# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_a _database_code_depnum_ccdc_archive 'CCDC 857963' #TrackingRef 'A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H21 N3 O2' _chemical_formula_sum 'C21 H21 N3 O2' _chemical_formula_weight 347.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.086(2) _cell_length_b 12.727(3) _cell_length_c 13.649(3) _cell_angle_alpha 73.23(3) _cell_angle_beta 84.08(3) _cell_angle_gamma 83.37(3) _cell_volume 1826.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5701 _cell_measurement_theta_min 1.5625 _cell_measurement_theta_max 27.4850 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6891 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13045 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0485 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6362 _reflns_number_gt 5553 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELX-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 2008)' _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^)+(0.0361P)^2^+0.9153P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6362 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0655 _refine_ls_wR_factor_ref 0.1364 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.00417(15) 0.53083(13) 0.10203(13) 0.0395(4) Uani 1 1 d . . . O2 O 1.20299(15) 0.35121(14) 0.15966(13) 0.0407(4) Uani 1 1 d . . . O3 O 1.25184(15) 0.65219(15) 0.11136(13) 0.0421(4) Uani 1 1 d . . . O4 O 1.07447(15) 0.77561(14) -0.03552(12) 0.0405(4) Uani 1 1 d . . . N1 N 0.88708(17) 0.38741(15) 0.18518(14) 0.0302(4) Uani 1 1 d . . . N2 N 0.84171(18) 0.20355(16) 0.29002(15) 0.0372(5) Uani 1 1 d . . . N3 N 1.03871(17) 0.25418(16) 0.23504(15) 0.0350(5) Uani 1 1 d . . . N4 N 1.09519(17) 0.68827(16) 0.22726(14) 0.0320(4) Uani 1 1 d . . . N5 N 0.91023(17) 0.74925(16) 0.29857(15) 0.0351(5) Uani 1 1 d . . . N6 N 0.95969(17) 0.78354(15) 0.11431(14) 0.0309(4) Uani 1 1 d . . . C1 C 0.7693(2) 0.44835(17) 0.16880(17) 0.0302(5) Uani 1 1 d . . . C2 C 0.7352(2) 0.48709(19) 0.06926(18) 0.0346(5) Uani 1 1 d . . . H2 H 0.7884 0.4749 0.0137 0.042 Uiso 1 1 calc R . . C3 C 0.6216(2) 0.5441(2) 0.0523(2) 0.0446(7) Uani 1 1 d . . . H3 H 0.5965 0.5721 -0.0155 0.054 Uiso 1 1 calc R . . C4 C 0.5448(2) 0.5603(2) 0.1340(2) 0.0493(7) Uani 1 1 d . . . H4 H 0.4663 0.5981 0.1221 0.059 Uiso 1 1 calc R . . C5 C 0.5811(2) 0.5221(2) 0.2326(2) 0.0449(6) Uani 1 1 d . . . H5 H 0.5278 0.5336 0.2884 0.054 Uiso 1 1 calc R . . C6 C 0.6953(2) 0.46689(19) 0.25022(19) 0.0366(6) Uani 1 1 d . . . H6 H 0.7221 0.4422 0.3177 0.044 Uiso 1 1 calc R . . C7 C 0.7128(2) 0.21735(18) 0.28916(18) 0.0330(5) Uani 1 1 d . . . C8 C 0.6559(2) 0.23146(19) 0.1996(2) 0.0407(6) Uani 1 1 d . . . H8 H 0.7029 0.2337 0.1368 0.049 Uiso 1 1 calc R . . C9 C 0.5302(3) 0.2422(2) 0.2028(2) 0.0529(8) Uani 1 1 d . . . H9 H 0.4910 0.2534 0.1414 0.064 Uiso 1 1 calc R . . C10 C 0.4608(3) 0.2368(2) 0.2937(3) 0.0583(8) Uani 1 1 d . . . H10 H 0.3745 0.2452 0.2947 0.070 Uiso 1 1 calc R . . C11 C 0.5172(3) 0.2192(2) 0.3832(2) 0.0508(7) Uani 1 1 d . . . H11 H 0.4700 0.2144 0.4462 0.061 Uiso 1 1 calc R . . C12 C 0.6432(2) 0.20859(19) 0.3806(2) 0.0393(6) Uani 1 1 d . . . H12 H 0.6822 0.1951 0.4425 0.047 Uiso 1 1 calc R . . C13 C 0.9113(2) 0.27517(18) 0.24056(17) 0.0323(5) Uani 1 1 d . . . C14 C 0.9937(2) 0.43571(19) 0.14795(18) 0.0323(5) Uani 1 1 d . . . C15 C 1.0954(2) 0.34382(19) 0.17960(18) 0.0331(5) Uani 1 1 d . . . C16 C 1.1077(2) 0.14617(19) 0.27625(18) 0.0361(6) Uani 1 1 d . . . H16 H 1.1948 0.1560 0.2513 0.043 Uiso 1 1 calc R . . C17 C 1.1033(3) 0.1138(2) 0.39190(19) 0.0442(7) Uani 1 1 d . . . H17A H 1.0182 0.1039 0.4204 0.053 Uiso 1 1 calc R . . H17B H 1.1319 0.1733 0.4145 0.053 Uiso 1 1 calc R . . C18 C 1.1835(3) 0.0065(2) 0.4328(2) 0.0458(7) Uani 1 1 d . . . H18A H 1.1735 -0.0170 0.5087 0.055 Uiso 1 1 calc R . . H18B H 1.2701 0.0191 0.4121 0.055 Uiso 1 1 calc R . . C19 C 1.1487(3) -0.0845(2) 0.3908(2) 0.0504(7) Uani 1 1 d . . . H19B H 1.2052 -0.1514 0.4140 0.061 Uiso 1 1 calc R . . H19A H 1.0654 -0.1033 0.4187 0.061 Uiso 1 1 calc R . . C20 C 1.1533(2) -0.0493(2) 0.27539(19) 0.0417(6) Uani 1 1 d . . . H20A H 1.1272 -0.1088 0.2512 0.050 Uiso 1 1 calc R . . H20B H 1.2381 -0.0372 0.2474 0.050 Uiso 1 1 calc R . . C21 C 1.0711(2) 0.05618(18) 0.23550(18) 0.0347(5) Uani 1 1 d . . . H21B H 1.0788 0.0795 0.1596 0.042 Uiso 1 1 calc R . . H21A H 0.9851 0.0428 0.2583 0.042 Uiso 1 1 calc R . . C22 C 0.8558(2) 0.85077(19) 0.06696(17) 0.0314(5) Uani 1 1 d . . . C23 C 0.7823(2) 0.8045(2) 0.01771(19) 0.0422(6) Uani 1 1 d . . . H23 H 0.7978 0.7295 0.0174 0.051 Uiso 1 1 calc R . . C24 C 0.6854(2) 0.8706(3) -0.0313(2) 0.0537(8) Uani 1 1 d . . . H24 H 0.6336 0.8404 -0.0653 0.064 Uiso 1 1 calc R . . C25 C 0.6630(2) 0.9795(3) -0.0313(2) 0.0531(8) Uani 1 1 d . . . H25 H 0.5962 1.0237 -0.0651 0.064 Uiso 1 1 calc R . . C26 C 0.7375(2) 1.0240(2) 0.0177(2) 0.0465(7) Uani 1 1 d . . . H26 H 0.7216 1.0988 0.0182 0.056 Uiso 1 1 calc R . . C27 C 0.8358(2) 0.95981(19) 0.06630(18) 0.0360(6) Uani 1 1 d . . . H27 H 0.8887 0.9907 0.0987 0.043 Uiso 1 1 calc R . . C28 C 0.7880(2) 0.79638(19) 0.29855(17) 0.0330(5) Uani 1 1 d . . . C29 C 0.6974(2) 0.7525(2) 0.26416(19) 0.0388(6) Uani 1 1 d . . . H29 H 0.7172 0.6912 0.2371 0.047 Uiso 1 1 calc R . . C30 C 0.5786(2) 0.7978(2) 0.2692(2) 0.0489(7) Uani 1 1 d . . . H30 H 0.5168 0.7675 0.2453 0.059 Uiso 1 1 calc R . . C31 C 0.5483(3) 0.8868(2) 0.3085(2) 0.0523(7) Uani 1 1 d . . . H31 H 0.4664 0.9182 0.3110 0.063 Uiso 1 1 calc R . . C32 C 0.6379(3) 0.9293(2) 0.3439(2) 0.0500(7) Uani 1 1 d . . . H32 H 0.6177 0.9904 0.3712 0.060 Uiso 1 1 calc R . . C33 C 0.7567(2) 0.8841(2) 0.34020(19) 0.0413(6) Uani 1 1 d . . . H33 H 0.8176 0.9131 0.3663 0.050 Uiso 1 1 calc R . . C34 C 0.9768(2) 0.74226(18) 0.22003(17) 0.0304(5) Uani 1 1 d . . . C35 C 1.0601(2) 0.75406(19) 0.05672(17) 0.0329(5) Uani 1 1 d . . . C36 C 1.1512(2) 0.68979(19) 0.13312(18) 0.0327(5) Uani 1 1 d . . . C37 C 1.1420(2) 0.6274(2) 0.32774(17) 0.0352(6) Uani 1 1 d . . . H37 H 1.0904 0.6538 0.3819 0.042 Uiso 1 1 calc R . . C38 C 1.1314(3) 0.5040(2) 0.3502(2) 0.0460(7) Uani 1 1 d . . . H38A H 1.1812 0.4756 0.2973 0.055 Uiso 1 1 calc R . . H38B H 1.0455 0.4910 0.3477 0.055 Uiso 1 1 calc R . . C39 C 1.1749(3) 0.4426(3) 0.4564(2) 0.0578(8) Uani 1 1 d . . . H39A H 1.1194 0.4654 0.5097 0.069 Uiso 1 1 calc R . . H39B H 1.1723 0.3624 0.4682 0.069 Uiso 1 1 calc R . . C40 C 1.3037(3) 0.4662(2) 0.4659(2) 0.0542(8) Uani 1 1 d . . . H40A H 1.3269 0.4300 0.5368 0.065 Uiso 1 1 calc R . . H40B H 1.3608 0.4349 0.4187 0.065 Uiso 1 1 calc R . . C41 C 1.3142(3) 0.5892(2) 0.4407(2) 0.0481(7) Uani 1 1 d . . . H41A H 1.3999 0.6022 0.4440 0.058 Uiso 1 1 calc R . . H41B H 1.2635 0.6191 0.4922 0.058 Uiso 1 1 calc R . . C42 C 1.2730(2) 0.6493(2) 0.33360(19) 0.0385(6) Uani 1 1 d . . . H42A H 1.2785 0.7294 0.3195 0.046 Uiso 1 1 calc R . . H42B H 1.3267 0.6230 0.2813 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0400(10) 0.0286(9) 0.0479(10) -0.0052(8) -0.0073(8) -0.0054(7) O2 0.0308(10) 0.0404(10) 0.0501(11) -0.0105(8) -0.0062(8) -0.0030(7) O3 0.0330(10) 0.0530(11) 0.0420(10) -0.0198(8) -0.0001(8) 0.0038(8) O4 0.0419(10) 0.0466(10) 0.0301(9) -0.0097(8) 0.0015(7) 0.0019(8) N1 0.0298(10) 0.0258(10) 0.0347(10) -0.0070(8) -0.0070(8) -0.0007(8) N2 0.0330(11) 0.0324(11) 0.0427(12) -0.0042(9) -0.0058(9) -0.0021(9) N3 0.0285(11) 0.0294(11) 0.0450(12) -0.0061(9) -0.0098(9) 0.0012(8) N4 0.0285(10) 0.0375(11) 0.0298(10) -0.0111(9) -0.0033(8) 0.0027(8) N5 0.0319(11) 0.0397(12) 0.0332(11) -0.0120(9) 0.0010(9) -0.0001(9) N6 0.0309(10) 0.0299(10) 0.0316(10) -0.0097(8) -0.0023(8) 0.0013(8) C1 0.0294(12) 0.0228(11) 0.0386(13) -0.0078(10) -0.0063(10) -0.0012(9) C2 0.0339(13) 0.0327(13) 0.0368(13) -0.0079(11) -0.0043(11) -0.0043(10) C3 0.0384(15) 0.0378(14) 0.0527(16) -0.0010(12) -0.0148(13) -0.0030(11) C4 0.0284(14) 0.0376(15) 0.078(2) -0.0105(14) -0.0058(14) 0.0025(11) C5 0.0366(14) 0.0383(14) 0.0592(17) -0.0175(13) 0.0077(13) -0.0005(11) C6 0.0422(14) 0.0298(13) 0.0393(14) -0.0116(11) -0.0024(11) -0.0046(11) C7 0.0350(13) 0.0234(12) 0.0392(13) -0.0053(10) -0.0057(11) -0.0035(10) C8 0.0496(16) 0.0322(13) 0.0421(14) -0.0098(11) -0.0106(12) -0.0070(11) C9 0.0580(19) 0.0420(16) 0.0605(19) -0.0047(14) -0.0294(16) -0.0138(14) C10 0.0379(16) 0.0449(17) 0.087(2) -0.0045(16) -0.0161(16) -0.0064(13) C11 0.0460(16) 0.0390(15) 0.0583(18) -0.0035(13) 0.0063(14) -0.0018(12) C12 0.0400(14) 0.0319(13) 0.0426(14) -0.0044(11) -0.0082(12) -0.0010(11) C13 0.0363(13) 0.0274(12) 0.0339(12) -0.0077(10) -0.0084(10) -0.0022(10) C14 0.0314(13) 0.0326(13) 0.0349(13) -0.0109(11) -0.0062(10) -0.0033(10) C15 0.0340(14) 0.0309(13) 0.0369(13) -0.0118(10) -0.0067(11) -0.0037(10) C16 0.0344(13) 0.0307(13) 0.0425(14) -0.0090(11) -0.0098(11) 0.0027(10) C17 0.0592(17) 0.0343(14) 0.0399(14) -0.0139(12) -0.0098(13) 0.0065(12) C18 0.0619(18) 0.0371(14) 0.0383(14) -0.0103(12) -0.0168(13) 0.0072(13) C19 0.073(2) 0.0333(14) 0.0429(15) -0.0085(12) -0.0144(14) 0.0082(13) C20 0.0501(16) 0.0333(14) 0.0438(15) -0.0129(11) -0.0142(12) 0.0032(12) C21 0.0352(13) 0.0320(13) 0.0369(13) -0.0088(10) -0.0090(11) 0.0001(10) C22 0.0290(12) 0.0346(13) 0.0306(12) -0.0098(10) 0.0004(10) -0.0036(10) C23 0.0412(15) 0.0486(16) 0.0421(14) -0.0185(12) -0.0013(12) -0.0122(12) C24 0.0368(15) 0.083(2) 0.0478(16) -0.0230(16) -0.0097(13) -0.0140(15) C25 0.0327(15) 0.075(2) 0.0429(15) -0.0056(15) -0.0073(12) 0.0072(14) C26 0.0451(16) 0.0421(15) 0.0449(15) -0.0062(12) -0.0009(13) 0.0091(12) C27 0.0335(13) 0.0362(13) 0.0396(13) -0.0125(11) -0.0036(11) -0.0021(10) C28 0.0315(13) 0.0349(13) 0.0297(12) -0.0069(10) 0.0034(10) -0.0022(10) C29 0.0375(14) 0.0351(14) 0.0458(15) -0.0153(11) 0.0022(11) -0.0062(11) C30 0.0338(15) 0.0563(18) 0.0571(17) -0.0157(14) -0.0011(13) -0.0085(13) C31 0.0370(15) 0.0513(17) 0.0624(18) -0.0128(15) 0.0040(13) 0.0067(13) C32 0.0495(17) 0.0412(15) 0.0591(17) -0.0214(14) 0.0117(14) 0.0021(13) C33 0.0403(15) 0.0449(15) 0.0426(14) -0.0195(12) 0.0043(12) -0.0071(12) C34 0.0307(12) 0.0300(12) 0.0326(12) -0.0113(10) -0.0026(10) -0.0051(10) C35 0.0380(14) 0.0309(13) 0.0304(13) -0.0104(10) 0.0024(10) -0.0049(10) C36 0.0319(13) 0.0335(13) 0.0348(13) -0.0137(10) -0.0018(10) -0.0021(10) C37 0.0360(13) 0.0404(14) 0.0291(12) -0.0117(11) -0.0037(10) 0.0030(11) C38 0.0497(16) 0.0437(16) 0.0420(15) -0.0060(12) -0.0037(12) -0.0092(12) C39 0.068(2) 0.0531(18) 0.0430(16) 0.0027(14) -0.0072(15) -0.0068(15) C40 0.0590(19) 0.0552(18) 0.0411(15) -0.0050(13) -0.0121(14) 0.0108(14) C41 0.0436(16) 0.0583(18) 0.0452(15) -0.0200(13) -0.0132(12) 0.0076(13) C42 0.0392(14) 0.0380(14) 0.0406(14) -0.0150(11) -0.0083(11) 0.0023(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C14 1.205(3) . ? O2 C15 1.204(3) . ? O3 C36 1.205(3) . ? O4 C35 1.206(3) . ? N1 C14 1.378(3) . ? N1 C13 1.419(3) . ? N1 C1 1.443(3) . ? N2 C13 1.258(3) . ? N2 C7 1.421(3) . ? N3 C15 1.356(3) . ? N3 C13 1.405(3) . ? N3 C16 1.480(3) . ? N4 C36 1.364(3) . ? N4 C34 1.409(3) . ? N4 C37 1.480(3) . ? N5 C34 1.256(3) . ? N5 C28 1.417(3) . ? N6 C35 1.375(3) . ? N6 C34 1.411(3) . ? N6 C22 1.443(3) . ? C1 C6 1.372(3) . ? C1 C2 1.381(3) . ? C2 C3 1.384(3) . ? C2 H2 0.9500 . ? C3 C4 1.380(4) . ? C3 H3 0.9500 . ? C4 C5 1.378(4) . ? C4 H4 0.9500 . ? C5 C6 1.383(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.381(3) . ? C7 C8 1.390(3) . ? C8 C9 1.382(4) . ? C8 H8 0.9500 . ? C9 C10 1.379(4) . ? C9 H9 0.9500 . ? C10 C11 1.378(4) . ? C10 H10 0.9500 . ? C11 C12 1.386(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C14 C15 1.526(3) . ? C16 C17 1.509(3) . ? C16 C21 1.519(3) . ? C16 H16 1.0000 . ? C17 C18 1.532(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.533(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.506(3) . ? C19 H19B 0.9900 . ? C19 H19A 0.9900 . ? C20 C21 1.526(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21B 0.9900 . ? C21 H21A 0.9900 . ? C22 C27 1.377(3) . ? C22 C23 1.384(3) . ? C23 C24 1.387(4) . ? C23 H23 0.9500 . ? C24 C25 1.380(4) . ? C24 H24 0.9500 . ? C25 C26 1.374(4) . ? C25 H25 0.9500 . ? C26 C27 1.388(3) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C29 1.385(3) . ? C28 C33 1.388(3) . ? C29 C30 1.379(3) . ? C29 H29 0.9500 . ? C30 C31 1.381(4) . ? C30 H30 0.9500 . ? C31 C32 1.374(4) . ? C31 H31 0.9500 . ? C32 C33 1.377(4) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C35 C36 1.520(3) . ? C37 C42 1.524(3) . ? C37 C38 1.527(3) . ? C37 H37 1.0000 . ? C38 C39 1.533(4) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.518(4) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.518(4) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.530(3) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? 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 C14 N1 C13 110.96(18) . . ? C14 N1 C1 121.96(18) . . ? C13 N1 C1 127.07(19) . . ? C13 N2 C7 124.4(2) . . ? C15 N3 C13 112.39(19) . . ? C15 N3 C16 121.5(2) . . ? C13 N3 C16 125.9(2) . . ? C36 N4 C34 111.89(18) . . ? C36 N4 C37 126.28(19) . . ? C34 N4 C37 121.44(19) . . ? C34 N5 C28 125.1(2) . . ? C35 N6 C34 110.80(18) . . ? C35 N6 C22 121.61(19) . . ? C34 N6 C22 127.57(19) . . ? C6 C1 C2 121.9(2) . . ? C6 C1 N1 120.3(2) . . ? C2 C1 N1 117.7(2) . . ? C1 C2 C3 118.5(2) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 120.1(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 119.9(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 119.0(2) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C12 C7 C8 119.6(2) . . ? C12 C7 N2 119.0(2) . . ? C8 C7 N2 121.2(2) . . ? C9 C8 C7 119.2(3) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C10 C9 C8 121.0(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C11 C10 C9 119.8(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 119.6(3) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C7 C12 C11 120.7(2) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? N2 C13 N3 122.5(2) . . ? N2 C13 N1 131.6(2) . . ? N3 C13 N1 105.80(19) . . ? O1 C14 N1 127.1(2) . . ? O1 C14 C15 127.5(2) . . ? N1 C14 C15 105.35(19) . . ? O2 C15 N3 128.1(2) . . ? O2 C15 C14 126.5(2) . . ? N3 C15 C14 105.4(2) . . ? N3 C16 C17 111.5(2) . . ? N3 C16 C21 113.09(18) . . ? C17 C16 C21 112.5(2) . . ? N3 C16 H16 106.4 . . ? C17 C16 H16 106.4 . . ? C21 C16 H16 106.4 . . ? C16 C17 C18 110.8(2) . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 C19 110.5(2) . . ? C17 C18 H18A 109.5 . . ? C19 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? C20 C19 C18 111.6(2) . . ? C20 C19 H19B 109.3 . . ? C18 C19 H19B 109.3 . . ? C20 C19 H19A 109.3 . . ? C18 C19 H19A 109.3 . . ? H19B C19 H19A 108.0 . . ? C19 C20 C21 111.4(2) . . ? C19 C20 H20A 109.4 . . ? C21 C20 H20A 109.4 . . ? C19 C20 H20B 109.4 . . ? C21 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? C16 C21 C20 109.37(19) . . ? C16 C21 H21B 109.8 . . ? C20 C21 H21B 109.8 . . ? C16 C21 H21A 109.8 . . ? C20 C21 H21A 109.8 . . ? H21B C21 H21A 108.2 . . ? C27 C22 C23 121.6(2) . . ? C27 C22 N6 120.1(2) . . ? C23 C22 N6 118.2(2) . . ? C22 C23 C24 118.1(3) . . ? C22 C23 H23 121.0 . . ? C24 C23 H23 121.0 . . ? C25 C24 C23 121.0(3) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C26 C25 C24 119.9(3) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C27 120.1(3) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C22 C27 C26 119.2(2) . . ? C22 C27 H27 120.4 . . ? C26 C27 H27 120.4 . . ? C29 C28 C33 119.1(2) . . ? C29 C28 N5 121.6(2) . . ? C33 C28 N5 119.2(2) . . ? C30 C29 C28 119.9(2) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C29 C30 C31 120.8(3) . . ? C29 C30 H30 119.6 . . ? C31 C30 H30 119.6 . . ? C32 C31 C30 119.3(3) . . ? C32 C31 H31 120.4 . . ? C30 C31 H31 120.4 . . ? C31 C32 C33 120.5(3) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C32 C33 C28 120.4(2) . . ? C32 C33 H33 119.8 . . ? C28 C33 H33 119.8 . . ? N5 C34 N4 121.5(2) . . ? N5 C34 N6 132.3(2) . . ? N4 C34 N6 106.17(18) . . ? O4 C35 N6 127.4(2) . . ? O4 C35 C36 126.6(2) . . ? N6 C35 C36 105.91(19) . . ? O3 C36 N4 129.3(2) . . ? O3 C36 C35 125.4(2) . . ? N4 C36 C35 105.18(19) . . ? N4 C37 C42 111.8(2) . . ? N4 C37 C38 110.8(2) . . ? C42 C37 C38 110.6(2) . . ? N4 C37 H37 107.8 . . ? C42 C37 H37 107.8 . . ? C38 C37 H37 107.8 . . ? C37 C38 C39 110.2(2) . . ? C37 C38 H38A 109.6 . . ? C39 C38 H38A 109.6 . . ? C37 C38 H38B 109.6 . . ? C39 C38 H38B 109.6 . . ? H38A C38 H38B 108.1 . . ? C40 C39 C38 111.3(2) . . ? C40 C39 H39A 109.4 . . ? C38 C39 H39A 109.4 . . ? C40 C39 H39B 109.4 . . ? C38 C39 H39B 109.4 . . ? H39A C39 H39B 108.0 . . ? C41 C40 C39 111.2(2) . . ? C41 C40 H40A 109.4 . . ? C39 C40 H40A 109.4 . . ? C41 C40 H40B 109.4 . . ? C39 C40 H40B 109.4 . . ? H40A C40 H40B 108.0 . . ? C40 C41 C42 111.2(2) . . ? C40 C41 H41A 109.4 . . ? C42 C41 H41A 109.4 . . ? C40 C41 H41B 109.4 . . ? C42 C41 H41B 109.4 . . ? H41A C41 H41B 108.0 . . ? C37 C42 C41 109.4(2) . . ? C37 C42 H42A 109.8 . . ? C41 C42 H42A 109.8 . . ? C37 C42 H42B 109.8 . . ? C41 C42 H42B 109.8 . . ? H42A C42 H42B 108.2 . . ? 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 C14 N1 C1 C6 -114.3(3) . . . . ? C13 N1 C1 C6 64.5(3) . . . . ? C14 N1 C1 C2 65.3(3) . . . . ? C13 N1 C1 C2 -115.9(3) . . . . ? C6 C1 C2 C3 -1.4(4) . . . . ? N1 C1 C2 C3 178.9(2) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 C5 1.4(4) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C2 C1 C6 C5 2.7(4) . . . . ? N1 C1 C6 C5 -177.7(2) . . . . ? C4 C5 C6 C1 -1.9(4) . . . . ? C13 N2 C7 C12 -121.3(3) . . . . ? C13 N2 C7 C8 63.4(3) . . . . ? C12 C7 C8 C9 3.3(4) . . . . ? N2 C7 C8 C9 178.6(2) . . . . ? C7 C8 C9 C10 -1.4(4) . . . . ? C8 C9 C10 C11 -0.8(4) . . . . ? C9 C10 C11 C12 0.9(4) . . . . ? C8 C7 C12 C11 -3.3(4) . . . . ? N2 C7 C12 C11 -178.6(2) . . . . ? C10 C11 C12 C7 1.1(4) . . . . ? C7 N2 C13 N3 -173.3(2) . . . . ? C7 N2 C13 N1 9.6(4) . . . . ? C15 N3 C13 N2 -178.6(2) . . . . ? C16 N3 C13 N2 6.1(4) . . . . ? C15 N3 C13 N1 -0.8(3) . . . . ? C16 N3 C13 N1 -176.1(2) . . . . ? C14 N1 C13 N2 176.5(3) . . . . ? C1 N1 C13 N2 -2.4(4) . . . . ? C14 N1 C13 N3 -1.0(2) . . . . ? C1 N1 C13 N3 -179.9(2) . . . . ? C13 N1 C14 O1 -176.4(2) . . . . ? C1 N1 C14 O1 2.5(4) . . . . ? C13 N1 C14 C15 2.2(2) . . . . ? C1 N1 C14 C15 -178.84(19) . . . . ? C13 N3 C15 O2 -178.5(2) . . . . ? C16 N3 C15 O2 -3.0(4) . . . . ? C13 N3 C15 C14 2.1(3) . . . . ? C16 N3 C15 C14 177.64(19) . . . . ? O1 C14 C15 O2 -3.3(4) . . . . ? N1 C14 C15 O2 178.0(2) . . . . ? O1 C14 C15 N3 176.0(2) . . . . ? N1 C14 C15 N3 -2.6(2) . . . . ? C15 N3 C16 C17 112.6(3) . . . . ? C13 N3 C16 C17 -72.5(3) . . . . ? C15 N3 C16 C21 -119.4(2) . . . . ? C13 N3 C16 C21 55.5(3) . . . . ? N3 C16 C17 C18 -175.4(2) . . . . ? C21 C16 C17 C18 56.3(3) . . . . ? C16 C17 C18 C19 -54.0(3) . . . . ? C17 C18 C19 C20 54.9(3) . . . . ? C18 C19 C20 C21 -56.8(3) . . . . ? N3 C16 C21 C20 175.6(2) . . . . ? C17 C16 C21 C20 -56.9(3) . . . . ? C19 C20 C21 C16 56.7(3) . . . . ? C35 N6 C22 C27 -105.4(3) . . . . ? C34 N6 C22 C27 72.5(3) . . . . ? C35 N6 C22 C23 70.8(3) . . . . ? C34 N6 C22 C23 -111.2(3) . . . . ? C27 C22 C23 C24 -1.2(4) . . . . ? N6 C22 C23 C24 -177.5(2) . . . . ? C22 C23 C24 C25 0.2(4) . . . . ? C23 C24 C25 C26 0.1(4) . . . . ? C24 C25 C26 C27 0.6(4) . . . . ? C23 C22 C27 C26 1.9(4) . . . . ? N6 C22 C27 C26 178.1(2) . . . . ? C25 C26 C27 C22 -1.6(4) . . . . ? C34 N5 C28 C29 62.6(3) . . . . ? C34 N5 C28 C33 -121.8(3) . . . . ? C33 C28 C29 C30 1.7(4) . . . . ? N5 C28 C29 C30 177.3(2) . . . . ? C28 C29 C30 C31 -0.2(4) . . . . ? C29 C30 C31 C32 -0.8(4) . . . . ? C30 C31 C32 C33 0.2(4) . . . . ? C31 C32 C33 C28 1.4(4) . . . . ? C29 C28 C33 C32 -2.3(4) . . . . ? N5 C28 C33 C32 -178.1(2) . . . . ? C28 N5 C34 N4 -176.2(2) . . . . ? C28 N5 C34 N6 6.4(4) . . . . ? C36 N4 C34 N5 179.7(2) . . . . ? C37 N4 C34 N5 6.4(3) . . . . ? C36 N4 C34 N6 -2.2(3) . . . . ? C37 N4 C34 N6 -175.52(19) . . . . ? C35 N6 C34 N5 179.9(2) . . . . ? C22 N6 C34 N5 1.7(4) . . . . ? C35 N6 C34 N4 2.2(2) . . . . ? C22 N6 C34 N4 -176.0(2) . . . . ? C34 N6 C35 O4 179.6(2) . . . . ? C22 N6 C35 O4 -2.2(4) . . . . ? C34 N6 C35 C36 -1.3(2) . . . . ? C22 N6 C35 C36 176.96(19) . . . . ? C34 N4 C36 O3 179.6(2) . . . . ? C37 N4 C36 O3 -7.5(4) . . . . ? C34 N4 C36 C35 1.4(3) . . . . ? C37 N4 C36 C35 174.3(2) . . . . ? O4 C35 C36 O3 0.8(4) . . . . ? N6 C35 C36 O3 -178.3(2) . . . . ? O4 C35 C36 N4 179.1(2) . . . . ? N6 C35 C36 N4 -0.1(2) . . . . ? C36 N4 C37 C42 50.3(3) . . . . ? C34 N4 C37 C42 -137.4(2) . . . . ? C36 N4 C37 C38 -73.5(3) . . . . ? C34 N4 C37 C38 98.8(3) . . . . ? N4 C37 C38 C39 -177.5(2) . . . . ? C42 C37 C38 C39 58.0(3) . . . . ? C37 C38 C39 C40 -55.6(3) . . . . ? C38 C39 C40 C41 54.8(3) . . . . ? C39 C40 C41 C42 -56.2(3) . . . . ? N4 C37 C42 C41 177.1(2) . . . . ? C38 C37 C42 C41 -59.0(3) . . . . ? C40 C41 C42 C37 57.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.380 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.040 data_4c _database_code_depnum_ccdc_archive 'CCDC 857964' #TrackingRef '4c-file.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 Br N3 O2' _chemical_formula_weight 352.23 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.8707(18) _cell_length_b 10.082(2) _cell_length_c 18.499(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1654.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 2.492 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.5218 _exptl_absorpt_correction_T_max 0.6356 _exptl_absorpt_process_details ; HIGASHI, T. (1995). Abscor-Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation,Tokyo,Japan. ; _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 graphite _diffrn_measurement_device_type 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method \W _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2200 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1443 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2177 _reflns_number_gt 883 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid-AUTO (Rigaku,2000)' _computing_cell_refinement Rapid-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)' _computing_structure_solution SHELXS-97,(Sheldrick,1997) _computing_structure_refinement SHELXL-97,(Sheldrick,1997) _computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)' _computing_publication_material SHELXL-97,(Sheldrick,1997) _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^)+(0.0000P)^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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0128(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.50(3) _refine_ls_number_reflns 2177 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1173 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.0610 _refine_ls_wR_factor_gt 0.0521 _refine_ls_goodness_of_fit_ref 0.735 _refine_ls_restrained_S_all 0.735 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 1.06189(9) 0.41319(7) 0.84258(3) 0.0873(3) Uani 1 1 d . . . C1 C 0.9114(6) 0.4829(6) 0.4712(3) 0.0415(14) Uani 1 1 d . . . C2 C 1.0889(6) 0.3803(6) 0.3975(3) 0.0471(16) Uani 1 1 d . . . C3 C 1.1425(7) 0.3776(6) 0.4766(3) 0.0467(16) Uani 1 1 d . . . C4 C 0.8552(6) 0.4711(6) 0.3375(2) 0.0526(15) Uani 1 1 d . . . H4 H 0.7607 0.5079 0.3563 0.063 Uiso 1 1 calc R . . C5 C 0.8162(8) 0.3500(6) 0.2959(3) 0.094(2) Uani 1 1 d . . . H5A H 0.7595 0.2906 0.3260 0.141 Uiso 1 1 calc R . . H5B H 0.9070 0.3070 0.2801 0.141 Uiso 1 1 calc R . . H5C H 0.7568 0.3741 0.2545 0.141 Uiso 1 1 calc R . . C6 C 0.9282(7) 0.5770(6) 0.2919(3) 0.106(2) Uani 1 1 d . . . H6A H 1.0281 0.5494 0.2786 0.160 Uiso 1 1 calc R . . H6B H 0.9338 0.6582 0.3189 0.160 Uiso 1 1 calc R . . H6C H 0.8694 0.5910 0.2490 0.160 Uiso 1 1 calc R . . C7 C 0.7352(6) 0.5979(6) 0.5496(2) 0.0493(15) Uani 1 1 d . . . H7 H 0.8161 0.5978 0.5857 0.059 Uiso 1 1 calc R . . C8 C 0.6039(6) 0.5130(6) 0.5758(3) 0.086(2) Uani 1 1 d . . . H8A H 0.6396 0.4255 0.5870 0.129 Uiso 1 1 calc R . . H8B H 0.5288 0.5077 0.5386 0.129 Uiso 1 1 calc R . . H8C H 0.5607 0.5522 0.6183 0.129 Uiso 1 1 calc R . . C9 C 0.6860(7) 0.7379(5) 0.5342(3) 0.075(2) Uani 1 1 d . . . H9A H 0.6198 0.7384 0.4931 0.112 Uiso 1 1 calc R . . H9B H 0.7728 0.7916 0.5241 0.112 Uiso 1 1 calc R . . H9C H 0.6339 0.7729 0.5755 0.112 Uiso 1 1 calc R . . C10 C 1.0379(6) 0.4392(6) 0.5936(2) 0.0364(14) Uani 1 1 d . . . C11 C 1.1362(6) 0.5206(5) 0.6296(2) 0.0441(15) Uani 1 1 d . . . H11 H 1.1971 0.5791 0.6039 0.053 Uiso 1 1 calc R . . C12 C 1.1448(6) 0.5154(5) 0.7055(2) 0.0481(16) Uani 1 1 d . . . H12 H 1.2093 0.5706 0.7313 0.058 Uiso 1 1 calc R . . C13 C 1.0538(7) 0.4253(6) 0.7397(2) 0.0503(15) Uani 1 1 d . . . C14 C 0.9541(7) 0.3426(6) 0.7047(3) 0.0589(17) Uani 1 1 d . . . H14 H 0.8906 0.2860 0.7301 0.071 Uiso 1 1 calc R . . C15 C 0.9529(7) 0.3479(5) 0.6288(2) 0.0465(15) Uani 1 1 d . . . H15 H 0.8938 0.2887 0.6027 0.056 Uiso 1 1 calc R . . N1 N 0.9522(5) 0.4410(4) 0.40037(19) 0.0423(11) Uani 1 1 d . . . N2 N 0.7905(5) 0.5428(4) 0.4810(2) 0.0440(12) Uani 1 1 d . . . N3 N 1.0346(4) 0.4428(4) 0.51547(19) 0.0407(12) Uani 1 1 d . . . O1 O 1.1529(4) 0.3348(4) 0.34587(17) 0.0633(11) Uani 1 1 d . . . O2 O 1.2581(4) 0.3279(4) 0.49784(17) 0.0698(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0814(5) 0.1378(7) 0.0427(3) 0.0140(5) -0.0033(5) 0.0049(7) C1 0.043(3) 0.041(4) 0.041(3) -0.002(3) 0.006(3) -0.003(4) C2 0.049(4) 0.051(4) 0.041(3) -0.002(3) -0.004(3) 0.009(4) C3 0.045(3) 0.052(5) 0.043(3) 0.001(3) -0.006(3) -0.004(4) C4 0.059(3) 0.062(4) 0.036(2) -0.002(3) -0.006(3) 0.008(3) C5 0.098(5) 0.095(5) 0.089(4) -0.015(5) -0.031(5) -0.025(5) C6 0.113(5) 0.098(5) 0.108(5) 0.058(5) -0.048(5) -0.026(6) C7 0.047(3) 0.060(4) 0.041(3) -0.003(4) -0.001(3) 0.016(4) C8 0.073(5) 0.102(6) 0.083(4) 0.005(4) 0.021(4) 0.002(5) C9 0.096(5) 0.055(4) 0.075(4) -0.011(4) -0.020(5) 0.025(5) C10 0.031(3) 0.044(4) 0.034(2) 0.001(3) -0.004(3) 0.005(4) C11 0.038(3) 0.055(4) 0.039(2) 0.007(3) -0.004(3) -0.003(4) C12 0.059(4) 0.038(4) 0.047(3) -0.003(3) -0.007(3) -0.002(4) C13 0.054(4) 0.057(4) 0.040(3) 0.011(3) -0.011(3) 0.004(5) C14 0.056(4) 0.069(4) 0.051(3) 0.021(3) 0.011(4) -0.002(5) C15 0.041(3) 0.054(4) 0.045(3) 0.001(3) -0.002(3) -0.013(4) N1 0.040(2) 0.052(3) 0.034(2) -0.003(2) 0.000(2) 0.003(3) N2 0.038(2) 0.055(3) 0.039(2) -0.007(2) 0.000(2) 0.009(3) N3 0.031(2) 0.053(3) 0.037(2) -0.004(2) -0.004(2) 0.004(3) O1 0.064(2) 0.080(3) 0.0467(17) -0.010(3) 0.011(2) 0.019(2) O2 0.057(3) 0.103(3) 0.049(2) -0.006(3) -0.009(2) 0.036(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 Br1 C13 1.909(4) . ? C1 N2 1.245(6) . ? C1 N1 1.423(5) . ? C1 N3 1.424(6) . ? C2 O1 1.202(5) . ? C2 N1 1.359(6) . ? C2 C3 1.539(7) . ? C3 O2 1.207(6) . ? C3 N3 1.366(6) . ? C4 N1 1.478(5) . ? C4 C5 1.485(6) . ? C4 C6 1.509(7) . ? C4 H4 0.9800 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N2 1.470(5) . ? C7 C9 1.504(6) . ? C7 C8 1.525(7) . ? C7 H7 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C15 1.356(6) . ? C10 C11 1.370(6) . ? C10 N3 1.446(5) . ? C11 C12 1.408(5) . ? C11 H11 0.9300 . ? C12 C13 1.369(7) . ? C12 H12 0.9300 . ? C13 C14 1.377(7) . ? C14 C15 1.405(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? 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 C1 N1 119.8(5) . . ? N2 C1 N3 135.7(5) . . ? N1 C1 N3 104.5(4) . . ? O1 C2 N1 128.7(5) . . ? O1 C2 C3 127.1(5) . . ? N1 C2 C3 104.2(4) . . ? O2 C3 N3 128.6(5) . . ? O2 C3 C2 125.4(5) . . ? N3 C3 C2 106.0(5) . . ? N1 C4 C5 112.1(4) . . ? N1 C4 C6 109.6(5) . . ? C5 C4 C6 113.0(4) . . ? N1 C4 H4 107.3 . . ? C5 C4 H4 107.3 . . ? C6 C4 H4 107.3 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C9 106.7(4) . . ? N2 C7 C8 108.5(5) . . ? C9 C7 C8 111.4(5) . . ? N2 C7 H7 110.1 . . ? C9 C7 H7 110.1 . . ? C8 C7 H7 110.1 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 121.8(4) . . ? C15 C10 N3 119.1(5) . . ? C11 C10 N3 118.9(5) . . ? C10 C11 C12 119.8(5) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C13 C12 C11 117.0(5) . . ? C13 C12 H12 121.5 . . ? C11 C12 H12 121.5 . . ? C12 C13 C14 124.3(4) . . ? C12 C13 Br1 118.7(4) . . ? C14 C13 Br1 117.0(4) . . ? C13 C14 C15 116.8(6) . . ? C13 C14 H14 121.6 . . ? C15 C14 H14 121.6 . . ? C10 C15 C14 120.1(6) . . ? C10 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C2 N1 C1 113.4(4) . . ? C2 N1 C4 125.5(4) . . ? C1 N1 C4 121.0(4) . . ? C1 N2 C7 126.6(5) . . ? C3 N3 C1 111.8(4) . . ? C3 N3 C10 120.0(5) . . ? C1 N3 C10 126.7(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.279 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.061 data_zf _database_code_depnum_ccdc_archive 'CCDC 857966' #TrackingRef 'zf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H19 N3 O2' _chemical_formula_weight 297.35 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 11.082(2) _cell_length_b 8.7000(17) _cell_length_c 16.612(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.67(3) _cell_angle_gamma 90.00 _cell_volume 1573.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9671 _exptl_absorpt_correction_T_max 0.9834 _exptl_absorpt_process_details ; HIGASHI, T. (1995). Abscor-Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation,Tokyo,Japan. ; _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 graphite _diffrn_measurement_device_type 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method \W _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6400 _diffrn_reflns_av_R_equivalents 0.0827 _diffrn_reflns_av_sigmaI/netI 0.2257 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3575 _reflns_number_gt 1353 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid-AUTO (Rigaku,2000)' _computing_cell_refinement Rapid-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)' _computing_structure_solution SHELXS-97,(Sheldrick,1997) _computing_structure_refinement SHELXL-97,(Sheldrick,1997) _computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)' _computing_publication_material SHELXL-97,(Sheldrick,1997) _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^)+(0.0200P)^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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0113(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3575 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1370 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1391 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0445(3) 0.8605(4) 0.1995(2) 0.0214(9) Uani 1 1 d . . . C2 C -0.2014(3) 0.7250(4) 0.2381(2) 0.0260(9) Uani 1 1 d . . . C3 C -0.2370(3) 0.7602(4) 0.1458(2) 0.0244(9) Uani 1 1 d . . . C4 C -0.0116(3) 0.7577(4) 0.3481(2) 0.0220(9) Uani 1 1 d . . . H4 H 0.0699 0.8019 0.3487 0.026 Uiso 1 1 calc R . . C5 C -0.0650(3) 0.8373(4) 0.4149(2) 0.0289(10) Uani 1 1 d . . . H5A H -0.0758 0.9447 0.4022 0.043 Uiso 1 1 calc R . . H5B H -0.0100 0.8254 0.4664 0.043 Uiso 1 1 calc R . . H5C H -0.1430 0.7923 0.4183 0.043 Uiso 1 1 calc R . . C6 C 0.0056(3) 0.5868(4) 0.3631(2) 0.0304(10) Uani 1 1 d . . . H6A H -0.0732 0.5383 0.3584 0.046 Uiso 1 1 calc R . . H6B H 0.0522 0.5700 0.4172 0.046 Uiso 1 1 calc R . . H6C H 0.0487 0.5438 0.3234 0.046 Uiso 1 1 calc R . . C7 C -0.1223(3) 0.8892(4) 0.0457(2) 0.0232(9) Uani 1 1 d . . . H7 H -0.0357 0.9152 0.0478 0.028 Uiso 1 1 calc R . . C8 C -0.1971(3) 1.0364(4) 0.0250(2) 0.0344(11) Uani 1 1 d . . . H8A H -0.2823 1.0154 0.0247 0.052 Uiso 1 1 calc R . . H8B H -0.1875 1.0727 -0.0280 0.052 Uiso 1 1 calc R . . H8C H -0.1686 1.1135 0.0654 0.052 Uiso 1 1 calc R . . C9 C -0.1569(3) 0.7666(4) -0.0202(2) 0.0321(10) Uani 1 1 d . . . H9A H -0.1084 0.6760 -0.0052 0.048 Uiso 1 1 calc R . . H9B H -0.1416 0.8049 -0.0716 0.048 Uiso 1 1 calc R . . H9C H -0.2424 0.7418 -0.0254 0.048 Uiso 1 1 calc R . . C10 C 0.1317(3) 0.9971(4) 0.2628(2) 0.0196(9) Uani 1 1 d . . . C11 C 0.2541(3) 0.9570(4) 0.2724(2) 0.0216(9) Uani 1 1 d . . . H11 H 0.2804 0.8900 0.2356 0.026 Uiso 1 1 calc R . . C12 C 0.3376(3) 1.0171(4) 0.3373(2) 0.0202(9) Uani 1 1 d . . . C13 C 0.2981(3) 1.1198(4) 0.3907(2) 0.0252(10) Uani 1 1 d . . . H13 H 0.3537 1.1599 0.4345 0.030 Uiso 1 1 calc R . . C14 C 0.1755(3) 1.1628(4) 0.3789(2) 0.0257(9) Uani 1 1 d . . . H14 H 0.1491 1.2327 0.4143 0.031 Uiso 1 1 calc R . . C15 C 0.0937(3) 1.1023(4) 0.3153(2) 0.0236(9) Uani 1 1 d . . . H15 H 0.0117 1.1321 0.3072 0.028 Uiso 1 1 calc R . . C16 C 0.4648(3) 0.9724(4) 0.3481(2) 0.0280(10) Uani 1 1 d . . . C17 C 0.5670(4) 0.9320(5) 0.3557(3) 0.0388(11) Uani 1 1 d . . . H17 H 0.6482 0.8999 0.3618 0.047 Uiso 1 1 calc R . . N1 N -0.0867(2) 0.7884(3) 0.26577(17) 0.0195(7) Uani 1 1 d . . . N2 N -0.1348(2) 0.8307(3) 0.12797(17) 0.0205(7) Uani 1 1 d . . . N3 N 0.0500(2) 0.9391(3) 0.19494(17) 0.0198(7) Uani 1 1 d . . . O1 O -0.2644(2) 0.6523(3) 0.27757(15) 0.0330(7) Uani 1 1 d . . . O2 O -0.3348(2) 0.7300(3) 0.10206(15) 0.0341(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.025(2) 0.026(2) 0.014(2) -0.0014(17) 0.0049(17) 0.0095(18) C2 0.027(2) 0.028(2) 0.023(2) -0.0022(19) 0.0060(18) -0.0035(19) C3 0.027(2) 0.025(2) 0.021(2) -0.0035(19) 0.0051(18) 0.0024(19) C4 0.017(2) 0.030(2) 0.018(2) 0.0002(19) 0.0021(16) -0.0018(18) C5 0.028(2) 0.035(2) 0.023(2) 0.000(2) 0.0023(18) 0.001(2) C6 0.029(2) 0.036(3) 0.024(2) 0.004(2) -0.0006(19) 0.005(2) C7 0.024(2) 0.029(2) 0.017(2) 0.0054(18) 0.0065(17) 0.0018(18) C8 0.042(3) 0.030(2) 0.030(3) 0.003(2) 0.007(2) 0.003(2) C9 0.042(3) 0.031(2) 0.024(2) -0.006(2) 0.0075(19) 0.002(2) C10 0.021(2) 0.023(2) 0.016(2) -0.0045(17) 0.0055(17) -0.0061(17) C11 0.019(2) 0.025(2) 0.021(2) -0.0041(18) 0.0033(17) -0.0037(17) C12 0.015(2) 0.021(2) 0.025(2) 0.0012(18) 0.0055(17) -0.0045(16) C13 0.026(2) 0.028(2) 0.021(2) -0.0028(18) 0.0011(18) -0.0055(18) C14 0.028(2) 0.024(2) 0.027(2) -0.0047(19) 0.0091(19) -0.0016(19) C15 0.019(2) 0.023(2) 0.029(2) -0.0024(18) 0.0067(18) -0.0020(17) C16 0.030(2) 0.030(2) 0.024(2) 0.0011(19) 0.005(2) -0.004(2) C17 0.035(3) 0.035(3) 0.048(3) 0.007(2) 0.011(2) 0.002(2) N1 0.0145(16) 0.0254(19) 0.0185(17) 0.0039(14) 0.0028(13) -0.0031(14) N2 0.0194(17) 0.0229(17) 0.0196(18) -0.0017(15) 0.0047(14) 0.0006(14) N3 0.0160(17) 0.0240(18) 0.0205(18) -0.0021(15) 0.0058(14) -0.0064(15) O1 0.0237(15) 0.0508(18) 0.0252(16) 0.0026(14) 0.0061(13) -0.0142(14) O2 0.0200(15) 0.0461(18) 0.0324(17) 0.0000(14) -0.0050(13) -0.0094(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N3 1.265(4) . ? C1 N1 1.419(4) . ? C1 N2 1.428(4) . ? C2 O1 1.220(4) . ? C2 N1 1.384(4) . ? C2 C3 1.541(5) . ? C3 O2 1.217(4) . ? C3 N2 1.368(4) . ? C4 N1 1.488(4) . ? C4 C6 1.514(4) . ? C4 C5 1.518(4) . ? C4 H4 0.9800 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N2 1.489(4) . ? C7 C9 1.526(5) . ? C7 C8 1.530(4) . ? C7 H7 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.381(4) . ? C10 C15 1.383(4) . ? C10 N3 1.403(4) . ? C11 C12 1.386(5) . ? C11 H11 0.9300 . ? C12 C13 1.387(4) . ? C12 C16 1.441(5) . ? C13 C14 1.388(5) . ? C13 H13 0.9300 . ? C14 C15 1.363(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.169(5) . ? C17 H17 0.9300 . ? 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 N3 C1 N1 132.9(3) . . ? N3 C1 N2 120.6(3) . . ? N1 C1 N2 106.5(3) . . ? O1 C2 N1 127.6(3) . . ? O1 C2 C3 124.8(3) . . ? N1 C2 C3 107.6(3) . . ? O2 C3 N2 130.5(3) . . ? O2 C3 C2 126.0(3) . . ? N2 C3 C2 103.6(3) . . ? N1 C4 C6 111.1(3) . . ? N1 C4 C5 111.3(3) . . ? C6 C4 C5 112.5(3) . . ? N1 C4 H4 107.3 . . ? C6 C4 H4 107.3 . . ? C5 C4 H4 107.3 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C9 111.5(3) . . ? N2 C7 C8 110.7(3) . . ? C9 C7 C8 111.8(3) . . ? N2 C7 H7 107.6 . . ? C9 C7 H7 107.6 . . ? C8 C7 H7 107.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 120.1(3) . . ? C11 C10 N3 118.4(3) . . ? C15 C10 N3 121.2(3) . . ? C10 C11 C12 119.6(3) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 119.8(3) . . ? C11 C12 C16 119.5(3) . . ? C13 C12 C16 120.8(3) . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 119.9(4) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C10 120.5(4) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? C17 C16 C12 178.0(5) . . ? C16 C17 H17 180.0 . . ? C2 N1 C1 109.4(3) . . ? C2 N1 C4 123.9(3) . . ? C1 N1 C4 125.7(3) . . ? C3 N2 C1 112.4(3) . . ? C3 N2 C7 125.0(3) . . ? C1 N2 C7 122.1(3) . . ? C1 N3 C10 124.4(3) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.367 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.066