Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Dr Jonathan Steed' _publ_contact_author_address ; Department of Chemistry University of Durham University Science Laboratories South Road Durham DH1 3LE ; _publ_contact_author_email JON.STEED@DUR.AC.UK _publ_section_title ; Anion and Cation Binding by A Pendant Arm Cyclam and its Macrobicyclic Derivatives ; loop_ _publ_author_name 'Jonathan Steed' 'A. Channa' data_ac49o _database_code_depnum_ccdc_archive 'CCDC 267665' _audit_creation_method SHELXL-97 _chemical_name_systematic '[nickel(II)tetrahydroxypropylcyclam][nitrate]' _chemical_name_common (nickel(ii)tetrahydroxypropylcyclam)(nitrate) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H48 N6 Ni O10' _chemical_formula_weight 615.37 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 15.4796(6) _cell_length_b 11.7954(6) _cell_length_c 15.1196(9) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 2760.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 22328 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 0.767 _exptl_absorpt_correction_type Scalepack _exptl_absorpt_correction_T_min 0.7003 _exptl_absorpt_correction_T_max 0.9342 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method '2 phi + omega scans 30 s/o' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16338 _diffrn_reflns_av_R_equivalents 0.1075 _diffrn_reflns_av_sigmaI/netI 0.1278 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6211 _reflns_number_gt 4793 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.0000P] 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 0.0043(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.016(13) _refine_ls_number_reflns 6211 _refine_ls_number_parameters 378 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.0852 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.02651(2) 0.77720(3) 0.44589(3) 0.01251(11) Uani 1 1 d . . . O1 O -0.04996(13) 0.66406(19) 0.38217(15) 0.0186(5) Uani 1 1 d . . . H1 H -0.0167 0.6116 0.3661 0.022 Uiso 1 1 calc R . . O2A O -0.2089(3) 0.4977(6) 0.6751(4) 0.0236(19) Uani 0.456(9) 1 d PU A 2 H2AC H -0.1807 0.4396 0.6612 0.028 Uiso 0.456(9) 1 calc PR A 2 O3 O 0.1732(2) 0.2383(3) 0.4964(3) 0.0613(11) Uani 1 1 d . . . O4 O 0.09281(17) 0.6585(2) 0.09718(17) 0.0299(6) Uani 1 1 d . . . H4 H 0.0929 0.6335 0.0452 0.036 Uiso 1 1 calc R . . O5 O 0.18026(18) 0.9565(2) 0.56118(18) 0.0360(7) Uani 1 1 d . . . O6 O 0.10204(14) 1.0867(2) 0.62440(17) 0.0303(6) Uani 1 1 d . . . O7 O 0.23333(16) 1.0585(2) 0.66607(18) 0.0374(7) Uani 1 1 d . . . O8 O -0.09572(17) 0.2836(2) 0.38280(18) 0.0306(6) Uani 1 1 d . . . O9 O -0.04243(18) 0.4241(2) 0.30860(16) 0.0342(7) Uani 1 1 d . . . O10 O -0.10287(13) 0.45522(19) 0.43592(18) 0.0230(5) Uani 1 1 d . . . N1 N -0.06930(16) 0.9055(2) 0.42630(16) 0.0132(6) Uani 1 1 d . . . N2 N -0.02097(16) 0.7689(2) 0.57887(18) 0.0147(6) Uani 1 1 d . . . N3 N 0.12650(16) 0.6545(2) 0.46700(16) 0.0151(6) Uani 1 1 d . . . N4 N 0.11212(16) 0.8440(2) 0.34803(17) 0.0142(6) Uani 1 1 d . . . N5 N 0.17221(18) 1.0332(3) 0.61780(19) 0.0220(7) Uani 1 1 d . . . N6 N -0.07982(18) 0.3860(2) 0.3750(2) 0.0199(6) Uani 1 1 d . . . C1 C -0.1202(2) 0.9064(3) 0.5105(2) 0.0176(8) Uani 1 1 d . . . H6 H -0.1661 0.8481 0.5076 0.021 Uiso 1 1 calc R . . H5 H -0.1482 0.9812 0.5181 0.021 Uiso 1 1 calc R . . C2 C -0.0623(2) 0.8829(3) 0.5882(2) 0.0166(7) Uani 1 1 d . . . H2A H -0.0171 0.9420 0.5918 0.020 Uiso 1 1 calc R . . H2B H -0.0966 0.8854 0.6435 0.020 Uiso 1 1 calc R . . C3 C 0.0497(2) 0.7612(3) 0.6465(2) 0.0189(8) Uani 1 1 d . . . H3A H 0.0228 0.7536 0.7056 0.023 Uiso 1 1 calc R . . H3B H 0.0822 0.8335 0.6460 0.023 Uiso 1 1 calc R . . C4 C 0.1132(2) 0.6652(3) 0.6344(2) 0.0208(8) Uani 1 1 d . . . H4A H 0.0807 0.5932 0.6296 0.025 Uiso 1 1 calc R . . H4B H 0.1502 0.6602 0.6877 0.025 Uiso 1 1 calc R . . C5 C 0.1711(2) 0.6778(3) 0.5530(2) 0.0180(8) Uani 1 1 d . . . H5A H 0.1944 0.7559 0.5517 0.022 Uiso 1 1 calc R . . H5B H 0.2206 0.6252 0.5589 0.022 Uiso 1 1 calc R . . C6 C 0.1913(2) 0.6730(3) 0.3948(2) 0.0173(7) Uani 1 1 d . . . H6A H 0.1735 0.6309 0.3412 0.021 Uiso 1 1 calc R . . H6B H 0.2484 0.6440 0.4138 0.021 Uiso 1 1 calc R . . C7 C 0.1980(2) 0.7983(3) 0.3739(2) 0.0175(7) Uani 1 1 d . . . H7A H 0.2196 0.8396 0.4264 0.021 Uiso 1 1 calc R . . H7B H 0.2396 0.8099 0.3250 0.021 Uiso 1 1 calc R . . C8 C 0.1197(2) 0.9707(3) 0.3482(2) 0.0180(7) Uani 1 1 d . . . H8A H 0.1579 0.9936 0.2988 0.022 Uiso 1 1 calc R . . H8B H 0.1479 0.9944 0.4040 0.022 Uiso 1 1 calc R . . C9 C 0.0343(2) 1.0344(3) 0.3394(2) 0.0191(7) Uani 1 1 d . . . H9A H 0.0468 1.1162 0.3318 0.023 Uiso 1 1 calc R . . H9B H 0.0045 1.0079 0.2853 0.023 Uiso 1 1 calc R . . C10 C -0.0262(2) 1.0198(3) 0.4177(2) 0.0179(7) Uani 1 1 d . . . H10A H 0.0070 1.0344 0.4726 0.021 Uiso 1 1 calc R . . H10B H -0.0718 1.0784 0.4138 0.021 Uiso 1 1 calc R . . C11 C -0.1312(2) 0.8940(3) 0.3507(2) 0.0176(8) Uani 1 1 d . . . H11A H -0.0999 0.9111 0.2952 0.021 Uiso 1 1 calc R . . H11B H -0.1770 0.9520 0.3577 0.021 Uiso 1 1 calc R . . C12 C -0.1742(2) 0.7785(3) 0.3411(2) 0.0190(7) Uani 1 1 d . . . H12A H -0.2008 0.7576 0.3984 0.023 Uiso 1 1 calc R . . H12B H -0.2212 0.7846 0.2969 0.023 Uiso 1 1 calc R . . C13 C -0.1137(2) 0.6852(3) 0.3132(2) 0.0204(8) Uani 1 1 d . . . H13A H -0.1470 0.6151 0.3018 0.025 Uiso 1 1 calc R . . H13B H -0.0840 0.7070 0.2578 0.025 Uiso 1 1 calc R . . C14 C -0.0853(2) 0.6757(3) 0.5930(2) 0.0177(8) Uani 1 1 d . A . H14A H -0.0537 0.6028 0.5951 0.021 Uiso 1 1 calc R . . H14B H -0.1241 0.6730 0.5409 0.021 Uiso 1 1 calc R . . C15 C -0.1412(2) 0.6846(3) 0.6762(3) 0.0243(9) Uani 1 1 d . . . H15A H -0.1049 0.7048 0.7277 0.029 Uiso 1 1 calc R A 1 H15B H -0.1855 0.7443 0.6684 0.029 Uiso 1 1 calc R A 1 C17 C 0.09458(19) 0.5356(3) 0.4625(2) 0.0179(8) Uani 1 1 d . . . H17A H 0.0743 0.5213 0.4015 0.022 Uiso 1 1 calc R . . H17B H 0.0438 0.5292 0.5020 0.022 Uiso 1 1 calc R . . C18 C 0.1586(2) 0.4411(3) 0.4874(3) 0.0239(8) Uani 1 1 d . . . H18A H 0.2124 0.4498 0.4527 0.029 Uiso 1 1 calc R . . H18B H 0.1734 0.4468 0.5510 0.029 Uiso 1 1 calc R . . C19 C 0.1185(2) 0.3263(3) 0.4686(3) 0.0403(13) Uani 1 1 d . . . H19A H 0.0624 0.3203 0.4997 0.048 Uiso 1 1 calc R . . H19B H 0.1075 0.3190 0.4043 0.048 Uiso 1 1 calc R . . C20 C 0.0843(2) 0.7996(3) 0.2586(2) 0.0149(8) Uani 1 1 d . . . H20A H 0.0294 0.8373 0.2424 0.018 Uiso 1 1 calc R . . H20B H 0.0720 0.7176 0.2647 0.018 Uiso 1 1 calc R . . C21 C 0.1474(2) 0.8151(3) 0.1828(2) 0.0201(8) Uani 1 1 d . . . H21A H 0.2002 0.7701 0.1944 0.024 Uiso 1 1 calc R . . H21B H 0.1643 0.8959 0.1787 0.024 Uiso 1 1 calc R . . C22 C 0.1076(2) 0.7777(3) 0.0959(2) 0.0219(8) Uani 1 1 d . . . H22A H 0.0523 0.8181 0.0864 0.026 Uiso 1 1 calc R . . H22B H 0.1470 0.7970 0.0465 0.026 Uiso 1 1 calc R . . O2 O -0.1265(4) 0.4903(5) 0.7254(3) 0.0344(18) Uani 0.544(9) 1 d PU A 1 H2 H -0.0796 0.5221 0.7381 0.041 Uiso 0.544(9) 1 calc PR A 1 C16 C -0.1843(6) 0.5707(10) 0.6914(7) 0.032(3) Uani 0.544(9) 1 d PU A 1 H16A H -0.2329 0.5804 0.7333 0.039 Uiso 0.544(9) 1 calc PR A 1 H16B H -0.2082 0.5427 0.6348 0.039 Uiso 0.544(9) 1 calc PR A 1 C16A C -0.1566(6) 0.5701(11) 0.7271(6) 0.019(3) Uani 0.456(9) 1 d PU A 2 H16C H -0.1005 0.5329 0.7393 0.022 Uiso 0.456(9) 1 calc PR A 2 H16D H -0.1854 0.5855 0.7843 0.022 Uiso 0.456(9) 1 calc PR A 2 H3AC H 0.145(2) 0.197(3) 0.537(2) 0.022 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01468(18) 0.01264(19) 0.01020(18) 0.0000(2) 0.0002(2) 0.00105(16) O1 0.0181(11) 0.0179(12) 0.0198(13) -0.0023(11) -0.0074(10) 0.0057(10) O2A 0.023(3) 0.020(4) 0.027(3) -0.009(3) 0.003(2) -0.008(2) O3 0.047(2) 0.0365(19) 0.101(3) 0.0368(19) 0.036(2) 0.0193(15) O4 0.0479(16) 0.0233(15) 0.0186(14) -0.0031(11) -0.0018(12) 0.0000(12) O5 0.0550(19) 0.0279(15) 0.0252(16) -0.0125(13) 0.0044(13) -0.0028(13) O6 0.0220(13) 0.0382(17) 0.0306(15) 0.0021(13) -0.0012(11) 0.0087(12) O7 0.0253(15) 0.0480(18) 0.0388(18) -0.0163(14) -0.0041(13) 0.0040(13) O8 0.0403(16) 0.0135(14) 0.0381(17) -0.0005(12) 0.0019(13) -0.0008(12) O9 0.0476(16) 0.0355(16) 0.0196(14) 0.0002(13) 0.0092(12) -0.0137(13) O10 0.0262(11) 0.0210(12) 0.0217(14) -0.0016(13) 0.0007(12) 0.0028(9) N1 0.0190(13) 0.0130(13) 0.0077(15) -0.0013(11) 0.0020(10) 0.0023(11) N2 0.0187(14) 0.0124(14) 0.0131(13) -0.0003(12) 0.0002(11) 0.0004(12) N3 0.0161(13) 0.0170(15) 0.0120(17) 0.0006(11) 0.0011(10) -0.0001(11) N4 0.0134(13) 0.0148(15) 0.0145(14) -0.0038(12) 0.0002(11) 0.0006(12) N5 0.0309(17) 0.0183(16) 0.0169(17) 0.0022(13) 0.0038(14) -0.0008(13) N6 0.0217(14) 0.0153(16) 0.0227(17) 0.0000(13) -0.0019(13) -0.0032(13) C1 0.0198(17) 0.0182(19) 0.0148(18) 0.0004(15) 0.0055(14) 0.0015(15) C2 0.0238(17) 0.0113(16) 0.0148(18) -0.0009(14) 0.0032(14) -0.0024(14) C3 0.0215(18) 0.024(2) 0.0109(18) 0.0032(15) -0.0047(14) 0.0010(15) C4 0.0246(17) 0.024(2) 0.0141(18) 0.0026(15) -0.0032(15) 0.0031(16) C5 0.0164(17) 0.024(2) 0.0136(18) -0.0009(15) -0.0031(14) 0.0036(14) C6 0.0153(16) 0.0208(19) 0.0158(19) -0.0023(15) 0.0039(14) 0.0054(14) C7 0.0164(16) 0.0225(19) 0.0134(17) -0.0017(15) -0.0005(14) -0.0035(14) C8 0.0225(17) 0.0153(18) 0.0161(17) -0.0005(14) 0.0052(14) -0.0060(15) C9 0.0247(18) 0.0151(17) 0.0176(18) -0.0001(14) -0.0009(15) 0.0034(14) C10 0.0242(17) 0.0116(16) 0.0179(18) 0.0013(12) 0.0032(14) 0.0018(14) C11 0.0165(17) 0.0210(19) 0.0152(18) 0.0029(15) -0.0036(14) 0.0086(15) C12 0.0177(16) 0.0216(19) 0.0177(18) 0.0018(16) -0.0042(13) -0.0013(15) C13 0.0174(18) 0.023(2) 0.0207(19) -0.0004(16) -0.0035(16) -0.0004(15) C14 0.0201(18) 0.0129(17) 0.0201(19) 0.0016(15) 0.0025(15) -0.0017(14) C15 0.029(2) 0.0139(19) 0.030(2) 0.0023(16) 0.0120(16) 0.0016(15) C17 0.0133(14) 0.0146(17) 0.026(2) 0.0014(15) -0.0016(14) 0.0016(13) C18 0.0231(18) 0.022(2) 0.027(2) 0.0006(16) 0.0003(16) 0.0072(16) C19 0.0269(19) 0.0159(19) 0.078(4) 0.008(2) 0.014(2) 0.0086(16) C20 0.0196(18) 0.0158(19) 0.0093(17) 0.0007(14) -0.0001(14) 0.0008(14) C21 0.0225(18) 0.023(2) 0.0152(19) -0.0010(15) 0.0022(14) 0.0003(15) C22 0.0291(18) 0.0222(19) 0.0144(18) 0.0028(16) 0.0007(15) 0.0035(16) O2 0.049(3) 0.031(4) 0.023(3) 0.006(2) 0.002(2) 0.005(3) C16 0.028(5) 0.035(6) 0.034(5) 0.006(5) 0.018(4) 0.005(4) C16A 0.018(5) 0.028(6) 0.010(4) 0.004(4) -0.008(3) -0.005(4) _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 Ni1 O1 2.027(2) . ? Ni1 N4 2.137(3) . ? Ni1 N1 2.140(2) . ? Ni1 N2 2.143(3) . ? Ni1 N3 2.143(3) . ? O1 C13 1.457(4) . ? O2A C16A 1.414(12) . ? O3 C19 1.404(5) . ? O4 C22 1.425(4) . ? O5 N5 1.252(4) . ? O6 N5 1.260(4) . ? O7 N5 1.231(3) . ? O8 N6 1.238(3) . ? O9 N6 1.243(4) . ? O10 N6 1.281(4) . ? N1 C1 1.498(4) . ? N1 C11 1.498(4) . ? N1 C10 1.510(4) . ? N2 C2 1.496(4) . ? N2 C14 1.499(4) . ? N2 C3 1.500(4) . ? N3 C17 1.489(4) . ? N3 C5 1.497(4) . ? N3 C6 1.498(4) . ? N4 C7 1.487(4) . ? N4 C8 1.498(4) . ? N4 C20 1.512(4) . ? C1 C2 1.503(5) . ? C3 C4 1.511(5) . ? C4 C5 1.530(5) . ? C6 C7 1.514(5) . ? C8 C9 1.527(5) . ? C9 C10 1.520(4) . ? C11 C12 1.523(5) . ? C12 C13 1.506(5) . ? C14 C15 1.530(5) . ? C15 C16 1.518(12) . ? C15 C16A 1.573(12) . ? C17 C18 1.538(4) . ? C18 C19 1.516(5) . ? C20 C21 1.518(5) . ? C21 C22 1.517(5) . ? O2 C16 1.401(11) . ? 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 Ni1 N4 106.01(10) . . ? O1 Ni1 N1 89.72(9) . . ? N4 Ni1 N1 94.19(10) . . ? O1 Ni1 N2 102.45(10) . . ? N4 Ni1 N2 151.54(10) . . ? N1 Ni1 N2 85.66(10) . . ? O1 Ni1 N3 92.75(9) . . ? N4 Ni1 N3 84.51(10) . . ? N1 Ni1 N3 177.45(10) . . ? N2 Ni1 N3 94.43(10) . . ? C13 O1 Ni1 128.5(2) . . ? C1 N1 C11 108.2(2) . . ? C1 N1 C10 107.4(2) . . ? C11 N1 C10 107.4(2) . . ? C1 N1 Ni1 104.59(18) . . ? C11 N1 Ni1 119.04(19) . . ? C10 N1 Ni1 109.70(18) . . ? C2 N2 C14 111.2(2) . . ? C2 N2 C3 107.6(2) . . ? C14 N2 C3 110.1(3) . . ? C2 N2 Ni1 101.21(19) . . ? C14 N2 Ni1 113.3(2) . . ? C3 N2 Ni1 113.09(19) . . ? C17 N3 C5 111.4(3) . . ? C17 N3 C6 109.0(2) . . ? C5 N3 C6 107.3(2) . . ? C17 N3 Ni1 112.94(17) . . ? C5 N3 Ni1 109.80(19) . . ? C6 N3 Ni1 106.08(18) . . ? C7 N4 C8 106.9(2) . . ? C7 N4 C20 111.4(2) . . ? C8 N4 C20 111.7(3) . . ? C7 N4 Ni1 103.79(19) . . ? C8 N4 Ni1 114.53(18) . . ? C20 N4 Ni1 108.31(18) . . ? O7 N5 O5 120.2(3) . . ? O7 N5 O6 119.6(3) . . ? O5 N5 O6 120.1(3) . . ? O8 N6 O9 121.4(3) . . ? O8 N6 O10 119.9(3) . . ? O9 N6 O10 118.7(3) . . ? N1 C1 C2 110.5(3) . . ? N2 C2 C1 110.3(3) . . ? N2 C3 C4 115.9(3) . . ? C3 C4 C5 113.9(3) . . ? N3 C5 C4 114.3(3) . . ? N3 C6 C7 109.9(2) . . ? N4 C7 C6 110.4(3) . . ? N4 C8 C9 115.0(3) . . ? C10 C9 C8 114.2(3) . . ? N1 C10 C9 116.1(3) . . ? N1 C11 C12 115.7(3) . . ? C13 C12 C11 114.1(3) . . ? O1 C13 C12 110.2(3) . . ? N2 C14 C15 116.2(3) . . ? C16 C15 C14 108.2(4) . . ? C16 C15 C16A 25.7(4) . . ? C14 C15 C16A 115.4(5) . . ? N3 C17 C18 117.3(3) . . ? C19 C18 C17 109.7(3) . . ? O3 C19 C18 110.9(3) . . ? N4 C20 C21 116.7(3) . . ? C20 C21 C22 111.0(3) . . ? O4 C22 C21 109.9(3) . . ? O2 C16 C15 112.0(8) . . ? O2A C16A C15 109.5(7) . . ? 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 N4 Ni1 O1 C13 -65.6(3) . . . . ? N1 Ni1 O1 C13 28.7(3) . . . . ? N2 Ni1 O1 C13 114.2(3) . . . . ? N3 Ni1 O1 C13 -150.7(3) . . . . ? O1 Ni1 N1 C1 96.10(19) . . . . ? N4 Ni1 N1 C1 -157.86(19) . . . . ? N2 Ni1 N1 C1 -6.40(19) . . . . ? N3 Ni1 N1 C1 -99(2) . . . . ? O1 Ni1 N1 C11 -24.8(2) . . . . ? N4 Ni1 N1 C11 81.2(2) . . . . ? N2 Ni1 N1 C11 -127.3(2) . . . . ? N3 Ni1 N1 C11 141(2) . . . . ? O1 Ni1 N1 C10 -148.98(18) . . . . ? N4 Ni1 N1 C10 -42.94(19) . . . . ? N2 Ni1 N1 C10 108.52(19) . . . . ? N3 Ni1 N1 C10 16(2) . . . . ? O1 Ni1 N2 C2 -111.10(18) . . . . ? N4 Ni1 N2 C2 68.5(3) . . . . ? N1 Ni1 N2 C2 -22.35(18) . . . . ? N3 Ni1 N2 C2 155.09(18) . . . . ? O1 Ni1 N2 C14 8.0(2) . . . . ? N4 Ni1 N2 C14 -172.4(2) . . . . ? N1 Ni1 N2 C14 96.8(2) . . . . ? N3 Ni1 N2 C14 -85.8(2) . . . . ? O1 Ni1 N2 C3 134.1(2) . . . . ? N4 Ni1 N2 C3 -46.3(3) . . . . ? N1 Ni1 N2 C3 -137.1(2) . . . . ? N3 Ni1 N2 C3 40.3(2) . . . . ? O1 Ni1 N3 C17 -21.8(2) . . . . ? N4 Ni1 N3 C17 -127.6(2) . . . . ? N1 Ni1 N3 C17 173(2) . . . . ? N2 Ni1 N3 C17 81.0(2) . . . . ? O1 Ni1 N3 C5 -146.7(2) . . . . ? N4 Ni1 N3 C5 107.4(2) . . . . ? N1 Ni1 N3 C5 48(2) . . . . ? N2 Ni1 N3 C5 -44.0(2) . . . . ? O1 Ni1 N3 C6 97.63(19) . . . . ? N4 Ni1 N3 C6 -8.20(19) . . . . ? N1 Ni1 N3 C6 -68(2) . . . . ? N2 Ni1 N3 C6 -159.65(19) . . . . ? O1 Ni1 N4 C7 -111.51(19) . . . . ? N1 Ni1 N4 C7 157.58(19) . . . . ? N2 Ni1 N4 C7 68.9(3) . . . . ? N3 Ni1 N4 C7 -20.21(19) . . . . ? O1 Ni1 N4 C8 132.3(2) . . . . ? N1 Ni1 N4 C8 41.4(2) . . . . ? N2 Ni1 N4 C8 -47.3(3) . . . . ? N3 Ni1 N4 C8 -136.4(2) . . . . ? O1 Ni1 N4 C20 6.9(2) . . . . ? N1 Ni1 N4 C20 -84.0(2) . . . . ? N2 Ni1 N4 C20 -172.6(2) . . . . ? N3 Ni1 N4 C20 98.2(2) . . . . ? C11 N1 C1 C2 163.2(3) . . . . ? C10 N1 C1 C2 -81.2(3) . . . . ? Ni1 N1 C1 C2 35.3(3) . . . . ? C14 N2 C2 C1 -71.7(3) . . . . ? C3 N2 C2 C1 167.7(3) . . . . ? Ni1 N2 C2 C1 48.9(3) . . . . ? N1 C1 C2 N2 -60.5(3) . . . . ? C2 N2 C3 C4 -166.0(3) . . . . ? C14 N2 C3 C4 72.7(4) . . . . ? Ni1 N2 C3 C4 -55.1(3) . . . . ? N2 C3 C4 C5 68.3(4) . . . . ? C17 N3 C5 C4 -61.9(4) . . . . ? C6 N3 C5 C4 178.8(3) . . . . ? Ni1 N3 C5 C4 63.9(3) . . . . ? C3 C4 C5 N3 -74.4(4) . . . . ? C17 N3 C6 C7 157.5(2) . . . . ? C5 N3 C6 C7 -81.7(3) . . . . ? Ni1 N3 C6 C7 35.6(3) . . . . ? C8 N4 C7 C6 167.7(3) . . . . ? C20 N4 C7 C6 -70.1(3) . . . . ? Ni1 N4 C7 C6 46.2(3) . . . . ? N3 C6 C7 N4 -57.6(3) . . . . ? C7 N4 C8 C9 -169.6(3) . . . . ? C20 N4 C8 C9 68.4(3) . . . . ? Ni1 N4 C8 C9 -55.2(3) . . . . ? N4 C8 C9 C10 66.2(4) . . . . ? C1 N1 C10 C9 175.8(3) . . . . ? C11 N1 C10 C9 -68.0(3) . . . . ? Ni1 N1 C10 C9 62.7(3) . . . . ? C8 C9 C10 N1 -72.6(4) . . . . ? C1 N1 C11 C12 -71.1(3) . . . . ? C10 N1 C11 C12 173.3(3) . . . . ? Ni1 N1 C11 C12 48.0(3) . . . . ? N1 C11 C12 C13 -68.9(4) . . . . ? Ni1 O1 C13 C12 -50.5(4) . . . . ? C11 C12 C13 O1 65.6(4) . . . . ? C2 N2 C14 C15 -49.7(4) . . . . ? C3 N2 C14 C15 69.4(4) . . . . ? Ni1 N2 C14 C15 -162.9(2) . . . . ? N2 C14 C15 C16 -165.5(5) . . . . ? N2 C14 C15 C16A -139.0(5) . . . . ? C5 N3 C17 C18 -48.9(4) . . . . ? C6 N3 C17 C18 69.3(3) . . . . ? Ni1 N3 C17 C18 -173.0(2) . . . . ? N3 C17 C18 C19 -173.3(3) . . . . ? C17 C18 C19 O3 -175.9(3) . . . . ? C7 N4 C20 C21 -53.3(4) . . . . ? C8 N4 C20 C21 66.2(3) . . . . ? Ni1 N4 C20 C21 -166.8(2) . . . . ? N4 C20 C21 C22 -174.3(3) . . . . ? C20 C21 C22 O4 -66.1(4) . . . . ? C14 C15 C16 O2 75.3(8) . . . . ? C16A C15 C16 O2 -35.7(12) . . . . ? C16 C15 C16A O2A 10.9(9) . . . . ? C14 C15 C16A O2A -68.1(8) . . . . ? 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 H1 O10 0.84 2.51 2.720(3) 95.4 . O4 H4 O10 0.84 1.96 2.787(4) 167.4 2_564 O3 H3AC O6 0.90(4) 1.96(4) 2.855(4) 169(3) 1_545 O2 H2 O9 0.84 2.26 3.073(6) 163.1 2_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.550 _refine_diff_density_min -0.979 _refine_diff_density_rms 0.187 data_d:\structs\asif\ac21\ac21 _database_code_depnum_ccdc_archive 'CCDC 267666' _audit_creation_method SHELXL-97 _chemical_name_systematic 3-tetrahydroxypropylcyclam _chemical_name_common 3-tetrahydroxypropylcyclam _chemical_melting_point ? _chemical_formula_moiety 'C22 H50 B2 F8 N4 O4' _chemical_formula_sum 'C22 H50 B2 F8 N4 O4' _chemical_formula_weight 608.28 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.8652(10) _cell_length_b 11.9557(8) _cell_length_c 11.4131(9) _cell_angle_alpha 90.0 _cell_angle_beta 103.732(4) _cell_angle_gamma 90.0 _cell_volume 1440.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description cube _exptl_crystal_colour colourless _exptl_crystal_size_max 2.00 _exptl_crystal_size_mid 2.00 _exptl_crystal_size_min 2.00 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type SCALEPACK _exptl_absorpt_correction_T_min 0.7846 _exptl_absorpt_correction_T_max 0.7846 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 KappaCCD _diffrn_measurement_method '2o phi + omega scans 2s/o' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7921 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3193 _reflns_number_gt 2177 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0693P)^2^+0.1995P] 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 0.008(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3193 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0884 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1404 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.36030(14) 0.06888(10) 1.15175(11) 0.0502(4) Uani 1 1 d . . . O1 O 0.38052(14) -0.40099(12) 0.48675(12) 0.0339(4) Uani 1 1 d . . . H1 H 0.3585 -0.4430 0.5372 0.041 Uiso 1 1 calc R . . N1 N 0.24550(14) -0.09218(12) 0.58944(14) 0.0202(4) Uani 1 1 d . . . C1 C 0.47589(18) -0.32551(16) 0.54816(18) 0.0293(5) Uani 1 1 d . . . H1A H 0.5497 -0.3285 0.5114 0.035 Uiso 1 1 calc R . . H1B H 0.5046 -0.3480 0.6338 0.035 Uiso 1 1 calc R . . B1 B 0.2998(2) 0.01244(18) 1.22842(18) 0.0242(5) Uani 1 1 d . . . F2 F 0.25687(14) 0.08576(11) 1.30297(11) 0.0466(4) Uani 1 1 d . . . O2 O 0.16520(12) -0.11321(10) 0.80552(12) 0.0265(3) Uani 1 1 d . . . H2 H 0.2282 -0.1147 0.8647 0.032 Uiso 1 1 calc R . . N2 N 0.14597(13) 0.11626(11) 0.64818(13) 0.0198(3) Uani 1 1 d . . . C2 C 0.42432(18) -0.20730(16) 0.54055(18) 0.0283(5) Uani 1 1 d . . . H2A H 0.3795 -0.1908 0.4562 0.034 Uiso 1 1 calc R . . H2B H 0.4955 -0.1539 0.5642 0.034 Uiso 1 1 calc R . . F3 F 0.38231(12) -0.06433(11) 1.29483(12) 0.0474(4) Uani 1 1 d . . . C3 C 0.33347(17) -0.19152(15) 0.62257(17) 0.0235(4) Uani 1 1 d . . . H3A H 0.2818 -0.2601 0.6197 0.028 Uiso 1 1 calc R . . H3B H 0.3835 -0.1821 0.7066 0.028 Uiso 1 1 calc R . . F4 F 0.19664(12) -0.04636(11) 1.15822(12) 0.0492(4) Uani 1 1 d . . . C4 C 0.14226(17) -0.11038(15) 0.47778(16) 0.0215(4) Uani 1 1 d . . . H4A H 0.1802 -0.1365 0.4119 0.026 Uiso 1 1 calc R . . H4B H 0.0990 -0.0384 0.4525 0.026 Uiso 1 1 calc R . . C5 C 0.31945(17) 0.01315(15) 0.58530(18) 0.0250(4) Uani 1 1 d . . . H5A H 0.3595 0.0090 0.5160 0.030 Uiso 1 1 calc R . . H5B H 0.3880 0.0182 0.6597 0.030 Uiso 1 1 calc R . . C6 C 0.23917(17) 0.11843(15) 0.57372(17) 0.0243(4) Uani 1 1 d . . . H6A H 0.2956 0.1838 0.5973 0.029 Uiso 1 1 calc R . . H6B H 0.1940 0.1283 0.4882 0.029 Uiso 1 1 calc R . . C7 C 0.05946(17) 0.21283(14) 0.61668(16) 0.0225(4) Uani 1 1 d . . . H7A H 0.1097 0.2795 0.6059 0.027 Uiso 1 1 calc R . . H7B H 0.0200 0.2281 0.6848 0.027 Uiso 1 1 calc R . . C8 C -0.04548(17) 0.19580(14) 0.50215(16) 0.0215(4) Uani 1 1 d . . . H8A H -0.0884 0.2680 0.4775 0.026 Uiso 1 1 calc R . . H8B H -0.0076 0.1699 0.4361 0.026 Uiso 1 1 calc R . . C9 C 0.20995(17) 0.12178(15) 0.77764(16) 0.0237(4) Uani 1 1 d . . . H9A H 0.2360 0.2000 0.7987 0.028 Uiso 1 1 calc R . . H9B H 0.2876 0.0754 0.7924 0.028 Uiso 1 1 calc R . . C10 C 0.12718(18) 0.08184(15) 0.85938(16) 0.0255(4) Uani 1 1 d . . . H10A H 0.0561 0.1350 0.8536 0.031 Uiso 1 1 calc R . . H10B H 0.1778 0.0823 0.9439 0.031 Uiso 1 1 calc R . . C11 C 0.07356(18) -0.03489(15) 0.82865(17) 0.0255(4) Uani 1 1 d . . . H11A H 0.0398 -0.0630 0.8964 0.031 Uiso 1 1 calc R . . H11B H 0.0021 -0.0304 0.7565 0.031 Uiso 1 1 calc R . . H3 H 0.211(2) -0.0858(18) 0.651(2) 0.035(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0745(10) 0.0403(7) 0.0444(8) 0.0023(6) 0.0309(7) -0.0096(7) O1 0.0355(8) 0.0322(8) 0.0321(8) -0.0004(6) 0.0043(7) -0.0050(6) N1 0.0163(8) 0.0196(8) 0.0248(8) -0.0002(6) 0.0051(7) 0.0003(6) C1 0.0224(10) 0.0297(10) 0.0341(10) -0.0055(9) 0.0036(8) 0.0032(8) B1 0.0268(11) 0.0266(11) 0.0197(10) 0.0044(9) 0.0066(9) 0.0043(9) F2 0.0648(9) 0.0413(7) 0.0378(7) -0.0064(6) 0.0203(7) 0.0034(7) O2 0.0253(7) 0.0250(7) 0.0293(7) 0.0001(6) 0.0069(6) 0.0027(6) N2 0.0186(8) 0.0188(7) 0.0215(7) -0.0002(6) 0.0035(6) 0.0004(6) C2 0.0212(10) 0.0256(10) 0.0393(11) 0.0002(8) 0.0094(9) 0.0041(8) F3 0.0402(8) 0.0540(8) 0.0463(8) 0.0165(6) 0.0070(6) 0.0128(6) C3 0.0184(9) 0.0226(9) 0.0294(10) 0.0036(8) 0.0057(8) 0.0033(7) F4 0.0305(7) 0.0572(8) 0.0578(8) -0.0191(7) 0.0066(6) -0.0015(6) C4 0.0204(9) 0.0218(9) 0.0214(9) 0.0022(8) 0.0031(8) 0.0006(7) C5 0.0217(10) 0.0206(9) 0.0340(10) -0.0018(8) 0.0093(8) -0.0044(8) C6 0.0232(10) 0.0191(9) 0.0326(10) -0.0002(8) 0.0108(8) -0.0044(8) C7 0.0221(9) 0.0182(9) 0.0257(9) -0.0006(7) 0.0028(8) 0.0004(7) C8 0.0225(9) 0.0175(9) 0.0242(9) 0.0024(7) 0.0045(8) 0.0001(7) C9 0.0218(9) 0.0198(9) 0.0264(10) -0.0046(8) -0.0005(8) -0.0017(8) C10 0.0304(11) 0.0243(10) 0.0202(9) -0.0012(8) 0.0025(8) 0.0040(8) C11 0.0234(10) 0.0282(10) 0.0258(9) 0.0022(8) 0.0080(8) 0.0044(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 F1 B1 1.388(2) . ? O1 C1 1.426(2) . ? N1 C4 1.500(2) . ? N1 C5 1.501(2) . ? N1 C3 1.515(2) . ? C1 C2 1.515(3) . ? B1 F3 1.378(2) . ? B1 F2 1.378(2) . ? B1 F4 1.402(3) . ? O2 C11 1.436(2) . ? N2 C6 1.469(2) . ? N2 C9 1.478(2) . ? N2 C7 1.478(2) . ? C2 C3 1.525(3) . ? C4 C8 1.522(2) 3_556 ? C5 C6 1.519(2) . ? C7 C8 1.531(2) . ? C8 C4 1.522(2) 3_556 ? C9 C10 1.518(3) . ? C10 C11 1.521(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 C4 N1 C5 113.14(14) . . ? C4 N1 C3 113.48(13) . . ? C5 N1 C3 110.79(14) . . ? O1 C1 C2 110.26(16) . . ? F3 B1 F2 110.83(16) . . ? F3 B1 F1 109.10(16) . . ? F2 B1 F1 111.13(17) . . ? F3 B1 F4 107.92(17) . . ? F2 B1 F4 109.26(16) . . ? F1 B1 F4 108.52(16) . . ? C6 N2 C9 110.64(14) . . ? C6 N2 C7 109.35(13) . . ? C9 N2 C7 109.23(13) . . ? C1 C2 C3 111.39(16) . . ? N1 C3 C2 113.94(14) . . ? N1 C4 C8 111.93(14) . 3_556 ? N1 C5 C6 113.41(14) . . ? N2 C6 C5 113.30(14) . . ? N2 C7 C8 113.92(14) . . ? C4 C8 C7 111.23(15) 3_556 . ? N2 C9 C10 113.18(15) . . ? C9 C10 C11 113.40(15) . . ? O2 C11 C10 113.35(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 O1 C1 C2 C3 73.6(2) . . . . ? C4 N1 C3 C2 73.46(19) . . . . ? C5 N1 C3 C2 -55.1(2) . . . . ? C1 C2 C3 N1 -160.12(15) . . . . ? C5 N1 C4 C8 -162.95(15) . . . 3_556 ? C3 N1 C4 C8 69.72(19) . . . 3_556 ? C4 N1 C5 C6 61.1(2) . . . . ? C3 N1 C5 C6 -170.18(15) . . . . ? C9 N2 C6 C5 68.60(19) . . . . ? C7 N2 C6 C5 -171.04(15) . . . . ? N1 C5 C6 N2 40.8(2) . . . . ? C6 N2 C7 C8 79.98(18) . . . . ? C9 N2 C7 C8 -158.81(15) . . . . ? N2 C7 C8 C4 70.44(19) . . . 3_556 ? C6 N2 C9 C10 -160.85(14) . . . . ? C7 N2 C9 C10 78.72(18) . . . . ? N2 C9 C10 C11 54.4(2) . . . . ? C9 C10 C11 O2 44.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 F1 0.84 1.99 2.7963(19) 160.3 4 O1 H1 F4 0.84 2.48 3.174(2) 140.0 4 O2 H2 O1 0.84 1.90 2.7356(19) 171.0 4_556 N1 H3 O2 0.88(2) 1.97(2) 2.816(2) 162(2) . C5 H5A F2 0.99 2.59 3.249(2) 124.0 1_554 C6 H6B F2 0.99 2.42 3.165(2) 131.2 1_554 C2 H2A F3 0.99 2.39 3.223(2) 141.5 1_554 C5 H5A F3 0.99 2.74 3.659(2) 154.8 1_554 _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.272 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.093 data_g:\structs\asif\ac202a\ac202a _database_code_depnum_ccdc_archive 'CCDC 267667' _audit_creation_method SHELXL-97 _chemical_name_systematic 'tetrahydroxypropylcyclam diperchlorate' _chemical_name_common 'tetrahydroxypropylcyclam diperchlorate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H50 Cl2 N4 O12' _chemical_formula_weight 633.56 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' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.9260(4) _cell_length_b 11.9504(8) _cell_length_c 11.5955(6) _cell_angle_alpha 90.0 _cell_angle_beta 104.449(3) _cell_angle_gamma 90.0 _cell_volume 1466.14(14) _cell_formula_units_Z 2 _cell_measurement_temperature 101(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description cube _exptl_crystal_colour 'pale pink' _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.80 _exptl_crystal_size_min 0.70 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_correction_type SCALEPACK _exptl_absorpt_correction_T_min 0.7818 _exptl_absorpt_correction_T_max 0.8240 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 101(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 KappaCCD _diffrn_measurement_method '2 phi + omega scans 4.5 s/o' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7090 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0619 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2574 _reflns_number_gt 2278 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0333P)^2^+0.7403P] 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 0.014(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2574 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0887 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.20312(3) 0.01236(3) 0.27452(3) 0.01620(15) Uani 1 1 d . . . O1 O -0.88485(10) -0.40085(10) 0.01420(10) 0.0207(3) Uani 1 1 d . . . H1 H -0.8844 -0.4569 -0.0264 0.025 Uiso 1 1 d R . . N1 N -0.74573(11) -0.09433(11) -0.08967(11) 0.0130(3) Uani 1 1 d . . . C1 C -0.97873(14) -0.32438(14) -0.04937(14) 0.0180(4) Uani 1 1 d . . . H1A H -1.0515 -0.3254 -0.0155 0.022 Uiso 1 1 d R . . H1B H -1.0065 -0.3472 -0.1321 0.022 Uiso 1 1 d R . . O2 O -0.33078(10) 0.11603(9) 0.30337(10) 0.0178(3) Uani 1 1 d . . . H2 H -0.2665 0.1120 0.3578 0.021 Uiso 1 1 d R . . N2 N -0.35350(11) -0.11503(11) 0.14739(11) 0.0134(3) Uani 1 1 d . . . C2 C -0.92476(14) -0.20721(14) -0.04189(14) 0.0174(4) Uani 1 1 d . . . H2A H -0.8809 -0.1909 0.0399 0.021 Uiso 1 1 d R . . H2B H -0.9933 -0.1538 -0.0662 0.021 Uiso 1 1 d R . . O3 O 0.24380(12) 0.08933(11) 0.19617(10) 0.0270(3) Uani 1 1 d . . . C3 C -0.83344(14) -0.19375(14) -0.12120(14) 0.0151(3) Uani 1 1 d . . . H3A H -0.7830 -0.2612 -0.1156 0.018 Uiso 1 1 d R . . H3B H -0.8819 -0.1865 -0.2032 0.018 Uiso 1 1 d R . . O4 O 0.13491(12) 0.07277(11) 0.34730(11) 0.0294(3) Uani 1 1 d . . . C4 C -0.81950(14) 0.01134(13) -0.08622(15) 0.0159(4) Uani 1 1 d . . . H4A H -0.8577 0.0073 -0.0193 0.019 Uiso 1 1 d R . . H4B H -0.8873 0.0161 -0.1583 0.019 Uiso 1 1 d R . . O5 O 0.12042(11) -0.06998(11) 0.20571(11) 0.0281(3) Uani 1 1 d . . . C5 C -0.64170(14) -0.11203(13) 0.02120(13) 0.0142(3) Uani 1 1 d . . . H5A H -0.6780 -0.1389 0.0843 0.017 Uiso 1 1 d R . . H5B H -0.6006 -0.0411 0.0465 0.017 Uiso 1 1 d R . . O6 O 0.31037(11) -0.04189(12) 0.35056(11) 0.0279(3) Uani 1 1 d . . . C6 C -0.54429(14) -0.19553(14) 0.00181(14) 0.0151(3) Uani 1 1 d . . . H6A H -0.5079 -0.1688 -0.0613 0.018 Uiso 1 1 d R . . H6B H -0.5851 -0.2667 -0.0231 0.018 Uiso 1 1 d R . . C7 C -0.43897(14) -0.21205(13) 0.11530(13) 0.0151(3) Uani 1 1 d . . . H7A H -0.4771 -0.2278 0.1806 0.018 Uiso 1 1 d R . . H7B H -0.3893 -0.2769 0.1051 0.018 Uiso 1 1 d R . . C8 C -0.26068(14) -0.11712(13) 0.07482(14) 0.0157(4) Uani 1 1 d . . . H8A H -0.3051 -0.1272 -0.0081 0.019 Uiso 1 1 d R . . H8B H -0.2052 -0.1809 0.0985 0.019 Uiso 1 1 d R . . C9 C -0.28923(14) -0.12009(14) 0.27550(13) 0.0153(4) Uani 1 1 d . . . H9A H -0.2130 -0.0751 0.2901 0.018 Uiso 1 1 d R . . H9B H -0.2643 -0.1968 0.2964 0.018 Uiso 1 1 d R . . C10 C -0.37130(15) -0.07908(14) 0.35526(14) 0.0179(4) Uani 1 1 d . . . H10A H -0.3217 -0.0802 0.4373 0.022 Uiso 1 1 d R . . H10B H -0.4414 -0.1304 0.3489 0.022 Uiso 1 1 d R . . C11 C -0.42341(15) 0.03822(14) 0.32527(14) 0.0178(4) Uani 1 1 d . . . H11A H -0.4936 0.0347 0.2550 0.021 Uiso 1 1 d R . . H11B H -0.4557 0.0660 0.3905 0.021 Uiso 1 1 d R . . H3 H -0.7046 -0.0945 -0.1494 0.031(5) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0168(2) 0.0164(3) 0.0153(2) -0.00119(15) 0.00387(16) -0.00010(14) O1 0.0225(6) 0.0182(7) 0.0203(6) -0.0014(5) 0.0033(5) 0.0023(5) N1 0.0099(6) 0.0140(7) 0.0149(7) -0.0003(5) 0.0030(5) -0.0006(5) C1 0.0119(7) 0.0214(10) 0.0199(8) 0.0018(7) 0.0026(6) -0.0018(6) O2 0.0166(5) 0.0172(7) 0.0192(6) 0.0004(5) 0.0038(5) -0.0017(4) N2 0.0121(6) 0.0125(7) 0.0151(7) 0.0001(5) 0.0025(5) -0.0009(5) C2 0.0137(7) 0.0174(9) 0.0223(8) -0.0014(7) 0.0067(6) -0.0008(6) O3 0.0361(7) 0.0249(7) 0.0225(6) 0.0056(5) 0.0120(5) -0.0026(6) C3 0.0128(7) 0.0147(9) 0.0175(8) -0.0030(6) 0.0030(6) -0.0038(6) O4 0.0418(8) 0.0252(8) 0.0265(7) -0.0025(6) 0.0185(6) 0.0078(6) C4 0.0129(8) 0.0137(9) 0.0216(8) 0.0015(6) 0.0054(6) 0.0025(6) O5 0.0237(6) 0.0307(8) 0.0282(7) -0.0101(6) 0.0031(5) -0.0085(5) C5 0.0128(7) 0.0143(9) 0.0137(8) -0.0009(6) -0.0001(6) -0.0008(6) O6 0.0171(6) 0.0339(8) 0.0303(7) 0.0103(6) 0.0013(5) 0.0021(5) C6 0.0143(7) 0.0131(9) 0.0169(8) -0.0016(6) 0.0020(6) -0.0007(6) C7 0.0144(8) 0.0116(8) 0.0181(8) 0.0010(6) 0.0017(6) -0.0007(6) C8 0.0147(8) 0.0139(9) 0.0194(8) 0.0009(6) 0.0060(6) 0.0029(6) C9 0.0145(7) 0.0130(9) 0.0158(8) 0.0019(6) -0.0007(6) 0.0010(6) C10 0.0204(8) 0.0183(9) 0.0135(8) 0.0008(7) 0.0013(6) -0.0039(7) C11 0.0166(8) 0.0187(9) 0.0196(8) -0.0023(7) 0.0074(6) -0.0022(7) _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 Cl1 O6 1.4337(12) . ? Cl1 O5 1.4358(13) . ? Cl1 O3 1.4389(12) . ? Cl1 O4 1.4500(12) . ? O1 C1 1.4329(19) . ? N1 C5 1.5034(19) . ? N1 C4 1.504(2) . ? N1 C3 1.5129(19) . ? C1 C2 1.513(2) . ? O2 C11 1.4427(19) . ? N2 C8 1.4707(19) . ? N2 C7 1.4770(19) . ? N2 C9 1.4775(19) . ? C2 C3 1.525(2) . ? C4 C8 1.525(2) 3_455 ? C5 C6 1.516(2) . ? C6 C7 1.529(2) . ? C8 C4 1.525(2) 3_455 ? C9 C10 1.521(2) . ? C10 C11 1.520(2) . ? 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 Cl1 O5 109.65(8) . . ? O6 Cl1 O3 110.09(7) . . ? O5 Cl1 O3 109.75(7) . . ? O6 Cl1 O4 109.09(8) . . ? O5 Cl1 O4 108.73(8) . . ? O3 Cl1 O4 109.50(8) . . ? C5 N1 C4 113.03(12) . . ? C5 N1 C3 113.22(12) . . ? C4 N1 C3 110.76(11) . . ? O1 C1 C2 110.00(12) . . ? C8 N2 C7 108.99(12) . . ? C8 N2 C9 110.61(12) . . ? C7 N2 C9 109.46(12) . . ? C1 C2 C3 111.55(13) . . ? N1 C3 C2 114.05(13) . . ? N1 C4 C8 113.46(12) . 3_455 ? N1 C5 C6 112.01(12) . . ? C5 C6 C7 111.26(13) . . ? N2 C7 C6 114.09(13) . . ? N2 C8 C4 113.56(13) . 3_455 ? N2 C9 C10 113.19(12) . . ? C11 C10 C9 113.70(13) . . ? O2 C11 C10 113.29(13) . . ? 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 O1 C1 C2 C3 74.05(16) . . . . ? C5 N1 C3 C2 74.64(16) . . . . ? C4 N1 C3 C2 -53.53(17) . . . . ? C1 C2 C3 N1 -161.40(13) . . . . ? C5 N1 C4 C8 61.04(17) . . . 3_455 ? C3 N1 C4 C8 -170.69(12) . . . 3_455 ? C4 N1 C5 C6 -161.83(13) . . . . ? C3 N1 C5 C6 71.19(16) . . . . ? N1 C5 C6 C7 179.74(12) . . . . ? C8 N2 C7 C6 -80.34(15) . . . . ? C9 N2 C7 C6 158.56(13) . . . . ? C5 C6 C7 N2 -70.86(17) . . . . ? C7 N2 C8 C4 170.97(12) . . . 3_455 ? C9 N2 C8 C4 -68.64(16) . . . 3_455 ? C8 N2 C9 C10 160.31(13) . . . . ? C7 N2 C9 C10 -79.58(16) . . . . ? N2 C9 C10 C11 -54.99(18) . . . . ? C9 C10 C11 O2 -44.08(18) . . . . ? 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 H1 O4 0.82 2.06 2.8674(17) 166.5 4_455 O2 H2 O1 0.82 1.93 2.7531(15) 178.8 2_455 N1 H3 O2 0.92 1.94 2.8179(16) 161.3 3_455 C2 H2A O5 0.97 2.40 3.236(2) 143.8 1_455 C8 H8A O3 0.97 2.48 3.2105(19) 132.2 3 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.494 _refine_diff_density_min -0.857 _refine_diff_density_rms 0.186 data_L1-4H2O _database_code_depnum_ccdc_archive 'CCDC 267668' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common L1.4H2O _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H56 N4 O8' _chemical_formula_weight 504.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7258(15) _cell_length_b 7.9552(16) _cell_length_c 25.987(5) _cell_angle_alpha 91.77(3) _cell_angle_beta 90.64(3) _cell_angle_gamma 111.41(3) _cell_volume 1485.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10794 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.128 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9204 _exptl_absorpt_correction_T_max 0.9941 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method '1.3 phi + omega scans 30 s/o' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7779 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0661 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5589 _reflns_number_gt 4283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed(Barbour 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0715P)^2^+0.2132P] 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 0.070(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5589 _refine_ls_number_parameters 532 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0822 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1628 _refine_ls_wR_factor_gt 0.1349 _refine_ls_goodness_of_fit_ref 1.255 _refine_ls_restrained_S_all 1.255 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O -0.3212(2) 0.2316(2) 0.40414(5) 0.0216(4) Uani 1 1 d . . . O1B O 0.8125(2) 1.2176(2) 0.10579(5) 0.0225(4) Uani 1 1 d . . . O2A O 0.0373(2) 0.5628(2) 0.24301(5) 0.0256(4) Uani 1 1 d . . . O2B O 0.3584(2) 0.7864(2) 0.19919(5) 0.0223(4) Uani 1 1 d . . . O3 O -0.2833(3) 0.0653(2) 0.31165(7) 0.0322(4) Uani 1 1 d . . . O4 O 0.0963(3) 0.2263(3) 0.26697(8) 0.0413(5) Uani 1 1 d . . . O5 O 0.4151(3) 1.1161(2) 0.24524(6) 0.0293(4) Uani 1 1 d . . . O6 O 0.6857(3) 1.3589(2) 0.18873(6) 0.0274(4) Uani 1 1 d . . . N1A N -0.7229(2) 0.3156(2) 0.43097(6) 0.0160(4) Uani 1 1 d . . . N1B N 1.2269(2) 1.1599(2) 0.07018(6) 0.0157(4) Uani 1 1 d . . . N2A N -0.3434(2) 0.5732(2) 0.39780(6) 0.0157(4) Uani 1 1 d . . . N2B N 0.8517(2) 0.8856(2) 0.09958(6) 0.0146(4) Uani 1 1 d . . . C1A C -0.7163(3) 0.4785(3) 0.40472(7) 0.0180(4) Uani 1 1 d . . . C1B C 1.2235(3) 0.9849(3) 0.08777(7) 0.0169(4) Uani 1 1 d . . . C2A C -0.5319(3) 0.5648(3) 0.37314(7) 0.0186(5) Uani 1 1 d . . . C2B C 1.0423(3) 0.8837(3) 0.11959(7) 0.0169(4) Uani 1 1 d . . . C3A C -0.3108(3) 0.6667(3) 0.44908(7) 0.0169(4) Uani 1 1 d . . . C3B C 0.8132(3) 0.8125(3) 0.04573(7) 0.0163(4) Uani 1 1 d . . . C4A C -0.1548(3) 0.6303(3) 0.48195(7) 0.0188(5) Uani 1 1 d . . . C4B C 0.6414(3) 0.8438(3) 0.01898(7) 0.0180(5) Uani 1 1 d . . . C5A C -0.8892(3) 0.2607(3) 0.46683(7) 0.0185(5) Uani 1 1 d . . . C5B C 1.3952(3) 1.2387(3) 0.03572(7) 0.0173(4) Uani 1 1 d . . . C6A C -0.7417(3) 0.1668(3) 0.39396(7) 0.0211(5) Uani 1 1 d . . . C6B C 1.2366(3) 1.2867(3) 0.11338(7) 0.0188(5) Uani 1 1 d . . . C7A C -0.6633(3) 0.0298(3) 0.41672(9) 0.0257(5) Uani 1 1 d . . . C7B C 1.1540(3) 1.4294(3) 0.09790(8) 0.0226(5) Uani 1 1 d . . . C8A C -0.4553(3) 0.1195(3) 0.43968(8) 0.0221(5) Uani 1 1 d . . . C8B C 0.9476(3) 1.3470(3) 0.07395(8) 0.0217(5) Uani 1 1 d . . . C9A C -0.1765(3) 0.6705(3) 0.36437(7) 0.0180(5) Uani 1 1 d . . . C9B C 0.6898(3) 0.7758(3) 0.13233(7) 0.0170(5) Uani 1 1 d . . . C10A C -0.1640(3) 0.5652(3) 0.31537(7) 0.0201(5) Uani 1 1 d . . . C10B C 0.7100(3) 0.8365(3) 0.18870(7) 0.0189(5) Uani 1 1 d . . . C11A C 0.0260(3) 0.6641(3) 0.28851(7) 0.0211(5) Uani 1 1 d . . . C11B C 0.5209(3) 0.7393(3) 0.21707(7) 0.0207(5) Uani 1 1 d . . . H1A1 H -0.837(4) 0.455(3) 0.3827(9) 0.031(6) Uiso 1 1 d . . . H1A2 H -0.726(3) 0.567(3) 0.4313(9) 0.028(6) Uiso 1 1 d . . . H1B1 H 1.346(3) 0.991(3) 0.1083(9) 0.024(6) Uiso 1 1 d . . . H1B2 H 1.233(3) 0.912(3) 0.0559(9) 0.024(6) Uiso 1 1 d . . . H2A1 H -0.525(4) 0.686(4) 0.3652(9) 0.035(7) Uiso 1 1 d . . . H2A2 H -0.545(3) 0.501(3) 0.3396(9) 0.027(6) Uiso 1 1 d . . . H2B1 H 1.061(3) 0.936(3) 0.1553(8) 0.017(5) Uiso 1 1 d . . . H2B2 H 1.032(3) 0.753(3) 0.1220(9) 0.023(6) Uiso 1 1 d . . . H3A H -0.374(5) 0.087(4) 0.2966(12) 0.055(10) Uiso 1 1 d . . . H3A1 H -0.269(3) 0.802(3) 0.4454(8) 0.019(6) Uiso 1 1 d . . . H3A2 H -0.437(3) 0.634(3) 0.4663(8) 0.022(6) Uiso 1 1 d . . . H3B H -0.289(4) 0.116(4) 0.3397(12) 0.046(9) Uiso 1 1 d . . . H3B1 H 0.934(3) 0.873(3) 0.0278(8) 0.021(6) Uiso 1 1 d . . . H3B2 H 0.792(3) 0.679(3) 0.0449(8) 0.020(6) Uiso 1 1 d . . . H4A H -0.006(6) 0.177(5) 0.2789(14) 0.069(12) Uiso 1 1 d . . . H4A1 H -0.201(3) 0.502(3) 0.4883(8) 0.014(5) Uiso 1 1 d . . . H4A2 H -0.032(3) 0.659(3) 0.4643(9) 0.024(6) Uiso 1 1 d . . . H4B H 0.084(4) 0.309(5) 0.2566(12) 0.048(10) Uiso 1 1 d . . . H4B1 H 0.514(3) 0.796(3) 0.0380(9) 0.025(6) Uiso 1 1 d . . . H4B2 H 0.660(3) 0.977(4) 0.0193(9) 0.028(6) Uiso 1 1 d . . . H5A H 0.320(5) 1.142(4) 0.2527(11) 0.044(9) Uiso 1 1 d . . . H5A1 H -1.014(3) 0.263(3) 0.4501(9) 0.024(6) Uiso 1 1 d . . . H5A2 H -0.920(3) 0.129(3) 0.4753(8) 0.021(6) Uiso 1 1 d . . . H5B H 0.485(5) 1.201(5) 0.2282(12) 0.052(9) Uiso 1 1 d . . . H5B1 H 1.421(3) 1.376(3) 0.0349(9) 0.029(6) Uiso 1 1 d . . . H5B2 H 1.522(3) 1.229(3) 0.0499(8) 0.020(6) Uiso 1 1 d . . . H6A H 0.722(4) 1.310(4) 0.1656(12) 0.042(8) Uiso 1 1 d . . . H6A1 H -0.881(3) 0.105(3) 0.3807(8) 0.021(6) Uiso 1 1 d . . . H6A2 H -0.665(3) 0.216(3) 0.3627(8) 0.012(5) Uiso 1 1 d . . . H6B H 0.793(5) 1.423(4) 0.2061(12) 0.047(9) Uiso 1 1 d . . . H6B1 H 1.154(3) 1.217(3) 0.1425(8) 0.016(5) Uiso 1 1 d . . . H6B2 H 1.366(4) 1.348(3) 0.1280(9) 0.031(7) Uiso 1 1 d . . . H7A1 H -0.749(4) -0.037(4) 0.4435(10) 0.035(7) Uiso 1 1 d . . . H7A2 H -0.660(4) -0.056(4) 0.3872(10) 0.034(7) Uiso 1 1 d . . . H7B1 H 1.156(3) 1.500(3) 0.1276(9) 0.024(6) Uiso 1 1 d . . . H7B2 H 1.244(3) 1.515(3) 0.0729(8) 0.021(6) Uiso 1 1 d . . . H8A1 H -0.399(3) 0.025(3) 0.4494(8) 0.022(6) Uiso 1 1 d . . . H8A2 H -0.455(3) 0.183(3) 0.4703(9) 0.022(6) Uiso 1 1 d . . . H8B1 H 0.947(3) 1.294(3) 0.0395(9) 0.027(6) Uiso 1 1 d . . . H8B2 H 0.893(3) 1.437(3) 0.0684(9) 0.024(6) Uiso 1 1 d . . . H9A1 H -0.184(4) 0.791(4) 0.3549(10) 0.036(7) Uiso 1 1 d . . . H9A2 H -0.058(4) 0.690(3) 0.3824(9) 0.027(6) Uiso 1 1 d . . . H9B1 H 0.677(3) 0.645(3) 0.1311(9) 0.026(6) Uiso 1 1 d . . . H9B2 H 0.569(3) 0.780(3) 0.1211(8) 0.013(5) Uiso 1 1 d . . . H10A H -0.165(3) 0.444(3) 0.3255(9) 0.030(6) Uiso 1 1 d . . . H10B H -0.271(4) 0.545(3) 0.2900(10) 0.032(7) Uiso 1 1 d . . . H10C H 0.818(3) 0.808(3) 0.2044(9) 0.023(6) Uiso 1 1 d . . . H10D H 0.740(3) 0.963(3) 0.1934(9) 0.025(6) Uiso 1 1 d . . . H11A H 0.028(3) 0.781(3) 0.2784(9) 0.024(6) Uiso 1 1 d . . . H11B H 0.138(4) 0.682(3) 0.3104(10) 0.034(7) Uiso 1 1 d . . . H11C H 0.544(3) 0.758(3) 0.2534(9) 0.020(6) Uiso 1 1 d . . . H11D H 0.481(3) 0.599(3) 0.2081(9) 0.025(6) Uiso 1 1 d . . . H22 H -0.338(4) 0.324(4) 0.4045(10) 0.033(7) Uiso 1 1 d . . . H46 H 0.837(4) 1.115(4) 0.1014(10) 0.036(7) Uiso 1 1 d . . . H54 H 0.367(5) 0.888(5) 0.2153(13) 0.064(10) Uiso 1 1 d . . . H56 H 0.130(4) 0.626(4) 0.2290(11) 0.048(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.0275(10) 0.0186(8) 0.0211(7) 0.0014(6) 0.0034(6) 0.0112(7) O1B 0.0261(9) 0.0183(8) 0.0251(7) -0.0020(6) 0.0038(6) 0.0108(7) O2A 0.0264(10) 0.0266(9) 0.0182(7) -0.0029(6) 0.0094(6) 0.0030(8) O2B 0.0235(9) 0.0244(8) 0.0188(7) 0.0018(6) 0.0056(6) 0.0083(7) O3 0.0473(13) 0.0301(9) 0.0234(8) -0.0032(7) 0.0031(8) 0.0195(9) O4 0.0435(14) 0.0435(12) 0.0464(11) 0.0136(10) 0.0143(9) 0.0257(11) O5 0.0333(11) 0.0257(9) 0.0312(9) 0.0026(7) 0.0079(7) 0.0133(8) O6 0.0292(11) 0.0296(9) 0.0228(8) -0.0048(7) 0.0029(7) 0.0103(8) N1A 0.0192(10) 0.0166(9) 0.0119(7) -0.0003(6) 0.0008(6) 0.0063(7) N1B 0.0208(10) 0.0141(8) 0.0126(7) -0.0002(6) 0.0012(6) 0.0070(7) N2A 0.0170(10) 0.0165(8) 0.0127(7) 0.0003(6) 0.0024(6) 0.0050(7) N2B 0.0165(10) 0.0151(8) 0.0116(7) 0.0000(6) 0.0023(6) 0.0051(7) C1A 0.0182(12) 0.0216(10) 0.0161(9) 0.0020(8) -0.0009(8) 0.0097(9) C1B 0.0191(12) 0.0183(10) 0.0165(9) 0.0012(8) 0.0000(8) 0.0105(9) C2A 0.0233(13) 0.0196(10) 0.0146(9) 0.0019(8) 0.0012(8) 0.0097(9) C2B 0.0188(12) 0.0167(10) 0.0160(9) 0.0031(8) 0.0013(8) 0.0072(9) C3A 0.0205(12) 0.0186(10) 0.0130(8) -0.0012(8) 0.0025(8) 0.0088(9) C3B 0.0214(12) 0.0156(10) 0.0129(8) -0.0007(8) 0.0015(8) 0.0083(9) C4A 0.0196(13) 0.0219(11) 0.0160(9) 0.0020(8) 0.0024(8) 0.0086(9) C4B 0.0194(12) 0.0213(11) 0.0144(9) 0.0008(8) 0.0021(8) 0.0088(9) C5A 0.0169(12) 0.0216(11) 0.0144(9) -0.0009(8) 0.0010(8) 0.0042(9) C5B 0.0168(12) 0.0183(10) 0.0143(9) -0.0007(8) 0.0000(8) 0.0038(9) C6A 0.0223(13) 0.0221(11) 0.0174(9) -0.0042(8) -0.0015(8) 0.0069(10) C6B 0.0217(13) 0.0184(10) 0.0163(9) -0.0045(8) -0.0027(8) 0.0078(9) C7A 0.0306(15) 0.0164(10) 0.0278(11) -0.0015(9) 0.0038(10) 0.0060(10) C7B 0.0258(14) 0.0152(10) 0.0259(11) -0.0044(9) -0.0011(9) 0.0071(10) C8A 0.0333(14) 0.0188(10) 0.0177(9) 0.0023(8) 0.0033(9) 0.0135(10) C8B 0.0294(14) 0.0165(10) 0.0217(10) 0.0007(8) -0.0003(9) 0.0115(10) C9A 0.0215(13) 0.0167(10) 0.0141(9) 0.0011(8) 0.0042(8) 0.0050(9) C9B 0.0188(13) 0.0163(10) 0.0146(9) 0.0016(8) 0.0023(8) 0.0049(9) C10A 0.0228(13) 0.0204(11) 0.0155(9) 0.0000(8) 0.0047(8) 0.0060(10) C10B 0.0204(13) 0.0210(11) 0.0144(9) 0.0006(8) 0.0011(8) 0.0063(10) C11A 0.0245(13) 0.0246(11) 0.0132(9) -0.0004(8) 0.0029(8) 0.0079(10) C11B 0.0254(13) 0.0238(11) 0.0144(9) 0.0037(8) 0.0042(8) 0.0104(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 O1A C8A 1.456(3) . ? O1B C8B 1.456(3) . ? O2A C11A 1.432(2) . ? O2B C11B 1.508(3) . ? N1A C6A 1.466(3) . ? N1A C1A 1.467(2) . ? N1A C5A 1.533(3) . ? N1B C1B 1.470(2) . ? N1B C6B 1.469(2) . ? N1B C5B 1.533(3) . ? N2A C3A 1.479(2) . ? N2A C9A 1.534(3) . ? N2A C2A 1.562(3) . ? N2B C3B 1.483(2) . ? N2B C9B 1.524(3) . ? N2B C2B 1.562(3) . ? C1A C2A 1.588(3) . ? C1B C2B 1.592(3) . ? C3A C4A 1.585(3) . ? C3B C4B 1.593(3) . ? C4A C5A 1.530(3) 2_466 ? C4B C5B 1.526(3) 2_775 ? C5A C4A 1.530(3) 2_466 ? C5B C4B 1.526(3) 2_775 ? C6A C7A 1.555(3) . ? C6B C7B 1.553(3) . ? C7A C8A 1.601(3) . ? C7B C8B 1.597(3) . ? C9A C10A 1.526(3) . ? C9B C10B 1.517(3) . ? C10A C11A 1.573(3) . ? C10B C11B 1.584(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 C6A N1A C1A 111.30(15) . . ? C6A N1A C5A 109.81(16) . . ? C1A N1A C5A 108.40(16) . . ? C1B N1B C6B 112.08(14) . . ? C1B N1B C5B 108.23(16) . . ? C6B N1B C5B 110.29(15) . . ? C3A N2A C9A 108.15(15) . . ? C3A N2A C2A 111.01(16) . . ? C9A N2A C2A 112.60(14) . . ? C3B N2B C9B 108.30(15) . . ? C3B N2B C2B 110.54(15) . . ? C9B N2B C2B 112.60(14) . . ? N1A C1A C2A 112.59(17) . . ? N1B C1B C2B 111.86(16) . . ? N2A C2A C1A 118.55(15) . . ? N2B C2B C1B 118.47(14) . . ? N2A C3A C4A 112.51(17) . . ? N2B C3B C4B 113.54(16) . . ? C5A C4A C3A 112.21(18) 2_466 . ? C5B C4B C3B 111.26(17) 2_775 . ? C4A C5A N1A 112.40(16) 2_466 . ? C4B C5B N1B 112.53(16) 2_775 . ? N1A C6A C7A 111.47(16) . . ? N1B C6B C7B 111.40(16) . . ? C6A C7A C8A 114.26(18) . . ? C6B C7B C8B 114.63(17) . . ? O1A C8A C7A 114.60(16) . . ? O1B C8B C7B 114.93(16) . . ? C10A C9A N2A 114.66(17) . . ? C10B C9B N2B 114.15(16) . . ? C9A C10A C11A 110.16(17) . . ? C9B C10B C11B 110.14(17) . . ? O2A C11A C10A 109.64(17) . . ? O2B C11B C10B 115.55(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 C6A N1A C1A C2A -68.0(2) . . . . ? C5A N1A C1A C2A 171.17(16) . . . . ? C6B N1B C1B C2B 63.6(2) . . . . ? C5B N1B C1B C2B -174.60(15) . . . . ? C3A N2A C2A C1A -55.0(2) . . . . ? C9A N2A C2A C1A -176.41(16) . . . . ? N1A C1A C2A N2A -41.2(2) . . . . ? C3B N2B C2B C1B 55.9(2) . . . . ? C9B N2B C2B C1B 177.14(16) . . . . ? N1B C1B C2B N2B 42.0(2) . . . . ? C9A N2A C3A C4A -72.4(2) . . . . ? C2A N2A C3A C4A 163.59(16) . . . . ? C9B N2B C3B C4B 67.08(19) . . . . ? C2B N2B C3B C4B -169.13(15) . . . . ? N2A C3A C4A C5A 175.44(16) . . . 2_466 ? N2B C3B C4B C5B -178.38(15) . . . 2_775 ? C6A N1A C5A C4A 156.77(16) . . . 2_466 ? C1A N1A C5A C4A -81.5(2) . . . 2_466 ? C1B N1B C5B C4B 80.08(19) . . . 2_775 ? C6B N1B C5B C4B -156.99(16) . . . 2_775 ? C1A N1A C6A C7A 154.73(18) . . . . ? C5A N1A C6A C7A -85.2(2) . . . . ? C1B N1B C6B C7B -154.60(18) . . . . ? C5B N1B C6B C7B 84.7(2) . . . . ? N1A C6A C7A C8A -52.5(2) . . . . ? N1B C6B C7B C8B 53.9(2) . . . . ? C6A C7A C8A O1A -53.7(2) . . . . ? C6B C7B C8B O1B 54.6(2) . . . . ? C3A N2A C9A C10A 165.37(17) . . . . ? C2A N2A C9A C10A -71.6(2) . . . . ? C3B N2B C9B C10B -179.72(16) . . . . ? C2B N2B C9B C10B 57.7(2) . . . . ? N2A C9A C10A C11A -171.79(16) . . . . ? N2B C9B C10B C11B 169.63(16) . . . . ? C9A C10A C11A O2A 179.19(17) . . . . ? C9B C10B C11B O2B -64.8(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3B O1A 0.83(3) 1.95(3) 2.777(2) 176(3) . O3 H3A O5 0.88(3) 2.17(3) 3.035(3) 168(3) 1_445 O4 H4A O3 0.82(4) 2.19(4) 3.003(3) 175(4) . O4 H4B O2A 0.76(4) 2.21(4) 2.958(3) 168(3) . O5 H5A O4 0.86(4) 2.10(4) 2.954(3) 175(3) 1_565 O5 H5B O6 0.84(3) 1.93(3) 2.748(3) 165(3) . O6 H6A O1B 0.81(3) 1.94(3) 2.752(2) 174(3) . O6 H6B O2A 0.91(3) 2.02(3) 2.925(3) 178(3) 1_665 O1A H22 N2A 0.79(3) 2.01(3) 2.794(2) 170(3) . O1B H46 N2B 0.91(3) 1.87(3) 2.766(2) 170(2) . O2B H54 O5 0.88(4) 1.86(4) 2.731(2) 172(3) . O2A H56 O2B 0.81(3) 1.95(3) 2.753(2) 176(3) . _diffrn_measured_fraction_theta_max 0.820 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.820 _refine_diff_density_max 0.400 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.148 data_AC20 _database_code_depnum_ccdc_archive 'CCDC 267669' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nickel(II)3-hydroxypropylcyclam diperchlorate ; _chemical_name_common 'nickel(ii)3-hydroxypropylcyclam diperchlorate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H50 Cl5 N4 Ni O12.50' _chemical_formula_weight 818.63 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' Ni Ni 0.3393 1.1124 '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 9.7140(11) _cell_length_b 10.3555(7) _cell_length_c 18.0585(13) _cell_angle_alpha 101.519(5) _cell_angle_beta 104.520(5) _cell_angle_gamma 100.024(5) _cell_volume 1674.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 858 _exptl_absorpt_coefficient_mu 1.044 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4889 _exptl_absorpt_correction_T_max 0.9794 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method '2o phi + omega scans 3.5 s/o' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9847 _diffrn_reflns_av_R_equivalents 0.0903 _diffrn_reflns_av_sigmaI/netI 0.1206 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5882 _reflns_number_gt 4328 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo-SMN _computing_data_reduction Denzo-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed interface to POVRay' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0822P)^2^+9.1500P] 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 0.010(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5882 _refine_ls_number_parameters 431 _refine_ls_number_restraints 186 _refine_ls_R_factor_all 0.1193 _refine_ls_R_factor_gt 0.0837 _refine_ls_wR_factor_ref 0.2180 _refine_ls_wR_factor_gt 0.1958 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.72604(8) 0.09271(7) 0.25934(4) 0.0226(3) Uani 1 1 d . . . Cl1 Cl 0.22302(19) -0.07384(19) 0.11400(10) 0.0425(5) Uani 1 1 d U . . O1 O 0.9685(6) -0.3769(5) 0.2856(3) 0.0470(13) Uani 1 1 d U A . H1 H 1.0467 -0.3851 0.3151 0.056 Uiso 1 1 calc R . . N1 N 0.7114(5) -0.1121(5) 0.2041(3) 0.0237(11) Uani 1 1 d . A . C1 C 0.6907(14) -0.1065(12) 0.1223(6) 0.036(3) Uiso 0.660(6) 1 d P A 1 H1A H 0.5929 -0.0905 0.1003 0.044 Uiso 0.660(6) 1 calc PR A 1 H1B H 0.6958 -0.1943 0.0904 0.044 Uiso 0.660(6) 1 calc PR A 1 Cl2 Cl 1.32938(18) -0.40553(17) 0.40840(10) 0.0381(4) Uani 1 1 d U . . O2 O 0.9348(5) 0.1522(4) 0.3312(2) 0.0295(10) Uani 1 1 d U A . N2 N 0.7932(6) 0.1530(6) 0.1644(3) 0.0372(13) Uani 1 1 d . A . C2 C 0.8106(13) 0.0092(11) 0.1175(7) 0.043(3) Uiso 0.660(6) 1 d P A 1 H2A H 0.8005 0.0085 0.0615 0.052 Uiso 0.660(6) 1 calc PR A 1 H2B H 0.9088 -0.0044 0.1415 0.052 Uiso 0.660(6) 1 calc PR A 1 Cl3 Cl 0.2786(3) -0.4985(3) 0.16912(16) 0.0714(7) Uani 1 1 d U . . O3 O 0.7657(7) 0.7143(6) 0.4693(3) 0.0211(14) Uiso 0.660(6) 1 d P A 1 H3 H 0.6840 0.6874 0.4759 0.025 Uiso 0.660(6) 1 calc PR A 1 N3 N 0.6337(6) 0.2636(5) 0.2776(3) 0.0300(12) Uani 1 1 d . A . C3 C 0.6871(13) 0.1928(12) 0.1106(7) 0.047(3) Uiso 0.660(6) 1 d P A 1 H3A H 0.5966 0.1193 0.0891 0.056 Uiso 0.660(6) 1 calc PR A 1 H3B H 0.7236 0.2085 0.0658 0.056 Uiso 0.660(6) 1 calc PR A 1 Cl4 Cl 0.3580(4) -0.4953(4) 0.0260(2) 0.1237(15) Uani 1 1 d U . . O4 O 0.9183(5) -0.0437(5) 0.5625(3) 0.0330(10) Uani 1 1 d U A . H4 H 0.8738 -0.1124 0.5249 0.040 Uiso 1 1 calc R . . N4 N 0.6361(9) 0.0466(9) 0.3549(5) 0.024(2) Uiso 0.660(6) 1 d P A 1 C4 C 0.6525(14) 0.3215(12) 0.1506(7) 0.049(3) Uiso 0.660(6) 1 d P A 1 H4A H 0.6030 0.3616 0.1091 0.059 Uiso 0.660(6) 1 calc PR A 1 H4B H 0.7460 0.3871 0.1819 0.059 Uiso 0.660(6) 1 calc PR A 1 Cl5 Cl 0.0710(6) -0.6236(6) 0.0194(2) 0.193(3) Uani 1 1 d U . . O5 O 0.3661(7) -0.0066(7) 0.1206(4) 0.084(2) Uani 1 1 d U A . C5 C 0.5572(16) 0.3044(13) 0.2050(7) 0.045(3) Uiso 0.660(6) 1 d P A 1 H5A H 0.5297 0.3908 0.2218 0.054 Uiso 0.660(6) 1 calc PR A 1 H5B H 0.4660 0.2344 0.1752 0.054 Uiso 0.660(6) 1 calc PR A 1 O6 O 0.1080(11) -0.0640(15) 0.0554(6) 0.074(3) Uani 0.660(6) 1 d PU A 1 C6 C 0.5059(13) 0.2189(12) 0.3112(8) 0.034(3) Uiso 0.660(6) 1 d P A 1 H6A H 0.4662 0.2975 0.3287 0.041 Uiso 0.660(6) 1 calc PR A 1 H6B H 0.4262 0.1491 0.2698 0.041 Uiso 0.660(6) 1 calc PR A 1 O7 O 0.2341(12) -0.2160(10) 0.0985(9) 0.087(4) Uani 0.660(6) 1 d PU A 1 C7 C 0.5628(14) 0.1627(11) 0.3793(7) 0.039(3) Uiso 0.660(6) 1 d P A 1 H7A H 0.4813 0.1281 0.3991 0.047 Uiso 0.660(6) 1 calc PR A 1 H7B H 0.6350 0.2357 0.4226 0.047 Uiso 0.660(6) 1 calc PR A 1 O8 O 0.1992(19) -0.059(2) 0.1885(8) 0.050(4) Uani 0.660(6) 1 d PU A 1 C8 C 0.5178(11) -0.0798(10) 0.3248(6) 0.035(2) Uiso 0.660(6) 1 d P A 1 H8A H 0.4377 -0.0670 0.2827 0.042 Uiso 0.660(6) 1 calc PR A 1 H8B H 0.4779 -0.0959 0.3684 0.042 Uiso 0.660(6) 1 calc PR A 1 O9 O 1.2883(11) -0.4060(17) 0.3315(5) 0.178(6) Uani 1 1 d U . . C9 C 0.5672(12) -0.2041(10) 0.2919(6) 0.034(2) Uiso 0.660(6) 1 d P A 1 H9A H 0.6617 -0.2047 0.3286 0.041 Uiso 0.660(6) 1 calc PR A 1 H9B H 0.4946 -0.2863 0.2891 0.041 Uiso 0.660(6) 1 calc PR A 1 O10 O 1.2127(6) -0.3851(5) 0.4404(4) 0.0576(15) Uani 1 1 d U . . C10 C 0.5852(13) -0.2097(12) 0.2109(8) 0.030(3) Uiso 0.660(6) 1 d P A 1 H10A H 0.5929 -0.3026 0.1883 0.036 Uiso 0.660(6) 1 calc PR A 1 H10B H 0.4943 -0.1960 0.1771 0.036 Uiso 0.660(6) 1 calc PR A 1 O11 O 1.4610(6) -0.3084(5) 0.4515(4) 0.0559(15) Uani 1 1 d U . . C11 C 0.8533(8) -0.1527(7) 0.2303(5) 0.0458(19) Uani 1 1 d U . . H11A H 0.8683 -0.1604 0.2854 0.055 Uiso 1 1 calc R A . H11B H 0.9336 -0.0788 0.2309 0.055 Uiso 1 1 calc R . . O12 O 1.3503(8) -0.5363(6) 0.4091(7) 0.139(5) Uani 1 1 d U . . C12 C 0.8667(9) -0.2852(8) 0.1804(5) 0.0483(19) Uani 1 1 d U A . H12A H 0.7764 -0.3562 0.1695 0.058 Uiso 1 1 calc R . . H12B H 0.8770 -0.2717 0.1291 0.058 Uiso 1 1 calc R . . C13 C 0.9963(9) -0.3318(8) 0.2218(6) 0.055(2) Uani 1 1 d U . . H13A H 1.0145 -0.4062 0.1845 0.066 Uiso 1 1 calc R A . H13B H 1.0845 -0.2559 0.2409 0.066 Uiso 1 1 calc R . . C15 C 1.0665(12) 0.2228(13) 0.2464(6) 0.033(3) Uiso 0.660(6) 1 d P A 1 H15A H 1.0907 0.1332 0.2358 0.039 Uiso 0.660(6) 1 calc PR A 1 H15B H 1.1529 0.2905 0.2472 0.039 Uiso 0.660(6) 1 calc PR A 1 C17 C 0.7457(7) 0.3784(6) 0.3403(4) 0.0340(15) Uani 1 1 d U . . H17A H 0.7896 0.3415 0.3848 0.041 Uiso 1 1 calc R A . H17B H 0.8247 0.4099 0.3179 0.041 Uiso 1 1 calc R . . C18 C 0.6946(8) 0.5003(7) 0.3737(4) 0.0408(17) Uani 1 1 d U A . H18A H 0.6576 0.5433 0.3309 0.049 Uiso 1 1 calc R . . H18B H 0.6128 0.4707 0.3946 0.049 Uiso 1 1 calc R . . C19 C 0.8154(8) 0.6029(6) 0.4389(4) 0.0386(16) Uani 1 1 d U . . H19A H 0.8530 0.5601 0.4817 0.046 Uiso 1 1 calc R A 1 H19B H 0.8970 0.6336 0.4180 0.046 Uiso 1 1 calc R A 1 C20 C 0.7537(7) 0.0545(7) 0.4295(4) 0.0283(14) Uani 1 1 d U . . H20A H 0.8182 0.1470 0.4480 0.034 Uiso 1 1 calc R A 1 H20B H 0.8140 -0.0096 0.4166 0.034 Uiso 1 1 calc R A 1 C21 C 0.6982(6) 0.0228(6) 0.4969(3) 0.0238(12) Uani 1 1 d U A . H21A H 0.6311 0.0811 0.5076 0.029 Uiso 1 1 calc R . . H21B H 0.6425 -0.0729 0.4813 0.029 Uiso 1 1 calc R . . C22 C 0.8228(7) 0.0463(6) 0.5709(4) 0.0293(14) Uani 1 1 d U . . H22A H 0.8804 0.1411 0.5849 0.035 Uiso 1 1 calc R A . H22B H 0.7825 0.0340 0.6149 0.035 Uiso 1 1 calc R . . C16A C 1.0783(17) 0.1827(16) 0.3031(9) 0.016(3) Uiso 0.340(6) 1 d P A 2 H16A H 1.1644 0.2305 0.3492 0.019 Uiso 0.340(6) 1 calc PR A 2 H16B H 1.0973 0.0967 0.2771 0.019 Uiso 0.340(6) 1 calc PR A 2 O1S O -0.2203(11) -0.2396(10) -0.0578(6) 0.044(2) Uani 0.50 1 d PU . . C1S C 0.2222(13) -0.5052(19) 0.0717(6) 0.128(6) Uani 1 1 d U . . H1S H 0.1911 -0.4183 0.0707 0.154 Uiso 1 1 calc R . . H2 H 0.9835 0.1121 0.3658 0.154 Uiso 1 1 d R . . C3A C 0.6974(17) 0.0839(15) 0.0845(9) 0.016(3) Uiso 0.340(6) 1 d P A 2 H3A1 H 0.7278 0.1281 0.0454 0.019 Uiso 0.340(6) 1 calc PR A 2 H3A2 H 0.5950 0.0880 0.0809 0.019 Uiso 0.340(6) 1 calc PR A 2 C2A C 0.7099(17) -0.0619(15) 0.0678(9) 0.017(3) Uiso 0.340(6) 1 d P A 2 H2A1 H 0.8146 -0.0636 0.0835 0.020 Uiso 0.340(6) 1 calc PR A 2 H2A2 H 0.6695 -0.1035 0.0101 0.020 Uiso 0.340(6) 1 calc PR A 2 C9A C 0.6567(17) -0.1387(14) 0.3255(8) 0.013(3) Uiso 0.340(6) 1 d P A 2 H9A1 H 0.5883 -0.1877 0.3486 0.016 Uiso 0.340(6) 1 calc PR A 2 H9A2 H 0.7552 -0.1528 0.3479 0.016 Uiso 0.340(6) 1 calc PR A 2 C4A C 0.7538(18) 0.3057(15) 0.1734(9) 0.018(3) Uiso 0.340(6) 1 d P A 2 H4A1 H 0.8377 0.3752 0.2122 0.021 Uiso 0.340(6) 1 calc PR A 2 H4A2 H 0.7376 0.3290 0.1218 0.021 Uiso 0.340(6) 1 calc PR A 2 C8A C 0.5039(16) 0.0226(14) 0.3405(8) 0.011(3) Uiso 0.340(6) 1 d P A 2 H8A1 H 0.4390 -0.0278 0.2871 0.013 Uiso 0.340(6) 1 calc PR A 2 H8A2 H 0.4693 -0.0197 0.3791 0.013 Uiso 0.340(6) 1 calc PR A 2 C7A C 0.488(2) 0.1653(16) 0.3554(10) 0.021(4) Uiso 0.340(6) 1 d P A 2 H7A1 H 0.5658 0.2205 0.4037 0.026 Uiso 0.340(6) 1 calc PR A 2 H7A2 H 0.3926 0.1672 0.3655 0.026 Uiso 0.340(6) 1 calc PR A 2 C1A C 0.628(2) -0.1489(18) 0.1119(9) 0.017(4) Uiso 0.340(6) 1 d P A 2 H1A1 H 0.6194 -0.2462 0.0887 0.020 Uiso 0.340(6) 1 calc PR A 2 H1A2 H 0.5283 -0.1340 0.1043 0.020 Uiso 0.340(6) 1 calc PR A 2 C5A C 0.618(2) 0.3068(16) 0.2006(9) 0.016(4) Uiso 0.340(6) 1 d P A 2 H5A1 H 0.5323 0.2445 0.1591 0.019 Uiso 0.340(6) 1 calc PR A 2 H5A2 H 0.6006 0.3992 0.2083 0.019 Uiso 0.340(6) 1 calc PR A 2 C10A C 0.609(2) -0.194(2) 0.2379(13) 0.022(5) Uiso 0.340(6) 1 d P A 2 H10C H 0.5069 -0.1871 0.2154 0.026 Uiso 0.340(6) 1 calc PR A 2 H10D H 0.6116 -0.2907 0.2244 0.026 Uiso 0.340(6) 1 calc PR A 2 C6A C 0.496(2) 0.230(2) 0.2874(13) 0.022(5) Uiso 0.340(6) 1 d P A 2 H6A1 H 0.4292 0.1668 0.2376 0.027 Uiso 0.340(6) 1 calc PR A 2 H6A2 H 0.4589 0.3134 0.2957 0.027 Uiso 0.340(6) 1 calc PR A 2 C15A C 1.053(2) 0.270(2) 0.2456(10) 0.021(4) Uiso 0.340(6) 1 d P A 2 H15C H 1.0342 0.3544 0.2738 0.025 Uiso 0.340(6) 1 calc PR A 2 H15D H 1.1457 0.2961 0.2330 0.025 Uiso 0.340(6) 1 calc PR A 2 N4A N 0.6606(15) 0.0057(15) 0.3460(8) 0.013(3) Uiso 0.340(6) 1 d P A 2 O6A O 0.167(2) 0.044(3) 0.0878(13) 0.072(6) Uani 0.340(6) 1 d PU A 2 O7A O 0.145(4) -0.188(2) 0.0518(16) 0.097(8) Uani 0.340(6) 1 d PU A 2 O8A O 0.177(6) -0.041(6) 0.183(3) 0.104(17) Uani 0.340(6) 1 d PU A 2 C16 C 1.0535(12) 0.2510(11) 0.3278(6) 0.037(2) Uiso 0.660(6) 1 d P A 1 H16C H 1.1455 0.2478 0.3657 0.044 Uiso 0.660(6) 1 calc PR A 1 H16D H 1.0362 0.3428 0.3427 0.044 Uiso 0.660(6) 1 calc PR A 1 C14 C 0.9447(8) 0.2211(10) 0.1759(5) 0.064(3) Uani 1 1 d U . . H14A H 0.9430 0.3170 0.1776 0.077 Uiso 1 1 d R A . H14B H 0.9712 0.1846 0.1277 0.077 Uiso 1 1 d R . . O3A O 0.8625(8) 0.7154(10) 0.4133(5) 0.143(11) Uiso 0.340(6) 1 d PR A 2 H3A3 H 0.8960 0.6920 0.3755 0.171 Uiso 0.340(6) 1 calc PR A 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 Ni1 0.0204(4) 0.0208(4) 0.0256(4) 0.0080(3) 0.0052(3) 0.0023(3) Cl1 0.0331(10) 0.0588(11) 0.0368(9) 0.0113(8) 0.0136(7) 0.0104(8) O1 0.039(3) 0.035(3) 0.069(4) 0.018(3) 0.015(3) 0.010(2) N1 0.018(3) 0.026(3) 0.028(3) 0.006(2) 0.009(2) 0.004(2) Cl2 0.0295(9) 0.0379(9) 0.0429(9) -0.0005(7) 0.0129(7) 0.0071(7) O2 0.022(2) 0.026(2) 0.036(2) 0.0133(18) 0.0026(18) -0.0038(17) N2 0.029(3) 0.047(3) 0.031(3) 0.011(3) 0.006(2) -0.001(3) Cl3 0.0621(15) 0.0716(15) 0.0846(17) 0.0208(13) 0.0300(13) 0.0128(12) N3 0.033(3) 0.025(3) 0.034(3) 0.010(2) 0.010(2) 0.006(2) Cl4 0.110(3) 0.128(3) 0.105(2) -0.030(2) 0.076(2) -0.039(2) O4 0.025(2) 0.043(3) 0.033(2) 0.011(2) 0.0074(19) 0.013(2) Cl5 0.148(4) 0.246(6) 0.098(3) -0.034(3) 0.055(3) -0.112(4) O5 0.054(4) 0.095(5) 0.103(5) 0.008(4) 0.050(4) -0.006(4) O6 0.049(6) 0.125(10) 0.053(6) 0.042(7) 0.002(5) 0.026(7) O7 0.049(6) 0.048(6) 0.145(11) -0.001(6) 0.019(7) 0.009(5) O8 0.023(5) 0.104(12) 0.026(5) 0.025(6) 0.010(4) 0.012(6) O9 0.090(7) 0.373(18) 0.073(6) 0.081(8) 0.025(5) 0.029(9) O10 0.041(3) 0.049(3) 0.090(4) 0.009(3) 0.038(3) 0.011(2) O11 0.038(3) 0.039(3) 0.080(4) -0.009(3) 0.021(3) 0.001(2) C11 0.023(4) 0.027(3) 0.083(6) 0.010(4) 0.012(4) 0.005(3) O12 0.044(4) 0.034(3) 0.307(13) -0.024(5) 0.052(6) 0.007(3) C12 0.057(5) 0.041(4) 0.064(5) 0.016(4) 0.036(4) 0.025(4) C13 0.040(5) 0.043(4) 0.107(7) 0.032(5) 0.046(5) 0.020(4) C17 0.032(4) 0.029(3) 0.042(4) 0.007(3) 0.013(3) 0.009(3) C18 0.038(4) 0.026(3) 0.054(4) 0.006(3) 0.006(3) 0.013(3) C19 0.043(4) 0.029(3) 0.044(4) 0.011(3) 0.011(3) 0.009(3) C20 0.019(3) 0.038(3) 0.031(3) 0.011(3) 0.011(3) 0.008(3) C21 0.016(3) 0.029(3) 0.028(3) 0.012(3) 0.005(2) 0.007(2) C22 0.024(3) 0.030(3) 0.034(3) 0.011(3) 0.010(3) 0.001(3) O1S 0.045(6) 0.046(6) 0.037(5) 0.009(4) 0.011(5) 0.001(5) C1S 0.068(8) 0.220(16) 0.061(7) -0.003(8) 0.030(6) -0.030(9) O6A 0.070(14) 0.099(15) 0.072(13) 0.057(12) 0.022(11) 0.039(12) O7A 0.13(2) 0.060(13) 0.103(17) 0.005(12) 0.057(16) 0.024(14) O8A 0.09(3) 0.10(2) 0.13(3) -0.01(2) 0.07(2) 0.038(19) C14 0.030(4) 0.099(7) 0.069(5) 0.061(5) 0.008(4) -0.008(4) _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 Ni1 O2 2.026(4) . ? Ni1 N1 2.120(5) . ? Ni1 N3 2.124(5) . ? Ni1 N4A 2.128(13) . ? Ni1 N2 2.145(6) . ? Ni1 N4 2.216(8) . ? Cl1 O6 1.367(9) . ? Cl1 O7A 1.40(2) . ? Cl1 O8 1.404(15) . ? Cl1 O5 1.407(6) . ? Cl1 O8A 1.42(5) . ? Cl1 O7 1.470(10) . ? Cl1 O6A 1.530(19) . ? O1 C13 1.395(10) . ? N1 C1 1.454(12) . ? N1 C10 1.494(12) . ? N1 C11 1.502(8) . ? N1 C10A 1.52(2) . ? N1 C1A 1.592(17) . ? C1 C2 1.551(17) . ? Cl2 O9 1.344(9) . ? Cl2 O12 1.406(7) . ? Cl2 O11 1.412(5) . ? Cl2 O10 1.424(5) . ? O2 C16 1.425(11) . ? O2 C16A 1.603(16) . ? N2 C3 1.409(13) . ? N2 C14 1.461(9) . ? N2 C3A 1.464(15) . ? N2 C2 1.618(12) . ? N2 C4A 1.678(16) . ? Cl3 C1S 1.690(12) . ? O3 C19 1.394(8) . ? N3 C6A 1.39(2) . ? N3 C17 1.508(8) . ? N3 C5 1.515(13) . ? N3 C5A 1.524(17) . ? N3 C6 1.553(13) . ? C3 C4 1.518(16) . ? Cl4 C1S 1.721(11) . ? O4 C22 1.438(7) . ? N4 C8 1.486(13) . ? N4 C20 1.509(10) . ? N4 C7 1.546(15) . ? C4 C5 1.524(18) . ? Cl5 C1S 1.664(13) . ? C6 C7 1.487(18) . ? C8 C9 1.513(14) . ? C9 C10 1.507(15) . ? C11 C12 1.529(10) . ? C12 C13 1.503(11) . ? C15 C16 1.484(15) . ? C15 C14 1.500(13) . ? C17 C18 1.506(9) . ? C18 C19 1.504(10) . ? C19 O3A 1.383(10) . ? C20 N4A 1.483(14) . ? C20 C21 1.519(8) . ? C21 C22 1.505(8) . ? C16A C15A 1.51(2) . ? C3A C2A 1.51(2) . ? C2A C1A 1.56(2) . ? C9A N4A 1.46(2) . ? C9A C10A 1.49(3) . ? C4A C5A 1.52(2) . ? C8A C7A 1.49(2) . ? C8A N4A 1.54(2) . ? C7A C6A 1.52(3) . ? C15A C14 1.357(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 O2 Ni1 N1 102.10(18) . . ? O2 Ni1 N3 106.25(19) . . ? N1 Ni1 N3 151.6(2) . . ? O2 Ni1 N4A 89.6(4) . . ? N1 Ni1 N4A 82.8(4) . . ? N3 Ni1 N4A 96.9(5) . . ? O2 Ni1 N2 91.32(19) . . ? N1 Ni1 N2 89.4(2) . . ? N3 Ni1 N2 90.3(2) . . ? N4A Ni1 N2 172.1(4) . . ? O2 Ni1 N4 93.1(2) . . ? N1 Ni1 N4 95.4(3) . . ? N3 Ni1 N4 82.9(3) . . ? N4A Ni1 N4 14.0(4) . . ? N2 Ni1 N4 172.7(3) . . ? O6 Cl1 O7A 60.2(14) . . ? O6 Cl1 O8 114.4(9) . . ? O7A Cl1 O8 120.5(13) . . ? O6 Cl1 O5 119.7(6) . . ? O7A Cl1 O5 121.7(11) . . ? O8 Cl1 O5 111.2(8) . . ? O6 Cl1 O8A 103(2) . . ? O7A Cl1 O8A 121(3) . . ? O8 Cl1 O8A 13(3) . . ? O5 Cl1 O8A 116(2) . . ? O6 Cl1 O7 107.9(8) . . ? O7A Cl1 O7 47.8(12) . . ? O8 Cl1 O7 99.5(11) . . ? O5 Cl1 O7 101.1(5) . . ? O8A Cl1 O7 109(3) . . ? O6 Cl1 O6A 45.3(9) . . ? O7A Cl1 O6A 104.5(16) . . ? O8 Cl1 O6A 101.2(12) . . ? O5 Cl1 O6A 89.3(10) . . ? O8A Cl1 O6A 89(2) . . ? O7 Cl1 O6A 151.7(11) . . ? C1 N1 C10 110.6(8) . . ? C1 N1 C11 106.6(7) . . ? C10 N1 C11 112.2(6) . . ? C1 N1 C10A 128.2(10) . . ? C10 N1 C10A 17.7(8) . . ? C11 N1 C10A 104.3(9) . . ? C1 N1 C1A 23.8(6) . . ? C10 N1 C1A 86.8(9) . . ? C11 N1 C1A 118.5(8) . . ? C10A N1 C1A 104.4(11) . . ? C1 N1 Ni1 101.0(5) . . ? C10 N1 Ni1 113.6(5) . . ? C11 N1 Ni1 112.2(4) . . ? C10A N1 Ni1 104.5(8) . . ? C1A N1 Ni1 111.5(6) . . ? N1 C1 C2 110.1(9) . . ? O9 Cl2 O12 105.0(9) . . ? O9 Cl2 O11 112.4(6) . . ? O12 Cl2 O11 109.5(4) . . ? O9 Cl2 O10 108.7(6) . . ? O12 Cl2 O10 109.1(5) . . ? O11 Cl2 O10 111.9(3) . . ? C16 O2 C16A 32.5(6) . . ? C16 O2 Ni1 128.6(5) . . ? C16A O2 Ni1 125.5(6) . . ? C3 N2 C14 115.2(7) . . ? C3 N2 C3A 47.8(7) . . ? C14 N2 C3A 119.8(8) . . ? C3 N2 C2 106.4(7) . . ? C14 N2 C2 93.2(7) . . ? C3A N2 C2 59.0(7) . . ? C3 N2 C4A 52.4(7) . . ? C14 N2 C4A 87.7(7) . . ? C3A N2 C4A 99.9(9) . . ? C2 N2 C4A 155.8(8) . . ? C3 N2 Ni1 115.4(6) . . ? C14 N2 Ni1 121.1(4) . . ? C3A N2 Ni1 116.0(7) . . ? C2 N2 Ni1 99.8(5) . . ? C4A N2 Ni1 100.4(6) . . ? C1 C2 N2 109.1(8) . . ? C6A N3 C17 117.3(9) . . ? C6A N3 C5 85.7(11) . . ? C17 N3 C5 114.1(6) . . ? C6A N3 C5A 108.6(13) . . ? C17 N3 C5A 105.4(8) . . ? C5 N3 C5A 23.3(7) . . ? C6A N3 C6 16.8(9) . . ? C17 N3 C6 108.0(6) . . ? C5 N3 C6 102.4(8) . . ? C5A N3 C6 125.4(10) . . ? C6A N3 Ni1 112.2(9) . . ? C17 N3 Ni1 108.9(4) . . ? C5 N3 Ni1 117.3(6) . . ? C5A N3 Ni1 103.3(7) . . ? C6 N3 Ni1 105.1(5) . . ? N2 C3 C4 110.9(9) . . ? C8 N4 C20 115.7(7) . . ? C8 N4 C7 106.2(8) . . ? C20 N4 C7 104.1(7) . . ? C8 N4 Ni1 110.9(6) . . ? C20 N4 Ni1 112.8(5) . . ? C7 N4 Ni1 106.3(6) . . ? C3 C4 C5 115.7(10) . . ? N3 C5 C4 112.4(11) . . ? C7 C6 N3 108.4(9) . . ? C6 C7 N4 111.1(9) . . ? N4 C8 C9 113.8(9) . . ? C10 C9 C8 113.0(9) . . ? N1 C10 C9 118.2(9) . . ? N1 C11 C12 116.3(6) . . ? C13 C12 C11 111.5(7) . . ? O1 C13 C12 109.3(6) . . ? C16 C15 C14 122.4(10) . . ? C18 C17 N3 117.7(5) . . ? C19 C18 C17 111.9(6) . . ? O3A C19 O3 67.6(6) . . ? O3A C19 C18 110.7(7) . . ? O3 C19 C18 111.0(6) . . ? N4A C20 N4 20.7(5) . . ? N4A C20 C21 121.7(7) . . ? N4 C20 C21 115.1(5) . . ? C22 C21 C20 111.1(5) . . ? O4 C22 C21 112.9(5) . . ? C15A C16A O2 108.1(12) . . ? Cl5 C1S Cl3 115.1(8) . . ? Cl5 C1S Cl4 113.7(7) . . ? Cl3 C1S Cl4 115.2(8) . . ? N2 C3A C2A 107.6(11) . . ? C3A C2A C1A 113.5(13) . . ? N4A C9A C10A 110.5(13) . . ? C5A C4A N2 111.0(11) . . ? C7A C8A N4A 115.4(13) . . ? C8A C7A C6A 113.9(14) . . ? C2A C1A N1 112.1(13) . . ? C4A C5A N3 111.7(13) . . ? C9A C10A N1 108.1(14) . . ? N3 C6A C7A 115.7(17) . . ? C14 C15A C16A 120.0(16) . . ? C9A N4A C20 104.0(11) . . ? C9A N4A C8A 108.7(12) . . ? C20 N4A C8A 109.8(11) . . ? C9A N4A Ni1 108.3(10) . . ? C20 N4A Ni1 118.9(8) . . ? C8A N4A Ni1 106.7(9) . . ? O2 C16 C15 109.3(8) . . ? C15A C14 N2 126.9(10) . . ? C15A C14 C15 20.6(8) . . ? N2 C14 C15 121.9(7) . . ? 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 O2 Ni1 N1 C1 -114.8(6) . . . . ? N3 Ni1 N1 C1 65.9(7) . . . . ? N4A Ni1 N1 C1 157.1(7) . . . . ? N2 Ni1 N1 C1 -23.6(6) . . . . ? N4 Ni1 N1 C1 150.8(6) . . . . ? O2 Ni1 N1 C10 126.8(6) . . . . ? N3 Ni1 N1 C10 -52.5(8) . . . . ? N4A Ni1 N1 C10 38.7(7) . . . . ? N2 Ni1 N1 C10 -142.0(6) . . . . ? N4 Ni1 N1 C10 32.4(6) . . . . ? O2 Ni1 N1 C11 -1.7(5) . . . . ? N3 Ni1 N1 C11 179.1(5) . . . . ? N4A Ni1 N1 C11 -89.8(6) . . . . ? N2 Ni1 N1 C11 89.5(5) . . . . ? N4 Ni1 N1 C11 -96.0(5) . . . . ? O2 Ni1 N1 C10A 110.7(9) . . . . ? N3 Ni1 N1 C10A -68.6(10) . . . . ? N4A Ni1 N1 C10A 22.6(9) . . . . ? N2 Ni1 N1 C10A -158.1(9) . . . . ? N4 Ni1 N1 C10A 16.3(9) . . . . ? O2 Ni1 N1 C1A -137.2(8) . . . . ? N3 Ni1 N1 C1A 43.6(9) . . . . ? N4A Ni1 N1 C1A 134.8(9) . . . . ? N2 Ni1 N1 C1A -45.9(8) . . . . ? N4 Ni1 N1 C1A 128.5(8) . . . . ? C10 N1 C1 C2 172.0(8) . . . . ? C11 N1 C1 C2 -65.8(9) . . . . ? C10A N1 C1 C2 170.0(11) . . . . ? C1A N1 C1 C2 170(2) . . . . ? Ni1 N1 C1 C2 51.5(8) . . . . ? N1 Ni1 O2 C16 114.7(7) . . . . ? N3 Ni1 O2 C16 -65.7(7) . . . . ? N4A Ni1 O2 C16 -162.8(8) . . . . ? N2 Ni1 O2 C16 25.1(7) . . . . ? N4 Ni1 O2 C16 -149.2(7) . . . . ? N1 Ni1 O2 C16A 73.8(8) . . . . ? N3 Ni1 O2 C16A -106.5(8) . . . . ? N4A Ni1 O2 C16A 156.4(9) . . . . ? N2 Ni1 O2 C16A -15.8(8) . . . . ? N4 Ni1 O2 C16A 170.0(8) . . . . ? O2 Ni1 N2 C3 -151.4(6) . . . . ? N1 Ni1 N2 C3 106.5(6) . . . . ? N3 Ni1 N2 C3 -45.1(6) . . . . ? N4A Ni1 N2 C3 112(3) . . . . ? N4 Ni1 N2 C3 -24(2) . . . . ? O2 Ni1 N2 C14 -4.7(6) . . . . ? N1 Ni1 N2 C14 -106.8(6) . . . . ? N3 Ni1 N2 C14 101.5(6) . . . . ? N4A Ni1 N2 C14 -102(3) . . . . ? N4 Ni1 N2 C14 123(2) . . . . ? O2 Ni1 N2 C3A 155.2(7) . . . . ? N1 Ni1 N2 C3A 53.1(8) . . . . ? N3 Ni1 N2 C3A -98.5(8) . . . . ? N4A Ni1 N2 C3A 58(3) . . . . ? N4 Ni1 N2 C3A -77(2) . . . . ? O2 Ni1 N2 C2 95.1(5) . . . . ? N1 Ni1 N2 C2 -7.0(5) . . . . ? N3 Ni1 N2 C2 -158.6(5) . . . . ? N4A Ni1 N2 C2 -2(3) . . . . ? N4 Ni1 N2 C2 -137(2) . . . . ? O2 Ni1 N2 C4A -98.3(6) . . . . ? N1 Ni1 N2 C4A 159.6(6) . . . . ? N3 Ni1 N2 C4A 8.0(6) . . . . ? N4A Ni1 N2 C4A 165(3) . . . . ? N4 Ni1 N2 C4A 29(2) . . . . ? N1 C1 C2 N2 -63.5(10) . . . . ? C3 N2 C2 C1 -84.5(10) . . . . ? C14 N2 C2 C1 158.1(8) . . . . ? C3A N2 C2 C1 -78.7(11) . . . . ? C4A N2 C2 C1 -110.4(19) . . . . ? Ni1 N2 C2 C1 35.8(8) . . . . ? O2 Ni1 N3 C6A -133.6(11) . . . . ? N1 Ni1 N3 C6A 45.6(12) . . . . ? N4A Ni1 N3 C6A -42.0(11) . . . . ? N2 Ni1 N3 C6A 134.9(11) . . . . ? N4 Ni1 N3 C6A -42.4(11) . . . . ? O2 Ni1 N3 C17 -2.1(4) . . . . ? N1 Ni1 N3 C17 177.2(4) . . . . ? N4A Ni1 N3 C17 89.6(5) . . . . ? N2 Ni1 N3 C17 -93.5(4) . . . . ? N4 Ni1 N3 C17 89.1(4) . . . . ? O2 Ni1 N3 C5 129.5(7) . . . . ? N1 Ni1 N3 C5 -51.2(9) . . . . ? N4A Ni1 N3 C5 -138.8(8) . . . . ? N2 Ni1 N3 C5 38.1(7) . . . . ? N4 Ni1 N3 C5 -139.3(7) . . . . ? O2 Ni1 N3 C5A 109.6(8) . . . . ? N1 Ni1 N3 C5A -71.1(9) . . . . ? N4A Ni1 N3 C5A -158.7(8) . . . . ? N2 Ni1 N3 C5A 18.2(8) . . . . ? N4 Ni1 N3 C5A -159.2(8) . . . . ? O2 Ni1 N3 C6 -117.5(6) . . . . ? N1 Ni1 N3 C6 61.7(7) . . . . ? N4A Ni1 N3 C6 -25.9(7) . . . . ? N2 Ni1 N3 C6 151.0(6) . . . . ? N4 Ni1 N3 C6 -26.4(6) . . . . ? C14 N2 C3 C4 -83.1(11) . . . . ? C3A N2 C3 C4 168.6(15) . . . . ? C2 N2 C3 C4 175.2(9) . . . . ? C4A N2 C3 C4 -17.9(9) . . . . ? Ni1 N2 C3 C4 65.6(10) . . . . ? O2 Ni1 N4 C8 -139.7(7) . . . . ? N1 Ni1 N4 C8 -37.2(7) . . . . ? N3 Ni1 N4 C8 114.3(7) . . . . ? N4A Ni1 N4 C8 -63.8(19) . . . . ? N2 Ni1 N4 C8 93(2) . . . . ? O2 Ni1 N4 C20 -8.2(6) . . . . ? N1 Ni1 N4 C20 94.3(6) . . . . ? N3 Ni1 N4 C20 -114.2(6) . . . . ? N4A Ni1 N4 C20 67.8(19) . . . . ? N2 Ni1 N4 C20 -135.5(18) . . . . ? O2 Ni1 N4 C7 105.3(6) . . . . ? N1 Ni1 N4 C7 -152.3(6) . . . . ? N3 Ni1 N4 C7 -0.7(6) . . . . ? N4A Ni1 N4 C7 -179(2) . . . . ? N2 Ni1 N4 C7 -22(2) . . . . ? N2 C3 C4 C5 -75.4(13) . . . . ? C6A N3 C5 C4 -165.0(12) . . . . ? C17 N3 C5 C4 77.0(10) . . . . ? C5A N3 C5 C4 4.7(18) . . . . ? C6 N3 C5 C4 -166.7(9) . . . . ? Ni1 N3 C5 C4 -52.2(11) . . . . ? C3 C4 C5 N3 66.8(13) . . . . ? C6A N3 C6 C7 169(4) . . . . ? C17 N3 C6 C7 -64.8(9) . . . . ? C5 N3 C6 C7 174.5(9) . . . . ? C5A N3 C6 C7 170.3(10) . . . . ? Ni1 N3 C6 C7 51.4(9) . . . . ? N3 C6 C7 N4 -55.4(11) . . . . ? C8 N4 C7 C6 -88.0(11) . . . . ? C20 N4 C7 C6 149.4(9) . . . . ? Ni1 N4 C7 C6 30.1(10) . . . . ? C20 N4 C8 C9 -69.7(10) . . . . ? C7 N4 C8 C9 175.4(8) . . . . ? Ni1 N4 C8 C9 60.4(9) . . . . ? N4 C8 C9 C10 -76.5(11) . . . . ? C1 N1 C10 C9 -164.8(9) . . . . ? C11 N1 C10 C9 76.4(10) . . . . ? C10A N1 C10 C9 10(3) . . . . ? C1A N1 C10 C9 -164.1(10) . . . . ? Ni1 N1 C10 C9 -52.1(10) . . . . ? C8 C9 C10 N1 71.5(12) . . . . ? C1 N1 C11 C12 -56.1(9) . . . . ? C10 N1 C11 C12 65.1(9) . . . . ? C10A N1 C11 C12 81.8(11) . . . . ? C1A N1 C11 C12 -33.7(11) . . . . ? Ni1 N1 C11 C12 -165.7(5) . . . . ? N1 C11 C12 C13 -166.9(6) . . . . ? C11 C12 C13 O1 70.9(8) . . . . ? C6A N3 C17 C18 -39.8(13) . . . . ? C5 N3 C17 C18 58.1(9) . . . . ? C5A N3 C17 C18 81.1(10) . . . . ? C6 N3 C17 C18 -55.0(8) . . . . ? Ni1 N3 C17 C18 -168.6(5) . . . . ? N3 C17 C18 C19 176.6(6) . . . . ? C17 C18 C19 O3A 107.4(8) . . . . ? C17 C18 C19 O3 -179.6(6) . . . . ? C8 N4 C20 N4A 63.3(19) . . . . ? C7 N4 C20 N4A 179(2) . . . . ? Ni1 N4 C20 N4A -65.8(19) . . . . ? C8 N4 C20 C21 -50.5(10) . . . . ? C7 N4 C20 C21 65.6(8) . . . . ? Ni1 N4 C20 C21 -179.6(5) . . . . ? N4A C20 C21 C22 163.2(9) . . . . ? N4 C20 C21 C22 -174.5(6) . . . . ? C20 C21 C22 O4 -64.5(6) . . . . ? C16 O2 C16A C15A -61.7(14) . . . . ? Ni1 O2 C16A C15A 46.3(14) . . . . ? C3 N2 C3A C2A -170.6(17) . . . . ? C14 N2 C3A C2A 91.2(12) . . . . ? C2 N2 C3A C2A 16.8(9) . . . . ? C4A N2 C3A C2A -175.8(11) . . . . ? Ni1 N2 C3A C2A -69.0(12) . . . . ? N2 C3A C2A C1A 74.5(16) . . . . ? C3 N2 C4A C5A 79.7(13) . . . . ? C14 N2 C4A C5A -155.7(11) . . . . ? C3A N2 C4A C5A 84.5(13) . . . . ? C2 N2 C4A C5A 111.7(19) . . . . ? Ni1 N2 C4A C5A -34.4(12) . . . . ? N4A C8A C7A C6A 74.4(19) . . . . ? C3A C2A C1A N1 -72.9(16) . . . . ? C1 N1 C1A C2A -6.0(14) . . . . ? C10 N1 C1A C2A 175.7(12) . . . . ? C11 N1 C1A C2A -70.8(13) . . . . ? C10A N1 C1A C2A 173.8(13) . . . . ? Ni1 N1 C1A C2A 61.6(12) . . . . ? N2 C4A C5A N3 55.8(14) . . . . ? C6A N3 C5A C4A -163.4(13) . . . . ? C17 N3 C5A C4A 70.1(12) . . . . ? C5 N3 C5A C4A -174(3) . . . . ? C6 N3 C5A C4A -163.9(10) . . . . ? Ni1 N3 C5A C4A -44.2(12) . . . . ? N4A C9A C10A N1 56.5(17) . . . . ? C1 N1 C10A C9A -164.6(10) . . . . ? C10 N1 C10A C9A -171(4) . . . . ? C11 N1 C10A C9A 70.3(13) . . . . ? C1A N1 C10A C9A -164.7(12) . . . . ? Ni1 N1 C10A C9A -47.6(13) . . . . ? C17 N3 C6A C7A -69.1(16) . . . . ? C5 N3 C6A C7A 175.9(15) . . . . ? C5A N3 C6A C7A 171.6(13) . . . . ? C6 N3 C6A C7A -10(3) . . . . ? Ni1 N3 C6A C7A 58.1(16) . . . . ? C8A C7A C6A N3 -73(2) . . . . ? O2 C16A C15A C14 -63.2(19) . . . . ? C10A C9A N4A C20 -162.0(12) . . . . ? C10A C9A N4A C8A 81.0(15) . . . . ? C10A C9A N4A Ni1 -34.5(15) . . . . ? N4 C20 N4A C9A -151(3) . . . . ? C21 C20 N4A C9A -74.1(12) . . . . ? N4 C20 N4A C8A -34.8(16) . . . . ? C21 C20 N4A C8A 42.1(13) . . . . ? N4 C20 N4A Ni1 88(2) . . . . ? C21 C20 N4A Ni1 165.3(6) . . . . ? C7A C8A N4A C9A -176.6(12) . . . . ? C7A C8A N4A C20 70.1(15) . . . . ? C7A C8A N4A Ni1 -60.0(14) . . . . ? O2 Ni1 N4A C9A -96.5(10) . . . . ? N1 Ni1 N4A C9A 5.7(9) . . . . ? N3 Ni1 N4A C9A 157.1(9) . . . . ? N2 Ni1 N4A C9A 1(4) . . . . ? N4 Ni1 N4A C9A 159(3) . . . . ? O2 Ni1 N4A C20 21.8(10) . . . . ? N1 Ni1 N4A C20 124.1(10) . . . . ? N3 Ni1 N4A C20 -84.5(10) . . . . ? N2 Ni1 N4A C20 119(3) . . . . ? N4 Ni1 N4A C20 -83(2) . . . . ? O2 Ni1 N4A C8A 146.6(9) . . . . ? N1 Ni1 N4A C8A -111.2(9) . . . . ? N3 Ni1 N4A C8A 40.2(9) . . . . ? N2 Ni1 N4A C8A -116(3) . . . . ? N4 Ni1 N4A C8A 42.2(17) . . . . ? C16A O2 C16 C15 46.6(12) . . . . ? Ni1 O2 C16 C15 -50.8(11) . . . . ? C14 C15 C16 O2 59.7(14) . . . . ? C16A C15A C14 N2 48(2) . . . . ? C16A C15A C14 C15 -35(2) . . . . ? C3 N2 C14 C15A 137.4(15) . . . . ? C3A N2 C14 C15A -168.5(15) . . . . ? C2 N2 C14 C15A -112.8(15) . . . . ? C4A N2 C14 C15A 91.4(16) . . . . ? Ni1 N2 C14 C15A -9.3(17) . . . . ? C3 N2 C14 C15 161.7(10) . . . . ? C3A N2 C14 C15 -144.2(11) . . . . ? C2 N2 C14 C15 -88.5(11) . . . . ? C4A N2 C14 C15 115.7(11) . . . . ? Ni1 N2 C14 C15 15.0(13) . . . . ? C16 C15 C14 C15A 66(3) . . . . ? C16 C15 C14 N2 -44.8(16) . . . . ? 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 H1 O9 0.84 2.34 3.093(12) 148.7 . O1 H1 O10 0.84 2.43 3.206(8) 154.8 . O2 H2 O4 0.90 1.75 2.650(6) 176.4 2_756 O4 H4 O3 0.84 1.85 2.660(7) 161.3 1_545 O3 H3 O11 0.84 2.11 2.857(8) 148.2 1_465 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.921 _refine_diff_density_min -1.378 _refine_diff_density_rms 0.141 data_AC41NEW _database_code_depnum_ccdc_archive 'CCDC 267670' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Copper(ii)(THPC)diacetate.chloride _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24.60 H52.30 Cl0.70 Cu N4 O6.80' _chemical_formula_weight 601.36 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.0421(15) _cell_length_b 8.2819(6) _cell_length_c 20.5152(15) _cell_angle_alpha 90.00 _cell_angle_beta 105.080(4) _cell_angle_gamma 90.00 _cell_volume 2795.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1293 _exptl_absorpt_coefficient_mu 0.897 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6626 _exptl_absorpt_correction_T_max 0.9157 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17013 _diffrn_reflns_av_R_equivalents 0.0999 _diffrn_reflns_av_sigmaI/netI 0.1226 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6347 _reflns_number_gt 4427 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed interface to POVRay' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0203P)^2^+4.8615P] 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 0.0020(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6347 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1142 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.23081(2) 0.48914(5) 0.21122(2) 0.01604(14) Uani 1 1 d . . . Cl1 Cl 0.10735(12) 0.0787(2) 0.20222(9) 0.0234(3) Uani 0.70 1 d P A 2 O1 O 0.29876(14) 0.7207(3) 0.20741(11) 0.0191(5) Uani 1 1 d . . . O2 O 0.50100(17) 0.4913(4) 0.10447(17) 0.0453(8) Uani 1 1 d . . . O3 O 0.18538(15) 0.9159(3) -0.01009(12) 0.0237(6) Uani 1 1 d . . . O4 O 0.22544(19) 0.8786(4) 0.43786(15) 0.0234(7) Uiso 0.80 1 d P B 1 O5 O 0.31648(14) 0.8738(3) 0.09734(12) 0.0213(6) Uani 1 1 d . . . O6 O 0.44382(15) 0.7861(3) 0.13139(13) 0.0281(6) Uani 1 1 d . . . O7 O 0.0458(5) 0.0591(10) 0.1423(4) 0.0253(19) Uiso 0.30 1 d P C 1 O8 O 0.1373(7) 0.1192(14) 0.2228(6) 0.032(3) Uiso 0.30 1 d P C 1 N1 N 0.33035(17) 0.4038(3) 0.28779(14) 0.0186(6) Uani 1 1 d . . . N2 N 0.27579(17) 0.3445(3) 0.14545(13) 0.0161(6) Uani 1 1 d . . . N3 N 0.13008(17) 0.5741(3) 0.13506(14) 0.0177(6) Uani 1 1 d . . . N4 N 0.15871(17) 0.5332(3) 0.27699(14) 0.0190(7) Uani 1 1 d . . . C1 C 0.3786(2) 0.2994(4) 0.25248(17) 0.0209(8) Uani 1 1 d . . . H1A H 0.4187 0.3663 0.2374 0.025 Uiso 1 1 calc R . . H1B H 0.4086 0.2164 0.2840 0.025 Uiso 1 1 calc R . . C2 C 0.3224(2) 0.2191(4) 0.19271(17) 0.0197(8) Uani 1 1 d . . . H2A H 0.3542 0.1518 0.1689 0.024 Uiso 1 1 calc R . . H2B H 0.2841 0.1479 0.2081 0.024 Uiso 1 1 calc R . . C3 C 0.2123(2) 0.2555(4) 0.09418(17) 0.0192(8) Uani 1 1 d . . . H3A H 0.1859 0.1764 0.1177 0.023 Uiso 1 1 calc R . . H3B H 0.2390 0.1944 0.0644 0.023 Uiso 1 1 calc R . . C4 C 0.1470(2) 0.3641(4) 0.05052(17) 0.0191(8) Uani 1 1 d . . . H4A H 0.1736 0.4515 0.0311 0.023 Uiso 1 1 calc R . . H4B H 0.1136 0.3000 0.0126 0.023 Uiso 1 1 calc R . . C5 C 0.0920(2) 0.4385(4) 0.08988(17) 0.0195(8) Uani 1 1 d . . . H5A H 0.0421 0.4788 0.0575 0.023 Uiso 1 1 calc R . . H5B H 0.0756 0.3534 0.1176 0.023 Uiso 1 1 calc R . . C6 C 0.0689(2) 0.6331(4) 0.17104(17) 0.0205(8) Uani 1 1 d . . . H6A H 0.0803 0.7471 0.1849 0.025 Uiso 1 1 calc R . . H6B H 0.0134 0.6267 0.1406 0.025 Uiso 1 1 calc R . . C7 C 0.0750(2) 0.5290(4) 0.23200(17) 0.0216(8) Uani 1 1 d . . . H7A H 0.0361 0.5678 0.2570 0.026 Uiso 1 1 calc R . . H7B H 0.0604 0.4164 0.2176 0.026 Uiso 1 1 calc R . . C8 C 0.1619(2) 0.4081(4) 0.33018(17) 0.0216(8) Uani 1 1 d . . . H8A H 0.1374 0.3073 0.3079 0.026 Uiso 1 1 calc R . . H8B H 0.1279 0.4451 0.3598 0.026 Uiso 1 1 calc R . . C9 C 0.2460(2) 0.3699(5) 0.37380(18) 0.0240(8) Uani 1 1 d . . . H9A H 0.2411 0.2954 0.4103 0.029 Uiso 1 1 calc R . . H9B H 0.2714 0.4708 0.3952 0.029 Uiso 1 1 calc R . . C10 C 0.3016(2) 0.2939(5) 0.33537(17) 0.0225(8) Uani 1 1 d . . . H10A H 0.3499 0.2503 0.3686 0.027 Uiso 1 1 calc R . . H10B H 0.2727 0.2016 0.3091 0.027 Uiso 1 1 calc R . . C11 C 0.3874(2) 0.5253(4) 0.33034(17) 0.0225(8) Uani 1 1 d . . . H11A H 0.4334 0.4654 0.3598 0.027 Uiso 1 1 calc R . . H11B H 0.3582 0.5795 0.3601 0.027 Uiso 1 1 calc R . . C12 C 0.4222(2) 0.6548(4) 0.29388(18) 0.0234(8) Uani 1 1 d . . . H12A H 0.4687 0.7060 0.3265 0.028 Uiso 1 1 calc R . . H12B H 0.4433 0.6027 0.2585 0.028 Uiso 1 1 calc R . . C13 C 0.3630(2) 0.7849(4) 0.26148(17) 0.0219(8) Uani 1 1 d . . . H13A H 0.3392 0.8343 0.2959 0.026 Uiso 1 1 calc R . . H13B H 0.3922 0.8705 0.2435 0.026 Uiso 1 1 calc R . . C14 C 0.3303(2) 0.4375(4) 0.11161(17) 0.0176(7) Uani 1 1 d . . . H14A H 0.3713 0.4954 0.1469 0.021 Uiso 1 1 calc R . . H14B H 0.2969 0.5200 0.0819 0.021 Uiso 1 1 calc R . . C15 C 0.3751(2) 0.3380(4) 0.06930(19) 0.0243(8) Uani 1 1 d . . . H15A H 0.4016 0.2440 0.0960 0.029 Uiso 1 1 calc R . . H15B H 0.3355 0.2967 0.0285 0.029 Uiso 1 1 calc R . . C16 C 0.4386(3) 0.4389(5) 0.0485(2) 0.0357(10) Uani 1 1 d . . . H16A H 0.4628 0.3746 0.0181 0.043 Uiso 1 1 calc R . . H16B H 0.4120 0.5344 0.0231 0.043 Uiso 1 1 calc R . . C17 C 0.1513(2) 0.7116(4) 0.09534(17) 0.0173(7) Uani 1 1 d . . . H17A H 0.1994 0.6800 0.0797 0.021 Uiso 1 1 calc R . . H17B H 0.1672 0.8049 0.1261 0.021 Uiso 1 1 calc R . . C18 C 0.0850(2) 0.7667(4) 0.03424(17) 0.0190(8) Uani 1 1 d . . . H18A H 0.0765 0.6835 -0.0016 0.023 Uiso 1 1 calc R . . H18B H 0.0333 0.7810 0.0471 0.023 Uiso 1 1 calc R . . C19 C 0.1095(2) 0.9251(4) 0.00788(18) 0.0203(8) Uani 1 1 d . . . H19A H 0.0664 0.9585 -0.0323 0.024 Uiso 1 1 calc R . . H19B H 0.1137 1.0092 0.0429 0.024 Uiso 1 1 calc R . . C20 C 0.1807(2) 0.6976(4) 0.30709(17) 0.0200(8) Uani 1 1 d . . . H20A H 0.1903 0.7694 0.2713 0.024 Uiso 1 1 calc R . . H20B H 0.2327 0.6885 0.3423 0.024 Uiso 1 1 calc R . . C21 C 0.1188(2) 0.7791(5) 0.33838(18) 0.0241(8) Uani 1 1 d . . . H21A H 0.0986 0.7008 0.3667 0.029 Uiso 1 1 calc R D 1 H21B H 0.0719 0.8178 0.3023 0.029 Uiso 1 1 calc R D 1 C22 C 0.1608(4) 0.9256(8) 0.3828(3) 0.0220(16) Uiso 0.80 1 d P B 1 H22A H 0.1817 1.0014 0.3540 0.026 Uiso 0.80 1 calc PR B 1 H22B H 0.1196 0.9837 0.4001 0.026 Uiso 0.80 1 calc PR B 1 C23 C 0.3981(2) 0.8919(5) 0.01963(19) 0.0302(9) Uani 1 1 d . . . H23A H 0.4553 0.8781 0.0201 0.045 Uiso 1 1 calc R . . H23B H 0.3821 1.0047 0.0094 0.045 Uiso 1 1 calc R . . H23C H 0.3643 0.8217 -0.0150 0.045 Uiso 1 1 calc R . . C24 C 0.3863(2) 0.8476(4) 0.08814(18) 0.0195(8) Uani 1 1 d . . . C25 C 0.0879(6) 0.0432(11) 0.1871(4) 0.017(5) Uiso 0.30 1 d P C 1 H1 H 0.3143 0.7589 0.1673 0.020 Uiso 1 1 d R . . H3 H 0.2243 0.9195 0.0326 0.020 Uiso 1 1 d R . . H4 H 0.2174 0.8063 0.4535 0.020 Uiso 0.80 1 d PR E 1 H2 H 0.4855 0.5973 0.1101 0.020 Uiso 1 1 d R . . O4A O 0.1879(6) 1.0108(11) 0.3533(4) 0.045(4) Uiso 0.20 1 d PR B 2 H4A1 H 0.2365 1.0076 0.3760 0.054 Uiso 0.20 1 calc PR F 2 O1S O 0.3453(6) 0.9116(11) 0.4213(4) 0.072(6) Uiso 0.20 1 d PR G 2 C22A C 0.1430(15) 0.897(3) 0.3779(12) 0.017(6) Uiso 0.20 1 d P B 2 H22C H 0.1768 0.8547 0.4213 0.021 Uiso 0.20 1 calc PR B 2 H22D H 0.0952 0.9508 0.3871 0.021 Uiso 0.20 1 calc PR B 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 Cu1 0.0142(2) 0.0197(2) 0.0136(2) -0.00075(18) 0.00254(15) 0.00065(19) Cl1 0.0268(9) 0.0242(8) 0.0216(8) 0.0013(8) 0.0104(8) -0.0048(8) O1 0.0160(13) 0.0248(14) 0.0157(13) -0.0029(10) 0.0024(10) -0.0050(10) O2 0.0217(15) 0.0327(17) 0.082(2) 0.0109(17) 0.0142(15) 0.0029(14) O3 0.0261(15) 0.0246(14) 0.0192(13) 0.0002(11) 0.0037(11) -0.0051(11) O5 0.0166(14) 0.0236(14) 0.0231(14) -0.0003(11) 0.0039(11) -0.0012(10) O6 0.0190(14) 0.0361(16) 0.0260(15) 0.0030(12) 0.0002(12) -0.0017(12) N1 0.0180(16) 0.0210(16) 0.0154(15) -0.0007(12) 0.0020(12) 0.0042(13) N2 0.0172(16) 0.0166(15) 0.0136(15) 0.0007(12) 0.0023(12) -0.0030(12) N3 0.0169(16) 0.0190(15) 0.0162(15) -0.0005(12) 0.0024(12) -0.0044(12) N4 0.0167(15) 0.0220(17) 0.0174(15) 0.0015(12) 0.0028(12) 0.0017(12) C1 0.0187(19) 0.024(2) 0.0199(19) -0.0005(15) 0.0051(15) 0.0058(15) C2 0.023(2) 0.0185(19) 0.0177(19) 0.0017(15) 0.0062(16) 0.0029(15) C3 0.022(2) 0.0186(18) 0.0167(18) -0.0038(14) 0.0041(15) -0.0054(15) C4 0.023(2) 0.0161(18) 0.0150(18) -0.0003(14) -0.0006(15) -0.0084(15) C5 0.0161(18) 0.0197(18) 0.0182(18) 0.0031(14) -0.0033(15) -0.0034(15) C6 0.0119(18) 0.028(2) 0.0198(19) -0.0018(15) 0.0019(15) 0.0029(15) C7 0.0155(18) 0.027(2) 0.0221(19) 0.0023(15) 0.0045(15) 0.0018(15) C8 0.024(2) 0.024(2) 0.0192(19) 0.0044(15) 0.0091(16) 0.0026(16) C9 0.027(2) 0.030(2) 0.0157(19) 0.0047(16) 0.0058(16) 0.0028(17) C10 0.022(2) 0.027(2) 0.0158(18) 0.0058(15) 0.0005(15) 0.0065(16) C11 0.0189(19) 0.029(2) 0.0156(18) -0.0063(16) -0.0019(15) 0.0033(16) C12 0.0164(19) 0.028(2) 0.021(2) -0.0073(16) -0.0037(15) 0.0013(16) C13 0.022(2) 0.024(2) 0.0184(19) -0.0082(15) 0.0023(16) -0.0058(16) C14 0.0169(18) 0.0189(18) 0.0161(18) -0.0002(14) 0.0024(15) -0.0016(14) C15 0.030(2) 0.0190(19) 0.028(2) -0.0007(16) 0.0137(18) 0.0019(16) C16 0.039(3) 0.029(2) 0.047(3) 0.0030(19) 0.025(2) 0.0015(19) C17 0.0155(18) 0.0126(17) 0.0216(19) 0.0002(14) 0.0011(15) -0.0034(14) C18 0.0185(19) 0.0201(19) 0.0164(18) -0.0001(15) 0.0010(15) -0.0015(15) C19 0.0187(19) 0.0204(18) 0.0196(19) -0.0006(15) 0.0009(15) 0.0002(15) C20 0.0178(19) 0.026(2) 0.0155(18) -0.0003(15) 0.0032(15) 0.0036(15) C21 0.026(2) 0.030(2) 0.0181(19) 0.0040(16) 0.0099(16) 0.0059(17) C23 0.029(2) 0.036(2) 0.028(2) 0.0050(18) 0.0123(18) 0.0009(18) C24 0.019(2) 0.0164(18) 0.022(2) -0.0032(15) 0.0035(16) -0.0043(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 2.080(3) . ? Cu1 N2 2.093(3) . ? Cu1 N1 2.111(3) . ? Cu1 N3 2.118(3) . ? Cu1 O1 2.252(2) . ? O1 C13 1.442(4) . ? O2 C16 1.415(5) . ? O3 C19 1.436(4) . ? O4 C22 1.412(7) . ? O5 C24 1.271(4) . ? O6 C24 1.247(4) . ? O7 C25 1.017(11) . ? O8 C25 1.150(14) . ? N1 C1 1.503(4) . ? N1 C10 1.507(4) . ? N1 C11 1.509(4) . ? N2 C3 1.493(4) . ? N2 C2 1.499(4) . ? N2 C14 1.507(4) . ? N3 C5 1.493(4) . ? N3 C17 1.498(4) . ? N3 C6 1.507(4) . ? N4 C7 1.485(4) . ? N4 C8 1.496(4) . ? N4 C20 1.502(4) . ? C1 C2 1.501(5) . ? C3 C4 1.527(5) . ? C4 C5 1.518(5) . ? C6 C7 1.501(5) . ? C8 C9 1.514(5) . ? C9 C10 1.517(5) . ? C11 C12 1.514(5) . ? C12 C13 1.508(5) . ? C14 C15 1.537(5) . ? C15 C16 1.513(5) . ? C17 C18 1.523(5) . ? C18 C19 1.518(5) . ? C20 C21 1.527(5) . ? C21 C22A 1.27(2) . ? C21 C22 1.573(7) . ? C23 C24 1.516(5) . ? O4A C22A 1.39(2) . ? 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 N4 Cu1 N2 153.62(11) . . ? N4 Cu1 N1 94.12(11) . . ? N2 Cu1 N1 85.99(11) . . ? N4 Cu1 N3 85.30(11) . . ? N2 Cu1 N3 94.42(11) . . ? N1 Cu1 N3 179.37(11) . . ? N4 Cu1 O1 105.60(10) . . ? N2 Cu1 O1 100.78(9) . . ? N1 Cu1 O1 89.42(10) . . ? N3 Cu1 O1 90.98(10) . . ? C13 O1 Cu1 125.6(2) . . ? C1 N1 C10 106.0(3) . . ? C1 N1 C11 108.1(3) . . ? C10 N1 C11 107.3(3) . . ? C1 N1 Cu1 105.6(2) . . ? C10 N1 Cu1 110.5(2) . . ? C11 N1 Cu1 118.6(2) . . ? C3 N2 C2 106.2(3) . . ? C3 N2 C14 110.4(2) . . ? C2 N2 C14 111.5(3) . . ? C3 N2 Cu1 114.6(2) . . ? C2 N2 Cu1 101.57(19) . . ? C14 N2 Cu1 112.2(2) . . ? C5 N3 C17 111.2(3) . . ? C5 N3 C6 107.7(3) . . ? C17 N3 C6 108.4(3) . . ? C5 N3 Cu1 110.3(2) . . ? C17 N3 Cu1 112.9(2) . . ? C6 N3 Cu1 106.11(19) . . ? C7 N4 C8 106.5(3) . . ? C7 N4 C20 111.9(3) . . ? C8 N4 C20 111.7(3) . . ? C7 N4 Cu1 103.13(19) . . ? C8 N4 Cu1 115.9(2) . . ? C20 N4 Cu1 107.4(2) . . ? C2 C1 N1 109.6(3) . . ? N2 C2 C1 109.9(3) . . ? N2 C3 C4 114.0(3) . . ? C5 C4 C3 112.6(3) . . ? N3 C5 C4 114.0(3) . . ? C7 C6 N3 108.4(3) . . ? N4 C7 C6 110.5(3) . . ? N4 C8 C9 115.1(3) . . ? C8 C9 C10 113.8(3) . . ? N1 C10 C9 116.0(3) . . ? N1 C11 C12 117.5(3) . . ? C13 C12 C11 114.9(3) . . ? O1 C13 C12 111.2(3) . . ? N2 C14 C15 116.2(3) . . ? C16 C15 C14 111.1(3) . . ? O2 C16 C15 112.5(3) . . ? N3 C17 C18 116.3(3) . . ? C19 C18 C17 109.8(3) . . ? O3 C19 C18 113.3(3) . . ? N4 C20 C21 116.6(3) . . ? C22A C21 C20 117.6(11) . . ? C22A C21 C22 9.0(11) . . ? C20 C21 C22 108.9(3) . . ? O4 C22 C21 113.2(4) . . ? O6 C24 O5 123.9(3) . . ? O6 C24 C23 119.3(3) . . ? O5 C24 C23 116.8(3) . . ? O7 C25 O8 137.1(12) . . ? C21 C22A O4A 114.1(16) . . ? 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 N4 Cu1 O1 C13 70.4(3) . . . . ? N2 Cu1 O1 C13 -109.5(2) . . . . ? N1 Cu1 O1 C13 -23.7(2) . . . . ? N3 Cu1 O1 C13 155.8(2) . . . . ? N4 Cu1 N1 C1 156.9(2) . . . . ? N2 Cu1 N1 C1 3.4(2) . . . . ? N3 Cu1 N1 C1 133(11) . . . . ? O1 Cu1 N1 C1 -97.5(2) . . . . ? N4 Cu1 N1 C10 42.7(2) . . . . ? N2 Cu1 N1 C10 -110.8(2) . . . . ? N3 Cu1 N1 C10 19(11) . . . . ? O1 Cu1 N1 C10 148.3(2) . . . . ? N4 Cu1 N1 C11 -81.7(2) . . . . ? N2 Cu1 N1 C11 124.7(2) . . . . ? N3 Cu1 N1 C11 -105(11) . . . . ? O1 Cu1 N1 C11 23.9(2) . . . . ? N4 Cu1 N2 C3 47.7(4) . . . . ? N1 Cu1 N2 C3 138.9(2) . . . . ? N3 Cu1 N2 C3 -40.6(2) . . . . ? O1 Cu1 N2 C3 -132.5(2) . . . . ? N4 Cu1 N2 C2 -66.3(3) . . . . ? N1 Cu1 N2 C2 24.9(2) . . . . ? N3 Cu1 N2 C2 -154.6(2) . . . . ? O1 Cu1 N2 C2 113.53(19) . . . . ? N4 Cu1 N2 C14 174.6(2) . . . . ? N1 Cu1 N2 C14 -94.2(2) . . . . ? N3 Cu1 N2 C14 86.2(2) . . . . ? O1 Cu1 N2 C14 -5.6(2) . . . . ? N4 Cu1 N3 C5 -110.6(2) . . . . ? N2 Cu1 N3 C5 43.0(2) . . . . ? N1 Cu1 N3 C5 -87(11) . . . . ? O1 Cu1 N3 C5 143.9(2) . . . . ? N4 Cu1 N3 C17 124.4(2) . . . . ? N2 Cu1 N3 C17 -82.1(2) . . . . ? N1 Cu1 N3 C17 148(11) . . . . ? O1 Cu1 N3 C17 18.8(2) . . . . ? N4 Cu1 N3 C6 5.8(2) . . . . ? N2 Cu1 N3 C6 159.3(2) . . . . ? N1 Cu1 N3 C6 29(11) . . . . ? O1 Cu1 N3 C6 -99.8(2) . . . . ? N2 Cu1 N4 C7 -67.8(3) . . . . ? N1 Cu1 N4 C7 -157.1(2) . . . . ? N3 Cu1 N4 C7 22.7(2) . . . . ? O1 Cu1 N4 C7 112.4(2) . . . . ? N2 Cu1 N4 C8 48.1(4) . . . . ? N1 Cu1 N4 C8 -41.2(2) . . . . ? N3 Cu1 N4 C8 138.6(2) . . . . ? O1 Cu1 N4 C8 -131.7(2) . . . . ? N2 Cu1 N4 C20 173.8(2) . . . . ? N1 Cu1 N4 C20 84.6(2) . . . . ? N3 Cu1 N4 C20 -95.7(2) . . . . ? O1 Cu1 N4 C20 -6.0(2) . . . . ? C10 N1 C1 C2 85.1(3) . . . . ? C11 N1 C1 C2 -160.1(3) . . . . ? Cu1 N1 C1 C2 -32.1(3) . . . . ? C3 N2 C2 C1 -170.8(3) . . . . ? C14 N2 C2 C1 69.0(3) . . . . ? Cu1 N2 C2 C1 -50.6(3) . . . . ? N1 C1 C2 N2 58.4(4) . . . . ? C2 N2 C3 C4 167.5(3) . . . . ? C14 N2 C3 C4 -71.6(3) . . . . ? Cu1 N2 C3 C4 56.2(3) . . . . ? N2 C3 C4 C5 -69.4(4) . . . . ? C17 N3 C5 C4 62.2(4) . . . . ? C6 N3 C5 C4 -179.2(3) . . . . ? Cu1 N3 C5 C4 -63.9(3) . . . . ? C3 C4 C5 N3 75.6(4) . . . . ? C5 N3 C6 C7 84.5(3) . . . . ? C17 N3 C6 C7 -155.1(3) . . . . ? Cu1 N3 C6 C7 -33.6(3) . . . . ? C8 N4 C7 C6 -171.7(3) . . . . ? C20 N4 C7 C6 66.0(3) . . . . ? Cu1 N4 C7 C6 -49.2(3) . . . . ? N3 C6 C7 N4 57.8(4) . . . . ? C7 N4 C8 C9 169.0(3) . . . . ? C20 N4 C8 C9 -68.5(4) . . . . ? Cu1 N4 C8 C9 55.0(4) . . . . ? N4 C8 C9 C10 -64.7(4) . . . . ? C1 N1 C10 C9 -175.9(3) . . . . ? C11 N1 C10 C9 68.7(4) . . . . ? Cu1 N1 C10 C9 -62.0(3) . . . . ? C8 C9 C10 N1 71.0(4) . . . . ? C1 N1 C11 C12 68.5(4) . . . . ? C10 N1 C11 C12 -177.5(3) . . . . ? Cu1 N1 C11 C12 -51.5(4) . . . . ? N1 C11 C12 C13 73.4(4) . . . . ? Cu1 O1 C13 C12 44.2(4) . . . . ? C11 C12 C13 O1 -65.5(4) . . . . ? C3 N2 C14 C15 -58.4(4) . . . . ? C2 N2 C14 C15 59.3(4) . . . . ? Cu1 N2 C14 C15 172.5(2) . . . . ? N2 C14 C15 C16 -169.9(3) . . . . ? C14 C15 C16 O2 63.8(4) . . . . ? C5 N3 C17 C18 48.3(4) . . . . ? C6 N3 C17 C18 -69.9(4) . . . . ? Cu1 N3 C17 C18 172.9(2) . . . . ? N3 C17 C18 C19 169.0(3) . . . . ? C17 C18 C19 O3 57.6(4) . . . . ? C7 N4 C20 C21 48.2(4) . . . . ? C8 N4 C20 C21 -71.1(4) . . . . ? Cu1 N4 C20 C21 160.7(2) . . . . ? N4 C20 C21 C22A 163.2(12) . . . . ? N4 C20 C21 C22 165.6(3) . . . . ? C22A C21 C22 O4 103(8) . . . . ? C20 C21 C22 O4 -63.1(5) . . . . ? C20 C21 C22A O4A 47(2) . . . . ? C22 C21 C22A O4A 33(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O5 0.98 1.73 2.675(3) 160.4 . O1 H1 O6 0.98 2.51 3.293(3) 136.5 . O3 H3 O5 0.95 1.81 2.722(3) 158.6 . O2 H2 O6 0.93 1.82 2.738(4) 168.7 . O4A H4A1 O1S 0.84 2.01 2.807 158.2 . O4 H4 O3 0.71 2.11 2.816(4) 173.9 4_576 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.595 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.085