# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email zdenek.travnicek@upol.cz _publ_contact_author_name 'Zdenek Travnicek' loop_ _publ_author_name 'Roman Buchtik' 'Zdenek Travnicek' 'Jan Vanco' 'Radovan Herchel' 'Zdenek Dvorak' data_r _database_code_depnum_ccdc_archive 'CCDC 822513' #TrackingRef '- deposit_Hqui.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 N O2' _chemical_formula_weight 237.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' 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' _cell_length_a 9.8636(3) _cell_length_b 12.9003(4) _cell_length_c 17.8871(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2276.02(12) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13100 _cell_measurement_theta_min 3.0643 _cell_measurement_theta_max 33.3172 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9817 _exptl_absorpt_correction_T_max 0.9963 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3611 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20502 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3776 _reflns_number_gt 3384 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0440P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 3776 _refine_ls_number_parameters 326 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0612 _refine_ls_wR_factor_gt 0.0601 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _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 N1 N 0.57376(13) 0.17606(9) 0.49658(7) 0.0157(3) Uani 1 1 d . . . H1A H 0.5466 0.1140 0.5104 0.019 Uiso 1 1 calc R . . O1 O 0.77996(11) 0.38237(8) 0.57126(6) 0.0194(3) Uani 1 1 d . . . H1 H 0.8208 0.4289 0.5474 0.023 Uiso 1 1 calc R . . O2 O 0.67272(11) 0.47374(7) 0.44632(6) 0.0201(3) Uani 1 1 d . . . N1A N 1.04513(13) 0.83413(9) 0.49347(7) 0.0174(3) Uani 1 1 d . . . H1AA H 1.0568 0.9015 0.4890 0.021 Uiso 1 1 calc R . . O1A O 0.83484(10) 0.63557(8) 0.41311(6) 0.0198(3) Uani 1 1 d . . . H1B H 0.8147 0.5777 0.4315 0.024 Uiso 1 1 calc R . . O2A O 0.97611(10) 0.52490(7) 0.51647(6) 0.0181(2) Uani 1 1 d . . . C13 C 0.64553(16) 0.37884(11) 0.45903(8) 0.0155(3) Uani 1 1 d . . . C13A C 1.00452(16) 0.62064(11) 0.50818(9) 0.0158(3) Uani 1 1 d . . . C14 C 0.69655(15) 0.32876(12) 0.52373(8) 0.0156(3) Uani 1 1 d . . . C14A C 0.93176(16) 0.68130(11) 0.45571(8) 0.0159(3) Uani 1 1 d . . . C15 C 0.65844(14) 0.22946(11) 0.54248(8) 0.0149(3) Uani 1 1 d . . . C15A C 0.95148(16) 0.78698(12) 0.44902(8) 0.0164(3) Uani 1 1 d . . . C16 C 0.52881(15) 0.21482(11) 0.42968(8) 0.0147(3) Uani 1 1 d . . . C16A C 1.12178(16) 0.78151(11) 0.54468(8) 0.0165(3) Uani 1 1 d . . . C17 C 0.56470(15) 0.31642(11) 0.40926(9) 0.0151(3) Uani 1 1 d . . . C17A C 1.10654(15) 0.67329(11) 0.55182(8) 0.0155(3) Uani 1 1 d . . . C18 C 0.52058(17) 0.35352(12) 0.33901(9) 0.0199(4) Uani 1 1 d . . . H18A H 0.5427 0.4222 0.3242 0.024 Uiso 1 1 calc R . . C18A C 1.19074(16) 0.62097(12) 0.60258(8) 0.0185(4) Uani 1 1 d . . . H18B H 1.1819 0.5481 0.6082 0.022 Uiso 1 1 calc R . . C19 C 0.44656(16) 0.29206(13) 0.29220(9) 0.0215(4) Uani 1 1 d . . . H19A H 0.4189 0.3177 0.2448 0.026 Uiso 1 1 calc R . . C19A C 1.28519(17) 0.67281(13) 0.64409(9) 0.0201(4) Uani 1 1 d . . . H19B H 1.3435 0.6356 0.6768 0.024 Uiso 1 1 calc R . . C20 C 0.41133(16) 0.19122(12) 0.31387(9) 0.0199(4) Uani 1 1 d . . . H20A H 0.3592 0.1491 0.2811 0.024 Uiso 1 1 calc R . . C20A C 1.29612(16) 0.78131(12) 0.63840(9) 0.0197(4) Uani 1 1 d . . . H20B H 1.3600 0.8175 0.6684 0.024 Uiso 1 1 calc R . . C21 C 0.45092(16) 0.15283(12) 0.38143(9) 0.0187(4) Uani 1 1 d . . . H21A H 0.4260 0.0846 0.3958 0.022 Uiso 1 1 calc R . . C21A C 1.21513(16) 0.83478(12) 0.58981(8) 0.0185(4) Uani 1 1 d . . . H21B H 1.2220 0.9081 0.5866 0.022 Uiso 1 1 calc R . . C22 C 0.69946(16) 0.17630(11) 0.61246(8) 0.0164(3) Uani 1 1 d . . . C22A C 0.87263(15) 0.85469(12) 0.39883(8) 0.0174(4) Uani 1 1 d . . . C23 C 0.60163(17) 0.13970(11) 0.66183(9) 0.0184(4) Uani 1 1 d . . . H23A H 0.5082 0.1477 0.6503 0.022 Uiso 1 1 calc R . . C23A C 0.82866(16) 0.95170(12) 0.42296(9) 0.0222(4) Uani 1 1 d . . . H23B H 0.8497 0.9744 0.4721 0.027 Uiso 1 1 calc R . . C24 C 0.63988(18) 0.09172(12) 0.72775(9) 0.0216(4) Uani 1 1 d . . . H24A H 0.5727 0.0671 0.7614 0.026 Uiso 1 1 calc R . . C24A C 0.75493(17) 1.01495(13) 0.37604(10) 0.0276(4) Uani 1 1 d . . . H24B H 0.7262 1.0812 0.3930 0.033 Uiso 1 1 calc R . . C25 C 0.77556(18) 0.07961(13) 0.74475(9) 0.0256(4) Uani 1 1 d . . . H25A H 0.8016 0.0482 0.7906 0.031 Uiso 1 1 calc R . . C25A C 0.72234(17) 0.98274(14) 0.30442(10) 0.0286(4) Uani 1 1 d . . . H25B H 0.6703 1.0262 0.2725 0.034 Uiso 1 1 calc R . . C26 C 0.87349(18) 0.11322(13) 0.69507(10) 0.0266(4) Uani 1 1 d . . . H26A H 0.9667 0.1030 0.7061 0.032 Uiso 1 1 calc R . . C26A C 0.76606(18) 0.88716(14) 0.27973(10) 0.0284(4) Uani 1 1 d . . . H26B H 0.7450 0.8649 0.2304 0.034 Uiso 1 1 calc R . . C27 C 0.83592(18) 0.16180(12) 0.62912(9) 0.0221(4) Uani 1 1 d . . . H27A H 0.9035 0.1852 0.5952 0.026 Uiso 1 1 calc R . . C27A C 0.84051(18) 0.82355(13) 0.32663(9) 0.0240(4) Uani 1 1 d . . . H27B H 0.8700 0.7577 0.3092 0.029 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 N1 0.0172(7) 0.0120(6) 0.0177(7) 0.0011(6) 0.0001(6) -0.0020(5) O1 0.0217(6) 0.0145(6) 0.0219(6) -0.0001(5) -0.0028(5) -0.0070(5) O2 0.0203(6) 0.0120(5) 0.0278(6) 0.0023(5) -0.0014(5) -0.0019(5) N1A 0.0199(7) 0.0108(6) 0.0215(7) 0.0002(6) 0.0003(6) -0.0015(6) O1A 0.0232(6) 0.0147(5) 0.0215(6) 0.0040(4) -0.0032(5) -0.0063(5) O2A 0.0196(6) 0.0104(5) 0.0244(6) 0.0007(5) -0.0007(5) 0.0007(4) C13 0.0131(8) 0.0125(8) 0.0209(9) 0.0011(7) 0.0041(7) 0.0007(7) C13A 0.0172(8) 0.0141(8) 0.0163(8) -0.0009(7) 0.0051(7) 0.0018(6) C14 0.0134(8) 0.0167(8) 0.0167(8) -0.0033(6) 0.0011(6) -0.0012(6) C14A 0.0167(8) 0.0160(8) 0.0149(8) -0.0007(7) 0.0016(7) 0.0000(7) C15 0.0133(8) 0.0141(8) 0.0173(8) -0.0013(6) -0.0004(7) 0.0021(6) C15A 0.0179(9) 0.0165(8) 0.0147(8) -0.0017(7) 0.0047(7) -0.0002(7) C16 0.0133(8) 0.0157(8) 0.0151(8) 0.0007(7) 0.0022(6) 0.0017(7) C16A 0.0169(8) 0.0163(7) 0.0164(8) 0.0001(7) 0.0048(7) 0.0006(7) C17 0.0125(8) 0.0147(8) 0.0182(8) -0.0001(7) 0.0019(7) 0.0010(6) C17A 0.0173(8) 0.0156(8) 0.0137(7) -0.0007(7) 0.0046(7) 0.0009(6) C18 0.0211(9) 0.0168(8) 0.0218(8) 0.0041(7) 0.0023(7) -0.0003(7) C18A 0.0221(9) 0.0150(8) 0.0185(9) 0.0005(7) 0.0024(7) 0.0006(7) C19 0.0226(9) 0.0241(9) 0.0177(8) 0.0049(7) -0.0022(7) -0.0008(7) C19A 0.0208(8) 0.0226(9) 0.0169(8) 0.0021(7) 0.0006(7) 0.0008(7) C20 0.0176(8) 0.0216(8) 0.0204(9) -0.0028(7) -0.0026(7) -0.0026(7) C20A 0.0177(9) 0.0249(9) 0.0163(8) -0.0020(7) 0.0021(7) -0.0051(7) C21 0.0187(9) 0.0147(8) 0.0226(9) 0.0008(7) 0.0011(7) -0.0019(7) C21A 0.0206(8) 0.0146(8) 0.0202(8) -0.0018(7) 0.0050(7) -0.0053(7) C22 0.0201(9) 0.0102(7) 0.0187(8) -0.0023(7) -0.0023(7) -0.0015(6) C22A 0.0151(8) 0.0153(8) 0.0219(9) 0.0035(7) 0.0031(7) -0.0033(7) C23 0.0204(9) 0.0136(8) 0.0211(9) -0.0032(6) -0.0013(7) 0.0003(7) C23A 0.0219(9) 0.0209(9) 0.0239(9) -0.0008(7) 0.0047(7) 0.0011(7) C24 0.0322(10) 0.0153(8) 0.0174(8) -0.0008(7) 0.0014(7) 0.0009(7) C24A 0.0241(9) 0.0230(9) 0.0357(11) 0.0059(8) 0.0080(8) 0.0086(8) C25 0.0388(11) 0.0196(9) 0.0184(9) -0.0001(7) -0.0056(8) 0.0062(8) C25A 0.0207(9) 0.0303(10) 0.0348(11) 0.0138(8) -0.0022(8) 0.0031(8) C26 0.0239(9) 0.0222(9) 0.0338(10) -0.0042(8) -0.0121(8) 0.0041(8) C26A 0.0308(10) 0.0292(10) 0.0251(10) 0.0049(8) -0.0060(8) -0.0047(8) C27 0.0220(9) 0.0202(9) 0.0240(9) -0.0010(7) -0.0012(7) -0.0015(7) C27A 0.0303(10) 0.0174(8) 0.0242(9) 0.0022(7) -0.0005(8) -0.0024(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 N1 C15 1.3588(19) . ? N1 C16 1.371(2) . ? N1 H1A 0.8800 . ? O1 C14 1.3704(18) . ? O1 H1 0.8400 . ? O2 C13 1.2738(17) . ? N1A C15A 1.362(2) . ? N1A C16A 1.3680(19) . ? N1A H1AA 0.8800 . ? O1A C14A 1.3573(18) . ? O1A H1B 0.8400 . ? O2A C13A 1.2752(16) . ? C13 C14 1.418(2) . ? C13 C17 1.441(2) . ? C13A C14A 1.417(2) . ? C13A C17A 1.443(2) . ? C14 C15 1.377(2) . ? C14A C15A 1.382(2) . ? C15 C22 1.484(2) . ? C15A C22A 1.474(2) . ? C16 C21 1.405(2) . ? C16 C17 1.406(2) . ? C16A C21A 1.404(2) . ? C16A C17A 1.410(2) . ? C17 C18 1.413(2) . ? C17A C18A 1.403(2) . ? C18 C19 1.365(2) . ? C18 H18A 0.9500 . ? C18A C19A 1.366(2) . ? C18A H18B 0.9500 . ? C19 C20 1.401(2) . ? C19 H19A 0.9500 . ? C19A C20A 1.408(2) . ? C19A H19B 0.9500 . ? C20 C21 1.363(2) . ? C20 H20A 0.9500 . ? C20A C21A 1.367(2) . ? C20A H20B 0.9500 . ? C21 H21A 0.9500 . ? C21A H21B 0.9500 . ? C22 C23 1.391(2) . ? C22 C27 1.391(2) . ? C22A C27A 1.389(2) . ? C22A C23A 1.393(2) . ? C23 C24 1.384(2) . ? C23 H23A 0.9500 . ? C23A C24A 1.378(2) . ? C23A H23B 0.9500 . ? C24 C25 1.381(2) . ? C24 H24A 0.9500 . ? C24A C25A 1.385(3) . ? C24A H24B 0.9500 . ? C25 C26 1.382(2) . ? C25 H25A 0.9500 . ? C25A C26A 1.379(3) . ? C25A H25B 0.9500 . ? C26 C27 1.386(2) . ? C26 H26A 0.9500 . ? C26A C27A 1.384(2) . ? C26A H26B 0.9500 . ? C27 H27A 0.9500 . ? C27A H27B 0.9500 . ? 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 C15 N1 C16 122.78(12) . . ? C15 N1 H1A 118.6 . . ? C16 N1 H1A 118.6 . . ? C14 O1 H1 109.5 . . ? C15A N1A C16A 122.97(12) . . ? C15A N1A H1AA 118.5 . . ? C16A N1A H1AA 118.5 . . ? C14A O1A H1B 109.5 . . ? O2 C13 C14 120.59(14) . . ? O2 C13 C17 122.91(13) . . ? C14 C13 C17 116.49(13) . . ? O2A C13A C14A 120.04(14) . . ? O2A C13A C17A 123.10(14) . . ? C14A C13A C17A 116.83(12) . . ? O1 C14 C15 118.84(13) . . ? O1 C14 C13 119.31(13) . . ? C15 C14 C13 121.74(14) . . ? O1A C14A C15A 118.63(13) . . ? O1A C14A C13A 119.24(13) . . ? C15A C14A C13A 122.05(14) . . ? N1 C15 C14 119.50(13) . . ? N1 C15 C22 116.30(13) . . ? C14 C15 C22 124.15(14) . . ? N1A C15A C14A 119.03(14) . . ? N1A C15A C22A 116.66(13) . . ? C14A C15A C22A 124.25(14) . . ? N1 C16 C21 120.37(13) . . ? N1 C16 C17 119.04(13) . . ? C21 C16 C17 120.57(13) . . ? N1A C16A C21A 120.31(13) . . ? N1A C16A C17A 119.54(14) . . ? C21A C16A C17A 120.16(14) . . ? C16 C17 C18 117.98(13) . . ? C16 C17 C13 119.99(13) . . ? C18 C17 C13 122.03(13) . . ? C18A C17A C16A 118.14(14) . . ? C18A C17A C13A 122.42(13) . . ? C16A C17A C13A 119.43(14) . . ? C19 C18 C17 120.90(14) . . ? C19 C18 H18A 119.5 . . ? C17 C18 H18A 119.5 . . ? C19A C18A C17A 121.31(14) . . ? C19A C18A H18B 119.3 . . ? C17A C18A H18B 119.3 . . ? C18 C19 C20 120.14(15) . . ? C18 C19 H19A 119.9 . . ? C20 C19 H19A 119.9 . . ? C18A C19A C20A 119.98(15) . . ? C18A C19A H19B 120.0 . . ? C20A C19A H19B 120.0 . . ? C21 C20 C19 120.77(14) . . ? C21 C20 H20A 119.6 . . ? C19 C20 H20A 119.6 . . ? C21A C20A C19A 120.19(15) . . ? C21A C20A H20B 119.9 . . ? C19A C20A H20B 119.9 . . ? C20 C21 C16 119.63(14) . . ? C20 C21 H21A 120.2 . . ? C16 C21 H21A 120.2 . . ? C20A C21A C16A 120.11(14) . . ? C20A C21A H21B 119.9 . . ? C16A C21A H21B 119.9 . . ? C23 C22 C27 119.32(14) . . ? C23 C22 C15 120.23(14) . . ? C27 C22 C15 120.45(14) . . ? C27A C22A C23A 118.48(14) . . ? C27A C22A C15A 121.01(14) . . ? C23A C22A C15A 120.51(14) . . ? C24 C23 C22 120.24(15) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C24A C23A C22A 120.50(15) . . ? C24A C23A H23B 119.7 . . ? C22A C23A H23B 119.7 . . ? C25 C24 C23 120.15(16) . . ? C25 C24 H24A 119.9 . . ? C23 C24 H24A 119.9 . . ? C23A C24A C25A 120.55(16) . . ? C23A C24A H24B 119.7 . . ? C25A C24A H24B 119.7 . . ? C24 C25 C26 120.01(15) . . ? C24 C25 H25A 120.0 . . ? C26 C25 H25A 120.0 . . ? C26A C25A C24A 119.48(16) . . ? C26A C25A H25B 120.3 . . ? C24A C25A H25B 120.3 . . ? C25 C26 C27 120.14(16) . . ? C25 C26 H26A 119.9 . . ? C27 C26 H26A 119.9 . . ? C25A C26A C27A 120.12(16) . . ? C25A C26A H26B 119.9 . . ? C27A C26A H26B 119.9 . . ? C26 C27 C22 120.11(16) . . ? C26 C27 H27A 119.9 . . ? C22 C27 H27A 119.9 . . ? C26A C27A C22A 120.86(16) . . ? C26A C27A H27B 119.6 . . ? C22A C27A H27B 119.6 . . ? 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 H1A O2A 0.88 1.92 2.7883(15) 166.7 3_455 O1A H1B O2 0.84 1.96 2.6960(14) 146.2 . O1 H1 O2A 0.84 2.05 2.8432(14) 158.3 . N1A H1AA O2 0.88 2.12 2.9049(16) 148.7 3_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.158 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.030 # Attachment '- deposit_complex_2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 822514' #TrackingRef '- deposit_complex_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H20 Cu N4 O6' _chemical_formula_weight 560.01 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' 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 17.5992(5) _cell_length_b 7.17851(19) _cell_length_c 19.0423(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.443(3) _cell_angle_gamma 90.00 _cell_volume 2239.19(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10866 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 33.30 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1148 _exptl_absorpt_coefficient_mu 1.032 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7140 _exptl_absorpt_correction_T_max 0.9038 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _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 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3611 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18461 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3939 _reflns_number_gt 2967 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0527P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3939 _refine_ls_number_parameters 353 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0817 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.952 _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 Cu1 Cu 0.556078(17) 0.20541(4) 0.947325(16) 0.01162(11) Uani 1 1 d . . . N2 N 0.66655(12) 0.2148(3) 0.94293(11) 0.0112(4) Uani 1 1 d . . . N3 N 0.52544(12) 0.1141(3) 0.84200(11) 0.0109(5) Uani 1 1 d . . . N1 N 0.45852(12) 0.3967(3) 1.15099(11) 0.0115(5) Uani 1 1 d . . . H1 H 0.4617 0.4395 1.1953 0.014 Uiso 1 1 calc R . . N4 N 0.54253(13) 0.4329(3) 0.65120(13) 0.0207(5) Uani 1 1 d . . . O2 O 0.44880(9) 0.1868(2) 0.95052(9) 0.0129(4) Uani 1 1 d . . . O1 O 0.58916(9) 0.3051(2) 1.04597(9) 0.0117(4) Uani 1 1 d . . . O3 O 0.47027(13) 0.4671(4) 0.61281(12) 0.0523(7) Uani 1 1 d . . . O4 O 0.58390(12) 0.3419(3) 0.62299(10) 0.0283(5) Uani 1 1 d . . . O5 O 0.57336(11) 0.4871(3) 0.71788(11) 0.0355(6) Uani 1 1 d . . . O6 O 0.51200(18) 0.1835(6) 0.47654(14) 0.0628(9) Uani 1 1 d D . . H1W H 0.528(2) 0.242(5) 0.5188(15) 0.075 Uiso 1 1 d D . . H1V H 0.516(5) 0.067(5) 0.493(4) 0.075 Uiso 0.63(5) 1 d PD A 1 H1U H 0.515(7) 0.291(9) 0.454(6) 0.075 Uiso 0.37(5) 1 d PD A 2 C1 C 0.73644(15) 0.2701(3) 0.99585(14) 0.0143(6) Uani 1 1 d . . . H1A H 0.7356 0.3196 1.0418 0.017 Uiso 1 1 calc R . . C2 C 0.81067(15) 0.2572(3) 0.98544(14) 0.0165(6) Uani 1 1 d . . . H2A H 0.8596 0.2961 1.0243 0.020 Uiso 1 1 calc R . . C3 C 0.81312(16) 0.1886(3) 0.91942(14) 0.0172(6) Uani 1 1 d . . . H3A H 0.8638 0.1786 0.9125 0.021 Uiso 1 1 calc R . . C4 C 0.73988(15) 0.1324(4) 0.86131(14) 0.0151(6) Uani 1 1 d . . . C5 C 0.66849(15) 0.1489(3) 0.87686(13) 0.0129(6) Uani 1 1 d . . . C6 C 0.59171(15) 0.0950(3) 0.82151(13) 0.0125(6) Uani 1 1 d . . . C7 C 0.58695(15) 0.0281(4) 0.75127(14) 0.0154(6) Uani 1 1 d . . . C8 C 0.66161(16) 0.0109(4) 0.73733(14) 0.0189(6) Uani 1 1 d . . . H8A H 0.6597 -0.0349 0.6899 0.023 Uiso 1 1 calc R . . C9 C 0.73432(16) 0.0583(4) 0.79004(14) 0.0191(6) Uani 1 1 d . . . H9A H 0.7827 0.0421 0.7795 0.023 Uiso 1 1 calc R . . C10 C 0.45219(15) 0.0705(3) 0.79149(14) 0.0149(6) Uani 1 1 d . . . H10A H 0.4055 0.0832 0.8048 0.018 Uiso 1 1 calc R . . C11 C 0.44252(16) 0.0067(4) 0.71962(14) 0.0178(6) Uani 1 1 d . . . H11A H 0.3894 -0.0211 0.6846 0.021 Uiso 1 1 calc R . . C12 C 0.50900(16) -0.0163(4) 0.69894(14) 0.0188(6) Uani 1 1 d . . . H12A H 0.5024 -0.0614 0.6502 0.023 Uiso 1 1 calc R . . C13 C 0.44897(15) 0.2549(3) 1.01355(13) 0.0112(6) Uani 1 1 d . . . C14 C 0.52519(14) 0.3197(3) 1.06671(13) 0.0102(5) Uani 1 1 d . . . C15 C 0.52863(14) 0.3918(3) 1.13532(13) 0.0095(5) Uani 1 1 d . . . C16 C 0.38354(15) 0.3387(3) 1.10171(13) 0.0117(6) Uani 1 1 d . . . C17 C 0.37714(14) 0.2677(3) 1.03106(13) 0.0107(5) Uani 1 1 d . . . C18 C 0.29891(14) 0.2147(3) 0.97959(13) 0.0127(5) Uani 1 1 d . . . H18A H 0.2932 0.1675 0.9313 0.015 Uiso 1 1 calc R . . C19 C 0.23184(15) 0.2311(3) 0.99908(14) 0.0149(6) Uani 1 1 d . . . H19A H 0.1796 0.1965 0.9641 0.018 Uiso 1 1 calc R . . C20 C 0.23977(15) 0.2989(3) 1.07073(14) 0.0147(6) Uani 1 1 d . . . H20A H 0.1928 0.3084 1.0838 0.018 Uiso 1 1 calc R . . C21 C 0.31442(15) 0.3517(3) 1.12199(14) 0.0137(6) Uani 1 1 d . . . H21A H 0.3193 0.3963 1.1704 0.016 Uiso 1 1 calc R . . C22 C 0.60279(14) 0.4665(3) 1.19443(13) 0.0102(5) Uani 1 1 d . . . C23 C 0.60937(15) 0.4697(3) 1.26942(13) 0.0123(6) Uani 1 1 d . . . H23A H 0.5668 0.4188 1.2829 0.015 Uiso 1 1 calc R . . C24 C 0.67717(15) 0.5462(3) 1.32454(14) 0.0132(6) Uani 1 1 d . . . H24A H 0.6805 0.5484 1.3755 0.016 Uiso 1 1 calc R . . C25 C 0.74014(15) 0.6194(3) 1.30616(14) 0.0151(6) Uani 1 1 d . . . H25A H 0.7871 0.6697 1.3443 0.018 Uiso 1 1 calc R . . C26 C 0.73388(15) 0.6185(4) 1.23163(14) 0.0148(6) Uani 1 1 d . . . H26A H 0.7766 0.6705 1.2185 0.018 Uiso 1 1 calc R . . C27 C 0.66599(15) 0.5424(3) 1.17563(14) 0.0125(6) Uani 1 1 d . . . H27A H 0.6625 0.5421 1.1247 0.015 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 Cu1 0.00945(17) 0.01670(18) 0.00961(17) -0.00067(13) 0.00455(12) 0.00022(14) N2 0.0147(11) 0.0121(11) 0.0077(10) 0.0018(9) 0.0051(9) 0.0001(9) N3 0.0078(11) 0.0124(11) 0.0130(11) 0.0013(9) 0.0043(9) 0.0010(9) N1 0.0102(11) 0.0172(12) 0.0076(11) -0.0024(9) 0.0040(9) -0.0007(9) N4 0.0135(13) 0.0317(14) 0.0193(13) 0.0000(11) 0.0087(11) -0.0037(11) O2 0.0115(9) 0.0199(10) 0.0085(9) -0.0027(7) 0.0052(7) -0.0004(8) O1 0.0053(8) 0.0194(10) 0.0117(9) -0.0012(7) 0.0046(7) -0.0005(7) O3 0.0223(13) 0.112(2) 0.0234(12) -0.0022(13) 0.0087(10) 0.0178(13) O4 0.0275(11) 0.0390(13) 0.0231(11) -0.0054(9) 0.0149(9) 0.0062(9) O5 0.0176(11) 0.0694(16) 0.0224(12) -0.0254(11) 0.0108(9) -0.0119(10) O6 0.0522(17) 0.110(3) 0.0248(14) 0.0007(16) 0.0127(12) 0.030(2) C1 0.0153(14) 0.0153(14) 0.0107(13) 0.0015(10) 0.0028(11) 0.0002(11) C2 0.0117(14) 0.0172(15) 0.0189(15) 0.0041(11) 0.0033(11) -0.0017(11) C3 0.0131(14) 0.0199(15) 0.0218(15) 0.0079(12) 0.0103(11) 0.0021(12) C4 0.0150(14) 0.0167(14) 0.0154(14) 0.0057(11) 0.0077(11) 0.0022(11) C5 0.0130(14) 0.0145(14) 0.0130(13) 0.0055(10) 0.0068(11) 0.0033(11) C6 0.0148(14) 0.0119(14) 0.0119(13) 0.0032(10) 0.0062(11) 0.0029(11) C7 0.0179(15) 0.0173(14) 0.0131(14) 0.0019(11) 0.0081(11) 0.0028(11) C8 0.0227(16) 0.0237(16) 0.0146(14) 0.0010(12) 0.0118(12) 0.0047(12) C9 0.0188(15) 0.0229(15) 0.0222(16) 0.0051(12) 0.0152(13) 0.0061(12) C10 0.0138(14) 0.0136(14) 0.0181(15) 0.0029(11) 0.0068(12) 0.0002(11) C11 0.0165(14) 0.0197(15) 0.0147(14) -0.0025(11) 0.0028(11) -0.0022(12) C12 0.0261(16) 0.0207(15) 0.0100(14) 0.0004(11) 0.0071(12) 0.0010(12) C13 0.0115(13) 0.0124(14) 0.0096(13) 0.0030(10) 0.0039(10) 0.0026(10) C14 0.0087(12) 0.0106(14) 0.0106(13) 0.0035(10) 0.0029(10) 0.0025(10) C15 0.0089(13) 0.0101(13) 0.0102(13) 0.0023(10) 0.0041(10) 0.0005(10) C16 0.0105(13) 0.0127(14) 0.0111(13) 0.0039(10) 0.0028(10) 0.0010(10) C17 0.0117(13) 0.0089(13) 0.0112(13) 0.0023(10) 0.0037(10) -0.0003(10) C18 0.0146(13) 0.0134(13) 0.0095(12) 0.0013(11) 0.0036(10) 0.0005(11) C19 0.0076(13) 0.0176(14) 0.0159(14) 0.0022(11) -0.0001(10) -0.0020(11) C20 0.0112(13) 0.0168(14) 0.0196(14) 0.0034(12) 0.0096(11) 0.0005(12) C21 0.0145(14) 0.0161(14) 0.0133(14) 0.0015(11) 0.0083(11) -0.0007(11) C22 0.0091(13) 0.0099(13) 0.0114(13) 0.0007(10) 0.0036(10) 0.0037(10) C23 0.0106(13) 0.0125(14) 0.0154(14) 0.0021(11) 0.0067(11) 0.0037(11) C24 0.0139(14) 0.0152(14) 0.0092(13) -0.0020(10) 0.0026(11) 0.0034(11) C25 0.0116(14) 0.0135(14) 0.0160(14) -0.0021(11) -0.0001(11) 0.0002(11) C26 0.0094(13) 0.0164(14) 0.0192(15) 0.0007(11) 0.0058(11) -0.0004(11) C27 0.0126(13) 0.0127(14) 0.0119(13) 0.0013(10) 0.0042(11) 0.0029(11) _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 Cu1 O1 1.8919(16) . ? Cu1 O2 1.9157(16) . ? Cu1 N2 1.978(2) . ? Cu1 N3 1.9880(19) . ? N2 C1 1.334(3) . ? N2 C5 1.356(3) . ? N3 C10 1.334(3) . ? N3 C6 1.365(3) . ? N1 C15 1.372(3) . ? N1 C16 1.375(3) . ? N1 H1 0.8800 . ? N4 O3 1.238(3) . ? N4 O4 1.237(3) . ? N4 O5 1.247(3) . ? O2 C13 1.295(3) . ? O1 C14 1.327(3) . ? O6 H1W 0.857(19) . ? O6 H1V 0.89(2) . ? O6 H1U 0.90(2) . ? C1 C2 1.394(4) . ? C1 H1A 0.9500 . ? C2 C3 1.365(4) . ? C2 H2A 0.9500 . ? C3 C4 1.416(4) . ? C3 H3A 0.9500 . ? C4 C5 1.397(3) . ? C4 C9 1.427(4) . ? C5 C6 1.430(3) . ? C6 C7 1.394(3) . ? C7 C12 1.406(4) . ? C7 C8 1.438(4) . ? C8 C9 1.350(4) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C11 1.393(3) . ? C10 H10A 0.9500 . ? C11 C12 1.374(4) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C17 1.423(3) . ? C13 C14 1.431(3) . ? C14 C15 1.386(3) . ? C15 C22 1.478(3) . ? C16 C17 1.404(3) . ? C16 C21 1.408(3) . ? C17 C18 1.419(3) . ? C18 C19 1.366(3) . ? C18 H18A 0.9500 . ? C19 C20 1.407(3) . ? C19 H19A 0.9500 . ? C20 C21 1.373(3) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C23 1.390(3) . ? C22 C27 1.398(3) . ? C23 C24 1.382(3) . ? C23 H23A 0.9500 . ? C24 C25 1.382(4) . ? C24 H24A 0.9500 . ? C25 C26 1.383(3) . ? C25 H25A 0.9500 . ? C26 C27 1.390(3) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? 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 O1 Cu1 O2 86.80(7) . . ? O1 Cu1 N2 94.51(7) . . ? O2 Cu1 N2 177.87(8) . . ? O1 Cu1 N3 176.22(8) . . ? O2 Cu1 N3 95.85(7) . . ? N2 Cu1 N3 82.92(8) . . ? C1 N2 C5 118.4(2) . . ? C1 N2 Cu1 128.86(17) . . ? C5 N2 Cu1 112.70(15) . . ? C10 N3 C6 118.1(2) . . ? C10 N3 Cu1 129.73(17) . . ? C6 N3 Cu1 112.12(15) . . ? C15 N1 C16 124.0(2) . . ? C15 N1 H1 118.0 . . ? C16 N1 H1 118.0 . . ? O3 N4 O4 119.3(2) . . ? O3 N4 O5 120.7(2) . . ? O4 N4 O5 120.1(2) . . ? C13 O2 Cu1 109.55(14) . . ? C14 O1 Cu1 109.81(14) . . ? H1W O6 H1V 100(6) . . ? H1W O6 H1U 88(8) . . ? H1V O6 H1U 167(8) . . ? N2 C1 C2 121.7(2) . . ? N2 C1 H1A 119.1 . . ? C2 C1 H1A 119.1 . . ? C3 C2 C1 120.1(2) . . ? C3 C2 H2A 119.9 . . ? C1 C2 H2A 119.9 . . ? C2 C3 C4 119.7(2) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C5 C4 C3 116.2(2) . . ? C5 C4 C9 118.6(2) . . ? C3 C4 C9 125.1(2) . . ? N2 C5 C4 123.8(2) . . ? N2 C5 C6 116.1(2) . . ? C4 C5 C6 120.1(2) . . ? N3 C6 C7 123.4(2) . . ? N3 C6 C5 116.0(2) . . ? C7 C6 C5 120.6(2) . . ? C6 C7 C12 117.3(2) . . ? C6 C7 C8 117.9(2) . . ? C12 C7 C8 124.8(2) . . ? C9 C8 C7 121.5(2) . . ? C9 C8 H8A 119.2 . . ? C7 C8 H8A 119.2 . . ? C8 C9 C4 121.2(2) . . ? C8 C9 H9A 119.4 . . ? C4 C9 H9A 119.4 . . ? N3 C10 C11 121.6(2) . . ? N3 C10 H10A 119.2 . . ? C11 C10 H10A 119.2 . . ? C12 C11 C10 120.7(2) . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C11 C12 C7 118.8(2) . . ? C11 C12 H12A 120.6 . . ? C7 C12 H12A 120.6 . . ? O2 C13 C17 122.7(2) . . ? O2 C13 C14 117.5(2) . . ? C17 C13 C14 119.8(2) . . ? O1 C14 C15 124.1(2) . . ? O1 C14 C13 116.2(2) . . ? C15 C14 C13 119.7(2) . . ? N1 C15 C14 118.8(2) . . ? N1 C15 C22 116.1(2) . . ? C14 C15 C22 125.1(2) . . ? N1 C16 C17 119.0(2) . . ? N1 C16 C21 120.2(2) . . ? C17 C16 C21 120.8(2) . . ? C16 C17 C18 118.5(2) . . ? C16 C17 C13 118.7(2) . . ? C18 C17 C13 122.8(2) . . ? C19 C18 C17 120.4(2) . . ? C19 C18 H18A 119.8 . . ? C17 C18 H18A 119.8 . . ? C18 C19 C20 120.3(2) . . ? C18 C19 H19A 119.9 . . ? C20 C19 H19A 119.9 . . ? C21 C20 C19 121.0(2) . . ? C21 C20 H20A 119.5 . . ? C19 C20 H20A 119.5 . . ? C20 C21 C16 119.0(2) . . ? C20 C21 H21A 120.5 . . ? C16 C21 H21A 120.5 . . ? C23 C22 C27 118.8(2) . . ? C23 C22 C15 120.5(2) . . ? C27 C22 C15 120.7(2) . . ? C24 C23 C22 120.7(2) . . ? C24 C23 H23A 119.6 . . ? C22 C23 H23A 119.6 . . ? C23 C24 C25 120.5(2) . . ? C23 C24 H24A 119.7 . . ? C25 C24 H24A 119.7 . . ? C26 C25 C24 119.2(2) . . ? C26 C25 H25A 120.4 . . ? C24 C25 H25A 120.4 . . ? C25 C26 C27 120.9(2) . . ? C25 C26 H26A 119.6 . . ? C27 C26 H26A 119.6 . . ? C26 C27 C22 119.9(2) . . ? C26 C27 H27A 120.1 . . ? C22 C27 H27A 120.1 . . ? 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 H1 O5 0.88 2.03 2.876(3) 159.6 3_667 O6 H1V O6 0.89(2) 2.00(3) 2.862(9) 163(7) 3_656 O6 H1U O3 0.90(2) 2.22(3) 3.110(5) 172(11) 3_666 O6 H1W O4 0.857(19) 2.00(2) 2.845(3) 169(4) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.538 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.074 # Attachment '- deposit_complex_3a.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 822515' #TrackingRef '- deposit_complex_3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H19 Cu N5 O5' _chemical_formula_weight 532.99 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc 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' _cell_length_a 14.0853(7) _cell_length_b 22.5202(11) _cell_length_c 6.8273(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.373(5) _cell_angle_gamma 90.00 _cell_volume 2156.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10113 _cell_measurement_theta_min 2.9027 _cell_measurement_theta_max 33.2312 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1092 _exptl_absorpt_coefficient_mu 1.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8152 _exptl_absorpt_correction_T_max 0.9010 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3611 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9658 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3083 _reflns_number_gt 2932 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0605P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3083 _refine_ls_number_parameters 325 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0316 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0750 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.041 _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 Cu1 Cu 0.34856(3) 0.534774(15) 0.38037(4) 0.01604(12) Uani 1 1 d . . . O1 O 0.40780(18) 0.46188(10) 0.4714(4) 0.0211(6) Uani 1 1 d . . . O2 O 0.46965(16) 0.57002(10) 0.4856(3) 0.0178(5) Uani 1 1 d . . . O3 O 0.81185(16) 0.34611(11) 0.6530(4) 0.0255(5) Uani 1 1 d . . . O4 O 0.94069(17) 0.33654(11) 0.5052(4) 0.0270(6) Uani 1 1 d . . . O5 O 0.93952(18) 0.39474(10) 0.7582(4) 0.0285(6) Uani 1 1 d . . . N1 N 0.6559(2) 0.43614(13) 0.6295(4) 0.0173(6) Uani 1 1 d . . . H1B H 0.6963 0.4067 0.6541 0.021 Uiso 1 1 calc R . . N2 N 0.2306(2) 0.49058(13) 0.2840(4) 0.0169(6) Uani 1 1 d . . . N3 N 0.28818(19) 0.61347(11) 0.3241(4) 0.0150(6) Uani 1 1 d . . . N4 N 0.1334(2) 0.57593(13) 0.2238(4) 0.0196(6) Uani 1 1 d . . . H4B H 0.0751 0.5871 0.1825 0.023 Uiso 1 1 calc R . . N5 N 0.89748(19) 0.35890(11) 0.6385(4) 0.0203(6) Uani 1 1 d . . . C1 C 0.2362(3) 0.43031(16) 0.2828(5) 0.0211(7) Uani 1 1 d . . . H1A H 0.2962 0.4124 0.3211 0.025 Uiso 1 1 calc R . . C2 C 0.1590(3) 0.39327(18) 0.2288(5) 0.0227(8) Uani 1 1 d . . . H2A H 0.1658 0.3513 0.2289 0.027 Uiso 1 1 calc R . . C3 C 0.0709(3) 0.42036(17) 0.1742(6) 0.0239(9) Uani 1 1 d . . . H3A H 0.0163 0.3967 0.1375 0.029 Uiso 1 1 calc R . . C4 C 0.0636(3) 0.48051(17) 0.1736(5) 0.0214(8) Uani 1 1 d . . . H4A H 0.0040 0.4989 0.1348 0.026 Uiso 1 1 calc R . . C5 C 0.1454(3) 0.5162(2) 0.2313(5) 0.0193(8) Uani 1 1 d . . . C6 C 0.1947(2) 0.62229(15) 0.2681(5) 0.0178(7) Uani 1 1 d . . . C7 C 0.1545(3) 0.67914(16) 0.2531(5) 0.0226(8) Uani 1 1 d . . . H7A H 0.0893 0.6841 0.2063 0.027 Uiso 1 1 calc R . . C8 C 0.2104(3) 0.72795(16) 0.3069(5) 0.0260(8) Uani 1 1 d . . . H8A H 0.1835 0.7666 0.3074 0.031 Uiso 1 1 calc R . . C9 C 0.3070(2) 0.71907(15) 0.3602(5) 0.0227(8) Uani 1 1 d . . . H9A H 0.3481 0.7519 0.3909 0.027 Uiso 1 1 calc R . . C10 C 0.3425(3) 0.66208(13) 0.3681(6) 0.0202(7) Uani 1 1 d . . . H10A H 0.4085 0.6566 0.4065 0.024 Uiso 1 1 calc R . . C13 C 0.5315(3) 0.52813(17) 0.5388(5) 0.0184(9) Uani 1 1 d . . . C14 C 0.4993(3) 0.47008(15) 0.5231(5) 0.0163(8) Uani 1 1 d . . . C15 C 0.5644(2) 0.42241(16) 0.5674(5) 0.0167(7) Uani 1 1 d . . . C16 C 0.6894(2) 0.49308(15) 0.6565(5) 0.0161(7) Uani 1 1 d . . . C17 C 0.6283(2) 0.54081(15) 0.6087(5) 0.0158(7) Uani 1 1 d . . . C18 C 0.6651(2) 0.59936(15) 0.6351(5) 0.0192(7) Uani 1 1 d . . . H18A H 0.6243 0.6324 0.6062 0.023 Uiso 1 1 calc R . . C19 C 0.7578(2) 0.60849(15) 0.7013(5) 0.0208(8) Uani 1 1 d . . . H19A H 0.7821 0.6477 0.7154 0.025 Uiso 1 1 calc R . . C20 C 0.8180(2) 0.55926(16) 0.7492(5) 0.0199(7) Uani 1 1 d . . . H20A H 0.8827 0.5660 0.7967 0.024 Uiso 1 1 calc R . . C21 C 0.7855(2) 0.50293(15) 0.7288(5) 0.0191(7) Uani 1 1 d . . . H21A H 0.8267 0.4704 0.7626 0.023 Uiso 1 1 calc R . . C22 C 0.5371(2) 0.35945(15) 0.5525(5) 0.0173(7) Uani 1 1 d . . . C23 C 0.5742(2) 0.31822(14) 0.6899(5) 0.0202(7) Uani 1 1 d . . . H23A H 0.6215 0.3301 0.7906 0.024 Uiso 1 1 calc R . . C24 C 0.5430(3) 0.25989(15) 0.6820(5) 0.0248(8) Uani 1 1 d . . . H24A H 0.5686 0.2322 0.7777 0.030 Uiso 1 1 calc R . . C25 C 0.4750(3) 0.24192(16) 0.5360(5) 0.0277(8) Uani 1 1 d . . . H25A H 0.4518 0.2023 0.5343 0.033 Uiso 1 1 calc R . . C26 C 0.4406(3) 0.28133(15) 0.3928(5) 0.0251(8) Uani 1 1 d . . . H26A H 0.3963 0.2681 0.2884 0.030 Uiso 1 1 calc R . . C27 C 0.4697(2) 0.34035(15) 0.3987(5) 0.0223(8) Uani 1 1 d . . . H27A H 0.4446 0.3675 0.3007 0.027 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 Cu1 0.0088(2) 0.01460(18) 0.0249(2) -0.00037(19) 0.00291(14) 0.00019(17) O1 0.0094(13) 0.0163(13) 0.0371(15) 0.0008(10) -0.0008(11) -0.0019(9) O2 0.0106(12) 0.0179(12) 0.0254(12) -0.0004(10) 0.0041(10) 0.0029(10) O3 0.0087(12) 0.0251(13) 0.0433(14) 0.0024(11) 0.0051(10) -0.0012(10) O4 0.0170(13) 0.0263(13) 0.0384(15) -0.0063(11) 0.0058(11) 0.0016(11) O5 0.0175(13) 0.0234(13) 0.0433(15) -0.0090(11) -0.0034(11) -0.0006(10) N1 0.0121(15) 0.0180(16) 0.0222(15) 0.0011(12) 0.0040(12) 0.0049(12) N2 0.0116(16) 0.0172(16) 0.0225(15) -0.0021(13) 0.0050(12) -0.0006(12) N3 0.0088(14) 0.0159(14) 0.0210(14) 0.0009(11) 0.0053(11) 0.0002(11) N4 0.0075(14) 0.0219(15) 0.0291(16) 0.0008(12) 0.0009(11) 0.0022(12) N5 0.0138(15) 0.0152(13) 0.0311(16) 0.0035(12) -0.0024(12) 0.0001(12) C1 0.0129(17) 0.025(2) 0.0257(18) -0.0025(15) 0.0039(14) -0.0010(15) C2 0.021(2) 0.0218(19) 0.025(2) -0.0052(16) 0.0017(15) -0.0067(16) C3 0.013(2) 0.032(2) 0.027(2) -0.0079(17) 0.0057(15) -0.0109(16) C4 0.0097(18) 0.0282(19) 0.0263(19) -0.0028(15) 0.0010(15) -0.0068(15) C5 0.015(2) 0.030(2) 0.0140(18) -0.0015(16) 0.0065(14) 0.0016(17) C6 0.0138(17) 0.0222(18) 0.0183(17) 0.0012(14) 0.0055(14) -0.0049(14) C7 0.0112(17) 0.0237(18) 0.033(2) 0.0040(15) 0.0025(15) 0.0003(14) C8 0.0223(19) 0.0199(17) 0.037(2) 0.0065(16) 0.0072(16) 0.0030(16) C9 0.0142(17) 0.0201(16) 0.034(2) 0.0009(14) 0.0017(16) -0.0056(14) C10 0.0118(16) 0.0193(14) 0.0296(17) -0.0019(17) 0.0031(13) -0.0007(17) C13 0.015(2) 0.029(2) 0.0135(17) -0.0010(14) 0.0093(15) -0.0019(15) C14 0.0098(18) 0.026(2) 0.0137(18) -0.0022(13) 0.0021(14) -0.0018(14) C15 0.0151(19) 0.0225(19) 0.0130(16) 0.0024(14) 0.0041(13) 0.0044(15) C16 0.0160(18) 0.0194(17) 0.0142(16) 0.0011(14) 0.0086(14) 0.0039(14) C17 0.0101(17) 0.0239(18) 0.0135(16) -0.0025(13) 0.0021(13) -0.0011(13) C18 0.0152(18) 0.0199(17) 0.0230(17) 0.0002(14) 0.0039(14) 0.0048(14) C19 0.0193(19) 0.0184(17) 0.0258(19) -0.0024(14) 0.0076(15) -0.0055(14) C20 0.0092(16) 0.0298(18) 0.0209(17) -0.0036(15) 0.0028(13) -0.0010(14) C21 0.0149(18) 0.0233(18) 0.0204(17) -0.0015(14) 0.0081(14) 0.0035(14) C22 0.0130(17) 0.0180(17) 0.0221(17) -0.0015(14) 0.0072(14) 0.0034(14) C23 0.0157(17) 0.0217(17) 0.0239(17) -0.0002(14) 0.0057(14) 0.0060(14) C24 0.026(2) 0.0178(17) 0.0315(19) 0.0044(15) 0.0088(16) 0.0069(15) C25 0.032(2) 0.0181(17) 0.035(2) -0.0012(15) 0.0123(17) 0.0019(15) C26 0.0197(19) 0.0233(18) 0.0325(19) -0.0057(15) 0.0039(16) -0.0002(15) C27 0.0217(19) 0.0214(18) 0.0243(18) 0.0022(14) 0.0058(15) 0.0058(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.918(2) . ? Cu1 O2 1.956(2) . ? Cu1 N3 1.988(3) . ? Cu1 N2 1.995(3) . ? O1 C14 1.317(5) . ? O2 C13 1.312(5) . ? O3 N5 1.253(3) . ? O4 N5 1.247(4) . ? O5 N5 1.257(4) . ? N1 C15 1.354(5) . ? N1 C16 1.373(5) . ? N1 H1B 0.8800 . ? N2 C5 1.350(5) . ? N2 C1 1.360(5) . ? N3 C6 1.351(4) . ? N3 C10 1.353(4) . ? N4 C5 1.356(5) . ? N4 C6 1.370(4) . ? N4 H4B 0.8800 . ? C1 C2 1.393(5) . ? C1 H1A 0.9500 . ? C2 C3 1.401(6) . ? C2 H2A 0.9500 . ? C3 C4 1.359(5) . ? C3 H3A 0.9500 . ? C4 C5 1.430(5) . ? C4 H4A 0.9500 . ? C6 C7 1.400(5) . ? C7 C8 1.382(5) . ? C7 H7A 0.9500 . ? C8 C9 1.390(5) . ? C8 H8A 0.9500 . ? C9 C10 1.376(5) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C13 C14 1.385(5) . ? C13 C17 1.430(6) . ? C14 C15 1.425(5) . ? C15 C22 1.470(5) . ? C16 C17 1.396(5) . ? C16 C21 1.414(5) . ? C17 C18 1.422(5) . ? C18 C19 1.357(5) . ? C18 H18A 0.9500 . ? C19 C20 1.415(5) . ? C19 H19A 0.9500 . ? C20 C21 1.351(5) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C23 1.387(5) . ? C22 C27 1.415(5) . ? C23 C24 1.385(5) . ? C23 H23A 0.9500 . ? C24 C25 1.377(5) . ? C24 H24A 0.9500 . ? C25 C26 1.375(5) . ? C25 H25A 0.9500 . ? C26 C27 1.390(5) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? 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 O1 Cu1 O2 83.71(10) . . ? O1 Cu1 N3 172.26(11) . . ? O2 Cu1 N3 92.97(10) . . ? O1 Cu1 N2 90.20(12) . . ? O2 Cu1 N2 173.90(11) . . ? N3 Cu1 N2 93.03(12) . . ? C14 O1 Cu1 110.6(2) . . ? C13 O2 Cu1 110.1(2) . . ? C15 N1 C16 124.1(3) . . ? C15 N1 H1B 117.9 . . ? C16 N1 H1B 117.9 . . ? C5 N2 C1 118.4(3) . . ? C5 N2 Cu1 124.5(3) . . ? C1 N2 Cu1 116.9(2) . . ? C6 N3 C10 117.4(3) . . ? C6 N3 Cu1 125.0(2) . . ? C10 N3 Cu1 117.1(2) . . ? C5 N4 C6 132.4(3) . . ? C5 N4 H4B 113.8 . . ? C6 N4 H4B 113.8 . . ? O4 N5 O3 120.3(3) . . ? O4 N5 O5 120.1(3) . . ? O3 N5 O5 119.7(3) . . ? N2 C1 C2 123.7(3) . . ? N2 C1 H1A 118.1 . . ? C2 C1 H1A 118.1 . . ? C1 C2 C3 117.4(4) . . ? C1 C2 H2A 121.3 . . ? C3 C2 H2A 121.3 . . ? C4 C3 C2 120.0(3) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C3 C4 C5 120.0(4) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? N2 C5 N4 122.6(3) . . ? N2 C5 C4 120.4(4) . . ? N4 C5 C4 117.0(3) . . ? N3 C6 N4 121.8(3) . . ? N3 C6 C7 122.2(3) . . ? N4 C6 C7 116.0(3) . . ? C8 C7 C6 119.4(3) . . ? C8 C7 H7A 120.3 . . ? C6 C7 H7A 120.3 . . ? C7 C8 C9 118.4(3) . . ? C7 C8 H8A 120.8 . . ? C9 C8 H8A 120.8 . . ? C10 C9 C8 119.2(3) . . ? C10 C9 H9A 120.4 . . ? C8 C9 H9A 120.4 . . ? N3 C10 C9 123.4(4) . . ? N3 C10 H10A 118.3 . . ? C9 C10 H10A 118.3 . . ? O2 C13 C14 116.9(4) . . ? O2 C13 C17 122.4(3) . . ? C14 C13 C17 120.6(3) . . ? O1 C14 C13 117.3(3) . . ? O1 C14 C15 123.0(3) . . ? C13 C14 C15 119.7(4) . . ? N1 C15 C14 117.9(3) . . ? N1 C15 C22 118.5(3) . . ? C14 C15 C22 123.6(3) . . ? N1 C16 C17 119.4(3) . . ? N1 C16 C21 120.0(3) . . ? C17 C16 C21 120.7(3) . . ? C16 C17 C18 118.3(3) . . ? C16 C17 C13 118.1(3) . . ? C18 C17 C13 123.5(3) . . ? C19 C18 C17 120.7(3) . . ? C19 C18 H18A 119.7 . . ? C17 C18 H18A 119.7 . . ? C18 C19 C20 119.7(3) . . ? C18 C19 H19A 120.1 . . ? C20 C19 H19A 120.1 . . ? C21 C20 C19 121.4(3) . . ? C21 C20 H20A 119.3 . . ? C19 C20 H20A 119.3 . . ? C20 C21 C16 119.1(3) . . ? C20 C21 H21A 120.4 . . ? C16 C21 H21A 120.4 . . ? C23 C22 C27 118.8(3) . . ? C23 C22 C15 121.3(3) . . ? C27 C22 C15 119.8(3) . . ? C24 C23 C22 120.7(3) . . ? C24 C23 H23A 119.7 . . ? C22 C23 H23A 119.7 . . ? C25 C24 C23 120.3(3) . . ? C25 C24 H24A 119.9 . . ? C23 C24 H24A 119.9 . . ? C26 C25 C24 120.0(3) . . ? C26 C25 H25A 120.0 . . ? C24 C25 H25A 120.0 . . ? C25 C26 C27 120.9(3) . . ? C25 C26 H26A 119.6 . . ? C27 C26 H26A 119.6 . . ? C26 C27 C22 119.2(3) . . ? C26 C27 H27A 120.4 . . ? C22 C27 H27A 120.4 . . ? 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 O3 0.88 2.12 2.983(4) 165.0 . N4 H4B O5 0.88 2.07 2.841(4) 146.5 2_464 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.675 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.072