# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_1 _audit_creation_date 2013-12-12 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H52 N4 O10 Sm, 2(N O3)' _chemical_formula_sum 'C24 H52 N6 O16 Sm' _chemical_formula_weight 831.06 _chemical_melting_point ? _chemical_oxdiff_formula C24H52O16N6Sm1 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sm Sm -5.3236 12.2178 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.9512(4) _cell_length_b 27.0203(9) _cell_length_c 13.0160(4) _cell_angle_alpha 90 _cell_angle_beta 101.549(3) _cell_angle_gamma 90 _cell_volume 3773.5(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8383 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 69.6230 _cell_measurement_theta_min 3.2570 _exptl_absorpt_coefficient_mu 12.306 _exptl_absorpt_correction_T_max 0.650 _exptl_absorpt_correction_T_min 0.137 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'clear yellowish' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier yellowish _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description needle _exptl_crystal_F_000 1712 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.1016 _diffrn_reflns_av_unetI/netI 0.0898 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 22645 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.106 _diffrn_reflns_theta_min 3.271 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.3200 _diffrn_measured_fraction_theta_full 0.9981 _diffrn_measured_fraction_theta_max 0.9888 _diffrn_measurement_details ? _diffrn_measurement_device_type 'SuperNova, Single source at offset, Titan' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1304224000 _diffrn_orient_matrix_UB_12 -0.0136737000 _diffrn_orient_matrix_UB_13 -0.0186619000 _diffrn_orient_matrix_UB_21 0.0304483000 _diffrn_orient_matrix_UB_22 0.0553125000 _diffrn_orient_matrix_UB_23 -0.0085913000 _diffrn_orient_matrix_UB_31 0.0518541000 _diffrn_orient_matrix_UB_32 0.0018823000 _diffrn_orient_matrix_UB_33 0.1190342000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 5015 _reflns_number_total 7091 _reflns_odcompleteness_completeness 99.81 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 1.193 _refine_diff_density_min -1.403 _refine_diff_density_rms 0.134 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 446 _refine_ls_number_reflns 7091 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1076 _refine_ls_R_factor_gt 0.0774 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0987P)^2^+16.3796P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1987 _refine_ls_wR_factor_ref 0.2243 _refine_special_details ; ? ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups, All O(H,H) groups 2. Restrained distances O7-H7 0.85 with sigma of 0.01 O5-H5 0.85 with sigma of 0.01 O2-H2 0.85 with sigma of 0.01 C18-H7 1.888778 with sigma of 0.02 Sm-H7 3.043107 with sigma of 0.02 C10-H5 1.858612 with sigma of 0.02 Sm-H5 3.122561 with sigma of 0.02 C1-H2 1.909073 with sigma of 0.02 Sm-H2 3.043974 with sigma of 0.02 3.a Rotating group: O1(H1A,H1B) 3.b Ternary CH refined with riding coordinates: C22(H22), C6(H6), C3(H3), C11(H11), C14(H14), C19(H19) 3.c Secondary CH2 refined with riding coordinates: C1(H1C,H1D), C18(H18A,H18B) 3.d Aromatic/amide H refined with riding coordinates: C10(H10) 3.e Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C24(H24A,H24B,H24C), C20(H20A,H20B, H20C), C16(H16A,H16B,H16C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C), C5(H5A,H5B,H5C), C15(H15A,H15B,H15C), C4(H4A,H4B,H4C), C12(H12A,H12B,H12C), C23(H23A,H23B,H23C) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary iterative _atom_sites_solution_secondary ? 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Sm Sm 0.38995(5) 0.58865(2) 0.76384(4) 0.0476(2) Uani 1 1 d D . . . . O15 O 0.6404(13) 0.5930(3) 0.5245(8) 0.109(4) Uani 1 1 d . . . . . O4 O 0.2045(6) 0.6382(3) 0.7315(5) 0.0589(17) Uani 1 1 d . . . . . N2 N 0.0209(9) 0.6647(3) 0.7562(6) 0.065(2) Uani 1 1 d . . . . . O8 O 0.5592(7) 0.6003(3) 0.9256(6) 0.0633(19) Uani 1 1 d . . . . . O13 O 0.6749(10) 0.4598(3) 0.7579(6) 0.085(3) Uani 1 1 d . . . . . O7 O 0.4527(6) 0.5101(3) 0.8556(6) 0.0616(18) Uani 1 1 d D . . . . H7 H 0.5279(14) 0.5008(15) 0.877(7) 0.092 Uiso 1 1 d D U . . . O5 O 0.2899(7) 0.6082(3) 0.9180(5) 0.0630(19) Uani 1 1 d D . . . . H5 H 0.309(6) 0.595(3) 0.979(3) 0.094 Uiso 1 1 d D U . . . O9 O 0.4897(9) 0.6676(3) 0.8465(6) 0.073(2) Uani 1 1 d . . . . . N3 N 0.1512(8) 0.4536(3) 0.7968(6) 0.056(2) Uani 1 1 d . . . . . O2 O 0.3078(8) 0.5630(2) 0.5819(5) 0.0626(19) Uani 1 1 d D . . . . H2 H 0.296(8) 0.5328(7) 0.5622(17) 0.094 Uiso 1 1 d D U . . . N1 N 0.4099(9) 0.6727(3) 0.4650(6) 0.058(2) Uani 1 1 d . . . . . N6 N 0.6677(11) 0.5569(4) 0.4795(8) 0.079(3) Uani 1 1 d . . . . . C13 C -0.0300(14) 0.6309(6) 0.5730(9) 0.097(5) Uani 1 1 d . . . . . H13A H 0.0524 0.6175 0.5792 0.145 Uiso 1 1 calc R U . . . H13B H -0.0620 0.6401 0.5014 0.145 Uiso 1 1 calc R U . . . H13C H -0.0834 0.6065 0.5945 0.145 Uiso 1 1 calc R U . . . O1 O 0.5764(8) 0.5580(3) 0.7105(6) 0.076(2) Uani 1 1 d . . . . . H1A H 0.5912 0.5266 0.7295 0.114 Uiso 1 1 d R U . . . H1B H 0.5900 0.5654 0.6496 0.114 Uiso 1 1 d R U . . . O6 O 0.2301(7) 0.5274(3) 0.7645(5) 0.0606(18) Uani 1 1 d . . . . . O11 O 0.6699(8) 0.4602(3) 0.9235(6) 0.077(2) Uani 1 1 d . . . . . C21 C 0.0087(15) 0.4784(6) 0.6290(10) 0.101(5) Uani 1 1 d . . . . . H21A H 0.0581 0.5067 0.6197 0.152 Uiso 1 1 calc R U . . . H21B H -0.0771 0.4848 0.5984 0.152 Uiso 1 1 calc R U . . . H21C H 0.0370 0.4502 0.5953 0.152 Uiso 1 1 calc R U . . . C24 C 0.138(2) 0.3641(6) 0.7486(14) 0.130(7) Uani 1 1 d . . . . . H24A H 0.0503 0.3660 0.7180 0.195 Uiso 1 1 calc R U . . . H24B H 0.1572 0.3315 0.7762 0.195 Uiso 1 1 calc R U . . . H24C H 0.1854 0.3711 0.6961 0.195 Uiso 1 1 calc R U . . . C22 C 0.1689(12) 0.4018(4) 0.8369(10) 0.071(3) Uani 1 1 d . . . . . H22 H 0.2576 0.3979 0.8679 0.085 Uiso 1 1 calc R U . . . N4 N 0.5592(8) 0.6470(4) 0.9238(7) 0.058(2) Uani 1 1 d . . . . . C20 C -0.0260(14) 0.5100(6) 0.8038(13) 0.098(4) Uani 1 1 d . . . . . H20A H -0.0171 0.5014 0.8765 0.147 Uiso 1 1 calc R U . . . H20B H -0.1123 0.5159 0.7743 0.147 Uiso 1 1 calc R U . . . H20C H 0.0214 0.5393 0.7976 0.147 Uiso 1 1 calc R U . . . C16 C -0.1819(11) 0.6388(7) 0.7941(12) 0.099(5) Uani 1 1 d . . . . . H16A H -0.2361 0.6508 0.7318 0.149 Uiso 1 1 calc R U . . . H16B H -0.2266 0.6375 0.8504 0.149 Uiso 1 1 calc R U . . . H16C H -0.1530 0.6063 0.7814 0.149 Uiso 1 1 calc R U . . . C6 C 0.4698(11) 0.7203(4) 0.5016(9) 0.063(3) Uani 1 1 d . . . . . H6 H 0.4780 0.7389 0.4386 0.076 Uiso 1 1 calc R U . . . C3 C 0.3775(13) 0.6642(5) 0.3491(8) 0.075(3) Uani 1 1 d . . . . . H3 H 0.3438 0.6306 0.3374 0.090 Uiso 1 1 calc R U . . . O3 O 0.4202(7) 0.6450(2) 0.6284(5) 0.0573(18) Uani 1 1 d . . . . . C11 C -0.0250(11) 0.6762(5) 0.6424(8) 0.073(3) Uani 1 1 d . . . . . H11 H -0.1102 0.6889 0.6346 0.088 Uiso 1 1 calc R U . . . O10 O 0.6243(11) 0.6702(4) 0.9927(7) 0.105(3) Uani 1 1 d . . . . . C1 C 0.3254(13) 0.5911(4) 0.4904(8) 0.066(3) Uani 1 1 d D . . . . H1C H 0.2458 0.5978 0.4445 0.079 Uiso 1 1 calc R U . . . H1D H 0.3774 0.5729 0.4514 0.079 Uiso 1 1 calc R U . . . N5 N 0.7070(9) 0.4411(4) 0.8464(7) 0.069(2) Uani 1 1 d . . . . . C17 C 0.2431(10) 0.4842(4) 0.8008(7) 0.054(2) Uani 1 1 d . . . . . C10 C 0.1728(11) 0.6297(4) 0.9060(8) 0.064(3) Uani 1 1 d D . . . . H10 H 0.1287 0.6340 0.9594 0.077 Uiso 1 1 calc R U . . . C2 C 0.3872(10) 0.6380(4) 0.5323(7) 0.054(2) Uani 1 1 d . . . . . C8 C 0.6006(14) 0.7140(5) 0.5658(11) 0.096(5) Uani 1 1 d . . . . . H8A H 0.5962 0.7014 0.6339 0.144 Uiso 1 1 calc R U . . . H8B H 0.6423 0.7454 0.5730 0.144 Uiso 1 1 calc R U . . . H8C H 0.6459 0.6912 0.5310 0.144 Uiso 1 1 calc R U . . . C9 C 0.1262(10) 0.6455(4) 0.7897(8) 0.055(2) Uani 1 1 d . . . . . C7 C 0.3855(16) 0.7507(5) 0.5565(11) 0.091(4) Uani 1 1 d . . . . . H7A H 0.3063 0.7553 0.5102 0.137 Uiso 1 1 calc R U . . . H7B H 0.4231 0.7824 0.5755 0.137 Uiso 1 1 calc R U . . . H7C H 0.3737 0.7337 0.6185 0.137 Uiso 1 1 calc R U . . . O12 O 0.7777(10) 0.4050(4) 0.8613(8) 0.094(3) Uani 1 1 d . . . . . C5 C 0.2741(15) 0.7006(6) 0.2997(9) 0.098(5) Uani 1 1 d . . . . . H5A H 0.2123 0.7024 0.3425 0.147 Uiso 1 1 calc R U . . . H5B H 0.2360 0.6894 0.2308 0.147 Uiso 1 1 calc R U . . . H5C H 0.3095 0.7328 0.2950 0.147 Uiso 1 1 calc R U . . . C18 C 0.3732(10) 0.4680(4) 0.8520(8) 0.057(2) Uani 1 1 d D . . . . H18A H 0.3743 0.4559 0.9223 0.069 Uiso 1 1 calc R U . . . H18B H 0.4012 0.4416 0.8116 0.069 Uiso 1 1 calc R U . . . C14 C -0.0721(11) 0.6731(5) 0.8233(10) 0.077(3) Uani 1 1 d . . . . . H14 H -0.0310 0.6645 0.8950 0.092 Uiso 1 1 calc R U . . . C19 C 0.0214(11) 0.4678(5) 0.7454(10) 0.071(3) Uani 1 1 d . . . . . H19 H -0.0316 0.4391 0.7512 0.086 Uiso 1 1 calc R U . . . C15 C -0.1078(17) 0.7272(6) 0.8252(14) 0.113(6) Uani 1 1 d . . . . . H15A H -0.0339 0.7469 0.8451 0.170 Uiso 1 1 calc R U . . . H15B H -0.1607 0.7320 0.8749 0.170 Uiso 1 1 calc R U . . . H15C H -0.1514 0.7371 0.7568 0.170 Uiso 1 1 calc R U . . . C4 C 0.4926(16) 0.6673(6) 0.3014(11) 0.106(5) Uani 1 1 d . . . . . H4A H 0.5165 0.7013 0.2974 0.158 Uiso 1 1 calc R U . . . H4B H 0.4748 0.6533 0.2323 0.158 Uiso 1 1 calc R U . . . H4C H 0.5594 0.6493 0.3444 0.158 Uiso 1 1 calc R U . . . C12 C 0.0560(16) 0.7182(6) 0.6097(11) 0.110(6) Uani 1 1 d . . . . . H12A H 0.0657 0.7442 0.6610 0.166 Uiso 1 1 calc R U . . . H12B H 0.0159 0.7311 0.5427 0.166 Uiso 1 1 calc R U . . . H12C H 0.1364 0.7053 0.6051 0.166 Uiso 1 1 calc R U . . . C23 C 0.0974(17) 0.3931(7) 0.9233(13) 0.118(6) Uani 1 1 d . . . . . H23A H 0.1161 0.4190 0.9745 0.177 Uiso 1 1 calc R U . . . H23B H 0.1211 0.3618 0.9561 0.177 Uiso 1 1 calc R U . . . H23C H 0.0096 0.3930 0.8942 0.177 Uiso 1 1 calc R U . . . O16 O 0.6721(18) 0.5559(6) 0.3892(10) 0.180(8) Uani 1 1 d . . . . . O14 O 0.6947(16) 0.5197(4) 0.5286(10) 0.139(5) 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 Sm 0.0566(3) 0.0465(3) 0.0397(3) 0.0055(2) 0.0094(2) -0.0007(2) O15 0.172(12) 0.076(6) 0.091(7) 0.007(5) 0.057(7) 0.033(7) O4 0.048(4) 0.074(5) 0.056(4) 0.007(3) 0.012(3) 0.005(3) N2 0.079(7) 0.064(6) 0.048(5) 0.003(4) 0.007(5) 0.013(5) O8 0.060(4) 0.060(5) 0.063(5) 0.000(3) -0.004(3) 0.001(4) O13 0.104(7) 0.091(6) 0.059(5) 0.017(4) 0.015(5) 0.018(6) O7 0.047(4) 0.060(4) 0.075(5) 0.012(3) 0.004(3) -0.003(3) O5 0.063(4) 0.087(5) 0.040(4) 0.015(3) 0.012(3) 0.013(4) O9 0.106(7) 0.058(4) 0.054(4) 0.000(3) 0.013(4) 0.004(4) N3 0.060(5) 0.053(5) 0.051(5) 0.008(4) 0.004(4) -0.001(4) O2 0.091(6) 0.044(4) 0.053(4) 0.001(3) 0.016(4) -0.007(4) N1 0.077(6) 0.053(5) 0.043(4) 0.008(4) 0.012(4) -0.001(4) N6 0.101(8) 0.072(7) 0.067(7) 0.001(5) 0.028(6) 0.020(6) C13 0.091(10) 0.141(14) 0.047(7) -0.016(8) -0.012(6) 0.005(10) O1 0.091(6) 0.077(6) 0.064(5) 0.022(4) 0.028(4) 0.014(5) O6 0.062(4) 0.059(4) 0.062(4) 0.024(3) 0.013(3) 0.002(3) O11 0.071(5) 0.098(6) 0.062(5) 0.008(4) 0.013(4) 0.021(5) C21 0.113(12) 0.103(11) 0.069(8) 0.027(7) -0.026(8) -0.017(9) C24 0.18(2) 0.059(9) 0.136(15) -0.008(9) -0.004(14) -0.010(11) C22 0.072(8) 0.058(7) 0.081(8) 0.021(6) 0.011(6) -0.008(6) N4 0.056(5) 0.070(6) 0.046(5) -0.009(4) 0.003(4) 0.005(4) C20 0.069(8) 0.087(10) 0.141(13) 0.005(9) 0.028(9) 0.009(8) C16 0.045(6) 0.142(14) 0.109(11) 0.024(10) 0.011(7) 0.007(8) C6 0.081(8) 0.049(6) 0.062(6) 0.017(5) 0.018(6) 0.006(5) C3 0.104(10) 0.081(8) 0.040(6) 0.015(5) 0.016(6) 0.009(7) O3 0.083(5) 0.054(4) 0.033(4) 0.005(3) 0.010(3) -0.008(4) C11 0.062(7) 0.104(10) 0.047(6) 0.013(6) -0.004(5) 0.013(7) O10 0.123(9) 0.089(7) 0.083(6) -0.029(5) -0.025(6) 0.018(6) C1 0.099(9) 0.062(6) 0.038(5) 0.010(4) 0.017(5) -0.011(6) N5 0.064(6) 0.083(7) 0.060(6) 0.013(5) 0.013(5) 0.006(5) C17 0.066(6) 0.051(5) 0.044(5) 0.004(4) 0.010(5) -0.002(5) C10 0.070(7) 0.082(8) 0.039(5) 0.013(5) 0.009(5) 0.015(6) C2 0.070(7) 0.053(5) 0.038(5) 0.008(4) 0.009(5) 0.002(5) C8 0.102(11) 0.075(9) 0.105(11) 0.025(8) 0.002(9) -0.015(8) C9 0.065(6) 0.046(5) 0.054(6) 0.002(4) 0.010(5) 0.005(5) C7 0.134(14) 0.061(7) 0.087(9) 0.004(6) 0.044(9) 0.009(8) O12 0.100(7) 0.097(7) 0.087(6) 0.015(5) 0.023(5) 0.041(6) C5 0.115(12) 0.120(12) 0.048(7) 0.013(7) -0.010(7) -0.003(10) C18 0.065(6) 0.054(6) 0.054(6) 0.013(4) 0.013(5) 0.005(5) C14 0.058(7) 0.107(10) 0.062(7) -0.004(7) 0.006(6) 0.015(7) C19 0.061(7) 0.068(7) 0.084(8) 0.010(6) 0.010(6) -0.002(6) C15 0.119(14) 0.106(12) 0.115(13) -0.028(10) 0.021(10) 0.034(11) C4 0.152(16) 0.110(12) 0.066(8) 0.024(8) 0.049(9) 0.029(11) C12 0.116(13) 0.125(13) 0.078(9) 0.052(9) -0.009(9) 0.003(11) C23 0.117(14) 0.139(14) 0.100(11) 0.061(11) 0.028(10) -0.006(12) O16 0.30(2) 0.176(14) 0.080(8) 0.000(8) 0.075(11) 0.064(15) O14 0.231(17) 0.069(7) 0.122(9) 0.007(6) 0.044(10) 0.016(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sm O4 2.398(7) . ? Sm O8 2.531(7) . ? Sm O7 2.464(7) . ? Sm O5 2.527(7) . ? Sm O9 2.535(8) . ? Sm O2 2.458(7) . ? Sm O1 2.430(8) . ? Sm O6 2.409(7) . ? Sm N4 2.951(9) . ? Sm O3 2.401(6) . ? O15 N6 1.205(13) . ? O4 C9 1.268(12) . ? N2 C11 1.498(13) . ? N2 C9 1.260(13) . ? N2 C14 1.487(14) . ? O8 N4 1.261(11) . ? O13 N5 1.242(11) . ? O7 C18 1.429(12) . ? O5 C10 1.388(13) . ? O9 N4 1.262(11) . ? N3 C22 1.494(13) . ? N3 C17 1.294(13) . ? N3 C19 1.494(14) . ? O2 C1 1.456(11) . ? N1 C6 1.480(14) . ? N1 C3 1.496(13) . ? N1 C2 1.341(12) . ? N6 O16 1.187(14) . ? N6 O14 1.198(14) . ? C13 C11 1.515(18) . ? O6 C17 1.259(11) . ? O11 N5 1.266(12) . ? C21 C19 1.521(17) . ? C24 C22 1.522(19) . ? C22 C23 1.513(18) . ? N4 O10 1.204(12) . ? C20 C19 1.518(18) . ? C16 C14 1.506(19) . ? C6 C8 1.516(18) . ? C6 C7 1.517(17) . ? C3 C5 1.541(18) . ? C3 C4 1.515(19) . ? O3 C2 1.244(11) . ? C11 C12 1.550(19) . ? C1 C2 1.488(14) . ? N5 O12 1.237(12) . ? C17 C18 1.511(14) . ? C10 C9 1.557(14) . ? C14 C15 1.515(19) . ? 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 Sm O8 122.0(2) . . ? O4 Sm O7 135.2(2) . . ? O4 Sm O5 62.4(2) . . ? O4 Sm O9 83.3(3) . . ? O4 Sm O2 81.6(3) . . ? O4 Sm O1 150.5(2) . . ? O4 Sm O6 78.1(3) . . ? O4 Sm N4 102.5(2) . . ? O4 Sm O3 75.7(2) . . ? O8 Sm O9 50.2(2) . . ? O8 Sm N4 25.1(2) . . ? O7 Sm O8 67.5(2) . . ? O7 Sm O5 85.3(2) . . ? O7 Sm O9 117.6(3) . . ? O7 Sm N4 92.5(3) . . ? O5 Sm O8 71.0(3) . . ? O5 Sm O9 72.9(3) . . ? O5 Sm N4 68.8(3) . . ? O9 Sm N4 25.2(2) . . ? O2 Sm O8 154.5(3) . . ? O2 Sm O7 103.7(2) . . ? O2 Sm O5 133.7(3) . . ? O2 Sm O9 133.6(2) . . ? O2 Sm N4 152.5(3) . . ? O1 Sm O8 76.3(3) . . ? O1 Sm O7 71.1(2) . . ? O1 Sm O5 145.2(3) . . ? O1 Sm O9 95.3(3) . . ? O1 Sm O2 78.2(3) . . ? O1 Sm N4 86.5(3) . . ? O6 Sm O8 119.6(2) . . ? O6 Sm O7 62.6(2) . . ? O6 Sm O5 73.1(3) . . ? O6 Sm O9 145.8(3) . . ? O6 Sm O2 71.6(2) . . ? O6 Sm O1 114.8(3) . . ? O6 Sm N4 135.9(2) . . ? O3 Sm O8 110.3(3) . . ? O3 Sm O7 146.6(3) . . ? O3 Sm O5 126.6(2) . . ? O3 Sm O9 70.6(2) . . ? O3 Sm O2 63.2(2) . . ? O3 Sm O1 76.0(3) . . ? O3 Sm O6 130.1(2) . . ? O3 Sm N4 91.1(2) . . ? C9 O4 Sm 129.2(6) . . ? C9 N2 C11 122.0(10) . . ? C9 N2 C14 123.2(9) . . ? C14 N2 C11 114.5(10) . . ? N4 O8 Sm 96.4(6) . . ? C18 O7 Sm 124.2(6) . . ? C10 O5 Sm 122.4(6) . . ? N4 O9 Sm 96.2(6) . . ? C17 N3 C22 122.5(9) . . ? C17 N3 C19 121.2(9) . . ? C19 N3 C22 116.2(9) . . ? C1 O2 Sm 123.9(6) . . ? C6 N1 C3 117.3(8) . . ? C2 N1 C6 121.8(8) . . ? C2 N1 C3 120.9(9) . . ? O16 N6 O15 124.3(13) . . ? O16 N6 O14 117.0(13) . . ? O14 N6 O15 118.7(12) . . ? C17 O6 Sm 127.7(7) . . ? N3 C22 C24 111.7(11) . . ? N3 C22 C23 110.8(12) . . ? C23 C22 C24 112.7(13) . . ? O8 N4 Sm 58.4(5) . . ? O8 N4 O9 116.9(8) . . ? O9 N4 Sm 58.6(5) . . ? O10 N4 Sm 176.6(9) . . ? O10 N4 O8 120.6(9) . . ? O10 N4 O9 122.5(10) . . ? N1 C6 C8 112.9(9) . . ? N1 C6 C7 110.5(10) . . ? C8 C6 C7 113.5(12) . . ? N1 C3 C5 109.2(10) . . ? N1 C3 C4 110.8(11) . . ? C4 C3 C5 113.3(11) . . ? C2 O3 Sm 125.9(6) . . ? N2 C11 C13 112.7(11) . . ? N2 C11 C12 109.1(10) . . ? C13 C11 C12 112.4(12) . . ? O2 C1 C2 105.6(8) . . ? O13 N5 O11 119.6(10) . . ? O12 N5 O13 121.2(10) . . ? O12 N5 O11 119.2(9) . . ? N3 C17 C18 119.4(9) . . ? O6 C17 N3 123.3(10) . . ? O6 C17 C18 117.4(9) . . ? O5 C10 C9 109.9(8) . . ? N1 C2 C1 119.1(8) . . ? O3 C2 N1 119.7(9) . . ? O3 C2 C1 121.1(8) . . ? O4 C9 C10 114.1(9) . . ? N2 C9 O4 122.6(10) . . ? N2 C9 C10 123.3(10) . . ? O7 C18 C17 107.4(8) . . ? N2 C14 C16 111.3(11) . . ? N2 C14 C15 111.6(12) . . ? C16 C14 C15 113.8(13) . . ? N3 C19 C21 112.5(11) . . ? N3 C19 C20 111.0(11) . . ? C20 C19 C21 112.7(12) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 7 -2 0 0.0180 7.0170 -1.9706 -0.0090 0.9423 0.1047 0.3591 -7 2 0 0.0201 -7.0170 1.9706 0.0090 -0.9423 -0.1047 -0.3591 -7 1 0 0.0228 -7.0171 0.9709 0.0089 -0.9286 -0.1600 -0.3610 7 -1 0 0.0228 7.0171 -0.9709 -0.0089 0.9286 0.1600 0.3610 -3 -15 3 0.0564 -3.0079 -15.0035 3.0026 -0.2432 -0.9473 0.1732 3 15 -3 0.1304 3.0079 15.0035 -3.0026 0.2432 0.9473 -0.1732 -3 -14 -2 0.0559 -3.0097 -14.0119 -1.9965 -0.1637 -0.8495 -0.4201 3 14 2 0.0531 3.0097 14.0119 1.9965 0.1637 0.8495 0.4201 1 -16 3 0.0457 1.0018 -15.9867 2.9975 0.2933 -0.8795 0.3787 0 -17 -3 0.0545 -0.0030 -17.0004 -3.0002 0.2881 -0.9146 -0.3893 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-4 _database_code_depnum_ccdc_archive 'CCDC 977001' ####################################################################### # # 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_2 _audit_creation_date 2013-12-12 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C24 H53 Eu N4 O10, 2(N O3)' _chemical_formula_sum 'C24 H53 Eu N6 O16' _chemical_formula_weight 833.68 _chemical_melting_point ? _chemical_oxdiff_formula C34H51O15N6Eu1 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -8.9294 11.1857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.9253(2) _cell_length_b 26.9890(5) _cell_length_c 13.0207(3) _cell_angle_alpha 90 _cell_angle_beta 101.5301(19) _cell_angle_gamma 90 _cell_volume 3761.85(14) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8545 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 69.7920 _cell_measurement_theta_min 3.8100 _exptl_absorpt_coefficient_mu 12.557 _exptl_absorpt_correction_T_max 0.359 _exptl_absorpt_correction_T_min 0.058 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 1720 _exptl_crystal_preparation ? _exptl_crystal_recrystallization_method ? _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0843 _diffrn_reflns_av_unetI/netI 0.0663 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 23590 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.033 _diffrn_reflns_theta_min 3.275 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.3200 _diffrn_measured_fraction_theta_full 0.9997 _diffrn_measured_fraction_theta_max 0.9926 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -62.00 -37.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -178.0000 -120.0000 25 #__ type_ start__ end____ width___ exp.time_ 2 omega -100.00 -35.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -178.0000 60.0000 65 #__ type_ start__ end____ width___ exp.time_ 3 omega -81.00 -38.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 178.0000 -150.0000 43 #__ type_ start__ end____ width___ exp.time_ 4 omega 34.00 101.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -178.0000 90.0000 67 #__ type_ start__ end____ width___ exp.time_ 5 omega -122.00 -32.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - -54.7289 126.0000 0.0000 90 #__ type_ start__ end____ width___ exp.time_ 6 omega -153.00 -105.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - -54.7289 -95.0000 30.0000 48 #__ type_ start__ end____ width___ exp.time_ 7 omega -50.00 33.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - -54.7289 30.0000 60.0000 83 #__ type_ start__ end____ width___ exp.time_ 8 omega -151.00 -118.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - -54.7289 -95.0000 90.0000 33 #__ type_ start__ end____ width___ exp.time_ 9 omega -135.00 -93.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - -54.7289 -95.0000 -60.0000 42 #__ type_ start__ end____ width___ exp.time_ 10 omega -122.00 -97.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - -54.7289 126.0000 -60.0000 25 #__ type_ start__ end____ width___ exp.time_ 11 omega -142.00 -80.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - -54.7289 -95.0000 -180.0000 62 #__ type_ start__ end____ width___ exp.time_ 12 omega -73.00 -44.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - -54.7289 126.0000 -60.0000 29 #__ type_ start__ end____ width___ exp.time_ 13 omega 4.00 157.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 54.7289 77.0000 -30.0000 153 #__ type_ start__ end____ width___ exp.time_ 14 omega 91.00 142.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 54.7289 126.0000 -120.0000 51 #__ type_ start__ end____ width___ exp.time_ 15 omega 8.00 142.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 -77.0000 120.0000 134 #__ type_ start__ end____ width___ exp.time_ 16 omega 97.00 155.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 38.0000 60.0000 58 #__ type_ start__ end____ width___ exp.time_ 17 omega 11.00 83.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 -50.0000 120.0000 72 #__ type_ start__ end____ width___ exp.time_ 18 omega 80.00 114.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 38.0000 120.0000 34 #__ type_ start__ end____ width___ exp.time_ 19 omega 124.00 158.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 -12.0000 120.0000 34 #__ type_ start__ end____ width___ exp.time_ 20 omega 48.00 146.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 178.0000 150.0000 98 #__ type_ start__ end____ width___ exp.time_ 21 omega 10.00 36.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 -25.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 22 omega 66.00 156.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 50.0000 -90.0000 90 #__ type_ start__ end____ width___ exp.time_ 23 omega 86.00 142.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 64.0000 120.0000 56 #__ type_ start__ end____ width___ exp.time_ 24 omega 86.00 112.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 38.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 25 omega 15.00 77.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 -50.0000 -120.0000 62 #__ type_ start__ end____ width___ exp.time_ 26 omega 52.00 77.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 38.0000 60.0000 25 #__ type_ start__ end____ width___ exp.time_ 27 omega 66.00 144.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 64.0000 -60.0000 78 #__ type_ start__ end____ width___ exp.time_ 28 omega 49.00 75.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 38.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 29 omega 39.00 64.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 -50.0000 150.0000 25 #__ type_ start__ end____ width___ exp.time_ 30 omega 13.00 111.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 -112.0000 120.0000 98 #__ type_ start__ end____ width___ exp.time_ 31 omega 12.00 105.00 1.0000 3.1900 omega____ theta____ kappa____ phi______ frames - 109.4577 -12.0000 120.0000 93 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset, Titan' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1059660000 _diffrn_orient_matrix_UB_12 -0.0326228000 _diffrn_orient_matrix_UB_13 -0.0250918000 _diffrn_orient_matrix_UB_21 0.0963669000 _diffrn_orient_matrix_UB_22 0.0394389000 _diffrn_orient_matrix_UB_23 0.0484431000 _diffrn_orient_matrix_UB_31 0.0135177000 _diffrn_orient_matrix_UB_32 -0.0253169000 _diffrn_orient_matrix_UB_33 0.1077083000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 5568 _reflns_number_total 7093 _reflns_odcompleteness_completeness 99.97 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.668 _refine_diff_density_min -1.966 _refine_diff_density_rms 0.126 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 446 _refine_ls_number_reflns 7093 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0801 _refine_ls_R_factor_gt 0.0656 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1673 _refine_ls_wR_factor_ref 0.1851 _refine_special_details ; ? ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups, All O(H,H) groups 2. Restrained distances O6-H6 0.85 with sigma of 0.01 O3-H3 0.85 with sigma of 0.01 O5-H5 0.85 with sigma of 0.01 C17-H6 1.888518 with sigma of 0.02 Eu1-H6 3.040192 with sigma of 0.02 C2-H3 1.906208 with sigma of 0.02 Eu1-H3 3.045405 with sigma of 0.02 C10-H5 1.891808 with sigma of 0.02 Eu1-H5 3.11487 with sigma of 0.02 3.a Rotating group: O1(H1A,H1B) 3.b Ternary CH refined with riding coordinates: C22(H22), C19(H19), C11(H11), C3(H3A), C14(H14), C6(H6A) 3.c Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C17(H17A,H17B), C10(H10A,H10B) 3.d Idealised Me refined as rotating group: C24(H24A,H24B,H24C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C20(H20A,H20B,H20C), C4(H4A,H4B,H4C), C21(H21A,H21B,H21C), C15(H15A,H15B,H15C), C12(H12A,H12B,H12C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary ? 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Eu1 Eu 0.11102(3) 0.41161(2) 0.73582(3) 0.04646(15) Uani 1 1 d D . . . . O6 O 0.0481(4) 0.48997(17) 0.6443(4) 0.0619(11) Uani 1 1 d D . . . . H6 H -0.0271(15) 0.4985(12) 0.619(6) 0.093 Uiso 1 1 d D U . . . O8 O -0.0556(5) 0.40000(19) 0.5755(4) 0.0658(13) Uani 1 1 d . . . . . O12 O -0.2757(7) 0.5952(2) 0.6403(5) 0.094(2) Uani 1 1 d . . . . . O4 O 0.2945(5) 0.36264(18) 0.7684(3) 0.0622(12) Uani 1 1 d . . . . . O13 O -0.1734(6) 0.5400(2) 0.7429(4) 0.0859(17) Uani 1 1 d . . . . . O9 O 0.0134(5) 0.33252(18) 0.6527(4) 0.0722(14) Uani 1 1 d . . . . . O3 O 0.1943(5) 0.43679(17) 0.9171(3) 0.0626(12) Uani 1 1 d D . . . . H3 H 0.209(7) 0.4669(7) 0.9367(16) 0.094 Uiso 1 1 d D U . . . O1 O -0.0755(5) 0.4415(2) 0.7897(4) 0.0766(14) Uani 1 1 d . . . . . H1A H -0.0743 0.4335 0.8543 0.115 Uiso 1 1 d R U . . . H1B H -0.0886 0.4721 0.7711 0.115 Uiso 1 1 d R U . . . O11 O -0.1693(5) 0.5397(2) 0.5774(4) 0.0781(15) Uani 1 1 d . . . . . O16 O -0.1386(8) 0.4064(2) 0.9742(6) 0.101(2) Uani 1 1 d . . . . . O2 O 0.0811(5) 0.35562(17) 0.8698(3) 0.0604(11) Uani 1 1 d . . . . . O7 O 0.2699(4) 0.47307(17) 0.7361(4) 0.0616(12) Uani 1 1 d . . . . . O5 O 0.2100(4) 0.3928(2) 0.5817(3) 0.0630(12) Uani 1 1 d D . . . . H5 H 0.198(4) 0.4093(19) 0.524(2) 0.094 Uiso 1 1 d D U . . . O10 O -0.1234(6) 0.3298(2) 0.5078(5) 0.098(2) Uani 1 1 d . . . . . N2 N 0.4812(5) 0.3362(2) 0.7429(4) 0.0595(14) Uani 1 1 d . . . . . N1 N 0.0911(6) 0.3274(2) 1.0333(4) 0.0580(13) Uani 1 1 d . . . . . N6 N -0.2072(6) 0.5588(3) 0.6544(5) 0.0675(15) Uani 1 1 d . . . . . N3 N 0.3498(5) 0.5468(2) 0.7042(4) 0.0568(13) Uani 1 1 d . . . . . N5 N -0.1665(7) 0.4435(3) 1.0205(5) 0.0763(18) Uani 1 1 d . . . . . N4 N -0.0564(5) 0.3536(2) 0.5762(5) 0.0618(14) Uani 1 1 d . . . . . C24 C 0.4006(11) 0.6074(5) 0.5755(9) 0.119(4) Uani 1 1 d . . . . . H24A H 0.4885 0.6093 0.6045 0.178 Uiso 1 1 calc R U . . . H24B H 0.3734 0.6379 0.5403 0.178 Uiso 1 1 calc R U . . . H24C H 0.3850 0.5805 0.5265 0.178 Uiso 1 1 calc R U . . . C22 C 0.3296(8) 0.5987(3) 0.6631(7) 0.073(2) Uani 1 1 d . . . . . H22 H 0.2404 0.6025 0.6332 0.087 Uiso 1 1 calc R U . . . C19 C 0.4808(7) 0.5321(3) 0.7549(6) 0.0687(19) Uani 1 1 d . . . . . H19 H 0.5346 0.5607 0.7490 0.082 Uiso 1 1 calc R U . . . C11 C 0.5724(7) 0.3277(3) 0.6751(6) 0.075(2) Uani 1 1 d . . . . . H11 H 0.5315 0.3366 0.6035 0.090 Uiso 1 1 calc R U . . . C3 C 0.1229(9) 0.3356(3) 1.1488(5) 0.074(2) Uani 1 1 d . . . . . H3A H 0.1564 0.3693 1.1604 0.088 Uiso 1 1 calc R U . . . C5 C 0.2259(9) 0.3001(4) 1.1987(6) 0.095(3) Uani 1 1 d . . . . . H5A H 0.1933 0.2670 1.1959 0.142 Uiso 1 1 calc R U . . . H5B H 0.2564 0.3094 1.2704 0.142 Uiso 1 1 calc R U . . . H5C H 0.2930 0.3014 1.1611 0.142 Uiso 1 1 calc R U . . . C7 C 0.1148(10) 0.2490(3) 0.9393(8) 0.088(3) Uani 1 1 d . . . . . H7A H 0.1170 0.2638 0.8727 0.132 Uiso 1 1 calc R U . . . H7B H 0.0833 0.2158 0.9287 0.132 Uiso 1 1 calc R U . . . H7C H 0.1976 0.2483 0.9814 0.132 Uiso 1 1 calc R U . . . C20 C 0.5255(9) 0.4901(4) 0.6956(9) 0.102(3) Uani 1 1 d . . . . . H20A H 0.4817 0.4603 0.7064 0.153 Uiso 1 1 calc R U . . . H20B H 0.6135 0.4853 0.7206 0.153 Uiso 1 1 calc R U . . . H20C H 0.5099 0.4979 0.6222 0.153 Uiso 1 1 calc R U . . . C4 C 0.0103(10) 0.3326(4) 1.1981(7) 0.103(3) Uani 1 1 d . . . . . H4A H -0.0512 0.3561 1.1651 0.155 Uiso 1 1 calc R U . . . H4B H 0.0340 0.3401 1.2715 0.155 Uiso 1 1 calc R U . . . H4C H -0.0241 0.2998 1.1893 0.155 Uiso 1 1 calc R U . . . C21 C 0.4906(9) 0.5222(4) 0.8716(7) 0.101(3) Uani 1 1 d . . . . . H21A H 0.4677 0.5515 0.9050 0.151 Uiso 1 1 calc R U . . . H21B H 0.5749 0.5132 0.9026 0.151 Uiso 1 1 calc R U . . . H21C H 0.4353 0.4956 0.8807 0.151 Uiso 1 1 calc R U . . . C15 C 0.5297(10) 0.3700(4) 0.9249(6) 0.098(3) Uani 1 1 d . . . . . H15A H 0.5794 0.3949 0.9000 0.147 Uiso 1 1 calc R U . . . H15B H 0.5662 0.3619 0.9962 0.147 Uiso 1 1 calc R U . . . H15C H 0.4466 0.3824 0.9212 0.147 Uiso 1 1 calc R U . . . C12 C 0.6844(8) 0.3618(4) 0.7067(8) 0.094(3) Uani 1 1 d . . . . . H12A H 0.6560 0.3953 0.7109 0.142 Uiso 1 1 calc R U . . . H12B H 0.7362 0.3599 0.6553 0.142 Uiso 1 1 calc R U . . . H12C H 0.7318 0.3518 0.7737 0.142 Uiso 1 1 calc R U . . . C8 C -0.0997(8) 0.2858(3) 0.9319(8) 0.095(3) Uani 1 1 d . . . . . H8A H -0.1429 0.3100 0.9654 0.142 Uiso 1 1 calc R U . . . H8B H -0.1436 0.2549 0.9275 0.142 Uiso 1 1 calc R U . . . H8C H -0.0956 0.2970 0.8627 0.142 Uiso 1 1 calc R U . . . C13 C 0.6109(11) 0.2729(4) 0.6735(8) 0.107(3) Uani 1 1 d . . . . . H13A H 0.6525 0.2630 0.7425 0.160 Uiso 1 1 calc R U . . . H13B H 0.6663 0.2687 0.6255 0.160 Uiso 1 1 calc R U . . . H13C H 0.5378 0.2528 0.6514 0.160 Uiso 1 1 calc R U . . . C16 C 0.4470(10) 0.2822(4) 0.8893(8) 0.106(3) Uani 1 1 d . . . . . H16A H 0.3648 0.2945 0.8907 0.159 Uiso 1 1 calc R U . . . H16B H 0.4856 0.2706 0.9578 0.159 Uiso 1 1 calc R U . . . H16C H 0.4410 0.2554 0.8400 0.159 Uiso 1 1 calc R U . . . C23 C 0.3635(13) 0.6365(4) 0.7517(9) 0.124(5) Uani 1 1 d . . . . . H23A H 0.3218 0.6280 0.8076 0.185 Uiso 1 1 calc R U . . . H23B H 0.3377 0.6689 0.7258 0.185 Uiso 1 1 calc R U . . . H23C H 0.4522 0.6362 0.7774 0.185 Uiso 1 1 calc R U . . . C1 C 0.1127(6) 0.3613(2) 0.9659(4) 0.0516(14) Uani 1 1 d . . . . . C2 C 0.1758(9) 0.4089(2) 1.0064(6) 0.066(2) Uani 1 1 d D . . . . H2A H 0.1239 0.4274 1.0453 0.080 Uiso 1 1 calc R U . . . H2B H 0.2554 0.4022 1.0525 0.080 Uiso 1 1 calc R U . . . C17 C 0.1262(6) 0.5326(2) 0.6476(5) 0.0592(16) Uani 1 1 d D . . . . H17A H 0.0975 0.5589 0.6876 0.071 Uiso 1 1 calc R U . . . H17B H 0.1258 0.5446 0.5773 0.071 Uiso 1 1 calc R U . . . C9 C 0.3693(6) 0.3557(2) 0.7097(5) 0.0550(15) Uani 1 1 d . . . . . C18 C 0.2556(6) 0.5160(2) 0.6996(5) 0.0524(14) Uani 1 1 d . . . . . C10 C 0.3300(6) 0.3703(3) 0.5944(5) 0.0599(16) Uani 1 1 d D . . . . H10A H 0.3896 0.3935 0.5754 0.072 Uiso 1 1 calc R U . . . H10B H 0.3262 0.3413 0.5500 0.072 Uiso 1 1 calc R U . . . C14 C 0.5250(7) 0.3235(3) 0.8567(5) 0.0694(19) Uani 1 1 d . . . . . H14 H 0.6107 0.3110 0.8650 0.083 Uiso 1 1 calc R U . . . C6 C 0.0302(7) 0.2790(3) 0.9947(6) 0.0673(18) Uani 1 1 d . . . . . H6A H 0.0220 0.2601 1.0572 0.081 Uiso 1 1 calc R U . . . O14 O -0.1948(11) 0.4805(3) 0.9697(6) 0.142(4) Uani 1 1 d . . . . . O15 O -0.1727(12) 0.4442(4) 1.1110(6) 0.173(5) 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 0.0513(2) 0.0500(2) 0.0373(2) 0.00480(13) 0.00681(15) -0.00016(14) O6 0.053(2) 0.065(3) 0.065(3) 0.008(2) 0.006(2) -0.005(2) O8 0.069(3) 0.064(3) 0.058(3) -0.003(2) -0.004(2) 0.006(2) O12 0.104(5) 0.109(5) 0.068(4) 0.016(3) 0.014(3) 0.045(4) O4 0.068(3) 0.078(3) 0.040(2) 0.011(2) 0.009(2) 0.000(2) O13 0.107(5) 0.095(4) 0.054(3) 0.018(3) 0.012(3) 0.021(4) O9 0.085(4) 0.066(3) 0.061(3) 0.006(2) 0.004(3) 0.000(3) O3 0.087(3) 0.057(3) 0.044(2) -0.001(2) 0.013(2) -0.013(2) O1 0.088(4) 0.087(4) 0.059(3) 0.022(3) 0.025(3) 0.010(3) O11 0.075(3) 0.109(4) 0.051(3) 0.008(3) 0.013(2) 0.024(3) O16 0.141(7) 0.076(4) 0.097(5) 0.007(3) 0.048(5) 0.030(4) O2 0.075(3) 0.059(3) 0.046(2) -0.001(2) 0.010(2) -0.008(2) O7 0.062(3) 0.059(3) 0.059(3) 0.015(2) 0.002(2) 0.003(2) O5 0.061(3) 0.089(3) 0.039(2) 0.015(2) 0.010(2) 0.015(2) O10 0.097(4) 0.088(4) 0.090(4) -0.037(3) -0.027(3) 0.015(3) N2 0.054(3) 0.073(4) 0.047(3) -0.002(3) -0.001(2) 0.011(3) N1 0.076(4) 0.056(3) 0.042(3) 0.012(2) 0.013(3) 0.006(3) N6 0.057(3) 0.087(4) 0.055(3) 0.013(3) 0.004(3) 0.000(3) N3 0.064(3) 0.054(3) 0.049(3) 0.005(2) 0.005(2) -0.003(2) N5 0.086(5) 0.080(4) 0.070(4) 0.002(4) 0.033(4) 0.015(4) N4 0.057(3) 0.069(4) 0.056(3) -0.013(3) 0.003(3) 0.004(3) C24 0.106(8) 0.145(9) 0.112(8) 0.076(8) 0.037(6) 0.008(7) C22 0.078(5) 0.065(4) 0.070(5) 0.016(4) 0.005(4) -0.008(4) C19 0.062(4) 0.067(4) 0.070(5) 0.016(4) -0.004(3) -0.017(3) C11 0.065(4) 0.101(6) 0.057(4) 0.003(4) 0.008(3) 0.022(4) C3 0.109(6) 0.076(5) 0.037(3) 0.013(3) 0.015(4) 0.003(4) C5 0.102(7) 0.111(7) 0.062(5) 0.024(5) -0.006(5) 0.005(6) C7 0.116(8) 0.060(4) 0.092(6) 0.000(4) 0.033(5) 0.005(5) C20 0.081(6) 0.089(6) 0.137(9) -0.004(6) 0.027(6) 0.006(5) C4 0.128(9) 0.131(8) 0.062(5) 0.027(5) 0.045(5) 0.032(7) C21 0.093(7) 0.107(7) 0.082(6) 0.022(5) -0.031(5) -0.023(6) C15 0.098(7) 0.139(9) 0.048(4) -0.014(5) -0.005(4) 0.006(6) C12 0.061(5) 0.121(8) 0.104(7) 0.027(6) 0.024(5) 0.015(5) C8 0.082(6) 0.080(5) 0.111(7) 0.036(5) -0.009(5) -0.013(5) C13 0.110(8) 0.107(7) 0.097(7) -0.016(6) 0.006(6) 0.031(6) C16 0.097(7) 0.122(8) 0.089(6) 0.053(6) -0.006(5) -0.008(6) C23 0.165(12) 0.069(6) 0.125(10) -0.013(5) -0.001(9) -0.021(7) C1 0.061(4) 0.058(3) 0.035(3) 0.004(3) 0.006(3) 0.008(3) C2 0.091(6) 0.062(4) 0.044(4) 0.006(3) 0.006(4) -0.009(3) C17 0.064(4) 0.060(4) 0.054(4) 0.011(3) 0.011(3) -0.006(3) C9 0.059(4) 0.059(4) 0.043(3) 0.000(3) 0.002(3) -0.005(3) C18 0.059(4) 0.058(4) 0.040(3) 0.003(3) 0.008(3) 0.001(3) C10 0.055(4) 0.079(4) 0.045(3) 0.007(3) 0.007(3) 0.004(3) C14 0.057(4) 0.093(5) 0.051(4) 0.010(4) -0.005(3) 0.005(4) C6 0.079(5) 0.059(4) 0.063(4) 0.018(3) 0.012(4) 0.000(4) O14 0.235(11) 0.078(4) 0.117(6) 0.011(4) 0.046(6) 0.024(6) O15 0.262(13) 0.199(10) 0.074(5) -0.005(6) 0.075(7) 0.046(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O6 2.457(5) . ? Eu1 O8 2.500(5) . ? Eu1 O4 2.368(5) . ? Eu1 O9 2.531(5) . ? Eu1 O3 2.451(4) . ? Eu1 O1 2.422(5) . ? Eu1 O2 2.380(4) . ? Eu1 O7 2.400(5) . ? Eu1 O5 2.514(5) . ? Eu1 N4 2.932(6) . ? O6 C17 1.428(8) . ? O8 N4 1.252(7) . ? O12 N6 1.226(8) . ? O4 C9 1.240(8) . ? O13 N6 1.245(7) . ? O9 N4 1.262(7) . ? O3 C2 1.432(8) . ? O11 N6 1.268(8) . ? O16 N5 1.237(8) . ? O2 C1 1.239(7) . ? O7 C18 1.251(7) . ? O5 C10 1.423(8) . ? O10 N4 1.217(7) . ? N2 C11 1.475(9) . ? N2 C9 1.322(8) . ? N2 C14 1.502(8) . ? N1 C3 1.490(8) . ? N1 C1 1.321(8) . ? N1 C6 1.505(9) . ? N3 C22 1.500(8) . ? N3 C19 1.505(9) . ? N3 C18 1.315(8) . ? N5 O14 1.205(9) . ? N5 O15 1.194(9) . ? C24 C22 1.520(12) . ? C22 C23 1.527(12) . ? C19 C20 1.507(12) . ? C19 C21 1.526(11) . ? C11 C12 1.522(12) . ? C11 C13 1.538(12) . ? C3 C5 1.522(11) . ? C3 C4 1.500(12) . ? C7 C6 1.516(12) . ? C15 C14 1.534(12) . ? C8 C6 1.501(11) . ? C16 C14 1.513(11) . ? C1 C2 1.504(9) . ? C17 C18 1.508(9) . ? C9 C10 1.528(8) . ? 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 Eu1 O8 67.45(16) . . ? O6 Eu1 O9 117.72(17) . . ? O6 Eu1 O5 84.85(16) . . ? O6 Eu1 N4 92.36(16) . . ? O8 Eu1 O9 50.41(16) . . ? O8 Eu1 O5 70.47(17) . . ? O8 Eu1 N4 25.07(15) . . ? O4 Eu1 O6 135.41(16) . . ? O4 Eu1 O8 121.92(17) . . ? O4 Eu1 O9 82.84(17) . . ? O4 Eu1 O3 81.02(16) . . ? O4 Eu1 O1 149.91(16) . . ? O4 Eu1 O2 75.50(16) . . ? O4 Eu1 O7 78.43(17) . . ? O4 Eu1 O5 63.02(14) . . ? O4 Eu1 N4 102.42(16) . . ? O9 Eu1 N4 25.38(15) . . ? O3 Eu1 O6 104.05(16) . . ? O3 Eu1 O8 155.16(19) . . ? O3 Eu1 O9 133.60(15) . . ? O3 Eu1 O5 133.53(17) . . ? O3 Eu1 N4 152.87(17) . . ? O1 Eu1 O6 71.56(17) . . ? O1 Eu1 O8 76.67(19) . . ? O1 Eu1 O9 95.6(2) . . ? O1 Eu1 O3 78.49(19) . . ? O1 Eu1 O5 145.03(16) . . ? O1 Eu1 N4 86.65(19) . . ? O2 Eu1 O6 146.73(17) . . ? O2 Eu1 O8 110.41(17) . . ? O2 Eu1 O9 70.73(16) . . ? O2 Eu1 O3 63.18(15) . . ? O2 Eu1 O1 75.67(17) . . ? O2 Eu1 O7 130.02(15) . . ? O2 Eu1 O5 126.91(16) . . ? O2 Eu1 N4 91.31(17) . . ? O7 Eu1 O6 62.49(15) . . ? O7 Eu1 O8 119.57(16) . . ? O7 Eu1 O9 145.73(18) . . ? O7 Eu1 O3 71.19(16) . . ? O7 Eu1 O1 114.78(18) . . ? O7 Eu1 O5 73.43(18) . . ? O7 Eu1 N4 135.94(17) . . ? O5 Eu1 O9 72.53(18) . . ? O5 Eu1 N4 68.48(17) . . ? C17 O6 Eu1 124.8(4) . . ? N4 O8 Eu1 97.2(4) . . ? C9 O4 Eu1 127.8(4) . . ? N4 O9 Eu1 95.4(4) . . ? C2 O3 Eu1 123.4(4) . . ? C1 O2 Eu1 127.6(4) . . ? C18 O7 Eu1 127.2(4) . . ? C10 O5 Eu1 121.8(3) . . ? C11 N2 C14 115.7(6) . . ? C9 N2 C11 123.8(6) . . ? C9 N2 C14 120.4(6) . . ? C3 N1 C6 117.7(6) . . ? C1 N1 C3 122.1(6) . . ? C1 N1 C6 120.2(5) . . ? O12 N6 O13 121.5(7) . . ? O12 N6 O11 119.6(6) . . ? O13 N6 O11 118.9(7) . . ? C22 N3 C19 117.5(6) . . ? C18 N3 C22 121.1(6) . . ? C18 N3 C19 121.4(5) . . ? O14 N5 O16 117.7(8) . . ? O15 N5 O16 124.3(9) . . ? O15 N5 O14 117.9(9) . . ? O8 N4 Eu1 57.8(3) . . ? O8 N4 O9 116.9(5) . . ? O9 N4 Eu1 59.2(3) . . ? O10 N4 Eu1 177.9(6) . . ? O10 N4 O8 121.8(6) . . ? O10 N4 O9 121.3(6) . . ? N3 C22 C24 110.5(8) . . ? N3 C22 C23 110.9(7) . . ? C24 C22 C23 112.4(9) . . ? N3 C19 C20 110.6(7) . . ? N3 C19 C21 110.7(7) . . ? C20 C19 C21 114.3(8) . . ? N2 C11 C12 110.3(7) . . ? N2 C11 C13 112.1(8) . . ? C12 C11 C13 112.2(7) . . ? N1 C3 C5 109.9(7) . . ? N1 C3 C4 112.2(7) . . ? C4 C3 C5 112.5(7) . . ? O2 C1 N1 122.3(6) . . ? O2 C1 C2 118.4(6) . . ? N1 C1 C2 119.3(6) . . ? O3 C2 C1 107.1(5) . . ? O6 C17 C18 106.0(5) . . ? O4 C9 N2 122.6(6) . . ? O4 C9 C10 118.4(6) . . ? N2 C9 C10 119.0(6) . . ? O7 C18 N3 122.1(6) . . ? O7 C18 C17 118.7(6) . . ? N3 C18 C17 119.2(6) . . ? O5 C10 C9 107.2(5) . . ? N2 C14 C15 110.6(6) . . ? N2 C14 C16 111.0(6) . . ? C16 C14 C15 113.3(8) . . ? N1 C6 C7 110.7(7) . . ? C8 C6 N1 112.5(6) . . ? C8 C6 C7 114.0(8) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 18 0 0.0807 0.0573 17.9884 -0.0429 -0.5797 0.7129 -0.4593 7 5 0 0.0604 7.0184 4.8949 -0.0210 0.5845 0.8684 -0.0313 2 0 -8 0.2756 1.9915 -0.0708 -8.0053 0.4142 -0.1987 -0.8335 1 -17 0 0.0345 0.9462 -17.0036 0.0392 0.6540 -0.5775 0.4475 -1 -7 8 0.1953 -1.0135 -6.9392 8.0207 -0.0823 0.0172 1.0259 -7 -2 1 0.0639 -7.0077 -1.8916 1.0142 -0.7063 -0.7008 0.0624 -5 1 6 0.1255 -4.9917 1.1034 6.0061 -0.7157 -0.1466 0.5515 -5 -6 6 0.1341 -5.0140 -5.8921 6.0228 -0.4902 -0.4238 0.7301 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-4 _database_code_depnum_ccdc_archive 'CCDC 977002'