data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Vincent Levacher' _publ_contact_author_address ; Organic chemistry CNRS Rue tesnieres Rouen 76000 FRANCE ; _publ_contact_author_email VINCENT.LEVACHER@INSA-ROUEN.FR _publ_section_title ; Preparation of new axially chiral bridged 2,2'-bipyridines and Pyridyl monooxazoline (Pymox). Evaluation in copper (I)-catalyzed enantioselective cyclopropanation. ; loop_ _publ_author_name 'Vincent Levacher' 'Alexis Bouet' 'Georges Dupas' 'Barbara Heller' 'Francis Marsais' 'Sylvain Oudeyer' ; C.Papamicael ; data_ks466 _database_code_depnum_ccdc_archive 'CCDC 637822' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H21 N3 O2' _chemical_formula_weight 419.47 _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 10.052(2) _cell_length_b 15.052(3) _cell_length_c 42.205(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6386(2) _cell_formula_units_Z 12 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used all _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2640 _exptl_absorpt_coefficient_mu 0.084 _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 200(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 'STOE-IPDS II' _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 62075 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 46 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 23.00 _reflns_number_total 8869 _reflns_number_gt 6461 _reflns_threshold_expression >2sigma(I) _computing_data_collection STOE-X-AREA _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _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 Rfactors 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^)+(0.1343P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0085(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(18) _refine_ls_number_reflns 8869 _refine_ls_number_parameters 832 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.1931 _refine_ls_wR_factor_gt 0.1820 _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 C24 C -1.1950(4) -0.1932(3) -0.43016(10) 0.0409(10) Uani 1 1 d . . . H24 H -1.1327 -0.2300 -0.4408 0.049 Uiso 1 1 calc R . . N3 N -1.2435(3) -0.0540(2) -0.40609(8) 0.0398(8) Uani 1 1 d . . . C51 C 0.2407(7) -0.6910(4) -0.40225(12) 0.0770(17) Uani 1 1 d . . . H51 H 0.1829 -0.7279 -0.3903 0.092 Uiso 1 1 calc R . . N6 N 0.2804(4) -0.5519(3) -0.42799(9) 0.0577(10) Uani 1 1 d . . . C78 C -0.2603(7) -0.8136(4) -0.26342(12) 0.0773(17) Uani 1 1 d . . . H78 H -0.3171 -0.7771 -0.2758 0.093 Uiso 1 1 calc R . . N9 N -0.2225(5) -0.9520(3) -0.23730(10) 0.0695(12) Uani 1 1 d . . . C4 C -0.4075(3) 0.1208(3) -0.48694(8) 0.0365(9) Uani 1 1 d D . . C7 C -0.3638(6) 0.2947(4) -0.50784(11) 0.0823(19) Uani 1 1 d D . . H7 H -0.3498 0.3542 -0.5147 0.099 Uiso 1 1 calc R A 1 C5A C -0.3416(8) 0.1804(4) -0.46793(19) 0.065(2) Uiso 0.601(6) 1 d PD B 1 H5A H -0.3106 0.1630 -0.4476 0.078 Uiso 0.601(6) 1 calc PR B 1 C6A C -0.3210(11) 0.2655(6) -0.47871(19) 0.098(3) Uiso 0.601(6) 1 d PD B 1 H6A H -0.2750 0.3061 -0.4654 0.118 Uiso 0.601(6) 1 calc PR B 1 C8A C -0.4277(7) 0.2336(3) -0.52657(18) 0.057(2) Uiso 0.601(6) 1 d PD B 1 H8A H -0.4590 0.2510 -0.5469 0.068 Uiso 0.601(6) 1 calc PR B 1 C9A C -0.4474(7) 0.1477(4) -0.51656(12) 0.0470(19) Uiso 0.601(6) 1 d PD B 1 H9A H -0.4892 0.1063 -0.5303 0.056 Uiso 0.601(6) 1 calc PR B 1 C5B C -0.2808(8) 0.1564(8) -0.4872(3) 0.069(4) Uiso 0.399(6) 1 d PD B 2 H5B H -0.2083 0.1228 -0.4791 0.083 Uiso 0.399(6) 1 calc PR B 2 C6B C -0.2590(11) 0.2405(7) -0.4992(4) 0.076(4) Uiso 0.399(6) 1 d PD B 2 H6B H -0.1704 0.2614 -0.5016 0.091 Uiso 0.399(6) 1 calc PR B 2 C8B C -0.4916(9) 0.2611(7) -0.5075(3) 0.073(4) Uiso 0.399(6) 1 d PD B 2 H8B H -0.5640 0.2942 -0.5158 0.088 Uiso 0.399(6) 1 calc PR B 2 C9B C -0.5104(9) 0.1776(5) -0.4947(3) 0.055(3) Uiso 0.399(6) 1 d PD B 2 H9B H -0.5990 0.1582 -0.4910 0.066 Uiso 0.399(6) 1 calc PR B 2 C58A C -1.0759(7) -1.1156(2) -0.31869(15) 0.0612(14) Uiso 0.543(8) 1 d PGD C 1 C59A C -1.2061(6) -1.1453(4) -0.3218(2) 0.089(4) Uiso 0.543(8) 1 d PG C 1 H59A H -1.2780 -1.1077 -0.3160 0.107 Uiso 0.543(8) 1 calc PR C 1 C60A C -1.2312(5) -1.2301(4) -0.3334(2) 0.093(4) Uiso 0.543(8) 1 d PG C 1 H60A H -1.3202 -1.2504 -0.3356 0.112 Uiso 0.543(8) 1 calc PR C 1 C61A C -1.1261(8) -1.2851(3) -0.34198(17) 0.097(2) Uiso 0.543(8) 1 d PG C 1 H61A H -1.1432 -1.3430 -0.3499 0.116 Uiso 0.543(8) 1 calc PR C 1 C62A C -0.9958(6) -1.2553(3) -0.33887(18) 0.073(3) Uiso 0.543(8) 1 d PG C 1 H62A H -0.9240 -1.2929 -0.3447 0.087 Uiso 0.543(8) 1 calc PR C 1 C63A C -0.9707(5) -1.1705(4) -0.32723(18) 0.061(3) Uiso 0.543(8) 1 d PG C 1 H63A H -0.8817 -1.1502 -0.3251 0.073 Uiso 0.543(8) 1 calc PR C 1 C58B C -1.0553(9) -1.1163(3) -0.31977(18) 0.0612(14) Uiso 0.457(8) 1 d PGD C 2 C59B C -1.1537(10) -1.1631(5) -0.30370(19) 0.107(5) Uiso 0.457(8) 1 d PG C 2 H59B H -1.1958 -1.1374 -0.2858 0.129 Uiso 0.457(8) 1 calc PR C 2 C60B C -1.1904(10) -1.2474(5) -0.3139(2) 0.115(6) Uiso 0.457(8) 1 d PG C 2 H60B H -1.2576 -1.2793 -0.3029 0.138 Uiso 0.457(8) 1 calc PR C 2 C61B C -1.1287(9) -1.2850(3) -0.3401(2) 0.097(2) Uiso 0.457(8) 1 d PG C 2 H61B H -1.1538 -1.3427 -0.3471 0.116 Uiso 0.457(8) 1 calc PR C 2 C62B C -1.0303(8) -1.2383(4) -0.35620(17) 0.058(3) Uiso 0.457(8) 1 d PG C 2 H62B H -0.9882 -1.2640 -0.3741 0.069 Uiso 0.457(8) 1 calc PR C 2 C63B C -0.9936(7) -1.1540(4) -0.34602(18) 0.048(3) Uiso 0.457(8) 1 d PG C 2 H63B H -0.9264 -1.1220 -0.3570 0.057 Uiso 0.457(8) 1 calc PR C 2 C1 C -0.6069(3) -0.0665(3) -0.49642(9) 0.0308(9) Uani 1 1 d . B . C2 C -0.3790(4) -0.0444(3) -0.49840(10) 0.0439(10) Uani 1 1 d . . . H2A H -0.3062 -0.0217 -0.5120 0.053 Uiso 1 1 calc R B . H2B H -0.3473 -0.0979 -0.4870 0.053 Uiso 1 1 calc R . . C3 C -0.4246(3) 0.0263(3) -0.47521(9) 0.0364(9) Uani 1 1 d . B . H3 H -0.3762 0.0188 -0.4547 0.044 Uiso 1 1 calc R . . C10 C -0.6325(3) 0.0209(2) -0.44479(9) 0.0286(8) Uani 1 1 d . B . C11 C -0.7720(3) -0.0144(2) -0.44056(8) 0.0257(8) Uani 1 1 d . . . C12 C -0.8112(3) -0.1021(2) -0.44622(8) 0.0290(9) Uani 1 1 d . . . C13 C -0.7228(3) -0.1728(2) -0.45821(8) 0.0287(8) Uani 1 1 d . . . C14 C -0.7367(3) -0.2591(2) -0.44644(10) 0.0338(9) Uani 1 1 d . . . H14 H -0.8023 -0.2701 -0.4307 0.041 Uiso 1 1 calc R . . C15 C -0.6600(4) -0.3285(3) -0.45657(9) 0.0421(10) Uani 1 1 d . . . H15 H -0.6707 -0.3860 -0.4476 0.051 Uiso 1 1 calc R . . C16 C -0.5657(4) -0.3137(3) -0.48029(10) 0.0453(10) Uani 1 1 d . . . H16 H -0.5123 -0.3612 -0.4879 0.054 Uiso 1 1 calc R . . C17 C -0.5509(4) -0.2288(3) -0.49264(9) 0.0405(10) Uani 1 1 d . . . H17 H -0.4875 -0.2191 -0.5090 0.049 Uiso 1 1 calc R . . C18 C -0.6259(3) -0.1581(2) -0.48189(9) 0.0334(9) Uani 1 1 d . . . C19 C -0.7238(3) -0.0351(3) -0.51583(9) 0.0350(9) Uani 1 1 d . . . H19A H -0.8041 -0.0353 -0.5027 0.052 Uiso 1 1 calc R . . H19B H -0.7365 -0.0749 -0.5340 0.052 Uiso 1 1 calc R . . H19C H -0.7067 0.0253 -0.5235 0.052 Uiso 1 1 calc R . . C20 C -0.8646(3) 0.0438(2) -0.42807(8) 0.0284(8) Uani 1 1 d . . . H20 H -0.8400 0.1035 -0.4238 0.034 Uiso 1 1 calc R . . C21 C -0.9940(3) 0.0152(2) -0.42170(8) 0.0280(8) Uani 1 1 d . . . H21 H -1.0589 0.0548 -0.4134 0.034 Uiso 1 1 calc R . . C22 C -1.0246(3) -0.0730(2) -0.42787(8) 0.0264(8) Uani 1 1 d . . . C23 C -1.1607(3) -0.1087(2) -0.42104(9) 0.0291(8) Uani 1 1 d . . . C27 C -1.3664(4) -0.0861(3) -0.40030(12) 0.0514(12) Uani 1 1 d . . . H27 H -1.4278 -0.0479 -0.3899 0.062 Uiso 1 1 calc R . . C26 C -1.4083(4) -0.1669(3) -0.40804(12) 0.0534(12) Uani 1 1 d . . . H26 H -1.4962 -0.1850 -0.4030 0.064 Uiso 1 1 calc R . . C25 C -1.3237(4) -0.2243(3) -0.42347(11) 0.0497(12) Uani 1 1 d . . . H25 H -1.3511 -0.2824 -0.4293 0.060 Uiso 1 1 calc R . . C28 C -0.3535(5) -0.5707(3) -0.33630(10) 0.0586(13) Uani 1 1 d . . . C29 C -0.5828(6) -0.5528(3) -0.33326(12) 0.0661(14) Uani 1 1 d . . . H29A H -0.6538 -0.5293 -0.3193 0.079 Uiso 1 1 calc R . . H29B H -0.6160 -0.6067 -0.3441 0.079 Uiso 1 1 calc R . . C30 C -0.5378(5) -0.4825(3) -0.35729(10) 0.0562(12) Uani 1 1 d . . . H30 H -0.5847 -0.4929 -0.3779 0.067 Uiso 1 1 calc R . . C31 C -0.5638(5) -0.3882(3) -0.34649(10) 0.0517(11) Uani 1 1 d . . . C32 C -0.6375(5) -0.3284(4) -0.36551(12) 0.0723(16) Uani 1 1 d . . . H32 H -0.6700 -0.3477 -0.3855 0.087 Uiso 1 1 calc R . . C33 C -0.6630(6) -0.2425(4) -0.35568(13) 0.0833(19) Uani 1 1 d . . . H33 H -0.7115 -0.2030 -0.3689 0.100 Uiso 1 1 calc R . . C34 C -0.6184(6) -0.2156(4) -0.32712(14) 0.0861(19) Uani 1 1 d . . . H34 H -0.6322 -0.1558 -0.3208 0.103 Uiso 1 1 calc R . . C35 C -0.5548(6) -0.2714(3) -0.30743(13) 0.0711(15) Uani 1 1 d . . . H35 H -0.5276 -0.2520 -0.2870 0.085 Uiso 1 1 calc R . . C36 C -0.5298(6) -0.3563(3) -0.31707(12) 0.0744(17) Uani 1 1 d . . . H36 H -0.4866 -0.3954 -0.3027 0.089 Uiso 1 1 calc R . . C37 C -0.3300(5) -0.4824(3) -0.38710(10) 0.0548(12) Uani 1 1 d . . . C38 C -0.1903(5) -0.5148(3) -0.39148(9) 0.0481(11) Uani 1 1 d . . . C39 C -0.1486(6) -0.6038(3) -0.38691(10) 0.0547(13) Uani 1 1 d . . . C40 C -0.2372(5) -0.6752(3) -0.37516(10) 0.0520(12) Uani 1 1 d . . . C41 C -0.2247(5) -0.7603(3) -0.38858(12) 0.0616(14) Uani 1 1 d . . . H41 H -0.1613 -0.7697 -0.4049 0.074 Uiso 1 1 calc R . . C42 C -0.3022(5) -0.8306(3) -0.37862(13) 0.0635(14) Uani 1 1 d . . . H42 H -0.2925 -0.8875 -0.3880 0.076 Uiso 1 1 calc R . . C43 C -0.3937(6) -0.8169(3) -0.35484(14) 0.0701(15) Uani 1 1 d . . . H43 H -0.4473 -0.8650 -0.3478 0.084 Uiso 1 1 calc R . . C44 C -0.4084(6) -0.7344(3) -0.34118(12) 0.0661(14) Uani 1 1 d . . . H44 H -0.4708 -0.7267 -0.3245 0.079 Uiso 1 1 calc R . . C45 C -0.3334(5) -0.6621(3) -0.35135(10) 0.0561(12) Uani 1 1 d . . . C46 C -0.2362(5) -0.5401(3) -0.31665(10) 0.0624(14) Uani 1 1 d . . . H46A H -0.1562 -0.5385 -0.3299 0.094 Uiso 1 1 calc R . . H46B H -0.2224 -0.5814 -0.2990 0.094 Uiso 1 1 calc R . . H46C H -0.2540 -0.4805 -0.3083 0.094 Uiso 1 1 calc R . . C47 C -0.0985(5) -0.4558(3) -0.40371(10) 0.0554(13) Uani 1 1 d . . . H47 H -0.1241 -0.3962 -0.4080 0.067 Uiso 1 1 calc R . . C48 C 0.0299(5) -0.4826(3) -0.40982(11) 0.0549(12) Uani 1 1 d . . . H48 H 0.0942 -0.4413 -0.4173 0.066 Uiso 1 1 calc R . . C49 C 0.0640(5) -0.5713(3) -0.40487(10) 0.0563(12) Uani 1 1 d . . . C50 C 0.1998(5) -0.6058(3) -0.41212(11) 0.0575(13) Uani 1 1 d . . . C54 C 0.4014(5) -0.5822(4) -0.43453(13) 0.0708(15) Uani 1 1 d . . . H54 H 0.4598 -0.5440 -0.4458 0.085 Uiso 1 1 calc R . . C53 C 0.4479(6) -0.6635(4) -0.42634(15) 0.0816(18) Uani 1 1 d . . . H53 H 0.5359 -0.6810 -0.4317 0.098 Uiso 1 1 calc R . . C52 C 0.3659(7) -0.7197(4) -0.41034(15) 0.087(2) Uani 1 1 d . . . H52 H 0.3948 -0.7778 -0.4048 0.104 Uiso 1 1 calc R . . C55 C -0.8537(6) -0.9316(4) -0.32933(11) 0.0681(15) Uani 1 1 d . C . C56 C -1.0795(7) -0.9496(4) -0.33272(14) 0.084(2) Uani 1 1 d . C . H56A H -1.1513 -0.9726 -0.3465 0.101 Uiso 1 1 calc R . . H56B H -1.1111 -0.8946 -0.3222 0.101 Uiso 1 1 calc R . . C57 C -1.0390(6) -1.0194(4) -0.30797(12) 0.0709(15) Uani 1 1 d D . . H57A H -1.0855 -1.0061 -0.2876 0.085 Uiso 0.543(8) 1 calc PR C 1 H57B H -1.0875 -1.0100 -0.2876 0.085 Uiso 0.457(8) 1 d PR C 2 C64 C -0.8312(6) -1.0203(3) -0.27813(12) 0.0637(14) Uani 1 1 d . . . C65 C -0.6918(5) -0.9876(3) -0.27384(10) 0.0577(13) Uani 1 1 d . C . C66 C -0.6505(7) -0.8980(3) -0.27866(10) 0.0635(15) Uani 1 1 d . . . C67 C -0.7420(6) -0.8278(3) -0.29023(11) 0.0668(15) Uani 1 1 d . C . C68 C -0.7301(6) -0.7437(3) -0.27666(13) 0.0732(16) Uani 1 1 d . . . H68 H -0.6674 -0.7344 -0.2602 0.088 Uiso 1 1 calc R C . C69 C -0.8077(7) -0.6738(4) -0.28677(14) 0.0787(17) Uani 1 1 d . C . H69 H -0.7989 -0.6172 -0.2770 0.094 Uiso 1 1 calc R . . C70 C -0.8977(7) -0.6857(4) -0.31089(15) 0.0796(17) Uani 1 1 d . . . H70 H -0.9501 -0.6373 -0.3182 0.095 Uiso 1 1 calc R C . C71 C -0.9115(7) -0.7697(4) -0.32458(13) 0.0821(19) Uani 1 1 d . C . H71 H -0.9737 -0.7783 -0.3412 0.099 Uiso 1 1 calc R . . C72 C -0.8348(6) -0.8408(4) -0.31406(11) 0.0714(16) Uani 1 1 d . . . C73 C -0.7369(6) -0.9616(4) -0.34878(11) 0.0757(17) Uani 1 1 d . . . H73A H -0.6567 -0.9619 -0.3356 0.114 Uiso 1 1 calc R C . H73B H -0.7244 -0.9209 -0.3666 0.114 Uiso 1 1 calc R . . H73C H -0.7535 -1.0217 -0.3568 0.114 Uiso 1 1 calc R . . C74 C -0.5994(6) -1.0470(3) -0.26226(11) 0.0625(14) Uani 1 1 d . . . H74 H -0.6249 -1.1068 -0.2584 0.075 Uiso 1 1 calc R C . C75 C -0.4721(6) -1.0211(3) -0.25626(11) 0.0617(14) Uani 1 1 d . C . H75 H -0.4078 -1.0623 -0.2487 0.074 Uiso 1 1 calc R . . C76 C -0.4384(6) -0.9316(3) -0.26159(10) 0.0611(14) Uani 1 1 d . . . C77 C -0.3027(6) -0.8974(3) -0.25384(11) 0.0628(14) Uani 1 1 d . C . C81 C -0.1025(7) -0.9209(4) -0.22955(13) 0.0769(16) Uani 1 1 d . . . H81 H -0.0450 -0.9586 -0.2178 0.092 Uiso 1 1 calc R . . C80 C -0.0573(7) -0.8383(4) -0.23746(13) 0.0781(17) Uani 1 1 d . . . H80 H 0.0284 -0.8192 -0.2308 0.094 Uiso 1 1 calc R . . C79 C -0.1365(7) -0.7836(4) -0.25496(14) 0.0797(18) Uani 1 1 d . . . H79 H -0.1067 -0.7262 -0.2611 0.096 Uiso 1 1 calc R . . N1 N -0.5662(2) -0.0020(2) -0.47125(7) 0.0289(7) Uani 1 1 d . . . N2 N -0.9370(2) -0.13103(19) -0.43909(7) 0.0270(7) Uani 1 1 d . . . N4 N -0.3969(4) -0.5060(2) -0.36090(8) 0.0516(10) Uani 1 1 d . . . N5 N -0.0234(5) -0.6306(2) -0.39357(9) 0.0568(11) Uani 1 1 d . . . N7 N -0.8982(4) -0.9972(2) -0.30464(9) 0.0613(11) Uani 1 1 d . C . N8 N -0.5250(5) -0.8725(2) -0.27220(9) 0.0582(11) Uani 1 1 d . C . O1 O -0.5850(2) 0.07075(17) -0.42463(6) 0.0377(7) Uani 1 1 d . . . O2 O -0.4950(2) -0.06451(18) -0.51709(6) 0.0384(6) Uani 1 1 d . B . O3 O -0.3794(3) -0.4318(2) -0.40708(7) 0.0595(9) Uani 1 1 d . . . O4 O -0.4640(4) -0.5719(2) -0.31539(7) 0.0641(9) Uani 1 1 d . . . O5 O -0.8811(4) -1.0704(2) -0.25814(8) 0.0684(10) Uani 1 1 d . C . O6 O -0.9644(5) -0.9330(3) -0.35031(8) 0.0803(12) 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 C24 0.0235(19) 0.041(2) 0.059(3) 0.002(2) -0.0064(18) -0.0027(16) N3 0.0234(17) 0.040(2) 0.057(2) -0.0032(17) 0.0119(15) 0.0073(14) C51 0.123(5) 0.054(3) 0.054(3) -0.002(3) -0.011(3) 0.025(3) N6 0.071(3) 0.048(2) 0.053(2) -0.003(2) -0.010(2) 0.014(2) C78 0.128(5) 0.052(3) 0.052(3) -0.002(3) -0.008(3) 0.005(3) N9 0.107(4) 0.044(3) 0.058(3) -0.002(2) -0.014(3) 0.005(2) C4 0.0223(19) 0.049(3) 0.038(2) -0.0006(18) 0.0076(16) -0.0209(16) C7 0.125(5) 0.064(4) 0.058(3) 0.014(3) 0.021(3) -0.051(4) C1 0.0171(17) 0.041(2) 0.034(2) -0.0039(18) 0.0089(14) 0.0009(15) C2 0.033(2) 0.045(3) 0.053(3) 0.011(2) 0.0105(19) -0.0063(18) C3 0.0129(16) 0.054(3) 0.042(2) 0.005(2) 0.0010(15) -0.0084(16) C10 0.0189(17) 0.032(2) 0.035(2) 0.0045(18) -0.0044(16) 0.0015(15) C11 0.0089(15) 0.037(2) 0.0314(19) -0.0007(17) 0.0018(14) -0.0114(14) C12 0.0239(19) 0.035(2) 0.0280(19) 0.0016(17) -0.0033(15) 0.0072(15) C13 0.0169(17) 0.035(2) 0.034(2) 0.0008(17) 0.0031(14) 0.0004(15) C14 0.0235(18) 0.025(2) 0.052(2) -0.0005(19) 0.0061(17) 0.0009(15) C15 0.036(2) 0.046(3) 0.044(2) 0.002(2) 0.0089(18) -0.0045(19) C16 0.038(2) 0.037(2) 0.061(3) -0.010(2) 0.008(2) 0.0062(18) C17 0.0257(19) 0.055(3) 0.041(2) -0.006(2) 0.0058(16) 0.0003(18) C18 0.0257(18) 0.034(2) 0.040(2) -0.0059(18) 0.0001(16) -0.0012(16) C19 0.0283(19) 0.041(2) 0.035(2) 0.0013(18) -0.0014(16) 0.0001(16) C20 0.0277(19) 0.023(2) 0.034(2) -0.0008(16) -0.0014(15) 0.0000(15) C21 0.0124(15) 0.035(2) 0.037(2) 0.0043(17) 0.0057(14) -0.0007(15) C22 0.0204(17) 0.028(2) 0.0304(19) -0.0024(16) -0.0054(14) 0.0093(15) C23 0.0158(16) 0.031(2) 0.040(2) 0.0112(17) -0.0027(15) -0.0042(15) C27 0.019(2) 0.052(3) 0.083(3) 0.011(3) 0.023(2) -0.0035(19) C26 0.022(2) 0.052(3) 0.086(3) 0.005(3) 0.012(2) -0.002(2) C25 0.027(2) 0.043(3) 0.079(3) 0.013(2) -0.005(2) -0.0175(19) C28 0.090(4) 0.051(3) 0.035(2) 0.002(2) -0.002(2) -0.001(3) C29 0.097(4) 0.044(3) 0.057(3) -0.003(2) -0.001(3) -0.003(3) C30 0.073(3) 0.057(3) 0.039(2) -0.003(2) -0.007(2) -0.005(2) C31 0.062(3) 0.056(3) 0.037(2) 0.002(2) 0.003(2) 0.005(2) C32 0.081(4) 0.093(4) 0.043(3) -0.014(3) 0.004(3) 0.032(3) C33 0.093(4) 0.104(5) 0.053(3) -0.008(3) 0.009(3) 0.051(4) C34 0.109(5) 0.077(4) 0.073(4) 0.002(3) 0.039(4) 0.033(4) C35 0.102(4) 0.054(3) 0.058(3) 0.004(3) -0.008(3) 0.007(3) C36 0.127(5) 0.043(3) 0.054(3) 0.001(2) -0.020(3) 0.001(3) C37 0.088(4) 0.035(3) 0.041(3) -0.010(2) -0.005(2) 0.000(2) C38 0.083(3) 0.033(3) 0.028(2) -0.0014(19) -0.004(2) 0.013(2) C39 0.094(4) 0.036(3) 0.034(2) 0.000(2) -0.016(2) -0.001(2) C40 0.076(3) 0.037(3) 0.043(3) 0.003(2) -0.016(2) 0.001(2) C41 0.083(3) 0.045(3) 0.057(3) -0.001(2) -0.021(3) 0.016(3) C42 0.077(4) 0.036(3) 0.078(4) -0.001(3) -0.019(3) 0.009(3) C43 0.080(4) 0.044(3) 0.086(4) 0.012(3) -0.024(3) 0.002(3) C44 0.095(4) 0.045(3) 0.059(3) 0.008(3) -0.016(3) 0.001(3) C45 0.083(3) 0.047(3) 0.039(3) 0.007(2) -0.018(2) 0.003(3) C46 0.092(4) 0.059(3) 0.036(3) 0.002(2) -0.012(2) 0.001(3) C47 0.094(4) 0.030(2) 0.042(3) 0.000(2) 0.004(2) 0.008(2) C48 0.079(3) 0.039(3) 0.048(3) 0.001(2) 0.008(2) 0.011(2) C49 0.091(4) 0.040(3) 0.037(2) 0.000(2) -0.001(2) 0.015(3) C50 0.085(4) 0.050(3) 0.038(2) -0.006(2) -0.003(2) 0.020(3) C54 0.071(3) 0.067(4) 0.075(4) -0.003(3) -0.026(3) 0.018(3) C53 0.076(4) 0.079(4) 0.090(4) -0.020(4) -0.026(3) 0.028(3) C52 0.111(5) 0.064(4) 0.085(4) -0.015(3) -0.041(4) 0.053(4) C55 0.108(4) 0.055(3) 0.041(3) -0.003(2) -0.021(3) 0.015(3) C56 0.117(5) 0.071(4) 0.065(4) -0.017(3) -0.039(4) 0.040(4) C57 0.094(4) 0.070(4) 0.048(3) -0.011(3) -0.010(3) 0.030(3) C64 0.113(4) 0.034(3) 0.044(3) -0.005(2) -0.020(3) 0.013(3) C65 0.097(4) 0.041(3) 0.035(2) -0.005(2) -0.023(2) 0.009(3) C66 0.120(5) 0.041(3) 0.030(2) 0.003(2) -0.003(3) 0.019(3) C67 0.113(4) 0.043(3) 0.044(3) 0.010(2) -0.004(3) 0.009(3) C68 0.126(5) 0.036(3) 0.058(3) 0.004(3) 0.001(3) 0.003(3) C69 0.127(5) 0.035(3) 0.073(4) 0.007(3) 0.009(4) 0.015(3) C70 0.111(5) 0.044(3) 0.084(4) 0.013(3) 0.004(4) 0.024(3) C71 0.136(6) 0.050(3) 0.061(3) 0.013(3) -0.013(3) 0.028(3) C72 0.119(5) 0.057(3) 0.038(3) 0.008(2) -0.013(3) 0.015(3) C73 0.125(5) 0.062(4) 0.040(3) -0.007(2) -0.010(3) 0.028(3) C74 0.107(4) 0.037(3) 0.044(3) 0.001(2) -0.022(3) 0.002(3) C75 0.108(4) 0.032(3) 0.046(3) -0.001(2) -0.014(3) 0.005(3) C76 0.112(4) 0.039(3) 0.033(2) -0.003(2) -0.005(2) 0.009(3) C77 0.109(4) 0.037(3) 0.043(3) -0.005(2) -0.004(3) 0.006(3) C81 0.107(5) 0.067(4) 0.056(3) -0.001(3) -0.016(3) -0.001(3) C80 0.120(5) 0.056(4) 0.059(3) -0.005(3) -0.004(3) -0.025(3) C79 0.122(5) 0.047(3) 0.070(4) -0.001(3) -0.013(4) -0.018(3) N1 0.0068(12) 0.0403(18) 0.0396(18) 0.0044(15) 0.0093(12) -0.0094(12) N2 0.0092(13) 0.0342(18) 0.0375(17) 0.0039(14) 0.0037(12) -0.0061(12) N4 0.077(3) 0.045(2) 0.0325(19) 0.0040(17) -0.0069(18) 0.0063(19) N5 0.088(3) 0.040(2) 0.042(2) -0.0032(18) -0.006(2) 0.013(2) N7 0.094(3) 0.042(2) 0.048(2) -0.0089(19) -0.025(2) 0.024(2) N8 0.096(3) 0.038(2) 0.041(2) -0.0038(17) -0.010(2) 0.004(2) O1 0.0252(13) 0.0449(16) 0.0428(16) -0.0062(13) 0.0001(11) -0.0124(12) O2 0.0282(13) 0.0534(17) 0.0335(14) 0.0028(13) 0.0072(11) -0.0040(12) O3 0.090(2) 0.0463(19) 0.0420(18) 0.0153(16) -0.0087(16) 0.0093(17) O4 0.098(3) 0.054(2) 0.0397(18) 0.0027(15) 0.0034(18) -0.0026(19) O5 0.107(3) 0.048(2) 0.051(2) 0.0073(17) -0.0231(19) 0.0027(19) O6 0.119(3) 0.076(3) 0.046(2) -0.0047(18) -0.021(2) 0.034(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 C24 C23 1.373(5) . ? C24 C25 1.405(6) . ? N3 C23 1.330(5) . ? N3 C27 1.349(5) . ? C51 C52 1.373(9) . ? C51 C50 1.410(7) . ? N6 C50 1.328(7) . ? N6 C54 1.328(6) . ? C78 C79 1.371(8) . ? C78 C77 1.392(7) . ? N9 C81 1.335(7) . ? N9 C77 1.346(6) . ? C4 C5A 1.374(3) . ? C4 C9A 1.374(3) . ? C4 C9B 1.381(5) . ? C4 C5B 1.382(5) . ? C4 C3 1.516(5) . ? C7 C8A 1.373(3) . ? C7 C6A 1.375(3) . ? C7 C8B 1.381(5) . ? C7 C6B 1.381(5) . ? C5A C6A 1.375(3) . ? C8A C9A 1.374(3) . ? C5B C6B 1.382(5) . ? C8B C9B 1.381(5) . ? C58A C59A 1.3900 . ? C58A C63A 1.3900 . ? C58A C57 1.561(6) . ? C59A C60A 1.3900 . ? C60A C61A 1.3900 . ? C61A C62A 1.3900 . ? C62A C63A 1.3900 . ? C58B C59B 1.3900 . ? C58B C63B 1.3900 . ? C58B C57 1.550(6) . ? C59B C60B 1.3900 . ? C60B C61B 1.3900 . ? C61B C62B 1.3900 . ? C62B C63B 1.3900 . ? C1 O2 1.424(4) . ? C1 N1 1.496(5) . ? C1 C19 1.508(5) . ? C1 C18 1.521(5) . ? C2 O2 1.440(5) . ? C2 C3 1.516(6) . ? C3 N1 1.495(4) . ? C10 O1 1.231(4) . ? C10 N1 1.346(5) . ? C10 C11 1.510(5) . ? C11 C20 1.382(5) . ? C11 C12 1.399(5) . ? C12 N2 1.371(4) . ? C12 C13 1.475(5) . ? C13 C14 1.399(5) . ? C13 C18 1.413(5) . ? C14 C15 1.367(5) . ? C15 C16 1.396(6) . ? C16 C17 1.389(6) . ? C17 C18 1.380(5) . ? C20 C21 1.396(5) . ? C21 C22 1.388(5) . ? C22 N2 1.327(4) . ? C22 C23 1.498(5) . ? C27 C26 1.328(6) . ? C26 C25 1.376(6) . ? C28 O4 1.419(6) . ? C28 N4 1.489(6) . ? C28 C46 1.513(7) . ? C28 C45 1.528(7) . ? C29 O4 1.442(6) . ? C29 C30 1.534(7) . ? C30 N4 1.468(6) . ? C30 C31 1.513(6) . ? C31 C36 1.374(6) . ? C31 C32 1.416(7) . ? C32 C33 1.381(8) . ? C33 C34 1.348(8) . ? C34 C35 1.343(7) . ? C35 C36 1.364(7) . ? C37 O3 1.240(5) . ? C37 N4 1.342(6) . ? C37 C38 1.498(7) . ? C38 C47 1.381(7) . ? C38 C39 1.417(6) . ? C39 N5 1.351(7) . ? C39 C40 1.480(7) . ? C40 C41 1.407(6) . ? C40 C45 1.408(7) . ? C41 C42 1.378(7) . ? C42 C43 1.377(8) . ? C43 C44 1.377(7) . ? C44 C45 1.393(7) . ? C47 C48 1.376(7) . ? C48 C49 1.395(6) . ? C49 N5 1.340(6) . ? C49 C50 1.492(7) . ? C54 C53 1.355(8) . ? C53 C52 1.360(9) . ? C55 O6 1.422(6) . ? C55 C73 1.502(8) . ? C55 N7 1.503(7) . ? C55 C72 1.523(7) . ? C56 O6 1.398(8) . ? C56 C57 1.537(7) . ? C57 N7 1.461(7) . ? C64 O5 1.238(6) . ? C64 N7 1.352(6) . ? C64 C65 1.496(8) . ? C65 C74 1.380(7) . ? C65 C66 1.426(7) . ? C66 N8 1.346(7) . ? C66 C67 1.484(7) . ? C67 C72 1.386(7) . ? C67 C68 1.394(7) . ? C68 C69 1.377(8) . ? C69 C70 1.374(8) . ? C70 C71 1.397(8) . ? C71 C72 1.392(7) . ? C74 C75 1.361(7) . ? C75 C76 1.407(7) . ? C76 N8 1.322(6) . ? C76 C77 1.494(8) . ? C81 C80 1.366(8) . ? C80 C79 1.363(8) . ? 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 C23 C24 C25 118.9(4) . . ? C23 N3 C27 115.9(4) . . ? C52 C51 C50 118.7(6) . . ? C50 N6 C54 117.0(4) . . ? C79 C78 C77 120.1(6) . . ? C81 N9 C77 117.0(5) . . ? C5A C4 C9A 118.7(5) . . ? C5A C4 C9B 95.5(6) . . ? C9A C4 C9B 52.0(5) . . ? C5A C4 C5B 46.1(6) . . ? C9A C4 C5B 98.5(6) . . ? C9B C4 C5B 116.7(8) . . ? C5A C4 C3 118.5(4) . . ? C9A C4 C3 122.7(4) . . ? C9B C4 C3 124.9(5) . . ? C5B C4 C3 118.1(6) . . ? C8A C7 C6A 116.5(6) . . ? C8A C7 C8B 47.5(6) . . ? C6A C7 C8B 99.4(8) . . ? C8A C7 C6B 96.4(8) . . ? C6A C7 C6B 48.4(7) . . ? C8B C7 C6B 119.3(9) . . ? C4 C5A C6A 119.2(7) . . ? C7 C6A C5A 123.1(8) . . ? C7 C8A C9A 121.4(6) . . ? C8A C9A C4 121.0(6) . . ? C6B C5B C4 120.3(10) . . ? C7 C6B C5B 121.2(10) . . ? C7 C8B C9B 117.8(9) . . ? C4 C9B C8B 123.5(9) . . ? C59A C58A C63A 120.0 . . ? C59A C58A C57 123.4(5) . . ? C63A C58A C57 116.5(5) . . ? C58A C59A C60A 120.0 . . ? C61A C60A C59A 120.0 . . ? C60A C61A C62A 120.0 . . ? C61A C62A C63A 120.0 . . ? C62A C63A C58A 120.0 . . ? C59B C58B C63B 120.0 . . ? C59B C58B C57 113.3(6) . . ? C63B C58B C57 126.3(6) . . ? C58B C59B C60B 120.0 . . ? C59B C60B C61B 120.0 . . ? C62B C61B C60B 120.0 . . ? C61B C62B C63B 120.0 . . ? C62B C63B C58B 120.0 . . ? O2 C1 N1 101.8(3) . . ? O2 C1 C19 106.0(3) . . ? N1 C1 C19 113.3(3) . . ? O2 C1 C18 111.4(3) . . ? N1 C1 C18 109.6(3) . . ? C19 C1 C18 114.0(3) . . ? O2 C2 C3 104.8(3) . . ? N1 C3 C4 114.3(3) . . ? N1 C3 C2 99.2(3) . . ? C4 C3 C2 114.4(3) . . ? O1 C10 N1 122.5(3) . . ? O1 C10 C11 119.6(3) . . ? N1 C10 C11 117.9(3) . . ? C20 C11 C12 118.2(3) . . ? C20 C11 C10 116.6(3) . . ? C12 C11 C10 125.0(3) . . ? N2 C12 C11 121.5(3) . . ? N2 C12 C13 113.7(3) . . ? C11 C12 C13 124.7(3) . . ? C14 C13 C18 117.7(3) . . ? C14 C13 C12 119.2(3) . . ? C18 C13 C12 123.1(3) . . ? C15 C14 C13 122.9(4) . . ? C14 C15 C16 119.0(4) . . ? C17 C16 C15 119.2(4) . . ? C18 C17 C16 121.9(4) . . ? C17 C18 C13 119.3(4) . . ? C17 C18 C1 119.9(3) . . ? C13 C18 C1 120.9(3) . . ? C11 C20 C21 120.4(3) . . ? C22 C21 C20 117.7(3) . . ? N2 C22 C21 123.4(3) . . ? N2 C22 C23 116.0(3) . . ? C21 C22 C23 120.6(3) . . ? N3 C23 C24 123.4(3) . . ? N3 C23 C22 116.2(3) . . ? C24 C23 C22 120.5(3) . . ? C26 C27 N3 125.0(4) . . ? C27 C26 C25 119.7(4) . . ? C26 C25 C24 117.1(4) . . ? O4 C28 N4 102.3(4) . . ? O4 C28 C46 105.9(4) . . ? N4 C28 C46 114.3(4) . . ? O4 C28 C45 110.5(4) . . ? N4 C28 C45 109.7(3) . . ? C46 C28 C45 113.5(4) . . ? O4 C29 C30 103.8(4) . . ? N4 C30 C31 115.1(4) . . ? N4 C30 C29 100.8(4) . . ? C31 C30 C29 113.4(4) . . ? C36 C31 C32 114.8(5) . . ? C36 C31 C30 123.8(4) . . ? C32 C31 C30 121.1(4) . . ? C33 C32 C31 121.5(5) . . ? C34 C33 C32 119.2(5) . . ? C35 C34 C33 121.6(6) . . ? C34 C35 C36 119.3(5) . . ? C35 C36 C31 123.4(5) . . ? O3 C37 N4 121.5(5) . . ? O3 C37 C38 119.4(4) . . ? N4 C37 C38 119.0(4) . . ? C47 C38 C39 117.5(5) . . ? C47 C38 C37 117.6(4) . . ? C39 C38 C37 124.6(5) . . ? N5 C39 C38 121.9(5) . . ? N5 C39 C40 114.4(4) . . ? C38 C39 C40 123.6(5) . . ? C41 C40 C45 118.4(5) . . ? C41 C40 C39 118.2(5) . . ? C45 C40 C39 123.4(4) . . ? C42 C41 C40 121.7(5) . . ? C43 C42 C41 119.0(5) . . ? C44 C43 C42 120.8(5) . . ? C43 C44 C45 121.2(6) . . ? C44 C45 C40 118.9(5) . . ? C44 C45 C28 120.3(5) . . ? C40 C45 C28 120.9(4) . . ? C48 C47 C38 120.5(4) . . ? C47 C48 C49 118.9(5) . . ? N5 C49 C48 122.0(5) . . ? N5 C49 C50 116.2(4) . . ? C48 C49 C50 121.8(5) . . ? N6 C50 C51 121.7(5) . . ? N6 C50 C49 116.7(4) . . ? C51 C50 C49 121.5(5) . . ? N6 C54 C53 124.9(6) . . ? C54 C53 C52 118.6(6) . . ? C53 C52 C51 118.9(5) . . ? O6 C55 C73 105.5(4) . . ? O6 C55 N7 100.9(5) . . ? C73 C55 N7 114.4(4) . . ? O6 C55 C72 112.0(4) . . ? C73 C55 C72 113.8(5) . . ? N7 C55 C72 109.4(4) . . ? O6 C56 C57 105.3(5) . . ? N7 C57 C56 99.5(5) . . ? N7 C57 C58B 110.4(5) . . ? C56 C57 C58B 113.4(5) . . ? N7 C57 C58A 118.1(4) . . ? C56 C57 C58A 112.0(5) . . ? C58B C57 C58A 7.8(5) . . ? O5 C64 N7 121.3(5) . . ? O5 C64 C65 119.8(4) . . ? N7 C64 C65 118.8(5) . . ? C74 C65 C66 117.9(5) . . ? C74 C65 C64 117.4(4) . . ? C66 C65 C64 124.6(5) . . ? N8 C66 C65 120.9(5) . . ? N8 C66 C67 116.4(5) . . ? C65 C66 C67 122.7(6) . . ? C72 C67 C68 118.9(5) . . ? C72 C67 C66 123.8(5) . . ? C68 C67 C66 117.3(5) . . ? C69 C68 C67 121.2(6) . . ? C70 C69 C68 120.2(5) . . ? C69 C70 C71 119.3(5) . . ? C72 C71 C70 120.6(6) . . ? C67 C72 C71 119.7(5) . . ? C67 C72 C55 121.2(4) . . ? C71 C72 C55 119.1(5) . . ? C75 C74 C65 120.9(5) . . ? C74 C75 C76 118.1(5) . . ? N8 C76 C75 122.7(5) . . ? N8 C76 C77 116.3(4) . . ? C75 C76 C77 120.9(5) . . ? N9 C77 C78 121.4(6) . . ? N9 C77 C76 116.7(4) . . ? C78 C77 C76 121.9(5) . . ? N9 C81 C80 124.1(6) . . ? C79 C80 C81 119.2(6) . . ? C80 C79 C78 118.2(5) . . ? C10 N1 C3 119.4(3) . . ? C10 N1 C1 128.3(3) . . ? C3 N1 C1 111.5(3) . . ? C22 N2 C12 118.8(3) . . ? C37 N4 C30 120.3(4) . . ? C37 N4 C28 126.9(4) . . ? C30 N4 C28 111.6(4) . . ? C49 N5 C39 119.1(4) . . ? C64 N7 C57 120.2(5) . . ? C64 N7 C55 126.5(5) . . ? C57 N7 C55 111.8(4) . . ? C76 N8 C66 119.6(4) . . ? C1 O2 C2 108.0(3) . . ? C28 O4 C29 108.7(3) . . ? C56 O6 C55 108.6(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.446 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.088