# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12srv147 _audit_creation_date 2012-07-22 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H33 Br3 Eu N6 O6 P3, 2(H2 O)' _chemical_formula_sum 'C27 H37 Br3 Eu N6 O8 P3' _chemical_formula_weight 1058.23 _chemical_melting_point ? 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' Br Br -0.2901 2.4595 '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' 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.8356(4) _cell_length_b 12.3427(5) _cell_length_c 17.2609(8) _cell_angle_alpha 107.259(4) _cell_angle_beta 97.936(4) _cell_angle_gamma 105.863(4) _cell_volume 1869.30(14) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6712 _cell_measurement_temperature 120 _cell_measurement_theta_max 32.5660 _cell_measurement_theta_min 2.5559 _exptl_absorpt_coefficient_mu 5.065 _exptl_absorpt_correction_T_max 0.723 _exptl_absorpt_correction_T_min 0.437 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.8 (release 13-04-2012 CrysAlis171 .NET) (compiled Apr 13 2012,18:42:44) 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 1.880 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 1036 _exptl_crystal_size_max 0.2852 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.0992 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_unetI/netI 0.0703 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 21350 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 2.56 _diffrn_ambient_temperature 120 _diffrn_detector CCD _diffrn_detector_area_resol_mean 16.1511 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -91.00 8.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -26.1867 -19.0000 -90.0000 99 #__ type_ start__ end____ width___ exp.time_ 2 omega -48.00 43.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -26.1867 57.0000 90.0000 91 #__ type_ start__ end____ width___ exp.time_ 3 omega -95.00 -5.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -26.1867 -57.0000 -150.0000 90 #__ type_ start__ end____ width___ exp.time_ 4 omega 4.00 74.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -108.0000 171.0000 70 #__ type_ start__ end____ width___ exp.time_ 5 omega 73.00 103.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 179.0000 60.0000 30 #__ type_ start__ end____ width___ exp.time_ 6 omega -48.00 -23.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -26.1867 57.0000 -120.0000 25 #__ type_ start__ end____ width___ exp.time_ 7 omega -95.00 -5.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -26.1867 -57.0000 90.0000 90 ; _diffrn_measurement_device '3-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method \w-scan _diffrn_orient_matrix_UB_11 -0.0170463000 _diffrn_orient_matrix_UB_12 -0.0200041000 _diffrn_orient_matrix_UB_13 0.0331038000 _diffrn_orient_matrix_UB_21 0.0233082000 _diffrn_orient_matrix_UB_22 0.0605638000 _diffrn_orient_matrix_UB_23 0.0275949000 _diffrn_orient_matrix_UB_31 -0.0715955000 _diffrn_orient_matrix_UB_32 0.0016186000 _diffrn_orient_matrix_UB_33 -0.0102969000 _diffrn_radiation_collimation monochromator _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_xray_symbol Mo _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_type 'sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 8528 _reflns_number_total 10802 _reflns_odcompleteness_completeness 98.96 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.44 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.8 (release 13-04-2012 CrysAlis171 .NET) (compiled Apr 13 2012,18:42:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.8 (release 13-04-2012 CrysAlis171 .NET) (compiled Apr 13 2012,18:42:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.8 (release 13-04-2012 CrysAlis171 .NET) (compiled Apr 13 2012,18:42:44) ; _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 ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 1.760 _refine_diff_density_min -1.014 _refine_diff_density_rms 0.163 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 442 _refine_ls_number_reflns 10802 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0429 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0333P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0832 _refine_ls_wR_factor_ref 0.0918 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.23593(2) 0.368089(17) 0.212678(12) 0.01452(5) Uani 1 1 d . . . Br1 Br 0.88145(5) 0.85702(4) 0.48858(4) 0.04342(15) Uani 1 1 d . . . Br2 Br 0.07114(5) 0.22398(4) -0.23832(3) 0.02937(11) Uani 1 1 d . . . Br3 Br -0.31843(5) 0.08430(4) 0.39511(3) 0.02972(11) Uani 1 1 d . . . P1 P 0.39926(11) 0.65795(9) 0.20947(6) 0.0170(2) Uani 1 1 d . . . P2 P -0.09640(11) 0.30493(9) 0.07058(6) 0.0158(2) Uani 1 1 d . . . P3 P 0.12058(11) 0.49100(9) 0.39258(6) 0.01480(19) Uani 1 1 d . . . O1 O 0.2929(3) 0.5311(2) 0.16621(16) 0.0206(6) Uani 1 1 d . . . O2 O 0.4802(3) 0.7180(3) 0.15829(19) 0.0246(6) Uani 1 1 d . . . O3 O -0.0093(3) 0.3333(3) 0.15717(17) 0.0204(6) Uani 1 1 d . . . O4 O -0.2326(3) 0.1982(3) 0.03683(18) 0.0234(6) Uani 1 1 d . . . O5 O 0.2161(3) 0.5023(2) 0.33176(17) 0.0195(6) Uani 1 1 d . . . O6 O 0.1932(3) 0.5309(2) 0.48245(16) 0.0198(6) Uani 1 1 d . . . O7 O 0.4113(3) 0.9007(3) 0.12131(19) 0.0271(7) Uani 1 1 d G . . H7C H 0.3660 0.8730 0.0702 0.041 Uiso 1 1 d G . . H7D H 0.4311 0.8448 0.1348 0.041 Uiso 1 1 d G . . O8 O -0.3097(4) 0.0206(4) 0.1103(3) 0.0427(9) Uani 1 1 d G . . H8A H -0.3013 0.0748 0.0886 0.064 Uiso 1 1 d G . . H8B H -0.3955 -0.0020 0.1173 0.064 Uiso 1 1 d G . . N1 N 0.4311(4) 0.3093(3) 0.3037(2) 0.0182(7) Uani 1 1 d . . . N2 N 0.4100(4) 0.2752(3) 0.1277(2) 0.0183(7) Uani 1 1 d . . . N3 N 0.1758(4) 0.1301(3) 0.1794(2) 0.0185(7) Uani 1 1 d . . . N4 N 0.4848(3) 0.5385(3) 0.3026(2) 0.0160(6) Uani 1 1 d . . . N5 N 0.1670(3) 0.3017(3) 0.0478(2) 0.0163(6) Uani 1 1 d . . . N6 N 0.0571(3) 0.2637(3) 0.29005(19) 0.0156(6) Uani 1 1 d . . . C1 C 0.5506(4) 0.2851(4) 0.2635(3) 0.0210(8) Uani 1 1 d . . . H1A H 0.5376 0.2000 0.2478 0.025 Uiso 1 1 calc R . . H1B H 0.6431 0.3289 0.3041 0.025 Uiso 1 1 calc R . . C2 C 0.5563(4) 0.3207(4) 0.1862(3) 0.0214(8) Uani 1 1 d . . . H2A H 0.5940 0.4077 0.2035 0.026 Uiso 1 1 calc R . . H2B H 0.6224 0.2887 0.1574 0.026 Uiso 1 1 calc R . . C3 C 0.3562(5) 0.1403(4) 0.0908(3) 0.0230(9) Uani 1 1 d . . . H3A H 0.4206 0.1102 0.1198 0.028 Uiso 1 1 calc R . . H3B H 0.3611 0.1161 0.0327 0.028 Uiso 1 1 calc R . . C4 C 0.2015(4) 0.0823(4) 0.0956(3) 0.0212(8) Uani 1 1 d . . . H4A H 0.1345 0.0953 0.0553 0.025 Uiso 1 1 calc R . . H4B H 0.1812 -0.0038 0.0803 0.025 Uiso 1 1 calc R . . C5 C 0.2624(4) 0.0979(3) 0.2419(3) 0.0206(8) Uani 1 1 d . . . H5A H 0.3295 0.0631 0.2161 0.025 Uiso 1 1 calc R . . H5B H 0.1968 0.0368 0.2566 0.025 Uiso 1 1 calc R . . C6 C 0.3484(4) 0.2032(3) 0.3214(2) 0.0192(8) Uani 1 1 d . . . H6A H 0.2820 0.2251 0.3549 0.023 Uiso 1 1 calc R . . H6B H 0.4156 0.1790 0.3537 0.023 Uiso 1 1 calc R . . C7 C 0.4964(4) 0.4118(3) 0.3844(2) 0.0185(8) Uani 1 1 d . . . H7A H 0.5731 0.3969 0.4171 0.022 Uiso 1 1 calc R . . H7B H 0.4226 0.4181 0.4158 0.022 Uiso 1 1 calc R . . C8 C 0.5580(4) 0.5277(3) 0.3702(2) 0.0177(8) Uani 1 1 d . . . C9 C 0.6772(4) 0.6204(3) 0.4272(3) 0.0201(8) Uani 1 1 d . . . H9 H 0.7275 0.6100 0.4727 0.024 Uiso 1 1 calc R . . C10 C 0.7184(4) 0.7284(4) 0.4139(3) 0.0232(9) Uani 1 1 d . . . C11 C 0.6418(4) 0.7428(4) 0.3463(3) 0.0216(8) Uani 1 1 d . . . H11 H 0.6683 0.8154 0.3371 0.026 Uiso 1 1 calc R . . C12 C 0.5239(4) 0.6450(3) 0.2923(2) 0.0168(8) Uani 1 1 d . . . C13 C 0.3101(5) 0.7514(4) 0.2679(3) 0.0239(9) Uani 1 1 d . . . H13A H 0.2370 0.7611 0.2301 0.036 Uiso 1 1 calc R . . H13B H 0.3803 0.8288 0.3010 0.036 Uiso 1 1 calc R . . H13C H 0.2654 0.7144 0.3039 0.036 Uiso 1 1 calc R . . C14 C 0.4220(4) 0.3252(4) 0.0596(2) 0.0203(8) Uani 1 1 d . . . H14A H 0.4799 0.2903 0.0250 0.024 Uiso 1 1 calc R . . H14B H 0.4708 0.4116 0.0834 0.024 Uiso 1 1 calc R . . C15 C 0.2722(4) 0.2979(3) 0.0064(2) 0.0178(8) Uani 1 1 d . . . C16 C 0.2488(4) 0.2751(3) -0.0792(3) 0.0207(8) Uani 1 1 d . . . H16 H 0.3237 0.2734 -0.1065 0.025 Uiso 1 1 calc R . . C17 C 0.1090(4) 0.2550(3) -0.1220(2) 0.0183(8) Uani 1 1 d . . . C18 C -0.0012(4) 0.2579(3) -0.0808(2) 0.0185(8) Uani 1 1 d . . . H18 H -0.0955 0.2431 -0.1095 0.022 Uiso 1 1 calc R . . C19 C 0.0329(4) 0.2838(3) 0.0049(2) 0.0167(8) Uani 1 1 d . . . C20 C -0.1323(5) 0.4369(4) 0.0632(3) 0.0280(10) Uani 1 1 d . . . H20A H -0.1945 0.4575 0.0993 0.042 Uiso 1 1 calc R . . H20B H -0.1795 0.4215 0.0066 0.042 Uiso 1 1 calc R . . H20C H -0.0423 0.5025 0.0798 0.042 Uiso 1 1 calc R . . C21 C 0.0190(4) 0.0804(4) 0.1751(3) 0.0213(8) Uani 1 1 d . . . H21A H -0.0067 -0.0046 0.1668 0.026 Uiso 1 1 calc R . . H21B H -0.0373 0.0886 0.1277 0.026 Uiso 1 1 calc R . . C22 C -0.0188(4) 0.1450(3) 0.2545(2) 0.0186(8) Uani 1 1 d . . . C23 C -0.1299(4) 0.0879(3) 0.2842(3) 0.0198(8) Uani 1 1 d . . . H23 H -0.1784 0.0055 0.2596 0.024 Uiso 1 1 calc R . . C24 C -0.1667(4) 0.1568(4) 0.3516(3) 0.0193(8) Uani 1 1 d . . . C25 C -0.0947(4) 0.2797(3) 0.3874(2) 0.0182(8) Uani 1 1 d . . . H25 H -0.1208 0.3270 0.4318 0.022 Uiso 1 1 calc R . . C26 C 0.0179(4) 0.3300(3) 0.3546(2) 0.0148(7) Uani 1 1 d . . . C27 C -0.0131(4) 0.5607(4) 0.3765(3) 0.0231(9) Uani 1 1 d . . . H27A H 0.0337 0.6460 0.3933 0.035 Uiso 1 1 calc R . . H27B H -0.0826 0.5444 0.4090 0.035 Uiso 1 1 calc R . . H27C H -0.0622 0.5291 0.3184 0.035 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 Eu1 0.01399(10) 0.01310(9) 0.01663(10) 0.00526(7) 0.00573(7) 0.00365(7) Br1 0.0304(3) 0.0210(2) 0.0602(4) 0.0143(2) -0.0180(2) -0.00612(19) Br2 0.0326(3) 0.0434(3) 0.0207(2) 0.0153(2) 0.01231(19) 0.0184(2) Br3 0.0280(2) 0.0227(2) 0.0420(3) 0.0154(2) 0.0200(2) 0.00375(18) P1 0.0161(5) 0.0162(5) 0.0226(5) 0.0105(4) 0.0077(4) 0.0059(4) P2 0.0146(5) 0.0150(5) 0.0193(5) 0.0076(4) 0.0066(4) 0.0045(4) P3 0.0147(5) 0.0133(4) 0.0157(5) 0.0045(4) 0.0048(4) 0.0037(4) O1 0.0226(15) 0.0195(14) 0.0176(14) 0.0075(12) 0.0017(12) 0.0041(12) O2 0.0244(16) 0.0267(16) 0.0350(17) 0.0220(14) 0.0153(14) 0.0112(13) O3 0.0176(14) 0.0250(15) 0.0186(14) 0.0066(12) 0.0064(12) 0.0072(12) O4 0.0183(15) 0.0221(15) 0.0263(16) 0.0094(12) 0.0072(13) -0.0006(12) O5 0.0210(15) 0.0139(13) 0.0191(14) 0.0020(11) 0.0084(12) 0.0010(11) O6 0.0212(15) 0.0181(14) 0.0170(14) 0.0040(11) 0.0045(12) 0.0043(12) O7 0.0305(18) 0.0217(15) 0.0307(17) 0.0130(13) 0.0029(14) 0.0092(14) O8 0.0232(18) 0.053(2) 0.053(2) 0.0360(19) 0.0020(17) -0.0002(17) N1 0.0175(17) 0.0142(15) 0.0253(18) 0.0096(14) 0.0080(14) 0.0048(13) N2 0.0176(17) 0.0172(16) 0.0202(17) 0.0057(14) 0.0062(14) 0.0062(14) N3 0.0173(17) 0.0153(15) 0.0212(17) 0.0033(13) 0.0079(14) 0.0042(13) N4 0.0130(16) 0.0157(15) 0.0218(17) 0.0092(13) 0.0065(13) 0.0046(13) N5 0.0158(16) 0.0155(15) 0.0175(16) 0.0050(13) 0.0059(13) 0.0047(13) N6 0.0140(16) 0.0138(15) 0.0172(16) 0.0044(13) 0.0045(13) 0.0027(13) C1 0.017(2) 0.0198(19) 0.029(2) 0.0111(17) 0.0061(17) 0.0076(16) C2 0.016(2) 0.022(2) 0.030(2) 0.0115(18) 0.0094(17) 0.0074(16) C3 0.025(2) 0.0180(19) 0.028(2) 0.0066(17) 0.0119(18) 0.0088(17) C4 0.022(2) 0.0164(18) 0.026(2) 0.0060(16) 0.0108(18) 0.0067(16) C5 0.018(2) 0.0168(18) 0.029(2) 0.0097(17) 0.0087(17) 0.0056(16) C6 0.018(2) 0.0181(18) 0.025(2) 0.0125(16) 0.0072(17) 0.0053(16) C7 0.0144(19) 0.0177(18) 0.024(2) 0.0111(16) 0.0039(16) 0.0021(15) C8 0.0159(19) 0.0165(18) 0.023(2) 0.0097(16) 0.0092(16) 0.0046(15) C9 0.0153(19) 0.0180(19) 0.026(2) 0.0083(17) 0.0006(17) 0.0057(16) C10 0.015(2) 0.0171(19) 0.031(2) 0.0065(17) -0.0007(17) 0.0013(16) C11 0.016(2) 0.0173(19) 0.032(2) 0.0117(17) 0.0047(17) 0.0038(16) C12 0.0131(18) 0.0155(18) 0.025(2) 0.0102(16) 0.0078(16) 0.0046(15) C13 0.023(2) 0.026(2) 0.027(2) 0.0094(18) 0.0080(18) 0.0136(18) C14 0.019(2) 0.0202(19) 0.024(2) 0.0094(17) 0.0093(17) 0.0056(16) C15 0.019(2) 0.0147(17) 0.022(2) 0.0079(15) 0.0092(16) 0.0056(15) C16 0.024(2) 0.0126(17) 0.029(2) 0.0092(16) 0.0140(18) 0.0060(16) C17 0.025(2) 0.0169(18) 0.0146(19) 0.0061(15) 0.0083(16) 0.0072(16) C18 0.022(2) 0.0141(17) 0.023(2) 0.0086(16) 0.0094(17) 0.0061(16) C19 0.0168(19) 0.0125(17) 0.021(2) 0.0068(15) 0.0085(16) 0.0029(15) C20 0.034(3) 0.026(2) 0.034(3) 0.015(2) 0.019(2) 0.017(2) C21 0.020(2) 0.0165(19) 0.023(2) 0.0039(16) 0.0056(17) 0.0012(16) C22 0.019(2) 0.0147(18) 0.022(2) 0.0078(16) 0.0062(16) 0.0031(15) C23 0.018(2) 0.0130(17) 0.029(2) 0.0092(16) 0.0061(17) 0.0022(15) C24 0.0144(19) 0.0219(19) 0.024(2) 0.0127(17) 0.0064(16) 0.0029(16) C25 0.019(2) 0.0179(18) 0.019(2) 0.0090(16) 0.0090(16) 0.0043(16) C26 0.0153(18) 0.0154(17) 0.0148(18) 0.0065(14) 0.0044(15) 0.0049(15) C27 0.019(2) 0.025(2) 0.028(2) 0.0125(18) 0.0048(18) 0.0084(17) _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 O1 2.339(3) . ? Eu1 O3 2.339(3) . ? Eu1 O5 2.296(3) . ? Eu1 N1 2.699(3) . ? Eu1 N2 2.677(3) . ? Eu1 N3 2.695(3) . ? Eu1 N4 2.650(3) . ? Eu1 N5 2.648(3) . ? Eu1 N6 2.640(3) . ? Br1 C10 1.891(4) . ? Br2 C17 1.892(4) . ? Br3 C24 1.890(4) . ? P1 O1 1.516(3) . ? P1 O2 1.491(3) . ? P1 C12 1.826(4) . ? P1 C13 1.795(4) . ? P2 O3 1.504(3) . ? P2 O4 1.495(3) . ? P2 C19 1.837(4) . ? P2 C20 1.795(4) . ? P3 O5 1.514(3) . ? P3 O6 1.486(3) . ? P3 C26 1.829(4) . ? P3 C27 1.791(4) . ? O7 H7C 0.8502 . ? O7 H7D 0.8500 . ? O8 H8A 0.8499 . ? O8 H8B 0.8499 . ? N1 C1 1.499(5) . ? N1 C6 1.481(5) . ? N1 C7 1.488(5) . ? N2 C2 1.492(5) . ? N2 C3 1.502(5) . ? N2 C14 1.485(5) . ? N3 C4 1.478(5) . ? N3 C5 1.494(5) . ? N3 C21 1.478(5) . ? N4 C8 1.346(5) . ? N4 C12 1.336(5) . ? N5 C15 1.339(5) . ? N5 C19 1.346(5) . ? N6 C22 1.350(5) . ? N6 C26 1.345(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 C2 1.527(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 C4 1.519(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 C6 1.520(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.500(5) . ? C8 C9 1.390(5) . ? C9 H9 0.9300 . ? C9 C10 1.380(5) . ? C10 C11 1.384(6) . ? C11 H11 0.9300 . ? C11 C12 1.393(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 C15 1.516(5) . ? C15 C16 1.393(6) . ? C16 H16 0.9300 . ? C16 C17 1.387(6) . ? C17 C18 1.379(5) . ? C18 H18 0.9300 . ? C18 C19 1.387(5) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 C22 1.518(5) . ? C22 C23 1.379(5) . ? C23 H23 0.9300 . ? C23 C24 1.381(5) . ? C24 C25 1.385(5) . ? C25 H25 0.9300 . ? C25 C26 1.392(5) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Eu1 O3 87.68(10) . . ? O1 Eu1 N1 124.86(10) . . ? O1 Eu1 N2 90.27(10) . . ? O1 Eu1 N3 148.66(10) . . ? O1 Eu1 N4 67.05(9) . . ? O1 Eu1 N5 67.19(9) . . ? O1 Eu1 N6 142.31(9) . . ? O3 Eu1 N1 147.18(10) . . ? O3 Eu1 N2 124.66(10) . . ? O3 Eu1 N3 89.51(10) . . ? O3 Eu1 N4 143.50(9) . . ? O3 Eu1 N5 66.59(9) . . ? O3 Eu1 N6 66.35(9) . . ? O5 Eu1 O1 85.57(9) . . ? O5 Eu1 O3 87.34(9) . . ? O5 Eu1 N1 90.79(9) . . ? O5 Eu1 N2 147.58(10) . . ? O5 Eu1 N3 125.48(10) . . ? O5 Eu1 N4 65.71(10) . . ? O5 Eu1 N5 142.11(9) . . ? O5 Eu1 N6 67.23(9) . . ? N2 Eu1 N1 65.56(10) . . ? N2 Eu1 N3 66.06(10) . . ? N3 Eu1 N1 65.25(10) . . ? N4 Eu1 N1 61.60(9) . . ? N4 Eu1 N2 83.06(10) . . ? N4 Eu1 N3 125.83(9) . . ? N5 Eu1 N1 126.11(9) . . ? N5 Eu1 N2 61.91(9) . . ? N5 Eu1 N3 83.09(10) . . ? N5 Eu1 N4 120.87(10) . . ? N6 Eu1 N1 82.75(9) . . ? N6 Eu1 N2 126.68(10) . . ? N6 Eu1 N3 61.89(9) . . ? N6 Eu1 N4 118.94(10) . . ? N6 Eu1 N5 120.19(10) . . ? O1 P1 Eu1 30.32(10) . . ? O1 P1 C12 103.78(16) . . ? O1 P1 C13 109.49(19) . . ? O2 P1 Eu1 140.11(12) . . ? O2 P1 O1 118.31(17) . . ? O2 P1 C12 111.19(17) . . ? O2 P1 C13 110.66(18) . . ? C12 P1 Eu1 75.21(12) . . ? C13 P1 Eu1 105.91(15) . . ? C13 P1 C12 102.00(18) . . ? O3 P2 Eu1 28.66(10) . . ? O3 P2 C19 103.67(17) . . ? O3 P2 C20 109.29(19) . . ? O4 P2 Eu1 132.26(12) . . ? O4 P2 O3 117.93(17) . . ? O4 P2 C19 109.86(17) . . ? O4 P2 C20 110.7(2) . . ? C19 P2 Eu1 75.18(12) . . ? C20 P2 Eu1 113.70(16) . . ? C20 P2 C19 104.33(19) . . ? O5 P3 Eu1 28.30(10) . . ? O5 P3 C26 103.40(16) . . ? O5 P3 C27 108.72(18) . . ? O6 P3 Eu1 130.58(11) . . ? O6 P3 O5 117.86(16) . . ? O6 P3 C26 109.37(16) . . ? O6 P3 C27 111.69(18) . . ? C26 P3 Eu1 75.17(12) . . ? C27 P3 Eu1 114.39(14) . . ? C27 P3 C26 104.70(19) . . ? P1 O1 Eu1 130.58(15) . . ? P2 O3 Eu1 133.37(16) . . ? P3 O5 Eu1 133.48(16) . . ? H7C O7 H7D 109.5 . . ? H8A O8 H8B 109.5 . . ? C1 N1 Eu1 114.7(2) . . ? C6 N1 Eu1 107.0(2) . . ? C6 N1 C1 110.9(3) . . ? C6 N1 C7 108.1(3) . . ? C7 N1 Eu1 106.9(2) . . ? C7 N1 C1 108.9(3) . . ? C2 N2 Eu1 107.0(2) . . ? C2 N2 C3 110.9(3) . . ? C3 N2 Eu1 114.3(2) . . ? C14 N2 Eu1 106.7(2) . . ? C14 N2 C2 108.5(3) . . ? C14 N2 C3 109.3(3) . . ? C4 N3 Eu1 105.5(2) . . ? C4 N3 C5 111.1(3) . . ? C4 N3 C21 108.9(3) . . ? C5 N3 Eu1 114.9(2) . . ? C21 N3 Eu1 106.4(2) . . ? C21 N3 C5 109.9(3) . . ? C8 N4 Eu1 119.4(2) . . ? C12 N4 Eu1 120.8(2) . . ? C12 N4 C8 118.4(3) . . ? C15 N5 Eu1 119.0(2) . . ? C15 N5 C19 118.6(3) . . ? C19 N5 Eu1 122.1(2) . . ? C22 N6 Eu1 119.4(2) . . ? C26 N6 Eu1 120.7(2) . . ? C26 N6 C22 118.5(3) . . ? N1 C1 H1A 108.8 . . ? N1 C1 H1B 108.8 . . ? N1 C1 C2 113.6(3) . . ? H1A C1 H1B 107.7 . . ? C2 C1 H1A 108.8 . . ? C2 C1 H1B 108.8 . . ? N2 C2 C1 112.0(3) . . ? N2 C2 H2A 109.2 . . ? N2 C2 H2B 109.2 . . ? C1 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? N2 C3 H3A 108.8 . . ? N2 C3 H3B 108.8 . . ? N2 C3 C4 113.9(3) . . ? H3A C3 H3B 107.7 . . ? C4 C3 H3A 108.8 . . ? C4 C3 H3B 108.8 . . ? N3 C4 C3 113.0(3) . . ? N3 C4 H4A 109.0 . . ? N3 C4 H4B 109.0 . . ? C3 C4 H4A 109.0 . . ? C3 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? N3 C5 H5A 108.7 . . ? N3 C5 H5B 108.7 . . ? N3 C5 C6 114.2(3) . . ? H5A C5 H5B 107.6 . . ? C6 C5 H5A 108.7 . . ? C6 C5 H5B 108.7 . . ? N1 C6 C5 112.1(3) . . ? N1 C6 H6A 109.2 . . ? N1 C6 H6B 109.2 . . ? C5 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? N1 C7 H7A 109.4 . . ? N1 C7 H7B 109.4 . . ? N1 C7 C8 111.1(3) . . ? H7A C7 H7B 108.0 . . ? C8 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? N4 C8 C7 115.8(3) . . ? N4 C8 C9 122.8(4) . . ? C9 C8 C7 121.3(3) . . ? C8 C9 H9 121.2 . . ? C10 C9 C8 117.7(4) . . ? C10 C9 H9 121.2 . . ? C9 C10 Br1 119.5(3) . . ? C9 C10 C11 120.5(4) . . ? C11 C10 Br1 120.0(3) . . ? C10 C11 H11 121.1 . . ? C10 C11 C12 117.9(4) . . ? C12 C11 H11 121.1 . . ? N4 C12 P1 114.9(3) . . ? N4 C12 C11 122.6(3) . . ? C11 C12 P1 122.1(3) . . ? P1 C13 H13A 109.5 . . ? P1 C13 H13B 109.5 . . ? P1 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 H14A 109.6 . . ? N2 C14 H14B 109.6 . . ? N2 C14 C15 110.3(3) . . ? H14A C14 H14B 108.1 . . ? C15 C14 H14A 109.6 . . ? C15 C14 H14B 109.6 . . ? N5 C15 C14 115.6(3) . . ? N5 C15 C16 123.0(4) . . ? C16 C15 C14 121.4(3) . . ? C15 C16 H16 121.4 . . ? C17 C16 C15 117.2(4) . . ? C17 C16 H16 121.4 . . ? C16 C17 Br2 118.9(3) . . ? C18 C17 Br2 120.2(3) . . ? C18 C17 C16 120.9(4) . . ? C17 C18 H18 121.0 . . ? C17 C18 C19 117.9(4) . . ? C19 C18 H18 121.0 . . ? N5 C19 P2 114.0(3) . . ? N5 C19 C18 122.5(4) . . ? C18 C19 P2 123.5(3) . . ? P2 C20 H20A 109.5 . . ? P2 C20 H20B 109.5 . . ? P2 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N3 C21 H21A 109.4 . . ? N3 C21 H21B 109.4 . . ? N3 C21 C22 111.1(3) . . ? H21A C21 H21B 108.0 . . ? C22 C21 H21A 109.4 . . ? C22 C21 H21B 109.4 . . ? N6 C22 C21 115.1(3) . . ? N6 C22 C23 122.7(4) . . ? C23 C22 C21 122.0(4) . . ? C22 C23 H23 121.0 . . ? C22 C23 C24 117.9(4) . . ? C24 C23 H23 121.0 . . ? C23 C24 Br3 120.1(3) . . ? C23 C24 C25 120.7(4) . . ? C25 C24 Br3 119.2(3) . . ? C24 C25 H25 121.1 . . ? C24 C25 C26 117.8(4) . . ? C26 C25 H25 121.1 . . ? N6 C26 P3 114.3(3) . . ? N6 C26 C25 122.3(4) . . ? C25 C26 P3 123.4(3) . . ? P3 C27 H27A 109.5 . . ? P3 C27 H27B 109.5 . . ? P3 C27 H27C 109.5 . . ? H27A C27 H27B 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? 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 O7 H7C O4 0.85 1.91 2.749(4) 169.3 2_565 O7 H7D O2 0.85 1.89 2.742(4) 176.2 . O8 H8A O4 0.85 2.00 2.827(5) 165.7 . O8 H8B O7 0.85 1.97 2.801(5) 163.8 1_445 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 -6 -5 23 0.0194 -5.9931 -5.0019 22.9726 0.9627 0.1913 0.1844 12 -6 -12 0.1116 11.9852 -5.9875 -12.0019 -0.4818 -0.4145 -0.7442 -10 5 17 0.0673 -9.9863 4.9842 16.9990 0.6333 0.5382 0.5480 6 11 2 0.0792 6.0008 10.9694 2.0346 -0.2544 0.8604 -0.4328 -2 -16 4 0.0624 -2.0052 -15.9664 3.9527 0.4844 -0.9047 0.0770 10 -5 13 0.1367 9.9922 -5.0074 12.9899 0.3599 0.2881 -0.8573 -1 17 -7 0.0884 -0.9925 16.9690 -6.9514 -0.5527 0.8128 0.1701 2 0 -23 0.0395 1.9939 0.0161 -22.9898 -0.7954 -0.5869 0.0940 0 0 22 0.0688 0.0043 -0.0170 21.9918 0.7283 0.6059 -0.2268 -13 7 -4 0.1265 -12.9871 6.9985 -3.9903 -0.0507 0.0110 0.9822 _database_code_depnum_ccdc_archive 'CCDC 948247'