# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Dy _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H48 Dy N19 O17' _chemical_formula_weight 1037.31 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' Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' 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 24.461(6) _cell_length_b 12.134(3) _cell_length_c 14.921(4) _cell_angle_alpha 90.00 _cell_angle_beta 114.525(4) _cell_angle_gamma 90.00 _cell_volume 4029.1(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9930 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 27.43 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.710 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2108 _exptl_absorpt_coefficient_mu 1.949 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5656 _exptl_absorpt_correction_T_max 0.8290 _exptl_absorpt_process_details '(SADABS; Bruker 2008)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17134 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0124 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4581 _reflns_number_gt 4318 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0612P)^2^+7.1442P] 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 4581 _refine_ls_number_parameters 286 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0864 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.019 _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 Dy1 Dy 0.0000 0.363930(13) 0.2500 0.03520(8) Uani 1 2 d S . . O1 O -0.05086(11) 0.4201(2) 0.34827(18) 0.0525(5) Uani 1 1 d . . . O2 O -0.00556(10) 0.20385(19) 0.34094(17) 0.0483(5) Uani 1 1 d . . . O4 O 0.05334(9) 0.52065(19) 0.33878(18) 0.0506(5) Uani 1 1 d . . . O3 O 0.10106(9) 0.30694(18) 0.33910(17) 0.0468(5) Uani 1 1 d . . . O5 O 0.0000 -0.2211(17) 0.2500 0.90(6) Uani 1 2 d SD . . O6 O -0.0222(6) -0.1181(13) 0.1896(12) 0.364(14) Uani 1 1 d D . . O7 O -0.2795(12) 0.398(2) 0.2808(18) 0.255(13) Uani 0.50 1 d P . . O7A O -0.2836(8) 0.3068(17) 0.2101(16) 0.229(9) Uani 0.50 1 d P . . O8 O -0.2288(7) 0.3932(8) 0.2097(10) 0.267(7) Uani 1 1 d . . . O9 O -0.2169(6) 0.3522(9) 0.3337(12) 0.304(9) Uani 1 1 d . . . N2 N -0.11541(17) 0.5150(3) 0.3962(3) 0.0752(10) Uani 1 1 d . . . H2A H -0.1366 0.4596 0.3991 0.090 Uiso 1 1 calc R . . N1 N -0.04257(19) 0.6039(3) 0.3837(4) 0.0757(11) Uani 1 1 d . . . H1A H -0.0112 0.6158 0.3729 0.091 Uiso 1 1 calc R . . N4 N -0.04489(18) 0.0473(3) 0.3773(3) 0.0741(10) Uani 1 1 d . . . H4A H -0.0189 0.0015 0.3743 0.089 Uiso 1 1 calc R . . N3 N -0.08696(19) 0.2033(3) 0.3806(4) 0.0805(12) Uani 1 1 d . . . H3A H -0.0935 0.2732 0.3758 0.097 Uiso 1 1 calc R . . N7 N 0.15371(13) 0.5282(3) 0.3714(3) 0.0597(8) Uani 1 1 d . . . H7A H 0.1592 0.4590 0.3659 0.072 Uiso 1 1 calc R . . N8 N 0.10859(15) 0.6804(3) 0.3816(3) 0.0719(10) Uani 1 1 d . . . H8A H 0.0813 0.7228 0.3849 0.086 Uiso 1 1 calc R . . N6 N 0.19080(14) 0.2154(3) 0.3857(3) 0.0727(10) Uani 1 1 d . . . H6A H 0.2128 0.2713 0.3875 0.087 Uiso 1 1 calc R . . N5 N 0.11325(17) 0.1242(3) 0.3805(4) 0.0697(11) Uani 1 1 d . . . H5A H 0.0772 0.1116 0.3738 0.084 Uiso 1 1 calc R . . N9 N 0.0000 -0.13329(18) 0.2500 0.0157(5) Uani 1 2 d SD . . N10 N -0.24534(17) 0.3656(3) 0.2556(4) 0.0619(10) Uani 1 1 d . . . C1 C -0.06805(14) 0.5072(3) 0.3737(2) 0.0458(6) Uani 1 1 d . . . C2 C -0.1267(3) 0.6275(4) 0.4151(4) 0.0772(14) Uani 1 1 d . . . H2B H -0.1289 0.6342 0.4783 0.093 Uiso 1 1 calc R . . H2C H -0.1638 0.6548 0.3638 0.093 Uiso 1 1 calc R . . C3 C -0.0724(2) 0.6889(4) 0.4148(4) 0.0747(12) Uani 1 1 d . . . H3B H -0.0845 0.7499 0.3687 0.090 Uiso 1 1 calc R . . H3C H -0.0468 0.7163 0.4799 0.090 Uiso 1 1 calc R . . C4 C -0.04319(16) 0.1558(3) 0.3641(2) 0.0449(7) Uani 1 1 d . . . C5 C -0.0960(2) 0.0160(4) 0.3975(4) 0.0810(13) Uani 1 1 d . . . H5B H -0.0834 -0.0263 0.4579 0.097 Uiso 1 1 calc R . . H5C H -0.1248 -0.0269 0.3437 0.097 Uiso 1 1 calc R . . C6 C -0.1225(3) 0.1263(4) 0.4073(6) 0.0883(19) Uani 1 1 d . . . H6B H -0.1647 0.1312 0.3627 0.106 Uiso 1 1 calc R . . H6C H -0.1181 0.1385 0.4742 0.106 Uiso 1 1 calc R . . C10 C 0.10151(13) 0.5716(3) 0.3614(2) 0.0439(6) Uani 1 1 d . . . C11 C 0.20039(18) 0.6108(4) 0.3926(4) 0.0713(12) Uani 1 1 d . . . H11A H 0.2145 0.6141 0.3408 0.086 Uiso 1 1 calc R . . H11B H 0.2342 0.5962 0.4549 0.086 Uiso 1 1 calc R . . C12 C 0.1684(2) 0.7164(4) 0.3970(5) 0.0839(15) Uani 1 1 d . . . H12A H 0.1884 0.7519 0.4606 0.101 Uiso 1 1 calc R . . H12B H 0.1667 0.7673 0.3459 0.101 Uiso 1 1 calc R . . C7 C 0.13210(13) 0.2217(3) 0.3653(2) 0.0418(6) Uani 1 1 d . . . C9 C 0.2126(2) 0.1037(4) 0.4044(5) 0.0809(15) Uani 1 1 d . . . H9A H 0.2481 0.0982 0.4660 0.097 Uiso 1 1 calc R . . H9B H 0.2219 0.0760 0.3514 0.097 Uiso 1 1 calc R . . C8 C 0.1597(2) 0.0414(4) 0.4096(5) 0.0835(15) Uani 1 1 d . . . H8B H 0.1479 -0.0207 0.3646 0.100 Uiso 1 1 calc R . . H8C H 0.1693 0.0152 0.4759 0.100 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 Dy1 0.03092(11) 0.03188(11) 0.04056(12) 0.000 0.01261(8) 0.000 O1 0.0590(13) 0.0451(12) 0.0616(14) -0.0095(10) 0.0333(11) -0.0033(10) O2 0.0468(11) 0.0478(12) 0.0553(12) 0.0073(10) 0.0263(10) 0.0006(9) O4 0.0359(10) 0.0437(12) 0.0645(14) -0.0093(10) 0.0132(9) -0.0051(9) O3 0.0375(10) 0.0417(11) 0.0533(12) 0.0056(9) 0.0111(9) 0.0055(8) O5 0.32(4) 1.27(14) 0.60(6) 0.000 -0.31(4) 0.000 O6 0.32(2) 0.346(16) 0.53(4) -0.023(15) 0.28(2) -0.171(14) O7 0.27(2) 0.33(3) 0.24(2) 0.13(2) 0.19(2) 0.19(2) O7A 0.163(13) 0.24(2) 0.256(19) -0.110(17) 0.057(13) -0.129(14) O8 0.47(2) 0.155(7) 0.339(15) -0.016(9) 0.330(17) -0.034(10) O9 0.223(12) 0.201(11) 0.336(17) 0.104(10) -0.033(12) -0.081(8) N2 0.075(2) 0.074(2) 0.097(3) -0.026(2) 0.057(2) -0.0106(18) N1 0.079(2) 0.0503(18) 0.119(3) -0.021(2) 0.062(2) -0.0069(18) N4 0.092(3) 0.0506(18) 0.106(3) 0.0179(18) 0.067(2) 0.0044(17) N3 0.088(3) 0.0511(19) 0.139(4) 0.006(2) 0.084(3) 0.0004(17) N7 0.0388(14) 0.0416(15) 0.092(2) -0.0045(14) 0.0206(14) -0.0017(11) N8 0.0463(16) 0.0433(17) 0.115(3) -0.0239(18) 0.0222(18) -0.0072(13) N6 0.0402(15) 0.064(2) 0.111(3) 0.030(2) 0.0278(17) 0.0104(14) N5 0.0495(18) 0.0492(18) 0.111(3) 0.0278(17) 0.034(2) 0.0109(13) N9 0.0148(11) 0.0062(10) 0.0328(13) 0.000 0.0164(10) 0.000 N10 0.0506(19) 0.0495(18) 0.098(3) -0.0235(17) 0.042(2) -0.0084(12) C1 0.0481(16) 0.0505(17) 0.0382(14) -0.0081(12) 0.0175(12) -0.0014(13) C2 0.087(4) 0.083(3) 0.078(3) -0.014(2) 0.051(3) 0.014(2) C3 0.084(3) 0.058(2) 0.081(3) -0.023(2) 0.034(2) 0.005(2) C4 0.0484(17) 0.0478(16) 0.0384(15) 0.0023(12) 0.0180(13) -0.0013(13) C5 0.086(3) 0.067(3) 0.109(4) 0.019(3) 0.059(3) -0.006(2) C6 0.100(4) 0.072(3) 0.132(5) 0.005(3) 0.086(4) -0.011(2) C10 0.0357(13) 0.0424(16) 0.0445(15) -0.0039(12) 0.0076(11) -0.0021(11) C11 0.0408(18) 0.055(2) 0.108(4) -0.001(2) 0.021(2) -0.0085(16) C12 0.056(2) 0.052(2) 0.141(5) -0.022(3) 0.039(3) -0.0169(18) C7 0.0371(13) 0.0444(15) 0.0401(14) 0.0059(11) 0.0123(11) 0.0038(11) C9 0.052(2) 0.065(3) 0.125(4) 0.026(3) 0.036(3) 0.020(2) C8 0.068(3) 0.061(3) 0.131(4) 0.043(3) 0.051(3) 0.027(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Dy1 O3 2.372(2) 2 ? Dy1 O3 2.372(2) . ? Dy1 O4 2.375(2) . ? Dy1 O4 2.375(2) 2 ? Dy1 O1 2.383(2) . ? Dy1 O1 2.383(2) 2 ? Dy1 O2 2.405(2) 2 ? Dy1 O2 2.405(2) . ? O1 C1 1.253(4) . ? O2 C4 1.253(4) . ? O4 C10 1.247(4) . ? O3 C7 1.246(4) . ? O5 N9 1.07(2) . ? O6 N9 0.857(15) . ? O7 N10 1.120(16) . ? O7A N10 1.149(11) . ? O8 N10 0.987(9) . ? O9 N10 1.093(14) . ? N2 C1 1.337(4) . ? N2 C2 1.444(6) . ? N2 H2A 0.8600 . ? N1 C1 1.308(5) . ? N1 C3 1.446(5) . ? N1 H1A 0.8600 . ? N4 C4 1.334(5) . ? N4 C5 1.453(5) . ? N4 H4A 0.8600 . ? N3 C4 1.326(5) . ? N3 C6 1.442(5) . ? N3 H3A 0.8600 . ? N7 C10 1.331(4) . ? N7 C11 1.452(5) . ? N7 H7A 0.8600 . ? N8 C10 1.349(5) . ? N8 C12 1.449(5) . ? N8 H8A 0.8600 . ? N6 C7 1.340(4) . ? N6 C9 1.441(6) . ? N6 H6A 0.8600 . ? N5 C7 1.323(4) . ? N5 C8 1.442(5) . ? N5 H5A 0.8600 . ? N9 O6 0.857(15) 2 ? C2 C3 1.525(7) . ? C2 H2B 0.9700 . ? C2 H2C 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C5 C6 1.520(7) . ? C5 H5B 0.9700 . ? C5 H5C 0.9700 . ? C6 H6B 0.9700 . ? C6 H6C 0.9700 . ? C11 C12 1.517(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C9 C8 1.529(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? 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 O3 Dy1 O3 146.10(11) 2 . ? O3 Dy1 O4 138.55(8) 2 . ? O3 Dy1 O4 73.59(8) . . ? O3 Dy1 O4 73.59(8) 2 2 ? O3 Dy1 O4 138.55(8) . 2 ? O4 Dy1 O4 73.57(12) . 2 ? O3 Dy1 O1 74.90(8) 2 . ? O3 Dy1 O1 115.30(9) . . ? O4 Dy1 O1 74.56(8) . . ? O4 Dy1 O1 78.91(9) 2 . ? O3 Dy1 O1 115.30(9) 2 2 ? O3 Dy1 O1 74.90(8) . 2 ? O4 Dy1 O1 78.91(9) . 2 ? O4 Dy1 O1 74.56(8) 2 2 ? O1 Dy1 O1 146.73(12) . 2 ? O3 Dy1 O2 74.82(8) 2 2 ? O3 Dy1 O2 77.94(8) . 2 ? O4 Dy1 O2 144.57(8) . 2 ? O4 Dy1 O2 118.60(9) 2 2 ? O1 Dy1 O2 138.12(8) . 2 ? O1 Dy1 O2 73.61(8) 2 2 ? O3 Dy1 O2 77.94(8) 2 . ? O3 Dy1 O2 74.82(8) . . ? O4 Dy1 O2 118.60(9) . . ? O4 Dy1 O2 144.57(8) 2 . ? O1 Dy1 O2 73.61(8) . . ? O1 Dy1 O2 138.12(8) 2 . ? O2 Dy1 O2 72.29(11) 2 . ? C1 O1 Dy1 139.0(2) . . ? C4 O2 Dy1 138.7(2) . . ? C10 O4 Dy1 141.9(2) . . ? C7 O3 Dy1 140.8(2) . . ? C1 N2 C2 111.9(4) . . ? C1 N2 H2A 124.1 . . ? C2 N2 H2A 124.1 . . ? C1 N1 C3 113.4(4) . . ? C1 N1 H1A 123.3 . . ? C3 N1 H1A 123.3 . . ? C4 N4 C5 111.7(4) . . ? C4 N4 H4A 124.1 . . ? C5 N4 H4A 124.1 . . ? C4 N3 C6 113.3(4) . . ? C4 N3 H3A 123.3 . . ? C6 N3 H3A 123.3 . . ? C10 N7 C11 112.5(3) . . ? C10 N7 H7A 123.8 . . ? C11 N7 H7A 123.8 . . ? C10 N8 C12 110.9(3) . . ? C10 N8 H8A 124.5 . . ? C12 N8 H8A 124.5 . . ? C7 N6 C9 111.9(3) . . ? C7 N6 H6A 124.0 . . ? C9 N6 H6A 124.0 . . ? C7 N5 C8 112.8(3) . . ? C7 N5 H5A 123.6 . . ? C8 N5 H5A 123.6 . . ? O6 N9 O6 155(2) 2 . ? O6 N9 O5 102.4(11) 2 . ? O6 N9 O5 102.4(11) . . ? O8 N10 O9 121.9(13) . . ? O8 N10 O7 133.8(14) . . ? O9 N10 O7 85.8(15) . . ? O8 N10 O7A 105.6(15) . . ? O9 N10 O7A 122.7(14) . . ? O7 N10 O7A 82.9(18) . . ? O1 C1 N1 126.0(3) . . ? O1 C1 N2 124.8(3) . . ? N1 C1 N2 109.2(3) . . ? N2 C2 C3 102.9(4) . . ? N2 C2 H2B 111.2 . . ? C3 C2 H2B 111.2 . . ? N2 C2 H2C 111.2 . . ? C3 C2 H2C 111.2 . . ? H2B C2 H2C 109.1 . . ? N1 C3 C2 102.1(4) . . ? N1 C3 H3B 111.4 . . ? C2 C3 H3B 111.4 . . ? N1 C3 H3C 111.4 . . ? C2 C3 H3C 111.4 . . ? H3B C3 H3C 109.2 . . ? O2 C4 N3 126.2(3) . . ? O2 C4 N4 124.9(3) . . ? N3 C4 N4 108.9(3) . . ? N4 C5 C6 103.2(4) . . ? N4 C5 H5B 111.1 . . ? C6 C5 H5B 111.1 . . ? N4 C5 H5C 111.1 . . ? C6 C5 H5C 111.1 . . ? H5B C5 H5C 109.1 . . ? N3 C6 C5 102.3(4) . . ? N3 C6 H6B 111.3 . . ? C5 C6 H6B 111.3 . . ? N3 C6 H6C 111.3 . . ? C5 C6 H6C 111.3 . . ? H6B C6 H6C 109.2 . . ? O4 C10 N7 126.1(3) . . ? O4 C10 N8 124.4(3) . . ? N7 C10 N8 109.5(3) . . ? N7 C11 C12 102.6(3) . . ? N7 C11 H11A 111.2 . . ? C12 C11 H11A 111.2 . . ? N7 C11 H11B 111.2 . . ? C12 C11 H11B 111.2 . . ? H11A C11 H11B 109.2 . . ? N8 C12 C11 104.2(3) . . ? N8 C12 H12A 110.9 . . ? C11 C12 H12A 110.9 . . ? N8 C12 H12B 110.9 . . ? C11 C12 H12B 110.9 . . ? H12A C12 H12B 108.9 . . ? O3 C7 N5 125.8(3) . . ? O3 C7 N6 125.1(3) . . ? N5 C7 N6 109.1(3) . . ? N6 C9 C8 102.8(3) . . ? N6 C9 H9A 111.2 . . ? C8 C9 H9A 111.2 . . ? N6 C9 H9B 111.2 . . ? C8 C9 H9B 111.2 . . ? H9A C9 H9B 109.1 . . ? N5 C8 C9 102.6(3) . . ? N5 C8 H8B 111.3 . . ? C9 C8 H8B 111.3 . . ? N5 C8 H8C 111.3 . . ? C9 C8 H8C 111.3 . . ? H8B C8 H8C 109.2 . . ? 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 O4 0.86 2.18 2.878(4) 138.1 . N2 H2A O9 0.86 2.22 3.003(11) 151.5 . N3 H3A O1 0.86 2.19 2.879(4) 137.1 . N4 H4A O6 0.86 2.19 3.013(10) 158.7 2 N5 H5A O2 0.86 2.18 2.882(4) 138.2 . N6 H6A O8 0.86 2.22 2.940(11) 141.7 2 N7 H7A O3 0.86 2.26 2.930(4) 134.6 . N8 H8A O5 0.86 2.27 2.830(9) 122.9 1_565 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.440 _refine_diff_density_min -0.777 _refine_diff_density_rms 0.088 _database_code_depnum_ccdc_archive 'CCDC 951608' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Tb _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H48 N19 O17 Tb' _chemical_formula_weight 1033.73 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' Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' 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 24.3791(12) _cell_length_b 12.1598(6) _cell_length_c 14.8200(7) _cell_angle_alpha 90.00 _cell_angle_beta 114.3940(10) _cell_angle_gamma 90.00 _cell_volume 4001.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9907 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 29.55 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.716 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2104 _exptl_absorpt_coefficient_mu 1.863 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6050 _exptl_absorpt_correction_T_max 0.7070 _exptl_absorpt_process_details '(SADABS; Bruker 2008)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18969 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 29.65 _reflns_number_total 5319 _reflns_number_gt 4890 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0723P)^2^+3.9201P] 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 5319 _refine_ls_number_parameters 286 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0965 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.012 _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 Tb1 Tb 0.0000 0.363784(13) 0.2500 0.03763(8) Uani 1 2 d S . . O1 O -0.05116(11) 0.42034(19) 0.34856(18) 0.0550(5) Uani 1 1 d . . . O2 O -0.00550(10) 0.20316(19) 0.34135(16) 0.0506(5) Uani 1 1 d . . . O4 O 0.05344(9) 0.52084(19) 0.33935(18) 0.0535(5) Uani 1 1 d . . . O3 O 0.10151(9) 0.30700(18) 0.33955(16) 0.0497(5) Uani 1 1 d . . . O5 O 0.0000 -0.2206(17) 0.2500 0.74(4) Uani 1 2 d SD . . O6 O 0.0239(6) -0.1131(14) 0.3101(12) 0.369(12) Uani 1 1 d D . . O7 O -0.2797(12) 0.398(2) 0.2791(19) 0.262(14) Uani 0.50 1 d P . . O7A O -0.2849(8) 0.3100(17) 0.2087(16) 0.224(9) Uani 0.50 1 d P . . O8 O -0.2275(7) 0.3952(9) 0.2115(10) 0.255(7) Uani 1 1 d . . . O9 O -0.2166(7) 0.3516(9) 0.3331(12) 0.307(10) Uani 1 1 d . . . N2 N -0.11542(17) 0.5149(3) 0.3968(3) 0.0777(10) Uani 1 1 d . . . H2A H -0.1365 0.4597 0.4002 0.093 Uiso 1 1 calc R . . N1 N -0.04303(19) 0.6035(3) 0.3836(4) 0.0777(11) Uani 1 1 d . . . H1A H -0.0116 0.6155 0.3726 0.093 Uiso 1 1 calc R . . N4 N -0.04500(18) 0.0469(3) 0.3784(3) 0.0737(9) Uani 1 1 d . . . H4A H -0.0187 0.0010 0.3762 0.088 Uiso 1 1 calc R . . N3 N -0.08741(19) 0.2029(3) 0.3805(4) 0.0827(12) Uani 1 1 d . . . H3A H -0.0942 0.2725 0.3755 0.099 Uiso 1 1 calc R . . N7 N 0.15364(13) 0.5286(3) 0.3714(3) 0.0617(7) Uani 1 1 d . . . H7A H 0.1592 0.4596 0.3656 0.074 Uiso 1 1 calc R . . N8 N 0.10884(14) 0.6801(3) 0.3824(3) 0.0736(10) Uani 1 1 d . . . H8A H 0.0815 0.7223 0.3860 0.088 Uiso 1 1 calc R . . N6 N 0.19123(14) 0.2156(3) 0.3862(3) 0.0715(9) Uani 1 1 d . . . H6A H 0.2133 0.2714 0.3878 0.086 Uiso 1 1 calc R . . N5 N 0.11346(17) 0.1236(3) 0.3805(4) 0.0719(11) Uani 1 1 d . . . H5A H 0.0772 0.1106 0.3731 0.086 Uiso 1 1 calc R . . N9 N 0.0000 -0.13451(19) 0.2500 0.0236(5) Uani 1 2 d SD . . N10 N -0.24556(17) 0.3662(3) 0.2554(4) 0.0662(10) Uani 1 1 d . . . C1 C -0.06801(14) 0.5071(3) 0.3739(2) 0.0486(6) Uani 1 1 d . . . C2 C -0.1271(3) 0.6278(4) 0.4151(4) 0.0794(14) Uani 1 1 d . . . H2B H -0.1295 0.6349 0.4785 0.095 Uiso 1 1 calc R . . H2C H -0.1642 0.6546 0.3633 0.095 Uiso 1 1 calc R . . C3 C -0.0730(2) 0.6886(4) 0.4147(4) 0.0773(12) Uani 1 1 d . . . H3B H -0.0852 0.7494 0.3681 0.093 Uiso 1 1 calc R . . H3C H -0.0475 0.7161 0.4801 0.093 Uiso 1 1 calc R . . C4 C -0.04305(16) 0.1555(3) 0.3644(2) 0.0480(6) Uani 1 1 d . . . C5 C -0.0963(2) 0.0161(4) 0.3974(4) 0.0822(13) Uani 1 1 d . . . H5B H -0.0841 -0.0264 0.4580 0.099 Uiso 1 1 calc R . . H5C H -0.1249 -0.0264 0.3429 0.099 Uiso 1 1 calc R . . C6 C -0.1227(3) 0.1262(4) 0.4072(6) 0.0910(19) Uani 1 1 d . . . H6B H -0.1650 0.1311 0.3624 0.109 Uiso 1 1 calc R . . H6C H -0.1184 0.1383 0.4745 0.109 Uiso 1 1 calc R . . C10 C 0.10172(13) 0.5715(3) 0.3618(2) 0.0459(6) Uani 1 1 d . . . C11 C 0.20043(18) 0.6116(4) 0.3929(5) 0.0739(12) Uani 1 1 d . . . H11A H 0.2147 0.6149 0.3408 0.089 Uiso 1 1 calc R . . H11B H 0.2342 0.5969 0.4556 0.089 Uiso 1 1 calc R . . C12 C 0.1688(2) 0.7160(4) 0.3975(5) 0.0854(14) Uani 1 1 d . . . H12A H 0.1890 0.7516 0.4614 0.102 Uiso 1 1 calc R . . H12B H 0.1671 0.7668 0.3459 0.102 Uiso 1 1 calc R . . C7 C 0.13230(13) 0.2216(3) 0.3655(2) 0.0451(6) Uani 1 1 d . . . C9 C 0.2130(2) 0.1042(4) 0.4053(5) 0.0834(14) Uani 1 1 d . . . H9A H 0.2484 0.0989 0.4674 0.100 Uiso 1 1 calc R . . H9B H 0.2227 0.0765 0.3522 0.100 Uiso 1 1 calc R . . C8 C 0.1598(2) 0.0419(4) 0.4102(5) 0.0871(15) Uani 1 1 d . . . H8B H 0.1483 -0.0203 0.3651 0.104 Uiso 1 1 calc R . . H8C H 0.1692 0.0159 0.4768 0.104 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 Tb1 0.03141(10) 0.03534(11) 0.04413(11) 0.000 0.01359(7) 0.000 O1 0.0593(13) 0.0487(12) 0.0650(12) -0.0101(10) 0.0336(11) -0.0041(10) O2 0.0473(11) 0.0519(12) 0.0576(11) 0.0066(9) 0.0266(9) 0.0003(9) O4 0.0363(10) 0.0493(11) 0.0676(13) -0.0093(10) 0.0141(9) -0.0065(8) O3 0.0387(10) 0.0463(11) 0.0574(11) 0.0052(9) 0.0130(8) 0.0048(8) O5 0.22(2) 1.29(13) 0.41(4) 0.000 -0.17(3) 0.000 O6 0.314(19) 0.402(18) 0.46(3) 0.035(16) 0.23(2) 0.221(16) O7 0.28(2) 0.34(3) 0.25(2) 0.14(2) 0.20(2) 0.20(2) O7A 0.150(13) 0.24(2) 0.232(17) -0.094(16) 0.028(12) -0.111(14) O8 0.426(19) 0.171(7) 0.310(13) -0.045(9) 0.293(15) -0.077(10) O9 0.233(13) 0.212(11) 0.331(17) 0.115(10) -0.030(12) -0.080(8) N2 0.074(2) 0.081(2) 0.099(2) -0.027(2) 0.057(2) -0.0089(18) N1 0.080(2) 0.0543(17) 0.118(3) -0.021(2) 0.060(2) -0.0052(18) N4 0.089(2) 0.0513(16) 0.106(3) 0.0169(17) 0.065(2) 0.0038(16) N3 0.084(2) 0.0583(19) 0.142(4) 0.008(2) 0.083(3) -0.0002(17) N7 0.0388(13) 0.0468(14) 0.095(2) -0.0056(14) 0.0231(13) -0.0029(11) N8 0.0475(16) 0.0472(16) 0.115(3) -0.0219(18) 0.0229(17) -0.0055(13) N6 0.0397(14) 0.067(2) 0.107(2) 0.0264(18) 0.0287(15) 0.0096(13) N5 0.0506(18) 0.0528(17) 0.113(3) 0.0283(17) 0.0346(19) 0.0112(12) N9 0.0217(11) 0.0122(9) 0.0435(13) 0.000 0.0200(10) 0.000 N10 0.0523(19) 0.0563(19) 0.102(3) -0.0238(17) 0.044(2) -0.0096(13) C1 0.0497(15) 0.0552(17) 0.0409(12) -0.0071(11) 0.0187(11) -0.0011(12) C2 0.085(3) 0.088(3) 0.080(3) -0.014(2) 0.049(3) 0.016(2) C3 0.084(3) 0.063(2) 0.086(3) -0.023(2) 0.036(2) 0.004(2) C4 0.0495(16) 0.0522(16) 0.0433(13) 0.0024(11) 0.0200(12) -0.0012(13) C5 0.085(3) 0.071(3) 0.108(3) 0.016(2) 0.057(3) -0.009(2) C6 0.100(4) 0.077(3) 0.132(5) 0.006(3) 0.085(4) -0.013(2) C10 0.0358(12) 0.0437(15) 0.0495(13) -0.0036(11) 0.0089(10) -0.0027(10) C11 0.0410(17) 0.059(2) 0.113(4) -0.002(2) 0.023(2) -0.0092(15) C12 0.056(2) 0.057(2) 0.138(4) -0.021(3) 0.036(2) -0.0159(18) C7 0.0365(13) 0.0498(15) 0.0455(13) 0.0061(11) 0.0133(10) 0.0040(11) C9 0.053(2) 0.069(2) 0.128(4) 0.026(3) 0.037(2) 0.021(2) C8 0.067(3) 0.065(2) 0.139(4) 0.042(3) 0.053(3) 0.025(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Tb1 O3 2.377(2) 2 ? Tb1 O3 2.377(2) . ? Tb1 O1 2.381(2) . ? Tb1 O1 2.381(2) 2 ? Tb1 O4 2.382(2) . ? Tb1 O4 2.382(2) 2 ? Tb1 O2 2.411(2) 2 ? Tb1 O2 2.411(2) . ? O1 C1 1.245(4) . ? O2 C4 1.245(4) . ? O4 C10 1.246(4) . ? O3 C7 1.246(4) . ? O5 N9 1.05(2) . ? O6 N9 0.879(15) . ? O7 N10 1.098(16) . ? O7A N10 1.148(12) . ? O8 N10 0.990(9) . ? O9 N10 1.088(14) . ? N2 C1 1.335(4) . ? N2 C2 1.449(6) . ? N2 H2A 0.8600 . ? N1 C1 1.302(5) . ? N1 C3 1.447(5) . ? N1 H1A 0.8600 . ? N4 C4 1.340(4) . ? N4 C5 1.440(5) . ? N4 H4A 0.8600 . ? N3 C4 1.331(5) . ? N3 C6 1.431(5) . ? N3 H3A 0.8600 . ? N7 C10 1.321(4) . ? N7 C11 1.456(5) . ? N7 H7A 0.8600 . ? N8 C10 1.350(5) . ? N8 C12 1.451(5) . ? N8 H8A 0.8600 . ? N6 C7 1.341(4) . ? N6 C9 1.439(6) . ? N6 H6A 0.8600 . ? N5 C7 1.328(4) . ? N5 C8 1.431(5) . ? N5 H5A 0.8600 . ? N9 O6 0.879(15) 2 ? C2 C3 1.513(8) . ? C2 H2B 0.9700 . ? C2 H2C 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C5 C6 1.519(7) . ? C5 H5B 0.9700 . ? C5 H5C 0.9700 . ? C6 H6B 0.9700 . ? C6 H6C 0.9700 . ? C11 C12 1.503(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C9 C8 1.530(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? 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 O3 Tb1 O3 146.23(11) 2 . ? O3 Tb1 O1 74.81(8) 2 . ? O3 Tb1 O1 115.46(8) . . ? O3 Tb1 O1 115.46(8) 2 2 ? O3 Tb1 O1 74.81(8) . 2 ? O1 Tb1 O1 146.42(11) . 2 ? O3 Tb1 O4 138.39(7) 2 . ? O3 Tb1 O4 73.63(7) . . ? O1 Tb1 O4 74.46(8) . . ? O1 Tb1 O4 78.73(8) 2 . ? O3 Tb1 O4 73.63(7) 2 2 ? O3 Tb1 O4 138.39(7) . 2 ? O1 Tb1 O4 78.73(8) . 2 ? O1 Tb1 O4 74.46(8) 2 2 ? O4 Tb1 O4 73.39(11) . 2 ? O3 Tb1 O2 74.80(7) 2 2 ? O3 Tb1 O2 77.98(8) . 2 ? O1 Tb1 O2 138.00(7) . 2 ? O1 Tb1 O2 74.03(8) 2 2 ? O4 Tb1 O2 144.79(7) . 2 ? O4 Tb1 O2 118.80(8) 2 2 ? O3 Tb1 O2 77.98(8) 2 . ? O3 Tb1 O2 74.80(7) . . ? O1 Tb1 O2 74.03(8) . . ? O1 Tb1 O2 138.00(7) 2 . ? O4 Tb1 O2 118.80(8) . . ? O4 Tb1 O2 144.79(7) 2 . ? O2 Tb1 O2 71.82(11) 2 . ? C1 O1 Tb1 138.8(2) . . ? C4 O2 Tb1 138.5(2) . . ? C10 O4 Tb1 141.7(2) . . ? C7 O3 Tb1 140.4(2) . . ? N10 O8 O9 32.2(7) . . ? N10 O9 O8 29.0(7) . . ? C1 N2 C2 111.8(4) . . ? C1 N2 H2A 124.1 . . ? C2 N2 H2A 124.1 . . ? C1 N1 C3 113.9(4) . . ? C1 N1 H1A 123.1 . . ? C3 N1 H1A 123.1 . . ? C4 N4 C5 112.1(4) . . ? C4 N4 H4A 124.0 . . ? C5 N4 H4A 124.0 . . ? C4 N3 C6 113.2(4) . . ? C4 N3 H3A 123.4 . . ? C6 N3 H3A 123.4 . . ? C10 N7 C11 112.3(3) . . ? C10 N7 H7A 123.8 . . ? C11 N7 H7A 123.8 . . ? C10 N8 C12 110.9(3) . . ? C10 N8 H8A 124.6 . . ? C12 N8 H8A 124.6 . . ? C7 N6 C9 111.7(3) . . ? C7 N6 H6A 124.2 . . ? C9 N6 H6A 124.2 . . ? C7 N5 C8 113.0(4) . . ? C7 N5 H5A 123.5 . . ? C8 N5 H5A 123.5 . . ? O6 N9 O6 146(2) 2 . ? O6 N9 O5 107.2(12) 2 . ? O6 N9 O5 107.2(12) . . ? O8 N10 O9 118.9(13) . . ? O8 N10 O7 133.5(14) . . ? O9 N10 O7 88.1(15) . . ? O8 N10 O7A 107.7(15) . . ? O9 N10 O7A 123.8(15) . . ? O7 N10 O7A 81.2(19) . . ? O1 C1 N1 126.8(3) . . ? O1 C1 N2 124.4(3) . . ? N1 C1 N2 108.8(3) . . ? N2 C2 C3 103.0(4) . . ? N2 C2 H2B 111.2 . . ? C3 C2 H2B 111.2 . . ? N2 C2 H2C 111.2 . . ? C3 C2 H2C 111.2 . . ? H2B C2 H2C 109.1 . . ? N1 C3 C2 101.9(4) . . ? N1 C3 H3B 111.4 . . ? C2 C3 H3B 111.4 . . ? N1 C3 H3C 111.4 . . ? C2 C3 H3C 111.4 . . ? H3B C3 H3C 109.3 . . ? O2 C4 N3 126.3(3) . . ? O2 C4 N4 125.3(3) . . ? N3 C4 N4 108.4(3) . . ? N4 C5 C6 103.1(4) . . ? N4 C5 H5B 111.2 . . ? C6 C5 H5B 111.2 . . ? N4 C5 H5C 111.2 . . ? C6 C5 H5C 111.2 . . ? H5B C5 H5C 109.1 . . ? N3 C6 C5 102.7(4) . . ? N3 C6 H6B 111.2 . . ? C5 C6 H6B 111.2 . . ? N3 C6 H6C 111.2 . . ? C5 C6 H6C 111.2 . . ? H6B C6 H6C 109.1 . . ? O4 C10 N7 126.2(3) . . ? O4 C10 N8 124.3(3) . . ? N7 C10 N8 109.5(3) . . ? N7 C11 C12 103.0(3) . . ? N7 C11 H11A 111.2 . . ? C12 C11 H11A 111.2 . . ? N7 C11 H11B 111.2 . . ? C12 C11 H11B 111.2 . . ? H11A C11 H11B 109.1 . . ? N8 C12 C11 104.0(3) . . ? N8 C12 H12A 111.0 . . ? C11 C12 H12A 111.0 . . ? N8 C12 H12B 111.0 . . ? C11 C12 H12B 111.0 . . ? H12A C12 H12B 109.0 . . ? O3 C7 N5 126.4(3) . . ? O3 C7 N6 124.6(3) . . ? N5 C7 N6 108.9(3) . . ? N6 C9 C8 103.0(3) . . ? N6 C9 H9A 111.2 . . ? C8 C9 H9A 111.2 . . ? N6 C9 H9B 111.2 . . ? C8 C9 H9B 111.2 . . ? H9A C9 H9B 109.1 . . ? N5 C8 C9 102.6(3) . . ? N5 C8 H8B 111.2 . . ? C9 C8 H8B 111.2 . . ? N5 C8 H8C 111.2 . . ? C9 C8 H8C 111.2 . . ? H8B C8 H8C 109.2 . . ? 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 O4 0.86 2.17 2.872(4) 138.1 . N2 H2A O9 0.86 2.22 2.999(12) 150.8 . N3 H3A O1 0.86 2.20 2.888(4) 137.1 . N4 H4A O6 0.86 2.19 3.006(10) 157.7 . N5 H5A O2 0.86 2.18 2.880(4) 137.9 . N6 H6A O8 0.86 2.23 2.950(11) 141.2 2 N7 H7A O3 0.86 2.26 2.934(4) 134.9 . N8 H8A O5 0.86 2.28 2.837(9) 122.8 1_565 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 29.65 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 1.377 _refine_diff_density_min -0.948 _refine_diff_density_rms 0.116 #===END OF 2 _database_code_depnum_ccdc_archive 'CCDC 951609'