# 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_1a _database_code_depnum_ccdc_archive 'CCDC 914120' #TrackingRef '1-4PF6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3.43 H3.33 F1.14 N0.48 O0.10 P0.19' _chemical_formula_weight 80.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.958(13) _cell_length_b 11.539(13) _cell_length_c 16.667(19) _cell_angle_alpha 75.826(13) _cell_angle_beta 82.501(13) _cell_angle_gamma 65.070(12) _cell_volume 1852(4) _cell_formula_units_Z 21 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9787 _exptl_absorpt_correction_T_max 0.9935 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method multi-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10277 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.01 _reflns_number_total 7067 _reflns_number_gt 5576 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1393P)^2^+1.7347P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7067 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.2335 _refine_ls_wR_factor_gt 0.2161 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.5388(4) 0.7191(4) 0.4520(2) 0.0524(8) Uani 1 1 d . . . H1A H 0.4869 0.8010 0.4212 0.063 Uiso 1 1 calc R . . C2 C 0.6681(4) 0.6449(4) 0.4205(2) 0.0600(9) Uani 1 1 d . . . H2A H 0.7005 0.6797 0.3704 0.072 Uiso 1 1 calc R . . C3 C 0.7442(4) 0.5249(4) 0.4625(2) 0.0548(9) Uani 1 1 d . . . H3A H 0.8287 0.4777 0.4412 0.066 Uiso 1 1 calc R . . C4 C 0.6963(3) 0.4691(3) 0.53975(19) 0.0442(7) Uani 1 1 d . . . C5 C 0.5682(3) 0.5452(3) 0.57351(18) 0.0395(7) Uani 1 1 d . . . C6 C 0.4892(3) 0.6726(3) 0.52660(19) 0.0426(7) Uani 1 1 d . . . C7 C 0.7649(3) 0.3417(3) 0.5827(2) 0.0458(7) Uani 1 1 d . . . H7A H 0.8478 0.2893 0.5622 0.055 Uiso 1 1 calc R . . C8 C 0.7101(3) 0.2918(3) 0.65648(19) 0.0420(7) Uani 1 1 d . . . C9 C 0.5853(3) 0.3787(3) 0.68731(18) 0.0363(6) Uani 1 1 d . . . C10 C 0.5308(3) 0.3319(3) 0.76592(18) 0.0387(6) Uani 1 1 d . . . C11 C 0.5948(4) 0.2057(3) 0.8065(2) 0.0470(7) Uani 1 1 d . . . H11A H 0.5588 0.1756 0.8568 0.056 Uiso 1 1 calc R . . C12 C 0.7152(4) 0.1191(3) 0.7736(2) 0.0547(9) Uani 1 1 d . . . H12A H 0.7561 0.0327 0.8018 0.066 Uiso 1 1 calc R . . C13 C 0.7714(4) 0.1611(3) 0.7012(2) 0.0532(8) Uani 1 1 d . . . H13A H 0.8511 0.1035 0.6807 0.064 Uiso 1 1 calc R . . C14 C 0.4065(3) 0.4248(3) 0.80256(19) 0.0405(7) Uani 1 1 d . . . H14A H 0.3432 0.4795 0.7592 0.049 Uiso 1 1 calc R . . H14B H 0.3642 0.3755 0.8427 0.049 Uiso 1 1 calc R . . C15 C 0.5483(3) 0.5324(3) 0.83051(18) 0.0385(6) Uani 1 1 d . . . H15A H 0.6182 0.4986 0.7934 0.046 Uiso 1 1 calc R . . C16 C 0.3573(3) 0.5747(3) 0.90388(18) 0.0381(6) Uani 1 1 d . . . C17 C 0.2330(3) 0.5821(3) 0.9402(2) 0.0474(8) Uani 1 1 d . . . H17A H 0.1870 0.5391 0.9254 0.057 Uiso 1 1 calc R . . C18 C 0.1824(4) 0.6570(4) 0.9995(2) 0.0597(10) Uani 1 1 d . . . H18A H 0.1000 0.6642 1.0257 0.072 Uiso 1 1 calc R . . C19 C 0.2509(4) 0.7221(4) 1.0214(2) 0.0584(10) Uani 1 1 d . . . H19A H 0.2124 0.7718 1.0616 0.070 Uiso 1 1 calc R . . C20 C 0.3735(4) 0.7154(3) 0.9856(2) 0.0498(8) Uani 1 1 d . . . H20A H 0.4191 0.7586 1.0007 0.060 Uiso 1 1 calc R . . C21 C 0.4254(3) 0.6405(3) 0.92570(18) 0.0393(7) Uani 1 1 d . . . C22 C 0.6543(3) 0.6554(3) 0.8778(2) 0.0432(7) Uani 1 1 d . . . H22A H 0.7409 0.5830 0.8748 0.052 Uiso 1 1 calc R . . H22B H 0.6488 0.6830 0.9292 0.052 Uiso 1 1 calc R . . C23 C 0.6440(3) 0.7677(3) 0.8053(2) 0.0444(7) Uani 1 1 d . . . H23A H 0.6351 0.7443 0.7550 0.053 Uiso 1 1 calc R . . H23B H 0.7268 0.7808 0.7999 0.053 Uiso 1 1 calc R . . C24 C 0.5254(3) 0.8958(3) 0.8140(2) 0.0442(7) Uani 1 1 d . . . H24A H 0.4577 0.8761 0.8513 0.053 Uiso 1 1 calc R . . H24B H 0.5562 0.9460 0.8389 0.053 Uiso 1 1 calc R . . C25 C 0.4609(4) 0.9793(3) 0.7322(2) 0.0463(7) Uani 1 1 d . . . H25A H 0.3972 1.0648 0.7405 0.056 Uiso 1 1 calc R . . H25B H 0.5298 0.9911 0.6924 0.056 Uiso 1 1 calc R . . C26 C 0.2746(3) 0.8995(3) 0.73585(19) 0.0399(6) Uani 1 1 d . . . C27 C 0.1934(3) 0.9377(3) 0.8048(2) 0.0477(8) Uani 1 1 d . . . H27A H 0.2120 0.9833 0.8371 0.057 Uiso 1 1 calc R . . C28 C 0.0848(3) 0.9045(4) 0.8222(2) 0.0563(9) Uani 1 1 d . . . H28A H 0.0293 0.9273 0.8680 0.068 Uiso 1 1 calc R . . C29 C 0.0554(4) 0.8380(4) 0.7735(3) 0.0583(9) Uani 1 1 d . . . H29A H -0.0197 0.8183 0.7875 0.070 Uiso 1 1 calc R . . C30 C 0.1342(3) 0.8002(3) 0.7049(2) 0.0508(8) Uani 1 1 d . . . H30A H 0.1141 0.7561 0.6723 0.061 Uiso 1 1 calc R . . C31 C 0.2465(3) 0.8323(3) 0.68740(19) 0.0403(7) Uani 1 1 d . . . C32 C 0.4286(3) 0.8619(3) 0.63436(18) 0.0415(7) Uani 1 1 d . . . H32A H 0.5029 0.8604 0.5998 0.050 Uiso 1 1 calc R . . C33 C 0.3495(3) 0.7477(3) 0.55648(19) 0.0437(7) Uani 1 1 d . . . H33A H 0.3004 0.8152 0.5107 0.052 Uiso 1 1 calc R . . H33B H 0.3040 0.6891 0.5746 0.052 Uiso 1 1 calc R . . C34 C 0.0511(4) 0.5891(5) 0.2538(3) 0.0685(11) Uani 1 1 d . . . C35 C -0.0350(5) 0.7130(6) 0.2804(5) 0.107(2) Uani 1 1 d . . . H35A H 0.0167 0.7636 0.2775 0.160 Uiso 1 1 calc R . . H35B H -0.0673 0.6940 0.3363 0.160 Uiso 1 1 calc R . . H35C H -0.1100 0.7618 0.2447 0.160 Uiso 1 1 calc R . . C36 C -0.0116(6) 0.4968(6) 0.2539(4) 0.1044(19) Uani 1 1 d . . . H36A H 0.0542 0.4205 0.2359 0.157 Uiso 1 1 calc R . . H36B H -0.0854 0.5388 0.2168 0.157 Uiso 1 1 calc R . . H36C H -0.0441 0.4717 0.3088 0.157 Uiso 1 1 calc R . . N1 N 0.5165(2) 0.5021(2) 0.64685(15) 0.0375(5) Uani 1 1 d . . . N2 N 0.3459(3) 0.8091(2) 0.62536(15) 0.0397(6) Uani 1 1 d . . . N3 N 0.3905(3) 0.9168(2) 0.69944(16) 0.0409(6) Uani 1 1 d . . . N4 N 0.5452(3) 0.6113(2) 0.87792(15) 0.0384(6) Uani 1 1 d . . . N5 N 0.4377(2) 0.5084(2) 0.84336(15) 0.0362(5) Uani 1 1 d . . . O1 O 0.1650(4) 0.5673(5) 0.2319(3) 0.1167(15) Uani 1 1 d . . . P1 P 0.76149(9) 0.83599(9) 0.03364(6) 0.0469(3) Uani 1 1 d . . . P2 P 0.18336(10) 0.15341(10) 0.45570(7) 0.0607(3) Uani 1 1 d . . . F1 F 0.6748(4) 0.9843(3) 0.0066(3) 0.1431(17) Uani 1 1 d . . . F2 F 0.8459(3) 0.6858(3) 0.0641(2) 0.1116(11) Uani 1 1 d . . . F3 F 0.8847(3) 0.8643(4) 0.0475(2) 0.1092(12) Uani 1 1 d . . . F4 F 0.7059(3) 0.8472(4) 0.12627(19) 0.1080(12) Uani 1 1 d . . . F5 F 0.6379(3) 0.8033(3) 0.02353(18) 0.0883(9) Uani 1 1 d . . . F6 F 0.8130(4) 0.8243(4) -0.05704(18) 0.1111(12) Uani 1 1 d . . . F7 F 0.0373(4) 0.2539(4) 0.4435(3) 0.168(2) Uani 1 1 d . . . F8 F 0.3307(4) 0.0441(4) 0.4593(4) 0.174(2) Uani 1 1 d . . . F9 F 0.2469(3) 0.2556(3) 0.4150(2) 0.1082(11) Uani 1 1 d . . . F10 F 0.1887(9) 0.1715(10) 0.5399(3) 0.266(4) Uani 1 1 d . . . F11 F 0.1300(4) 0.0476(4) 0.4933(4) 0.193(3) Uani 1 1 d . . . F12 F 0.1787(6) 0.1431(6) 0.3629(3) 0.169(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.070(2) 0.0476(18) 0.0410(17) -0.0068(14) -0.0017(16) -0.0258(17) C2 0.075(3) 0.066(2) 0.0439(18) -0.0109(17) 0.0106(17) -0.038(2) C3 0.058(2) 0.064(2) 0.0464(18) -0.0203(17) 0.0114(16) -0.0281(18) C4 0.0473(17) 0.0506(18) 0.0393(16) -0.0160(14) 0.0023(13) -0.0217(14) C5 0.0460(16) 0.0414(16) 0.0366(15) -0.0157(12) 0.0015(12) -0.0196(13) C6 0.0524(18) 0.0413(16) 0.0386(15) -0.0126(13) -0.0041(13) -0.0203(14) C7 0.0398(16) 0.0506(18) 0.0466(17) -0.0226(14) 0.0040(13) -0.0127(14) C8 0.0420(16) 0.0417(16) 0.0426(16) -0.0156(13) -0.0029(13) -0.0130(13) C9 0.0384(15) 0.0353(14) 0.0388(15) -0.0138(12) -0.0013(12) -0.0150(12) C10 0.0440(16) 0.0373(15) 0.0418(16) -0.0127(12) 0.0002(13) -0.0212(13) C11 0.0566(19) 0.0401(16) 0.0489(18) -0.0084(14) -0.0002(15) -0.0248(15) C12 0.058(2) 0.0335(16) 0.065(2) -0.0059(15) -0.0065(17) -0.0124(15) C13 0.0463(18) 0.0413(17) 0.066(2) -0.0206(16) -0.0027(16) -0.0071(14) C14 0.0415(16) 0.0420(16) 0.0446(16) -0.0131(13) 0.0043(13) -0.0225(13) C15 0.0401(15) 0.0388(15) 0.0397(15) -0.0138(12) 0.0072(12) -0.0184(12) C16 0.0398(15) 0.0330(14) 0.0355(14) -0.0062(11) 0.0034(12) -0.0111(12) C17 0.0407(16) 0.0449(17) 0.0485(18) -0.0046(14) 0.0045(14) -0.0140(14) C18 0.0482(19) 0.054(2) 0.058(2) -0.0092(17) 0.0171(16) -0.0088(16) C19 0.068(2) 0.0472(19) 0.0456(18) -0.0167(15) 0.0127(17) -0.0098(17) C20 0.065(2) 0.0403(16) 0.0395(16) -0.0114(13) 0.0019(15) -0.0160(15) C21 0.0439(16) 0.0334(14) 0.0349(14) -0.0052(11) 0.0021(12) -0.0122(12) C22 0.0440(16) 0.0437(17) 0.0463(17) -0.0093(13) -0.0059(13) -0.0209(14) C23 0.0456(17) 0.0457(17) 0.0492(17) -0.0133(14) 0.0021(14) -0.0246(14) C24 0.0537(18) 0.0403(16) 0.0462(17) -0.0116(13) -0.0015(14) -0.0250(14) C25 0.060(2) 0.0383(16) 0.0495(18) -0.0094(13) -0.0026(15) -0.0277(15) C26 0.0428(16) 0.0345(14) 0.0398(15) -0.0058(12) -0.0043(12) -0.0132(12) C27 0.0494(18) 0.0441(17) 0.0451(17) -0.0146(14) -0.0004(14) -0.0122(14) C28 0.0413(17) 0.059(2) 0.057(2) -0.0159(17) 0.0061(15) -0.0097(15) C29 0.0404(18) 0.061(2) 0.072(2) -0.0142(19) 0.0022(16) -0.0198(16) C30 0.0445(17) 0.0514(19) 0.060(2) -0.0144(16) -0.0057(15) -0.0200(15) C31 0.0393(15) 0.0351(14) 0.0419(16) -0.0065(12) -0.0066(12) -0.0099(12) C32 0.0483(17) 0.0392(15) 0.0364(15) -0.0068(12) -0.0018(13) -0.0175(13) C33 0.0510(18) 0.0397(16) 0.0405(16) -0.0135(13) -0.0078(13) -0.0140(14) C34 0.051(2) 0.085(3) 0.059(2) -0.011(2) 0.0064(18) -0.022(2) C35 0.068(3) 0.110(5) 0.152(6) -0.057(4) 0.001(3) -0.030(3) C36 0.097(4) 0.094(4) 0.126(5) -0.017(4) 0.015(4) -0.050(3) N1 0.0421(13) 0.0364(13) 0.0357(12) -0.0112(10) -0.0004(10) -0.0158(10) N2 0.0444(14) 0.0366(13) 0.0367(13) -0.0079(10) -0.0053(10) -0.0138(11) N3 0.0480(14) 0.0388(13) 0.0388(13) -0.0100(10) -0.0013(11) -0.0194(11) N4 0.0430(13) 0.0372(13) 0.0402(13) -0.0132(10) 0.0045(10) -0.0200(11) N5 0.0366(12) 0.0354(12) 0.0377(12) -0.0105(10) 0.0032(10) -0.0154(10) O1 0.061(2) 0.160(4) 0.150(4) -0.084(3) 0.043(2) -0.051(2) P1 0.0463(5) 0.0465(5) 0.0537(5) -0.0192(4) 0.0032(4) -0.0210(4) P2 0.0508(6) 0.0590(6) 0.0626(6) -0.0035(5) 0.0006(4) -0.0188(5) F1 0.102(3) 0.0568(18) 0.229(5) -0.004(2) 0.004(3) -0.0099(17) F2 0.103(2) 0.0566(16) 0.142(3) 0.0002(17) 0.002(2) -0.0137(15) F3 0.0648(16) 0.135(3) 0.171(3) -0.089(3) 0.0214(18) -0.0579(18) F4 0.094(2) 0.183(3) 0.0855(19) -0.086(2) 0.0266(16) -0.070(2) F5 0.0794(17) 0.138(3) 0.0882(18) -0.0549(18) 0.0112(14) -0.0705(18) F6 0.132(3) 0.164(3) 0.0638(17) -0.0401(19) 0.0346(17) -0.087(3) F7 0.083(2) 0.114(3) 0.205(5) 0.023(3) 0.030(3) 0.015(2) F8 0.074(2) 0.114(3) 0.246(5) 0.060(3) 0.013(3) -0.013(2) F9 0.107(2) 0.085(2) 0.136(3) -0.0068(19) 0.003(2) -0.0531(19) F10 0.397(10) 0.453(12) 0.102(3) -0.133(6) 0.064(5) -0.301(10) F11 0.091(3) 0.113(3) 0.321(7) 0.068(4) 0.008(3) -0.054(2) F12 0.212(5) 0.244(6) 0.113(3) -0.069(4) 0.008(3) -0.137(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 C1 C6 1.369(5) . ? C1 C2 1.420(6) . ? C2 C3 1.344(6) . ? C3 C4 1.432(5) . ? C4 C7 1.390(5) . ? C4 C5 1.433(4) . ? C5 N1 1.350(4) . ? C5 C6 1.436(5) . ? C6 C33 1.496(5) . ? C7 C8 1.399(5) . ? C8 C13 1.416(5) . ? C8 C9 1.433(4) . ? C9 N1 1.344(4) . ? C9 C10 1.445(4) . ? C10 C11 1.360(5) . ? C10 C14 1.500(4) . ? C11 C12 1.418(5) . ? C12 C13 1.357(5) . ? C14 N5 1.473(4) . ? C15 N5 1.333(4) . ? C15 N4 1.332(4) . ? C16 C21 1.395(5) . ? C16 C17 1.393(5) . ? C16 N5 1.399(4) . ? C17 C18 1.379(5) . ? C18 C19 1.394(6) . ? C19 C20 1.376(6) . ? C20 C21 1.388(5) . ? C21 N4 1.399(4) . ? C22 N4 1.483(4) . ? C22 C23 1.516(5) . ? C23 C24 1.527(5) . ? C24 C25 1.523(5) . ? C25 N3 1.478(4) . ? C26 C31 1.387(4) . ? C26 C27 1.399(5) . ? C26 N3 1.404(4) . ? C27 C28 1.373(5) . ? C28 C29 1.391(6) . ? C29 C30 1.382(5) . ? C30 C31 1.405(5) . ? C31 N2 1.387(4) . ? C32 N3 1.322(4) . ? C32 N2 1.327(4) . ? C33 N2 1.479(4) . ? C34 O1 1.189(5) . ? C34 C36 1.491(7) . ? C34 C35 1.482(7) . ? P1 F1 1.549(4) . ? P1 F6 1.560(3) . ? P1 F2 1.568(3) . ? P1 F3 1.573(3) . ? P1 F5 1.590(3) . ? P1 F4 1.599(3) . ? P2 F10 1.481(5) . ? P2 F11 1.535(4) . ? P2 F7 1.534(4) . ? P2 F8 1.572(4) . ? P2 F9 1.585(3) . ? P2 F12 1.590(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.3(3) . . ? C3 C2 C1 120.7(3) . . ? C2 C3 C4 120.6(3) . . ? C7 C4 C3 123.4(3) . . ? C7 C4 C5 117.5(3) . . ? C3 C4 C5 119.0(3) . . ? N1 C5 C4 123.2(3) . . ? N1 C5 C6 118.0(3) . . ? C4 C5 C6 118.7(3) . . ? C1 C6 C5 119.5(3) . . ? C1 C6 C33 120.8(3) . . ? C5 C6 C33 119.5(3) . . ? C4 C7 C8 120.5(3) . . ? C7 C8 C13 123.4(3) . . ? C7 C8 C9 117.4(3) . . ? C13 C8 C9 119.2(3) . . ? N1 C9 C8 123.3(3) . . ? N1 C9 C10 118.3(3) . . ? C8 C9 C10 118.5(3) . . ? C11 C10 C9 119.6(3) . . ? C11 C10 C14 121.2(3) . . ? C9 C10 C14 119.2(3) . . ? C10 C11 C12 121.3(3) . . ? C13 C12 C11 120.6(3) . . ? C12 C13 C8 120.8(3) . . ? N5 C14 C10 111.6(2) . . ? N5 C15 N4 111.0(3) . . ? C21 C16 C17 121.8(3) . . ? C21 C16 N5 106.7(3) . . ? C17 C16 N5 131.5(3) . . ? C18 C17 C16 116.0(3) . . ? C17 C18 C19 122.1(3) . . ? C20 C19 C18 122.2(3) . . ? C19 C20 C21 116.2(3) . . ? C20 C21 C16 121.7(3) . . ? C20 C21 N4 131.8(3) . . ? C16 C21 N4 106.5(3) . . ? N4 C22 C23 111.3(3) . . ? C22 C23 C24 113.4(3) . . ? C25 C24 C23 113.7(3) . . ? N3 C25 C24 110.7(3) . . ? C31 C26 C27 121.7(3) . . ? C31 C26 N3 105.8(3) . . ? C27 C26 N3 132.5(3) . . ? C28 C27 C26 116.5(3) . . ? C27 C28 C29 122.1(3) . . ? C30 C29 C28 122.1(3) . . ? C29 C30 C31 116.1(3) . . ? N2 C31 C26 107.0(3) . . ? N2 C31 C30 131.6(3) . . ? C26 C31 C30 121.5(3) . . ? N3 C32 N2 110.3(3) . . ? N2 C33 C6 113.2(3) . . ? O1 C34 C36 122.4(5) . . ? O1 C34 C35 120.1(5) . . ? C36 C34 C35 117.5(4) . . ? C9 N1 C5 117.9(3) . . ? C32 N2 C31 108.5(3) . . ? C32 N2 C33 126.3(3) . . ? C31 N2 C33 125.0(3) . . ? C32 N3 C26 108.4(3) . . ? C32 N3 C25 126.5(3) . . ? C26 N3 C25 125.0(3) . . ? C15 N4 C21 108.0(3) . . ? C15 N4 C22 123.7(3) . . ? C21 N4 C22 128.4(3) . . ? C15 N5 C16 107.8(2) . . ? C15 N5 C14 126.3(2) . . ? C16 N5 C14 125.8(2) . . ? F1 P1 F6 92.1(2) . . ? F1 P1 F2 177.8(2) . . ? F6 P1 F2 89.9(2) . . ? F1 P1 F3 90.8(2) . . ? F6 P1 F3 90.2(2) . . ? F2 P1 F3 90.0(2) . . ? F1 P1 F5 90.9(2) . . ? F6 P1 F5 91.66(17) . . ? F2 P1 F5 88.3(2) . . ? F3 P1 F5 177.5(2) . . ? F1 P1 F4 87.9(2) . . ? F6 P1 F4 178.70(17) . . ? F2 P1 F4 90.0(2) . . ? F3 P1 F4 91.11(18) . . ? F5 P1 F4 87.05(16) . . ? F10 P2 F11 89.5(4) . . ? F10 P2 F7 94.0(4) . . ? F11 P2 F7 88.7(3) . . ? F10 P2 F8 92.6(5) . . ? F11 P2 F8 89.3(2) . . ? F7 P2 F8 173.1(3) . . ? F10 P2 F9 92.0(3) . . ? F11 P2 F9 176.3(2) . . ? F7 P2 F9 94.5(3) . . ? F8 P2 F9 87.3(2) . . ? F10 P2 F12 176.1(4) . . ? F11 P2 F12 94.3(4) . . ? F7 P2 F12 85.2(3) . . ? F8 P2 F12 88.4(3) . . ? F9 P2 F12 84.3(2) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 1.004 _refine_diff_density_min -0.692 _refine_diff_density_rms 0.086 data_2a _database_code_depnum_ccdc_archive 'CCDC 914121' #TrackingRef '2-5PF6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C68 H56 F24 N10 O P4' _chemical_formula_weight 1609.11 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 9.6585(4) _cell_length_b 25.7091(12) _cell_length_c 14.0835(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.542(2) _cell_angle_gamma 90.00 _cell_volume 3493.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3622 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 18.51 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1636 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9020 _exptl_absorpt_correction_T_max 0.9492 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 47852 _diffrn_reflns_av_R_equivalents 0.0917 _diffrn_reflns_av_sigmaI/netI 0.0863 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 28.33 _reflns_number_total 8538 _reflns_number_gt 3392 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0863P)^2^+2.3917P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8538 _refine_ls_number_parameters 552 _refine_ls_number_restraints 63 _refine_ls_R_factor_all 0.2034 _refine_ls_R_factor_gt 0.0815 _refine_ls_wR_factor_ref 0.2533 _refine_ls_wR_factor_gt 0.2006 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.111 _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 0.9558(6) 0.1293(3) 0.0641(5) 0.100(2) Uani 1 1 d . . . H1A H 0.9828 0.1302 0.0016 0.120 Uiso 1 1 calc R . . C2 C 0.7374(6) 0.25560(19) 0.2295(4) 0.0878(17) Uani 1 1 d . . . H2A H 0.7108 0.2726 0.2874 0.105 Uiso 1 1 calc R . . H2B H 0.8129 0.2754 0.2042 0.105 Uiso 1 1 calc R . . C3 C 0.9812(6) 0.0857(3) 0.1177(5) 0.101(2) Uani 1 1 d . . . H3A H 1.0263 0.0580 0.0900 0.121 Uiso 1 1 calc R . . C4 C 0.5151(6) 0.2180(2) 0.1596(5) 0.107(2) Uani 1 1 d . . . H4A H 0.5163 0.1929 0.2071 0.129 Uiso 1 1 calc R . . C5 C 0.6192(7) 0.2567(2) 0.1604(5) 0.113(2) Uani 1 1 d . . . H5A H 0.6126 0.2834 0.1160 0.136 Uiso 1 1 calc R . . C6 C 0.7170(8) 0.1480(2) 0.6523(4) 0.097(2) Uani 1 1 d . . . H6A H 0.7533 0.1661 0.7048 0.117 Uiso 1 1 calc R . . C7 C 0.9435(5) 0.0806(2) 0.2105(5) 0.0828(16) Uani 1 1 d . . . H7A H 0.9614 0.0506 0.2458 0.099 Uiso 1 1 calc R . . C8 C 0.4048(6) 0.2172(2) 0.0841(4) 0.0904(18) Uani 1 1 d . . . H8A H 0.3930 0.2456 0.0437 0.108 Uiso 1 1 calc R . . C9 C 0.5456(5) 0.1156(2) -0.0451(3) 0.0726(14) Uani 1 1 d . . . H9A H 0.5116 0.1439 -0.0802 0.087 Uiso 1 1 calc R . . C10 C 0.6533(6) 0.0858(2) -0.0747(4) 0.0795(15) Uani 1 1 d . . . H10A H 0.6948 0.0947 -0.1308 0.095 Uiso 1 1 calc R . . C11 C 0.7030(5) 0.0425(2) -0.0240(4) 0.0790(15) Uani 1 1 d . . . H11A H 0.7756 0.0234 -0.0476 0.095 Uiso 1 1 calc R . . C12 C 0.3124(5) 0.17150(19) 0.0721(4) 0.0792(15) Uani 1 1 d . . . H12A H 0.2363 0.1748 0.1144 0.095 Uiso 1 1 calc R . . H12B H 0.2736 0.1708 0.0074 0.095 Uiso 1 1 calc R . . C13 C 0.8915(6) 0.1716(3) 0.1007(4) 0.0852(16) Uani 1 1 d . . . H13A H 0.8747 0.2016 0.0650 0.102 Uiso 1 1 calc R . . C14 C 0.5838(7) 0.1326(2) 0.6496(3) 0.0862(17) Uani 1 1 d . . . H14A H 0.5286 0.1401 0.7003 0.103 Uiso 1 1 calc R . . C15 C 0.8770(4) 0.12333(18) 0.2474(3) 0.0597(12) Uani 1 1 d . . . C16 C 0.8021(6) 0.1367(2) 0.5759(4) 0.0858(17) Uani 1 1 d . . . H16A H 0.8943 0.1472 0.5798 0.103 Uiso 1 1 calc R . . C17 C 0.8526(5) 0.16764(19) 0.1939(4) 0.0637(12) Uani 1 1 d . . . C18 C 0.7755(5) 0.17983(19) 0.3373(3) 0.0624(12) Uani 1 1 d . . . H18A H 0.7361 0.1952 0.3894 0.075 Uiso 1 1 calc R . . C19 C 0.2098(5) 0.0350(2) 0.4762(4) 0.0727(14) Uani 1 1 d . . . H19A H 0.1488 0.0394 0.5249 0.087 Uiso 1 1 calc R . . C20 C 0.3923(5) 0.08509(19) 0.5636(3) 0.0658(13) Uani 1 1 d . . . H20A H 0.3340 0.0906 0.6134 0.079 Uiso 1 1 calc R . . C21 C 0.4837(5) 0.01452(17) 0.2465(3) 0.0597(12) Uani 1 1 d . . . H21A H 0.5790 0.0148 0.2712 0.072 Uiso 1 1 calc R . . H21B H 0.4656 -0.0192 0.2176 0.072 Uiso 1 1 calc R . . C22 C 0.1701(5) 0.0078(2) 0.3992(4) 0.0776(15) Uani 1 1 d . . . H22A H 0.0820 -0.0068 0.3950 0.093 Uiso 1 1 calc R . . C23 C 0.4902(5) 0.10116(18) 0.0406(3) 0.0596(12) Uani 1 1 d . . . C24 C 0.2593(5) 0.00107(18) 0.3241(4) 0.0685(13) Uani 1 1 d . . . H24A H 0.2291 -0.0181 0.2711 0.082 Uiso 1 1 calc R . . C25 C 0.7533(5) 0.11095(17) 0.4968(3) 0.0601(12) Uani 1 1 d . . . C26 C 0.6478(5) 0.02751(18) 0.0595(3) 0.0620(12) Uani 1 1 d . . . H26A H 0.6798 -0.0016 0.0931 0.074 Uiso 1 1 calc R . . C27 C 0.5409(4) 0.05843(17) 0.0911(3) 0.0526(10) Uani 1 1 d . . . C28 C 0.8455(4) 0.09797(19) 0.4191(3) 0.0667(13) Uani 1 1 d . . . H28A H 0.9410 0.0999 0.4431 0.080 Uiso 1 1 calc R . . H28B H 0.8276 0.0624 0.3989 0.080 Uiso 1 1 calc R . . C29 C 0.3758(5) 0.09442(17) 0.1704(3) 0.0591(11) Uani 1 1 d . . . H29A H 0.3138 0.1012 0.2176 0.071 Uiso 1 1 calc R . . C30 C 0.5268(5) 0.10483(18) 0.5692(3) 0.0626(12) Uani 1 1 d . . . C31 C 0.3893(4) 0.02196(16) 0.3270(3) 0.0531(10) Uani 1 1 d . . . C32 C 0.4371(4) 0.05010(16) 0.4091(3) 0.0490(10) Uani 1 1 d . . . C33 C 0.3449(4) 0.05736(17) 0.4847(3) 0.0560(11) Uani 1 1 d . . . C34 C 0.6123(4) 0.09431(16) 0.4914(3) 0.0509(10) Uani 1 1 d . . . N5 N 0.5673(3) 0.06840(13) 0.4124(2) 0.0480(8) Uani 1 1 d . . . N1 N 0.3861(4) 0.12234(14) 0.0924(3) 0.0635(10) Uani 1 1 d . . . N2 N 0.7875(4) 0.20250(14) 0.2532(3) 0.0647(10) Uani 1 1 d . . . N3 N 0.8273(3) 0.13243(14) 0.3365(3) 0.0558(9) Uani 1 1 d . . . N4 N 0.4654(4) 0.05564(13) 0.1725(2) 0.0545(9) Uani 1 1 d . . . F1 F -0.0190(4) 0.0634(2) 0.8053(4) 0.202(3) Uani 1 1 d D B . F2 F 0.2610(4) 0.1162(2) 0.7890(4) 0.190(2) Uani 1 1 d D B . F3 F 0.0559(6) 0.14095(14) 0.8328(3) 0.163(2) Uani 1 1 d D B . P2 P 0.2018(7) 0.2042(4) 0.3748(5) 0.072(2) Uani 0.554(13) 1 d PD A 1 F9 F 0.3523(7) 0.1861(5) 0.3594(9) 0.139(6) Uani 0.554(13) 1 d PD A 1 F11 F 0.0551(8) 0.2172(5) 0.3931(10) 0.173(7) Uani 0.554(13) 1 d PD A 1 F4 F 0.0911(5) 0.10757(19) 0.6938(2) 0.161(2) Uani 1 1 d D B 1 F5 F 0.1547(5) 0.07419(17) 0.9013(2) 0.1498(18) Uani 1 1 d D B 1 F7 F 0.2210(19) 0.1816(6) 0.4774(7) 0.216(9) Uani 0.554(13) 1 d PD A 1 F8 F 0.1935(18) 0.2246(6) 0.2731(6) 0.214(11) Uani 0.554(13) 1 d PD A 1 F10 F 0.1595(10) 0.1494(4) 0.3373(12) 0.176(7) Uani 0.554(13) 1 d PD A 1 F12 F 0.2460(12) 0.2573(3) 0.4132(10) 0.157(6) Uani 0.554(13) 1 d PD A 1 P2' P 0.2084(12) 0.2132(5) 0.3709(9) 0.113(5) Uani 0.446(13) 1 d PD A 2 F9' F 0.300(2) 0.1677(6) 0.3381(12) 0.237(14) Uani 0.446(13) 1 d PD A 2 F11' F 0.123(2) 0.2582(7) 0.4081(10) 0.247(13) Uani 0.446(13) 1 d PD A 2 F7' F 0.2865(12) 0.2093(7) 0.4685(8) 0.145(7) Uani 0.446(13) 1 d PD A 2 F8' F 0.1299(17) 0.2136(9) 0.2756(9) 0.219(13) Uani 0.446(13) 1 d PD A 2 F10' F 0.1040(17) 0.1745(9) 0.4102(11) 0.229(14) Uani 0.446(13) 1 d PD A 2 F12' F 0.3115(13) 0.2518(5) 0.3323(12) 0.166(7) Uani 0.446(13) 1 d PD A 2 F6 F 0.1888(5) 0.03993(13) 0.7608(3) 0.1363(16) Uani 1 1 d D B . P1 P 0.11947(13) 0.09015(5) 0.79699(8) 0.0604(4) Uani 1 1 d D . . O1 O 0.5807(6) 0.2437(3) 0.4630(6) 0.097(3) Uani 0.50 1 d P . . 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 0.079(4) 0.132(6) 0.089(4) -0.025(5) 0.014(3) -0.005(4) C2 0.108(4) 0.047(3) 0.108(4) 0.013(3) -0.001(3) -0.003(3) C3 0.067(4) 0.123(6) 0.112(5) -0.050(5) 0.003(4) 0.008(4) C4 0.104(5) 0.092(4) 0.122(5) 0.039(4) -0.033(4) -0.031(4) C5 0.128(5) 0.055(4) 0.151(6) 0.028(4) -0.061(5) -0.004(4) C6 0.138(6) 0.080(4) 0.070(4) -0.004(3) -0.027(4) -0.024(4) C7 0.058(3) 0.075(4) 0.114(5) -0.017(3) -0.011(3) 0.005(3) C8 0.100(4) 0.062(4) 0.106(4) 0.015(3) -0.030(3) 0.009(3) C9 0.082(4) 0.072(3) 0.063(3) -0.002(3) -0.005(3) -0.001(3) C10 0.087(4) 0.093(4) 0.059(3) -0.010(3) 0.006(3) -0.016(3) C11 0.071(3) 0.096(4) 0.071(3) -0.019(3) 0.009(3) 0.003(3) C12 0.077(3) 0.064(3) 0.096(4) 0.016(3) -0.002(3) 0.019(3) C13 0.076(4) 0.103(5) 0.078(4) 0.003(3) 0.008(3) -0.016(3) C14 0.134(6) 0.075(4) 0.049(3) -0.005(3) 0.000(3) 0.002(4) C15 0.042(2) 0.059(3) 0.077(3) -0.007(3) -0.002(2) -0.004(2) C16 0.094(4) 0.071(4) 0.089(4) 0.017(3) -0.032(3) -0.023(3) C17 0.056(3) 0.060(3) 0.076(3) 0.000(3) 0.005(2) -0.009(2) C18 0.060(3) 0.055(3) 0.072(3) 0.007(2) 0.007(2) -0.001(2) C19 0.051(3) 0.085(4) 0.083(4) 0.027(3) 0.015(3) 0.005(3) C20 0.076(3) 0.073(3) 0.050(3) 0.008(2) 0.020(2) 0.017(3) C21 0.070(3) 0.048(3) 0.060(3) -0.002(2) -0.005(2) 0.009(2) C22 0.048(3) 0.080(4) 0.104(4) 0.030(3) -0.002(3) -0.009(3) C23 0.060(3) 0.060(3) 0.058(3) 0.000(2) -0.004(2) -0.003(2) C24 0.064(3) 0.055(3) 0.085(3) 0.006(2) -0.016(3) -0.010(2) C25 0.058(3) 0.054(3) 0.067(3) 0.013(2) -0.011(2) -0.007(2) C26 0.063(3) 0.058(3) 0.064(3) -0.011(2) -0.003(2) 0.008(2) C27 0.051(2) 0.054(3) 0.052(2) -0.006(2) -0.003(2) -0.002(2) C28 0.046(3) 0.062(3) 0.092(3) 0.021(3) -0.007(2) -0.005(2) C29 0.061(3) 0.050(3) 0.067(3) 0.000(2) 0.007(2) 0.001(2) C30 0.079(3) 0.058(3) 0.050(3) 0.001(2) 0.001(2) 0.003(2) C31 0.055(3) 0.045(2) 0.059(3) 0.005(2) -0.006(2) -0.001(2) C32 0.047(2) 0.049(3) 0.051(2) 0.0100(19) 0.0017(19) 0.003(2) C33 0.052(3) 0.055(3) 0.062(3) 0.015(2) 0.013(2) 0.005(2) C34 0.060(3) 0.045(2) 0.047(2) 0.0049(19) -0.0025(19) 0.002(2) N5 0.0462(19) 0.050(2) 0.0482(19) 0.0038(16) 0.0007(15) 0.0004(16) N1 0.064(2) 0.055(2) 0.072(3) 0.005(2) 0.0041(19) 0.0064(19) N2 0.074(3) 0.045(2) 0.075(3) 0.007(2) 0.001(2) -0.0039(19) N3 0.049(2) 0.046(2) 0.073(3) 0.0060(18) 0.0029(18) -0.0013(17) N4 0.058(2) 0.049(2) 0.057(2) -0.0020(17) 0.0002(17) 0.0055(18) F1 0.109(3) 0.257(6) 0.243(6) -0.052(5) 0.041(4) -0.091(4) F2 0.117(3) 0.253(6) 0.204(5) -0.043(4) 0.043(3) -0.089(4) F3 0.270(6) 0.095(3) 0.131(3) 0.015(2) 0.079(3) 0.077(3) P2 0.061(3) 0.091(4) 0.064(3) -0.016(2) 0.003(2) -0.016(3) F9 0.055(5) 0.176(13) 0.185(11) -0.005(8) 0.000(5) 0.003(5) F11 0.066(5) 0.214(14) 0.242(16) -0.123(12) 0.032(6) 0.004(7) F4 0.200(4) 0.210(5) 0.074(2) 0.035(3) 0.017(2) 0.114(4) F5 0.200(4) 0.182(4) 0.068(2) 0.012(2) 0.016(2) 0.100(3) F7 0.35(2) 0.191(14) 0.118(9) 0.036(9) 0.086(13) 0.109(14) F8 0.27(2) 0.30(2) 0.075(8) 0.024(9) 0.049(9) 0.158(18) F10 0.115(7) 0.146(9) 0.269(17) -0.108(11) 0.028(9) -0.041(6) F12 0.160(11) 0.090(7) 0.219(15) -0.048(9) -0.016(11) -0.049(7) P2' 0.111(7) 0.122(8) 0.109(8) -0.046(5) 0.030(5) -0.045(5) F9' 0.43(4) 0.128(13) 0.166(15) -0.007(11) 0.14(2) 0.10(2) F11' 0.36(3) 0.23(2) 0.156(14) -0.025(12) 0.101(19) 0.15(2) F7' 0.117(8) 0.22(2) 0.094(9) 0.007(9) -0.038(7) -0.042(9) F8' 0.180(15) 0.36(3) 0.109(12) 0.006(13) -0.056(11) -0.120(18) F10' 0.18(2) 0.34(4) 0.162(16) 0.06(2) 0.025(14) -0.18(2) F12' 0.156(11) 0.168(13) 0.178(14) 0.042(10) 0.057(10) -0.056(9) F6 0.207(4) 0.092(3) 0.114(3) 0.007(2) 0.055(3) 0.057(3) P1 0.0614(8) 0.0595(8) 0.0606(7) 0.0011(6) 0.0061(6) 0.0051(6) O1 0.042(3) 0.113(6) 0.138(6) -0.090(5) 0.011(4) 0.000(4) _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 C13 1.365(8) . ? C1 C3 1.367(9) . ? C1 H1A 0.9300 . ? C2 C5 1.467(8) . ? C2 N2 1.482(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C7 1.379(8) . ? C3 H3A 0.9300 . ? C4 C5 1.413(8) . ? C4 C8 1.471(7) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C14 1.344(8) . ? C6 C16 1.412(8) . ? C6 H6A 0.9300 . ? C7 C15 1.386(7) . ? C7 H7A 0.9300 . ? C8 C12 1.480(7) . ? C8 H8A 0.9300 . ? C9 C10 1.373(7) . ? C9 C23 1.392(6) . ? C9 H9A 0.9300 . ? C10 C11 1.395(7) . ? C10 H10A 0.9300 . ? C11 C26 1.368(7) . ? C11 H11A 0.9300 . ? C12 N1 1.472(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C17 1.385(7) . ? C13 H13A 0.9300 . ? C14 C30 1.429(7) . ? C14 H14A 0.9300 . ? C15 C17 1.381(6) . ? C15 N3 1.382(6) . ? C16 C25 1.362(7) . ? C16 H16A 0.9300 . ? C17 N2 1.394(6) . ? C18 N3 1.318(5) . ? C18 N2 1.330(5) . ? C18 H18A 0.9300 . ? C19 C22 1.333(7) . ? C19 C33 1.427(6) . ? C19 H19A 0.9300 . ? C20 C33 1.380(6) . ? C20 C30 1.393(7) . ? C20 H20A 0.9300 . ? C21 N4 1.489(5) . ? C21 C31 1.498(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C24 1.404(7) . ? C22 H22A 0.9300 . ? C23 N1 1.380(6) . ? C23 C27 1.386(6) . ? C24 C31 1.364(6) . ? C24 H24A 0.9300 . ? C25 C34 1.426(6) . ? C25 C28 1.480(6) . ? C26 C27 1.392(6) . ? C26 H26A 0.9300 . ? C27 N4 1.387(5) . ? C28 N3 1.466(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 N4 1.320(5) . ? C29 N1 1.320(5) . ? C29 H29A 0.9300 . ? C30 C34 1.426(6) . ? C31 C32 1.423(6) . ? C32 N5 1.342(5) . ? C32 C33 1.431(6) . ? C34 N5 1.353(5) . ? F1 P1 1.513(4) . ? F2 P1 1.530(4) . ? F3 P1 1.537(3) . ? P2 F11 1.490(9) . ? P2 F12 1.523(10) . ? P2 F8 1.523(10) . ? P2 F9 1.551(9) . ? P2 F10 1.551(10) . ? P2 F7 1.562(10) . ? F4 P1 1.534(3) . ? F5 P1 1.549(3) . ? P2' F8' 1.512(13) . ? P2' F12' 1.522(13) . ? P2' F11' 1.524(13) . ? P2' F10' 1.538(13) . ? P2' F7' 1.542(12) . ? P2' F9' 1.549(13) . ? F6 P1 1.551(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 C13 C1 C3 121.2(6) . . ? C13 C1 H1A 119.4 . . ? C3 C1 H1A 119.4 . . ? C5 C2 N2 113.8(4) . . ? C5 C2 H2A 108.8 . . ? N2 C2 H2A 108.8 . . ? C5 C2 H2B 108.8 . . ? N2 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C1 C3 C7 123.6(6) . . ? C1 C3 H3A 118.2 . . ? C7 C3 H3A 118.2 . . ? C5 C4 C8 120.5(5) . . ? C5 C4 H4A 119.7 . . ? C8 C4 H4A 119.7 . . ? C4 C5 C2 121.6(5) . . ? C4 C5 H5A 119.2 . . ? C2 C5 H5A 119.2 . . ? C14 C6 C16 120.4(5) . . ? C14 C6 H6A 119.8 . . ? C16 C6 H6A 119.8 . . ? C3 C7 C15 115.2(6) . . ? C3 C7 H7A 122.4 . . ? C15 C7 H7A 122.4 . . ? C4 C8 C12 120.5(5) . . ? C4 C8 H8A 119.8 . . ? C12 C8 H8A 119.8 . . ? C10 C9 C23 116.1(5) . . ? C10 C9 H9A 121.9 . . ? C23 C9 H9A 121.9 . . ? C9 C10 C11 122.5(5) . . ? C9 C10 H10A 118.7 . . ? C11 C10 H10A 118.7 . . ? C26 C11 C10 121.8(5) . . ? C26 C11 H11A 119.1 . . ? C10 C11 H11A 119.1 . . ? N1 C12 C8 112.1(4) . . ? N1 C12 H12A 109.2 . . ? C8 C12 H12A 109.2 . . ? N1 C12 H12B 109.2 . . ? C8 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C1 C13 C17 116.5(6) . . ? C1 C13 H13A 121.8 . . ? C17 C13 H13A 121.8 . . ? C6 C14 C30 120.3(5) . . ? C6 C14 H14A 119.9 . . ? C30 C14 H14A 119.9 . . ? C17 C15 N3 107.4(4) . . ? C17 C15 C7 121.3(5) . . ? N3 C15 C7 131.3(5) . . ? C25 C16 C6 122.1(5) . . ? C25 C16 H16A 119.0 . . ? C6 C16 H16A 119.0 . . ? C15 C17 C13 122.2(5) . . ? C15 C17 N2 105.9(4) . . ? C13 C17 N2 132.0(5) . . ? N3 C18 N2 110.4(4) . . ? N3 C18 H18A 124.8 . . ? N2 C18 H18A 124.8 . . ? C22 C19 C33 120.6(5) . . ? C22 C19 H19A 119.7 . . ? C33 C19 H19A 119.7 . . ? C33 C20 C30 120.6(4) . . ? C33 C20 H20A 119.7 . . ? C30 C20 H20A 119.7 . . ? N4 C21 C31 112.4(3) . . ? N4 C21 H21A 109.1 . . ? C31 C21 H21A 109.1 . . ? N4 C21 H21B 109.1 . . ? C31 C21 H21B 109.1 . . ? H21A C21 H21B 107.9 . . ? C19 C22 C24 120.9(5) . . ? C19 C22 H22A 119.5 . . ? C24 C22 H22A 119.5 . . ? N1 C23 C27 106.9(4) . . ? N1 C23 C9 132.1(4) . . ? C27 C23 C9 121.0(4) . . ? C31 C24 C22 121.5(5) . . ? C31 C24 H24A 119.2 . . ? C22 C24 H24A 119.2 . . ? C16 C25 C34 119.0(5) . . ? C16 C25 C28 121.2(5) . . ? C34 C25 C28 119.8(4) . . ? C11 C26 C27 115.9(5) . . ? C11 C26 H26A 122.1 . . ? C27 C26 H26A 122.1 . . ? C23 C27 N4 106.1(4) . . ? C23 C27 C26 122.6(4) . . ? N4 C27 C26 131.3(4) . . ? N3 C28 C25 113.3(4) . . ? N3 C28 H28A 108.9 . . ? C25 C28 H28A 108.9 . . ? N3 C28 H28B 108.9 . . ? C25 C28 H28B 108.9 . . ? H28A C28 H28B 107.7 . . ? N4 C29 N1 110.8(4) . . ? N4 C29 H29A 124.6 . . ? N1 C29 H29A 124.6 . . ? C20 C30 C34 117.2(4) . . ? C20 C30 C14 123.5(5) . . ? C34 C30 C14 119.2(5) . . ? C24 C31 C32 119.3(4) . . ? C24 C31 C21 121.1(4) . . ? C32 C31 C21 119.6(4) . . ? N5 C32 C31 118.4(4) . . ? N5 C32 C33 122.8(4) . . ? C31 C32 C33 118.8(4) . . ? C20 C33 C19 123.1(4) . . ? C20 C33 C32 118.1(4) . . ? C19 C33 C32 118.8(4) . . ? N5 C34 C25 117.6(4) . . ? N5 C34 C30 123.3(4) . . ? C25 C34 C30 119.1(4) . . ? C32 N5 C34 117.9(3) . . ? C29 N1 C23 108.0(4) . . ? C29 N1 C12 125.1(4) . . ? C23 N1 C12 126.4(4) . . ? C18 N2 C17 108.2(4) . . ? C18 N2 C2 124.3(4) . . ? C17 N2 C2 127.5(4) . . ? C18 N3 C15 108.2(4) . . ? C18 N3 C28 125.7(4) . . ? C15 N3 C28 125.7(4) . . ? C29 N4 C27 108.1(4) . . ? C29 N4 C21 127.5(4) . . ? C27 N4 C21 124.4(3) . . ? F11 P2 F12 89.4(7) . . ? F11 P2 F8 94.3(7) . . ? F12 P2 F8 91.6(8) . . ? F11 P2 F9 175.3(10) . . ? F12 P2 F9 93.9(7) . . ? F8 P2 F9 89.0(7) . . ? F11 P2 F10 91.5(6) . . ? F12 P2 F10 178.6(8) . . ? F8 P2 F10 89.5(8) . . ? F9 P2 F10 85.2(6) . . ? F11 P2 F7 89.9(8) . . ? F12 P2 F7 89.1(7) . . ? F8 P2 F7 175.8(8) . . ? F9 P2 F7 86.8(7) . . ? F10 P2 F7 89.8(8) . . ? F8' P2' F12' 89.4(9) . . ? F8' P2' F11' 92.5(10) . . ? F12' P2' F11' 90.0(10) . . ? F8' P2' F10' 90.7(9) . . ? F12' P2' F10' 179.7(13) . . ? F11' P2' F10' 89.7(10) . . ? F8' P2' F7' 176.5(12) . . ? F12' P2' F7' 93.4(9) . . ? F11' P2' F7' 89.6(9) . . ? F10' P2' F7' 86.5(9) . . ? F8' P2' F9' 90.6(10) . . ? F12' P2' F9' 89.6(9) . . ? F11' P2' F9' 176.9(12) . . ? F10' P2' F9' 90.6(10) . . ? F7' P2' F9' 87.3(9) . . ? F1 P1 F2 178.8(4) . . ? F1 P1 F4 94.9(3) . . ? F2 P1 F4 85.7(3) . . ? F1 P1 F3 89.6(3) . . ? F2 P1 F3 91.4(3) . . ? F4 P1 F3 90.3(2) . . ? F1 P1 F5 87.9(3) . . ? F2 P1 F5 91.5(3) . . ? F4 P1 F5 177.2(3) . . ? F3 P1 F5 89.3(2) . . ? F1 P1 F6 92.5(3) . . ? F2 P1 F6 86.5(3) . . ? F4 P1 F6 89.6(2) . . ? F3 P1 F6 177.9(3) . . ? F5 P1 F6 90.6(2) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.604 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.064 data_1b _database_code_depnum_ccdc_archive 'CCDC 914123' #TrackingRef '4-5Br.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H15.50 Br N2.50 O1.50' _chemical_formula_weight 358.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 14.481(3) _cell_length_b 13.824(3) _cell_length_c 16.878(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.685(3) _cell_angle_gamma 90.00 _cell_volume 3181.2(11) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.65 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 2.591 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2837 _exptl_absorpt_correction_T_max 0.5636 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22227 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.1145 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 27.60 _reflns_number_total 13934 _reflns_number_gt 10002 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0950P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 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 0.00(2) _refine_ls_number_reflns 13934 _refine_ls_number_parameters 794 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1060 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1815 _refine_ls_wR_factor_gt 0.1537 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.89606(6) 0.77930(6) 0.70176(4) 0.03155(18) Uani 1 1 d . . . Br2 Br 0.28642(6) 0.28492(6) 0.05475(4) 0.0349(2) Uani 1 1 d . . . Br3 Br 0.46135(6) 0.67750(6) 0.64490(5) 0.0365(2) Uani 1 1 d . . . Br4 Br 0.87070(7) 0.99549(6) 0.33031(8) 0.0538(3) Uani 1 1 d . . . C49 C 0.8717(5) 0.5989(5) 0.3619(4) 0.0203(15) Uani 1 1 d . . . H49A H 0.8603 0.5997 0.4142 0.024 Uiso 1 1 calc R . . C43 C 0.6336(5) 0.6560(4) 0.3727(4) 0.0166(13) Uani 1 1 d . . . N6 N 0.5868(4) 0.5949(4) 0.3111(3) 0.0179(12) Uani 1 1 d . . . N10 N 0.8187(4) 0.6482(4) 0.2938(3) 0.0181(12) Uani 1 1 d . . . C39 C 0.5122(5) 0.5394(5) 0.3200(4) 0.0169(14) Uani 1 1 d . . . C9 C 0.5226(5) 0.3034(4) 0.8305(4) 0.0209(15) Uani 1 1 d . . . C67 C 0.6086(5) 0.4901(5) 0.0532(4) 0.0237(15) Uani 1 1 d . . . H67A H 0.5578 0.5371 0.0363 0.028 Uiso 1 1 calc R . . N1 N 0.5969(4) 0.2487(4) 0.8231(4) 0.0205(12) Uani 1 1 d . . . N2 N 0.8179(4) 0.1940(4) 0.7945(4) 0.0223(12) Uani 1 1 d . . . N3 N 0.9398(4) 0.2966(4) 0.8320(4) 0.0245(13) Uani 1 1 d . . . C38 C 0.4843(5) 0.5438(5) 0.3931(4) 0.0188(14) Uani 1 1 d . . . C4 C 0.6191(5) 0.1815(5) 0.9614(4) 0.0255(15) Uani 1 1 d . . . C47 C 0.7082(5) 0.7189(5) 0.3618(4) 0.0220(15) Uani 1 1 d . . . C8 C 0.4930(5) 0.3004(5) 0.9029(4) 0.0219(15) Uani 1 1 d . . . N9 N 0.9416(4) 0.5490(4) 0.3474(3) 0.0194(12) Uani 1 1 d . . . N4 N 0.6859(4) 0.5409(4) 0.7247(4) 0.0214(12) Uani 1 1 d . . . C42 C 0.6094(5) 0.6672(5) 0.4474(4) 0.0215(14) Uani 1 1 d . . . C58 C 0.8744(6) 0.3541(6) 0.3364(5) 0.0297(17) Uani 1 1 d . . . H58A H 0.8305 0.4076 0.3074 0.036 Uiso 1 1 calc R . . H58B H 0.9118 0.3333 0.3000 0.036 Uiso 1 1 calc R . . C40 C 0.4588(5) 0.4769(5) 0.2536(4) 0.0201(14) Uani 1 1 d . . . C36 C 0.3602(5) 0.4219(5) 0.3353(4) 0.0256(16) Uani 1 1 d . . . H36A H 0.3092 0.3814 0.3397 0.031 Uiso 1 1 calc R . . C6 C 0.7195(5) 0.1258(5) 0.8781(5) 0.0249(16) Uani 1 1 d . . . N7 N 0.5672(4) 0.4200(4) 0.1758(3) 0.0174(12) Uani 1 1 d . . . N5 N 0.5770(4) 0.4262(4) 0.6869(3) 0.0195(12) Uani 1 1 d . . . C13 C 0.4701(5) 0.3639(5) 0.7614(4) 0.0242(16) Uani 1 1 d . . . C15 C 0.6133(5) 0.4962(5) 0.7425(4) 0.0180(13) Uani 1 1 d . . . H15A H 0.5913 0.5120 0.7880 0.022 Uiso 1 1 calc R . . C48 C 0.7352(5) 0.7136(5) 0.2834(5) 0.0230(15) Uani 1 1 d . . . H48A H 0.6779 0.6905 0.2361 0.028 Uiso 1 1 calc R . . H48B H 0.7522 0.7791 0.2691 0.028 Uiso 1 1 calc R . . C62 C 0.4794(5) 0.4771(5) 0.1713(4) 0.0198(14) Uani 1 1 d . . . H62A H 0.4220 0.4503 0.1263 0.024 Uiso 1 1 calc R . . H62B H 0.4888 0.5446 0.1560 0.024 Uiso 1 1 calc R . . N8 N 0.6813(4) 0.3100(4) 0.2138(4) 0.0221(13) Uani 1 1 d . . . C53 C 0.9624(6) 0.5575(5) 0.1349(4) 0.0253(16) Uani 1 1 d . . . H53A H 0.9981 0.5350 0.1005 0.030 Uiso 1 1 calc R . . C52 C 0.8850(6) 0.6237(5) 0.1010(4) 0.0258(16) Uani 1 1 d . . . H52A H 0.8697 0.6438 0.0442 0.031 Uiso 1 1 calc R . . C51 C 0.8307(5) 0.6602(5) 0.1476(4) 0.0247(15) Uani 1 1 d . . . H51A H 0.7795 0.7058 0.1249 0.030 Uiso 1 1 calc R . . C5 C 0.6434(5) 0.1892(5) 0.8869(4) 0.0217(14) Uani 1 1 d . . . C12 C 0.3940(6) 0.4215(5) 0.7678(5) 0.0287(17) Uani 1 1 d . . . H12A H 0.3605 0.4633 0.7226 0.034 Uiso 1 1 calc R . . C60 C 0.7449(6) 0.2314(5) 0.2641(5) 0.0308(18) Uani 1 1 d . . . H60A H 0.7847 0.2037 0.2322 0.037 Uiso 1 1 calc R . . H60B H 0.7032 0.1792 0.2741 0.037 Uiso 1 1 calc R . . O1 O 0.0560(5) 0.7397(5) 0.9537(4) 0.0540(18) Uani 1 1 d . . . C28 C 0.7410(6) 0.1243(6) 0.7976(5) 0.0307(17) Uani 1 1 d . . . H28A H 0.7620 0.0583 0.7886 0.037 Uiso 1 1 calc R . . H28B H 0.6798 0.1388 0.7507 0.037 Uiso 1 1 calc R . . O2 O 0.0585(5) 0.1315(5) 0.4475(4) 0.0441(15) Uani 1 1 d . . . C22 C 0.7476(6) 0.6182(5) 0.7772(5) 0.0271(17) Uani 1 1 d . . . H22A H 0.7059 0.6627 0.7964 0.033 Uiso 1 1 calc R . . H22B H 0.7785 0.6560 0.7430 0.033 Uiso 1 1 calc R . . C61 C 0.6061(5) 0.3483(5) 0.2305(4) 0.0204(14) Uani 1 1 d . . . H61A H 0.5832 0.3282 0.2745 0.024 Uiso 1 1 calc R . . C35 C 0.3863(5) 0.4197(5) 0.2615(5) 0.0232(15) Uani 1 1 d . . . H35A H 0.3524 0.3774 0.2168 0.028 Uiso 1 1 calc R . . C50 C 0.8556(5) 0.6262(5) 0.2301(4) 0.0193(14) Uani 1 1 d . . . C20 C 0.7599(6) 0.5189(5) 0.6102(5) 0.0288(17) Uani 1 1 d . . . H20A H 0.8079 0.5686 0.6272 0.035 Uiso 1 1 calc R . . C7 C 0.5420(6) 0.2381(5) 0.9684(4) 0.0274(17) Uani 1 1 d . . . H7A H 0.5234 0.2340 1.0172 0.033 Uiso 1 1 calc R . . C29 C 0.9228(5) 0.2752(6) 0.7484(4) 0.0261(14) Uani 1 1 d . . . C21 C 0.6968(5) 0.4987(5) 0.6538(4) 0.0198(14) Uani 1 1 d . . . C16 C 0.6253(5) 0.4254(5) 0.6289(4) 0.0189(14) Uani 1 1 d . . . O3 O 0.7220(7) 0.0273(5) 0.4499(5) 0.073(2) Uani 1 1 d . . . O4 O 0.4770(5) 0.1417(5) 0.1457(4) 0.0478(16) Uani 1 1 d . . . C68 C 0.6198(5) 0.4285(5) 0.1222(4) 0.0186(14) Uani 1 1 d . . . C17 C 0.6130(6) 0.3690(5) 0.5583(5) 0.0267(16) Uani 1 1 d . . . H17A H 0.5642 0.3201 0.5414 0.032 Uiso 1 1 calc R . . C27 C 0.8761(5) 0.2476(5) 0.8585(5) 0.0236(15) Uani 1 1 d . . . H27A H 0.8725 0.2502 0.9136 0.028 Uiso 1 1 calc R . . O6 O 0.0744(5) 0.6413(5) 0.8112(4) 0.0475(16) Uani 1 1 d . . . C55 C 0.9332(5) 0.5622(5) 0.2625(4) 0.0177(13) Uani 1 1 d . . . C66 C 0.6747(6) 0.4790(6) 0.0115(5) 0.0341(19) Uani 1 1 d . . . H66A H 0.6701 0.5195 -0.0352 0.041 Uiso 1 1 calc R . . C46 C 0.7521(5) 0.7857(6) 0.4233(5) 0.0312(16) Uani 1 1 d . . . H46A H 0.8010 0.8269 0.4158 0.037 Uiso 1 1 calc R . . O5 O 0.1091(5) 0.3649(5) 0.1168(4) 0.0484(16) Uani 1 1 d . . . C30 C 0.9688(6) 0.3039(5) 0.6920(5) 0.0326(19) Uani 1 1 d . . . H30A H 1.0210 0.3494 0.7074 0.039 Uiso 1 1 calc R . . C34 C 0.8440(5) 0.2087(5) 0.7238(4) 0.0202(14) Uani 1 1 d . . . C31 C 0.9352(7) 0.2631(6) 0.6127(5) 0.042(2) Uani 1 1 d . . . H31A H 0.9659 0.2807 0.5731 0.050 Uiso 1 1 calc R . . C57 C 0.9469(6) 0.3923(5) 0.4203(5) 0.0279(16) Uani 1 1 d . . . H57A H 0.9101 0.4124 0.4575 0.033 Uiso 1 1 calc R . . H57B H 0.9924 0.3397 0.4489 0.033 Uiso 1 1 calc R . . C11 C 0.3655(6) 0.4194(6) 0.8402(5) 0.0327(18) Uani 1 1 d . . . H11A H 0.3124 0.4584 0.8425 0.039 Uiso 1 1 calc R . . C10 C 0.4138(6) 0.3617(5) 0.9064(5) 0.0278(17) Uani 1 1 d . . . H10A H 0.3952 0.3616 0.9553 0.033 Uiso 1 1 calc R . . C14 C 0.4930(5) 0.3642(6) 0.6814(4) 0.0260(16) Uani 1 1 d . . . H14A H 0.5072 0.2973 0.6682 0.031 Uiso 1 1 calc R . . H14B H 0.4348 0.3872 0.6350 0.031 Uiso 1 1 calc R . . C37 C 0.4083(5) 0.4823(5) 0.3995(4) 0.0245(15) Uani 1 1 d . . . H37A H 0.3911 0.4833 0.4491 0.029 Uiso 1 1 calc R . . C32 C 0.8572(7) 0.1964(6) 0.5884(5) 0.040(2) Uani 1 1 d . . . H32A H 0.8365 0.1702 0.5331 0.048 Uiso 1 1 calc R . . C41 C 0.5336(6) 0.6088(5) 0.4563(4) 0.0228(15) Uani 1 1 d . . . H41A H 0.5162 0.6138 0.5056 0.027 Uiso 1 1 calc R . . C54 C 0.9874(6) 0.5249(5) 0.2155(5) 0.0264(16) Uani 1 1 d . . . H54A H 1.0388 0.4795 0.2382 0.032 Uiso 1 1 calc R . . C25 C 0.9612(6) 0.4510(5) 0.9068(5) 0.0319(18) Uani 1 1 d . . . H25A H 1.0105 0.4996 0.9376 0.038 Uiso 1 1 calc R . . H25B H 0.9269 0.4279 0.9450 0.038 Uiso 1 1 calc R . . C1 C 0.7664(6) 0.0649(6) 0.9411(5) 0.0343(19) Uani 1 1 d . . . H1A H 0.8169 0.0247 0.9352 0.041 Uiso 1 1 calc R . . C59 C 0.8117(6) 0.2693(6) 0.3473(5) 0.0346(18) Uani 1 1 d . . . H59A H 0.8553 0.2165 0.3781 0.042 Uiso 1 1 calc R . . H59B H 0.7718 0.2906 0.3815 0.042 Uiso 1 1 calc R . . C26 C 1.0122(6) 0.3675(6) 0.8824(5) 0.0321(18) Uani 1 1 d . . . H26A H 1.0524 0.3914 0.8493 0.039 Uiso 1 1 calc R . . H26B H 1.0565 0.3357 0.9337 0.039 Uiso 1 1 calc R . . C44 C 0.6588(6) 0.7369(5) 0.5094(4) 0.0303(18) Uani 1 1 d . . . H44A H 0.6435 0.7421 0.5597 0.036 Uiso 1 1 calc R . . C65 C 0.7491(6) 0.4086(6) 0.0370(5) 0.0331(18) Uani 1 1 d . . . H65A H 0.7930 0.4030 0.0063 0.040 Uiso 1 1 calc R . . C64 C 0.7615(6) 0.3476(6) 0.1042(5) 0.0289(17) Uani 1 1 d . . . H64A H 0.8125 0.3008 0.1208 0.035 Uiso 1 1 calc R . . C56 C 1.0052(5) 0.4773(5) 0.4058(4) 0.0243(16) Uani 1 1 d . . . H56A H 1.0398 0.5091 0.4604 0.029 Uiso 1 1 calc R . . H56B H 1.0552 0.4536 0.3825 0.029 Uiso 1 1 calc R . . C23 C 0.8266(6) 0.5763(5) 0.8528(5) 0.0336(18) Uani 1 1 d . . . H23A H 0.7955 0.5485 0.8917 0.040 Uiso 1 1 calc R . . H23B H 0.8707 0.6291 0.8830 0.040 Uiso 1 1 calc R . . C18 C 0.6758(6) 0.3877(6) 0.5134(5) 0.0353(19) Uani 1 1 d . . . H18A H 0.6701 0.3508 0.4645 0.042 Uiso 1 1 calc R . . C19 C 0.7486(6) 0.4615(6) 0.5396(5) 0.036(2) Uani 1 1 d . . . H19A H 0.7909 0.4719 0.5079 0.043 Uiso 1 1 calc R . . C3 C 0.6693(6) 0.1162(6) 1.0259(5) 0.0323(19) Uani 1 1 d . . . H3A H 0.6529 0.1118 1.0758 0.039 Uiso 1 1 calc R . . C63 C 0.6935(5) 0.3591(5) 0.1468(4) 0.0198(14) Uani 1 1 d . . . C33 C 0.8102(6) 0.1683(6) 0.6438(4) 0.0310(17) Uani 1 1 d . . . H33A H 0.7573 0.1235 0.6278 0.037 Uiso 1 1 calc R . . C45 C 0.7276(6) 0.7956(5) 0.4972(5) 0.0326(18) Uani 1 1 d . . . H45A H 0.7592 0.8431 0.5379 0.039 Uiso 1 1 calc R . . C2 C 0.7428(7) 0.0588(6) 1.0158(5) 0.039(2) Uani 1 1 d . . . H2A H 0.7775 0.0152 1.0591 0.047 Uiso 1 1 calc R . . C24 C 0.8876(6) 0.4981(6) 0.8301(5) 0.0341(18) Uani 1 1 d . . . H24A H 0.8431 0.4478 0.7960 0.041 Uiso 1 1 calc R . . H24B H 0.9232 0.5271 0.7951 0.041 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 Br1 0.0349(4) 0.0323(4) 0.0297(4) 0.0015(3) 0.0137(3) -0.0083(3) Br2 0.0507(5) 0.0366(4) 0.0220(3) -0.0062(3) 0.0181(3) -0.0111(4) Br3 0.0456(5) 0.0427(5) 0.0261(4) -0.0048(3) 0.0184(4) 0.0078(4) Br4 0.0348(5) 0.0260(4) 0.0963(9) 0.0026(5) 0.0166(5) 0.0031(4) C49 0.024(4) 0.020(3) 0.021(4) 0.011(3) 0.012(3) 0.004(3) C43 0.023(4) 0.013(3) 0.015(3) 0.000(2) 0.009(3) 0.007(2) N6 0.022(3) 0.018(3) 0.015(3) 0.003(2) 0.008(2) 0.009(2) N10 0.021(3) 0.016(3) 0.018(3) 0.004(2) 0.007(2) 0.005(2) C39 0.027(4) 0.016(3) 0.009(3) 0.006(2) 0.007(3) 0.011(3) C9 0.030(4) 0.015(4) 0.021(3) -0.009(2) 0.013(3) -0.012(3) C67 0.031(4) 0.022(3) 0.014(3) 0.001(3) 0.003(3) 0.002(3) N1 0.026(3) 0.023(3) 0.017(3) -0.006(2) 0.013(3) -0.012(2) N2 0.022(3) 0.018(3) 0.028(3) -0.003(2) 0.010(3) -0.002(2) N3 0.029(3) 0.019(3) 0.028(3) -0.003(2) 0.012(3) -0.009(2) C38 0.017(4) 0.027(4) 0.014(3) 0.007(3) 0.006(3) 0.011(3) C4 0.035(4) 0.022(3) 0.020(3) -0.006(3) 0.010(3) -0.013(3) C47 0.020(4) 0.023(4) 0.022(4) 0.004(3) 0.006(3) 0.005(3) C8 0.030(4) 0.019(4) 0.020(3) -0.008(3) 0.014(3) -0.016(3) N9 0.018(3) 0.024(3) 0.017(3) 0.007(2) 0.008(3) 0.007(2) N4 0.025(3) 0.017(3) 0.023(3) -0.001(2) 0.009(3) -0.002(2) C42 0.027(4) 0.016(3) 0.017(3) 0.002(3) 0.001(3) 0.008(3) C58 0.032(5) 0.032(4) 0.028(4) 0.006(3) 0.014(4) 0.003(3) C40 0.017(3) 0.024(4) 0.017(3) 0.004(3) 0.003(3) 0.013(3) C36 0.022(4) 0.029(4) 0.026(4) 0.005(3) 0.010(3) 0.003(3) C6 0.025(4) 0.022(4) 0.030(4) -0.002(3) 0.013(3) -0.010(3) N7 0.022(3) 0.017(3) 0.014(3) -0.003(2) 0.007(2) 0.003(2) N5 0.021(3) 0.021(3) 0.017(3) 0.002(2) 0.008(3) -0.005(2) C13 0.020(4) 0.035(4) 0.019(4) -0.008(3) 0.008(3) -0.014(3) C15 0.025(4) 0.018(3) 0.014(3) 0.002(3) 0.010(3) -0.002(3) C48 0.015(4) 0.026(4) 0.026(4) 0.009(3) 0.006(3) 0.010(3) C62 0.022(4) 0.025(4) 0.010(3) 0.000(3) 0.003(3) 0.008(3) N8 0.028(3) 0.019(3) 0.024(3) 0.003(2) 0.014(3) 0.004(2) C53 0.032(4) 0.032(4) 0.015(3) -0.005(3) 0.011(3) -0.004(3) C52 0.037(5) 0.022(4) 0.016(3) 0.000(3) 0.007(3) -0.001(3) C51 0.029(4) 0.027(4) 0.015(3) 0.000(3) 0.004(3) -0.003(3) C5 0.031(4) 0.013(3) 0.021(3) -0.006(3) 0.009(3) -0.010(3) C12 0.030(4) 0.027(4) 0.028(4) -0.005(3) 0.008(4) -0.005(3) C60 0.035(5) 0.016(4) 0.044(5) 0.010(3) 0.016(4) 0.005(3) O1 0.045(4) 0.077(5) 0.041(4) 0.004(3) 0.016(3) 0.000(3) C28 0.028(4) 0.032(4) 0.037(4) -0.015(3) 0.018(4) -0.010(3) O2 0.044(4) 0.056(4) 0.030(3) 0.007(3) 0.010(3) 0.003(3) C22 0.033(4) 0.014(3) 0.040(4) -0.006(3) 0.019(4) -0.006(3) C61 0.026(4) 0.016(3) 0.021(4) 0.001(3) 0.010(3) 0.003(3) C35 0.027(4) 0.017(3) 0.026(4) 0.001(3) 0.010(3) 0.004(3) C50 0.023(4) 0.019(3) 0.015(3) 0.002(3) 0.006(3) 0.001(3) C20 0.027(4) 0.028(4) 0.036(4) 0.005(3) 0.016(4) 0.003(3) C7 0.043(5) 0.032(4) 0.014(3) -0.006(3) 0.018(3) -0.013(3) C29 0.022(4) 0.030(4) 0.026(4) 0.005(3) 0.008(3) 0.002(3) C21 0.018(3) 0.019(3) 0.025(4) 0.007(3) 0.009(3) 0.002(3) C16 0.024(4) 0.019(3) 0.016(3) 0.002(3) 0.008(3) 0.003(3) O3 0.115(7) 0.043(4) 0.059(5) 0.010(3) 0.025(5) 0.012(4) O4 0.052(4) 0.057(4) 0.037(3) -0.001(3) 0.019(3) -0.001(3) C68 0.019(4) 0.015(3) 0.024(4) -0.008(3) 0.010(3) -0.001(2) C17 0.032(4) 0.018(4) 0.030(4) 0.001(3) 0.011(4) 0.005(3) C27 0.023(4) 0.025(4) 0.022(4) -0.006(3) 0.007(3) -0.004(3) O6 0.037(4) 0.066(4) 0.039(3) 0.007(3) 0.011(3) 0.001(3) C55 0.017(3) 0.024(3) 0.012(3) 0.005(3) 0.005(3) 0.000(3) C66 0.040(5) 0.038(5) 0.032(4) 0.008(3) 0.022(4) -0.004(4) C46 0.030(4) 0.018(3) 0.041(4) 0.000(4) 0.007(3) 0.000(3) O5 0.061(4) 0.046(4) 0.047(4) 0.007(3) 0.030(4) 0.011(3) C30 0.038(5) 0.029(4) 0.037(4) 0.016(3) 0.020(4) 0.003(3) C34 0.022(4) 0.021(3) 0.021(3) 0.004(3) 0.012(3) 0.003(3) C31 0.056(6) 0.047(6) 0.032(4) 0.023(4) 0.026(4) 0.015(4) C57 0.029(4) 0.027(4) 0.030(4) 0.010(3) 0.014(3) 0.005(3) C11 0.029(4) 0.036(4) 0.034(4) -0.016(4) 0.012(4) -0.006(3) C10 0.036(5) 0.025(4) 0.030(4) -0.016(3) 0.021(4) -0.010(3) C14 0.019(4) 0.038(4) 0.016(4) -0.004(3) -0.001(3) -0.013(3) C37 0.030(4) 0.029(4) 0.018(3) 0.008(3) 0.012(3) 0.009(3) C32 0.049(5) 0.046(5) 0.021(4) 0.007(3) 0.006(4) 0.017(4) C41 0.036(4) 0.021(3) 0.017(3) 0.003(3) 0.016(3) 0.010(3) C54 0.035(4) 0.019(4) 0.025(4) -0.001(3) 0.009(3) 0.001(3) C25 0.038(5) 0.020(4) 0.032(4) -0.002(3) 0.004(4) -0.012(3) C1 0.032(5) 0.024(4) 0.042(5) -0.002(3) 0.007(4) -0.006(3) C59 0.041(5) 0.028(4) 0.043(4) 0.014(4) 0.024(4) 0.009(3) C26 0.019(4) 0.034(4) 0.036(5) -0.002(3) 0.001(4) -0.009(3) C44 0.049(5) 0.027(4) 0.013(3) -0.003(3) 0.008(4) 0.005(3) C65 0.030(4) 0.041(5) 0.036(4) -0.002(4) 0.022(4) -0.006(3) C64 0.029(4) 0.033(4) 0.031(4) -0.005(3) 0.018(4) 0.002(3) C56 0.025(4) 0.025(4) 0.021(4) 0.006(3) 0.006(3) 0.007(3) C23 0.037(5) 0.019(4) 0.041(5) -0.003(3) 0.009(4) -0.003(3) C18 0.046(5) 0.035(4) 0.026(4) -0.001(3) 0.015(4) 0.016(4) C19 0.030(5) 0.046(5) 0.045(5) 0.008(4) 0.031(4) 0.010(4) C3 0.051(5) 0.028(4) 0.022(4) -0.001(3) 0.017(4) -0.009(4) C63 0.022(4) 0.018(3) 0.021(3) -0.006(3) 0.010(3) 0.001(3) C33 0.033(4) 0.034(4) 0.024(4) 0.000(3) 0.006(3) 0.006(3) C45 0.038(5) 0.023(4) 0.027(4) -0.004(3) -0.002(3) 0.005(3) C2 0.047(6) 0.032(4) 0.034(5) 0.007(3) 0.008(4) -0.009(4) C24 0.047(5) 0.023(4) 0.034(4) -0.002(3) 0.015(4) -0.002(4) _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 C49 N9 1.316(9) . ? C49 N10 1.335(8) . ? C43 N6 1.333(8) . ? C43 C42 1.426(9) . ? C43 C47 1.446(10) . ? N6 C39 1.373(9) . ? N10 C50 1.385(8) . ? N10 C48 1.472(8) . ? C39 C40 1.420(10) . ? C39 C38 1.424(9) . ? C9 N1 1.355(9) . ? C9 C8 1.425(9) . ? C9 C13 1.429(10) . ? C67 C66 1.375(10) . ? C67 C68 1.407(10) . ? N1 C5 1.342(9) . ? N2 C27 1.346(9) . ? N2 C34 1.383(9) . ? N2 C28 1.486(9) . ? N3 C27 1.337(9) . ? N3 C29 1.382(9) . ? N3 C26 1.476(9) . ? C38 C41 1.394(10) . ? C38 C37 1.423(10) . ? C4 C7 1.400(11) . ? C4 C3 1.412(11) . ? C4 C5 1.419(9) . ? C47 C46 1.374(10) . ? C47 C48 1.503(10) . ? C8 C7 1.393(10) . ? C8 C10 1.444(10) . ? N9 C55 1.407(8) . ? N9 C56 1.480(8) . ? N4 C15 1.338(9) . ? N4 C21 1.386(9) . ? N4 C22 1.481(9) . ? C42 C41 1.411(10) . ? C42 C44 1.425(10) . ? C58 C59 1.530(11) . ? C58 C57 1.544(11) . ? C40 C35 1.356(10) . ? C40 C62 1.517(9) . ? C36 C37 1.360(11) . ? C36 C35 1.419(10) . ? C6 C1 1.347(11) . ? C6 C5 1.455(10) . ? C6 C28 1.494(10) . ? N7 C61 1.343(9) . ? N7 C68 1.370(8) . ? N7 C62 1.475(8) . ? N5 C15 1.328(9) . ? N5 C16 1.381(8) . ? N5 C14 1.466(9) . ? C13 C12 1.393(11) . ? C13 C14 1.494(10) . ? N8 C61 1.325(9) . ? N8 C63 1.380(9) . ? N8 C60 1.490(9) . ? C53 C54 1.361(10) . ? C53 C52 1.409(11) . ? C52 C51 1.382(10) . ? C51 C50 1.397(9) . ? C12 C11 1.416(11) . ? C60 C59 1.505(12) . ? C22 C23 1.513(12) . ? C50 C55 1.389(9) . ? C20 C21 1.382(10) . ? C20 C19 1.394(11) . ? C29 C30 1.390(10) . ? C29 C34 1.414(10) . ? C21 C16 1.407(10) . ? C16 C17 1.385(10) . ? C68 C63 1.390(9) . ? C17 C18 1.390(11) . ? C55 C54 1.390(10) . ? C66 C65 1.407(12) . ? C46 C45 1.413(11) . ? C30 C31 1.381(12) . ? C34 C33 1.390(10) . ? C31 C32 1.409(13) . ? C57 C56 1.515(10) . ? C11 C10 1.359(12) . ? C32 C33 1.385(11) . ? C25 C26 1.501(11) . ? C25 C24 1.519(11) . ? C1 C2 1.416(12) . ? C44 C45 1.353(11) . ? C65 C64 1.375(11) . ? C64 C63 1.410(10) . ? C23 C24 1.525(11) . ? C18 C19 1.427(13) . ? C3 C2 1.383(12) . ? 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 N9 C49 N10 111.2(6) . . ? N6 C43 C42 123.1(6) . . ? N6 C43 C47 119.2(6) . . ? C42 C43 C47 117.6(6) . . ? C43 N6 C39 118.7(5) . . ? C49 N10 C50 107.3(5) . . ? C49 N10 C48 128.8(6) . . ? C50 N10 C48 123.9(5) . . ? N6 C39 C40 119.6(6) . . ? N6 C39 C38 122.3(6) . . ? C40 C39 C38 118.1(6) . . ? N1 C9 C8 122.7(6) . . ? N1 C9 C13 118.1(6) . . ? C8 C9 C13 119.1(6) . . ? C66 C67 C68 116.8(7) . . ? C5 N1 C9 117.8(6) . . ? C27 N2 C34 109.4(6) . . ? C27 N2 C28 127.1(6) . . ? C34 N2 C28 123.4(6) . . ? C27 N3 C29 109.0(6) . . ? C27 N3 C26 125.4(6) . . ? C29 N3 C26 125.4(6) . . ? C41 C38 C37 122.5(6) . . ? C41 C38 C39 118.0(6) . . ? C37 C38 C39 119.6(6) . . ? C7 C4 C3 120.7(6) . . ? C7 C4 C5 118.4(7) . . ? C3 C4 C5 120.9(7) . . ? C46 C47 C43 119.0(6) . . ? C46 C47 C48 120.4(7) . . ? C43 C47 C48 120.6(6) . . ? C7 C8 C9 118.6(7) . . ? C7 C8 C10 122.0(6) . . ? C9 C8 C10 119.4(6) . . ? C49 N9 C55 108.3(5) . . ? C49 N9 C56 124.8(6) . . ? C55 N9 C56 125.9(6) . . ? C15 N4 C21 109.0(6) . . ? C15 N4 C22 124.1(6) . . ? C21 N4 C22 126.8(6) . . ? C41 C42 C44 121.6(6) . . ? C41 C42 C43 117.6(6) . . ? C44 C42 C43 120.7(7) . . ? C59 C58 C57 113.5(6) . . ? C35 C40 C39 120.8(6) . . ? C35 C40 C62 119.3(6) . . ? C39 C40 C62 119.9(6) . . ? C37 C36 C35 119.8(7) . . ? C1 C6 C5 119.6(7) . . ? C1 C6 C28 120.4(7) . . ? C5 C6 C28 119.9(7) . . ? C61 N7 C68 108.6(6) . . ? C61 N7 C62 125.8(6) . . ? C68 N7 C62 125.5(5) . . ? C15 N5 C16 109.4(5) . . ? C15 N5 C14 126.4(6) . . ? C16 N5 C14 124.0(6) . . ? C12 C13 C9 119.2(6) . . ? C12 C13 C14 119.4(7) . . ? C9 C13 C14 121.4(7) . . ? N5 C15 N4 109.3(6) . . ? N10 C48 C47 111.9(5) . . ? N7 C62 C40 112.5(5) . . ? C61 N8 C63 108.6(6) . . ? C61 N8 C60 124.4(6) . . ? C63 N8 C60 126.9(6) . . ? C54 C53 C52 121.9(7) . . ? C51 C52 C53 122.2(6) . . ? C52 C51 C50 116.0(7) . . ? N1 C5 C4 123.4(7) . . ? N1 C5 C6 118.6(6) . . ? C4 C5 C6 117.9(6) . . ? C13 C12 C11 121.6(7) . . ? N8 C60 C59 110.9(6) . . ? N2 C28 C6 114.2(6) . . ? N4 C22 C23 111.2(6) . . ? N8 C61 N7 109.5(6) . . ? C40 C35 C36 121.2(7) . . ? N10 C50 C55 107.8(6) . . ? N10 C50 C51 131.4(6) . . ? C55 C50 C51 120.7(6) . . ? C21 C20 C19 115.6(7) . . ? C8 C7 C4 119.1(6) . . ? N3 C29 C30 132.5(7) . . ? N3 C29 C34 106.7(6) . . ? C30 C29 C34 120.7(7) . . ? C20 C21 N4 131.5(7) . . ? C20 C21 C16 122.5(7) . . ? N4 C21 C16 106.0(6) . . ? N5 C16 C17 131.7(7) . . ? N5 C16 C21 106.2(6) . . ? C17 C16 C21 122.1(6) . . ? N7 C68 C63 106.6(6) . . ? N7 C68 C67 131.5(6) . . ? C63 C68 C67 121.8(6) . . ? C16 C17 C18 116.5(7) . . ? N3 C27 N2 109.2(6) . . ? C50 C55 C54 123.3(6) . . ? C50 C55 N9 105.4(6) . . ? C54 C55 N9 131.4(6) . . ? C67 C66 C65 120.9(7) . . ? C47 C46 C45 122.7(7) . . ? C31 C30 C29 116.9(8) . . ? N2 C34 C33 132.1(7) . . ? N2 C34 C29 105.7(6) . . ? C33 C34 C29 122.1(6) . . ? C30 C31 C32 122.4(7) . . ? C56 C57 C58 111.2(6) . . ? C10 C11 C12 120.2(7) . . ? C11 C10 C8 120.4(7) . . ? N5 C14 C13 112.2(6) . . ? C36 C37 C38 120.5(6) . . ? C33 C32 C31 121.0(8) . . ? C38 C41 C42 120.3(6) . . ? C53 C54 C55 115.9(7) . . ? C26 C25 C24 111.4(7) . . ? C6 C1 C2 122.0(8) . . ? C60 C59 C58 112.1(6) . . ? N3 C26 C25 110.4(6) . . ? C45 C44 C42 120.4(7) . . ? C64 C65 C66 123.4(7) . . ? C65 C64 C63 115.6(7) . . ? N9 C56 C57 111.8(6) . . ? C22 C23 C24 113.3(7) . . ? C17 C18 C19 121.0(7) . . ? C20 C19 C18 122.3(7) . . ? C2 C3 C4 119.3(7) . . ? N8 C63 C68 106.7(6) . . ? N8 C63 C64 131.8(7) . . ? C68 C63 C64 121.5(7) . . ? C32 C33 C34 116.8(8) . . ? C44 C45 C46 119.6(7) . . ? C3 C2 C1 120.2(8) . . ? C25 C24 C23 112.9(7) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.174 _refine_diff_density_min -1.397 _refine_diff_density_rms 0.159 data_1c _database_code_depnum_ccdc_archive 'CCDC 914124' #TrackingRef '5-Jian Br.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4.11 H3.22 Br0.22 N0.56 O0.06' _chemical_formula_weight 79.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8544(15) _cell_length_b 11.0995(19) _cell_length_c 16.475(3) _cell_angle_alpha 91.233(2) _cell_angle_beta 90.453(2) _cell_angle_gamma 105.781(2) _cell_volume 1557.6(5) _cell_formula_units_Z 18 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1186 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 23.55 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.170 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.040 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 2.640 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9091 _exptl_absorpt_correction_T_max 0.9645 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9828 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0708 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.55 _reflns_number_total 6931 _reflns_number_gt 3938 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1073P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6931 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1144 _refine_ls_R_factor_gt 0.0630 _refine_ls_wR_factor_ref 0.2112 _refine_ls_wR_factor_gt 0.1865 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.50307(8) 0.15169(6) 0.33523(4) 0.0624(2) Uani 1 1 d . . . Br2 Br 0.31619(8) 0.62362(7) 0.06488(5) 0.0712(3) Uani 1 1 d . . . N1 N 0.7604(5) 0.8866(3) 0.3930(2) 0.0337(9) Uani 1 1 d . . . N5 N 0.6372(5) 0.5208(4) 0.2057(2) 0.0344(9) Uani 1 1 d . . . N4 N 0.8183(5) 0.6298(4) 0.1276(2) 0.0340(9) Uani 1 1 d . . . N3 N 0.9048(4) 0.9343(4) 0.1147(2) 0.0340(9) Uani 1 1 d . . . N2 N 0.9753(5) 0.9513(4) 0.3229(2) 0.0346(9) Uani 1 1 d . . . C6 C 0.5128(5) 0.7192(4) 0.4023(3) 0.0312(10) Uani 1 1 d . . . C36 C 0.8928(6) 0.6124(4) 0.1991(3) 0.0336(11) Uani 1 1 d . . . C14 C 1.0169(6) 0.9007(4) 0.3949(3) 0.0342(11) Uani 1 1 d . . . C31 C 0.7795(5) 0.5422(4) 0.2484(3) 0.0311(10) Uani 1 1 d . . . C2 C 0.4584(5) 0.5322(4) 0.3171(3) 0.0312(10) Uani 1 1 d . . . C23 C 0.7395(6) 0.9737(5) 0.0051(3) 0.0372(11) Uani 1 1 d . . . C25 C 0.8017(6) 0.7717(4) 0.0145(3) 0.0342(11) Uani 1 1 d . . . C8 C 0.8210(6) 0.9414(4) 0.3246(3) 0.0359(11) Uani 1 1 d . . . H8A H 0.7646 0.9686 0.2843 0.043 Uiso 1 1 calc R . . C21 C 0.9270(6) 1.0535(4) 0.1404(3) 0.0358(11) Uani 1 1 d . . . C30 C 0.6669(6) 0.5742(4) 0.1347(3) 0.0355(11) Uani 1 1 d . . . H30A H 0.5914 0.5728 0.0949 0.043 Uiso 1 1 calc R . . C13 C 1.1608(6) 0.8926(5) 0.4241(3) 0.0408(12) Uani 1 1 d . . . H13A H 1.2522 0.9196 0.3944 0.049 Uiso 1 1 calc R . . C24 C 0.8178(5) 0.8965(4) 0.0466(3) 0.0342(11) Uani 1 1 d . . . C22 C 0.7618(6) 1.0960(5) 0.0327(3) 0.0435(13) Uani 1 1 d . . . H22A H 0.7118 1.1484 0.0068 0.052 Uiso 1 1 calc R . . C9 C 0.8806(6) 0.8601(4) 0.4383(3) 0.0334(11) Uani 1 1 d . . . C35 C 1.0496(6) 0.6543(5) 0.2245(3) 0.0412(12) Uani 1 1 d . . . H35A H 1.1274 0.7007 0.1913 0.049 Uiso 1 1 calc R . . C29 C 0.8940(6) 0.6910(5) 0.0524(3) 0.0383(12) Uani 1 1 d . . . H29A H 0.9031 0.6268 0.0133 0.046 Uiso 1 1 calc R . . H29B H 0.9990 0.7421 0.0659 0.046 Uiso 1 1 calc R . . C5 C 0.4243(6) 0.6519(5) 0.4619(3) 0.0370(11) Uani 1 1 d . . . H5A H 0.4144 0.6908 0.5114 0.044 Uiso 1 1 calc R . . C3 C 0.3691(5) 0.4663(4) 0.3778(3) 0.0357(11) Uani 1 1 d . . . H3A H 0.3224 0.3809 0.3703 0.043 Uiso 1 1 calc R . . C16 C 1.0244(6) 1.0971(5) 0.2107(3) 0.0415(12) Uani 1 1 d . . . C7 C 0.5944(5) 0.8571(4) 0.4152(3) 0.0400(12) Uani 1 1 d . . . H7A H 0.5421 0.9059 0.3826 0.048 Uiso 1 1 calc R . . H7B H 0.5867 0.8805 0.4718 0.048 Uiso 1 1 calc R . . C28 C 0.6426(7) 0.9240(6) -0.0642(3) 0.0507(14) Uani 1 1 d . . . H28A H 0.5889 0.9732 -0.0909 0.061 Uiso 1 1 calc R . . C1 C 0.5271(5) 0.6604(4) 0.3294(3) 0.0344(11) Uani 1 1 d . . . H1A H 0.5833 0.7067 0.2878 0.041 Uiso 1 1 calc R . . C12 C 1.1602(7) 0.8424(5) 0.4992(3) 0.0457(13) Uani 1 1 d . . . H12A H 1.2547 0.8373 0.5219 0.055 Uiso 1 1 calc R . . C18 C 0.9941(8) 1.3060(6) 0.1921(4) 0.0614(18) Uani 1 1 d . . . H18A H 1.0207 1.3897 0.2090 0.074 Uiso 1 1 calc R . . C10 C 0.8814(7) 0.8072(5) 0.5137(3) 0.0431(13) Uani 1 1 d . . . H10A H 0.7899 0.7788 0.5431 0.052 Uiso 1 1 calc R . . C15 C 1.0863(6) 1.0084(5) 0.2578(3) 0.0401(12) Uani 1 1 d . . . H15A H 1.1870 1.0522 0.2821 0.048 Uiso 1 1 calc R . . H15B H 1.1022 0.9428 0.2217 0.048 Uiso 1 1 calc R . . C20 C 0.8603(6) 1.1400(5) 0.0999(3) 0.0406(12) Uani 1 1 d . . . C11 C 1.0234(7) 0.7988(5) 0.5426(3) 0.0487(14) Uani 1 1 d . . . H11A H 1.0282 0.7629 0.5927 0.058 Uiso 1 1 calc R . . C26 C 0.7111(6) 0.7317(5) -0.0532(3) 0.0447(13) Uani 1 1 d . . . H26A H 0.7041 0.6522 -0.0747 0.054 Uiso 1 1 calc R . . C32 C 0.8133(6) 0.5065(5) 0.3255(3) 0.0442(13) Uani 1 1 d . . . H32A H 0.7370 0.4565 0.3579 0.053 Uiso 1 1 calc R . . C37 C 0.4797(6) 0.4645(5) 0.2394(3) 0.0390(12) Uani 1 1 d . . . H37A H 0.4678 0.3768 0.2501 0.047 Uiso 1 1 calc R . . H37B H 0.3996 0.4694 0.2001 0.047 Uiso 1 1 calc R . . C4 C 0.3480(6) 0.5244(5) 0.4491(3) 0.0408(12) Uani 1 1 d . . . H4A H 0.2836 0.4798 0.4888 0.049 Uiso 1 1 calc R . . C17 C 1.0584(7) 1.2198(5) 0.2339(3) 0.0514(15) Uani 1 1 d . . . H17A H 1.1254 1.2483 0.2781 0.062 Uiso 1 1 calc R . . C33 C 0.9676(7) 0.5506(6) 0.3502(3) 0.0512(15) Uani 1 1 d . . . H33A H 0.9959 0.5308 0.4016 0.061 Uiso 1 1 calc R . . C19 C 0.8943(8) 1.2668(5) 0.1278(4) 0.0527(15) Uani 1 1 d . . . H19A H 0.8486 1.3224 0.1023 0.063 Uiso 1 1 calc R . . C34 C 1.0820(6) 0.6226(5) 0.3020(3) 0.0497(15) Uani 1 1 d . . . H34A H 1.1842 0.6508 0.3223 0.060 Uiso 1 1 calc R . . C27 C 0.6291(7) 0.8051(6) -0.0911(4) 0.0558(16) Uani 1 1 d . . . H27A H 0.5640 0.7726 -0.1355 0.067 Uiso 1 1 calc R . . O1 O 0.5207(9) 0.8872(8) 0.2078(5) 0.059(2) Uani 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0652(4) 0.0509(4) 0.0671(5) 0.0093(3) -0.0180(3) 0.0090(3) Br2 0.0613(4) 0.0763(5) 0.0885(6) 0.0317(4) 0.0108(4) 0.0373(4) N1 0.033(2) 0.029(2) 0.036(2) 0.0027(17) 0.0013(18) 0.0026(17) N5 0.038(2) 0.032(2) 0.032(2) 0.0012(17) 0.0036(18) 0.0077(17) N4 0.036(2) 0.033(2) 0.035(2) 0.0000(17) -0.0035(18) 0.0128(18) N3 0.034(2) 0.035(2) 0.033(2) 0.0039(17) 0.0002(18) 0.0087(17) N2 0.035(2) 0.037(2) 0.030(2) 0.0024(17) -0.0046(18) 0.0066(17) C6 0.024(2) 0.030(2) 0.040(3) 0.002(2) -0.002(2) 0.0080(19) C36 0.040(3) 0.034(3) 0.031(3) -0.005(2) 0.000(2) 0.017(2) C14 0.045(3) 0.028(2) 0.029(3) -0.0028(19) -0.001(2) 0.009(2) C31 0.034(3) 0.031(2) 0.030(3) -0.001(2) -0.002(2) 0.013(2) C2 0.026(2) 0.033(3) 0.033(3) 0.001(2) 0.000(2) 0.0068(19) C23 0.041(3) 0.044(3) 0.030(3) 0.010(2) 0.005(2) 0.016(2) C25 0.036(3) 0.034(3) 0.032(3) 0.000(2) 0.001(2) 0.008(2) C8 0.036(3) 0.035(3) 0.033(3) 0.001(2) -0.005(2) 0.005(2) C21 0.043(3) 0.031(3) 0.032(3) 0.005(2) 0.004(2) 0.007(2) C30 0.040(3) 0.033(3) 0.033(3) 0.001(2) -0.003(2) 0.010(2) C13 0.039(3) 0.042(3) 0.043(3) -0.004(2) -0.004(2) 0.016(2) C24 0.032(3) 0.039(3) 0.032(3) 0.006(2) 0.004(2) 0.010(2) C22 0.048(3) 0.047(3) 0.038(3) 0.017(2) 0.004(3) 0.017(3) C9 0.037(3) 0.024(2) 0.038(3) -0.001(2) 0.002(2) 0.007(2) C35 0.040(3) 0.039(3) 0.048(3) -0.003(2) 0.000(2) 0.016(2) C29 0.044(3) 0.041(3) 0.033(3) 0.007(2) 0.012(2) 0.015(2) C5 0.036(3) 0.040(3) 0.037(3) 0.003(2) 0.002(2) 0.015(2) C3 0.035(3) 0.029(2) 0.038(3) 0.004(2) 0.000(2) 0.000(2) C16 0.045(3) 0.041(3) 0.035(3) 0.001(2) 0.005(2) 0.005(2) C7 0.032(3) 0.038(3) 0.049(3) -0.001(2) 0.003(2) 0.009(2) C28 0.054(3) 0.063(4) 0.039(3) 0.008(3) -0.010(3) 0.022(3) C1 0.028(2) 0.035(3) 0.039(3) 0.005(2) 0.003(2) 0.007(2) C12 0.051(3) 0.044(3) 0.048(3) -0.001(3) -0.011(3) 0.025(3) C18 0.084(5) 0.036(3) 0.058(4) -0.007(3) 0.019(4) 0.006(3) C10 0.053(3) 0.035(3) 0.042(3) 0.010(2) 0.006(3) 0.012(2) C15 0.036(3) 0.050(3) 0.029(3) 0.000(2) 0.003(2) 0.003(2) C20 0.052(3) 0.036(3) 0.034(3) 0.006(2) 0.010(2) 0.012(2) C11 0.069(4) 0.042(3) 0.041(3) 0.008(2) -0.003(3) 0.025(3) C26 0.054(3) 0.044(3) 0.035(3) 0.000(2) 0.001(3) 0.012(3) C32 0.051(3) 0.055(3) 0.033(3) 0.003(2) -0.002(2) 0.024(3) C37 0.038(3) 0.035(3) 0.038(3) 0.002(2) 0.001(2) 0.001(2) C4 0.042(3) 0.037(3) 0.040(3) 0.006(2) 0.004(2) 0.004(2) C17 0.061(4) 0.047(3) 0.037(3) -0.006(3) 0.007(3) -0.001(3) C33 0.060(4) 0.071(4) 0.033(3) -0.001(3) -0.007(3) 0.034(3) C19 0.081(4) 0.037(3) 0.043(3) 0.009(3) 0.018(3) 0.021(3) C34 0.041(3) 0.059(4) 0.056(4) -0.014(3) -0.016(3) 0.027(3) C27 0.063(4) 0.059(4) 0.042(3) -0.005(3) -0.015(3) 0.011(3) O1 0.054(5) 0.080(6) 0.053(5) 0.023(4) -0.026(4) 0.035(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C8 1.337(6) . ? N1 C9 1.395(6) . ? N1 C7 1.467(6) . ? N5 C30 1.318(6) . ? N5 C31 1.398(6) . ? N5 C37 1.482(6) . ? N4 C30 1.322(6) . ? N4 C36 1.388(6) . ? N4 C29 1.499(6) . ? N3 C21 1.342(6) . ? N3 C24 1.348(6) . ? N2 C8 1.342(6) . ? N2 C14 1.411(6) . ? N2 C15 1.491(6) . ? C6 C5 1.364(7) . ? C6 C1 1.377(7) . ? C6 C7 1.515(6) . ? C36 C31 1.374(7) . ? C36 C35 1.397(7) . ? C14 C9 1.378(7) . ? C14 C13 1.385(7) . ? C31 C32 1.393(7) . ? C2 C3 1.375(6) . ? C2 C1 1.396(6) . ? C2 C37 1.510(7) . ? C23 C22 1.383(7) . ? C23 C24 1.423(7) . ? C23 C28 1.430(7) . ? C25 C26 1.362(7) . ? C25 C24 1.442(7) . ? C25 C29 1.507(7) . ? C8 H8A 0.9300 . ? C21 C20 1.430(7) . ? C21 C16 1.433(7) . ? C30 H30A 0.9300 . ? C13 C12 1.368(7) . ? C13 H13A 0.9300 . ? C22 C20 1.398(8) . ? C22 H22A 0.9300 . ? C9 C10 1.386(7) . ? C35 C34 1.380(7) . ? C35 H35A 0.9300 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C5 C4 1.402(7) . ? C5 H5A 0.9300 . ? C3 C4 1.366(7) . ? C3 H3A 0.9300 . ? C16 C17 1.359(7) . ? C16 C15 1.480(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C28 C27 1.357(8) . ? C28 H28A 0.9300 . ? C1 H1A 0.9300 . ? C12 C11 1.387(8) . ? C12 H12A 0.9300 . ? C18 C19 1.360(9) . ? C18 C17 1.425(9) . ? C18 H18A 0.9300 . ? C10 C11 1.368(7) . ? C10 H10A 0.9300 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C20 C19 1.422(7) . ? C11 H11A 0.9300 . ? C26 C27 1.385(8) . ? C26 H26A 0.9300 . ? C32 C33 1.375(8) . ? C32 H32A 0.9300 . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C4 H4A 0.9300 . ? C17 H17A 0.9300 . ? C33 C34 1.376(8) . ? C33 H33A 0.9300 . ? C19 H19A 0.9300 . ? C34 H34A 0.9300 . ? C27 H27A 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 C8 N1 C9 108.5(4) . . ? C8 N1 C7 125.4(4) . . ? C9 N1 C7 126.1(4) . . ? C30 N5 C31 107.8(4) . . ? C30 N5 C37 126.2(4) . . ? C31 N5 C37 125.5(4) . . ? C30 N4 C36 107.7(4) . . ? C30 N4 C29 125.0(4) . . ? C36 N4 C29 127.2(4) . . ? C21 N3 C24 117.7(4) . . ? C8 N2 C14 108.2(4) . . ? C8 N2 C15 126.6(4) . . ? C14 N2 C15 125.3(4) . . ? C5 C6 C1 119.2(4) . . ? C5 C6 C7 120.9(4) . . ? C1 C6 C7 119.8(4) . . ? C31 C36 N4 107.1(4) . . ? C31 C36 C35 121.4(5) . . ? N4 C36 C35 131.5(5) . . ? C9 C14 C13 122.4(5) . . ? C9 C14 N2 106.3(4) . . ? C13 C14 N2 131.2(5) . . ? C36 C31 C32 122.6(5) . . ? C36 C31 N5 106.3(4) . . ? C32 C31 N5 131.0(5) . . ? C3 C2 C1 118.7(4) . . ? C3 C2 C37 119.3(4) . . ? C1 C2 C37 121.9(4) . . ? C22 C23 C24 118.5(5) . . ? C22 C23 C28 122.0(5) . . ? C24 C23 C28 119.5(5) . . ? C26 C25 C24 119.2(5) . . ? C26 C25 C29 120.9(4) . . ? C24 C25 C29 119.8(4) . . ? N1 C8 N2 109.7(4) . . ? N1 C8 H8A 125.2 . . ? N2 C8 H8A 125.2 . . ? N3 C21 C20 123.1(5) . . ? N3 C21 C16 118.6(5) . . ? C20 C21 C16 118.3(4) . . ? N5 C30 N4 111.1(4) . . ? N5 C30 H30A 124.5 . . ? N4 C30 H30A 124.5 . . ? C12 C13 C14 115.9(5) . . ? C12 C13 H13A 122.1 . . ? C14 C13 H13A 122.1 . . ? N3 C24 C23 123.1(4) . . ? N3 C24 C25 118.8(4) . . ? C23 C24 C25 118.2(4) . . ? C23 C22 C20 119.4(5) . . ? C23 C22 H22A 120.3 . . ? C20 C22 H22A 120.3 . . ? C14 C9 C10 121.0(5) . . ? C14 C9 N1 107.3(4) . . ? C10 C9 N1 131.6(5) . . ? C34 C35 C36 115.9(5) . . ? C34 C35 H35A 122.0 . . ? C36 C35 H35A 122.0 . . ? N4 C29 C25 112.1(4) . . ? N4 C29 H29A 109.2 . . ? C25 C29 H29A 109.2 . . ? N4 C29 H29B 109.2 . . ? C25 C29 H29B 109.2 . . ? H29A C29 H29B 107.9 . . ? C6 C5 C4 120.5(5) . . ? C6 C5 H5A 119.8 . . ? C4 C5 H5A 119.8 . . ? C4 C3 C2 120.9(4) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C17 C16 C21 119.5(5) . . ? C17 C16 C15 120.5(5) . . ? C21 C16 C15 120.0(4) . . ? N1 C7 C6 111.6(4) . . ? N1 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? N1 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C27 C28 C23 119.9(5) . . ? C27 C28 H28A 120.0 . . ? C23 C28 H28A 120.0 . . ? C6 C1 C2 121.0(5) . . ? C6 C1 H1A 119.5 . . ? C2 C1 H1A 119.5 . . ? C13 C12 C11 122.2(5) . . ? C13 C12 H12A 118.9 . . ? C11 C12 H12A 118.9 . . ? C19 C18 C17 120.5(5) . . ? C19 C18 H18A 119.7 . . ? C17 C18 H18A 119.7 . . ? C11 C10 C9 116.7(5) . . ? C11 C10 H10A 121.6 . . ? C9 C10 H10A 121.6 . . ? C16 C15 N2 110.8(4) . . ? C16 C15 H15A 109.5 . . ? N2 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? N2 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C22 C20 C19 121.6(5) . . ? C22 C20 C21 118.0(5) . . ? C19 C20 C21 120.4(5) . . ? C10 C11 C12 121.7(5) . . ? C10 C11 H11A 119.1 . . ? C12 C11 H11A 119.1 . . ? C25 C26 C27 122.4(5) . . ? C25 C26 H26A 118.8 . . ? C27 C26 H26A 118.8 . . ? C33 C32 C31 115.2(5) . . ? C33 C32 H32A 122.4 . . ? C31 C32 H32A 122.4 . . ? N5 C37 C2 110.4(4) . . ? N5 C37 H37A 109.6 . . ? C2 C37 H37A 109.6 . . ? N5 C37 H37B 109.6 . . ? C2 C37 H37B 109.6 . . ? H37A C37 H37B 108.1 . . ? C3 C4 C5 119.5(5) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C16 C17 C18 121.7(6) . . ? C16 C17 H17A 119.1 . . ? C18 C17 H17A 119.1 . . ? C32 C33 C34 122.9(5) . . ? C32 C33 H33A 118.6 . . ? C34 C33 H33A 118.6 . . ? C18 C19 C20 119.4(6) . . ? C18 C19 H19A 120.3 . . ? C20 C19 H19A 120.3 . . ? C33 C34 C35 121.9(5) . . ? C33 C34 H34A 119.0 . . ? C35 C34 H34A 119.0 . . ? C28 C27 C26 120.7(5) . . ? C28 C27 H27A 119.7 . . ? C26 C27 H27A 119.7 . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.033 _refine_diff_density_min -0.817 _refine_diff_density_rms 0.097