# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email cmukhop@yahoo.co.in _publ_contact_author_name 'Chhanda Mukhopadhyay' loop_ _publ_author_name 'Chhanda Mukhopadhyay' 'Paramita Das' 'Ray Butcher' # Attachment '- Supporting information 8 (CIF File of compound 5cb).cif' data_5cb _database_code_depnum_ccdc_archive 'CCDC 812619' #TrackingRef '- Supporting information 8 (CIF File of compound 5cb).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H19 N3' _chemical_formula_weight 301.38 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4865(4) _cell_length_b 9.9343(4) _cell_length_c 10.5514(5) _cell_angle_alpha 114.009(2) _cell_angle_beta 113.796(2) _cell_angle_gamma 90.405(2) _cell_volume 813.50(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 29.14 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9912 _exptl_absorpt_correction_T_max 0.9970 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12886 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 29.31 _reflns_number_total 4320 _reflns_number_gt 3149 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0785P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4320 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1610 _refine_ls_wR_factor_gt 0.1486 _refine_ls_goodness_of_fit_ref 1.290 _refine_ls_restrained_S_all 1.290 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.46431(17) 0.88119(15) 0.60900(15) 0.0479(3) Uani 1 1 d . . . N1 N 0.52197(19) 1.00368(15) 0.65597(15) 0.0728(4) Uani 1 1 d . . . C2 C 0.38811(14) 0.72830(13) 0.54888(14) 0.0383(3) Uani 1 1 d . . . N2 N -0.00267(16) 0.37225(13) 0.04962(14) 0.0582(4) Uani 1 1 d . . . N3 N 0.26330(14) 0.71419(13) 0.29285(13) 0.0511(3) Uani 1 1 d . . . H3A H 0.1971 0.6660 0.1966 0.061 Uiso 1 1 calc R . . H3B H 0.3161 0.8026 0.3277 0.061 Uiso 1 1 calc R . . C6 C 0.22107(14) 0.44082(13) 0.43794(14) 0.0355(3) Uani 1 1 d . . . C7 C 0.12296(14) 0.28958(13) 0.37539(14) 0.0377(3) Uani 1 1 d . . . C8 C 0.02112(16) 0.27187(14) 0.43486(16) 0.0450(3) Uani 1 1 d . . . H6 H 0.0098 0.3556 0.5100 0.054 Uiso 1 1 calc R . . C9 C -0.06364(16) 0.13070(15) 0.38313(16) 0.0479(3) Uani 1 1 d . . . H7 H -0.1307 0.1212 0.4247 0.057 Uiso 1 1 calc R . . C10 C -0.05077(16) 0.00320(14) 0.27072(15) 0.0457(3) Uani 1 1 d . . . C11 C -0.1390(2) -0.15011(16) 0.22027(19) 0.0635(4) Uani 1 1 d . . . H9A H -0.1768 -0.2085 0.1105 0.095 Uiso 1 1 calc R . . H9B H -0.2265 -0.1395 0.2449 0.095 Uiso 1 1 calc R . . H9C H -0.0699 -0.2000 0.2732 0.095 Uiso 1 1 calc R . . C5 C 0.08702(16) 0.42852(13) 0.17759(15) 0.0414(3) Uani 1 1 d . . . C14 C 0.32941(15) 0.51779(13) 0.59373(14) 0.0371(3) Uani 1 1 d . . . C15 C 0.41132(15) 0.66409(14) 0.65018(14) 0.0380(3) Uani 1 1 d . . . C16 C 0.51797(16) 0.75505(15) 0.82080(14) 0.0462(3) Uani 1 1 d . . . H14A H 0.5729 0.8477 0.8371 0.055 Uiso 1 1 calc R . . H14B H 0.5963 0.6988 0.8538 0.055 Uiso 1 1 calc R . . C17 C 0.43105(18) 0.79426(15) 0.92231(16) 0.0504(4) Uani 1 1 d . . . H15A H 0.4943 0.8830 1.0186 0.060 Uiso 1 1 calc R . . H15B H 0.3328 0.8198 0.8698 0.060 Uiso 1 1 calc R . . C18 C 0.39494(19) 0.66946(16) 0.96039(16) 0.0550(4) Uani 1 1 d . . . H16A H 0.4936 0.6478 1.0177 0.066 Uiso 1 1 calc R . . H16B H 0.3439 0.7062 1.0276 0.066 Uiso 1 1 calc R . . C19 C 0.29148(18) 0.52409(15) 0.82121(15) 0.0515(4) Uani 1 1 d . . . H17A H 0.1901 0.5443 0.7677 0.062 Uiso 1 1 calc R . . H17B H 0.2738 0.4532 0.8575 0.062 Uiso 1 1 calc R . . C20 C 0.35877(16) 0.45052(14) 0.70566(15) 0.0444(3) Uani 1 1 d . . . H18A H 0.4713 0.4610 0.7624 0.053 Uiso 1 1 calc R . . H18B H 0.3122 0.3438 0.6471 0.053 Uiso 1 1 calc R . . C12 C 0.04740(19) 0.02232(15) 0.20938(17) 0.0545(4) Uani 1 1 d . . . H19 H 0.0564 -0.0610 0.1322 0.065 Uiso 1 1 calc R . . C13 C 0.13269(18) 0.16291(14) 0.26036(17) 0.0505(4) Uani 1 1 d . . . H20 H 0.1976 0.1724 0.2166 0.061 Uiso 1 1 calc R . . C4 C 0.20020(14) 0.50606(13) 0.33704(14) 0.0363(3) Uani 1 1 d . . . C3 C 0.28431(14) 0.65088(13) 0.38927(14) 0.0370(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0559(8) 0.0456(8) 0.0339(7) 0.0189(6) 0.0117(6) -0.0099(6) N1 0.0976(11) 0.0515(8) 0.0490(7) 0.0216(6) 0.0158(7) -0.0246(7) C2 0.0414(7) 0.0372(6) 0.0340(6) 0.0161(5) 0.0148(5) -0.0019(5) N2 0.0732(9) 0.0473(7) 0.0365(7) 0.0147(6) 0.0128(6) -0.0067(6) N3 0.0629(8) 0.0454(6) 0.0353(6) 0.0210(5) 0.0105(5) -0.0115(5) C6 0.0415(7) 0.0305(6) 0.0356(6) 0.0138(5) 0.0192(5) 0.0053(5) C7 0.0431(7) 0.0326(6) 0.0354(6) 0.0163(5) 0.0147(6) 0.0024(5) C8 0.0505(8) 0.0374(7) 0.0456(7) 0.0146(6) 0.0243(6) 0.0037(5) C9 0.0443(7) 0.0496(8) 0.0507(8) 0.0243(7) 0.0203(6) -0.0008(6) C10 0.0487(8) 0.0378(7) 0.0396(7) 0.0186(6) 0.0086(6) -0.0035(5) C11 0.0692(10) 0.0458(8) 0.0578(9) 0.0212(7) 0.0146(8) -0.0137(7) C5 0.0506(7) 0.0360(6) 0.0354(7) 0.0153(5) 0.0181(6) 0.0007(5) C14 0.0416(7) 0.0348(6) 0.0368(6) 0.0180(5) 0.0173(5) 0.0054(5) C15 0.0400(6) 0.0381(6) 0.0336(6) 0.0166(5) 0.0137(5) 0.0003(5) C16 0.0486(7) 0.0462(7) 0.0346(7) 0.0196(6) 0.0089(6) -0.0076(6) C17 0.0653(9) 0.0436(7) 0.0333(7) 0.0155(6) 0.0158(6) -0.0023(6) C18 0.0703(10) 0.0535(8) 0.0393(8) 0.0223(7) 0.0214(7) -0.0037(7) C19 0.0622(9) 0.0501(8) 0.0424(8) 0.0250(7) 0.0196(7) -0.0047(6) C20 0.0502(8) 0.0391(7) 0.0417(7) 0.0231(6) 0.0136(6) 0.0029(5) C12 0.0780(10) 0.0326(7) 0.0479(8) 0.0101(6) 0.0318(8) 0.0012(6) C13 0.0687(9) 0.0372(7) 0.0526(8) 0.0173(6) 0.0364(8) 0.0046(6) C4 0.0422(7) 0.0327(6) 0.0318(6) 0.0125(5) 0.0165(5) 0.0016(5) C3 0.0418(7) 0.0354(6) 0.0335(6) 0.0157(5) 0.0162(5) 0.0014(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.1431(17) . ? C1 C2 1.4360(16) . ? C2 C15 1.4017(16) . ? C2 C3 1.4122(17) . ? N2 C5 1.1452(17) . ? N3 C3 1.3525(15) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? C6 C14 1.3949(18) . ? C6 C4 1.4092(16) . ? C6 C7 1.4956(15) . ? C7 C13 1.3836(18) . ? C7 C8 1.3910(17) . ? C8 C9 1.3850(17) . ? C8 H6 0.9300 . ? C9 C10 1.386(2) . ? C9 H7 0.9300 . ? C10 C12 1.3807(19) . ? C10 C11 1.5053(17) . ? C11 H9A 0.9600 . ? C11 H9B 0.9600 . ? C11 H9C 0.9600 . ? C5 C4 1.4328(17) . ? C14 C15 1.4060(16) . ? C14 C20 1.5161(16) . ? C15 C16 1.5082(17) . ? C16 C17 1.535(2) . ? C16 H14A 0.9700 . ? C16 H14B 0.9700 . ? C17 C18 1.5253(17) . ? C17 H15A 0.9700 . ? C17 H15B 0.9700 . ? C18 C19 1.515(2) . ? C18 H16A 0.9700 . ? C18 H16B 0.9700 . ? C19 C20 1.5289(19) . ? C19 H17A 0.9700 . ? C19 H17B 0.9700 . ? C20 H18A 0.9700 . ? C20 H18B 0.9700 . ? C12 C13 1.3842(18) . ? C12 H19 0.9300 . ? C13 H20 0.9300 . ? C4 C3 1.4121(15) . ? 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 C2 178.57(17) . . ? C15 C2 C3 122.30(10) . . ? C15 C2 C1 119.61(11) . . ? C3 C2 C1 117.98(10) . . ? C3 N3 H3A 120.0 . . ? C3 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C14 C6 C4 120.27(10) . . ? C14 C6 C7 120.96(10) . . ? C4 C6 C7 118.76(11) . . ? C13 C7 C8 117.88(11) . . ? C13 C7 C6 121.70(11) . . ? C8 C7 C6 120.40(11) . . ? C9 C8 C7 120.59(12) . . ? C9 C8 H6 119.7 . . ? C7 C8 H6 119.7 . . ? C8 C9 C10 121.51(12) . . ? C8 C9 H7 119.2 . . ? C10 C9 H7 119.2 . . ? C12 C10 C9 117.52(11) . . ? C12 C10 C11 121.68(13) . . ? C9 C10 C11 120.80(13) . . ? C10 C11 H9A 109.5 . . ? C10 C11 H9B 109.5 . . ? H9A C11 H9B 109.5 . . ? C10 C11 H9C 109.5 . . ? H9A C11 H9C 109.5 . . ? H9B C11 H9C 109.5 . . ? N2 C5 C4 177.01(12) . . ? C6 C14 C15 119.12(10) . . ? C6 C14 C20 122.14(10) . . ? C15 C14 C20 118.72(11) . . ? C2 C15 C14 119.94(11) . . ? C2 C15 C16 119.84(10) . . ? C14 C15 C16 120.15(10) . . ? C15 C16 C17 113.71(11) . . ? C15 C16 H14A 108.8 . . ? C17 C16 H14A 108.8 . . ? C15 C16 H14B 108.8 . . ? C17 C16 H14B 108.8 . . ? H14A C16 H14B 107.7 . . ? C18 C17 C16 114.79(12) . . ? C18 C17 H15A 108.6 . . ? C16 C17 H15A 108.6 . . ? C18 C17 H15B 108.6 . . ? C16 C17 H15B 108.6 . . ? H15A C17 H15B 107.5 . . ? C19 C18 C17 114.98(11) . . ? C19 C18 H16A 108.5 . . ? C17 C18 H16A 108.5 . . ? C19 C18 H16B 108.5 . . ? C17 C18 H16B 108.5 . . ? H16A C18 H16B 107.5 . . ? C18 C19 C20 114.56(12) . . ? C18 C19 H17A 108.6 . . ? C20 C19 H17A 108.6 . . ? C18 C19 H17B 108.6 . . ? C20 C19 H17B 108.6 . . ? H17A C19 H17B 107.6 . . ? C14 C20 C19 113.29(11) . . ? C14 C20 H18A 108.9 . . ? C19 C20 H18A 108.9 . . ? C14 C20 H18B 108.9 . . ? C19 C20 H18B 108.9 . . ? H18A C20 H18B 107.7 . . ? C10 C12 C13 121.40(13) . . ? C10 C12 H19 119.3 . . ? C13 C12 H19 119.3 . . ? C7 C13 C12 121.06(12) . . ? C7 C13 H20 119.5 . . ? C12 C13 H20 119.5 . . ? C6 C4 C3 121.88(11) . . ? C6 C4 C5 120.43(10) . . ? C3 C4 C5 117.65(10) . . ? N3 C3 C4 121.93(11) . . ? N3 C3 C2 121.65(10) . . ? C4 C3 C2 116.40(10) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 29.31 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.241 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.040 data_1 _database_code_depnum_ccdc_archive 'CCDC 836803' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H15 N5 O2' _chemical_formula_sum 'C19 H15 N5 O2' _chemical_formula_weight 345.36 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.1335(6) _cell_length_b 12.37744(18) _cell_length_c 13.4158(3) _cell_angle_alpha 90.00 _cell_angle_beta 119.443(3) _cell_angle_gamma 90.00 _cell_volume 3634.47(17) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 6588 _cell_measurement_theta_min 4.8599 _cell_measurement_theta_max 74.0206 _exptl_crystal_description 'irregular plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.702 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76172 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12576 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.86 _diffrn_reflns_theta_max 74.19 _reflns_number_total 3640 _reflns_number_gt 3009 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXLTL (Sheldrick, 2008)' _computing_publication_material SHELXLTL _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^)+(0.0593P)^2^+1.8150P] 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 SHELXL _refine_ls_extinction_coef 0.00114(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3640 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1250 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 0.57099(8) -0.05674(14) 0.71547(14) 0.0903(5) Uani 1 1 d . . . O2A O 0.59835(7) 0.10986(16) 0.74095(17) 0.1022(6) Uani 1 1 d . . . N1 N 0.37229(5) 0.28912(11) 0.17282(10) 0.0448(3) Uani 1 1 d . . . H1B H 0.3413 0.2733 0.1076 0.054 Uiso 1 1 calc R . . H1C H 0.4087 0.2836 0.1826 0.054 Uiso 1 1 calc R . . N2 N 0.52124(6) 0.28412(14) 0.38370(12) 0.0585(4) Uani 1 1 d . . . N3 N 0.43070(8) 0.56964(13) 0.36164(13) 0.0690(5) Uani 1 1 d . . . N4 N 0.21265(6) 0.29069(14) 0.06824(12) 0.0613(4) Uani 1 1 d . . . N5 N 0.56018(8) 0.03947(15) 0.69622(14) 0.0670(4) Uani 1 1 d . . . C2 C 0.42059(6) 0.35961(11) 0.36938(11) 0.0365(3) Uani 1 1 d . . . C3 C 0.36395(6) 0.32204(11) 0.25869(11) 0.0351(3) Uani 1 1 d . . . C4 C 0.30984(6) 0.33484(12) 0.25710(11) 0.0386(3) Uani 1 1 d . . . C1 C 0.41511(6) 0.33177(11) 0.47824(11) 0.0366(3) Uani 1 1 d . . . H1A H 0.4470 0.3728 0.5421 0.044 Uiso 1 1 calc R . . C5 C 0.30541(6) 0.37474(12) 0.35645(12) 0.0414(3) Uani 1 1 d . . . C6 C 0.24446(7) 0.41559(17) 0.33528(15) 0.0609(5) Uani 1 1 d . . . H6A H 0.2169 0.3549 0.3186 0.073 Uiso 1 1 calc R . . H6B H 0.2273 0.4626 0.2688 0.073 Uiso 1 1 calc R . . C7 C 0.24904(9) 0.4774(2) 0.43722(18) 0.0819(7) Uani 1 1 d . . . H7A H 0.2655 0.5488 0.4396 0.098 Uiso 1 1 calc R . . H7B H 0.2085 0.4861 0.4280 0.098 Uiso 1 1 calc R . . C8 C 0.28865(10) 0.4207(2) 0.54675(18) 0.0781(6) Uani 1 1 d . . . H8A H 0.2713 0.3503 0.5454 0.094 Uiso 1 1 calc R . . H8B H 0.2897 0.4616 0.6094 0.094 Uiso 1 1 calc R . . C9 C 0.35330(8) 0.40651(16) 0.56755(14) 0.0559(4) Uani 1 1 d . . . H9A H 0.3753 0.4741 0.5950 0.067 Uiso 1 1 calc R . . H9B H 0.3741 0.3525 0.6266 0.067 Uiso 1 1 calc R . . C10 C 0.35455(6) 0.37245(12) 0.46098(12) 0.0403(3) Uani 1 1 d . . . C11 C 0.47753(6) 0.31513(13) 0.37887(12) 0.0425(3) Uani 1 1 d . . . C12 C 0.42506(7) 0.47884(13) 0.36349(12) 0.0450(4) Uani 1 1 d . . . C13 C 0.25511(6) 0.31038(13) 0.15292(12) 0.0431(3) Uani 1 1 d . . . C14 C 0.42695(6) 0.21305(12) 0.51045(11) 0.0377(3) Uani 1 1 d . . . C15 C 0.38039(7) 0.13622(13) 0.46720(13) 0.0473(4) Uani 1 1 d . . . H15A H 0.3405 0.1575 0.4169 0.057 Uiso 1 1 calc R . . C16 C 0.39287(8) 0.02885(14) 0.49814(16) 0.0559(4) Uani 1 1 d . . . H16A H 0.3613 -0.0214 0.4685 0.067 Uiso 1 1 calc R . . C17 C 0.45161(9) -0.00445(14) 0.57244(15) 0.0558(4) Uani 1 1 d . . . H17A H 0.4603 -0.0768 0.5929 0.067 Uiso 1 1 calc R . . C18 C 0.49702(7) 0.07235(14) 0.61554(13) 0.0495(4) Uani 1 1 d . . . C19 C 0.48624(7) 0.18046(13) 0.58664(12) 0.0432(3) Uani 1 1 d . . . H19A H 0.5180 0.2303 0.6175 0.052 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 O1A 0.1010(11) 0.0896(11) 0.0840(10) 0.0333(8) 0.0483(9) 0.0513(9) O2A 0.0464(8) 0.1175(14) 0.1149(14) 0.0441(11) 0.0183(8) 0.0148(9) N1 0.0326(6) 0.0665(8) 0.0321(6) -0.0085(5) 0.0136(5) -0.0029(5) N2 0.0380(7) 0.0870(11) 0.0519(8) 0.0025(7) 0.0232(6) 0.0023(7) N3 0.0793(11) 0.0515(9) 0.0576(9) -0.0009(7) 0.0194(8) -0.0161(8) N4 0.0370(7) 0.0906(11) 0.0430(7) -0.0162(7) 0.0094(6) -0.0024(7) N5 0.0612(9) 0.0879(12) 0.0612(9) 0.0285(8) 0.0373(8) 0.0292(9) C2 0.0303(6) 0.0431(7) 0.0327(6) -0.0023(5) 0.0128(5) -0.0048(5) C3 0.0323(6) 0.0392(7) 0.0287(6) -0.0016(5) 0.0110(5) -0.0020(5) C4 0.0304(6) 0.0470(8) 0.0323(7) -0.0051(6) 0.0107(5) -0.0012(5) C1 0.0324(6) 0.0455(7) 0.0272(6) -0.0044(5) 0.0109(5) -0.0042(5) C5 0.0351(7) 0.0487(8) 0.0389(7) -0.0079(6) 0.0169(6) -0.0004(6) C6 0.0405(8) 0.0848(13) 0.0544(10) -0.0152(9) 0.0209(7) 0.0088(8) C7 0.0578(11) 0.1171(19) 0.0710(13) -0.0261(12) 0.0318(10) 0.0194(12) C8 0.0718(12) 0.1114(17) 0.0639(12) -0.0251(11) 0.0433(10) 0.0041(12) C9 0.0574(9) 0.0706(11) 0.0404(8) -0.0139(7) 0.0245(7) 0.0021(8) C10 0.0385(7) 0.0458(8) 0.0365(7) -0.0072(6) 0.0183(6) -0.0008(6) C11 0.0331(7) 0.0581(9) 0.0325(7) 0.0002(6) 0.0131(6) -0.0060(6) C12 0.0415(8) 0.0495(9) 0.0347(7) -0.0017(6) 0.0114(6) -0.0090(6) C13 0.0344(7) 0.0551(9) 0.0379(7) -0.0080(6) 0.0164(6) -0.0001(6) C14 0.0368(7) 0.0471(8) 0.0318(6) -0.0005(5) 0.0188(5) -0.0006(6) C15 0.0429(8) 0.0534(9) 0.0448(8) -0.0017(7) 0.0210(7) -0.0066(7) C16 0.0620(10) 0.0513(9) 0.0600(10) -0.0040(7) 0.0343(9) -0.0112(8) C17 0.0763(11) 0.0469(9) 0.0598(10) 0.0072(7) 0.0455(9) 0.0060(8) C18 0.0515(8) 0.0626(10) 0.0440(8) 0.0127(7) 0.0310(7) 0.0150(7) C19 0.0389(7) 0.0552(9) 0.0378(7) 0.0043(6) 0.0206(6) 0.0016(6) _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 O1A N5 1.220(2) . ? O2A N5 1.214(2) . ? N1 C3 1.3321(18) . ? N1 H1B 0.8600 . ? N1 H1C 0.8600 . ? N2 C11 1.135(2) . ? N3 C12 1.135(2) . ? N4 C13 1.1387(19) . ? N5 C18 1.473(2) . ? C2 C11 1.479(2) . ? C2 C12 1.485(2) . ? C2 C3 1.5394(17) . ? C2 C1 1.5711(19) . ? C3 C4 1.3588(19) . ? C4 C13 1.4309(18) . ? C4 C5 1.4761(19) . ? C1 C10 1.5092(19) . ? C1 C14 1.519(2) . ? C1 H1A 0.9800 . ? C5 C10 1.3379(19) . ? C5 C6 1.502(2) . ? C6 C7 1.521(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.485(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.518(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.506(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C14 C19 1.389(2) . ? C14 C15 1.394(2) . ? C15 C16 1.382(2) . ? C15 H15A 0.9300 . ? C16 C17 1.377(3) . ? C16 H16A 0.9300 . ? C17 C18 1.375(3) . ? C17 H17A 0.9300 . ? C18 C19 1.382(2) . ? C19 H19A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 H1B 120.0 . . ? C3 N1 H1C 120.0 . . ? H1B N1 H1C 120.0 . . ? O2A N5 O1A 123.79(18) . . ? O2A N5 C18 118.00(17) . . ? O1A N5 C18 118.20(19) . . ? C11 C2 C12 106.21(12) . . ? C11 C2 C3 111.56(11) . . ? C12 C2 C3 107.88(11) . . ? C11 C2 C1 111.19(11) . . ? C12 C2 C1 108.11(12) . . ? C3 C2 C1 111.62(10) . . ? N1 C3 C4 127.14(12) . . ? N1 C3 C2 117.55(12) . . ? C4 C3 C2 115.07(12) . . ? C3 C4 C13 117.70(12) . . ? C3 C4 C5 122.96(12) . . ? C13 C4 C5 119.32(12) . . ? C10 C1 C14 114.08(12) . . ? C10 C1 C2 109.08(11) . . ? C14 C1 C2 112.47(11) . . ? C10 C1 H1A 106.9 . . ? C14 C1 H1A 106.9 . . ? C2 C1 H1A 106.9 . . ? C10 C5 C4 119.92(13) . . ? C10 C5 C6 122.39(13) . . ? C4 C5 C6 117.69(12) . . ? C5 C6 C7 112.32(14) . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C6 111.70(18) . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C7 C8 C9 111.89(18) . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C8 112.21(14) . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C5 C10 C9 123.36(13) . . ? C5 C10 C1 120.64(12) . . ? C9 C10 C1 115.98(12) . . ? N2 C11 C2 177.43(17) . . ? N3 C12 C2 177.50(18) . . ? N4 C13 C4 177.76(16) . . ? C19 C14 C15 119.04(14) . . ? C19 C14 C1 118.63(13) . . ? C15 C14 C1 122.32(13) . . ? C16 C15 C14 120.74(15) . . ? C16 C15 H15A 119.6 . . ? C14 C15 H15A 119.6 . . ? C17 C16 C15 120.64(16) . . ? C17 C16 H16A 119.7 . . ? C15 C16 H16A 119.7 . . ? C18 C17 C16 118.05(16) . . ? C18 C17 H17A 121.0 . . ? C16 C17 H17A 121.0 . . ? C17 C18 C19 122.91(15) . . ? C17 C18 N5 119.34(16) . . ? C19 C18 N5 117.75(16) . . ? C18 C19 C14 118.61(15) . . ? C18 C19 H19A 120.7 . . ? C14 C19 H19A 120.7 . . ? 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 C11 C2 C3 N1 -21.68(18) . . . . ? C12 C2 C3 N1 94.61(15) . . . . ? C1 C2 C3 N1 -146.75(13) . . . . ? C11 C2 C3 C4 163.43(13) . . . . ? C12 C2 C3 C4 -80.28(15) . . . . ? C1 C2 C3 C4 38.35(17) . . . . ? N1 C3 C4 C13 0.3(2) . . . . ? C2 C3 C4 C13 174.60(13) . . . . ? N1 C3 C4 C5 -178.32(14) . . . . ? C2 C3 C4 C5 -4.0(2) . . . . ? C11 C2 C1 C10 -176.32(12) . . . . ? C12 C2 C1 C10 67.46(14) . . . . ? C3 C2 C1 C10 -51.04(15) . . . . ? C11 C2 C1 C14 -48.72(15) . . . . ? C12 C2 C1 C14 -164.94(11) . . . . ? C3 C2 C1 C14 76.56(14) . . . . ? C3 C4 C5 C10 -18.1(2) . . . . ? C13 C4 C5 C10 163.36(15) . . . . ? C3 C4 C5 C6 162.70(16) . . . . ? C13 C4 C5 C6 -15.9(2) . . . . ? C10 C5 C6 C7 13.9(3) . . . . ? C4 C5 C6 C7 -166.84(18) . . . . ? C5 C6 C7 C8 -44.6(3) . . . . ? C6 C7 C8 C9 60.1(3) . . . . ? C7 C8 C9 C10 -42.7(3) . . . . ? C4 C5 C10 C9 -176.97(15) . . . . ? C6 C5 C10 C9 2.2(3) . . . . ? C4 C5 C10 C1 1.4(2) . . . . ? C6 C5 C10 C1 -179.38(15) . . . . ? C8 C9 C10 C5 12.0(3) . . . . ? C8 C9 C10 C1 -166.46(16) . . . . ? C14 C1 C10 C5 -94.48(16) . . . . ? C2 C1 C10 C5 32.21(18) . . . . ? C14 C1 C10 C9 84.02(16) . . . . ? C2 C1 C10 C9 -149.29(13) . . . . ? C12 C2 C11 N2 -33(4) . . . . ? C3 C2 C11 N2 84(4) . . . . ? C1 C2 C11 N2 -150(4) . . . . ? C11 C2 C12 N3 -35(4) . . . . ? C3 C2 C12 N3 -155(4) . . . . ? C1 C2 C12 N3 84(4) . . . . ? C3 C4 C13 N4 -11(5) . . . . ? C5 C4 C13 N4 168(5) . . . . ? C10 C1 C14 C19 -144.25(13) . . . . ? C2 C1 C14 C19 90.85(14) . . . . ? C10 C1 C14 C15 35.08(18) . . . . ? C2 C1 C14 C15 -89.82(16) . . . . ? C19 C14 C15 C16 -0.9(2) . . . . ? C1 C14 C15 C16 179.82(14) . . . . ? C14 C15 C16 C17 0.0(3) . . . . ? C15 C16 C17 C18 0.7(3) . . . . ? C16 C17 C18 C19 -0.7(2) . . . . ? C16 C17 C18 N5 179.31(15) . . . . ? O2A N5 C18 C17 -173.44(18) . . . . ? O1A N5 C18 C17 5.6(2) . . . . ? O2A N5 C18 C19 6.5(2) . . . . ? O1A N5 C18 C19 -174.48(16) . . . . ? C17 C18 C19 C14 -0.2(2) . . . . ? N5 C18 C19 C14 179.87(13) . . . . ? C15 C14 C19 C18 0.9(2) . . . . ? C1 C14 C19 C18 -179.74(13) . . . . ? 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 N1 H1B N4 0.86 2.21 3.0340(17) 160.1 7 N1 H1C N2 0.86 2.33 3.1200(18) 152.6 2_655 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.282 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.032 # Attachment '- Supporting information 10 (CIF File of compound 5io).cif' data_5io _database_code_depnum_ccdc_archive 'CCDC 855038' #TrackingRef '- Supporting information 10 (CIF File of compound 5io).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 N4' _chemical_formula_weight 310.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'p 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 20.561(2) _cell_length_b 7.2280(8) _cell_length_c 24.638(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.8730(10) _cell_angle_gamma 90.00 _cell_volume 3373.7(7) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1316 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9913 _exptl_absorpt_correction_T_max 0.9971 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22598 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_max 25.19 _reflns_number_total 5995 _reflns_number_gt 3901 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1782P)^2^+1.9954P] 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 0.0014(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5995 _refine_ls_number_parameters 450 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.2011 _refine_ls_wR_factor_gt 0.1508 _refine_ls_goodness_of_fit_ref 0.683 _refine_ls_restrained_S_all 0.683 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C4 C 0.07266(10) 0.5886(3) 0.81214(9) 0.0458(5) Uani 1 1 d . . . C3 C 0.00941(10) 0.5358(3) 0.81771(9) 0.0464(5) Uani 1 1 d . . . N2 N -0.05234(10) 0.6254(3) 0.78871(9) 0.0567(5) Uani 1 1 d . . . C27 C 0.41206(10) 0.7449(3) 0.05890(10) 0.0491(5) Uani 1 1 d . . . N5 N 0.17610(10) 1.2942(3) 0.17533(10) 0.0676(6) Uani 1 1 d . . . C22 C 0.41921(10) 1.1912(3) 0.17414(9) 0.0461(5) Uani 1 1 d . . . N6 N 0.42374(12) 1.4693(3) 0.24082(11) 0.0759(7) Uani 1 1 d . . . N7 N 0.54292(10) 1.2351(3) 0.19519(10) 0.0613(6) Uani 1 1 d . . . H15 H 0.5411(16) 1.352(5) 0.2126(13) 0.092 Uiso 1 1 d . . . H16 H 0.5811(16) 1.214(4) 0.1859(13) 0.092 Uiso 1 1 d . . . N4 N 0.31892(10) 0.7094(3) 0.81987(9) 0.0656(6) Uani 1 1 d . . . C10 C 0.29521(13) 0.5405(4) 0.80341(12) 0.0708(7) Uani 1 1 d . . . H4 H 0.3190 0.4673 0.7861 0.085 Uiso 1 1 calc R . . C11 C 0.23716(13) 0.4656(4) 0.81037(12) 0.0681(7) Uani 1 1 d . . . H3 H 0.2227 0.3456 0.7979 0.082 Uiso 1 1 calc R . . C7 C 0.20083(10) 0.5711(3) 0.83616(9) 0.0503(5) Uani 1 1 d . . . C6 C 0.13702(10) 0.5007(3) 0.84393(9) 0.0482(5) Uani 1 1 d . . . C12 C 0.14097(11) 0.3565(3) 0.88268(10) 0.0517(5) Uani 1 1 d . . . C14 C 0.07866(11) 0.2968(3) 0.88721(9) 0.0481(5) Uani 1 1 d . . . C15 C 0.07948(11) 0.1421(3) 0.92751(10) 0.0508(5) Uani 1 1 d . . . C20 C 0.0675(2) -0.0349(4) 0.90754(13) 0.0989(12) Uani 1 1 d . . . H14 H 0.0567 -0.0594 0.8679 0.119 Uiso 1 1 calc R . . C19 C 0.0711(3) -0.1778(4) 0.94527(15) 0.1179(14) Uani 1 1 d . . . H13 H 0.0645 -0.2985 0.9311 0.142 Uiso 1 1 calc R . . C18 C 0.08410(15) -0.1465(4) 1.00234(13) 0.0754(8) Uani 1 1 d . . . H12 H 0.0854 -0.2442 1.0273 0.091 Uiso 1 1 calc R . . C8 C 0.22605(12) 0.7457(4) 0.85375(12) 0.0632(6) Uani 1 1 d . . . H6 H 0.2039 0.8217 0.8718 0.076 Uiso 1 1 calc R . . C9 C 0.28417(12) 0.8086(4) 0.84469(13) 0.0704(7) Uani 1 1 d . . . H5 H 0.2999 0.9282 0.8568 0.085 Uiso 1 1 calc R . . C2 C 0.01412(10) 0.3827(3) 0.85450(9) 0.0463(5) Uani 1 1 d . . . C13 C 0.21123(13) 0.2690(4) 0.92001(13) 0.0780(8) Uani 1 1 d . . . H8 H 0.2247 0.1835 0.8964 0.117 Uiso 1 1 calc R . . H7 H 0.2069 0.2044 0.9525 0.117 Uiso 1 1 calc R . . H9 H 0.2465 0.3637 0.9347 0.117 Uiso 1 1 calc R . . C17 C 0.09515(14) 0.0271(4) 1.02270(11) 0.0726(7) Uani 1 1 d . . . H11 H 0.1041 0.0500 1.0621 0.087 Uiso 1 1 calc R . . C16 C 0.09337(14) 0.1727(4) 0.98582(11) 0.0695(7) Uani 1 1 d . . . H10 H 0.1017 0.2925 1.0007 0.083 Uiso 1 1 calc R . . C1 C -0.04963(11) 0.3172(3) 0.85834(10) 0.0522(5) Uani 1 1 d . . . N1 N -0.10147(11) 0.2665(3) 0.85946(10) 0.0709(6) Uani 1 1 d . . . N3 N 0.06596(11) 0.8596(3) 0.74268(11) 0.0754(7) Uani 1 1 d . . . C30 C 0.40580(14) 0.4608(5) -0.01787(14) 0.0818(9) Uani 1 1 d . . . H19 H 0.4034 0.3652 -0.0438 0.098 Uiso 1 1 calc R . . C29 C 0.41522(15) 0.6403(5) -0.03183(12) 0.0827(9) Uani 1 1 d . . . H18 H 0.4197 0.6658 -0.0672 0.099 Uiso 1 1 calc R . . C28 C 0.41805(14) 0.7827(4) 0.00618(11) 0.0683(7) Uani 1 1 d . . . H17 H 0.4240 0.9039 -0.0037 0.082 Uiso 1 1 calc R . . C26 C 0.41358(11) 0.8978(3) 0.09987(9) 0.0471(5) Uani 1 1 d . . . C33 C 0.35185(11) 0.9507(3) 0.10721(10) 0.0510(5) Uani 1 1 d . . . C35 C 0.35574(10) 1.0967(3) 0.14518(9) 0.0466(5) Uani 1 1 d . . . C36 C 0.29213(10) 1.1616(3) 0.15469(10) 0.0487(5) Uani 1 1 d . . . C40 C 0.26400(12) 1.0639(4) 0.18798(12) 0.0648(7) Uani 1 1 d . . . H28 H 0.2836 0.9511 0.2045 0.078 Uiso 1 1 calc R . . C39 C 0.20634(14) 1.1338(4) 0.19697(12) 0.0711(7) Uani 1 1 d . . . H27 H 0.1878 1.0645 0.2194 0.085 Uiso 1 1 calc R . . C31 C 0.40006(17) 0.4243(4) 0.03387(15) 0.0858(9) Uani 1 1 d . . . H20 H 0.3937 0.3031 0.0435 0.103 Uiso 1 1 calc R . . C32 C 0.40359(15) 0.5652(3) 0.07227(12) 0.0694(7) Uani 1 1 d . . . H21 H 0.4002 0.5380 0.1080 0.083 Uiso 1 1 calc R . . C21 C 0.42117(11) 1.3448(3) 0.21166(10) 0.0540(6) Uani 1 1 d . . . C23 C 0.48177(10) 1.1435(3) 0.16693(9) 0.0474(5) Uani 1 1 d . . . C24 C 0.47703(10) 0.9911(3) 0.12989(9) 0.0469(5) Uani 1 1 d . . . C25 C 0.53987(11) 0.9313(3) 0.12319(11) 0.0548(6) Uani 1 1 d . . . N8 N 0.59080(11) 0.8859(3) 0.11916(12) 0.0811(7) Uani 1 1 d . . . C37 C 0.25998(13) 1.3259(3) 0.13108(12) 0.0653(7) Uani 1 1 d . . . H25 H 0.2764 1.3960 0.1074 0.078 Uiso 1 1 calc R . . C38 C 0.20324(14) 1.3860(4) 0.14276(13) 0.0744(8) Uani 1 1 d . . . H26 H 0.1827 1.4984 0.1267 0.089 Uiso 1 1 calc R . . C34 C 0.28192(12) 0.8584(4) 0.07251(13) 0.0756(8) Uani 1 1 d . . . H23 H 0.2716 0.7697 0.0970 0.113 Uiso 1 1 calc R . . H24 H 0.2845 0.7967 0.0389 0.113 Uiso 1 1 calc R . . H22 H 0.2453 0.9501 0.0596 0.113 Uiso 1 1 calc R . . C5 C 0.06967(11) 0.7379(3) 0.77308(10) 0.0535(6) Uani 1 1 d . . . H1 H -0.0876(14) 0.616(4) 0.8014(11) 0.072(8) Uiso 1 1 d . . . H2 H -0.0492(14) 0.747(4) 0.7724(12) 0.079(8) Uiso 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 C4 0.0436(11) 0.0460(12) 0.0542(12) -0.0003(9) 0.0260(9) -0.0006(9) C3 0.0413(10) 0.0503(12) 0.0518(11) -0.0015(10) 0.0226(9) 0.0013(9) N2 0.0416(10) 0.0651(13) 0.0701(12) 0.0167(10) 0.0289(9) 0.0071(9) C27 0.0424(10) 0.0488(12) 0.0589(13) -0.0072(10) 0.0228(9) -0.0004(9) N5 0.0522(11) 0.0726(15) 0.0911(15) -0.0088(12) 0.0421(11) -0.0002(10) C22 0.0463(11) 0.0443(11) 0.0560(12) -0.0037(9) 0.0290(9) -0.0029(9) N6 0.0733(14) 0.0788(15) 0.0935(16) -0.0352(14) 0.0518(12) -0.0171(12) N7 0.0449(10) 0.0662(13) 0.0819(14) -0.0220(11) 0.0346(10) -0.0108(9) N4 0.0460(10) 0.0811(16) 0.0773(14) 0.0051(11) 0.0321(10) -0.0036(10) C10 0.0566(14) 0.091(2) 0.0806(17) -0.0058(15) 0.0440(13) 0.0022(14) C11 0.0637(14) 0.0696(16) 0.0866(17) -0.0152(14) 0.0462(13) -0.0044(12) C7 0.0387(10) 0.0576(14) 0.0595(13) 0.0011(10) 0.0243(9) 0.0017(9) C6 0.0419(11) 0.0503(12) 0.0583(12) -0.0045(10) 0.0261(9) -0.0009(9) C12 0.0424(11) 0.0520(13) 0.0639(13) 0.0029(11) 0.0241(10) 0.0036(9) C14 0.0488(11) 0.0439(12) 0.0567(12) -0.0010(9) 0.0260(10) 0.0027(9) C15 0.0441(11) 0.0535(13) 0.0595(13) 0.0038(10) 0.0252(10) 0.0036(9) C20 0.190(4) 0.0512(16) 0.0690(18) -0.0024(14) 0.065(2) -0.0061(19) C19 0.227(5) 0.0526(17) 0.089(2) 0.0021(16) 0.078(3) -0.006(2) C18 0.0896(19) 0.0655(18) 0.0766(18) 0.0213(15) 0.0382(15) 0.0082(14) C8 0.0467(12) 0.0615(15) 0.0904(17) -0.0108(13) 0.0365(12) -0.0023(11) C9 0.0481(13) 0.0689(16) 0.1005(19) -0.0066(14) 0.0355(13) -0.0081(11) C2 0.0434(11) 0.0467(12) 0.0548(12) -0.0008(9) 0.0256(9) -0.0014(9) C13 0.0503(13) 0.0809(19) 0.103(2) 0.0292(16) 0.0307(14) 0.0131(13) C17 0.0718(16) 0.092(2) 0.0539(14) 0.0119(14) 0.0239(12) 0.0043(15) C16 0.0799(17) 0.0638(16) 0.0625(15) -0.0023(12) 0.0253(13) -0.0054(13) C1 0.0503(12) 0.0480(12) 0.0648(14) 0.0073(10) 0.0293(10) 0.0033(10) N1 0.0549(12) 0.0694(14) 0.1008(16) 0.0166(12) 0.0440(11) 0.0011(10) N3 0.0653(13) 0.0796(16) 0.0961(16) 0.0314(14) 0.0476(12) 0.0135(11) C30 0.0648(16) 0.087(2) 0.083(2) -0.0376(17) 0.0177(14) 0.0109(15) C29 0.0808(18) 0.110(3) 0.0555(15) -0.0116(16) 0.0242(13) 0.0153(17) C28 0.0771(16) 0.0702(17) 0.0602(14) 0.0012(13) 0.0294(12) 0.0071(13) C26 0.0491(11) 0.0406(11) 0.0574(12) 0.0010(9) 0.0269(10) 0.0001(9) C33 0.0418(11) 0.0463(12) 0.0686(14) -0.0029(10) 0.0256(10) -0.0020(9) C35 0.0428(11) 0.0446(12) 0.0591(12) 0.0020(10) 0.0271(9) 0.0005(9) C36 0.0403(10) 0.0488(12) 0.0640(13) -0.0078(10) 0.0279(10) -0.0045(9) C40 0.0580(13) 0.0631(15) 0.0883(17) 0.0108(13) 0.0450(13) 0.0039(11) C39 0.0643(15) 0.0811(19) 0.0869(18) 0.0028(15) 0.0501(14) -0.0040(14) C31 0.103(2) 0.0547(16) 0.100(2) -0.0168(16) 0.0391(18) 0.0010(15) C32 0.0899(18) 0.0504(15) 0.0770(17) -0.0032(13) 0.0424(14) -0.0020(13) C21 0.0459(11) 0.0614(14) 0.0658(14) -0.0089(12) 0.0338(10) -0.0062(10) C23 0.0450(11) 0.0468(12) 0.0567(12) -0.0028(10) 0.0268(9) -0.0048(9) C24 0.0422(10) 0.0444(12) 0.0616(12) -0.0023(10) 0.0283(9) -0.0017(9) C25 0.0488(12) 0.0498(13) 0.0748(15) -0.0136(11) 0.0337(11) -0.0089(10) N8 0.0586(12) 0.0763(15) 0.126(2) -0.0378(14) 0.0554(13) -0.0124(11) C37 0.0609(14) 0.0589(15) 0.0942(18) 0.0117(13) 0.0500(13) 0.0077(12) C38 0.0654(15) 0.0646(16) 0.110(2) 0.0104(15) 0.0522(16) 0.0137(12) C34 0.0500(13) 0.0715(17) 0.105(2) -0.0298(15) 0.0303(13) -0.0100(12) C5 0.0434(11) 0.0606(14) 0.0659(14) 0.0065(12) 0.0316(10) 0.0045(10) _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 C4 C6 1.401(3) . ? C4 C3 1.412(3) . ? C4 C5 1.432(3) . ? C3 N2 1.355(3) . ? C3 C2 1.410(3) . ? N2 H1 0.90(3) . ? N2 H2 0.98(3) . ? C27 C32 1.368(3) . ? C27 C28 1.379(3) . ? C27 C26 1.489(3) . ? N5 C38 1.321(3) . ? N5 C39 1.326(3) . ? C22 C35 1.398(3) . ? C22 C23 1.408(3) . ? C22 C21 1.436(3) . ? N6 C21 1.140(3) . ? N7 C23 1.350(3) . ? N7 H15 0.96(3) . ? N7 H16 0.91(3) . ? N4 C9 1.319(3) . ? N4 C10 1.319(4) . ? C10 C11 1.380(3) . ? C10 H4 0.9300 . ? C11 C7 1.383(3) . ? C11 H3 0.9300 . ? C7 C8 1.369(3) . ? C7 C6 1.487(3) . ? C6 C12 1.394(3) . ? C12 C14 1.397(3) . ? C12 C13 1.517(3) . ? C14 C2 1.402(3) . ? C14 C15 1.491(3) . ? C15 C20 1.359(4) . ? C15 C16 1.369(3) . ? C20 C19 1.372(4) . ? C20 H14 0.9300 . ? C19 C18 1.345(4) . ? C19 H13 0.9300 . ? C18 C17 1.338(4) . ? C18 H12 0.9300 . ? C8 C9 1.376(3) . ? C8 H6 0.9300 . ? C9 H5 0.9300 . ? C2 C1 1.431(3) . ? C13 H8 0.9600 . ? C13 H7 0.9600 . ? C13 H9 0.9600 . ? C17 C16 1.381(4) . ? C17 H11 0.9300 . ? C16 H10 0.9300 . ? C1 N1 1.138(3) . ? N3 C5 1.138(3) . ? C30 C31 1.351(4) . ? C30 C29 1.375(4) . ? C30 H19 0.9300 . ? C29 C28 1.377(4) . ? C29 H18 0.9300 . ? C28 H17 0.9300 . ? C26 C24 1.398(3) . ? C26 C33 1.403(3) . ? C33 C35 1.392(3) . ? C33 C34 1.513(3) . ? C35 C36 1.491(3) . ? C36 C40 1.369(3) . ? C36 C37 1.374(3) . ? C40 C39 1.383(3) . ? C40 H28 0.9300 . ? C39 H27 0.9300 . ? C31 C32 1.373(4) . ? C31 H20 0.9300 . ? C32 H21 0.9300 . ? C23 C24 1.410(3) . ? C24 C25 1.432(3) . ? C25 N8 1.138(3) . ? C37 C38 1.376(3) . ? C37 H25 0.9300 . ? C38 H26 0.9300 . ? C34 H23 0.9600 . ? C34 H24 0.9600 . ? C34 H22 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C4 C3 121.92(19) . . ? C6 C4 C5 120.14(18) . . ? C3 C4 C5 117.94(18) . . ? N2 C3 C2 122.04(19) . . ? N2 C3 C4 121.9(2) . . ? C2 C3 C4 116.02(18) . . ? C3 N2 H1 119.8(17) . . ? C3 N2 H2 116.6(16) . . ? H1 N2 H2 114(2) . . ? C32 C27 C28 118.8(2) . . ? C32 C27 C26 120.8(2) . . ? C28 C27 C26 120.4(2) . . ? C38 N5 C39 116.2(2) . . ? C35 C22 C23 122.25(19) . . ? C35 C22 C21 119.57(17) . . ? C23 C22 C21 118.17(18) . . ? C23 N7 H15 118.3(18) . . ? C23 N7 H16 120.7(19) . . ? H15 N7 H16 116(3) . . ? C9 N4 C10 116.4(2) . . ? N4 C10 C11 124.0(2) . . ? N4 C10 H4 118.0 . . ? C11 C10 H4 118.0 . . ? C10 C11 C7 119.3(2) . . ? C10 C11 H3 120.4 . . ? C7 C11 H3 120.4 . . ? C8 C7 C11 116.6(2) . . ? C8 C7 C6 121.26(19) . . ? C11 C7 C6 122.1(2) . . ? C12 C6 C4 120.84(18) . . ? C12 C6 C7 121.62(18) . . ? C4 C6 C7 117.51(19) . . ? C6 C12 C14 118.33(19) . . ? C6 C12 C13 121.01(19) . . ? C14 C12 C13 120.6(2) . . ? C12 C14 C2 120.7(2) . . ? C12 C14 C15 120.77(19) . . ? C2 C14 C15 118.57(18) . . ? C20 C15 C16 117.8(2) . . ? C20 C15 C14 120.8(2) . . ? C16 C15 C14 121.4(2) . . ? C15 C20 C19 120.6(3) . . ? C15 C20 H14 119.7 . . ? C19 C20 H14 119.7 . . ? C18 C19 C20 121.2(3) . . ? C18 C19 H13 119.4 . . ? C20 C19 H13 119.4 . . ? C17 C18 C19 119.0(3) . . ? C17 C18 H12 120.5 . . ? C19 C18 H12 120.5 . . ? C7 C8 C9 120.0(2) . . ? C7 C8 H6 120.0 . . ? C9 C8 H6 120.0 . . ? N4 C9 C8 123.8(3) . . ? N4 C9 H5 118.1 . . ? C8 C9 H5 118.1 . . ? C14 C2 C3 122.05(18) . . ? C14 C2 C1 120.16(19) . . ? C3 C2 C1 117.79(18) . . ? C12 C13 H8 109.5 . . ? C12 C13 H7 109.5 . . ? H8 C13 H7 109.5 . . ? C12 C13 H9 109.5 . . ? H8 C13 H9 109.5 . . ? H7 C13 H9 109.5 . . ? C18 C17 C16 120.7(3) . . ? C18 C17 H11 119.6 . . ? C16 C17 H11 119.6 . . ? C15 C16 C17 120.6(3) . . ? C15 C16 H10 119.7 . . ? C17 C16 H10 119.7 . . ? N1 C1 C2 177.7(3) . . ? C31 C30 C29 119.5(3) . . ? C31 C30 H19 120.2 . . ? C29 C30 H19 120.2 . . ? C30 C29 C28 120.5(3) . . ? C30 C29 H18 119.7 . . ? C28 C29 H18 119.7 . . ? C29 C28 C27 119.8(3) . . ? C29 C28 H17 120.1 . . ? C27 C28 H17 120.1 . . ? C24 C26 C33 120.36(19) . . ? C24 C26 C27 119.10(17) . . ? C33 C26 C27 120.52(18) . . ? C35 C33 C26 118.34(19) . . ? C35 C33 C34 120.53(19) . . ? C26 C33 C34 121.1(2) . . ? C33 C35 C22 120.77(18) . . ? C33 C35 C36 121.28(18) . . ? C22 C35 C36 117.91(18) . . ? C40 C36 C37 117.0(2) . . ? C40 C36 C35 122.2(2) . . ? C37 C36 C35 120.8(2) . . ? C36 C40 C39 119.7(2) . . ? C36 C40 H28 120.1 . . ? C39 C40 H28 120.1 . . ? N5 C39 C40 123.5(2) . . ? N5 C39 H27 118.2 . . ? C40 C39 H27 118.2 . . ? C30 C31 C32 120.3(3) . . ? C30 C31 H20 119.8 . . ? C32 C31 H20 119.8 . . ? C27 C32 C31 121.1(3) . . ? C27 C32 H21 119.5 . . ? C31 C32 H21 119.5 . . ? N6 C21 C22 178.2(2) . . ? N7 C23 C22 121.9(2) . . ? N7 C23 C24 122.23(19) . . ? C22 C23 C24 115.86(18) . . ? C26 C24 C23 122.36(18) . . ? C26 C24 C25 119.47(19) . . ? C23 C24 C25 118.18(18) . . ? N8 C25 C24 178.3(3) . . ? C36 C37 C38 119.5(2) . . ? C36 C37 H25 120.3 . . ? C38 C37 H25 120.3 . . ? N5 C38 C37 124.1(2) . . ? N5 C38 H26 117.9 . . ? C37 C38 H26 117.9 . . ? C33 C34 H23 109.5 . . ? C33 C34 H24 109.5 . . ? H23 C34 H24 109.5 . . ? C33 C34 H22 109.5 . . ? H23 C34 H22 109.5 . . ? H24 C34 H22 109.5 . . ? N3 C5 C4 177.9(2) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.162 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.030 # Attachment '- Supporting information 6 (CIF File of compound 4ie).cif' data_4ie _database_code_depnum_ccdc_archive 'CCDC 855039' #TrackingRef '- Supporting information 6 (CIF File of compound 4ie).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H20 N4 O2' _chemical_formula_weight 396.44 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 11.7899(3) _cell_length_b 14.3124(5) _cell_length_c 14.5079(4) _cell_angle_alpha 64.6170(10) _cell_angle_beta 78.2420(10) _cell_angle_gamma 76.1420(10) _cell_volume 2133.07(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9913 _exptl_absorpt_correction_T_max 0.9971 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26276 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 29.12 _reflns_number_total 11108 _reflns_number_gt 6993 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0023(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 11108 _refine_ls_number_parameters 548 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1578 _refine_ls_wR_factor_gt 0.1385 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.46524(14) -0.03185(11) 1.15156(12) 0.0853(4) Uani 1 1 d . . . O2 O 0.28635(10) 0.38827(11) 1.05599(11) 0.0694(4) Uani 1 1 d . . . O3 O 0.04535(12) 0.56243(9) 0.35959(11) 0.0708(4) Uani 1 1 d . . . O4 O 0.02533(10) 0.19428(9) 0.33203(9) 0.0566(3) Uani 1 1 d . . . C24 C 0.64680(12) 0.30506(11) 1.01181(11) 0.0417(3) Uani 1 1 d . . . C18 C 0.72511(12) 0.26625(11) 0.95074(11) 0.0398(3) Uani 1 1 d . . . C17 C 0.68767(12) 0.25677(11) 0.86417(11) 0.0384(3) Uani 1 1 d . . . C23 C 0.76371(12) 0.19092(11) 0.81832(12) 0.0420(3) Uani 1 1 d . . . N1 N 0.82529(12) 0.13945(12) 0.77966(12) 0.0595(4) Uani 1 1 d . . . C42 C 0.27894(13) 0.27734(14) 0.65180(13) 0.0518(4) Uani 1 1 d . . . C1 C 0.5861(2) -0.06160(17) 1.1234(2) 0.0969(8) Uani 1 1 d . . . H1A H 0.6322 -0.0444 1.1595 0.145 Uiso 1 1 calc R . . H1B H 0.6047 -0.0248 1.0507 0.145 Uiso 1 1 calc R . . H1C H 0.6034 -0.1358 1.1408 0.145 Uiso 1 1 calc R . . C2 C 0.42361(17) 0.07347(15) 1.12771(14) 0.0626(5) Uani 1 1 d . . . C3 C 0.49210(14) 0.15110(13) 1.07361(12) 0.0517(4) Uani 1 1 d . . . H3 H 0.5712 0.1324 1.0532 0.062 Uiso 1 1 calc R . . C4 C 0.44438(13) 0.25576(13) 1.04958(12) 0.0460(4) Uani 1 1 d . . . C5 C 0.51929(12) 0.34121(12) 0.99088(11) 0.0417(3) Uani 1 1 d . . . H5 H 0.4869 0.3985 1.0138 0.050 Uiso 1 1 calc R . . C6 C 0.85194(12) 0.22751(12) 0.96658(12) 0.0450(3) Uani 1 1 d . . . C7 C 0.88751(18) 0.13116(16) 1.04195(19) 0.0784(6) Uani 1 1 d . . . H7 H 0.8321 0.0902 1.0851 0.094 Uiso 1 1 calc R . . C8 C 1.0062(2) 0.0949(2) 1.0537(2) 0.1041(9) Uani 1 1 d . . . H8 H 1.0298 0.0295 1.1045 0.125 Uiso 1 1 calc R . . C9 C 1.0881(2) 0.1539(3) 0.9919(2) 0.1004(9) Uani 1 1 d . . . H9 H 1.1673 0.1292 1.0003 0.121 Uiso 1 1 calc R . . C10 C 0.32581(14) 0.28336(15) 1.08146(13) 0.0545(4) Uani 1 1 d . . . C11 C 0.25880(16) 0.20503(18) 1.13665(14) 0.0688(5) Uani 1 1 d . . . H11 H 0.1800 0.2230 1.1585 0.083 Uiso 1 1 calc R . . C12 C 0.30669(17) 0.10180(18) 1.15943(15) 0.0702(5) Uani 1 1 d . . . H12 H 0.2603 0.0503 1.1965 0.084 Uiso 1 1 calc R . . C13 C 0.16521(19) 0.4238(2) 1.0788(2) 0.1116(9) Uani 1 1 d . . . H13A H 0.1432 0.3921 1.1516 0.167 Uiso 1 1 calc R . . H13B H 0.1194 0.4046 1.0441 0.167 Uiso 1 1 calc R . . H13C H 0.1510 0.4988 1.0562 0.167 Uiso 1 1 calc R . . C14 C 0.51443(12) 0.38767(11) 0.87257(11) 0.0407(3) Uani 1 1 d . . . C15 C 0.57564(15) 0.47987(12) 0.82372(13) 0.0509(4) Uani 1 1 d . . . N3 N 0.62384(16) 0.54927(13) 0.78663(14) 0.0783(5) Uani 1 1 d . . . C16 C 0.58312(12) 0.30850(11) 0.82709(11) 0.0380(3) Uani 1 1 d . . . N2 N 0.54018(12) 0.30326(11) 0.75140(11) 0.0560(4) Uani 1 1 d . . . H18A H 0.5800 0.2639 0.7207 0.067 Uiso 1 1 calc R . . H18B H 0.4727 0.3392 0.7334 0.067 Uiso 1 1 calc R . . C19 C 0.67413(16) 0.31438(16) 1.10385(14) 0.0620(5) Uani 1 1 d . . . H19A H 0.7551 0.2850 1.1138 0.093 Uiso 1 1 calc R . . H19B H 0.6248 0.2770 1.1636 0.093 Uiso 1 1 calc R . . H19C H 0.6600 0.3870 1.0930 0.093 Uiso 1 1 calc R . . C20 C 1.05353(18) 0.2493(2) 0.9177(2) 0.0925(8) Uani 1 1 d . . . H20 H 1.1095 0.2900 0.8753 0.111 Uiso 1 1 calc R . . C21 C 0.93597(15) 0.28644(17) 0.90464(16) 0.0689(5) Uani 1 1 d . . . H21 H 0.9135 0.3519 0.8534 0.083 Uiso 1 1 calc R . . C22 C 0.39233(14) 0.42520(13) 0.84529(13) 0.0500(4) Uani 1 1 d . . . N4 N 0.30097(14) 0.45690(14) 0.82122(14) 0.0750(5) Uani 1 1 d . . . C25 C 0.14063(19) 0.56766(15) 0.40188(18) 0.0741(5) Uani 1 1 d . . . H24A H 0.2130 0.5543 0.3615 0.111 Uiso 1 1 calc R . . H24B H 0.1422 0.5159 0.4711 0.111 Uiso 1 1 calc R . . H24C H 0.1313 0.6363 0.4016 0.111 Uiso 1 1 calc R . . C26 C 0.04281(14) 0.46823(12) 0.35641(13) 0.0510(4) Uani 1 1 d . . . C27 C 0.12519(13) 0.37805(12) 0.39438(12) 0.0454(3) Uani 1 1 d . . . H26 H 0.1876 0.3797 0.4235 0.055 Uiso 1 1 calc R . . C28 C 0.11609(12) 0.28528(11) 0.38961(11) 0.0413(3) Uani 1 1 d . . . C33 C 0.20205(12) 0.18389(11) 0.43762(11) 0.0411(3) Uani 1 1 d . . . H28 H 0.2058 0.1399 0.4003 0.049 Uiso 1 1 calc R . . C39 C 0.32617(12) 0.19900(11) 0.43341(11) 0.0407(3) Uani 1 1 d . . . C38 C 0.35301(12) 0.21824(11) 0.50844(11) 0.0423(3) Uani 1 1 d . . . C43 C 0.47202(12) 0.23568(13) 0.51097(12) 0.0469(4) Uani 1 1 d . . . C44 C 0.54781(14) 0.15696(15) 0.57541(15) 0.0618(5) Uani 1 1 d . . . H32 H 0.5238 0.0931 0.6178 0.074 Uiso 1 1 calc R . . C45 C 0.65878(16) 0.17108(19) 0.57822(17) 0.0736(6) Uani 1 1 d . . . H33 H 0.7092 0.1167 0.6216 0.088 Uiso 1 1 calc R . . C46 C 0.69378(17) 0.2637(2) 0.51811(17) 0.0786(6) Uani 1 1 d . . . H34 H 0.7689 0.2729 0.5191 0.094 Uiso 1 1 calc R . . C29 C 0.02442(12) 0.28544(12) 0.34160(12) 0.0450(3) Uani 1 1 d . . . C32 C -0.06512(19) 0.19114(17) 0.28315(19) 0.0846(7) Uani 1 1 d . . . H36A H -0.0681 0.2486 0.2170 0.127 Uiso 1 1 calc R . . H36B H -0.1392 0.1966 0.3244 0.127 Uiso 1 1 calc R . . H36C H -0.0495 0.1261 0.2748 0.127 Uiso 1 1 calc R . . C30 C -0.05821(13) 0.37616(13) 0.30446(13) 0.0534(4) Uani 1 1 d . . . H37 H -0.1199 0.3758 0.2736 0.064 Uiso 1 1 calc R . . C31 C -0.04982(15) 0.46582(13) 0.31277(14) 0.0575(4) Uani 1 1 d . . . H38 H -0.1067 0.5255 0.2890 0.069 Uiso 1 1 calc R . . C34 C 0.15704(11) 0.12179(11) 0.55265(12) 0.0414(3) Uani 1 1 d . . . C41 C 0.23604(13) 0.01910(13) 0.59527(14) 0.0523(4) Uani 1 1 d . . . N7 N 0.29570(14) -0.05943(13) 0.63016(16) 0.0819(5) Uani 1 1 d . . . C35 C 0.03764(13) 0.09902(12) 0.56452(13) 0.0465(4) Uani 1 1 d . . . N8 N -0.05297(12) 0.07882(12) 0.57647(13) 0.0656(4) Uani 1 1 d . . . C36 C 0.16273(12) 0.18250(11) 0.61627(12) 0.0431(3) Uani 1 1 d . . . C37 C 0.26243(12) 0.22373(12) 0.59394(12) 0.0438(3) Uani 1 1 d . . . N5 N 0.29402(14) 0.31994(15) 0.69789(15) 0.0791(5) Uani 1 1 d . . . C47 C 0.6193(2) 0.3440(2) 0.4558(2) 0.1049(9) Uani 1 1 d . . . H47 H 0.6431 0.4084 0.4153 0.126 Uiso 1 1 calc R . . C48 C 0.50825(19) 0.32958(18) 0.45277(18) 0.0919(8) Uani 1 1 d . . . H48 H 0.4577 0.3848 0.4104 0.110 Uiso 1 1 calc R . . C40 C 0.41087(13) 0.18959(14) 0.34493(13) 0.0520(4) Uani 1 1 d . . . H49A H 0.4860 0.2016 0.3492 0.078 Uiso 1 1 calc R . . H49B H 0.3822 0.2407 0.2818 0.078 Uiso 1 1 calc R . . H49C H 0.4190 0.1204 0.3468 0.078 Uiso 1 1 calc R . . N6 N 0.07368(12) 0.18676(13) 0.68898(12) 0.0662(4) Uani 1 1 d . . . H50A H 0.0762 0.2181 0.7273 0.079 Uiso 1 1 calc R . . H50B H 0.0139 0.1581 0.6973 0.079 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 O1 0.0875(11) 0.0636(9) 0.0886(11) -0.0082(7) -0.0075(8) -0.0293(8) O2 0.0426(7) 0.0927(10) 0.0763(9) -0.0470(8) 0.0021(6) 0.0004(6) O3 0.0791(9) 0.0475(7) 0.0858(10) -0.0252(6) -0.0295(7) 0.0034(6) O4 0.0473(6) 0.0619(7) 0.0678(8) -0.0256(6) -0.0230(5) -0.0093(5) C24 0.0375(7) 0.0471(8) 0.0433(8) -0.0193(7) -0.0089(6) -0.0062(6) C18 0.0351(7) 0.0421(7) 0.0419(8) -0.0146(6) -0.0110(6) -0.0046(6) C17 0.0312(7) 0.0437(8) 0.0410(8) -0.0179(6) -0.0051(6) -0.0049(6) C23 0.0311(7) 0.0495(8) 0.0465(9) -0.0208(7) -0.0073(6) -0.0032(6) N1 0.0440(8) 0.0732(9) 0.0689(10) -0.0413(8) -0.0069(7) 0.0015(7) C42 0.0339(8) 0.0680(10) 0.0586(10) -0.0301(9) -0.0115(7) -0.0035(7) C1 0.0900(18) 0.0570(12) 0.122(2) -0.0144(13) -0.0195(15) -0.0093(11) C2 0.0653(12) 0.0703(12) 0.0502(10) -0.0139(9) -0.0075(9) -0.0272(9) C3 0.0448(9) 0.0625(10) 0.0451(9) -0.0177(8) -0.0031(7) -0.0138(7) C4 0.0396(8) 0.0638(10) 0.0388(8) -0.0230(7) -0.0045(6) -0.0117(7) C5 0.0344(7) 0.0521(8) 0.0443(8) -0.0261(7) -0.0051(6) -0.0039(6) C6 0.0344(7) 0.0545(9) 0.0504(9) -0.0253(7) -0.0139(7) 0.0008(6) C7 0.0618(12) 0.0647(12) 0.0943(16) -0.0166(11) -0.0321(11) 0.0050(9) C8 0.0840(18) 0.0954(18) 0.122(2) -0.0385(16) -0.0605(17) 0.0369(15) C9 0.0472(12) 0.164(3) 0.118(2) -0.093(2) -0.0390(14) 0.0267(15) C10 0.0409(9) 0.0803(12) 0.0473(9) -0.0321(9) -0.0035(7) -0.0082(8) C11 0.0428(10) 0.1142(18) 0.0561(11) -0.0369(11) 0.0036(8) -0.0275(11) C12 0.0589(12) 0.0955(15) 0.0555(11) -0.0183(10) -0.0023(9) -0.0386(11) C13 0.0512(13) 0.124(2) 0.131(2) -0.0493(18) 0.0181(14) 0.0103(13) C14 0.0329(7) 0.0448(8) 0.0452(8) -0.0200(7) -0.0091(6) -0.0006(6) C15 0.0543(10) 0.0452(9) 0.0533(10) -0.0194(7) -0.0127(8) -0.0039(7) N3 0.0880(12) 0.0576(10) 0.0864(13) -0.0190(9) -0.0149(10) -0.0223(9) C16 0.0321(7) 0.0434(7) 0.0396(8) -0.0176(6) -0.0044(6) -0.0061(6) N2 0.0449(7) 0.0753(9) 0.0616(9) -0.0441(8) -0.0191(6) 0.0081(6) C19 0.0526(10) 0.0879(13) 0.0591(11) -0.0419(10) -0.0148(8) -0.0054(9) C20 0.0382(11) 0.159(3) 0.0958(18) -0.0658(18) -0.0016(11) -0.0205(13) C21 0.0414(9) 0.0943(14) 0.0680(12) -0.0274(11) -0.0065(8) -0.0155(9) C22 0.0434(9) 0.0585(9) 0.0522(10) -0.0297(8) -0.0138(7) 0.0058(7) N4 0.0497(9) 0.1011(12) 0.0854(12) -0.0556(10) -0.0286(8) 0.0195(8) C25 0.0807(14) 0.0611(11) 0.0880(15) -0.0326(11) -0.0186(11) -0.0129(10) C26 0.0478(9) 0.0463(9) 0.0532(10) -0.0161(7) -0.0108(7) -0.0011(7) C27 0.0363(8) 0.0505(9) 0.0491(9) -0.0184(7) -0.0107(6) -0.0047(6) C28 0.0296(7) 0.0474(8) 0.0430(8) -0.0148(7) -0.0094(6) -0.0018(6) C33 0.0317(7) 0.0469(8) 0.0475(9) -0.0214(7) -0.0100(6) -0.0023(6) C39 0.0295(7) 0.0438(8) 0.0446(8) -0.0144(6) -0.0086(6) -0.0017(6) C38 0.0281(7) 0.0505(8) 0.0454(8) -0.0158(7) -0.0091(6) -0.0040(6) C43 0.0297(7) 0.0675(10) 0.0435(9) -0.0211(8) -0.0054(6) -0.0097(7) C44 0.0393(9) 0.0679(11) 0.0757(13) -0.0263(10) -0.0185(8) 0.0006(8) C45 0.0370(9) 0.1022(16) 0.0843(15) -0.0403(13) -0.0214(9) 0.0008(10) C46 0.0398(10) 0.1311(19) 0.0743(14) -0.0434(14) -0.0063(9) -0.0273(11) C29 0.0343(7) 0.0524(9) 0.0458(9) -0.0146(7) -0.0084(6) -0.0092(6) C32 0.0738(13) 0.0807(13) 0.1139(18) -0.0314(13) -0.0451(13) -0.0246(11) C30 0.0339(8) 0.0653(10) 0.0536(10) -0.0145(8) -0.0154(7) -0.0045(7) C31 0.0434(9) 0.0514(9) 0.0623(11) -0.0118(8) -0.0159(8) 0.0068(7) C34 0.0256(7) 0.0416(7) 0.0533(9) -0.0164(7) -0.0080(6) -0.0012(5) C41 0.0339(8) 0.0470(9) 0.0682(11) -0.0158(8) -0.0095(7) -0.0037(7) N7 0.0513(9) 0.0566(10) 0.1136(15) -0.0135(9) -0.0222(9) 0.0050(8) C35 0.0338(8) 0.0453(8) 0.0576(10) -0.0192(7) -0.0086(7) -0.0017(6) N8 0.0379(8) 0.0745(10) 0.0876(12) -0.0344(9) -0.0074(7) -0.0114(7) C36 0.0313(7) 0.0496(8) 0.0443(8) -0.0166(7) -0.0071(6) -0.0014(6) C37 0.0324(7) 0.0548(9) 0.0452(9) -0.0205(7) -0.0098(6) -0.0038(6) N5 0.0560(9) 0.1087(13) 0.1027(14) -0.0702(12) -0.0243(9) -0.0015(9) C47 0.0778(16) 0.116(2) 0.0985(18) 0.0036(15) -0.0203(14) -0.0574(15) C48 0.0682(13) 0.0929(15) 0.0886(16) 0.0136(12) -0.0373(12) -0.0391(12) C40 0.0376(8) 0.0654(10) 0.0530(10) -0.0260(8) -0.0024(7) -0.0070(7) N6 0.0440(8) 0.0969(11) 0.0723(10) -0.0498(9) 0.0109(7) -0.0219(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.379(2) . ? O1 C1 1.414(3) . ? O2 C10 1.367(2) . ? O2 C13 1.418(2) . ? O3 C26 1.376(2) . ? O3 C25 1.416(2) . ? O4 C29 1.3674(19) . ? O4 C32 1.4144(19) . ? C24 C18 1.338(2) . ? C24 C19 1.501(2) . ? C24 C5 1.516(2) . ? C18 C17 1.4803(19) . ? C18 C6 1.4932(19) . ? C17 C16 1.3596(19) . ? C17 C23 1.423(2) . ? C23 N1 1.1473(19) . ? C42 N5 1.140(2) . ? C42 C37 1.422(2) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C12 1.382(3) . ? C2 C3 1.388(2) . ? C3 C4 1.382(2) . ? C3 H3 0.9300 . ? C4 C10 1.397(2) . ? C4 C5 1.523(2) . ? C5 C14 1.560(2) . ? C5 H5 0.9800 . ? C6 C21 1.374(2) . ? C6 C7 1.375(3) . ? C7 C8 1.389(3) . ? C7 H7 0.9300 . ? C8 C9 1.355(4) . ? C8 H8 0.9300 . ? C9 C20 1.357(4) . ? C9 H9 0.9300 . ? C10 C11 1.385(3) . ? C11 C12 1.367(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C22 1.482(2) . ? C14 C15 1.487(2) . ? C14 C16 1.5358(19) . ? C15 N3 1.134(2) . ? C16 N2 1.3354(18) . ? N2 H18A 0.8600 . ? N2 H18B 0.8600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.381(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 N4 1.1275(19) . ? C25 H24A 0.9600 . ? C25 H24B 0.9600 . ? C25 H24C 0.9600 . ? C26 C31 1.383(2) . ? C26 C27 1.386(2) . ? C27 C28 1.389(2) . ? C27 H26 0.9300 . ? C28 C29 1.3991(19) . ? C28 C33 1.5279(19) . ? C33 C39 1.5152(18) . ? C33 C34 1.565(2) . ? C33 H28 0.9800 . ? C39 C38 1.341(2) . ? C39 C40 1.492(2) . ? C38 C37 1.480(2) . ? C38 C43 1.4929(19) . ? C43 C48 1.363(3) . ? C43 C44 1.377(2) . ? C44 C45 1.382(2) . ? C44 H32 0.9300 . ? C45 C46 1.346(3) . ? C45 H33 0.9300 . ? C46 C47 1.363(3) . ? C46 H34 0.9300 . ? C29 C30 1.391(2) . ? C32 H36A 0.9600 . ? C32 H36B 0.9600 . ? C32 H36C 0.9600 . ? C30 C31 1.367(2) . ? C30 H37 0.9300 . ? C31 H38 0.9300 . ? C34 C35 1.4800(19) . ? C34 C41 1.486(2) . ? C34 C36 1.534(2) . ? C41 N7 1.137(2) . ? C35 N8 1.1332(19) . ? C36 N6 1.339(2) . ? C36 C37 1.359(2) . ? C47 C48 1.386(3) . ? C47 H47 0.9300 . ? C48 H48 0.9300 . ? C40 H49A 0.9600 . ? C40 H49B 0.9600 . ? C40 H49C 0.9600 . ? N6 H50A 0.8600 . ? N6 H50B 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C1 117.35(15) . . ? C10 O2 C13 119.15(17) . . ? C26 O3 C25 117.39(13) . . ? C29 O4 C32 117.96(14) . . ? C18 C24 C19 124.90(14) . . ? C18 C24 C5 119.60(12) . . ? C19 C24 C5 115.48(13) . . ? C24 C18 C17 120.45(12) . . ? C24 C18 C6 123.16(13) . . ? C17 C18 C6 116.36(12) . . ? C16 C17 C23 118.83(12) . . ? C16 C17 C18 122.37(12) . . ? C23 C17 C18 118.80(12) . . ? N1 C23 C17 178.71(18) . . ? N5 C42 C37 178.94(17) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C12 117.22(16) . . ? O1 C2 C3 123.66(17) . . ? C12 C2 C3 119.12(18) . . ? C4 C3 C2 120.93(16) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C10 119.34(15) . . ? C3 C4 C5 121.17(13) . . ? C10 C4 C5 119.48(14) . . ? C24 C5 C4 113.19(13) . . ? C24 C5 C14 108.92(11) . . ? C4 C5 C14 112.43(11) . . ? C24 C5 H5 107.3 . . ? C4 C5 H5 107.3 . . ? C14 C5 H5 107.3 . . ? C21 C6 C7 118.52(16) . . ? C21 C6 C18 120.68(15) . . ? C7 C6 C18 120.78(16) . . ? C6 C7 C8 120.1(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 120.7(2) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C20 C9 C8 119.5(2) . . ? C20 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? O2 C10 C11 125.32(16) . . ? O2 C10 C4 115.51(15) . . ? C11 C10 C4 119.16(17) . . ? C12 C11 C10 121.02(17) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C2 120.41(17) . . ? C11 C12 H12 119.8 . . ? C2 C12 H12 119.8 . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C22 C14 C15 107.13(13) . . ? C22 C14 C16 111.92(11) . . ? C15 C14 C16 105.92(12) . . ? C22 C14 C5 112.43(12) . . ? C15 C14 C5 108.39(11) . . ? C16 C14 C5 110.71(11) . . ? N3 C15 C14 179.02(19) . . ? N2 C16 C17 126.96(13) . . ? N2 C16 C14 118.03(12) . . ? C17 C16 C14 114.78(12) . . ? C16 N2 H18A 120.0 . . ? C16 N2 H18B 120.0 . . ? H18A N2 H18B 120.0 . . ? C24 C19 H19A 109.5 . . ? C24 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C24 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C9 C20 C21 120.6(2) . . ? C9 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C6 C21 C20 120.6(2) . . ? C6 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? N4 C22 C14 177.3(2) . . ? O3 C25 H24A 109.5 . . ? O3 C25 H24B 109.5 . . ? H24A C25 H24B 109.5 . . ? O3 C25 H24C 109.5 . . ? H24A C25 H24C 109.5 . . ? H24B C25 H24C 109.5 . . ? O3 C26 C31 116.25(14) . . ? O3 C26 C27 124.34(15) . . ? C31 C26 C27 119.40(15) . . ? C26 C27 C28 121.12(14) . . ? C26 C27 H26 119.4 . . ? C28 C27 H26 119.4 . . ? C27 C28 C29 118.64(13) . . ? C27 C28 C33 121.29(12) . . ? C29 C28 C33 120.06(13) . . ? C39 C33 C28 114.72(12) . . ? C39 C33 C34 107.86(11) . . ? C28 C33 C34 110.79(11) . . ? C39 C33 H28 107.7 . . ? C28 C33 H28 107.7 . . ? C34 C33 H28 107.7 . . ? C38 C39 C40 124.67(13) . . ? C38 C39 C33 118.94(13) . . ? C40 C39 C33 116.38(12) . . ? C39 C38 C37 120.11(12) . . ? C39 C38 C43 123.26(13) . . ? C37 C38 C43 116.63(12) . . ? C48 C43 C44 117.81(15) . . ? C48 C43 C38 121.85(15) . . ? C44 C43 C38 120.31(15) . . ? C43 C44 C45 121.26(19) . . ? C43 C44 H32 119.4 . . ? C45 C44 H32 119.4 . . ? C46 C45 C44 119.85(19) . . ? C46 C45 H33 120.1 . . ? C44 C45 H33 120.1 . . ? C45 C46 C47 120.14(17) . . ? C45 C46 H34 119.9 . . ? C47 C46 H34 119.9 . . ? O4 C29 C30 124.30(13) . . ? O4 C29 C28 115.99(13) . . ? C30 C29 C28 119.68(14) . . ? O4 C32 H36A 109.5 . . ? O4 C32 H36B 109.5 . . ? H36A C32 H36B 109.5 . . ? O4 C32 H36C 109.5 . . ? H36A C32 H36C 109.5 . . ? H36B C32 H36C 109.5 . . ? C31 C30 C29 120.75(15) . . ? C31 C30 H37 119.6 . . ? C29 C30 H37 119.6 . . ? C30 C31 C26 120.32(15) . . ? C30 C31 H38 119.8 . . ? C26 C31 H38 119.8 . . ? C35 C34 C41 106.98(12) . . ? C35 C34 C36 111.83(12) . . ? C41 C34 C36 106.33(12) . . ? C35 C34 C33 112.03(12) . . ? C41 C34 C33 109.99(12) . . ? C36 C34 C33 109.48(11) . . ? N7 C41 C34 178.4(2) . . ? N8 C35 C34 177.76(18) . . ? N6 C36 C37 126.83(14) . . ? N6 C36 C34 118.28(13) . . ? C37 C36 C34 114.85(13) . . ? C36 C37 C42 119.35(14) . . ? C36 C37 C38 122.11(13) . . ? C42 C37 C38 118.50(13) . . ? C46 C47 C48 119.9(2) . . ? C46 C47 H47 120.0 . . ? C48 C47 H47 120.0 . . ? C43 C48 C47 121.0(2) . . ? C43 C48 H48 119.5 . . ? C47 C48 H48 119.5 . . ? C39 C40 H49A 109.5 . . ? C39 C40 H49B 109.5 . . ? H49A C40 H49B 109.5 . . ? C39 C40 H49C 109.5 . . ? H49A C40 H49C 109.5 . . ? H49B C40 H49C 109.5 . . ? C36 N6 H50A 120.0 . . ? C36 N6 H50B 120.0 . . ? H50A N6 H50B 120.0 . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 29.12 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.204 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.036