# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email northwindy@126.com _publ_contact_author_name 'Zheng-Qiang Xia' loop_ _publ_author_name 'Zheng-Qiang Xia ' 'San-Ping Chen' 'Qing Wei' 'Cheng-Fang Qiao' ; Yang Yang ; 'Lin-Qiang Duan' # Attachment '- H2BIC--874290.cif' data_xb4184 _database_code_depnum_ccdc_archive 'CCDC 874290' #TrackingRef '- H2BIC--874290.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 N2 O2, 2(H2 O)' _chemical_formula_sum 'C8 H10 N2 O4' _chemical_formula_weight 198.18 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 monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc ' 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 6.860(2) _cell_length_b 7.368(2) _cell_length_c 18.967(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.738(9) _cell_angle_gamma 90.00 _cell_volume 902.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 313 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 24.28 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 1.459 _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4373 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.0856 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.09 _reflns_number_total 1596 _reflns_number_gt 812 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0954P)^2^+0.1599P] 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 1596 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1331 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.2105 _refine_ls_wR_factor_gt 0.1680 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6336(3) 0.9877(3) 0.10315(11) 0.0562(7) Uani 1 1 d . . . O2 O 0.5353(3) 0.9099(3) 0.19975(11) 0.0594(7) Uani 1 1 d . . . N1 N 0.1599(3) 0.7749(3) 0.09808(12) 0.0418(7) Uani 1 1 d . . . H1A H 0.1638 0.7549 0.1432 0.050 Uiso 1 1 calc R . . N2 N 0.2517(4) 0.8594(3) 0.00427(12) 0.0421(7) Uani 1 1 d . . . H2 H 0.3240 0.9034 -0.0209 0.050 Uiso 1 1 calc R . . C2 C 0.3107(4) 0.8511(4) 0.07848(15) 0.0396(8) Uani 1 1 d . . . C3 C -0.0037(4) 0.7334(4) 0.03379(15) 0.0386(8) Uani 1 1 d . . . C6 C -0.2636(5) 0.6853(4) -0.11041(17) 0.0512(9) Uani 1 1 d . . . H6 H -0.3549 0.6677 -0.1589 0.061 Uiso 1 1 calc R . . C8 C 0.0544(4) 0.7856(4) -0.02619(15) 0.0397(8) Uani 1 1 d . . . C5 C -0.3239(5) 0.6323(4) -0.04940(17) 0.0508(9) Uani 1 1 d . . . H5 H -0.4538 0.5806 -0.0585 0.061 Uiso 1 1 calc R . . C4 C -0.1961(4) 0.6552(4) 0.02249(16) 0.0446(8) Uani 1 1 d . . . H4 H -0.2361 0.6197 0.0626 0.054 Uiso 1 1 calc R . . C7 C -0.0729(5) 0.7627(4) -0.10019(16) 0.0464(8) Uani 1 1 d . . . H7 H -0.0321 0.7974 -0.1403 0.056 Uiso 1 1 calc R . . C1 C 0.5129(5) 0.9234(4) 0.13229(16) 0.0450(9) Uani 1 1 d . . . O3 O 0.1513(3) 0.6739(3) 0.23461(11) 0.0596(7) Uani 1 1 d . . . H3A H 0.1811 0.6956 0.2811 0.089 Uiso 1 1 d R . . H3B H 0.1531 0.5595 0.2292 0.089 Uiso 1 1 d R . . O4 O 0.7601(4) 0.5331(4) 0.20669(14) 0.0781(8) Uani 1 1 d . . . H4A H 0.6859 0.6128 0.1774 0.117 Uiso 1 1 d R . . H4B H 0.7162 0.5215 0.2433 0.117 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0469(13) 0.0749(16) 0.0479(12) 0.0032(11) 0.0174(10) -0.0096(12) O2 0.0553(13) 0.0858(18) 0.0340(10) -0.0004(11) 0.0111(9) -0.0135(13) N1 0.0489(14) 0.0454(15) 0.0313(11) 0.0010(11) 0.0139(10) 0.0005(12) N2 0.0384(13) 0.0531(16) 0.0354(12) 0.0001(12) 0.0134(10) -0.0053(12) C2 0.0401(16) 0.0382(17) 0.0407(15) 0.0036(13) 0.0139(13) 0.0052(14) C3 0.0415(16) 0.0356(17) 0.0369(14) -0.0011(13) 0.0107(12) 0.0016(14) C6 0.0487(19) 0.053(2) 0.0445(16) -0.0006(15) 0.0060(15) 0.0000(16) C8 0.0472(17) 0.0346(16) 0.0367(14) 0.0011(13) 0.0132(13) 0.0028(14) C5 0.0458(18) 0.049(2) 0.0576(18) -0.0017(16) 0.0178(15) -0.0012(15) C4 0.0428(17) 0.0485(19) 0.0435(15) 0.0001(14) 0.0158(13) -0.0018(15) C7 0.0513(17) 0.051(2) 0.0367(14) 0.0006(14) 0.0150(13) 0.0031(16) C1 0.0483(18) 0.0446(19) 0.0415(16) -0.0023(14) 0.0142(14) -0.0005(15) O3 0.0744(15) 0.0644(15) 0.0394(11) 0.0054(11) 0.0185(10) 0.0055(12) O4 0.0666(16) 0.094(2) 0.0722(15) 0.0173(14) 0.0217(13) 0.0001(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.235(4) . ? O2 C1 1.240(4) . ? N1 C2 1.335(4) . ? N1 C3 1.384(3) . ? N1 H1A 0.8600 . ? N2 C2 1.328(3) . ? N2 C8 1.390(4) . ? N2 H2 0.8600 . ? C2 C1 1.514(4) . ? C3 C8 1.381(4) . ? C3 C4 1.389(4) . ? C6 C7 1.379(4) . ? C6 C5 1.409(5) . ? C6 H6 0.9300 . ? C8 C7 1.390(4) . ? C5 C4 1.360(4) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? C7 H7 0.9300 . ? O3 H3A 0.8500 . ? O3 H3B 0.8500 . ? O4 H4A 0.8501 . ? O4 H4B 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C3 108.7(2) . . ? C2 N1 H1A 125.6 . . ? C3 N1 H1A 125.6 . . ? C2 N2 C8 109.1(2) . . ? C2 N2 H2 125.4 . . ? C8 N2 H2 125.4 . . ? N2 C2 N1 109.1(2) . . ? N2 C2 C1 125.5(3) . . ? N1 C2 C1 125.4(3) . . ? C8 C3 N1 106.9(2) . . ? C8 C3 C4 120.8(3) . . ? N1 C3 C4 132.3(3) . . ? C7 C6 C5 121.8(3) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C3 C8 N2 106.1(2) . . ? C3 C8 C7 122.7(3) . . ? N2 C8 C7 131.2(3) . . ? C4 C5 C6 121.4(3) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C4 C3 117.6(3) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? C6 C7 C8 115.8(3) . . ? C6 C7 H7 122.1 . . ? C8 C7 H7 122.1 . . ? O1 C1 O2 128.6(3) . . ? O1 C1 C2 115.7(3) . . ? O2 C1 C2 115.7(3) . . ? H3A O3 H3B 107.7 . . ? H4A O4 H4B 107.7 . . ? 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 O3 0.86 1.86 2.714(3) 170.2 . N2 H2 O1 0.86 1.86 2.669(3) 155.6 3_675 O3 H3B O2 0.85 2.38 2.855(3) 116.0 2_645 O4 H4A O2 0.85 2.52 3.157(4) 132.9 . O4 H4B O2 0.85 2.47 3.242(4) 152.3 2_645 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.09 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.321 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.070 # Attachment '- Compound 2--874291.cif' data_xb4185_0m _database_code_depnum_ccdc_archive 'CCDC 874291' #TrackingRef '- Compound 2--874291.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H15 N6 O6 Tb' _chemical_formula_sum 'C24 H15 N6 O6 Tb' _chemical_formula_weight 642.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' 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 9.7089(14) _cell_length_b 8.9276(13) _cell_length_c 25.930(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.090(2) _cell_angle_gamma 90.00 _cell_volume 2247.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3824 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 25.49 _exptl_crystal_description flaky _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 1.899 _exptl_crystal_density_diffrn 1.899 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 3.204 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.361 _exptl_absorpt_correction_T_max 0.852 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10687 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3983 _reflns_number_gt 3375 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0362P)^2^+11.8919P] 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 3983 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1021 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.48919(3) -0.04769(3) 0.218594(11) 0.01804(12) Uani 1 1 d . . . C1 C 0.2364(6) 0.1479(8) 0.2624(3) 0.0243(14) Uani 1 1 d . . . C2 C 0.3316(7) 0.1262(8) 0.3080(2) 0.0258(15) Uani 1 1 d . . . C3 C 0.4924(7) 0.0330(9) 0.3564(3) 0.0313(16) Uani 1 1 d . . . C4 C 0.5975(7) -0.0522(10) 0.3801(3) 0.0372(18) Uani 1 1 d . . . H4 H 0.6372 -0.1331 0.3634 0.045 Uiso 1 1 calc R . . C5 C 0.6386(10) -0.0114(12) 0.4282(3) 0.058(3) Uani 1 1 d . . . H5 H 0.7072 -0.0668 0.4449 0.069 Uiso 1 1 calc R . . C6 C 0.5818(11) 0.1107(13) 0.4537(4) 0.068(3) Uani 1 1 d . . . H6 H 0.6153 0.1356 0.4864 0.081 Uiso 1 1 calc R . . C7 C 0.4780(10) 0.1953(11) 0.4320(3) 0.058(3) Uani 1 1 d . . . H7 H 0.4387 0.2756 0.4492 0.069 Uiso 1 1 calc R . . C8 C 0.4350(7) 0.1533(9) 0.3824(3) 0.0342(17) Uani 1 1 d . . . C9 C 0.4226(7) -0.0593(8) 0.0937(3) 0.0289(16) Uani 1 1 d . . . C10 C 0.5754(6) -0.0265(7) 0.0966(2) 0.0228(14) Uani 1 1 d . . . C11 C 0.7792(7) 0.0038(8) 0.1290(3) 0.0253(15) Uani 1 1 d . . . C12 C 0.7849(7) 0.0320(8) 0.0759(3) 0.0287(16) Uani 1 1 d . . . C13 C 0.8982(7) 0.0167(9) 0.1606(3) 0.0353(17) Uani 1 1 d . . . H13 H 0.8965 -0.0024 0.1958 0.042 Uiso 1 1 calc R . . C14 C 1.0172(7) 0.0589(10) 0.1364(3) 0.0393(19) Uani 1 1 d . . . H14 H 1.0973 0.0698 0.1563 0.047 Uiso 1 1 calc R . . C15 C 1.0231(8) 0.0863(10) 0.0834(3) 0.043(2) Uani 1 1 d . . . H15 H 1.1067 0.1120 0.0689 0.052 Uiso 1 1 calc R . . C16 C 0.9067(8) 0.0756(9) 0.0523(3) 0.0373(19) Uani 1 1 d . . . H16 H 0.9092 0.0965 0.0172 0.045 Uiso 1 1 calc R . . C17 C 0.7165(6) 0.2244(7) 0.2455(2) 0.0208(14) Uani 1 1 d . . . C18 C 0.6196(6) 0.2958(7) 0.2082(3) 0.0228(14) Uani 1 1 d . . . C19 C 0.4531(6) 0.3172(7) 0.1532(3) 0.0249(15) Uani 1 1 d . . . C20 C 0.3389(7) 0.2991(8) 0.1206(3) 0.0363(18) Uani 1 1 d . . . H20 H 0.2828 0.2150 0.1229 0.044 Uiso 1 1 calc R . . C21 C 0.3119(9) 0.4088(10) 0.0855(3) 0.050(2) Uani 1 1 d . . . H21 H 0.2357 0.3983 0.0635 0.060 Uiso 1 1 calc R . . C22 C 0.3940(9) 0.5363(10) 0.0811(3) 0.047(2) Uani 1 1 d . . . H22 H 0.3732 0.6065 0.0556 0.056 Uiso 1 1 calc R . . C23 C 0.5056(8) 0.5602(8) 0.1139(3) 0.0379(18) Uani 1 1 d . . . H23 H 0.5598 0.6458 0.1120 0.046 Uiso 1 1 calc R . . C24 C 0.5317(7) 0.4489(8) 0.1499(3) 0.0272(15) Uani 1 1 d . . . N1 N 0.6445(5) -0.0346(6) 0.1409(2) 0.0221(12) Uani 1 1 d . . . N2 N 0.6538(5) 0.0114(7) 0.0566(2) 0.0274(13) Uani 1 1 d . . . H2 H 0.6270 0.0210 0.0250 0.033 Uiso 1 1 calc R . . N3 N 0.5108(5) 0.2243(6) 0.1903(2) 0.0262(13) Uani 1 1 d . . . N4 N 0.6362(6) 0.4318(6) 0.1864(2) 0.0284(13) Uani 1 1 d . . . H4A H 0.6997 0.4958 0.1938 0.034 Uiso 1 1 calc R . . N5 N 0.4270(5) 0.0202(7) 0.3084(2) 0.0276(13) Uani 1 1 d . . . N6 N 0.3333(6) 0.2100(7) 0.3507(2) 0.0342(14) Uani 1 1 d . . . H6A H 0.2806 0.2849 0.3571 0.041 Uiso 1 1 calc R . . O1 O 0.3724(4) -0.0777(5) 0.13748(17) 0.0248(10) Uani 1 1 d . . . O2 O 0.3651(5) -0.0636(6) 0.05132(18) 0.0363(13) Uani 1 1 d . . . O3 O 0.2642(5) 0.0681(5) 0.22451(17) 0.0285(11) Uani 1 1 d . . . O4 O 0.1376(4) 0.2370(5) 0.26665(18) 0.0273(11) Uani 1 1 d . . . O5 O 0.6786(4) 0.0966(5) 0.25944(18) 0.0253(10) Uani 1 1 d . . . O6 O 0.8261(4) 0.2883(5) 0.25894(17) 0.0246(10) 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 Tb1 0.01554(17) 0.01735(18) 0.02116(19) -0.00017(13) -0.00151(11) -0.00045(12) C1 0.021(3) 0.023(4) 0.029(4) 0.003(3) 0.001(3) -0.002(3) C2 0.030(4) 0.023(4) 0.024(4) 0.004(3) 0.001(3) -0.001(3) C3 0.028(4) 0.045(5) 0.021(4) 0.011(3) -0.005(3) -0.007(3) C4 0.026(4) 0.051(5) 0.035(4) 0.009(4) -0.005(3) 0.009(3) C5 0.053(5) 0.085(8) 0.034(5) 0.012(5) -0.015(4) 0.008(5) C6 0.080(7) 0.086(8) 0.036(5) -0.004(5) -0.033(5) 0.008(6) C7 0.085(7) 0.052(6) 0.036(5) -0.014(4) -0.017(5) 0.016(5) C8 0.040(4) 0.035(4) 0.027(4) -0.007(3) -0.005(3) 0.008(3) C9 0.023(3) 0.030(4) 0.034(4) -0.004(3) 0.001(3) -0.003(3) C10 0.025(3) 0.023(4) 0.020(3) 0.000(3) 0.000(3) -0.002(3) C11 0.023(3) 0.029(4) 0.024(4) -0.002(3) 0.000(3) -0.001(3) C12 0.025(3) 0.034(4) 0.028(4) 0.002(3) 0.004(3) -0.002(3) C13 0.033(4) 0.045(5) 0.028(4) -0.001(3) -0.002(3) -0.001(3) C14 0.021(4) 0.059(5) 0.038(4) -0.001(4) -0.003(3) -0.007(3) C15 0.024(4) 0.058(6) 0.048(5) -0.004(4) 0.004(4) -0.008(4) C16 0.034(4) 0.053(5) 0.025(4) 0.004(3) 0.005(3) -0.006(4) C17 0.018(3) 0.022(4) 0.022(3) -0.005(3) -0.001(3) 0.004(3) C18 0.018(3) 0.018(3) 0.033(4) 0.000(3) -0.003(3) 0.000(3) C19 0.018(3) 0.023(4) 0.033(4) 0.001(3) -0.009(3) 0.002(3) C20 0.030(4) 0.029(4) 0.049(5) 0.005(4) -0.019(3) -0.003(3) C21 0.054(5) 0.050(6) 0.046(5) 0.003(4) -0.029(4) 0.003(4) C22 0.051(5) 0.048(5) 0.041(5) 0.009(4) -0.020(4) 0.010(4) C23 0.047(5) 0.024(4) 0.043(5) 0.012(3) -0.013(4) 0.000(3) C24 0.028(3) 0.023(4) 0.031(4) 0.002(3) -0.010(3) -0.001(3) N1 0.015(3) 0.032(3) 0.019(3) -0.002(2) 0.000(2) -0.001(2) N2 0.025(3) 0.039(4) 0.018(3) 0.004(2) -0.001(2) -0.004(3) N3 0.024(3) 0.016(3) 0.038(3) 0.007(2) -0.007(2) -0.001(2) N4 0.031(3) 0.019(3) 0.036(3) 0.003(2) -0.010(3) -0.006(2) N5 0.020(3) 0.034(3) 0.029(3) 0.000(3) -0.003(2) 0.003(2) N6 0.038(3) 0.032(4) 0.032(3) -0.007(3) -0.003(3) 0.013(3) O1 0.027(2) 0.027(3) 0.020(2) 0.0001(19) 0.0025(19) -0.0059(19) O2 0.028(3) 0.062(4) 0.019(3) 0.001(2) -0.005(2) -0.006(2) O3 0.028(2) 0.033(3) 0.025(3) -0.006(2) -0.003(2) 0.006(2) O4 0.019(2) 0.025(3) 0.038(3) -0.003(2) -0.003(2) 0.005(2) O5 0.023(2) 0.020(2) 0.033(3) 0.006(2) -0.008(2) -0.0034(19) O6 0.020(2) 0.018(2) 0.036(3) -0.004(2) -0.010(2) -0.0054(18) _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 O4 2.318(4) 2_545 ? Tb1 O6 2.379(4) 2_645 ? Tb1 O1 2.386(4) . ? Tb1 O3 2.424(4) . ? Tb1 O5 2.467(4) . ? Tb1 N5 2.493(6) . ? Tb1 N1 2.541(5) . ? Tb1 N3 2.546(5) . ? C1 O3 1.247(8) . ? C1 O4 1.253(8) . ? C1 C2 1.501(9) . ? C2 N5 1.324(9) . ? C2 N6 1.336(9) . ? C3 C8 1.391(10) . ? C3 N5 1.390(9) . ? C3 C4 1.404(10) . ? C4 C5 1.354(12) . ? C4 H4 0.9300 . ? C5 C6 1.393(14) . ? C5 H5 0.9300 . ? C6 C7 1.373(13) . ? C6 H6 0.9300 . ? C7 C8 1.394(11) . ? C7 H7 0.9300 . ? C8 N6 1.370(9) . ? C9 O2 1.224(8) . ? C9 O1 1.255(8) . ? C9 C10 1.512(9) . ? C10 N1 1.321(8) . ? C10 N2 1.342(8) . ? C11 N1 1.393(8) . ? C11 C12 1.401(9) . ? C11 C13 1.408(10) . ? C12 N2 1.372(9) . ? C12 C16 1.397(9) . ? C13 C14 1.377(10) . ? C13 H13 0.9300 . ? C14 C15 1.400(11) . ? C14 H14 0.9300 . ? C15 C16 1.378(11) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 O6 1.251(7) . ? C17 O5 1.254(8) . ? C17 C18 1.481(9) . ? C18 N3 1.312(8) . ? C18 N4 1.350(8) . ? C19 N3 1.381(8) . ? C19 C20 1.390(9) . ? C19 C24 1.406(9) . ? C20 C21 1.360(11) . ? C20 H20 0.9300 . ? C21 C22 1.396(12) . ? C21 H21 0.9300 . ? C22 C23 1.382(11) . ? C22 H22 0.9300 . ? C23 C24 1.382(10) . ? C23 H23 0.9300 . ? C24 N4 1.383(9) . ? N2 H2 0.8600 . ? N4 H4A 0.8600 . ? N6 H6A 0.8600 . ? O4 Tb1 2.318(4) 2 ? O6 Tb1 2.379(4) 2_655 ? 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 O4 Tb1 O6 81.33(15) 2_545 2_645 ? O4 Tb1 O1 78.89(15) 2_545 . ? O6 Tb1 O1 119.35(15) 2_645 . ? O4 Tb1 O3 82.02(16) 2_545 . ? O6 Tb1 O3 157.36(16) 2_645 . ? O1 Tb1 O3 71.93(15) . . ? O4 Tb1 O5 139.08(15) 2_545 . ? O6 Tb1 O5 70.36(15) 2_645 . ? O1 Tb1 O5 140.82(15) . . ? O3 Tb1 O5 114.56(15) . . ? O4 Tb1 N5 84.76(18) 2_545 . ? O6 Tb1 N5 96.65(17) 2_645 . ? O1 Tb1 N5 137.04(16) . . ? O3 Tb1 N5 66.58(16) . . ? O5 Tb1 N5 70.35(16) . . ? O4 Tb1 N1 119.57(17) 2_545 . ? O6 Tb1 N1 76.50(16) 2_645 . ? O1 Tb1 N1 65.52(15) . . ? O3 Tb1 N1 125.41(16) . . ? O5 Tb1 N1 82.40(16) . . ? N5 Tb1 N1 152.56(18) . . ? O4 Tb1 N3 152.26(16) 2_545 . ? O6 Tb1 N3 126.28(16) 2_645 . ? O1 Tb1 N3 83.88(17) . . ? O3 Tb1 N3 72.00(17) . . ? O5 Tb1 N3 63.99(16) . . ? N5 Tb1 N3 93.46(19) . . ? N1 Tb1 N3 71.00(18) . . ? O3 C1 O4 127.6(6) . . ? O3 C1 C2 114.1(6) . . ? O4 C1 C2 118.2(6) . . ? N5 C2 N6 113.3(6) . . ? N5 C2 C1 121.3(6) . . ? N6 C2 C1 125.4(6) . . ? C8 C3 N5 108.5(6) . . ? C8 C3 C4 120.1(7) . . ? N5 C3 C4 131.5(7) . . ? C5 C4 C3 117.2(8) . . ? C5 C4 H4 121.4 . . ? C3 C4 H4 121.4 . . ? C4 C5 C6 122.4(8) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C7 C6 C5 122.0(8) . . ? C7 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C6 C7 C8 115.8(8) . . ? C6 C7 H7 122.1 . . ? C8 C7 H7 122.1 . . ? N6 C8 C3 106.6(6) . . ? N6 C8 C7 130.8(7) . . ? C3 C8 C7 122.6(7) . . ? O2 C9 O1 129.0(6) . . ? O2 C9 C10 118.7(6) . . ? O1 C9 C10 112.2(6) . . ? N1 C10 N2 113.6(6) . . ? N1 C10 C9 120.9(6) . . ? N2 C10 C9 125.5(6) . . ? N1 C11 C12 108.5(6) . . ? N1 C11 C13 130.9(6) . . ? C12 C11 C13 120.6(6) . . ? N2 C12 C16 131.7(7) . . ? N2 C12 C11 106.3(6) . . ? C16 C12 C11 122.0(7) . . ? C14 C13 C11 116.4(7) . . ? C14 C13 H13 121.8 . . ? C11 C13 H13 121.8 . . ? C13 C14 C15 123.0(7) . . ? C13 C14 H14 118.5 . . ? C15 C14 H14 118.5 . . ? C16 C15 C14 120.9(7) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C12 117.1(7) . . ? C15 C16 H16 121.5 . . ? C12 C16 H16 121.5 . . ? O6 C17 O5 125.9(6) . . ? O6 C17 C18 120.8(6) . . ? O5 C17 C18 113.2(5) . . ? N3 C18 N4 113.0(6) . . ? N3 C18 C17 121.3(6) . . ? N4 C18 C17 125.5(6) . . ? N3 C19 C20 131.4(6) . . ? N3 C19 C24 109.4(5) . . ? C20 C19 C24 119.2(6) . . ? C21 C20 C19 117.7(7) . . ? C21 C20 H20 121.1 . . ? C19 C20 H20 121.1 . . ? C20 C21 C22 122.6(8) . . ? C20 C21 H21 118.7 . . ? C22 C21 H21 118.7 . . ? C23 C22 C21 121.2(8) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C22 C23 C24 115.9(7) . . ? C22 C23 H23 122.1 . . ? C24 C23 H23 122.1 . . ? C23 C24 N4 131.6(7) . . ? C23 C24 C19 123.3(6) . . ? N4 C24 C19 104.9(6) . . ? C10 N1 C11 104.9(5) . . ? C10 N1 Tb1 113.1(4) . . ? C11 N1 Tb1 139.5(4) . . ? C10 N2 C12 106.7(5) . . ? C10 N2 H2 126.6 . . ? C12 N2 H2 126.6 . . ? C18 N3 C19 105.5(5) . . ? C18 N3 Tb1 115.6(4) . . ? C19 N3 Tb1 137.6(4) . . ? C18 N4 C24 107.1(5) . . ? C18 N4 H4A 126.4 . . ? C24 N4 H4A 126.4 . . ? C2 N5 C3 104.9(6) . . ? C2 N5 Tb1 110.4(4) . . ? C3 N5 Tb1 137.9(4) . . ? C2 N6 C8 106.7(6) . . ? C2 N6 H6A 126.6 . . ? C8 N6 H6A 126.6 . . ? C9 O1 Tb1 126.6(4) . . ? C1 O3 Tb1 120.2(4) . . ? C1 O4 Tb1 162.0(4) . 2 ? C17 O5 Tb1 124.8(4) . . ? C17 O6 Tb1 169.2(4) . 2_655 ? 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 N2 H2 O2 0.86 2.02 2.839(7) 159.6 3_655 N4 H4A O5 0.86 1.90 2.697(7) 153.0 2_655 N6 H6A O1 0.86 1.93 2.774(7) 165.4 2 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.221 _refine_diff_density_min -1.662 _refine_diff_density_rms 0.153 data_xb4286_0m _database_code_depnum_ccdc_archive 'CCDC 874292' #TrackingRef '- Compound 1--874292.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H15 Eu N6 O6' _chemical_formula_sum 'C24 H15 Eu N6 O6' _chemical_formula_weight 635.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn ' 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 9.7575(10) _cell_length_b 8.9776(9) _cell_length_c 26.005(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.1130(10) _cell_angle_gamma 90.00 _cell_volume 2277.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4865 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.78 _exptl_crystal_description flaky _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 1.853 _exptl_crystal_density_diffrn 1.853 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 2.810 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.450 _exptl_absorpt_correction_T_max 0.799 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11759 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.99 _reflns_number_total 4461 _reflns_number_gt 3892 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0406P)^2^+0.6779P] 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 4461 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0785 _refine_ls_wR_factor_gt 0.0627 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 Eu1 Eu 0.489232(17) 0.44662(2) 0.218617(7) 0.01643(8) Uani 1 1 d . . . C1 C 0.2350(4) 0.6403(4) 0.26299(14) 0.0216(8) Uani 1 1 d . . . C2 C 0.3311(4) 0.6219(5) 0.30804(15) 0.0232(9) Uani 1 1 d . . . C3 C 0.4917(4) 0.5321(5) 0.35721(15) 0.0265(9) Uani 1 1 d . . . C4 C 0.4340(4) 0.6526(5) 0.38298(15) 0.0321(10) Uani 1 1 d . . . C5 C 0.5949(5) 0.4475(5) 0.38024(18) 0.0364(11) Uani 1 1 d . . . H5 H 0.6330 0.3659 0.3637 0.044 Uiso 1 1 calc R . . C6 C 0.6384(6) 0.4907(7) 0.4292(2) 0.0560(15) Uani 1 1 d . . . H6 H 0.7068 0.4364 0.4461 0.067 Uiso 1 1 calc R . . C7 C 0.5820(7) 0.6129(8) 0.4532(2) 0.0690(18) Uani 1 1 d . . . H7 H 0.6158 0.6396 0.4856 0.083 Uiso 1 1 calc R . . C8 C 0.4785(6) 0.6964(7) 0.43157(19) 0.0557(15) Uani 1 1 d . . . H8 H 0.4405 0.7775 0.4484 0.067 Uiso 1 1 calc R . . C9 C 0.7166(4) 0.7205(4) 0.24592(14) 0.0203(8) Uani 1 1 d . . . C10 C 0.6184(4) 0.7916(4) 0.20836(15) 0.0218(8) Uani 1 1 d . . . C11 C 0.5324(4) 0.9427(4) 0.15046(16) 0.0271(9) Uani 1 1 d . . . C12 C 0.5060(5) 1.0556(5) 0.11453(19) 0.0406(12) Uani 1 1 d . . . H12 H 0.5603 1.1406 0.1129 0.049 Uiso 1 1 calc R . . C13 C 0.3952(6) 1.0339(6) 0.0817(2) 0.0464(14) Uani 1 1 d . . . H13 H 0.3745 1.1050 0.0567 0.056 Uiso 1 1 calc R . . C14 C 0.3130(5) 0.9061(6) 0.08547(19) 0.0447(13) Uani 1 1 d . . . H14 H 0.2381 0.8958 0.0631 0.054 Uiso 1 1 calc R . . C15 C 0.3390(4) 0.7961(5) 0.12079(17) 0.0369(11) Uani 1 1 d . . . H15 H 0.2827 0.7128 0.1230 0.044 Uiso 1 1 calc R . . C16 C 0.4533(4) 0.8138(5) 0.15342(15) 0.0264(9) Uani 1 1 d . . . C17 C 0.4243(4) 0.4379(4) 0.09277(17) 0.0268(9) Uani 1 1 d . . . C18 C 0.5759(4) 0.4700(4) 0.09615(15) 0.0230(9) Uani 1 1 d . . . C19 C 0.7847(4) 0.5312(5) 0.07571(16) 0.0279(9) Uani 1 1 d . . . C20 C 0.9049(5) 0.5741(6) 0.05211(17) 0.0354(11) Uani 1 1 d . . . H20 H 0.9077 0.5945 0.0171 0.043 Uiso 1 1 calc R . . C21 C 1.0202(5) 0.5848(6) 0.08365(18) 0.0393(12) Uani 1 1 d . . . H21 H 1.1030 0.6127 0.0694 0.047 Uiso 1 1 calc R . . C22 C 1.0161(5) 0.5550(5) 0.13627(19) 0.0383(12) Uani 1 1 d . . . H22 H 1.0960 0.5641 0.1561 0.046 Uiso 1 1 calc R . . C23 C 0.8969(4) 0.5124(5) 0.15951(17) 0.0311(10) Uani 1 1 d . . . H23 H 0.8948 0.4919 0.1945 0.037 Uiso 1 1 calc R . . C24 C 0.7786(4) 0.5012(5) 0.12820(15) 0.0244(9) Uani 1 1 d . . . N1 N 0.5098(3) 0.7192(4) 0.19049(13) 0.0238(7) Uani 1 1 d . . . N2 N 0.6353(4) 0.9262(4) 0.18706(13) 0.0270(8) Uani 1 1 d . . . H2N H 0.6983 0.9899 0.1948 0.032 Uiso 1 1 calc R . . N3 N 0.6450(3) 0.4621(4) 0.14037(12) 0.0226(7) Uani 1 1 d . . . N4 N 0.6533(3) 0.5101(4) 0.05621(13) 0.0279(8) Uani 1 1 d . . . H4 H 0.6264 0.5206 0.0247 0.034 Uiso 1 1 calc R . . N5 N 0.4265(3) 0.5151(4) 0.30912(13) 0.0244(7) Uani 1 1 d . . . N6 N 0.3323(4) 0.7066(4) 0.35063(13) 0.0329(9) Uani 1 1 d . . . H6N H 0.2792 0.7808 0.3566 0.039 Uiso 1 1 calc R . . O1 O 0.3730(3) 0.4175(3) 0.13649(10) 0.0243(6) Uani 1 1 d . . . O2 O 0.3662(3) 0.4343(4) 0.05057(11) 0.0368(8) Uani 1 1 d . . . O3 O 0.2628(3) 0.5603(3) 0.22535(11) 0.0275(7) Uani 1 1 d . . . O4 O 0.1374(3) 0.7301(3) 0.26677(10) 0.0277(6) Uani 1 1 d . . . O5 O 0.6779(3) 0.5932(3) 0.25969(11) 0.0253(6) Uani 1 1 d . . . O6 O 0.8246(3) 0.7835(3) 0.25911(10) 0.0255(6) 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 Eu1 0.01544(12) 0.01703(12) 0.01673(12) 0.00000(7) -0.00146(7) -0.00036(7) C1 0.0181(18) 0.022(2) 0.025(2) -0.0029(17) 0.0005(15) -0.0001(16) C2 0.022(2) 0.026(2) 0.021(2) -0.0011(17) -0.0023(16) 0.0005(17) C3 0.024(2) 0.036(3) 0.019(2) -0.0031(17) -0.0009(16) 0.0034(18) C4 0.036(2) 0.035(3) 0.025(2) -0.0008(19) -0.0069(18) 0.005(2) C5 0.032(2) 0.049(3) 0.028(2) 0.004(2) -0.0043(19) 0.010(2) C6 0.053(4) 0.071(4) 0.042(3) 0.006(3) -0.023(3) 0.012(3) C7 0.086(5) 0.084(5) 0.035(3) -0.006(3) -0.034(3) 0.008(4) C8 0.081(4) 0.053(4) 0.032(3) -0.011(2) -0.020(3) 0.015(3) C9 0.0220(19) 0.019(2) 0.020(2) -0.0042(16) -0.0015(15) 0.0009(16) C10 0.0230(19) 0.0155(19) 0.027(2) -0.0019(16) -0.0053(16) 0.0004(15) C11 0.031(2) 0.020(2) 0.030(2) -0.0003(17) -0.0089(18) 0.0004(17) C12 0.047(3) 0.030(3) 0.044(3) 0.014(2) -0.014(2) -0.002(2) C13 0.056(3) 0.038(3) 0.045(3) 0.011(2) -0.019(3) 0.009(2) C14 0.046(3) 0.042(3) 0.045(3) -0.001(2) -0.028(2) 0.006(2) C15 0.034(2) 0.032(3) 0.045(3) -0.002(2) -0.015(2) -0.003(2) C16 0.025(2) 0.026(2) 0.028(2) 0.0010(18) -0.0065(16) -0.0007(17) C17 0.025(2) 0.028(2) 0.027(2) 0.0016(17) -0.0017(18) -0.0010(17) C18 0.022(2) 0.027(2) 0.020(2) 0.0002(16) -0.0010(16) -0.0012(16) C19 0.022(2) 0.037(3) 0.025(2) -0.0003(18) -0.0001(17) -0.0009(18) C20 0.029(2) 0.055(3) 0.022(2) 0.004(2) 0.0022(18) -0.005(2) C21 0.023(2) 0.060(3) 0.036(3) 0.001(2) 0.0057(19) -0.012(2) C22 0.023(2) 0.056(3) 0.036(3) -0.006(2) -0.0049(19) -0.004(2) C23 0.028(2) 0.042(3) 0.023(2) -0.002(2) -0.0042(18) 0.001(2) C24 0.021(2) 0.030(2) 0.023(2) 0.0021(18) 0.0012(16) 0.0004(17) N1 0.0212(16) 0.0191(17) 0.0309(19) 0.0013(14) -0.0073(14) -0.0016(14) N2 0.0257(18) 0.0196(18) 0.035(2) 0.0033(15) -0.0123(15) -0.0039(14) N3 0.0199(17) 0.032(2) 0.0162(17) 0.0010(14) 0.0001(13) 0.0007(14) N4 0.0232(18) 0.044(2) 0.0170(17) 0.0035(16) 0.0001(14) -0.0040(16) N5 0.0222(18) 0.0277(19) 0.0234(18) -0.0016(15) 0.0005(14) 0.0034(15) N6 0.038(2) 0.035(2) 0.0258(19) -0.0092(16) -0.0055(15) 0.0139(17) O1 0.0242(14) 0.0305(16) 0.0182(14) 0.0026(12) -0.0001(11) -0.0053(12) O2 0.0270(16) 0.064(2) 0.0185(16) 0.0056(14) -0.0076(13) -0.0083(15) O3 0.0221(15) 0.0364(18) 0.0239(15) -0.0069(13) -0.0020(12) 0.0066(12) O4 0.0245(14) 0.0265(16) 0.0320(16) -0.0043(13) -0.0019(12) 0.0080(12) O5 0.0223(14) 0.0221(15) 0.0310(16) 0.0033(12) -0.0088(12) -0.0023(12) O6 0.0209(14) 0.0208(14) 0.0343(16) -0.0019(12) -0.0084(12) -0.0034(12) _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 Eu1 O4 2.338(3) 2_545 ? Eu1 O6 2.396(3) 2_645 ? Eu1 O1 2.413(3) . ? Eu1 O3 2.443(3) . ? Eu1 O5 2.487(3) . ? Eu1 N5 2.519(3) . ? Eu1 N1 2.563(3) . ? Eu1 N3 2.567(3) . ? C1 O3 1.248(4) . ? C1 O4 1.253(4) . ? C1 C2 1.496(5) . ? C2 N5 1.336(5) . ? C2 N6 1.343(5) . ? C3 C5 1.388(6) . ? C3 C4 1.396(6) . ? C3 N5 1.400(5) . ? C4 N6 1.377(5) . ? C4 C8 1.385(6) . ? C5 C6 1.389(7) . ? C5 H5 0.9300 . ? C6 C7 1.383(9) . ? C6 H6 0.9300 . ? C7 C8 1.370(8) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 O6 1.239(4) . ? C9 O5 1.258(5) . ? C9 C10 1.497(5) . ? C10 N1 1.320(5) . ? C10 N2 1.341(5) . ? C11 N2 1.378(5) . ? C11 C16 1.394(6) . ? C11 C12 1.399(6) . ? C12 C13 1.379(7) . ? C12 H12 0.9300 . ? C13 C14 1.404(7) . ? C13 H13 0.9300 . ? C14 C15 1.369(7) . ? C14 H14 0.9300 . ? C15 C16 1.398(5) . ? C15 H15 0.9300 . ? C16 N1 1.390(5) . ? C17 O2 1.226(5) . ? C17 O1 1.264(5) . ? C17 C18 1.508(6) . ? C18 N3 1.323(5) . ? C18 N4 1.345(5) . ? C19 N4 1.382(5) . ? C19 C20 1.389(6) . ? C19 C24 1.394(6) . ? C20 C21 1.382(6) . ? C20 H20 0.9300 . ? C21 C22 1.396(7) . ? C21 H21 0.9300 . ? C22 C23 1.375(6) . ? C22 H22 0.9300 . ? C23 C24 1.404(6) . ? C23 H23 0.9300 . ? C24 N3 1.392(5) . ? N2 H2N 0.8600 . ? N4 H4 0.8600 . ? N6 H6N 0.8600 . ? O4 Eu1 2.338(3) 2 ? O6 Eu1 2.396(3) 2_655 ? 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 O4 Eu1 O6 81.55(9) 2_545 2_645 ? O4 Eu1 O1 79.23(9) 2_545 . ? O6 Eu1 O1 119.27(9) 2_645 . ? O4 Eu1 O3 81.59(9) 2_545 . ? O6 Eu1 O3 157.00(10) 2_645 . ? O1 Eu1 O3 72.45(9) . . ? O4 Eu1 O5 139.40(9) 2_545 . ? O6 Eu1 O5 70.63(9) 2_645 . ? O1 Eu1 O5 140.23(9) . . ? O3 Eu1 O5 114.28(9) . . ? O4 Eu1 N5 84.97(11) 2_545 . ? O6 Eu1 N5 96.91(10) 2_645 . ? O1 Eu1 N5 137.28(10) . . ? O3 Eu1 N5 66.09(10) . . ? O5 Eu1 N5 70.18(10) . . ? O4 Eu1 N1 152.20(10) 2_545 . ? O6 Eu1 N1 126.12(9) 2_645 . ? O1 Eu1 N1 83.62(10) . . ? O3 Eu1 N1 72.41(10) . . ? O5 Eu1 N1 63.63(9) . . ? N5 Eu1 N1 93.17(11) . . ? O4 Eu1 N3 119.79(10) 2_545 . ? O6 Eu1 N3 76.53(10) 2_645 . ? O1 Eu1 N3 65.13(10) . . ? O3 Eu1 N3 125.76(10) . . ? O5 Eu1 N3 82.36(10) . . ? N5 Eu1 N3 152.32(11) . . ? N1 Eu1 N3 70.80(11) . . ? O3 C1 O4 127.5(4) . . ? O3 C1 C2 114.1(3) . . ? O4 C1 C2 118.4(3) . . ? N5 C2 N6 113.2(3) . . ? N5 C2 C1 121.5(3) . . ? N6 C2 C1 125.3(4) . . ? C5 C3 C4 120.9(4) . . ? C5 C3 N5 129.7(4) . . ? C4 C3 N5 109.4(4) . . ? N6 C4 C8 131.8(4) . . ? N6 C4 C3 105.8(3) . . ? C8 C4 C3 122.4(4) . . ? C3 C5 C6 116.7(5) . . ? C3 C5 H5 121.7 . . ? C6 C5 H5 121.7 . . ? C7 C6 C5 121.2(5) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C8 C7 C6 123.0(5) . . ? C8 C7 H7 118.5 . . ? C6 C7 H7 118.5 . . ? C7 C8 C4 115.8(5) . . ? C7 C8 H8 122.1 . . ? C4 C8 H8 122.1 . . ? O6 C9 O5 126.4(4) . . ? O6 C9 C10 121.1(3) . . ? O5 C9 C10 112.4(3) . . ? N1 C10 N2 113.7(3) . . ? N1 C10 C9 121.2(3) . . ? N2 C10 C9 124.8(3) . . ? N2 C11 C16 105.6(3) . . ? N2 C11 C12 131.4(4) . . ? C16 C11 C12 122.9(4) . . ? C13 C12 C11 116.3(4) . . ? C13 C12 H12 121.8 . . ? C11 C12 H12 121.8 . . ? C12 C13 C14 120.9(4) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 122.6(4) . . ? C15 C14 H14 118.7 . . ? C13 C14 H14 118.7 . . ? C14 C15 C16 117.4(4) . . ? C14 C15 H15 121.3 . . ? C16 C15 H15 121.3 . . ? N1 C16 C11 109.4(3) . . ? N1 C16 C15 130.8(4) . . ? C11 C16 C15 119.8(4) . . ? O2 C17 O1 128.1(4) . . ? O2 C17 C18 119.5(4) . . ? O1 C17 C18 112.3(4) . . ? N3 C18 N4 113.7(4) . . ? N3 C18 C17 121.5(4) . . ? N4 C18 C17 124.8(4) . . ? N4 C19 C20 131.4(4) . . ? N4 C19 C24 106.0(3) . . ? C20 C19 C24 122.6(4) . . ? C21 C20 C19 116.2(4) . . ? C21 C20 H20 121.9 . . ? C19 C20 H20 121.9 . . ? C20 C21 C22 122.0(4) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C23 C22 C21 121.6(4) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C22 C23 C24 117.3(4) . . ? C22 C23 H23 121.4 . . ? C24 C23 H23 121.4 . . ? N3 C24 C19 109.2(3) . . ? N3 C24 C23 130.5(4) . . ? C19 C24 C23 120.2(4) . . ? C10 N1 C16 104.4(3) . . ? C10 N1 Eu1 115.9(2) . . ? C16 N1 Eu1 138.5(2) . . ? C10 N2 C11 106.8(3) . . ? C10 N2 H2N 126.6 . . ? C11 N2 H2N 126.6 . . ? C18 N3 C24 104.6(3) . . ? C18 N3 Eu1 113.1(3) . . ? C24 N3 Eu1 139.9(3) . . ? C18 N4 C19 106.5(3) . . ? C18 N4 H4 126.8 . . ? C19 N4 H4 126.8 . . ? C2 N5 C3 104.2(3) . . ? C2 N5 Eu1 109.7(2) . . ? C3 N5 Eu1 138.3(3) . . ? C2 N6 C4 107.4(3) . . ? C2 N6 H6N 126.3 . . ? C4 N6 H6N 126.3 . . ? C17 O1 Eu1 126.4(3) . . ? C1 O3 Eu1 120.5(2) . . ? C1 O4 Eu1 162.3(3) . 2 ? C9 O5 Eu1 125.6(2) . . ? C9 O6 Eu1 169.4(3) . 2_655 ? 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 N2 H2N O5 0.86 1.91 2.718(4) 154.8 2_655 N6 H6N O1 0.86 1.94 2.782(4) 166.6 2 N4 H4 O2 0.86 2.00 2.824(5) 159.5 3_665 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.877 _refine_diff_density_min -1.044 _refine_diff_density_rms 0.441 # Attachment '- Compound 4--874293.cif' data_xb4366_0m _database_code_depnum_ccdc_archive 'CCDC 874293' #TrackingRef '- Compound 4--874293.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H15 N6 O6 Pr' _chemical_formula_sum 'C24 H15 N6 O6 Pr' _chemical_formula_weight 624.33 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' Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn ' 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 9.8425(7) _cell_length_b 9.0698(7) _cell_length_c 26.084(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.2160(10) _cell_angle_gamma 90.00 _cell_volume 2327.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3711 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 26.99 _exptl_crystal_description flaky _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 1.781 _exptl_crystal_density_diffrn 1.781 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 2.147 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.491 _exptl_absorpt_correction_T_max 0.879 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11382 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.10 _reflns_number_total 4131 _reflns_number_gt 3605 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0277P)^2^+2.2832P] 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 4131 _refine_ls_number_parameters 338 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0661 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.003 _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 O6 O 0.8201(3) 0.7276(3) 0.25955(11) 0.0290(7) Uani 1 1 d . . . O5 O 0.1365(3) 0.7870(3) 0.26797(11) 0.0300(7) Uani 1 1 d . . . Pr1 Pr 0.489119(19) 1.06702(2) 0.218789(8) 0.01659(8) Uani 1 1 d . . . O1 O 0.6768(2) 0.9169(3) 0.26063(11) 0.0261(6) Uani 1 1 d . . . O3 O 0.3739(2) 1.0930(3) 0.13453(10) 0.0252(6) Uani 1 1 d . . . O2 O 0.2604(3) 0.9558(3) 0.22696(11) 0.0287(7) Uani 1 1 d . . . O4 O 0.3691(3) 1.0705(4) 0.04920(11) 0.0406(8) Uani 1 1 d . . . N2 N 0.6352(3) 0.5865(4) 0.18770(13) 0.0257(8) Uani 1 1 d . . . C12 C 0.5331(4) 0.5669(4) 0.15148(16) 0.0269(9) Uani 1 1 d . . . N5 N 0.6448(3) 1.0457(4) 0.13920(12) 0.0244(8) Uani 1 1 d . . . N4 N 0.3308(3) 0.8027(4) 0.35097(13) 0.0343(9) Uani 1 1 d . . . H4N H 0.2782 0.7288 0.3562 0.041 Uiso 1 1 calc R . . C18 C 0.3294(4) 0.8907(4) 0.30942(16) 0.0260(9) Uani 1 1 d . . . N3 N 0.4250(3) 0.9938(4) 0.31126(13) 0.0251(8) Uani 1 1 d . . . C23 C 0.5947(4) 1.0547(5) 0.38220(18) 0.0403(11) Uani 1 1 d . . . H23 H 0.6327 1.1368 0.3667 0.048 Uiso 1 1 calc R . . N6 N 0.6532(3) 0.9938(4) 0.05592(13) 0.0294(8) Uani 1 1 d . . . H6 H 0.6264 0.9821 0.0246 0.035 Uiso 1 1 calc R . . C16 C 0.7128(4) 0.7899(4) 0.24629(15) 0.0204(8) Uani 1 1 d . . . C17 C 0.2336(4) 0.8756(4) 0.26441(15) 0.0230(9) Uani 1 1 d . . . C24 C 0.4904(4) 0.9749(5) 0.35830(16) 0.0292(10) Uani 1 1 d . . . C6 C 0.7827(4) 0.9723(5) 0.07534(16) 0.0302(10) Uani 1 1 d . . . C7 C 0.5770(4) 1.0364(4) 0.09505(15) 0.0245(9) Uani 1 1 d . . . C5 C 0.7773(4) 1.0056(4) 0.12734(15) 0.0255(9) Uani 1 1 d . . . C3 C 1.0127(4) 0.9503(5) 0.13581(19) 0.0419(12) Uani 1 1 d . . . H3 H 1.0918 0.9421 0.1557 0.050 Uiso 1 1 calc R . . C15 C 0.6171(4) 0.7194(4) 0.20913(15) 0.0212(8) Uani 1 1 d . . . C2 C 1.0161(4) 0.9177(6) 0.08345(19) 0.0451(13) Uani 1 1 d . . . H2 H 1.0978 0.8882 0.0694 0.054 Uiso 1 1 calc R . . C4 C 0.8939(4) 0.9946(5) 0.15854(16) 0.0322(10) Uani 1 1 d . . . H4 H 0.8917 1.0162 0.1934 0.039 Uiso 1 1 calc R . . C8 C 0.4280(4) 1.0685(4) 0.09125(16) 0.0245(9) Uani 1 1 d . . . C19 C 0.4323(4) 0.8534(5) 0.38356(16) 0.0332(10) Uani 1 1 d . . . C1 C 0.9025(4) 0.9279(5) 0.05211(18) 0.0412(12) Uani 1 1 d . . . H1 H 0.9053 0.9063 0.0173 0.049 Uiso 1 1 calc R . . C13 C 0.4542(4) 0.6947(4) 0.15386(16) 0.0274(9) Uani 1 1 d . . . C14 C 0.3408(4) 0.7105(5) 0.12110(18) 0.0388(11) Uani 1 1 d . . . H14 H 0.2844 0.7925 0.1231 0.047 Uiso 1 1 calc R . . C11 C 0.5073(5) 0.4559(5) 0.11635(19) 0.0399(12) Uani 1 1 d . . . H11 H 0.5614 0.3720 0.1150 0.048 Uiso 1 1 calc R . . C9 C 0.3160(5) 0.6013(5) 0.0861(2) 0.0490(14) Uani 1 1 d . . . H9 H 0.2425 0.6110 0.0633 0.059 Uiso 1 1 calc R . . C10 C 0.3977(5) 0.4755(5) 0.0834(2) 0.0462(13) Uani 1 1 d . . . H10 H 0.3775 0.4039 0.0589 0.055 Uiso 1 1 calc R . . C22 C 0.6390(5) 1.0068(7) 0.4298(2) 0.0570(15) Uani 1 1 d . . . H22 H 0.7097 1.0567 0.4465 0.068 Uiso 1 1 calc R . . C20 C 0.4761(6) 0.8074(6) 0.4316(2) 0.0592(15) Uani 1 1 d . . . H20 H 0.4364 0.7277 0.4480 0.071 Uiso 1 1 calc R . . C21 C 0.5802(6) 0.8845(7) 0.4536(2) 0.0707(18) Uani 1 1 d . . . H21 H 0.6136 0.8552 0.4856 0.085 Uiso 1 1 calc R . . N1 N 0.5086(3) 0.7896(4) 0.19046(13) 0.0254(7) Uani 1 1 d . . . H2A H 0.695(4) 0.522(4) 0.1978(15) 0.017(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O6 0.0227(14) 0.0214(14) 0.0424(18) 0.0025(13) -0.0125(13) 0.0039(12) O5 0.0238(14) 0.0305(15) 0.0356(17) 0.0069(14) -0.0038(13) -0.0119(13) Pr1 0.01393(11) 0.01754(12) 0.01821(12) 0.00008(9) -0.00173(8) 0.00026(9) O1 0.0221(14) 0.0222(14) 0.0336(17) -0.0064(13) -0.0101(12) 0.0027(11) O3 0.0214(14) 0.0334(16) 0.0208(15) -0.0031(12) -0.0011(12) 0.0057(12) O2 0.0224(14) 0.0363(16) 0.0272(16) 0.0079(13) -0.0060(12) -0.0085(12) O4 0.0291(16) 0.070(2) 0.0229(17) -0.0051(16) -0.0088(14) 0.0116(15) N2 0.0230(17) 0.0214(18) 0.032(2) -0.0029(16) -0.0088(15) 0.0042(15) C12 0.027(2) 0.023(2) 0.031(2) -0.0004(19) -0.0089(18) -0.0037(18) N5 0.0200(16) 0.0350(19) 0.0181(18) -0.0010(15) -0.0025(14) 0.0012(14) N4 0.037(2) 0.038(2) 0.028(2) 0.0086(18) -0.0053(17) -0.0145(17) C18 0.022(2) 0.031(2) 0.026(2) 0.0044(18) 0.0022(18) -0.0003(17) N3 0.0216(17) 0.0310(18) 0.0225(19) 0.0010(16) -0.0013(15) -0.0059(15) C23 0.033(2) 0.053(3) 0.034(3) -0.003(2) -0.003(2) -0.012(2) N6 0.0258(18) 0.047(2) 0.0156(18) -0.0031(16) -0.0030(15) 0.0053(16) C16 0.0174(19) 0.0186(19) 0.025(2) 0.0063(17) -0.0026(16) -0.0021(16) C17 0.0185(19) 0.024(2) 0.026(2) -0.0001(18) -0.0009(17) 0.0017(17) C24 0.025(2) 0.040(3) 0.023(2) -0.0043(19) -0.0042(18) 0.0002(18) C6 0.024(2) 0.039(3) 0.027(2) -0.001(2) -0.0024(19) 0.0021(18) C7 0.024(2) 0.027(2) 0.021(2) -0.0024(17) -0.0028(18) 0.0022(17) C5 0.022(2) 0.032(2) 0.023(2) -0.0011(19) 0.0009(18) -0.0010(18) C3 0.025(2) 0.061(3) 0.039(3) 0.001(3) -0.008(2) 0.007(2) C15 0.022(2) 0.0170(18) 0.024(2) -0.0024(17) -0.0041(17) 0.0011(16) C2 0.025(2) 0.069(4) 0.042(3) -0.004(3) 0.007(2) 0.013(2) C4 0.030(2) 0.047(3) 0.019(2) 0.000(2) -0.0024(19) -0.001(2) C8 0.022(2) 0.028(2) 0.024(2) -0.0027(19) -0.0011(18) 0.0013(17) C19 0.037(2) 0.041(3) 0.022(2) 0.004(2) -0.002(2) -0.005(2) C1 0.033(2) 0.063(3) 0.028(2) -0.004(2) 0.006(2) 0.012(2) C13 0.026(2) 0.025(2) 0.031(2) 0.0011(19) -0.0089(18) -0.0037(18) C14 0.034(2) 0.032(2) 0.049(3) 0.000(2) -0.021(2) 0.002(2) C11 0.044(3) 0.028(2) 0.047(3) -0.008(2) -0.010(2) 0.003(2) C9 0.045(3) 0.049(3) 0.051(3) 0.000(3) -0.034(3) -0.004(2) C10 0.056(3) 0.038(3) 0.044(3) -0.011(2) -0.018(3) -0.008(2) C22 0.047(3) 0.081(4) 0.042(3) -0.010(3) -0.022(3) -0.009(3) C20 0.074(4) 0.066(4) 0.037(3) 0.018(3) -0.018(3) -0.013(3) C21 0.081(4) 0.089(5) 0.040(3) 0.011(3) -0.037(3) -0.008(4) N1 0.0214(17) 0.0291(18) 0.0255(19) -0.0056(16) -0.0039(14) 0.0010(15) _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 O6 C16 1.241(4) . ? O6 Pr1 2.433(2) 2_645 ? O5 C17 1.255(4) . ? O5 Pr1 2.376(3) 2_545 ? Pr1 O5 2.376(3) 2 ? Pr1 O6 2.433(2) 2_655 ? Pr1 O3 2.463(3) . ? Pr1 O2 2.480(3) . ? Pr1 O1 2.524(3) . ? Pr1 N3 2.593(3) . ? Pr1 N5 2.613(3) . ? Pr1 N1 2.631(3) . ? O1 C16 1.264(4) . ? O3 C8 1.278(5) . ? O2 C17 1.250(5) . ? O4 C8 1.230(5) . ? N2 C15 1.342(5) . ? N2 C12 1.376(5) . ? N2 H2A 0.86(4) . ? C12 C11 1.381(6) . ? C12 C13 1.398(5) . ? N5 C7 1.321(5) . ? N5 C5 1.395(5) . ? N4 C18 1.345(5) . ? N4 C19 1.377(5) . ? N4 H4N 0.8600 . ? C18 N3 1.326(5) . ? C18 C17 1.496(5) . ? N3 C24 1.384(5) . ? C23 C22 1.377(7) . ? C23 C24 1.392(6) . ? C23 H23 0.9300 . ? N6 C7 1.336(5) . ? N6 C6 1.375(5) . ? N6 H6 0.8600 . ? C16 C15 1.482(5) . ? C24 C19 1.411(6) . ? C6 C5 1.392(6) . ? C6 C1 1.397(6) . ? C7 C8 1.497(5) . ? C5 C4 1.397(5) . ? C3 C4 1.381(6) . ? C3 C2 1.399(7) . ? C3 H3 0.9300 . ? C15 N1 1.327(4) . ? C2 C1 1.374(6) . ? C2 H2 0.9300 . ? C4 H4 0.9300 . ? C19 C20 1.380(6) . ? C1 H1 0.9300 . ? C13 N1 1.385(5) . ? C13 C14 1.398(5) . ? C14 C9 1.366(6) . ? C14 H14 0.9300 . ? C11 C10 1.377(6) . ? C11 H11 0.9300 . ? C9 C10 1.398(7) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C22 C21 1.403(8) . ? C22 H22 0.9300 . ? C20 C21 1.358(7) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 O6 Pr1 170.3(2) . 2_645 ? C17 O5 Pr1 161.6(3) . 2_545 ? O5 Pr1 O6 82.24(9) 2 2_655 ? O5 Pr1 O3 79.54(9) 2 . ? O6 Pr1 O3 119.24(9) 2_655 . ? O5 Pr1 O2 81.55(9) 2 . ? O6 Pr1 O2 157.05(9) 2_655 . ? O3 Pr1 O2 73.39(9) . . ? O5 Pr1 O1 140.20(9) 2 . ? O6 Pr1 O1 70.64(8) 2_655 . ? O3 Pr1 O1 139.12(8) . . ? O2 Pr1 O1 113.61(9) . . ? O5 Pr1 N3 86.68(10) 2 . ? O6 Pr1 N3 98.00(10) 2_655 . ? O3 Pr1 N3 137.57(9) . . ? O2 Pr1 N3 64.94(9) . . ? O1 Pr1 N3 69.51(9) . . ? O5 Pr1 N5 119.56(10) 2 . ? O6 Pr1 N5 76.49(10) 2_655 . ? O3 Pr1 N5 64.19(9) . . ? O2 Pr1 N5 125.92(10) . . ? O1 Pr1 N5 82.39(9) . . ? N3 Pr1 N5 151.46(10) . . ? O5 Pr1 N1 152.29(9) 2 . ? O6 Pr1 N1 125.24(9) 2_655 . ? O3 Pr1 N1 82.86(9) . . ? O2 Pr1 N1 72.96(9) . . ? O1 Pr1 N1 63.14(9) . . ? N3 Pr1 N1 92.12(10) . . ? N5 Pr1 N1 70.02(10) . . ? C16 O1 Pr1 124.8(2) . . ? C8 O3 Pr1 125.4(2) . . ? C17 O2 Pr1 120.7(2) . . ? C15 N2 C12 107.5(3) . . ? C15 N2 H2A 125(3) . . ? C12 N2 H2A 127(3) . . ? N2 C12 C11 132.1(4) . . ? N2 C12 C13 105.1(3) . . ? C11 C12 C13 122.7(4) . . ? C7 N5 C5 104.3(3) . . ? C7 N5 Pr1 113.8(2) . . ? C5 N5 Pr1 139.7(3) . . ? C18 N4 C19 107.1(3) . . ? C18 N4 H4N 126.4 . . ? C19 N4 H4N 126.4 . . ? N3 C18 N4 113.2(4) . . ? N3 C18 C17 121.8(4) . . ? N4 C18 C17 125.0(4) . . ? C18 N3 C24 105.2(3) . . ? C18 N3 Pr1 109.5(3) . . ? C24 N3 Pr1 137.6(3) . . ? C22 C23 C24 117.2(5) . . ? C22 C23 H23 121.4 . . ? C24 C23 H23 121.4 . . ? C7 N6 C6 106.9(3) . . ? C7 N6 H6 126.6 . . ? C6 N6 H6 126.6 . . ? O6 C16 O1 125.1(3) . . ? O6 C16 C15 120.8(3) . . ? O1 C16 C15 114.1(3) . . ? O2 C17 O5 127.1(4) . . ? O2 C17 C18 114.9(3) . . ? O5 C17 C18 118.0(4) . . ? N3 C24 C23 131.1(4) . . ? N3 C24 C19 109.0(4) . . ? C23 C24 C19 119.9(4) . . ? N6 C6 C5 105.9(3) . . ? N6 C6 C1 131.7(4) . . ? C5 C6 C1 122.4(4) . . ? N5 C7 N6 113.8(3) . . ? N5 C7 C8 121.4(4) . . ? N6 C7 C8 124.8(4) . . ? C6 C5 N5 109.1(3) . . ? C6 C5 C4 120.3(4) . . ? N5 C5 C4 130.6(4) . . ? C4 C3 C2 121.3(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? N1 C15 N2 113.0(3) . . ? N1 C15 C16 121.9(3) . . ? N2 C15 C16 124.9(3) . . ? C1 C2 C3 122.0(4) . . ? C1 C2 H2 119.0 . . ? C3 C2 H2 119.0 . . ? C3 C4 C5 117.6(4) . . ? C3 C4 H4 121.2 . . ? C5 C4 H4 121.2 . . ? O4 C8 O3 126.0(4) . . ? O4 C8 C7 120.3(4) . . ? O3 C8 C7 113.7(3) . . ? N4 C19 C20 131.9(4) . . ? N4 C19 C24 105.6(3) . . ? C20 C19 C24 122.6(4) . . ? C2 C1 C6 116.4(4) . . ? C2 C1 H1 121.8 . . ? C6 C1 H1 121.8 . . ? N1 C13 C12 109.8(3) . . ? N1 C13 C14 130.5(4) . . ? C12 C13 C14 119.6(4) . . ? C9 C14 C13 117.6(4) . . ? C9 C14 H14 121.2 . . ? C13 C14 H14 121.2 . . ? C10 C11 C12 116.8(4) . . ? C10 C11 H11 121.6 . . ? C12 C11 H11 121.6 . . ? C14 C9 C10 122.0(4) . . ? C14 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C11 C10 C9 121.2(4) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C23 C22 C21 121.5(5) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C21 C20 C19 116.5(5) . . ? C21 C20 H20 121.7 . . ? C19 C20 H20 121.7 . . ? C20 C21 C22 122.3(5) . . ? C20 C21 H21 118.8 . . ? C22 C21 H21 118.8 . . ? C15 N1 C13 104.6(3) . . ? C15 N1 Pr1 114.8(2) . . ? C13 N1 Pr1 139.3(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 N4 H4N O3 0.86 1.96 2.803(4) 167.1 2_545 N2 H2A O1 0.86(4) 1.91(4) 2.739(4) 162(4) 2_645 N6 H6 O4 0.86 1.98 2.807(4) 159.8 3_675 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.896 _refine_diff_density_min -0.542 _refine_diff_density_rms 0.095 # Attachment '- Compound 5--874296.cif' data_xb4527 _database_code_depnum_ccdc_archive 'CCDC 874296' #TrackingRef '- Compound 5--874296.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H15 N6 Nd O6' _chemical_formula_sum 'C24 H15 N6 Nd O6' _chemical_formula_weight 627.66 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' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn ' 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 9.853(2) _cell_length_b 9.073(2) _cell_length_c 26.152(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.153(4) _cell_angle_gamma 90.00 _cell_volume 2337.3(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2473 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 23.52 _exptl_crystal_description flaky _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 1.784 _exptl_crystal_density_diffrn 1.784 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1236 _exptl_absorpt_coefficient_mu 2.276 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.483 _exptl_absorpt_correction_T_max 0.872 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11228 _diffrn_reflns_av_R_equivalents 0.0716 _diffrn_reflns_av_sigmaI/netI 0.0761 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.10 _reflns_number_total 4141 _reflns_number_gt 3396 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0288P)^2^+27.2895P] 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 4141 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0689 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1249 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 O3 O 0.8208(5) 0.7757(6) 0.2595(2) 0.0319(14) Uani 1 1 d . . . O2 O 0.1369(5) 0.7180(6) 0.2679(2) 0.0308(14) Uani 1 1 d . . . Nd1 Nd 0.48920(4) 0.43653(5) 0.218737(16) 0.01925(15) Uani 1 1 d . . . O4 O 0.6771(5) 0.5856(6) 0.2604(2) 0.0304(14) Uani 1 1 d . . . O5 O 0.3735(6) 0.4106(6) 0.1353(2) 0.0291(13) Uani 1 1 d . . . O6 O 0.3673(6) 0.4303(9) 0.0495(2) 0.0443(17) Uani 1 1 d . . . O1 O 0.2613(6) 0.5486(7) 0.2265(2) 0.0332(14) Uani 1 1 d . . . C5 C 0.5947(9) 0.4480(13) 0.3813(4) 0.044(2) Uani 1 1 d . . . H5 H 0.6331 0.3672 0.3652 0.053 Uiso 1 1 calc R . . C16 C 0.5333(8) 0.9367(10) 0.1512(3) 0.0288(19) Uani 1 1 d . . . C2 C 0.3308(8) 0.6137(9) 0.3089(3) 0.0282(19) Uani 1 1 d . . . N3 N 0.6454(7) 0.4554(8) 0.1394(3) 0.0297(16) Uani 1 1 d . . . N6 N 0.6353(7) 0.9164(7) 0.1874(3) 0.0275(16) Uani 1 1 d . . . H6 H 0.6992 0.9779 0.1948 0.033 Uiso 1 1 calc R . . N4 N 0.6529(7) 0.5066(9) 0.0562(3) 0.0332(18) Uani 1 1 d . . . H4 H 0.6263 0.5182 0.0249 0.040 Uiso 1 1 calc R . . N5 N 0.5113(7) 0.7163(8) 0.1901(3) 0.0288(17) Uani 1 1 d . . . C9 C 0.7146(8) 0.7146(8) 0.2460(3) 0.0233(18) Uani 1 1 d . . . N2 N 0.4252(7) 0.5091(8) 0.3108(3) 0.0280(16) Uani 1 1 d . . . C18 C 0.5762(8) 0.4647(9) 0.0951(3) 0.0279(19) Uani 1 1 d . . . C1 C 0.2350(8) 0.6279(9) 0.2641(3) 0.0272(19) Uani 1 1 d . . . N1 N 0.3309(7) 0.7014(8) 0.3512(3) 0.0352(18) Uani 1 1 d . . . H1 H 0.2780 0.7748 0.3569 0.042 Uiso 1 1 calc R . . C23 C 0.8940(9) 0.5081(11) 0.1589(4) 0.037(2) Uani 1 1 d . . . H23 H 0.8914 0.4882 0.1937 0.044 Uiso 1 1 calc R . . C4 C 0.4911(8) 0.5263(9) 0.3580(3) 0.0267(19) Uani 1 1 d . . . C19 C 0.7832(8) 0.5279(10) 0.0754(3) 0.030(2) Uani 1 1 d . . . C20 C 0.9027(9) 0.5733(13) 0.0522(4) 0.046(3) Uani 1 1 d . . . H20 H 0.9050 0.5962 0.0176 0.055 Uiso 1 1 calc R . . C17 C 0.4267(8) 0.4330(9) 0.0919(3) 0.0263(18) Uani 1 1 d . . . C22 C 1.0136(9) 0.5501(12) 0.1362(4) 0.044(2) Uani 1 1 d . . . H22 H 1.0927 0.5571 0.1561 0.053 Uiso 1 1 calc R . . C12 C 0.3399(9) 0.7901(10) 0.1210(4) 0.041(2) Uani 1 1 d . . . H12 H 0.2831 0.7086 0.1231 0.049 Uiso 1 1 calc R . . C24 C 0.7778(8) 0.4964(10) 0.1280(3) 0.0265(19) Uani 1 1 d . . . C11 C 0.4541(8) 0.8064(9) 0.1535(3) 0.0300(19) Uani 1 1 d . . . C3 C 0.4329(9) 0.6485(11) 0.3832(4) 0.038(2) Uani 1 1 d . . . C15 C 0.5064(10) 1.0454(10) 0.1156(4) 0.043(2) Uani 1 1 d . . . H15 H 0.5608 1.1289 0.1136 0.052 Uiso 1 1 calc R . . C7 C 0.5814(13) 0.6154(15) 0.4542(4) 0.068(4) Uani 1 1 d . . . H7 H 0.6143 0.6434 0.4863 0.082 Uiso 1 1 calc R . . C6 C 0.6402(12) 0.4925(15) 0.4292(4) 0.062(3) Uani 1 1 d . . . H6A H 0.7106 0.4411 0.4453 0.075 Uiso 1 1 calc R . . C14 C 0.3974(11) 1.0266(11) 0.0831(4) 0.049(3) Uani 1 1 d . . . H14 H 0.3771 1.0986 0.0589 0.058 Uiso 1 1 calc R . . C10 C 0.6171(8) 0.7829(9) 0.2092(3) 0.0252(18) Uani 1 1 d . . . C13 C 0.3161(11) 0.9014(11) 0.0858(4) 0.053(3) Uani 1 1 d . . . H13 H 0.2429 0.8922 0.0630 0.064 Uiso 1 1 calc R . . C8 C 0.4756(13) 0.6944(14) 0.4314(4) 0.066(3) Uani 1 1 d . . . H8 H 0.4355 0.7740 0.4476 0.079 Uiso 1 1 calc R . . C21 C 1.0178(9) 0.5825(13) 0.0836(4) 0.049(3) Uani 1 1 d . . . H21 H 1.0998 0.6108 0.0696 0.059 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 O3 0.020(3) 0.028(3) 0.047(4) -0.005(3) -0.014(3) -0.006(3) O2 0.024(3) 0.028(3) 0.040(4) -0.007(3) -0.003(3) 0.014(3) Nd1 0.0164(2) 0.0177(2) 0.0236(3) -0.0001(2) -0.00131(15) -0.00042(18) O4 0.027(3) 0.023(3) 0.040(4) 0.006(3) -0.011(3) -0.003(3) O5 0.028(3) 0.031(3) 0.029(3) 0.003(3) -0.002(3) -0.006(3) O6 0.033(3) 0.076(5) 0.024(3) 0.003(4) -0.008(3) -0.009(4) O1 0.031(3) 0.040(4) 0.029(3) -0.013(3) -0.004(3) 0.005(3) C5 0.033(5) 0.061(7) 0.037(6) -0.002(5) 0.001(4) 0.010(5) C16 0.025(4) 0.024(4) 0.037(5) -0.002(4) -0.008(4) -0.003(4) C2 0.026(4) 0.027(4) 0.032(5) -0.003(4) 0.005(4) -0.001(4) N3 0.025(4) 0.034(4) 0.029(4) 0.002(3) 0.002(3) 0.004(3) N6 0.028(4) 0.020(4) 0.034(4) 0.004(3) -0.008(3) -0.006(3) N4 0.028(4) 0.052(5) 0.019(4) 0.007(3) -0.001(3) -0.005(4) N5 0.028(4) 0.034(4) 0.025(4) 0.017(3) -0.001(3) -0.010(3) C9 0.030(4) 0.019(4) 0.021(4) -0.003(3) -0.002(3) 0.006(4) N2 0.024(4) 0.033(4) 0.027(4) -0.004(3) -0.004(3) 0.002(3) C18 0.032(5) 0.029(5) 0.023(5) -0.002(4) -0.005(4) -0.003(4) C1 0.023(4) 0.024(4) 0.034(5) 0.000(4) -0.001(4) -0.006(4) N1 0.040(4) 0.035(4) 0.030(4) -0.008(3) -0.005(3) 0.014(4) C23 0.034(5) 0.049(6) 0.028(5) -0.003(4) 0.003(4) 0.001(5) C4 0.028(4) 0.032(5) 0.020(4) 0.000(4) -0.002(3) 0.005(4) C19 0.024(4) 0.034(5) 0.033(5) 0.003(4) 0.002(4) 0.000(4) C20 0.036(5) 0.071(7) 0.031(5) 0.001(5) 0.006(4) -0.006(5) C17 0.022(4) 0.025(4) 0.031(5) 0.002(4) 0.004(4) 0.003(4) C22 0.024(4) 0.061(7) 0.046(6) -0.002(5) -0.006(4) -0.001(5) C12 0.038(5) 0.025(5) 0.059(7) -0.001(5) -0.018(5) 0.001(4) C24 0.022(4) 0.034(5) 0.023(5) 0.002(4) -0.003(3) 0.000(4) C11 0.030(4) 0.022(4) 0.037(5) -0.002(4) -0.010(4) 0.002(4) C3 0.037(5) 0.038(6) 0.038(6) -0.006(4) -0.005(4) 0.004(4) C15 0.050(6) 0.026(5) 0.054(7) 0.009(5) -0.008(5) -0.004(5) C7 0.083(9) 0.083(9) 0.037(7) -0.016(6) -0.024(6) 0.012(8) C6 0.060(7) 0.081(9) 0.045(7) 0.011(6) -0.019(6) 0.011(7) C14 0.071(7) 0.033(6) 0.041(6) 0.013(4) -0.017(5) 0.003(5) C10 0.023(4) 0.019(4) 0.033(5) 0.002(4) -0.004(4) -0.003(3) C13 0.065(7) 0.037(6) 0.057(7) 0.001(5) -0.035(6) 0.009(5) C8 0.081(9) 0.068(8) 0.047(7) -0.018(6) -0.017(6) 0.014(7) C21 0.028(5) 0.077(8) 0.042(6) 0.001(6) 0.007(4) -0.013(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C9 1.230(9) . ? O3 Nd1 2.432(5) 2_655 ? O2 C1 1.271(10) . ? O2 Nd1 2.370(5) 2 ? Nd1 O2 2.370(5) 2_545 ? Nd1 O3 2.432(5) 2_645 ? Nd1 O5 2.454(6) . ? Nd1 O1 2.477(6) . ? Nd1 O4 2.522(5) . ? Nd1 N2 2.586(7) . ? Nd1 N3 2.614(7) . ? Nd1 N5 2.656(7) . ? O4 C9 1.285(9) . ? O5 C17 1.276(10) . ? O6 C17 1.243(9) . ? O1 C1 1.250(10) . ? C5 C4 1.376(12) . ? C5 C6 1.382(14) . ? C5 H5 0.9300 . ? C16 N6 1.378(10) . ? C16 C15 1.379(12) . ? C16 C11 1.419(12) . ? C2 N2 1.329(10) . ? C2 N1 1.363(11) . ? C2 C1 1.495(12) . ? N3 C18 1.335(10) . ? N3 C24 1.394(10) . ? N6 C10 1.352(10) . ? N6 H6 0.8600 . ? N4 C18 1.335(10) . ? N4 C19 1.383(10) . ? N4 H4 0.8600 . ? N5 C10 1.297(10) . ? N5 C11 1.372(10) . ? C9 C10 1.482(11) . ? N2 C4 1.391(10) . ? C18 C17 1.501(11) . ? N1 C3 1.381(11) . ? N1 H1 0.8600 . ? C23 C22 1.383(13) . ? C23 C24 1.391(12) . ? C23 H23 0.9300 . ? C4 C3 1.417(12) . ? C19 C20 1.397(12) . ? C19 C24 1.407(11) . ? C20 C21 1.390(13) . ? C20 H20 0.9300 . ? C22 C21 1.408(13) . ? C22 H22 0.9300 . ? C12 C13 1.384(13) . ? C12 C11 1.404(12) . ? C12 H12 0.9300 . ? C3 C8 1.385(13) . ? C15 C14 1.365(13) . ? C15 H15 0.9300 . ? C7 C8 1.390(16) . ? C7 C6 1.423(16) . ? C7 H7 0.9300 . ? C6 H6A 0.9300 . ? C14 C13 1.392(14) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? C8 H8 0.9300 . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O3 Nd1 169.8(5) . 2_655 ? C1 O2 Nd1 162.1(5) . 2 ? O2 Nd1 O3 82.36(19) 2_545 2_645 ? O2 Nd1 O5 79.37(19) 2_545 . ? O3 Nd1 O5 119.5(2) 2_645 . ? O2 Nd1 O1 81.5(2) 2_545 . ? O3 Nd1 O1 157.2(2) 2_645 . ? O5 Nd1 O1 72.93(18) . . ? O2 Nd1 O4 140.14(19) 2_545 . ? O3 Nd1 O4 70.48(19) 2_645 . ? O5 Nd1 O4 139.39(18) . . ? O1 Nd1 O4 113.78(19) . . ? O2 Nd1 N2 86.4(2) 2_545 . ? O3 Nd1 N2 97.8(2) 2_645 . ? O5 Nd1 N2 137.3(2) . . ? O1 Nd1 N2 65.22(19) . . ? O4 Nd1 N2 69.7(2) . . ? O2 Nd1 N3 119.4(2) 2_545 . ? O3 Nd1 N3 76.2(2) 2_645 . ? O5 Nd1 N3 64.6(2) . . ? O1 Nd1 N3 126.0(2) . . ? O4 Nd1 N3 82.5(2) . . ? N2 Nd1 N3 151.7(2) . . ? O2 Nd1 N5 152.5(2) 2_545 . ? O3 Nd1 N5 124.9(2) 2_645 . ? O5 Nd1 N5 83.1(2) . . ? O1 Nd1 N5 73.2(2) . . ? O4 Nd1 N5 62.97(19) . . ? N2 Nd1 N5 92.4(2) . . ? N3 Nd1 N5 70.2(2) . . ? C9 O4 Nd1 125.1(5) . . ? C17 O5 Nd1 125.7(5) . . ? C1 O1 Nd1 120.2(5) . . ? C4 C5 C6 118.4(10) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? N6 C16 C15 133.4(8) . . ? N6 C16 C11 104.7(7) . . ? C15 C16 C11 121.7(8) . . ? N2 C2 N1 113.5(8) . . ? N2 C2 C1 121.4(7) . . ? N1 C2 C1 125.2(8) . . ? C18 N3 C24 105.2(7) . . ? C18 N3 Nd1 113.3(5) . . ? C24 N3 Nd1 139.0(5) . . ? C10 N6 C16 107.9(7) . . ? C10 N6 H6 126.0 . . ? C16 N6 H6 126.0 . . ? C18 N4 C19 107.4(7) . . ? C18 N4 H4 126.3 . . ? C19 N4 H4 126.3 . . ? C10 N5 C11 107.8(7) . . ? C10 N5 Nd1 114.0(5) . . ? C11 N5 Nd1 137.0(5) . . ? O3 C9 O4 125.0(7) . . ? O3 C9 C10 122.3(7) . . ? O4 C9 C10 112.6(7) . . ? C2 N2 C4 105.4(7) . . ? C2 N2 Nd1 109.3(5) . . ? C4 N2 Nd1 137.4(5) . . ? N4 C18 N3 113.1(7) . . ? N4 C18 C17 125.6(7) . . ? N3 C18 C17 121.3(7) . . ? O1 C1 O2 127.0(8) . . ? O1 C1 C2 115.4(7) . . ? O2 C1 C2 117.6(7) . . ? C2 N1 C3 106.1(7) . . ? C2 N1 H1 127.0 . . ? C3 N1 H1 127.0 . . ? C22 C23 C24 118.1(9) . . ? C22 C23 H23 121.0 . . ? C24 C23 H23 121.0 . . ? C5 C4 N2 131.6(8) . . ? C5 C4 C3 120.0(8) . . ? N2 C4 C3 108.4(7) . . ? N4 C19 C20 131.8(8) . . ? N4 C19 C24 105.9(7) . . ? C20 C19 C24 122.2(8) . . ? C21 C20 C19 116.5(9) . . ? C21 C20 H20 121.8 . . ? C19 C20 H20 121.8 . . ? O6 C17 O5 126.5(7) . . ? O6 C17 C18 119.8(7) . . ? O5 C17 C18 113.7(7) . . ? C23 C22 C21 121.2(9) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C13 C12 C11 116.7(9) . . ? C13 C12 H12 121.6 . . ? C11 C12 H12 121.6 . . ? C23 C24 N3 131.3(8) . . ? C23 C24 C19 120.3(8) . . ? N3 C24 C19 108.4(7) . . ? N5 C11 C12 132.3(8) . . ? N5 C11 C16 107.9(7) . . ? C12 C11 C16 119.8(8) . . ? N1 C3 C8 130.6(9) . . ? N1 C3 C4 106.6(8) . . ? C8 C3 C4 122.8(9) . . ? C14 C15 C16 118.0(9) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? C8 C7 C6 121.0(10) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C5 C6 C7 121.2(10) . . ? C5 C6 H6A 119.4 . . ? C7 C6 H6A 119.4 . . ? C15 C14 C13 121.2(9) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? N5 C10 N6 111.6(7) . . ? N5 C10 C9 124.1(7) . . ? N6 C10 C9 124.0(7) . . ? C12 C13 C14 122.5(9) . . ? C12 C13 H13 118.7 . . ? C14 C13 H13 118.7 . . ? C3 C8 C7 116.6(11) . . ? C3 C8 H8 121.7 . . ? C7 C8 H8 121.7 . . ? C20 C21 C22 121.7(9) . . ? C20 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? 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 H1 O5 0.86 1.95 2.795(9) 167.2 2 N4 H4 O6 0.86 2.00 2.826(9) 159.5 3_665 N6 H6 O4 0.86 1.94 2.745(8) 155.7 2_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.114 _refine_diff_density_min -2.281 _refine_diff_density_rms 0.159 # Attachment '- Compound 3--874299.cif' data_xb4736_0m _database_code_depnum_ccdc_archive 'CCDC 874299' #TrackingRef '- Compound 3--874299.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H15 Gd N6 O6' _chemical_formula_sum 'C24 H15 Gd N6 O6' _chemical_formula_weight 640.67 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' Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' 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 9.7434(11) _cell_length_b 8.9656(10) _cell_length_c 26.000(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.179(2) _cell_angle_gamma 90.00 _cell_volume 2270.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1865 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 23.72 _exptl_crystal_description flaky _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 1.874 _exptl_crystal_density_diffrn 1.874 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1252 _exptl_absorpt_coefficient_mu 2.977 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.369 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11088 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0647 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4012 _reflns_number_gt 3227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0251P)^2^+1.6354P] 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 4012 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 Gd1 Gd -0.01068(3) 0.44995(3) 0.218609(11) 0.01629(10) Uani 1 1 d . . . C1 C -0.2649(6) 0.6434(6) 0.2631(2) 0.0235(14) Uani 1 1 d . . . C2 C -0.1691(6) 0.6253(7) 0.3087(2) 0.0249(14) Uani 1 1 d . . . C3 C -0.0660(6) 0.6550(7) 0.3825(2) 0.0331(16) Uani 1 1 d . . . C4 C -0.0080(6) 0.5327(7) 0.3567(2) 0.0248(14) Uani 1 1 d . . . C5 C -0.0232(9) 0.6957(8) 0.4317(3) 0.057(2) Uani 1 1 d . . . H5 H -0.0631 0.7748 0.4490 0.068 Uiso 1 1 calc R . . C6 C 0.0812(9) 0.6129(10) 0.4534(3) 0.071(3) Uani 1 1 d . . . H6 H 0.1147 0.6389 0.4859 0.086 Uiso 1 1 calc R . . C7 C 0.1394(8) 0.4902(9) 0.4283(3) 0.054(2) Uani 1 1 d . . . H7 H 0.2092 0.4362 0.4446 0.065 Uiso 1 1 calc R . . C8 C 0.0946(6) 0.4494(8) 0.3802(3) 0.0382(17) Uani 1 1 d . . . H8 H 0.1322 0.3674 0.3637 0.046 Uiso 1 1 calc R . . C9 C -0.0750(6) 0.4405(6) 0.0930(2) 0.0233(13) Uani 1 1 d . . . C10 C 0.0761(6) 0.4720(6) 0.0964(2) 0.0232(14) Uani 1 1 d . . . C11 C 0.2782(6) 0.5020(6) 0.1288(2) 0.0220(14) Uani 1 1 d . . . C12 C 0.3967(6) 0.5151(7) 0.1602(3) 0.0312(16) Uani 1 1 d . . . H12 H 0.3946 0.4966 0.1954 0.037 Uiso 1 1 calc R . . C13 C 0.5164(6) 0.5565(8) 0.1366(3) 0.0393(17) Uani 1 1 d . . . H13 H 0.5968 0.5650 0.1563 0.047 Uiso 1 1 calc R . . C14 C 0.5200(7) 0.5860(8) 0.0837(3) 0.0428(19) Uani 1 1 d . . . H14 H 0.6028 0.6141 0.0695 0.051 Uiso 1 1 calc R . . C15 C 0.4063(6) 0.5750(7) 0.0524(3) 0.0363(17) Uani 1 1 d . . . H15 H 0.4094 0.5952 0.0174 0.044 Uiso 1 1 calc R . . C16 C 0.2849(6) 0.5316(7) 0.0759(2) 0.0264(14) Uani 1 1 d . . . C17 C 0.2165(5) 0.7221(6) 0.2454(2) 0.0197(13) Uani 1 1 d . . . C18 C 0.1191(6) 0.7929(6) 0.2083(2) 0.0211(13) Uani 1 1 d . . . C19 C 0.0329(6) 0.9457(6) 0.1503(2) 0.0255(14) Uani 1 1 d . . . C20 C 0.0052(7) 1.0587(7) 0.1143(3) 0.0410(18) Uani 1 1 d . . . H20 H 0.0582 1.1447 0.1126 0.049 Uiso 1 1 calc R . . C21 C -0.1054(7) 1.0345(8) 0.0815(3) 0.0445(19) Uani 1 1 d . . . H21 H -0.1263 1.1053 0.0564 0.053 Uiso 1 1 calc R . . C22 C -0.1866(7) 0.9076(7) 0.0847(3) 0.046(2) Uani 1 1 d . . . H22 H -0.2612 0.8968 0.0621 0.055 Uiso 1 1 calc R . . C23 C -0.1601(6) 0.7980(7) 0.1202(3) 0.0373(17) Uani 1 1 d . . . H23 H -0.2157 0.7140 0.1223 0.045 Uiso 1 1 calc R . . C24 C -0.0468(6) 0.8169(6) 0.1532(2) 0.0257(14) Uani 1 1 d . . . N1 N -0.0734(5) 0.5177(5) 0.30895(19) 0.0252(12) Uani 1 1 d . . . N2 N -0.1676(5) 0.7090(6) 0.35071(19) 0.0332(13) Uani 1 1 d . . . H2 H -0.2207 0.7833 0.3568 0.040 Uiso 1 1 calc R . . N3 N 0.0099(4) 0.7215(5) 0.19012(19) 0.0221(11) Uani 1 1 d . . . N4 N 0.1355(5) 0.9291(5) 0.18667(19) 0.0262(12) Uani 1 1 d . . . H4 H 0.1985 0.9930 0.1943 0.031 Uiso 1 1 calc R . . N5 N 0.1444(5) 0.4649(5) 0.14064(19) 0.0250(11) Uani 1 1 d . . . N6 N 0.1545(5) 0.5105(5) 0.05630(19) 0.0275(13) Uani 1 1 d . . . H6N H 0.1280 0.5199 0.0247 0.033 Uiso 1 1 calc R . . O1 O -0.1340(4) 0.4359(5) 0.05074(16) 0.0355(11) Uani 1 1 d . . . O2 O -0.1267(4) 0.4201(4) 0.13680(15) 0.0226(9) Uani 1 1 d . . . O3 O 0.1780(4) 0.5953(4) 0.25995(15) 0.0221(9) Uani 1 1 d . . . O4 O 0.3258(4) 0.7857(4) 0.25883(15) 0.0237(9) Uani 1 1 d . . . O5 O -0.2360(4) 0.5639(4) 0.22508(15) 0.0268(10) Uani 1 1 d . . . O6 O -0.3633(4) 0.7343(4) 0.26669(16) 0.0270(10) 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 Gd1 0.01476(15) 0.01679(15) 0.01725(16) -0.00003(14) -0.00167(11) -0.00051(13) C1 0.019(3) 0.022(3) 0.029(4) -0.001(3) -0.005(3) -0.003(3) C2 0.021(3) 0.032(4) 0.022(3) -0.001(3) 0.004(3) 0.001(3) C3 0.033(4) 0.042(4) 0.024(4) -0.005(3) -0.001(3) -0.001(3) C4 0.022(3) 0.029(3) 0.023(3) -0.002(3) -0.004(3) 0.004(3) C5 0.084(6) 0.048(5) 0.037(5) -0.016(4) -0.019(5) 0.011(4) C6 0.101(7) 0.078(6) 0.034(5) -0.011(5) -0.039(5) 0.016(6) C7 0.047(5) 0.068(6) 0.046(5) 0.014(4) -0.020(4) 0.009(4) C8 0.032(4) 0.047(4) 0.035(4) 0.005(4) -0.005(3) 0.007(3) C9 0.021(3) 0.020(3) 0.029(4) -0.002(3) 0.001(3) 0.004(3) C10 0.027(3) 0.026(3) 0.016(3) -0.002(3) 0.001(3) -0.005(3) C11 0.021(3) 0.020(3) 0.025(3) 0.002(3) 0.003(3) -0.002(2) C12 0.024(3) 0.047(4) 0.023(4) 0.005(3) -0.005(3) -0.008(3) C13 0.028(3) 0.062(5) 0.027(4) -0.006(4) -0.009(3) -0.005(4) C14 0.027(4) 0.059(5) 0.042(5) 0.001(4) 0.002(3) -0.016(3) C15 0.028(3) 0.060(5) 0.021(3) 0.007(3) 0.007(3) -0.002(3) C16 0.019(3) 0.034(4) 0.027(4) 0.001(3) 0.002(3) 0.001(3) C17 0.019(3) 0.020(3) 0.021(3) -0.003(3) -0.001(3) 0.003(3) C18 0.022(3) 0.017(3) 0.024(3) 0.000(3) -0.010(3) 0.002(2) C19 0.026(3) 0.019(3) 0.031(4) 0.001(3) -0.008(3) 0.002(3) C20 0.048(4) 0.021(3) 0.053(5) 0.008(4) -0.016(4) -0.001(3) C21 0.055(5) 0.039(4) 0.038(4) 0.016(4) -0.015(4) 0.000(4) C22 0.052(5) 0.041(4) 0.042(5) -0.005(4) -0.033(4) -0.002(4) C23 0.037(4) 0.030(4) 0.044(4) -0.005(3) -0.017(4) 0.000(3) C24 0.022(3) 0.022(3) 0.033(4) 0.001(3) -0.007(3) -0.001(3) N1 0.024(3) 0.026(3) 0.026(3) 0.001(2) 0.000(2) 0.002(2) N2 0.037(3) 0.036(3) 0.027(3) -0.014(3) -0.008(3) 0.015(3) N3 0.018(2) 0.015(2) 0.033(3) 0.002(2) -0.009(2) 0.000(2) N4 0.022(3) 0.022(3) 0.034(3) 0.004(2) -0.008(2) -0.005(2) N5 0.020(3) 0.033(3) 0.022(3) 0.004(2) 0.000(2) 0.000(2) N6 0.023(3) 0.045(3) 0.015(3) 0.002(2) -0.002(2) -0.009(2) O1 0.027(2) 0.057(3) 0.022(2) 0.003(2) -0.008(2) -0.008(2) O2 0.0165(19) 0.032(2) 0.019(2) -0.0001(19) -0.0008(18) -0.0063(17) O3 0.021(2) 0.019(2) 0.026(2) 0.0077(18) -0.0089(19) -0.0049(17) O4 0.022(2) 0.019(2) 0.030(3) -0.0009(19) -0.0079(19) -0.0016(17) O5 0.024(2) 0.034(2) 0.022(2) -0.007(2) -0.0048(19) 0.0062(19) O6 0.020(2) 0.024(2) 0.037(3) -0.006(2) -0.002(2) 0.0085(18) _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 Gd1 O6 2.326(4) 2_445 ? Gd1 O4 2.390(4) 2_545 ? Gd1 O2 2.403(4) . ? Gd1 O5 2.430(4) . ? Gd1 O3 2.480(4) . ? Gd1 N1 2.514(5) . ? Gd1 N3 2.554(4) . ? Gd1 N5 2.557(5) . ? C1 O5 1.255(7) . ? C1 O6 1.263(6) . ? C1 C2 1.504(8) . ? C2 N2 1.325(7) . ? C2 N1 1.342(7) . ? C3 N2 1.366(7) . ? C3 C5 1.386(9) . ? C3 C4 1.411(8) . ? C4 C8 1.380(8) . ? C4 N1 1.390(7) . ? C5 C6 1.371(10) . ? C5 H5 0.9300 . ? C6 C7 1.405(11) . ? C6 H6 0.9300 . ? C7 C8 1.366(10) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 O1 1.232(7) . ? C9 O2 1.267(7) . ? C9 C10 1.500(8) . ? C10 N5 1.318(7) . ? C10 N6 1.350(7) . ? C11 N5 1.386(7) . ? C11 C16 1.403(8) . ? C11 C12 1.404(8) . ? C12 C13 1.380(8) . ? C12 H12 0.9300 . ? C13 C14 1.401(9) . ? C13 H13 0.9300 . ? C14 C15 1.365(8) . ? C14 H14 0.9300 . ? C15 C16 1.398(8) . ? C15 H15 0.9300 . ? C16 N6 1.373(7) . ? C17 O4 1.251(6) . ? C17 O3 1.258(6) . ? C17 C18 1.482(7) . ? C18 N3 1.321(6) . ? C18 N4 1.356(7) . ? C19 N4 1.370(7) . ? C19 C24 1.395(8) . ? C19 C20 1.402(8) . ? C20 C21 1.378(8) . ? C20 H20 0.9300 . ? C21 C22 1.389(9) . ? C21 H21 0.9300 . ? C22 C23 1.370(9) . ? C22 H22 0.9300 . ? C23 C24 1.394(8) . ? C23 H23 0.9300 . ? C24 N3 1.391(7) . ? N2 H2 0.8600 . ? N4 H4 0.8600 . ? N6 H6N 0.8600 . ? O4 Gd1 2.390(4) 2 ? O6 Gd1 2.326(4) 2_455 ? 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 O6 Gd1 O4 81.09(12) 2_445 2_545 ? O6 Gd1 O2 79.20(13) 2_445 . ? O4 Gd1 O2 119.13(13) 2_545 . ? O6 Gd1 O5 81.80(13) 2_445 . ? O4 Gd1 O5 156.80(14) 2_545 . ? O2 Gd1 O5 72.49(13) . . ? O6 Gd1 O3 138.97(13) 2_445 . ? O4 Gd1 O3 70.70(12) 2_545 . ? O2 Gd1 O3 140.63(12) . . ? O5 Gd1 O3 114.31(13) . . ? O6 Gd1 N1 84.71(15) 2_445 . ? O4 Gd1 N1 96.65(14) 2_545 . ? O2 Gd1 N1 137.32(14) . . ? O5 Gd1 N1 66.21(14) . . ? O3 Gd1 N1 70.14(14) . . ? O6 Gd1 N3 152.23(13) 2_445 . ? O4 Gd1 N3 126.55(13) 2_545 . ? O2 Gd1 N3 83.56(14) . . ? O5 Gd1 N3 72.28(14) . . ? O3 Gd1 N3 64.09(13) . . ? N1 Gd1 N3 93.60(16) . . ? O6 Gd1 N5 119.76(15) 2_445 . ? O4 Gd1 N5 76.83(14) 2_545 . ? O2 Gd1 N5 65.09(13) . . ? O5 Gd1 N5 125.61(14) . . ? O3 Gd1 N5 82.61(14) . . ? N1 Gd1 N5 152.53(15) . . ? N3 Gd1 N5 70.67(16) . . ? O5 C1 O6 127.5(5) . . ? O5 C1 C2 114.4(5) . . ? O6 C1 C2 118.1(6) . . ? N2 C2 N1 114.1(5) . . ? N2 C2 C1 125.8(5) . . ? N1 C2 C1 120.1(5) . . ? N2 C3 C5 131.8(6) . . ? N2 C3 C4 106.2(5) . . ? C5 C3 C4 121.9(6) . . ? C8 C4 N1 131.1(6) . . ? C8 C4 C3 120.2(6) . . ? N1 C4 C3 108.7(5) . . ? C6 C5 C3 116.3(7) . . ? C6 C5 H5 121.8 . . ? C3 C5 H5 121.8 . . ? C5 C6 C7 122.4(7) . . ? C5 C6 H6 118.8 . . ? C7 C6 H6 118.8 . . ? C8 C7 C6 120.7(7) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C4 118.4(7) . . ? C7 C8 H8 120.8 . . ? C4 C8 H8 120.8 . . ? O1 C9 O2 127.6(5) . . ? O1 C9 C10 119.9(6) . . ? O2 C9 C10 112.5(5) . . ? N5 C10 N6 113.8(5) . . ? N5 C10 C9 121.3(5) . . ? N6 C10 C9 125.0(5) . . ? N5 C11 C16 109.0(5) . . ? N5 C11 C12 131.1(6) . . ? C16 C11 C12 119.9(5) . . ? C13 C12 C11 117.2(6) . . ? C13 C12 H12 121.4 . . ? C11 C12 H12 121.4 . . ? C12 C13 C14 121.7(6) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C15 C14 C13 122.4(6) . . ? C15 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C14 C15 C16 116.2(6) . . ? C14 C15 H15 121.9 . . ? C16 C15 H15 121.9 . . ? N6 C16 C15 131.3(6) . . ? N6 C16 C11 106.1(5) . . ? C15 C16 C11 122.6(6) . . ? O4 C17 O3 125.8(5) . . ? O4 C17 C18 121.1(5) . . ? O3 C17 C18 113.0(5) . . ? N3 C18 N4 112.9(5) . . ? N3 C18 C17 121.7(5) . . ? N4 C18 C17 125.2(5) . . ? N4 C19 C24 105.8(5) . . ? N4 C19 C20 131.9(6) . . ? C24 C19 C20 122.3(6) . . ? C21 C20 C19 115.9(6) . . ? C21 C20 H20 122.0 . . ? C19 C20 H20 122.0 . . ? C20 C21 C22 122.1(6) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C23 C22 C21 121.9(6) . . ? C23 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? C22 C23 C24 117.7(6) . . ? C22 C23 H23 121.2 . . ? C24 C23 H23 121.2 . . ? N3 C24 C23 130.4(5) . . ? N3 C24 C19 109.4(5) . . ? C23 C24 C19 120.1(6) . . ? C2 N1 C4 103.9(5) . . ? C2 N1 Gd1 110.6(4) . . ? C4 N1 Gd1 137.9(4) . . ? C2 N2 C3 107.1(5) . . ? C2 N2 H2 126.5 . . ? C3 N2 H2 126.5 . . ? C18 N3 C24 104.8(5) . . ? C18 N3 Gd1 115.2(3) . . ? C24 N3 Gd1 138.9(4) . . ? C18 N4 C19 107.1(5) . . ? C18 N4 H4 126.5 . . ? C19 N4 H4 126.5 . . ? C10 N5 C11 104.8(5) . . ? C10 N5 Gd1 113.5(4) . . ? C11 N5 Gd1 139.6(4) . . ? C10 N6 C16 106.4(5) . . ? C10 N6 H6N 126.8 . . ? C16 N6 H6N 126.8 . . ? C9 O2 Gd1 126.2(3) . . ? C17 O3 Gd1 124.6(3) . . ? C17 O4 Gd1 169.0(4) . 2 ? C1 O5 Gd1 120.7(3) . . ? C1 O6 Gd1 162.2(4) . 2_455 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N6 H6N O1 0.86 2.00 2.827(6) 160.1 3_565 N4 H4 O3 0.86 1.91 2.710(6) 154.4 2 N2 H2 O2 0.86 1.94 2.781(6) 166.3 2_455 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.203 _refine_diff_density_min -0.640 _refine_diff_density_rms 0.139