# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Jalal, R.' 'El Messaoudi, M.' 'Hasnaoui, A.' 'Esseffar, M.' 'Selkti, M.' 'Lavergne, J. P.' 'Compain, P.' _publ_contact_author_name 'Dr P. Compain' _publ_contact_author_address ; Institut de Chimie Organique et Analytique Universite d'Orleans BP 6759 Rue de Chartres Orleans cedex 2 45067 FRANCE ; _publ_contact_author_email 'PHILIPPE.COMPAIN@UNIV-ORLEANS.FR' _publ_section_title ; Synthesis of novel heterocyclic ring system: 1,3-dipolar cycloaddition of nitrilimines to 1,3,4-benzotriazepin-5-one derivatives. ; data_3aa _database_code_CSD 194488 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 N5 O3' _chemical_formula_sum 'C20 H21 N5 O3' _chemical_formula_weight 379.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 23.810(5) _cell_length_b 13.142(3) _cell_length_c 12.281(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.48(3) _cell_angle_gamma 90.00 _cell_volume 3790.3(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'thin plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 1.32 _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'flotation' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'KappaCCD (Nonius, 1998)' _diffrn_measurement_method 'CCD' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6392 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1011 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 24.71 _reflns_number_total 6392 _reflns_number_gt 3758 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep (Johnson, 1976)' _computing_publication_material 'WinGX - Version 1.63.02 (Farrugia, 1999)' _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^)+(0.0583P)^2^+3.2702P] 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 6392 _refine_ls_number_parameters 511 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1352 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.1637 _refine_ls_wR_factor_gt 0.1329 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.059 _refine_ls_shift/su_mean 0.001 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 N1_1 N 0.14318(12) 0.0752(2) -0.1758(2) 0.0252(7) Uani 1 1 d . . . N2_1 N 0.16932(12) 0.1338(2) -0.0889(2) 0.0243(7) Uani 1 1 d . . . C3_1 C 0.15823(15) 0.2272(3) -0.1180(3) 0.0224(8) Uani 1 1 d . . . N4_1 N 0.12662(12) 0.2349(2) -0.2248(2) 0.0237(7) Uani 1 1 d . . . N5_1 N 0.09402(12) 0.3204(2) -0.2623(2) 0.0243(7) Uani 1 1 d . . . C5_1 C 0.11796(16) 0.3862(3) -0.3395(3) 0.0308(9) Uani 1 1 d . . . H5A_1 H 0.0876 0.4183 -0.3887 0.046 Uiso 1 1 calc R . . H5B_1 H 0.1405 0.3461 -0.3814 0.046 Uiso 1 1 calc R . . H5C_1 H 0.1415 0.4374 -0.2990 0.046 Uiso 1 1 calc R . . C6_1 C 0.05261(15) 0.3534(3) -0.2068(3) 0.0243(8) Uani 1 1 d . . . O6_1 O 0.03251(11) 0.43951(18) -0.2236(2) 0.0306(6) Uani 1 1 d . . . C6A_1 C 0.03122(14) 0.2811(3) -0.1299(3) 0.0218(8) Uani 1 1 d . . . C7_1 C 0.01039(15) 0.3237(3) -0.0401(3) 0.0272(9) Uani 1 1 d . . . H7_1 H 0.0156 0.3928 -0.0255 0.033 Uiso 1 1 calc R . . C8_1 C -0.01785(16) 0.2651(3) 0.0274(3) 0.0316(9) Uani 1 1 d . . . H8_1 H -0.0310 0.2944 0.0875 0.038 Uiso 1 1 calc R . . C9_1 C -0.02635(16) 0.1627(3) 0.0047(3) 0.0290(9) Uani 1 1 d . . . H9_1 H -0.0465 0.1233 0.0481 0.035 Uiso 1 1 calc R . . C10_1 C -0.00508(15) 0.1188(3) -0.0821(3) 0.0285(9) Uani 1 1 d . . . H10_1 H -0.0109 0.0497 -0.0964 0.034 Uiso 1 1 calc R . . C10A_1 C 0.02503(14) 0.1763(3) -0.1490(3) 0.0227(8) Uani 1 1 d . . . N11_1 N 0.04315(12) 0.1291(2) -0.2401(2) 0.0243(7) Uani 1 1 d . . . H11_1 H 0.0190 0.0969 -0.2877 0.029 Uiso 1 1 calc R . . C11A_1 C 0.10217(15) 0.1347(2) -0.2537(3) 0.0241(8) Uani 1 1 d . . . H11A_1 H 0.1059 0.1177 -0.3298 0.029 Uiso 1 1 calc R . . C12_1 C 0.18113(15) 0.3161(3) -0.0526(3) 0.0283(9) Uani 1 1 d . . . O12A_1 O 0.17429(13) 0.4029(2) -0.0843(2) 0.0470(8) Uani 1 1 d . . . O12B_1 O 0.21024(11) 0.28910(19) 0.0452(2) 0.0325(6) Uani 1 1 d . . . C13_1 C 0.23711(17) 0.3717(3) 0.1142(3) 0.0375(10) Uani 1 1 d . . . H13A_1 H 0.2083 0.4162 0.1357 0.045 Uiso 1 1 calc R . . H13B_1 H 0.2612 0.4115 0.0739 0.045 Uiso 1 1 calc R . . C14_1 C 0.27203(18) 0.3249(4) 0.2144(3) 0.0517(13) Uani 1 1 d . . . H14A_1 H 0.2476 0.2874 0.2548 0.078 Uiso 1 1 calc R . . H14B_1 H 0.2911 0.3776 0.2605 0.078 Uiso 1 1 calc R . . H14C_1 H 0.2997 0.2798 0.1921 0.078 Uiso 1 1 calc R . . C15_1 C 0.14136(15) -0.0312(3) -0.1643(3) 0.0252(8) Uani 1 1 d . . . C16_1 C 0.11247(15) -0.0907(3) -0.2492(3) 0.0302(9) Uani 1 1 d . . . H16_1 H 0.0927 -0.0602 -0.3124 0.036 Uiso 1 1 calc R . . C17_1 C 0.17072(16) -0.0788(3) -0.0707(3) 0.0340(10) Uani 1 1 d . . . H17_1 H 0.1909 -0.0401 -0.0140 0.041 Uiso 1 1 calc R . . C18_1 C 0.11325(16) -0.1966(3) -0.2390(3) 0.0345(10) Uani 1 1 d . . . H18_1 H 0.0942 -0.2359 -0.2965 0.041 Uiso 1 1 calc R . . C19_1 C 0.16992(17) -0.1835(3) -0.0620(4) 0.0403(11) Uani 1 1 d . . . H19_1 H 0.1890 -0.2139 0.0019 0.048 Uiso 1 1 calc R . . C20_1 C 0.14169(16) -0.2448(3) -0.1454(4) 0.0365(10) Uani 1 1 d . . . C21_1 C 0.14206(18) -0.3601(3) -0.1347(4) 0.0491(12) Uani 1 1 d . . . H21A_1 H 0.1130 -0.3885 -0.1899 0.074 Uiso 1 1 calc R . . H21B_1 H 0.1348 -0.3787 -0.0627 0.074 Uiso 1 1 calc R . . H21C_1 H 0.1786 -0.3859 -0.1448 0.074 Uiso 1 1 calc R . . N1_2 N 0.42738(13) 0.5040(2) 0.4402(2) 0.0281(7) Uani 1 1 d . . . N2_2 N 0.41509(13) 0.4331(2) 0.3543(2) 0.0273(7) Uani 1 1 d . . . C3_2 C 0.44146(16) 0.4657(3) 0.2771(3) 0.0271(9) Uani 1 1 d . . . N4_2 N 0.47211(13) 0.5559(2) 0.3038(2) 0.0274(7) Uani 1 1 d . . . N5_2 N 0.48102(14) 0.6245(2) 0.2214(2) 0.0317(8) Uani 1 1 d . . . C5_2 C 0.53828(17) 0.6299(3) 0.1935(3) 0.0401(10) Uani 1 1 d . . . H5A_2 H 0.5408 0.5854 0.1325 0.060 Uiso 1 1 calc R . . H5B_2 H 0.5656 0.6094 0.2561 0.060 Uiso 1 1 calc R . . H5C_2 H 0.5461 0.6985 0.1736 0.060 Uiso 1 1 calc R . . C6_2 C 0.43591(18) 0.6586(3) 0.1481(3) 0.0357(10) Uani 1 1 d . . . O6_2 O 0.44405(14) 0.7003(2) 0.0621(2) 0.0511(9) Uani 1 1 d . . . C6A_2 C 0.37781(17) 0.6482(3) 0.1771(3) 0.0347(10) Uani 1 1 d . . . C7_2 C 0.3323(2) 0.6323(3) 0.0917(4) 0.0445(11) Uani 1 1 d . . . H7_2 H 0.3392 0.6215 0.0203 0.053 Uiso 1 1 calc R . . C8_2 C 0.2775(2) 0.6326(3) 0.1122(4) 0.0527(13) Uani 1 1 d . . . H8_2 H 0.2476 0.6197 0.0549 0.063 Uiso 1 1 calc R . . C9_2 C 0.26613(19) 0.6517(3) 0.2176(4) 0.0504(12) Uani 1 1 d . . . H9_2 H 0.2287 0.6541 0.2302 0.060 Uiso 1 1 calc R . . C10_2 C 0.31091(17) 0.6673(3) 0.3043(4) 0.0381(10) Uani 1 1 d . . . H10_2 H 0.3035 0.6796 0.3751 0.046 Uiso 1 1 calc R . . C10A_2 C 0.36695(16) 0.6644(3) 0.2849(3) 0.0291(9) Uani 1 1 d . . . N11_2 N 0.41329(12) 0.6815(2) 0.3705(2) 0.0260(7) Uani 1 1 d . . . H11_2 H 0.4180 0.7394 0.4035 0.031 Uiso 1 1 calc R . . C11A_2 C 0.45188(16) 0.5996(3) 0.4004(3) 0.0271(9) Uani 1 1 d . . . H11A_2 H 0.4843 0.6227 0.4545 0.033 Uiso 1 1 calc R . . C12_2 C 0.44349(17) 0.4119(3) 0.1713(3) 0.0323(9) Uani 1 1 d . . . O12A_2 O 0.47064(16) 0.4426(3) 0.1053(3) 0.0761(12) Uani 1 1 d . . . O12B_2 O 0.41117(12) 0.33025(19) 0.1586(2) 0.0390(7) Uani 1 1 d . . . C13_2 C 0.41115(18) 0.2746(3) 0.0551(3) 0.0409(11) Uani 1 1 d . . . H13A_2 H 0.4067 0.2024 0.0676 0.049 Uiso 1 1 calc R . . H13B_2 H 0.4473 0.2848 0.0299 0.049 Uiso 1 1 calc R . . C14_2 C 0.36344(18) 0.3112(3) -0.0318(3) 0.0456(11) Uani 1 1 d . . . H14A_2 H 0.3277 0.2991 -0.0077 0.068 Uiso 1 1 calc R . . H14B_2 H 0.3644 0.2750 -0.0994 0.068 Uiso 1 1 calc R . . H14C_2 H 0.3678 0.3827 -0.0438 0.068 Uiso 1 1 calc R . . C15_2 C 0.38931(16) 0.5100(3) 0.5171(3) 0.0245(8) Uani 1 1 d . . . C16_2 C 0.33897(16) 0.4545(3) 0.5054(3) 0.0296(9) Uani 1 1 d . . . H16_2 H 0.3285 0.4140 0.4433 0.035 Uiso 1 1 calc R . . C17_2 C 0.40370(17) 0.5709(3) 0.6099(3) 0.0317(9) Uani 1 1 d . . . H17_2 H 0.4374 0.6080 0.6195 0.038 Uiso 1 1 calc R . . C18_2 C 0.30431(16) 0.4590(3) 0.5851(3) 0.0331(10) Uani 1 1 d . . . H18_2 H 0.2713 0.4200 0.5767 0.040 Uiso 1 1 calc R . . C19_2 C 0.36796(18) 0.5767(3) 0.6883(3) 0.0355(10) Uani 1 1 d . . . H19_2 H 0.3778 0.6189 0.7492 0.043 Uiso 1 1 calc R . . C20_2 C 0.31780(17) 0.5209(3) 0.6778(3) 0.0346(10) Uani 1 1 d . . . C21_2 C 0.27892(19) 0.5281(3) 0.7634(4) 0.0505(12) Uani 1 1 d . . . H21A_2 H 0.3014 0.5296 0.8358 0.076 Uiso 1 1 calc R . . H21B_2 H 0.2541 0.4701 0.7571 0.076 Uiso 1 1 calc R . . H21C_2 H 0.2566 0.5892 0.7516 0.076 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 N1_1 0.0250(18) 0.0189(16) 0.0282(17) -0.0010(14) -0.0054(14) -0.0018(13) N2_1 0.0218(17) 0.0239(16) 0.0256(17) -0.0004(14) -0.0008(13) -0.0017(13) C3_1 0.021(2) 0.024(2) 0.0205(19) -0.0009(16) -0.0001(15) -0.0022(15) N4_1 0.0231(17) 0.0208(16) 0.0257(16) 0.0006(14) -0.0003(13) 0.0002(13) N5_1 0.0259(17) 0.0201(16) 0.0263(16) 0.0050(14) 0.0021(14) 0.0018(13) C5_1 0.030(2) 0.030(2) 0.033(2) 0.0042(18) 0.0044(18) -0.0029(17) C6_1 0.022(2) 0.025(2) 0.024(2) -0.0006(17) -0.0013(16) 0.0014(16) O6_1 0.0299(15) 0.0236(14) 0.0372(15) 0.0029(12) 0.0025(12) 0.0034(11) C6A_1 0.0191(19) 0.0228(19) 0.0225(19) 0.0035(16) 0.0008(15) -0.0001(15) C7_1 0.026(2) 0.025(2) 0.030(2) -0.0056(17) 0.0003(17) -0.0026(16) C8_1 0.030(2) 0.040(2) 0.025(2) -0.0061(19) 0.0033(17) -0.0019(18) C9_1 0.031(2) 0.033(2) 0.0219(19) 0.0037(17) 0.0006(17) -0.0030(17) C10_1 0.027(2) 0.027(2) 0.030(2) 0.0036(18) -0.0010(17) -0.0014(17) C10A_1 0.019(2) 0.0243(19) 0.0225(19) 0.0026(17) -0.0034(16) -0.0003(15) N11_1 0.0198(17) 0.0299(17) 0.0206(16) -0.0027(14) -0.0042(13) -0.0027(13) C11A_1 0.027(2) 0.0189(19) 0.026(2) -0.0006(16) 0.0018(16) 0.0003(15) C12_1 0.022(2) 0.032(2) 0.030(2) 0.0006(18) 0.0011(17) 0.0005(17) O12A_1 0.061(2) 0.0242(15) 0.0477(18) 0.0003(14) -0.0166(15) -0.0023(14) O12B_1 0.0358(16) 0.0312(15) 0.0269(14) -0.0029(12) -0.0055(12) -0.0062(12) C13_1 0.033(2) 0.042(2) 0.038(2) -0.019(2) 0.0054(19) -0.0099(19) C14_1 0.038(3) 0.089(4) 0.025(2) -0.011(2) -0.004(2) -0.012(3) C15_1 0.019(2) 0.0229(19) 0.033(2) 0.0002(18) 0.0027(16) -0.0025(16) C16_1 0.026(2) 0.026(2) 0.036(2) -0.0014(18) -0.0017(18) 0.0054(17) C17_1 0.032(2) 0.025(2) 0.041(2) -0.0032(19) -0.0039(19) 0.0005(17) C18_1 0.024(2) 0.029(2) 0.050(3) -0.013(2) 0.0015(19) -0.0008(17) C19_1 0.037(3) 0.024(2) 0.054(3) 0.005(2) -0.009(2) 0.0021(19) C20_1 0.024(2) 0.025(2) 0.059(3) 0.000(2) 0.001(2) 0.0029(17) C21_1 0.035(3) 0.027(2) 0.082(4) 0.001(2) 0.002(2) 0.0000(19) N1_2 0.0310(19) 0.0268(17) 0.0259(17) -0.0003(14) 0.0028(14) -0.0025(14) N2_2 0.0293(19) 0.0266(17) 0.0250(17) -0.0005(15) 0.0016(14) 0.0039(14) C3_2 0.028(2) 0.029(2) 0.024(2) 0.0010(17) 0.0023(17) 0.0005(17) N4_2 0.0334(19) 0.0259(17) 0.0236(16) 0.0003(14) 0.0071(14) -0.0020(14) N5_2 0.038(2) 0.0321(18) 0.0251(17) 0.0080(15) 0.0068(15) 0.0010(15) C5_2 0.040(3) 0.044(3) 0.040(2) 0.000(2) 0.017(2) -0.006(2) C6_2 0.053(3) 0.027(2) 0.029(2) -0.0032(19) 0.010(2) 0.0063(19) O6_2 0.082(2) 0.0452(18) 0.0294(16) 0.0124(15) 0.0178(16) 0.0183(16) C6A_2 0.041(3) 0.031(2) 0.029(2) -0.0031(18) -0.0045(19) 0.0069(18) C7_2 0.055(3) 0.034(2) 0.038(2) -0.003(2) -0.012(2) 0.009(2) C8_2 0.048(3) 0.038(3) 0.060(3) -0.001(2) -0.025(3) 0.009(2) C9_2 0.030(3) 0.037(3) 0.079(4) 0.005(3) -0.004(3) 0.006(2) C10_2 0.036(3) 0.031(2) 0.048(3) 0.005(2) 0.005(2) 0.0074(19) C10A_2 0.037(2) 0.0190(19) 0.030(2) -0.0004(17) 0.0022(18) 0.0033(17) N11_2 0.0342(19) 0.0170(15) 0.0250(16) -0.0023(13) -0.0009(14) -0.0020(13) C11A_2 0.029(2) 0.027(2) 0.025(2) 0.0020(17) 0.0058(17) -0.0027(17) C12_2 0.033(2) 0.031(2) 0.034(2) -0.0013(19) 0.0078(19) -0.0028(18) O12A_2 0.102(3) 0.072(2) 0.070(2) -0.036(2) 0.061(2) -0.050(2) O12B_2 0.0493(19) 0.0353(16) 0.0334(15) -0.0095(13) 0.0102(13) -0.0105(14) C13_2 0.049(3) 0.035(2) 0.038(2) -0.009(2) 0.006(2) -0.007(2) C14_2 0.039(3) 0.058(3) 0.039(2) -0.011(2) 0.006(2) -0.003(2) C15_2 0.030(2) 0.0204(19) 0.023(2) 0.0029(16) 0.0031(17) 0.0030(16) C16_2 0.026(2) 0.033(2) 0.027(2) 0.0012(18) -0.0031(17) 0.0000(17) C17_2 0.036(2) 0.030(2) 0.029(2) -0.0004(19) 0.0058(18) -0.0035(18) C18_2 0.025(2) 0.034(2) 0.039(2) 0.007(2) 0.0014(19) 0.0023(17) C19_2 0.047(3) 0.032(2) 0.029(2) -0.0022(18) 0.009(2) 0.0033(19) C20_2 0.037(2) 0.035(2) 0.032(2) 0.007(2) 0.0082(19) 0.0047(19) C21_2 0.051(3) 0.054(3) 0.051(3) -0.002(2) 0.024(2) 0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1_1 N2_1 1.379(4) . ? N1_1 C15_1 1.406(4) . ? N1_1 C11A_1 1.474(4) . ? N2_1 C3_1 1.293(4) . ? C3_1 N4_1 1.405(4) . ? C3_1 C12_1 1.471(5) . ? N4_1 N5_1 1.399(4) . ? N4_1 C11A_1 1.460(4) . ? N5_1 C6_1 1.359(4) . ? N5_1 C5_1 1.467(4) . ? C6_1 O6_1 1.233(4) . ? C6_1 C6A_1 1.488(5) . ? C6A_1 C7_1 1.398(5) . ? C6A_1 C10A_1 1.401(5) . ? C7_1 C8_1 1.384(5) . ? C8_1 C9_1 1.383(5) . ? C9_1 C10_1 1.381(5) . ? C10_1 C10A_1 1.398(5) . ? C10A_1 N11_1 1.407(4) . ? N11_1 C11A_1 1.444(4) . ? C12_1 O12A_1 1.207(4) . ? C12_1 O12B_1 1.333(4) . ? O12B_1 C13_1 1.458(4) . ? C13_1 C14_1 1.498(6) . ? C15_1 C17_1 1.392(5) . ? C15_1 C16_1 1.391(5) . ? C16_1 C18_1 1.397(5) . ? C17_1 C19_1 1.380(5) . ? C18_1 C20_1 1.387(5) . ? C19_1 C20_1 1.387(5) . ? C20_1 C21_1 1.520(5) . ? N1_2 N2_2 1.402(4) . ? N1_2 C15_2 1.415(4) . ? N1_2 C11A_2 1.501(4) . ? N2_2 C3_2 1.293(4) . ? C3_2 N4_2 1.403(4) . ? C3_2 C12_2 1.487(5) . ? N4_2 N5_2 1.398(4) . ? N4_2 C11A_2 1.469(4) . ? N5_2 C6_2 1.359(5) . ? N5_2 C5_2 1.461(5) . ? C6_2 O6_2 1.233(4) . ? C6_2 C6A_2 1.490(6) . ? C6A_2 C7_2 1.394(5) . ? C6A_2 C10A_2 1.406(5) . ? C7_2 C8_2 1.368(6) . ? C8_2 C9_2 1.389(6) . ? C9_2 C10_2 1.393(6) . ? C10_2 C10A_2 1.394(5) . ? C10A_2 N11_2 1.411(5) . ? N11_2 C11A_2 1.424(4) . ? C12_2 O12A_2 1.188(5) . ? C12_2 O12B_2 1.314(4) . ? O12B_2 C13_2 1.466(4) . ? C13_2 C14_2 1.504(5) . ? C15_2 C17_2 1.388(5) . ? C15_2 C16_2 1.390(5) . ? C16_2 C18_2 1.381(5) . ? C17_2 C19_2 1.388(5) . ? C18_2 C20_2 1.392(5) . ? C19_2 C20_2 1.389(5) . ? C20_2 C21_2 1.514(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2_1 N1_1 C15_1 119.7(3) . . ? N2_1 N1_1 C11A_1 111.8(2) . . ? C15_1 N1_1 C11A_1 124.4(3) . . ? C3_1 N2_1 N1_1 105.7(3) . . ? N2_1 C3_1 N4_1 112.3(3) . . ? N2_1 C3_1 C12_1 124.3(3) . . ? N4_1 C3_1 C12_1 123.1(3) . . ? N5_1 N4_1 C3_1 123.2(3) . . ? N5_1 N4_1 C11A_1 117.8(3) . . ? C3_1 N4_1 C11A_1 107.0(3) . . ? C6_1 N5_1 N4_1 120.0(3) . . ? C6_1 N5_1 C5_1 121.8(3) . . ? N4_1 N5_1 C5_1 115.6(3) . . ? O6_1 C6_1 N5_1 120.2(3) . . ? O6_1 C6_1 C6A_1 121.9(3) . . ? N5_1 C6_1 C6A_1 117.8(3) . . ? C7_1 C6A_1 C10A_1 119.0(3) . . ? C7_1 C6A_1 C6_1 116.6(3) . . ? C10A_1 C6A_1 C6_1 124.0(3) . . ? C8_1 C7_1 C6A_1 121.4(3) . . ? C9_1 C8_1 C7_1 119.3(3) . . ? C8_1 C9_1 C10_1 120.2(4) . . ? C9_1 C10_1 C10A_1 121.1(3) . . ? C10_1 C10A_1 C6A_1 118.9(3) . . ? C10_1 C10A_1 N11_1 118.9(3) . . ? C6A_1 C10A_1 N11_1 122.0(3) . . ? C10A_1 N11_1 C11A_1 120.1(3) . . ? N11_1 C11A_1 N4_1 112.0(3) . . ? N11_1 C11A_1 N1_1 116.8(3) . . ? N4_1 C11A_1 N1_1 97.3(3) . . ? O12A_1 C12_1 O12B_1 124.4(3) . . ? O12A_1 C12_1 C3_1 123.8(3) . . ? O12B_1 C12_1 C3_1 111.8(3) . . ? C12_1 O12B_1 C13_1 116.0(3) . . ? O12B_1 C13_1 C14_1 107.6(3) . . ? C17_1 C15_1 C16_1 119.0(3) . . ? C17_1 C15_1 N1_1 120.7(3) . . ? C16_1 C15_1 N1_1 120.3(3) . . ? C15_1 C16_1 C18_1 119.7(3) . . ? C19_1 C17_1 C15_1 120.1(4) . . ? C20_1 C18_1 C16_1 121.7(4) . . ? C17_1 C19_1 C20_1 122.3(4) . . ? C19_1 C20_1 C18_1 117.2(3) . . ? C19_1 C20_1 C21_1 121.4(4) . . ? C18_1 C20_1 C21_1 121.4(4) . . ? N2_2 N1_2 C15_2 117.5(3) . . ? N2_2 N1_2 C11A_2 110.8(3) . . ? C15_2 N1_2 C11A_2 119.8(3) . . ? C3_2 N2_2 N1_2 105.4(3) . . ? N2_2 C3_2 N4_2 113.9(3) . . ? N2_2 C3_2 C12_2 124.9(3) . . ? N4_2 C3_2 C12_2 121.0(3) . . ? N5_2 N4_2 C3_2 120.7(3) . . ? N5_2 N4_2 C11A_2 116.2(3) . . ? C3_2 N4_2 C11A_2 107.0(3) . . ? C6_2 N5_2 N4_2 119.7(3) . . ? C6_2 N5_2 C5_2 119.7(3) . . ? N4_2 N5_2 C5_2 117.4(3) . . ? O6_2 C6_2 N5_2 119.7(4) . . ? O6_2 C6_2 C6A_2 121.9(4) . . ? N5_2 C6_2 C6A_2 118.4(3) . . ? C7_2 C6A_2 C10A_2 119.3(4) . . ? C7_2 C6A_2 C6_2 118.1(4) . . ? C10A_2 C6A_2 C6_2 122.2(3) . . ? C8_2 C7_2 C6A_2 120.5(4) . . ? C7_2 C8_2 C9_2 120.7(4) . . ? C8_2 C9_2 C10_2 119.8(4) . . ? C9_2 C10_2 C10A_2 119.9(4) . . ? C10_2 C10A_2 C6A_2 119.7(4) . . ? C10_2 C10A_2 N11_2 121.4(3) . . ? C6A_2 C10A_2 N11_2 118.9(3) . . ? C10A_2 N11_2 C11A_2 117.7(3) . . ? N11_2 C11A_2 N4_2 111.8(3) . . ? N11_2 C11A_2 N1_2 116.6(3) . . ? N4_2 C11A_2 N1_2 97.6(3) . . ? O12A_2 C12_2 O12B_2 124.8(4) . . ? O12A_2 C12_2 C3_2 122.3(4) . . ? O12B_2 C12_2 C3_2 112.9(3) . . ? C12_2 O12B_2 C13_2 115.2(3) . . ? O12B_2 C13_2 C14_2 110.4(3) . . ? C17_2 C15_2 C16_2 118.6(3) . . ? C17_2 C15_2 N1_2 118.8(3) . . ? C16_2 C15_2 N1_2 122.5(3) . . ? C18_2 C16_2 C15_2 120.7(4) . . ? C15_2 C17_2 C19_2 120.3(4) . . ? C16_2 C18_2 C20_2 121.3(4) . . ? C17_2 C19_2 C20_2 121.5(4) . . ? C19_2 C20_2 C18_2 117.6(4) . . ? C19_2 C20_2 C21_2 121.1(4) . . ? C18_2 C20_2 C21_2 121.3(4) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.375 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.058 data_3ba _database_code_CSD 194489 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H25 N5 O3' _chemical_formula_sum 'C26 H25 N5 O3' _chemical_formula_weight 455.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.063(2) _cell_length_b 14.142(3) _cell_length_c 19.642(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.98(3) _cell_angle_gamma 90.00 _cell_volume 2236.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.225 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas 1.35 _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'flotation' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'KappaCCD (Nonius, 1998)' _diffrn_measurement_method 'CCD' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6961 _diffrn_reflns_av_R_equivalents 0.0792 _diffrn_reflns_av_sigmaI/netI 0.1030 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 24.70 _reflns_number_total 3662 _reflns_number_gt 2021 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep (Johnson, 1976)' _computing_publication_material 'WinGX - Version 1.63.02 (Farrugia, 1999)' _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^)+(0.0845P)^2^+0.5658P] 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 3662 _refine_ls_number_parameters 306 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1303 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.1882 _refine_ls_wR_factor_gt 0.1534 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.004 _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 N1 N 0.5384(3) -0.2928(2) 0.40182(16) 0.0308(8) Uani 1 1 d . . . N2 N 0.4369(3) -0.2824(2) 0.34264(16) 0.0329(8) Uani 1 1 d . . . C3 C 0.3146(4) -0.2295(3) 0.3592(2) 0.0324(9) Uani 1 1 d . . . N4 N 0.3233(3) -0.2039(2) 0.42804(16) 0.0319(8) Uani 1 1 d . . . N5 N 0.2526(4) -0.1209(2) 0.45173(17) 0.0362(8) Uani 1 1 d . . . C5 C 0.1125(5) -0.1320(3) 0.4953(2) 0.0465(12) Uani 1 1 d . . . H5A H 0.1047 -0.1968 0.5092 0.070 Uiso 1 1 calc R . . H5B H 0.0118 -0.1139 0.4704 0.070 Uiso 1 1 calc R . . H5C H 0.1289 -0.0925 0.5348 0.070 Uiso 1 1 calc R . . C6 C 0.2926(4) -0.0369(3) 0.4242(2) 0.0338(9) Uani 1 1 d . . . O6 O 0.2075(3) 0.0348(2) 0.43353(14) 0.0427(7) Uani 1 1 d . . . C6A C 0.4440(4) -0.0338(3) 0.3842(2) 0.0319(9) Uani 1 1 d . . . C7 C 0.4467(5) 0.0261(3) 0.3284(2) 0.0346(9) Uani 1 1 d . . . H7 H 0.3505 0.0582 0.3140 0.041 Uiso 1 1 calc R . . C8 C 0.5903(5) 0.0390(3) 0.2934(2) 0.0406(10) Uani 1 1 d . . . H8 H 0.5904 0.0785 0.2556 0.049 Uiso 1 1 calc R . . C9 C 0.7326(5) -0.0078(3) 0.3158(2) 0.0476(12) Uani 1 1 d . . . H9 H 0.8303 0.0014 0.2935 0.057 Uiso 1 1 calc R . . C10 C 0.7324(5) -0.0682(3) 0.3708(2) 0.0426(11) Uani 1 1 d . . . H10 H 0.8294 -0.1000 0.3847 0.051 Uiso 1 1 calc R . . C10A C 0.5890(4) -0.0823(3) 0.40578(19) 0.0304(9) Uani 1 1 d . . . N11 N 0.5876(4) -0.1428(2) 0.46305(16) 0.0352(8) Uani 1 1 d . . . H11 H 0.6428 -0.1288 0.5003 0.042 Uiso 1 1 calc R . . C11A C 0.4919(4) -0.2280(3) 0.4574(2) 0.0310(9) Uani 1 1 d . . . O12A O 0.0840(4) -0.1370(2) 0.3223(2) 0.0721(11) Uani 1 1 d . . . C12 C 0.1787(5) -0.2006(3) 0.3106(2) 0.0438(11) Uani 1 1 d D A . O12B O 0.1741(4) -0.2502(2) 0.25404(17) 0.0598(10) Uani 1 1 d D . . C131 C 0.0266(8) -0.2201(5) 0.2124(3) 0.041(2) Uiso 0.599(12) 1 d PD A 1 H13A H 0.0360 -0.1545 0.1987 0.049 Uiso 0.599(12) 1 calc PR A 1 H13B H -0.0735 -0.2277 0.2372 0.049 Uiso 0.599(12) 1 calc PR A 1 C141 C 0.0255(12) -0.2843(6) 0.1522(4) 0.065(3) Uiso 0.599(12) 1 d PD A 1 H14A H -0.0681 -0.2696 0.1218 0.098 Uiso 0.599(12) 1 calc PR A 1 H14B H 0.0178 -0.3487 0.1671 0.098 Uiso 0.599(12) 1 calc PR A 1 H14C H 0.1261 -0.2759 0.1288 0.098 Uiso 0.599(12) 1 calc PR A 1 C132 C 0.1020(13) -0.2125(8) 0.1864(5) 0.053(4) Uiso 0.401(12) 1 d PD A 2 H13C H 0.0853 -0.1446 0.1884 0.064 Uiso 0.401(12) 1 calc PR A 2 H13D H 0.1740 -0.2268 0.1497 0.064 Uiso 0.401(12) 1 calc PR A 2 C142 C -0.0602(15) -0.2635(11) 0.1769(8) 0.081(5) Uiso 0.401(12) 1 d PD A 2 H14D H -0.1164 -0.2432 0.1351 0.121 Uiso 0.401(12) 1 calc PR A 2 H14E H -0.1278 -0.2496 0.2144 0.121 Uiso 0.401(12) 1 calc PR A 2 H14F H -0.0403 -0.3303 0.1750 0.121 Uiso 0.401(12) 1 calc PR A 2 C15 C 0.6993(4) -0.3311(3) 0.39539(19) 0.0282(9) Uani 1 1 d . . . C16 C 0.7435(4) -0.3664(3) 0.3329(2) 0.0331(9) Uani 1 1 d . . . H16 H 0.6731 -0.3579 0.2944 0.040 Uiso 1 1 calc R . . C17 C 0.8093(4) -0.3417(3) 0.4520(2) 0.0344(9) Uani 1 1 d . . . H17 H 0.7830 -0.3172 0.4940 0.041 Uiso 1 1 calc R . . C18 C 0.8923(4) -0.4141(3) 0.3280(2) 0.0370(10) Uani 1 1 d . . . H18 H 0.9193 -0.4379 0.2858 0.044 Uiso 1 1 calc R . . C19 C 0.9579(4) -0.3891(3) 0.4452(2) 0.0358(10) Uani 1 1 d . . . H19 H 1.0306 -0.3953 0.4833 0.043 Uiso 1 1 calc R . . C20 C 1.0023(4) -0.4277(3) 0.3836(2) 0.0346(10) Uani 1 1 d . . . C21 C 1.1620(4) -0.4827(3) 0.3778(2) 0.0421(11) Uani 1 1 d . . . H21A H 1.2213 -0.4848 0.4214 0.063 Uiso 1 1 calc R . . H21B H 1.2294 -0.4523 0.3454 0.063 Uiso 1 1 calc R . . H21C H 1.1367 -0.5459 0.3628 0.063 Uiso 1 1 calc R . . C22 C 0.4827(4) -0.2786(3) 0.5252(2) 0.0325(9) Uani 1 1 d . . . C23 C 0.4254(5) -0.3709(3) 0.5260(2) 0.0406(10) Uani 1 1 d . . . H23 H 0.3974 -0.4015 0.4851 0.049 Uiso 1 1 calc R . . C24 C 0.5243(6) -0.2349(3) 0.5864(2) 0.0533(13) Uani 1 1 d . . . H24 H 0.5630 -0.1729 0.5868 0.064 Uiso 1 1 calc R . . C25 C 0.4092(5) -0.4184(3) 0.5870(2) 0.0473(11) Uani 1 1 d . . . H25 H 0.3692 -0.4801 0.5869 0.057 Uiso 1 1 calc R . . C26 C 0.5090(7) -0.2828(4) 0.6477(2) 0.0709(17) Uani 1 1 d . . . H26 H 0.5371 -0.2526 0.6888 0.085 Uiso 1 1 calc R . . C27 C 0.4525(6) -0.3744(3) 0.6478(2) 0.0573(13) Uani 1 1 d . . . H27 H 0.4435 -0.4065 0.6888 0.069 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 N1 0.0299(16) 0.034(2) 0.0289(18) -0.0052(15) 0.0027(13) 0.0056(14) N2 0.0298(16) 0.034(2) 0.034(2) -0.0030(16) -0.0033(13) 0.0042(14) C3 0.029(2) 0.031(2) 0.038(2) -0.0010(19) 0.0033(16) -0.0003(17) N4 0.0316(17) 0.0266(18) 0.038(2) -0.0027(16) 0.0071(14) 0.0038(13) N5 0.0373(18) 0.0252(19) 0.048(2) -0.0036(17) 0.0163(15) 0.0036(14) C5 0.041(2) 0.045(3) 0.056(3) 0.004(2) 0.025(2) 0.004(2) C6 0.040(2) 0.026(2) 0.036(2) -0.0020(19) 0.0080(18) 0.0000(18) O6 0.0478(16) 0.0342(17) 0.0470(19) 0.0008(14) 0.0113(13) 0.0072(14) C6A 0.037(2) 0.029(2) 0.031(2) -0.0025(19) 0.0063(16) -0.0017(17) C7 0.037(2) 0.032(2) 0.034(2) -0.003(2) 0.0015(17) -0.0006(17) C8 0.047(2) 0.046(3) 0.030(2) 0.009(2) 0.0068(18) 0.000(2) C9 0.040(2) 0.057(3) 0.047(3) 0.020(2) 0.0095(19) 0.000(2) C10 0.033(2) 0.050(3) 0.046(3) 0.011(2) 0.0041(19) -0.0020(19) C10A 0.038(2) 0.031(2) 0.022(2) 0.0042(18) -0.0002(16) -0.0043(17) N11 0.0426(19) 0.032(2) 0.031(2) 0.0033(16) -0.0021(14) -0.0081(15) C11A 0.032(2) 0.029(2) 0.032(2) -0.0019(19) 0.0044(16) -0.0001(17) O12A 0.0476(19) 0.062(2) 0.104(3) -0.014(2) -0.0166(18) 0.0237(18) C12 0.030(2) 0.038(3) 0.063(3) -0.002(2) -0.0084(19) 0.0010(19) O12B 0.064(2) 0.052(2) 0.059(2) -0.0125(18) -0.0354(16) 0.0120(15) C15 0.0267(19) 0.028(2) 0.030(2) 0.0023(18) 0.0030(16) 0.0019(15) C16 0.031(2) 0.040(2) 0.028(2) 0.0004(19) 0.0019(16) 0.0065(17) C17 0.033(2) 0.040(2) 0.031(2) -0.0010(19) -0.0004(16) 0.0012(18) C18 0.032(2) 0.048(3) 0.031(2) 0.001(2) 0.0078(17) 0.0040(18) C19 0.033(2) 0.037(2) 0.037(3) 0.002(2) -0.0018(17) 0.0010(18) C20 0.029(2) 0.032(2) 0.043(3) 0.001(2) 0.0058(17) -0.0003(17) C21 0.035(2) 0.039(3) 0.053(3) -0.003(2) 0.0026(19) 0.0047(18) C22 0.039(2) 0.027(2) 0.031(2) -0.0021(19) 0.0090(16) -0.0028(17) C23 0.050(2) 0.035(2) 0.038(3) -0.003(2) 0.0089(19) -0.0066(19) C24 0.100(4) 0.032(3) 0.030(3) 0.000(2) 0.019(2) -0.016(2) C25 0.061(3) 0.031(2) 0.050(3) 0.005(2) 0.011(2) -0.005(2) C26 0.134(5) 0.049(3) 0.031(3) -0.003(2) 0.019(3) -0.024(3) C27 0.090(4) 0.043(3) 0.040(3) 0.013(2) 0.021(3) -0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N2 1.394(4) . ? N1 C15 1.417(4) . ? N1 C11A 1.489(5) . ? N2 C3 1.293(5) . ? C3 N4 1.397(5) . ? C3 C12 1.474(5) . ? N4 N5 1.396(4) . ? N4 C11A 1.488(5) . ? N5 C6 1.351(5) . ? N5 C5 1.460(5) . ? C6 O6 1.243(4) . ? C6 C6A 1.486(5) . ? C6A C7 1.387(5) . ? C6A C10A 1.402(5) . ? C7 C8 1.389(5) . ? C8 C9 1.377(6) . ? C9 C10 1.376(6) . ? C10 C10A 1.390(5) . ? C10A N11 1.414(5) . ? N11 C11A 1.432(5) . ? C11A C22 1.515(5) . ? O12A C12 1.209(5) . ? C12 O12B 1.312(5) . ? O12B C131 1.471(6) . ? O12B C132 1.520(7) . ? C131 C141 1.492(7) . ? C132 C142 1.496(8) . ? C15 C16 1.388(5) . ? C15 C17 1.394(5) . ? C16 C18 1.385(5) . ? C17 C19 1.385(5) . ? C18 C20 1.385(5) . ? C19 C20 1.392(5) . ? C20 C21 1.514(5) . ? C22 C24 1.378(6) . ? C22 C23 1.386(5) . ? C23 C25 1.386(6) . ? C24 C26 1.393(6) . ? C25 C27 1.376(6) . ? C26 C27 1.372(7) . ? 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 N2 N1 C15 117.8(3) . . ? N2 N1 C11A 112.8(3) . . ? C15 N1 C11A 124.6(3) . . ? C3 N2 N1 105.8(3) . . ? N2 C3 N4 113.1(3) . . ? N2 C3 C12 123.2(4) . . ? N4 C3 C12 123.6(3) . . ? N5 N4 C3 122.7(3) . . ? N5 N4 C11A 116.4(3) . . ? C3 N4 C11A 108.4(3) . . ? C6 N5 N4 119.7(3) . . ? C6 N5 C5 122.5(3) . . ? N4 N5 C5 116.6(3) . . ? O6 C6 N5 120.9(3) . . ? O6 C6 C6A 121.9(4) . . ? N5 C6 C6A 117.2(3) . . ? C7 C6A C10A 119.4(3) . . ? C7 C6A C6 118.9(3) . . ? C10A C6A C6 121.4(3) . . ? C6A C7 C8 121.3(4) . . ? C9 C8 C7 118.8(4) . . ? C10 C9 C8 120.9(4) . . ? C9 C10 C10A 120.8(4) . . ? C10 C10A C6A 118.9(4) . . ? C10 C10A N11 121.4(3) . . ? C6A C10A N11 119.7(3) . . ? C10A N11 C11A 118.4(3) . . ? N11 C11A N1 114.8(3) . . ? N11 C11A N4 108.3(3) . . ? N1 C11A N4 96.7(3) . . ? N11 C11A C22 112.3(3) . . ? N1 C11A C22 112.3(3) . . ? N4 C11A C22 111.3(3) . . ? O12A C12 O12B 124.6(4) . . ? O12A C12 C3 122.5(4) . . ? O12B C12 C3 112.8(4) . . ? C12 O12B C131 107.6(4) . . ? C12 O12B C132 123.0(6) . . ? C131 O12B C132 31.8(4) . . ? O12B C131 C141 103.6(5) . . ? C142 C132 O12B 103.4(8) . . ? C16 C15 C17 119.0(3) . . ? C16 C15 N1 119.6(3) . . ? C17 C15 N1 121.2(3) . . ? C18 C16 C15 120.0(4) . . ? C19 C17 C15 119.6(4) . . ? C16 C18 C20 122.3(4) . . ? C17 C19 C20 122.4(4) . . ? C18 C20 C19 116.6(3) . . ? C18 C20 C21 121.6(4) . . ? C19 C20 C21 121.8(4) . . ? C24 C22 C23 118.6(4) . . ? C24 C22 C11A 122.3(4) . . ? C23 C22 C11A 119.1(4) . . ? C25 C23 C22 120.9(4) . . ? C22 C24 C26 120.5(4) . . ? C27 C25 C23 120.0(4) . . ? C27 C26 C24 120.3(5) . . ? C26 C27 C25 119.7(4) . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 24.70 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.347 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.057