# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Christian Bruckner' _publ_contact_author_email c.bruckner@uconn.edu _publ_section_title ; Porpholactams and chlorolactams: Replacement of a b,b'-double bond in meso-tetraphenyl-porphyrin and -chlorin by a lactam moiety ; loop_ _publ_author_name J.Akhigbe J.Haskoor M.Zeller C.Bruckner # end Validation Reply Form data_10mz481_0m _database_code_depnum_ccdc_archive 'CCDC 821398' #TrackingRef '- CC-5-19-2011(compounds 6,7,8).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H30 N6 O, 0.37(H2 O)' _chemical_formula_sum 'C43 H30.74 N6 O1.37' _chemical_formula_weight 653.34 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.737(4) _cell_length_b 12.257(4) _cell_length_c 13.154(4) _cell_angle_alpha 76.707(4) _cell_angle_beta 78.360(4) _cell_angle_gamma 65.649(4) _cell_volume 1665.6(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2668 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 29.93 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 683.1 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5694 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_process_details 'Apex2 v2009.7-0 (Bruker, 2009)' _exptl_special_details ; The structure exhibits disorder of one of the two pyrrole rings with the lactam ring in a ratio of 0.633(5) to 0.367(5). The disorder extends to one of the phenyl rings, and the minor moiety is accompanied with an interstitial water molecule. The two pyrrole ring that wer refined as not disordered shows signs of additional minor disorder as the largest residual electron density peaks are located where oxygen or nitrogen atoms of the lactam would be found if additional disorder were present (Q1 and Q2 with 0.76 and 0.60 electrons each). No attempts were made to refine this additional disorder. All pyrrole rings (including the disordered ones) were restrained to have similar geometries. The lactam rings were restrained to be flat. ADPs of overlapping atoms were constrained to be identical. The ADPs of the two oxygen atoms and of the two amino groups were also constrained to be identical. Amino and water H atoms were placed in meaningful positions and were restrained. The water H atoms were constrained to ride on the carrying O atom in the final refinement cycles. ; _diffrn_ambient_temperature 100(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 AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 12566 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5846 _reflns_number_gt 3393 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2009.7-0 (Bruker, 2009)' _computing_cell_refinement 'Apex2 v2009.7-0' _computing_data_reduction 'Apex2 v2009.7-0' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0944P)^2^+3.7220P] 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 0.016(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5846 _refine_ls_number_parameters 516 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.1432 _refine_ls_R_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.2608 _refine_ls_wR_factor_gt 0.2284 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.004 _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 0.1858(4) 0.3883(4) 0.0145(4) 0.0364(11) Uani 1 1 d D . . C4 C 0.1760(4) 0.3457(4) -0.1356(4) 0.0366(11) Uani 1 1 d D . . C5 C 0.1547(4) 0.2928(4) -0.2098(4) 0.0390(12) Uani 1 1 d D A . C6 C 0.0754(4) 0.2274(4) -0.1899(3) 0.0354(11) Uani 1 1 d D . . C7 C 0.0426(4) 0.1838(4) -0.2674(4) 0.0398(12) Uani 1 1 d D A . H7 H 0.0784 0.1839 -0.3390 0.048 Uiso 1 1 calc R . . C8 C -0.0487(4) 0.1422(4) -0.2200(3) 0.0359(11) Uani 1 1 d D . . H8 H -0.0888 0.1089 -0.2532 0.043 Uiso 1 1 calc R A . C9 C -0.0748(4) 0.1565(4) -0.1121(3) 0.0310(10) Uani 1 1 d D A . C10 C -0.1664(4) 0.1309(4) -0.0361(4) 0.0326(11) Uani 1 1 d . . . C11 C -0.1844(4) 0.1404(4) 0.0704(3) 0.0310(10) Uani 1 1 d D A . C14 C -0.1673(4) 0.1757(4) 0.2225(4) 0.0355(11) Uani 1 1 d D . . C15 C -0.1292(4) 0.2099(4) 0.3001(3) 0.0357(11) Uani 1 1 d . A . C16 C -0.0383(4) 0.2612(4) 0.2811(4) 0.0383(11) Uani 1 1 d D . . C17 C 0.0170(5) 0.2784(5) 0.3603(4) 0.0444(13) Uani 1 1 d D A . H17 H -0.0043 0.2608 0.4341 0.053 Uiso 1 1 calc R . . C18 C 0.1049(5) 0.3242(5) 0.3119(4) 0.0444(13) Uani 1 1 d D . . H18 H 0.1575 0.3427 0.3457 0.053 Uiso 1 1 calc R A . C19 C 0.1043(4) 0.3395(4) 0.2010(4) 0.0378(11) Uani 1 1 d D A . C20 C 0.1808(4) 0.3852(4) 0.1223(4) 0.0362(11) Uani 1 1 d . A . C21 C 0.2222(10) 0.2981(11) -0.3218(6) 0.043(2) Uani 0.633(5) 1 d PGD A 1 C22 C 0.3274(10) 0.2005(9) -0.3535(7) 0.071(4) Uani 0.633(5) 1 d PG A 1 H22 H 0.3575 0.1269 -0.3056 0.085 Uiso 0.633(5) 1 calc PR A 1 C23 C 0.3885(9) 0.2108(9) -0.4552(8) 0.088(5) Uani 0.633(5) 1 d PG A 1 H23 H 0.4605 0.1441 -0.4769 0.106 Uiso 0.633(5) 1 calc PR A 1 C24 C 0.3445(12) 0.3186(10) -0.5253(5) 0.078(5) Uani 0.633(5) 1 d PG A 1 H24 H 0.3862 0.3256 -0.5949 0.094 Uiso 0.633(5) 1 calc PR A 1 C25 C 0.2392(13) 0.4161(9) -0.4937(7) 0.074(5) Uani 0.633(5) 1 d PG A 1 H25 H 0.2091 0.4898 -0.5416 0.089 Uiso 0.633(5) 1 calc PR A 1 C26 C 0.1781(11) 0.4059(10) -0.3919(8) 0.057(4) Uani 0.633(5) 1 d PG A 1 H26 H 0.1061 0.4725 -0.3702 0.069 Uiso 0.633(5) 1 calc PR A 1 N5 N 0.2464(16) 0.4511(19) -0.0654(8) 0.039(4) Uani 0.633(5) 1 d PD A 1 C3B C 0.2417(19) 0.429(2) -0.1605(9) 0.036(4) Uani 0.633(5) 1 d PD A 1 N6 N 0.2835(9) 0.5367(8) -0.0492(7) 0.074(2) Uani 0.633(5) 1 d PD A 1 H6A H 0.278(8) 0.589(5) -0.107(3) 0.088 Uiso 0.633(5) 1 d PD A 1 H6B H 0.227(7) 0.575(5) -0.001(5) 0.088 Uiso 0.633(5) 1 d PD A 1 O1 O 0.2869(8) 0.4713(7) -0.2401(6) 0.084(2) Uani 0.633(5) 1 d PD A 1 C2 C 0.269(4) 0.431(5) -0.0634(15) 0.039(4) Uani 0.367(5) 1 d PD A 2 H2 H 0.3204 0.4695 -0.0518 0.047 Uiso 0.367(5) 1 calc PR A 2 C3 C 0.261(4) 0.408(4) -0.1567(13) 0.036(4) Uani 0.367(5) 1 d PD A 2 H3 H 0.3028 0.4279 -0.2234 0.043 Uiso 0.367(5) 1 calc PR A 2 N7 N -0.271(4) 0.135(4) 0.2395(18) 0.036(4) Uani 0.367(5) 1 d PD A 1 C12B C -0.271(2) 0.0991(19) 0.149(2) 0.0368(11) Uani 0.367(5) 1 d PD A 1 O2 O -0.3409(13) 0.0514(13) 0.1465(10) 0.084(2) Uani 0.367(5) 1 d PD A 1 N8 N -0.3320(16) 0.1146(14) 0.3321(12) 0.074(2) Uani 0.367(5) 1 d PD A 1 H8A H -0.408(5) 0.120(12) 0.326(6) 0.088 Uiso 0.367(5) 1 d PD A 1 H8B H -0.296(8) 0.038(5) 0.363(7) 0.088 Uiso 0.367(5) 1 d PD A 1 C13 C -0.252(3) 0.113(3) 0.2434(11) 0.036(4) Uani 0.633(5) 1 d PD A 2 H13 H -0.2887 0.0865 0.3104 0.043 Uiso 0.633(5) 1 calc PR A 2 C12 C -0.2685(13) 0.1001(12) 0.1484(13) 0.0368(11) Uani 0.633(5) 1 d PD A 2 H12 H -0.3260 0.0694 0.1362 0.044 Uiso 0.633(5) 1 calc PR A 2 C21B C 0.2072(19) 0.324(2) -0.3193(11) 0.043(2) Uani 0.367(5) 1 d PGD A 2 C22B C 0.3345(18) 0.2613(16) -0.3488(11) 0.063(7) Uani 0.367(5) 1 d PG A 2 H22B H 0.3846 0.1995 -0.2994 0.075 Uiso 0.367(5) 1 calc PR A 2 C23B C 0.3885(14) 0.2888(18) -0.4505(13) 0.085(9) Uani 0.367(5) 1 d PG A 2 H23B H 0.4755 0.2458 -0.4707 0.103 Uiso 0.367(5) 1 calc PR A 2 C24B C 0.315(2) 0.3792(19) -0.5228(9) 0.082(11) Uani 0.367(5) 1 d PG A 2 H24B H 0.3521 0.3980 -0.5923 0.098 Uiso 0.367(5) 1 calc PR A 2 C25B C 0.188(2) 0.4422(18) -0.4933(16) 0.085(10) Uani 0.367(5) 1 d PG A 2 H25B H 0.1377 0.5040 -0.5427 0.102 Uiso 0.367(5) 1 calc PR A 2 C26B C 0.1338(15) 0.415(2) -0.3916(18) 0.062(7) Uani 0.367(5) 1 d PG A 2 H26B H 0.0468 0.4578 -0.3715 0.075 Uiso 0.367(5) 1 calc PR A 2 O3 O 0.4528(19) 0.0620(18) 0.3914(9) 0.190(12) Uani 0.367(5) 1 d PD A 2 H3A H 0.5017 0.0214 0.4384 0.285 Uiso 0.184(2) 1 d PRD A 2 H3B H 0.3796 0.0732 0.4230 0.285 Uiso 0.367(5) 1 d PRD A 2 H3C H 0.4642 0.0212 0.3445 0.285 Uiso 0.184(2) 1 d PRD A 2 C27 C -0.2576(4) 0.0942(4) -0.0728(3) 0.0305(10) Uani 1 1 d . A . C28 C -0.2196(5) -0.0159(4) -0.1062(4) 0.0420(12) Uani 1 1 d . . . H28 H -0.1338 -0.0701 -0.1085 0.050 Uiso 1 1 calc R A . C29 C -0.3084(5) -0.0468(5) -0.1364(4) 0.0458(13) Uani 1 1 d . A . H29 H -0.2827 -0.1221 -0.1598 0.055 Uiso 1 1 calc R . . C30 C -0.4332(5) 0.0314(5) -0.1325(4) 0.0444(13) Uani 1 1 d . . . H30 H -0.4936 0.0092 -0.1517 0.053 Uiso 1 1 calc R A . C31 C -0.4703(5) 0.1419(5) -0.1005(4) 0.0426(12) Uani 1 1 d . A . H31 H -0.5560 0.1964 -0.0987 0.051 Uiso 1 1 calc R . . C32 C -0.3832(4) 0.1733(4) -0.0711(3) 0.0369(11) Uani 1 1 d . . . H32 H -0.4092 0.2496 -0.0495 0.044 Uiso 1 1 calc R A . C33 C -0.1906(5) 0.1952(5) 0.4103(4) 0.0414(12) Uani 1 1 d . . . C34 C -0.1656(6) 0.0831(5) 0.4733(4) 0.0550(15) Uani 1 1 d . A . H34 H -0.1090 0.0119 0.4458 0.066 Uiso 1 1 calc R . . C35 C -0.2221(6) 0.0734(6) 0.5755(5) 0.0670(18) Uani 1 1 d . . . H35 H -0.2052 -0.0045 0.6176 0.080 Uiso 1 1 calc R A . C36 C -0.3017(6) 0.1740(6) 0.6170(4) 0.0632(17) Uani 1 1 d . A . H36 H -0.3377 0.1666 0.6885 0.076 Uiso 1 1 calc R . . C37 C -0.3302(6) 0.2873(6) 0.5547(4) 0.0599(16) Uani 1 1 d . . . H37 H -0.3887 0.3577 0.5823 0.072 Uiso 1 1 calc R A . C38 C -0.2731(5) 0.2976(5) 0.4521(4) 0.0496(14) Uani 1 1 d . A . H38 H -0.2907 0.3756 0.4100 0.059 Uiso 1 1 calc R . . C39 C 0.2686(4) 0.4265(4) 0.1574(4) 0.0355(11) Uani 1 1 d . . . C40 C 0.2227(5) 0.5311(4) 0.2023(4) 0.0403(12) Uani 1 1 d . A . H40 H 0.1345 0.5760 0.2140 0.048 Uiso 1 1 calc R . . C41 C 0.3065(5) 0.5697(4) 0.2302(4) 0.0419(12) Uani 1 1 d . . . H41 H 0.2751 0.6419 0.2598 0.050 Uiso 1 1 calc R A . C42 C 0.4339(5) 0.5049(5) 0.2155(4) 0.0499(14) Uani 1 1 d . A . H42 H 0.4905 0.5320 0.2345 0.060 Uiso 1 1 calc R . . C43 C 0.4796(5) 0.3989(5) 0.1723(5) 0.0578(15) Uani 1 1 d . . . H43 H 0.5677 0.3528 0.1630 0.069 Uiso 1 1 calc R A . C44 C 0.3972(5) 0.3607(5) 0.1431(4) 0.0475(13) Uani 1 1 d . A . H44 H 0.4290 0.2887 0.1131 0.057 Uiso 1 1 calc R . . N1 N 0.1354(4) 0.3311(3) -0.0302(3) 0.0356(9) Uani 1 1 d . A . N2 N 0.0057(3) 0.2061(3) -0.0967(3) 0.0318(9) Uani 1 1 d . A . H2A H 0.0111 0.2216 -0.0362 0.038 Uiso 1 1 calc R . . N3 N -0.1219(3) 0.1849(3) 0.1175(3) 0.0319(9) Uani 1 1 d . A . N4 N 0.0183(4) 0.2977(3) 0.1863(3) 0.0372(10) Uani 1 1 d . A . H4 H 0.0020 0.2948 0.1248 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.042(3) 0.027(2) 0.042(3) 0.000(2) -0.007(2) -0.018(2) C4 0.040(3) 0.040(3) 0.032(3) 0.008(2) -0.012(2) -0.021(2) C5 0.033(2) 0.045(3) 0.036(3) 0.007(2) -0.009(2) -0.017(2) C6 0.032(2) 0.041(3) 0.033(3) 0.006(2) -0.010(2) -0.017(2) C7 0.044(3) 0.043(3) 0.032(3) -0.004(2) -0.005(2) -0.018(2) C8 0.038(3) 0.039(3) 0.037(3) -0.003(2) -0.006(2) -0.021(2) C9 0.032(2) 0.030(2) 0.032(2) 0.0037(19) -0.0079(19) -0.016(2) C10 0.032(2) 0.026(2) 0.040(3) 0.002(2) -0.012(2) -0.012(2) C11 0.034(2) 0.031(2) 0.032(3) -0.0014(19) -0.015(2) -0.013(2) C14 0.037(3) 0.034(3) 0.035(3) 0.000(2) -0.001(2) -0.018(2) C15 0.047(3) 0.040(3) 0.027(2) -0.006(2) -0.001(2) -0.024(2) C16 0.048(3) 0.039(3) 0.032(3) -0.004(2) -0.001(2) -0.023(2) C17 0.061(3) 0.056(3) 0.032(3) -0.012(2) -0.003(2) -0.038(3) C18 0.061(3) 0.049(3) 0.038(3) -0.012(2) -0.003(2) -0.034(3) C19 0.044(3) 0.037(3) 0.040(3) -0.009(2) -0.003(2) -0.024(2) C20 0.044(3) 0.029(2) 0.040(3) -0.006(2) -0.006(2) -0.018(2) C21 0.045(4) 0.063(7) 0.034(3) 0.000(3) -0.009(2) -0.036(4) C22 0.046(6) 0.102(11) 0.048(7) 0.010(7) -0.002(5) -0.025(7) C23 0.052(7) 0.145(14) 0.056(8) -0.007(9) 0.001(5) -0.036(8) C24 0.097(10) 0.142(16) 0.030(6) 0.008(7) -0.003(6) -0.095(11) C25 0.149(17) 0.070(9) 0.027(8) -0.003(7) -0.009(8) -0.068(10) C26 0.102(10) 0.047(7) 0.025(6) 0.010(5) -0.002(6) -0.041(7) N5 0.043(8) 0.031(8) 0.046(3) 0.008(3) -0.017(3) -0.018(8) C3B 0.038(7) 0.037(9) 0.033(3) 0.019(3) -0.012(3) -0.023(8) N6 0.097(6) 0.082(6) 0.059(5) 0.008(4) -0.012(4) -0.061(5) O1 0.104(5) 0.114(6) 0.063(4) 0.012(4) -0.025(4) -0.077(5) C2 0.043(8) 0.031(8) 0.046(3) 0.008(3) -0.017(3) -0.018(8) C3 0.038(7) 0.037(9) 0.033(3) 0.019(3) -0.012(3) -0.023(8) N7 0.037(8) 0.037(11) 0.032(3) 0.001(4) -0.006(3) -0.017(9) C12B 0.044(3) 0.044(3) 0.034(3) 0.000(2) -0.008(2) -0.029(2) O2 0.104(5) 0.114(6) 0.063(4) 0.012(4) -0.025(4) -0.077(5) N8 0.097(6) 0.082(6) 0.059(5) 0.008(4) -0.012(4) -0.061(5) C13 0.037(8) 0.037(11) 0.032(3) 0.001(4) -0.006(3) -0.017(9) C12 0.044(3) 0.044(3) 0.034(3) 0.000(2) -0.008(2) -0.029(2) C21B 0.045(4) 0.063(7) 0.034(3) 0.000(3) -0.009(2) -0.036(4) C22B 0.041(10) 0.12(2) 0.032(9) 0.003(10) -0.006(7) -0.038(13) C23B 0.048(11) 0.18(3) 0.042(12) -0.004(14) -0.014(9) -0.059(16) C24B 0.13(3) 0.13(3) 0.038(13) -0.035(14) 0.027(14) -0.10(2) C25B 0.14(3) 0.10(2) 0.039(14) 0.021(13) -0.002(12) -0.10(2) C26B 0.080(15) 0.069(15) 0.064(15) -0.004(12) -0.030(12) -0.048(13) O3 0.155(18) 0.30(3) 0.22(2) -0.16(2) 0.031(16) -0.15(2) C27 0.035(2) 0.035(3) 0.024(2) 0.0044(19) -0.0056(19) -0.020(2) C28 0.040(3) 0.035(3) 0.055(3) 0.002(2) -0.020(2) -0.017(2) C29 0.061(3) 0.039(3) 0.049(3) 0.002(2) -0.020(3) -0.030(3) C30 0.047(3) 0.061(4) 0.037(3) 0.010(2) -0.014(2) -0.037(3) C31 0.036(3) 0.056(3) 0.034(3) 0.002(2) -0.009(2) -0.020(3) C32 0.037(3) 0.043(3) 0.031(3) -0.003(2) -0.006(2) -0.016(2) C33 0.049(3) 0.048(3) 0.034(3) -0.008(2) -0.004(2) -0.025(3) C34 0.074(4) 0.048(3) 0.039(3) -0.002(3) 0.003(3) -0.026(3) C35 0.090(5) 0.057(4) 0.047(4) 0.003(3) 0.007(3) -0.033(4) C36 0.084(4) 0.077(5) 0.034(3) -0.007(3) 0.008(3) -0.044(4) C37 0.082(4) 0.061(4) 0.041(3) -0.018(3) 0.006(3) -0.033(3) C38 0.069(4) 0.050(3) 0.035(3) -0.005(2) -0.001(3) -0.031(3) C39 0.042(3) 0.034(3) 0.037(3) -0.003(2) -0.004(2) -0.023(2) C40 0.045(3) 0.036(3) 0.042(3) -0.003(2) -0.010(2) -0.017(2) C41 0.051(3) 0.032(3) 0.050(3) -0.008(2) -0.008(2) -0.022(2) C42 0.051(3) 0.052(3) 0.058(4) -0.011(3) -0.006(3) -0.030(3) C43 0.038(3) 0.057(4) 0.083(4) -0.023(3) -0.004(3) -0.019(3) C44 0.043(3) 0.042(3) 0.064(4) -0.020(3) -0.007(3) -0.016(2) N1 0.038(2) 0.032(2) 0.038(2) -0.0001(17) -0.0065(17) -0.0162(18) N2 0.034(2) 0.037(2) 0.029(2) 0.0011(16) -0.0100(16) -0.0194(18) N3 0.036(2) 0.033(2) 0.031(2) -0.0042(16) -0.0061(16) -0.0165(18) N4 0.048(2) 0.041(2) 0.034(2) -0.0062(18) -0.0045(18) -0.028(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.362(6) . ? C1 C20 1.400(7) . ? C1 N5 1.408(12) . ? C1 C2 1.435(16) . ? C4 N1 1.368(6) . ? C4 C5 1.399(7) . ? C4 C3 1.432(16) . ? C4 C3B 1.467(14) . ? C5 C6 1.414(6) . ? C5 C21B 1.479(12) . ? C5 C21 1.526(8) . ? C6 N2 1.365(6) . ? C6 C7 1.433(6) . ? C7 C8 1.353(6) . ? C7 H7 0.9500 . ? C8 C9 1.426(6) . ? C8 H8 0.9500 . ? C9 N2 1.382(5) . ? C9 C10 1.398(6) . ? C10 C11 1.399(6) . ? C10 C27 1.512(6) . ? C11 N3 1.375(5) . ? C11 C12 1.425(16) . ? C11 C12B 1.45(3) . ? C14 N3 1.373(6) . ? C14 C15 1.397(6) . ? C14 C13 1.437(15) . ? C14 N7 1.46(3) . ? C15 C16 1.404(6) . ? C15 C33 1.490(6) . ? C16 N4 1.359(6) . ? C16 C17 1.427(6) . ? C17 C18 1.353(6) . ? C17 H17 0.9500 . ? C18 C19 1.429(6) . ? C18 H18 0.9500 . ? C19 N4 1.367(6) . ? C19 C20 1.402(6) . ? C20 C39 1.503(6) . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C22 C23 1.3900 . ? C22 H22 0.9500 . ? C23 C24 1.3900 . ? C23 H23 0.9500 . ? C24 C25 1.3900 . ? C24 H24 0.9500 . ? C25 C26 1.3900 . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? N5 C3B 1.353(13) . ? N5 N6 1.361(14) . ? C3B O1 1.182(13) . ? N6 H6A 0.87(2) . ? N6 H6B 0.88(2) . ? C2 C3 1.358(16) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? N7 N8 1.31(3) . ? N7 C12B 1.37(3) . ? C12B O2 1.19(3) . ? N8 H8A 0.89(2) . ? N8 H8B 0.89(2) . ? C13 C12 1.357(16) . ? C13 H13 0.9500 . ? C12 H12 0.9500 . ? C21B C22B 1.3900 . ? C21B C26B 1.3900 . ? C22B C23B 1.3900 . ? C22B H22B 0.9500 . ? C23B C24B 1.3900 . ? C23B H23B 0.9500 . ? C24B C25B 1.3900 . ? C24B H24B 0.9500 . ? C25B C26B 1.3900 . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? O3 H3A 0.8524 . ? O3 H3B 0.8454 . ? O3 H3C 0.8376 . ? C27 C28 1.381(6) . ? C27 C32 1.390(6) . ? C28 C29 1.397(7) . ? C28 H28 0.9500 . ? C29 C30 1.379(7) . ? C29 H29 0.9500 . ? C30 C31 1.380(7) . ? C30 H30 0.9500 . ? C31 C32 1.375(7) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C34 1.380(7) . ? C33 C38 1.384(7) . ? C34 C35 1.376(8) . ? C34 H34 0.9500 . ? C35 C36 1.358(8) . ? C35 H35 0.9500 . ? C36 C37 1.385(8) . ? C36 H36 0.9500 . ? C37 C38 1.382(7) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C39 C44 1.384(7) . ? C39 C40 1.391(7) . ? C40 C41 1.391(7) . ? C40 H40 0.9500 . ? C41 C42 1.371(7) . ? C41 H41 0.9500 . ? C42 C43 1.392(7) . ? C42 H42 0.9500 . ? C43 C44 1.382(7) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? N2 H2A 0.8800 . ? N4 H4 0.8800 . ? 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 C20 126.4(4) . . ? N1 C1 N5 109.2(5) . . ? C20 C1 N5 124.4(5) . . ? N1 C1 C2 109.7(7) . . ? C20 C1 C2 122.7(8) . . ? N1 C4 C5 125.7(4) . . ? N1 C4 C3 109.6(7) . . ? C5 C4 C3 124.1(8) . . ? N1 C4 C3B 109.6(6) . . ? C5 C4 C3B 124.7(6) . . ? C4 C5 C6 125.2(4) . . ? C4 C5 C21B 115.1(9) . . ? C6 C5 C21B 119.2(9) . . ? C4 C5 C21 121.1(6) . . ? C6 C5 C21 113.7(6) . . ? N2 C6 C5 126.5(4) . . ? N2 C6 C7 107.5(4) . . ? C5 C6 C7 125.6(4) . . ? C8 C7 C6 107.4(4) . . ? C8 C7 H7 126.3 . . ? C6 C7 H7 126.3 . . ? C7 C8 C9 108.9(4) . . ? C7 C8 H8 125.6 . . ? C9 C8 H8 125.6 . . ? N2 C9 C10 125.6(4) . . ? N2 C9 C8 106.5(3) . . ? C10 C9 C8 127.9(4) . . ? C9 C10 C11 125.9(4) . . ? C9 C10 C27 117.2(4) . . ? C11 C10 C27 116.8(4) . . ? N3 C11 C10 126.2(4) . . ? N3 C11 C12 109.2(7) . . ? C10 C11 C12 124.5(7) . . ? N3 C11 C12B 110.1(12) . . ? C10 C11 C12B 123.6(12) . . ? N3 C14 C15 126.2(4) . . ? N3 C14 C13 109.3(7) . . ? C15 C14 C13 124.2(7) . . ? N3 C14 N7 109.0(10) . . ? C15 C14 N7 124.6(10) . . ? C14 C15 C16 124.4(4) . . ? C14 C15 C33 118.9(4) . . ? C16 C15 C33 116.7(4) . . ? N4 C16 C15 127.5(4) . . ? N4 C16 C17 107.2(4) . . ? C15 C16 C17 125.2(4) . . ? C18 C17 C16 108.1(4) . . ? C18 C17 H17 125.9 . . ? C16 C17 H17 125.9 . . ? C17 C18 C19 107.6(4) . . ? C17 C18 H18 126.2 . . ? C19 C18 H18 126.2 . . ? N4 C19 C20 126.7(4) . . ? N4 C19 C18 107.1(4) . . ? C20 C19 C18 126.1(4) . . ? C1 C20 C19 124.4(4) . . ? C1 C20 C39 118.3(4) . . ? C19 C20 C39 117.2(4) . . ? C22 C21 C26 120.0 . . ? C22 C21 C5 121.9(8) . . ? C26 C21 C5 118.0(7) . . ? C21 C22 C23 120.0 . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C24 C23 C22 120.0 . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.0 . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C25 C26 120.0 . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 120.0 . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? C3B N5 N6 125.5(11) . . ? C3B N5 C1 109.9(8) . . ? N6 N5 C1 123.6(8) . . ? O1 C3B N5 122.8(11) . . ? O1 C3B C4 133.1(10) . . ? N5 C3B C4 104.1(8) . . ? N5 N6 H6A 108(4) . . ? N5 N6 H6B 107(4) . . ? H6A N6 H6B 107(3) . . ? C3 C2 C1 106.8(10) . . ? C3 C2 H2 126.6 . . ? C1 C2 H2 126.6 . . ? C2 C3 C4 107.0(10) . . ? C2 C3 H3 126.5 . . ? C4 C3 H3 126.5 . . ? N8 N7 C12B 128(2) . . ? N8 N7 C14 123.5(19) . . ? C12B N7 C14 107.0(19) . . ? O2 C12B N7 119(3) . . ? O2 C12B C11 135(2) . . ? N7 C12B C11 105.9(18) . . ? N7 N8 H8A 111(5) . . ? N7 N8 H8B 111(5) . . ? H8A N8 H8B 103(3) . . ? C12 C13 C14 106.5(10) . . ? C12 C13 H13 126.8 . . ? C14 C13 H13 126.8 . . ? C13 C12 C11 107.7(10) . . ? C13 C12 H12 126.1 . . ? C11 C12 H12 126.1 . . ? C22B C21B C26B 120.0 . . ? C22B C21B C5 117.9(15) . . ? C26B C21B C5 122.1(15) . . ? C21B C22B C23B 120.0 . . ? C21B C22B H22B 120.0 . . ? C23B C22B H22B 120.0 . . ? C24B C23B C22B 120.0 . . ? C24B C23B H23B 120.0 . . ? C22B C23B H23B 120.0 . . ? C23B C24B C25B 120.0 . . ? C23B C24B H24B 120.0 . . ? C25B C24B H24B 120.0 . . ? C24B C25B C26B 120.0 . . ? C24B C25B H25B 120.0 . . ? C26B C25B H25B 120.0 . . ? C25B C26B C21B 120.0 . . ? C25B C26B H26B 120.0 . . ? C21B C26B H26B 120.0 . . ? H3A O3 H3B 104.7 . . ? H3A O3 H3C 111.1 . . ? H3B O3 H3C 106.7 . . ? C28 C27 C32 119.6(4) . . ? C28 C27 C10 121.8(4) . . ? C32 C27 C10 118.6(4) . . ? C27 C28 C29 119.5(5) . . ? C27 C28 H28 120.3 . . ? C29 C28 H28 120.3 . . ? C30 C29 C28 120.4(5) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C29 C30 C31 119.8(5) . . ? C29 C30 H30 120.1 . . ? C31 C30 H30 120.1 . . ? C32 C31 C30 120.1(5) . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C31 C32 C27 120.6(5) . . ? C31 C32 H32 119.7 . . ? C27 C32 H32 119.7 . . ? C34 C33 C38 118.7(5) . . ? C34 C33 C15 122.3(5) . . ? C38 C33 C15 119.0(4) . . ? C35 C34 C33 120.6(6) . . ? C35 C34 H34 119.7 . . ? C33 C34 H34 119.7 . . ? C36 C35 C34 120.7(6) . . ? C36 C35 H35 119.6 . . ? C34 C35 H35 119.6 . . ? C35 C36 C37 119.7(5) . . ? C35 C36 H36 120.1 . . ? C37 C36 H36 120.1 . . ? C38 C37 C36 119.7(6) . . ? C38 C37 H37 120.1 . . ? C36 C37 H37 120.1 . . ? C37 C38 C33 120.5(5) . . ? C37 C38 H38 119.7 . . ? C33 C38 H38 119.7 . . ? C44 C39 C40 119.4(4) . . ? C44 C39 C20 119.6(4) . . ? C40 C39 C20 121.0(4) . . ? C41 C40 C39 119.7(5) . . ? C41 C40 H40 120.2 . . ? C39 C40 H40 120.2 . . ? C42 C41 C40 120.8(5) . . ? C42 C41 H41 119.6 . . ? C40 C41 H41 119.6 . . ? C41 C42 C43 119.4(5) . . ? C41 C42 H42 120.3 . . ? C43 C42 H42 120.3 . . ? C44 C43 C42 120.2(5) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C43 C44 C39 120.4(5) . . ? C43 C44 H44 119.8 . . ? C39 C44 H44 119.8 . . ? C1 N1 C4 106.7(4) . . ? C6 N2 C9 109.5(4) . . ? C6 N2 H2A 125.2 . . ? C9 N2 H2A 125.2 . . ? C14 N3 C11 106.7(4) . . ? C16 N4 C19 109.8(4) . . ? C16 N4 H4 125.1 . . ? C19 N4 H4 125.1 . . ? 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 C4 C5 C6 7.9(8) . . . . ? C3 C4 C5 C6 178(2) . . . . ? C3B C4 C5 C6 -169.6(12) . . . . ? N1 C4 C5 C21B 179.2(11) . . . . ? C3 C4 C5 C21B -11(3) . . . . ? C3B C4 C5 C21B 1.7(16) . . . . ? N1 C4 C5 C21 -169.8(7) . . . . ? C3 C4 C5 C21 0(3) . . . . ? C3B C4 C5 C21 12.7(14) . . . . ? C4 C5 C6 N2 0.8(8) . . . . ? C21B C5 C6 N2 -170.1(11) . . . . ? C21 C5 C6 N2 178.7(6) . . . . ? C4 C5 C6 C7 173.2(5) . . . . ? C21B C5 C6 C7 2.2(13) . . . . ? C21 C5 C6 C7 -9.0(8) . . . . ? N2 C6 C7 C8 2.4(5) . . . . ? C5 C6 C7 C8 -171.2(5) . . . . ? C6 C7 C8 C9 -0.8(5) . . . . ? C7 C8 C9 N2 -1.0(5) . . . . ? C7 C8 C9 C10 176.7(4) . . . . ? N2 C9 C10 C11 -6.3(7) . . . . ? C8 C9 C10 C11 176.5(4) . . . . ? N2 C9 C10 C27 171.1(4) . . . . ? C8 C9 C10 C27 -6.1(7) . . . . ? C9 C10 C11 N3 5.1(7) . . . . ? C27 C10 C11 N3 -172.3(4) . . . . ? C9 C10 C11 C12 -172.2(8) . . . . ? C27 C10 C11 C12 10.3(9) . . . . ? C9 C10 C11 C12B -172.5(9) . . . . ? C27 C10 C11 C12B 10.1(10) . . . . ? N3 C14 C15 C16 0.8(8) . . . . ? C13 C14 C15 C16 174.1(18) . . . . ? N7 C14 C15 C16 -173(3) . . . . ? N3 C14 C15 C33 179.0(4) . . . . ? C13 C14 C15 C33 -7.7(18) . . . . ? N7 C14 C15 C33 5(3) . . . . ? C14 C15 C16 N4 7.3(8) . . . . ? C33 C15 C16 N4 -170.9(5) . . . . ? C14 C15 C16 C17 -169.1(5) . . . . ? C33 C15 C16 C17 12.7(7) . . . . ? N4 C16 C17 C18 -0.1(6) . . . . ? C15 C16 C17 C18 176.9(5) . . . . ? C16 C17 C18 C19 1.5(6) . . . . ? C17 C18 C19 N4 -2.3(6) . . . . ? C17 C18 C19 C20 179.7(5) . . . . ? N1 C1 C20 C19 -11.5(8) . . . . ? N5 C1 C20 C19 169.3(11) . . . . ? C2 C1 C20 C19 -177(3) . . . . ? N1 C1 C20 C39 164.6(4) . . . . ? N5 C1 C20 C39 -14.6(12) . . . . ? C2 C1 C20 C39 -1(3) . . . . ? N4 C19 C20 C1 -4.0(8) . . . . ? C18 C19 C20 C1 173.7(5) . . . . ? N4 C19 C20 C39 179.9(4) . . . . ? C18 C19 C20 C39 -2.4(7) . . . . ? C4 C5 C21 C22 99.9(8) . . . . ? C6 C5 C21 C22 -78.1(9) . . . . ? C21B C5 C21 C22 161(7) . . . . ? C4 C5 C21 C26 -77.9(8) . . . . ? C6 C5 C21 C26 104.1(6) . . . . ? C21B C5 C21 C26 -17(6) . . . . ? C26 C21 C22 C23 0.0 . . . . ? C5 C21 C22 C23 -177.7(9) . . . . ? C21 C22 C23 C24 0.0 . . . . ? C22 C23 C24 C25 0.0 . . . . ? C23 C24 C25 C26 0.0 . . . . ? C24 C25 C26 C21 0.0 . . . . ? C22 C21 C26 C25 0.0 . . . . ? C5 C21 C26 C25 177.8(9) . . . . ? N1 C1 N5 C3B -3.4(17) . . . . ? C20 C1 N5 C3B 175.8(12) . . . . ? C2 C1 N5 C3B 91(5) . . . . ? N1 C1 N5 N6 166.0(15) . . . . ? C20 C1 N5 N6 -15(2) . . . . ? C2 C1 N5 N6 -99(5) . . . . ? N6 N5 C3B O1 11(3) . . . . ? C1 N5 C3B O1 -179(2) . . . . ? N6 N5 C3B C4 -170.4(18) . . . . ? C1 N5 C3B C4 -1.3(19) . . . . ? N1 C4 C3B O1 -177(2) . . . . ? C5 C4 C3B O1 1(3) . . . . ? C3 C4 C3B O1 92(6) . . . . ? N1 C4 C3B N5 5.5(16) . . . . ? C5 C4 C3B N5 -176.6(11) . . . . ? C3 C4 C3B N5 -86(5) . . . . ? N1 C1 C2 C3 5(4) . . . . ? C20 C1 C2 C3 173(2) . . . . ? N5 C1 C2 C3 -85(5) . . . . ? C1 C2 C3 C4 -2(5) . . . . ? N1 C4 C3 C2 -1(4) . . . . ? C5 C4 C3 C2 -172(3) . . . . ? C3B C4 C3 C2 91(6) . . . . ? N3 C14 N7 N8 178(3) . . . . ? C15 C14 N7 N8 -7(6) . . . . ? C13 C14 N7 N8 85(8) . . . . ? N3 C14 N7 C12B 11(3) . . . . ? C15 C14 N7 C12B -174.4(15) . . . . ? C13 C14 N7 C12B -83(9) . . . . ? N8 N7 C12B O2 6(5) . . . . ? C14 N7 C12B O2 173(2) . . . . ? N8 N7 C12B C11 -178(4) . . . . ? C14 N7 C12B C11 -11(3) . . . . ? N3 C11 C12B O2 -177.2(15) . . . . ? C10 C11 C12B O2 1(2) . . . . ? C12 C11 C12B O2 -166(80) . . . . ? N3 C11 C12B N7 8(2) . . . . ? C10 C11 C12B N7 -174(2) . . . . ? C12 C11 C12B N7 19(78) . . . . ? N3 C14 C13 C12 -8(2) . . . . ? C15 C14 C13 C12 178.0(11) . . . . ? N7 C14 C13 C12 82(8) . . . . ? C14 C13 C12 C11 7(2) . . . . ? N3 C11 C12 C13 -3.6(16) . . . . ? C10 C11 C12 C13 174.2(15) . . . . ? C12B C11 C12 C13 -172(79) . . . . ? C4 C5 C21B C22B 81.0(15) . . . . ? C6 C5 C21B C22B -107.2(13) . . . . ? C21 C5 C21B C22B -43(5) . . . . ? C4 C5 C21B C26B -98.2(10) . . . . ? C6 C5 C21B C26B 73.7(13) . . . . ? C21 C5 C21B C26B 137(7) . . . . ? C26B C21B C22B C23B 0.0 . . . . ? C5 C21B C22B C23B -179.2(17) . . . . ? C21B C22B C23B C24B 0.0 . . . . ? C22B C23B C24B C25B 0.0 . . . . ? C23B C24B C25B C26B 0.0 . . . . ? C24B C25B C26B C21B 0.0 . . . . ? C22B C21B C26B C25B 0.0 . . . . ? C5 C21B C26B C25B 179.1(17) . . . . ? C9 C10 C27 C28 69.4(6) . . . . ? C11 C10 C27 C28 -112.9(5) . . . . ? C9 C10 C27 C32 -111.6(5) . . . . ? C11 C10 C27 C32 66.1(5) . . . . ? C32 C27 C28 C29 -0.8(7) . . . . ? C10 C27 C28 C29 178.2(4) . . . . ? C27 C28 C29 C30 -0.4(7) . . . . ? C28 C29 C30 C31 1.3(7) . . . . ? C29 C30 C31 C32 -1.0(7) . . . . ? C30 C31 C32 C27 -0.3(7) . . . . ? C28 C27 C32 C31 1.2(7) . . . . ? C10 C27 C32 C31 -177.8(4) . . . . ? C14 C15 C33 C34 73.4(7) . . . . ? C16 C15 C33 C34 -108.3(6) . . . . ? C14 C15 C33 C38 -108.2(5) . . . . ? C16 C15 C33 C38 70.1(6) . . . . ? C38 C33 C34 C35 0.1(8) . . . . ? C15 C33 C34 C35 178.6(5) . . . . ? C33 C34 C35 C36 -1.1(10) . . . . ? C34 C35 C36 C37 2.5(10) . . . . ? C35 C36 C37 C38 -2.8(9) . . . . ? C36 C37 C38 C33 1.9(9) . . . . ? C34 C33 C38 C37 -0.5(8) . . . . ? C15 C33 C38 C37 -179.0(5) . . . . ? C1 C20 C39 C44 -65.8(6) . . . . ? C19 C20 C39 C44 110.6(5) . . . . ? C1 C20 C39 C40 113.1(5) . . . . ? C19 C20 C39 C40 -70.5(6) . . . . ? C44 C39 C40 C41 1.4(7) . . . . ? C20 C39 C40 C41 -177.4(4) . . . . ? C39 C40 C41 C42 -1.0(7) . . . . ? C40 C41 C42 C43 -0.2(8) . . . . ? C41 C42 C43 C44 1.0(9) . . . . ? C42 C43 C44 C39 -0.6(9) . . . . ? C40 C39 C44 C43 -0.6(8) . . . . ? C20 C39 C44 C43 178.3(5) . . . . ? C20 C1 N1 C4 -172.4(5) . . . . ? N5 C1 N1 C4 6.8(10) . . . . ? C2 C1 N1 C4 -5(3) . . . . ? C5 C4 N1 C1 174.5(4) . . . . ? C3 C4 N1 C1 4(2) . . . . ? C3B C4 N1 C1 -7.7(11) . . . . ? C5 C6 N2 C9 170.4(4) . . . . ? C7 C6 N2 C9 -3.0(5) . . . . ? C10 C9 N2 C6 -175.2(4) . . . . ? C8 C9 N2 C6 2.5(5) . . . . ? C15 C14 N3 C11 179.6(4) . . . . ? C13 C14 N3 C11 5.5(16) . . . . ? N7 C14 N3 C11 -6(2) . . . . ? C10 C11 N3 C14 -179.0(4) . . . . ? C12 C11 N3 C14 -1.3(7) . . . . ? C12B C11 N3 C14 -1.1(9) . . . . ? C15 C16 N4 C19 -178.2(5) . . . . ? C17 C16 N4 C19 -1.3(5) . . . . ? C20 C19 N4 C16 -179.8(5) . . . . ? C18 C19 N4 C16 2.2(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4 N3 0.88 2.38 2.914(5) 119.3 . N4 H4 N1 0.88 2.38 2.919(5) 119.5 . N2 H2A N3 0.88 2.37 2.921(5) 120.9 . N2 H2A N1 0.88 2.38 2.918(5) 120.0 . O3 H3A O3 0.85 2.31 3.10(2) 154.4 2_656 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.825 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.094 data_10mz469_0m _database_code_depnum_ccdc_archive 'CCDC 821399' #TrackingRef '- CC-5-19-2011(compounds 6,7,8).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H32 N6 O, 2(C2 H6 O)' _chemical_formula_sum 'C47 H44 N6 O3' _chemical_formula_weight 740.88 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.805(2) _cell_length_b 12.627(2) _cell_length_c 13.460(2) _cell_angle_alpha 107.192(2) _cell_angle_beta 95.593(2) _cell_angle_gamma 90.383(3) _cell_volume 1906.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7477 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 30.95 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5968 _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_process_details 'Apex2 v2009.7-0 (Bruker, 2009)' _exptl_special_details ; The two ethanol solvent molecules are disordered over each two mutually exclusive positions. The occupancy ratios of the two neighboring sites are unrelated and are 0.753(7) to 0.247(7) and 0.637(8) to 0.363(8), respectively. The geometries of the four ethanol molecules were restrained to be similar. The positions of acidic H atoms were restrained based on hydrogen bonding considerations. ; _diffrn_ambient_temperature 100(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 AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 25313 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0407 _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 1.69 _diffrn_reflns_theta_max 27.87 _reflns_number_total 9008 _reflns_number_gt 7105 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2009.7-0 (Bruker, 2009)' _computing_cell_refinement 'Apex2 v2009.7-0' _computing_data_reduction 'Apex2 v2009.7-0' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0720P)^2^+1.1613P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9008 _refine_ls_number_parameters 569 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1640 _refine_ls_wR_factor_gt 0.1484 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.4831(4) 0.2400(4) 0.4588(3) 0.0507(9) Uani 0.753(7) 1 d PD A 1 H2A H 0.4598 0.2323 0.5134 0.076 Uiso 0.753(7) 1 calc PRD A 1 C45 C 0.5822(4) 0.1805(4) 0.4379(3) 0.0622(14) Uani 0.753(7) 1 d PD A 1 H45A H 0.5631 0.0999 0.4166 0.075 Uiso 0.753(7) 1 calc PR A 1 H45B H 0.6365 0.1986 0.5020 0.075 Uiso 0.753(7) 1 calc PR A 1 C46 C 0.6359(3) 0.2088(4) 0.3530(4) 0.0567(12) Uani 0.753(7) 1 d PD A 1 H46A H 0.6566 0.2882 0.3750 0.085 Uiso 0.753(7) 1 calc PR A 1 H46B H 0.5819 0.1909 0.2897 0.085 Uiso 0.753(7) 1 calc PR A 1 H46C H 0.7044 0.1660 0.3382 0.085 Uiso 0.753(7) 1 calc PR A 1 O3 O 0.3986(7) 0.2232(9) 0.6192(5) 0.069(2) Uani 0.637(8) 1 d PD B 1 H3 H 0.3506 0.2650 0.6516 0.104 Uiso 0.637(8) 1 calc PRD A 1 C47 C 0.4683(5) 0.1803(5) 0.6905(5) 0.077(2) Uani 0.637(8) 1 d PD B 1 H47A H 0.5206 0.1258 0.6520 0.093 Uiso 0.637(8) 1 calc PR B 1 H47B H 0.4199 0.1423 0.7266 0.093 Uiso 0.637(8) 1 calc PR B 1 C48 C 0.5349(10) 0.2742(8) 0.7683(9) 0.141(6) Uani 0.637(8) 1 d PD B 1 H48A H 0.4828 0.3304 0.8022 0.212 Uiso 0.637(8) 1 calc PR B 1 H48B H 0.5877 0.3069 0.7328 0.212 Uiso 0.637(8) 1 calc PR B 1 H48C H 0.5780 0.2469 0.8212 0.212 Uiso 0.637(8) 1 calc PR B 1 O2B O 0.4741(14) 0.2598(14) 0.4336(12) 0.0507(9) Uani 0.247(7) 1 d P A 2 H2B H 0.4860 0.2294 0.4811 0.076 Uiso 0.247(7) 1 calc PRD A 2 C45B C 0.5742(8) 0.2628(7) 0.3869(8) 0.036(3) Uani 0.247(7) 1 d P A 2 H45C H 0.6102 0.3382 0.4152 0.044 Uiso 0.247(7) 1 calc PR A 2 H45D H 0.5545 0.2487 0.3108 0.044 Uiso 0.247(7) 1 calc PR A 2 C46B C 0.6567(12) 0.1820(9) 0.4035(12) 0.048(3) Uani 0.247(7) 1 d P A 2 H46D H 0.6224 0.1069 0.3744 0.072 Uiso 0.247(7) 1 calc PR A 2 H46E H 0.6785 0.1967 0.4786 0.072 Uiso 0.247(7) 1 calc PR A 2 H46F H 0.7245 0.1882 0.3686 0.072 Uiso 0.247(7) 1 calc PR A 2 O3B O 0.4037(9) 0.2449(12) 0.6537(8) 0.049(3) Uani 0.363(8) 1 d PD B 2 H3B H 0.3575 0.2952 0.6541 0.074 Uiso 0.363(8) 1 calc PR A 2 C47B C 0.4774(6) 0.2749(8) 0.7525(6) 0.045(3) Uani 0.363(8) 1 d PD B 2 H47C H 0.4430 0.2473 0.8048 0.054 Uiso 0.363(8) 1 calc PR B 2 H47D H 0.4883 0.3566 0.7806 0.054 Uiso 0.363(8) 1 calc PR B 2 C48B C 0.5888(6) 0.2227(8) 0.7301(7) 0.043(2) Uani 0.363(8) 1 d PD B 2 H48D H 0.6277 0.2593 0.6873 0.064 Uiso 0.363(8) 1 calc PR B 2 H48E H 0.5756 0.1438 0.6921 0.064 Uiso 0.363(8) 1 calc PR B 2 H48F H 0.6363 0.2308 0.7960 0.064 Uiso 0.363(8) 1 calc PR B 2 C1 C 0.21407(16) 0.46910(15) 0.62699(14) 0.0229(4) Uani 1 1 d . A . C2 C 0.15007(15) 0.57003(15) 0.65690(13) 0.0211(4) Uani 1 1 d . . . C3 C 0.12148(15) 0.61826(14) 0.75849(13) 0.0198(3) Uani 1 1 d . . . C4 C 0.04843(15) 0.70714(14) 0.78654(13) 0.0198(3) Uani 1 1 d . . . C5 C 0.01404(16) 0.75873(15) 0.88776(13) 0.0224(4) Uani 1 1 d . . . H5 H 0.0405 0.7421 0.9502 0.027 Uiso 1 1 calc R . . C6 C -0.06375(15) 0.83638(15) 0.87928(13) 0.0218(4) Uani 1 1 d . . . H6 H -0.1010 0.8825 0.9349 0.026 Uiso 1 1 calc R . . C7 C -0.07937(15) 0.83621(14) 0.77282(13) 0.0197(3) Uani 1 1 d . . . C8 C -0.15338(15) 0.90262(14) 0.73019(13) 0.0200(3) Uani 1 1 d . . . C9 C -0.16058(15) 0.91104(15) 0.62893(13) 0.0209(4) Uani 1 1 d . . . C10 C -0.24260(18) 0.98702(17) 0.59305(14) 0.0287(4) Uani 1 1 d . . . H10A H -0.2323 1.0640 0.6401 0.034 Uiso 1 1 calc R . . H10B H -0.3226 0.9611 0.5900 0.034 Uiso 1 1 calc R . . C11 C -0.21031(19) 0.97932(18) 0.48439(15) 0.0312(4) Uani 1 1 d . . . H11A H -0.2775 0.9590 0.4315 0.037 Uiso 1 1 calc R . . H11B H -0.1755 1.0502 0.4827 0.037 Uiso 1 1 calc R . . C12 C -0.12510(16) 0.88853(15) 0.46619(14) 0.0223(4) Uani 1 1 d . . . C13 C -0.08263(16) 0.84542(15) 0.36871(13) 0.0214(4) Uani 1 1 d . . . C14 C 0.00160(16) 0.76676(15) 0.34652(13) 0.0226(4) Uani 1 1 d . . . C15 C 0.05627(17) 0.73360(16) 0.25213(14) 0.0261(4) Uani 1 1 d . . . H15 H 0.0405 0.7602 0.1934 0.031 Uiso 1 1 calc R . . C16 C 0.13462(17) 0.65745(17) 0.26117(14) 0.0262(4) Uani 1 1 d . . . H16 H 0.1841 0.6232 0.2104 0.031 Uiso 1 1 calc R . . C17 C 0.12977(16) 0.63784(16) 0.36005(13) 0.0232(4) Uani 1 1 d . . . C18 C 0.18983(16) 0.56049(15) 0.39679(13) 0.0227(4) Uani 1 1 d . . . C19 C 0.17937(16) 0.54359(15) 0.49441(14) 0.0226(4) Uani 1 1 d . A . C21 C 0.17779(16) 0.57881(14) 0.84494(13) 0.0208(4) Uani 1 1 d . . . C22 C 0.29401(16) 0.60125(16) 0.87263(14) 0.0248(4) Uani 1 1 d . . . H22 H 0.3352 0.6399 0.8360 0.030 Uiso 1 1 calc R . . C23 C 0.35049(19) 0.56795(18) 0.95300(16) 0.0321(4) Uani 1 1 d . . . H23 H 0.4298 0.5841 0.9714 0.038 Uiso 1 1 calc R . . C24 C 0.29098(19) 0.51109(18) 1.00648(16) 0.0325(5) Uani 1 1 d . . . H24 H 0.3294 0.4882 1.0616 0.039 Uiso 1 1 calc R . . C25 C 0.1756(2) 0.48789(18) 0.97912(16) 0.0326(5) Uani 1 1 d . . . H25 H 0.1349 0.4485 1.0154 0.039 Uiso 1 1 calc R . . C26 C 0.11894(17) 0.52161(16) 0.89908(15) 0.0269(4) Uani 1 1 d . . . H26 H 0.0395 0.5056 0.8811 0.032 Uiso 1 1 calc R . . C27 C -0.23324(16) 0.96941(15) 0.80244(13) 0.0210(4) Uani 1 1 d . . . C28 C -0.19466(17) 1.06496(16) 0.88256(14) 0.0260(4) Uani 1 1 d . . . H28 H -0.1167 1.0885 0.8919 0.031 Uiso 1 1 calc R . . C29 C -0.27042(19) 1.12585(17) 0.94875(15) 0.0313(4) Uani 1 1 d . . . H29 H -0.2437 1.1906 1.0032 0.038 Uiso 1 1 calc R . . C30 C -0.38380(19) 1.09286(18) 0.93575(16) 0.0323(5) Uani 1 1 d . . . H30 H -0.4351 1.1350 0.9808 0.039 Uiso 1 1 calc R . . C31 C -0.42287(18) 0.99792(18) 0.85662(16) 0.0311(4) Uani 1 1 d . . . H31 H -0.5009 0.9747 0.8478 0.037 Uiso 1 1 calc R . . C32 C -0.34788(17) 0.93670(16) 0.79027(15) 0.0263(4) Uani 1 1 d . . . H32 H -0.3752 0.8719 0.7361 0.032 Uiso 1 1 calc R . . C33 C -0.13773(16) 0.87654(15) 0.27665(13) 0.0223(4) Uani 1 1 d . . . C34 C -0.12847(17) 0.98252(16) 0.26562(15) 0.0261(4) Uani 1 1 d . . . H34 H -0.0850 1.0393 0.3182 0.031 Uiso 1 1 calc R . . C35 C -0.18218(18) 1.00590(17) 0.17850(16) 0.0288(4) Uani 1 1 d . . . H35 H -0.1746 1.0783 0.1716 0.035 Uiso 1 1 calc R . . C36 C -0.24697(18) 0.92420(18) 0.10142(15) 0.0293(4) Uani 1 1 d . . . H36 H -0.2845 0.9405 0.0423 0.035 Uiso 1 1 calc R . . C37 C -0.25623(19) 0.81836(18) 0.11174(15) 0.0321(5) Uani 1 1 d . . . H37 H -0.3002 0.7619 0.0592 0.039 Uiso 1 1 calc R . . C38 C -0.20164(18) 0.79455(17) 0.19834(14) 0.0282(4) Uani 1 1 d . . . H38 H -0.2079 0.7217 0.2043 0.034 Uiso 1 1 calc R . . C39 C 0.27144(16) 0.49239(15) 0.32804(14) 0.0224(4) Uani 1 1 d . . . C40 C 0.23173(16) 0.40651(15) 0.23926(13) 0.0232(4) Uani 1 1 d . . . H40 H 0.1521 0.3940 0.2199 0.028 Uiso 1 1 calc R . . C41 C 0.30727(17) 0.33922(16) 0.17901(14) 0.0262(4) Uani 1 1 d . . . H41 H 0.2793 0.2795 0.1199 0.031 Uiso 1 1 calc R . . C42 C 0.42261(19) 0.35869(18) 0.20459(18) 0.0351(5) Uani 1 1 d . . . H42 H 0.4744 0.3130 0.1629 0.042 Uiso 1 1 calc R . . C43 C 0.4631(2) 0.4455(2) 0.2917(2) 0.0497(7) Uani 1 1 d . . . H43 H 0.5428 0.4596 0.3090 0.060 Uiso 1 1 calc R . . C44 C 0.38771(18) 0.5120(2) 0.35372(19) 0.0396(5) Uani 1 1 d . . . H44 H 0.4160 0.5707 0.4136 0.047 Uiso 1 1 calc R . . N1 N 0.12743(13) 0.61017(13) 0.57359(11) 0.0210(3) Uani 1 1 d . . . N2 N -0.00901(13) 0.75812(12) 0.71995(11) 0.0199(3) Uani 1 1 d . . . H2 H -0.0015 0.7426 0.6528 0.024 Uiso 1 1 calc R . . N3 N -0.09634(13) 0.85532(12) 0.55188(11) 0.0209(3) Uani 1 1 d . . . N4 N 0.05004(13) 0.70838(13) 0.40962(11) 0.0225(3) Uani 1 1 d . . . H4 H 0.0327 0.7149 0.4732 0.027 Uiso 1 1 calc R . . O1 O 0.23978(14) 0.39798(12) 0.67493(11) 0.0341(3) Uani 1 1 d D . . N6 N 0.2664(2) 0.35965(17) 0.45994(14) 0.0421(5) Uani 1 1 d D A . H6A H 0.3391(15) 0.367(3) 0.474(3) 0.063 Uiso 1 1 d D . . H6B H 0.251(2) 0.303(2) 0.485(2) 0.063 Uiso 1 1 d D . . N5 N 0.23183(15) 0.45548(14) 0.52524(12) 0.0280(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 O2 0.0428(13) 0.057(2) 0.049(2) 0.0124(14) 0.0025(15) 0.0200(13) C45 0.060(3) 0.071(3) 0.047(2) 0.0049(19) 0.0059(19) 0.037(2) C46 0.041(2) 0.061(3) 0.062(3) 0.010(2) 0.0034(19) 0.003(2) O3 0.080(3) 0.084(4) 0.049(4) 0.026(3) 0.010(3) 0.041(3) C47 0.077(4) 0.074(4) 0.088(4) 0.045(4) -0.022(3) 0.000(3) C48 0.159(11) 0.120(9) 0.156(10) 0.096(8) -0.098(9) -0.076(9) O2B 0.0428(13) 0.057(2) 0.049(2) 0.0124(14) 0.0025(15) 0.0200(13) C45B 0.028(5) 0.027(5) 0.046(5) -0.002(4) 0.001(4) 0.006(4) C46B 0.058(8) 0.031(5) 0.059(8) 0.018(5) 0.012(6) 0.015(5) O3B 0.037(4) 0.074(7) 0.051(6) 0.037(6) 0.019(4) 0.031(4) C47B 0.042(4) 0.053(6) 0.049(5) 0.024(4) 0.021(4) 0.024(4) C48B 0.033(4) 0.056(5) 0.050(4) 0.029(4) 0.017(3) 0.024(3) C1 0.0253(9) 0.0232(9) 0.0169(8) 0.0008(7) 0.0021(7) 0.0051(7) C2 0.0212(8) 0.0221(8) 0.0186(8) 0.0042(7) 0.0017(6) 0.0030(7) C3 0.0221(8) 0.0195(8) 0.0174(8) 0.0044(6) 0.0033(6) 0.0014(7) C4 0.0212(8) 0.0201(8) 0.0172(8) 0.0040(6) 0.0034(6) 0.0005(7) C5 0.0248(9) 0.0261(9) 0.0155(8) 0.0048(7) 0.0025(7) 0.0020(7) C6 0.0231(9) 0.0250(9) 0.0157(8) 0.0030(7) 0.0035(6) 0.0023(7) C7 0.0214(8) 0.0204(8) 0.0157(7) 0.0024(6) 0.0037(6) 0.0017(7) C8 0.0220(8) 0.0195(8) 0.0155(7) 0.0002(6) 0.0035(6) 0.0024(7) C9 0.0226(9) 0.0209(8) 0.0176(8) 0.0029(6) 0.0020(6) 0.0019(7) C10 0.0355(11) 0.0321(10) 0.0181(8) 0.0063(7) 0.0039(7) 0.0109(8) C11 0.0382(11) 0.0364(11) 0.0189(9) 0.0070(8) 0.0060(8) 0.0153(9) C12 0.0234(9) 0.0242(9) 0.0177(8) 0.0040(7) 0.0016(7) 0.0028(7) C13 0.0267(9) 0.0200(8) 0.0167(8) 0.0040(6) 0.0033(7) 0.0020(7) C14 0.0250(9) 0.0251(9) 0.0163(8) 0.0038(7) 0.0022(7) 0.0021(7) C15 0.0299(10) 0.0310(10) 0.0186(8) 0.0080(7) 0.0065(7) 0.0036(8) C16 0.0276(10) 0.0333(10) 0.0173(8) 0.0055(7) 0.0062(7) 0.0051(8) C17 0.0235(9) 0.0281(9) 0.0146(8) 0.0007(7) 0.0030(6) 0.0042(7) C18 0.0224(9) 0.0256(9) 0.0161(8) 0.0003(7) 0.0016(6) 0.0033(7) C19 0.0233(9) 0.0240(9) 0.0174(8) 0.0018(7) -0.0003(7) 0.0051(7) C21 0.0253(9) 0.0196(8) 0.0161(8) 0.0029(6) 0.0037(6) 0.0047(7) C22 0.0258(9) 0.0277(9) 0.0220(8) 0.0077(7) 0.0053(7) 0.0056(7) C23 0.0303(10) 0.0372(11) 0.0275(10) 0.0085(8) 0.0004(8) 0.0080(9) C24 0.0424(12) 0.0342(11) 0.0223(9) 0.0108(8) 0.0021(8) 0.0125(9) C25 0.0444(12) 0.0320(11) 0.0260(10) 0.0138(8) 0.0097(9) 0.0054(9) C26 0.0298(10) 0.0263(9) 0.0247(9) 0.0071(7) 0.0050(7) 0.0007(8) C27 0.0252(9) 0.0208(8) 0.0166(8) 0.0044(7) 0.0046(7) 0.0065(7) C28 0.0290(10) 0.0252(9) 0.0210(8) 0.0025(7) 0.0028(7) 0.0043(8) C29 0.0392(11) 0.0273(10) 0.0218(9) -0.0017(8) 0.0035(8) 0.0076(8) C30 0.0375(11) 0.0359(11) 0.0241(9) 0.0071(8) 0.0108(8) 0.0155(9) C31 0.0257(10) 0.0393(11) 0.0305(10) 0.0115(9) 0.0090(8) 0.0066(8) C32 0.0279(10) 0.0266(9) 0.0231(9) 0.0046(7) 0.0047(7) 0.0038(8) C33 0.0257(9) 0.0253(9) 0.0161(8) 0.0060(7) 0.0039(7) 0.0037(7) C34 0.0265(9) 0.0283(10) 0.0238(9) 0.0080(7) 0.0031(7) -0.0007(8) C35 0.0327(10) 0.0288(10) 0.0295(10) 0.0145(8) 0.0067(8) 0.0040(8) C36 0.0319(10) 0.0396(11) 0.0196(8) 0.0131(8) 0.0038(7) 0.0055(9) C37 0.0415(12) 0.0350(11) 0.0172(8) 0.0052(8) -0.0016(8) -0.0015(9) C38 0.0413(11) 0.0251(9) 0.0178(8) 0.0061(7) 0.0017(8) 0.0014(8) C39 0.0230(9) 0.0238(9) 0.0190(8) 0.0037(7) 0.0041(7) 0.0039(7) C40 0.0237(9) 0.0272(9) 0.0173(8) 0.0037(7) 0.0038(7) 0.0003(7) C41 0.0354(10) 0.0242(9) 0.0172(8) 0.0022(7) 0.0073(7) 0.0022(8) C42 0.0310(11) 0.0317(11) 0.0393(11) 0.0013(9) 0.0167(9) 0.0063(9) C43 0.0220(10) 0.0465(14) 0.0638(17) -0.0107(12) 0.0087(11) 0.0021(10) C44 0.0258(10) 0.0379(12) 0.0399(12) -0.0107(9) 0.0006(9) 0.0017(9) N1 0.0219(7) 0.0240(8) 0.0157(7) 0.0032(6) 0.0029(5) 0.0031(6) N2 0.0231(7) 0.0210(7) 0.0146(6) 0.0031(6) 0.0045(5) 0.0038(6) N3 0.0234(7) 0.0222(7) 0.0150(7) 0.0025(6) 0.0016(6) 0.0017(6) N4 0.0256(8) 0.0268(8) 0.0140(7) 0.0035(6) 0.0044(6) 0.0064(6) O1 0.0488(9) 0.0289(7) 0.0272(7) 0.0107(6) 0.0088(6) 0.0087(7) N6 0.0690(14) 0.0374(11) 0.0248(9) 0.0115(8) 0.0183(9) 0.0311(10) N5 0.0355(9) 0.0249(8) 0.0205(7) 0.0022(6) 0.0020(7) 0.0061(7) _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 O2 C45 1.402(6) . ? O2 H2A 0.8400 . ? C45 C46 1.489(7) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? O3 C47 1.432(8) . ? O3 H3 0.8400 . ? C47 C48 1.487(9) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? O2B C45B 1.397(19) . ? O2B H2B 0.8400 . ? C45B C46B 1.466(15) . ? C45B H45C 0.9900 . ? C45B H45D 0.9900 . ? C46B H46D 0.9800 . ? C46B H46E 0.9800 . ? C46B H46F 0.9800 . ? O3B C47B 1.463(11) . ? O3B H3B 0.8400 . ? C47B C48B 1.492(8) . ? C47B H47C 0.9900 . ? C47B H47D 0.9900 . ? C48B H48D 0.9800 . ? C48B H48E 0.9800 . ? C48B H48F 0.9800 . ? C1 O1 1.274(2) . ? C1 N5 1.366(2) . ? C1 C2 1.458(3) . ? C2 N1 1.366(2) . ? C2 C3 1.398(2) . ? C3 C4 1.404(2) . ? C3 C21 1.497(2) . ? C4 N2 1.381(2) . ? C4 C5 1.425(2) . ? C5 C6 1.369(3) . ? C5 H5 0.9500 . ? C6 C7 1.426(2) . ? C6 H6 0.9500 . ? C7 N2 1.371(2) . ? C7 C8 1.411(3) . ? C8 C9 1.393(2) . ? C8 C27 1.500(2) . ? C9 N3 1.369(2) . ? C9 C10 1.512(3) . ? C10 C11 1.523(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.511(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N3 1.354(2) . ? C12 C13 1.407(2) . ? C13 C14 1.400(3) . ? C13 C33 1.499(2) . ? C14 N4 1.369(2) . ? C14 C15 1.433(2) . ? C15 C16 1.362(3) . ? C15 H15 0.9500 . ? C16 C17 1.430(2) . ? C16 H16 0.9500 . ? C17 N4 1.381(2) . ? C17 C18 1.388(3) . ? C18 C19 1.409(3) . ? C18 C39 1.496(2) . ? C19 N1 1.350(2) . ? C19 N5 1.423(2) . ? C21 C22 1.391(3) . ? C21 C26 1.392(3) . ? C22 C23 1.387(3) . ? C22 H22 0.9500 . ? C23 C24 1.387(3) . ? C23 H23 0.9500 . ? C24 C25 1.381(3) . ? C24 H24 0.9500 . ? C25 C26 1.387(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C32 1.392(3) . ? C27 C28 1.398(2) . ? C28 C29 1.394(3) . ? C28 H28 0.9500 . ? C29 C30 1.378(3) . ? C29 H29 0.9500 . ? C30 C31 1.388(3) . ? C30 H30 0.9500 . ? C31 C32 1.391(3) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C38 1.393(3) . ? C33 C34 1.394(3) . ? C34 C35 1.388(3) . ? C34 H34 0.9500 . ? C35 C36 1.388(3) . ? C35 H35 0.9500 . ? C36 C37 1.389(3) . ? C36 H36 0.9500 . ? C37 C38 1.388(3) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C39 C44 1.385(3) . ? C39 C40 1.393(2) . ? C40 C41 1.385(3) . ? C40 H40 0.9500 . ? C41 C42 1.374(3) . ? C41 H41 0.9500 . ? C42 C43 1.389(3) . ? C42 H42 0.9500 . ? C43 C44 1.391(3) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? N2 H2 0.8800 . ? N4 H4 0.8800 . ? N6 N5 1.361(2) . ? N6 H6A 0.859(17) . ? N6 H6B 0.906(17) . ? 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 O2 C45 C46 110.1(4) . . ? O2 C45 H45A 109.6 . . ? C46 C45 H45A 109.6 . . ? O2 C45 H45B 109.6 . . ? C46 C45 H45B 109.6 . . ? H45A C45 H45B 108.1 . . ? O3 C47 C48 108.6(6) . . ? O3 C47 H47A 110.0 . . ? C48 C47 H47A 110.0 . . ? O3 C47 H47B 110.0 . . ? C48 C47 H47B 110.0 . . ? H47A C47 H47B 108.4 . . ? C45B O2B H2B 109.5 . . ? O2B C45B C46B 113.7(10) . . ? O2B C45B H45C 108.8 . . ? C46B C45B H45C 108.8 . . ? O2B C45B H45D 108.8 . . ? C46B C45B H45D 108.8 . . ? H45C C45B H45D 107.7 . . ? C45B C46B H46D 109.5 . . ? C45B C46B H46E 109.5 . . ? H46D C46B H46E 109.5 . . ? C45B C46B H46F 109.5 . . ? H46D C46B H46F 109.5 . . ? H46E C46B H46F 109.5 . . ? C47B O3B H3B 109.5 . . ? O3B C47B C48B 107.1(7) . . ? O3B C47B H47C 110.3 . . ? C48B C47B H47C 110.3 . . ? O3B C47B H47D 110.3 . . ? C48B C47B H47D 110.3 . . ? H47C C47B H47D 108.6 . . ? C47B C48B H48D 109.5 . . ? C47B C48B H48E 109.5 . . ? H48D C48B H48E 109.5 . . ? C47B C48B H48F 109.5 . . ? H48D C48B H48F 109.5 . . ? H48E C48B H48F 109.5 . . ? O1 C1 N5 123.77(17) . . ? O1 C1 C2 131.13(17) . . ? N5 C1 C2 104.67(16) . . ? N1 C2 C3 126.53(16) . . ? N1 C2 C1 110.31(15) . . ? C3 C2 C1 123.12(16) . . ? C2 C3 C4 124.16(16) . . ? C2 C3 C21 118.58(16) . . ? C4 C3 C21 117.12(15) . . ? N2 C4 C3 126.49(15) . . ? N2 C4 C5 106.34(15) . . ? C3 C4 C5 127.09(17) . . ? C6 C5 C4 108.12(16) . . ? C6 C5 H5 125.9 . . ? C4 C5 H5 125.9 . . ? C5 C6 C7 108.41(15) . . ? C5 C6 H6 125.8 . . ? C7 C6 H6 125.8 . . ? N2 C7 C8 126.82(15) . . ? N2 C7 C6 106.41(15) . . ? C8 C7 C6 126.77(16) . . ? C9 C8 C7 126.95(16) . . ? C9 C8 C27 117.43(16) . . ? C7 C8 C27 115.61(15) . . ? N3 C9 C8 125.77(17) . . ? N3 C9 C10 112.32(15) . . ? C8 C9 C10 121.90(16) . . ? C9 C10 C11 103.10(15) . . ? C9 C10 H10A 111.1 . . ? C11 C10 H10A 111.1 . . ? C9 C10 H10B 111.1 . . ? C11 C10 H10B 111.1 . . ? H10A C10 H10B 109.1 . . ? C12 C11 C10 102.72(16) . . ? C12 C11 H11A 111.2 . . ? C10 C11 H11A 111.2 . . ? C12 C11 H11B 111.2 . . ? C10 C11 H11B 111.2 . . ? H11A C11 H11B 109.1 . . ? N3 C12 C13 125.35(17) . . ? N3 C12 C11 113.04(15) . . ? C13 C12 C11 121.61(16) . . ? C14 C13 C12 125.61(17) . . ? C14 C13 C33 115.44(15) . . ? C12 C13 C33 118.69(16) . . ? N4 C14 C13 127.80(16) . . ? N4 C14 C15 106.31(16) . . ? C13 C14 C15 125.88(17) . . ? C16 C15 C14 108.29(16) . . ? C16 C15 H15 125.9 . . ? C14 C15 H15 125.9 . . ? C15 C16 C17 108.44(16) . . ? C15 C16 H16 125.8 . . ? C17 C16 H16 125.8 . . ? N4 C17 C18 127.08(16) . . ? N4 C17 C16 106.00(16) . . ? C18 C17 C16 126.87(17) . . ? C17 C18 C19 124.11(16) . . ? C17 C18 C39 117.27(16) . . ? C19 C18 C39 118.62(17) . . ? N1 C19 C18 126.39(17) . . ? N1 C19 N5 110.50(16) . . ? C18 C19 N5 122.94(16) . . ? C22 C21 C26 118.76(17) . . ? C22 C21 C3 118.26(16) . . ? C26 C21 C3 122.97(17) . . ? C23 C22 C21 120.82(18) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C22 C23 C24 119.9(2) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C25 C24 C23 119.66(19) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 120.48(19) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 120.36(19) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? C32 C27 C28 118.86(17) . . ? C32 C27 C8 120.06(16) . . ? C28 C27 C8 121.08(16) . . ? C29 C28 C27 120.10(18) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C30 C29 C28 120.51(19) . . ? C30 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? C29 C30 C31 119.82(18) . . ? C29 C30 H30 120.1 . . ? C31 C30 H30 120.1 . . ? C30 C31 C32 120.03(19) . . ? C30 C31 H31 120.0 . . ? C32 C31 H31 120.0 . . ? C31 C32 C27 120.66(18) . . ? C31 C32 H32 119.7 . . ? C27 C32 H32 119.7 . . ? C38 C33 C34 118.68(17) . . ? C38 C33 C13 117.76(16) . . ? C34 C33 C13 123.57(16) . . ? C35 C34 C33 120.61(18) . . ? C35 C34 H34 119.7 . . ? C33 C34 H34 119.7 . . ? C34 C35 C36 120.42(18) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C35 C36 C37 119.26(18) . . ? C35 C36 H36 120.4 . . ? C37 C36 H36 120.4 . . ? C38 C37 C36 120.39(19) . . ? C38 C37 H37 119.8 . . ? C36 C37 H37 119.8 . . ? C37 C38 C33 120.63(18) . . ? C37 C38 H38 119.7 . . ? C33 C38 H38 119.7 . . ? C44 C39 C40 119.16(17) . . ? C44 C39 C18 120.23(17) . . ? C40 C39 C18 120.58(16) . . ? C41 C40 C39 120.62(18) . . ? C41 C40 H40 119.7 . . ? C39 C40 H40 119.7 . . ? C42 C41 C40 120.14(18) . . ? C42 C41 H41 119.9 . . ? C40 C41 H41 119.9 . . ? C41 C42 C43 119.68(19) . . ? C41 C42 H42 120.2 . . ? C43 C42 H42 120.2 . . ? C42 C43 C44 120.5(2) . . ? C42 C43 H43 119.8 . . ? C44 C43 H43 119.8 . . ? C39 C44 C43 119.9(2) . . ? C39 C44 H44 120.0 . . ? C43 C44 H44 120.0 . . ? C19 N1 C2 106.44(15) . . ? C7 N2 C4 110.68(14) . . ? C7 N2 H2 124.7 . . ? C4 N2 H2 124.7 . . ? C12 N3 C9 108.22(15) . . ? C14 N4 C17 110.88(15) . . ? C14 N4 H4 124.6 . . ? C17 N4 H4 124.6 . . ? C1 O1 H3B 128.8 . . ? C1 O1 H3 134.5 . . ? C1 O1 H2A 102.1 . . ? C1 O1 H2B 97.9 . . ? N5 N6 H6A 101(2) . . ? N5 N6 H6B 109(2) . . ? H6A N6 H6B 101(2) . . ? N6 N5 C1 123.93(17) . . ? N6 N5 C19 126.01(16) . . ? C1 N5 C19 107.97(15) . . ? 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 O1 C1 C2 N1 -169.8(2) . . . . ? N5 C1 C2 N1 2.6(2) . . . . ? O1 C1 C2 C3 12.4(3) . . . . ? N5 C1 C2 C3 -175.15(17) . . . . ? N1 C2 C3 C4 10.7(3) . . . . ? C1 C2 C3 C4 -171.86(17) . . . . ? N1 C2 C3 C21 -164.87(17) . . . . ? C1 C2 C3 C21 12.6(3) . . . . ? C2 C3 C4 N2 2.3(3) . . . . ? C21 C3 C4 N2 177.95(16) . . . . ? C2 C3 C4 C5 178.70(18) . . . . ? C21 C3 C4 C5 -5.7(3) . . . . ? N2 C4 C5 C6 1.3(2) . . . . ? C3 C4 C5 C6 -175.69(17) . . . . ? C4 C5 C6 C7 -0.5(2) . . . . ? C5 C6 C7 N2 -0.5(2) . . . . ? C5 C6 C7 C8 179.04(17) . . . . ? N2 C7 C8 C9 -7.7(3) . . . . ? C6 C7 C8 C9 172.92(18) . . . . ? N2 C7 C8 C27 171.39(16) . . . . ? C6 C7 C8 C27 -8.0(3) . . . . ? C7 C8 C9 N3 0.2(3) . . . . ? C27 C8 C9 N3 -178.90(16) . . . . ? C7 C8 C9 C10 -178.98(18) . . . . ? C27 C8 C9 C10 2.0(3) . . . . ? N3 C9 C10 C11 -5.9(2) . . . . ? C8 C9 C10 C11 173.35(17) . . . . ? C9 C10 C11 C12 7.3(2) . . . . ? C10 C11 C12 N3 -7.3(2) . . . . ? C10 C11 C12 C13 172.56(18) . . . . ? N3 C12 C13 C14 -4.5(3) . . . . ? C11 C12 C13 C14 175.61(18) . . . . ? N3 C12 C13 C33 169.40(17) . . . . ? C11 C12 C13 C33 -10.5(3) . . . . ? C12 C13 C14 N4 7.4(3) . . . . ? C33 C13 C14 N4 -166.67(17) . . . . ? C12 C13 C14 C15 -170.96(19) . . . . ? C33 C13 C14 C15 14.9(3) . . . . ? N4 C14 C15 C16 0.0(2) . . . . ? C13 C14 C15 C16 178.72(18) . . . . ? C14 C15 C16 C17 1.6(2) . . . . ? C15 C16 C17 N4 -2.6(2) . . . . ? C15 C16 C17 C18 175.15(19) . . . . ? N4 C17 C18 C19 -1.3(3) . . . . ? C16 C17 C18 C19 -178.57(19) . . . . ? N4 C17 C18 C39 179.43(17) . . . . ? C16 C17 C18 C39 2.2(3) . . . . ? C17 C18 C19 N1 -12.5(3) . . . . ? C39 C18 C19 N1 166.71(17) . . . . ? C17 C18 C19 N5 172.60(18) . . . . ? C39 C18 C19 N5 -8.2(3) . . . . ? C2 C3 C21 C22 67.4(2) . . . . ? C4 C3 C21 C22 -108.51(19) . . . . ? C2 C3 C21 C26 -113.1(2) . . . . ? C4 C3 C21 C26 71.0(2) . . . . ? C26 C21 C22 C23 -0.3(3) . . . . ? C3 C21 C22 C23 179.19(17) . . . . ? C21 C22 C23 C24 0.3(3) . . . . ? C22 C23 C24 C25 0.1(3) . . . . ? C23 C24 C25 C26 -0.4(3) . . . . ? C24 C25 C26 C21 0.3(3) . . . . ? C22 C21 C26 C25 0.0(3) . . . . ? C3 C21 C26 C25 -179.48(17) . . . . ? C9 C8 C27 C32 74.4(2) . . . . ? C7 C8 C27 C32 -104.8(2) . . . . ? C9 C8 C27 C28 -105.5(2) . . . . ? C7 C8 C27 C28 75.3(2) . . . . ? C32 C27 C28 C29 0.0(3) . . . . ? C8 C27 C28 C29 179.93(18) . . . . ? C27 C28 C29 C30 -0.2(3) . . . . ? C28 C29 C30 C31 0.4(3) . . . . ? C29 C30 C31 C32 -0.4(3) . . . . ? C30 C31 C32 C27 0.2(3) . . . . ? C28 C27 C32 C31 0.0(3) . . . . ? C8 C27 C32 C31 -179.93(17) . . . . ? C14 C13 C33 C38 64.8(2) . . . . ? C12 C13 C33 C38 -109.8(2) . . . . ? C14 C13 C33 C34 -115.3(2) . . . . ? C12 C13 C33 C34 70.1(2) . . . . ? C38 C33 C34 C35 0.2(3) . . . . ? C13 C33 C34 C35 -179.69(18) . . . . ? C33 C34 C35 C36 0.6(3) . . . . ? C34 C35 C36 C37 -0.8(3) . . . . ? C35 C36 C37 C38 0.2(3) . . . . ? C36 C37 C38 C33 0.6(3) . . . . ? C34 C33 C38 C37 -0.8(3) . . . . ? C13 C33 C38 C37 179.07(18) . . . . ? C17 C18 C39 C44 107.4(2) . . . . ? C19 C18 C39 C44 -71.9(3) . . . . ? C17 C18 C39 C40 -74.6(2) . . . . ? C19 C18 C39 C40 106.1(2) . . . . ? C44 C39 C40 C41 2.0(3) . . . . ? C18 C39 C40 C41 -176.15(17) . . . . ? C39 C40 C41 C42 -1.9(3) . . . . ? C40 C41 C42 C43 0.6(3) . . . . ? C41 C42 C43 C44 0.7(4) . . . . ? C40 C39 C44 C43 -0.6(4) . . . . ? C18 C39 C44 C43 177.5(2) . . . . ? C42 C43 C44 C39 -0.7(4) . . . . ? C18 C19 N1 C2 -172.45(18) . . . . ? N5 C19 N1 C2 2.9(2) . . . . ? C3 C2 N1 C19 174.25(18) . . . . ? C1 C2 N1 C19 -3.5(2) . . . . ? C8 C7 N2 C4 -178.19(17) . . . . ? C6 C7 N2 C4 1.31(19) . . . . ? C3 C4 N2 C7 175.39(17) . . . . ? C5 C4 N2 C7 -1.62(19) . . . . ? C13 C12 N3 C9 -176.04(18) . . . . ? C11 C12 N3 C9 3.8(2) . . . . ? C8 C9 N3 C12 -177.71(17) . . . . ? C10 C9 N3 C12 1.5(2) . . . . ? C13 C14 N4 C17 179.63(18) . . . . ? C15 C14 N4 C17 -1.7(2) . . . . ? C18 C17 N4 C14 -175.06(18) . . . . ? C16 C17 N4 C14 2.7(2) . . . . ? N5 C1 O1 H3B 29.6 . . . . ? C2 C1 O1 H3B -159.2 . . . . ? N5 C1 O1 H3 20.1 . . . . ? C2 C1 O1 H3 -168.7 . . . . ? N5 C1 O1 H2A 21.2 . . . . ? C2 C1 O1 H2A -167.7 . . . . ? N5 C1 O1 H2B 21.7 . . . . ? C2 C1 O1 H2B -167.1 . . . . ? O1 C1 N5 N6 8.0(3) . . . . ? C2 C1 N5 N6 -165.2(2) . . . . ? O1 C1 N5 C19 172.36(18) . . . . ? C2 C1 N5 C19 -0.8(2) . . . . ? N1 C19 N5 N6 162.7(2) . . . . ? C18 C19 N5 N6 -21.8(3) . . . . ? N1 C19 N5 C1 -1.3(2) . . . . ? C18 C19 N5 C1 174.27(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N6 H6B N3 0.906(17) 2.60(2) 3.322(3) 137(2) 2_566 N6 H6A O2 0.859(17) 2.33(3) 2.978(5) 133(3) . N6 H6A O2B 0.859(17) 2.11(3) 2.769(15) 134(3) . N4 H4 N3 0.88 2.41 2.947(2) 119.4 . N4 H4 N1 0.88 2.37 2.913(2) 120.3 . N2 H2 N3 0.88 2.45 2.982(2) 119.6 . N2 H2 N1 0.88 2.36 2.907(2) 120.9 . O3B H3B O1 0.84 1.89 2.719(12) 168.4 . O3 H3 O1 0.84 2.10 2.881(8) 153.6 . O2B H2B O3 0.84 2.23 2.892(16) 135.5 . O2 H2A O3B 0.84 2.02 2.854(12) 169.4 . O2B H2B O3B 0.84 2.56 3.212(18) 135.3 . O2 H2A O3 0.84 1.69 2.527(9) 173.3 . _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.408 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.059 # Attachment '- CC-5-19-2011(compounds 6,7,8).cif' data_11mz020_0m _database_code_depnum_ccdc_archive 'CCDC 821400' #TrackingRef '- CC-5-19-2011(compounds 6,7,8).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H29 N5 O' _chemical_formula_weight 631.71 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3503(15) _cell_length_b 10.384(3) _cell_length_c 12.353(3) _cell_angle_alpha 94.720(4) _cell_angle_beta 99.884(4) _cell_angle_gamma 100.532(4) _cell_volume 783.5(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 940 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 26.19 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 330 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6366 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'Apex2 v2009.7-0 (Bruker, 2009)' _exptl_special_details ; Reflection 0 0 1 was obstructed by the beam stop and was omitted from the refinement. The lactame moiety is disordered over four mutually exclusive positions with both of the pyrrole moieties, and across the crystallographic inversion centers. Occupancies for the four sites are 0.2353(15) for the A moiety, 0.118(2) for the B moiety, 0.108(2) for the C moiety, and 0.039(3) for the D moiety, thus summing up to 50% occupancy. The second half of the lactame moiety is created by the crystallographic inversion center. The remainder of each site is occupied by the three purrole units. Moieties A and B, and C and D each occupy the same sites but are flip disordered with each other. Overallping atoms in the disordered sites were constrained to have identical ADPs and identical positions (exceptions: atoms C7B and C3D whoose positions were allowed to refine but which were restrained to be in plane with their three next neighbor atoms and to have covalent bond lengths similar to those of the atoms of the other moieties they are disordered with). The ADPs of the oxygen atoms were constrained to be identical to those of the carbon atoms they are bonded to. The oxygen atoms of the four moieties were restrained to have similar C-O bond lengths and N...O distances. The largest residual electron density is located at the center of inversion in the middle of the molecule. The reduction of the hydrazine amide to the amide was accomplished using Raney Ni/SmI3, so some Ni might have been incorporated into the porphyrine like structure. Inclusion of a partially occuopied Ni atom resulted in marginally lower R values and an occupancy of 1.3% Ni at the center of the molecule. ; _diffrn_ambient_temperature 100(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 AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 8429 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0613 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3844 _reflns_number_gt 2446 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2009.7-0 (Bruker, 2009)' _computing_cell_refinement 'Apex2 v2009.7-0' _computing_data_reduction 'Apex2 v2009.7-0' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0695P)^2^+0.2590P] 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 3844 _refine_ls_number_parameters 247 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0984 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1591 _refine_ls_wR_factor_gt 0.1440 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.002 _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 0.4773(3) 1.0803(2) 0.74422(17) 0.0273(5) Uani 1 1 d . . . C2 C 0.3550(4) 1.0390(2) 0.82652(18) 0.0337(5) Uani 0.853(2) 1 d PD A 1 H2 H 0.3905 1.0708 0.9031 0.040 Uiso 0.853(2) 1 calc PR A 1 C3 C 0.1786(4) 0.9458(2) 0.77540(18) 0.0320(5) Uani 0.853(2) 1 d PD A 1 H3 H 0.0696 0.9003 0.8101 0.038 Uiso 0.853(2) 1 calc PR A 1 C2C C 0.3550(4) 1.0390(2) 0.82652(18) 0.0337(5) Uani 0.108(2) 1 d PD A 2 N3C N 0.1786(4) 0.9458(2) 0.77540(18) 0.0320(5) Uani 0.108(2) 1 d PD A 2 H3C H 0.0776 0.9036 0.8076 0.038 Uiso 0.108(2) 1 calc PR A 2 O1C O 0.395(2) 1.0469(13) 0.9291(8) 0.0337(5) Uani 0.108(2) 1 d PD A 2 N3D N 0.3550(4) 1.0390(2) 0.82652(18) 0.0337(5) Uani 0.039(3) 1 d PD A 3 H3D H 0.3949 1.0607 0.8985 0.040 Uiso 0.039(3) 1 calc PR A 3 C3D C 0.165(3) 0.960(2) 0.7723(15) 0.0320(5) Uani 0.039(3) 1 d PD A 3 O1D O 0.025(3) 0.934(3) 0.829(3) 0.0320(5) Uani 0.039(3) 1 d PD A 3 C4 C 0.1862(3) 0.92846(19) 0.66061(17) 0.0257(5) Uani 1 1 d D . . C5 C 0.0429(3) 0.83409(19) 0.58123(17) 0.0254(4) Uani 1 1 d . A . C6 C 0.0646(3) 0.80970(19) 0.47061(17) 0.0254(4) Uani 1 1 d D . . C7 C -0.0952(5) 0.7193(3) 0.3907(2) 0.0317(6) Uani 0.647(2) 1 d P A 1 H7 H -0.2283 0.6695 0.4030 0.038 Uiso 0.647(2) 1 calc PR A 1 C8 C -0.0215(3) 0.7178(2) 0.29347(17) 0.0332(5) Uani 0.647(2) 1 d P A 1 H8 H -0.0934 0.6675 0.2251 0.040 Uiso 0.647(2) 1 calc PR A 1 N3A N -0.0952(5) 0.7193(3) 0.3907(2) 0.0317(6) Uani 0.2353(15) 1 d PD A 2 H3A H -0.2185 0.6732 0.4021 0.038 Uiso 0.2353(15) 1 calc PR A 2 C8A C -0.0215(3) 0.7178(2) 0.29347(17) 0.0332(5) Uani 0.2353(15) 1 d PD A 2 O1A O -0.1354(10) 0.6375(6) 0.2183(5) 0.0332(5) Uani 0.2353(15) 1 d PD A 2 C7B C -0.105(3) 0.735(2) 0.3853(14) 0.0317(6) Uani 0.118(2) 1 d PD A 3 N3B N -0.0215(3) 0.7178(2) 0.29347(17) 0.0332(5) Uani 0.118(2) 1 d PD A 3 H3B H -0.0813 0.6632 0.2333 0.040 Uiso 0.118(2) 1 calc PR A 3 O1B O -0.2998(17) 0.6884(12) 0.3720(10) 0.0317(6) Uani 0.118(2) 1 d PD A 3 C9 C 0.1878(3) 0.8077(2) 0.31459(17) 0.0270(5) Uani 1 1 d D . . C10 C 0.3207(3) 0.8317(2) 0.23586(16) 0.0268(5) Uani 1 1 d . . . C11 C -0.1394(3) 0.7471(2) 0.61847(16) 0.0260(5) Uani 1 1 d . . . C12 C -0.1524(3) 0.6111(2) 0.61007(18) 0.0300(5) Uani 1 1 d . A . H12 H -0.0459 0.5740 0.5800 0.036 Uiso 1 1 calc R . . C13 C -0.3194(4) 0.5296(2) 0.64523(19) 0.0351(5) Uani 1 1 d . . . H13 H -0.3287 0.4368 0.6376 0.042 Uiso 1 1 calc R A . C14 C -0.4721(4) 0.5827(2) 0.69118(18) 0.0328(5) Uani 1 1 d . A . H14 H -0.5849 0.5268 0.7165 0.039 Uiso 1 1 calc R . . C15 C -0.4608(4) 0.7175(2) 0.70036(19) 0.0343(5) Uani 1 1 d . . . H15 H -0.5660 0.7542 0.7320 0.041 Uiso 1 1 calc R A . C16 C -0.2960(3) 0.7994(2) 0.66353(18) 0.0308(5) Uani 1 1 d . A . H16 H -0.2903 0.8918 0.6692 0.037 Uiso 1 1 calc R . . C17 C 0.2418(3) 0.7614(2) 0.12116(17) 0.0308(5) Uani 1 1 d . . . C18 C 0.0485(4) 0.7785(2) 0.05643(19) 0.0388(6) Uani 1 1 d . A . H18 H -0.0337 0.8369 0.0843 0.047 Uiso 1 1 calc R . . C19 C -0.0239(4) 0.7100(3) -0.0490(2) 0.0492(7) Uani 1 1 d . . . H19 H -0.1570 0.7206 -0.0924 0.059 Uiso 1 1 calc R A . C20 C 0.0961(5) 0.6270(3) -0.0907(2) 0.0519(7) Uani 1 1 d . A . H20 H 0.0460 0.5806 -0.1628 0.062 Uiso 1 1 calc R . . C21 C 0.2875(5) 0.6113(2) -0.0285(2) 0.0488(7) Uani 1 1 d . . . H21 H 0.3710 0.5548 -0.0579 0.059 Uiso 1 1 calc R A . C22 C 0.3605(4) 0.6773(2) 0.07734(19) 0.0399(6) Uani 1 1 d . A . H22 H 0.4929 0.6648 0.1202 0.048 Uiso 1 1 calc R . . N1 N 0.3685(3) 1.01228(16) 0.64412(14) 0.0259(4) Uani 1 1 d . A . H1 H 0.4090 1.0211 0.5801 0.031 Uiso 0.5690(16) 1 calc PR . . N2 N 0.2335(3) 0.86252(16) 0.42285(13) 0.0250(4) Uani 1 1 d . A . H2A H 0.3503 0.9210 0.4555 0.030 Uiso 0.4310(16) 1 calc PR . . 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 0.0259(11) 0.0255(10) 0.0279(11) -0.0010(8) 0.0012(8) 0.0038(9) C2 0.0343(12) 0.0373(12) 0.0266(10) -0.0011(9) 0.0045(9) 0.0030(10) C3 0.0278(11) 0.0341(12) 0.0318(11) 0.0018(9) 0.0070(9) 0.0005(9) C2C 0.0343(12) 0.0373(12) 0.0266(10) -0.0011(9) 0.0045(9) 0.0030(10) N3C 0.0278(11) 0.0341(12) 0.0318(11) 0.0018(9) 0.0070(9) 0.0005(9) O1C 0.0343(12) 0.0373(12) 0.0266(10) -0.0011(9) 0.0045(9) 0.0030(10) N3D 0.0343(12) 0.0373(12) 0.0266(10) -0.0011(9) 0.0045(9) 0.0030(10) C3D 0.0278(11) 0.0341(12) 0.0318(11) 0.0018(9) 0.0070(9) 0.0005(9) O1D 0.0278(11) 0.0341(12) 0.0318(11) 0.0018(9) 0.0070(9) 0.0005(9) C4 0.0245(11) 0.0228(10) 0.0294(11) 0.0043(8) 0.0038(8) 0.0042(8) C5 0.0226(10) 0.0232(10) 0.0299(11) 0.0048(8) 0.0024(8) 0.0046(8) C6 0.0213(10) 0.0229(10) 0.0300(11) 0.0034(8) 0.0012(8) 0.0026(8) C7 0.0213(10) 0.0290(13) 0.0409(12) 0.0000(10) 0.0048(9) -0.0018(9) C8 0.0289(11) 0.0346(11) 0.0292(11) -0.0037(8) -0.0028(8) -0.0002(9) N3A 0.0213(10) 0.0290(13) 0.0409(12) 0.0000(10) 0.0048(9) -0.0018(9) C8A 0.0289(11) 0.0346(11) 0.0292(11) -0.0037(8) -0.0028(8) -0.0002(9) O1A 0.0289(11) 0.0346(11) 0.0292(11) -0.0037(8) -0.0028(8) -0.0002(9) C7B 0.0213(10) 0.0290(13) 0.0409(12) 0.0000(10) 0.0048(9) -0.0018(9) N3B 0.0289(11) 0.0346(11) 0.0292(11) -0.0037(8) -0.0028(8) -0.0002(9) O1B 0.0213(10) 0.0290(13) 0.0409(12) 0.0000(10) 0.0048(9) -0.0018(9) C9 0.0262(11) 0.0251(10) 0.0269(10) 0.0007(8) 0.0000(8) 0.0038(8) C10 0.0276(11) 0.0242(10) 0.0261(10) 0.0011(8) 0.0001(8) 0.0038(8) C11 0.0228(10) 0.0266(10) 0.0255(10) 0.0039(8) -0.0001(8) 0.0010(8) C12 0.0285(11) 0.0255(11) 0.0356(12) 0.0041(9) 0.0053(9) 0.0049(9) C13 0.0361(13) 0.0237(11) 0.0415(13) 0.0054(9) 0.0032(10) -0.0011(9) C14 0.0268(11) 0.0342(12) 0.0325(12) 0.0077(9) 0.0023(9) -0.0049(9) C15 0.0254(11) 0.0412(13) 0.0371(12) 0.0060(10) 0.0067(9) 0.0073(10) C16 0.0278(11) 0.0270(11) 0.0374(12) 0.0050(9) 0.0053(9) 0.0055(9) C17 0.0309(12) 0.0315(11) 0.0241(11) 0.0002(9) 0.0034(9) -0.0060(9) C18 0.0356(13) 0.0432(13) 0.0316(12) 0.0071(10) 0.0007(10) -0.0031(11) C19 0.0470(15) 0.0552(16) 0.0321(13) 0.0163(12) -0.0088(11) -0.0134(13) C20 0.074(2) 0.0435(15) 0.0242(12) -0.0028(11) 0.0011(12) -0.0143(14) C21 0.0704(19) 0.0376(14) 0.0333(13) -0.0058(11) 0.0098(13) 0.0017(13) C22 0.0466(15) 0.0352(12) 0.0331(12) -0.0028(10) 0.0039(11) 0.0021(11) N1 0.0233(9) 0.0238(9) 0.0277(9) 0.0019(7) 0.0018(7) 0.0006(7) N2 0.0236(9) 0.0227(8) 0.0265(9) 0.0037(7) 0.0005(7) 0.0023(7) _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 1.375(3) . ? C1 C10 1.403(3) 2_676 ? C1 C2 1.429(3) . ? C2 C3 1.361(3) . ? C2 H2 0.9500 . ? C3 C4 1.425(3) . ? C3 H3 0.9500 . ? C3D O1D 1.229(17) . ? C3D C4 1.425(18) . ? C4 N1 1.371(3) . ? C4 C5 1.400(3) . ? C5 C6 1.404(3) . ? C5 C11 1.496(3) . ? C6 N2 1.362(3) . ? C6 C7 1.428(4) . ? C6 C7B 1.430(16) . ? C7 C8 1.362(4) . ? C7 H7 0.9500 . ? C8 C9 1.446(3) . ? C8 H8 0.9500 . ? C7B O1B 1.219(15) . ? C9 N2 1.370(3) . ? C9 C10 1.402(3) . ? C10 C1 1.403(3) 2_676 ? C10 C17 1.498(3) . ? C11 C16 1.390(3) . ? C11 C12 1.393(3) . ? C12 C13 1.386(3) . ? C12 H12 0.9500 . ? C13 C14 1.378(3) . ? C13 H13 0.9500 . ? C14 C15 1.383(3) . ? C14 H14 0.9500 . ? C15 C16 1.388(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.388(3) . ? C17 C18 1.394(3) . ? C18 C19 1.392(3) . ? C18 H18 0.9500 . ? C19 C20 1.375(4) . ? C19 H19 0.9500 . ? C20 C21 1.366(4) . ? C20 H20 0.9500 . ? C21 C22 1.386(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? N1 H1 0.8800 . ? N2 H2A 0.8800 . ? 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 C10 126.48(19) . 2_676 ? N1 C1 C2 107.81(18) . . ? C10 C1 C2 125.59(19) 2_676 . ? C3 C2 C1 107.59(19) . . ? C3 C2 H2 126.2 . . ? C1 C2 H2 126.2 . . ? C2 C3 C4 108.0(2) . . ? C2 C3 H3 126.0 . . ? C4 C3 H3 126.0 . . ? O1D C3D C4 137(2) . . ? N1 C4 C5 126.34(19) . . ? N1 C4 C3 107.89(18) . . ? C5 C4 C3 125.5(2) . . ? N1 C4 C3D 107.0(8) . . ? C5 C4 C3D 126.6(8) . . ? C4 C5 C6 124.92(19) . . ? C4 C5 C11 117.64(18) . . ? C6 C5 C11 117.34(17) . . ? N2 C6 C5 127.56(18) . . ? N2 C6 C7 109.72(19) . . ? C5 C6 C7 122.7(2) . . ? N2 C6 C7B 108.1(7) . . ? C5 C6 C7B 123.9(7) . . ? C8 C7 C6 107.3(2) . . ? C8 C7 H7 126.3 . . ? C6 C7 H7 126.3 . . ? C7 C8 C9 106.6(2) . . ? C7 C8 H8 126.7 . . ? C9 C8 H8 126.7 . . ? O1B C7B C6 138.5(15) . . ? N2 C9 C10 126.47(18) . . ? N2 C9 C8 108.99(18) . . ? C10 C9 C8 124.53(18) . . ? C1 C10 C9 124.68(19) 2_676 . ? C1 C10 C17 116.85(19) 2_676 . ? C9 C10 C17 118.46(18) . . ? C16 C11 C12 118.73(19) . . ? C16 C11 C5 121.23(18) . . ? C12 C11 C5 120.03(19) . . ? C13 C12 C11 120.6(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 120.2(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 119.9(2) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 120.2(2) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.5(2) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C22 C17 C18 118.7(2) . . ? C22 C17 C10 120.3(2) . . ? C18 C17 C10 121.0(2) . . ? C19 C18 C17 120.0(2) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 120.4(2) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 120.0(2) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 120.4(3) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C22 C17 120.6(2) . . ? C21 C22 H22 119.7 . . ? C17 C22 H22 119.7 . . ? C4 N1 C1 108.73(17) . . ? C4 N1 H1 125.6 . . ? C1 N1 H1 125.6 . . ? C6 N2 C9 107.33(16) . . ? C6 N2 H2A 126.3 . . ? C9 N2 H2A 126.3 . . ? 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 1.2(3) . . . . ? C10 C1 C2 C3 -175.1(2) 2_676 . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? C2 C3 C4 N1 -0.1(3) . . . . ? C2 C3 C4 C5 174.8(2) . . . . ? C2 C3 C4 C3D -84(6) . . . . ? O1D C3D C4 N1 167(3) . . . . ? O1D C3D C4 C5 -10(3) . . . . ? O1D C3D C4 C3 -95(7) . . . . ? N1 C4 C5 C6 0.4(3) . . . . ? C3 C4 C5 C6 -173.6(2) . . . . ? C3D C4 C5 C6 177.4(14) . . . . ? N1 C4 C5 C11 176.47(18) . . . . ? C3 C4 C5 C11 2.5(3) . . . . ? C3D C4 C5 C11 -6.5(14) . . . . ? C4 C5 C6 N2 6.3(3) . . . . ? C11 C5 C6 N2 -169.82(19) . . . . ? C4 C5 C6 C7 -175.0(2) . . . . ? C11 C5 C6 C7 8.8(3) . . . . ? C4 C5 C6 C7B -165.5(11) . . . . ? C11 C5 C6 C7B 18.4(11) . . . . ? N2 C6 C7 C8 0.0(3) . . . . ? C5 C6 C7 C8 -178.9(2) . . . . ? C7B C6 C7 C8 80(5) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? N2 C6 C7B O1B -163(2) . . . . ? C5 C6 C7B O1B 10(3) . . . . ? C7 C6 C7B O1B 94(6) . . . . ? C7 C8 C9 N2 -0.9(3) . . . . ? C7 C8 C9 C10 178.3(2) . . . . ? N2 C9 C10 C1 -1.5(3) . . . 2_676 ? C8 C9 C10 C1 179.4(2) . . . 2_676 ? N2 C9 C10 C17 179.77(19) . . . . ? C8 C9 C10 C17 0.7(3) . . . . ? C4 C5 C11 C16 60.7(3) . . . . ? C6 C5 C11 C16 -122.8(2) . . . . ? C4 C5 C11 C12 -118.2(2) . . . . ? C6 C5 C11 C12 58.3(3) . . . . ? C16 C11 C12 C13 0.5(3) . . . . ? C5 C11 C12 C13 179.4(2) . . . . ? C11 C12 C13 C14 -1.4(3) . . . . ? C12 C13 C14 C15 1.2(3) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C11 -0.8(3) . . . . ? C12 C11 C16 C15 0.6(3) . . . . ? C5 C11 C16 C15 -178.29(19) . . . . ? C1 C10 C17 C22 61.9(3) 2_676 . . . ? C9 C10 C17 C22 -119.3(2) . . . . ? C1 C10 C17 C18 -118.2(2) 2_676 . . . ? C9 C10 C17 C18 60.6(3) . . . . ? C22 C17 C18 C19 1.2(3) . . . . ? C10 C17 C18 C19 -178.6(2) . . . . ? C17 C18 C19 C20 -1.1(4) . . . . ? C18 C19 C20 C21 0.1(4) . . . . ? C19 C20 C21 C22 0.8(4) . . . . ? C20 C21 C22 C17 -0.7(4) . . . . ? C18 C17 C22 C21 -0.3(3) . . . . ? C10 C17 C22 C21 179.6(2) . . . . ? C5 C4 N1 C1 -174.01(19) . . . . ? C3 C4 N1 C1 0.8(2) . . . . ? C3D C4 N1 C1 8.5(12) . . . . ? C10 C1 N1 C4 175.0(2) 2_676 . . . ? C2 C1 N1 C4 -1.2(2) . . . . ? C5 C6 N2 C9 178.24(19) . . . . ? C7 C6 N2 C9 -0.6(2) . . . . ? C7B C6 N2 C9 -8.9(10) . . . . ? C10 C9 N2 C6 -178.3(2) . . . . ? C8 C9 N2 C6 0.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.826 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.051 # start Validation Reply Form _vrf_PLAT430_11mz020_0m ; PROBLEM: Short Inter D...A Contact O1C .. O1C .. 2.40 Ang. RESPONSE: O1C is only partially occupied with an occupancy rate of 10.8(2) %. ; _vrf_DIFMX01_11mz020_0m ; PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00 RESPONSE: The largest residual electron density is located at the center of inversion in the middle of the molecule. The reduction of the hydrazine amide to the amide was accomplished using Raney Ni/SmI3, so some Ni might have been incorporated into the porphyrine like structure. Inclusion of a partially occuopied Ni atom resulted in marginally lower R values and an occupancy of 1.3% Ni at the center of the molecule. ; _vrf_PLAT097_11mz020_0m ; PROBLEM: Large Reported Max. (Positive) Residual Density RESPONSE: The largest residual electron density is located at the center of inversion in the middle of the molecule. The reduction of the hydrazine amide to the amide was accomplished using Raney Ni/SmI3, so some Ni might have been incorporated into the porphyrine like structure. Inclusion of a partially occuopied Ni atom resulted in marginally lower R values and an occupancy of 1.3% Ni at the center of the molecule. ;