# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_product_5 _database_code_depnum_ccdc_archive 'CCDC 922313' #TrackingRef 'product_5.cif' #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C21 H29 N3 O3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C21 H29 N3 O3' _chemical_formula_weight 371.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _symmetry_Int_Tables_number 29 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,y,1/2+z 4 1/2+x,-y,z _cell_length_a 10.3528(4) _cell_length_b 10.3325(3) _cell_length_c 18.7803(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2008.94(12) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 9924 _cell_measurement_theta_min 1.97 _cell_measurement_theta_max 25.40 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method none _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6816 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_special_details ; Diffractometer operator E. Herdtweck scanspeed 30 s per frame dx 40 4510 frames measured in 9 data sets phi-scan with delta_phi = 0.50 omega-scans with delta_omega = 0.50 ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'rotating anode FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker APEX-II CCD ' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 63328 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0108 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.40 _reflns_number_total 3686 _reflns_number_gt 3564 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2010)' _computing_publication_material 'PLATON (Spek, 2010)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0354P)^2^+0.3238P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(7) _chemical_absolute_configuration unk _refine_ls_number_reflns 3686 _refine_ls_number_parameters 360 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0624 _refine_ls_wR_factor_gt 0.0609 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.149 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.029 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O10 O Uani 0.07104(9) 0.67500(10) -0.04771(5) 1.000 0.0297(3) . . O11 O Uani -0.19517(8) 0.42293(9) 0.08703(5) 1.000 0.0270(3) . . O16 O Uani 0.19985(8) 0.50748(10) 0.27255(5) 1.000 0.0282(3) . . N8 N Uani -0.06181(10) 0.52619(10) 0.00687(5) 1.000 0.0217(3) . . N12 N Uani -0.09816(10) 0.62062(11) 0.19003(6) 1.000 0.0199(3) . . N15 N Uani 0.10878(11) 0.70585(11) 0.26577(6) 1.000 0.0236(3) . . C1 C Uani 0.04123(13) 0.83743(13) 0.08415(7) 1.000 0.0247(4) . . C2 C Uani 0.01951(11) 0.69176(12) 0.07979(7) 1.000 0.0206(3) . . C3 C Uani -0.10616(11) 0.63851(12) 0.11348(6) 1.000 0.0195(3) . . C4 C Uani -0.22262(12) 0.72672(13) 0.09666(7) 1.000 0.0231(4) . . C5 C Uani -0.19448(14) 0.86791(13) 0.11291(8) 1.000 0.0272(4) . . C6 C Uani -0.08065(13) 0.91572(13) 0.06843(8) 1.000 0.0282(4) . . C7 C Uani 0.01557(11) 0.63648(12) 0.00500(7) 1.000 0.0214(3) . . C9 C Uani -0.12803(11) 0.51442(12) 0.07062(6) 1.000 0.0204(3) . . C13 C Uani -0.00560(13) 0.52422(13) 0.21489(7) 1.000 0.0231(3) . . C14 C Uani 0.11109(12) 0.57949(12) 0.25322(6) 1.000 0.0210(3) . . C17 C Uani 0.21411(13) 0.77290(15) 0.30211(7) 1.000 0.0281(4) . . C18 C Uani 0.32111(12) 0.81378(13) 0.25136(7) 1.000 0.0243(3) . . C19 C Uani 0.43978(15) 0.86319(18) 0.29094(8) 1.000 0.0351(5) . . C20 C Uani 0.55230(15) 0.89122(18) 0.24210(9) 1.000 0.0381(5) . . C21 C Uani -0.08462(12) 0.44170(13) -0.05493(7) 1.000 0.0246(4) . . C22 C Uani 0.01861(12) 0.34033(13) -0.06578(7) 1.000 0.0220(4) . . C23 C Uani 0.13031(13) 0.36908(13) -0.10419(7) 1.000 0.0240(4) . . C24 C Uani 0.22166(13) 0.27370(14) -0.11791(7) 1.000 0.0270(4) . . C25 C Uani 0.20205(14) 0.14904(14) -0.09358(7) 1.000 0.0289(4) . . C26 C Uani 0.09131(14) 0.11956(14) -0.05507(8) 1.000 0.0308(4) . . C27 C Uani 0.00001(13) 0.21498(13) -0.04123(7) 1.000 0.0272(4) . . H1 H Uiso -0.1751(16) 0.6043(15) 0.2067(8) 1.000 0.024(4) . . H2 H Uiso 0.0406(17) 0.7446(16) 0.2511(9) 1.000 0.030(4) . . H11 H Uiso 0.1124(15) 0.8610(14) 0.0513(8) 1.000 0.028(4) . . H12 H Uiso 0.0696(14) 0.8547(14) 0.1317(8) 1.000 0.019(4) . . H21 H Uiso 0.0888(14) 0.6496(13) 0.1035(8) 1.000 0.017(3) . . H41 H Uiso -0.2452(14) 0.7179(13) 0.0477(9) 1.000 0.023(4) . . H42 H Uiso -0.2948(14) 0.6961(15) 0.1243(8) 1.000 0.018(3) . . H51 H Uiso -0.1734(15) 0.8796(14) 0.1635(9) 1.000 0.030(4) . . H52 H Uiso -0.2703(18) 0.9175(16) 0.1029(9) 1.000 0.036(4) . . H61 H Uiso -0.0625(15) 1.0118(17) 0.0778(9) 1.000 0.033(4) . . H62 H Uiso -0.1020(15) 0.9057(14) 0.0184(9) 1.000 0.027(4) . . H131 H Uiso 0.0299(15) 0.4680(15) 0.1756(8) 1.000 0.027(4) . . H132 H Uiso -0.0485(14) 0.4663(15) 0.2486(9) 1.000 0.027(4) . . H171 H Uiso 0.2456(18) 0.7107(17) 0.3397(11) 1.000 0.046(5) . . H172 H Uiso 0.1759(16) 0.8512(17) 0.3255(9) 1.000 0.036(4) . . H181 H Uiso 0.2914(14) 0.8814(16) 0.2181(9) 1.000 0.033(4) . . H182 H Uiso 0.3431(14) 0.7402(14) 0.2219(8) 1.000 0.022(3) . . H191 H Uiso 0.414(2) 0.943(2) 0.3145(12) 1.000 0.059(6) . . H192 H Uiso 0.468(2) 0.798(2) 0.3291(13) 1.000 0.064(6) . . H201 H Uiso 0.577(2) 0.807(3) 0.2190(13) 1.000 0.072(7) . . H202 H Uiso 0.624(2) 0.927(2) 0.2661(12) 1.000 0.061(6) . . H203 H Uiso 0.5267(19) 0.9509(19) 0.2061(11) 1.000 0.052(6) . . H211 H Uiso -0.0892(14) 0.4978(16) -0.0978(9) 1.000 0.027(4) . . H212 H Uiso -0.1690(15) 0.3999(14) -0.0482(8) 1.000 0.028(4) . . H231 H Uiso 0.1453(16) 0.4559(17) -0.1236(8) 1.000 0.032(4) . . H241 H Uiso 0.3023(17) 0.2940(15) -0.1465(9) 1.000 0.034(4) . . H251 H Uiso 0.2644(17) 0.0798(17) -0.1059(9) 1.000 0.033(4) . . H261 H Uiso 0.0783(16) 0.0276(18) -0.0398(9) 1.000 0.038(4) . . H271 H Uiso -0.0764(16) 0.1913(16) -0.0132(10) 1.000 0.035(4) . . 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 O10 0.0311(5) 0.0352(5) 0.0227(5) 0.0034(4) 0.0069(4) -0.0017(4) O11 0.0253(5) 0.0281(5) 0.0277(5) -0.0013(4) 0.0017(4) -0.0082(4) O16 0.0253(4) 0.0371(5) 0.0221(5) 0.0032(4) -0.0006(4) 0.0089(4) N8 0.0217(5) 0.0257(5) 0.0178(5) -0.0016(4) -0.0004(4) -0.0003(4) N12 0.0175(5) 0.0235(5) 0.0186(5) 0.0013(4) 0.0009(4) 0.0006(4) N15 0.0191(5) 0.0282(6) 0.0236(6) 0.0002(4) -0.0028(4) -0.0006(4) C1 0.0242(6) 0.0259(7) 0.0240(7) 0.0023(5) 0.0015(6) -0.0049(5) C2 0.0168(6) 0.0246(6) 0.0205(6) 0.0019(5) 0.0014(5) -0.0002(5) C3 0.0165(6) 0.0239(6) 0.0181(6) 0.0016(5) 0.0003(5) -0.0010(4) C4 0.0185(6) 0.0292(7) 0.0217(7) 0.0024(5) 0.0004(5) 0.0018(5) C5 0.0267(7) 0.0258(7) 0.0291(7) 0.0018(6) 0.0010(5) 0.0055(5) C6 0.0339(7) 0.0239(7) 0.0268(7) 0.0044(6) 0.0004(6) 0.0011(5) C7 0.0175(6) 0.0245(6) 0.0222(6) 0.0016(5) 0.0011(5) 0.0027(5) C9 0.0151(5) 0.0268(6) 0.0192(6) 0.0008(5) -0.0012(5) 0.0013(5) C13 0.0251(6) 0.0227(6) 0.0214(6) 0.0015(6) 0.0004(5) 0.0004(5) C14 0.0211(6) 0.0289(6) 0.0131(6) 0.0029(5) 0.0041(4) 0.0027(5) C17 0.0247(7) 0.0374(8) 0.0223(7) -0.0044(6) -0.0005(5) -0.0051(6) C18 0.0254(6) 0.0242(6) 0.0233(6) -0.0009(6) 0.0004(5) 0.0001(5) C19 0.0286(8) 0.0479(9) 0.0288(8) -0.0049(7) 0.0011(6) -0.0081(6) C20 0.0306(8) 0.0466(9) 0.0371(9) 0.0056(8) -0.0007(7) -0.0094(7) C21 0.0224(6) 0.0337(7) 0.0178(6) -0.0029(6) -0.0037(5) 0.0008(5) C22 0.0238(6) 0.0274(7) 0.0149(6) -0.0044(5) -0.0034(5) -0.0018(5) C23 0.0275(7) 0.0249(7) 0.0196(6) 0.0004(5) -0.0014(5) -0.0030(5) C24 0.0247(7) 0.0327(7) 0.0236(7) -0.0045(5) 0.0025(5) -0.0033(5) C25 0.0320(7) 0.0296(7) 0.0251(7) -0.0057(6) -0.0012(6) 0.0045(6) C26 0.0405(8) 0.0254(7) 0.0265(7) 0.0010(6) 0.0015(6) -0.0024(6) C27 0.0290(6) 0.0321(7) 0.0204(6) 0.0005(6) 0.0027(5) -0.0058(6) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O10 C7 1.2117(16) . . yes O11 C9 1.2132(15) . . yes O16 C14 1.2369(15) . . yes N8 C7 1.3934(16) . . yes N8 C9 1.3850(15) . . yes N8 C21 1.4714(16) . . yes N12 C3 1.4518(16) . . yes N12 C13 1.4589(17) . . yes N15 C14 1.3269(17) . . yes N15 C17 1.4611(18) . . yes N12 H1 0.872(16) . . no N15 H2 0.857(17) . . no C1 C2 1.5240(18) . . no C1 C6 1.5276(19) . . no C2 C7 1.5168(18) . . no C2 C3 1.5478(17) . . no C3 C9 1.5307(17) . . no C3 C4 1.5441(17) . . no C4 C5 1.5186(19) . . no C5 C6 1.527(2) . . no C13 C14 1.5178(18) . . no C17 C18 1.5212(19) . . no C18 C19 1.524(2) . . no C19 C20 1.511(2) . . no C21 C22 1.5102(18) . . no C22 C27 1.3882(19) . . no C22 C23 1.3949(18) . . no C23 C24 1.3900(19) . . no C24 C25 1.382(2) . . no C25 C26 1.389(2) . . no C26 C27 1.390(2) . . no C1 H11 0.991(15) . . no C1 H12 0.957(15) . . no C2 H21 0.950(14) . . no C4 H41 0.953(17) . . no C4 H42 0.963(15) . . no C5 H51 0.982(17) . . no C5 H52 0.956(18) . . no C6 H61 1.026(18) . . no C6 H62 0.971(17) . . no C13 H131 1.009(15) . . no C13 H132 0.978(16) . . no C17 H171 1.009(19) . . no C17 H172 1.002(17) . . no C18 H181 0.986(17) . . no C18 H182 0.967(15) . . no C19 H191 0.97(2) . . no C19 H192 1.03(2) . . no C20 H201 1.01(3) . . no C20 H202 0.94(2) . . no C20 H203 0.95(2) . . no C21 H211 0.993(17) . . no C21 H212 0.983(15) . . no C23 H231 0.981(17) . . no C24 H241 1.015(17) . . no C25 H251 0.991(18) . . no C26 H261 1.002(18) . . no C27 H271 0.981(17) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N8 C9 112.22(10) . . . yes C7 N8 C21 123.89(10) . . . yes C9 N8 C21 123.39(10) . . . yes C3 N12 C13 116.19(10) . . . yes C14 N15 C17 122.42(11) . . . yes C3 N12 H1 109.1(10) . . . no C13 N12 H1 110.7(10) . . . no C17 N15 H2 122.9(11) . . . no C14 N15 H2 114.7(11) . . . no C2 C1 C6 113.00(11) . . . no C1 C2 C7 115.19(11) . . . no C3 C2 C7 102.83(9) . . . no C1 C2 C3 116.94(10) . . . no C2 C3 C9 101.95(9) . . . no C4 C3 C9 105.75(9) . . . no N12 C3 C2 113.71(10) . . . yes N12 C3 C4 108.80(10) . . . yes N12 C3 C9 114.99(10) . . . yes C2 C3 C4 111.28(10) . . . no C3 C4 C5 112.09(11) . . . no C4 C5 C6 110.42(11) . . . no C1 C6 C5 111.13(11) . . . no O10 C7 N8 124.17(12) . . . yes O10 C7 C2 128.32(11) . . . yes N8 C7 C2 107.46(10) . . . yes O11 C9 C3 127.15(11) . . . yes N8 C9 C3 107.93(10) . . . yes O11 C9 N8 124.86(11) . . . yes N12 C13 C14 114.69(11) . . . yes N15 C14 C13 116.11(11) . . . yes O16 C14 N15 123.58(12) . . . yes O16 C14 C13 120.28(11) . . . yes N15 C17 C18 112.49(11) . . . yes C17 C18 C19 111.99(11) . . . no C18 C19 C20 112.94(12) . . . no N8 C21 C22 113.85(10) . . . yes C21 C22 C23 120.58(12) . . . no C21 C22 C27 120.27(11) . . . no C23 C22 C27 119.04(12) . . . no C22 C23 C24 120.59(12) . . . no C23 C24 C25 119.98(13) . . . no C24 C25 C26 119.85(13) . . . no C25 C26 C27 120.19(13) . . . no C22 C27 C26 120.35(12) . . . no C2 C1 H11 108.6(8) . . . no C2 C1 H12 106.2(9) . . . no C6 C1 H11 111.3(9) . . . no C6 C1 H12 109.6(9) . . . no H11 C1 H12 107.9(12) . . . no C1 C2 H21 108.4(8) . . . no C3 C2 H21 106.3(9) . . . no C7 C2 H21 106.4(9) . . . no C3 C4 H41 109.4(9) . . . no C3 C4 H42 107.6(9) . . . no C5 C4 H41 109.4(8) . . . no C5 C4 H42 110.9(9) . . . no H41 C4 H42 107.4(13) . . . no C4 C5 H51 110.8(9) . . . no C4 C5 H52 108.5(10) . . . no C6 C5 H51 108.5(9) . . . no C6 C5 H52 110.7(10) . . . no H51 C5 H52 107.9(14) . . . no C1 C6 H61 109.2(9) . . . no C1 C6 H62 108.6(9) . . . no C5 C6 H61 111.2(9) . . . no C5 C6 H62 108.6(9) . . . no H61 C6 H62 108.1(13) . . . no N12 C13 H131 113.5(9) . . . no N12 C13 H132 109.1(9) . . . no C14 C13 H131 105.9(9) . . . no C14 C13 H132 106.5(9) . . . no H131 C13 H132 106.7(13) . . . no N15 C17 H171 105.4(10) . . . no N15 C17 H172 107.0(10) . . . no C18 C17 H171 112.3(11) . . . no C18 C17 H172 109.8(10) . . . no H171 C17 H172 109.6(15) . . . no C17 C18 H181 111.5(9) . . . no C17 C18 H182 108.2(9) . . . no C19 C18 H181 108.8(9) . . . no C19 C18 H182 110.6(9) . . . no H181 C18 H182 105.5(13) . . . no C18 C19 H191 106.5(12) . . . no C18 C19 H192 110.5(12) . . . no C20 C19 H191 109.0(12) . . . no C20 C19 H192 109.3(12) . . . no H191 C19 H192 108.5(18) . . . no C19 C20 H201 107.0(14) . . . no C19 C20 H202 113.1(13) . . . no C19 C20 H203 109.9(12) . . . no H201 C20 H202 110.2(17) . . . no H201 C20 H203 109.0(19) . . . no H202 C20 H203 107.7(18) . . . no N8 C21 H211 107.5(10) . . . no N8 C21 H212 107.6(9) . . . no C22 C21 H211 109.2(9) . . . no C22 C21 H212 110.0(9) . . . no H211 C21 H212 108.6(12) . . . no C22 C23 H231 121.2(10) . . . no C24 C23 H231 118.2(10) . . . no C23 C24 H241 120.8(9) . . . no C25 C24 H241 119.3(9) . . . no C24 C25 H251 120.0(10) . . . no C26 C25 H251 120.1(10) . . . no C25 C26 H261 117.9(10) . . . no C27 C26 H261 121.9(10) . . . no C22 C27 H271 121.5(10) . . . no C26 C27 H271 118.1(10) . . . no _iucr_refine_instructions_details ; ; data_product_12 _database_code_depnum_ccdc_archive 'CCDC 922314' #TrackingRef 'product_12.cif' #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C26 H28 N4 O2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C26 H28 N4 O2' _chemical_formula_weight 428.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z _cell_length_a 6.8229(1) _cell_length_b 19.0016(3) _cell_length_c 8.4335(1) _cell_angle_alpha 90 _cell_angle_beta 92.3910(7) _cell_angle_gamma 90 _cell_volume 1092.42(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 9155 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 25.52 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method none _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6898 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_special_details ; Diffractometer operator E. Herdtweck scanspeed 10 s per frame dx 50 3183 frames measured in 6 data sets phi-scan with delta_phi = 0.50 omega-scans with delta_omega = 0.50 ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker APEX-II CCD ' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 21939 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0110 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.52 _reflns_number_total 4057 _reflns_number_gt 4015 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2010)' _computing_publication_material 'PLATON (Spek, 2010)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0390P)^2^+0.1287P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(7) _chemical_absolute_configuration syn _refine_ls_number_reflns 4057 _refine_ls_number_parameters 401 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0239 _refine_ls_R_factor_gt 0.0236 _refine_ls_wR_factor_ref 0.0606 _refine_ls_wR_factor_gt 0.0604 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.52 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.169 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.029 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.81187(12) 0.09226(4) 1.10428(10) 1.000 0.0235(2) . . O2 O Uani 0.51367(13) 0.00274(5) 0.48514(10) 1.000 0.0276(3) . . N1 N Uani 0.38242(13) 0.04188(5) 0.87342(10) 1.000 0.0171(3) . . N2 N Uani 0.50908(14) 0.06331(5) 1.17658(12) 1.000 0.0197(3) . . N3 N Uani 0.08744(15) 0.19355(5) 1.01684(12) 1.000 0.0215(3) . . N4 N Uani 0.55768(14) -0.06453(5) 0.70436(12) 1.000 0.0210(3) . . C1 C Uani 0.23934(16) 0.07281(6) 0.97900(13) 1.000 0.0182(3) . . C2 C Uani 0.56827(16) 0.08156(6) 0.89276(13) 1.000 0.0183(3) . . C3 C Uani 0.63784(16) 0.07930(5) 1.06763(13) 1.000 0.0182(3) . . C4 C Uani 0.30086(16) 0.04866(6) 1.14585(13) 1.000 0.0206(3) . . C5 C Uani 0.55662(17) 0.15871(6) 0.83456(14) 1.000 0.0208(3) . . C6 C Uani 0.37768(17) 0.19190(6) 0.90070(13) 1.000 0.0202(3) . . C7 C Uani 0.23656(16) 0.15177(6) 0.96526(13) 1.000 0.0190(3) . . C8 C Uani 0.13041(18) 0.26235(7) 0.98237(14) 1.000 0.0231(3) . . C9 C Uani 0.31356(18) 0.26347(6) 0.90940(14) 1.000 0.0227(3) . . C10 C Uani 0.3920(2) 0.32831(7) 0.86404(15) 1.000 0.0300(4) . . C11 C Uani 0.2868(2) 0.38915(7) 0.89006(17) 1.000 0.0375(5) . . C12 C Uani 0.1058(2) 0.38691(7) 0.96253(16) 1.000 0.0360(4) . . C13 C Uani 0.0251(2) 0.32397(7) 1.01063(15) 1.000 0.0294(4) . . C14 C Uani 0.31335(16) 0.02795(6) 0.70941(13) 1.000 0.0195(3) . . C15 C Uani 0.12455(17) -0.01842(7) 0.68767(15) 1.000 0.0240(4) . . C16 C Uani 0.06486(19) 0.02578(8) 0.54006(16) 1.000 0.0312(4) . . C17 C Uani 0.20966(18) 0.08364(7) 0.59956(15) 1.000 0.0253(4) . . C18 C Uani 0.47478(16) -0.01119(6) 0.62263(13) 1.000 0.0196(3) . . C19 C Uani 0.68080(17) -0.11855(7) 0.63496(16) 1.000 0.0239(3) . . C20 C Uani 0.60209(18) -0.19187(7) 0.66656(15) 1.000 0.0260(4) . . C21 C Uani 0.40230(17) -0.20964(6) 0.59206(14) 1.000 0.0224(3) . . C22 C Uani 0.3092(2) -0.27067(7) 0.64084(16) 1.000 0.0302(4) . . C23 C Uani 0.1293(2) -0.29095(8) 0.57321(17) 1.000 0.0355(4) . . C24 C Uani 0.0380(2) -0.24972(8) 0.45639(17) 1.000 0.0340(4) . . C25 C Uani 0.1270(2) -0.18860(7) 0.40850(15) 1.000 0.0307(4) . . C26 C Uani 0.30833(19) -0.16860(6) 0.47537(14) 1.000 0.0248(3) . . H2 H Uiso 0.559(2) 0.0587(8) 1.2725(19) 1.000 0.025(3) . . H3 H Uiso -0.016(2) 0.1774(7) 1.0565(16) 1.000 0.019(3) . . H4 H Uiso 0.527(2) -0.0705(7) 0.7997(18) 1.000 0.018(3) . . H11 H Uiso 0.1103(18) 0.0545(7) 0.9569(14) 1.000 0.010(3) . . H21 H Uiso 0.6663(18) 0.0577(7) 0.8355(15) 1.000 0.011(3) . . H41 H Uiso 0.230(2) 0.0730(8) 1.2245(19) 1.000 0.026(4) . . H42 H Uiso 0.2759(19) -0.0033(8) 1.1545(15) 1.000 0.017(3) . . H51 H Uiso 0.679(2) 0.1823(8) 0.8707(16) 1.000 0.023(3) . . H52 H Uiso 0.5535(19) 0.1594(7) 0.7155(17) 1.000 0.018(3) . . H101 H Uiso 0.520(2) 0.3302(9) 0.8160(19) 1.000 0.036(4) . . H111 H Uiso 0.340(2) 0.4335(10) 0.8553(18) 1.000 0.036(4) . . H121 H Uiso 0.035(3) 0.4302(10) 0.979(2) 1.000 0.040(4) . . H131 H Uiso -0.099(2) 0.3209(9) 1.0622(19) 1.000 0.033(4) . . H151 H Uiso 0.145(2) -0.0676(9) 0.6710(17) 1.000 0.027(3) . . H152 H Uiso 0.033(2) -0.0107(8) 0.7726(17) 1.000 0.023(3) . . H161 H Uiso -0.080(2) 0.0387(9) 0.5278(19) 1.000 0.035(4) . . H162 H Uiso 0.107(2) 0.0059(8) 0.4413(18) 1.000 0.025(3) . . H171 H Uiso 0.143(2) 0.1178(8) 0.6643(17) 1.000 0.025(3) . . H172 H Uiso 0.293(2) 0.1083(8) 0.5222(18) 1.000 0.030(4) . . H191 H Uiso 0.813(2) -0.1149(8) 0.6861(16) 1.000 0.021(3) . . H192 H Uiso 0.6827(19) -0.1096(8) 0.5252(18) 1.000 0.021(3) . . H201 H Uiso 0.595(2) -0.1985(8) 0.7814(17) 1.000 0.020(3) . . H202 H Uiso 0.693(3) -0.2231(10) 0.625(2) 1.000 0.046(5) . . H221 H Uiso 0.370(2) -0.3009(9) 0.723(2) 1.000 0.035(4) . . H231 H Uiso 0.072(2) -0.3325(10) 0.606(2) 1.000 0.039(4) . . H241 H Uiso -0.086(3) -0.2630(9) 0.411(2) 1.000 0.038(4) . . H251 H Uiso 0.069(2) -0.1580(9) 0.3265(19) 1.000 0.036(4) . . H261 H Uiso 0.372(2) -0.1238(9) 0.4422(18) 1.000 0.034(4) . . 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 0.0191(4) 0.0262(4) 0.0251(4) -0.0013(3) -0.0015(3) -0.0025(3) O2 0.0327(5) 0.0326(5) 0.0178(4) 0.0035(3) 0.0054(3) -0.0005(4) N1 0.0164(4) 0.0187(5) 0.0162(4) -0.0004(4) 0.0013(3) -0.0026(4) N2 0.0213(5) 0.0210(5) 0.0167(5) 0.0011(4) -0.0003(4) 0.0001(4) N3 0.0184(5) 0.0213(5) 0.0250(5) -0.0020(4) 0.0023(4) -0.0008(4) N4 0.0235(5) 0.0224(5) 0.0171(5) -0.0021(4) 0.0028(4) -0.0003(4) C1 0.0174(5) 0.0176(5) 0.0197(5) 0.0006(4) 0.0029(4) -0.0027(4) C2 0.0157(5) 0.0205(6) 0.0188(5) -0.0009(4) 0.0036(4) -0.0012(4) C3 0.0196(5) 0.0133(5) 0.0216(5) -0.0011(4) 0.0010(4) 0.0019(4) C4 0.0211(5) 0.0213(6) 0.0196(5) -0.0006(4) 0.0052(4) -0.0017(4) C5 0.0196(5) 0.0218(6) 0.0211(6) 0.0029(4) 0.0027(4) -0.0033(4) C6 0.0226(5) 0.0198(6) 0.0180(5) 0.0015(4) -0.0018(4) -0.0024(4) C7 0.0185(5) 0.0192(6) 0.0193(5) -0.0003(4) -0.0006(4) 0.0000(4) C8 0.0283(6) 0.0219(6) 0.0186(5) -0.0026(5) -0.0061(5) 0.0012(5) C9 0.0287(6) 0.0209(6) 0.0182(5) 0.0001(4) -0.0033(5) -0.0002(5) C10 0.0437(8) 0.0203(6) 0.0258(6) -0.0002(5) -0.0008(5) -0.0070(5) C11 0.0635(10) 0.0174(6) 0.0312(7) 0.0003(5) -0.0034(6) -0.0041(6) C12 0.0565(9) 0.0218(6) 0.0288(7) -0.0059(5) -0.0086(6) 0.0100(6) C13 0.0362(7) 0.0254(6) 0.0261(6) -0.0065(5) -0.0057(5) 0.0084(5) C14 0.0195(5) 0.0215(5) 0.0173(5) 0.0011(4) -0.0006(4) -0.0029(4) C15 0.0206(6) 0.0278(7) 0.0235(6) -0.0026(5) 0.0006(5) -0.0061(5) C16 0.0250(6) 0.0433(8) 0.0248(6) 0.0012(6) -0.0052(5) -0.0048(6) C17 0.0241(6) 0.0295(7) 0.0219(6) 0.0039(5) -0.0035(5) 0.0016(5) C18 0.0197(5) 0.0201(5) 0.0188(5) -0.0016(4) -0.0003(4) -0.0066(4) C19 0.0198(6) 0.0262(6) 0.0258(6) -0.0050(5) 0.0017(5) -0.0006(5) C20 0.0241(6) 0.0243(6) 0.0294(7) -0.0008(5) -0.0025(5) 0.0044(5) C21 0.0250(6) 0.0213(6) 0.0209(6) -0.0043(4) 0.0013(5) 0.0016(4) C22 0.0375(7) 0.0251(6) 0.0276(6) 0.0035(5) -0.0031(5) -0.0010(5) C23 0.0389(8) 0.0315(7) 0.0362(7) 0.0007(6) 0.0014(6) -0.0130(6) C24 0.0287(7) 0.0385(8) 0.0343(7) -0.0082(6) -0.0043(6) -0.0066(6) C25 0.0362(7) 0.0305(7) 0.0247(6) -0.0049(5) -0.0072(5) 0.0006(6) C26 0.0311(6) 0.0219(6) 0.0212(6) -0.0029(5) -0.0009(5) -0.0020(5) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.2391(14) . . yes O2 C18 1.2291(14) . . yes N1 C1 1.4710(14) . . yes N1 C2 1.4784(14) . . yes N1 C14 1.4666(14) . . yes N2 C3 1.3326(15) . . yes N2 C4 1.4602(15) . . yes N3 C7 1.3754(15) . . yes N3 C8 1.3736(16) . . yes N4 C18 1.3378(15) . . yes N4 C19 1.4639(16) . . yes N2 H2 0.869(16) . . no N3 H3 0.851(14) . . no N4 H4 0.847(15) . . no C1 C4 1.5223(16) . . no C1 C7 1.5049(16) . . no C2 C3 1.5309(15) . . no C2 C5 1.5470(16) . . no C5 C6 1.5021(16) . . no C6 C9 1.4314(16) . . no C6 C7 1.3597(16) . . no C8 C9 1.4159(17) . . no C8 C13 1.3994(19) . . no C9 C10 1.4028(18) . . no C10 C11 1.3831(19) . . no C11 C12 1.4012(19) . . no C12 C13 1.3844(19) . . no C14 C18 1.5392(16) . . no C14 C17 1.5569(17) . . no C14 C15 1.5651(16) . . no C15 C16 1.5423(19) . . no C16 C17 1.5477(19) . . no C19 C20 1.5207(19) . . no C20 C21 1.5151(17) . . no C21 C26 1.3911(17) . . no C21 C22 1.3926(18) . . no C22 C23 1.3864(19) . . no C23 C24 1.386(2) . . no C24 C25 1.379(2) . . no C25 C26 1.3910(18) . . no C1 H11 0.958(12) . . no C2 H21 0.956(13) . . no C4 H41 0.956(15) . . no C4 H42 1.005(15) . . no C5 H51 0.985(14) . . no C5 H52 1.004(14) . . no C10 H101 0.979(14) . . no C11 H111 0.968(18) . . no C12 H121 0.967(19) . . no C13 H131 0.970(14) . . no C15 H151 0.956(17) . . no C15 H152 0.981(14) . . no C16 H161 1.020(14) . . no C16 H162 0.969(15) . . no C17 H171 0.973(15) . . no C17 H172 1.000(15) . . no C19 H191 0.986(14) . . no C19 H192 0.942(15) . . no C20 H201 0.980(14) . . no C20 H202 0.937(19) . . no C22 H221 0.979(17) . . no C23 H231 0.928(18) . . no C24 H241 0.95(2) . . no C25 H251 0.975(16) . . no C26 H261 1.001(16) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 108.50(8) . . . yes C1 N1 C14 116.60(8) . . . yes C2 N1 C14 115.88(8) . . . yes C3 N2 C4 125.85(10) . . . yes C7 N3 C8 108.37(10) . . . yes C18 N4 C19 124.24(10) . . . yes C3 N2 H2 114.9(9) . . . no C4 N2 H2 119.1(9) . . . no C7 N3 H3 123.6(9) . . . no C8 N3 H3 127.9(9) . . . no C19 N4 H4 117.0(9) . . . no C18 N4 H4 118.3(9) . . . no C4 C1 C7 111.95(9) . . . no N1 C1 C4 105.95(9) . . . yes N1 C1 C7 111.00(9) . . . yes N1 C2 C5 114.57(9) . . . yes C3 C2 C5 110.00(9) . . . no N1 C2 C3 108.78(9) . . . yes N2 C3 C2 118.93(10) . . . yes O1 C3 N2 121.72(10) . . . yes O1 C3 C2 119.35(10) . . . yes N2 C4 C1 109.59(9) . . . yes C2 C5 C6 108.17(9) . . . no C7 C6 C9 106.81(10) . . . no C5 C6 C7 120.89(10) . . . no C5 C6 C9 132.29(10) . . . no C1 C7 C6 125.67(10) . . . no N3 C7 C1 123.94(10) . . . yes N3 C7 C6 110.40(10) . . . yes N3 C8 C9 107.84(11) . . . yes N3 C8 C13 130.14(11) . . . yes C9 C8 C13 122.02(12) . . . no C6 C9 C8 106.57(10) . . . no C8 C9 C10 119.04(11) . . . no C6 C9 C10 134.39(12) . . . no C9 C10 C11 118.98(12) . . . no C10 C11 C12 121.10(12) . . . no C11 C12 C13 121.51(12) . . . no C8 C13 C12 117.36(12) . . . no N1 C14 C18 109.12(9) . . . yes N1 C14 C15 116.27(9) . . . yes N1 C14 C17 123.97(10) . . . yes C17 C14 C18 111.22(9) . . . no C15 C14 C17 87.80(9) . . . no C15 C14 C18 105.91(9) . . . no C14 C15 C16 88.64(9) . . . no C15 C16 C17 88.95(10) . . . no C14 C17 C16 88.75(10) . . . no O2 C18 N4 123.09(11) . . . yes N4 C18 C14 114.62(9) . . . yes O2 C18 C14 122.10(10) . . . yes N4 C19 C20 111.08(10) . . . yes C19 C20 C21 116.73(10) . . . no C20 C21 C22 118.47(11) . . . no C20 C21 C26 123.27(11) . . . no C22 C21 C26 118.25(11) . . . no C21 C22 C23 121.12(12) . . . no C22 C23 C24 119.95(13) . . . no C23 C24 C25 119.60(13) . . . no C24 C25 C26 120.43(12) . . . no C21 C26 C25 120.63(11) . . . no N1 C1 H11 111.4(7) . . . no C4 C1 H11 106.6(7) . . . no C7 C1 H11 109.8(8) . . . no N1 C2 H21 108.5(8) . . . no C3 C2 H21 106.2(8) . . . no C5 C2 H21 108.5(8) . . . no N2 C4 H41 107.5(9) . . . no N2 C4 H42 109.9(8) . . . no C1 C4 H41 111.6(9) . . . no C1 C4 H42 108.8(7) . . . no H41 C4 H42 109.4(12) . . . no C2 C5 H51 107.6(9) . . . no C2 C5 H52 109.2(8) . . . no C6 C5 H51 112.7(8) . . . no C6 C5 H52 112.5(8) . . . no H51 C5 H52 106.6(11) . . . no C9 C10 H101 120.2(10) . . . no C11 C10 H101 120.9(10) . . . no C10 C11 H111 118.4(9) . . . no C12 C11 H111 120.5(9) . . . no C11 C12 H121 119.4(12) . . . no C13 C12 H121 119.1(12) . . . no C8 C13 H131 119.4(10) . . . no C12 C13 H131 123.3(10) . . . no C14 C15 H151 116.3(8) . . . no C14 C15 H152 112.1(9) . . . no C16 C15 H151 116.7(9) . . . no C16 C15 H152 110.7(9) . . . no H151 C15 H152 110.8(12) . . . no C15 C16 H161 115.8(9) . . . no C15 C16 H162 113.8(9) . . . no C17 C16 H161 117.7(10) . . . no C17 C16 H162 110.3(9) . . . no H161 C16 H162 109.1(12) . . . no C14 C17 H171 109.3(9) . . . no C14 C17 H172 116.8(8) . . . no C16 C17 H171 110.4(8) . . . no C16 C17 H172 119.6(9) . . . no H171 C17 H172 110.2(12) . . . no N4 C19 H191 107.8(8) . . . no N4 C19 H192 107.3(9) . . . no C20 C19 H191 108.1(9) . . . no C20 C19 H192 110.9(9) . . . no H191 C19 H192 111.6(11) . . . no C19 C20 H201 108.9(9) . . . no C19 C20 H202 105.7(12) . . . no C21 C20 H201 107.5(8) . . . no C21 C20 H202 107.6(12) . . . no H201 C20 H202 110.4(14) . . . no C21 C22 H221 120.8(9) . . . no C23 C22 H221 118.0(9) . . . no C22 C23 H231 119.4(10) . . . no C24 C23 H231 120.7(9) . . . no C23 C24 H241 120.2(10) . . . no C25 C24 H241 120.2(10) . . . no C24 C25 H251 122.7(9) . . . no C26 C25 H251 116.9(9) . . . no C21 C26 H261 118.8(8) . . . no C25 C26 H261 120.5(8) . . . no _iucr_refine_instructions_details ; ; data_product_15 _database_code_depnum_ccdc_archive 'CCDC 922315' #TrackingRef 'product_15.cif' #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C25 H29 N3 O2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C25 H29 N3 O2' _chemical_formula_weight 403.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z _cell_length_a 7.9993(2) _cell_length_b 12.1497(2) _cell_length_c 21.7198(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2110.93(7) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 9827 _cell_measurement_theta_min 1.88 _cell_measurement_theta_max 25.42 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.61 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method none _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7029 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_special_details ; Diffractometer operator E. Herdtweck scanspeed 10 s per frame dx 50 3519 frames measured in 7 data sets phi-scan with delta_phi = 0.50 omega-scans with delta_omega = 0.50 ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker APEX-II CCD ' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 47715 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0066 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.42 _reflns_number_total 3904 _reflns_number_gt 3859 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2010)' _computing_publication_material 'PLATON (Spek, 2010)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0256P)^2^+0.4759P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0069(5) _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 -0.1(8) _chemical_absolute_configuration syn _refine_ls_number_reflns 3904 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0238 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0581 _refine_ls_wR_factor_gt 0.0577 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.42 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.174 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.026 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.10501(10) -0.00651(7) 0.25653(4) 1.000 0.0243(2) . . O2 O Uani -0.03220(10) 0.28902(7) 0.51157(3) 1.000 0.0221(2) . . N1 N Uani -0.06458(12) 0.14114(8) 0.27837(4) 1.000 0.0185(3) . . N2 N Uani 0.08460(11) 0.22197(7) 0.35361(4) 1.000 0.0157(2) . . N3 N Uani -0.19655(12) 0.23368(8) 0.43291(4) 1.000 0.0198(3) . . C1 C Uani 0.15279(13) 0.10997(9) 0.34735(5) 1.000 0.0173(3) . . C2 C Uani 0.06570(14) 0.07253(9) 0.28846(5) 1.000 0.0184(3) . . C3 C Uani -0.08288(14) 0.22207(9) 0.32720(5) 1.000 0.0172(3) . . C4 C Uani 0.34484(14) 0.11106(10) 0.34053(6) 1.000 0.0229(3) . . C5 C Uani 0.40188(16) 0.00077(11) 0.36610(7) 1.000 0.0319(4) . . C6 C Uani 0.28902(17) -0.01658(11) 0.42145(7) 1.000 0.0321(4) . . C7 C Uani 0.11750(15) 0.02598(10) 0.40077(5) 1.000 0.0215(3) . . C8 C Uani 0.09854(13) 0.27740(9) 0.41292(5) 1.000 0.0159(3) . . C9 C Uani -0.04980(13) 0.26409(9) 0.45677(5) 1.000 0.0173(3) . . C10 C Uani -0.21972(14) 0.18534(10) 0.37216(5) 1.000 0.0209(3) . . C11 C Uani -0.18834(15) 0.12498(10) 0.23014(5) 1.000 0.0218(3) . . C12 C Uani -0.19990(15) 0.22259(11) 0.18571(5) 1.000 0.0238(3) . . C13 C Uani -0.04085(15) 0.24422(9) 0.15040(5) 1.000 0.0226(3) . . C14 C Uani 0.09866(16) 0.28892(10) 0.17961(6) 1.000 0.0262(3) . . C15 C Uani 0.24324(18) 0.31102(11) 0.14707(7) 1.000 0.0334(4) . . C16 C Uani 0.25051(19) 0.29110(12) 0.08427(7) 1.000 0.0391(4) . . C17 C Uani 0.1131(2) 0.24640(12) 0.05461(6) 1.000 0.0365(4) . . C18 C Uani -0.03054(17) 0.22214(10) 0.08748(6) 1.000 0.0288(4) . . C19 C Uani 0.12489(14) 0.40321(9) 0.40346(5) 1.000 0.0193(3) . . C20 C Uani 0.30423(15) 0.43425(9) 0.39091(5) 1.000 0.0200(3) . . C21 C Uani 0.39598(16) 0.49037(11) 0.43547(6) 1.000 0.0280(3) . . C22 C Uani 0.55958(18) 0.52254(12) 0.42446(7) 1.000 0.0376(4) . . C23 C Uani 0.63488(17) 0.49897(12) 0.36862(7) 1.000 0.0370(4) . . C24 C Uani 0.54614(17) 0.44185(11) 0.32423(7) 1.000 0.0304(4) . . C25 C Uani 0.38211(15) 0.40938(10) 0.33523(6) 1.000 0.0225(3) . . H3 H Uiso -0.2840(18) 0.2325(11) 0.4573(6) 1.000 0.020(3) . . H31 H Uiso -0.1100(14) 0.2946(10) 0.3110(5) 1.000 0.009(3) . . H41 H Uiso 0.3753(17) 0.1235(11) 0.2980(7) 1.000 0.024(3) . . H42 H Uiso 0.3877(17) 0.1724(11) 0.3664(6) 1.000 0.022(3) . . H51 H Uiso 0.3812(18) -0.0583(12) 0.3351(7) 1.000 0.030(4) . . H52 H Uiso 0.522(2) 0.0032(13) 0.3782(6) 1.000 0.037(4) . . H61 H Uiso 0.3322(19) 0.0265(12) 0.4570(6) 1.000 0.031(4) . . H62 H Uiso 0.282(2) -0.0915(14) 0.4343(7) 1.000 0.043(4) . . H71 H Uiso 0.0605(18) 0.0610(11) 0.4351(7) 1.000 0.026(3) . . H72 H Uiso 0.0512(18) -0.0338(12) 0.3843(6) 1.000 0.027(4) . . H81 H Uiso 0.1966(15) 0.2494(10) 0.4343(5) 1.000 0.012(3) . . H101 H Uiso -0.3293(17) 0.2080(10) 0.3560(6) 1.000 0.015(3) . . H102 H Uiso -0.2172(17) 0.1032(11) 0.3747(6) 1.000 0.019(3) . . H111 H Uiso -0.2980(19) 0.1143(11) 0.2486(6) 1.000 0.024(3) . . H112 H Uiso -0.1565(17) 0.0570(11) 0.2076(6) 1.000 0.017(3) . . H121 H Uiso -0.2913(17) 0.2074(11) 0.1569(6) 1.000 0.023(3) . . H122 H Uiso -0.2330(17) 0.2865(12) 0.2081(6) 1.000 0.021(3) . . H141 H Uiso 0.0960(17) 0.3067(12) 0.2231(7) 1.000 0.028(4) . . H151 H Uiso 0.342(2) 0.3414(13) 0.1683(7) 1.000 0.036(4) . . H161 H Uiso 0.350(2) 0.3067(14) 0.0622(7) 1.000 0.040(4) . . H171 H Uiso 0.1187(19) 0.2328(14) 0.0100(8) 1.000 0.043(4) . . H181 H Uiso -0.1267(19) 0.1928(13) 0.0681(7) 1.000 0.034(4) . . H191 H Uiso 0.0523(18) 0.4282(11) 0.3683(6) 1.000 0.024(3) . . H192 H Uiso 0.0884(18) 0.4407(11) 0.4407(6) 1.000 0.024(3) . . H211 H Uiso 0.3446(18) 0.5057(12) 0.4744(7) 1.000 0.031(4) . . H221 H Uiso 0.617(2) 0.5620(14) 0.4577(8) 1.000 0.045(5) . . H231 H Uiso 0.747(2) 0.5223(13) 0.3598(7) 1.000 0.040(4) . . H241 H Uiso 0.597(2) 0.4250(13) 0.2846(8) 1.000 0.040(4) . . H251 H Uiso 0.323(2) 0.3711(12) 0.3040(7) 1.000 0.030(4) . . 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 0.0267(4) 0.0212(4) 0.0249(4) -0.0057(3) 0.0036(3) 0.0007(4) O2 0.0203(4) 0.0294(4) 0.0167(4) -0.0031(3) 0.0007(3) -0.0011(3) N1 0.0177(5) 0.0207(5) 0.0172(4) -0.0025(4) -0.0005(4) -0.0018(4) N2 0.0133(4) 0.0170(4) 0.0167(4) -0.0006(3) -0.0001(3) 0.0007(4) N3 0.0133(4) 0.0290(5) 0.0172(5) -0.0028(4) 0.0042(4) -0.0006(4) C1 0.0159(5) 0.0165(5) 0.0195(5) -0.0009(4) 0.0020(4) 0.0001(4) C2 0.0183(5) 0.0174(5) 0.0194(5) 0.0013(4) 0.0050(4) -0.0039(4) C3 0.0162(5) 0.0188(5) 0.0165(5) -0.0009(4) -0.0007(4) -0.0001(4) C4 0.0155(5) 0.0241(6) 0.0291(7) -0.0039(5) 0.0018(5) 0.0007(5) C5 0.0187(6) 0.0217(6) 0.0553(9) -0.0076(6) -0.0084(6) 0.0033(5) C6 0.0311(7) 0.0227(6) 0.0426(8) 0.0072(6) -0.0143(6) -0.0026(5) C7 0.0253(6) 0.0180(6) 0.0212(6) 0.0007(5) -0.0002(5) -0.0005(5) C8 0.0127(5) 0.0179(5) 0.0172(5) -0.0002(4) -0.0005(4) 0.0005(4) C9 0.0175(5) 0.0160(5) 0.0184(5) 0.0010(4) 0.0010(4) 0.0020(4) C10 0.0138(5) 0.0278(6) 0.0211(6) -0.0034(5) -0.0006(4) -0.0029(4) C11 0.0185(6) 0.0270(6) 0.0198(6) -0.0044(5) -0.0014(5) -0.0041(5) C12 0.0210(6) 0.0284(6) 0.0220(6) -0.0039(5) -0.0055(5) 0.0024(5) C13 0.0265(6) 0.0178(5) 0.0234(6) 0.0008(4) -0.0024(5) 0.0037(5) C14 0.0296(6) 0.0238(6) 0.0252(6) 0.0035(5) -0.0027(5) -0.0021(5) C15 0.0312(7) 0.0297(7) 0.0392(7) 0.0069(6) 0.0003(6) -0.0052(6) C16 0.0382(8) 0.0354(7) 0.0437(8) 0.0065(6) 0.0162(7) 0.0007(6) C17 0.0499(9) 0.0333(7) 0.0264(7) -0.0019(6) 0.0105(6) 0.0046(6) C18 0.0358(7) 0.0245(6) 0.0261(6) -0.0021(5) -0.0015(6) 0.0028(6) C19 0.0183(5) 0.0176(5) 0.0219(6) -0.0018(5) 0.0014(5) 0.0006(4) C20 0.0206(6) 0.0161(5) 0.0232(6) 0.0052(4) -0.0013(4) -0.0007(4) C21 0.0299(6) 0.0275(6) 0.0266(6) 0.0032(5) -0.0039(5) -0.0068(5) C22 0.0325(7) 0.0387(8) 0.0417(8) 0.0074(6) -0.0133(6) -0.0154(6) C23 0.0182(6) 0.0365(7) 0.0562(9) 0.0171(7) -0.0007(6) -0.0060(6) C24 0.0254(7) 0.0270(6) 0.0388(7) 0.0110(6) 0.0079(6) 0.0037(5) C25 0.0220(6) 0.0201(5) 0.0254(6) 0.0040(5) 0.0007(5) 0.0024(5) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.2256(14) . . yes O2 C9 1.2362(13) . . yes N1 C2 1.3524(15) . . yes N1 C3 1.4537(14) . . yes N1 C11 1.4546(15) . . yes N2 C1 1.4723(14) . . yes N2 C3 1.4574(14) . . yes N2 C8 1.4579(14) . . yes N3 C9 1.3353(14) . . yes N3 C10 1.4561(14) . . yes N3 H3 0.878(14) . . no C1 C2 1.5259(15) . . no C1 C4 1.5435(15) . . no C1 C7 1.5708(16) . . no C3 C10 1.5333(16) . . no C4 C5 1.5206(18) . . no C5 C6 1.518(2) . . no C6 C7 1.5335(18) . . no C8 C9 1.5301(15) . . no C8 C19 1.5566(15) . . no C11 C12 1.5317(17) . . no C12 C13 1.5086(17) . . no C13 C18 1.3951(17) . . no C13 C14 1.3939(17) . . no C14 C15 1.3817(19) . . no C15 C16 1.387(2) . . no C16 C17 1.385(2) . . no C17 C18 1.385(2) . . no C19 C20 1.5082(16) . . no C20 C25 1.3935(17) . . no C20 C21 1.3929(17) . . no C21 C22 1.3866(19) . . no C22 C23 1.384(2) . . no C23 C24 1.384(2) . . no C24 C25 1.3908(18) . . no C3 H31 0.973(12) . . no C4 H41 0.967(15) . . no C4 H42 0.994(13) . . no C5 H51 0.998(15) . . no C5 H52 0.997(16) . . no C6 H61 0.995(14) . . no C6 H62 0.954(17) . . no C7 H71 0.972(15) . . no C7 H72 0.968(14) . . no C8 H81 0.973(12) . . no C10 H101 0.984(13) . . no C10 H102 1.000(13) . . no C11 H111 0.973(15) . . no C11 H112 0.993(13) . . no C12 H121 0.980(13) . . no C12 H122 0.954(14) . . no C14 H141 0.969(15) . . no C15 H151 0.986(16) . . no C16 H161 0.948(16) . . no C17 H171 0.984(17) . . no C18 H181 0.947(15) . . no C19 H191 1.006(14) . . no C19 H192 0.973(13) . . no C21 H211 0.958(15) . . no C22 H221 0.981(17) . . no C23 H231 0.960(16) . . no C24 H241 0.974(17) . . no C25 H251 0.949(15) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C3 112.11(9) . . . yes C2 N1 C11 123.91(9) . . . yes C3 N1 C11 123.24(9) . . . yes C1 N2 C3 107.76(8) . . . yes C1 N2 C8 118.70(8) . . . yes C3 N2 C8 114.69(8) . . . yes C9 N3 C10 125.11(9) . . . yes C9 N3 H3 118.1(9) . . . no C10 N3 H3 116.0(9) . . . no N2 C1 C2 100.59(8) . . . yes C2 C1 C4 112.12(9) . . . no N2 C1 C4 111.70(9) . . . yes N2 C1 C7 117.75(9) . . . yes C4 C1 C7 104.79(9) . . . no C2 C1 C7 110.09(9) . . . no O1 C2 C1 126.21(10) . . . yes O1 C2 N1 126.09(10) . . . yes N1 C2 C1 107.69(9) . . . yes N1 C3 C10 109.86(9) . . . yes N1 C3 N2 101.19(8) . . . yes N2 C3 C10 113.91(9) . . . yes C1 C4 C5 104.84(10) . . . no C4 C5 C6 103.48(10) . . . no C5 C6 C7 104.67(11) . . . no C1 C7 C6 105.94(10) . . . no N2 C8 C9 116.22(9) . . . yes N2 C8 C19 110.32(9) . . . yes C9 C8 C19 106.92(9) . . . no O2 C9 N3 122.79(10) . . . yes N3 C9 C8 118.00(9) . . . yes O2 C9 C8 119.02(9) . . . yes N3 C10 C3 111.65(9) . . . yes N1 C11 C12 112.97(10) . . . yes C11 C12 C13 113.84(10) . . . no C12 C13 C18 120.95(11) . . . no C12 C13 C14 120.78(10) . . . no C14 C13 C18 118.26(11) . . . no C13 C14 C15 120.87(12) . . . no C14 C15 C16 120.29(13) . . . no C15 C16 C17 119.52(14) . . . no C16 C17 C18 120.15(13) . . . no C13 C18 C17 120.88(12) . . . no C8 C19 C20 113.47(9) . . . no C19 C20 C21 119.87(10) . . . no C21 C20 C25 118.27(11) . . . no C19 C20 C25 121.86(10) . . . no C20 C21 C22 121.03(12) . . . no C21 C22 C23 120.23(13) . . . no C22 C23 C24 119.41(13) . . . no C23 C24 C25 120.43(13) . . . no C20 C25 C24 120.62(12) . . . no N1 C3 H31 111.8(7) . . . no N2 C3 H31 110.4(7) . . . no C10 C3 H31 109.6(7) . . . no C1 C4 H41 110.1(8) . . . no C1 C4 H42 107.2(8) . . . no C5 C4 H41 114.3(8) . . . no C5 C4 H42 110.5(8) . . . no H41 C4 H42 109.6(11) . . . no C4 C5 H51 109.7(9) . . . no C4 C5 H52 111.1(9) . . . no C6 C5 H51 109.6(9) . . . no C6 C5 H52 111.6(8) . . . no H51 C5 H52 111.0(12) . . . no C5 C6 H61 109.6(8) . . . no C5 C6 H62 113.5(9) . . . no C7 C6 H61 111.1(9) . . . no C7 C6 H62 110.8(10) . . . no H61 C6 H62 107.2(12) . . . no C1 C7 H71 111.5(8) . . . no C1 C7 H72 108.2(8) . . . no C6 C7 H71 110.0(9) . . . no C6 C7 H72 110.2(9) . . . no H71 C7 H72 110.8(12) . . . no N2 C8 H81 108.8(7) . . . no C9 C8 H81 106.9(7) . . . no C19 C8 H81 107.3(7) . . . no N3 C10 H101 108.9(8) . . . no N3 C10 H102 110.5(8) . . . no C3 C10 H101 109.1(8) . . . no C3 C10 H102 108.1(8) . . . no H101 C10 H102 108.5(11) . . . no N1 C11 H111 109.6(8) . . . no N1 C11 H112 107.0(8) . . . no C12 C11 H111 108.0(8) . . . no C12 C11 H112 110.4(8) . . . no H111 C11 H112 108.9(11) . . . no C11 C12 H121 107.6(8) . . . no C11 C12 H122 109.0(8) . . . no C13 C12 H121 109.7(8) . . . no C13 C12 H122 110.6(8) . . . no H121 C12 H122 105.8(11) . . . no C13 C14 H141 120.9(8) . . . no C15 C14 H141 118.3(8) . . . no C14 C15 H151 120.3(9) . . . no C16 C15 H151 119.5(9) . . . no C15 C16 H161 119.8(10) . . . no C17 C16 H161 120.6(10) . . . no C16 C17 H171 119.2(9) . . . no C18 C17 H171 120.7(9) . . . no C13 C18 H181 117.4(9) . . . no C17 C18 H181 121.7(9) . . . no C8 C19 H191 108.6(8) . . . no C8 C19 H192 108.0(8) . . . no C20 C19 H191 109.7(8) . . . no C20 C19 H192 108.6(8) . . . no H191 C19 H192 108.5(11) . . . no C20 C21 H211 118.8(9) . . . no C22 C21 H211 120.1(9) . . . no C21 C22 H221 116.9(10) . . . no C23 C22 H221 122.8(10) . . . no C22 C23 H231 121.4(9) . . . no C24 C23 H231 119.2(9) . . . no C23 C24 H241 120.5(10) . . . no C25 C24 H241 119.1(10) . . . no C20 C25 H251 120.3(10) . . . no C24 C25 H251 119.1(10) . . . no _iucr_refine_instructions_details ; ; # End of Crystallographic Information File