# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Fielden, John' 'Long, De-Liang' 'Cronin, Leroy' _publ_contact_author_name 'Dr L Cronin' _publ_contact_author_address ; Department of Chemistry University of Glasgow Glasgow G12 8QQ UK ; _publ_contact_author_email L.Cronin@chem.gla.ac.uk _publ_section_title ; Solvent and Secondary Coordination Sphere Controlled Reversible Geometry Reorganisations in Copper(II) Complexes ; data_jf243x_syn _database_code_depnum_ccdc_archive 'CCDC 239722' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C12 H28 Cu1 F N4 O2 +), (F -), 2(C H4 O), (H2 O)' _chemical_formula_sum 'C14 H38 Cu F2 N4 O5' _chemical_formula_weight 444.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 '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' 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 10.2410(2) _cell_length_b 7.03400(10) _cell_length_c 14.9794(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.4970(10) _cell_angle_gamma 90.00 _cell_volume 1003.98(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6359 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 30.034 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 474 _exptl_absorpt_coefficient_mu 1.137 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.707 _exptl_absorpt_correction_T_max 0.854 _exptl_absorpt_process_details ; P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst. (1965), 18, 1035-1038 ; _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 Kappa CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 12637 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3615 _reflns_number_gt 3506 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 19' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0195P)^2^+0.4723P] 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 none _refine_ls_extinction_coef none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.002(8) _refine_ls_number_reflns 3615 _refine_ls_number_parameters 245 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0224 _refine_ls_R_factor_gt 0.0210 _refine_ls_wR_factor_ref 0.0525 _refine_ls_wR_factor_gt 0.0516 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.079695(14) 0.03841(2) 0.332780(13) 0.01179(4) Uani 1 1 d . . . F1 F 0.07955(11) 0.08748(16) 0.48417(7) 0.0277(2) Uani 1 1 d . . . F2 F 0.07992(10) 0.54550(12) 0.23757(7) 0.0235(2) Uani 1 1 d . . . N1 N 0.22461(13) 0.2463(2) 0.35792(10) 0.0155(3) Uani 1 1 d . . . H1A H 0.1849 0.3398 0.3133 0.019 Uiso 1 1 calc R . . H1B H 0.2355 0.2972 0.4168 0.019 Uiso 1 1 calc R . . N2 N 0.22743(14) -0.1696(2) 0.37205(10) 0.0177(4) Uani 1 1 d . . . H2A H 0.2374 -0.2051 0.4333 0.021 Uiso 1 1 calc R . . H2B H 0.1892 -0.2722 0.3332 0.021 Uiso 1 1 calc R . . N3 N -0.06897(14) 0.2438(2) 0.28290(10) 0.0170(3) Uani 1 1 d . . . H3A H -0.0796 0.2972 0.3359 0.020 Uiso 1 1 calc R . . H3B H -0.0308 0.3365 0.2566 0.020 Uiso 1 1 calc R . . N4 N -0.06581(14) -0.1721(2) 0.30050(11) 0.0185(4) Uani 1 1 d . . . H4A H -0.0264 -0.2754 0.2823 0.022 Uiso 1 1 calc R . . H4B H -0.0757 -0.2050 0.3571 0.022 Uiso 1 1 calc R . . O3 O 0.32018(15) -0.0010(2) 0.11785(11) 0.0384(4) Uani 1 1 d . . . H3 H 0.2854 -0.1028 0.0898 0.058 Uiso 1 1 calc R . . O4 O -0.16240(15) -0.0106(2) -0.00226(11) 0.0365(4) Uani 1 1 d . . . H4 H -0.1254 -0.1112 -0.0119 0.055 Uiso 1 1 calc R . . C11 C 0.36894(15) 0.2143(2) 0.35824(11) 0.0169(3) Uani 1 1 d . . . H11 H 0.4269 0.3285 0.3877 0.020 Uiso 1 1 calc R . . C12 C 0.43654(19) 0.0428(2) 0.41915(14) 0.0192(5) Uani 1 1 d . . . H12A H 0.4257 0.0534 0.4820 0.023 Uiso 1 1 calc R . . H12B H 0.5382 0.0428 0.4311 0.023 Uiso 1 1 calc R . . C13 C 0.37301(16) -0.1452(2) 0.37220(12) 0.0193(4) Uani 1 1 d . . . H13 H 0.4325 -0.2508 0.4108 0.023 Uiso 1 1 calc R . . C14 C 0.37222(17) -0.1587(2) 0.27046(13) 0.0234(4) Uani 1 1 d . . . H14A H 0.3236 -0.2772 0.2405 0.028 Uiso 1 1 calc R . . H14B H 0.4703 -0.1671 0.2736 0.028 Uiso 1 1 calc R . . C15 C 0.30075(19) 0.0093(3) 0.20709(13) 0.0230(4) Uani 1 1 d . . . H15 H 0.1982 0.0078 0.1954 0.028 Uiso 1 1 calc R . . C16 C 0.36494(17) 0.1950(2) 0.25547(12) 0.0204(4) Uani 1 1 d . . . H16A H 0.3103 0.3022 0.2168 0.024 Uiso 1 1 calc R . . H16B H 0.4619 0.2048 0.2564 0.024 Uiso 1 1 calc R . . C21 C -0.21287(16) 0.2074(2) 0.21239(11) 0.0179(4) Uani 1 1 d . . . H21 H -0.2723 0.3203 0.2124 0.021 Uiso 1 1 calc R . . C22 C -0.2775(2) 0.0339(3) 0.24120(14) 0.0187(5) Uani 1 1 d . . . H22A H -0.3792 0.0303 0.2023 0.022 Uiso 1 1 calc R . . H22B H -0.2666 0.0460 0.3094 0.022 Uiso 1 1 calc R . . C23 C -0.21066(16) -0.1522(2) 0.22750(12) 0.0190(4) Uani 1 1 d . . . H23 H -0.2686 -0.2592 0.2370 0.023 Uiso 1 1 calc R . . C24 C -0.20923(18) -0.1681(2) 0.12686(13) 0.0225(4) Uani 1 1 d . . . H24A H -0.3069 -0.1826 0.0810 0.027 Uiso 1 1 calc R . . H24B H -0.1571 -0.2843 0.1229 0.027 Uiso 1 1 calc R . . C25 C -0.14262(19) 0.0027(3) 0.09664(13) 0.0225(4) Uani 1 1 d . . . H25 H -0.0399 0.0060 0.1359 0.027 Uiso 1 1 calc R . . C26 C -0.21029(18) 0.1863(2) 0.11171(12) 0.0214(4) Uani 1 1 d . . . H26A H -0.3078 0.1918 0.0646 0.026 Uiso 1 1 calc R . . H26B H -0.1585 0.2952 0.0988 0.026 Uiso 1 1 calc R . . O1 O 0.31196(15) 0.5210(2) 0.52196(10) 0.0313(3) Uani 1 1 d . . . H1F H 0.2533 0.5050 0.5484 0.047 Uiso 1 1 calc R . . C1 C 0.4486(2) 0.4874(3) 0.58927(16) 0.0392(5) Uani 1 1 d . . . H1C H 0.5152 0.4838 0.5561 0.059 Uiso 1 1 calc R . . H1D H 0.4506 0.3655 0.6214 0.059 Uiso 1 1 calc R . . H1E H 0.4749 0.5897 0.6370 0.059 Uiso 1 1 calc R . . O2 O -0.15232(14) 0.52172(19) 0.40620(10) 0.0295(3) Uani 1 1 d . . . H2F H -0.0940 0.5062 0.4622 0.044 Uiso 1 1 calc R . . C2 C -0.2894(2) 0.4882(3) 0.40452(15) 0.0350(5) Uani 1 1 d . . . H2C H -0.3116 0.5816 0.4454 0.053 Uiso 1 1 calc R . . H2D H -0.2946 0.3598 0.4284 0.053 Uiso 1 1 calc R . . H2E H -0.3570 0.5000 0.3386 0.053 Uiso 1 1 calc R . . O O 0.08011(14) 0.43017(19) 0.56463(10) 0.0295(3) Uani 1 1 d D . . H1 H 0.077(2) 0.443(3) 0.6185(10) 0.044 Uiso 1 1 d D . . H2 H 0.073(2) 0.317(2) 0.5501(14) 0.044 Uiso 1 1 d 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 Cu 0.01080(7) 0.01331(7) 0.01130(7) 0.00051(9) 0.00410(5) -0.00015(10) F1 0.0264(5) 0.0433(6) 0.0154(5) 0.0017(4) 0.0100(4) 0.0000(5) F2 0.0288(5) 0.0166(5) 0.0257(5) 0.0010(4) 0.0108(4) 0.0008(4) N1 0.0139(6) 0.0149(7) 0.0171(7) -0.0019(5) 0.0050(5) 0.0007(5) N2 0.0161(7) 0.0172(7) 0.0205(7) 0.0036(6) 0.0077(6) 0.0022(5) N3 0.0148(7) 0.0162(7) 0.0186(7) -0.0017(5) 0.0045(6) 0.0005(5) N4 0.0148(7) 0.0168(8) 0.0219(8) 0.0040(6) 0.0044(6) 0.0005(6) O3 0.0278(7) 0.0740(10) 0.0181(7) -0.0145(7) 0.0139(6) -0.0124(7) O4 0.0267(7) 0.0693(10) 0.0133(6) -0.0041(6) 0.0072(6) 0.0100(6) C11 0.0126(7) 0.0192(8) 0.0191(8) -0.0038(6) 0.0061(6) -0.0055(6) C12 0.0113(8) 0.0280(10) 0.0158(8) -0.0019(7) 0.0020(7) -0.0009(7) C13 0.0133(7) 0.0203(8) 0.0248(8) 0.0049(6) 0.0075(6) 0.0034(6) C14 0.0205(8) 0.0210(8) 0.0329(9) -0.0085(7) 0.0147(7) -0.0031(6) C15 0.0185(8) 0.0384(10) 0.0150(8) -0.0042(7) 0.0096(7) -0.0023(7) C16 0.0191(7) 0.0235(8) 0.0217(8) 0.0049(6) 0.0111(6) 0.0013(6) C21 0.0134(7) 0.0202(8) 0.0175(8) -0.0004(6) 0.0027(6) 0.0041(6) C22 0.0119(8) 0.0300(11) 0.0151(9) -0.0035(7) 0.0059(7) -0.0019(7) C23 0.0123(7) 0.0221(8) 0.0199(8) 0.0020(6) 0.0028(6) -0.0042(6) C24 0.0190(8) 0.0225(8) 0.0213(8) -0.0041(7) 0.0019(7) 0.0034(7) C25 0.0173(8) 0.0350(10) 0.0141(9) -0.0032(7) 0.0044(7) 0.0030(7) C26 0.0193(8) 0.0230(8) 0.0188(8) 0.0039(7) 0.0034(7) -0.0014(6) O1 0.0323(7) 0.0396(7) 0.0236(7) 0.0017(6) 0.0122(6) -0.0059(6) C1 0.0291(10) 0.0629(14) 0.0259(10) -0.0081(9) 0.0103(8) -0.0045(9) O2 0.0301(7) 0.0351(7) 0.0239(7) 0.0059(5) 0.0107(5) 0.0016(6) C2 0.0291(10) 0.0518(12) 0.0253(10) -0.0033(9) 0.0112(8) 0.0010(9) O 0.0296(6) 0.0350(7) 0.0253(7) -0.0012(5) 0.0118(5) -0.0018(6) _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 Cu N1 2.0180(14) . ? Cu N4 2.0295(15) . ? Cu N2 2.0306(14) . ? Cu N3 2.0320(14) . ? Cu F1 2.2944(10) . ? N1 C11 1.493(2) . ? N2 C13 1.500(2) . ? N3 C21 1.4872(19) . ? N4 C23 1.492(2) . ? O3 C15 1.424(2) . ? O4 C25 1.423(2) . ? C11 C12 1.518(2) . ? C11 C16 1.531(2) . ? C12 C13 1.527(2) . ? C13 C14 1.524(2) . ? C14 C15 1.524(3) . ? C15 C16 1.522(2) . ? C21 C22 1.525(3) . ? C21 C26 1.525(2) . ? C22 C23 1.526(3) . ? C23 C24 1.517(2) . ? C24 C25 1.530(3) . ? C25 C26 1.521(2) . ? O1 C1 1.413(3) . ? O2 C2 1.415(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 N1 Cu N4 177.00(7) . . ? N1 Cu N2 92.81(6) . . ? N4 Cu N2 86.98(5) . . ? N1 Cu N3 87.38(5) . . ? N4 Cu N3 92.60(6) . . ? N2 Cu N3 175.58(6) . . ? N1 Cu F1 88.48(5) . . ? N4 Cu F1 94.53(5) . . ? N2 Cu F1 95.30(5) . . ? N3 Cu F1 89.12(5) . . ? C11 N1 Cu 123.43(10) . . ? C13 N2 Cu 123.55(11) . . ? C21 N3 Cu 123.56(11) . . ? C23 N4 Cu 123.51(11) . . ? N1 C11 C12 110.76(14) . . ? N1 C11 C16 110.39(12) . . ? C12 C11 C16 111.85(14) . . ? C11 C12 C13 112.82(14) . . ? N2 C13 C14 110.50(13) . . ? N2 C13 C12 110.82(14) . . ? C14 C13 C12 111.09(15) . . ? C13 C14 C15 113.57(14) . . ? O3 C15 C16 107.83(15) . . ? O3 C15 C14 110.18(15) . . ? C16 C15 C14 110.11(14) . . ? C15 C16 C11 113.75(14) . . ? N3 C21 C22 110.90(14) . . ? N3 C21 C26 110.32(14) . . ? C22 C21 C26 111.64(14) . . ? C21 C22 C23 112.70(17) . . ? N4 C23 C24 110.62(14) . . ? N4 C23 C22 110.89(14) . . ? C24 C23 C22 111.42(14) . . ? C23 C24 C25 113.82(14) . . ? O4 C25 C26 108.15(15) . . ? O4 C25 C24 110.34(15) . . ? C26 C25 C24 110.26(15) . . ? C25 C26 C21 113.77(14) . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.29 _refine_diff_density_min -0.28 _refine_diff_density_rms 0.04 data_JF243RR_anti _database_code_depnum_ccdc_archive 'CCDC 239723' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H28 Cu N4 O2 2+), 2(F 1-), 2(H2 O)' _chemical_formula_sum 'C12 H32 Cu F2 N4 O4' _chemical_formula_weight 397.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 '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' 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' 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' _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 7.0993(2) _cell_length_b 7.1315(2) _cell_length_c 10.0059(3) _cell_angle_alpha 108.5670(10) _cell_angle_beta 92.2330(10) _cell_angle_gamma 112.9120(10) _cell_volume 434.56(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5333 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 211 _exptl_absorpt_coefficient_mu 1.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 1.045 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Kappa CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 7086 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1974 _reflns_number_gt 1942 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 19' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0208P)^2^+0.2299P] 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 none _refine_ls_extinction_coef none _refine_ls_number_reflns 1974 _refine_ls_number_parameters 115 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0202 _refine_ls_R_factor_gt 0.0197 _refine_ls_wR_factor_ref 0.0524 _refine_ls_wR_factor_gt 0.0522 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.068 _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 Cu Cu 0.0000 0.0000 0.0000 0.01128(7) Uani 1 2 d S . . N1 N 0.09146(16) -0.10552(17) 0.14456(11) 0.0142(2) Uani 1 1 d . . . H1A H -0.0163 -0.2290 0.1401 0.017 Uiso 1 1 calc R . . H1B H 0.1942 -0.1428 0.1146 0.017 Uiso 1 1 calc R . . N2 N -0.13083(16) 0.15708(17) 0.14370(11) 0.0144(2) Uani 1 1 d . . . H2A H -0.1452 0.2575 0.1132 0.017 Uiso 1 1 calc R . . H2B H -0.2600 0.0590 0.1392 0.017 Uiso 1 1 calc R . . C1 C 0.16590(19) 0.0389(2) 0.29894(13) 0.0156(2) Uani 1 1 d . . . H1C H 0.1919 -0.0449 0.3526 0.019 Uiso 1 1 calc R . . C2 C 0.0009(2) 0.1114(2) 0.35891(14) 0.0177(3) Uani 1 1 d . . . H2C H -0.1303 -0.0162 0.3371 0.021 Uiso 1 1 calc R . . H2D H 0.0414 0.1808 0.4625 0.021 Uiso 1 1 calc R . . C3 C -0.02962(19) 0.2697(2) 0.29779(13) 0.0152(2) Uani 1 1 d . . . H3 H -0.1215 0.3257 0.3507 0.018 Uiso 1 1 calc R . . C4 C 0.1768(2) 0.4640(2) 0.31543(14) 0.0171(3) Uani 1 1 d . . . H4A H 0.1531 0.5528 0.2667 0.020 Uiso 1 1 calc R . . H4B H 0.2267 0.5533 0.4166 0.020 Uiso 1 1 calc R . . C5 C 0.34390(19) 0.3954(2) 0.25593(13) 0.0155(2) Uani 1 1 d . . . H5 H 0.3032 0.3248 0.1513 0.019 Uiso 1 1 calc R . . C6 C 0.37018(19) 0.2358(2) 0.31807(14) 0.0173(3) Uani 1 1 d . . . H6A H 0.4292 0.3120 0.4196 0.021 Uiso 1 1 calc R . . H6B H 0.4677 0.1847 0.2718 0.021 Uiso 1 1 calc R . . O1 O 0.53297(14) 0.58886(15) 0.29112(11) 0.0205(2) Uani 1 1 d D . . H1 H 0.614(3) 0.554(3) 0.2440(19) 0.031 Uiso 1 1 d D . . O2 O 0.46750(16) 0.79324(17) 0.10778(12) 0.0239(2) Uani 1 1 d D . . H2E H 0.400(3) 0.693(3) 0.0315(18) 0.036 Uiso 1 1 d D . . H2F H 0.485(3) 0.740(3) 0.164(2) 0.036 Uiso 1 1 d D . . F F 0.22189(12) 0.49917(13) -0.12899(9) 0.02267(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.01087(11) 0.01059(11) 0.01203(11) 0.00386(8) 0.00193(7) 0.00440(8) N1 0.0148(5) 0.0124(5) 0.0149(5) 0.0049(4) 0.0018(4) 0.0054(4) N2 0.0135(5) 0.0153(5) 0.0148(5) 0.0052(4) 0.0030(4) 0.0068(4) C1 0.0178(6) 0.0155(6) 0.0137(6) 0.0067(5) 0.0013(5) 0.0063(5) C2 0.0190(6) 0.0193(6) 0.0141(6) 0.0073(5) 0.0054(5) 0.0061(5) C3 0.0151(6) 0.0165(6) 0.0129(6) 0.0034(5) 0.0049(5) 0.0071(5) C4 0.0172(6) 0.0138(6) 0.0177(6) 0.0034(5) 0.0023(5) 0.0060(5) C5 0.0129(5) 0.0126(6) 0.0155(6) 0.0026(5) 0.0014(4) 0.0020(5) C6 0.0143(6) 0.0162(6) 0.0184(6) 0.0037(5) -0.0007(5) 0.0059(5) O1 0.0147(4) 0.0147(5) 0.0240(5) 0.0038(4) 0.0035(4) 0.0006(4) O2 0.0210(5) 0.0186(5) 0.0312(6) 0.0104(4) 0.0027(4) 0.0067(4) F 0.0177(4) 0.0177(4) 0.0325(4) 0.0102(3) 0.0054(3) 0.0063(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N2 2.0182(10) . ? Cu N2 2.0182(10) 2 ? Cu N1 2.0200(10) 2 ? Cu N1 2.0200(10) . ? N1 C1 1.4918(16) . ? N2 C3 1.4881(16) . ? C1 C2 1.5262(17) . ? C1 C6 1.5276(17) . ? C2 C3 1.5216(18) . ? C3 C4 1.5305(17) . ? C4 C5 1.5237(17) . ? C5 O1 1.4286(15) . ? C5 C6 1.5247(18) . ? 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 N2 Cu N2 180.00(6) . 2 ? N2 Cu N1 88.92(4) . 2 ? N2 Cu N1 91.08(4) 2 2 ? N2 Cu N1 91.08(4) . . ? N2 Cu N1 88.92(4) 2 . ? N1 Cu N1 180.00(5) 2 . ? C1 N1 Cu 120.39(8) . . ? C3 N2 Cu 120.50(8) . . ? N1 C1 C2 110.86(10) . . ? N1 C1 C6 110.37(10) . . ? C2 C1 C6 110.97(10) . . ? C3 C2 C1 112.56(10) . . ? N2 C3 C2 110.90(10) . . ? N2 C3 C4 109.86(10) . . ? C2 C3 C4 111.54(10) . . ? C5 C4 C3 112.99(10) . . ? O1 C5 C4 107.58(10) . . ? O1 C5 C6 111.18(10) . . ? C4 C5 C6 110.82(10) . . ? C5 C6 C1 113.10(10) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.39 _refine_diff_density_min -0.28 _refine_diff_density_rms 0.05