Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Loic Charbonniere' _publ_contact_author_address ; LCM-ECPM CNRS 25, rue Becquerel Strasbourg 67000 FRANCE ; _publ_contact_author_email CHARBONN@CHIMIE.U-STRASBG.FR _publ_section_title ; A dissymetric terpyridine based ligand for the formation of luminescent di-aquo lanthanide complexes ; loop_ _publ_author_name 'Loic Charbonniere' 'David Flot' 'Samir Mameri' 'Fanny Waltz' 'Christelle Zandanel' 'Raymond Ziessel' data_cz45 _database_code_depnum_ccdc_archive 'CCDC 633962' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H15 O6 N4 Gd, 8 (H2O)' _chemical_formula_sum 'C21 H15 Gd N4 O14' _chemical_formula_weight 704.62 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' Gd Gd -0.1917 5.5316 '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 monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.277(3) _cell_length_b 12.8610(9) _cell_length_c 16.837(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.572(8) _cell_angle_gamma 90.00 _cell_volume 2628.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 17869 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 29.91 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.008 _exptl_crystal_size_min 0.002 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.780 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1380 _exptl_absorpt_coefficient_mu 4.261 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.873 _diffrn_radiation_type ? _diffrn_radiation_source synchrotron _diffrn_source_type 'ESRF-ID23-2 gemini microfocus beamline' _diffrn_radiation_monochromator 'Si 111' _diffrn_measurement_device_type 'ESRF/EMBL microdiffractometer MD2M' _diffrn_measurement_method oscillation _diffrn_detector_type 'marMOSAIC 225' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28952 _diffrn_reflns_av_R_equivalents 0.0764 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 29.91 _reflns_number_total 3872 _reflns_number_gt 3426 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'enCIFer, WinGx' _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^)+(0.0556P)^2^+14.3632P] 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 3872 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.0999 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O5 O 0.9633(3) 0.5822(3) 0.0301(2) 0.0148(9) Uani 1 1 d . . . O6 O 0.8304(4) 0.6980(3) -0.0068(3) 0.0244(11) Uani 1 1 d . . . O7 O 1.0910(4) 0.4253(4) 0.1398(3) 0.0249(11) Uani 1 1 d . . . O8 O 1.3748(5) 1.0519(4) 0.1320(3) 0.0457(15) Uani 1 1 d . . . O9 O 1.5311(4) 0.8973(4) 0.0067(3) 0.0345(12) Uani 1 1 d . . . O10 O 1.0912(6) 0.5225(5) 0.4606(4) 0.0602(18) Uani 1 1 d . . . O11 O 1.1662(5) 0.3271(4) 0.2775(3) 0.0472(15) Uani 1 1 d . . . O12 O 0.7481(4) 0.8688(4) 0.0631(3) 0.0433(14) Uani 1 1 d . . . O13 O 0.7800(5) 0.8040(4) -0.1585(3) 0.0467(15) Uani 1 1 d . . . O14 O 1.0482(6) 0.4364(6) -0.3230(5) 0.081(2) Uani 1 1 d . . . Gd1 Gd 1.16548(2) 0.54577(2) 0.052114(16) 0.01355(14) Uani 1 1 d . . . O1 O 1.1259(3) 0.6109(3) -0.0825(2) 0.0178(10) Uani 1 1 d . . . O2 O 1.1325(5) 0.5880(4) -0.2130(3) 0.0348(13) Uani 1 1 d . . . O3 O 1.2955(4) 0.6843(3) 0.0491(2) 0.0203(10) Uani 1 1 d . . . O4 O 1.3700(4) 0.8385(4) 0.0877(3) 0.0295(11) Uani 1 1 d . . . N1 N 1.2918(4) 0.4796(4) -0.0406(3) 0.0153(12) Uani 1 1 d . . . N2 N 1.3484(4) 0.4589(4) 0.1169(3) 0.0150(11) Uani 1 1 d . . . N3 N 1.2324(4) 0.5817(4) 0.2015(3) 0.0135(11) Uani 1 1 d . . . N4 N 1.1040(4) 0.7235(4) 0.1080(3) 0.0170(12) Uani 1 1 d . . . C1 C 1.1675(6) 0.5715(5) -0.1411(4) 0.0227(16) Uani 1 1 d . . . C2 C 1.2631(6) 0.4986(5) -0.1204(4) 0.0195(15) Uani 1 1 d . . . C3 C 1.3185(6) 0.4536(5) -0.1781(4) 0.0255(16) Uani 1 1 d . . . H3 H 1.2961 0.4676 -0.2335 0.031 Uiso 1 1 calc R . . C4 C 1.4046(6) 0.3896(5) -0.1542(4) 0.0270(16) Uani 1 1 d . . . H4 H 1.4425 0.3574 -0.1928 0.032 Uiso 1 1 calc R . . C5 C 1.4372(6) 0.3713(5) -0.0731(4) 0.0244(15) Uani 1 1 d . . . H5 H 1.4991 0.3283 -0.0557 0.029 Uiso 1 1 calc R . . C6 C 1.3790(5) 0.4163(5) -0.0174(4) 0.0186(14) Uani 1 1 d . . . C7 C 1.4078(5) 0.4015(5) 0.0707(4) 0.0169(14) Uani 1 1 d . . . C8 C 1.4921(6) 0.3349(5) 0.1046(4) 0.0277(17) Uani 1 1 d . . . H8 H 1.5320 0.2947 0.0714 0.033 Uiso 1 1 calc R . . C9 C 1.5160(6) 0.3286(5) 0.1868(4) 0.0268(17) Uani 1 1 d . . . H9 H 1.5711 0.2818 0.2109 0.032 Uiso 1 1 calc R . . C10 C 1.4601(6) 0.3904(5) 0.2345(4) 0.0232(16) Uani 1 1 d . . . H10 H 1.4779 0.3882 0.2914 0.028 Uiso 1 1 calc R . . C11 C 1.3771(5) 0.4558(5) 0.1977(4) 0.0176(14) Uani 1 1 d . . . C12 C 1.3177(6) 0.5299(5) 0.2435(4) 0.0175(14) Uani 1 1 d . . . C13 C 1.3465(6) 0.5477(5) 0.3260(4) 0.0263(17) Uani 1 1 d . . . H13 H 1.4083 0.5130 0.3551 0.032 Uiso 1 1 calc R . . C14 C 1.2855(6) 0.6153(5) 0.3648(4) 0.0233(16) Uani 1 1 d . . . H14 H 1.3048 0.6274 0.4208 0.028 Uiso 1 1 calc R . . C15 C 1.1959(5) 0.6655(5) 0.3219(4) 0.0200(15) Uani 1 1 d . . . H15 H 1.1521 0.7116 0.3478 0.024 Uiso 1 1 calc R . . C16 C 1.1713(5) 0.6466(5) 0.2394(4) 0.0177(14) Uani 1 1 d . . . C17 C 1.0747(5) 0.6959(5) 0.1883(4) 0.0193(14) Uani 1 1 d . . . H17A H 1.0116 0.6471 0.1815 0.023 Uiso 1 1 calc R . . H17B H 1.0524 0.7594 0.2150 0.023 Uiso 1 1 calc R . . C18 C 1.1912(5) 0.8032(5) 0.1163(4) 0.0201(15) Uani 1 1 d . . . H18A H 1.2127 0.8190 0.1741 0.024 Uiso 1 1 calc R . . H18B H 1.1608 0.8676 0.0895 0.024 Uiso 1 1 calc R . . C19 C 1.2932(5) 0.7721(5) 0.0814(4) 0.0188(15) Uani 1 1 d . . . C20 C 1.0050(5) 0.7621(5) 0.0550(4) 0.0174(14) Uani 1 1 d . . . H20A H 1.0283 0.7982 0.0084 0.021 Uiso 1 1 calc R . . H20B H 0.9666 0.8133 0.0848 0.021 Uiso 1 1 calc R . . C21 C 0.9255(5) 0.6758(5) 0.0248(3) 0.0160(14) 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 O5 0.016(3) 0.014(2) 0.014(2) 0.0025(17) 0.0021(17) -0.0010(18) O6 0.011(3) 0.028(3) 0.031(3) 0.005(2) -0.007(2) 0.0010(19) O7 0.025(3) 0.028(3) 0.021(2) 0.003(2) -0.001(2) -0.006(2) O8 0.054(4) 0.044(4) 0.039(3) 0.005(3) 0.008(3) 0.003(3) O9 0.032(3) 0.035(3) 0.037(3) -0.001(2) 0.006(2) 0.001(2) O10 0.083(5) 0.043(4) 0.060(4) -0.012(3) 0.028(4) -0.016(3) O11 0.049(4) 0.048(4) 0.041(3) 0.013(3) -0.005(3) -0.006(3) O12 0.037(3) 0.047(3) 0.044(3) -0.011(3) 0.001(3) 0.009(3) O13 0.053(4) 0.048(4) 0.038(3) 0.012(3) 0.002(3) 0.007(3) O14 0.063(5) 0.065(5) 0.109(6) -0.019(4) -0.009(5) -0.008(4) Gd1 0.0128(2) 0.01542(19) 0.01172(18) -0.00067(12) -0.00059(12) 0.00070(12) O1 0.018(3) 0.020(2) 0.017(2) 0.0046(18) 0.0055(18) 0.0012(18) O2 0.052(4) 0.035(3) 0.017(3) 0.009(2) 0.003(2) 0.008(3) O3 0.016(3) 0.023(3) 0.023(2) -0.0028(19) 0.0027(19) -0.0013(19) O4 0.024(3) 0.029(3) 0.037(3) -0.005(2) 0.009(2) -0.006(2) N1 0.016(3) 0.012(3) 0.018(3) 0.000(2) 0.002(2) -0.004(2) N2 0.011(3) 0.016(3) 0.018(3) -0.004(2) 0.000(2) -0.003(2) N3 0.016(3) 0.018(3) 0.006(2) -0.001(2) -0.002(2) 0.003(2) N4 0.013(3) 0.019(3) 0.018(3) 0.003(2) -0.002(2) -0.001(2) C1 0.037(5) 0.013(3) 0.018(4) 0.004(3) 0.006(3) -0.003(3) C2 0.026(4) 0.015(3) 0.019(3) 0.000(3) 0.005(3) -0.006(3) C3 0.029(5) 0.028(4) 0.021(3) -0.001(3) 0.010(3) -0.008(3) C4 0.026(4) 0.026(4) 0.032(4) -0.009(3) 0.013(3) -0.001(3) C5 0.016(4) 0.023(4) 0.035(4) -0.006(3) 0.008(3) 0.004(3) C6 0.014(4) 0.014(3) 0.028(4) -0.006(3) 0.004(3) -0.005(3) C7 0.008(3) 0.017(3) 0.024(3) -0.004(3) -0.001(3) -0.003(3) C8 0.026(4) 0.016(4) 0.037(4) -0.011(3) -0.007(3) 0.007(3) C9 0.022(4) 0.019(4) 0.035(4) 0.002(3) -0.009(3) 0.008(3) C10 0.022(4) 0.022(4) 0.022(3) 0.005(3) -0.008(3) -0.002(3) C11 0.017(4) 0.014(3) 0.020(3) 0.003(3) -0.003(3) -0.003(3) C12 0.021(4) 0.019(3) 0.012(3) 0.001(2) 0.001(3) -0.003(3) C13 0.027(4) 0.029(4) 0.019(3) 0.005(3) -0.011(3) -0.005(3) C14 0.027(4) 0.027(4) 0.014(3) -0.001(3) -0.003(3) -0.005(3) C15 0.020(4) 0.020(3) 0.020(3) -0.003(3) 0.004(3) -0.001(3) C16 0.022(4) 0.014(3) 0.016(3) -0.002(3) 0.000(3) -0.005(3) C17 0.016(4) 0.018(3) 0.023(3) -0.006(3) 0.000(3) 0.001(3) C18 0.017(4) 0.020(3) 0.023(3) 0.005(3) -0.001(3) -0.003(3) C19 0.022(4) 0.017(4) 0.016(3) 0.005(3) -0.005(3) -0.003(3) C20 0.015(4) 0.015(3) 0.021(3) 0.000(3) 0.001(3) 0.003(3) C21 0.017(4) 0.017(3) 0.015(3) 0.005(2) 0.004(3) 0.000(3) _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 O5 C21 1.288(7) . ? O5 Gd1 2.499(4) . ? O5 Gd1 2.544(4) 3_765 ? O6 C21 1.241(7) . ? O7 Gd1 2.413(5) . ? Gd1 O3 2.398(4) . ? Gd1 O1 2.397(4) . ? Gd1 N1 2.507(5) . ? Gd1 O5 2.544(4) 3_765 ? Gd1 N3 2.569(4) . ? Gd1 N2 2.598(5) . ? Gd1 N4 2.625(5) . ? O1 C1 1.282(8) . ? O2 C1 1.241(8) . ? O3 C19 1.255(7) . ? O4 C19 1.265(8) . ? N1 C6 1.355(9) . ? N1 C2 1.360(8) . ? N2 C11 1.355(8) . ? N2 C7 1.360(8) . ? N3 C16 1.345(8) . ? N3 C12 1.349(8) . ? N4 C18 1.473(8) . ? N4 C20 1.483(8) . ? N4 C17 1.492(8) . ? C1 C2 1.502(10) . ? C2 C3 1.393(10) . ? C3 C4 1.352(10) . ? C3 H3 0.9500 . ? C4 C5 1.385(10) . ? C4 H4 0.9500 . ? C5 C6 1.387(9) . ? C5 H5 0.9500 . ? C6 C7 1.485(9) . ? C7 C8 1.398(9) . ? C8 C9 1.374(10) . ? C8 H8 0.9500 . ? C9 C10 1.383(10) . ? C9 H9 0.9500 . ? C10 C11 1.394(9) . ? C10 H10 0.9500 . ? C11 C12 1.484(9) . ? C12 C13 1.399(9) . ? C13 C14 1.375(10) . ? C13 H13 0.9500 . ? C14 C15 1.383(9) . ? C14 H14 0.9500 . ? C15 C16 1.397(9) . ? C15 H15 0.9500 . ? C16 C17 1.499(9) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.515(10) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C20 C21 1.515(9) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? 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 C21 O5 Gd1 121.7(4) . . ? C21 O5 Gd1 112.2(4) . 3_765 ? Gd1 O5 Gd1 118.84(16) . 3_765 ? O3 Gd1 O1 76.23(14) . . ? O3 Gd1 O7 143.57(14) . . ? O1 Gd1 O7 139.57(14) . . ? O3 Gd1 O5 120.48(14) . . ? O1 Gd1 O5 74.76(14) . . ? O7 Gd1 O5 75.66(14) . . ? O3 Gd1 N1 76.33(15) . . ? O1 Gd1 N1 65.63(15) . . ? O7 Gd1 N1 119.27(16) . . ? O5 Gd1 N1 131.63(15) . . ? O3 Gd1 O5 146.19(13) . 3_765 ? O1 Gd1 O5 71.93(13) . 3_765 ? O7 Gd1 O5 69.88(14) . 3_765 ? O5 Gd1 O5 61.16(16) . 3_765 ? N1 Gd1 O5 80.42(15) . 3_765 ? O3 Gd1 N3 76.71(15) . . ? O1 Gd1 N3 148.53(15) . . ? O7 Gd1 N3 67.14(15) . . ? O5 Gd1 N3 106.10(14) . . ? N1 Gd1 N3 122.22(16) . . ? O5 Gd1 N3 137.00(15) 3_765 . ? O3 Gd1 N2 78.01(15) . . ? O1 Gd1 N2 126.02(16) . . ? O7 Gd1 N2 81.35(16) . . ? O5 Gd1 N2 156.95(15) . . ? N1 Gd1 N2 62.56(16) . . ? O5 Gd1 N2 112.22(14) 3_765 . ? N3 Gd1 N2 62.36(16) . . ? O3 Gd1 N4 65.69(15) . . ? O1 Gd1 N4 90.34(15) . . ? O7 Gd1 N4 100.63(16) . . ? O5 Gd1 N4 63.75(14) . . ? N1 Gd1 N4 139.14(16) . . ? O5 Gd1 N4 124.75(14) 3_765 . ? N3 Gd1 N4 63.85(15) . . ? N2 Gd1 N4 120.03(15) . . ? C1 O1 Gd1 122.8(4) . . ? C19 O3 Gd1 126.9(4) . . ? C6 N1 C2 118.1(5) . . ? C6 N1 Gd1 124.1(4) . . ? C2 N1 Gd1 117.4(4) . . ? C11 N2 C7 118.5(5) . . ? C11 N2 Gd1 120.9(4) . . ? C7 N2 Gd1 119.8(4) . . ? C16 N3 C12 120.1(5) . . ? C16 N3 Gd1 117.2(4) . . ? C12 N3 Gd1 122.3(4) . . ? C18 N4 C20 110.1(5) . . ? C18 N4 C17 110.4(5) . . ? C20 N4 C17 109.7(5) . . ? C18 N4 Gd1 113.3(4) . . ? C20 N4 Gd1 109.2(3) . . ? C17 N4 Gd1 103.8(3) . . ? O2 C1 O1 124.3(6) . . ? O2 C1 C2 118.6(6) . . ? O1 C1 C2 117.1(5) . . ? N1 C2 C3 122.2(6) . . ? N1 C2 C1 114.9(6) . . ? C3 C2 C1 122.9(6) . . ? C4 C3 C2 119.1(6) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 119.7(6) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 119.6(6) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? N1 C6 C5 121.3(6) . . ? N1 C6 C7 115.1(6) . . ? C5 C6 C7 123.5(6) . . ? N2 C7 C8 121.8(6) . . ? N2 C7 C6 115.7(5) . . ? C8 C7 C6 122.5(6) . . ? C9 C8 C7 118.8(7) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 120.1(6) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C11 118.8(6) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? N2 C11 C10 121.8(6) . . ? N2 C11 C12 115.4(5) . . ? C10 C11 C12 122.7(6) . . ? N3 C12 C13 120.1(6) . . ? N3 C12 C11 116.6(5) . . ? C13 C12 C11 123.3(6) . . ? C14 C13 C12 120.0(6) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 119.6(6) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C16 118.4(6) . . ? C14 C15 H15 120.8 . . ? C16 C15 H15 120.8 . . ? N3 C16 C15 121.8(6) . . ? N3 C16 C17 116.0(5) . . ? C15 C16 C17 122.2(6) . . ? N4 C17 C16 110.1(5) . . ? N4 C17 H17A 109.6 . . ? C16 C17 H17A 109.6 . . ? N4 C17 H17B 109.6 . . ? C16 C17 H17B 109.6 . . ? H17A C17 H17B 108.2 . . ? N4 C18 C19 114.2(5) . . ? N4 C18 H18A 108.7 . . ? C19 C18 H18A 108.7 . . ? N4 C18 H18B 108.7 . . ? C19 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? O3 C19 O4 125.4(6) . . ? O3 C19 C18 118.6(6) . . ? O4 C19 C18 116.0(6) . . ? N4 C20 C21 112.7(5) . . ? N4 C20 H20A 109.0 . . ? C21 C20 H20A 109.0 . . ? N4 C20 H20B 109.0 . . ? C21 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? O6 C21 O5 123.4(6) . . ? O6 C21 C20 119.5(5) . . ? O5 C21 C20 117.0(5) . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 29.91 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 1.652 _refine_diff_density_min -1.188 _refine_diff_density_rms 0.143