# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Robin D. Rogers' _publ_contact_author_address ;205 AIME 720 2nd Street The University of Alabama Tuscaloosa, AL 35487 ; _publ_contact_author_email RDRogers@bama.ua.edu _publ_contact_author_phone 1(205)348-4323 _publ_contact_author_fax 1(205)348-0823 loop_ _publ_author_name _publ_author_address C.C.Hines ;205 AIME 720 2nd Street The University of Alabama Tuscaloosa, AL 35487 ; V.A.Cocalia ;205 AIME 720 2nd Street The University of Alabama Tuscaloosa, AL 35487 ; R.D.Rogers ;205 AIME 720 2nd Street The University of Alabama Tuscaloosa, AL 35487 ; data_c1 _database_code_depnum_ccdc_archive 'CCDC 656211' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Form I' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H30 Cl5 Er N4 O4' _chemical_formula_weight 638.91 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7022(6) _cell_length_b 8.8756(6) _cell_length_c 18.1830(12) _cell_angle_alpha 78.3420(10) _cell_angle_beta 83.5100(10) _cell_angle_gamma 60.5170(10) _cell_volume 1197.17(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7111 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.18 _exptl_crystal_description fragment _exptl_crystal_colour pink _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.772 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 630 _exptl_absorpt_coefficient_mu 4.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details '(SADABS, Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7812 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 28.18 _reflns_number_total 5240 _reflns_number_gt 5079 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0462P)^2^+2.9165P] 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 SHELXL _refine_ls_extinction_coef 0.0329(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5240 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.015 _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 Er1 Er 0.849576(19) -0.119169(19) 0.743737(8) 0.01481(9) Uani 1 1 d . . . Cl1 Cl 0.8511(2) -0.1635(2) 0.88987(6) 0.0481(3) Uani 1 1 d . . . Cl2 Cl 0.86471(16) -0.11079(18) 0.59993(6) 0.0381(3) Uani 1 1 d . . . Cl3 Cl 0.67707(13) 0.22972(12) 0.72098(6) 0.0244(2) Uani 1 1 d . . . Cl4 Cl 1.14865(13) -0.71797(13) 0.73534(7) 0.0283(2) Uani 1 1 d . . . Cl5 Cl 1.44195(13) -0.32502(13) 0.78802(6) 0.0275(2) Uani 1 1 d . . . O1 O 1.0637(5) -0.0335(5) 0.7430(2) 0.0276(7) Uani 1 1 d . . . H1O1 H 1.044(7) 0.056(8) 0.737(3) 0.021(13) Uiso 1 1 d . . . H2O1 H 1.160(10) -0.097(9) 0.755(4) 0.044(18) Uiso 1 1 d . . . O2 O 1.1326(4) -0.3676(4) 0.7440(2) 0.0254(7) Uani 1 1 d . . . H1O2 H 1.139(7) -0.453(8) 0.740(3) 0.023(13) Uiso 1 1 d . . . H2O2 H 1.206(8) -0.367(7) 0.758(3) 0.023(14) Uiso 1 1 d . . . O3 O 0.8163(5) -0.3707(5) 0.7553(3) 0.0373(9) Uani 1 1 d . . . H1O3 H 0.888(8) -0.455(8) 0.751(3) 0.018(12) Uiso 1 1 d . . . H2O3 H 0.741(10) -0.367(9) 0.765(4) 0.035(18) Uiso 1 1 d . . . O4 O 0.5493(4) -0.0350(4) 0.7533(2) 0.0306(7) Uani 1 1 d . . . H1O4 H 0.509(8) -0.106(8) 0.764(3) 0.032(15) Uiso 1 1 d . . . H2O4 H 0.480(9) 0.068(10) 0.741(4) 0.046(19) Uiso 1 1 d . . . N1 N 0.5090(5) 0.3032(5) 0.45804(19) 0.0214(7) Uani 1 1 d . . . N2 N 0.2448(5) 0.5179(5) 0.46627(19) 0.0221(7) Uani 1 1 d . . . N3 N 0.4952(10) 0.2644(9) 0.9512(3) 0.0677(17) Uani 1 1 d . B . N4 N 0.7383(11) 0.2712(10) 0.9520(3) 0.077(2) Uani 1 1 d . C . C1 C 0.3704(6) 0.4289(5) 0.4188(2) 0.0220(8) Uani 1 1 d . . . H1A H 0.3620 0.4517 0.3657 0.026 Uiso 1 1 calc R . . C2 C 0.3057(6) 0.4461(6) 0.5383(2) 0.0266(9) Uani 1 1 d . . . H2A H 0.2436 0.4846 0.5831 0.032 Uiso 1 1 calc R . . C3 C 0.4719(6) 0.3094(6) 0.5335(2) 0.0255(8) Uani 1 1 d . . . H3A H 0.5472 0.2334 0.5741 0.031 Uiso 1 1 calc R . . C4 C 0.6706(6) 0.1724(6) 0.4244(3) 0.0290(9) Uani 1 1 d . . . H4A H 0.7728 0.1328 0.4565 0.035 Uiso 1 1 calc R . . H4B H 0.6933 0.2273 0.3743 0.035 Uiso 1 1 calc R . . C5 C 0.6515(6) 0.0172(6) 0.4167(3) 0.0319(10) Uani 1 1 d . . . H5A H 0.7517 -0.0592 0.3876 0.048 Uiso 1 1 calc R . . H5B H 0.5415 0.0580 0.3909 0.048 Uiso 1 1 calc R . . H5C H 0.6489 -0.0485 0.4667 0.048 Uiso 1 1 calc R . . C6 C 0.0743(7) 0.6704(7) 0.4439(3) 0.0336(10) Uani 1 1 d . . . H6A H 0.050(9) 0.645(9) 0.410(4) 0.050 Uiso 1 1 d . . . H6B H -0.007(9) 0.670(9) 0.488(4) 0.050 Uiso 1 1 d . . . H6C H 0.085(9) 0.764(10) 0.433(4) 0.050 Uiso 1 1 d . . . C7 C 0.6268(13) 0.2738(9) 0.9102(4) 0.072(2) Uani 1 1 d . . . H7A H 0.6377 0.2814 0.8572 0.086 Uiso 1 1 calc R . . C8 C 0.6757(14) 0.2635(14) 1.0250(4) 0.082(3) Uani 1 1 d . . . H8A H 0.7292 0.2633 1.0678 0.098 Uiso 1 1 calc R . . C9 C 0.5265(13) 0.2562(13) 1.0246(4) 0.075(2) Uani 1 1 d . . . H9A H 0.4553 0.2471 1.0670 0.090 Uiso 1 1 calc R . . C10 C 0.3499(16) 0.2569(16) 0.9222(6) 0.103(3) Uani 1 1 d . . . H10A H 0.3745 0.2383 0.8693 0.124 Uiso 0.60 1 calc PR A 1 H10B H 0.3350 0.1585 0.9522 0.124 Uiso 0.60 1 calc PR A 1 H10C H 0.2705 0.2490 0.9637 0.154 Uiso 0.40 1 calc PR A 2 H10D H 0.3971 0.1534 0.8978 0.154 Uiso 0.40 1 calc PR A 2 H10E H 0.2845 0.3632 0.8856 0.154 Uiso 0.40 1 calc PR A 2 C11 C 0.208(2) 0.405(2) 0.9267(7) 0.069(3) Uani 0.60 1 d P B 1 H11A H 0.1103 0.4070 0.9038 0.103 Uiso 0.60 1 calc PR B 1 H11B H 0.2280 0.5015 0.9001 0.103 Uiso 0.60 1 calc PR B 1 H11C H 0.1799 0.4169 0.9796 0.103 Uiso 0.60 1 calc PR B 1 C11A C 1.009(4) 0.124(4) 0.9274(11) 0.091(9) Uani 0.40 1 d P C 2 H11D H 1.1217 0.1128 0.9060 0.137 Uiso 0.40 1 calc PR C 2 H11E H 0.9656 0.0708 0.8986 0.137 Uiso 0.40 1 calc PR C 2 H11F H 1.0250 0.0645 0.9798 0.137 Uiso 0.40 1 calc PR C 2 C12 C 0.8924(17) 0.293(2) 0.9246(8) 0.138(6) Uani 1 1 d . . . H12A H 0.9572 0.2836 0.9674 0.208 Uiso 0.60 1 calc PR C 1 H12B H 0.8535 0.4078 0.8929 0.208 Uiso 0.60 1 calc PR C 1 H12C H 0.9696 0.2003 0.8953 0.208 Uiso 0.60 1 calc PR C 1 H12D H 0.8768 0.3595 0.8729 0.166 Uiso 0.40 1 calc PR C 2 H12E H 0.9229 0.3482 0.9584 0.166 Uiso 0.40 1 calc PR C 2 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 Er1 0.01455(12) 0.01347(12) 0.01288(11) 0.00073(6) -0.00451(6) -0.00431(8) Cl1 0.0641(9) 0.0560(8) 0.0138(5) 0.0026(5) -0.0036(5) -0.0235(7) Cl2 0.0344(6) 0.0462(7) 0.0159(5) -0.0078(4) -0.0081(4) -0.0035(5) Cl3 0.0267(5) 0.0139(4) 0.0243(5) 0.0014(3) -0.0040(4) -0.0046(4) Cl4 0.0201(5) 0.0166(4) 0.0461(6) -0.0104(4) -0.0046(4) -0.0046(4) Cl5 0.0178(5) 0.0220(5) 0.0407(6) 0.0013(4) -0.0089(4) -0.0089(4) O1 0.0218(17) 0.0143(15) 0.045(2) 0.0006(13) -0.0078(14) -0.0080(13) O2 0.0164(14) 0.0142(15) 0.0450(19) -0.0020(12) -0.0120(13) -0.0059(12) O3 0.0156(16) 0.0164(17) 0.076(3) -0.0106(16) 0.0057(17) -0.0047(14) O4 0.0181(15) 0.0150(15) 0.053(2) -0.0031(14) -0.0053(14) -0.0040(13) N1 0.0225(17) 0.0213(16) 0.0180(16) 0.0012(13) -0.0041(13) -0.0096(14) N2 0.0230(17) 0.0184(16) 0.0193(16) -0.0018(13) -0.0047(13) -0.0054(14) N3 0.104(5) 0.075(4) 0.034(3) -0.004(3) -0.004(3) -0.052(4) N4 0.100(5) 0.093(5) 0.037(3) -0.011(3) 0.019(3) -0.049(4) C1 0.025(2) 0.0210(19) 0.0140(17) -0.0006(14) -0.0057(14) -0.0067(16) C2 0.035(2) 0.028(2) 0.0160(18) -0.0021(16) -0.0036(16) -0.0152(19) C3 0.035(2) 0.026(2) 0.0153(18) 0.0049(15) -0.0088(16) -0.0154(18) C4 0.021(2) 0.028(2) 0.028(2) 0.0013(17) -0.0010(16) -0.0065(17) C5 0.027(2) 0.031(2) 0.026(2) -0.0063(18) -0.0050(17) -0.0035(19) C6 0.028(2) 0.026(2) 0.033(3) -0.0033(19) -0.0064(19) -0.0027(19) C7 0.124(7) 0.043(4) 0.027(3) -0.005(3) 0.017(4) -0.028(4) C8 0.108(7) 0.128(8) 0.033(3) -0.014(4) 0.010(4) -0.076(7) C9 0.099(6) 0.117(7) 0.028(3) -0.015(4) 0.015(3) -0.067(6) C10 0.140(10) 0.121(9) 0.076(6) -0.010(6) -0.026(6) -0.082(8) C11 0.078(9) 0.086(10) 0.052(7) 0.006(6) -0.009(6) -0.051(8) C11A 0.14(2) 0.14(2) 0.050(11) 0.018(12) -0.034(12) -0.11(2) C12 0.086(8) 0.173(15) 0.114(10) 0.022(10) 0.027(7) -0.054(9) _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 Er1 O1 2.332(3) . ? Er1 O4 2.333(3) . ? Er1 O3 2.354(3) . ? Er1 O2 2.362(3) . ? Er1 Cl2 2.5910(11) . ? Er1 Cl1 2.6069(12) . ? Er1 Cl3 2.6572(9) . ? N1 C1 1.325(5) . ? N1 C3 1.379(5) . ? N1 C4 1.478(5) . ? N2 C1 1.333(5) . ? N2 C2 1.374(5) . ? N2 C6 1.462(6) . ? N3 C7 1.323(11) . ? N3 C9 1.373(9) . ? N3 C10 1.459(12) . ? N4 C7 1.287(12) . ? N4 C8 1.378(9) . ? N4 C12 1.464(14) . ? C2 C3 1.363(7) . ? C4 C5 1.501(7) . ? C8 C9 1.332(12) . ? C10 C11 1.293(18) . ? C11A C12 1.32(3) . ? 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 Er1 O4 146.38(12) . . ? O1 Er1 O3 141.77(14) . . ? O4 Er1 O3 71.15(13) . . ? O1 Er1 O2 70.75(12) . . ? O4 Er1 O2 142.46(12) . . ? O3 Er1 O2 71.33(13) . . ? O1 Er1 Cl2 94.75(9) . . ? O4 Er1 Cl2 93.88(10) . . ? O3 Er1 Cl2 86.61(12) . . ? O2 Er1 Cl2 85.01(9) . . ? O1 Er1 Cl1 87.12(10) . . ? O4 Er1 Cl1 87.65(10) . . ? O3 Er1 Cl1 88.38(12) . . ? O2 Er1 Cl1 90.22(9) . . ? Cl2 Er1 Cl1 173.97(4) . . ? O1 Er1 Cl3 74.22(9) . . ? O4 Er1 Cl3 73.43(9) . . ? O3 Er1 Cl3 144.00(10) . . ? O2 Er1 Cl3 143.91(8) . . ? Cl2 Er1 Cl3 89.54(4) . . ? Cl1 Er1 Cl3 96.48(4) . . ? C1 N1 C3 109.1(4) . . ? C1 N1 C4 124.0(3) . . ? C3 N1 C4 126.8(4) . . ? C1 N2 C2 108.6(4) . . ? C1 N2 C6 124.8(4) . . ? C2 N2 C6 126.6(4) . . ? C7 N3 C9 107.1(7) . . ? C7 N3 C10 125.2(7) . . ? C9 N3 C10 127.7(8) . . ? C7 N4 C8 107.7(7) . . ? C7 N4 C12 125.1(8) . . ? C8 N4 C12 126.8(10) . . ? N1 C1 N2 108.7(3) . . ? C3 C2 N2 107.2(4) . . ? C2 C3 N1 106.4(4) . . ? N1 C4 C5 110.7(4) . . ? N4 C7 N3 110.7(6) . . ? C9 C8 N4 107.4(7) . . ? C8 C9 N3 107.0(6) . . ? C11 C10 N3 107.6(10) . . ? C11A C12 N4 97.8(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C4 C5 -87.0(5) . . . . ? C7 N3 C10 C11 -110.1(11) . . . . ? C7 N4 C12 C11A -92.6(14) . . . . ? 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 O1 H2O1 Cl5 0.77(8) 2.33(8) 3.093(4) 170(7) . O2 H1O2 Cl4 0.76(6) 2.33(6) 3.079(3) 175(5) . O3 H1O3 Cl4 0.71(6) 2.36(6) 3.072(4) 172(5) . O3 H2O3 Cl5 0.65(7) 2.44(7) 3.081(4) 173(8) 1_455 O2 H2O2 Cl5 0.71(6) 2.40(6) 3.105(3) 171(6) . O4 H1O4 Cl5 0.84(6) 2.24(6) 3.078(4) 171(5) 1_455 O4 H2O4 Cl4 0.81(7) 2.56(7) 3.227(3) 141(6) 1_465 C7 H7A Cl3 0.95 2.56 3.496(7) 166.8 . O1 H1O1 Cl4 0.71(6) 2.58(6) 3.204(3) 149(5) 1_565 C11A H11E Cl1 0.98 2.75 3.64(2) 151.2 . _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.694 _refine_diff_density_min -2.564 _refine_diff_density_rms 0.152 # Attachment 'Form_II.cif' data_c3 _database_code_depnum_ccdc_archive 'CCDC 656212' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Form II' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H30 Cl5 Er N4 O4' _chemical_formula_weight 638.91 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5226(5) _cell_length_b 8.6848(5) _cell_length_c 18.5977(11) _cell_angle_alpha 76.7750(10) _cell_angle_beta 87.9760(10) _cell_angle_gamma 61.2210(10) _cell_volume 1170.00(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7108 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 28.27 _exptl_crystal_description hex.plate _exptl_crystal_colour pink _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.814 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 630 _exptl_absorpt_coefficient_mu 4.180 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details '(SADABS; Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8053 _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 28.27 _reflns_number_total 5326 _reflns_number_gt 5112 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details '0.0387, 2.0951' _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 5326 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0265 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0661 _refine_ls_wR_factor_gt 0.0654 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 Er1 Er 0.182128(16) 0.087836(16) 0.249438(7) 0.01761(5) Uani 1 1 d . . . Cl1 Cl 0.17019(12) 0.15542(12) 0.10379(4) 0.03045(17) Uani 1 1 d . . . Cl2 Cl 0.16013(13) 0.09208(14) 0.38896(5) 0.03640(19) Uani 1 1 d . . . Cl3 Cl 0.35773(12) -0.26983(11) 0.27919(6) 0.0366(2) Uani 1 1 d . . . Cl4 Cl -0.10807(10) 0.66901(10) 0.28120(4) 0.02379(15) Uani 1 1 d . . . N1 N 0.5812(6) -0.3034(6) 0.5424(2) 0.0530(10) Uani 1 1 d . . . N2 N 0.8076(4) -0.5480(4) 0.52689(17) 0.0316(6) Uani 1 1 d . . . N3 N 0.0283(4) 0.2207(4) -0.08810(15) 0.0249(5) Uani 1 1 d . . . N4 N 0.2804(4) 0.2223(4) -0.09109(15) 0.0253(5) Uani 1 1 d . . . O4 O -0.0354(4) 0.0018(3) 0.24552(15) 0.0282(5) Uani 1 1 d . . . H1O4 H -0.009(7) -0.113(8) 0.253(3) 0.047(14) Uiso 1 1 d . . . H2O4 H -0.138(11) 0.065(11) 0.235(4) 0.10(3) Uiso 1 1 d . . . O3 O -0.1056(3) 0.3497(3) 0.23272(15) 0.0264(5) Uani 1 1 d . . . H1O3 H -0.119(5) 0.437(6) 0.245(2) 0.021(9) Uiso 1 1 d . . . H2O3 H -0.194(7) 0.350(7) 0.230(3) 0.041(14) Uiso 1 1 d . . . O2 O 0.2158(4) 0.3481(3) 0.23680(16) 0.0300(5) Uani 1 1 d . . . H1O2 H 0.303(6) 0.351(6) 0.229(2) 0.027(11) Uiso 1 1 d . . . H2O2 H 0.143(7) 0.435(7) 0.248(2) 0.031(11) Uiso 1 1 d . . . O1 O 0.4869(4) 0.0020(4) 0.25523(17) 0.0318(6) Uani 1 1 d . . . H1O1 H 0.562(7) -0.086(7) 0.261(3) 0.033(13) Uiso 1 1 d . . . H2O1 H 0.519(7) 0.067(7) 0.235(3) 0.035(12) Uiso 1 1 d . . . C1 C 0.7244(6) -0.4559(6) 0.5765(2) 0.0470(11) Uani 1 1 d . . . H1A H 0.7610 -0.4926 0.6280 0.056 Uiso 1 1 calc R . . C2 C 0.7085(7) -0.4545(6) 0.4594(2) 0.0442(10) Uani 1 1 d . . . H2A H 0.7377 -0.4890 0.4138 0.053 Uiso 1 1 calc R . . C3 C 0.5635(7) -0.3059(6) 0.4699(2) 0.0497(11) Uani 1 1 d . . . H3A H 0.4670 -0.2190 0.4340 0.060 Uiso 1 1 calc R . . C4 C 0.4536(8) -0.1521(8) 0.5778(4) 0.0633(14) Uani 1 1 d . . . H4A H 0.5195 -0.1416 0.6175 0.076 Uiso 1 1 calc R . . H4B H 0.3966 -0.0352 0.5402 0.076 Uiso 1 1 calc R . . C5 C 0.3195(9) -0.1985(9) 0.6080(3) 0.0704(16) Uani 1 1 d . . . H5A H 0.2399 -0.1093 0.6350 0.106 Uiso 1 1 calc R . . H5B H 0.3785 -0.3190 0.6420 0.106 Uiso 1 1 calc R . . H5C H 0.2488 -0.1987 0.5676 0.106 Uiso 1 1 calc R . . C6 C 0.9725(6) -0.7223(6) 0.5432(3) 0.0466(10) Uani 1 1 d . . . H6A H 1.0447 -0.7297 0.5850 0.070 Uiso 1 1 calc R . . H6B H 1.0413 -0.7341 0.4995 0.070 Uiso 1 1 calc R . . H6C H 0.9421 -0.8201 0.5560 0.070 Uiso 1 1 calc R . . C7 C 0.1040(5) 0.3234(4) -0.09011(17) 0.0248(6) Uani 1 1 d . . . H7A H 0.0425 0.4486 -0.0908 0.030 Uiso 1 1 calc R . . C8 C 0.3177(5) 0.0494(5) -0.09085(19) 0.0285(7) Uani 1 1 d . . . H8A H 0.4328 -0.0504 -0.0920 0.034 Uiso 1 1 calc R . . C9 C 0.1594(5) 0.0482(5) -0.08860(18) 0.0282(7) Uani 1 1 d . . . H9A H 0.1423 -0.0526 -0.0876 0.034 Uiso 1 1 calc R . . C10 C -0.1653(5) 0.2806(5) -0.0864(2) 0.0349(8) Uani 1 1 d . . . H10A H -0.1834 0.1744 -0.0681 0.042 Uiso 1 1 calc R . . H10B H -0.2259 0.3423 -0.1371 0.042 Uiso 1 1 calc R . . C11 C -0.2463(6) 0.4103(7) -0.0354(3) 0.0514(11) Uani 1 1 d . . . H11A H -0.3715 0.4388 -0.0296 0.077 Uiso 1 1 calc R . . H11B H -0.2420 0.5221 -0.0572 0.077 Uiso 1 1 calc R . . H11C H -0.1774 0.3532 0.0132 0.077 Uiso 1 1 calc R . . C12 C 0.4139(5) 0.2840(6) -0.0937(2) 0.0390(8) Uani 1 1 d . . . H12A H 0.3652 0.3933 -0.0749 0.059 Uiso 1 1 calc R . . H12B H 0.4421 0.3111 -0.1451 0.059 Uiso 1 1 calc R . . H12C H 0.5235 0.1887 -0.0630 0.059 Uiso 1 1 calc R . . Cl5 Cl 0.58105(10) 0.29971(10) 0.18372(5) 0.02864(17) 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 Er1 0.01804(8) 0.01514(7) 0.01772(8) -0.00309(5) 0.00095(5) -0.00692(6) Cl1 0.0388(4) 0.0295(4) 0.0188(3) -0.0042(3) 0.0022(3) -0.0139(4) Cl2 0.0383(5) 0.0476(5) 0.0208(4) -0.0096(3) 0.0033(3) -0.0184(4) Cl3 0.0312(4) 0.0164(3) 0.0543(6) -0.0035(3) -0.0018(4) -0.0073(3) Cl4 0.0231(3) 0.0178(3) 0.0297(4) -0.0079(3) 0.0040(3) -0.0085(3) N1 0.048(2) 0.051(2) 0.038(2) -0.0162(17) -0.0001(16) -0.0046(18) N2 0.0401(17) 0.0300(15) 0.0264(14) -0.0077(12) 0.0089(12) -0.0184(14) N3 0.0300(14) 0.0250(13) 0.0192(12) -0.0031(10) 0.0036(10) -0.0142(12) N4 0.0305(14) 0.0243(13) 0.0197(13) -0.0042(10) 0.0016(10) -0.0128(12) O4 0.0246(12) 0.0178(11) 0.0407(14) -0.0029(10) -0.0021(10) -0.0105(10) O3 0.0218(12) 0.0204(11) 0.0398(14) -0.0112(10) -0.0003(10) -0.0105(10) O2 0.0202(12) 0.0208(12) 0.0519(16) -0.0143(11) 0.0118(11) -0.0104(10) O1 0.0192(12) 0.0163(12) 0.0510(16) -0.0022(11) 0.0052(11) -0.0045(11) C1 0.044(2) 0.049(2) 0.0246(18) -0.0100(17) 0.0040(16) -0.005(2) C2 0.073(3) 0.043(2) 0.0234(18) -0.0087(16) 0.0068(18) -0.033(2) C3 0.065(3) 0.034(2) 0.035(2) -0.0048(17) -0.015(2) -0.014(2) C4 0.056(3) 0.065(3) 0.076(4) -0.016(3) -0.004(3) -0.035(3) C5 0.083(4) 0.075(4) 0.058(3) -0.003(3) -0.001(3) -0.047(4) C6 0.039(2) 0.038(2) 0.057(3) -0.023(2) 0.0071(19) -0.0099(18) C7 0.0316(17) 0.0230(15) 0.0187(14) -0.0041(12) 0.0033(12) -0.0129(14) C8 0.0332(18) 0.0226(15) 0.0226(15) -0.0051(12) 0.0039(13) -0.0084(14) C9 0.0406(19) 0.0224(15) 0.0212(15) -0.0039(12) 0.0032(13) -0.0156(15) C10 0.0294(18) 0.038(2) 0.038(2) -0.0040(16) 0.0048(14) -0.0190(16) C11 0.039(2) 0.056(3) 0.059(3) -0.014(2) 0.009(2) -0.023(2) C12 0.033(2) 0.040(2) 0.045(2) -0.0069(17) 0.0000(16) -0.0205(18) Cl5 0.0197(3) 0.0208(3) 0.0446(5) -0.0059(3) 0.0006(3) -0.0100(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Er1 O4 2.317(2) . ? Er1 O1 2.331(3) . ? Er1 O2 2.372(2) . ? Er1 O3 2.375(2) . ? Er1 Cl2 2.6023(9) . ? Er1 Cl1 2.6318(8) . ? Er1 Cl3 2.6440(8) . ? N1 C1 1.326(6) . ? N1 C3 1.368(6) . ? N1 C4 1.520(7) . ? N2 C1 1.319(5) . ? N2 C2 1.377(5) . ? N2 C6 1.459(5) . ? N3 C7 1.324(4) . ? N3 C9 1.374(4) . ? N3 C10 1.473(5) . ? N4 C7 1.329(4) . ? N4 C8 1.376(4) . ? N4 C12 1.468(5) . ? C2 C3 1.340(7) . ? C4 C5 1.442(8) . ? C8 C9 1.353(5) . ? C10 C11 1.530(6) . ? 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 Er1 O1 147.51(10) . . ? O4 Er1 O2 141.62(9) . . ? O1 Er1 O2 70.62(10) . . ? O4 Er1 O3 71.31(9) . . ? O1 Er1 O3 141.00(9) . . ? O2 Er1 O3 70.40(9) . . ? O4 Er1 Cl2 94.26(7) . . ? O1 Er1 Cl2 93.08(8) . . ? O2 Er1 Cl2 84.53(7) . . ? O3 Er1 Cl2 84.31(7) . . ? O4 Er1 Cl1 89.14(7) . . ? O1 Er1 Cl1 89.96(8) . . ? O2 Er1 Cl1 85.91(7) . . ? O3 Er1 Cl1 86.27(7) . . ? Cl2 Er1 Cl1 168.37(3) . . ? O4 Er1 Cl3 74.31(7) . . ? O1 Er1 Cl3 73.74(7) . . ? O2 Er1 Cl3 144.06(7) . . ? O3 Er1 Cl3 145.18(6) . . ? Cl2 Er1 Cl3 92.99(3) . . ? Cl1 Er1 Cl3 98.64(3) . . ? C1 N1 C3 108.7(4) . . ? C1 N1 C4 126.2(4) . . ? C3 N1 C4 125.1(4) . . ? C1 N2 C2 108.2(4) . . ? C1 N2 C6 124.7(4) . . ? C2 N2 C6 127.1(3) . . ? C7 N3 C9 109.0(3) . . ? C7 N3 C10 125.9(3) . . ? C9 N3 C10 125.1(3) . . ? C7 N4 C8 108.5(3) . . ? C7 N4 C12 126.2(3) . . ? C8 N4 C12 125.3(3) . . ? N2 C1 N1 108.6(4) . . ? C3 C2 N2 107.4(4) . . ? C2 C3 N1 106.7(4) . . ? C5 C4 N1 106.8(5) . . ? N3 C7 N4 108.6(3) . . ? C9 C8 N4 107.1(3) . . ? C8 C9 N3 106.8(3) . . ? N3 C10 C11 109.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C4 C5 -86.8(7) . . . . ? C7 N3 C10 C11 -40.2(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 C3 H3A Cl2 0.95 2.68 3.546(5) 152.7 . O2 H2O2 Cl4 0.77(5) 2.33(5) 3.091(3) 170(4) . O1 H2O1 Cl5 0.76(5) 2.32(5) 3.073(3) 171(5) . O3 H1O3 Cl4 0.80(4) 2.31(4) 3.097(3) 171(4) . O2 H1O2 Cl5 0.76(5) 2.36(5) 3.091(3) 162(4) . O4 H1O4 Cl4 0.89(6) 2.37(5) 3.161(2) 148(5) 1_545 O3 H2O3 Cl5 0.76(5) 2.38(5) 3.102(3) 158(5) 1_455 O1 H1O1 Cl4 0.71(5) 2.55(5) 3.222(3) 158(5) 1_645 O4 H2O4 Cl5 0.78(8) 2.32(8) 3.076(3) 165(8) 1_455 _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.862 _refine_diff_density_min -1.953 _refine_diff_density_rms 0.116