# 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_imine_1 _database_code_depnum_ccdc_archive 'CCDC 925536' #TrackingRef 'imine_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H27 N' _chemical_formula_sum 'C25 H27 N' _chemical_formula_weight 341.48 _chemical_absolute_configuration . 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' _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 8.1508(5) _cell_length_b 17.5996(11) _cell_length_c 28.8453(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4137.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8209 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 22.89 _exptl_crystal_description prisms _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.096 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9605 _exptl_absorpt_correction_T_max 0.9827 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48283 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 28.30 _reflns_number_total 9725 _reflns_number_gt 5544 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Brukar SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.0514P)^2^+0.5737P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 4(4) _refine_ls_number_reflns 9725 _refine_ls_number_parameters 475 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1132 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 C1A C 0.5659(3) 0.27519(11) 0.22633(7) 0.0464(5) Uani 1 1 d . . . C2A C 0.6668(2) 0.26335(12) 0.26907(7) 0.0462(5) Uani 1 1 d . . . C3A C 0.6919(3) 0.19176(14) 0.28743(8) 0.0595(6) Uani 1 1 d . . . H3A H 0.6502 0.1494 0.2722 0.071 Uiso 1 1 calc R . . C4A C 0.7783(4) 0.18249(18) 0.32818(10) 0.0787(8) Uani 1 1 d . . . H4A H 0.7942 0.1339 0.3401 0.094 Uiso 1 1 calc R . . C5A C 0.8405(3) 0.2436(2) 0.35111(9) 0.0798(8) Uani 1 1 d . . . H5A H 0.8977 0.2368 0.3787 0.096 Uiso 1 1 calc R . . C6A C 0.8188(3) 0.31539(18) 0.33347(9) 0.0725(7) Uani 1 1 d . . . H6A H 0.8612 0.3573 0.3490 0.087 Uiso 1 1 calc R . . C7A C 0.7337(3) 0.32504(14) 0.29249(8) 0.0574(6) Uani 1 1 d . . . H7A H 0.7210 0.3736 0.2804 0.069 Uiso 1 1 calc R . . C8A C 0.6532(3) 0.27038(14) 0.17945(8) 0.0609(6) Uani 1 1 d . . . C9A C 0.7107(5) 0.18878(16) 0.17212(10) 0.1036(12) Uani 1 1 d . . . H9A1 H 0.7577 0.1839 0.1417 0.155 Uiso 1 1 calc R . . H9A2 H 0.6190 0.1549 0.1750 0.155 Uiso 1 1 calc R . . H9A3 H 0.7917 0.1762 0.1950 0.155 Uiso 1 1 calc R . . C10A C 0.8041(4) 0.32184(18) 0.17934(10) 0.0921(10) Uani 1 1 d . . . H10A H 0.8775 0.3065 0.2036 0.138 Uiso 1 1 calc R . . H10B H 0.7707 0.3735 0.1844 0.138 Uiso 1 1 calc R . . H10C H 0.8588 0.3179 0.1500 0.138 Uiso 1 1 calc R . . C11A C 0.5382(5) 0.2934(2) 0.14048(9) 0.1237(14) Uani 1 1 d . . . H11A H 0.5013 0.3445 0.1454 0.186 Uiso 1 1 calc R . . H11B H 0.4454 0.2598 0.1400 0.186 Uiso 1 1 calc R . . H11C H 0.5951 0.2903 0.1114 0.186 Uiso 1 1 calc R . . N1A N 0.4131(2) 0.28888(10) 0.22716(6) 0.0523(4) Uani 1 1 d . . . C12A C 0.3222(3) 0.29059(13) 0.27086(8) 0.0552(6) Uani 1 1 d . . . H12A H 0.3979 0.2808 0.2966 0.066 Uiso 1 1 calc R . . C13A C 0.2425(3) 0.36749(13) 0.27757(8) 0.0549(6) Uani 1 1 d . . . C14A C 0.1568(3) 0.40289(15) 0.24219(9) 0.0698(7) Uani 1 1 d . . . H14A H 0.1524 0.3807 0.2130 0.084 Uiso 1 1 calc R . . C15A C 0.0778(4) 0.47122(17) 0.25028(12) 0.0845(8) Uani 1 1 d . . . H15A H 0.0183 0.4940 0.2265 0.101 Uiso 1 1 calc R . . C16A C 0.0861(4) 0.50536(17) 0.29223(13) 0.0894(9) Uani 1 1 d . . . H16A H 0.0330 0.5514 0.2973 0.107 Uiso 1 1 calc R . . C17A C 0.1730(4) 0.47163(18) 0.32702(12) 0.0957(9) Uani 1 1 d . . . H17A H 0.1803 0.4951 0.3558 0.115 Uiso 1 1 calc R . . C18A C 0.2498(3) 0.40314(16) 0.31974(10) 0.0751(8) Uani 1 1 d . . . H18A H 0.3077 0.3806 0.3439 0.090 Uiso 1 1 calc R . . C19A C 0.1932(3) 0.22633(15) 0.26874(11) 0.0774(8) Uani 1 1 d . . . H19A H 0.1139 0.2337 0.2934 0.093 Uiso 1 1 calc R . . H19B H 0.1351 0.2293 0.2395 0.093 Uiso 1 1 calc R . . C20A C 0.2684(3) 0.14877(15) 0.27344(11) 0.0679(7) Uani 1 1 d . . . C21A C 0.3228(3) 0.10783(16) 0.23550(10) 0.0762(8) Uani 1 1 d . . . H21A H 0.3034 0.1264 0.2058 0.091 Uiso 1 1 calc R . . C22A C 0.4049(4) 0.04027(17) 0.24089(13) 0.0871(9) Uani 1 1 d . . . H22A H 0.4425 0.0145 0.2148 0.105 Uiso 1 1 calc R . . C23A C 0.4319(4) 0.01059(16) 0.28364(14) 0.0905(9) Uani 1 1 d . . . H23A H 0.4871 -0.0353 0.2869 0.109 Uiso 1 1 calc R . . C24A C 0.3766(4) 0.04937(17) 0.32208(12) 0.0927(10) Uani 1 1 d . . . H24A H 0.3934 0.0295 0.3516 0.111 Uiso 1 1 calc R . . C25A C 0.2962(4) 0.11786(16) 0.31670(11) 0.0845(9) Uani 1 1 d . . . H25A H 0.2598 0.1438 0.3429 0.101 Uiso 1 1 calc R . . C1B C 0.1680(3) 0.47984(11) 0.02105(7) 0.0437(5) Uani 1 1 d . . . C2B C 0.0723(2) 0.49269(12) -0.02260(7) 0.0448(5) Uani 1 1 d . . . C3B C 0.0425(3) 0.56504(14) -0.03968(8) 0.0558(6) Uani 1 1 d . . . H3B H 0.0816 0.6070 -0.0235 0.067 Uiso 1 1 calc R . . C4B C -0.0444(3) 0.57572(17) -0.08025(9) 0.0699(7) Uani 1 1 d . . . H4B H -0.0635 0.6246 -0.0912 0.084 Uiso 1 1 calc R . . C5B C -0.1023(3) 0.5143(2) -0.10432(9) 0.0784(8) Uani 1 1 d . . . H5B H -0.1613 0.5216 -0.1316 0.094 Uiso 1 1 calc R . . C6B C -0.0735(3) 0.44215(18) -0.08839(9) 0.0767(8) Uani 1 1 d . . . H6B H -0.1120 0.4005 -0.1050 0.092 Uiso 1 1 calc R . . C7B C 0.0126(3) 0.43113(14) -0.04771(8) 0.0588(6) Uani 1 1 d . . . H7B H 0.0309 0.3820 -0.0370 0.071 Uiso 1 1 calc R . . C8B C 0.0739(3) 0.48466(13) 0.06700(7) 0.0556(6) Uani 1 1 d . . . C9B C 0.0074(4) 0.56554(15) 0.07314(9) 0.0778(8) Uani 1 1 d . . . H9B1 H 0.0960 0.6013 0.0705 0.117 Uiso 1 1 calc R . . H9B2 H -0.0424 0.5702 0.1032 0.117 Uiso 1 1 calc R . . H9B3 H -0.0729 0.5758 0.0496 0.117 Uiso 1 1 calc R . . C10B C -0.0714(4) 0.43002(16) 0.06584(10) 0.0785(8) Uani 1 1 d . . . H10D H -0.1403 0.4420 0.0399 0.118 Uiso 1 1 calc R . . H10E H -0.1333 0.4349 0.0940 0.118 Uiso 1 1 calc R . . H10F H -0.0319 0.3789 0.0629 0.118 Uiso 1 1 calc R . . C11B C 0.1843(4) 0.46514(19) 0.10761(8) 0.0948(10) Uani 1 1 d . . . H11D H 0.2257 0.4144 0.1039 0.142 Uiso 1 1 calc R . . H11E H 0.1228 0.4684 0.1359 0.142 Uiso 1 1 calc R . . H11F H 0.2743 0.5003 0.1087 0.142 Uiso 1 1 calc R . . N1B N 0.3206(2) 0.46446(10) 0.02197(6) 0.0517(4) Uani 1 1 d . . . C12B C 0.4174(3) 0.46464(12) -0.02062(8) 0.0524(5) Uani 1 1 d . . . H12B H 0.3470 0.4764 -0.0472 0.063 Uiso 1 1 calc R . . C13B C 0.5005(3) 0.38850(12) -0.02772(8) 0.0525(6) Uani 1 1 d . . . C14B C 0.5729(3) 0.34964(13) 0.00857(9) 0.0640(6) Uani 1 1 d . . . H14B H 0.5618 0.3681 0.0386 0.077 Uiso 1 1 calc R . . C15B C 0.6612(3) 0.28407(14) 0.00103(12) 0.0769(8) Uani 1 1 d . . . H15B H 0.7109 0.2593 0.0258 0.092 Uiso 1 1 calc R . . C16B C 0.6759(4) 0.25543(15) -0.04279(12) 0.0812(8) Uani 1 1 d . . . H16B H 0.7354 0.2111 -0.0479 0.097 Uiso 1 1 calc R . . C17B C 0.6031(4) 0.29187(17) -0.07909(11) 0.0838(8) Uani 1 1 d . . . H17B H 0.6117 0.2721 -0.1089 0.101 Uiso 1 1 calc R . . C18B C 0.5161(3) 0.35868(15) -0.07151(9) 0.0703(7) Uani 1 1 d . . . H18B H 0.4678 0.3835 -0.0965 0.084 Uiso 1 1 calc R . . C19B C 0.5503(3) 0.52670(13) -0.01502(10) 0.0719(7) Uani 1 1 d . . . H19C H 0.6154 0.5155 0.0123 0.086 Uiso 1 1 calc R . . H19D H 0.6228 0.5252 -0.0417 0.086 Uiso 1 1 calc R . . C20B C 0.4805(3) 0.60531(14) -0.01052(10) 0.0635(7) Uani 1 1 d . . . C21B C 0.4571(4) 0.63785(16) 0.03216(11) 0.0879(9) Uani 1 1 d . . . H21B H 0.4884 0.6115 0.0587 0.106 Uiso 1 1 calc R . . C22B C 0.3877(5) 0.7091(2) 0.03646(15) 0.1136(13) Uani 1 1 d . . . H22B H 0.3739 0.7305 0.0657 0.136 Uiso 1 1 calc R . . C23B C 0.3400(5) 0.7478(2) -0.0015(2) 0.1158(14) Uani 1 1 d . . . H23B H 0.2914 0.7954 0.0016 0.139 Uiso 1 1 calc R . . C24B C 0.3627(4) 0.71769(19) -0.04397(15) 0.1035(11) Uani 1 1 d . . . H24B H 0.3312 0.7448 -0.0702 0.124 Uiso 1 1 calc R . . C25B C 0.4328(3) 0.64624(16) -0.04870(11) 0.0815(8) Uani 1 1 d . . . H25B H 0.4477 0.6258 -0.0781 0.098 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 C1A 0.0493(12) 0.0420(12) 0.0478(12) 0.0031(9) 0.0016(10) 0.0012(10) C2A 0.0375(11) 0.0503(13) 0.0509(12) 0.0048(10) 0.0054(10) 0.0011(10) C3A 0.0544(14) 0.0600(15) 0.0642(15) 0.0146(12) -0.0081(12) -0.0043(12) C4A 0.0706(18) 0.085(2) 0.0799(19) 0.0332(16) -0.0106(15) -0.0040(16) C5A 0.0591(16) 0.115(3) 0.0651(17) 0.0129(17) -0.0097(14) 0.0015(18) C6A 0.0577(15) 0.092(2) 0.0675(16) -0.0211(15) -0.0087(14) 0.0044(15) C7A 0.0518(13) 0.0533(15) 0.0670(15) -0.0046(12) 0.0004(12) 0.0035(11) C8A 0.0675(16) 0.0647(16) 0.0506(13) 0.0044(11) 0.0106(12) 0.0107(13) C9A 0.147(3) 0.077(2) 0.088(2) -0.0077(16) 0.050(2) 0.022(2) C10A 0.095(2) 0.099(2) 0.083(2) 0.0195(17) 0.0366(18) -0.0048(19) C11A 0.125(3) 0.200(4) 0.0460(15) 0.014(2) -0.0077(18) 0.051(3) N1A 0.0453(10) 0.0530(11) 0.0586(11) 0.0009(9) -0.0040(9) 0.0023(9) C12A 0.0412(11) 0.0582(15) 0.0663(14) 0.0026(11) 0.0061(12) 0.0020(11) C13A 0.0406(11) 0.0529(15) 0.0712(15) -0.0003(12) 0.0066(12) -0.0025(11) C14A 0.0632(16) 0.0684(18) 0.0779(17) -0.0003(14) -0.0018(14) 0.0090(14) C15A 0.0746(19) 0.0693(19) 0.109(2) 0.0112(17) -0.0084(18) 0.0142(17) C16A 0.081(2) 0.0614(19) 0.126(3) -0.0107(19) 0.006(2) 0.0056(16) C17A 0.105(2) 0.082(2) 0.100(2) -0.0303(18) -0.001(2) 0.009(2) C18A 0.0750(18) 0.0696(19) 0.0806(18) -0.0116(14) -0.0081(15) 0.0072(15) C19A 0.0462(13) 0.0624(17) 0.124(2) 0.0054(15) 0.0165(15) -0.0047(13) C20A 0.0501(13) 0.0550(16) 0.099(2) 0.0058(15) 0.0143(14) -0.0116(12) C21A 0.0699(17) 0.0673(19) 0.091(2) -0.0108(15) -0.0015(16) -0.0124(16) C22A 0.088(2) 0.0575(19) 0.116(3) -0.0193(17) 0.0144(19) -0.0122(17) C23A 0.084(2) 0.0515(17) 0.136(3) 0.0034(19) 0.013(2) -0.0030(15) C24A 0.103(2) 0.071(2) 0.104(2) 0.0202(18) 0.025(2) -0.0073(18) C25A 0.090(2) 0.0609(19) 0.103(2) 0.0010(16) 0.0343(18) -0.0023(17) C1B 0.0425(12) 0.0353(11) 0.0532(12) 0.0004(9) -0.0002(10) -0.0031(9) C2B 0.0350(10) 0.0494(13) 0.0501(12) -0.0007(10) 0.0025(9) -0.0007(10) C3B 0.0520(14) 0.0568(14) 0.0585(14) 0.0056(11) 0.0041(11) 0.0007(11) C4B 0.0694(17) 0.082(2) 0.0579(15) 0.0173(14) 0.0040(14) 0.0125(15) C5B 0.0706(17) 0.114(3) 0.0507(15) 0.0006(16) -0.0072(13) 0.0187(18) C6B 0.0667(17) 0.093(2) 0.0707(17) -0.0267(16) -0.0079(14) -0.0035(16) C7B 0.0569(14) 0.0540(14) 0.0655(15) -0.0107(12) -0.0024(13) 0.0025(12) C8B 0.0575(14) 0.0589(15) 0.0503(13) 0.0005(11) 0.0026(11) 0.0045(12) C9B 0.095(2) 0.0696(18) 0.0689(16) -0.0082(13) 0.0218(16) 0.0124(16) C10B 0.0741(18) 0.0780(19) 0.0834(18) 0.0123(15) 0.0239(15) -0.0047(16) C11B 0.102(2) 0.131(3) 0.0518(15) 0.0056(16) -0.0053(16) 0.027(2) N1B 0.0446(10) 0.0495(11) 0.0611(11) -0.0012(9) -0.0010(10) 0.0017(9) C12B 0.0403(11) 0.0484(13) 0.0685(14) 0.0027(11) 0.0047(11) 0.0010(11) C13B 0.0370(11) 0.0456(13) 0.0750(16) -0.0022(12) -0.0003(12) -0.0038(10) C14B 0.0609(15) 0.0533(15) 0.0777(17) 0.0002(12) -0.0006(14) 0.0037(13) C15B 0.0677(17) 0.0547(16) 0.108(2) 0.0056(16) -0.0070(16) 0.0098(14) C16B 0.0628(17) 0.0525(17) 0.128(3) -0.0155(18) -0.0066(19) 0.0122(14) C17B 0.0791(19) 0.0717(19) 0.101(2) -0.0322(17) -0.0101(18) 0.0034(17) C18B 0.0638(15) 0.0647(18) 0.0825(18) -0.0142(14) -0.0123(14) 0.0067(14) C19B 0.0485(14) 0.0525(15) 0.115(2) -0.0062(14) 0.0111(15) -0.0031(12) C20B 0.0485(13) 0.0487(14) 0.0934(19) 0.0008(14) 0.0154(13) -0.0074(11) C21B 0.106(2) 0.0607(19) 0.098(2) -0.0045(16) 0.0169(19) -0.0185(18) C22B 0.132(3) 0.068(2) 0.140(3) -0.032(2) 0.061(3) -0.021(2) C23B 0.091(2) 0.055(2) 0.202(4) 0.002(3) 0.055(3) -0.0007(18) C24B 0.084(2) 0.069(2) 0.158(3) 0.037(2) 0.017(2) -0.0031(18) C25B 0.0763(18) 0.0645(19) 0.104(2) 0.0074(16) 0.0218(17) -0.0062(16) _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 C1A N1A 1.269(3) . ? C1A C2A 1.497(3) . ? C1A C8A 1.530(3) . ? C2A C3A 1.382(3) . ? C2A C7A 1.390(3) . ? C3A C4A 1.380(3) . ? C3A H3A 0.9300 . ? C4A C5A 1.361(4) . ? C4A H4A 0.9300 . ? C5A C6A 1.373(4) . ? C5A H5A 0.9300 . ? C6A C7A 1.381(3) . ? C6A H6A 0.9300 . ? C7A H7A 0.9300 . ? C8A C11A 1.519(4) . ? C8A C9A 1.525(4) . ? C8A C10A 1.528(4) . ? C9A H9A1 0.9600 . ? C9A H9A2 0.9600 . ? C9A H9A3 0.9600 . ? C10A H10A 0.9600 . ? C10A H10B 0.9600 . ? C10A H10C 0.9600 . ? C11A H11A 0.9600 . ? C11A H11B 0.9600 . ? C11A H11C 0.9600 . ? N1A C12A 1.462(3) . ? C12A C13A 1.514(3) . ? C12A C19A 1.546(3) . ? C12A H12A 0.9800 . ? C13A C18A 1.370(3) . ? C13A C14A 1.385(3) . ? C14A C15A 1.384(4) . ? C14A H14A 0.9300 . ? C15A C16A 1.353(4) . ? C15A H15A 0.9300 . ? C16A C17A 1.364(4) . ? C16A H16A 0.9300 . ? C17A C18A 1.374(4) . ? C17A H17A 0.9300 . ? C18A H18A 0.9300 . ? C19A C20A 1.503(4) . ? C19A H19A 0.9700 . ? C19A H19B 0.9700 . ? C20A C25A 1.380(4) . ? C20A C21A 1.383(4) . ? C21A C22A 1.373(4) . ? C21A H21A 0.9300 . ? C22A C23A 1.357(4) . ? C22A H22A 0.9300 . ? C23A C24A 1.378(4) . ? C23A H23A 0.9300 . ? C24A C25A 1.381(4) . ? C24A H24A 0.9300 . ? C25A H25A 0.9300 . ? C1B N1B 1.273(3) . ? C1B C2B 1.499(3) . ? C1B C8B 1.534(3) . ? C2B C3B 1.387(3) . ? C2B C7B 1.391(3) . ? C3B C4B 1.380(3) . ? C3B H3B 0.9300 . ? C4B C5B 1.368(4) . ? C4B H4B 0.9300 . ? C5B C6B 1.371(4) . ? C5B H5B 0.9300 . ? C6B C7B 1.381(3) . ? C6B H6B 0.9300 . ? C7B H7B 0.9300 . ? C8B C11B 1.517(3) . ? C8B C10B 1.525(3) . ? C8B C9B 1.533(3) . ? C9B H9B1 0.9600 . ? C9B H9B2 0.9600 . ? C9B H9B3 0.9600 . ? C10B H10D 0.9600 . ? C10B H10E 0.9600 . ? C10B H10F 0.9600 . ? C11B H11D 0.9600 . ? C11B H11E 0.9600 . ? C11B H11F 0.9600 . ? N1B C12B 1.460(3) . ? C12B C13B 1.515(3) . ? C12B C19B 1.547(3) . ? C12B H12B 0.9800 . ? C13B C18B 1.374(3) . ? C13B C14B 1.383(3) . ? C14B C15B 1.377(3) . ? C14B H14B 0.9300 . ? C15B C16B 1.366(4) . ? C15B H15B 0.9300 . ? C16B C17B 1.363(4) . ? C16B H16B 0.9300 . ? C17B C18B 1.390(4) . ? C17B H17B 0.9300 . ? C18B H18B 0.9300 . ? C19B C20B 1.502(3) . ? C19B H19C 0.9700 . ? C19B H19D 0.9700 . ? C20B C21B 1.371(4) . ? C20B C25B 1.372(4) . ? C21B C22B 1.382(4) . ? C21B H21B 0.9300 . ? C22B C23B 1.347(6) . ? C22B H22B 0.9300 . ? C23B C24B 1.348(5) . ? C23B H23B 0.9300 . ? C24B C25B 1.388(4) . ? C24B H24B 0.9300 . ? C25B H25B 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 N1A C1A C2A 123.4(2) . . ? N1A C1A C8A 118.9(2) . . ? C2A C1A C8A 117.68(18) . . ? C3A C2A C7A 117.9(2) . . ? C3A C2A C1A 121.6(2) . . ? C7A C2A C1A 120.5(2) . . ? C4A C3A C2A 120.7(2) . . ? C4A C3A H3A 119.7 . . ? C2A C3A H3A 119.7 . . ? C5A C4A C3A 120.7(3) . . ? C5A C4A H4A 119.7 . . ? C3A C4A H4A 119.7 . . ? C4A C5A C6A 119.9(3) . . ? C4A C5A H5A 120.0 . . ? C6A C5A H5A 120.0 . . ? C5A C6A C7A 119.7(3) . . ? C5A C6A H6A 120.2 . . ? C7A C6A H6A 120.2 . . ? C6A C7A C2A 121.1(2) . . ? C6A C7A H7A 119.4 . . ? C2A C7A H7A 119.4 . . ? C11A C8A C9A 109.8(3) . . ? C11A C8A C10A 109.7(2) . . ? C9A C8A C10A 108.1(2) . . ? C11A C8A C1A 110.6(2) . . ? C9A C8A C1A 108.52(19) . . ? C10A C8A C1A 110.1(2) . . ? C8A C9A H9A1 109.5 . . ? C8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? C8A C10A H10A 109.5 . . ? C8A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C8A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C8A C11A H11A 109.5 . . ? C8A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C8A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C1A N1A C12A 121.16(19) . . ? N1A C12A C13A 110.26(18) . . ? N1A C12A C19A 107.2(2) . . ? C13A C12A C19A 111.54(18) . . ? N1A C12A H12A 109.3 . . ? C13A C12A H12A 109.3 . . ? C19A C12A H12A 109.3 . . ? C18A C13A C14A 118.0(2) . . ? C18A C13A C12A 120.3(2) . . ? C14A C13A C12A 121.6(2) . . ? C15A C14A C13A 120.1(3) . . ? C15A C14A H14A 120.0 . . ? C13A C14A H14A 120.0 . . ? C16A C15A C14A 120.9(3) . . ? C16A C15A H15A 119.5 . . ? C14A C15A H15A 119.5 . . ? C15A C16A C17A 119.4(3) . . ? C15A C16A H16A 120.3 . . ? C17A C16A H16A 120.3 . . ? C16A C17A C18A 120.4(3) . . ? C16A C17A H17A 119.8 . . ? C18A C17A H17A 119.8 . . ? C13A C18A C17A 121.2(3) . . ? C13A C18A H18A 119.4 . . ? C17A C18A H18A 119.4 . . ? C20A C19A C12A 112.5(2) . . ? C20A C19A H19A 109.1 . . ? C12A C19A H19A 109.1 . . ? C20A C19A H19B 109.1 . . ? C12A C19A H19B 109.1 . . ? H19A C19A H19B 107.8 . . ? C25A C20A C21A 117.2(3) . . ? C25A C20A C19A 120.4(3) . . ? C21A C20A C19A 122.2(3) . . ? C22A C21A C20A 121.2(3) . . ? C22A C21A H21A 119.4 . . ? C20A C21A H21A 119.4 . . ? C23A C22A C21A 121.0(3) . . ? C23A C22A H22A 119.5 . . ? C21A C22A H22A 119.5 . . ? C22A C23A C24A 119.2(3) . . ? C22A C23A H23A 120.4 . . ? C24A C23A H23A 120.4 . . ? C23A C24A C25A 119.8(3) . . ? C23A C24A H24A 120.1 . . ? C25A C24A H24A 120.1 . . ? C20A C25A C24A 121.6(3) . . ? C20A C25A H25A 119.2 . . ? C24A C25A H25A 119.2 . . ? N1B C1B C2B 123.94(19) . . ? N1B C1B C8B 118.86(19) . . ? C2B C1B C8B 117.20(17) . . ? C3B C2B C7B 118.0(2) . . ? C3B C2B C1B 121.90(19) . . ? C7B C2B C1B 120.14(19) . . ? C4B C3B C2B 121.1(2) . . ? C4B C3B H3B 119.5 . . ? C2B C3B H3B 119.5 . . ? C5B C4B C3B 120.0(3) . . ? C5B C4B H4B 120.0 . . ? C3B C4B H4B 120.0 . . ? C4B C5B C6B 120.2(2) . . ? C4B C5B H5B 119.9 . . ? C6B C5B H5B 119.9 . . ? C5B C6B C7B 120.1(3) . . ? C5B C6B H6B 119.9 . . ? C7B C6B H6B 119.9 . . ? C6B C7B C2B 120.7(2) . . ? C6B C7B H7B 119.6 . . ? C2B C7B H7B 119.6 . . ? C11B C8B C10B 109.6(2) . . ? C11B C8B C9B 109.3(2) . . ? C10B C8B C9B 108.3(2) . . ? C11B C8B C1B 111.0(2) . . ? C10B C8B C1B 109.54(19) . . ? C9B C8B C1B 109.14(18) . . ? C8B C9B H9B1 109.5 . . ? C8B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C8B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? C8B C10B H10D 109.5 . . ? C8B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C8B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? C8B C11B H11D 109.5 . . ? C8B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? C8B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? C1B N1B C12B 120.66(18) . . ? N1B C12B C13B 110.68(18) . . ? N1B C12B C19B 106.98(19) . . ? C13B C12B C19B 109.02(17) . . ? N1B C12B H12B 110.0 . . ? C13B C12B H12B 110.0 . . ? C19B C12B H12B 110.0 . . ? C18B C13B C14B 117.9(2) . . ? C18B C13B C12B 120.2(2) . . ? C14B C13B C12B 121.7(2) . . ? C15B C14B C13B 121.2(3) . . ? C15B C14B H14B 119.4 . . ? C13B C14B H14B 119.4 . . ? C16B C15B C14B 120.0(3) . . ? C16B C15B H15B 120.0 . . ? C14B C15B H15B 120.0 . . ? C17B C16B C15B 119.9(3) . . ? C17B C16B H16B 120.0 . . ? C15B C16B H16B 120.0 . . ? C16B C17B C18B 119.9(3) . . ? C16B C17B H17B 120.0 . . ? C18B C17B H17B 120.0 . . ? C13B C18B C17B 121.0(3) . . ? C13B C18B H18B 119.5 . . ? C17B C18B H18B 119.5 . . ? C20B C19B C12B 113.21(19) . . ? C20B C19B H19C 108.9 . . ? C12B C19B H19C 108.9 . . ? C20B C19B H19D 108.9 . . ? C12B C19B H19D 108.9 . . ? H19C C19B H19D 107.8 . . ? C21B C20B C25B 117.5(3) . . ? C21B C20B C19B 121.0(3) . . ? C25B C20B C19B 121.4(3) . . ? C20B C21B C22B 121.1(3) . . ? C20B C21B H21B 119.4 . . ? C22B C21B H21B 119.4 . . ? C23B C22B C21B 120.3(4) . . ? C23B C22B H22B 119.9 . . ? C21B C22B H22B 119.9 . . ? C22B C23B C24B 120.0(3) . . ? C22B C23B H23B 120.0 . . ? C24B C23B H23B 120.0 . . ? C23B C24B C25B 120.1(4) . . ? C23B C24B H24B 119.9 . . ? C25B C24B H24B 119.9 . . ? C20B C25B C24B 120.9(3) . . ? C20B C25B H25B 119.6 . . ? C24B C25B H25B 119.6 . . ? 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 N1A C1A C2A C3A 91.8(3) . . . . ? C8A C1A C2A C3A -88.2(3) . . . . ? N1A C1A C2A C7A -85.9(3) . . . . ? C8A C1A C2A C7A 94.1(2) . . . . ? C7A C2A C3A C4A 1.1(3) . . . . ? C1A C2A C3A C4A -176.6(2) . . . . ? C2A C3A C4A C5A 0.0(4) . . . . ? C3A C4A C5A C6A -0.6(4) . . . . ? C4A C5A C6A C7A 0.0(4) . . . . ? C5A C6A C7A C2A 1.2(4) . . . . ? C3A C2A C7A C6A -1.7(3) . . . . ? C1A C2A C7A C6A 176.1(2) . . . . ? N1A C1A C8A C11A 7.1(3) . . . . ? C2A C1A C8A C11A -172.9(2) . . . . ? N1A C1A C8A C9A -113.4(3) . . . . ? C2A C1A C8A C9A 66.6(3) . . . . ? N1A C1A C8A C10A 128.5(2) . . . . ? C2A C1A C8A C10A -51.5(3) . . . . ? C2A C1A N1A C12A -2.9(3) . . . . ? C8A C1A N1A C12A 177.13(19) . . . . ? C1A N1A C12A C13A 121.1(2) . . . . ? C1A N1A C12A C19A -117.3(2) . . . . ? N1A C12A C13A C18A -135.6(2) . . . . ? C19A C12A C13A C18A 105.5(3) . . . . ? N1A C12A C13A C14A 46.3(3) . . . . ? C19A C12A C13A C14A -72.7(3) . . . . ? C18A C13A C14A C15A -1.8(4) . . . . ? C12A C13A C14A C15A 176.4(2) . . . . ? C13A C14A C15A C16A 1.6(4) . . . . ? C14A C15A C16A C17A -0.3(5) . . . . ? C15A C16A C17A C18A -0.8(5) . . . . ? C14A C13A C18A C17A 0.7(4) . . . . ? C12A C13A C18A C17A -177.6(3) . . . . ? C16A C17A C18A C13A 0.6(5) . . . . ? N1A C12A C19A C20A 72.8(3) . . . . ? C13A C12A C19A C20A -166.4(2) . . . . ? C12A C19A C20A C25A 86.2(3) . . . . ? C12A C19A C20A C21A -89.3(3) . . . . ? C25A C20A C21A C22A -1.8(4) . . . . ? C19A C20A C21A C22A 173.9(2) . . . . ? C20A C21A C22A C23A 1.6(4) . . . . ? C21A C22A C23A C24A -0.4(5) . . . . ? C22A C23A C24A C25A -0.6(5) . . . . ? C21A C20A C25A C24A 0.8(4) . . . . ? C19A C20A C25A C24A -174.9(2) . . . . ? C23A C24A C25A C20A 0.4(5) . . . . ? N1B C1B C2B C3B -96.4(3) . . . . ? C8B C1B C2B C3B 84.4(2) . . . . ? N1B C1B C2B C7B 82.5(3) . . . . ? C8B C1B C2B C7B -96.6(2) . . . . ? C7B C2B C3B C4B 0.3(3) . . . . ? C1B C2B C3B C4B 179.2(2) . . . . ? C2B C3B C4B C5B -0.1(4) . . . . ? C3B C4B C5B C6B -0.4(4) . . . . ? C4B C5B C6B C7B 0.7(4) . . . . ? C5B C6B C7B C2B -0.5(4) . . . . ? C3B C2B C7B C6B 0.1(3) . . . . ? C1B C2B C7B C6B -178.9(2) . . . . ? N1B C1B C8B C11B -3.0(3) . . . . ? C2B C1B C8B C11B 176.1(2) . . . . ? N1B C1B C8B C10B -124.1(2) . . . . ? C2B C1B C8B C10B 55.0(3) . . . . ? N1B C1B C8B C9B 117.5(2) . . . . ? C2B C1B C8B C9B -63.4(3) . . . . ? C2B C1B N1B C12B 5.3(3) . . . . ? C8B C1B N1B C12B -175.61(18) . . . . ? C1B N1B C12B C13B -123.3(2) . . . . ? C1B N1B C12B C19B 118.1(2) . . . . ? N1B C12B C13B C18B 143.0(2) . . . . ? C19B C12B C13B C18B -99.6(3) . . . . ? N1B C12B C13B C14B -41.8(3) . . . . ? C19B C12B C13B C14B 75.6(3) . . . . ? C18B C13B C14B C15B 1.5(4) . . . . ? C12B C13B C14B C15B -173.8(2) . . . . ? C13B C14B C15B C16B -1.3(4) . . . . ? C14B C15B C16B C17B 0.1(4) . . . . ? C15B C16B C17B C18B 0.9(5) . . . . ? C14B C13B C18B C17B -0.5(4) . . . . ? C12B C13B C18B C17B 174.9(2) . . . . ? C16B C17B C18B C13B -0.7(4) . . . . ? N1B C12B C19B C20B -63.6(3) . . . . ? C13B C12B C19B C20B 176.7(2) . . . . ? C12B C19B C20B C21B 96.4(3) . . . . ? C12B C19B C20B C25B -81.4(3) . . . . ? C25B C20B C21B C22B 0.1(4) . . . . ? C19B C20B C21B C22B -177.8(3) . . . . ? C20B C21B C22B C23B 0.7(5) . . . . ? C21B C22B C23B C24B -1.3(6) . . . . ? C22B C23B C24B C25B 1.0(6) . . . . ? C21B C20B C25B C24B -0.4(4) . . . . ? C19B C20B C25B C24B 177.5(2) . . . . ? C23B C24B C25B C20B -0.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.141 _refine_diff_density_min -0.113 _refine_diff_density_rms 0.029 data_imine_2 _database_code_depnum_ccdc_archive 'CCDC 925537' #TrackingRef 'imine_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H26 F N' _chemical_formula_sum 'C25 H26 F N' _chemical_formula_weight 359.47 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' F F 0.0171 0.0103 '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 9.2834(9) _cell_length_b 17.7729(16) _cell_length_c 12.4895(11) _cell_angle_alpha 90.00 _cell_angle_beta 96.089(2) _cell_angle_gamma 90.00 _cell_volume 2049.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6583 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 25.97 _exptl_crystal_description 'hexagonal prisms' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9732 _exptl_absorpt_correction_T_max 0.9850 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22802 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4730 _reflns_number_gt 3238 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.0532P)^2^+0.4698P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4730 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1213 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.72030(15) -0.91953(9) -0.62523(12) 0.0441(3) Uani 1 1 d . . . C2 C 0.77190(17) -0.89111(10) -0.52591(13) 0.0537(4) Uani 1 1 d . . . F1 F 0.77191(13) -0.81574(6) -0.51216(9) 0.0767(3) Uani 1 1 d . . . C3 C 0.8252(2) -0.93543(14) -0.44066(15) 0.0727(6) Uani 1 1 d . . . H3 H 0.8594 -0.9140 -0.3749 0.087 Uiso 1 1 calc R . . C4 C 0.8270(2) -1.01187(14) -0.45442(18) 0.0781(6) Uani 1 1 d . . . H4 H 0.8619 -1.0428 -0.3974 0.094 Uiso 1 1 calc R . . C5 C 0.7774(2) -1.04296(11) -0.55172(18) 0.0720(6) Uani 1 1 d . . . H5 H 0.7789 -1.0949 -0.5606 0.086 Uiso 1 1 calc R . . C6 C 0.72516(18) -0.99724(9) -0.63690(14) 0.0557(4) Uani 1 1 d . . . H6 H 0.6928 -1.0189 -0.7029 0.067 Uiso 1 1 calc R . . C7 C 0.66526(15) -0.86856(8) -0.71688(11) 0.0397(3) Uani 1 1 d . . . C8 C 0.50154(16) -0.85318(9) -0.73180(13) 0.0496(4) Uani 1 1 d . . . C9 C 0.42107(19) -0.92700(11) -0.75959(18) 0.0729(5) Uani 1 1 d . . . H9A H 0.3190 -0.9173 -0.7728 0.109 Uiso 1 1 calc R . . H9B H 0.4388 -0.9615 -0.7005 0.109 Uiso 1 1 calc R . . H9C H 0.4549 -0.9485 -0.8228 0.109 Uiso 1 1 calc R . . C10 C 0.4538(2) -0.82259(12) -0.62629(16) 0.0704(5) Uani 1 1 d . . . H10A H 0.5087 -0.7783 -0.6052 0.106 Uiso 1 1 calc R . . H10B H 0.4703 -0.8601 -0.5710 0.106 Uiso 1 1 calc R . . H10C H 0.3526 -0.8103 -0.6366 0.106 Uiso 1 1 calc R . . C11 C 0.4638(2) -0.79637(12) -0.82173(17) 0.0717(5) Uani 1 1 d . . . H11A H 0.5176 -0.7509 -0.8060 0.108 Uiso 1 1 calc R . . H11B H 0.3619 -0.7856 -0.8272 0.108 Uiso 1 1 calc R . . H11C H 0.4880 -0.8169 -0.8886 0.108 Uiso 1 1 calc R . . N1 N 0.74572(13) -0.83845(7) -0.78073(9) 0.0424(3) Uani 1 1 d . . . C12 C 0.90277(15) -0.85175(8) -0.76868(12) 0.0427(3) Uani 1 1 d . . . H12 H 0.9270 -0.8868 -0.7088 0.051 Uiso 1 1 calc R . . C13 C 0.97884(15) -0.77753(9) -0.74263(13) 0.0459(4) Uani 1 1 d . . . C14 C 0.9777(2) -0.72013(10) -0.81779(16) 0.0661(5) Uani 1 1 d . . . H14 H 0.9289 -0.7269 -0.8861 0.079 Uiso 1 1 calc R . . C15 C 1.0478(2) -0.65328(11) -0.7926(2) 0.0779(6) Uani 1 1 d . . . H15 H 1.0461 -0.6153 -0.8439 0.093 Uiso 1 1 calc R . . C16 C 1.1205(2) -0.64231(11) -0.6922(2) 0.0778(6) Uani 1 1 d . . . H16 H 1.1693 -0.5974 -0.6757 0.093 Uiso 1 1 calc R . . C17 C 1.1205(2) -0.69795(11) -0.61652(19) 0.0722(6) Uani 1 1 d . . . H17 H 1.1681 -0.6905 -0.5480 0.087 Uiso 1 1 calc R . . C18 C 1.05008(18) -0.76521(10) -0.64147(15) 0.0572(4) Uani 1 1 d . . . H18 H 1.0507 -0.8027 -0.5894 0.069 Uiso 1 1 calc R . . C19 C 0.94442(18) -0.88777(9) -0.87318(13) 0.0507(4) Uani 1 1 d . . . H19A H 0.9018 -0.8588 -0.9343 0.061 Uiso 1 1 calc R . . H19B H 1.0489 -0.8861 -0.8732 0.061 Uiso 1 1 calc R . . C20 C 0.89405(18) -0.96803(9) -0.88509(12) 0.0490(4) Uani 1 1 d . . . C21 C 0.7554(2) -0.98605(11) -0.92969(14) 0.0613(5) Uani 1 1 d . . . H21 H 0.6934 -0.9481 -0.9575 0.074 Uiso 1 1 calc R . . C22 C 0.7085(2) -1.05972(13) -0.93326(16) 0.0773(6) Uani 1 1 d . . . H22 H 0.6147 -1.0710 -0.9628 0.093 Uiso 1 1 calc R . . C23 C 0.7989(3) -1.11657(12) -0.89357(18) 0.0845(7) Uani 1 1 d . . . H23 H 0.7667 -1.1662 -0.8956 0.101 Uiso 1 1 calc R . . C24 C 0.9375(3) -1.09948(11) -0.85086(18) 0.0799(6) Uani 1 1 d . . . H24 H 1.0000 -1.1377 -0.8248 0.096 Uiso 1 1 calc R . . C25 C 0.9839(2) -1.02605(10) -0.84650(14) 0.0609(5) Uani 1 1 d . . . H25 H 1.0778 -1.0152 -0.8170 0.073 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 C1 0.0388(8) 0.0509(9) 0.0435(8) 0.0081(6) 0.0084(6) -0.0006(6) C2 0.0491(9) 0.0656(11) 0.0468(9) 0.0035(8) 0.0071(7) -0.0003(8) F1 0.0890(8) 0.0755(8) 0.0635(7) -0.0138(5) -0.0025(6) -0.0070(6) C3 0.0584(11) 0.1135(18) 0.0459(10) 0.0129(11) 0.0033(8) 0.0094(11) C4 0.0684(12) 0.1017(17) 0.0654(13) 0.0395(12) 0.0128(10) 0.0217(11) C5 0.0697(12) 0.0641(12) 0.0844(15) 0.0302(10) 0.0189(10) 0.0114(9) C6 0.0567(10) 0.0525(10) 0.0591(10) 0.0116(8) 0.0118(8) 0.0012(8) C7 0.0416(8) 0.0374(7) 0.0399(7) -0.0010(6) 0.0035(6) -0.0017(6) C8 0.0396(8) 0.0529(9) 0.0559(9) 0.0054(7) 0.0038(7) 0.0024(7) C9 0.0486(10) 0.0713(12) 0.0966(15) 0.0010(11) -0.0031(9) -0.0107(9) C10 0.0551(11) 0.0816(13) 0.0772(13) -0.0007(10) 0.0191(9) 0.0130(9) C11 0.0530(10) 0.0801(13) 0.0799(13) 0.0221(10) -0.0019(9) 0.0127(9) N1 0.0426(7) 0.0409(7) 0.0435(7) 0.0040(5) 0.0033(5) 0.0001(5) C12 0.0396(8) 0.0449(8) 0.0438(8) 0.0090(6) 0.0047(6) -0.0007(6) C13 0.0384(8) 0.0457(8) 0.0548(9) 0.0016(7) 0.0104(7) -0.0001(6) C14 0.0772(13) 0.0568(11) 0.0653(11) 0.0098(9) 0.0129(9) -0.0122(9) C15 0.0871(15) 0.0530(11) 0.0979(16) 0.0080(11) 0.0299(13) -0.0155(10) C16 0.0599(12) 0.0540(11) 0.1223(19) -0.0160(12) 0.0231(12) -0.0138(9) C17 0.0551(11) 0.0654(12) 0.0933(15) -0.0206(11) -0.0055(10) 0.0000(9) C18 0.0484(9) 0.0538(10) 0.0681(11) -0.0006(8) 0.0000(8) 0.0024(7) C19 0.0494(9) 0.0547(9) 0.0494(9) 0.0057(7) 0.0111(7) 0.0006(7) C20 0.0561(9) 0.0531(9) 0.0387(8) -0.0007(7) 0.0096(7) 0.0027(7) C21 0.0631(11) 0.0686(12) 0.0507(10) -0.0019(8) -0.0010(8) -0.0027(9) C22 0.0789(14) 0.0876(15) 0.0641(12) -0.0193(11) 0.0021(10) -0.0207(12) C23 0.119(2) 0.0556(12) 0.0802(14) -0.0172(11) 0.0186(13) -0.0183(13) C24 0.1037(17) 0.0526(12) 0.0830(14) -0.0058(10) 0.0077(12) 0.0099(11) C25 0.0652(11) 0.0578(11) 0.0597(10) -0.0052(8) 0.0056(8) 0.0071(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.377(2) . ? C1 C6 1.390(2) . ? C1 C7 1.506(2) . ? C2 F1 1.350(2) . ? C2 C3 1.374(2) . ? C3 C4 1.370(3) . ? C4 C5 1.369(3) . ? C5 C6 1.385(2) . ? C7 N1 1.2674(18) . ? C7 C8 1.536(2) . ? C8 C11 1.523(2) . ? C8 C9 1.531(2) . ? C8 C10 1.534(2) . ? N1 C12 1.4689(18) . ? C12 C13 1.515(2) . ? C12 C19 1.539(2) . ? C13 C18 1.380(2) . ? C13 C14 1.386(2) . ? C14 C15 1.375(3) . ? C15 C16 1.374(3) . ? C16 C17 1.368(3) . ? C17 C18 1.382(2) . ? C19 C20 1.504(2) . ? C20 C25 1.381(2) . ? C20 C21 1.384(2) . ? C21 C22 1.379(3) . ? C22 C23 1.372(3) . ? C23 C24 1.373(3) . ? C24 C25 1.374(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 116.54(15) . . ? C2 C1 C7 121.43(14) . . ? C6 C1 C7 122.02(14) . . ? F1 C2 C3 118.37(17) . . ? F1 C2 C1 118.27(14) . . ? C3 C2 C1 123.36(18) . . ? C4 C3 C2 118.67(19) . . ? C5 C4 C3 120.28(18) . . ? C4 C5 C6 120.15(19) . . ? C5 C6 C1 121.00(18) . . ? N1 C7 C1 123.86(13) . . ? N1 C7 C8 119.35(13) . . ? C1 C7 C8 116.79(12) . . ? C11 C8 C9 109.40(15) . . ? C11 C8 C10 109.49(15) . . ? C9 C8 C10 108.67(15) . . ? C11 C8 C7 110.78(13) . . ? C9 C8 C7 109.13(13) . . ? C10 C8 C7 109.33(13) . . ? C7 N1 C12 120.82(12) . . ? N1 C12 C13 108.47(12) . . ? N1 C12 C19 108.41(12) . . ? C13 C12 C19 113.00(12) . . ? C18 C13 C14 118.16(16) . . ? C18 C13 C12 120.12(14) . . ? C14 C13 C12 121.71(15) . . ? C15 C14 C13 120.77(19) . . ? C16 C15 C14 120.4(2) . . ? C17 C16 C15 119.49(18) . . ? C16 C17 C18 120.3(2) . . ? C13 C18 C17 120.86(18) . . ? C20 C19 C12 112.02(12) . . ? C25 C20 C21 117.97(16) . . ? C25 C20 C19 120.26(15) . . ? C21 C20 C19 121.69(15) . . ? C22 C21 C20 120.65(18) . . ? C23 C22 C21 120.5(2) . . ? C22 C23 C24 119.3(2) . . ? C23 C24 C25 120.2(2) . . ? C24 C25 C20 121.35(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 F1 178.57(14) . . . . ? C7 C1 C2 F1 0.1(2) . . . . ? C6 C1 C2 C3 -0.5(2) . . . . ? C7 C1 C2 C3 -178.94(15) . . . . ? F1 C2 C3 C4 -179.29(16) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C4 C5 C6 C1 -0.7(3) . . . . ? C2 C1 C6 C5 1.0(2) . . . . ? C7 C1 C6 C5 179.41(15) . . . . ? C2 C1 C7 N1 85.91(19) . . . . ? C6 C1 C7 N1 -92.46(19) . . . . ? C2 C1 C7 C8 -94.08(17) . . . . ? C6 C1 C7 C8 87.55(18) . . . . ? N1 C7 C8 C11 -4.3(2) . . . . ? C1 C7 C8 C11 175.73(14) . . . . ? N1 C7 C8 C9 116.25(16) . . . . ? C1 C7 C8 C9 -63.76(18) . . . . ? N1 C7 C8 C10 -125.01(16) . . . . ? C1 C7 C8 C10 54.98(18) . . . . ? C1 C7 N1 C12 -0.1(2) . . . . ? C8 C7 N1 C12 179.84(13) . . . . ? C7 N1 C12 C13 -116.41(15) . . . . ? C7 N1 C12 C19 120.53(14) . . . . ? N1 C12 C13 C18 110.21(15) . . . . ? C19 C12 C13 C18 -129.55(15) . . . . ? N1 C12 C13 C14 -68.88(18) . . . . ? C19 C12 C13 C14 51.4(2) . . . . ? C18 C13 C14 C15 1.1(3) . . . . ? C12 C13 C14 C15 -179.79(17) . . . . ? C13 C14 C15 C16 0.0(3) . . . . ? C14 C15 C16 C17 -1.2(3) . . . . ? C15 C16 C17 C18 1.1(3) . . . . ? C14 C13 C18 C17 -1.1(2) . . . . ? C12 C13 C18 C17 179.74(15) . . . . ? C16 C17 C18 C13 0.0(3) . . . . ? N1 C12 C19 C20 -72.07(16) . . . . ? C13 C12 C19 C20 167.66(13) . . . . ? C12 C19 C20 C25 -91.61(18) . . . . ? C12 C19 C20 C21 85.20(18) . . . . ? C25 C20 C21 C22 1.2(3) . . . . ? C19 C20 C21 C22 -175.65(16) . . . . ? C20 C21 C22 C23 -0.6(3) . . . . ? C21 C22 C23 C24 -0.5(3) . . . . ? C22 C23 C24 C25 1.0(3) . . . . ? C23 C24 C25 C20 -0.4(3) . . . . ? C21 C20 C25 C24 -0.7(3) . . . . ? C19 C20 C25 C24 176.22(17) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.180 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.030 data_imine_3 _database_code_depnum_ccdc_archive 'CCDC 925538' #TrackingRef 'imine_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H26 F N' _chemical_formula_sum 'C25 H26 F N' _chemical_formula_weight 359.47 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.282(2) _cell_length_b 13.625(2) _cell_length_c 11.116(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.879(3) _cell_angle_gamma 90.00 _cell_volume 2137.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2618 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 22.86 _exptl_crystal_description 'hexagonal prisms' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.117 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9782 _exptl_absorpt_correction_T_max 0.9803 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17498 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0619 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 28.35 _reflns_number_total 5086 _reflns_number_gt 2170 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Brukar SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.1186P)^2^+0.6213P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4886 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1816 _refine_ls_R_factor_gt 0.0896 _refine_ls_wR_factor_ref 0.2790 _refine_ls_wR_factor_gt 0.2297 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.7670(2) 0.0692(2) 0.0118(3) 0.0544(8) Uani 1 1 d . . . C2 C 0.8463(2) 0.1245(2) 0.0873(3) 0.0612(9) Uani 1 1 d . . . C3 C 0.8930(2) 0.0864(3) 0.1954(3) 0.0762(10) Uani 1 1 d . . . H3 H 0.8778 0.0245 0.2219 0.091 Uiso 1 1 calc R . . C4 C 0.9608(3) 0.1409(5) 0.2616(4) 0.1026(15) Uani 1 1 d . . . F1 F 1.0074(2) 0.1044(3) 0.3647(3) 0.1765(16) Uani 1 1 d . . . C5 C 0.9879(3) 0.2317(6) 0.2299(7) 0.131(3) Uani 1 1 d . . . H5 H 1.0359 0.2658 0.2787 0.157 Uiso 1 1 calc R . . C6 C 0.9423(4) 0.2713(4) 0.1243(6) 0.1179(19) Uani 1 1 d . . . H6 H 0.9584 0.3337 0.1008 0.142 Uiso 1 1 calc R . . C7 C 0.8705(3) 0.2177(3) 0.0505(4) 0.0835(11) Uani 1 1 d . . . H7 H 0.8347 0.2488 -0.0339 0.100 Uiso 1 1 calc R . . C8 C 0.7937(2) -0.0016(3) -0.0847(3) 0.0675(9) Uani 1 1 d . . . C9 C 0.8586(3) -0.0824(3) -0.0221(4) 0.0934(12) Uani 1 1 d . . . H9A H 0.8742 -0.1276 -0.0822 0.140 Uiso 1 1 calc R . . H9B H 0.8265 -0.1167 0.0350 0.140 Uiso 1 1 calc R . . H9C H 0.9156 -0.0533 0.0200 0.140 Uiso 1 1 calc R . . C10 C 0.8478(3) 0.0546(3) -0.1721(4) 0.1039(14) Uani 1 1 d . . . H10A H 0.8088 0.1069 -0.2099 0.156 Uiso 1 1 calc R . . H10B H 0.8633 0.0107 -0.2336 0.156 Uiso 1 1 calc R . . H10C H 0.9049 0.0814 -0.1274 0.156 Uiso 1 1 calc R . . C11 C 0.7040(3) -0.0494(3) -0.1554(4) 0.1048(15) Uani 1 1 d . . . H11A H 0.6618 0.0009 -0.1919 0.157 Uiso 1 1 calc R . . H11B H 0.6731 -0.0875 -0.1006 0.157 Uiso 1 1 calc R . . H11C H 0.7214 -0.0912 -0.2179 0.157 Uiso 1 1 calc R . . N1 N 0.68031(16) 0.07822(17) 0.0242(2) 0.0564(7) Uani 1 1 d . . . C12 C 0.65187(19) 0.1416(2) 0.1179(3) 0.0558(8) Uani 1 1 d . . . H12 H 0.7079 0.1730 0.1642 0.067 Uiso 1 1 calc R . . C13 C 0.58283(19) 0.2190(2) 0.0623(3) 0.0543(8) Uani 1 1 d . . . C14 C 0.5244(2) 0.2066(2) -0.0481(3) 0.0728(10) Uani 1 1 d . . . H14 H 0.5296 0.1500 -0.0935 0.087 Uiso 1 1 calc R . . C15 C 0.4576(3) 0.2781(3) -0.0922(4) 0.0904(12) Uani 1 1 d . . . H15 H 0.4186 0.2691 -0.1665 0.109 Uiso 1 1 calc R . . C16 C 0.4498(3) 0.3618(3) -0.0255(5) 0.0899(12) Uani 1 1 d . . . H16 H 0.4045 0.4089 -0.0535 0.108 Uiso 1 1 calc R . . C17 C 0.5089(3) 0.3756(3) 0.0821(4) 0.0925(12) Uani 1 1 d . . . H17 H 0.5048 0.4330 0.1263 0.111 Uiso 1 1 calc R . . C18 C 0.5746(3) 0.3048(3) 0.1255(3) 0.0787(10) Uani 1 1 d . . . H18 H 0.6142 0.3153 0.1990 0.094 Uiso 1 1 calc R . . C19 C 0.6034(2) 0.0757(2) 0.2033(3) 0.0721(10) Uani 1 1 d . . . H19A H 0.5720 0.1170 0.2560 0.086 Uiso 1 1 calc R . . H19B H 0.5553 0.0361 0.1547 0.086 Uiso 1 1 calc R . . C20 C 0.6725(2) 0.0090(2) 0.2806(3) 0.0638(9) Uani 1 1 d . . . C21 C 0.6942(2) -0.0825(3) 0.2394(4) 0.0751(10) Uani 1 1 d . . . H21 H 0.6642 -0.1040 0.1637 0.090 Uiso 1 1 calc R . . C22 C 0.7598(3) -0.1432(3) 0.3085(5) 0.0984(13) Uani 1 1 d . . . H22 H 0.7733 -0.2048 0.2796 0.118 Uiso 1 1 calc R . . C23 C 0.8041(3) -0.1117(4) 0.4189(5) 0.1104(16) Uani 1 1 d . . . H23 H 0.8481 -0.1520 0.4655 0.132 Uiso 1 1 calc R . . C24 C 0.7846(3) -0.0219(5) 0.4613(4) 0.1078(15) Uani 1 1 d . . . H24 H 0.8157 -0.0009 0.5366 0.129 Uiso 1 1 calc R . . C25 C 0.7186(3) 0.0388(3) 0.3938(4) 0.0876(11) Uani 1 1 d . . . H25 H 0.7052 0.0999 0.4244 0.105 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 C1 0.0503(17) 0.0555(18) 0.0576(18) 0.0005(14) 0.0088(14) 0.0054(14) C2 0.0441(16) 0.071(2) 0.073(2) -0.0172(17) 0.0213(16) 0.0022(15) C3 0.0500(18) 0.106(3) 0.072(2) -0.021(2) 0.0065(17) 0.0062(19) C4 0.056(2) 0.154(5) 0.092(3) -0.047(3) -0.006(2) 0.009(3) F1 0.116(2) 0.283(5) 0.116(2) -0.045(3) -0.0280(19) 0.020(3) C5 0.060(3) 0.173(6) 0.163(6) -0.106(5) 0.030(3) -0.025(3) C6 0.080(3) 0.119(4) 0.164(5) -0.058(4) 0.050(3) -0.026(3) C7 0.074(2) 0.079(3) 0.104(3) -0.019(2) 0.031(2) -0.006(2) C8 0.0609(19) 0.074(2) 0.067(2) -0.0157(17) 0.0084(16) 0.0104(16) C9 0.095(3) 0.085(3) 0.100(3) -0.021(2) 0.014(2) 0.034(2) C10 0.115(3) 0.127(4) 0.079(3) -0.009(3) 0.045(2) 0.012(3) C11 0.094(3) 0.108(3) 0.106(3) -0.053(3) -0.007(2) 0.011(2) N1 0.0507(14) 0.0540(15) 0.0650(16) -0.0035(12) 0.0108(12) 0.0050(11) C12 0.0441(15) 0.0571(18) 0.0683(19) 0.0006(15) 0.0153(14) 0.0007(13) C13 0.0452(15) 0.0525(17) 0.069(2) -0.0003(15) 0.0217(15) 0.0026(13) C14 0.0591(19) 0.063(2) 0.093(3) 0.0002(19) 0.0028(19) 0.0042(16) C15 0.072(2) 0.079(3) 0.113(3) 0.017(2) -0.009(2) 0.002(2) C16 0.070(2) 0.067(2) 0.135(4) 0.017(3) 0.026(3) 0.0154(19) C17 0.102(3) 0.066(2) 0.115(3) -0.003(2) 0.032(3) 0.026(2) C18 0.087(3) 0.070(2) 0.081(2) -0.005(2) 0.018(2) 0.012(2) C19 0.0571(19) 0.072(2) 0.091(3) 0.0131(19) 0.0256(18) 0.0086(17) C20 0.0553(18) 0.068(2) 0.071(2) 0.0117(18) 0.0178(16) -0.0022(15) C21 0.064(2) 0.072(2) 0.087(2) 0.013(2) 0.0032(18) -0.0028(18) C22 0.081(3) 0.081(3) 0.130(4) 0.023(3) 0.005(3) 0.010(2) C23 0.093(3) 0.121(4) 0.110(4) 0.039(3) -0.007(3) 0.001(3) C24 0.106(4) 0.147(5) 0.066(3) 0.017(3) -0.001(2) -0.019(3) C25 0.094(3) 0.095(3) 0.076(3) 0.003(2) 0.022(2) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.272(3) . ? C1 C2 1.503(4) . ? C1 C8 1.534(4) . ? C2 C3 1.383(5) . ? C2 C7 1.395(5) . ? C3 C4 1.345(6) . ? C3 H3 0.9300 . ? C4 F1 1.330(5) . ? C4 C5 1.360(8) . ? C5 C6 1.362(8) . ? C5 H5 0.9300 . ? C6 C7 1.413(6) . ? C6 H6 0.9300 . ? C7 H7 1.0830 . ? C8 C9 1.534(5) . ? C8 C10 1.536(5) . ? C8 C11 1.539(5) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N1 C12 1.458(4) . ? C12 C13 1.510(4) . ? C12 C19 1.545(4) . ? C12 H12 0.9800 . ? C13 C18 1.379(4) . ? C13 C14 1.384(4) . ? C14 C15 1.398(5) . ? C14 H14 0.9300 . ? C15 C16 1.374(6) . ? C15 H15 0.9300 . ? C16 C17 1.366(5) . ? C16 H16 0.9300 . ? C17 C18 1.380(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.509(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.381(5) . ? C20 C25 1.388(5) . ? C21 C22 1.389(5) . ? C21 H21 0.9300 . ? C22 C23 1.360(6) . ? C22 H22 0.9300 . ? C23 C24 1.356(7) . ? C23 H23 0.9300 . ? C24 C25 1.384(6) . ? C24 H24 0.9300 . ? C25 H25 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 N1 C1 C2 123.6(3) . . ? N1 C1 C8 119.1(3) . . ? C2 C1 C8 117.3(2) . . ? C3 C2 C7 119.3(3) . . ? C3 C2 C1 121.2(3) . . ? C7 C2 C1 119.5(3) . . ? C4 C3 C2 118.6(4) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? F1 C4 C3 119.2(6) . . ? F1 C4 C5 116.0(5) . . ? C3 C4 C5 124.8(5) . . ? C4 C5 C6 117.7(5) . . ? C4 C5 H5 121.1 . . ? C6 C5 H5 121.1 . . ? C5 C6 C7 120.3(5) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C2 C7 C6 119.4(5) . . ? C2 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C1 C8 C9 109.4(3) . . ? C1 C8 C10 109.3(3) . . ? C9 C8 C10 108.5(3) . . ? C1 C8 C11 110.2(3) . . ? C9 C8 C11 109.0(3) . . ? C10 C8 C11 110.4(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 N1 C12 121.1(2) . . ? N1 C12 C13 110.9(2) . . ? N1 C12 C19 107.2(2) . . ? C13 C12 C19 109.3(2) . . ? N1 C12 H12 109.8 . . ? C13 C12 H12 109.8 . . ? C19 C12 H12 109.8 . . ? C18 C13 C14 117.9(3) . . ? C18 C13 C12 119.1(3) . . ? C14 C13 C12 123.0(3) . . ? C13 C14 C15 120.8(3) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 119.8(4) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C17 C16 C15 119.8(4) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.3(4) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C13 C18 C17 121.5(4) . . ? C13 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C20 C19 C12 112.6(2) . . ? C20 C19 H19A 109.1 . . ? C12 C19 H19A 109.1 . . ? C20 C19 H19B 109.1 . . ? C12 C19 H19B 109.1 . . ? H19A C19 H19B 107.8 . . ? C21 C20 C25 117.8(3) . . ? C21 C20 C19 121.0(3) . . ? C25 C20 C19 121.2(3) . . ? C20 C21 C22 121.4(4) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C23 C22 C21 119.4(4) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C24 C23 C22 120.4(4) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 120.7(4) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C24 C25 C20 120.3(4) . . ? C24 C25 H25 119.8 . . ? C20 C25 H25 119.8 . . ? 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 N1 C1 C2 C3 90.1(4) . . . . ? C8 C1 C2 C3 -89.7(4) . . . . ? N1 C1 C2 C7 -86.9(4) . . . . ? C8 C1 C2 C7 93.2(3) . . . . ? C7 C2 C3 C4 -0.2(5) . . . . ? C1 C2 C3 C4 -177.3(3) . . . . ? C2 C3 C4 F1 -178.8(3) . . . . ? C2 C3 C4 C5 -0.3(6) . . . . ? F1 C4 C5 C6 179.5(4) . . . . ? C3 C4 C5 C6 0.9(7) . . . . ? C4 C5 C6 C7 -1.1(7) . . . . ? C3 C2 C7 C6 0.1(5) . . . . ? C1 C2 C7 C6 177.2(3) . . . . ? C5 C6 C7 C2 0.6(6) . . . . ? N1 C1 C8 C9 -118.1(3) . . . . ? C2 C1 C8 C9 61.8(4) . . . . ? N1 C1 C8 C10 123.2(3) . . . . ? C2 C1 C8 C10 -56.9(4) . . . . ? N1 C1 C8 C11 1.7(4) . . . . ? C2 C1 C8 C11 -178.4(3) . . . . ? C2 C1 N1 C12 -2.4(4) . . . . ? C8 C1 N1 C12 177.4(3) . . . . ? C1 N1 C12 C13 121.9(3) . . . . ? C1 N1 C12 C19 -118.8(3) . . . . ? N1 C12 C13 C18 -156.3(3) . . . . ? C19 C12 C13 C18 85.7(4) . . . . ? N1 C12 C13 C14 26.0(4) . . . . ? C19 C12 C13 C14 -92.0(3) . . . . ? C18 C13 C14 C15 -1.6(5) . . . . ? C12 C13 C14 C15 176.1(3) . . . . ? C13 C14 C15 C16 0.1(6) . . . . ? C14 C15 C16 C17 1.5(6) . . . . ? C15 C16 C17 C18 -1.7(6) . . . . ? C14 C13 C18 C17 1.5(5) . . . . ? C12 C13 C18 C17 -176.3(3) . . . . ? C16 C17 C18 C13 0.1(6) . . . . ? N1 C12 C19 C20 70.6(3) . . . . ? C13 C12 C19 C20 -169.0(3) . . . . ? C12 C19 C20 C21 -88.4(4) . . . . ? C12 C19 C20 C25 89.5(4) . . . . ? C25 C20 C21 C22 0.1(5) . . . . ? C19 C20 C21 C22 178.1(3) . . . . ? C20 C21 C22 C23 -0.4(6) . . . . ? C21 C22 C23 C24 0.0(7) . . . . ? C22 C23 C24 C25 0.6(7) . . . . ? C23 C24 C25 C20 -0.9(6) . . . . ? C21 C20 C25 C24 0.5(5) . . . . ? C19 C20 C25 C24 -177.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.616 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.042 data_imine_10 _database_code_depnum_ccdc_archive 'CCDC 925539' #TrackingRef 'imine_10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H25 N O3' _chemical_formula_sum 'C21 H25 N O3' _chemical_formula_weight 339.42 _chemical_absolute_configuration syn 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 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 9.746(2) _cell_length_b 17.508(3) _cell_length_c 25.813(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4404.8(18) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 41 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 12.50 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.024 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4 diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5397 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 24.99 _reflns_number_total 5159 _reflns_number_gt 2646 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.1888P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -3(4) _refine_ls_number_reflns 5159 _refine_ls_number_parameters 461 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1699 _refine_ls_R_factor_gt 0.0967 _refine_ls_wR_factor_ref 0.3081 _refine_ls_wR_factor_gt 0.2539 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 C1A C 0.2783(8) -1.0617(4) -1.2373(3) 0.0541(19) Uani 1 1 d . . . C2A C 0.2915(9) -0.9881(5) -1.2560(4) 0.066(2) Uani 1 1 d . . . H2A H 0.2980 -0.9472 -1.2331 0.079 Uiso 1 1 calc R . . C3A C 0.2950(10) -0.9755(7) -1.3082(5) 0.090(3) Uani 1 1 d . . . H3A H 0.3049 -0.9260 -1.3207 0.107 Uiso 1 1 calc R . . C4A C 0.2837(10) -1.0360(8) -1.3429(4) 0.091(3) Uani 1 1 d . . . H4A H 0.2866 -1.0270 -1.3784 0.109 Uiso 1 1 calc R . . C5A C 0.2686(11) -1.1076(7) -1.3248(4) 0.086(3) Uani 1 1 d . . . H5A H 0.2595 -1.1481 -1.3479 0.103 Uiso 1 1 calc R . . C6A C 0.2666(9) -1.1212(5) -1.2727(3) 0.069(2) Uani 1 1 d . . . H6A H 0.2571 -1.1710 -1.2607 0.083 Uiso 1 1 calc R . . C7A C 0.2803(8) -1.0792(4) -1.1801(3) 0.0523(19) Uani 1 1 d . . . C8A C 0.1444(9) -1.0748(5) -1.1494(4) 0.071(3) Uani 1 1 d . . . C9A C 0.0884(14) -0.9909(6) -1.1524(6) 0.133(5) Uani 1 1 d . . . H9A1 H 0.0577 -0.9804 -1.1870 0.199 Uiso 1 1 calc R . . H9A2 H 0.1602 -0.9558 -1.1432 0.199 Uiso 1 1 calc R . . H9A3 H 0.0131 -0.9852 -1.1287 0.199 Uiso 1 1 calc R . . C10A C 0.0388(10) -1.1290(6) -1.1737(5) 0.093(3) Uani 1 1 d . . . H10A H 0.0724 -1.1805 -1.1720 0.139 Uiso 1 1 calc R . . H10B H 0.0240 -1.1150 -1.2092 0.139 Uiso 1 1 calc R . . H10C H -0.0461 -1.1254 -1.1550 0.139 Uiso 1 1 calc R . . C11A C 0.1640(12) -1.0989(8) -1.0935(4) 0.104(4) Uani 1 1 d . . . H11A H 0.2243 -1.0635 -1.0765 0.156 Uiso 1 1 calc R . . H11B H 0.2033 -1.1491 -1.0924 0.156 Uiso 1 1 calc R . . H11C H 0.0768 -1.0992 -1.0762 0.156 Uiso 1 1 calc R . . N1A N 0.3886(7) -1.0976(4) -1.1557(2) 0.0563(17) Uani 1 1 d . . . C12A C 0.5205(8) -1.0992(4) -1.1817(3) 0.056(2) Uani 1 1 d . . . H12A H 0.5088 -1.0805 -1.2172 0.068 Uiso 1 1 calc R . . C13A C 0.5735(9) -1.1804(5) -1.1836(3) 0.058(2) Uani 1 1 d . . . O13A O 0.5081(7) -1.2363(3) -1.1747(3) 0.093(2) Uani 1 1 d . . . C14A C 0.7608(11) -1.2595(5) -1.2072(5) 0.097(3) Uani 1 1 d . . . H14A H 0.7061 -1.2880 -1.2314 0.146 Uiso 1 1 calc R . . H14B H 0.7631 -1.2858 -1.1746 0.146 Uiso 1 1 calc R . . H1C H 0.8525 -1.2545 -1.2204 0.146 Uiso 1 1 calc R . . O14A O 0.7011(6) -1.1836(3) -1.2000(2) 0.0698(16) Uani 1 1 d . . . C15A C 0.6209(9) -1.0454(4) -1.1526(3) 0.065(2) Uani 1 1 d . . . H15A H 0.6277 -1.0614 -1.1167 0.078 Uiso 1 1 calc R . . H15B H 0.7114 -1.0494 -1.1680 0.078 Uiso 1 1 calc R . . C16A C 0.5735(9) -0.9630(4) -1.1547(3) 0.056(2) Uani 1 1 d . . . C17A C 0.4881(10) -0.9317(5) -1.1183(3) 0.068(2) Uani 1 1 d . . . H17A H 0.4607 -0.9619 -1.0905 0.082 Uiso 1 1 calc R . . C18A C 0.4411(10) -0.8579(5) -1.1209(3) 0.067(2) Uani 1 1 d . . . H18A H 0.3835 -0.8390 -1.0952 0.080 Uiso 1 1 calc R . . C19A C 0.4796(8) -0.8121(4) -1.1617(3) 0.057(2) Uani 1 1 d . . . O19A O 0.4358(7) -0.7377(3) -1.1663(3) 0.0770(18) Uani 1 1 d . . . H19A H 0.4725 -0.7179 -1.1916 0.116 Uiso 1 1 calc R . . C20A C 0.5644(9) -0.8409(4) -1.1991(3) 0.063(2) Uani 1 1 d . . . H20A H 0.5899 -0.8105 -1.2271 0.075 Uiso 1 1 calc R . . C21A C 0.6130(8) -0.9160(5) -1.1955(3) 0.062(2) Uani 1 1 d . . . H21A H 0.6725 -0.9346 -1.2206 0.074 Uiso 1 1 calc R . . C1B C 0.0999(9) -1.5790(5) -1.0417(3) 0.062(2) Uani 1 1 d . . . C2B C 0.0843(13) -1.5020(6) -1.0488(4) 0.096(3) Uani 1 1 d . . . H2B H 0.1545 -1.4713 -1.0616 0.115 Uiso 1 1 calc R . . C3B C -0.051(2) -1.4713(10) -1.0350(6) 0.149(8) Uani 1 1 d . . . H3B H -0.0658 -1.4190 -1.0383 0.178 Uiso 1 1 calc R . . C4B C -0.1554(18) -1.5145(17) -1.0178(6) 0.156(10) Uani 1 1 d . . . H4B H -0.2399 -1.4928 -1.0098 0.187 Uiso 1 1 calc R . . C5B C -0.1336(16) -1.5920(14) -1.0122(5) 0.139(7) Uani 1 1 d . . . H5B H -0.2035 -1.6234 -0.9999 0.167 Uiso 1 1 calc R . . C6B C -0.0103(11) -1.6221(8) -1.0246(4) 0.088(3) Uani 1 1 d . . . H6B H 0.0012 -1.6746 -1.0215 0.105 Uiso 1 1 calc R . . C7B C 0.2301(9) -1.6163(4) -1.0560(3) 0.058(2) Uani 1 1 d . . . C8B C 0.3446(10) -1.6192(6) -1.0166(4) 0.077(3) Uani 1 1 d . . . C9B C 0.3863(19) -1.5322(9) -1.0047(8) 0.193(9) Uani 1 1 d . . . H9B1 H 0.3049 -1.5015 -1.0024 0.290 Uiso 1 1 calc R . . H9B2 H 0.4435 -1.5133 -1.0322 0.290 Uiso 1 1 calc R . . H9B3 H 0.4355 -1.5298 -0.9725 0.290 Uiso 1 1 calc R . . C10B C 0.2922(15) -1.6668(11) -0.9695(5) 0.166(7) Uani 1 1 d . . . H10D H 0.2816 -1.7192 -0.9797 0.249 Uiso 1 1 calc R . . H10E H 0.2053 -1.6470 -0.9582 0.249 Uiso 1 1 calc R . . H10F H 0.3573 -1.6635 -0.9417 0.249 Uiso 1 1 calc R . . C11B C 0.4712(12) -1.6589(8) -1.0369(4) 0.109(4) Uani 1 1 d . . . H11D H 0.5094 -1.6297 -1.0649 0.164 Uiso 1 1 calc R . . H11E H 0.4470 -1.7089 -1.0491 0.164 Uiso 1 1 calc R . . H11F H 0.5377 -1.6633 -1.0096 0.164 Uiso 1 1 calc R . . N1B N 0.2475(6) -1.6507(3) -1.0988(3) 0.0533(16) Uani 1 1 d . . . C12B C 0.1371(8) -1.6492(4) -1.1377(3) 0.0518(19) Uani 1 1 d . . . H12B H 0.0609 -1.6189 -1.1239 0.062 Uiso 1 1 calc R . . C13B C 0.0882(9) -1.7307(5) -1.1453(3) 0.057(2) Uani 1 1 d . . . O13B O 0.1134(9) -1.7826(4) -1.1186(3) 0.105(3) Uani 1 1 d . . . C14B C -0.0633(12) -1.8073(5) -1.1946(5) 0.105(4) Uani 1 1 d . . . H14D H -0.1268 -1.8175 -1.1671 0.157 Uiso 1 1 calc R . . H14E H 0.0043 -1.8471 -1.1959 0.157 Uiso 1 1 calc R . . H1F H -0.1117 -1.8053 -1.2270 0.157 Uiso 1 1 calc R . . O14B O 0.0031(7) -1.7355(3) -1.1855(3) 0.0838(19) Uani 1 1 d . . . C15B C 0.1895(9) -1.6109(4) -1.1878(3) 0.060(2) Uani 1 1 d . . . H15C H 0.2767 -1.6335 -1.1976 0.072 Uiso 1 1 calc R . . H15D H 0.1248 -1.6205 -1.2156 0.072 Uiso 1 1 calc R . . C16B C 0.2076(8) -1.5253(4) -1.1812(3) 0.0520(19) Uani 1 1 d . . . C17B C 0.3308(9) -1.4929(4) -1.1698(3) 0.062(2) Uani 1 1 d . . . H17B H 0.4074 -1.5241 -1.1660 0.075 Uiso 1 1 calc R . . C18B C 0.3452(9) -1.4136(5) -1.1636(4) 0.073(3) Uani 1 1 d . . . H18B H 0.4308 -1.3929 -1.1562 0.088 Uiso 1 1 calc R . . C19B C 0.2337(9) -1.3668(4) -1.1686(4) 0.070(2) Uani 1 1 d . . . O19B O 0.2380(8) -1.2899(3) -1.1640(4) 0.108(3) Uani 1 1 d . . . H19B H 0.3166 -1.2764 -1.1573 0.162 Uiso 1 1 calc R . . C20B C 0.1063(9) -1.3998(5) -1.1788(4) 0.080(3) Uani 1 1 d . . . H20B H 0.0293 -1.3687 -1.1815 0.096 Uiso 1 1 calc R . . C21B C 0.0925(9) -1.4769(5) -1.1851(3) 0.068(2) Uani 1 1 d . . . H21B H 0.0065 -1.4976 -1.1919 0.082 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 C1A 0.042(4) 0.060(5) 0.060(5) -0.003(4) -0.011(4) -0.001(4) C2A 0.061(5) 0.063(5) 0.073(6) 0.001(4) -0.005(5) 0.002(5) C3A 0.057(6) 0.093(7) 0.118(9) 0.028(7) -0.008(6) -0.003(6) C4A 0.058(6) 0.138(10) 0.076(6) 0.002(8) 0.005(5) 0.000(7) C5A 0.087(7) 0.102(8) 0.069(6) -0.022(6) -0.007(6) -0.013(7) C6A 0.075(6) 0.058(5) 0.074(6) -0.013(4) -0.006(5) -0.010(5) C7A 0.048(4) 0.040(4) 0.069(5) -0.010(4) 0.000(4) -0.006(4) C8A 0.052(5) 0.066(5) 0.094(7) -0.019(5) 0.011(5) 0.002(4) C9A 0.110(10) 0.075(7) 0.213(15) -0.022(8) 0.062(11) 0.018(7) C10A 0.060(6) 0.104(8) 0.115(8) -0.012(7) -0.007(6) -0.017(6) C11A 0.093(8) 0.156(10) 0.063(6) -0.001(7) 0.021(6) -0.007(8) N1A 0.050(4) 0.060(4) 0.059(4) -0.005(3) -0.002(3) -0.004(3) C12A 0.047(4) 0.055(5) 0.068(5) -0.001(4) -0.010(4) 0.001(4) C13A 0.055(5) 0.056(5) 0.064(5) -0.002(4) -0.004(4) -0.013(4) O13A 0.079(4) 0.060(4) 0.139(6) 0.000(4) 0.017(5) -0.014(4) C14A 0.082(7) 0.059(5) 0.151(10) -0.014(6) 0.009(8) 0.017(5) O14A 0.058(4) 0.052(3) 0.100(4) 0.010(3) 0.012(3) 0.002(3) C15A 0.060(5) 0.055(5) 0.079(6) 0.000(4) -0.017(5) 0.000(4) C16A 0.058(5) 0.050(4) 0.060(5) -0.005(4) -0.009(5) -0.005(4) C17A 0.092(7) 0.061(5) 0.051(5) 0.000(4) -0.001(5) 0.000(5) C18A 0.079(6) 0.051(5) 0.070(5) -0.009(4) 0.006(5) 0.000(5) C19A 0.051(5) 0.060(5) 0.059(5) -0.008(4) 0.003(4) 0.002(4) O19A 0.081(4) 0.055(3) 0.095(5) 0.011(3) 0.008(4) 0.012(3) C20A 0.064(5) 0.050(5) 0.074(5) 0.010(4) 0.010(5) -0.009(4) C21A 0.052(5) 0.060(5) 0.074(6) -0.005(4) 0.007(4) -0.007(4) C1B 0.064(6) 0.075(6) 0.046(4) -0.015(4) -0.011(4) 0.016(5) C2B 0.100(9) 0.088(8) 0.100(8) -0.027(6) 0.000(7) 0.031(7) C3B 0.183(18) 0.127(12) 0.136(13) -0.068(10) -0.066(13) 0.094(14) C4B 0.077(9) 0.31(3) 0.083(9) -0.073(15) -0.016(8) 0.039(16) C5B 0.079(10) 0.26(2) 0.075(8) -0.005(12) 0.011(7) 0.022(13) C6B 0.062(6) 0.141(10) 0.060(5) -0.002(6) 0.001(5) 0.003(7) C7B 0.062(5) 0.051(4) 0.061(5) 0.000(4) -0.003(4) -0.002(4) C8B 0.066(6) 0.090(7) 0.074(6) -0.017(5) -0.025(5) 0.003(6) C9B 0.162(15) 0.130(12) 0.29(2) -0.085(13) -0.146(16) 0.033(11) C10B 0.103(10) 0.31(2) 0.085(8) 0.062(11) -0.010(7) 0.038(14) C11B 0.075(7) 0.160(12) 0.093(7) -0.003(8) -0.029(6) 0.016(9) N1B 0.046(4) 0.052(3) 0.061(4) 0.001(3) -0.003(3) 0.002(3) C12B 0.050(5) 0.049(4) 0.056(5) 0.000(4) -0.006(4) 0.000(4) C13B 0.059(5) 0.052(5) 0.062(5) 0.003(4) -0.009(5) 0.002(4) O13B 0.123(6) 0.066(4) 0.125(6) 0.024(4) -0.048(5) -0.017(5) C14B 0.095(8) 0.066(6) 0.154(11) -0.005(6) -0.030(8) -0.017(6) O14B 0.082(4) 0.062(4) 0.107(5) -0.001(3) -0.039(4) -0.011(3) C15B 0.064(5) 0.067(5) 0.050(4) 0.003(4) 0.002(4) 0.008(4) C16B 0.049(5) 0.050(4) 0.057(4) 0.009(4) 0.001(4) -0.003(4) C17B 0.050(5) 0.057(5) 0.080(6) 0.004(5) 0.002(4) 0.011(4) C18B 0.055(5) 0.056(5) 0.108(7) -0.001(5) 0.006(5) -0.011(5) C19B 0.062(6) 0.048(5) 0.099(7) 0.014(5) 0.010(5) 0.004(5) O19B 0.093(5) 0.048(3) 0.183(7) 0.007(4) 0.020(6) 0.001(4) C20B 0.051(5) 0.058(5) 0.129(8) 0.032(5) 0.008(6) 0.010(5) C21B 0.044(5) 0.076(6) 0.084(6) 0.026(5) 0.001(5) -0.001(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A C2A 1.382(11) . ? C1A C6A 1.391(11) . ? C1A C7A 1.508(11) . ? C2A C3A 1.367(14) . ? C2A H2A 0.9300 . ? C3A C4A 1.391(15) . ? C3A H3A 0.9300 . ? C4A C5A 1.346(14) . ? C4A H4A 0.9300 . ? C5A C6A 1.366(13) . ? C5A H5A 0.9300 . ? C6A H6A 0.9300 . ? C7A N1A 1.272(10) . ? C7A C8A 1.545(12) . ? C8A C11A 1.516(14) . ? C8A C10A 1.533(12) . ? C8A C9A 1.569(14) . ? C9A H9A1 0.9600 . ? C9A H9A2 0.9600 . ? C9A H9A3 0.9600 . ? C10A H10A 0.9600 . ? C10A H10B 0.9600 . ? C10A H10C 0.9600 . ? C11A H11A 0.9600 . ? C11A H11B 0.9600 . ? C11A H11C 0.9600 . ? N1A C12A 1.451(10) . ? C12A C13A 1.513(11) . ? C12A C15A 1.553(11) . ? C12A H12A 0.9800 . ? C13A O13A 1.190(9) . ? C13A O14A 1.315(10) . ? C14A O14A 1.463(10) . ? C14A H14A 0.9600 . ? C14A H14B 0.9600 . ? C14A H1C 0.9600 . ? C15A C16A 1.516(11) . ? C15A H15A 0.9700 . ? C15A H15B 0.9700 . ? C16A C17A 1.369(11) . ? C16A C21A 1.390(11) . ? C17A C18A 1.372(11) . ? C17A H17A 0.9300 . ? C18A C19A 1.376(11) . ? C18A H18A 0.9300 . ? C19A C20A 1.368(11) . ? C19A O19A 1.376(9) . ? O19A H19A 0.8200 . ? C20A C21A 1.401(11) . ? C20A H20A 0.9300 . ? C21A H21A 0.9300 . ? C1B C2B 1.368(14) . ? C1B C6B 1.384(14) . ? C1B C7B 1.475(12) . ? C2B C3B 1.47(2) . ? C2B H2B 0.9300 . ? C3B C4B 1.34(3) . ? C3B H3B 0.9300 . ? C4B C5B 1.38(2) . ? C4B H4B 0.9300 . ? C5B C6B 1.351(19) . ? C5B H5B 0.9300 . ? C6B H6B 0.9300 . ? C7B N1B 1.269(10) . ? C7B C8B 1.512(12) . ? C8B C11B 1.511(15) . ? C8B C10B 1.559(15) . ? C8B C9B 1.605(17) . ? C9B H9B1 0.9600 . ? C9B H9B2 0.9600 . ? C9B H9B3 0.9600 . ? C10B H10D 0.9600 . ? C10B H10E 0.9600 . ? C10B H10F 0.9600 . ? C11B H11D 0.9600 . ? C11B H11E 0.9600 . ? C11B H11F 0.9600 . ? N1B C12B 1.471(9) . ? C12B C13B 1.518(11) . ? C12B C15B 1.545(10) . ? C12B H12B 0.9800 . ? C13B O13B 1.167(9) . ? C13B O14B 1.331(10) . ? C14B O14B 1.432(11) . ? C14B H14D 0.9600 . ? C14B H14E 0.9600 . ? C14B H1F 0.9600 . ? C15B C16B 1.519(11) . ? C15B H15C 0.9700 . ? C15B H15D 0.9700 . ? C16B C17B 1.359(11) . ? C16B C21B 1.409(11) . ? C17B C18B 1.405(11) . ? C17B H17B 0.9300 . ? C18B C19B 1.367(12) . ? C18B H18B 0.9300 . ? C19B O19B 1.353(9) . ? C19B C20B 1.394(12) . ? O19B H19B 0.8200 . ? C20B C21B 1.367(12) . ? C20B H20B 0.9300 . ? C21B H21B 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 C2A C1A C6A 118.5(8) . . ? C2A C1A C7A 122.0(7) . . ? C6A C1A C7A 119.4(7) . . ? C3A C2A C1A 119.8(9) . . ? C3A C2A H2A 120.1 . . ? C1A C2A H2A 120.1 . . ? C2A C3A C4A 120.7(10) . . ? C2A C3A H3A 119.7 . . ? C4A C3A H3A 119.7 . . ? C5A C4A C3A 119.7(10) . . ? C5A C4A H4A 120.2 . . ? C3A C4A H4A 120.2 . . ? C4A C5A C6A 120.4(9) . . ? C4A C5A H5A 119.8 . . ? C6A C5A H5A 119.8 . . ? C5A C6A C1A 121.0(9) . . ? C5A C6A H6A 119.5 . . ? C1A C6A H6A 119.5 . . ? N1A C7A C1A 123.2(7) . . ? N1A C7A C8A 118.0(7) . . ? C1A C7A C8A 118.8(8) . . ? C11A C8A C10A 107.6(9) . . ? C11A C8A C7A 111.5(8) . . ? C10A C8A C7A 109.6(7) . . ? C11A C8A C9A 110.5(9) . . ? C10A C8A C9A 109.0(9) . . ? C7A C8A C9A 108.7(8) . . ? C8A C9A H9A1 109.5 . . ? C8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? C8A C10A H10A 109.5 . . ? C8A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C8A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C8A C11A H11A 109.5 . . ? C8A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C8A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C7A N1A C12A 120.7(7) . . ? N1A C12A C13A 109.6(6) . . ? N1A C12A C15A 108.8(6) . . ? C13A C12A C15A 111.7(6) . . ? N1A C12A H12A 108.9 . . ? C13A C12A H12A 108.9 . . ? C15A C12A H12A 108.9 . . ? O13A C13A O14A 122.2(8) . . ? O13A C13A C12A 125.7(8) . . ? O14A C13A C12A 111.9(7) . . ? O14A C14A H14A 109.5 . . ? O14A C14A H14B 109.5 . . ? H14A C14A H14B 109.5 . . ? O14A C14A H1C 109.5 . . ? H14A C14A H1C 109.5 . . ? H14B C14A H1C 109.5 . . ? C13A O14A C14A 117.2(7) . . ? C16A C15A C12A 111.6(7) . . ? C16A C15A H15A 109.3 . . ? C12A C15A H15A 109.3 . . ? C16A C15A H15B 109.3 . . ? C12A C15A H15B 109.3 . . ? H15A C15A H15B 108.0 . . ? C17A C16A C21A 116.8(8) . . ? C17A C16A C15A 122.7(8) . . ? C21A C16A C15A 120.5(8) . . ? C16A C17A C18A 123.1(8) . . ? C16A C17A H17A 118.4 . . ? C18A C17A H17A 118.4 . . ? C17A C18A C19A 119.6(8) . . ? C17A C18A H18A 120.2 . . ? C19A C18A H18A 120.2 . . ? C20A C19A O19A 118.3(7) . . ? C20A C19A C18A 119.4(8) . . ? O19A C19A C18A 122.3(7) . . ? C19A O19A H19A 109.5 . . ? C19A C20A C21A 120.2(8) . . ? C19A C20A H20A 119.9 . . ? C21A C20A H20A 119.9 . . ? C16A C21A C20A 120.9(8) . . ? C16A C21A H21A 119.6 . . ? C20A C21A H21A 119.6 . . ? C2B C1B C6B 119.6(10) . . ? C2B C1B C7B 119.8(10) . . ? C6B C1B C7B 120.4(9) . . ? C1B C2B C3B 115.2(14) . . ? C1B C2B H2B 122.4 . . ? C3B C2B H2B 122.4 . . ? C4B C3B C2B 123.7(16) . . ? C4B C3B H3B 118.2 . . ? C2B C3B H3B 118.2 . . ? C3B C4B C5B 118.2(18) . . ? C3B C4B H4B 120.9 . . ? C5B C4B H4B 120.9 . . ? C6B C5B C4B 119.6(19) . . ? C6B C5B H5B 120.2 . . ? C4B C5B H5B 120.2 . . ? C5B C6B C1B 123.6(15) . . ? C5B C6B H6B 118.2 . . ? C1B C6B H6B 118.2 . . ? N1B C7B C1B 122.9(7) . . ? N1B C7B C8B 118.2(8) . . ? C1B C7B C8B 118.7(7) . . ? C11B C8B C7B 112.6(7) . . ? C11B C8B C10B 107.0(10) . . ? C7B C8B C10B 107.5(8) . . ? C11B C8B C9B 107.2(11) . . ? C7B C8B C9B 106.5(9) . . ? C10B C8B C9B 116.2(12) . . ? C8B C9B H9B1 109.5 . . ? C8B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C8B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? C8B C10B H10D 109.5 . . ? C8B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C8B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? C8B C11B H11D 109.5 . . ? C8B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? C8B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? C7B N1B C12B 119.2(7) . . ? N1B C12B C13B 107.5(6) . . ? N1B C12B C15B 109.7(6) . . ? C13B C12B C15B 113.8(6) . . ? N1B C12B H12B 108.6 . . ? C13B C12B H12B 108.6 . . ? C15B C12B H12B 108.6 . . ? O13B C13B O14B 122.8(8) . . ? O13B C13B C12B 126.1(8) . . ? O14B C13B C12B 110.9(7) . . ? O14B C14B H14D 109.5 . . ? O14B C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? O14B C14B H1F 109.5 . . ? H14D C14B H1F 109.5 . . ? H14E C14B H1F 109.5 . . ? C13B O14B C14B 117.7(7) . . ? C16B C15B C12B 111.8(6) . . ? C16B C15B H15C 109.3 . . ? C12B C15B H15C 109.3 . . ? C16B C15B H15D 109.3 . . ? C12B C15B H15D 109.3 . . ? H15C C15B H15D 107.9 . . ? C17B C16B C21B 117.9(7) . . ? C17B C16B C15B 122.6(7) . . ? C21B C16B C15B 119.5(7) . . ? C16B C17B C18B 121.6(8) . . ? C16B C17B H17B 119.2 . . ? C18B C17B H17B 119.2 . . ? C19B C18B C17B 120.1(8) . . ? C19B C18B H18B 119.9 . . ? C17B C18B H18B 119.9 . . ? O19B C19B C18B 124.3(9) . . ? O19B C19B C20B 117.2(8) . . ? C18B C19B C20B 118.5(7) . . ? C19B O19B H19B 109.5 . . ? C21B C20B C19B 121.3(8) . . ? C21B C20B H20B 119.4 . . ? C19B C20B H20B 119.4 . . ? C20B C21B C16B 120.4(8) . . ? C20B C21B H21B 119.8 . . ? C16B C21B H21B 119.8 . . ? 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 C6A C1A C2A C3A -1.1(13) . . . . ? C7A C1A C2A C3A 177.2(8) . . . . ? C1A C2A C3A C4A 0.8(15) . . . . ? C2A C3A C4A C5A 0.3(16) . . . . ? C3A C4A C5A C6A -1.1(17) . . . . ? C4A C5A C6A C1A 0.7(17) . . . . ? C2A C1A C6A C5A 0.3(14) . . . . ? C7A C1A C6A C5A -178.0(9) . . . . ? C2A C1A C7A N1A -93.3(10) . . . . ? C6A C1A C7A N1A 85.0(10) . . . . ? C2A C1A C7A C8A 86.7(10) . . . . ? C6A C1A C7A C8A -95.0(9) . . . . ? N1A C7A C8A C11A -3.5(11) . . . . ? C1A C7A C8A C11A 176.5(8) . . . . ? N1A C7A C8A C10A -122.5(8) . . . . ? C1A C7A C8A C10A 57.5(10) . . . . ? N1A C7A C8A C9A 118.5(10) . . . . ? C1A C7A C8A C9A -61.5(10) . . . . ? C1A C7A N1A C12A 2.9(11) . . . . ? C8A C7A N1A C12A -177.1(6) . . . . ? C7A N1A C12A C13A -114.3(8) . . . . ? C7A N1A C12A C15A 123.3(7) . . . . ? N1A C12A C13A O13A 13.7(12) . . . . ? C15A C12A C13A O13A 134.3(9) . . . . ? N1A C12A C13A O14A -170.8(7) . . . . ? C15A C12A C13A O14A -50.2(10) . . . . ? O13A C13A O14A C14A 0.1(13) . . . . ? C12A C13A O14A C14A -175.6(8) . . . . ? N1A C12A C15A C16A -63.7(9) . . . . ? C13A C12A C15A C16A 175.1(7) . . . . ? C12A C15A C16A C17A 89.5(10) . . . . ? C12A C15A C16A C21A -88.6(9) . . . . ? C21A C16A C17A C18A 0.4(13) . . . . ? C15A C16A C17A C18A -177.8(8) . . . . ? C16A C17A C18A C19A 0.3(14) . . . . ? C17A C18A C19A C20A 0.0(13) . . . . ? C17A C18A C19A O19A -179.9(8) . . . . ? O19A C19A C20A C21A 179.0(8) . . . . ? C18A C19A C20A C21A -0.9(12) . . . . ? C17A C16A C21A C20A -1.3(12) . . . . ? C15A C16A C21A C20A 176.9(7) . . . . ? C19A C20A C21A C16A 1.6(12) . . . . ? C6B C1B C2B C3B 2.6(14) . . . . ? C7B C1B C2B C3B 177.8(9) . . . . ? C1B C2B C3B C4B -2(2) . . . . ? C2B C3B C4B C5B 1(3) . . . . ? C3B C4B C5B C6B -1(2) . . . . ? C4B C5B C6B C1B 2(2) . . . . ? C2B C1B C6B C5B -2.9(16) . . . . ? C7B C1B C6B C5B -178.1(10) . . . . ? C2B C1B C7B N1B -97.4(10) . . . . ? C6B C1B C7B N1B 77.8(11) . . . . ? C2B C1B C7B C8B 87.5(11) . . . . ? C6B C1B C7B C8B -97.4(10) . . . . ? N1B C7B C8B C11B 4.8(13) . . . . ? C1B C7B C8B C11B -179.8(9) . . . . ? N1B C7B C8B C10B -112.8(10) . . . . ? C1B C7B C8B C10B 62.6(12) . . . . ? N1B C7B C8B C9B 122.0(12) . . . . ? C1B C7B C8B C9B -62.6(13) . . . . ? C1B C7B N1B C12B 4.4(11) . . . . ? C8B C7B N1B C12B 179.6(7) . . . . ? C7B N1B C12B C13B -116.4(8) . . . . ? C7B N1B C12B C15B 119.4(7) . . . . ? N1B C12B C13B O13B 13.6(12) . . . . ? C15B C12B C13B O13B 135.4(10) . . . . ? N1B C12B C13B O14B -170.5(7) . . . . ? C15B C12B C13B O14B -48.8(9) . . . . ? O13B C13B O14B C14B 2.3(14) . . . . ? C12B C13B O14B C14B -173.7(8) . . . . ? N1B C12B C15B C16B -72.0(8) . . . . ? C13B C12B C15B C16B 167.5(7) . . . . ? C12B C15B C16B C17B 96.7(10) . . . . ? C12B C15B C16B C21B -81.0(9) . . . . ? C21B C16B C17B C18B -2.0(13) . . . . ? C15B C16B C17B C18B -179.8(8) . . . . ? C16B C17B C18B C19B 0.6(15) . . . . ? C17B C18B C19B O19B -179.1(9) . . . . ? C17B C18B C19B C20B 1.2(15) . . . . ? O19B C19B C20B C21B 178.8(9) . . . . ? C18B C19B C20B C21B -1.5(16) . . . . ? C19B C20B C21B C16B 0.1(16) . . . . ? C17B C16B C21B C20B 1.7(13) . . . . ? C15B C16B C21B C20B 179.5(8) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.717 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.105