# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_shelxl _database_code_depnum_ccdc_archive 'CCDC 914779' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (CuCl(3GCage)) _chemical_melting_point ? _chemical_formula_moiety 'C21 H20 Cl Cu N5 O3, 2(C2 H6 O)' _chemical_formula_sum 'C25 H32 Cl Cu N5 O5' _chemical_formula_weight 581.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 '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 10.6787(10) _cell_length_b 11.3255(9) _cell_length_c 12.1898(12) _cell_angle_alpha 113.135(9) _cell_angle_beta 99.670(8) _cell_angle_gamma 98.548(7) _cell_volume 1298.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4683 _cell_measurement_theta_min 4.0643 _cell_measurement_theta_max 75.8890 _exptl_crystal_description prism _exptl_crystal_colour green-blue _exptl_crystal_size_max 0.5440 _exptl_crystal_size_mid 0.3597 _exptl_crystal_size_min 0.1705 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 2.520 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.419 _exptl_absorpt_correction_T_max 0.704 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8680 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 75.78 _reflns_number_total 5179 _reflns_number_gt 4600 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.1313P)^2^+0.5613P] 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 5179 _refine_ls_number_parameters 321 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1876 _refine_ls_wR_factor_gt 0.1822 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.115 _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 0.59887(4) 0.37835(4) 0.77477(3) 0.03079(18) Uani 1 1 d . . . Cl Cl 0.44377(7) 0.27015(7) 0.86381(6) 0.0359(2) Uani 1 1 d . . . O1 O 0.4131(2) 0.2611(2) 0.41924(19) 0.0380(5) Uani 1 1 d . . . O2 O 0.1534(3) 0.4595(4) 0.3308(3) 0.0618(7) Uani 1 1 d . . . O3 O 0.2624(2) 0.6053(3) 0.5130(3) 0.0525(6) Uani 1 1 d . . . N1 N 0.6393(2) 0.2200(2) 0.6430(2) 0.0311(5) Uani 1 1 d . . . N2 N 0.4769(2) 0.3696(2) 0.6307(2) 0.0300(5) Uani 1 1 d . . . N3 N 0.6183(2) 0.5742(2) 0.8747(2) 0.0313(5) Uani 1 1 d . . . H3B H 0.5767 0.5822 0.9375 0.038 Uiso 1 1 calc R . . N4 N 0.7469(2) 0.4147(3) 0.9235(2) 0.0350(5) Uani 1 1 d . . . N5 N 0.1946(3) 0.4951(3) 0.4419(3) 0.0445(7) Uani 1 1 d . . . C1 C 0.7230(3) 0.1454(3) 0.6552(3) 0.0360(6) Uani 1 1 d . . . H1A H 0.7747 0.1669 0.7350 0.043 Uiso 1 1 calc R . . C2 C 0.7364(3) 0.0379(3) 0.5552(3) 0.0404(7) Uani 1 1 d . . . H2A H 0.7944 -0.0145 0.5669 0.048 Uiso 1 1 calc R . . C3 C 0.6638(3) 0.0082(3) 0.4377(3) 0.0398(7) Uani 1 1 d . . . H3A H 0.6718 -0.0643 0.3677 0.048 Uiso 1 1 calc R . . C4 C 0.5793(3) 0.0869(3) 0.4249(3) 0.0369(6) Uani 1 1 d . . . H4A H 0.5293 0.0699 0.3458 0.044 Uiso 1 1 calc R . . C5 C 0.5690(3) 0.1908(3) 0.5296(3) 0.0320(6) Uani 1 1 d . . . C6 C 0.4782(3) 0.2786(3) 0.5220(3) 0.0311(5) Uani 1 1 d . . . C7 C 0.3933(3) 0.4596(3) 0.6250(3) 0.0309(5) Uani 1 1 d . . . H7A H 0.4152 0.4949 0.5653 0.037 Uiso 1 1 calc R . . C8 C 0.2488(3) 0.3861(3) 0.5792(3) 0.0331(6) Uani 1 1 d . . . C9 C 0.1574(3) 0.4011(3) 0.4927(3) 0.0371(6) Uani 1 1 d . . . C10 C 0.0273(3) 0.3314(4) 0.4501(3) 0.0463(7) Uani 1 1 d . . . H10A H -0.0312 0.3428 0.3891 0.056 Uiso 1 1 calc R . . C11 C -0.0151(3) 0.2455(4) 0.4979(4) 0.0508(8) Uani 1 1 d . . . H11A H -0.1043 0.1992 0.4721 0.061 Uiso 1 1 calc R . . C12 C 0.0722(3) 0.2267(3) 0.5836(3) 0.0441(7) Uani 1 1 d . . . H12A H 0.0430 0.1662 0.6153 0.053 Uiso 1 1 calc R . . C13 C 0.2035(3) 0.2964(3) 0.6239(3) 0.0375(6) Uani 1 1 d . . . H13A H 0.2625 0.2821 0.6825 0.045 Uiso 1 1 calc R . . C14 C 0.4154(3) 0.5765(3) 0.7507(3) 0.0364(6) Uani 1 1 d . . . H14A H 0.3670 0.6412 0.7407 0.044 Uiso 1 1 calc R . . H14B H 0.3799 0.5445 0.8066 0.044 Uiso 1 1 calc R . . C15 C 0.5595(3) 0.6453(3) 0.8089(3) 0.0363(6) Uani 1 1 d . . . H15A H 0.6048 0.6451 0.7444 0.044 Uiso 1 1 calc R . . H15B H 0.5686 0.7382 0.8672 0.044 Uiso 1 1 calc R . . C16 C 0.7585(3) 0.6323(3) 0.9339(3) 0.0350(6) Uani 1 1 d . . . H16A H 0.7717 0.7226 0.9994 0.042 Uiso 1 1 calc R . . H16B H 0.8065 0.6376 0.8725 0.042 Uiso 1 1 calc R . . C17 C 0.8070(3) 0.5438(3) 0.9879(3) 0.0333(6) Uani 1 1 d . . . C18 C 0.9023(3) 0.5900(3) 1.0967(3) 0.0418(7) Uani 1 1 d . . . H18A H 0.9439 0.6814 1.1398 0.050 Uiso 1 1 calc R . . C19 C 0.9364(3) 0.5016(4) 1.1419(3) 0.0465(8) Uani 1 1 d . . . H19A H 1.0021 0.5312 1.2161 0.056 Uiso 1 1 calc R . . C20 C 0.8733(3) 0.3697(4) 1.0771(3) 0.0468(8) Uani 1 1 d . . . H20A H 0.8948 0.3072 1.1066 0.056 Uiso 1 1 calc R . . C21 C 0.7787(3) 0.3293(3) 0.9691(3) 0.0404(7) Uani 1 1 d . . . H21A H 0.7348 0.2385 0.9255 0.048 Uiso 1 1 calc R . . O11S O 0.0220(6) -0.0957(7) 0.1739(6) 0.0459(8) Uani 0.371(4) 1 d PD A 1 H11D H 0.0968 -0.0446 0.2070 0.069 Uiso 0.371(4) 1 calc PR A 1 C11S C -0.065(2) -0.0321(14) 0.2113(14) 0.124(5) Uani 0.371(4) 1 d PD A 1 H11B H -0.0311 0.0255 0.3006 0.149 Uiso 0.371(4) 1 calc PR A 1 H11C H -0.1442 -0.0970 0.2008 0.149 Uiso 0.371(4) 1 calc PR A 1 C12S C -0.106(2) 0.056(2) 0.145(2) 0.115(4) Uani 0.371(4) 1 d PD A 1 H12B H -0.1930 0.0687 0.1527 0.173 Uiso 0.371(4) 1 calc PR A 1 H12C H -0.1064 0.0117 0.0577 0.173 Uiso 0.371(4) 1 calc PR A 1 H12D H -0.0427 0.1418 0.1835 0.173 Uiso 0.371(4) 1 calc PR A 1 O21S O 0.2645(4) 0.0518(4) 0.2035(4) 0.0459(8) Uani 0.629(4) 1 d PD A 2 H21D H 0.3180 0.1147 0.2644 0.069 Uiso 0.629(4) 1 calc PR A 2 C21S C 0.1613(15) 0.0838(8) 0.1834(9) 0.124(5) Uani 0.629(4) 1 d PD A 2 H21B H 0.1571 0.1081 0.1134 0.149 Uiso 0.629(4) 1 calc PR A 2 H21C H 0.1599 0.1629 0.2566 0.149 Uiso 0.629(4) 1 calc PR A 2 C22S C 0.0340(12) -0.0315(15) 0.1519(13) 0.115(4) Uani 0.629(4) 1 d PD A 2 H22A H -0.0435 0.0052 0.1546 0.173 Uiso 0.629(4) 1 calc PR A 2 H22B H 0.0454 -0.0682 0.2126 0.173 Uiso 0.629(4) 1 calc PR A 2 H22C H 0.0229 -0.1016 0.0694 0.173 Uiso 0.629(4) 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 Cu 0.0348(3) 0.0273(3) 0.0263(3) 0.00890(18) 0.00218(18) 0.00954(18) Cl 0.0409(4) 0.0344(4) 0.0281(4) 0.0103(3) 0.0085(3) 0.0062(3) O1 0.0396(11) 0.0411(11) 0.0272(10) 0.0099(8) 0.0022(8) 0.0126(9) O2 0.0669(17) 0.094(2) 0.0467(14) 0.0449(15) 0.0164(13) 0.0370(16) O3 0.0384(12) 0.0596(16) 0.0728(17) 0.0440(14) 0.0091(12) 0.0109(11) N1 0.0334(11) 0.0240(10) 0.0305(11) 0.0077(9) 0.0053(9) 0.0058(8) N2 0.0316(11) 0.0300(11) 0.0272(11) 0.0108(9) 0.0058(9) 0.0099(9) N3 0.0338(12) 0.0286(11) 0.0282(11) 0.0088(9) 0.0063(9) 0.0088(9) N4 0.0369(12) 0.0367(12) 0.0297(12) 0.0132(10) 0.0057(10) 0.0102(10) N5 0.0356(13) 0.0650(19) 0.0507(16) 0.0368(15) 0.0145(12) 0.0245(13) C1 0.0327(13) 0.0324(13) 0.0399(15) 0.0141(12) 0.0035(11) 0.0092(11) C2 0.0358(14) 0.0290(13) 0.0523(18) 0.0135(13) 0.0097(13) 0.0086(11) C3 0.0358(14) 0.0262(13) 0.0433(17) 0.0020(12) 0.0078(12) 0.0051(11) C4 0.0345(14) 0.0319(14) 0.0337(14) 0.0054(12) 0.0055(11) 0.0055(11) C5 0.0298(12) 0.0270(12) 0.0331(14) 0.0085(11) 0.0052(10) 0.0048(10) C6 0.0287(12) 0.0305(13) 0.0297(13) 0.0112(11) 0.0029(10) 0.0046(10) C7 0.0324(13) 0.0332(13) 0.0279(13) 0.0134(11) 0.0053(10) 0.0121(11) C8 0.0352(14) 0.0337(13) 0.0303(14) 0.0116(11) 0.0099(11) 0.0116(11) C9 0.0341(14) 0.0457(16) 0.0376(15) 0.0212(13) 0.0099(12) 0.0162(12) C10 0.0347(15) 0.060(2) 0.0443(18) 0.0237(16) 0.0049(13) 0.0153(14) C11 0.0316(15) 0.061(2) 0.055(2) 0.0236(18) 0.0067(14) 0.0042(14) C12 0.0426(16) 0.0433(16) 0.0456(18) 0.0203(14) 0.0099(14) 0.0051(13) C13 0.0407(15) 0.0373(14) 0.0366(15) 0.0165(12) 0.0093(12) 0.0135(12) C14 0.0394(15) 0.0331(14) 0.0348(15) 0.0110(12) 0.0069(12) 0.0162(12) C15 0.0414(15) 0.0272(12) 0.0353(15) 0.0102(11) 0.0035(12) 0.0098(11) C16 0.0341(14) 0.0323(13) 0.0317(14) 0.0088(11) 0.0043(11) 0.0064(11) C17 0.0302(12) 0.0361(14) 0.0313(14) 0.0106(11) 0.0083(11) 0.0111(11) C18 0.0374(14) 0.0436(16) 0.0350(15) 0.0079(13) 0.0048(12) 0.0131(12) C19 0.0401(16) 0.060(2) 0.0349(16) 0.0156(15) 0.0012(13) 0.0205(15) C20 0.0513(18) 0.056(2) 0.0399(17) 0.0251(15) 0.0085(14) 0.0224(15) C21 0.0439(16) 0.0409(15) 0.0386(16) 0.0194(13) 0.0074(13) 0.0136(13) O11S 0.0416(16) 0.0381(16) 0.0383(17) 0.0087(13) -0.0102(13) -0.0026(13) C11S 0.246(15) 0.043(4) 0.056(4) 0.006(3) 0.033(6) 0.003(6) C12S 0.106(7) 0.129(9) 0.112(8) 0.069(8) -0.004(6) 0.016(6) O21S 0.0416(16) 0.0381(16) 0.0383(17) 0.0087(13) -0.0102(13) -0.0026(13) C21S 0.246(15) 0.043(4) 0.056(4) 0.006(3) 0.033(6) 0.003(6) C22S 0.106(7) 0.129(9) 0.112(8) 0.069(8) -0.004(6) 0.016(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 N2 1.961(2) . ? Cu N3 2.025(2) . ? Cu N1 2.045(2) . ? Cu N4 2.053(3) . ? Cu Cl 2.5433(8) . ? O1 C6 1.251(4) . ? O2 N5 1.228(4) . ? O3 N5 1.227(4) . ? N1 C5 1.342(4) . ? N1 C1 1.347(4) . ? N2 C6 1.325(4) . ? N2 C7 1.466(3) . ? N3 C16 1.472(4) . ? N3 C15 1.474(4) . ? N3 H3B 0.9300 . ? N4 C21 1.347(4) . ? N4 C17 1.348(4) . ? N5 C9 1.466(4) . ? C1 C2 1.391(4) . ? C1 H1A 0.9500 . ? C2 C3 1.391(5) . ? C2 H2A 0.9500 . ? C3 C4 1.391(4) . ? C3 H3A 0.9500 . ? C4 C5 1.389(4) . ? C4 H4A 0.9500 . ? C5 C6 1.505(4) . ? C7 C8 1.532(4) . ? C7 C14 1.532(4) . ? C7 H7A 1.0000 . ? C8 C9 1.392(4) . ? C8 C13 1.394(4) . ? C9 C10 1.390(5) . ? C10 C11 1.377(5) . ? C10 H10A 0.9500 . ? C11 C12 1.382(5) . ? C11 H11A 0.9500 . ? C12 C13 1.402(5) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.524(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.505(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.382(4) . ? C18 C19 1.383(5) . ? C18 H18A 0.9500 . ? C19 C20 1.380(6) . ? C19 H19A 0.9500 . ? C20 C21 1.381(5) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? O11S C11S 1.292(19) . ? O11S H11D 0.8400 . ? C11S C12S 1.573(19) . ? C11S H11B 0.9900 . ? C11S H11C 0.9900 . ? C12S H12B 0.9800 . ? C12S H12C 0.9800 . ? C12S H12D 0.9800 . ? O21S C21S 1.227(15) . ? O21S H21D 0.8400 . ? C21S C22S 1.614(16) . ? C21S H21B 0.9900 . ? C21S H21C 0.9900 . ? C22S H22A 0.9800 . ? C22S H22B 0.9800 . ? C22S H22C 0.9800 . ? 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 N3 94.20(10) . . ? N2 Cu N1 81.81(10) . . ? N3 Cu N1 153.48(10) . . ? N2 Cu N4 169.91(10) . . ? N3 Cu N4 79.59(10) . . ? N1 Cu N4 100.17(10) . . ? N2 Cu Cl 100.90(7) . . ? N3 Cu Cl 103.65(7) . . ? N1 Cu Cl 102.85(7) . . ? N4 Cu Cl 88.36(7) . . ? C5 N1 C1 118.4(2) . . ? C5 N1 Cu 111.95(18) . . ? C1 N1 Cu 129.6(2) . . ? C6 N2 C7 114.5(2) . . ? C6 N2 Cu 116.57(19) . . ? C7 N2 Cu 128.57(18) . . ? C16 N3 C15 113.0(2) . . ? C16 N3 Cu 106.81(17) . . ? C15 N3 Cu 116.50(17) . . ? C16 N3 H3B 106.6 . . ? C15 N3 H3B 106.6 . . ? Cu N3 H3B 106.6 . . ? C21 N4 C17 118.6(3) . . ? C21 N4 Cu 128.0(2) . . ? C17 N4 Cu 113.0(2) . . ? O3 N5 O2 123.9(3) . . ? O3 N5 C9 118.3(3) . . ? O2 N5 C9 117.8(3) . . ? N1 C1 C2 122.2(3) . . ? N1 C1 H1A 118.9 . . ? C2 C1 H1A 118.9 . . ? C1 C2 C3 119.2(3) . . ? C1 C2 H2A 120.4 . . ? C3 C2 H2A 120.4 . . ? C2 C3 C4 118.5(3) . . ? C2 C3 H3A 120.8 . . ? C4 C3 H3A 120.8 . . ? C5 C4 C3 119.0(3) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? N1 C5 C4 122.6(3) . . ? N1 C5 C6 115.8(2) . . ? C4 C5 C6 121.5(3) . . ? O1 C6 N2 126.5(3) . . ? O1 C6 C5 119.8(3) . . ? N2 C6 C5 113.7(2) . . ? N2 C7 C8 110.6(2) . . ? N2 C7 C14 111.6(2) . . ? C8 C7 C14 109.4(2) . . ? N2 C7 H7A 108.4 . . ? C8 C7 H7A 108.4 . . ? C14 C7 H7A 108.4 . . ? C9 C8 C13 116.5(3) . . ? C9 C8 C7 124.2(3) . . ? C13 C8 C7 119.3(3) . . ? C10 C9 C8 123.4(3) . . ? C10 C9 N5 115.9(3) . . ? C8 C9 N5 120.7(3) . . ? C11 C10 C9 118.8(3) . . ? C11 C10 H10A 120.6 . . ? C9 C10 H10A 120.6 . . ? C10 C11 C12 119.9(3) . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C11 C12 C13 120.5(3) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? C8 C13 C12 120.9(3) . . ? C8 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C15 C14 C7 112.4(2) . . ? C15 C14 H14A 109.1 . . ? C7 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? C7 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? N3 C15 C14 108.6(2) . . ? N3 C15 H15A 110.0 . . ? C14 C15 H15A 110.0 . . ? N3 C15 H15B 110.0 . . ? C14 C15 H15B 110.0 . . ? H15A C15 H15B 108.3 . . ? N3 C16 C17 107.0(2) . . ? N3 C16 H16A 110.3 . . ? C17 C16 H16A 110.3 . . ? N3 C16 H16B 110.3 . . ? C17 C16 H16B 110.3 . . ? H16A C16 H16B 108.6 . . ? N4 C17 C18 122.0(3) . . ? N4 C17 C16 114.6(2) . . ? C18 C17 C16 123.4(3) . . ? C17 C18 C19 119.2(3) . . ? C17 C18 H18A 120.4 . . ? C19 C18 H18A 120.4 . . ? C20 C19 C18 118.8(3) . . ? C20 C19 H19A 120.6 . . ? C18 C19 H19A 120.6 . . ? C19 C20 C21 119.4(3) . . ? C19 C20 H20A 120.3 . . ? C21 C20 H20A 120.3 . . ? N4 C21 C20 122.0(3) . . ? N4 C21 H21A 119.0 . . ? C20 C21 H21A 119.0 . . ? O11S C11S C12S 116.1(16) . . ? O11S C11S H11B 108.3 . . ? C12S C11S H11B 108.3 . . ? O11S C11S H11C 108.3 . . ? C12S C11S H11C 108.3 . . ? H11B C11S H11C 107.4 . . ? C21S O21S H21D 109.5 . . ? O21S C21S C22S 113.2(9) . . ? O21S C21S H21B 108.9 . . ? C22S C21S H21B 108.9 . . ? O21S C21S H21C 108.9 . . ? C22S C21S H21C 108.9 . . ? H21B C21S H21C 107.7 . . ? C21S C22S H22A 109.5 . . ? C21S C22S H22B 109.5 . . ? H22A C22S H22B 109.5 . . ? C21S C22S H22C 109.5 . . ? H22A C22S H22C 109.5 . . ? H22B C22S H22C 109.5 . . ? 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 N2 Cu N1 C5 1.06(19) . . . . ? N3 Cu N1 C5 -81.9(3) . . . . ? N4 Cu N1 C5 -168.92(19) . . . . ? Cl Cu N1 C5 100.45(18) . . . . ? N2 Cu N1 C1 -178.9(3) . . . . ? N3 Cu N1 C1 98.1(3) . . . . ? N4 Cu N1 C1 11.1(3) . . . . ? Cl Cu N1 C1 -79.5(2) . . . . ? N3 Cu N2 C6 150.9(2) . . . . ? N1 Cu N2 C6 -2.8(2) . . . . ? N4 Cu N2 C6 99.3(6) . . . . ? Cl Cu N2 C6 -104.4(2) . . . . ? N3 Cu N2 C7 -21.9(2) . . . . ? N1 Cu N2 C7 -175.5(2) . . . . ? N4 Cu N2 C7 -73.5(6) . . . . ? Cl Cu N2 C7 82.9(2) . . . . ? N2 Cu N3 C16 -136.23(18) . . . . ? N1 Cu N3 C16 -56.2(3) . . . . ? N4 Cu N3 C16 35.76(18) . . . . ? Cl Cu N3 C16 121.48(17) . . . . ? N2 Cu N3 C15 -8.8(2) . . . . ? N1 Cu N3 C15 71.2(3) . . . . ? N4 Cu N3 C15 163.1(2) . . . . ? Cl Cu N3 C15 -111.1(2) . . . . ? N2 Cu N4 C21 -153.9(5) . . . . ? N3 Cu N4 C21 153.5(3) . . . . ? N1 Cu N4 C21 -53.4(3) . . . . ? Cl Cu N4 C21 49.3(3) . . . . ? N2 Cu N4 C17 33.9(7) . . . . ? N3 Cu N4 C17 -18.6(2) . . . . ? N1 Cu N4 C17 134.4(2) . . . . ? Cl Cu N4 C17 -122.8(2) . . . . ? C5 N1 C1 C2 -1.6(4) . . . . ? Cu N1 C1 C2 178.4(2) . . . . ? N1 C1 C2 C3 1.9(5) . . . . ? C1 C2 C3 C4 -0.5(5) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C1 N1 C5 C4 0.1(4) . . . . ? Cu N1 C5 C4 -179.9(2) . . . . ? C1 N1 C5 C6 -179.5(2) . . . . ? Cu N1 C5 C6 0.6(3) . . . . ? C3 C4 C5 N1 1.2(4) . . . . ? C3 C4 C5 C6 -179.3(3) . . . . ? C7 N2 C6 O1 -2.6(4) . . . . ? Cu N2 C6 O1 -176.4(2) . . . . ? C7 N2 C6 C5 177.5(2) . . . . ? Cu N2 C6 C5 3.7(3) . . . . ? N1 C5 C6 O1 177.3(3) . . . . ? C4 C5 C6 O1 -2.3(4) . . . . ? N1 C5 C6 N2 -2.8(3) . . . . ? C4 C5 C6 N2 177.6(3) . . . . ? C6 N2 C7 C8 68.4(3) . . . . ? Cu N2 C7 C8 -118.7(2) . . . . ? C6 N2 C7 C14 -169.6(2) . . . . ? Cu N2 C7 C14 3.3(3) . . . . ? N2 C7 C8 C9 -136.4(3) . . . . ? C14 C7 C8 C9 100.4(3) . . . . ? N2 C7 C8 C13 42.6(3) . . . . ? C14 C7 C8 C13 -80.6(3) . . . . ? C13 C8 C9 C10 -0.5(5) . . . . ? C7 C8 C9 C10 178.5(3) . . . . ? C13 C8 C9 N5 178.7(3) . . . . ? C7 C8 C9 N5 -2.2(5) . . . . ? O3 N5 C9 C10 135.1(3) . . . . ? O2 N5 C9 C10 -43.2(4) . . . . ? O3 N5 C9 C8 -44.2(4) . . . . ? O2 N5 C9 C8 137.5(3) . . . . ? C8 C9 C10 C11 1.9(5) . . . . ? N5 C9 C10 C11 -177.4(3) . . . . ? C9 C10 C11 C12 -2.1(6) . . . . ? C10 C11 C12 C13 1.1(6) . . . . ? C9 C8 C13 C12 -0.6(4) . . . . ? C7 C8 C13 C12 -179.6(3) . . . . ? C11 C12 C13 C8 0.3(5) . . . . ? N2 C7 C14 C15 50.9(3) . . . . ? C8 C7 C14 C15 173.5(2) . . . . ? C16 N3 C15 C14 179.6(2) . . . . ? Cu N3 C15 C14 55.3(3) . . . . ? C7 C14 C15 N3 -84.6(3) . . . . ? C15 N3 C16 C17 -175.5(2) . . . . ? Cu N3 C16 C17 -46.1(2) . . . . ? C21 N4 C17 C18 1.9(4) . . . . ? Cu N4 C17 C18 174.9(2) . . . . ? C21 N4 C17 C16 -176.2(3) . . . . ? Cu N4 C17 C16 -3.2(3) . . . . ? N3 C16 C17 N4 32.8(3) . . . . ? N3 C16 C17 C18 -145.2(3) . . . . ? N4 C17 C18 C19 -0.7(5) . . . . ? C16 C17 C18 C19 177.2(3) . . . . ? C17 C18 C19 C20 -0.4(5) . . . . ? C18 C19 C20 C21 0.3(5) . . . . ? C17 N4 C21 C20 -2.0(5) . . . . ? Cu N4 C21 C20 -173.8(2) . . . . ? C19 C20 C21 N4 0.9(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3B Cl 0.93 2.41 3.218(2) 145.0 2_667 O21S H21D O1 0.84 1.93 2.762(4) 169.0 . C15 H15A O1 0.99 2.60 3.383(4) 136.5 2_666 C16 H16B O2 0.99 2.43 3.324(4) 150.4 2_666 C18 H18A O11S 0.95 2.38 3.286(8) 158.9 1_666 _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.144 _refine_diff_density_min -0.579 _refine_diff_density_rms 0.114 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 1.000 0.500 71 22 ' ' _platon_squeeze_details ; There was one disordered ethanol molecule located on a center of inversion which could not be modeled. It was removed using the SQUEEZE routine contained in Platon [P. van der Sluis and A. L. Spek, Acta Cryst. (1990). A46, 194-201] ; _iucr_refine_instructions_details ; TITL kf12-1 in P-1 CELL 1.54184 10.678715 11.325485 12.189805 113.1351 99.6695 98.5476 ZERR 2.00 0.000970 0.000927 0.001240 0.0087 0.0080 0.0071 LATT 1 SFAC C H N O CL CU UNIT 50 64 10 10 2 2 temp -150 l.s. 8 rem damp 200 acta 135 conf bond $h htab N3 Cl_$1 eqiv $1 [ -x+1, -y+1, -z+2 ] htab O21S O1 htab c15 o1_$2 eqiv $2 1-x, 1-y, 1-z htab c16 o2_$2 htab c18 o11s_$3 eqiv $3 1+x, 1+y, 1+z eadp o11s o21s eadp c11s c21s eadp c12s c22s WGHT 0.131300 0.561300 FVAR 17.42876 0.37085 CU 6 0.598866 0.378350 0.774772 11.00000 0.03482 0.02731 = 0.02631 0.00890 0.00218 0.00954 CL 5 0.443769 0.270154 0.863811 11.00000 0.04092 0.03443 = 0.02815 0.01033 0.00845 0.00618 O1 4 0.413055 0.261094 0.419244 11.00000 0.03957 0.04112 = 0.02723 0.00987 0.00218 0.01261 O2 4 0.153388 0.459485 0.330828 11.00000 0.06688 0.09365 = 0.04673 0.04491 0.01636 0.03701 O3 4 0.262420 0.605348 0.512967 11.00000 0.03838 0.05955 = 0.07278 0.04400 0.00906 0.01094 N1 3 0.639252 0.219963 0.642987 11.00000 0.03340 0.02402 = 0.03051 0.00772 0.00528 0.00577 N2 3 0.476906 0.369608 0.630728 11.00000 0.03162 0.03002 = 0.02717 0.01080 0.00579 0.00987 N3 3 0.618324 0.574162 0.874650 11.00000 0.03375 0.02863 = 0.02821 0.00881 0.00634 0.00881 AFIX 13 H3B 2 0.576694 0.582204 0.937520 11.00000 -1.20000 AFIX 0 N4 3 0.746889 0.414661 0.923545 11.00000 0.03694 0.03674 = 0.02971 0.01317 0.00570 0.01024 N5 3 0.194638 0.495094 0.441892 11.00000 0.03565 0.06496 = 0.05072 0.03680 0.01447 0.02455 C1 1 0.722992 0.145351 0.655247 11.00000 0.03270 0.03240 = 0.03992 0.01409 0.00350 0.00924 AFIX 43 H1A 2 0.774655 0.166880 0.735000 11.00000 -1.20000 AFIX 0 C2 1 0.736389 0.037906 0.555158 11.00000 0.03583 0.02904 = 0.05226 0.01348 0.00973 0.00859 AFIX 43 H2A 2 0.794363 -0.014531 0.566858 11.00000 -1.20000 AFIX 0 C3 1 0.663822 0.008160 0.437662 11.00000 0.03580 0.02616 = 0.04332 0.00203 0.00783 0.00513 AFIX 43 H3A 2 0.671815 -0.064265 0.367736 11.00000 -1.20000 AFIX 0 C4 1 0.579280 0.086912 0.424921 11.00000 0.03451 0.03190 = 0.03372 0.00537 0.00552 0.00552 AFIX 43 H4A 2 0.529306 0.069904 0.345808 11.00000 -1.20000 AFIX 0 C5 1 0.569029 0.190790 0.529610 11.00000 0.02980 0.02698 = 0.03308 0.00847 0.00524 0.00476 C6 1 0.478240 0.278605 0.522045 11.00000 0.02874 0.03053 = 0.02966 0.01117 0.00294 0.00458 C7 1 0.393265 0.459635 0.624956 11.00000 0.03243 0.03320 = 0.02793 0.01338 0.00527 0.01211 AFIX 13 H7A 2 0.415179 0.494909 0.565337 11.00000 -1.20000 AFIX 0 C8 1 0.248828 0.386114 0.579171 11.00000 0.03517 0.03374 = 0.03031 0.01158 0.00989 0.01164 C9 1 0.157403 0.401121 0.492662 11.00000 0.03407 0.04570 = 0.03756 0.02115 0.00985 0.01618 C10 1 0.027328 0.331385 0.450094 11.00000 0.03471 0.06049 = 0.04432 0.02374 0.00487 0.01531 AFIX 43 H10A 2 -0.031179 0.342785 0.389140 11.00000 -1.20000 AFIX 0 C11 1 -0.015127 0.245476 0.497933 11.00000 0.03157 0.06085 = 0.05477 0.02358 0.00667 0.00421 AFIX 43 H11A 2 -0.104320 0.199153 0.472119 11.00000 -1.20000 AFIX 0 C12 1 0.072185 0.226725 0.583551 11.00000 0.04258 0.04328 = 0.04564 0.02035 0.00986 0.00510 AFIX 43 H12A 2 0.042988 0.166200 0.615309 11.00000 -1.20000 AFIX 0 C13 1 0.203531 0.296352 0.623898 11.00000 0.04069 0.03726 = 0.03659 0.01655 0.00928 0.01352 AFIX 43 H13A 2 0.262480 0.282150 0.682545 11.00000 -1.20000 AFIX 0 C14 1 0.415428 0.576501 0.750708 11.00000 0.03940 0.03315 = 0.03481 0.01097 0.00693 0.01620 AFIX 23 H14A 2 0.366960 0.641151 0.740748 11.00000 -1.20000 H14B 2 0.379905 0.544474 0.806615 11.00000 -1.20000 AFIX 0 C15 1 0.559539 0.645274 0.808945 11.00000 0.04141 0.02720 = 0.03529 0.01025 0.00353 0.00984 AFIX 23 H15A 2 0.604786 0.645123 0.744367 11.00000 -1.20000 H15B 2 0.568622 0.738169 0.867215 11.00000 -1.20000 AFIX 0 C16 1 0.758479 0.632317 0.933863 11.00000 0.03406 0.03232 = 0.03171 0.00880 0.00434 0.00639 AFIX 23 H16A 2 0.771735 0.722551 0.999400 11.00000 -1.20000 H16B 2 0.806480 0.637632 0.872538 11.00000 -1.20000 AFIX 0 C17 1 0.806954 0.543817 0.987899 11.00000 0.03019 0.03605 = 0.03132 0.01063 0.00826 0.01111 C18 1 0.902307 0.590050 1.096663 11.00000 0.03738 0.04363 = 0.03501 0.00785 0.00478 0.01312 AFIX 43 H18A 2 0.943903 0.681449 1.139846 11.00000 -1.20000 AFIX 0 C19 1 0.936431 0.501628 1.141866 11.00000 0.04009 0.05982 = 0.03491 0.01561 0.00118 0.02052 AFIX 43 H19A 2 1.002110 0.531192 1.216146 11.00000 -1.20000 AFIX 0 C20 1 0.873333 0.369671 1.077103 11.00000 0.05128 0.05591 = 0.03987 0.02506 0.00848 0.02239 AFIX 43 H20A 2 0.894796 0.307220 1.106606 11.00000 -1.20000 AFIX 0 C21 1 0.778744 0.329270 0.969055 11.00000 0.04392 0.04093 = 0.03864 0.01940 0.00740 0.01363 AFIX 43 H21A 2 0.734805 0.238523 0.925499 11.00000 -1.20000 AFIX 0 PART 1 O11S 4 0.022011 -0.095691 0.173940 21.00000 0.04159 0.03808 = 0.03832 0.00874 -0.01015 -0.00259 AFIX 147 H11D 2 0.096770 -0.044643 0.206980 21.00000 -1.50000 AFIX 0 C11S 1 -0.064787 -0.032074 0.211314 21.00000 0.24584 0.04321 = 0.05597 0.00571 0.03302 0.00341 AFIX 23 H11B 2 -0.031093 0.025502 0.300593 21.00000 -1.20000 H11C 2 -0.144218 -0.096973 0.200776 21.00000 -1.20000 AFIX 0 C12S 1 -0.105581 0.055805 0.145070 21.00000 0.10558 0.12867 = 0.11166 0.06901 -0.00440 0.01597 AFIX 137 H12B 2 -0.193002 0.068668 0.152718 21.00000 -1.50000 H12C 2 -0.106445 0.011680 0.057738 21.00000 -1.50000 H12D 2 -0.042712 0.141813 0.183485 21.00000 -1.50000 AFIX 0 PART 2 same o11s > c12s O21S 4 0.264541 0.051820 0.203548 -21.00000 0.04159 0.03808 = 0.03832 0.00874 -0.01015 -0.00259 AFIX 147 H21D 2 0.317998 0.114727 0.264437 -21.00000 -1.50000 AFIX 0 C21S 1 0.161307 0.083807 0.183391 -21.00000 0.24584 0.04321 = 0.05597 0.00571 0.03302 0.00341 AFIX 23 H21B 2 0.157134 0.108109 0.113441 -21.00000 -1.20000 H21C 2 0.159875 0.162944 0.256603 -21.00000 -1.20000 AFIX 0 C22S 1 0.034019 -0.031529 0.151907 -21.00000 0.10558 0.12867 = 0.11166 0.06901 -0.00440 0.01597 AFIX 137 H22A 2 -0.043532 0.005170 0.154640 -21.00000 -1.50000 H22B 2 0.045371 -0.068203 0.212578 -21.00000 -1.50000 H22C 2 0.022919 -0.101596 0.069383 -21.00000 -1.50000 PART 0 HKLF 4 REM kf12-1 in P-1 REM R1 = 0.0611 for 4600 Fo > 4sig(Fo) and 0.0651 for all 5179 data REM 321 parameters refined using 3 restraints END WGHT 0.1313 0.5613 REM Highest difference peak 1.144, deepest hole -0.579, 1-sigma level 0.114 Q1 1 0.5418 0.3356 0.8099 11.00000 0.05 1.14 Q2 1 0.6588 0.4199 0.7477 11.00000 0.05 1.07 Q3 1 -0.2097 -0.0422 0.1975 11.00000 0.05 1.03 Q4 1 -0.2773 0.0942 0.1807 11.00000 0.05 1.01 Q5 1 0.5431 0.3521 0.6958 11.00000 0.05 0.66 Q6 1 0.6496 0.3986 0.8551 11.00000 0.05 0.65 Q7 1 0.3795 0.2194 0.8843 11.00000 0.05 0.55 Q8 1 0.4953 0.2860 0.9278 11.00000 0.05 0.48 Q9 1 0.1253 0.0757 0.2226 11.00000 0.05 0.42 Q10 1 0.3070 0.4200 0.5961 11.00000 0.05 0.41 Q11 1 0.5575 0.3966 0.6247 11.00000 0.05 0.41 Q12 1 0.6870 0.3736 0.9254 11.00000 0.05 0.39 Q13 1 0.2327 0.3403 0.6023 11.00000 0.05 0.38 Q14 1 0.1418 0.2670 0.5850 11.00000 0.05 0.38 Q15 1 0.2547 0.5491 0.4433 11.00000 0.05 0.35 Q16 1 0.4292 0.3188 0.6536 11.00000 0.05 0.35 Q17 1 0.6438 0.4195 0.6569 11.00000 0.05 0.35 Q18 1 0.0934 -0.0425 0.1113 11.00000 0.05 0.34 Q19 1 0.5820 0.1802 0.6733 11.00000 0.05 0.33 Q20 1 0.2128 0.3913 0.5367 11.00000 0.05 0.32 ;