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 Petr Hermann' _publ_contact_author_address ; Department of Inorganic Chemistry Universita Karlova Hlavova 2030 Prague 2 128 40 CZECH REPUBLIC ; _publ_contact_author_email PETRH@NATUR.CUNI.CZ _publ_section_title ; Cyclam (1,4,8,11-tetraazacyclotetradecane) with one methylphosphonate pendant arm: a new ligand for selective copper(II) binding ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, p. 435. Coppens, P. (1970). Crystallographic Computing, edited by F.R. Ahmed, S.R.Hall & C.P. Huber, pp. 255-270, Copenhagen, Munksgaard. Hooft, R.W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods Enzymol. 276, 307--326. Sheldrick, G. M. (1997). SHELXL97. University of G\"ottingen, Germany. Spek, A.L. (1999). PLATON. Version 1999. Utrecht University, The Netherlands. ; loop_ _publ_author_name 'Petr Hermann' 'Koen Binnemans' 'Ivana Cisarova' 'Silvia Fuzerova' 'Jan Kotek' 'Ivan Lukes' data_monop _database_code_depnum_ccdc_archive 'CCDC 272438' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (1,4,8,11-tetraazacyclotetradecane-1-yl)methylphosphonic acid tribromide tetrahydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C11 H30 N4 O3 P, 3(Br), 4(H2 O)' _chemical_formula_sum 'C11 H38 Br3 N4 O7 P' _chemical_formula_weight 606.63 _chemical_compound_source 'synthesized by the authors' 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 19.8259(4) _cell_length_b 7.6318(2) _cell_length_c 16.3772(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.0446(17) _cell_angle_gamma 90.00 _cell_volume 2356.15(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 89248 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.710 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1222 _exptl_absorpt_coefficient_mu 5.240 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.17849 _exptl_absorpt_correction_T_max 0.89669 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34460 _diffrn_reflns_av_R_equivalents 0.0783 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.10 _reflns_number_total 5190 _reflns_number_gt 4022 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1106P)^2^+15.9853P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5190 _refine_ls_number_parameters 243 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.2085 _refine_ls_wR_factor_gt 0.1932 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.19187(5) 0.50767(9) 0.25005(4) 0.0396(2) Uani 1 1 d . . . Br2 Br 0.01464(4) 0.73112(9) 0.09138(5) 0.0352(2) Uani 1 1 d . . . Br3 Br 0.23245(5) 0.14579(10) 0.04224(5) 0.0462(3) Uani 1 1 d . . . N1 N 0.3494(4) 0.0333(10) 0.3627(5) 0.0489(18) Uani 1 1 d D . . C2 C 0.2809(4) -0.0686(9) 0.3363(5) 0.0342(15) Uani 1 1 d . A . H21 H 0.2609 -0.0697 0.3833 0.041 Uiso 1 1 calc R . . H22 H 0.2905 -0.1889 0.3243 0.041 Uiso 1 1 calc R . . C3 C 0.2273(4) 0.0103(9) 0.2571(4) 0.0307(14) Uani 1 1 d . . . H31 H 0.2231 0.1350 0.2659 0.037 Uiso 1 1 calc R A . H32 H 0.2442 -0.0049 0.2079 0.037 Uiso 1 1 calc R . . N4 N 0.1555(3) -0.0743(7) 0.2388(4) 0.0306(12) Uani 1 1 d . A . H41 H 0.1600 -0.1887 0.2282 0.037 Uiso 1 1 calc R . . H42 H 0.1264 -0.0266 0.1905 0.037 Uiso 1 1 calc R . . C5 C 0.1202(4) -0.0604(9) 0.3080(5) 0.0327(15) Uani 1 1 d . . . H51 H 0.0744 -0.1179 0.2886 0.039 Uiso 1 1 calc R A . H52 H 0.1490 -0.1208 0.3590 0.039 Uiso 1 1 calc R . . C6 C 0.1102(5) 0.1260(9) 0.3303(5) 0.0391(17) Uani 1 1 d . A . H61 H 0.0783 0.1839 0.2805 0.047 Uiso 1 1 calc R . . H62 H 0.1555 0.1863 0.3451 0.047 Uiso 1 1 calc R . . C7 C 0.0806(4) 0.1392(9) 0.4041(5) 0.0328(15) Uani 1 1 d . . . H71 H 0.1114 0.0772 0.4533 0.039 Uiso 1 1 calc R A . H72 H 0.0343 0.0840 0.3885 0.039 Uiso 1 1 calc R . . N8 N 0.0741(3) 0.3271(8) 0.4280(4) 0.0342(13) Uani 1 1 d . A . H81 H 0.0431 0.3808 0.3829 0.041 Uiso 1 1 calc R . . H82 H 0.0552 0.3290 0.4715 0.041 Uiso 1 1 calc R . . C9 C 0.1411(4) 0.4322(9) 0.4544(4) 0.0343(15) Uani 1 1 d . . . H91 H 0.1304 0.5515 0.4667 0.041 Uiso 1 1 calc R A . H92 H 0.1612 0.4355 0.4075 0.041 Uiso 1 1 calc R . . C10 C 0.1948(4) 0.3547(10) 0.5331(5) 0.0400(17) Uani 1 1 d . A . H101 H 0.1775 0.3674 0.5820 0.048 Uiso 1 1 calc R . . H102 H 0.1999 0.2305 0.5238 0.048 Uiso 1 1 calc R . . N11 N 0.2650(4) 0.4403(9) 0.5524(4) 0.0428(16) Uani 1 1 d . . . H111 H 0.2938 0.3941 0.6014 0.051 Uiso 1 1 calc R A . H112 H 0.2597 0.5548 0.5622 0.051 Uiso 1 1 calc R . . C12 C 0.3008(4) 0.4248(11) 0.4840(5) 0.0422(18) Uani 1 1 d . A . H121 H 0.3463 0.4842 0.5030 0.051 Uiso 1 1 calc R . . H122 H 0.2719 0.4819 0.4320 0.051 Uiso 1 1 calc R . . C13 C 0.3122(6) 0.2332(11) 0.4644(6) 0.051(2) Uani 1 1 d . . . H131 H 0.3449 0.1790 0.5148 0.062 Uiso 1 1 calc R A . H132 H 0.2675 0.1709 0.4508 0.062 Uiso 1 1 calc R . . C14 C 0.3419(5) 0.2185(12) 0.3894(6) 0.048(2) Uani 1 1 d . A . H141 H 0.3108 0.2814 0.3407 0.057 Uiso 1 1 calc R . . H142 H 0.3880 0.2748 0.4050 0.057 Uiso 1 1 calc R . . C15A C 0.3774(15) 0.051(2) 0.2835(14) 0.099(9) Uiso 0.50 1 d PD A 1 H15A H 0.4183 0.1285 0.2991 0.119 Uiso 0.50 1 calc PR A 1 H15X H 0.3409 0.1074 0.2372 0.119 Uiso 0.50 1 calc PR A 1 P1A P 0.4015(4) -0.1460(15) 0.2448(6) 0.121(4) Uani 0.50 1 d PD A 1 O11A O 0.4629(15) -0.099(5) 0.213(2) 0.27(2) Uiso 0.50 1 d PD . 1 O12A O 0.3454(7) -0.2369(19) 0.1868(9) 0.067(4) Uiso 0.50 1 d PD A 1 O13A O 0.432(2) -0.268(4) 0.3200(19) 0.24(2) Uiso 0.50 1 d PD A 1 O4WA O 0.4542(12) -0.195(3) 0.5043(16) 0.091(6) Uiso 0.50 1 d P B 1 O5WX O 0.4691(9) -0.111(2) 0.5169(11) 0.069(4) Uiso 0.50 1 d P B 1 O5WY O 0.4415(7) -0.1682(18) 0.5420(9) 0.049(3) Uiso 0.50 1 d P B 1 C15B C 0.3929(12) -0.071(3) 0.4436(12) 0.080(7) Uiso 0.50 1 d PD A 2 H15B H 0.3600 -0.1137 0.4722 0.095 Uiso 0.50 1 calc PR A 2 H15Y H 0.4246 0.0110 0.4825 0.095 Uiso 0.50 1 calc PR A 2 P1B P 0.4461(4) -0.2571(10) 0.4279(6) 0.092(2) Uani 0.50 1 d PD A 2 O11B O 0.3971(10) -0.369(3) 0.3562(12) 0.105(6) Uiso 0.50 1 d PD A 2 O12B O 0.4766(17) -0.377(4) 0.5080(17) 0.175(12) Uiso 0.50 1 d PD A 2 O13B O 0.5035(15) -0.183(4) 0.396(2) 0.171(12) Uiso 0.50 1 d PD A 2 O4WB O 0.3814(8) -0.333(2) 0.2221(10) 0.070(4) Uiso 0.50 1 d P . 2 O1W O 0.0000 0.4614(10) 0.2500 0.0436(18) Uani 1 2 d S . . O2W O 0.0864(3) 0.2038(7) 0.1248(3) 0.0377(11) Uani 1 1 d . . . O3W O 0.4104(7) 0.500(2) 0.1637(9) 0.078(5) Uani 0.50 1 d P . . 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 Br1 0.0666(5) 0.0205(3) 0.0311(4) 0.0009(3) 0.0143(3) -0.0029(3) Br2 0.0387(4) 0.0291(4) 0.0411(4) -0.0054(3) 0.0170(3) -0.0037(3) Br3 0.0803(6) 0.0293(4) 0.0348(4) -0.0017(3) 0.0261(4) 0.0000(4) N1 0.036(4) 0.050(4) 0.060(4) -0.023(3) 0.014(3) -0.004(3) C2 0.040(4) 0.025(3) 0.036(4) -0.004(3) 0.011(3) 0.000(3) C3 0.038(4) 0.027(3) 0.031(3) -0.004(3) 0.017(3) -0.004(3) N4 0.043(3) 0.021(3) 0.028(3) -0.007(2) 0.011(2) 0.000(2) C5 0.036(4) 0.027(3) 0.042(4) -0.004(3) 0.022(3) -0.004(3) C6 0.060(5) 0.030(4) 0.035(4) 0.005(3) 0.028(3) 0.011(3) C7 0.040(4) 0.024(3) 0.037(4) -0.006(3) 0.017(3) 0.000(3) N8 0.045(3) 0.030(3) 0.031(3) -0.004(2) 0.016(3) 0.004(3) C9 0.046(4) 0.028(3) 0.032(3) -0.005(3) 0.015(3) 0.005(3) C10 0.055(5) 0.039(4) 0.027(3) -0.003(3) 0.015(3) 0.006(3) N11 0.050(4) 0.036(3) 0.034(3) -0.010(3) -0.001(3) 0.010(3) C12 0.038(4) 0.037(4) 0.048(4) -0.009(3) 0.007(3) -0.007(3) C13 0.073(6) 0.032(4) 0.055(5) -0.006(4) 0.027(5) 0.001(4) C14 0.042(4) 0.048(5) 0.051(5) -0.019(4) 0.011(4) -0.012(4) P1A 0.056(4) 0.207(11) 0.113(6) -0.071(7) 0.045(4) -0.007(5) P1B 0.058(4) 0.075(4) 0.139(7) -0.003(4) 0.023(4) 0.006(3) O1W 0.071(5) 0.027(4) 0.035(4) 0.000 0.020(4) 0.000 O2W 0.044(3) 0.041(3) 0.030(2) 0.000(2) 0.014(2) -0.003(2) O3W 0.042(7) 0.109(12) 0.053(7) 0.037(8) -0.031(6) -0.037(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 N1 C14 1.500(11) . ? N1 C2 1.508(10) . ? N1 C15B 1.555(16) . ? N1 C15A 1.567(17) . ? C2 C3 1.523(10) . ? C2 H21 0.9700 . ? C2 H22 0.9700 . ? C3 N4 1.506(9) . ? C3 H31 0.9700 . ? C3 H32 0.9700 . ? N4 C5 1.508(9) . ? N4 H41 0.9000 . ? N4 H42 0.9000 . ? C5 C6 1.497(9) . ? C5 H51 0.9700 . ? C5 H52 0.9700 . ? C6 C7 1.502(10) . ? C6 H61 0.9700 . ? C6 H62 0.9700 . ? C7 N8 1.503(8) . ? C7 H71 0.9700 . ? C7 H72 0.9700 . ? N8 C9 1.497(10) . ? N8 H81 0.9000 . ? N8 H82 0.9000 . ? C9 C10 1.514(10) . ? C9 H91 0.9700 . ? C9 H92 0.9700 . ? C10 N11 1.479(11) . ? C10 H101 0.9700 . ? C10 H102 0.9700 . ? N11 C12 1.506(11) . ? N11 H111 0.9000 . ? N11 H112 0.9000 . ? C12 C13 1.529(11) . ? C12 H121 0.9700 . ? C12 H122 0.9700 . ? C13 C14 1.521(12) . ? C13 H131 0.9700 . ? C13 H132 0.9700 . ? C14 H141 0.9700 . ? C14 H142 0.9700 . ? C15A P1A 1.757(16) . ? C15A H15A 0.9700 . ? C15A H15X 0.9700 . ? P1A O12A 1.402(12) . ? P1A O11A 1.507(17) . ? P1A O13A 1.515(17) . ? O11A O11A 1.58(7) 2_655 ? O4WA O5WX 0.70(2) . ? O4WA O5WY 0.76(2) . ? O5WX O5WY 0.89(2) . ? C15B P1B 1.837(16) . ? C15B H15B 0.9700 . ? C15B H15Y 0.9700 . ? P1B O13B 1.504(18) . ? P1B O11B 1.532(15) . ? P1B O12B 1.559(18) . ? O4WB O3W 1.79(2) 1_545 ? O3W O4WB 1.79(2) 1_565 ? 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 C14 N1 C2 114.0(6) . . ? C14 N1 C15B 108.2(9) . . ? C2 N1 C15B 101.1(11) . . ? C14 N1 C15A 104.5(9) . . ? C2 N1 C15A 109.0(11) . . ? C15B N1 C15A 120.4(13) . . ? N1 C2 C3 111.7(6) . . ? N1 C2 H21 109.3 . . ? C3 C2 H21 109.3 . . ? N1 C2 H22 109.3 . . ? C3 C2 H22 109.3 . . ? H21 C2 H22 107.9 . . ? N4 C3 C2 111.5(6) . . ? N4 C3 H31 109.3 . . ? C2 C3 H31 109.3 . . ? N4 C3 H32 109.3 . . ? C2 C3 H32 109.3 . . ? H31 C3 H32 108.0 . . ? C3 N4 C5 116.7(5) . . ? C3 N4 H41 108.1 . . ? C5 N4 H41 108.1 . . ? C3 N4 H42 108.1 . . ? C5 N4 H42 108.1 . . ? H41 N4 H42 107.3 . . ? C6 C5 N4 112.2(6) . . ? C6 C5 H51 109.2 . . ? N4 C5 H51 109.2 . . ? C6 C5 H52 109.2 . . ? N4 C5 H52 109.2 . . ? H51 C5 H52 107.9 . . ? C5 C6 C7 112.0(6) . . ? C5 C6 H61 109.2 . . ? C7 C6 H61 109.2 . . ? C5 C6 H62 109.2 . . ? C7 C6 H62 109.2 . . ? H61 C6 H62 107.9 . . ? C6 C7 N8 111.1(6) . . ? C6 C7 H71 109.4 . . ? N8 C7 H71 109.4 . . ? C6 C7 H72 109.4 . . ? N8 C7 H72 109.4 . . ? H71 C7 H72 108.0 . . ? C9 N8 C7 116.5(6) . . ? C9 N8 H81 108.2 . . ? C7 N8 H81 108.2 . . ? C9 N8 H82 108.2 . . ? C7 N8 H82 108.2 . . ? H81 N8 H82 107.3 . . ? N8 C9 C10 111.4(6) . . ? N8 C9 H91 109.4 . . ? C10 C9 H91 109.4 . . ? N8 C9 H92 109.4 . . ? C10 C9 H92 109.4 . . ? H91 C9 H92 108.0 . . ? N11 C10 C9 112.1(6) . . ? N11 C10 H101 109.2 . . ? C9 C10 H101 109.2 . . ? N11 C10 H102 109.2 . . ? C9 C10 H102 109.2 . . ? H101 C10 H102 107.9 . . ? C10 N11 C12 115.7(6) . . ? C10 N11 H111 108.3 . . ? C12 N11 H111 108.3 . . ? C10 N11 H112 108.3 . . ? C12 N11 H112 108.3 . . ? H111 N11 H112 107.4 . . ? N11 C12 C13 111.5(7) . . ? N11 C12 H121 109.3 . . ? C13 C12 H121 109.3 . . ? N11 C12 H122 109.3 . . ? C13 C12 H122 109.3 . . ? H121 C12 H122 108.0 . . ? C14 C13 C12 111.1(7) . . ? C14 C13 H131 109.4 . . ? C12 C13 H131 109.4 . . ? C14 C13 H132 109.4 . . ? C12 C13 H132 109.4 . . ? H131 C13 H132 108.0 . . ? N1 C14 C13 113.7(7) . . ? N1 C14 H141 108.8 . . ? C13 C14 H141 108.8 . . ? N1 C14 H142 108.8 . . ? C13 C14 H142 108.8 . . ? H141 C14 H142 107.7 . . ? N1 C15A P1A 115.4(12) . . ? N1 C15A H15A 108.4 . . ? P1A C15A H15A 108.4 . . ? N1 C15A H15X 108.4 . . ? P1A C15A H15X 108.4 . . ? H15A C15A H15X 107.5 . . ? O12A P1A O11A 116.2(16) . . ? O12A P1A O13A 106.3(17) . . ? O11A P1A O13A 105.1(18) . . ? O12A P1A C15A 115.0(12) . . ? O11A P1A C15A 104.9(16) . . ? O13A P1A C15A 108.8(16) . . ? P1A O11A O11A 113(3) . 2_655 ? O5WX O4WA O5WY 75(3) . . ? O4WA O5WX O5WY 55(2) . . ? O4WA O5WY O5WX 50(2) . . ? N1 C15B P1B 117.9(12) . . ? N1 C15B H15B 107.8 . . ? P1B C15B H15B 107.8 . . ? N1 C15B H15Y 107.8 . . ? P1B C15B H15Y 107.8 . . ? H15B C15B H15Y 107.2 . . ? O13B P1B O11B 108.2(17) . . ? O13B P1B O12B 112.2(19) . . ? O11B P1B O12B 107.8(16) . . ? O13B P1B C15B 106.6(16) . . ? O11B P1B C15B 106.5(11) . . ? O12B P1B C15B 115.3(15) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.123 _refine_diff_density_min -1.060 _refine_diff_density_rms 0.180 _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, p. 435. Coppens, P. (1970). Crystallographic Computing, edited by F.R. Ahmed, S.R.Hall & C.P. Huber, pp. 255-270, Copenhagen, Munksgaard. Hooft, R.W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods Enzymol. 276, 307--326. Sheldrick, G. M. (1997). SHELXL97. University of G\"ottingen, Germany. Spek, A.L. (1999). PLATON. Version 1999. Utrecht University, The Netherlands. ; data_cumon _database_code_depnum_ccdc_archive 'CCDC 272439' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; trans-Br,O-(bromo-((1,4,8,11-tetraazacyclotetradecane-1- yl)methylphosphonate) copper(ii)) hydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C11 H26 Br Cu N4 O3 P, H2 O' _chemical_formula_sum 'C11 H28 Br Cu N4 O4 P' _chemical_formula_weight 454.79 _chemical_compound_source 'synthesized by the authors' 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1457(3) _cell_length_b 8.7318(2) _cell_length_c 13.6044(3) _cell_angle_alpha 79.9760(17) _cell_angle_beta 75.3510(16) _cell_angle_gamma 67.2382(15) _cell_volume 860.12(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10241 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour violet _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.756 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 466 _exptl_absorpt_coefficient_mu 3.707 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.37195 _exptl_absorpt_correction_T_max 0.79542 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15592 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.60 _reflns_number_total 3965 _reflns_number_gt 3522 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0279P)^2^+0.7423P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0049(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3965 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0644 _refine_ls_wR_factor_gt 0.0612 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.75852(3) 0.23090(3) 0.030883(16) 0.02136(8) Uani 1 1 d . . . Cu1 Cu 0.89232(3) 0.21494(3) 0.225384(18) 0.01260(8) Uani 1 1 d . . . N1 N 0.6800(2) 0.4295(2) 0.27688(13) 0.0147(4) Uani 1 1 d . . . C2 C 0.7019(3) 0.5631(3) 0.19582(17) 0.0195(4) Uani 1 1 d . . . H21 H 0.6339 0.6713 0.2223 0.023 Uiso 1 1 calc R . . H22 H 0.6535 0.5585 0.1386 0.023 Uiso 1 1 calc R . . C3 C 0.9005(3) 0.5419(3) 0.16014(16) 0.0182(4) Uani 1 1 d . . . H31 H 0.9151 0.6221 0.1028 0.022 Uiso 1 1 calc R . . H32 H 0.9459 0.5604 0.2147 0.022 Uiso 1 1 calc R . . N4 N 1.0034(2) 0.3706(2) 0.12948(13) 0.0154(4) Uani 1 1 d . . . H41 H 0.9808 0.3703 0.0673 0.018 Uiso 1 1 calc R . . C5 C 1.2023(3) 0.3260(3) 0.11377(17) 0.0207(5) Uani 1 1 d . . . H51 H 1.2329 0.3303 0.1774 0.025 Uiso 1 1 calc R . . H52 H 1.2384 0.4072 0.0640 0.025 Uiso 1 1 calc R . . C6 C 1.3074(3) 0.1532(3) 0.07704(17) 0.0213(5) Uani 1 1 d . . . H61 H 1.4357 0.1373 0.0583 0.026 Uiso 1 1 calc R . . H62 H 1.2697 0.1478 0.0160 0.026 Uiso 1 1 calc R . . C7 C 1.2838(3) 0.0104(3) 0.15401(17) 0.0202(5) Uani 1 1 d . . . H71 H 1.3707 -0.0946 0.1291 0.024 Uiso 1 1 calc R . . H72 H 1.3087 0.0213 0.2180 0.024 Uiso 1 1 calc R . . N8 N 1.0981(2) 0.0093(2) 0.17163(13) 0.0149(4) Uani 1 1 d . . . H81 H 1.0803 -0.0024 0.1104 0.018 Uiso 1 1 calc R . . C9 C 1.0744(3) -0.1340(3) 0.24172(17) 0.0201(5) Uani 1 1 d . . . H91 H 1.1169 -0.1410 0.3034 0.024 Uiso 1 1 calc R . . H92 H 1.1436 -0.2370 0.2094 0.024 Uiso 1 1 calc R . . C10 C 0.8746(3) -0.1069(3) 0.26697(18) 0.0204(5) Uani 1 1 d . . . H101 H 0.8356 -0.1115 0.2062 0.025 Uiso 1 1 calc R . . H102 H 0.8525 -0.1940 0.3173 0.025 Uiso 1 1 calc R . . N11 N 0.7705(2) 0.0584(2) 0.30771(14) 0.0165(4) Uani 1 1 d . . . H111 H 0.7845 0.0487 0.3730 0.020 Uiso 1 1 calc R . . C12 C 0.5743(3) 0.1075(3) 0.31071(18) 0.0228(5) Uani 1 1 d . . . H121 H 0.5313 0.0228 0.3521 0.027 Uiso 1 1 calc R . . H122 H 0.5561 0.1133 0.2422 0.027 Uiso 1 1 calc R . . C13 C 0.4634(3) 0.2741(3) 0.35385(18) 0.0239(5) Uani 1 1 d . . . H131 H 0.4909 0.2705 0.4197 0.029 Uiso 1 1 calc R . . H132 H 0.3354 0.2907 0.3649 0.029 Uiso 1 1 calc R . . C14 C 0.4956(3) 0.4230(3) 0.28696(18) 0.0218(5) Uani 1 1 d . . . H141 H 0.4774 0.4214 0.2194 0.026 Uiso 1 1 calc R . . H142 H 0.4050 0.5243 0.3149 0.026 Uiso 1 1 calc R . . P1 P 0.92482(7) 0.38087(6) 0.40555(4) 0.01390(12) Uani 1 1 d . . . O11 O 1.0247(2) 0.22027(18) 0.35571(11) 0.0185(3) Uani 1 1 d . . . O12 O 0.8811(2) 0.3459(2) 0.52459(11) 0.0211(3) Uani 1 1 d . . . H12O H 0.917(5) 0.394(5) 0.559(3) 0.072(13) Uiso 1 1 d . . . O13 O 1.0132(2) 0.51016(19) 0.37572(11) 0.0185(3) Uani 1 1 d . . . C15 C 0.6969(3) 0.4640(3) 0.37713(16) 0.0176(4) Uani 1 1 d . . . H151 H 0.6192 0.4197 0.4308 0.021 Uiso 1 1 calc R . . H152 H 0.6499 0.5839 0.3801 0.021 Uiso 1 1 calc R . . O1W O 0.7582(3) 0.0579(3) 0.53621(14) 0.0279(4) Uani 1 1 d . . . H1W1 H 0.823(5) -0.028(4) 0.570(3) 0.045(9) Uiso 1 1 d . . . H1W2 H 0.795(5) 0.116(4) 0.537(3) 0.039(11) 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 Br1 0.02217(13) 0.02538(13) 0.01933(13) -0.00651(9) -0.00529(9) -0.00895(9) Cu1 0.01232(14) 0.01120(13) 0.01358(14) -0.00255(9) -0.00081(10) -0.00399(10) N1 0.0128(8) 0.0163(8) 0.0138(8) -0.0036(7) -0.0023(7) -0.0031(7) C2 0.0243(12) 0.0126(10) 0.0183(11) -0.0010(8) -0.0072(9) -0.0013(9) C3 0.0271(12) 0.0128(10) 0.0150(10) 0.0005(8) -0.0046(9) -0.0080(9) N4 0.0175(9) 0.0160(8) 0.0128(8) -0.0024(7) -0.0017(7) -0.0066(7) C5 0.0182(11) 0.0240(11) 0.0218(11) -0.0045(9) -0.0002(9) -0.0110(9) C6 0.0159(11) 0.0265(11) 0.0201(11) -0.0052(9) 0.0016(9) -0.0082(9) C7 0.0117(10) 0.0232(11) 0.0223(11) -0.0053(9) -0.0032(9) -0.0016(9) N8 0.0162(9) 0.0152(8) 0.0128(8) -0.0029(7) -0.0031(7) -0.0043(7) C9 0.0255(12) 0.0135(10) 0.0191(11) -0.0015(8) -0.0056(9) -0.0041(9) C10 0.0269(12) 0.0142(10) 0.0224(11) -0.0011(9) -0.0047(9) -0.0101(9) N11 0.0180(9) 0.0171(9) 0.0161(9) -0.0027(7) -0.0027(7) -0.0081(7) C12 0.0182(11) 0.0287(12) 0.0259(12) -0.0041(10) -0.0006(9) -0.0147(10) C13 0.0145(11) 0.0301(12) 0.0268(12) -0.0072(10) 0.0009(9) -0.0088(9) C14 0.0128(10) 0.0249(11) 0.0252(12) -0.0074(9) -0.0048(9) -0.0014(9) P1 0.0172(3) 0.0149(2) 0.0110(2) -0.0018(2) -0.0028(2) -0.0071(2) O11 0.0215(8) 0.0172(7) 0.0175(8) -0.0048(6) -0.0075(6) -0.0041(6) O12 0.0335(9) 0.0252(8) 0.0111(7) -0.0010(6) -0.0038(7) -0.0183(7) O13 0.0248(8) 0.0215(8) 0.0138(7) -0.0007(6) -0.0049(6) -0.0131(7) C15 0.0172(11) 0.0203(10) 0.0141(10) -0.0087(8) 0.0005(8) -0.0045(8) O1W 0.0309(10) 0.0277(10) 0.0300(10) 0.0068(8) -0.0135(8) -0.0150(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N11 2.0155(17) . ? Cu1 N8 2.0189(17) . ? Cu1 N4 2.0257(17) . ? Cu1 N1 2.0805(17) . ? Cu1 O11 2.3114(15) . ? N1 C2 1.491(3) . ? N1 C14 1.495(3) . ? N1 C15 1.497(3) . ? C2 C3 1.513(3) . ? C2 H21 0.9700 . ? C2 H22 0.9700 . ? C3 N4 1.478(3) . ? C3 H31 0.9700 . ? C3 H32 0.9700 . ? N4 C5 1.479(3) . ? N4 H41 0.9100 . ? C5 C6 1.518(3) . ? C5 H51 0.9700 . ? C5 H52 0.9700 . ? C6 C7 1.522(3) . ? C6 H61 0.9700 . ? C6 H62 0.9700 . ? C7 N8 1.474(3) . ? C7 H71 0.9700 . ? C7 H72 0.9700 . ? N8 C9 1.480(3) . ? N8 H81 0.9100 . ? C9 C10 1.506(3) . ? C9 H91 0.9700 . ? C9 H92 0.9700 . ? C10 N11 1.485(3) . ? C10 H101 0.9700 . ? C10 H102 0.9700 . ? N11 C12 1.478(3) . ? N11 H111 0.9100 . ? C12 C13 1.513(3) . ? C12 H121 0.9700 . ? C12 H122 0.9700 . ? C13 C14 1.523(3) . ? C13 H131 0.9700 . ? C13 H132 0.9700 . ? C14 H141 0.9700 . ? C14 H142 0.9700 . ? P1 O11 1.5025(15) . ? P1 O13 1.5097(15) . ? P1 O12 1.5695(16) . ? P1 C15 1.829(2) . ? O12 H12O 0.85(4) . ? C15 H151 0.9700 . ? C15 H152 0.9700 . ? O1W H1W1 0.86(4) . ? O1W H1W2 0.68(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 N11 Cu1 N8 86.38(7) . . ? N11 Cu1 N4 173.59(7) . . ? N8 Cu1 N4 92.83(7) . . ? N11 Cu1 N1 94.53(7) . . ? N8 Cu1 N1 178.50(7) . . ? N4 Cu1 N1 86.13(7) . . ? N11 Cu1 O11 93.55(6) . . ? N8 Cu1 O11 93.68(6) . . ? N4 Cu1 O11 92.85(6) . . ? N1 Cu1 O11 87.46(6) . . ? C2 N1 C14 108.41(17) . . ? C2 N1 C15 111.04(16) . . ? C14 N1 C15 109.17(16) . . ? C2 N1 Cu1 103.97(12) . . ? C14 N1 Cu1 113.69(13) . . ? C15 N1 Cu1 110.47(12) . . ? N1 C2 C3 110.50(17) . . ? N1 C2 H21 109.6 . . ? C3 C2 H21 109.6 . . ? N1 C2 H22 109.6 . . ? C3 C2 H22 109.6 . . ? H21 C2 H22 108.1 . . ? N4 C3 C2 108.37(17) . . ? N4 C3 H31 110.0 . . ? C2 C3 H31 110.0 . . ? N4 C3 H32 110.0 . . ? C2 C3 H32 110.0 . . ? H31 C3 H32 108.4 . . ? C3 N4 C5 112.37(16) . . ? C3 N4 Cu1 108.40(13) . . ? C5 N4 Cu1 117.53(13) . . ? C3 N4 H41 105.9 . . ? C5 N4 H41 105.9 . . ? Cu1 N4 H41 105.9 . . ? N4 C5 C6 112.13(17) . . ? N4 C5 H51 109.2 . . ? C6 C5 H51 109.2 . . ? N4 C5 H52 109.2 . . ? C6 C5 H52 109.2 . . ? H51 C5 H52 107.9 . . ? C5 C6 C7 114.99(18) . . ? C5 C6 H61 108.5 . . ? C7 C6 H61 108.5 . . ? C5 C6 H62 108.5 . . ? C7 C6 H62 108.5 . . ? H61 C6 H62 107.5 . . ? N8 C7 C6 111.40(17) . . ? N8 C7 H71 109.3 . . ? C6 C7 H71 109.3 . . ? N8 C7 H72 109.3 . . ? C6 C7 H72 109.3 . . ? H71 C7 H72 108.0 . . ? C7 N8 C9 112.52(17) . . ? C7 N8 Cu1 116.79(13) . . ? C9 N8 Cu1 106.51(13) . . ? C7 N8 H81 106.8 . . ? C9 N8 H81 106.8 . . ? Cu1 N8 H81 106.8 . . ? N8 C9 C10 107.53(17) . . ? N8 C9 H91 110.2 . . ? C10 C9 H91 110.2 . . ? N8 C9 H92 110.2 . . ? C10 C9 H92 110.2 . . ? H91 C9 H92 108.5 . . ? N11 C10 C9 109.11(17) . . ? N11 C10 H101 109.9 . . ? C9 C10 H101 109.9 . . ? N11 C10 H102 109.9 . . ? C9 C10 H102 109.9 . . ? H101 C10 H102 108.3 . . ? C12 N11 C10 110.90(17) . . ? C12 N11 Cu1 116.69(14) . . ? C10 N11 Cu1 106.43(13) . . ? C12 N11 H111 107.5 . . ? C10 N11 H111 107.5 . . ? Cu1 N11 H111 107.5 . . ? N11 C12 C13 112.34(18) . . ? N11 C12 H121 109.1 . . ? C13 C12 H121 109.1 . . ? N11 C12 H122 109.1 . . ? C13 C12 H122 109.1 . . ? H121 C12 H122 107.9 . . ? C12 C13 C14 114.71(19) . . ? C12 C13 H131 108.6 . . ? C14 C13 H131 108.6 . . ? C12 C13 H132 108.6 . . ? C14 C13 H132 108.6 . . ? H131 C13 H132 107.6 . . ? N1 C14 C13 114.92(18) . . ? N1 C14 H141 108.5 . . ? C13 C14 H141 108.5 . . ? N1 C14 H142 108.5 . . ? C13 C14 H142 108.5 . . ? H141 C14 H142 107.5 . . ? O11 P1 O13 116.12(9) . . ? O11 P1 O12 110.53(9) . . ? O13 P1 O12 110.47(9) . . ? O11 P1 C15 106.56(9) . . ? O13 P1 C15 110.69(10) . . ? O12 P1 C15 101.41(10) . . ? P1 O11 Cu1 110.55(8) . . ? P1 O12 H12O 117(3) . . ? N1 C15 P1 117.03(14) . . ? N1 C15 H151 108.0 . . ? P1 C15 H151 108.0 . . ? N1 C15 H152 108.0 . . ? P1 C15 H152 108.0 . . ? H151 C15 H152 107.3 . . ? H1W1 O1W H1W2 103(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.532 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.082 _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, p. 435. Coppens, P. (1970). Crystallographic Computing, edited by F.R. Ahmed, S.R.Hall & C.P. Huber, pp. 255-270, Copenhagen, Munksgaard. Hooft, R.W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods Enzymol. 276, 307--326. Sheldrick, G. M. (1997). SHELXL97. University of G\"ottingen, Germany. Spek, A.L. (1999). PLATON. Version 1999. Utrecht University, The Netherlands. ; data_cum _database_code_depnum_ccdc_archive 'CCDC 272440' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; bis(((1,4,8,11-tetraazacyclotetradecane-1- yl)methylphosphonate)copper(ii)) trihydrobromide hexahydrate ; _chemical_melting_point ? _chemical_formula_moiety ; C11 H27 Cu N4 O3 P, C11 H26 Cu N4 O3 P, 6(H2 O), 3(Br) ; _chemical_formula_sum 'C22 H65 Br3 Cu2 N8 O12 P2' _chemical_formula_weight 1062.57 _chemical_compound_source 'synthesized by the authors' 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' P P 0.1023 0.0942 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P m' _symmetry_space_group_name_Hall 'P -2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z' _cell_length_a 9.06410(10) _cell_length_b 26.5943(4) _cell_length_c 9.47850(10) _cell_angle_alpha 90.00 _cell_angle_beta 117.0439(8) _cell_angle_gamma 90.00 _cell_volume 2035.00(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 31385 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour violet _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.734 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 4.130 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.24603 _exptl_absorpt_correction_T_max 0.72643 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33661 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 27.50 _reflns_number_total 9505 _reflns_number_gt 8908 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0194P)^2^+1.2920P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.005(19) _refine_ls_number_reflns 9505 _refine_ls_number_parameters 524 _refine_ls_number_restraints 22 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0541 _refine_ls_wR_factor_gt 0.0528 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 4.542 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1A Cu 0.48428(17) 0.62370(5) 0.24170(15) 0.0146(3) Uani 1 1 d . . . N1A N 0.7159(12) 0.6504(4) 0.2791(11) 0.017(2) Uani 1 1 d . . . C2A C 0.8323(15) 0.6255(5) 0.4294(14) 0.023(3) Uani 1 1 d . . . H21A H 0.9375 0.6431 0.4747 0.028 Uiso 1 1 calc R . . H22A H 0.8518 0.5912 0.4078 0.028 Uiso 1 1 calc R . . C3A C 0.7614(16) 0.6256(5) 0.5456(15) 0.023(3) Uani 1 1 d . . . H31A H 0.8350 0.6079 0.6414 0.028 Uiso 1 1 calc R . . H32A H 0.7487 0.6599 0.5735 0.028 Uiso 1 1 calc R . . N4A N 0.5988(12) 0.6004(4) 0.4699(11) 0.017(2) Uani 1 1 d . . . H41A H 0.6190 0.5669 0.4682 0.020 Uiso 1 1 calc R . . C5A C 0.5054(16) 0.6063(5) 0.5618(14) 0.021(3) Uani 1 1 d . . . H51A H 0.4866 0.6418 0.5710 0.026 Uiso 1 1 calc R . . H52A H 0.5706 0.5931 0.6678 0.026 Uiso 1 1 calc R . . C6A C 0.3397(16) 0.5792(5) 0.4849(15) 0.023(3) Uani 1 1 d . . . H61A H 0.2935 0.5784 0.5592 0.027 Uiso 1 1 calc R . . H62A H 0.3586 0.5446 0.4642 0.027 Uiso 1 1 calc R . . C7A C 0.2133(16) 0.6027(5) 0.3307(15) 0.023(3) Uani 1 1 d . . . H71A H 0.1063 0.5871 0.2995 0.027 Uiso 1 1 calc R . . H72A H 0.2027 0.6382 0.3478 0.027 Uiso 1 1 calc R . . N8A N 0.2604(13) 0.5969(4) 0.2016(11) 0.019(2) Uani 1 1 d . . . H81A H 0.2607 0.5633 0.1830 0.022 Uiso 1 1 calc R . . C9A C 0.1400(16) 0.6202(5) 0.0519(15) 0.024(3) Uani 1 1 d . . . H91A H 0.1233 0.6553 0.0687 0.029 Uiso 1 1 calc R . . H92A H 0.0342 0.6030 0.0113 0.029 Uiso 1 1 calc R . . C10A C 0.2120(17) 0.6156(6) -0.0637(15) 0.026(3) Uani 1 1 d . . . H10A H 0.2209 0.5805 -0.0861 0.031 Uiso 1 1 calc R . . H10X H 0.1405 0.6323 -0.1625 0.031 Uiso 1 1 calc RD . . N11A N 0.3773(13) 0.6392(4) 0.0077(11) 0.017(2) Uani 1 1 d . . . H11A H 0.3611 0.6730 -0.0024 0.020 Uiso 1 1 calc R . . C12A C 0.4707(18) 0.6255(5) -0.0805(15) 0.023(3) Uani 1 1 d . . . H12A H 0.4062 0.6345 -0.1911 0.027 Uiso 1 1 calc R . . H12X H 0.4884 0.5894 -0.0744 0.027 Uiso 1 1 calc R . . C13A C 0.6376(17) 0.6523(5) -0.0133(15) 0.025(3) Uani 1 1 d . . . H13A H 0.6862 0.6470 -0.0846 0.030 Uiso 1 1 calc R . . H13X H 0.6190 0.6882 -0.0106 0.030 Uiso 1 1 calc R . . C14A C 0.7603(17) 0.6355(5) 0.1506(15) 0.022(3) Uani 1 1 d . . . H14A H 0.7700 0.5992 0.1508 0.027 Uiso 1 1 calc R . . H14X H 0.8679 0.6496 0.1747 0.027 Uiso 1 1 calc R . . C15A C 0.7299(16) 0.7065(5) 0.2986(16) 0.024(3) Uani 1 1 d . . . H15A H 0.7288 0.7208 0.2039 0.029 Uiso 1 1 calc R . . H15X H 0.8369 0.7142 0.3863 0.029 Uiso 1 1 calc R . . P1A P 0.5716(4) 0.73822(12) 0.3335(4) 0.0161(6) Uani 1 1 d . . . O11A O 0.4430(10) 0.7008(3) 0.3224(9) 0.0175(17) Uani 1 1 d . . . O12A O 0.6613(12) 0.7654(4) 0.4922(10) 0.024(2) Uani 1 1 d D . . H12P H 0.65(3) 0.757(8) 0.583(17) 0.07(7) Uiso 1 1 d D . . O13A O 0.5027(12) 0.7810(4) 0.2095(11) 0.028(2) Uani 1 1 d D . . H13P H 0.437(19) 0.768(6) 0.115(13) 0.05(5) Uiso 1 1 d D . . Cu1B Cu 0.26879(17) 0.87630(5) 0.65919(15) 0.0140(3) Uani 1 1 d . . . N1B N 0.0676(12) 0.8532(4) 0.6943(11) 0.015(2) Uani 1 1 d . . . C2B C 0.0926(16) 0.8812(5) 0.8404(15) 0.021(3) Uani 1 1 d . . . H21B H 0.0259 0.8661 0.8852 0.025 Uiso 1 1 calc R . . H22B H 0.0576 0.9158 0.8136 0.025 Uiso 1 1 calc R . . C3B C 0.2727(18) 0.8796(5) 0.9600(15) 0.022(3) Uani 1 1 d . . . H31B H 0.2904 0.8991 1.0528 0.027 Uiso 1 1 calc R . . H32B H 0.3065 0.8452 0.9928 0.027 Uiso 1 1 calc R . . N4B N 0.3706(12) 0.9009(4) 0.8848(11) 0.016(2) Uani 1 1 d . . . H41B H 0.3550 0.9348 0.8805 0.019 Uiso 1 1 calc R . . C5B C 0.5499(16) 0.8923(5) 0.9806(15) 0.023(3) Uani 1 1 d . . . H51B H 0.5722 0.8564 0.9885 0.027 Uiso 1 1 calc R . . H52B H 0.5848 0.9051 1.0868 0.027 Uiso 1 1 calc R . . C6B C 0.6486(16) 0.9180(5) 0.9074(15) 0.025(3) Uani 1 1 d . . . H61B H 0.7651 0.9171 0.9829 0.030 Uiso 1 1 calc R . . H62B H 0.6154 0.9530 0.8881 0.030 Uiso 1 1 calc R . . C7B C 0.6269(15) 0.8944(5) 0.7525(15) 0.023(3) Uani 1 1 d . . . H71B H 0.7061 0.9093 0.7223 0.027 Uiso 1 1 calc R . . H72B H 0.6504 0.8587 0.7688 0.027 Uiso 1 1 calc R . . N8B N 0.4585(12) 0.9015(4) 0.6231(12) 0.018(2) Uani 1 1 d . . . H81B H 0.4436 0.9352 0.6061 0.021 Uiso 1 1 calc R . . C9B C 0.4383(18) 0.8789(5) 0.4728(16) 0.025(3) Uani 1 1 d . . . H91B H 0.4724 0.8439 0.4893 0.030 Uiso 1 1 calc R . . H92B H 0.5063 0.8966 0.4342 0.030 Uiso 1 1 calc R . . C10B C 0.2587(18) 0.8827(5) 0.3545(15) 0.026(3) Uani 1 1 d . . . H10B H 0.2284 0.9177 0.3280 0.031 Uiso 1 1 calc R . . H10Y H 0.2390 0.8649 0.2582 0.031 Uiso 1 1 calc R . . N11B N 0.1574(13) 0.8603(4) 0.4253(11) 0.019(2) Uani 1 1 d . . . H11B H 0.1633 0.8263 0.4169 0.022 Uiso 1 1 calc R . . C12B C -0.0192(17) 0.8741(5) 0.3331(15) 0.025(3) Uani 1 1 d . . . H12B H -0.0582 0.8639 0.2237 0.030 Uiso 1 1 calc R . . H12Y H -0.0305 0.9104 0.3351 0.030 Uiso 1 1 calc R . . C13B C -0.1245(16) 0.8494(5) 0.3997(15) 0.026(3) Uani 1 1 d . . . H13B H -0.2402 0.8547 0.3260 0.032 Uiso 1 1 calc R . . H13Y H -0.1042 0.8134 0.4061 0.032 Uiso 1 1 calc R . . C14B C -0.0951(16) 0.8679(5) 0.5611(15) 0.023(3) Uani 1 1 d . . . H14B H -0.1028 0.9043 0.5579 0.027 Uiso 1 1 calc R . . H14Y H -0.1829 0.8552 0.5830 0.027 Uiso 1 1 calc R . . C15B C 0.0668(15) 0.7978(5) 0.7219(15) 0.021(3) Uani 1 1 d . . . H15B H -0.0210 0.7829 0.6278 0.025 Uiso 1 1 calc R . . H15Y H 0.0386 0.7927 0.8081 0.025 Uiso 1 1 calc R . . P1B P 0.2577(4) 0.76344(12) 0.7687(3) 0.0162(6) Uani 1 1 d . . . O11B O 0.3663(10) 0.7964(3) 0.7256(9) 0.0181(17) Uani 1 1 d . . . O12B O 0.1996(12) 0.7158(4) 0.6567(10) 0.025(2) Uani 1 1 d D . . H12Q H 0.20(2) 0.720(7) 0.561(14) 0.06(6) Uiso 1 1 d D . . O13B O 0.3303(11) 0.7441(4) 0.9348(10) 0.024(2) Uani 1 1 d . . . Br1 Br 0.91379(19) 0.77154(7) 0.04168(17) 0.0402(4) Uani 1 1 d . . . Br2A Br 0.1597(2) 1.0000 0.6047(2) 0.0232(4) Uani 1 2 d S . . Br2B Br 0.5404(2) 0.5000 0.1920(2) 0.0243(4) Uani 1 2 d S . . Br3A Br 0.4317(3) 1.0000 1.1565(2) 0.0300(5) Uani 1 2 d S . . Br3B Br 0.7987(3) 0.5000 0.7301(2) 0.0316(5) Uani 1 2 d S . . O1W O 1.1913(13) 0.7379(4) 0.3827(11) 0.031(2) Uani 1 1 d D . . H1W1 H 1.281(17) 0.729(6) 0.37(2) 0.05(5) Uiso 1 1 d D . . H1W2 H 1.129(19) 0.748(6) 0.280(12) 0.04(5) Uiso 1 1 d D . . O2W O 0.6092(12) 0.7455(4) -0.2848(11) 0.024(2) Uani 1 1 d D . . H2W1 H 0.705(17) 0.750(9) -0.195(17) 0.08(7) Uiso 1 1 d D . . H2W2 H 0.54(2) 0.767(7) -0.27(3) 0.07(7) Uiso 1 1 d D . . O3W O -0.1284(19) 1.0000 0.728(2) 0.038(4) Uani 1 2 d SD . . H3W1 H -0.05(2) 1.0000 0.69(3) 0.05(7) Uiso 1 2 d SD . . H3W2 H -0.06(4) 1.0000 0.839(12) 0.10(13) Uiso 1 2 d SD . . O4W O 1.0844(17) 0.5000 1.1075(16) 0.027(3) Uani 1 2 d SD . . H4W1 H 0.994(18) 0.5000 1.008(14) 0.02(5) Uiso 1 2 d SD . . H4W2 H 1.04(3) 0.5000 1.18(3) 0.06(9) Uiso 1 2 d SD . . O5W O 0.5387(18) 1.0000 1.5396(17) 0.026(3) Uani 1 2 d SD . . H5W1 H 0.52(4) 1.0000 1.435(15) 0.07(10) Uiso 1 2 d SD . . H5W2 H 0.653(13) 1.0000 1.57(4) 0.09(11) Uiso 1 2 d SD . . O6W O -0.155(2) 1.0000 0.2344(19) 0.040(4) Uani 1 2 d SD . . H6W1 H -0.257(19) 1.0000 0.24(3) 0.05(8) Uiso 1 2 d SD . . H6W2 H -0.10(4) 1.0000 0.344(11) 0.08(10) Uiso 1 2 d SD . . O7W O 0.459(2) 0.5000 -0.1915(18) 0.037(4) Uani 1 2 d SD . . H7W1 H 0.55(2) 0.5000 -0.21(3) 0.05(8) Uiso 1 2 d SD . . H7W2 H 0.50(3) 0.5000 -0.084(11) 0.05(7) Uiso 1 2 d SD . . O8W O 0.944(2) 0.5000 0.309(2) 0.043(4) Uani 1 2 d SD . . H8W1 H 0.834(11) 0.5000 0.27(3) 0.04(6) Uiso 1 2 d SD . . H8W2 H 1.01(2) 0.5000 0.414(11) 0.02(5) Uiso 1 2 d SD . . O9W O 0.021(2) 1.0000 1.051(2) 0.106(11) Uani 1 2 d S . . O10W O 1.109(3) 0.5000 0.631(2) 0.119(13) Uani 1 2 d SD . . 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 Cu1A 0.0153(7) 0.0158(7) 0.0125(6) 0.0000(5) 0.0062(5) -0.0010(6) N1A 0.019(5) 0.017(5) 0.016(5) -0.001(4) 0.009(4) -0.001(4) C2A 0.017(6) 0.031(7) 0.018(6) 0.003(5) 0.004(5) 0.000(6) C3A 0.019(6) 0.030(7) 0.015(6) 0.000(5) 0.004(5) -0.005(5) N4A 0.020(5) 0.016(5) 0.015(5) 0.000(4) 0.007(4) -0.001(4) C5A 0.028(7) 0.023(7) 0.015(6) 0.001(5) 0.010(5) 0.000(5) C6A 0.028(7) 0.022(7) 0.024(6) 0.000(5) 0.017(6) -0.003(5) C7A 0.022(6) 0.024(7) 0.026(6) -0.003(5) 0.015(5) -0.004(5) N8A 0.019(5) 0.016(5) 0.019(5) -0.001(4) 0.007(4) -0.002(4) C9A 0.015(6) 0.029(7) 0.023(6) 0.003(5) 0.003(5) -0.003(5) C10A 0.025(7) 0.031(8) 0.014(6) 0.000(5) 0.001(5) -0.005(6) N11A 0.020(5) 0.017(5) 0.014(5) 0.001(4) 0.008(4) -0.002(4) C12A 0.032(8) 0.025(7) 0.015(6) -0.003(5) 0.013(6) 0.001(6) C13A 0.032(7) 0.029(7) 0.022(6) 0.001(5) 0.019(6) 0.003(6) C14A 0.022(6) 0.025(7) 0.025(6) -0.002(6) 0.015(5) 0.003(6) C15A 0.030(7) 0.019(6) 0.034(7) -0.006(5) 0.023(6) -0.007(5) P1A 0.0174(14) 0.0138(14) 0.0158(14) -0.0003(11) 0.0065(11) -0.0003(12) O11A 0.018(4) 0.015(4) 0.019(4) -0.002(3) 0.009(3) -0.002(3) O12A 0.028(5) 0.029(5) 0.020(5) -0.008(4) 0.014(4) -0.008(4) O13A 0.027(5) 0.022(5) 0.026(5) 0.007(4) 0.003(4) -0.002(4) Cu1B 0.0148(6) 0.0154(7) 0.0120(6) 0.0010(5) 0.0063(5) -0.0005(6) N1B 0.016(5) 0.015(5) 0.016(5) 0.003(4) 0.008(4) 0.001(4) C2B 0.023(6) 0.022(7) 0.023(6) -0.001(5) 0.016(5) 0.002(5) C3B 0.031(7) 0.023(7) 0.014(6) 0.000(5) 0.011(5) -0.005(6) N4B 0.018(5) 0.016(5) 0.012(4) 0.000(4) 0.006(4) -0.002(4) C5B 0.019(6) 0.026(7) 0.016(6) 0.001(5) 0.001(5) 0.000(5) C6B 0.018(6) 0.023(7) 0.025(6) 0.000(5) 0.003(5) -0.001(5) C7B 0.013(6) 0.022(6) 0.032(7) 0.002(5) 0.009(5) 0.000(5) N8B 0.021(5) 0.013(5) 0.023(5) 0.002(4) 0.013(4) 0.002(4) C9B 0.034(8) 0.023(7) 0.028(7) 0.000(5) 0.023(6) 0.000(6) C10B 0.036(8) 0.029(8) 0.018(6) 0.001(5) 0.018(6) -0.003(6) N11B 0.024(5) 0.017(5) 0.014(5) 0.000(4) 0.008(4) -0.003(4) C12B 0.025(7) 0.029(8) 0.012(6) 0.004(5) 0.001(5) -0.001(6) C13B 0.020(6) 0.030(8) 0.020(6) 0.004(5) 0.002(5) -0.004(6) C14B 0.013(6) 0.025(7) 0.026(6) 0.004(5) 0.006(5) 0.005(5) C15B 0.020(6) 0.018(6) 0.025(6) 0.004(5) 0.010(5) -0.002(5) P1B 0.0200(15) 0.0130(14) 0.0159(14) 0.0019(12) 0.0083(12) 0.0011(12) O11B 0.017(4) 0.015(4) 0.022(4) 0.003(3) 0.008(3) 0.000(3) O12B 0.036(5) 0.017(5) 0.027(5) -0.005(4) 0.018(4) -0.004(4) O13B 0.029(5) 0.022(5) 0.019(4) 0.005(4) 0.009(4) 0.004(4) Br1 0.0327(8) 0.0590(11) 0.0239(7) 0.0073(7) 0.0085(6) -0.0068(7) Br2A 0.0213(9) 0.0255(9) 0.0219(9) 0.000 0.0091(7) 0.000 Br2B 0.0236(9) 0.0285(10) 0.0217(9) 0.000 0.0110(7) 0.000 Br3A 0.0336(11) 0.0274(10) 0.0276(10) 0.000 0.0128(9) 0.000 Br3B 0.0326(11) 0.0313(11) 0.0264(10) 0.000 0.0093(8) 0.000 O1W 0.029(5) 0.043(6) 0.023(5) -0.001(4) 0.012(4) 0.011(5) O2W 0.025(5) 0.028(5) 0.021(5) 0.002(4) 0.013(4) 0.006(4) O3W 0.023(8) 0.049(10) 0.046(10) 0.000 0.018(7) 0.000 O4W 0.024(7) 0.027(8) 0.027(7) 0.000 0.009(6) 0.000 O5W 0.030(8) 0.023(7) 0.030(7) 0.000 0.018(6) 0.000 O6W 0.034(9) 0.047(10) 0.032(8) 0.000 0.009(7) 0.000 O7W 0.050(10) 0.035(9) 0.026(7) 0.000 0.018(7) 0.000 O8W 0.025(9) 0.070(12) 0.037(9) 0.000 0.015(7) 0.000 O9W 0.029(11) 0.25(4) 0.036(10) 0.000 0.009(9) 0.000 O10W 0.052(14) 0.28(4) 0.034(11) 0.000 0.027(10) 0.000 _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 Cu1A N8A 2.017(10) . ? Cu1A N11A 2.019(9) . ? Cu1A N4A 2.025(10) . ? Cu1A N1A 2.089(10) . ? Cu1A O11A 2.279(8) . ? N1A C2A 1.488(15) . ? N1A C14A 1.499(16) . ? N1A C15A 1.501(15) . ? C2A C3A 1.506(19) . ? C2A H21A 0.9700 . ? C2A H22A 0.9700 . ? C3A N4A 1.475(16) . ? C3A H31A 0.9700 . ? C3A H32A 0.9700 . ? N4A C5A 1.474(16) . ? N4A H41A 0.9100 . ? C5A C6A 1.520(18) . ? C5A H51A 0.9700 . ? C5A H52A 0.9700 . ? C6A C7A 1.522(18) . ? C6A H61A 0.9700 . ? C6A H62A 0.9700 . ? C7A N8A 1.476(16) . ? C7A H71A 0.9700 . ? C7A H72A 0.9700 . ? N8A C9A 1.477(16) . ? N8A H81A 0.9100 . ? C9A C10A 1.51(2) . ? C9A H91A 0.9700 . ? C9A H92A 0.9700 . ? C10A N11A 1.474(17) . ? C10A H10A 0.9700 . ? C10A H10X 0.9700 . ? N11A C12A 1.480(17) . ? N11A H11A 0.9100 . ? C12A C13A 1.53(2) . ? C12A H12A 0.9700 . ? C12A H12X 0.9700 . ? C13A C14A 1.509(18) . ? C13A H13A 0.9700 . ? C13A H13X 0.9700 . ? C14A H14A 0.9700 . ? C14A H14X 0.9700 . ? C15A P1A 1.819(13) . ? C15A H15A 0.9700 . ? C15A H15X 0.9700 . ? P1A O11A 1.500(9) . ? P1A O12A 1.528(9) . ? P1A O13A 1.550(9) . ? O12A H12P 0.96(8) . ? O13A H13P 0.89(8) . ? Cu1B N8B 2.014(10) . ? Cu1B N4B 2.014(9) . ? Cu1B N11B 2.020(9) . ? Cu1B N1B 2.090(10) . ? Cu1B O11B 2.277(8) . ? N1B C14B 1.493(15) . ? N1B C2B 1.495(16) . ? N1B C15B 1.496(15) . ? C2B C3B 1.506(19) . ? C2B H21B 0.9700 . ? C2B H22B 0.9700 . ? C3B N4B 1.480(16) . ? C3B H31B 0.9700 . ? C3B H32B 0.9700 . ? N4B C5B 1.476(16) . ? N4B H41B 0.9100 . ? C5B C6B 1.522(19) . ? C5B H51B 0.9700 . ? C5B H52B 0.9700 . ? C6B C7B 1.524(18) . ? C6B H61B 0.9700 . ? C6B H62B 0.9700 . ? C7B N8B 1.472(15) . ? C7B H71B 0.9700 . ? C7B H72B 0.9700 . ? N8B C9B 1.479(16) . ? N8B H81B 0.9100 . ? C9B C10B 1.50(2) . ? C9B H91B 0.9700 . ? C9B H92B 0.9700 . ? C10B N11B 1.486(17) . ? C10B H10B 0.9700 . ? C10B H10Y 0.9700 . ? N11B C12B 1.480(17) . ? N11B H11B 0.9100 . ? C12B C13B 1.513(19) . ? C12B H12B 0.9700 . ? C12B H12Y 0.9700 . ? C13B C14B 1.512(18) . ? C13B H13B 0.9700 . ? C13B H13Y 0.9700 . ? C14B H14B 0.9700 . ? C14B H14Y 0.9700 . ? C15B P1B 1.824(12) . ? C15B H15B 0.9700 . ? C15B H15Y 0.9700 . ? P1B O13B 1.494(9) . ? P1B O11B 1.508(9) . ? P1B O12B 1.581(9) . ? O12B H12Q 0.93(8) . ? O1W H1W1 0.92(8) . ? O1W H1W2 0.92(8) . ? O2W H2W1 0.91(8) . ? O2W H2W2 0.91(8) . ? O3W H3W1 0.92(9) . ? O3W H3W2 0.94(9) . ? O4W H4W1 0.93(8) . ? O4W H4W2 0.93(9) . ? O5W H5W1 0.93(9) . ? O5W H5W2 0.94(9) . ? O6W H6W1 0.93(9) . ? O6W H6W2 0.93(9) . ? O7W H7W1 0.92(9) . ? O7W H7W2 0.91(9) . ? O8W H8W1 0.89(9) . ? O8W H8W2 0.89(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N8A Cu1A N11A 85.7(4) . . ? N8A Cu1A N4A 94.4(4) . . ? N11A Cu1A N4A 173.4(4) . . ? N8A Cu1A N1A 178.7(4) . . ? N11A Cu1A N1A 93.5(4) . . ? N4A Cu1A N1A 86.3(4) . . ? N8A Cu1A O11A 94.4(4) . . ? N11A Cu1A O11A 96.6(4) . . ? N4A Cu1A O11A 90.0(4) . . ? N1A Cu1A O11A 86.7(3) . . ? C2A N1A C14A 108.9(10) . . ? C2A N1A C15A 110.0(10) . . ? C14A N1A C15A 108.9(9) . . ? C2A N1A Cu1A 103.3(7) . . ? C14A N1A Cu1A 113.1(8) . . ? C15A N1A Cu1A 112.4(7) . . ? N1A C2A C3A 110.3(11) . . ? N1A C2A H21A 109.6 . . ? C3A C2A H21A 109.6 . . ? N1A C2A H22A 109.6 . . ? C3A C2A H22A 109.6 . . ? H21A C2A H22A 108.1 . . ? N4A C3A C2A 107.9(10) . . ? N4A C3A H31A 110.1 . . ? C2A C3A H31A 110.1 . . ? N4A C3A H32A 110.1 . . ? C2A C3A H32A 110.1 . . ? H31A C3A H32A 108.4 . . ? C5A N4A C3A 112.3(10) . . ? C5A N4A Cu1A 116.4(8) . . ? C3A N4A Cu1A 107.1(8) . . ? C5A N4A H41A 106.8 . . ? C3A N4A H41A 106.8 . . ? Cu1A N4A H41A 106.8 . . ? N4A C5A C6A 111.9(10) . . ? N4A C5A H51A 109.2 . . ? C6A C5A H51A 109.2 . . ? N4A C5A H52A 109.2 . . ? C6A C5A H52A 109.2 . . ? H51A C5A H52A 107.9 . . ? C5A C6A C7A 114.4(11) . . ? C5A C6A H61A 108.7 . . ? C7A C6A H61A 108.7 . . ? C5A C6A H62A 108.7 . . ? C7A C6A H62A 108.7 . . ? H61A C6A H62A 107.6 . . ? N8A C7A C6A 112.2(11) . . ? N8A C7A H71A 109.2 . . ? C6A C7A H71A 109.2 . . ? N8A C7A H72A 109.2 . . ? C6A C7A H72A 109.2 . . ? H71A C7A H72A 107.9 . . ? C7A N8A C9A 112.8(10) . . ? C7A N8A Cu1A 116.9(8) . . ? C9A N8A Cu1A 105.8(8) . . ? C7A N8A H81A 106.9 . . ? C9A N8A H81A 106.9 . . ? Cu1A N8A H81A 106.9 . . ? N8A C9A C10A 106.7(11) . . ? N8A C9A H91A 110.4 . . ? C10A C9A H91A 110.4 . . ? N8A C9A H92A 110.4 . . ? C10A C9A H92A 110.4 . . ? H91A C9A H92A 108.6 . . ? N11A C10A C9A 108.4(10) . . ? N11A C10A H10A 110.0 . . ? C9A C10A H10A 110.0 . . ? N11A C10A H10X 110.0 . . ? C9A C10A H10X 110.0 . . ? H10A C10A H10X 108.4 . . ? C10A N11A C12A 111.0(10) . . ? C10A N11A Cu1A 107.3(7) . . ? C12A N11A Cu1A 117.3(8) . . ? C10A N11A H11A 106.9 . . ? C12A N11A H11A 106.9 . . ? Cu1A N11A H11A 106.9 . . ? N11A C12A C13A 111.3(10) . . ? N11A C12A H12A 109.4 . . ? C13A C12A H12A 109.4 . . ? N11A C12A H12X 109.4 . . ? C13A C12A H12X 109.4 . . ? H12A C12A H12X 108.0 . . ? C14A C13A C12A 114.7(11) . . ? C14A C13A H13A 108.6 . . ? C12A C13A H13A 108.6 . . ? C14A C13A H13X 108.6 . . ? C12A C13A H13X 108.6 . . ? H13A C13A H13X 107.6 . . ? N1A C14A C13A 114.4(10) . . ? N1A C14A H14A 108.6 . . ? C13A C14A H14A 108.6 . . ? N1A C14A H14X 108.6 . . ? C13A C14A H14X 108.6 . . ? H14A C14A H14X 107.6 . . ? N1A C15A P1A 117.0(8) . . ? N1A C15A H15A 108.1 . . ? P1A C15A H15A 108.1 . . ? N1A C15A H15X 108.1 . . ? P1A C15A H15X 108.1 . . ? H15A C15A H15X 107.3 . . ? O11A P1A O12A 115.6(5) . . ? O11A P1A O13A 113.7(5) . . ? O12A P1A O13A 104.4(5) . . ? O11A P1A C15A 109.4(5) . . ? O12A P1A C15A 106.8(6) . . ? O13A P1A C15A 106.4(6) . . ? P1A O11A Cu1A 112.3(4) . . ? P1A O12A H12P 123(10) . . ? P1A O13A H13P 109(10) . . ? N8B Cu1B N4B 93.4(4) . . ? N8B Cu1B N11B 85.6(4) . . ? N4B Cu1B N11B 173.1(4) . . ? N8B Cu1B N1B 177.6(4) . . ? N4B Cu1B N1B 86.4(4) . . ? N11B Cu1B N1B 94.4(4) . . ? N8B Cu1B O11B 95.9(4) . . ? N4B Cu1B O11B 94.4(4) . . ? N11B Cu1B O11B 92.5(4) . . ? N1B Cu1B O11B 86.5(3) . . ? C14B N1B C2B 109.2(9) . . ? C14B N1B C15B 109.0(9) . . ? C2B N1B C15B 109.8(9) . . ? C14B N1B Cu1B 112.7(7) . . ? C2B N1B Cu1B 103.0(7) . . ? C15B N1B Cu1B 113.0(7) . . ? N1B C2B C3B 109.8(10) . . ? N1B C2B H21B 109.7 . . ? C3B C2B H21B 109.7 . . ? N1B C2B H22B 109.7 . . ? C3B C2B H22B 109.7 . . ? H21B C2B H22B 108.2 . . ? N4B C3B C2B 108.0(10) . . ? N4B C3B H31B 110.1 . . ? C2B C3B H31B 110.1 . . ? N4B C3B H32B 110.1 . . ? C2B C3B H32B 110.1 . . ? H31B C3B H32B 108.4 . . ? C5B N4B C3B 112.2(10) . . ? C5B N4B Cu1B 116.6(8) . . ? C3B N4B Cu1B 107.6(7) . . ? C5B N4B H41B 106.6 . . ? C3B N4B H41B 106.6 . . ? Cu1B N4B H41B 106.6 . . ? N4B C5B C6B 111.2(10) . . ? N4B C5B H51B 109.4 . . ? C6B C5B H51B 109.4 . . ? N4B C5B H52B 109.4 . . ? C6B C5B H52B 109.4 . . ? H51B C5B H52B 108.0 . . ? C5B C6B C7B 114.1(11) . . ? C5B C6B H61B 108.7 . . ? C7B C6B H61B 108.7 . . ? C5B C6B H62B 108.7 . . ? C7B C6B H62B 108.7 . . ? H61B C6B H62B 107.6 . . ? N8B C7B C6B 112.4(10) . . ? N8B C7B H71B 109.1 . . ? C6B C7B H71B 109.1 . . ? N8B C7B H72B 109.1 . . ? C6B C7B H72B 109.1 . . ? H71B C7B H72B 107.9 . . ? C7B N8B C9B 112.2(10) . . ? C7B N8B Cu1B 117.2(8) . . ? C9B N8B Cu1B 106.7(8) . . ? C7B N8B H81B 106.7 . . ? C9B N8B H81B 106.7 . . ? Cu1B N8B H81B 106.7 . . ? N8B C9B C10B 108.0(11) . . ? N8B C9B H91B 110.1 . . ? C10B C9B H91B 110.1 . . ? N8B C9B H92B 110.1 . . ? C10B C9B H92B 110.1 . . ? H91B C9B H92B 108.4 . . ? N11B C10B C9B 108.5(10) . . ? N11B C10B H10B 110.0 . . ? C9B C10B H10B 110.0 . . ? N11B C10B H10Y 110.0 . . ? C9B C10B H10Y 110.0 . . ? H10B C10B H10Y 108.4 . . ? C12B N11B C10B 111.0(10) . . ? C12B N11B Cu1B 117.5(8) . . ? C10B N11B Cu1B 107.9(8) . . ? C12B N11B H11B 106.6 . . ? C10B N11B H11B 106.6 . . ? Cu1B N11B H11B 106.6 . . ? N11B C12B C13B 111.3(10) . . ? N11B C12B H12B 109.4 . . ? C13B C12B H12B 109.4 . . ? N11B C12B H12Y 109.4 . . ? C13B C12B H12Y 109.4 . . ? H12B C12B H12Y 108.0 . . ? C14B C13B C12B 115.2(11) . . ? C14B C13B H13B 108.5 . . ? C12B C13B H13B 108.5 . . ? C14B C13B H13Y 108.5 . . ? C12B C13B H13Y 108.5 . . ? H13B C13B H13Y 107.5 . . ? N1B C14B C13B 115.0(10) . . ? N1B C14B H14B 108.5 . . ? C13B C14B H14B 108.5 . . ? N1B C14B H14Y 108.5 . . ? C13B C14B H14Y 108.5 . . ? H14B C14B H14Y 107.5 . . ? N1B C15B P1B 117.1(8) . . ? N1B C15B H15B 108.0 . . ? P1B C15B H15B 108.0 . . ? N1B C15B H15Y 108.0 . . ? P1B C15B H15Y 108.0 . . ? H15B C15B H15Y 107.3 . . ? O13B P1B O11B 117.2(5) . . ? O13B P1B O12B 106.6(5) . . ? O11B P1B O12B 110.1(5) . . ? O13B P1B C15B 110.1(6) . . ? O11B P1B C15B 107.9(5) . . ? O12B P1B C15B 104.4(6) . . ? P1B O11B Cu1B 113.5(5) . . ? P1B O12B H12Q 114(10) . . ? H1W1 O1W H1W2 94(10) . . ? H2W1 O2W H2W2 104(10) . . ? H3W1 O3W H3W2 104(10) . . ? H4W1 O4W H4W2 108(10) . . ? H5W1 O5W H5W2 89(10) . . ? H6W1 O6W H6W2 88(10) . . ? H7W1 O7W H7W2 104(10) . . ? H8W1 O8W H8W2 119(10) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.513 _refine_diff_density_min -0.538 _refine_diff_density_rms 0.066