# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2009 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Bhanuprakash Kotamarthi' _publ_contact_author_email BHANU2505@YAHOO.CO.IN _publ_section_title ; Synthesis and characterization of 9,10- bis(2-phenyl-1,3,4-oxadiazole) derivatives of anthracene: Efficient n-type emitter for organic light-emitting diodes. ; _publ_author_name 'Bhanuprakash Kotamarthi' data_ac24m #(Molcule 5) _database_code_depnum_ccdc_archive 'CCDC 725026' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C38 H34 N4 O2), C7 H8' _chemical_formula_sum 'C83 H76 N8 O4' _chemical_formula_weight 1249.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.6784(10) _cell_length_b 13.4373(11) _cell_length_c 14.2959(12) _cell_angle_alpha 64.349(1) _cell_angle_beta 66.210(1) _cell_angle_gamma 64.589(1) _cell_volume 1760.2(3) _cell_formula_units_Z 1 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 6958 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 27.18 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 662 _exptl_absorpt_coefficient_mu 0.073 _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 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17066 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6166 _reflns_number_gt 5004 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0886P)^2^+0.2658P] 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 6166 _refine_ls_number_parameters 448 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1510 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.37056(15) 0.24255(14) -0.04913(12) 0.0495(4) Uani 1 1 d . . . C2 C 0.40455(19) 0.34336(16) -0.09264(16) 0.0659(5) Uani 1 1 d . . . H2 H 0.3660 0.4064 -0.1443 0.079 Uiso 1 1 calc R . . C3 C 0.4959(2) 0.35007(19) -0.05914(19) 0.0795(6) Uani 1 1 d . . . H3 H 0.5182 0.4182 -0.0883 0.095 Uiso 1 1 calc R . . C4 C 0.5540(2) 0.2581(2) 0.01614(17) 0.0781(6) Uani 1 1 d . . . H4 H 0.6154 0.2634 0.0382 0.094 Uiso 1 1 calc R . . C5 C 0.5212(2) 0.15768(19) 0.05905(16) 0.0758(6) Uani 1 1 d . . . H5 H 0.5608 0.0948 0.1102 0.091 Uiso 1 1 calc R . . C6 C 0.43002(18) 0.14943(16) 0.02687(14) 0.0619(4) Uani 1 1 d . . . H6 H 0.4084 0.0810 0.0563 0.074 Uiso 1 1 calc R . . C7 C 0.27469(15) 0.23492(13) -0.08484(12) 0.0470(4) Uani 1 1 d . . . C8 C 0.14447(14) 0.16211(13) -0.08410(12) 0.0469(4) Uani 1 1 d . . . C9 C 0.07037(15) 0.07880(13) -0.04232(12) 0.0468(4) Uani 1 1 d . . . C10 C 0.10929(14) -0.00447(13) -0.09186(12) 0.0460(4) Uani 1 1 d . . . C11 C -0.03764(14) 0.08569(13) 0.04856(12) 0.0467(4) Uani 1 1 d . . . C12 C -0.07944(15) 0.17096(14) 0.09911(13) 0.0521(4) Uani 1 1 d . . . H12 H -0.0338 0.2244 0.0702 0.062 Uiso 1 1 calc R . . C13 C -0.18309(16) 0.17769(14) 0.18779(13) 0.0523(4) Uani 1 1 d . . . C14 C -0.25128(16) 0.09440(15) 0.23050(14) 0.0567(4) Uani 1 1 d . . . H14 H -0.3216 0.0965 0.2918 0.068 Uiso 1 1 calc R . . C15 C -0.21721(15) 0.01269(14) 0.18498(13) 0.0529(4) Uani 1 1 d . . . H15 H -0.2651 -0.0392 0.2150 0.063 Uiso 1 1 calc R . . C16 C -0.22815(19) 0.26837(16) 0.24282(15) 0.0655(5) Uani 1 1 d . . . C17 C -0.3739(2) 0.3363(2) 0.2478(2) 0.0958(8) Uani 1 1 d . . . H17A H -0.4036 0.3924 0.2839 0.144 Uiso 1 1 calc R . . H17B H -0.4250 0.2836 0.2867 0.144 Uiso 1 1 calc R . . H17C H -0.3842 0.3754 0.1761 0.144 Uiso 1 1 calc R . . C18 C -0.1507(2) 0.35505(19) 0.18278(19) 0.0812(6) Uani 1 1 d . . . H18A H -0.0593 0.3147 0.1797 0.122 Uiso 1 1 calc R . . H18B H -0.1832 0.4107 0.2198 0.122 Uiso 1 1 calc R . . H18C H -0.1608 0.3943 0.1110 0.122 Uiso 1 1 calc R . . C19 C -0.2105(3) 0.2057(2) 0.3568(2) 0.1154(10) Uani 1 1 d . . . H19A H -0.1185 0.1692 0.3529 0.173 Uiso 1 1 calc R . . H19B H -0.2549 0.1478 0.3937 0.173 Uiso 1 1 calc R . . H19C H -0.2471 0.2607 0.3952 0.173 Uiso 1 1 calc R . . N1 N 0.22006(16) 0.30697(13) -0.16040(13) 0.0673(4) Uani 1 1 d . . . N2 N 0.13343(15) 0.25873(13) -0.16007(13) 0.0672(4) Uani 1 1 d . . . O1 O 0.23255(10) 0.13973(8) -0.03253(8) 0.0477(3) Uani 1 1 d . . . C20 C 0.21194(18) 0.88080(15) 0.30491(14) 0.0597(4) Uani 1 1 d . . . C21 C 0.0973(2) 0.8934(2) 0.38635(18) 0.0792(6) Uani 1 1 d . . . H21 H 0.0872 0.9232 0.4380 0.095 Uiso 1 1 calc R . . C22 C -0.0033(2) 0.8609(3) 0.3903(2) 0.1022(8) Uani 1 1 d . . . H22 H -0.0811 0.8689 0.4450 0.123 Uiso 1 1 calc R . . C23 C 0.0115(3) 0.8175(2) 0.3143(3) 0.1047(9) Uani 1 1 d . . . H23 H -0.0556 0.7947 0.3184 0.126 Uiso 1 1 calc R . . C24 C 0.1242(3) 0.8073(2) 0.2321(2) 0.0978(8) Uani 1 1 d . . . H24 H 0.1330 0.7788 0.1800 0.117 Uiso 1 1 calc R . . C25 C 0.2244(2) 0.83917(19) 0.22652(18) 0.0782(6) Uani 1 1 d . . . H25 H 0.3007 0.8329 0.1702 0.094 Uiso 1 1 calc R . . C26 C 0.32533(16) 0.90235(14) 0.30250(12) 0.0518(4) Uani 1 1 d . . . C27 C 0.44236(15) 0.93968(14) 0.35764(13) 0.0509(4) Uani 1 1 d . . . C28 C 0.47325(15) 0.97128(14) 0.42937(13) 0.0511(4) Uani 1 1 d . . . C29 C 0.56195(15) 0.88684(14) 0.49011(13) 0.0529(4) Uani 1 1 d . . . C30 C 0.62582(19) 0.77169(16) 0.48486(16) 0.0664(5) Uani 1 1 d . . . H30 H 0.6125 0.7509 0.4368 0.080 Uiso 1 1 calc R . . C31 C 0.7056(2) 0.69192(17) 0.54845(17) 0.0726(5) Uani 1 1 d . . . H31 H 0.7462 0.6177 0.5421 0.087 Uiso 1 1 calc R . . C32 C 0.73011(17) 0.71655(16) 0.62463(15) 0.0617(4) Uani 1 1 d . . . C33 C 0.67186(16) 0.82725(15) 0.62931(14) 0.0570(4) Uani 1 1 d . . . H33 H 0.6872 0.8459 0.6778 0.068 Uiso 1 1 calc R . . C34 C 0.58847(15) 0.91546(14) 0.56315(13) 0.0511(4) Uani 1 1 d . . . C35 C 0.81465(19) 0.61946(17) 0.69871(18) 0.0732(5) Uani 1 1 d . . . C36 C 0.9444(3) 0.5611(3) 0.6317(3) 0.1595(16) Uani 1 1 d . . . H36A H 0.9283 0.5325 0.5886 0.239 Uiso 1 1 calc R . . H36B H 0.9956 0.4976 0.6783 0.239 Uiso 1 1 calc R . . H36C H 0.9916 0.6162 0.5855 0.239 Uiso 1 1 calc R . . C37 C 0.7426(3) 0.5303(2) 0.7745(3) 0.1182(10) Uani 1 1 d . . . H37A H 0.7265 0.4997 0.7331 0.177 Uiso 1 1 calc R . . H37B H 0.6604 0.5666 0.8176 0.177 Uiso 1 1 calc R . . H37C H 0.7957 0.4683 0.8205 0.177 Uiso 1 1 calc R . . C38 C 0.8380(3) 0.6628(2) 0.7693(3) 0.1276(11) Uani 1 1 d . . . H38A H 0.8920 0.5992 0.8137 0.191 Uiso 1 1 calc R . . H38B H 0.7552 0.6959 0.8142 0.191 Uiso 1 1 calc R . . H38C H 0.8816 0.7208 0.7247 0.191 Uiso 1 1 calc R . . N3 N 0.51745(14) 0.91090(14) 0.27333(12) 0.0633(4) Uani 1 1 d . . . N4 N 0.44042(15) 0.88676(14) 0.23625(11) 0.0635(4) Uani 1 1 d . . . O2 O 0.31779(10) 0.93703(10) 0.38188(9) 0.0555(3) Uani 1 1 d . . . C39 C 0.5684(7) 0.4045(5) 0.5994(5) 0.0989(15) Uani 0.50 1 d P . . C40 C 0.5474(5) 0.5594(2) 0.4096(2) 0.1065(9) Uani 1 1 d . . . C41 C 0.6718(9) 0.5131(6) 0.4274(6) 0.118(2) Uani 0.50 1 d P . . C42 C 0.6878(5) 0.4284(4) 0.5281(5) 0.1568(15) Uani 1 1 d . . . C43 C 0.5756(8) 0.4731(5) 0.5055(7) 0.112(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 C1 0.0524(9) 0.0544(9) 0.0510(8) -0.0188(7) -0.0079(7) -0.0278(7) C2 0.0743(12) 0.0593(10) 0.0785(12) -0.0132(9) -0.0257(10) -0.0369(9) C3 0.0874(14) 0.0780(13) 0.1003(15) -0.0235(12) -0.0277(12) -0.0513(12) C4 0.0791(13) 0.1026(16) 0.0818(13) -0.0281(12) -0.0271(11) -0.0491(12) C5 0.0829(13) 0.0903(14) 0.0705(12) -0.0120(10) -0.0335(10) -0.0424(11) C6 0.0703(11) 0.0667(11) 0.0599(10) -0.0101(8) -0.0206(9) -0.0377(9) C7 0.0500(8) 0.0460(8) 0.0498(8) -0.0120(7) -0.0095(7) -0.0255(7) C8 0.0446(8) 0.0532(9) 0.0494(8) -0.0129(7) -0.0125(7) -0.0240(7) C9 0.0454(8) 0.0517(8) 0.0493(8) -0.0099(7) -0.0145(7) -0.0245(7) C10 0.0419(8) 0.0523(8) 0.0496(8) -0.0111(7) -0.0144(6) -0.0226(7) C11 0.0443(8) 0.0532(9) 0.0497(8) -0.0121(7) -0.0153(7) -0.0228(7) C12 0.0525(9) 0.0547(9) 0.0585(9) -0.0150(7) -0.0153(8) -0.0272(7) C13 0.0510(9) 0.0577(9) 0.0542(9) -0.0174(7) -0.0143(7) -0.0220(7) C14 0.0512(9) 0.0661(10) 0.0553(9) -0.0205(8) -0.0050(7) -0.0273(8) C15 0.0473(9) 0.0601(10) 0.0559(9) -0.0140(8) -0.0091(7) -0.0291(7) C16 0.0709(12) 0.0673(11) 0.0666(11) -0.0277(9) -0.0123(9) -0.0275(9) C17 0.0688(13) 0.0846(15) 0.134(2) -0.0583(15) 0.0021(13) -0.0267(11) C18 0.0792(13) 0.0821(14) 0.1027(16) -0.0482(12) -0.0104(12) -0.0362(11) C19 0.187(3) 0.1059(19) 0.0777(15) -0.0355(14) -0.0432(18) -0.053(2) N1 0.0776(10) 0.0600(9) 0.0747(10) 0.0024(7) -0.0333(8) -0.0420(8) N2 0.0741(10) 0.0648(9) 0.0737(10) 0.0028(7) -0.0355(8) -0.0413(8) O1 0.0515(6) 0.0487(6) 0.0505(6) -0.0088(5) -0.0142(5) -0.0286(5) C20 0.0656(11) 0.0584(10) 0.0632(10) -0.0111(8) -0.0287(9) -0.0238(8) C21 0.0639(12) 0.1000(15) 0.0820(13) -0.0269(12) -0.0211(11) -0.0327(11) C22 0.0705(14) 0.124(2) 0.1108(19) -0.0142(16) -0.0320(13) -0.0443(14) C23 0.106(2) 0.0973(18) 0.142(2) -0.0051(16) -0.081(2) -0.0470(15) C24 0.113(2) 0.0933(17) 0.126(2) -0.0276(15) -0.0745(19) -0.0332(15) C25 0.0917(14) 0.0833(13) 0.0840(14) -0.0263(11) -0.0444(12) -0.0288(11) C26 0.0613(10) 0.0530(9) 0.0488(8) -0.0159(7) -0.0155(8) -0.0237(8) C27 0.0500(9) 0.0550(9) 0.0538(9) -0.0199(7) -0.0069(7) -0.0251(7) C28 0.0491(9) 0.0580(9) 0.0551(9) -0.0232(7) -0.0061(7) -0.0260(7) C29 0.0498(9) 0.0579(9) 0.0593(9) -0.0250(8) -0.0067(7) -0.0245(7) C30 0.0714(12) 0.0632(11) 0.0792(12) -0.0344(9) -0.0222(10) -0.0196(9) C31 0.0754(12) 0.0589(11) 0.0913(14) -0.0354(10) -0.0262(11) -0.0119(9) C32 0.0509(9) 0.0619(10) 0.0757(11) -0.0238(9) -0.0138(8) -0.0212(8) C33 0.0520(9) 0.0647(10) 0.0643(10) -0.0233(8) -0.0122(8) -0.0269(8) C34 0.0457(8) 0.0574(9) 0.0573(9) -0.0228(7) -0.0054(7) -0.0251(7) C35 0.0652(11) 0.0666(12) 0.0904(14) -0.0226(10) -0.0276(10) -0.0185(9) C36 0.0839(19) 0.166(3) 0.129(2) -0.033(2) -0.0303(18) 0.036(2) C37 0.135(2) 0.0954(18) 0.128(2) 0.0056(16) -0.063(2) -0.0540(17) C38 0.152(3) 0.0926(18) 0.179(3) -0.0274(19) -0.118(3) -0.0210(17) N3 0.0624(9) 0.0820(10) 0.0605(9) -0.0334(8) -0.0010(7) -0.0384(8) N4 0.0683(9) 0.0797(10) 0.0571(8) -0.0312(8) -0.0060(7) -0.0358(8) O2 0.0523(6) 0.0712(7) 0.0551(6) -0.0287(6) -0.0073(5) -0.0272(5) C39 0.115(5) 0.072(3) 0.102(4) -0.036(3) -0.017(4) -0.025(3) C40 0.168(3) 0.0731(17) 0.0855(17) -0.0281(14) -0.032(2) -0.043(2) C41 0.179(7) 0.084(4) 0.112(5) -0.044(4) -0.026(5) -0.057(5) C42 0.190(4) 0.111(3) 0.207(5) -0.078(3) -0.083(4) -0.024(3) C43 0.146(6) 0.073(3) 0.161(7) -0.064(4) -0.092(6) 0.003(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 C2 1.383(2) . ? C1 C6 1.384(2) . ? C1 C7 1.459(2) . ? C2 C3 1.382(3) . ? C2 H2 0.9300 . ? C3 C4 1.365(3) . ? C3 H3 0.9300 . ? C4 C5 1.371(3) . ? C4 H4 0.9300 . ? C5 C6 1.378(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.277(2) . ? C7 O1 1.3611(17) . ? C8 N2 1.277(2) . ? C8 O1 1.3589(17) . ? C8 C9 1.481(2) . ? C9 C10 1.396(2) . ? C9 C11 1.403(2) . ? C10 C15 1.424(2) 2 ? C10 C11 1.434(2) 2 ? C11 C12 1.423(2) . ? C11 C10 1.434(2) 2 ? C12 C13 1.359(2) . ? C12 H12 0.9300 . ? C13 C14 1.429(2) . ? C13 C16 1.525(2) . ? C14 C15 1.350(2) . ? C14 H14 0.9300 . ? C15 C10 1.424(2) 2 ? C15 H15 0.9300 . ? C16 C18 1.525(3) . ? C16 C19 1.529(3) . ? C16 C17 1.537(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N1 N2 1.4144(19) . ? C20 C21 1.376(3) . ? C20 C25 1.390(3) . ? C20 C26 1.457(2) . ? C21 C22 1.394(3) . ? C21 H21 0.9300 . ? C22 C23 1.365(4) . ? C22 H22 0.9300 . ? C23 C24 1.367(4) . ? C23 H23 0.9300 . ? C24 C25 1.372(3) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 N4 1.285(2) . ? C26 O2 1.3618(18) . ? C27 N3 1.277(2) . ? C27 O2 1.3656(18) . ? C27 C28 1.473(2) . ? C28 C29 1.407(2) . ? C28 C34 1.409(2) 2_676 ? C29 C30 1.422(2) . ? C29 C34 1.430(2) . ? C30 C31 1.351(3) . ? C30 H30 0.9300 . ? C31 C32 1.422(3) . ? C31 H31 0.9300 . ? C32 C33 1.364(2) . ? C32 C35 1.530(3) . ? C33 C34 1.425(2) . ? C33 H33 0.9300 . ? C34 C28 1.409(2) 2_676 ? C35 C36 1.513(3) . ? C35 C38 1.517(3) . ? C35 C37 1.524(3) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? N3 N4 1.4070(19) . ? C39 C43 1.250(9) . ? C39 C40 1.266(8) 2_666 ? C39 C42 1.428(8) . ? C40 C39 1.266(8) 2_666 ? C40 C41 1.395(9) . ? C40 C43 1.412(8) . ? C40 C43 1.550(10) 2_666 ? C41 C43 1.335(11) . ? C41 C42 1.421(8) . ? C42 C43 1.295(7) . ? C43 C40 1.550(10) 2_666 ? C43 C43 1.643(14) 2_666 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.11(15) . . ? C2 C1 C7 119.92(15) . . ? C6 C1 C7 120.96(14) . . ? C3 C2 C1 119.78(18) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 120.88(18) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.55(18) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 120.43(19) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 120.25(16) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? N1 C7 O1 112.07(13) . . ? N1 C7 C1 129.37(14) . . ? O1 C7 C1 118.56(13) . . ? N2 C8 O1 112.63(13) . . ? N2 C8 C9 129.40(14) . . ? O1 C8 C9 117.84(13) . . ? C10 C9 C11 121.79(13) . . ? C10 C9 C8 120.31(13) . . ? C11 C9 C8 117.89(14) . . ? C9 C10 C15 123.15(13) . 2 ? C9 C10 C11 119.26(14) . 2 ? C15 C10 C11 117.59(14) 2 2 ? C9 C11 C12 122.43(13) . . ? C9 C11 C10 118.94(14) . 2 ? C12 C11 C10 118.63(14) . 2 ? C13 C12 C11 122.91(14) . . ? C13 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? C12 C13 C14 117.33(15) . . ? C12 C13 C16 123.28(14) . . ? C14 C13 C16 119.39(14) . . ? C15 C14 C13 122.32(15) . . ? C15 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C14 C15 C10 121.21(14) . 2 ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.4 2 . ? C18 C16 C13 112.54(15) . . ? C18 C16 C19 109.01(18) . . ? C13 C16 C19 108.40(17) . . ? C18 C16 C17 107.96(17) . . ? C13 C16 C17 108.96(16) . . ? C19 C16 C17 110.0(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C7 N1 N2 106.55(12) . . ? C8 N2 N1 105.86(13) . . ? C8 O1 C7 102.89(11) . . ? C21 C20 C25 119.89(18) . . ? C21 C20 C26 121.55(17) . . ? C25 C20 C26 118.42(18) . . ? C20 C21 C22 119.0(2) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C23 C22 C21 120.4(3) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 120.4(2) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C23 C24 C25 120.1(2) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C25 C20 120.1(2) . . ? C24 C25 H25 120.0 . . ? C20 C25 H25 120.0 . . ? N4 C26 O2 112.13(14) . . ? N4 C26 C20 128.28(15) . . ? O2 C26 C20 119.47(15) . . ? N3 C27 O2 112.27(14) . . ? N3 C27 C28 129.24(15) . . ? O2 C27 C28 118.47(13) . . ? C29 C28 C34 121.70(14) . 2_676 ? C29 C28 C27 119.06(14) . . ? C34 C28 C27 119.22(15) 2_676 . ? C28 C29 C30 123.28(15) . . ? C28 C29 C34 119.41(14) . . ? C30 C29 C34 117.29(16) . . ? C31 C30 C29 121.19(17) . . ? C31 C30 H30 119.4 . . ? C29 C30 H30 119.4 . . ? C30 C31 C32 122.83(17) . . ? C30 C31 H31 118.6 . . ? C32 C31 H31 118.6 . . ? C33 C32 C31 116.85(17) . . ? C33 C32 C35 123.45(17) . . ? C31 C32 C35 119.66(16) . . ? C32 C33 C34 122.81(16) . . ? C32 C33 H33 118.6 . . ? C34 C33 H33 118.6 . . ? C28 C34 C33 122.10(15) 2_676 . ? C28 C34 C29 118.87(15) 2_676 . ? C33 C34 C29 118.97(15) . . ? C36 C35 C38 110.3(3) . . ? C36 C35 C37 109.0(3) . . ? C38 C35 C37 106.5(2) . . ? C36 C35 C32 109.5(2) . . ? C38 C35 C32 112.50(18) . . ? C37 C35 C32 108.88(17) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C35 C38 H38A 109.5 . . ? C35 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C35 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C27 N3 N4 106.51(13) . . ? C26 N4 N3 106.32(13) . . ? C26 O2 C27 102.76(12) . . ? C43 C39 C40 76.0(6) . 2_666 ? C43 C39 C42 57.4(5) . . ? C40 C39 C42 133.4(6) 2_666 . ? C39 C40 C41 175.4(5) 2_666 . ? C39 C40 C43 118.6(6) 2_666 . ? C41 C40 C43 56.8(4) . . ? C39 C40 C43 51.5(4) 2_666 2_666 ? C41 C40 C43 123.9(4) . 2_666 ? C43 C40 C43 67.2(5) . 2_666 ? C43 C41 C40 62.2(5) . . ? C43 C41 C42 55.9(4) . . ? C40 C41 C42 118.2(7) . . ? C43 C42 C41 58.7(6) . . ? C43 C42 C39 54.4(5) . . ? C41 C42 C39 113.0(6) . . ? C39 C43 C42 68.2(5) . . ? C39 C43 C41 133.5(8) . . ? C42 C43 C41 65.4(6) . . ? C39 C43 C40 164.9(9) . . ? C42 C43 C40 126.3(9) . . ? C41 C43 C40 61.0(6) . . ? C39 C43 C40 52.5(6) . 2_666 ? C42 C43 C40 120.7(7) . 2_666 ? C41 C43 C40 173.2(7) . 2_666 ? C40 C43 C40 112.8(5) . 2_666 ? C39 C43 C43 104.8(10) . 2_666 ? C42 C43 C43 172.3(11) . 2_666 ? C41 C43 C43 121.3(9) . 2_666 ? C40 C43 C43 60.4(5) . 2_666 ? C40 C43 C43 52.4(6) 2_666 2_666 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.6(3) . . . . ? C7 C1 C2 C3 -179.61(17) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? C7 C1 C6 C5 179.43(17) . . . . ? C2 C1 C7 N1 6.3(3) . . . . ? C6 C1 C7 N1 -172.70(17) . . . . ? C2 C1 C7 O1 -172.98(15) . . . . ? C6 C1 C7 O1 8.0(2) . . . . ? N2 C8 C9 C10 84.7(2) . . . . ? O1 C8 C9 C10 -99.81(17) . . . . ? N2 C8 C9 C11 -96.2(2) . . . . ? O1 C8 C9 C11 79.28(18) . . . . ? C11 C9 C10 C15 179.10(14) . . . 2 ? C8 C9 C10 C15 -1.8(2) . . . 2 ? C11 C9 C10 C11 -0.3(2) . . . 2 ? C8 C9 C10 C11 178.71(13) . . . 2 ? C10 C9 C11 C12 -179.21(14) . . . . ? C8 C9 C11 C12 1.7(2) . . . . ? C10 C9 C11 C10 0.3(2) . . . 2 ? C8 C9 C11 C10 -178.73(13) . . . 2 ? C9 C11 C12 C13 -179.33(15) . . . . ? C10 C11 C12 C13 1.1(2) 2 . . . ? C11 C12 C13 C14 0.0(2) . . . . ? C11 C12 C13 C16 179.68(15) . . . . ? C12 C13 C14 C15 -1.0(3) . . . . ? C16 C13 C14 C15 179.31(16) . . . . ? C13 C14 C15 C10 0.8(3) . . . 2 ? C12 C13 C16 C18 4.1(3) . . . . ? C14 C13 C16 C18 -176.23(16) . . . . ? C12 C13 C16 C19 -116.5(2) . . . . ? C14 C13 C16 C19 63.1(2) . . . . ? C12 C13 C16 C17 123.84(19) . . . . ? C14 C13 C16 C17 -56.5(2) . . . . ? O1 C7 N1 N2 0.36(19) . . . . ? C1 C7 N1 N2 -178.97(16) . . . . ? O1 C8 N2 N1 -0.4(2) . . . . ? C9 C8 N2 N1 175.30(16) . . . . ? C7 N1 N2 C8 0.0(2) . . . . ? N2 C8 O1 C7 0.58(18) . . . . ? C9 C8 O1 C7 -175.65(13) . . . . ? N1 C7 O1 C8 -0.56(17) . . . . ? C1 C7 O1 C8 178.84(13) . . . . ? C25 C20 C21 C22 1.8(3) . . . . ? C26 C20 C21 C22 -173.86(19) . . . . ? C20 C21 C22 C23 -0.2(4) . . . . ? C21 C22 C23 C24 -1.2(4) . . . . ? C22 C23 C24 C25 1.0(4) . . . . ? C23 C24 C25 C20 0.6(4) . . . . ? C21 C20 C25 C24 -2.0(3) . . . . ? C26 C20 C25 C24 173.75(19) . . . . ? C21 C20 C26 N4 174.92(19) . . . . ? C25 C20 C26 N4 -0.8(3) . . . . ? C21 C20 C26 O2 -0.7(3) . . . . ? C25 C20 C26 O2 -176.40(16) . . . . ? N3 C27 C28 C29 -65.5(2) . . . . ? O2 C27 C28 C29 113.00(17) . . . . ? N3 C27 C28 C34 115.6(2) . . . 2_676 ? O2 C27 C28 C34 -65.9(2) . . . 2_676 ? C34 C28 C29 C30 179.85(16) 2_676 . . . ? C27 C28 C29 C30 1.0(2) . . . . ? C34 C28 C29 C34 1.3(3) 2_676 . . . ? C27 C28 C29 C34 -177.53(14) . . . . ? C28 C29 C30 C31 -176.87(17) . . . . ? C34 C29 C30 C31 1.7(3) . . . . ? C29 C30 C31 C32 0.6(3) . . . . ? C30 C31 C32 C33 -1.9(3) . . . . ? C30 C31 C32 C35 176.10(18) . . . . ? C31 C32 C33 C34 0.8(3) . . . . ? C35 C32 C33 C34 -177.04(16) . . . . ? C32 C33 C34 C28 178.58(15) . . . 2_676 ? C32 C33 C34 C29 1.4(2) . . . . ? C28 C29 C34 C28 -1.3(2) . . . 2_676 ? C30 C29 C34 C28 -179.90(15) . . . 2_676 ? C28 C29 C34 C33 176.01(14) . . . . ? C30 C29 C34 C33 -2.6(2) . . . . ? C33 C32 C35 C36 -129.0(3) . . . . ? C31 C32 C35 C36 53.1(3) . . . . ? C33 C32 C35 C38 -6.0(3) . . . . ? C31 C32 C35 C38 176.2(2) . . . . ? C33 C32 C35 C37 111.9(2) . . . . ? C31 C32 C35 C37 -66.0(3) . . . . ? O2 C27 N3 N4 0.08(19) . . . . ? C28 C27 N3 N4 178.68(16) . . . . ? O2 C26 N4 N3 0.77(19) . . . . ? C20 C26 N4 N3 -175.13(16) . . . . ? C27 N3 N4 C26 -0.52(19) . . . . ? N4 C26 O2 C27 -0.71(18) . . . . ? C20 C26 O2 C27 175.59(14) . . . . ? N3 C27 O2 C26 0.35(18) . . . . ? C28 C27 O2 C26 -178.41(14) . . . . ? C43 C40 C41 C43 3.3(6) 2_666 . . . ? C43 C40 C41 C42 -1.3(3) . . . . ? C43 C40 C41 C42 2.1(6) 2_666 . . . ? C40 C41 C42 C43 1.4(4) . . . . ? C43 C41 C42 C39 -2.7(4) . . . . ? C40 C41 C42 C39 -1.3(6) . . . . ? C40 C39 C42 C43 -0.5(5) 2_666 . . . ? C43 C39 C42 C41 2.8(4) . . . . ? C40 C39 C42 C41 2.4(8) 2_666 . . . ? C40 C39 C43 C42 179.6(4) 2_666 . . . ? C40 C39 C43 C41 175.8(7) 2_666 . . . ? C42 C39 C43 C41 -3.8(6) . . . . ? C40 C39 C43 C40 14(2) 2_666 . . . ? C42 C39 C43 C40 -165.8(19) . . . . ? C42 C39 C43 C40 -179.6(4) . . . 2_666 ? C40 C39 C43 C43 3.2(4) 2_666 . . 2_666 ? C42 C39 C43 C43 -176.5(5) . . . 2_666 ? C41 C42 C43 C39 -176.9(5) . . . . ? C39 C42 C43 C41 176.9(5) . . . . ? C41 C42 C43 C40 -1.5(4) . . . . ? C39 C42 C43 C40 175.4(6) . . . . ? C41 C42 C43 C40 -176.6(5) . . . 2_666 ? C39 C42 C43 C40 0.3(4) . . . 2_666 ? C40 C41 C43 C39 -174.7(7) . . . . ? C42 C41 C43 C39 3.9(6) . . . . ? C40 C41 C43 C42 -178.6(4) . . . . ? C42 C41 C43 C40 178.6(4) . . . . ? C40 C41 C43 C43 -3.1(5) . . . 2_666 ? C42 C41 C43 C43 175.6(6) . . . 2_666 ? C39 C40 C43 C39 -15(2) 2_666 . . . ? C41 C40 C43 C39 165(2) . . . . ? C43 C40 C43 C39 -11.9(17) 2_666 . . . ? C39 C40 C43 C42 -178.9(5) 2_666 . . . ? C41 C40 C43 C42 1.6(4) . . . . ? C43 C40 C43 C42 -175.4(7) 2_666 . . . ? C39 C40 C43 C41 179.5(5) 2_666 . . . ? C43 C40 C43 C41 -177.0(5) 2_666 . . . ? C39 C40 C43 C40 -3.5(5) 2_666 . . 2_666 ? C41 C40 C43 C40 177.0(5) . . . 2_666 ? C43 C40 C43 C40 -0.005(1) 2_666 . . 2_666 ? C39 C40 C43 C43 -3.5(5) 2_666 . . 2_666 ? C41 C40 C43 C43 177.0(5) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.319 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.052 data_ac75m #(Molecule 10) _database_code_depnum_ccdc_archive 'CCDC 725027' # start Validation Reply Form _vrf_PLAT220_ac75m ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.80 Ratio RESPONSE: The side chain (C8-C13 and C33-C38) atoms exhibit a high degree of thermal motion but no model for disorder could be found ; _vrf_PLAT222_ac75m ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.31 Ratio RESPONSE: The side chain (C8-C13 and C33-C38) atoms exhibit a high degree of thermal motion ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H58 N4 O2' _chemical_formula_sum 'C50 H58 N4 O2' _chemical_formula_weight 747.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.4303(7) _cell_length_b 14.1082(8) _cell_length_c 14.3536(8) _cell_angle_alpha 107.583(1) _cell_angle_beta 111.517(1) _cell_angle_gamma 105.634(1) _cell_volume 2178.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 6103 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 24.58 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.139 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 0.069 _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 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21117 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7641 _reflns_number_gt 5571 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.1097P)^2^+0.6263P] 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 7641 _refine_ls_number_parameters 505 _refine_ls_number_restraints 94 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.2115 _refine_ls_wR_factor_gt 0.1924 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.102 _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 0.3798(2) 0.47431(19) 0.16356(19) 0.0525(6) Uani 1 1 d . . . C2 C 0.4995(2) 0.50820(19) 0.17989(19) 0.0543(6) Uani 1 1 d . . . C3 C 0.5430(3) 0.5787(3) 0.1417(3) 0.0877(10) Uani 1 1 d . . . H3 H 0.4951 0.6066 0.1044 0.105 Uiso 1 1 calc R . . C4 C 0.6567(3) 0.6086(3) 0.1577(3) 0.1007(12) Uani 1 1 d . . . H4 H 0.6837 0.6556 0.1300 0.121 Uiso 1 1 calc R . . C5 C 0.7306(3) 0.5713(3) 0.2130(3) 0.0845(9) Uani 1 1 d U . . C6 C 0.6872(2) 0.5016(3) 0.2518(2) 0.0753(8) Uani 1 1 d . . . H6 H 0.7360 0.4748 0.2899 0.090 Uiso 1 1 calc R . . C7 C 0.5745(2) 0.4700(2) 0.2364(2) 0.0634(7) Uani 1 1 d . . . H7 H 0.5480 0.4227 0.2640 0.076 Uiso 1 1 calc R . . C8 C 0.8523(3) 0.5989(5) 0.2237(4) 0.1322(13) Uani 1 1 d U . . H8A H 0.8867 0.5594 0.2606 0.159 Uiso 1 1 calc R . . H8B H 0.8414 0.5687 0.1485 0.159 Uiso 1 1 calc R . . C9 C 0.9361(4) 0.7078(5) 0.2793(5) 0.1640(19) Uani 1 1 d U . . H9A H 0.9060 0.7487 0.2418 0.197 Uiso 1 1 calc R . . H9B H 1.0078 0.7106 0.2763 0.197 Uiso 1 1 calc R . . C10 C 0.9640(5) 0.7589(5) 0.3953(5) 0.1517(16) Uani 1 1 d U . . H10A H 0.9775 0.7099 0.4286 0.182 Uiso 1 1 calc R . . H10B H 0.8974 0.7709 0.3987 0.182 Uiso 1 1 calc R . . C11 C 1.0752(5) 0.8697(6) 0.4626(6) 0.174(2) Uani 1 1 d U . . H11A H 1.1385 0.8572 0.4515 0.209 Uiso 1 1 calc R . . H11B H 1.0581 0.9190 0.4310 0.209 Uiso 1 1 calc R . . C12 C 1.1187(6) 0.9252(6) 0.5813(6) 0.191(2) Uani 1 1 d U . . H12A H 1.1323 0.8730 0.6096 0.229 Uiso 1 1 calc R . . H12B H 1.0528 0.9346 0.5892 0.229 Uiso 1 1 calc R . . C13 C 1.2252(5) 1.0334(6) 0.6627(6) 0.199(3) Uani 1 1 d U . . H13A H 1.2942 1.0278 0.6609 0.299 Uiso 1 1 calc R . . H13B H 1.2360 1.0515 0.7368 0.299 Uiso 1 1 calc R . . H13C H 1.2135 1.0899 0.6423 0.299 Uiso 1 1 calc R . . C14 C 0.2043(2) 0.46278(19) 0.1071(2) 0.0544(6) Uani 1 1 d . . . C15 C 0.1000(2) 0.48162(19) 0.0507(2) 0.0530(6) Uani 1 1 d . . . C16 C -0.0096(2) 0.39123(19) -0.0268(2) 0.0531(6) Uani 1 1 d . . . C17 C -0.0242(2) 0.2804(2) -0.0602(2) 0.0644(7) Uani 1 1 d . . . H17 H 0.0411 0.2664 -0.0293 0.077 Uiso 1 1 calc R . . C18 C 0.1118(2) 0.59080(19) 0.07847(19) 0.0527(6) Uani 1 1 d . . . C19 C 0.2220(2) 0.6844(2) 0.1582(2) 0.0557(6) Uani 1 1 d . . . H19 H 0.2883 0.6730 0.1922 0.067 Uiso 1 1 calc R . . C20 C 0.2342(2) 0.7892(2) 0.1867(2) 0.0575(6) Uani 1 1 d . . . C21 C 0.1312(2) 0.8049(2) 0.1358(2) 0.0669(7) Uani 1 1 d . . . H21 H 0.1376 0.8763 0.1552 0.080 Uiso 1 1 calc R . . C22 C 0.3520(2) 0.8893(2) 0.2722(2) 0.0668(7) Uani 1 1 d . . . C23 C 0.4543(3) 0.8581(3) 0.3110(3) 0.0877(10) Uani 1 1 d . . . H23A H 0.4420 0.8149 0.3495 0.132 Uiso 1 1 calc R . . H23B H 0.5271 0.9236 0.3607 0.132 Uiso 1 1 calc R . . H23C H 0.4586 0.8160 0.2472 0.132 Uiso 1 1 calc R . . C24 C 0.3402(3) 0.9494(3) 0.3731(3) 0.0992(11) Uani 1 1 d . . . H24A H 0.2713 0.9634 0.3481 0.149 Uiso 1 1 calc R . . H24B H 0.4093 1.0179 0.4235 0.149 Uiso 1 1 calc R . . H24C H 0.3325 0.9045 0.4111 0.149 Uiso 1 1 calc R . . C25 C 0.3807(3) 0.9676(3) 0.2220(3) 0.0974(11) Uani 1 1 d . . . H25A H 0.3910 0.9315 0.1601 0.146 Uiso 1 1 calc R . . H25B H 0.4523 1.0323 0.2780 0.146 Uiso 1 1 calc R . . H25C H 0.3168 0.9880 0.1963 0.146 Uiso 1 1 calc R . . C26 C 0.3800(2) 0.18014(19) 0.02098(19) 0.0521(6) Uani 1 1 d . . . C27 C 0.4987(2) 0.1861(2) 0.0546(2) 0.0561(6) Uani 1 1 d . . . C28 C 0.5706(3) 0.2436(3) 0.0243(3) 0.0754(8) Uani 1 1 d . . . H28 H 0.5437 0.2799 -0.0166 0.090 Uiso 1 1 calc R . . C29 C 0.6825(3) 0.2481(3) 0.0537(3) 0.0825(9) Uani 1 1 d . . . H29 H 0.7298 0.2886 0.0330 0.099 Uiso 1 1 calc R . . C30 C 0.7255(3) 0.1954(3) 0.1120(3) 0.0756(8) Uani 1 1 d U . . C31 C 0.6538(3) 0.1389(3) 0.1427(3) 0.1014(12) Uani 1 1 d . . . H31 H 0.6810 0.1022 0.1832 0.122 Uiso 1 1 calc R . . C32 C 0.5424(3) 0.1346(3) 0.1156(3) 0.0926(11) Uani 1 1 d . . . H32 H 0.4965 0.0962 0.1388 0.111 Uiso 1 1 calc R . . C33 C 0.8447(3) 0.1946(3) 0.1371(4) 0.1040(10) Uani 1 1 d U . . H33A H 0.8630 0.1616 0.1878 0.125 Uiso 1 1 calc R . . H33B H 0.8378 0.1471 0.0679 0.125 Uiso 1 1 calc R . . C34 C 0.9468(3) 0.3027(4) 0.1869(4) 0.1279(14) Uani 1 1 d U . . H34A H 1.0140 0.2892 0.1870 0.153 Uiso 1 1 calc R . . H34B H 0.9269 0.3376 0.1383 0.153 Uiso 1 1 calc R . . C35 C 0.9837(3) 0.3797(4) 0.2993(4) 0.1215(13) Uani 1 1 d U . . H35A H 1.0027 0.3442 0.3475 0.146 Uiso 1 1 calc R . . H35B H 0.9164 0.3932 0.2987 0.146 Uiso 1 1 calc R . . C36 C 1.0870(3) 0.4892(4) 0.3519(4) 0.1267(14) Uani 1 1 d U . . H36A H 1.1506 0.4756 0.3426 0.152 Uiso 1 1 calc R . . H36B H 1.0636 0.5287 0.3095 0.152 Uiso 1 1 calc R . . C37 C 1.1345(5) 0.5605(5) 0.4677(5) 0.173(2) Uani 1 1 d U . . H37A H 1.1511 0.5193 0.5100 0.207 Uiso 1 1 calc R . . H37B H 1.0740 0.5812 0.4763 0.207 Uiso 1 1 calc R . . C38 C 1.2476(5) 0.6664(5) 0.5201(6) 0.220(3) Uani 1 1 d U . . H38A H 1.3155 0.6507 0.5436 0.329 Uiso 1 1 calc R . . H38B H 1.2535 0.7210 0.5836 0.329 Uiso 1 1 calc R . . H38C H 1.2445 0.6935 0.4657 0.329 Uiso 1 1 calc R . . C39 C 0.20392(19) 0.12781(19) -0.00369(18) 0.0499(5) Uani 1 1 d . . . C40 C 0.09891(19) 0.06418(18) -0.00157(18) 0.0477(5) Uani 1 1 d . . . C41 C 0.10476(18) 0.07887(17) 0.10235(18) 0.0458(5) Uani 1 1 d . . . C42 C 0.2069(2) 0.16029(19) 0.20655(19) 0.0516(6) Uani 1 1 d . . . H42 H 0.2715 0.2043 0.2054 0.062 Uiso 1 1 calc R . . C43 C 0.2134(2) 0.17608(19) 0.30725(19) 0.0534(6) Uani 1 1 d . . . C44 C 0.1136(2) 0.1076(2) 0.3059(2) 0.0667(7) Uani 1 1 d . . . H44 H 0.1166 0.1160 0.3738 0.080 Uiso 1 1 calc R . . C45 C 0.0142(2) 0.0305(2) 0.2101(2) 0.0610(6) Uani 1 1 d . . . H45 H -0.0492 -0.0119 0.2139 0.073 Uiso 1 1 calc R . . C46 C 0.00428(19) 0.01279(18) 0.10331(18) 0.0484(5) Uani 1 1 d . . . C47 C 0.3213(2) 0.2683(2) 0.4182(2) 0.0624(7) Uani 1 1 d . . . C48 C 0.2989(4) 0.3710(3) 0.4426(3) 0.1090(13) Uani 1 1 d . . . H48A H 0.2315 0.3581 0.4541 0.163 Uiso 1 1 calc R . . H48B H 0.2840 0.3880 0.3803 0.163 Uiso 1 1 calc R . . H48C H 0.3673 0.4316 0.5086 0.163 Uiso 1 1 calc R . . C49 C 0.4340(3) 0.2944(4) 0.4098(3) 0.1175(14) Uani 1 1 d . . . H49A H 0.5005 0.3467 0.4821 0.176 Uiso 1 1 calc R . . H49B H 0.4288 0.3248 0.3577 0.176 Uiso 1 1 calc R . . H49C H 0.4439 0.2282 0.3844 0.176 Uiso 1 1 calc R . . C50 C 0.3391(3) 0.2395(3) 0.5152(2) 0.0938(10) Uani 1 1 d . . . H50A H 0.4122 0.2948 0.5807 0.141 Uiso 1 1 calc R . . H50B H 0.3420 0.1693 0.4962 0.141 Uiso 1 1 calc R . . H50C H 0.2745 0.2363 0.5301 0.141 Uiso 1 1 calc R . . N1 N 0.33123(19) 0.4159(2) 0.2014(2) 0.0722(6) Uani 1 1 d . . . N2 N 0.21540(19) 0.4085(2) 0.1647(2) 0.0729(6) Uani 1 1 d . . . N3 N 0.33186(19) 0.22966(19) -0.0298(2) 0.0675(6) Uani 1 1 d . . . N4 N 0.21615(19) 0.19507(19) -0.0459(2) 0.0669(6) Uani 1 1 d . . . O1 O 0.30466(14) 0.50640(13) 0.10129(13) 0.0549(4) Uani 1 1 d . . . O2 O 0.30469(13) 0.11372(13) 0.04100(13) 0.0536(4) 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 0.0514(13) 0.0517(13) 0.0556(14) 0.0262(11) 0.0205(11) 0.0292(11) C2 0.0527(14) 0.0531(13) 0.0532(13) 0.0227(11) 0.0202(11) 0.0266(11) C3 0.0670(19) 0.111(2) 0.116(3) 0.083(2) 0.0410(18) 0.0480(18) C4 0.072(2) 0.130(3) 0.130(3) 0.096(3) 0.049(2) 0.041(2) C5 0.0669(15) 0.124(3) 0.0780(19) 0.0553(19) 0.0357(15) 0.0491(16) C6 0.0615(17) 0.100(2) 0.0778(18) 0.0479(17) 0.0302(15) 0.0494(16) C7 0.0589(15) 0.0696(16) 0.0699(16) 0.0376(14) 0.0280(13) 0.0362(13) C8 0.071(2) 0.208(3) 0.140(3) 0.105(2) 0.056(2) 0.054(2) C9 0.099(3) 0.222(4) 0.168(3) 0.096(3) 0.076(3) 0.039(2) C10 0.127(3) 0.189(4) 0.171(3) 0.094(3) 0.093(3) 0.066(2) C11 0.120(3) 0.211(4) 0.190(3) 0.092(3) 0.081(3) 0.058(3) C12 0.148(4) 0.201(5) 0.197(4) 0.068(3) 0.095(4) 0.050(3) C13 0.145(5) 0.209(6) 0.209(5) 0.086(4) 0.086(4) 0.038(3) C14 0.0489(13) 0.0562(14) 0.0621(14) 0.0282(12) 0.0250(11) 0.0290(11) C15 0.0532(14) 0.0591(14) 0.0576(14) 0.0306(12) 0.0269(11) 0.0339(12) C16 0.0521(13) 0.0552(14) 0.0601(14) 0.0288(12) 0.0271(11) 0.0307(11) C17 0.0616(16) 0.0606(15) 0.0763(17) 0.0328(14) 0.0285(14) 0.0380(13) C18 0.0530(14) 0.0574(14) 0.0568(14) 0.0284(11) 0.0279(11) 0.0311(12) C19 0.0517(14) 0.0609(15) 0.0582(14) 0.0272(12) 0.0246(11) 0.0317(12) C20 0.0604(15) 0.0554(14) 0.0574(14) 0.0241(12) 0.0269(12) 0.0294(12) C21 0.0682(17) 0.0500(14) 0.0762(17) 0.0246(13) 0.0268(14) 0.0328(13) C22 0.0632(16) 0.0592(15) 0.0605(15) 0.0156(13) 0.0220(13) 0.0267(13) C23 0.0601(17) 0.0730(19) 0.089(2) 0.0132(16) 0.0172(15) 0.0258(15) C24 0.091(2) 0.099(2) 0.070(2) 0.0075(18) 0.0281(18) 0.040(2) C25 0.094(2) 0.0654(19) 0.095(2) 0.0299(18) 0.0303(19) 0.0125(17) C26 0.0494(13) 0.0531(13) 0.0512(13) 0.0239(11) 0.0246(11) 0.0177(11) C27 0.0500(13) 0.0581(14) 0.0566(14) 0.0237(12) 0.0264(11) 0.0201(11) C28 0.0692(18) 0.093(2) 0.090(2) 0.0570(18) 0.0488(16) 0.0379(16) C29 0.0682(19) 0.101(2) 0.105(2) 0.057(2) 0.0592(18) 0.0360(17) C30 0.0618(14) 0.0806(19) 0.0846(19) 0.0320(16) 0.0386(15) 0.0322(14) C31 0.068(2) 0.126(3) 0.143(3) 0.092(3) 0.050(2) 0.051(2) C32 0.0600(18) 0.123(3) 0.129(3) 0.092(2) 0.0491(19) 0.0399(18) C33 0.0732(17) 0.123(2) 0.126(3) 0.0505(19) 0.0540(18) 0.0533(15) C34 0.0667(18) 0.149(3) 0.138(3) 0.036(2) 0.050(2) 0.0376(16) C35 0.072(2) 0.149(3) 0.124(2) 0.0423(19) 0.0405(19) 0.0530(16) C36 0.076(2) 0.135(3) 0.149(3) 0.046(2) 0.041(2) 0.0575(16) C37 0.112(3) 0.163(4) 0.161(3) 0.016(3) 0.031(3) 0.062(2) C38 0.108(4) 0.178(5) 0.228(6) 0.000(4) 0.028(4) 0.045(3) C39 0.0470(13) 0.0540(13) 0.0471(12) 0.0222(11) 0.0204(10) 0.0237(11) C40 0.0442(12) 0.0508(12) 0.0510(13) 0.0243(10) 0.0215(10) 0.0250(10) C41 0.0447(12) 0.0489(12) 0.0474(12) 0.0224(10) 0.0209(10) 0.0263(10) C42 0.0479(13) 0.0525(13) 0.0519(13) 0.0231(11) 0.0213(11) 0.0230(11) C43 0.0527(14) 0.0541(13) 0.0501(13) 0.0208(11) 0.0210(11) 0.0273(11) C44 0.0631(16) 0.0835(19) 0.0483(14) 0.0267(13) 0.0273(13) 0.0274(14) C45 0.0534(14) 0.0755(17) 0.0520(14) 0.0278(13) 0.0274(12) 0.0235(13) C46 0.0464(12) 0.0536(13) 0.0490(13) 0.0237(11) 0.0226(10) 0.0269(11) C47 0.0610(15) 0.0604(15) 0.0481(13) 0.0175(12) 0.0159(12) 0.0253(12) C48 0.130(3) 0.070(2) 0.081(2) 0.0167(17) 0.017(2) 0.048(2) C49 0.0562(19) 0.142(3) 0.072(2) 0.003(2) 0.0133(16) 0.008(2) C50 0.100(2) 0.083(2) 0.0549(17) 0.0270(16) 0.0088(16) 0.0250(18) N1 0.0587(13) 0.0919(16) 0.0916(17) 0.0622(14) 0.0348(12) 0.0451(12) N2 0.0605(13) 0.0955(17) 0.0935(17) 0.0651(15) 0.0390(12) 0.0470(13) N3 0.0556(13) 0.0777(15) 0.0834(15) 0.0509(13) 0.0356(11) 0.0283(11) N4 0.0584(13) 0.0742(14) 0.0821(15) 0.0486(13) 0.0341(11) 0.0319(11) O1 0.0519(9) 0.0592(10) 0.0621(10) 0.0332(8) 0.0247(8) 0.0329(8) O2 0.0450(9) 0.0616(10) 0.0619(10) 0.0348(8) 0.0266(8) 0.0243(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.281(3) . ? C1 O1 1.361(3) . ? C1 C2 1.453(3) . ? C2 C3 1.372(4) . ? C2 C7 1.385(3) . ? C3 C4 1.378(4) . ? C3 H3 0.9300 . ? C4 C5 1.359(4) . ? C4 H4 0.9300 . ? C5 C6 1.369(4) . ? C5 C8 1.512(5) . ? C6 C7 1.367(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.390(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.450(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.543(8) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.440(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.504(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N2 1.282(3) . ? C14 O1 1.368(3) . ? C14 C15 1.479(3) . ? C15 C16 1.400(3) . ? C15 C18 1.417(3) . ? C16 C17 1.423(3) . ? C16 C18 1.433(3) 2_565 ? C17 C21 1.351(4) 2_565 ? C17 H17 0.9300 . ? C18 C19 1.427(3) . ? C18 C16 1.433(3) 2_565 ? C19 C20 1.354(3) . ? C19 H19 0.9300 . ? C20 C21 1.421(3) . ? C20 C22 1.525(4) . ? C21 C17 1.351(4) 2_565 ? C21 H21 0.9300 . ? C22 C23 1.519(4) . ? C22 C24 1.530(4) . ? C22 C25 1.531(4) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 N3 1.281(3) . ? C26 O2 1.359(3) . ? C26 C27 1.457(3) . ? C27 C28 1.370(4) . ? C27 C32 1.370(4) . ? C28 C29 1.380(4) . ? C28 H28 0.9300 . ? C29 C30 1.357(4) . ? C29 H29 0.9300 . ? C30 C31 1.366(4) . ? C30 C33 1.511(4) . ? C31 C32 1.380(4) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 C34 1.488(5) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.447(6) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.501(6) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.431(7) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.538(7) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 N4 1.277(3) . ? C39 O2 1.367(3) . ? C39 C40 1.470(3) . ? C40 C46 1.407(3) 2 ? C40 C41 1.412(3) . ? C41 C46 1.426(3) . ? C41 C42 1.430(3) . ? C42 C43 1.360(3) . ? C42 H42 0.9300 . ? C43 C44 1.414(4) . ? C43 C47 1.539(3) . ? C44 C45 1.350(3) . ? C44 H44 0.9300 . ? C45 C46 1.425(3) . ? C45 H45 0.9300 . ? C46 C40 1.407(3) 2 ? C47 C48 1.521(4) . ? C47 C49 1.517(4) . ? C47 C50 1.521(4) . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? C49 H49A 0.9600 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 0.9600 . ? N1 N2 1.409(3) . ? N3 N4 1.402(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 N1 C1 O1 112.0(2) . . ? N1 C1 C2 128.5(2) . . ? O1 C1 C2 119.4(2) . . ? C3 C2 C7 117.6(2) . . ? C3 C2 C1 122.2(2) . . ? C7 C2 C1 120.2(2) . . ? C2 C3 C4 120.8(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 121.8(3) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 117.3(3) . . ? C4 C5 C8 121.2(3) . . ? C6 C5 C8 121.4(3) . . ? C5 C6 C7 122.1(3) . . ? C5 C6 H6 118.9 . . ? C7 C6 H6 118.9 . . ? C6 C7 C2 120.4(3) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? C9 C8 C5 120.3(5) . . ? C9 C8 H8A 107.3 . . ? C5 C8 H8A 107.3 . . ? C9 C8 H8B 107.3 . . ? C5 C8 H8B 107.3 . . ? H8A C8 H8B 106.9 . . ? C8 C9 C10 111.6(5) . . ? C8 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C11 111.1(5) . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 116.9(6) . . ? C12 C11 H11A 108.1 . . ? C10 C11 H11A 108.1 . . ? C12 C11 H11B 108.1 . . ? C10 C11 H11B 108.1 . . ? H11A C11 H11B 107.3 . . ? C11 C12 C13 126.0(6) . . ? C11 C12 H12A 105.8 . . ? C13 C12 H12A 105.8 . . ? C11 C12 H12B 105.8 . . ? C13 C12 H12B 105.8 . . ? H12A C12 H12B 106.2 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 O1 112.2(2) . . ? N2 C14 C15 128.0(2) . . ? O1 C14 C15 119.8(2) . . ? C16 C15 C18 121.1(2) . . ? C16 C15 C14 119.4(2) . . ? C18 C15 C14 119.5(2) . . ? C15 C16 C17 122.8(2) . . ? C15 C16 C18 119.6(2) . 2_565 ? C17 C16 C18 117.6(2) . 2_565 ? C21 C17 C16 121.3(2) 2_565 . ? C21 C17 H17 119.4 2_565 . ? C16 C17 H17 119.4 . . ? C15 C18 C19 122.3(2) . . ? C15 C18 C16 119.4(2) . 2_565 ? C19 C18 C16 118.4(2) . 2_565 ? C20 C19 C18 122.9(2) . . ? C20 C19 H19 118.5 . . ? C18 C19 H19 118.5 . . ? C19 C20 C21 117.6(2) . . ? C19 C20 C22 123.0(2) . . ? C21 C20 C22 119.4(2) . . ? C17 C21 C20 122.2(2) 2_565 . ? C17 C21 H21 118.9 2_565 . ? C20 C21 H21 118.9 . . ? C23 C22 C20 112.4(2) . . ? C23 C22 C24 109.2(2) . . ? C20 C22 C24 108.0(2) . . ? C23 C22 C25 108.0(3) . . ? C20 C22 C25 110.3(2) . . ? C24 C22 C25 108.8(3) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N3 C26 O2 112.0(2) . . ? N3 C26 C27 128.1(2) . . ? O2 C26 C27 119.9(2) . . ? C28 C27 C32 117.5(2) . . ? C28 C27 C26 120.2(2) . . ? C32 C27 C26 122.2(2) . . ? C27 C28 C29 120.9(3) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C30 C29 C28 122.0(3) . . ? C30 C29 H29 119.0 . . ? C28 C29 H29 119.0 . . ? C29 C30 C31 116.9(3) . . ? C29 C30 C33 121.6(3) . . ? C31 C30 C33 121.5(3) . . ? C30 C31 C32 122.0(3) . . ? C30 C31 H31 119.0 . . ? C32 C31 H31 119.0 . . ? C27 C32 C31 120.7(3) . . ? C27 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C34 C33 C30 116.9(3) . . ? C34 C33 H33A 108.1 . . ? C30 C33 H33A 108.1 . . ? C34 C33 H33B 108.1 . . ? C30 C33 H33B 108.1 . . ? H33A C33 H33B 107.3 . . ? C35 C34 C33 116.6(4) . . ? C35 C34 H34A 108.1 . . ? C33 C34 H34A 108.1 . . ? C35 C34 H34B 108.1 . . ? C33 C34 H34B 108.1 . . ? H34A C34 H34B 107.3 . . ? C34 C35 C36 117.8(4) . . ? C34 C35 H35A 107.9 . . ? C36 C35 H35A 107.9 . . ? C34 C35 H35B 107.9 . . ? C36 C35 H35B 107.9 . . ? H35A C35 H35B 107.2 . . ? C37 C36 C35 118.5(5) . . ? C37 C36 H36A 107.7 . . ? C35 C36 H36A 107.7 . . ? C37 C36 H36B 107.7 . . ? C35 C36 H36B 107.7 . . ? H36A C36 H36B 107.1 . . ? C36 C37 C38 116.3(6) . . ? C36 C37 H37A 108.2 . . ? C38 C37 H37A 108.2 . . ? C36 C37 H37B 108.2 . . ? C38 C37 H37B 108.2 . . ? H37A C37 H37B 107.4 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N4 C39 O2 111.9(2) . . ? N4 C39 C40 129.3(2) . . ? O2 C39 C40 118.76(19) . . ? C46 C40 C41 121.3(2) 2 . ? C46 C40 C39 119.3(2) 2 . ? C41 C40 C39 119.4(2) . . ? C40 C41 C46 118.9(2) . . ? C40 C41 C42 122.0(2) . . ? C46 C41 C42 119.0(2) . . ? C43 C42 C41 122.7(2) . . ? C43 C42 H42 118.6 . . ? C41 C42 H42 118.6 . . ? C42 C43 C44 117.1(2) . . ? C42 C43 C47 121.9(2) . . ? C44 C43 C47 120.9(2) . . ? C45 C44 C43 122.7(2) . . ? C45 C44 H44 118.6 . . ? C43 C44 H44 118.6 . . ? C44 C45 C46 121.4(2) . . ? C44 C45 H45 119.3 . . ? C46 C45 H45 119.3 . . ? C40 C46 C45 123.2(2) 2 . ? C40 C46 C41 119.8(2) 2 . ? C45 C46 C41 117.0(2) . . ? C48 C47 C49 108.1(3) . . ? C48 C47 C50 108.7(3) . . ? C49 C47 C50 108.8(3) . . ? C48 C47 C43 107.4(2) . . ? C49 C47 C43 111.5(2) . . ? C50 C47 C43 112.1(2) . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C47 C49 H49A 109.5 . . ? C47 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C47 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C47 C50 H50A 109.5 . . ? C47 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C47 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C1 N1 N2 106.75(19) . . ? C14 N2 N1 106.1(2) . . ? C26 N3 N4 106.51(19) . . ? C39 N4 N3 106.7(2) . . ? C1 O1 C14 102.91(18) . . ? C26 O2 C39 102.94(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -174.6(3) . . . . ? O1 C1 C2 C3 5.0(4) . . . . ? N1 C1 C2 C7 4.9(4) . . . . ? O1 C1 C2 C7 -175.5(2) . . . . ? C7 C2 C3 C4 1.0(5) . . . . ? C1 C2 C3 C4 -179.5(3) . . . . ? C2 C3 C4 C5 -1.0(6) . . . . ? C3 C4 C5 C6 0.5(6) . . . . ? C3 C4 C5 C8 176.1(4) . . . . ? C4 C5 C6 C7 -0.1(5) . . . . ? C8 C5 C6 C7 -175.6(3) . . . . ? C5 C6 C7 C2 0.1(5) . . . . ? C3 C2 C7 C6 -0.6(4) . . . . ? C1 C2 C7 C6 179.9(2) . . . . ? C4 C5 C8 C9 61.7(6) . . . . ? C6 C5 C8 C9 -122.9(5) . . . . ? C5 C8 C9 C10 60.6(7) . . . . ? C8 C9 C10 C11 167.6(5) . . . . ? C9 C10 C11 C12 -175.1(6) . . . . ? C10 C11 C12 C13 179.8(6) . . . . ? N2 C14 C15 C16 -55.6(4) . . . . ? O1 C14 C15 C16 124.6(2) . . . . ? N2 C14 C15 C18 122.4(3) . . . . ? O1 C14 C15 C18 -57.4(3) . . . . ? C18 C15 C16 C17 177.6(2) . . . . ? C14 C15 C16 C17 -4.4(4) . . . . ? C18 C15 C16 C18 -0.4(4) . . . 2_565 ? C14 C15 C16 C18 177.6(2) . . . 2_565 ? C15 C16 C17 C21 -179.5(3) . . . 2_565 ? C18 C16 C17 C21 -1.5(4) 2_565 . . 2_565 ? C16 C15 C18 C19 179.1(2) . . . . ? C14 C15 C18 C19 1.2(4) . . . . ? C16 C15 C18 C16 0.4(4) . . . 2_565 ? C14 C15 C18 C16 -177.6(2) . . . 2_565 ? C15 C18 C19 C20 -179.2(2) . . . . ? C16 C18 C19 C20 -0.4(4) 2_565 . . . ? C18 C19 C20 C21 1.5(4) . . . . ? C18 C19 C20 C22 179.8(2) . . . . ? C19 C20 C21 C17 -1.1(4) . . . 2_565 ? C22 C20 C21 C17 -179.5(3) . . . 2_565 ? C19 C20 C22 C23 6.3(4) . . . . ? C21 C20 C22 C23 -175.3(3) . . . . ? C19 C20 C22 C24 -114.3(3) . . . . ? C21 C20 C22 C24 64.1(3) . . . . ? C19 C20 C22 C25 126.9(3) . . . . ? C21 C20 C22 C25 -54.8(3) . . . . ? N3 C26 C27 C28 -5.4(4) . . . . ? O2 C26 C27 C28 173.1(2) . . . . ? N3 C26 C27 C32 175.4(3) . . . . ? O2 C26 C27 C32 -6.1(4) . . . . ? C32 C27 C28 C29 0.5(5) . . . . ? C26 C27 C28 C29 -178.7(3) . . . . ? C27 C28 C29 C30 0.9(5) . . . . ? C28 C29 C30 C31 -1.3(5) . . . . ? C28 C29 C30 C33 175.8(3) . . . . ? C29 C30 C31 C32 0.4(6) . . . . ? C33 C30 C31 C32 -176.8(4) . . . . ? C28 C27 C32 C31 -1.4(5) . . . . ? C26 C27 C32 C31 177.8(3) . . . . ? C30 C31 C32 C27 1.0(6) . . . . ? C29 C30 C33 C34 50.1(5) . . . . ? C31 C30 C33 C34 -132.8(4) . . . . ? C30 C33 C34 C35 67.2(5) . . . . ? C33 C34 C35 C36 179.6(4) . . . . ? C34 C35 C36 C37 -172.0(4) . . . . ? C35 C36 C37 C38 174.2(4) . . . . ? N4 C39 C40 C46 61.1(3) . . . 2 ? O2 C39 C40 C46 -116.2(2) . . . 2 ? N4 C39 C40 C41 -120.9(3) . . . . ? O2 C39 C40 C41 61.8(3) . . . . ? C46 C40 C41 C46 1.0(3) 2 . . . ? C39 C40 C41 C46 -176.92(19) . . . . ? C46 C40 C41 C42 -177.0(2) 2 . . . ? C39 C40 C41 C42 5.1(3) . . . . ? C40 C41 C42 C43 179.4(2) . . . . ? C46 C41 C42 C43 1.4(3) . . . . ? C41 C42 C43 C44 0.1(3) . . . . ? C41 C42 C43 C47 -176.6(2) . . . . ? C42 C43 C44 C45 -1.1(4) . . . . ? C47 C43 C44 C45 175.6(2) . . . . ? C43 C44 C45 C46 0.6(4) . . . . ? C44 C45 C46 C40 -177.9(2) . . . 2 ? C44 C45 C46 C41 1.0(4) . . . . ? C40 C41 C46 C40 -1.0(3) . . . 2 ? C42 C41 C46 C40 177.1(2) . . . 2 ? C40 C41 C46 C45 -180.0(2) . . . . ? C42 C41 C46 C45 -1.9(3) . . . . ? C42 C43 C47 C48 88.3(3) . . . . ? C44 C43 C47 C48 -88.3(3) . . . . ? C42 C43 C47 C49 -30.0(4) . . . . ? C44 C43 C47 C49 153.4(3) . . . . ? C42 C43 C47 C50 -152.3(3) . . . . ? C44 C43 C47 C50 31.1(3) . . . . ? O1 C1 N1 N2 -1.1(3) . . . . ? C2 C1 N1 N2 178.5(2) . . . . ? O1 C14 N2 N1 0.4(3) . . . . ? C15 C14 N2 N1 -179.4(2) . . . . ? C1 N1 N2 C14 0.4(3) . . . . ? O2 C26 N3 N4 -0.1(3) . . . . ? C27 C26 N3 N4 178.5(2) . . . . ? O2 C39 N4 N3 0.1(3) . . . . ? C40 C39 N4 N3 -177.4(2) . . . . ? C26 N3 N4 C39 0.0(3) . . . . ? N1 C1 O1 C14 1.3(3) . . . . ? C2 C1 O1 C14 -178.4(2) . . . . ? N2 C14 O1 C1 -1.0(3) . . . . ? C15 C14 O1 C1 178.8(2) . . . . ? N3 C26 O2 C39 0.1(3) . . . . ? C27 C26 O2 C39 -178.6(2) . . . . ? N4 C39 O2 C26 -0.1(3) . . . . ? C40 C39 O2 C26 177.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.483 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.043 #===END