5) C29_2 0.0205(6) 0.0254(6) 0.0231(6) 0.0000(5) 0.0017(5) 0.0009(5) C31_2 0.0205(6) 0.0309(7) 0.0237(6) 0.0058(5) 0.0027(5) 0.0016(5) O31_2 0.0202(5) 0.0553(7) 0.0256(5) 0.0036(5) 0.0048(4) -0.0005(4) C32_2 0.0180(6) 0.0461(8) 0.0241(7) 0.0020(6) -0.0023(5) -0.0003(5) C33_2 0.0192(6) 0.0432(8) 0.0224(6) -0.0005(6) -0.0020(5) 0.0013(5) C34_2 0.0189(6) 0.0270(6) 0.0239(6) 0.0019(5) 0.0008(5) 0.0011(5) C35_2 0.0192(6) 0.0298(7) 0.0240(6) -0.0012(5) -0.0010(5) -0.0014(5) C36_2 0.0237(7) 0.0318(7) 0.0214(6) 0.0003(5) 0.0003(5) -0.0006(5) C37_2 0.0204(6) 0.0313(7) 0.0215(6) -0.0007(5) 0.0013(5) 0.0003(5) _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 N11_1 C16_1 1.3896(17) . ? N11_1 C12_1 1.3993(18) . ? N11_1 C11_1 1.4633(17) . ? C11_1 H11A_1 0.9800 . ? C11_1 H11B_1 0.9800 . ? C11_1 H11C_1 0.9800 . ? C12_1 O12_1 1.2124(16) . ? C12_1 N13_1 1.3692(17) . ? N13_1 C14_1 1.3676(17) . ? N13_1 C13_1 1.4594(17) . ? C13_1 H13A_1 0.9800 . ? C13_1 H13B_1 0.9800 . ? C13_1 H13C_1 0.9800 . ? C14_1 N19_1 1.3527(17) . ? C14_1 C15_1 1.3698(19) . ? C15_1 N17_1 1.3841(16) . ? C15_1 C16_1 1.4169(19) . ? C16_1 O16_1 1.2347(17) . ? N17_1 C18_1 1.3461(17) . ? N17_1 C17_1 1.4449(17) . ? C17_1 H17A_1 0.9800 . ? C17_1 H17B_1 0.9800 . ? C17_1 H17C_1 0.9800 . ? C18_1 N19_1 1.3280(18) . ? C18_1 H18_1 0.9500 . ? C21_1 O21_1 1.3662(16) . ? C21_1 C22_1 1.3854(19) . ? C21_1 C26_1 1.3878(19) . ? O21_1 C27_1 1.4218(17) . ? C22_1 C23_1 1.3888(18) . ? C22_1 H22_1 0.9500 . ? C23_1 O23_1 1.3695(16) . ? C23_1 C24_1 1.3836(18) . ? O23_1 C28_1 1.4219(17) . ? C24_1 C25_1 1.3997(18) . ? C24_1 H24_1 0.9500 . ? C25_1 C26_1 1.3903(18) . ? C25_1 C29_1 1.4617(18) . ? C26_1 H26_1 0.9500 . ? C27_1 H27A_1 0.9800 . ? C27_1 H27B_1 0.9800 . ? C27_1 H27C_1 0.9800 . ? C28_1 H28A_1 0.9800 . ? C28_1 H28B_1 0.9800 . ? C28_1 H28C_1 0.9800 . ? C29_1 C37_1 1.3359(19) . ? C29_1 H29_1 0.9500 . ? C31_1 O31_1 1.3584(16) . ? C31_1 C32_1 1.3787(19) . ? C31_1 C36_1 1.3882(19) . ? O31_1 H31_1 0.95(2) . ? C32_1 C33_1 1.3794(19) . ? C32_1 H32_1 0.9500 . ? C33_1 C34_1 1.3981(18) . ? C33_1 H33_1 0.9500 . ? C34_1 C35_1 1.3975(18) . ? C34_1 C37_1 1.4588(18) . ? C35_1 C36_1 1.3818(19) . ? C35_1 H35_1 0.9500 . ? C36_1 H36_1 0.9500 . ? C37_1 H37_1 0.9500 . ? N11_2 C16_2 1.3899(17) . ? N11_2 C12_2 1.3972(18) . ? N11_2 C11_2 1.4635(17) . ? C11_2 H11A_2 0.9800 . ? C11_2 H11B_2 0.9800 . ? C11_2 H11C_2 0.9800 . ? C12_2 O12_2 1.2183(16) . ? C12_2 N13_2 1.3677(17) . ? N13_2 C14_2 1.3584(17) . ? N13_2 C13_2 1.4619(17) . ? C13_2 H13A_2 0.9800 . ? C13_2 H13B_2 0.9800 . ? C13_2 H13C_2 0.9800 . ? C14_2 N19_2 1.3536(17) . ? C14_2 C15_2 1.3742(18) . ? C15_2 N17_2 1.3791(16) . ? C15_2 C16_2 1.4155(18) . ? C16_2 O16_2 1.2364(16) . ? N17_2 C18_2 1.3426(17) . ? N17_2 C17_2 1.4502(17) . ? C17_2 H17A_2 0.9800 . ? C17_2 H17B_2 0.9800 . ? C17_2 H17C_2 0.9800 . ? C18_2 N19_2 1.3292(18) . ? C18_2 H18_2 0.9500 . ? C21_2 O21_2 1.3584(16) . ? C21_2 C22_2 1.3869(19) . ? C21_2 C26_2 1.3921(19) . ? O21_2 C27_2 1.4163(17) . ? C22_2 C23_2 1.3887(19) . ? C22_2 H22_2 0.9500 . ? C23_2 O23_2 1.3712(16) . ? C23_2 C24_2 1.3812(19) . ? O23_2 C28_2 1.4197(17) . ? C24_2 C25_2 1.4024(18) . ? C24_2 H24_2 0.9500 . ? C25_2 C26_2 1.3836(18) . ? C25_2 C29_2 1.4651(19) . ? C26_2 H26_2 0.9500 . ? C27_2 H27A_2 0.9800 . ? C27_2 H27B_2 0.9800 . ? C27_2 H27C_2 0.9800 . ? C28_2 H28A_2 0.9800 . ? C28_2 H28B_2 0.9800 . ? C28_2 H28C_2 0.9800 . ? C29_2 C37_2 1.3353(19) . ? C29_2 H29_2 0.9500 . ? C31_2 O31_2 1.3583(17) . ? C31_2 C32_2 1.3820(19) . ? C31_2 C36_2 1.3865(19) . ? O31_2 H31_2 0.96(2) . ? C32_2 C33_2 1.3803(19) . ? C32_2 H32_2 0.9500 . ? C33_2 C34_2 1.3983(19) . ? C33_2 H33_2 0.9500 . ? C34_2 C35_2 1.3973(19) . ? C34_2 C37_2 1.4608(19) . ? C35_2 C36_2 1.3837(19) . ? C35_2 H35_2 0.9500 . ? C36_2 H36_2 0.9500 . ? C37_2 H37_2 0.9500 . ? 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 C16_1 N11_1 C12_1 126.87(11) . . ? C16_1 N11_1 C11_1 117.85(12) . . ? C12_1 N11_1 C11_1 115.29(11) . . ? N11_1 C11_1 H11A_1 109.5 . . ? N11_1 C11_1 H11B_1 109.5 . . ? H11A_1 C11_1 H11B_1 109.5 . . ? N11_1 C11_1 H11C_1 109.5 . . ? H11A_1 C11_1 H11C_1 109.5 . . ? H11B_1 C11_1 H11C_1 109.5 . . ? O12_1 C12_1 N13_1 121.30(13) . . ? O12_1 C12_1 N11_1 121.59(12) . . ? N13_1 C12_1 N11_1 117.11(11) . . ? C14_1 N13_1 C12_1 119.54(11) . . ? C14_1 N13_1 C13_1 121.68(12) . . ? C12_1 N13_1 C13_1 118.78(11) . . ? N13_1 C13_1 H13A_1 109.5 . . ? N13_1 C13_1 H13B_1 109.5 . . ? H13A_1 C13_1 H13B_1 109.5 . . ? N13_1 C13_1 H13C_1 109.5 . . ? H13A_1 C13_1 H13C_1 109.5 . . ? H13B_1 C13_1 H13C_1 109.5 . . ? N19_1 C14_1 N13_1 125.80(12) . . ? N19_1 C14_1 C15_1 112.47(12) . . ? N13_1 C14_1 C15_1 121.71(12) . . ? C14_1 C15_1 N17_1 105.00(11) . . ? C14_1 C15_1 C16_1 122.93(12) . . ? N17_1 C15_1 C16_1 132.04(12) . . ? O16_1 C16_1 N11_1 120.46(12) . . ? O16_1 C16_1 C15_1 127.72(13) . . ? N11_1 C16_1 C15_1 111.83(12) . . ? C18_1 N17_1 C15_1 105.37(11) . . ? C18_1 N17_1 C17_1 126.70(12) . . ? C15_1 N17_1 C17_1 127.92(12) . . ? N17_1 C17_1 H17A_1 109.5 . . ? N17_1 C17_1 H17B_1 109.5 . . ? H17A_1 C17_1 H17B_1 109.5 . . ? N17_1 C17_1 H17C_1 109.5 . . ? H17A_1 C17_1 H17C_1 109.5 . . ? H17B_1 C17_1 H17C_1 109.5 . . ? N19_1 C18_1 N17_1 114.32(12) . . ? N19_1 C18_1 H18_1 122.8 . . ? N17_1 C18_1 H18_1 122.8 . . ? C18_1 N19_1 C14_1 102.84(12) . . ? O21_1 C21_1 C22_1 123.52(12) . . ? O21_1 C21_1 C26_1 114.97(12) . . ? C22_1 C21_1 C26_1 121.51(12) . . ? C21_1 O21_1 C27_1 117.80(11) . . ? C21_1 C22_1 C23_1 118.28(12) . . ? C21_1 C22_1 H22_1 120.9 . . ? C23_1 C22_1 H22_1 120.9 . . ? O23_1 C23_1 C24_1 123.88(12) . . ? O23_1 C23_1 C22_1 114.93(11) . . ? C24_1 C23_1 C22_1 121.18(12) . . ? C23_1 O23_1 C28_1 116.24(10) . . ? C23_1 C24_1 C25_1 120.09(12) . . ? C23_1 C24_1 H24_1 120.0 . . ? C25_1 C24_1 H24_1 120.0 . . ? C26_1 C25_1 C24_1 119.07(12) . . ? C26_1 C25_1 C29_1 122.68(12) . . ? C24_1 C25_1 C29_1 118.18(12) . . ? C21_1 C26_1 C25_1 119.88(12) . . ? C21_1 C26_1 H26_1 120.1 . . ? C25_1 C26_1 H26_1 120.1 . . ? O21_1 C27_1 H27A_1 109.5 . . ? O21_1 C27_1 H27B_1 109.5 . . ? H27A_1 C27_1 H27B_1 109.5 . . ? O21_1 C27_1 H27C_1 109.5 . . ? H27A_1 C27_1 H27C_1 109.5 . . ? H27B_1 C27_1 H27C_1 109.5 . . ? O23_1 C28_1 H28A_1 109.5 . . ? O23_1 C28_1 H28B_1 109.5 . . ? H28A_1 C28_1 H28B_1 109.5 . . ? O23_1 C28_1 H28C_1 109.5 . . ? H28A_1 C28_1 H28C_1 109.5 . . ? H28B_1 C28_1 H28C_1 109.5 . . ? C37_1 C29_1 C25_1 125.93(13) . . ? C37_1 C29_1 H29_1 117.0 . . ? C25_1 C29_1 H29_1 117.0 . . ? O31_1 C31_1 C32_1 117.86(13) . . ? O31_1 C31_1 C36_1 122.73(13) . . ? C32_1 C31_1 C36_1 119.40(13) . . ? C31_1 O31_1 H31_1 108.1(12) . . ? C31_1 C32_1 C33_1 119.94(13) . . ? C31_1 C32_1 H32_1 120.0 . . ? C33_1 C32_1 H32_1 120.0 . . ? C32_1 C33_1 C34_1 122.05(13) . . ? C32_1 C33_1 H33_1 119.0 . . ? C34_1 C33_1 H33_1 119.0 . . ? C35_1 C34_1 C33_1 116.92(12) . . ? C35_1 C34_1 C37_1 123.77(12) . . ? C33_1 C34_1 C37_1 119.27(12) . . ? C36_1 C35_1 C34_1 121.29(12) . . ? C36_1 C35_1 H35_1 119.4 . . ? C34_1 C35_1 H35_1 119.4 . . ? C35_1 C36_1 C31_1 120.38(13) . . ? C35_1 C36_1 H36_1 119.8 . . ? C31_1 C36_1 H36_1 119.8 . . ? C29_1 C37_1 C34_1 127.41(13) . . ? C29_1 C37_1 H37_1 116.3 . . ? C34_1 C37_1 H37_1 116.3 . . ? C16_2 N11_2 C12_2 126.58(11) . . ? C16_2 N11_2 C11_2 117.43(11) . . ? C12_2 N11_2 C11_2 115.94(11) . . ? N11_2 C11_2 H11A_2 109.5 . . ? N11_2 C11_2 H11B_2 109.5 . . ? H11A_2 C11_2 H11B_2 109.5 . . ? N11_2 C11_2 H11C_2 109.5 . . ? H11A_2 C11_2 H11C_2 109.5 . . ? H11B_2 C11_2 H11C_2 109.5 . . ? O12_2 C12_2 N13_2 121.17(13) . . ? O12_2 C12_2 N11_2 121.71(12) . . ? N13_2 C12_2 N11_2 117.11(11) . . ? C14_2 N13_2 C12_2 119.83(11) . . ? C14_2 N13_2 C13_2 121.30(12) . . ? C12_2 N13_2 C13_2 118.65(11) . . ? N13_2 C13_2 H13A_2 109.5 . . ? N13_2 C13_2 H13B_2 109.5 . . ? H13A_2 C13_2 H13B_2 109.5 . . ? N13_2 C13_2 H13C_2 109.5 . . ? H13A_2 C13_2 H13C_2 109.5 . . ? H13B_2 C13_2 H13C_2 109.5 . . ? N19_2 C14_2 N13_2 125.96(12) . . ? N19_2 C14_2 C15_2 112.28(12) . . ? N13_2 C14_2 C15_2 121.77(12) . . ? C14_2 C15_2 N17_2 105.15(11) . . ? C14_2 C15_2 C16_2 122.54(12) . . ? N17_2 C15_2 C16_2 132.31(12) . . ? O16_2 C16_2 N11_2 120.05(12) . . ? O16_2 C16_2 C15_2 127.82(13) . . ? N11_2 C16_2 C15_2 112.13(12) . . ? C18_2 N17_2 C15_2 105.33(11) . . ? C18_2 N17_2 C17_2 126.83(12) . . ? C15_2 N17_2 C17_2 127.82(12) . . ? N17_2 C17_2 H17A_2 109.5 . . ? N17_2 C17_2 H17B_2 109.5 . . ? H17A_2 C17_2 H17B_2 109.5 . . ? N17_2 C17_2 H17C_2 109.5 . . ? H17A_2 C17_2 H17C_2 109.5 . . ? H17B_2 C17_2 H17C_2 109.5 . . ? N19_2 C18_2 N17_2 114.66(12) . . ? N19_2 C18_2 H18_2 122.7 . . ? N17_2 C18_2 H18_2 122.7 . . ? C18_2 N19_2 C14_2 102.58(11) . . ? O21_2 C21_2 C22_2 124.08(12) . . ? O21_2 C21_2 C26_2 114.90(12) . . ? C22_2 C21_2 C26_2 121.00(13) . . ? C21_2 O21_2 C27_2 117.85(11) . . ? C21_2 C22_2 C23_2 118.30(12) . . ? C21_2 C22_2 H22_2 120.8 . . ? C23_2 C22_2 H22_2 120.8 . . ? O23_2 C23_2 C24_2 123.94(12) . . ? O23_2 C23_2 C22_2 114.71(12) . . ? C24_2 C23_2 C22_2 121.33(12) . . ? C23_2 O23_2 C28_2 116.13(11) . . ? C23_2 C24_2 C25_2 120.11(13) . . ? C23_2 C24_2 H24_2 119.9 . . ? C25_2 C24_2 H24_2 119.9 . . ? C26_2 C25_2 C24_2 118.83(12) . . ? C26_2 C25_2 C29_2 122.60(12) . . ? C24_2 C25_2 C29_2 118.51(12) . . ? C25_2 C26_2 C21_2 120.42(13) . . ? C25_2 C26_2 H26_2 119.8 . . ? C21_2 C26_2 H26_2 119.8 . . ? O21_2 C27_2 H27A_2 109.5 . . ? O21_2 C27_2 H27B_2 109.5 . . ? H27A_2 C27_2 H27B_2 109.5 . . ? O21_2 C27_2 H27C_2 109.5 . . ? H27A_2 C27_2 H27C_2 109.5 . . ? H27B_2 C27_2 H27C_2 109.5 . . ? O23_2 C28_2 H28A_2 109.5 . . ? O23_2 C28_2 H28B_2 109.5 . . ? H28A_2 C28_2 H28B_2 109.5 . . ? O23_2 C28_2 H28C_2 109.5 . . ? H28A_2 C28_2 H28C_2 109.5 . . ? H28B_2 C28_2 H28C_2 109.5 . . ? C37_2 C29_2 C25_2 125.16(13) . . ? C37_2 C29_2 H29_2 117.4 . . ? C25_2 C29_2 H29_2 117.4 . . ? O31_2 C31_2 C32_2 117.45(13) . . ? O31_2 C31_2 C36_2 123.02(13) . . ? C32_2 C31_2 C36_2 119.52(13) . . ? C31_2 O31_2 H31_2 108.9(12) . . ? C33_2 C32_2 C31_2 119.99(13) . . ? C33_2 C32_2 H32_2 120.0 . . ? C31_2 C32_2 H32_2 120.0 . . ? C32_2 C33_2 C34_2 121.72(13) . . ? C32_2 C33_2 H33_2 119.1 . . ? C34_2 C33_2 H33_2 119.1 . . ? C35_2 C34_2 C33_2 117.27(12) . . ? C35_2 C34_2 C37_2 123.61(12) . . ? C33_2 C34_2 C37_2 119.11(12) . . ? C36_2 C35_2 C34_2 121.19(12) . . ? C36_2 C35_2 H35_2 119.4 . . ? C34_2 C35_2 H35_2 119.4 . . ? C35_2 C36_2 C31_2 120.28(13) . . ? C35_2 C36_2 H36_2 119.9 . . ? C31_2 C36_2 H36_2 119.9 . . ? C29_2 C37_2 C34_2 127.59(13) . . ? C29_2 C37_2 H37_2 116.2 . . ? C34_2 C37_2 H37_2 116.2 . . ? 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 C16_1 N11_1 C12_1 O12_1 -178.72(12) . . . . ? C11_1 N11_1 C12_1 O12_1 1.22(18) . . . . ? C16_1 N11_1 C12_1 N13_1 1.43(19) . . . . ? C11_1 N11_1 C12_1 N13_1 -178.63(11) . . . . ? O12_1 C12_1 N13_1 C14_1 178.89(12) . . . . ? N11_1 C12_1 N13_1 C14_1 -1.25(17) . . . . ? O12_1 C12_1 N13_1 C13_1 -1.08(18) . . . . ? N11_1 C12_1 N13_1 C13_1 178.77(11) . . . . ? C12_1 N13_1 C14_1 N19_1 -177.84(12) . . . . ? C13_1 N13_1 C14_1 N19_1 2.1(2) . . . . ? C12_1 N13_1 C14_1 C15_1 0.19(19) . . . . ? C13_1 N13_1 C14_1 C15_1 -179.83(12) . . . . ? N19_1 C14_1 C15_1 N17_1 1.10(15) . . . . ? N13_1 C14_1 C15_1 N17_1 -177.17(12) . . . . ? N19_1 C14_1 C15_1 C16_1 179.18(12) . . . . ? N13_1 C14_1 C15_1 C16_1 0.9(2) . . . . ? C12_1 N11_1 C16_1 O16_1 179.58(12) . . . . ? C11_1 N11_1 C16_1 O16_1 -0.36(18) . . . . ? C12_1 N11_1 C16_1 C15_1 -0.40(18) . . . . ? C11_1 N11_1 C16_1 C15_1 179.65(11) . . . . ? C14_1 C15_1 C16_1 O16_1 179.24(13) . . . . ? N17_1 C15_1 C16_1 O16_1 -3.3(2) . . . . ? C14_1 C15_1 C16_1 N11_1 -0.77(18) . . . . ? N17_1 C15_1 C16_1 N11_1 176.73(13) . . . . ? C14_1 C15_1 N17_1 C18_1 -0.89(14) . . . . ? C16_1 C15_1 N17_1 C18_1 -178.72(14) . . . . ? C14_1 C15_1 N17_1 C17_1 178.51(13) . . . . ? C16_1 C15_1 N17_1 C17_1 0.7(2) . . . . ? C15_1 N17_1 C18_1 N19_1 0.44(17) . . . . ? C17_1 N17_1 C18_1 N19_1 -178.97(13) . . . . ? N17_1 C18_1 N19_1 C14_1 0.22(16) . . . . ? N13_1 C14_1 N19_1 C18_1 177.36(13) . . . . ? C15_1 C14_1 N19_1 C18_1 -0.83(15) . . . . ? C22_1 C21_1 O21_1 C27_1 -7.88(19) . . . . ? C26_1 C21_1 O21_1 C27_1 171.71(12) . . . . ? O21_1 C21_1 C22_1 C23_1 179.39(12) . . . . ? C26_1 C21_1 C22_1 C23_1 -0.18(19) . . . . ? C21_1 C22_1 C23_1 O23_1 -178.87(11) . . . . ? C21_1 C22_1 C23_1 C24_1 0.21(19) . . . . ? C24_1 C23_1 O23_1 C28_1 -4.81(18) . . . . ? C22_1 C23_1 O23_1 C28_1 174.24(12) . . . . ? O23_1 C23_1 C24_1 C25_1 179.02(11) . . . . ? C22_1 C23_1 C24_1 C25_1 0.03(19) . . . . ? C23_1 C24_1 C25_1 C26_1 -0.30(18) . . . . ? C23_1 C24_1 C25_1 C29_1 -177.24(12) . . . . ? O21_1 C21_1 C26_1 C25_1 -179.69(11) . . . . ? C22_1 C21_1 C26_1 C25_1 -0.09(19) . . . . ? C24_1 C25_1 C26_1 C21_1 0.33(19) . . . . ? C29_1 C25_1 C26_1 C21_1 177.13(12) . . . . ? C26_1 C25_1 C29_1 C37_1 1.8(2) . . . . ? C24_1 C25_1 C29_1 C37_1 178.67(13) . . . . ? O31_1 C31_1 C32_1 C33_1 177.06(13) . . . . ? C36_1 C31_1 C32_1 C33_1 -1.7(2) . . . . ? C31_1 C32_1 C33_1 C34_1 0.8(2) . . . . ? C32_1 C33_1 C34_1 C35_1 0.6(2) . . . . ? C32_1 C33_1 C34_1 C37_1 -177.11(13) . . . . ? C33_1 C34_1 C35_1 C36_1 -1.08(19) . . . . ? C37_1 C34_1 C35_1 C36_1 176.47(13) . . . . ? C34_1 C35_1 C36_1 C31_1 0.2(2) . . . . ? O31_1 C31_1 C36_1 C35_1 -177.51(13) . . . . ? C32_1 C31_1 C36_1 C35_1 1.2(2) . . . . ? C25_1 C29_1 C37_1 C34_1 -172.97(13) . . . . ? C35_1 C34_1 C37_1 C29_1 1.6(2) . . . . ? C33_1 C34_1 C37_1 C29_1 179.10(13) . . . . ? C16_2 N11_2 C12_2 O12_2 177.52(12) . . . . ? C11_2 N11_2 C12_2 O12_2 0.00(18) . . . . ? C16_2 N11_2 C12_2 N13_2 -2.16(18) . . . . ? C11_2 N11_2 C12_2 N13_2 -179.68(11) . . . . ? O12_2 C12_2 N13_2 C14_2 -177.29(12) . . . . ? N11_2 C12_2 N13_2 C14_2 2.39(17) . . . . ? O12_2 C12_2 N13_2 C13_2 -2.66(18) . . . . ? N11_2 C12_2 N13_2 C13_2 177.02(11) . . . . ? C12_2 N13_2 C14_2 N19_2 178.84(12) . . . . ? C13_2 N13_2 C14_2 N19_2 4.4(2) . . . . ? C12_2 N13_2 C14_2 C15_2 -1.48(18) . . . . ? C13_2 N13_2 C14_2 C15_2 -175.97(12) . . . . ? N19_2 C14_2 C15_2 N17_2 -0.32(15) . . . . ? N13_2 C14_2 C15_2 N17_2 179.96(11) . . . . ? N19_2 C14_2 C15_2 C16_2 179.78(12) . . . . ? N13_2 C14_2 C15_2 C16_2 0.1(2) . . . . ? C12_2 N11_2 C16_2 O16_2 -179.08(12) . . . . ? C11_2 N11_2 C16_2 O16_2 -1.59(18) . . . . ? C12_2 N11_2 C16_2 C15_2 0.79(17) . . . . ? C11_2 N11_2 C16_2 C15_2 178.28(11) . . . . ? C14_2 C15_2 C16_2 O16_2 -179.85(13) . . . . ? N17_2 C15_2 C16_2 O16_2 0.3(2) . . . . ? C14_2 C15_2 C16_2 N11_2 0.29(17) . . . . ? N17_2 C15_2 C16_2 N11_2 -179.58(13) . . . . ? C14_2 C15_2 N17_2 C18_2 0.15(14) . . . . ? C16_2 C15_2 N17_2 C18_2 -179.96(14) . . . . ? C14_2 C15_2 N17_2 C17_2 -178.22(13) . . . . ? C16_2 C15_2 N17_2 C17_2 1.7(2) . . . . ? C15_2 N17_2 C18_2 N19_2 0.06(16) . . . . ? C17_2 N17_2 C18_2 N19_2 178.45(13) . . . . ? N17_2 C18_2 N19_2 C14_2 -0.25(16) . . . . ? N13_2 C14_2 N19_2 C18_2 -179.95(13) . . . . ? C15_2 C14_2 N19_2 C18_2 0.34(15) . . . . ? C22_2 C21_2 O21_2 C27_2 0.4(2) . . . . ? C26_2 C21_2 O21_2 C27_2 178.72(12) . . . . ? O21_2 C21_2 C22_2 C23_2 177.84(12) . . . . ? C26_2 C21_2 C22_2 C23_2 -0.4(2) . . . . ? C21_2 C22_2 C23_2 O23_2 -177.65(12) . . . . ? C21_2 C22_2 C23_2 C24_2 0.91(19) . . . . ? C24_2 C23_2 O23_2 C28_2 -12.45(18) . . . . ? C22_2 C23_2 O23_2 C28_2 166.07(12) . . . . ? O23_2 C23_2 C24_2 C25_2 177.37(12) . . . . ? C22_2 C23_2 C24_2 C25_2 -1.06(19) . . . . ? C23_2 C24_2 C25_2 C26_2 0.62(19) . . . . ? C23_2 C24_2 C25_2 C29_2 -176.57(12) . . . . ? C24_2 C25_2 C26_2 C21_2 -0.08(19) . . . . ? C29_2 C25_2 C26_2 C21_2 176.99(12) . . . . ? O21_2 C21_2 C26_2 C25_2 -178.40(11) . . . . ? C22_2 C21_2 C26_2 C25_2 0.0(2) . . . . ? C26_2 C25_2 C29_2 C37_2 -0.9(2) . . . . ? C24_2 C25_2 C29_2 C37_2 176.15(13) . . . . ? O31_2 C31_2 C32_2 C33_2 177.13(13) . . . . ? C36_2 C31_2 C32_2 C33_2 -1.8(2) . . . . ? C31_2 C32_2 C33_2 C34_2 1.0(2) . . . . ? C32_2 C33_2 C34_2 C35_2 0.6(2) . . . . ? C32_2 C33_2 C34_2 C37_2 -178.22(13) . . . . ? C33_2 C34_2 C35_2 C36_2 -1.5(2) . . . . ? C37_2 C34_2 C35_2 C36_2 177.30(13) . . . . ? C34_2 C35_2 C36_2 C31_2 0.7(2) . . . . ? O31_2 C31_2 C36_2 C35_2 -177.92(12) . . . . ? C32_2 C31_2 C36_2 C35_2 1.0(2) . . . . ? C25_2 C29_2 C37_2 C34_2 -173.82(12) . . . . ? C35_2 C34_2 C37_2 C29_2 12.3(2) . . . . ? C33_2 C34_2 C37_2 C29_2 -168.91(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O31_1 H31_1 O16_1 0.95(2) 1.80(2) 2.7331(15) 168.9(18) . O31_2 H31_2 O16_2 0.96(2) 1.76(2) 2.7112(15) 169.0(17) . _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.620 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.061 # Attachment '2.cif' data_204542 _database_code_depnum_ccdc_archive 'CCDC 764872' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 204542 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C16 H16 O3) (C8 H10 N4 O2) ; _chemical_formula_sum 'C24 H26 N4 O5' _chemical_formula_weight 450.49 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.424(2) _cell_length_b 26.809(4) _cell_length_c 18.546(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.225(5) _cell_angle_gamma 90.00 _cell_volume 8663.1(18) _cell_formula_units_Z 16 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9845 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 31.31 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3808 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 99700 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.0688 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 0.76 _diffrn_reflns_theta_max 32.03 _reflns_number_total 28191 _reflns_number_gt 16287 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0850P)^2^+4.0000P] 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 28191 _refine_ls_number_parameters 1222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1316 _refine_ls_R_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.2094 _refine_ls_wR_factor_gt 0.1796 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 N11_1 N 0.32556(10) 0.19049(7) 0.79350(11) 0.0325(4) Uani 1 1 d . . . C11_1 C 0.24240(13) 0.18260(11) 0.79568(16) 0.0448(6) Uani 1 1 d . . . H11A_1 H 0.2239 0.1734 0.7475 0.067 Uiso 1 1 calc R . . H11B_1 H 0.2171 0.2134 0.8113 0.067 Uiso 1 1 calc R . . H11C_1 H 0.2306 0.1557 0.8297 0.067 Uiso 1 1 calc R . . C12_1 C 0.36237(13) 0.19237(9) 0.85986(13) 0.0343(5) Uani 1 1 d . . . O12_1 O 0.32728(10) 0.18825(7) 0.91643(10) 0.0452(4) Uani 1 1 d . . . N13_1 N 0.44021(11) 0.19872(8) 0.85974(10) 0.0338(4) Uani 1 1 d . . . C13_1 C 0.48121(15) 0.19916(11) 0.92818(13) 0.0424(6) Uani 1 1 d . . . H13A_1 H 0.5340 0.2106 0.9205 0.064 Uiso 1 1 calc R . . H13B_1 H 0.4820 0.1654 0.9484 0.064 Uiso 1 1 calc R . . H13C_1 H 0.4553 0.2218 0.9617 0.064 Uiso 1 1 calc R . . C14_1 C 0.47792(12) 0.20226(9) 0.79613(12) 0.0308(5) Uani 1 1 d . . . C15_1 C 0.43946(12) 0.20081(9) 0.73099(12) 0.0292(4) Uani 1 1 d . . . C16_1 C 0.35915(12) 0.19485(9) 0.72620(12) 0.0308(5) Uani 1 1 d . . . O16_1 O 0.31930(9) 0.19343(7) 0.67096(9) 0.0395(4) Uani 1 1 d . . . N17_1 N 0.49578(10) 0.20599(8) 0.67966(10) 0.0314(4) Uani 1 1 d . . . C17_1 C 0.48628(15) 0.20531(10) 0.60148(12) 0.0390(5) Uani 1 1 d . . . H17A_1 H 0.5362 0.2103 0.5785 0.058 Uiso 1 1 calc R . . H17B_1 H 0.4512 0.2321 0.5869 0.058 Uiso 1 1 calc R . . H17C_1 H 0.4650 0.1731 0.5865 0.058 Uiso 1 1 calc R . . C18_1 C 0.56152(12) 0.20971(9) 0.71606(13) 0.0346(5) Uani 1 1 d . . . H18_1 H 0.6098 0.2135 0.6930 0.041 Uiso 1 1 calc R . . N19_1 N 0.55425(10) 0.20774(8) 0.78676(10) 0.0353(4) Uani 1 1 d . . . C21_1 C -0.14795(13) 0.18031(9) 0.23318(12) 0.0323(5) Uani 1 1 d . . . O21_1 O -0.13467(10) 0.17846(8) 0.16064(9) 0.0473(5) Uani 1 1 d . . . C22_1 C -0.21934(13) 0.18552(9) 0.26364(13) 0.0338(5) Uani 1 1 d . . . H22_1 H -0.2640 0.1881 0.2343 0.041 Uiso 1 1 calc R . . C23_1 C -0.22459(12) 0.18688(9) 0.33820(13) 0.0311(5) Uani 1 1 d . . . O23_1 O -0.29709(9) 0.19300(7) 0.36464(9) 0.0408(4) Uani 1 1 d . . . C24_1 C -0.15975(12) 0.18223(9) 0.38137(12) 0.0309(5) Uani 1 1 d . . . H24_1 H -0.1644 0.1826 0.4324 0.037 Uiso 1 1 calc R . . C25_1 C -0.08775(12) 0.17697(8) 0.34956(12) 0.0288(4) Uani 1 1 d . . . C26_1 C -0.08229(12) 0.17607(9) 0.27547(12) 0.0315(5) Uani 1 1 d . . . H26_1 H -0.0335 0.1726 0.2533 0.038 Uiso 1 1 calc R . . C27_1 C -0.19778(15) 0.18462(12) 0.11308(14) 0.0484(7) Uani 1 1 d . . . H27A_1 H -0.2359 0.1585 0.1223 0.073 Uiso 1 1 calc R . . H27B_1 H -0.1800 0.1821 0.0631 0.073 Uiso 1 1 calc R . . H27C_1 H -0.2211 0.2174 0.1209 0.073 Uiso 1 1 calc R . . C28_1 C -0.30319(14) 0.20507(11) 0.43917(13) 0.0415(6) Uani 1 1 d . . . H28A_1 H -0.2891 0.1759 0.4682 0.062 Uiso 1 1 calc R . . H28B_1 H -0.3561 0.2148 0.4500 0.062 Uiso 1 1 calc R . . H28C_1 H -0.2685 0.2328 0.4506 0.062 Uiso 1 1 calc R . . C29_1 C -0.01991(12) 0.17406(9) 0.39631(12) 0.0303(5) Uani 1 1 d . . . H29_1 H -0.0281 0.1745 0.4469 0.036 Uiso 1 1 calc R . . C31_1 C 0.25981(12) 0.16850(9) 0.49462(12) 0.0331(5) Uani 1 1 d . . . O31_1 O 0.32873(10) 0.16800(8) 0.52953(10) 0.0451(4) Uani 1 1 d . . . H31_1 H 0.3240(18) 0.1780(12) 0.5767(18) 0.054 Uiso 1 1 d . . . C32_1 C 0.25916(13) 0.15695(11) 0.42269(13) 0.0393(6) Uani 1 1 d . . . H32_1 H 0.3056 0.1481 0.3992 0.047 Uiso 1 1 calc R . . C33_1 C 0.19121(13) 0.15820(10) 0.38426(12) 0.0377(5) Uani 1 1 d . . . H33_1 H 0.1917 0.1509 0.3341 0.045 Uiso 1 1 calc R . . C34_1 C 0.12199(12) 0.16988(9) 0.41742(12) 0.0296(4) Uani 1 1 d . . . C35_1 C 0.12335(13) 0.18041(9) 0.49112(12) 0.0328(5) Uani 1 1 d . . . H35_1 H 0.0769 0.1880 0.5154 0.039 Uiso 1 1 calc R . . C36_1 C 0.19168(13) 0.17992(9) 0.52917(12) 0.0329(5) Uani 1 1 d . . . H36_1 H 0.1919 0.1875 0.5792 0.040 Uiso 1 1 calc R . . C37_1 C 0.05215(12) 0.17090(9) 0.37357(12) 0.0329(5) Uani 1 1 d . . . H37_1 H 0.0591 0.1691 0.3229 0.039 Uiso 1 1 calc R . . N11_2 N 0.91268(10) 0.05344(7) 0.21950(11) 0.0321(4) Uani 1 1 d . . . C11_2 C 0.82883(13) 0.05588(10) 0.21640(15) 0.0417(6) Uani 1 1 d . . . H11A_2 H 0.8129 0.0742 0.1732 0.062 Uiso 1 1 calc R . . H11B_2 H 0.8096 0.0730 0.2594 0.062 Uiso 1 1 calc R . . H11C_2 H 0.8078 0.0220 0.2146 0.062 Uiso 1 1 calc R . . C12_2 C 0.95031(13) 0.05196(9) 0.15328(13) 0.0332(5) Uani 1 1 d . . . O12_2 O 0.91582(11) 0.05388(7) 0.09621(9) 0.0444(4) Uani 1 1 d . . . N13_2 N 1.02862(11) 0.04834(8) 0.15470(10) 0.0335(4) Uani 1 1 d . . . C13_2 C 1.07064(16) 0.04456(11) 0.08614(12) 0.0414(6) Uani 1 1 d . . . H13A_2 H 1.0693 0.0768 0.0614 0.062 Uiso 1 1 calc R . . H13B_2 H 1.0465 0.0192 0.0556 0.062 Uiso 1 1 calc R . . H13C_2 H 1.1240 0.0352 0.0959 0.062 Uiso 1 1 calc R . . C14_2 C 1.06572(13) 0.04549(9) 0.21929(12) 0.0309(5) Uani 1 1 d . . . C15_2 C 1.02743(12) 0.04699(8) 0.28337(12) 0.0300(4) Uani 1 1 d . . . C16_2 C 0.94627(12) 0.05017(8) 0.28757(12) 0.0297(4) Uani 1 1 d . . . O16_2 O 0.90592(9) 0.04968(7) 0.34187(9) 0.0397(4) Uani 1 1 d . . . N17_2 N 1.08361(10) 0.04137(8) 0.33552(10) 0.0325(4) Uani 1 1 d . . . C17_2 C 1.07347(15) 0.03960(11) 0.41315(12) 0.0396(6) Uani 1 1 d . . . H17A_2 H 1.1236 0.0357 0.4367 0.059 Uiso 1 1 calc R . . H17B_2 H 1.0405 0.0113 0.4256 0.059 Uiso 1 1 calc R . . H17C_2 H 1.0495 0.0706 0.4295 0.059 Uiso 1 1 calc R . . C18_2 C 1.14962(13) 0.03763(10) 0.29928(13) 0.0367(5) Uani 1 1 d . . . H18_2 H 1.1978 0.0338 0.3227 0.044 Uiso 1 1 calc R . . N19_2 N 1.14259(11) 0.03969(8) 0.22828(11) 0.0370(4) Uani 1 1 d . . . C21_2 C 0.43882(13) 0.07548(9) 0.78167(12) 0.0325(5) Uani 1 1 d . . . O21_2 O 0.45168(10) 0.07750(8) 0.85423(9) 0.0440(4) Uani 1 1 d . . . C22_2 C 0.36711(13) 0.06848(9) 0.75079(13) 0.0330(5) Uani 1 1 d . . . H22_2 H 0.3227 0.0654 0.7800 0.040 Uiso 1 1 calc R . . C23_2 C 0.36173(12) 0.06613(9) 0.67617(13) 0.0324(5) Uani 1 1 d . . . O23_2 O 0.28953(9) 0.05781(7) 0.65010(10) 0.0431(4) Uani 1 1 d . . . C24_2 C 0.42591(13) 0.07166(9) 0.63355(12) 0.0326(5) Uani 1 1 d . . . H24_2 H 0.4210 0.0709 0.5825 0.039 Uiso 1 1 calc R . . C25_2 C 0.49785(12) 0.07841(8) 0.66495(12) 0.0292(4) Uani 1 1 d . . . C26_2 C 0.50388(12) 0.08048(9) 0.73966(12) 0.0319(5) Uani 1 1 d . . . H26_2 H 0.5526 0.0853 0.7618 0.038 Uiso 1 1 calc R . . C27_2 C 0.39047(15) 0.06486(12) 0.90091(14) 0.0460(6) Uani 1 1 d . . . H27A_2 H 0.3697 0.0322 0.8872 0.069 Uiso 1 1 calc R . . H27B_2 H 0.3500 0.0901 0.8971 0.069 Uiso 1 1 calc R . . H27C_2 H 0.4094 0.0635 0.9507 0.069 Uiso 1 1 calc R . . C28_2 C 0.28404(15) 0.04551(12) 0.57557(15) 0.0462(6) Uani 1 1 d . . . H28A_2 H 0.3207 0.0189 0.5643 0.069 Uiso 1 1 calc R . . H28B_2 H 0.2958 0.0750 0.5465 0.069 Uiso 1 1 calc R . . H28C_2 H 0.2319 0.0341 0.5646 0.069 Uiso 1 1 calc R . . C29_2 C 0.56526(12) 0.08131(9) 0.61811(12) 0.0310(5) Uani 1 1 d . . . H29_2 H 0.5564 0.0808 0.5675 0.037 Uiso 1 1 calc R . . C31_2 C 0.84454(13) 0.07551(9) 0.51927(12) 0.0314(5) Uani 1 1 d . . . O31_2 O 0.91288(10) 0.07142(8) 0.48530(10) 0.0426(4) Uani 1 1 d . . . H31_2 H 0.9071(18) 0.0683(12) 0.4438(17) 0.051 Uiso 1 1 d . . . C32_2 C 0.84592(13) 0.08019(10) 0.59348(13) 0.0380(5) Uani 1 1 d . . . H32_2 H 0.8936 0.0810 0.6185 0.046 Uiso 1 1 calc R . . C33_2 C 0.77834(13) 0.08369(10) 0.63113(12) 0.0368(5) Uani 1 1 d . . . H33_2 H 0.7802 0.0868 0.6821 0.044 Uiso 1 1 calc R . . C34_2 C 0.70719(12) 0.08273(9) 0.59655(12) 0.0299(4) Uani 1 1 d . . . C35_2 C 0.70708(13) 0.07848(9) 0.52198(12) 0.0324(5) Uani 1 1 d . . . H35_2 H 0.6595 0.0780 0.4969 0.039 Uiso 1 1 calc R . . C36_2 C 0.77423(13) 0.07492(9) 0.48351(12) 0.0338(5) Uani 1 1 d . . . H36_2 H 0.7726 0.0721 0.4325 0.041 Uiso 1 1 calc R . . C37_2 C 0.63760(12) 0.08457(9) 0.64021(12) 0.0329(5) Uani 1 1 d . . . H37_2 H 0.6451 0.0886 0.6906 0.040 Uiso 1 1 calc R . . N11_3 N -0.02409(10) 0.20400(7) 0.72244(11) 0.0322(4) Uani 1 1 d . . . C11_3 C 0.05978(13) 0.19994(10) 0.72045(16) 0.0421(6) Uani 1 1 d . . . H11A_3 H 0.0775 0.1795 0.7610 0.063 Uiso 1 1 calc R . . H11B_3 H 0.0825 0.2333 0.7240 0.063 Uiso 1 1 calc R . . H11C_3 H 0.0754 0.1843 0.6750 0.063 Uiso 1 1 calc R . . C12_3 C -0.06101(14) 0.20530(9) 0.65571(13) 0.0334(5) Uani 1 1 d . . . O12_3 O -0.02635(11) 0.20379(7) 0.59899(10) 0.0451(4) Uani 1 1 d . . . N13_3 N -0.13957(11) 0.20815(8) 0.65673(10) 0.0338(4) Uani 1 1 d . . . C13_3 C -0.18206(15) 0.21098(11) 0.58818(12) 0.0411(6) Uani 1 1 d . . . H13A_3 H -0.2360 0.2187 0.5978 0.062 Uiso 1 1 calc R . . H13B_3 H -0.1786 0.1789 0.5631 0.062 Uiso 1 1 calc R . . H13C_3 H -0.1599 0.2372 0.5579 0.062 Uiso 1 1 calc R . . C14_3 C -0.17671(13) 0.21068(9) 0.72132(12) 0.0306(5) Uani 1 1 d . . . C15_3 C -0.13856(12) 0.21004(8) 0.78551(12) 0.0293(4) Uani 1 1 d . . . C16_3 C -0.05715(12) 0.20660(8) 0.78982(12) 0.0298(4) Uani 1 1 d . . . O16_3 O -0.01748(9) 0.20676(7) 0.84476(9) 0.0372(4) Uani 1 1 d . . . N17_3 N -0.19442(11) 0.21500(8) 0.83744(10) 0.0334(4) Uani 1 1 d . . . C17_3 C -0.18449(14) 0.21686(11) 0.91454(12) 0.0389(5) Uani 1 1 d . . . H17A_3 H -0.2342 0.2230 0.9375 0.058 Uiso 1 1 calc R . . H17B_3 H -0.1489 0.2439 0.9270 0.058 Uiso 1 1 calc R . . H17C_3 H -0.1636 0.1850 0.9316 0.058 Uiso 1 1 calc R . . C18_3 C -0.26106(13) 0.21758(10) 0.80054(13) 0.0377(5) Uani 1 1 d . . . H18_3 H -0.3094 0.2208 0.8235 0.045 Uiso 1 1 calc R . . N19_3 N -0.25363(11) 0.21535(8) 0.72976(11) 0.0384(5) Uani 1 1 d . . . C21_3 C 0.44923(13) 0.16622(9) 1.28651(12) 0.0327(5) Uani 1 1 d . . . O21_3 O 0.43753(10) 0.16382(8) 1.35917(9) 0.0422(4) Uani 1 1 d . . . C22_3 C 0.52059(12) 0.17239(8) 1.25502(12) 0.0304(5) Uani 1 1 d . . . H22_3 H 0.5655 0.1749 1.2839 0.036 Uiso 1 1 calc R . . C23_3 C 0.52507(12) 0.17484(9) 1.18080(12) 0.0311(5) Uani 1 1 d . . . O23_3 O 0.59709(9) 0.18236(7) 1.15366(9) 0.0389(4) Uani 1 1 d . . . C24_3 C 0.45988(12) 0.17039(9) 1.13802(12) 0.0299(4) Uani 1 1 d . . . H24_3 H 0.4641 0.1713 1.0870 0.036 Uiso 1 1 calc R . . C25_3 C 0.38850(12) 0.16463(8) 1.16986(12) 0.0287(4) Uani 1 1 d . . . C26_3 C 0.38302(12) 0.16218(9) 1.24471(12) 0.0307(5) Uani 1 1 d . . . H26_3 H 0.3345 0.1578 1.2670 0.037 Uiso 1 1 calc R . . C27_3 C 0.49939(15) 0.17581(11) 1.40569(14) 0.0442(6) Uani 1 1 d . . . H27A_3 H 0.5404 0.1511 1.3999 0.066 Uiso 1 1 calc R . . H27B_3 H 0.4816 0.1756 1.4558 0.066 Uiso 1 1 calc R . . H27C_3 H 0.5190 0.2090 1.3936 0.066 Uiso 1 1 calc R . . C28_3 C 0.60126(14) 0.19664(11) 1.07951(14) 0.0416(6) Uani 1 1 d . . . H28A_3 H 0.5849 0.1687 1.0491 0.062 Uiso 1 1 calc R . . H28B_3 H 0.6542 0.2057 1.0677 0.062 Uiso 1 1 calc R . . H28C_3 H 0.5675 0.2253 1.0709 0.062 Uiso 1 1 calc R . . C29_3 C 0.32031(12) 0.16331(9) 1.12329(12) 0.0305(5) Uani 1 1 d . . . H29_3 H 0.3286 0.1619 1.0727 0.037 Uiso 1 1 calc R . . C31_3 C 0.04200(12) 0.17867(9) 1.02276(12) 0.0301(5) Uani 1 1 d . . . O31_3 O -0.02543(9) 0.18463(7) 0.98759(9) 0.0419(4) Uani 1 1 d . . . H31_3 H -0.0207(17) 0.1907(11) 0.9321(17) 0.050 Uiso 1 1 d . . . C32_3 C 0.04027(12) 0.17292(10) 1.09706(12) 0.0339(5) Uani 1 1 d . . . H32_3 H -0.0074 0.1727 1.1217 0.041 Uiso 1 1 calc R . . C33_3 C 0.10774(12) 0.16750(10) 1.13509(12) 0.0342(5) Uani 1 1 d . . . H33_3 H 0.1056 0.1635 1.1859 0.041 Uiso 1 1 calc R . . C34_3 C 0.17888(11) 0.16767(8) 1.10142(11) 0.0274(4) Uani 1 1 d . . . C35_3 C 0.17964(12) 0.17330(9) 1.02657(12) 0.0322(5) Uani 1 1 d . . . H35_3 H 0.2273 0.1733 1.0018 0.039 Uiso 1 1 calc R . . C36_3 C 0.11206(12) 0.17884(9) 0.98783(12) 0.0304(5) Uani 1 1 d . . . H36_3 H 0.1138 0.1828 0.9370 0.036 Uiso 1 1 calc R . . C37_3 C 0.24822(12) 0.16390(9) 1.14540(12) 0.0320(5) Uani 1 1 d . . . H37_3 H 0.2407 0.1616 1.1960 0.038 Uiso 1 1 calc R . . N11_4 N 0.56360(10) 0.05270(7) 1.28806(10) 0.0311(4) Uani 1 1 d . . . C11_4 C 0.64624(13) 0.06365(11) 1.29024(15) 0.0429(6) Uani 1 1 d . . . H11A_4 H 0.6563 0.0897 1.3261 0.064 Uiso 1 1 calc R . . H11B_4 H 0.6630 0.0752 1.2427 0.064 Uiso 1 1 calc R . . H11C_4 H 0.6745 0.0334 1.3034 0.064 Uiso 1 1 calc R . . C12_4 C 0.52744(13) 0.05008(9) 1.35522(13) 0.0328(5) Uani 1 1 d . . . O12_4 O 0.56325(10) 0.05425(7) 1.41127(9) 0.0452(4) Uani 1 1 d . . . N13_4 N 0.45010(11) 0.04284(8) 1.35505(10) 0.0337(4) Uani 1 1 d . . . C13_4 C 0.40900(16) 0.04235(11) 1.42416(13) 0.0425(6) Uani 1 1 d . . . H13A_4 H 0.4374 0.0219 1.4590 0.064 Uiso 1 1 calc R . . H13B_4 H 0.3576 0.0283 1.4170 0.064 Uiso 1 1 calc R . . H13C_4 H 0.4047 0.0765 1.4425 0.064 Uiso 1 1 calc R . . C14_4 C 0.41177(12) 0.03935(9) 1.29125(12) 0.0323(5) Uani 1 1 d . . . C15_4 C 0.44869(12) 0.04104(9) 1.22652(12) 0.0303(4) Uani 1 1 d . . . C16_4 C 0.52900(13) 0.04808(8) 1.22093(12) 0.0308(4) Uani 1 1 d . . . O16_4 O 0.56823(9) 0.05072(7) 1.16557(9) 0.0394(4) Uani 1 1 d . . . N17_4 N 0.39213(10) 0.03564(8) 1.17506(10) 0.0326(4) Uani 1 1 d . . . C17_4 C 0.40116(16) 0.03658(11) 1.09757(13) 0.0429(6) Uani 1 1 d . . . H17A_4 H 0.3525 0.0274 1.0744 0.064 Uiso 1 1 calc R . . H17B_4 H 0.4411 0.0128 1.0835 0.064 Uiso 1 1 calc R . . H17C_4 H 0.4160 0.0702 1.0823 0.064 Uiso 1 1 calc R . . C18_4 C 0.32663(13) 0.03189(10) 1.21249(14) 0.0392(5) Uani 1 1 d . . . H18_4 H 0.2780 0.0283 1.1897 0.047 Uiso 1 1 calc R . . N19_4 N 0.33468(11) 0.03347(8) 1.28319(12) 0.0394(5) Uani 1 1 d . . . C21_4 C 1.03510(13) 0.07649(9) 0.73143(12) 0.0314(5) Uani 1 1 d . . . O21_4 O 1.02215(10) 0.07894(8) 0.65894(9) 0.0447(5) Uani 1 1 d . . . C22_4 C 1.10679(12) 0.07013(9) 0.76230(12) 0.0304(4) Uani 1 1 d . . . H22_4 H 1.1513 0.0669 0.7332 0.037 Uiso 1 1 calc R . . C23_4 C 1.11186(12) 0.06858(8) 0.83716(12) 0.0298(4) Uani 1 1 d . . . O23_4 O 1.18414(9) 0.06131(7) 0.86360(9) 0.0376(4) Uani 1 1 d . . . C24_4 C 1.04713(12) 0.07371(8) 0.87975(12) 0.0291(4) Uani 1 1 d . . . H24_4 H 1.0518 0.0731 0.9308 0.035 Uiso 1 1 calc R . . C25_4 C 0.97511(12) 0.07984(8) 0.84774(11) 0.0277(4) Uani 1 1 d . . . C26_4 C 0.96964(12) 0.08113(9) 0.77306(12) 0.0304(4) Uani 1 1 d . . . H26_4 H 0.9210 0.0852 0.7505 0.036 Uiso 1 1 calc R . . C27_4 C 1.08574(16) 0.07360(12) 0.61174(13) 0.0470(7) Uani 1 1 d . . . H27A_4 H 1.1091 0.0407 0.6188 0.070 Uiso 1 1 calc R . . H27B_4 H 1.1237 0.0996 0.6222 0.070 Uiso 1 1 calc R . . H27C_4 H 1.0682 0.0768 0.5617 0.070 Uiso 1 1 calc R . . C28_4 C 1.19017(13) 0.04955(10) 0.93817(13) 0.0383(5) Uani 1 1 d . . . H28A_4 H 1.1536 0.0230 0.9500 0.057 Uiso 1 1 calc R . . H28B_4 H 1.1786 0.0793 0.9669 0.057 Uiso 1 1 calc R . . H28C_4 H 1.2424 0.0382 0.9490 0.057 Uiso 1 1 calc R . . C29_4 C 0.90741(12) 0.08312(8) 0.89424(11) 0.0288(4) Uani 1 1 d . . . H29_4 H 0.9159 0.0836 0.9449 0.035 Uiso 1 1 calc R . . C31_4 C 0.62772(12) 0.08021(9) 0.99091(12) 0.0315(5) Uani 1 1 d . . . O31_4 O 0.55868(10) 0.07682(8) 1.02429(10) 0.0434(4) Uani 1 1 d . . . H31_4 H 0.5640(18) 0.0680(12) 1.0658(17) 0.052 Uiso 1 1 d . . . C32_4 C 0.62739(13) 0.09188(10) 0.91870(13) 0.0374(5) Uani 1 1 d . . . H32_4 H 0.5802 0.0985 0.8947 0.045 Uiso 1 1 calc R . . C33_4 C 0.69530(13) 0.09399(10) 0.88123(12) 0.0365(5) Uani 1 1 d . . . H33_4 H 0.6942 0.1018 0.8313 0.044 Uiso 1 1 calc R . . C34_4 C 0.76564(12) 0.08492(8) 0.91460(12) 0.0295(4) Uani 1 1 d . . . C35_4 C 0.76501(13) 0.07491(9) 0.98799(12) 0.0324(5) Uani 1 1 d . . . H35_4 H 0.8123 0.0698 1.0126 0.039 Uiso 1 1 calc R . . C36_4 C 0.69685(13) 0.07221(9) 1.02606(12) 0.0327(5) Uani 1 1 d . . . H36_4 H 0.6976 0.0649 1.0762 0.039 Uiso 1 1 calc R . . C37_4 C 0.83559(12) 0.08545(9) 0.87135(12) 0.0318(5) Uani 1 1 d . . . H37_4 H 0.8286 0.0877 0.8206 0.038 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 N11_1 0.0205(8) 0.0386(11) 0.0384(10) 0.0016(8) -0.0006(7) -0.0001(7) C11_1 0.0212(11) 0.0564(17) 0.0569(16) 0.0027(13) 0.0053(10) -0.0017(10) C12_1 0.0283(11) 0.0380(13) 0.0368(12) 0.0027(10) 0.0043(9) 0.0040(9) O12_1 0.0399(10) 0.0593(12) 0.0366(10) 0.0058(8) 0.0105(8) 0.0027(8) N13_1 0.0275(9) 0.0492(12) 0.0248(9) 0.0013(8) 0.0011(7) 0.0030(8) C13_1 0.0415(13) 0.0560(17) 0.0296(12) 0.0019(11) -0.0032(10) 0.0035(12) C14_1 0.0239(10) 0.0384(12) 0.0300(11) 0.0007(9) 0.0023(8) 0.0010(9) C15_1 0.0237(10) 0.0345(12) 0.0294(11) 0.0014(9) 0.0010(8) -0.0003(8) C16_1 0.0250(10) 0.0323(12) 0.0351(12) -0.0012(9) 0.0008(8) 0.0030(8) O16_1 0.0269(8) 0.0522(11) 0.0394(9) -0.0021(8) -0.0068(7) -0.0008(7) N17_1 0.0260(9) 0.0425(11) 0.0256(9) -0.0009(8) -0.0018(7) -0.0004(8) C17_1 0.0372(12) 0.0532(16) 0.0265(11) 0.0026(10) -0.0022(9) -0.0044(11) C18_1 0.0220(10) 0.0487(14) 0.0329(12) -0.0017(10) 0.0007(8) -0.0030(9) N19_1 0.0219(8) 0.0520(13) 0.0320(10) -0.0028(9) -0.0028(7) -0.0011(8) C21_1 0.0276(10) 0.0422(13) 0.0269(11) 0.0015(9) -0.0038(8) -0.0015(9) O21_1 0.0299(8) 0.0862(15) 0.0256(8) -0.0041(9) -0.0053(7) -0.0004(9) C22_1 0.0242(10) 0.0418(13) 0.0353(12) -0.0025(10) -0.0052(8) -0.0011(9) C23_1 0.0204(9) 0.0364(12) 0.0366(12) -0.0026(9) 0.0020(8) -0.0010(8) O23_1 0.0241(8) 0.0620(12) 0.0362(9) -0.0060(8) -0.0001(7) 0.0000(7) C24_1 0.0257(10) 0.0386(13) 0.0283(11) -0.0002(9) -0.0014(8) -0.0008(9) C25_1 0.0236(9) 0.0335(12) 0.0292(10) 0.0007(9) -0.0031(8) -0.0003(8) C26_1 0.0207(9) 0.0447(13) 0.0290(11) -0.0007(9) -0.0011(8) -0.0011(9) C27_1 0.0374(13) 0.077(2) 0.0311(12) -0.0001(12) -0.0122(10) -0.0053(13) C28_1 0.0298(11) 0.0572(17) 0.0377(13) -0.0089(11) 0.0050(10) 0.0032(11) C29_1 0.0264(10) 0.0377(12) 0.0268(10) 0.0016(9) -0.0035(8) 0.0003(9) C31_1 0.0227(10) 0.0443(14) 0.0322(11) 0.0046(10) -0.0026(8) -0.0013(9) O31_1 0.0265(8) 0.0738(14) 0.0349(9) -0.0020(9) -0.0079(7) -0.0009(8) C32_1 0.0237(10) 0.0631(17) 0.0312(12) -0.0007(11) 0.0004(8) 0.0037(10) C33_1 0.0309(11) 0.0574(16) 0.0248(11) -0.0014(10) -0.0034(9) -0.0005(11) C34_1 0.0228(9) 0.0391(12) 0.0268(10) 0.0003(9) -0.0011(8) 0.0002(8) C35_1 0.0258(10) 0.0411(13) 0.0315(11) -0.0019(9) -0.0022(8) 0.0009(9) C36_1 0.0304(11) 0.0430(13) 0.0254(10) -0.0011(9) -0.0030(8) -0.0007(9) C37_1 0.0265(10) 0.0448(14) 0.0272(11) 0.0005(9) -0.0052(8) 0.0008(9) N11_2 0.0226(8) 0.0359(11) 0.0376(10) -0.0014(8) -0.0055(7) 0.0015(7) C11_2 0.0244(11) 0.0485(15) 0.0521(15) -0.0031(12) -0.0063(10) 0.0050(10) C12_2 0.0315(11) 0.0316(12) 0.0365(12) 0.0010(9) -0.0057(9) -0.0021(9) O12_2 0.0458(10) 0.0501(11) 0.0373(9) 0.0023(8) -0.0136(8) 0.0008(8) N13_2 0.0310(9) 0.0412(11) 0.0282(9) 0.0012(8) -0.0014(7) -0.0036(8) C13_2 0.0498(15) 0.0510(16) 0.0233(11) 0.0028(10) 0.0013(10) -0.0027(12) C14_2 0.0289(10) 0.0349(12) 0.0287(11) 0.0021(9) -0.0022(8) -0.0021(9) C15_2 0.0272(10) 0.0322(12) 0.0306(11) -0.0010(9) -0.0068(8) -0.0002(8) C16_2 0.0287(10) 0.0297(11) 0.0308(11) -0.0027(9) -0.0032(8) 0.0024(8) O16_2 0.0320(8) 0.0492(11) 0.0379(9) -0.0030(8) 0.0029(7) 0.0018(7) N17_2 0.0267(9) 0.0451(12) 0.0257(9) -0.0001(8) -0.0011(7) 0.0013(8) C17_2 0.0382(12) 0.0566(16) 0.0240(11) 0.0030(10) 0.0021(9) 0.0033(11) C18_2 0.0239(10) 0.0515(15) 0.0348(12) -0.0010(10) 0.0011(9) 0.0010(10) N19_2 0.0240(9) 0.0479(12) 0.0392(11) 0.0012(9) -0.0019(8) -0.0020(8) C21_2 0.0299(11) 0.0374(13) 0.0302(11) -0.0012(9) 0.0015(9) -0.0005(9) O21_2 0.0335(9) 0.0716(13) 0.0268(8) -0.0006(8) 0.0035(7) -0.0092(8) C22_2 0.0250(10) 0.0350(12) 0.0388(12) -0.0011(10) 0.0050(9) 0.0018(9) C23_2 0.0231(10) 0.0364(12) 0.0376(12) -0.0035(9) -0.0031(8) 0.0032(9) O23_2 0.0247(8) 0.0608(12) 0.0439(10) -0.0075(8) -0.0028(7) 0.0007(8) C24_2 0.0284(10) 0.0387(13) 0.0306(11) 0.0001(9) -0.0004(8) 0.0008(9) C25_2 0.0261(10) 0.0313(11) 0.0302(11) 0.0002(9) 0.0016(8) 0.0015(8) C26_2 0.0240(10) 0.0395(13) 0.0321(11) 0.0001(9) -0.0016(8) -0.0013(9) C27_2 0.0409(14) 0.0600(17) 0.0370(13) 0.0020(12) 0.0123(11) -0.0041(12) C28_2 0.0301(12) 0.0608(18) 0.0476(15) -0.0109(13) -0.0087(10) -0.0005(11) C29_2 0.0282(10) 0.0384(13) 0.0264(10) 0.0006(9) 0.0018(8) 0.0007(9) C31_2 0.0289(11) 0.0353(12) 0.0299(11) 0.0012(9) 0.0056(8) 0.0007(9) O31_2 0.0312(9) 0.0652(12) 0.0315(9) 0.0000(9) 0.0063(7) 0.0015(8) C32_2 0.0254(10) 0.0580(16) 0.0307(11) 0.0012(11) -0.0022(9) 0.0027(10) C33_2 0.0294(11) 0.0555(16) 0.0253(11) -0.0020(10) -0.0008(8) -0.0005(10) C34_2 0.0263(10) 0.0362(12) 0.0272(10) 0.0010(9) 0.0019(8) -0.0010(8) C35_2 0.0249(10) 0.0429(13) 0.0292(11) 0.0011(9) -0.0022(8) -0.0064(9) C36_2 0.0329(11) 0.0426(13) 0.0260(10) -0.0002(9) 0.0001(9) -0.0046(10) C37_2 0.0271(10) 0.0435(14) 0.0283(11) -0.0018(9) 0.0029(8) -0.0013(9) N11_3 0.0246(9) 0.0360(11) 0.0359(10) 0.0022(8) 0.0044(7) 0.0014(7) C11_3 0.0217(10) 0.0483(15) 0.0564(16) 0.0041(12) 0.0038(10) 0.0030(10) C12_3 0.0353(12) 0.0325(12) 0.0323(12) -0.0003(9) 0.0020(9) 0.0002(9) O12_3 0.0463(10) 0.0516(11) 0.0377(10) -0.0008(8) 0.0142(8) 0.0008(8) N13_3 0.0292(9) 0.0452(12) 0.0271(9) -0.0021(8) 0.0005(7) -0.0013(8) C13_3 0.0451(14) 0.0544(16) 0.0239(11) -0.0026(10) -0.0018(10) -0.0031(12) C14_3 0.0285(10) 0.0329(12) 0.0303(11) 0.0000(9) -0.0016(8) -0.0018(8) C15_3 0.0253(10) 0.0340(12) 0.0285(11) 0.0004(9) 0.0019(8) -0.0003(8) C16_3 0.0286(10) 0.0291(11) 0.0316(11) 0.0028(9) -0.0031(8) 0.0002(8) O16_3 0.0300(8) 0.0463(10) 0.0354(9) 0.0033(7) -0.0074(7) -0.0003(7) N17_3 0.0274(9) 0.0450(12) 0.0279(9) 0.0012(8) 0.0025(7) 0.0006(8) C17_3 0.0362(12) 0.0543(16) 0.0261(11) 0.0005(10) 0.0015(9) 0.0043(11) C18_3 0.0207(10) 0.0547(15) 0.0379(13) 0.0028(11) -0.0024(9) 0.0009(10) N19_3 0.0225(9) 0.0522(13) 0.0405(11) 0.0008(9) 0.0000(8) -0.0014(8) C21_3 0.0329(11) 0.0377(13) 0.0275(11) -0.0009(9) -0.0020(9) -0.0004(9) O21_3 0.0325(8) 0.0698(13) 0.0244(8) 0.0020(8) -0.0037(6) -0.0069(8) C22_3 0.0260(10) 0.0330(12) 0.0321(11) 0.0002(9) -0.0052(8) 0.0004(8) C23_3 0.0227(10) 0.0359(12) 0.0348(11) -0.0008(9) -0.0007(8) 0.0010(8) O23_3 0.0231(7) 0.0572(11) 0.0365(9) 0.0015(8) -0.0014(6) -0.0016(7) C24_3 0.0276(10) 0.0373(12) 0.0249(10) -0.0020(9) -0.0021(8) 0.0015(9) C25_3 0.0242(10) 0.0321(11) 0.0298(11) 0.0000(9) -0.0033(8) 0.0008(8) C26_3 0.0252(10) 0.0372(12) 0.0297(11) -0.0004(9) -0.0028(8) 0.0003(9) C27_3 0.0394(13) 0.0615(18) 0.0316(12) -0.0033(11) -0.0113(10) -0.0013(12) C28_3 0.0284(11) 0.0569(16) 0.0395(13) 0.0036(12) 0.0027(10) -0.0003(11) C29_3 0.0246(10) 0.0384(12) 0.0284(10) -0.0018(9) -0.0040(8) 0.0002(9) C31_3 0.0246(10) 0.0354(12) 0.0303(11) -0.0012(9) -0.0057(8) 0.0013(8) O31_3 0.0277(8) 0.0653(12) 0.0326(9) 0.0031(8) -0.0090(7) 0.0033(8) C32_3 0.0218(10) 0.0496(14) 0.0304(11) 0.0014(10) 0.0019(8) 0.0010(9) C33_3 0.0263(10) 0.0530(15) 0.0235(10) 0.0008(10) -0.0005(8) 0.0006(10) C34_3 0.0219(9) 0.0343(12) 0.0260(10) -0.0019(8) -0.0013(7) -0.0018(8) C35_3 0.0235(10) 0.0432(13) 0.0298(11) 0.0008(9) 0.0010(8) -0.0025(9) C36_3 0.0288(10) 0.0377(12) 0.0245(10) 0.0027(9) -0.0020(8) -0.0023(9) C37_3 0.0281(10) 0.0422(13) 0.0256(10) 0.0012(9) -0.0024(8) -0.0017(9) N11_4 0.0194(8) 0.0377(11) 0.0363(10) 0.0004(8) -0.0023(7) 0.0004(7) C11_4 0.0193(10) 0.0533(16) 0.0559(16) 0.0044(12) -0.0031(10) -0.0026(10) C12_4 0.0280(11) 0.0334(12) 0.0369(12) -0.0026(9) -0.0024(9) 0.0026(9) O12_4 0.0416(10) 0.0562(12) 0.0378(9) -0.0047(8) -0.0122(8) 0.0010(8) N13_4 0.0286(9) 0.0456(12) 0.0271(9) -0.0002(8) 0.0017(7) 0.0018(8) C13_4 0.0470(14) 0.0525(16) 0.0279(12) 0.0004(11) 0.0028(10) 0.0030(12) C14_4 0.0265(10) 0.0371(12) 0.0333(11) 0.0015(9) -0.0004(8) 0.0013(9) C15_4 0.0259(10) 0.0344(12) 0.0306(11) 0.0010(9) -0.0048(8) 0.0009(8) C16_4 0.0291(10) 0.0307(11) 0.0326(11) 0.0013(9) -0.0011(9) 0.0036(9) O16_4 0.0316(8) 0.0473(10) 0.0394(9) 0.0031(8) 0.0056(7) 0.0026(7) N17_4 0.0260(9) 0.0443(12) 0.0275(9) 0.0011(8) -0.0010(7) -0.0026(8) C17_4 0.0443(14) 0.0555(17) 0.0288(12) -0.0042(11) 0.0011(10) -0.0051(12) C18_4 0.0248(11) 0.0536(15) 0.0392(13) 0.0012(11) 0.0002(9) -0.0026(10) N19_4 0.0225(9) 0.0520(13) 0.0437(12) 0.0043(10) -0.0022(8) -0.0014(8) C21_4 0.0306(11) 0.0373(12) 0.0263(10) 0.0005(9) 0.0016(8) -0.0023(9) O21_4 0.0318(9) 0.0786(14) 0.0238(8) 0.0047(8) 0.0022(6) -0.0027(9) C22_4 0.0267(10) 0.0342(12) 0.0304(11) 0.0014(9) 0.0057(8) -0.0005(8) C23_4 0.0245(10) 0.0308(11) 0.0341(11) -0.0001(9) -0.0008(8) -0.0009(8) O23_4 0.0242(7) 0.0541(11) 0.0346(9) 0.0044(7) -0.0009(6) 0.0024(7) C24_4 0.0259(10) 0.0348(12) 0.0266(10) -0.0022(9) 0.0001(8) 0.0000(8) C25_4 0.0274(10) 0.0283(11) 0.0274(10) -0.0007(8) 0.0010(8) -0.0008(8) C26_4 0.0237(10) 0.0381(12) 0.0293(11) 0.0004(9) -0.0004(8) -0.0012(9) C27_4 0.0437(14) 0.0685(19) 0.0288(12) 0.0034(12) 0.0093(10) -0.0082(13) C28_4 0.0271(11) 0.0518(15) 0.0361(12) 0.0031(11) -0.0041(9) 0.0006(10) C29_4 0.0262(10) 0.0350(12) 0.0252(10) -0.0019(8) 0.0021(8) -0.0007(8) C31_4 0.0253(10) 0.0390(13) 0.0303(11) -0.0017(9) 0.0034(8) 0.0000(9) O31_4 0.0276(8) 0.0680(13) 0.0347(9) 0.0040(9) 0.0050(7) -0.0015(8) C32_4 0.0233(10) 0.0573(16) 0.0316(11) -0.0015(11) -0.0029(8) 0.0016(10) C33_4 0.0276(11) 0.0572(16) 0.0248(10) 0.0014(10) -0.0010(8) -0.0003(10) C34_4 0.0237(10) 0.0346(12) 0.0302(11) -0.0014(9) -0.0015(8) 0.0004(8) C35_4 0.0280(10) 0.0420(13) 0.0272(10) 0.0019(9) -0.0028(8) 0.0022(9) C36_4 0.0319(11) 0.0405(13) 0.0257(10) 0.0018(9) 0.0008(8) -0.0003(9) C37_4 0.0267(10) 0.0435(13) 0.0252(10) 0.0010(9) 0.0010(8) 0.0004(9) _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 N11_1 C16_1 1.386(3) . ? N11_1 C12_1 1.386(3) . ? N11_1 C11_1 1.465(3) . ? C11_1 H11A_1 0.9800 . ? C11_1 H11B_1 0.9800 . ? C11_1 H11C_1 0.9800 . ? C12_1 O12_1 1.221(3) . ? C12_1 N13_1 1.367(3) . ? N13_1 C14_1 1.356(3) . ? N13_1 C13_1 1.454(3) . ? C13_1 H13A_1 0.9800 . ? C13_1 H13B_1 0.9800 . ? C13_1 H13C_1 0.9800 . ? C14_1 N19_1 1.350(3) . ? C14_1 C15_1 1.380(3) . ? C15_1 N17_1 1.377(3) . ? C15_1 C16_1 1.411(3) . ? C16_1 O16_1 1.236(3) . ? N17_1 C18_1 1.331(3) . ? N17_1 C17_1 1.459(3) . ? C17_1 H17A_1 0.9800 . ? C17_1 H17B_1 0.9800 . ? C17_1 H17C_1 0.9800 . ? C18_1 N19_1 1.319(3) . ? C18_1 H18_1 0.9500 . ? C21_1 O21_1 1.367(3) . ? C21_1 C22_1 1.375(3) . ? C21_1 C26_1 1.389(3) . ? O21_1 C27_1 1.417(3) . ? C22_1 C23_1 1.387(3) . ? C22_1 H22_1 0.9500 . ? C23_1 O23_1 1.367(3) . ? C23_1 C24_1 1.388(3) . ? O23_1 C28_1 1.424(3) . ? C24_1 C25_1 1.396(3) . ? C24_1 H24_1 0.9500 . ? C25_1 C26_1 1.378(3) . ? C25_1 C29_1 1.465(3) . ? C26_1 H26_1 0.9500 . ? C27_1 H27A_1 0.9800 . ? C27_1 H27B_1 0.9800 . ? C27_1 H27C_1 0.9800 . ? C28_1 H28A_1 0.9800 . ? C28_1 H28B_1 0.9800 . ? C28_1 H28C_1 0.9800 . ? C29_1 C37_1 1.329(3) . ? C29_1 H29_1 0.9500 . ? C31_1 O31_1 1.362(3) . ? C31_1 C32_1 1.369(3) . ? C31_1 C36_1 1.386(3) . ? O31_1 H31_1 0.92(3) . ? C32_1 C33_1 1.380(3) . ? C32_1 H32_1 0.9500 . ? C33_1 C34_1 1.392(3) . ? C33_1 H33_1 0.9500 . ? C34_1 C35_1 1.396(3) . ? C34_1 C37_1 1.461(3) . ? C35_1 C36_1 1.382(3) . ? C35_1 H35_1 0.9500 . ? C36_1 H36_1 0.9500 . ? C37_1 H37_1 0.9500 . ? N11_2 C16_2 1.392(3) . ? N11_2 C12_2 1.395(3) . ? N11_2 C11_2 1.463(3) . ? C11_2 H11A_2 0.9800 . ? C11_2 H11B_2 0.9800 . ? C11_2 H11C_2 0.9800 . ? C12_2 O12_2 1.216(3) . ? C12_2 N13_2 1.368(3) . ? N13_2 C14_2 1.361(3) . ? N13_2 C13_2 1.473(3) . ? C13_2 H13A_2 0.9800 . ? C13_2 H13B_2 0.9800 . ? C13_2 H13C_2 0.9800 . ? C14_2 N19_2 1.358(3) . ? C14_2 C15_2 1.366(3) . ? C15_2 N17_2 1.382(3) . ? C15_2 C16_2 1.419(3) . ? C16_2 O16_2 1.230(3) . ? N17_2 C18_2 1.338(3) . ? N17_2 C17_2 1.452(3) . ? C17_2 H17A_2 0.9800 . ? C17_2 H17B_2 0.9800 . ? C17_2 H17C_2 0.9800 . ? C18_2 N19_2 1.323(3) . ? C18_2 H18_2 0.9500 . ? C21_2 O21_2 1.365(3) . ? C21_2 C26_2 1.385(3) . ? C21_2 C22_2 1.385(3) . ? O21_2 C27_2 1.417(3) . ? C22_2 C23_2 1.388(3) . ? C22_2 H22_2 0.9500 . ? C23_2 O23_2 1.364(3) . ? C23_2 C24_2 1.380(3) . ? O23_2 C28_2 1.424(3) . ? C24_2 C25_2 1.392(3) . ? C24_2 H24_2 0.9500 . ? C25_2 C26_2 1.390(3) . ? C25_2 C29_2 1.466(3) . ? C26_2 H26_2 0.9500 . ? C27_2 H27A_2 0.9800 . ? C27_2 H27B_2 0.9800 . ? C27_2 H27C_2 0.9800 . ? C28_2 H28A_2 0.9800 . ? C28_2 H28B_2 0.9800 . ? C28_2 H28C_2 0.9800 . ? C29_2 C37_2 1.327(3) . ? C29_2 H29_2 0.9500 . ? C31_2 O31_2 1.354(3) . ? C31_2 C32_2 1.382(3) . ? C31_2 C36_2 1.391(3) . ? O31_2 H31_2 0.78(3) . ? C32_2 C33_2 1.375(3) . ? C32_2 H32_2 0.9500 . ? C33_2 C34_2 1.394(3) . ? C33_2 H33_2 0.9500 . ? C34_2 C35_2 1.388(3) . ? C34_2 C37_2 1.461(3) . ? C35_2 C36_2 1.376(3) . ? C35_2 H35_2 0.9500 . ? C36_2 H36_2 0.9500 . ? C37_2 H37_2 0.9500 . ? N11_3 C16_3 1.380(3) . ? N11_3 C12_3 1.393(3) . ? N11_3 C11_3 1.466(3) . ? C11_3 H11A_3 0.9800 . ? C11_3 H11B_3 0.9800 . ? C11_3 H11C_3 0.9800 . ? C12_3 O12_3 1.216(3) . ? C12_3 N13_3 1.371(3) . ? N13_3 C14_3 1.365(3) . ? N13_3 C13_3 1.471(3) . ? C13_3 H13A_3 0.9800 . ? C13_3 H13B_3 0.9800 . ? C13_3 H13C_3 0.9800 . ? C14_3 N19_3 1.356(3) . ? C14_3 C15_3 1.361(3) . ? C15_3 N17_3 1.378(3) . ? C15_3 C16_3 1.423(3) . ? C16_3 O16_3 1.229(3) . ? N17_3 C18_3 1.347(3) . ? N17_3 C17_3 1.441(3) . ? C17_3 H17A_3 0.9800 . ? C17_3 H17B_3 0.9800 . ? C17_3 H17C_3 0.9800 . ? C18_3 N19_3 1.321(3) . ? C18_3 H18_3 0.9500 . ? C21_3 O21_3 1.365(3) . ? C21_3 C22_3 1.386(3) . ? C21_3 C26_3 1.392(3) . ? O21_3 C27_3 1.415(3) . ? C22_3 C23_3 1.381(3) . ? C22_3 H22_3 0.9500 . ? C23_3 O23_3 1.369(3) . ? C23_3 C24_3 1.388(3) . ? O23_3 C28_3 1.429(3) . ? C24_3 C25_3 1.387(3) . ? C24_3 H24_3 0.9500 . ? C25_3 C26_3 1.393(3) . ? C25_3 C29_3 1.467(3) . ? C26_3 H26_3 0.9500 . ? C27_3 H27A_3 0.9800 . ? C27_3 H27B_3 0.9800 . ? C27_3 H27C_3 0.9800 . ? C28_3 H28A_3 0.9800 . ? C28_3 H28B_3 0.9800 . ? C28_3 H28C_3 0.9800 . ? C29_3 C37_3 1.323(3) . ? C29_3 H29_3 0.9500 . ? C31_3 O31_3 1.351(3) . ? C31_3 C36_3 1.384(3) . ? C31_3 C32_3 1.387(3) . ? O31_3 H31_3 1.04(3) . ? C32_3 C33_3 1.376(3) . ? C32_3 H32_3 0.9500 . ? C33_3 C34_3 1.390(3) . ? C33_3 H33_3 0.9500 . ? C34_3 C35_3 1.396(3) . ? C34_3 C37_3 1.459(3) . ? C35_3 C36_3 1.385(3) . ? C35_3 H35_3 0.9500 . ? C36_3 H36_3 0.9500 . ? C37_3 H37_3 0.9500 . ? N11_4 C16_4 1.387(3) . ? N11_4 C12_4 1.400(3) . ? N11_4 C11_4 1.470(3) . ? C11_4 H11A_4 0.9800 . ? C11_4 H11B_4 0.9800 . ? C11_4 H11C_4 0.9800 . ? C12_4 O12_4 1.215(3) . ? C12_4 N13_4 1.361(3) . ? N13_4 C14_4 1.360(3) . ? N13_4 C13_4 1.471(3) . ? C13_4 H13A_4 0.9800 . ? C13_4 H13B_4 0.9800 . ? C13_4 H13C_4 0.9800 . ? C14_4 N19_4 1.360(3) . ? C14_4 C15_4 1.365(3) . ? C15_4 N17_4 1.377(3) . ? C15_4 C16_4 1.416(3) . ? C16_4 O16_4 1.238(3) . ? N17_4 C18_4 1.342(3) . ? N17_4 C17_4 1.446(3) . ? C17_4 H17A_4 0.9800 . ? C17_4 H17B_4 0.9800 . ? C17_4 H17C_4 0.9800 . ? C18_4 N19_4 1.319(3) . ? C18_4 H18_4 0.9500 . ? C21_4 O21_4 1.364(3) . ? C21_4 C22_4 1.383(3) . ? C21_4 C26_4 1.385(3) . ? O21_4 C27_4 1.422(3) . ? C22_4 C23_4 1.391(3) . ? C22_4 H22_4 0.9500 . ? C23_4 O23_4 1.364(3) . ? C23_4 C24_4 1.386(3) . ? O23_4 C28_4 1.422(3) . ? C24_4 C25_4 1.396(3) . ? C24_4 H24_4 0.9500 . ? C25_4 C26_4 1.388(3) . ? C25_4 C29_4 1.467(3) . ? C26_4 H26_4 0.9500 . ? C27_4 H27A_4 0.9800 . ? C27_4 H27B_4 0.9800 . ? C27_4 H27C_4 0.9800 . ? C28_4 H28A_4 0.9800 . ? C28_4 H28B_4 0.9800 . ? C28_4 H28C_4 0.9800 . ? C29_4 C37_4 1.321(3) . ? C29_4 H29_4 0.9500 . ? C31_4 O31_4 1.358(3) . ? C31_4 C32_4 1.375(3) . ? C31_4 C36_4 1.384(3) . ? O31_4 H31_4 0.81(3) . ? C32_4 C33_4 1.376(3) . ? C32_4 H32_4 0.9500 . ? C33_4 C34_4 1.392(3) . ? C33_4 H33_4 0.9500 . ? C34_4 C35_4 1.387(3) . ? C34_4 C37_4 1.462(3) . ? C35_4 C36_4 1.386(3) . ? C35_4 H35_4 0.9500 . ? C36_4 H36_4 0.9500 . ? C37_4 H37_4 0.9500 . ? 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 C16_1 N11_1 C12_1 126.94(19) . . ? C16_1 N11_1 C11_1 117.3(2) . . ? C12_1 N11_1 C11_1 115.8(2) . . ? N11_1 C11_1 H11A_1 109.5 . . ? N11_1 C11_1 H11B_1 109.5 . . ? H11A_1 C11_1 H11B_1 109.5 . . ? N11_1 C11_1 H11C_1 109.5 . . ? H11A_1 C11_1 H11C_1 109.5 . . ? H11B_1 C11_1 H11C_1 109.5 . . ? O12_1 C12_1 N13_1 120.8(2) . . ? O12_1 C12_1 N11_1 121.9(2) . . ? N13_1 C12_1 N11_1 117.3(2) . . ? C14_1 N13_1 C12_1 119.6(2) . . ? C14_1 N13_1 C13_1 121.38(19) . . ? C12_1 N13_1 C13_1 118.9(2) . . ? N13_1 C13_1 H13A_1 109.5 . . ? N13_1 C13_1 H13B_1 109.5 . . ? H13A_1 C13_1 H13B_1 109.5 . . ? N13_1 C13_1 H13C_1 109.5 . . ? H13A_1 C13_1 H13C_1 109.5 . . ? H13B_1 C13_1 H13C_1 109.5 . . ? N19_1 C14_1 N13_1 126.9(2) . . ? N19_1 C14_1 C15_1 111.45(19) . . ? N13_1 C14_1 C15_1 121.6(2) . . ? N17_1 C15_1 C14_1 104.92(18) . . ? N17_1 C15_1 C16_1 132.6(2) . . ? C14_1 C15_1 C16_1 122.4(2) . . ? O16_1 C16_1 N11_1 120.4(2) . . ? O16_1 C16_1 C15_1 127.5(2) . . ? N11_1 C16_1 C15_1 112.04(19) . . ? C18_1 N17_1 C15_1 105.73(18) . . ? C18_1 N17_1 C17_1 126.8(2) . . ? C15_1 N17_1 C17_1 127.41(19) . . ? N17_1 C17_1 H17A_1 109.5 . . ? N17_1 C17_1 H17B_1 109.5 . . ? H17A_1 C17_1 H17B_1 109.5 . . ? N17_1 C17_1 H17C_1 109.5 . . ? H17A_1 C17_1 H17C_1 109.5 . . ? H17B_1 C17_1 H17C_1 109.5 . . ? N19_1 C18_1 N17_1 114.5(2) . . ? N19_1 C18_1 H18_1 122.7 . . ? N17_1 C18_1 H18_1 122.7 . . ? C18_1 N19_1 C14_1 103.35(18) . . ? O21_1 C21_1 C22_1 124.4(2) . . ? O21_1 C21_1 C26_1 114.2(2) . . ? C22_1 C21_1 C26_1 121.4(2) . . ? C21_1 O21_1 C27_1 118.3(2) . . ? C21_1 C22_1 C23_1 118.4(2) . . ? C21_1 C22_1 H22_1 120.8 . . ? C23_1 C22_1 H22_1 120.8 . . ? O23_1 C23_1 C22_1 115.18(19) . . ? O23_1 C23_1 C24_1 123.7(2) . . ? C22_1 C23_1 C24_1 121.1(2) . . ? C23_1 O23_1 C28_1 116.63(18) . . ? C23_1 C24_1 C25_1 119.8(2) . . ? C23_1 C24_1 H24_1 120.1 . . ? C25_1 C24_1 H24_1 120.1 . . ? C26_1 C25_1 C24_1 119.28(19) . . ? C26_1 C25_1 C29_1 122.0(2) . . ? C24_1 C25_1 C29_1 118.7(2) . . ? C25_1 C26_1 C21_1 120.1(2) . . ? C25_1 C26_1 H26_1 119.9 . . ? C21_1 C26_1 H26_1 119.9 . . ? O21_1 C27_1 H27A_1 109.5 . . ? O21_1 C27_1 H27B_1 109.5 . . ? H27A_1 C27_1 H27B_1 109.5 . . ? O21_1 C27_1 H27C_1 109.5 . . ? H27A_1 C27_1 H27C_1 109.5 . . ? H27B_1 C27_1 H27C_1 109.5 . . ? O23_1 C28_1 H28A_1 109.5 . . ? O23_1 C28_1 H28B_1 109.5 . . ? H28A_1 C28_1 H28B_1 109.5 . . ? O23_1 C28_1 H28C_1 109.5 . . ? H28A_1 C28_1 H28C_1 109.5 . . ? H28B_1 C28_1 H28C_1 109.5 . . ? C37_1 C29_1 C25_1 125.2(2) . . ? C37_1 C29_1 H29_1 117.4 . . ? C25_1 C29_1 H29_1 117.4 . . ? O31_1 C31_1 C32_1 117.7(2) . . ? O31_1 C31_1 C36_1 122.5(2) . . ? C32_1 C31_1 C36_1 119.8(2) . . ? C31_1 O31_1 H31_1 112(2) . . ? C31_1 C32_1 C33_1 120.1(2) . . ? C31_1 C32_1 H32_1 120.0 . . ? C33_1 C32_1 H32_1 120.0 . . ? C32_1 C33_1 C34_1 121.4(2) . . ? C32_1 C33_1 H33_1 119.3 . . ? C34_1 C33_1 H33_1 119.3 . . ? C33_1 C34_1 C35_1 117.82(19) . . ? C33_1 C34_1 C37_1 118.7(2) . . ? C35_1 C34_1 C37_1 123.5(2) . . ? C36_1 C35_1 C34_1 120.6(2) . . ? C36_1 C35_1 H35_1 119.7 . . ? C34_1 C35_1 H35_1 119.7 . . ? C35_1 C36_1 C31_1 120.3(2) . . ? C35_1 C36_1 H36_1 119.9 . . ? C31_1 C36_1 H36_1 119.9 . . ? C29_1 C37_1 C34_1 127.6(2) . . ? C29_1 C37_1 H37_1 116.2 . . ? C34_1 C37_1 H37_1 116.2 . . ? C16_2 N11_2 C12_2 126.82(18) . . ? C16_2 N11_2 C11_2 117.0(2) . . ? C12_2 N11_2 C11_2 116.06(19) . . ? N11_2 C11_2 H11A_2 109.5 . . ? N11_2 C11_2 H11B_2 109.5 . . ? H11A_2 C11_2 H11B_2 109.5 . . ? N11_2 C11_2 H11C_2 109.5 . . ? H11A_2 C11_2 H11C_2 109.5 . . ? H11B_2 C11_2 H11C_2 109.5 . . ? O12_2 C12_2 N13_2 120.6(2) . . ? O12_2 C12_2 N11_2 122.2(2) . . ? N13_2 C12_2 N11_2 117.20(19) . . ? C14_2 N13_2 C12_2 119.42(19) . . ? C14_2 N13_2 C13_2 121.33(19) . . ? C12_2 N13_2 C13_2 119.15(19) . . ? N13_2 C13_2 H13A_2 109.5 . . ? N13_2 C13_2 H13B_2 109.5 . . ? H13A_2 C13_2 H13B_2 109.5 . . ? N13_2 C13_2 H13C_2 109.5 . . ? H13A_2 C13_2 H13C_2 109.5 . . ? H13B_2 C13_2 H13C_2 109.5 . . ? N19_2 C14_2 N13_2 125.4(2) . . ? N19_2 C14_2 C15_2 112.4(2) . . ? N13_2 C14_2 C15_2 122.2(2) . . ? C14_2 C15_2 N17_2 105.00(19) . . ? C14_2 C15_2 C16_2 122.7(2) . . ? N17_2 C15_2 C16_2 132.2(2) . . ? O16_2 C16_2 N11_2 120.2(2) . . ? O16_2 C16_2 C15_2 128.1(2) . . ? N11_2 C16_2 C15_2 111.67(19) . . ? C18_2 N17_2 C15_2 105.34(18) . . ? C18_2 N17_2 C17_2 127.14(19) . . ? C15_2 N17_2 C17_2 127.52(19) . . ? N17_2 C17_2 H17A_2 109.5 . . ? N17_2 C17_2 H17B_2 109.5 . . ? H17A_2 C17_2 H17B_2 109.5 . . ? N17_2 C17_2 H17C_2 109.5 . . ? H17A_2 C17_2 H17C_2 109.5 . . ? H17B_2 C17_2 H17C_2 109.5 . . ? N19_2 C18_2 N17_2 114.9(2) . . ? N19_2 C18_2 H18_2 122.6 . . ? N17_2 C18_2 H18_2 122.6 . . ? C18_2 N19_2 C14_2 102.38(19) . . ? O21_2 C21_2 C26_2 114.8(2) . . ? O21_2 C21_2 C22_2 123.9(2) . . ? C26_2 C21_2 C22_2 121.3(2) . . ? C21_2 O21_2 C27_2 118.16(19) . . ? C21_2 C22_2 C23_2 118.4(2) . . ? C21_2 C22_2 H22_2 120.8 . . ? C23_2 C22_2 H22_2 120.8 . . ? O23_2 C23_2 C24_2 124.3(2) . . ? O23_2 C23_2 C22_2 114.8(2) . . ? C24_2 C23_2 C22_2 121.0(2) . . ? C23_2 O23_2 C28_2 116.12(19) . . ? C23_2 C24_2 C25_2 120.3(2) . . ? C23_2 C24_2 H24_2 119.8 . . ? C25_2 C24_2 H24_2 119.8 . . ? C26_2 C25_2 C24_2 119.1(2) . . ? C26_2 C25_2 C29_2 122.1(2) . . ? C24_2 C25_2 C29_2 118.8(2) . . ? C21_2 C26_2 C25_2 119.9(2) . . ? C21_2 C26_2 H26_2 120.1 . . ? C25_2 C26_2 H26_2 120.1 . . ? O21_2 C27_2 H27A_2 109.5 . . ? O21_2 C27_2 H27B_2 109.5 . . ? H27A_2 C27_2 H27B_2 109.5 . . ? O21_2 C27_2 H27C_2 109.5 . . ? H27A_2 C27_2 H27C_2 109.5 . . ? H27B_2 C27_2 H27C_2 109.5 . . ? O23_2 C28_2 H28A_2 109.5 . . ? O23_2 C28_2 H28B_2 109.5 . . ? H28A_2 C28_2 H28B_2 109.5 . . ? O23_2 C28_2 H28C_2 109.5 . . ? H28A_2 C28_2 H28C_2 109.5 . . ? H28B_2 C28_2 H28C_2 109.5 . . ? C37_2 C29_2 C25_2 125.7(2) . . ? C37_2 C29_2 H29_2 117.2 . . ? C25_2 C29_2 H29_2 117.2 . . ? O31_2 C31_2 C32_2 117.3(2) . . ? O31_2 C31_2 C36_2 123.5(2) . . ? C32_2 C31_2 C36_2 119.2(2) . . ? C31_2 O31_2 H31_2 111(2) . . ? C33_2 C32_2 C31_2 120.0(2) . . ? C33_2 C32_2 H32_2 120.0 . . ? C31_2 C32_2 H32_2 120.0 . . ? C32_2 C33_2 C34_2 121.8(2) . . ? C32_2 C33_2 H33_2 119.1 . . ? C34_2 C33_2 H33_2 119.1 . . ? C35_2 C34_2 C33_2 117.2(2) . . ? C35_2 C34_2 C37_2 123.9(2) . . ? C33_2 C34_2 C37_2 118.9(2) . . ? C36_2 C35_2 C34_2 121.6(2) . . ? C36_2 C35_2 H35_2 119.2 . . ? C34_2 C35_2 H35_2 119.2 . . ? C35_2 C36_2 C31_2 120.1(2) . . ? C35_2 C36_2 H36_2 120.0 . . ? C31_2 C36_2 H36_2 120.0 . . ? C29_2 C37_2 C34_2 128.0(2) . . ? C29_2 C37_2 H37_2 116.0 . . ? C34_2 C37_2 H37_2 116.0 . . ? C16_3 N11_3 C12_3 127.62(19) . . ? C16_3 N11_3 C11_3 116.5(2) . . ? C12_3 N11_3 C11_3 115.9(2) . . ? N11_3 C11_3 H11A_3 109.5 . . ? N11_3 C11_3 H11B_3 109.5 . . ? H11A_3 C11_3 H11B_3 109.5 . . ? N11_3 C11_3 H11C_3 109.5 . . ? H11A_3 C11_3 H11C_3 109.5 . . ? H11B_3 C11_3 H11C_3 109.5 . . ? O12_3 C12_3 N13_3 120.9(2) . . ? O12_3 C12_3 N11_3 122.6(2) . . ? N13_3 C12_3 N11_3 116.5(2) . . ? C14_3 N13_3 C12_3 119.45(19) . . ? C14_3 N13_3 C13_3 121.13(19) . . ? C12_3 N13_3 C13_3 119.34(19) . . ? N13_3 C13_3 H13A_3 109.5 . . ? N13_3 C13_3 H13B_3 109.5 . . ? H13A_3 C13_3 H13B_3 109.5 . . ? N13_3 C13_3 H13C_3 109.5 . . ? H13A_3 C13_3 H13C_3 109.5 . . ? H13B_3 C13_3 H13C_3 109.5 . . ? N19_3 C14_3 C15_3 112.3(2) . . ? N19_3 C14_3 N13_3 125.3(2) . . ? C15_3 C14_3 N13_3 122.3(2) . . ? C14_3 C15_3 N17_3 105.43(19) . . ? C14_3 C15_3 C16_3 122.2(2) . . ? N17_3 C15_3 C16_3 132.3(2) . . ? O16_3 C16_3 N11_3 121.0(2) . . ? O16_3 C16_3 C15_3 127.1(2) . . ? N11_3 C16_3 C15_3 111.83(19) . . ? C18_3 N17_3 C15_3 105.04(19) . . ? C18_3 N17_3 C17_3 127.0(2) . . ? C15_3 N17_3 C17_3 127.92(19) . . ? N17_3 C17_3 H17A_3 109.5 . . ? N17_3 C17_3 H17B_3 109.5 . . ? H17A_3 C17_3 H17B_3 109.5 . . ? N17_3 C17_3 H17C_3 109.5 . . ? H17A_3 C17_3 H17C_3 109.5 . . ? H17B_3 C17_3 H17C_3 109.5 . . ? N19_3 C18_3 N17_3 114.5(2) . . ? N19_3 C18_3 H18_3 122.7 . . ? N17_3 C18_3 H18_3 122.7 . . ? C18_3 N19_3 C14_3 102.69(19) . . ? O21_3 C21_3 C22_3 124.0(2) . . ? O21_3 C21_3 C26_3 114.8(2) . . ? C22_3 C21_3 C26_3 121.2(2) . . ? C21_3 O21_3 C27_3 118.35(19) . . ? C23_3 C22_3 C21_3 118.7(2) . . ? C23_3 C22_3 H22_3 120.6 . . ? C21_3 C22_3 H22_3 120.6 . . ? O23_3 C23_3 C22_3 115.42(19) . . ? O23_3 C23_3 C24_3 123.5(2) . . ? C22_3 C23_3 C24_3 121.1(2) . . ? C23_3 O23_3 C28_3 116.32(18) . . ? C25_3 C24_3 C23_3 120.0(2) . . ? C25_3 C24_3 H24_3 120.0 . . ? C23_3 C24_3 H24_3 120.0 . . ? C24_3 C25_3 C26_3 119.62(19) . . ? C24_3 C25_3 C29_3 118.52(19) . . ? C26_3 C25_3 C29_3 121.8(2) . . ? C21_3 C26_3 C25_3 119.4(2) . . ? C21_3 C26_3 H26_3 120.3 . . ? C25_3 C26_3 H26_3 120.3 . . ? O21_3 C27_3 H27A_3 109.5 . . ? O21_3 C27_3 H27B_3 109.5 . . ? H27A_3 C27_3 H27B_3 109.5 . . ? O21_3 C27_3 H27C_3 109.5 . . ? H27A_3 C27_3 H27C_3 109.5 . . ? H27B_3 C27_3 H27C_3 109.5 . . ? O23_3 C28_3 H28A_3 109.5 . . ? O23_3 C28_3 H28B_3 109.5 . . ? H28A_3 C28_3 H28B_3 109.5 . . ? O23_3 C28_3 H28C_3 109.5 . . ? H28A_3 C28_3 H28C_3 109.5 . . ? H28B_3 C28_3 H28C_3 109.5 . . ? C37_3 C29_3 C25_3 125.8(2) . . ? C37_3 C29_3 H29_3 117.1 . . ? C25_3 C29_3 H29_3 117.1 . . ? O31_3 C31_3 C36_3 122.7(2) . . ? O31_3 C31_3 C32_3 118.1(2) . . ? C36_3 C31_3 C32_3 119.21(19) . . ? C31_3 O31_3 H31_3 115.0(16) . . ? C33_3 C32_3 C31_3 119.9(2) . . ? C33_3 C32_3 H32_3 120.0 . . ? C31_3 C32_3 H32_3 120.0 . . ? C32_3 C33_3 C34_3 122.1(2) . . ? C32_3 C33_3 H33_3 119.0 . . ? C34_3 C33_3 H33_3 119.0 . . ? C33_3 C34_3 C35_3 117.32(19) . . ? C33_3 C34_3 C37_3 119.12(19) . . ? C35_3 C34_3 C37_3 123.53(19) . . ? C36_3 C35_3 C34_3 121.1(2) . . ? C36_3 C35_3 H35_3 119.5 . . ? C34_3 C35_3 H35_3 119.5 . . ? C31_3 C36_3 C35_3 120.4(2) . . ? C31_3 C36_3 H36_3 119.8 . . ? C35_3 C36_3 H36_3 119.8 . . ? C29_3 C37_3 C34_3 127.8(2) . . ? C29_3 C37_3 H37_3 116.1 . . ? C34_3 C37_3 H37_3 116.1 . . ? C16_4 N11_4 C12_4 126.78(18) . . ? C16_4 N11_4 C11_4 117.70(19) . . ? C12_4 N11_4 C11_4 115.46(19) . . ? N11_4 C11_4 H11A_4 109.5 . . ? N11_4 C11_4 H11B_4 109.5 . . ? H11A_4 C11_4 H11B_4 109.5 . . ? N11_4 C11_4 H11C_4 109.5 . . ? H11A_4 C11_4 H11C_4 109.5 . . ? H11B_4 C11_4 H11C_4 109.5 . . ? O12_4 C12_4 N13_4 121.3(2) . . ? O12_4 C12_4 N11_4 121.7(2) . . ? N13_4 C12_4 N11_4 117.00(19) . . ? C14_4 N13_4 C12_4 119.66(19) . . ? C14_4 N13_4 C13_4 121.23(19) . . ? C12_4 N13_4 C13_4 119.0(2) . . ? N13_4 C13_4 H13A_4 109.5 . . ? N13_4 C13_4 H13B_4 109.5 . . ? H13A_4 C13_4 H13B_4 109.5 . . ? N13_4 C13_4 H13C_4 109.5 . . ? H13A_4 C13_4 H13C_4 109.5 . . ? H13B_4 C13_4 H13C_4 109.5 . . ? N13_4 C14_4 N19_4 125.8(2) . . ? N13_4 C14_4 C15_4 122.1(2) . . ? N19_4 C14_4 C15_4 112.1(2) . . ? C14_4 C15_4 N17_4 105.53(19) . . ? C14_4 C15_4 C16_4 122.5(2) . . ? N17_4 C15_4 C16_4 131.9(2) . . ? O16_4 C16_4 N11_4 120.0(2) . . ? O16_4 C16_4 C15_4 128.1(2) . . ? N11_4 C16_4 C15_4 111.87(19) . . ? C18_4 N17_4 C15_4 104.90(19) . . ? C18_4 N17_4 C17_4 127.7(2) . . ? C15_4 N17_4 C17_4 127.3(2) . . ? N17_4 C17_4 H17A_4 109.5 . . ? N17_4 C17_4 H17B_4 109.5 . . ? H17A_4 C17_4 H17B_4 109.5 . . ? N17_4 C17_4 H17C_4 109.5 . . ? H17A_4 C17_4 H17C_4 109.5 . . ? H17B_4 C17_4 H17C_4 109.5 . . ? N19_4 C18_4 N17_4 115.1(2) . . ? N19_4 C18_4 H18_4 122.4 . . ? N17_4 C18_4 H18_4 122.4 . . ? C18_4 N19_4 C14_4 102.4(2) . . ? O21_4 C21_4 C22_4 124.0(2) . . ? O21_4 C21_4 C26_4 114.3(2) . . ? C22_4 C21_4 C26_4 121.7(2) . . ? C21_4 O21_4 C27_4 118.41(19) . . ? C21_4 C22_4 C23_4 118.1(2) . . ? C21_4 C22_4 H22_4 121.0 . . ? C23_4 C22_4 H22_4 121.0 . . ? O23_4 C23_4 C24_4 124.2(2) . . ? O23_4 C23_4 C22_4 114.71(19) . . ? C24_4 C23_4 C22_4 121.1(2) . . ? C23_4 O23_4 C28_4 116.49(17) . . ? C23_4 C24_4 C25_4 120.1(2) . . ? C23_4 C24_4 H24_4 120.0 . . ? C25_4 C24_4 H24_4 120.0 . . ? C26_4 C25_4 C24_4 119.0(2) . . ? C26_4 C25_4 C29_4 122.20(19) . . ? C24_4 C25_4 C29_4 118.73(19) . . ? C21_4 C26_4 C25_4 120.0(2) . . ? C21_4 C26_4 H26_4 120.0 . . ? C25_4 C26_4 H26_4 120.0 . . ? O21_4 C27_4 H27A_4 109.5 . . ? O21_4 C27_4 H27B_4 109.5 . . ? H27A_4 C27_4 H27B_4 109.5 . . ? O21_4 C27_4 H27C_4 109.5 . . ? H27A_4 C27_4 H27C_4 109.5 . . ? H27B_4 C27_4 H27C_4 109.5 . . ? O23_4 C28_4 H28A_4 109.5 . . ? O23_4 C28_4 H28B_4 109.5 . . ? H28A_4 C28_4 H28B_4 109.5 . . ? O23_4 C28_4 H28C_4 109.5 . . ? H28A_4 C28_4 H28C_4 109.5 . . ? H28B_4 C28_4 H28C_4 109.5 . . ? C37_4 C29_4 C25_4 125.2(2) . . ? C37_4 C29_4 H29_4 117.4 . . ? C25_4 C29_4 H29_4 117.4 . . ? O31_4 C31_4 C32_4 117.3(2) . . ? O31_4 C31_4 C36_4 123.1(2) . . ? C32_4 C31_4 C36_4 119.6(2) . . ? C31_4 O31_4 H31_4 111(2) . . ? C31_4 C32_4 C33_4 120.1(2) . . ? C31_4 C32_4 H32_4 120.0 . . ? C33_4 C32_4 H32_4 120.0 . . ? C32_4 C33_4 C34_4 121.7(2) . . ? C32_4 C33_4 H33_4 119.1 . . ? C34_4 C33_4 H33_4 119.1 . . ? C35_4 C34_4 C33_4 117.4(2) . . ? C35_4 C34_4 C37_4 123.4(2) . . ? C33_4 C34_4 C37_4 119.3(2) . . ? C36_4 C35_4 C34_4 121.3(2) . . ? C36_4 C35_4 H35_4 119.3 . . ? C34_4 C35_4 H35_4 119.3 . . ? C31_4 C36_4 C35_4 119.9(2) . . ? C31_4 C36_4 H36_4 120.1 . . ? C35_4 C36_4 H36_4 120.1 . . ? C29_4 C37_4 C34_4 127.9(2) . . ? C29_4 C37_4 H37_4 116.1 . . ? C34_4 C37_4 H37_4 116.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16_1 N11_1 C12_1 O12_1 179.8(2) . . . . ? C11_1 N11_1 C12_1 O12_1 -0.8(3) . . . . ? C16_1 N11_1 C12_1 N13_1 -0.7(4) . . . . ? C11_1 N11_1 C12_1 N13_1 178.8(2) . . . . ? O12_1 C12_1 N13_1 C14_1 178.8(2) . . . . ? N11_1 C12_1 N13_1 C14_1 -0.8(3) . . . . ? O12_1 C12_1 N13_1 C13_1 1.7(4) . . . . ? N11_1 C12_1 N13_1 C13_1 -177.9(2) . . . . ? C12_1 N13_1 C14_1 N19_1 -178.9(2) . . . . ? C13_1 N13_1 C14_1 N19_1 -1.8(4) . . . . ? C12_1 N13_1 C14_1 C15_1 1.6(3) . . . . ? C13_1 N13_1 C14_1 C15_1 178.6(2) . . . . ? N19_1 C14_1 C15_1 N17_1 -0.3(3) . . . . ? N13_1 C14_1 C15_1 N17_1 179.3(2) . . . . ? N19_1 C14_1 C15_1 C16_1 179.4(2) . . . . ? N13_1 C14_1 C15_1 C16_1 -1.0(4) . . . . ? C12_1 N11_1 C16_1 O16_1 -178.6(2) . . . . ? C11_1 N11_1 C16_1 O16_1 1.9(3) . . . . ? C12_1 N11_1 C16_1 C15_1 1.2(3) . . . . ? C11_1 N11_1 C16_1 C15_1 -178.2(2) . . . . ? N17_1 C15_1 C16_1 O16_1 -0.9(4) . . . . ? C14_1 C15_1 C16_1 O16_1 179.5(2) . . . . ? N17_1 C15_1 C16_1 N11_1 179.3(2) . . . . ? C14_1 C15_1 C16_1 N11_1 -0.4(3) . . . . ? C14_1 C15_1 N17_1 C18_1 0.4(3) . . . . ? C16_1 C15_1 N17_1 C18_1 -179.3(3) . . . . ? C14_1 C15_1 N17_1 C17_1 177.9(2) . . . . ? C16_1 C15_1 N17_1 C17_1 -1.8(4) . . . . ? C15_1 N17_1 C18_1 N19_1 -0.3(3) . . . . ? C17_1 N17_1 C18_1 N19_1 -177.8(2) . . . . ? N17_1 C18_1 N19_1 C14_1 0.1(3) . . . . ? N13_1 C14_1 N19_1 C18_1 -179.4(2) . . . . ? C15_1 C14_1 N19_1 C18_1 0.1(3) . . . . ? C22_1 C21_1 O21_1 C27_1 3.1(4) . . . . ? C26_1 C21_1 O21_1 C27_1 -177.3(2) . . . . ? O21_1 C21_1 C22_1 C23_1 -180.0(2) . . . . ? C26_1 C21_1 C22_1 C23_1 0.5(4) . . . . ? C21_1 C22_1 C23_1 O23_1 178.9(2) . . . . ? C21_1 C22_1 C23_1 C24_1 -1.1(4) . . . . ? C22_1 C23_1 O23_1 C28_1 -167.1(2) . . . . ? C24_1 C23_1 O23_1 C28_1 12.9(3) . . . . ? O23_1 C23_1 C24_1 C25_1 -178.9(2) . . . . ? C22_1 C23_1 C24_1 C25_1 1.1(4) . . . . ? C23_1 C24_1 C25_1 C26_1 -0.5(3) . . . . ? C23_1 C24_1 C25_1 C29_1 177.7(2) . . . . ? C24_1 C25_1 C26_1 C21_1 -0.1(4) . . . . ? C29_1 C25_1 C26_1 C21_1 -178.2(2) . . . . ? O21_1 C21_1 C26_1 C25_1 -179.5(2) . . . . ? C22_1 C21_1 C26_1 C25_1 0.1(4) . . . . ? C26_1 C25_1 C29_1 C37_1 0.8(4) . . . . ? C24_1 C25_1 C29_1 C37_1 -177.4(2) . . . . ? O31_1 C31_1 C32_1 C33_1 -178.3(2) . . . . ? C36_1 C31_1 C32_1 C33_1 2.0(4) . . . . ? C31_1 C32_1 C33_1 C34_1 -1.6(4) . . . . ? C32_1 C33_1 C34_1 C35_1 0.0(4) . . . . ? C32_1 C33_1 C34_1 C37_1 179.6(2) . . . . ? C33_1 C34_1 C35_1 C36_1 1.0(4) . . . . ? C37_1 C34_1 C35_1 C36_1 -178.5(2) . . . . ? C34_1 C35_1 C36_1 C31_1 -0.6(4) . . . . ? O31_1 C31_1 C36_1 C35_1 179.3(2) . . . . ? C32_1 C31_1 C36_1 C35_1 -0.9(4) . . . . ? C25_1 C29_1 C37_1 C34_1 177.4(2) . . . . ? C33_1 C34_1 C37_1 C29_1 169.5(3) . . . . ? C35_1 C34_1 C37_1 C29_1 -11.0(4) . . . . ? C16_2 N11_2 C12_2 O12_2 178.2(2) . . . . ? C11_2 N11_2 C12_2 O12_2 1.8(3) . . . . ? C16_2 N11_2 C12_2 N13_2 -2.0(3) . . . . ? C11_2 N11_2 C12_2 N13_2 -178.3(2) . . . . ? O12_2 C12_2 N13_2 C14_2 -179.0(2) . . . . ? N11_2 C12_2 N13_2 C14_2 1.1(3) . . . . ? O12_2 C12_2 N13_2 C13_2 -2.6(3) . . . . ? N11_2 C12_2 N13_2 C13_2 177.5(2) . . . . ? C12_2 N13_2 C14_2 N19_2 177.1(2) . . . . ? C13_2 N13_2 C14_2 N19_2 0.8(4) . . . . ? C12_2 N13_2 C14_2 C15_2 -1.1(3) . . . . ? C13_2 N13_2 C14_2 C15_2 -177.4(2) . . . . ? N19_2 C14_2 C15_2 N17_2 -0.5(3) . . . . ? N13_2 C14_2 C15_2 N17_2 177.9(2) . . . . ? N19_2 C14_2 C15_2 C16_2 -176.6(2) . . . . ? N13_2 C14_2 C15_2 C16_2 1.8(4) . . . . ? C12_2 N11_2 C16_2 O16_2 -176.7(2) . . . . ? C11_2 N11_2 C16_2 O16_2 -0.4(3) . . . . ? C12_2 N11_2 C16_2 C15_2 2.5(3) . . . . ? C11_2 N11_2 C16_2 C15_2 178.8(2) . . . . ? C14_2 C15_2 C16_2 O16_2 176.7(2) . . . . ? N17_2 C15_2 C16_2 O16_2 1.9(4) . . . . ? C14_2 C15_2 C16_2 N11_2 -2.3(3) . . . . ? N17_2 C15_2 C16_2 N11_2 -177.2(2) . . . . ? C14_2 C15_2 N17_2 C18_2 0.7(3) . . . . ? C16_2 C15_2 N17_2 C18_2 176.2(3) . . . . ? C14_2 C15_2 N17_2 C17_2 -179.0(2) . . . . ? C16_2 C15_2 N17_2 C17_2 -3.5(4) . . . . ? C15_2 N17_2 C18_2 N19_2 -0.7(3) . . . . ? C17_2 N17_2 C18_2 N19_2 179.0(2) . . . . ? N17_2 C18_2 N19_2 C14_2 0.4(3) . . . . ? N13_2 C14_2 N19_2 C18_2 -178.2(2) . . . . ? C15_2 C14_2 N19_2 C18_2 0.1(3) . . . . ? C26_2 C21_2 O21_2 C27_2 -170.2(2) . . . . ? C22_2 C21_2 O21_2 C27_2 9.2(4) . . . . ? O21_2 C21_2 C22_2 C23_2 -178.8(2) . . . . ? C26_2 C21_2 C22_2 C23_2 0.5(4) . . . . ? C21_2 C22_2 C23_2 O23_2 178.3(2) . . . . ? C21_2 C22_2 C23_2 C24_2 -1.3(4) . . . . ? C24_2 C23_2 O23_2 C28_2 11.5(4) . . . . ? C22_2 C23_2 O23_2 C28_2 -168.1(2) . . . . ? O23_2 C23_2 C24_2 C25_2 -177.9(2) . . . . ? C22_2 C23_2 C24_2 C25_2 1.7(4) . . . . ? C23_2 C24_2 C25_2 C26_2 -1.3(4) . . . . ? C23_2 C24_2 C25_2 C29_2 176.6(2) . . . . ? O21_2 C21_2 C26_2 C25_2 179.2(2) . . . . ? C22_2 C21_2 C26_2 C25_2 -0.1(4) . . . . ? C24_2 C25_2 C26_2 C21_2 0.5(3) . . . . ? C29_2 C25_2 C26_2 C21_2 -177.3(2) . . . . ? C26_2 C25_2 C29_2 C37_2 2.1(4) . . . . ? C24_2 C25_2 C29_2 C37_2 -175.6(2) . . . . ? O31_2 C31_2 C32_2 C33_2 -179.0(2) . . . . ? C36_2 C31_2 C32_2 C33_2 0.7(4) . . . . ? C31_2 C32_2 C33_2 C34_2 -0.1(4) . . . . ? C32_2 C33_2 C34_2 C35_2 -0.5(4) . . . . ? C32_2 C33_2 C34_2 C37_2 177.5(2) . . . . ? C33_2 C34_2 C35_2 C36_2 0.5(4) . . . . ? C37_2 C34_2 C35_2 C36_2 -177.4(2) . . . . ? C34_2 C35_2 C36_2 C31_2 0.1(4) . . . . ? O31_2 C31_2 C36_2 C35_2 179.0(2) . . . . ? C32_2 C31_2 C36_2 C35_2 -0.7(4) . . . . ? C25_2 C29_2 C37_2 C34_2 173.5(2) . . . . ? C35_2 C34_2 C37_2 C29_2 1.9(4) . . . . ? C33_2 C34_2 C37_2 C29_2 -175.9(3) . . . . ? C16_3 N11_3 C12_3 O12_3 178.4(2) . . . . ? C11_3 N11_3 C12_3 O12_3 -0.9(3) . . . . ? C16_3 N11_3 C12_3 N13_3 -1.9(3) . . . . ? C11_3 N11_3 C12_3 N13_3 178.8(2) . . . . ? O12_3 C12_3 N13_3 C14_3 -178.8(2) . . . . ? N11_3 C12_3 N13_3 C14_3 1.5(3) . . . . ? O12_3 C12_3 N13_3 C13_3 -1.9(4) . . . . ? N11_3 C12_3 N13_3 C13_3 178.4(2) . . . . ? C12_3 N13_3 C14_3 N19_3 177.6(2) . . . . ? C13_3 N13_3 C14_3 N19_3 0.7(4) . . . . ? C12_3 N13_3 C14_3 C15_3 -0.6(3) . . . . ? C13_3 N13_3 C14_3 C15_3 -177.5(2) . . . . ? N19_3 C14_3 C15_3 N17_3 -0.5(3) . . . . ? N13_3 C14_3 C15_3 N17_3 177.9(2) . . . . ? N19_3 C14_3 C15_3 C16_3 -178.5(2) . . . . ? N13_3 C14_3 C15_3 C16_3 -0.1(4) . . . . ? C12_3 N11_3 C16_3 O16_3 -177.5(2) . . . . ? C11_3 N11_3 C16_3 O16_3 1.8(3) . . . . ? C12_3 N11_3 C16_3 C15_3 1.2(3) . . . . ? C11_3 N11_3 C16_3 C15_3 -179.5(2) . . . . ? C14_3 C15_3 C16_3 O16_3 178.4(2) . . . . ? N17_3 C15_3 C16_3 O16_3 1.0(4) . . . . ? C14_3 C15_3 C16_3 N11_3 -0.2(3) . . . . ? N17_3 C15_3 C16_3 N11_3 -177.5(2) . . . . ? C14_3 C15_3 N17_3 C18_3 0.7(3) . . . . ? C16_3 C15_3 N17_3 C18_3 178.4(3) . . . . ? C14_3 C15_3 N17_3 C17_3 -179.5(2) . . . . ? C16_3 C15_3 N17_3 C17_3 -1.8(4) . . . . ? C15_3 N17_3 C18_3 N19_3 -0.7(3) . . . . ? C17_3 N17_3 C18_3 N19_3 179.5(2) . . . . ? N17_3 C18_3 N19_3 C14_3 0.4(3) . . . . ? C15_3 C14_3 N19_3 C18_3 0.1(3) . . . . ? N13_3 C14_3 N19_3 C18_3 -178.3(2) . . . . ? C22_3 C21_3 O21_3 C27_3 10.1(4) . . . . ? C26_3 C21_3 O21_3 C27_3 -169.7(2) . . . . ? O21_3 C21_3 C22_3 C23_3 -179.3(2) . . . . ? C26_3 C21_3 C22_3 C23_3 0.4(4) . . . . ? C21_3 C22_3 C23_3 O23_3 178.2(2) . . . . ? C21_3 C22_3 C23_3 C24_3 -1.1(3) . . . . ? C22_3 C23_3 O23_3 C28_3 -165.8(2) . . . . ? C24_3 C23_3 O23_3 C28_3 13.5(3) . . . . ? O23_3 C23_3 C24_3 C25_3 -177.6(2) . . . . ? C22_3 C23_3 C24_3 C25_3 1.6(4) . . . . ? C23_3 C24_3 C25_3 C26_3 -1.5(3) . . . . ? C23_3 C24_3 C25_3 C29_3 176.1(2) . . . . ? O21_3 C21_3 C26_3 C25_3 179.4(2) . . . . ? C22_3 C21_3 C26_3 C25_3 -0.3(4) . . . . ? C24_3 C25_3 C26_3 C21_3 0.9(3) . . . . ? C29_3 C25_3 C26_3 C21_3 -176.6(2) . . . . ? C24_3 C25_3 C29_3 C37_3 -171.6(2) . . . . ? C26_3 C25_3 C29_3 C37_3 5.9(4) . . . . ? O31_3 C31_3 C32_3 C33_3 -179.0(2) . . . . ? C36_3 C31_3 C32_3 C33_3 0.1(4) . . . . ? C31_3 C32_3 C33_3 C34_3 0.1(4) . . . . ? C32_3 C33_3 C34_3 C35_3 -0.4(4) . . . . ? C32_3 C33_3 C34_3 C37_3 177.4(2) . . . . ? C33_3 C34_3 C35_3 C36_3 0.5(3) . . . . ? C37_3 C34_3 C35_3 C36_3 -177.2(2) . . . . ? O31_3 C31_3 C36_3 C35_3 179.1(2) . . . . ? C32_3 C31_3 C36_3 C35_3 0.0(4) . . . . ? C34_3 C35_3 C36_3 C31_3 -0.3(4) . . . . ? C25_3 C29_3 C37_3 C34_3 173.3(2) . . . . ? C33_3 C34_3 C37_3 C29_3 179.8(2) . . . . ? C35_3 C34_3 C37_3 C29_3 -2.6(4) . . . . ? C16_4 N11_4 C12_4 O12_4 179.4(2) . . . . ? C11_4 N11_4 C12_4 O12_4 -3.4(3) . . . . ? C16_4 N11_4 C12_4 N13_4 -0.9(3) . . . . ? C11_4 N11_4 C12_4 N13_4 176.3(2) . . . . ? O12_4 C12_4 N13_4 C14_4 178.7(2) . . . . ? N11_4 C12_4 N13_4 C14_4 -1.0(3) . . . . ? O12_4 C12_4 N13_4 C13_4 2.8(4) . . . . ? N11_4 C12_4 N13_4 C13_4 -177.0(2) . . . . ? C12_4 N13_4 C14_4 N19_4 -178.2(2) . . . . ? C13_4 N13_4 C14_4 N19_4 -2.3(4) . . . . ? C12_4 N13_4 C14_4 C15_4 2.4(4) . . . . ? C13_4 N13_4 C14_4 C15_4 178.3(2) . . . . ? N13_4 C14_4 C15_4 N17_4 179.1(2) . . . . ? N19_4 C14_4 C15_4 N17_4 -0.4(3) . . . . ? N13_4 C14_4 C15_4 C16_4 -2.0(4) . . . . ? N19_4 C14_4 C15_4 C16_4 178.5(2) . . . . ? C12_4 N11_4 C16_4 O16_4 -179.3(2) . . . . ? C11_4 N11_4 C16_4 O16_4 3.5(3) . . . . ? C12_4 N11_4 C16_4 C15_4 1.3(3) . . . . ? C11_4 N11_4 C16_4 C15_4 -175.9(2) . . . . ? C14_4 C15_4 C16_4 O16_4 -179.2(2) . . . . ? N17_4 C15_4 C16_4 O16_4 -0.6(4) . . . . ? C14_4 C15_4 C16_4 N11_4 0.2(3) . . . . ? N17_4 C15_4 C16_4 N11_4 178.8(2) . . . . ? C14_4 C15_4 N17_4 C18_4 0.8(3) . . . . ? C16_4 C15_4 N17_4 C18_4 -178.0(3) . . . . ? C14_4 C15_4 N17_4 C17_4 177.8(2) . . . . ? C16_4 C15_4 N17_4 C17_4 -1.0(4) . . . . ? C15_4 N17_4 C18_4 N19_4 -1.0(3) . . . . ? C17_4 N17_4 C18_4 N19_4 -178.0(2) . . . . ? N17_4 C18_4 N19_4 C14_4 0.8(3) . . . . ? N13_4 C14_4 N19_4 C18_4 -179.6(2) . . . . ? C15_4 C14_4 N19_4 C18_4 -0.2(3) . . . . ? C22_4 C21_4 O21_4 C27_4 1.4(4) . . . . ? C26_4 C21_4 O21_4 C27_4 -178.8(2) . . . . ? O21_4 C21_4 C22_4 C23_4 179.6(2) . . . . ? C26_4 C21_4 C22_4 C23_4 -0.1(3) . . . . ? C21_4 C22_4 C23_4 O23_4 178.9(2) . . . . ? C21_4 C22_4 C23_4 C24_4 -0.6(3) . . . . ? C24_4 C23_4 O23_4 C28_4 11.6(3) . . . . ? C22_4 C23_4 O23_4 C28_4 -167.8(2) . . . . ? O23_4 C23_4 C24_4 C25_4 -178.5(2) . . . . ? C22_4 C23_4 C24_4 C25_4 1.0(3) . . . . ? C23_4 C24_4 C25_4 C26_4 -0.5(3) . . . . ? C23_4 C24_4 C25_4 C29_4 177.5(2) . . . . ? O21_4 C21_4 C26_4 C25_4 -179.3(2) . . . . ? C22_4 C21_4 C26_4 C25_4 0.5(4) . . . . ? C24_4 C25_4 C26_4 C21_4 -0.2(3) . . . . ? C29_4 C25_4 C26_4 C21_4 -178.2(2) . . . . ? C26_4 C25_4 C29_4 C37_4 3.0(4) . . . . ? C24_4 C25_4 C29_4 C37_4 -175.1(2) . . . . ? O31_4 C31_4 C32_4 C33_4 -177.5(2) . . . . ? C36_4 C31_4 C32_4 C33_4 2.1(4) . . . . ? C31_4 C32_4 C33_4 C34_4 -0.5(4) . . . . ? C32_4 C33_4 C34_4 C35_4 -1.7(4) . . . . ? C32_4 C33_4 C34_4 C37_4 177.2(2) . . . . ? C33_4 C34_4 C35_4 C36_4 2.4(4) . . . . ? C37_4 C34_4 C35_4 C36_4 -176.5(2) . . . . ? O31_4 C31_4 C36_4 C35_4 178.1(2) . . . . ? C32_4 C31_4 C36_4 C35_4 -1.4(4) . . . . ? C34_4 C35_4 C36_4 C31_4 -0.8(4) . . . . ? C25_4 C29_4 C37_4 C34_4 174.9(2) . . . . ? C35_4 C34_4 C37_4 C29_4 -9.1(4) . . . . ? C33_4 C34_4 C37_4 C29_4 172.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O31_1 H31_1 O16_1 0.92(3) 1.80(3) 2.716(3) 175(3) . O31_2 H31_2 O16_2 0.78(3) 1.96(3) 2.725(2) 169(3) . O31_3 H31_3 O16_3 1.04(3) 1.68(3) 2.719(2) 174(3) . O31_4 H31_4 O16_4 0.81(3) 1.91(3) 2.716(3) 175(3) . _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.469 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.064 # Attachment '3.cif' data_205650 _database_code_depnum_ccdc_archive 'CCDC 764873' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 205650 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C15 H12 N2 O1) (C16 H16 O3) ; _chemical_formula_sum 'C31 H28 N2 O4' _chemical_formula_weight 492.55 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 38.809(3) _cell_length_b 5.3921(4) _cell_length_c 26.7284(17) _cell_angle_alpha 90.00 _cell_angle_beta 117.306(3) _cell_angle_gamma 90.00 _cell_volume 4969.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6151 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 31.68 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29297 _diffrn_reflns_av_R_equivalents 0.0616 _diffrn_reflns_av_sigmaI/netI 0.0660 _diffrn_reflns_limit_h_min -56 _diffrn_reflns_limit_h_max 56 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 32.54 _reflns_number_total 8372 _reflns_number_gt 5455 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0600P)^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 8372 _refine_ls_number_parameters 345 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0882 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1361 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 C11 C 0.28077(3) 0.3513(3) 0.65520(5) 0.0200(3) Uani 1 1 d . . . C12 C 0.28942(3) 0.5117(3) 0.70071(5) 0.0218(3) Uani 1 1 d . . . C13 C 0.32570(4) 0.4821(3) 0.74810(5) 0.0267(3) Uani 1 1 d . . . H13 H 0.3330 0.5929 0.7789 0.032 Uiso 1 1 calc R . . C14 C 0.35090(4) 0.2957(3) 0.75088(5) 0.0296(3) Uani 1 1 d . . . H14 H 0.3752 0.2790 0.7834 0.035 Uiso 1 1 calc R . . C15 C 0.34076(4) 0.1328(3) 0.70620(6) 0.0287(3) Uani 1 1 d . . . H15 H 0.3578 0.0019 0.7085 0.034 Uiso 1 1 calc R . . C16 C 0.30559(4) 0.1616(3) 0.65809(5) 0.0248(3) Uani 1 1 d . . . H16 H 0.2986 0.0513 0.6272 0.030 Uiso 1 1 calc R . . C17 C 0.26237(4) 0.6997(3) 0.70089(5) 0.0245(3) Uani 1 1 d . . . H17 H 0.2736 0.8435 0.7229 0.029 Uiso 1 1 calc R . . C21 C 0.20992(3) 0.3444(2) 0.60387(5) 0.0186(3) Uani 1 1 d . . . C22 C 0.19881(3) 0.4952(2) 0.63660(5) 0.0199(3) Uani 1 1 d . . . C23 C 0.16231(4) 0.4500(3) 0.63367(5) 0.0236(3) Uani 1 1 d . . . H23 H 0.1534 0.5534 0.6541 0.028 Uiso 1 1 calc R . . C24 C 0.13909(3) 0.2582(3) 0.60163(5) 0.0236(3) Uani 1 1 d . . . H24 H 0.1147 0.2293 0.6009 0.028 Uiso 1 1 calc R . . C25 C 0.15113(3) 0.1072(3) 0.57049(5) 0.0233(3) Uani 1 1 d . . . H25 H 0.1351 -0.0250 0.5486 0.028 Uiso 1 1 calc R . . C26 C 0.18672(3) 0.1513(2) 0.57172(5) 0.0210(3) Uani 1 1 d . . . H26 H 0.1952 0.0492 0.5506 0.025 Uiso 1 1 calc R . . C27 C 0.22346(4) 0.6922(3) 0.67341(5) 0.0227(3) Uani 1 1 d . . . H27 H 0.2103 0.8313 0.6785 0.027 Uiso 1 1 calc R . . N28 N 0.24616(3) 0.3927(2) 0.60352(4) 0.0195(2) Uani 1 1 d . . . C31 C 0.24668(3) 0.5305(2) 0.56086(5) 0.0197(3) Uani 1 1 d . . . N31 N 0.28142(3) 0.5907(2) 0.56523(5) 0.0268(3) Uani 1 1 d . . . H31A H 0.2834(4) 0.680(3) 0.5391(7) 0.032 Uiso 1 1 d . . . H31B H 0.3028(5) 0.540(3) 0.5930(7) 0.032 Uiso 1 1 d . . . O32 O 0.21592(2) 0.59532(18) 0.51973(3) 0.0249(2) Uani 1 1 d . . . C41 C 0.11838(3) 0.5408(3) 0.42892(5) 0.0226(3) Uani 1 1 d . . . O41 O 0.13777(3) 0.66503(19) 0.47855(4) 0.0310(2) Uani 1 1 d . . . C42 C 0.08273(4) 0.6346(3) 0.38973(6) 0.0274(3) Uani 1 1 d . . . H42 H 0.0724 0.7787 0.3984 0.033 Uiso 1 1 calc R . . C43 C 0.06230(4) 0.5186(3) 0.33827(5) 0.0266(3) Uani 1 1 d . . . H43 H 0.0381 0.5853 0.3119 0.032 Uiso 1 1 calc R . . C44 C 0.07631(3) 0.3064(3) 0.32410(5) 0.0221(3) Uani 1 1 d . . . C45 C 0.11178(4) 0.2112(3) 0.36493(5) 0.0237(3) Uani 1 1 d . . . H45 H 0.1217 0.0636 0.3569 0.028 Uiso 1 1 calc R . . C46 C 0.13269(4) 0.3259(3) 0.41642(5) 0.0232(3) Uani 1 1 d . . . H46 H 0.1567 0.2582 0.4432 0.028 Uiso 1 1 calc R . . C47 C 0.05511(4) 0.1988(3) 0.26755(5) 0.0242(3) Uani 1 1 d . . . H47 H 0.0322 0.2819 0.2418 0.029 Uiso 1 1 calc R . . C51 C 0.04764(3) -0.1057(3) 0.19179(5) 0.0225(3) Uani 1 1 d . . . C52 C 0.01421(3) -0.0031(3) 0.14725(5) 0.0225(3) Uani 1 1 d . . . H52 H 0.0008 0.1301 0.1538 0.027 Uiso 1 1 calc R . . C53 C 0.00136(3) -0.1007(3) 0.09367(5) 0.0219(3) Uani 1 1 d . . . O53 O -0.03024(2) -0.01471(19) 0.04683(4) 0.0276(2) Uani 1 1 d . . . C54 C 0.02052(3) -0.2977(3) 0.08298(5) 0.0215(3) Uani 1 1 d . . . H54 H 0.0114 -0.3608 0.0459 0.026 Uiso 1 1 calc R . . C55 C 0.05277(3) -0.3990(2) 0.12706(5) 0.0214(3) Uani 1 1 d . . . O55 O 0.07417(2) -0.59127(18) 0.12222(4) 0.0257(2) Uani 1 1 d . . . C56 C 0.06619(4) -0.3033(3) 0.18134(5) 0.0240(3) Uani 1 1 d . . . H56 H 0.0884 -0.3747 0.2115 0.029 Uiso 1 1 calc R . . C57 C 0.06510(4) -0.0052(3) 0.24919(5) 0.0252(3) Uani 1 1 d . . . H57 H 0.0862 -0.0970 0.2767 0.030 Uiso 1 1 calc R . . C58 C -0.05023(4) 0.1948(3) 0.05398(5) 0.0254(3) Uani 1 1 d . . . H58A H -0.0719 0.2398 0.0176 0.038 Uiso 1 1 calc R . . H58B H -0.0323 0.3351 0.0686 0.038 Uiso 1 1 calc R . . H58C H -0.0602 0.1527 0.0806 0.038 Uiso 1 1 calc R . . C59 C 0.06138(4) -0.6987(3) 0.06776(5) 0.0270(3) Uani 1 1 d . . . H59A H 0.0787 -0.8355 0.0701 0.041 Uiso 1 1 calc R . . H59B H 0.0618 -0.5726 0.0416 0.041 Uiso 1 1 calc R . . H59C H 0.0349 -0.7618 0.0542 0.041 Uiso 1 1 calc R . . H41 H 0.1624(5) 0.610(3) 0.4960(6) 0.032 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.0152(5) 0.0267(7) 0.0170(5) 0.0056(5) 0.0065(4) 0.0002(5) C12 0.0201(6) 0.0255(7) 0.0194(5) 0.0037(5) 0.0088(5) -0.0030(5) C13 0.0219(6) 0.0365(8) 0.0190(6) 0.0022(5) 0.0072(5) -0.0053(6) C14 0.0192(6) 0.0438(9) 0.0215(6) 0.0105(6) 0.0057(5) -0.0008(6) C15 0.0216(6) 0.0327(8) 0.0308(7) 0.0121(6) 0.0112(5) 0.0070(5) C16 0.0221(6) 0.0281(8) 0.0243(6) 0.0038(5) 0.0108(5) 0.0007(5) C17 0.0268(6) 0.0234(7) 0.0225(6) -0.0033(5) 0.0106(5) -0.0050(5) C21 0.0150(5) 0.0231(7) 0.0167(5) 0.0039(4) 0.0064(4) 0.0014(5) C22 0.0193(5) 0.0206(7) 0.0183(5) 0.0018(5) 0.0073(5) 0.0020(5) C23 0.0220(6) 0.0287(8) 0.0214(6) -0.0007(5) 0.0110(5) 0.0023(5) C24 0.0172(5) 0.0276(8) 0.0261(6) 0.0021(5) 0.0100(5) 0.0004(5) C25 0.0205(6) 0.0227(7) 0.0230(6) -0.0016(5) 0.0067(5) -0.0017(5) C26 0.0207(6) 0.0231(7) 0.0179(5) -0.0006(5) 0.0076(5) 0.0025(5) C27 0.0242(6) 0.0219(7) 0.0228(6) -0.0011(5) 0.0115(5) 0.0004(5) N28 0.0158(4) 0.0255(6) 0.0163(4) 0.0030(4) 0.0066(4) 0.0012(4) C31 0.0208(5) 0.0205(7) 0.0179(5) -0.0007(5) 0.0089(5) -0.0002(5) N31 0.0186(5) 0.0392(8) 0.0216(5) 0.0101(5) 0.0082(4) 0.0002(5) O32 0.0197(4) 0.0329(6) 0.0193(4) 0.0069(4) 0.0065(3) 0.0010(4) C41 0.0205(6) 0.0231(7) 0.0228(6) -0.0038(5) 0.0088(5) -0.0043(5) O41 0.0235(5) 0.0319(6) 0.0293(5) -0.0122(4) 0.0050(4) 0.0001(4) C42 0.0253(6) 0.0179(7) 0.0338(7) -0.0034(5) 0.0089(5) 0.0002(5) C43 0.0202(6) 0.0256(8) 0.0267(6) 0.0024(5) 0.0046(5) 0.0001(5) C44 0.0195(5) 0.0263(7) 0.0196(5) 0.0012(5) 0.0080(5) -0.0037(5) C45 0.0234(6) 0.0269(8) 0.0219(6) -0.0024(5) 0.0113(5) 0.0020(5) C46 0.0182(5) 0.0285(8) 0.0206(6) -0.0007(5) 0.0070(5) 0.0023(5) C47 0.0196(6) 0.0287(8) 0.0209(6) 0.0016(5) 0.0065(5) -0.0013(5) C51 0.0207(6) 0.0276(7) 0.0181(5) 0.0002(5) 0.0078(5) -0.0044(5) C52 0.0191(6) 0.0262(7) 0.0207(6) -0.0004(5) 0.0078(5) -0.0015(5) C53 0.0172(5) 0.0250(7) 0.0196(5) 0.0026(5) 0.0051(5) -0.0001(5) O53 0.0218(4) 0.0350(6) 0.0196(4) 0.0005(4) 0.0039(4) 0.0081(4) C54 0.0194(6) 0.0254(7) 0.0176(5) -0.0006(5) 0.0068(5) -0.0032(5) C55 0.0192(6) 0.0222(7) 0.0229(6) 0.0007(5) 0.0099(5) -0.0021(5) O55 0.0227(4) 0.0287(6) 0.0218(4) 0.0000(4) 0.0069(4) 0.0041(4) C56 0.0205(6) 0.0281(8) 0.0185(5) 0.0027(5) 0.0049(5) 0.0001(5) C57 0.0218(6) 0.0306(8) 0.0188(6) 0.0023(5) 0.0057(5) 0.0011(5) C58 0.0211(6) 0.0263(8) 0.0256(6) 0.0037(5) 0.0079(5) 0.0030(5) C59 0.0277(6) 0.0272(8) 0.0246(6) -0.0019(5) 0.0107(5) 0.0009(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 C11 C16 1.3829(18) . ? C11 C12 1.4018(18) . ? C11 N28 1.4352(14) . ? C12 C13 1.4056(17) . ? C12 C17 1.4608(19) . ? C13 C14 1.380(2) . ? C13 H13 0.9500 . ? C14 C15 1.386(2) . ? C14 H14 0.9500 . ? C15 C16 1.3894(17) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C27 1.3432(17) . ? C17 H17 0.9500 . ? C21 C26 1.3867(18) . ? C21 C22 1.3995(18) . ? C21 N28 1.4346(15) . ? C22 C23 1.4040(17) . ? C22 C27 1.4655(18) . ? C23 C24 1.3808(19) . ? C23 H23 0.9500 . ? C24 C25 1.3897(19) . ? C24 H24 0.9500 . ? C25 C26 1.3870(17) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? N28 C31 1.3690(16) . ? C31 O32 1.2456(14) . ? C31 N31 1.3389(16) . ? N31 H31A 0.880(17) . ? N31 H31B 0.865(16) . ? C41 O41 1.3634(15) . ? C41 C46 1.3902(19) . ? C41 C42 1.3921(18) . ? O41 H41 0.900(16) . ? C42 C43 1.3825(19) . ? C42 H42 0.9500 . ? C43 C44 1.3918(19) . ? C43 H43 0.9500 . ? C44 C45 1.4040(17) . ? C44 C47 1.4689(17) . ? C45 C46 1.3823(17) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 C57 1.333(2) . ? C47 H47 0.9500 . ? C51 C56 1.3839(19) . ? C51 C52 1.4104(17) . ? C51 C57 1.4672(17) . ? C52 C53 1.3864(17) . ? C52 H52 0.9500 . ? C53 O53 1.3704(14) . ? C53 C54 1.3989(18) . ? O53 C58 1.4319(16) . ? C54 C55 1.3784(17) . ? C54 H54 0.9500 . ? C55 O55 1.3710(15) . ? C55 C56 1.3963(17) . ? O55 C59 1.4276(15) . ? C56 H56 0.9500 . ? C57 H57 0.9500 . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 0.9800 . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 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 C16 C11 C12 121.63(11) . . ? C16 C11 N28 119.27(11) . . ? C12 C11 N28 119.03(11) . . ? C11 C12 C13 117.00(12) . . ? C11 C12 C17 122.99(11) . . ? C13 C12 C17 120.00(12) . . ? C14 C13 C12 121.55(13) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 120.07(11) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 119.76(13) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 119.86(13) . . ? C11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C27 C17 C12 127.35(12) . . ? C27 C17 H17 116.3 . . ? C12 C17 H17 116.3 . . ? C26 C21 C22 121.68(11) . . ? C26 C21 N28 119.46(11) . . ? C22 C21 N28 118.85(11) . . ? C21 C22 C23 117.16(11) . . ? C21 C22 C27 123.21(11) . . ? C23 C22 C27 119.63(12) . . ? C24 C23 C22 121.27(12) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 C25 120.51(12) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C26 C25 C24 119.33(12) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? C21 C26 C25 119.99(12) . . ? C21 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C17 C27 C22 127.79(13) . . ? C17 C27 H27 116.1 . . ? C22 C27 H27 116.1 . . ? C31 N28 C21 119.54(9) . . ? C31 N28 C11 121.40(10) . . ? C21 N28 C11 116.94(9) . . ? O32 C31 N31 121.88(12) . . ? O32 C31 N28 120.87(11) . . ? N31 C31 N28 117.25(11) . . ? C31 N31 H31A 121.0(10) . . ? C31 N31 H31B 121.9(11) . . ? H31A N31 H31B 117.1(15) . . ? O41 C41 C46 122.71(11) . . ? O41 C41 C42 117.90(12) . . ? C46 C41 C42 119.39(12) . . ? C41 O41 H41 108.8(10) . . ? C43 C42 C41 120.17(13) . . ? C43 C42 H42 119.9 . . ? C41 C42 H42 119.9 . . ? C42 C43 C44 121.69(12) . . ? C42 C43 H43 119.2 . . ? C44 C43 H43 119.2 . . ? C43 C44 C45 117.09(11) . . ? C43 C44 C47 120.03(11) . . ? C45 C44 C47 122.82(12) . . ? C46 C45 C44 121.91(13) . . ? C46 C45 H45 119.0 . . ? C44 C45 H45 119.0 . . ? C45 C46 C41 119.71(11) . . ? C45 C46 H46 120.1 . . ? C41 C46 H46 120.1 . . ? C57 C47 C44 125.78(12) . . ? C57 C47 H47 117.1 . . ? C44 C47 H47 117.1 . . ? C56 C51 C52 119.60(11) . . ? C56 C51 C57 117.50(11) . . ? C52 C51 C57 122.85(12) . . ? C53 C52 C51 118.59(12) . . ? C53 C52 H52 120.7 . . ? C51 C52 H52 120.7 . . ? O53 C53 C52 124.21(12) . . ? O53 C53 C54 114.03(11) . . ? C52 C53 C54 121.75(11) . . ? C53 O53 C58 117.24(10) . . ? C55 C54 C53 119.05(11) . . ? C55 C54 H54 120.5 . . ? C53 C54 H54 120.5 . . ? O55 C55 C54 124.81(11) . . ? O55 C55 C56 115.11(10) . . ? C54 C55 C56 120.08(12) . . ? C55 O55 C59 117.43(9) . . ? C51 C56 C55 120.91(11) . . ? C51 C56 H56 119.5 . . ? C55 C56 H56 119.5 . . ? C47 C57 C51 128.10(12) . . ? C47 C57 H57 115.9 . . ? C51 C57 H57 115.9 . . ? O53 C58 H58A 109.5 . . ? O53 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? O53 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? O55 C59 H59A 109.5 . . ? O55 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? O55 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 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 C16 C11 C12 C13 4.23(19) . . . . ? N28 C11 C12 C13 -172.82(11) . . . . ? C16 C11 C12 C17 -174.45(12) . . . . ? N28 C11 C12 C17 8.50(19) . . . . ? C11 C12 C13 C14 -3.11(19) . . . . ? C17 C12 C13 C14 175.61(13) . . . . ? C12 C13 C14 C15 0.3(2) . . . . ? C13 C14 C15 C16 1.6(2) . . . . ? C12 C11 C16 C15 -2.5(2) . . . . ? N28 C11 C16 C15 174.54(12) . . . . ? C14 C15 C16 C11 -0.5(2) . . . . ? C11 C12 C17 C27 28.7(2) . . . . ? C13 C12 C17 C27 -149.96(14) . . . . ? C26 C21 C22 C23 -2.72(18) . . . . ? N28 C21 C22 C23 176.92(11) . . . . ? C26 C21 C22 C27 176.60(12) . . . . ? N28 C21 C22 C27 -3.76(18) . . . . ? C21 C22 C23 C24 2.59(18) . . . . ? C27 C22 C23 C24 -176.76(12) . . . . ? C22 C23 C24 C25 -1.2(2) . . . . ? C23 C24 C25 C26 -0.18(19) . . . . ? C22 C21 C26 C25 1.44(19) . . . . ? N28 C21 C26 C25 -178.19(11) . . . . ? C24 C25 C26 C21 0.07(19) . . . . ? C12 C17 C27 C22 -0.3(2) . . . . ? C21 C22 C27 C17 -30.8(2) . . . . ? C23 C22 C27 C17 148.47(14) . . . . ? C26 C21 N28 C31 82.60(15) . . . . ? C22 C21 N28 C31 -97.05(14) . . . . ? C26 C21 N28 C11 -113.70(13) . . . . ? C22 C21 N28 C11 66.66(15) . . . . ? C16 C11 N28 C31 -83.61(16) . . . . ? C12 C11 N28 C31 93.51(15) . . . . ? C16 C11 N28 C21 113.00(13) . . . . ? C12 C11 N28 C21 -69.87(16) . . . . ? C21 N28 C31 O32 -6.61(19) . . . . ? C11 N28 C31 O32 -169.57(12) . . . . ? C21 N28 C31 N31 173.70(12) . . . . ? C11 N28 C31 N31 10.74(18) . . . . ? O41 C41 C42 C43 178.61(12) . . . . ? C46 C41 C42 C43 -1.7(2) . . . . ? C41 C42 C43 C44 0.3(2) . . . . ? C42 C43 C44 C45 1.5(2) . . . . ? C42 C43 C44 C47 -175.67(13) . . . . ? C43 C44 C45 C46 -1.9(2) . . . . ? C47 C44 C45 C46 175.15(13) . . . . ? C44 C45 C46 C41 0.6(2) . . . . ? O41 C41 C46 C45 -179.05(13) . . . . ? C42 C41 C46 C45 1.3(2) . . . . ? C43 C44 C47 C57 -178.81(14) . . . . ? C45 C44 C47 C57 4.2(2) . . . . ? C56 C51 C52 C53 -1.41(19) . . . . ? C57 C51 C52 C53 175.75(12) . . . . ? C51 C52 C53 O53 -178.79(12) . . . . ? C51 C52 C53 C54 0.4(2) . . . . ? C52 C53 O53 C58 2.15(19) . . . . ? C54 C53 O53 C58 -177.06(11) . . . . ? O53 C53 C54 C55 179.94(11) . . . . ? C52 C53 C54 C55 0.7(2) . . . . ? C53 C54 C55 O55 -179.74(12) . . . . ? C53 C54 C55 C56 -0.72(19) . . . . ? C54 C55 O55 C59 -1.89(18) . . . . ? C56 C55 O55 C59 179.05(11) . . . . ? C52 C51 C56 C55 1.4(2) . . . . ? C57 C51 C56 C55 -175.89(12) . . . . ? O55 C55 C56 C51 178.77(12) . . . . ? C54 C55 C56 C51 -0.3(2) . . . . ? C44 C47 C57 C51 -172.66(13) . . . . ? C56 C51 C57 C47 171.83(14) . . . . ? C52 C51 C57 C47 -5.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O41 H41 O32 0.900(16) 1.875(16) 2.7365(13) 159.6(15) . N31 H31A O32 0.880(17) 1.995(17) 2.8722(15) 174.4(15) 7_566 _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.386 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.055