data_global _audit_creation_method 'APEX2 v2011.2-0' _publ_requested_journal ? _publ_contact_author_name ? _publ_contact_author_address ; ; _publ_contact_author_email ? _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ; ; _publ_section_abstract ; ; _publ_section_references ; ; _publ_section_comment ; ; data_I _chemical_name_systematic ? _chemical_name_common: Ass. Prof Saleh, Morsy_02_10_11 _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 N2 O4' _chemical_formula_iupac ? _chemical_formula_weight 362.37 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.9130(6) _cell_length_b 18.8065(12) _cell_length_c 19.3890(10) _cell_angle_alpha 90 _cell_angle_beta 92.030(4) _cell_angle_gamma 90 _cell_volume 3612.4(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 1764 _cell_measurement_theta_min 4.5639 _cell_measurement_theta_max 59.8940 _cell_measurement_temperature 296.(2) _exptl_crystal_description Block _exptl_crystal_colour 'clear light colourless' _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.040 _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.767 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.60 _exptl_absorpt_correction_T_max 0.97 _exptl_special_details ; ; _diffrn_ambient_temperature 296.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 21126 _diffrn_reflns_av_R_equivalents 0.1260 _diffrn_reflns_av_sigmaI/netI 0.1359 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 66.44 _diffrn_reflns_theta_full 66.44 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measured_fraction_theta_full 0.978 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _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. ; _reflns_number_total 6218 _reflns_number_gt 3121 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1662 _refine_ls_R_factor_gt 0.0915 _refine_ls_wR_factor_gt 0.2511 _refine_ls_wR_factor_ref 0.3125 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_number_reflns 6218 _refine_ls_number_parameters 491 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1761P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.385 _refine_diff_density_min -0.432 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service v2011.2.0.0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.5749(6) 0.0360(3) 0.2909(3) 0.137(2) Uani d . 1 . . N N1 0.3112(3) 0.2643(2) 0.25296(18) 0.0579(10) Uani d . 1 . . O O4 0.1871(4) 0.2607(2) 0.41653(18) 0.0894(12) Uani d . 1 . . N N4 0.7831(3) 0.3046(2) 0.47847(18) 0.0598(10) Uani d . 1 . . O O7 1.0295(4) 0.1837(2) 0.5442(2) 0.0860(11) Uani d . 1 . . O O8 0.6173(3) 0.2893(3) 0.31974(19) 0.0972(14) Uani d . 1 . . C C8 0.4418(4) 0.2708(3) 0.1551(2) 0.0535(11) Uani d . 1 . . N N2 0.4074(3) 0.2324(2) 0.21695(17) 0.0554(9) Uani d . 1 . . O O3 0.5494(4) 0.1415(2) 0.1918(2) 0.0873(12) Uani d . 1 . . C C29 0.9320(4) 0.3163(3) 0.5746(2) 0.0553(11) Uani d . 1 . . N N5 0.8886(3) 0.2758(2) 0.51440(18) 0.0567(10) Uani d . 1 . . O O6 1.0056(10) 0.1037(5) 0.3555(3) 0.209(4) Uani d . 1 . . C C1 0.7694(7) -0.0362(5) 0.2968(5) 0.137(3) Uani d . 1 . . H H1A 0.7678 -0.0312 0.2476 0.205 Uiso calc R 1 . . H H1B 0.8037 -0.0824 0.3093 0.205 Uiso calc R 1 . . H H1C 0.8265 -0.0002 0.3175 0.205 Uiso calc R 1 . . C C2 0.6387(8) -0.0287(5) 0.3204(5) 0.143(4) Uani d . 1 . . H H2A 0.6417 -0.0257 0.3704 0.171 Uiso calc R 1 . . H H2B 0.5853 -0.0701 0.307 0.171 Uiso calc R 1 . . C C3 0.5071(6) 0.0751(4) 0.3300(3) 0.0870(17) Uani d . 1 . . C C4 0.4394(4) 0.1391(3) 0.3000(2) 0.0659(13) Uani d . 1 . . C C5 0.3468(5) 0.1717(3) 0.3364(2) 0.0689(14) Uani d . 1 . . H H5 0.3249 0.1532 0.379 0.083 Uiso calc R 1 . . C C6 0.2807(4) 0.2339(3) 0.3120(2) 0.0631(13) Uani d . 1 . . C C14 0.1794(4) 0.2717(3) 0.3537(3) 0.0688(13) Uani d . 1 . . C C15 0.0766(4) 0.3174(3) 0.3227(2) 0.0668(13) Uani d . 1 . . C C16 0.0225(5) 0.3720(4) 0.3620(3) 0.0798(16) Uani d . 1 . . H H9 0.056 0.3793 0.4069 0.096 Uiso calc R 1 . . C C17 -0.0776(5) 0.4144(4) 0.3364(3) 0.0838(16) Uani d . 1 . . H H10 -0.1114 0.4502 0.3639 0.101 Uiso calc R 1 . . C C18 -0.1314(5) 0.4054(3) 0.2691(3) 0.0825(16) Uani d . 1 . . C C21 -0.2442(5) 0.4528(4) 0.2416(4) 0.110(2) Uani d . 1 . . H H12A -0.3104 0.4245 0.2169 0.164 Uiso calc R 1 . . H H12B -0.2082 0.4876 0.2111 0.164 Uiso calc R 1 . . H H12C -0.2856 0.4763 0.2794 0.164 Uiso calc R 1 . . C C11 0.5056(5) 0.3458(3) 0.0396(2) 0.0788(16) Uani d . 1 . . H H13 0.5276 0.3709 0.0002 0.095 Uiso calc R 1 . . C C12 0.6054(4) 0.3273(3) 0.0877(2) 0.0704(14) Uani d . 1 . . H H14 0.6945 0.3401 0.0807 0.084 Uiso calc R 1 . . C C13 0.5741(4) 0.2900(3) 0.1462(2) 0.0594(12) Uani d . 1 . . H H15 0.641 0.2779 0.1789 0.071 Uiso calc R 1 . . C C7 0.4729(4) 0.1673(3) 0.2323(2) 0.0622(12) Uani d . 1 . . O O2 0.4985(12) 0.0593(5) 0.3870(3) 0.258(6) Uani d . 1 . . C C19 -0.0788(5) 0.3517(4) 0.2299(3) 0.0870(18) Uani d . 1 . . H H18 -0.1125 0.3445 0.1851 0.104 Uiso calc R 1 . . C C20 0.0229(4) 0.3087(3) 0.2560(3) 0.0735(15) Uani d . 1 . . H H19 0.0566 0.2729 0.2284 0.088 Uiso calc R 1 . . C C9 0.3405(4) 0.2905(3) 0.1082(2) 0.0661(13) Uani d . 1 . . H H20 0.251 0.2791 0.116 0.079 Uiso calc R 1 . . C C10 0.3735(5) 0.3271(3) 0.0499(2) 0.0781(16) Uani d . 1 . . H H21 0.3064 0.3393 0.0173 0.094 Uiso calc R 1 . . C C32 1.0141(5) 0.3921(3) 0.6890(3) 0.0816(16) Uani d . 1 . . H H22 1.0422 0.4178 0.7279 0.098 Uiso calc R 1 . . C C31 1.1076(5) 0.3717(3) 0.6413(3) 0.0761(15) Uani d . 1 . . H H23 1.1981 0.3835 0.6487 0.091 Uiso calc R 1 . . C C30 1.0674(4) 0.3340(3) 0.5828(2) 0.0641(13) Uani d . 1 . . H H24 1.1291 0.3209 0.5501 0.077 Uiso calc R 1 . . C C27 0.7413(4) 0.2715(3) 0.4219(2) 0.0635(13) Uani d . 1 . . C C35 0.6272(4) 0.3051(3) 0.3821(2) 0.0723(15) Uani d . 1 . . C C36 0.5319(4) 0.3543(3) 0.4137(2) 0.0675(14) Uani d . 1 . . C C41 0.4694(6) 0.4062(4) 0.3724(3) 0.096(2) Uani d . 1 . . H H28 0.4895 0.4094 0.3261 0.115 Uiso calc R 1 . . C C40 0.3780(6) 0.4526(4) 0.3996(3) 0.097(2) Uani d . 1 . . H H29 0.3376 0.487 0.3712 0.117 Uiso calc R 1 . . C C39 0.3448(5) 0.4494(3) 0.4685(3) 0.0792(15) Uani d . 1 . . C C42 0.2439(6) 0.4995(4) 0.4960(4) 0.102(2) Uani d . 1 . . H H31A 0.2452 0.5431 0.4703 0.152 Uiso calc R 1 . . H H31B 0.2659 0.5091 0.5437 0.152 Uiso calc R 1 . . H H31C 0.1556 0.4786 0.4918 0.152 Uiso calc R 1 . . C C33 0.8819(5) 0.3748(3) 0.6792(3) 0.0764(15) Uani d . 1 . . H H32 0.8198 0.3882 0.7116 0.092 Uiso calc R 1 . . C C34 0.8395(4) 0.3373(3) 0.6213(2) 0.0667(13) Uani d . 1 . . H H33 0.7487 0.3263 0.614 0.08 Uiso calc R 1 . . C C28 0.8078(5) 0.2103(3) 0.3980(3) 0.0742(15) Uani d . 1 . . H H34 0.781 0.1907 0.3557 0.089 Uiso calc R 1 . . C C25 0.9090(5) 0.1799(3) 0.4353(3) 0.0716(14) Uani d . 1 . . C C26 0.9510(4) 0.2100(3) 0.5023(3) 0.0662(13) Uani d . 1 . . C C24 0.9835(6) 0.1192(4) 0.4082(3) 0.0905(18) Uani d . 1 . . O O5 1.0384(12) 0.0772(5) 0.4515(4) 0.251(6) Uani d . 1 . . C C37 0.4995(4) 0.3508(3) 0.4826(3) 0.0699(14) Uani d . 1 . . H H39 0.5408 0.3172 0.5116 0.084 Uiso calc R 1 . . C C38 0.4060(4) 0.3971(3) 0.5078(3) 0.0784(15) Uani d . 1 . . H H40 0.3831 0.3929 0.5538 0.094 Uiso calc R 1 . . C C22 1.2185(16) -0.0033(8) 0.4788(9) 0.248(8) Uani d . 1 . . H H22A 1.2838 0.0337 0.4728 0.372 Uiso calc R 1 . . H H22B 1.2586 -0.0485 0.4692 0.372 Uiso calc R 1 . . H H22C 1.1894 -0.0027 0.5255 0.372 Uiso calc R 1 . . C C23 1.097(3) 0.0090(10) 0.4294(8) 0.371(16) Uani d . 1 . . H H23A 1.1251 0.0119 0.382 0.446 Uiso calc R 1 . . H H23B 1.0319 -0.0292 0.4329 0.446 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.176(4) 0.135(5) 0.102(4) 0.075(4) 0.035(3) 0.044(3) N1 0.0535(16) 0.072(3) 0.0486(18) -0.0043(16) 0.0063(14) -0.0015(18) O4 0.092(2) 0.122(4) 0.0550(19) 0.011(2) 0.0193(16) 0.006(2) N4 0.0511(16) 0.075(3) 0.0539(19) -0.0008(16) 0.0017(14) -0.0005(19) O7 0.088(2) 0.078(3) 0.091(3) 0.0186(19) -0.008(2) 0.004(2) O8 0.086(2) 0.142(4) 0.063(2) 0.002(2) -0.0138(17) -0.021(2) C8 0.0550(19) 0.063(3) 0.0431(19) -0.0015(18) 0.0020(16) 0.000(2) N2 0.0540(16) 0.065(3) 0.0477(17) -0.0026(16) 0.0064(14) 0.0006(18) O3 0.102(2) 0.082(3) 0.079(2) 0.025(2) 0.0327(19) 0.014(2) C29 0.059(2) 0.059(3) 0.048(2) 0.0055(18) 0.0024(17) -0.001(2) N5 0.0521(16) 0.065(3) 0.0531(19) 0.0029(16) 0.0036(14) -0.0028(18) O6 0.347(11) 0.182(9) 0.102(5) 0.082(8) 0.048(6) -0.041(5) C1 0.103(4) 0.119(8) 0.189(9) 0.027(4) 0.011(5) 0.027(6) C2 0.157(6) 0.136(8) 0.137(7) 0.071(6) 0.031(5) 0.061(6) C3 0.111(4) 0.093(5) 0.058(3) 0.020(3) 0.008(3) 0.005(3) C4 0.070(2) 0.077(4) 0.050(2) 0.000(2) 0.0007(19) 0.004(2) C5 0.080(3) 0.074(4) 0.053(2) -0.003(3) 0.006(2) 0.007(2) C6 0.059(2) 0.079(4) 0.051(2) -0.006(2) 0.0076(18) -0.003(2) C14 0.066(2) 0.076(4) 0.065(3) -0.008(2) 0.016(2) -0.001(3) C15 0.061(2) 0.079(4) 0.062(3) -0.007(2) 0.0175(19) -0.006(3) C16 0.086(3) 0.089(5) 0.065(3) 0.003(3) 0.017(2) -0.009(3) C17 0.090(3) 0.079(5) 0.083(4) 0.010(3) 0.021(3) -0.013(3) C18 0.063(2) 0.080(5) 0.105(4) -0.001(2) 0.016(3) 0.004(4) C21 0.079(3) 0.116(6) 0.133(6) 0.018(3) -0.002(3) -0.004(5) C11 0.096(3) 0.092(5) 0.050(2) -0.009(3) 0.009(2) 0.007(3) C12 0.068(2) 0.084(4) 0.060(3) -0.007(2) 0.015(2) 0.001(3) C13 0.059(2) 0.069(4) 0.050(2) -0.004(2) 0.0033(17) 0.000(2) C7 0.061(2) 0.062(4) 0.064(3) 0.001(2) 0.007(2) 0.002(2) O2 0.490(15) 0.210(9) 0.075(3) 0.217(10) 0.037(6) 0.028(4) C19 0.065(3) 0.107(5) 0.089(4) -0.001(3) 0.004(2) -0.019(4) C20 0.054(2) 0.089(4) 0.077(3) -0.003(2) 0.006(2) -0.019(3) C9 0.062(2) 0.079(4) 0.056(2) -0.007(2) -0.0033(19) -0.004(2) C10 0.088(3) 0.100(5) 0.045(2) -0.009(3) -0.010(2) 0.005(3) C32 0.100(3) 0.086(5) 0.059(3) -0.012(3) -0.001(3) -0.006(3) C31 0.069(2) 0.084(5) 0.073(3) -0.008(2) -0.012(2) -0.001(3) C30 0.055(2) 0.075(4) 0.062(2) 0.001(2) -0.0004(18) 0.004(2) C27 0.056(2) 0.081(4) 0.053(2) -0.003(2) 0.0031(18) -0.003(2) C35 0.060(2) 0.094(5) 0.063(3) -0.011(2) -0.002(2) -0.002(3) C36 0.053(2) 0.089(4) 0.061(3) -0.005(2) -0.0032(19) -0.001(3) C41 0.097(4) 0.121(6) 0.068(3) 0.011(4) -0.006(3) 0.018(4) C40 0.091(3) 0.111(6) 0.090(4) 0.029(3) -0.007(3) 0.014(4) C39 0.077(3) 0.071(4) 0.090(4) -0.005(3) 0.000(3) 0.003(3) C42 0.100(4) 0.084(5) 0.121(5) 0.014(3) 0.008(4) 0.001(4) C33 0.085(3) 0.087(5) 0.059(3) -0.004(3) 0.017(2) -0.005(3) C34 0.061(2) 0.077(4) 0.063(3) -0.003(2) 0.0097(19) -0.003(3) C28 0.074(3) 0.087(5) 0.062(3) -0.011(3) 0.007(2) -0.016(3) C25 0.073(3) 0.070(4) 0.073(3) 0.002(2) 0.017(2) -0.007(3) C26 0.063(2) 0.067(4) 0.068(3) -0.002(2) 0.009(2) -0.008(3) C24 0.120(4) 0.085(5) 0.066(3) 0.012(3) -0.004(3) -0.006(3) O5 0.439(15) 0.171(8) 0.142(6) 0.173(10) -0.002(8) -0.023(6) C37 0.056(2) 0.083(4) 0.071(3) -0.002(2) 0.002(2) 0.010(3) C38 0.070(3) 0.087(5) 0.078(3) -0.004(3) 0.010(2) 0.009(3) C22 0.313(18) 0.145(14) 0.28(2) 0.045(13) -0.020(16) -0.022(13) C23 0.64(4) 0.28(2) 0.186(14) 0.34(3) -0.100(19) -0.080(14) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C3 . 1.266(8) ? O1 C2 . 1.478(9) ? N1 C6 . 1.325(6) ? N1 N2 . 1.343(5) ? O4 C14 . 1.235(6) ? N4 C27 . 1.315(6) ? N4 N5 . 1.350(5) ? O7 C26 . 1.211(6) ? O8 C35 . 1.245(6) ? C8 C13 . 1.377(6) ? C8 C9 . 1.381(6) ? C8 N2 . 1.450(5) ? N2 C7 . 1.412(6) ? O3 C7 . 1.213(6) ? C29 C34 . 1.370(6) ? C29 C30 . 1.386(6) ? C29 N5 . 1.446(6) ? N5 C26 . 1.407(7) ? O6 C24 . 1.091(8) ? C1 C2 . 1.396(9) ? C1 H1A . 0.96 ? C1 H1B . 0.96 ? C1 H1C . 0.96 ? C2 H2A . 0.97 ? C2 H2B . 0.97 ? C3 O2 . 1.151(8) ? C3 C4 . 1.486(8) ? C4 C5 . 1.328(7) ? C4 C7 . 1.464(6) ? C5 C6 . 1.413(7) ? C5 H5 . 0.93 ? C6 C14 . 1.492(7) ? C14 C15 . 1.449(7) ? C15 C20 . 1.390(7) ? C15 C16 . 1.397(8) ? C16 C17 . 1.354(8) ? C16 H9 . 0.93 ? C17 C18 . 1.402(8) ? C17 H10 . 0.93 ? C18 C19 . 1.377(8) ? C18 C21 . 1.511(8) ? C21 H12A . 0.96 ? C21 H12B . 0.96 ? C21 H12C . 0.96 ? C11 C10 . 1.377(7) ? C11 C12 . 1.381(7) ? C11 H13 . 0.93 ? C12 C13 . 1.377(7) ? C12 H14 . 0.93 ? C13 H15 . 0.93 ? C19 C20 . 1.375(8) ? C19 H18 . 0.93 ? C20 H19 . 0.93 ? C9 C10 . 1.372(7) ? C9 H20 . 0.93 ? C10 H21 . 0.93 ? C32 C33 . 1.358(7) ? C32 C31 . 1.385(7) ? C32 H22 . 0.93 ? C31 C30 . 1.385(7) ? C31 H23 . 0.93 ? C30 H24 . 0.93 ? C27 C28 . 1.412(8) ? C27 C35 . 1.488(7) ? C35 C36 . 1.471(8) ? C36 C37 . 1.386(7) ? C36 C41 . 1.394(8) ? C41 C40 . 1.377(9) ? C41 H28 . 0.93 ? C40 C39 . 1.387(8) ? C40 H29 . 0.93 ? C39 C38 . 1.372(8) ? C39 C42 . 1.487(8) ? C42 H31A . 0.96 ? C42 H31B . 0.96 ? C42 H31C . 0.96 ? C33 C34 . 1.378(7) ? C33 H32 . 0.93 ? C34 H33 . 0.93 ? C28 C25 . 1.342(7) ? C28 H34 . 0.93 ? C25 C26 . 1.464(7) ? C25 C24 . 1.468(9) ? C24 O5 . 1.262(9) ? O5 C23 . 1.477(13) ? C37 C38 . 1.375(8) ? C37 H39 . 0.93 ? C38 H40 . 0.93 ? C22 C23 . 1.531(18) ? C22 H22A . 0.96 ? C22 H22B . 0.96 ? C22 H22C . 0.96 ? C23 H23A . 0.97 ? C23 H23B . 0.97 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C3 O1 C2 . . 118.4(6) ? C6 N1 N2 . . 116.4(4) ? C27 N4 N5 . . 117.1(4) ? C13 C8 C9 . . 121.3(4) ? C13 C8 N2 . . 119.1(4) ? C9 C8 N2 . . 119.4(3) ? N1 N2 C7 . . 127.3(3) ? N1 N2 C8 . . 113.6(4) ? C7 N2 C8 . . 119.1(3) ? C34 C29 C30 . . 121.5(4) ? C34 C29 N5 . . 119.9(4) ? C30 C29 N5 . . 118.6(4) ? N4 N5 C26 . . 127.2(4) ? N4 N5 C29 . . 114.1(4) ? C26 N5 C29 . . 118.6(3) ? C2 C1 H1A . . 109.5 ? C2 C1 H1B . . 109.5 ? H1A C1 H1B . . 109.5 ? C2 C1 H1C . . 109.5 ? H1A C1 H1C . . 109.5 ? H1B C1 H1C . . 109.5 ? C1 C2 O1 . . 110.2(7) ? C1 C2 H2A . . 109.6 ? O1 C2 H2A . . 109.6 ? C1 C2 H2B . . 109.6 ? O1 C2 H2B . . 109.6 ? H2A C2 H2B . . 108.1 ? O2 C3 O1 . . 119.0(7) ? O2 C3 C4 . . 122.5(6) ? O1 C3 C4 . . 118.5(5) ? C5 C4 C7 . . 119.4(5) ? C5 C4 C3 . . 118.5(4) ? C7 C4 C3 . . 122.1(4) ? C4 C5 C6 . . 121.7(4) ? C4 C5 H5 . . 119.1 ? C6 C5 H5 . . 119.1 ? N1 C6 C5 . . 121.9(4) ? N1 C6 C14 . . 116.2(5) ? C5 C6 C14 . . 121.8(4) ? O4 C14 C15 . . 121.8(4) ? O4 C14 C6 . . 115.8(5) ? C15 C14 C6 . . 122.4(4) ? C20 C15 C16 . . 116.9(5) ? C20 C15 C14 . . 123.9(5) ? C16 C15 C14 . . 119.2(5) ? C17 C16 C15 . . 121.5(5) ? C17 C16 H9 . . 119.2 ? C15 C16 H9 . . 119.2 ? C16 C17 C18 . . 121.3(5) ? C16 C17 H10 . . 119.3 ? C18 C17 H10 . . 119.3 ? C19 C18 C17 . . 117.6(5) ? C19 C18 C21 . . 121.8(6) ? C17 C18 C21 . . 120.6(6) ? C18 C21 H12A . . 109.5 ? C18 C21 H12B . . 109.5 ? H12A C21 H12B . . 109.5 ? C18 C21 H12C . . 109.5 ? H12A C21 H12C . . 109.5 ? H12B C21 H12C . . 109.5 ? C10 C11 C12 . . 120.0(5) ? C10 C11 H13 . . 120.0 ? C12 C11 H13 . . 120.0 ? C13 C12 C11 . . 120.5(4) ? C13 C12 H14 . . 119.7 ? C11 C12 H14 . . 119.7 ? C12 C13 C8 . . 118.7(4) ? C12 C13 H15 . . 120.7 ? C8 C13 H15 . . 120.7 ? O3 C7 N2 . . 120.2(4) ? O3 C7 C4 . . 127.0(5) ? N2 C7 C4 . . 112.7(4) ? C20 C19 C18 . . 121.0(6) ? C20 C19 H18 . . 119.5 ? C18 C19 H18 . . 119.5 ? C19 C20 C15 . . 121.6(5) ? C19 C20 H19 . . 119.2 ? C15 C20 H19 . . 119.2 ? C10 C9 C8 . . 119.2(4) ? C10 C9 H20 . . 120.4 ? C8 C9 H20 . . 120.4 ? C9 C10 C11 . . 120.2(4) ? C9 C10 H21 . . 119.9 ? C11 C10 H21 . . 119.9 ? C33 C32 C31 . . 120.4(5) ? C33 C32 H22 . . 119.8 ? C31 C32 H22 . . 119.8 ? C32 C31 C30 . . 120.5(4) ? C32 C31 H23 . . 119.7 ? C30 C31 H23 . . 119.7 ? C31 C30 C29 . . 117.8(4) ? C31 C30 H24 . . 121.1 ? C29 C30 H24 . . 121.1 ? N4 C27 C28 . . 121.5(4) ? N4 C27 C35 . . 116.3(5) ? C28 C27 C35 . . 122.1(4) ? O8 C35 C36 . . 121.7(5) ? O8 C35 C27 . . 115.7(5) ? C36 C35 C27 . . 122.6(4) ? C37 C36 C41 . . 118.2(5) ? C37 C36 C35 . . 123.1(5) ? C41 C36 C35 . . 118.6(5) ? C40 C41 C36 . . 120.6(6) ? C40 C41 H28 . . 119.7 ? C36 C41 H28 . . 119.7 ? C41 C40 C39 . . 121.5(6) ? C41 C40 H29 . . 119.3 ? C39 C40 H29 . . 119.3 ? C38 C39 C40 . . 116.9(6) ? C38 C39 C42 . . 122.9(6) ? C40 C39 C42 . . 120.2(6) ? C39 C42 H31A . . 109.5 ? C39 C42 H31B . . 109.5 ? H31A C42 H31B . . 109.5 ? C39 C42 H31C . . 109.5 ? H31A C42 H31C . . 109.5 ? H31B C42 H31C . . 109.5 ? C32 C33 C34 . . 120.1(5) ? C32 C33 H32 . . 120.0 ? C34 C33 H32 . . 120.0 ? C29 C34 C33 . . 119.6(4) ? C29 C34 H33 . . 120.2 ? C33 C34 H33 . . 120.2 ? C25 C28 C27 . . 121.3(5) ? C25 C28 H34 . . 119.3 ? C27 C28 H34 . . 119.3 ? C28 C25 C26 . . 119.8(5) ? C28 C25 C24 . . 121.0(5) ? C26 C25 C24 . . 119.2(5) ? O7 C26 N5 . . 121.5(5) ? O7 C26 C25 . . 126.5(5) ? N5 C26 C25 . . 112.0(4) ? O6 C24 O5 . . 111.0(8) ? O6 C24 C25 . . 131.5(8) ? O5 C24 C25 . . 117.4(6) ? C24 O5 C23 . . 121.0(9) ? C38 C37 C36 . . 119.6(5) ? C38 C37 H39 . . 120.2 ? C36 C37 H39 . . 120.2 ? C39 C38 C37 . . 123.1(5) ? C39 C38 H40 . . 118.5 ? C37 C38 H40 . . 118.5 ? C23 C22 H22A . . 109.5 ? C23 C22 H22B . . 109.5 ? H22A C22 H22B . . 109.5 ? C23 C22 H22C . . 109.5 ? H22A C22 H22C . . 109.5 ? H22B C22 H22C . . 109.5 ? O5 C23 C22 . . 104.9(13) ? O5 C23 H23A . . 110.8 ? C22 C23 H23A . . 110.8 ? O5 C23 H23B . . 110.8 ? C22 C23 H23B . . 110.8 ? H23A C23 H23B . . 108.8 ?