Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Bencini, Andrea' 'Bazzicalupi, Carla' 'Bellusci, Annalisa' 'Berni, Emanuela' 'Bianchi, Antonio' 'Ciattini, Samuele' 'Giorgi, Claudia' 'Valtancoli, Barbara' _publ_contact_author_name 'Dr Andrea Bencini' _publ_contact_author_address ; Dept of Chemistry University of Florence Via della Lastruccia 3 Sesto Fiorentino Firenze 50019 ITALY ; _publ_contact_author_email 'ANDREA.BENCINI@UNIFI.IT' _publ_section_title ; A New Dipyridine-containing Cryptand for both Proton and Cu(II) Encapsulation. A Solution and Solid State Study ; data_[CuLH](ClO4)3.2H2O _database_code_CSD 177616 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C24 H37 N6 Cu 3+), (Cl O4 1-)3, (H2 O)2 ; _chemical_formula_sum 'C24 H41 Cl3 Cu N6 O14' _chemical_formula_weight 807.52 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 monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.500(7) _cell_length_b 17.825(7) _cell_length_c 13.781(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.193(10) _cell_angle_gamma 90.00 _cell_volume 7025(4) _cell_formula_units_Z 8 _cell_measurement_temperature 298 _cell_measurement_reflns_used 21 _cell_measurement_theta_min 15 _cell_measurement_theta_max 45 _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3352 _exptl_absorpt_coefficient_mu 3.606 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.27 _exptl_absorpt_correction_T_max 0.47 _exptl_absorpt_process_details 'PSI-scan' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SIEMENS P4' _diffrn_measurement_method '\q/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11338 _diffrn_reflns_av_R_equivalents 0.0105 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 60.83 _reflns_number_total 4936 _reflns_number_gt 4390 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS-Bruker' _computing_cell_refinement 'XSCANS-Bruker' _computing_data_reduction 'XSCANS-Bruker' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Ver. 1.01\b) (Farrugia, 1997)' _computing_publication_material 'Parst97 (Nardelli, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Two perchlorate anions (Cl1 and Cl2) are located in special position on crystallographic axis (symmetry opertaion: -x+1, y, -z+0.5 for Cl1 and -x+1, y, -z+1.5 for Cl2). In particular, the Cl1 perchlorate is disordered, with the crystallographic axis passing along the Cl1-O11 bond, and the crystallographic symmetry is simulated by two different tetrahedrons which have in common the Cl1-O1 bond. ; _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^)+(0.1328P)^2^+49.7003P] 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 _atom_sites_solution_H100 geom _refine_ls_H100_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4936 _refine_ls_number_parameters 463 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0782 _refine_ls_wR_factor_ref 0.2302 _refine_ls_wR_factor_gt 0.2193 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.009 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.40499(3) 0.24265(4) 0.49903(6) 0.0422(3) Uani 1 1 d . . . N1 N 0.46794(17) 0.2093(3) 0.5026(3) 0.0490(12) Uani 1 1 d . . . N2 N 0.43894(15) 0.3336(3) 0.5478(3) 0.0450(11) Uani 1 1 d . . . C1 C 0.4860(2) 0.3316(4) 0.5628(4) 0.0545(15) Uani 1 1 d . . . C2 C 0.5033(2) 0.2585(4) 0.5359(4) 0.0509(15) Uani 1 1 d . . . C3 C 0.4750(2) 0.1413(4) 0.4702(4) 0.0554(15) Uani 1 1 d . . . C4 C 0.5198(3) 0.1172(5) 0.4711(5) 0.070(2) Uani 1 1 d . . . H4 H 0.5249 0.0697 0.4480 0.084 Uiso 1 1 calc R . . C5 C 0.5563(3) 0.1648(5) 0.5068(5) 0.075(2) Uani 1 1 d . . . H5 H 0.5866 0.1489 0.5097 0.090 Uiso 1 1 calc R . . C6 C 0.5490(2) 0.2367(5) 0.5389(5) 0.068(2) Uani 1 1 d . . . H6 H 0.5739 0.2694 0.5618 0.082 Uiso 1 1 calc R . . C7 C 0.5122(3) 0.3949(5) 0.5963(5) 0.074(2) Uani 1 1 d . . . H7 H 0.5446 0.3949 0.6066 0.089 Uiso 1 1 calc R . . C8 C 0.4883(3) 0.4583(5) 0.6137(6) 0.085(2) Uani 1 1 d . . . H8 H 0.5052 0.5011 0.6386 0.103 Uiso 1 1 calc R . . C9 C 0.4402(3) 0.4598(4) 0.5954(5) 0.0683(18) Uani 1 1 d . . . H9 H 0.4244 0.5031 0.6059 0.082 Uiso 1 1 calc R . . C10 C 0.4162(2) 0.3947(3) 0.5608(4) 0.0518(14) Uani 1 1 d . . . C11 C 0.3641(2) 0.3857(4) 0.5395(5) 0.0564(15) Uani 1 1 d . . . H11A H 0.3492 0.4295 0.5035 0.068 Uiso 1 1 calc R . . H11B H 0.3549 0.3828 0.6023 0.068 Uiso 1 1 calc R . . N3 N 0.34763(16) 0.3165(3) 0.4787(3) 0.0480(11) Uani 1 1 d . . . C12 C 0.3119(2) 0.2763(4) 0.5178(5) 0.0600(16) Uani 1 1 d . . . H12A H 0.2964 0.2398 0.4686 0.072 Uiso 1 1 calc R . . H12B H 0.2885 0.3120 0.5275 0.072 Uiso 1 1 calc R . . C13 C 0.3326(3) 0.2365(5) 0.6161(5) 0.072(2) Uani 1 1 d . . . H13A H 0.3400 0.2734 0.6694 0.087 Uiso 1 1 calc R . . H13B H 0.3093 0.2027 0.6307 0.087 Uiso 1 1 calc R . . N4 N 0.37535(19) 0.1933(3) 0.6148(4) 0.0581(13) Uani 1 1 d . . . C14 C 0.3666(3) 0.1135(4) 0.5842(5) 0.073(2) Uani 1 1 d . . . H14A H 0.3420 0.0937 0.6124 0.088 Uiso 1 1 calc R . . H14B H 0.3947 0.0844 0.6107 0.088 Uiso 1 1 calc R . . C15 C 0.3524(3) 0.1055(4) 0.4713(5) 0.0671(18) Uani 1 1 d . . . H15A H 0.3497 0.0527 0.4540 0.081 Uiso 1 1 calc R . . H15B H 0.3220 0.1285 0.4459 0.081 Uiso 1 1 calc R . . N5 N 0.38719(17) 0.1417(3) 0.4227(4) 0.0505(12) Uani 1 1 d . . . C16 C 0.4312(2) 0.0944(4) 0.4399(5) 0.0642(17) Uani 1 1 d . . . H16A H 0.4310 0.0578 0.4920 0.077 Uiso 1 1 calc R . . H16B H 0.4315 0.0673 0.3790 0.077 Uiso 1 1 calc R . . C17 C 0.4077(3) 0.1962(5) 0.7153(5) 0.082(2) Uani 1 1 d . . . H17A H 0.4112 0.2473 0.7382 0.123 Uiso 1 1 calc R . . H17B H 0.4377 0.1768 0.7120 0.123 Uiso 1 1 calc R . . H17C H 0.3954 0.1665 0.7610 0.123 Uiso 1 1 calc R . . C18 C 0.3281(2) 0.3368(4) 0.3716(4) 0.0522(14) Uani 1 1 d . . . H18A H 0.3060 0.3775 0.3677 0.063 Uiso 1 1 calc R . . H18B H 0.3114 0.2940 0.3365 0.063 Uiso 1 1 calc R . . C19 C 0.3658(2) 0.3604(3) 0.3202(4) 0.0517(14) Uani 1 1 d . . . H19A H 0.3760 0.4108 0.3418 0.062 Uiso 1 1 calc R . . H19B H 0.3925 0.3273 0.3418 0.062 Uiso 1 1 calc R . . C20 C 0.3506(2) 0.3591(4) 0.2073(5) 0.0587(16) Uani 1 1 d . . . H20A H 0.3246 0.3935 0.1864 0.070 Uiso 1 1 calc R . . H20B H 0.3761 0.3784 0.1815 0.070 Uiso 1 1 calc R . . N6 N 0.3363(2) 0.2850(4) 0.1590(4) 0.0585(15) Uani 1 1 d . . . C21 C 0.3739(3) 0.2273(4) 0.1608(5) 0.0679(18) Uani 1 1 d . . . H21A H 0.3976 0.2500 0.1325 0.081 Uiso 1 1 calc R . . H21B H 0.3601 0.1864 0.1169 0.081 Uiso 1 1 calc R . . C22 C 0.3980(2) 0.1940(4) 0.2613(5) 0.0611(16) Uani 1 1 d . . . H22A H 0.4128 0.2343 0.3050 0.073 Uiso 1 1 calc R . . H22B H 0.4226 0.1607 0.2518 0.073 Uiso 1 1 calc R . . C23 C 0.3666(2) 0.1508(4) 0.3135(4) 0.0579(16) Uani 1 1 d . . . H23A H 0.3369 0.1768 0.3036 0.070 Uiso 1 1 calc R . . H23B H 0.3605 0.1015 0.2831 0.070 Uiso 1 1 calc R . . C24 C 0.3117(3) 0.2979(6) 0.0502(5) 0.089(3) Uani 1 1 d . . . H24A H 0.2877 0.3350 0.0459 0.133 Uiso 1 1 calc R . . H24B H 0.2979 0.2518 0.0212 0.133 Uiso 1 1 calc R . . H24C H 0.3339 0.3151 0.0146 0.133 Uiso 1 1 calc R . . Cl1 Cl 0.5000 0.33731(12) 0.2500 0.0613(6) Uani 1 2 d S . . O11 O 0.5000 0.2591(5) 0.2500 0.142(5) Uani 1 2 d S . . O12 O 0.4618(4) 0.3801(8) 0.2493(18) 0.109(5) Uani 0.50 1 d P . . O13 O 0.4780(6) 0.3546(9) 0.3267(11) 0.107(5) Uani 0.50 1 d P . . O14 O 0.4625(6) 0.3567(9) 0.1557(11) 0.119(5) Uani 0.50 1 d P . . Cl2 Cl 0.5000 0.01759(14) 0.7500 0.0676(7) Uani 1 2 d S . . O21 O 0.5004(3) 0.0589(5) 0.8349(4) 0.123(3) Uani 1 1 d . . . O22 O 0.5403(4) -0.0265(6) 0.7713(6) 0.167(4) Uani 1 1 d . . . Cl3 Cl 0.34639(7) 0.41829(10) 0.82956(15) 0.0738(5) Uani 1 1 d . . . O31 O 0.3502(4) 0.3430(4) 0.8349(7) 0.149(3) Uani 1 1 d . . . O32 O 0.3731(4) 0.4500(5) 0.7709(7) 0.175(4) Uani 1 1 d . . . O33 O 0.3573(8) 0.4482(8) 0.9185(10) 0.305(11) Uani 1 1 d . . . O34 O 0.3055(6) 0.4323(15) 0.793(2) 0.419(17) Uani 1 1 d . . . Cl4 Cl 0.30601(7) -0.10210(11) 0.36185(17) 0.0835(6) Uani 1 1 d . . . O41 O 0.3204(4) -0.1776(5) 0.3563(11) 0.207(6) Uani 1 1 d . . . O42 O 0.3362(4) -0.0573(5) 0.3250(9) 0.180(4) Uani 1 1 d . . . O43 O 0.3159(7) -0.0895(8) 0.4599(10) 0.256(8) Uani 1 1 d . . . O44 O 0.2634(3) -0.0914(12) 0.3317(17) 0.363(13) Uani 1 1 d . . . O100 O 0.2577(2) 0.2145(4) 0.2038(5) 0.109(2) Uani 1 1 d . . . O200 O 0.2445(5) 0.0520(12) 0.487(2) 0.244(16) Uani 0.50 1 d P . . O300 O 0.2247(8) 0.447(2) 0.851(2) 0.230(12) Uani 0.50 1 d P . . H100 H 0.3175(17) 0.269(3) 0.175(3) 0.010(13) 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 Cu1 0.0394(5) 0.0397(5) 0.0461(5) -0.0061(3) 0.0077(4) -0.0012(3) N1 0.053(3) 0.052(3) 0.041(2) 0.001(2) 0.010(2) 0.000(2) N2 0.039(2) 0.047(3) 0.048(3) -0.008(2) 0.008(2) -0.005(2) C1 0.059(4) 0.061(4) 0.042(3) -0.005(3) 0.008(3) -0.015(3) C2 0.041(3) 0.071(4) 0.040(3) 0.007(3) 0.008(2) 0.004(3) C3 0.067(4) 0.057(4) 0.039(3) 0.004(3) 0.006(3) 0.017(3) C4 0.078(5) 0.081(5) 0.055(4) 0.014(3) 0.022(4) 0.046(4) C5 0.054(4) 0.112(7) 0.060(4) 0.016(4) 0.016(3) 0.032(4) C6 0.044(4) 0.109(6) 0.048(4) 0.018(4) 0.005(3) -0.001(4) C7 0.067(4) 0.083(5) 0.068(4) -0.009(4) 0.009(4) -0.027(4) C8 0.106(7) 0.070(5) 0.081(5) -0.021(4) 0.024(5) -0.039(5) C9 0.082(5) 0.049(4) 0.076(4) -0.018(3) 0.025(4) -0.012(3) C10 0.064(4) 0.045(4) 0.046(3) -0.009(3) 0.014(3) -0.004(3) C11 0.056(4) 0.052(4) 0.063(4) -0.013(3) 0.017(3) 0.009(3) N3 0.047(3) 0.052(3) 0.046(2) -0.002(2) 0.014(2) -0.001(2) C12 0.049(3) 0.069(4) 0.068(4) 0.001(3) 0.027(3) 0.005(3) C13 0.077(5) 0.087(5) 0.061(4) 0.004(4) 0.033(4) -0.003(4) N4 0.071(3) 0.058(3) 0.046(3) 0.001(2) 0.015(2) -0.004(3) C14 0.101(6) 0.055(4) 0.069(4) 0.008(3) 0.031(4) -0.013(4) C15 0.088(5) 0.047(4) 0.067(4) -0.002(3) 0.020(4) -0.019(3) N5 0.060(3) 0.040(3) 0.050(3) 0.000(2) 0.011(2) -0.004(2) C16 0.081(5) 0.049(4) 0.062(4) -0.007(3) 0.015(3) 0.020(3) C17 0.101(6) 0.091(6) 0.048(4) 0.003(4) 0.007(4) -0.001(5) C18 0.045(3) 0.061(4) 0.051(3) 0.004(3) 0.011(3) 0.004(3) C19 0.051(3) 0.047(3) 0.058(3) -0.001(3) 0.016(3) -0.002(3) C20 0.059(4) 0.055(4) 0.061(4) 0.012(3) 0.013(3) 0.003(3) N6 0.054(3) 0.076(4) 0.047(3) 0.007(3) 0.016(3) -0.008(3) C21 0.072(4) 0.075(5) 0.061(4) -0.007(3) 0.024(3) 0.008(4) C22 0.061(4) 0.063(4) 0.061(4) -0.005(3) 0.018(3) 0.007(3) C23 0.065(4) 0.053(4) 0.051(3) -0.007(3) 0.006(3) -0.002(3) C24 0.086(5) 0.131(8) 0.042(4) 0.008(4) 0.004(3) 0.003(5) Cl1 0.0616(13) 0.0501(13) 0.0772(15) 0.000 0.0268(11) 0.000 O11 0.101(7) 0.066(6) 0.263(16) 0.000 0.054(9) 0.000 O12 0.045(6) 0.096(9) 0.194(18) -0.003(11) 0.046(9) 0.019(6) O13 0.137(13) 0.112(11) 0.087(9) -0.025(8) 0.058(9) -0.019(9) O14 0.121(12) 0.126(11) 0.091(9) 0.023(8) -0.007(8) -0.010(9) Cl2 0.0881(17) 0.0725(15) 0.0429(11) 0.000 0.0172(10) 0.000 O21 0.148(6) 0.146(6) 0.070(4) -0.039(4) 0.017(4) 0.029(5) O22 0.192(8) 0.192(9) 0.127(6) 0.032(6) 0.062(6) 0.120(7) Cl3 0.0780(12) 0.0539(10) 0.0911(13) -0.0059(9) 0.0238(10) 0.0038(8) O31 0.216(9) 0.070(4) 0.169(8) -0.015(4) 0.063(7) 0.008(5) O32 0.255(12) 0.151(8) 0.161(8) -0.020(6) 0.132(8) -0.078(8) O33 0.62(3) 0.185(11) 0.177(11) -0.110(9) 0.228(16) -0.184(17) O34 0.172(14) 0.40(3) 0.63(5) 0.20(3) 0.01(2) 0.119(17) Cl4 0.0853(13) 0.0693(13) 0.0985(14) -0.0158(10) 0.0278(11) -0.0071(10) O41 0.221(11) 0.091(6) 0.354(17) -0.031(8) 0.156(12) -0.024(6) O42 0.245(12) 0.120(7) 0.222(11) -0.027(7) 0.148(10) -0.051(7) O43 0.45(3) 0.184(11) 0.157(10) -0.033(9) 0.125(13) -0.046(14) O44 0.066(6) 0.44(3) 0.52(3) 0.20(2) -0.062(10) 0.024(10) O100 0.073(4) 0.116(5) 0.123(5) 0.024(4) -0.002(3) -0.025(3) O200 0.085(10) 0.137(15) 0.52(5) -0.12(2) 0.097(18) 0.015(10) O300 0.135(16) 0.32(3) 0.22(2) -0.07(2) 0.007(15) 0.004(19) _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. Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric.Sci.(1965),15(II-A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d Plane 1 m1 = .27666( .00162) m2 = .34909( .00156) m3 = -.89532( .00082) D = -1.38361( .02438) Atom d s d/s (d/s)**2 N1 * .0233 .0043 5.431 29.490 N2 * -.0228 .0042 -5.390 29.047 N3 * .0167 .0043 3.910 15.286 N5 * -.0260 .0053 -4.865 23.670 Cu1 -.2369 .0008 -289.170 83619.230 #=========== Sum((d/s)**2) for starred atoms 97.494 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarity Plane 2 m1 = .22662( .00105) m2 = .33244( .00139) m3 = -.91549( .00055) D = -2.09307( .01627) Atom d s d/s (d/s)**2 N1 * -.0706 .0042 -16.635 276.733 N2 * -.1153 .0042 -27.404 750.998 C7 * .1073 .0071 15.122 228.669 C6 * .1619 .0069 23.336 544.554 N3 * .0710 .0042 16.799 282.202 N5 * .0275 .0053 5.141 26.431 #=========== Sum((d/s)**2) for starred atoms 2109.585 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity Plane 3 m1 = .13238( .00233) m2 = .31603( .00175) m3 = -.93947( .00071) D = -3.52715( .03523) Atom d s d/s (d/s)**2 N1 * .0003 .0042 .072 .005 N2 * -.0003 .0042 -.072 .005 C7 * .0007 .0070 .095 .009 C6 * -.0007 .0069 -.094 .009 #=========== Sum((d/s)**2) for starred atoms .028 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms does not deviate significantly from planarity Plane 4 m1 = .91102( .00087) m2 = .34077( .00197) m3 = .23221( .00278) D = 11.27695( .01204) Atom d s d/s (d/s)**2 N3 * .0000 .0049 .000 .000 N4 * .0000 .0057 .000 .000 N5 * .0000 .0052 .000 .000 #=========== Sum((d/s)**2) for starred atoms .000 Plane 5 m1 = -.92010( .00079) m2 = -.36215( .00185) m3 = -.14921( .00132) D = -10.87335( .00650) Atom d s d/s (d/s)**2 N3 * -.0718 .0049 -14.692 215.856 N4 * .1228 .0057 21.523 463.229 N5 * -.0796 .0052 -15.246 232.429 N6 * .0827 .0062 13.347 178.141 #=========== Sum((d/s)**2) for starred atoms 1089.655 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarity Plane 6 m1 = .12090( .00342) m2 = .35786( .00358) m3 = -.92591( .00149) D = -3.41877( .05410) Atom d s d/s (d/s)**2 N1 * .0000 .0042 .000 .000 C6 * .0000 .0070 .000 .000 C4 * .0000 .0070 .000 .000 #=========== Sum((d/s)**2) for starred atoms .000 Plane 7 m1 = -.15627( .00378) m2 = -.27665( .00306) m3 = .94818( .00097) D = 3.56026( .05001) Atom d s d/s (d/s)**2 N2 * .0000 .0041 .000 .000 C7 * .0000 .0069 .000 .000 C9 * .0000 .0068 .000 .000 #=========== Sum((d/s)**2) for starred atoms .000 Weighted least-squares lines through the starred atoms (Schoemaker,Waser,Marsh & Bergman,Acta Cryst.(1959).12,600) m1,m2,m3 are the direction cosines referred to the X,Y,Z orthogonal axes. X0,Y0,Z0 are the coordinates of the centroid of the set of atoms. Equation of the line: (X-X0)/m1=(Y-Y0)/m2=(Z-Z0)/m3 Line 1 m1 = .57956( .00216) X0 = 9.62862( .00292) m2 = .40287( .00223) Y0 = 3.88540( .00270) m3 = -.70838( .00172) Z0 = 7.44067( .00270) Atom d s d/s (d/s)**2 N4 * .0000 .0078 .000 .000 Cu1 * .0000 .0012 .003 .000 #=========== Sum((d/s)**2) for starred atoms .000 Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 3.24( .11) 176.76( .11) 1 3 8.86( .17) 171.14( .17) 1 4 80.61( .17) 99.39( .17) 1 5 75.68( .12) 104.32( .12) 1 6 9.12( .22) 170.88( .22) 1 7 8.61( .20) 171.39( .20) 2 3 5.65( .14) 174.35( .14) 2 4 83.85( .16) 96.15( .16) 2 5 78.91( .10) 101.09( .10) 2 6 6.26( .20) 173.74( .20) 2 7 5.48( .20) 174.52( .20) 3 4 89.42( .21) 90.58( .21) 3 5 84.49( .15) 95.51( .15) 3 6 2.60( .23) 177.40( .23) 3 7 2.69( .23) 177.31( .23) 4 5 4.94( .18) 175.06( .18) 4 6 89.02( .25) 90.98( .25) 4 7 89.06( .25) 90.94( .25) 5 6 84.11( .21) 95.89( .21) 5 7 84.12( .22) 95.88( .22) 6 7 5.24( .26) 174.76( .26) Angles formed by lines and normals to planes Line - plane angle (s.u.) angle (s.u.) 1 1 20.74( .14) 159.26( .14) 1 2 23.97( .13) 156.03( .13) 1 3 29.59( .17) 150.41( .17) 1 4 59.95( .20) 120.05( .20) 1 5 55.01( .14) 124.99( .14) 1 6 29.53( .24) 150.47( .24) 1 7 29.11( .23) 150.89( .23) ; 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 N2 1.937(4) . ? Cu1 N1 1.939(5) . ? Cu1 N5 2.085(5) . ? Cu1 N3 2.107(5) . ? Cu1 N4 2.183(5) . ? N1 C3 1.326(8) . ? N1 C2 1.354(8) . ? N2 C10 1.315(8) . ? N2 C1 1.352(8) . ? C1 C7 1.382(9) . ? C1 C2 1.480(9) . ? C2 C6 1.393(9) . ? C3 C4 1.389(9) . ? C3 C16 1.508(10) . ? C4 C5 1.364(11) . ? C4 H4 0.9300 . ? C5 C6 1.390(11) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.384(12) . ? C7 H7 0.9300 . ? C8 C9 1.380(11) . ? C8 H8 0.9300 . ? C9 C10 1.381(9) . ? C9 H9 0.9300 . ? C10 C11 1.502(9) . ? C11 N3 1.504(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? N3 C12 1.481(8) . ? N3 C18 1.491(7) . ? C12 C13 1.518(10) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N4 1.483(9) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? N4 C14 1.487(9) . ? N4 C17 1.478(8) . ? C14 C15 1.515(10) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N5 1.502(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? N5 C23 1.487(8) . ? N5 C16 1.518(8) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.517(8) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.511(9) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 N6 1.494(9) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? N6 C21 1.508(9) . ? N6 C24 1.514(8) . ? N6 H100 0.70(5) . ? C21 C22 1.514(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.516(9) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? Cl1 O12 1.360(10) . ? Cl1 O12 1.360(10) 2_655 ? Cl1 O13 1.403(12) . ? Cl1 O13 1.403(12) 2_655 ? Cl1 O11 1.395(9) . ? Cl1 O14 1.526(13) . ? Cl1 O14 1.526(13) 2_655 ? O12 O13 1.150(19) . ? O12 O14 1.36(2) . ? O13 O14 1.71(2) 2_655 ? O14 O13 1.71(2) 2_655 ? Cl2 O21 1.381(6) . ? Cl2 O21 1.381(6) 2_656 ? Cl2 O22 1.393(8) 2_656 ? Cl2 O22 1.393(8) . ? Cl3 O34 1.216(15) . ? Cl3 O33 1.302(10) . ? Cl3 O31 1.347(7) . ? Cl3 O32 1.381(7) . ? Cl4 O44 1.237(9) . ? Cl4 O43 1.330(12) . ? Cl4 O42 1.382(8) . ? Cl4 O41 1.419(10) . ? 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 Cu1 N1 80.6(2) . . ? N2 Cu1 N5 160.4(2) . . ? N1 Cu1 N5 82.5(2) . . ? N2 Cu1 N3 81.59(19) . . ? N1 Cu1 N3 158.0(2) . . ? N5 Cu1 N3 112.15(19) . . ? N2 Cu1 N4 110.5(2) . . ? N1 Cu1 N4 114.2(2) . . ? N5 Cu1 N4 85.65(19) . . ? N3 Cu1 N4 84.1(2) . . ? C3 N1 C2 122.3(5) . . ? C3 N1 Cu1 120.0(4) . . ? C2 N1 Cu1 117.7(4) . . ? C10 N2 C1 122.6(5) . . ? C10 N2 Cu1 120.3(4) . . ? C1 N2 Cu1 117.1(4) . . ? N2 C1 C7 120.0(6) . . ? N2 C1 C2 112.9(5) . . ? C7 C1 C2 127.1(6) . . ? N1 C2 C6 119.3(6) . . ? N1 C2 C1 111.7(5) . . ? C6 C2 C1 129.0(6) . . ? N1 C3 C4 120.5(7) . . ? N1 C3 C16 114.0(5) . . ? C4 C3 C16 125.4(6) . . ? C5 C4 C3 118.5(7) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? C4 C5 C6 121.2(6) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C2 C6 C5 118.1(7) . . ? C2 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? C8 C7 C1 117.1(7) . . ? C8 C7 H7 121.4 . . ? C1 C7 H7 121.4 . . ? C7 C8 C9 122.1(7) . . ? C7 C8 H8 119.0 . . ? C9 C8 H8 119.0 . . ? C10 C9 C8 117.5(7) . . ? C10 C9 H9 121.2 . . ? C8 C9 H9 121.2 . . ? N2 C10 C9 120.6(6) . . ? N2 C10 C11 114.6(5) . . ? C9 C10 C11 124.7(6) . . ? C10 C11 N3 111.9(5) . . ? C10 C11 H11A 109.2 . . ? N3 C11 H11A 109.2 . . ? C10 C11 H11B 109.2 . . ? N3 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C12 N3 C18 110.0(5) . . ? C12 N3 C11 110.8(5) . . ? C18 N3 C11 110.2(5) . . ? C12 N3 Cu1 105.7(4) . . ? C18 N3 Cu1 112.7(3) . . ? C11 N3 Cu1 107.4(3) . . ? N3 C12 C13 112.6(5) . . ? N3 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? N3 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? N4 C13 C12 112.9(5) . . ? N4 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? N4 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C13 N4 C14 114.3(6) . . ? C13 N4 C17 109.1(6) . . ? C14 N4 C17 109.1(6) . . ? C13 N4 Cu1 107.1(4) . . ? C14 N4 Cu1 104.6(4) . . ? C17 N4 Cu1 112.8(4) . . ? N4 C14 C15 111.5(5) . . ? N4 C14 H14A 109.3 . . ? C15 C14 H14A 109.3 . . ? N4 C14 H14B 109.3 . . ? C15 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? N5 C15 C14 111.8(6) . . ? N5 C15 H15A 109.3 . . ? C14 C15 H15A 109.3 . . ? N5 C15 H15B 109.3 . . ? C14 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? C23 N5 C15 110.1(5) . . ? C23 N5 C16 109.9(5) . . ? C15 N5 C16 110.1(5) . . ? C23 N5 Cu1 114.0(4) . . ? C15 N5 Cu1 105.1(4) . . ? C16 N5 Cu1 107.5(4) . . ? C3 C16 N5 112.1(5) . . ? C3 C16 H16A 109.2 . . ? N5 C16 H16A 109.2 . . ? C3 C16 H16B 109.2 . . ? N5 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? N4 C17 H17A 109.5 . . ? N4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N3 C18 C19 112.3(5) . . ? N3 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? N3 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C20 C19 C18 114.2(5) . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19B 108.7 . . ? C18 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? N6 C20 C19 116.9(5) . . ? N6 C20 H20A 108.1 . . ? C19 C20 H20A 108.1 . . ? N6 C20 H20B 108.1 . . ? C19 C20 H20B 108.1 . . ? H20A C20 H20B 107.3 . . ? C20 N6 C21 118.0(6) . . ? C20 N6 C24 108.7(6) . . ? C21 N6 C24 107.0(6) . . ? C20 N6 H100 113(4) . . ? C21 N6 H100 110(4) . . ? C24 N6 H100 98(4) . . ? N6 C21 C22 117.5(5) . . ? N6 C21 H21A 107.9 . . ? C22 C21 H21A 107.9 . . ? N6 C21 H21B 107.9 . . ? C22 C21 H21B 107.9 . . ? H21A C21 H21B 107.2 . . ? C21 C22 C23 115.3(6) . . ? C21 C22 H22A 108.4 . . ? C23 C22 H22A 108.4 . . ? C21 C22 H22B 108.4 . . ? C23 C22 H22B 108.4 . . ? H22A C22 H22B 107.5 . . ? N5 C23 C22 112.9(5) . . ? N5 C23 H23A 109.0 . . ? C22 C23 H23A 109.0 . . ? N5 C23 H23B 109.0 . . ? C22 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? N6 C24 H24A 109.5 . . ? N6 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N6 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O12 Cl1 O12 111.8(12) . 2_655 ? O12 Cl1 O13 49.2(9) . . ? O12 Cl1 O13 114.0(10) 2_655 . ? O12 Cl1 O13 114.0(10) . 2_655 ? O12 Cl1 O13 49.2(9) 2_655 2_655 ? O13 Cl1 O13 154.6(13) . 2_655 ? O12 Cl1 O11 124.1(6) . . ? O12 Cl1 O11 124.1(6) 2_655 . ? O13 Cl1 O11 102.7(7) . . ? O13 Cl1 O11 102.7(7) 2_655 . ? O12 Cl1 O14 55.9(10) . . ? O12 Cl1 O14 107.8(10) 2_655 . ? O13 Cl1 O14 102.7(10) . . ? O13 Cl1 O14 71.4(9) 2_655 . ? O11 Cl1 O14 103.1(6) . . ? O12 Cl1 O14 107.8(10) . 2_655 ? O12 Cl1 O14 55.9(10) 2_655 2_655 ? O13 Cl1 O14 71.4(9) . 2_655 ? O13 Cl1 O14 102.7(10) 2_655 2_655 ? O11 Cl1 O14 103.1(6) . 2_655 ? O14 Cl1 O14 153.8(13) . 2_655 ? O13 O12 O14 131.2(15) . . ? O13 O12 Cl1 67.4(9) . . ? O14 O12 Cl1 68.2(9) . . ? O12 O13 Cl1 63.4(8) . . ? O12 O13 O14 107.6(12) . 2_655 ? Cl1 O13 O14 57.7(7) . 2_655 ? O12 O14 Cl1 55.8(7) . . ? O12 O14 O13 97.2(10) . 2_655 ? Cl1 O14 O13 51.0(6) . 2_655 ? O21 Cl2 O21 115.5(7) . 2_656 ? O21 Cl2 O22 108.0(5) . 2_656 ? O21 Cl2 O22 107.0(5) 2_656 2_656 ? O21 Cl2 O22 107.0(5) . . ? O21 Cl2 O22 108.0(5) 2_656 . ? O22 Cl2 O22 111.4(11) 2_656 . ? O34 Cl3 O33 107.4(18) . . ? O34 Cl3 O31 106.8(14) . . ? O33 Cl3 O31 111.0(9) . . ? O34 Cl3 O32 108.8(14) . . ? O33 Cl3 O32 109.8(7) . . ? O31 Cl3 O32 112.9(6) . . ? O44 Cl4 O43 105.5(15) . . ? O44 Cl4 O42 118.7(11) . . ? O43 Cl4 O42 105.9(9) . . ? O44 Cl4 O41 114.8(12) . . ? O43 Cl4 O41 102.7(9) . . ? O42 Cl4 O41 107.5(6) . . ? _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 60.83 _diffrn_measured_fraction_theta_full 0.920 _refine_diff_density_max 0.786 _refine_diff_density_min -0.891 _refine_diff_density_rms 0.093 #===END data_[CuL1](ClO4)2 _database_code_CSD 177617 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C17 H23 N5 Cu 2+), (Cl O4 1-)2 ; _chemical_formula_sum 'C17 H23 Cl2 Cu N5 O8' _chemical_formula_weight 559.84 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 monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.1570(10) _cell_length_b 8.8210(10) _cell_length_c 20.685(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.973(9) _cell_angle_gamma 90.00 _cell_volume 2177.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used 22 _cell_measurement_theta_min 12 _cell_measurement_theta_max 42 _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1148 _exptl_absorpt_coefficient_mu 4.186 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.27 _exptl_absorpt_correction_T_max 0.42 _exptl_absorpt_process_details 'PSI-scan' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SIEMENS P4' _diffrn_measurement_method '\q/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4100 _diffrn_reflns_av_R_equivalents 0.0743 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 59.99 _reflns_number_total 3034 _reflns_number_gt 2568 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS-Bruker' _computing_cell_refinement 'XSCANS-Bruker' _computing_data_reduction 'XSCANS-Bruker' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Ver. 1.01\b) (Farrugia, 1997)' _computing_publication_material 'Parst97 (Nardelli, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1214P)^2^+4.0446P] 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 _atom_sites_solution_H1N3 geom _refine_ls_H1N3_treatment refall _atom_sites_solution_H1N5 geom _refine_ls_H1N5_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0058(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3034 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.2012 _refine_ls_wR_factor_gt 0.1885 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 Cu1 Cu 0.73805(6) 0.10878(9) 0.12495(3) 0.0417(4) Uani 1 1 d . . . N1 N 0.7006(4) 0.0544(5) 0.0317(2) 0.0463(11) Uani 1 1 d . . . N2 N 0.5948(3) 0.2115(5) 0.09951(19) 0.0420(10) Uani 1 1 d . . . C1 C 0.7635(5) -0.0448(7) 0.0066(3) 0.0509(14) Uani 1 1 d . . . C2 C 0.7389(6) -0.0702(8) -0.0624(3) 0.0662(19) Uani 1 1 d . . . H2 H 0.7806 -0.1401 -0.0813 0.079 Uiso 1 1 calc R . . C3 C 0.6546(7) 0.0073(8) -0.1007(3) 0.069(2) Uani 1 1 d . . . H3 H 0.6409 -0.0067 -0.1461 0.083 Uiso 1 1 calc R . . C4 C 0.5890(6) 0.1066(7) -0.0733(3) 0.0562(16) Uani 1 1 d . . . H4 H 0.5297 0.1578 -0.0993 0.067 Uiso 1 1 calc R . . C5 C 0.6143(5) 0.1277(6) -0.0057(2) 0.0454(13) Uani 1 1 d . . . C6 C 0.5523(4) 0.2247(6) 0.0345(2) 0.0439(13) Uani 1 1 d . . . C7 C 0.4589(5) 0.3138(8) 0.0132(3) 0.0568(15) Uani 1 1 d . . . H7 H 0.4280 0.3224 -0.0314 0.068 Uiso 1 1 calc R . . C8 C 0.4122(5) 0.3904(7) 0.0606(3) 0.0590(16) Uani 1 1 d . . . H8 H 0.3502 0.4525 0.0474 0.071 Uiso 1 1 calc R . . C9 C 0.4572(5) 0.3750(7) 0.1267(3) 0.0533(15) Uani 1 1 d . . . H9 H 0.4257 0.4260 0.1581 0.064 Uiso 1 1 calc R . . C10 C 0.5492(4) 0.2831(6) 0.1456(3) 0.0433(12) Uani 1 1 d . . . C11 C 0.6085(5) 0.2446(7) 0.2140(3) 0.0493(14) Uani 1 1 d . . . H11A H 0.6052 0.3303 0.2429 0.059 Uiso 1 1 calc R . . H11B H 0.5718 0.1593 0.2305 0.059 Uiso 1 1 calc R . . N3 N 0.7274(4) 0.2059(6) 0.2137(2) 0.0453(11) Uani 1 1 d . . . H1N3 H 0.755(6) 0.145(8) 0.249(3) 0.056(18) Uiso 1 1 d . . . C12 C 0.7948(5) 0.3471(7) 0.2207(3) 0.0499(14) Uani 1 1 d . . . H12A H 0.8111 0.3773 0.2666 0.060 Uiso 1 1 calc R . . H12B H 0.7518 0.4276 0.1957 0.060 Uiso 1 1 calc R . . C13 C 0.9045(5) 0.3254(8) 0.1962(3) 0.0529(14) Uani 1 1 d . . . H13A H 0.9449 0.4206 0.1986 0.063 Uiso 1 1 calc R . . H13B H 0.9512 0.2520 0.2237 0.063 Uiso 1 1 calc R . . N4 N 0.8789(4) 0.2711(6) 0.1272(2) 0.0453(11) Uani 1 1 d . . . C14 C 0.8495(6) 0.4019(7) 0.0815(3) 0.0584(16) Uani 1 1 d . . . H14A H 0.7886 0.4575 0.0935 0.088 Uiso 1 1 calc R . . H14B H 0.8276 0.3651 0.0372 0.088 Uiso 1 1 calc R . . H14C H 0.9134 0.4672 0.0842 0.088 Uiso 1 1 calc R . . C15 C 0.9719(5) 0.1837(8) 0.1100(3) 0.0575(15) Uani 1 1 d . . . H15A H 1.0419 0.2363 0.1257 0.069 Uiso 1 1 calc R . . H15B H 0.9618 0.1744 0.0625 0.069 Uiso 1 1 calc R . . C16 C 0.9764(5) 0.0269(8) 0.1409(3) 0.0594(16) Uani 1 1 d . . . H16A H 1.0343 -0.0326 0.1264 0.071 Uiso 1 1 calc R . . H16B H 0.9954 0.0359 0.1884 0.071 Uiso 1 1 calc R . . N5 N 0.8676(4) -0.0509(7) 0.1221(3) 0.0560(13) Uani 1 1 d . . . H1N5 H 0.859(6) -0.119(8) 0.142(3) 0.06(2) Uiso 1 1 d . . . C17 C 0.8492(6) -0.1245(8) 0.0553(4) 0.0691(19) Uani 1 1 d . . . H17A H 0.9194 -0.1259 0.0395 0.083 Uiso 1 1 calc R . . H17B H 0.8258 -0.2287 0.0592 0.083 Uiso 1 1 calc R . . Cl2 Cl 0.68411(12) -0.25423(16) 0.21178(7) 0.0548(5) Uani 1 1 d . . . O21 O 0.6352(6) -0.3529(7) 0.2505(4) 0.115(2) Uani 1 1 d . . . O22 O 0.6714(7) -0.3133(9) 0.1466(3) 0.127(3) Uani 1 1 d . . . O23 O 0.6345(7) -0.1094(6) 0.2071(4) 0.108(2) Uani 1 1 d . . . O24 O 0.7982(5) -0.2509(11) 0.2342(4) 0.144(3) Uani 1 1 d . . . Cl1 Cl 0.84655(12) 0.38305(18) -0.11152(6) 0.0546(5) Uani 1 1 d . . . O11 O 0.7316(4) 0.3565(6) -0.1405(2) 0.0744(14) Uani 1 1 d . . . O12 O 0.8561(4) 0.5218(6) -0.0760(2) 0.0772(14) Uani 1 1 d . . . O13 O 0.9125(5) 0.3840(8) -0.1620(3) 0.105(2) Uani 1 1 d . . . O14 O 0.8811(5) 0.2593(7) -0.0668(2) 0.0944(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 Cu1 0.0444(5) 0.0482(6) 0.0349(5) -0.0025(3) 0.0140(3) 0.0027(3) N1 0.050(3) 0.049(3) 0.044(2) -0.008(2) 0.018(2) -0.005(2) N2 0.044(2) 0.048(3) 0.036(2) -0.0036(19) 0.0111(18) -0.004(2) C1 0.057(3) 0.051(3) 0.053(3) -0.013(3) 0.030(3) -0.011(3) C2 0.084(5) 0.064(4) 0.064(4) -0.023(4) 0.050(4) -0.022(4) C3 0.096(5) 0.075(5) 0.041(3) -0.017(3) 0.025(3) -0.032(4) C4 0.068(4) 0.062(4) 0.040(3) -0.005(3) 0.014(3) -0.021(3) C5 0.054(3) 0.050(3) 0.035(3) -0.001(2) 0.016(2) -0.014(3) C6 0.041(3) 0.053(3) 0.039(3) 0.002(2) 0.013(2) -0.011(2) C7 0.050(3) 0.065(4) 0.051(3) 0.011(3) 0.000(3) -0.004(3) C8 0.049(3) 0.056(4) 0.074(4) 0.009(3) 0.017(3) 0.010(3) C9 0.052(3) 0.051(3) 0.062(4) -0.004(3) 0.026(3) 0.006(3) C10 0.046(3) 0.042(3) 0.045(3) -0.001(2) 0.020(2) -0.004(2) C11 0.056(3) 0.052(3) 0.045(3) -0.005(3) 0.023(3) 0.001(3) N3 0.052(3) 0.051(3) 0.035(2) 0.002(2) 0.015(2) 0.002(2) C12 0.059(3) 0.054(3) 0.039(3) -0.007(3) 0.015(2) -0.014(3) C13 0.055(3) 0.066(4) 0.038(3) -0.001(3) 0.009(2) -0.008(3) N4 0.047(2) 0.058(3) 0.034(2) 0.002(2) 0.0156(19) 0.001(2) C14 0.070(4) 0.054(4) 0.053(3) 0.010(3) 0.017(3) -0.001(3) C15 0.056(3) 0.066(4) 0.056(3) -0.001(3) 0.025(3) 0.005(3) C16 0.051(3) 0.068(4) 0.061(4) 0.010(3) 0.013(3) 0.008(3) N5 0.061(3) 0.051(3) 0.061(3) 0.010(3) 0.026(3) 0.005(3) C17 0.069(4) 0.066(4) 0.079(5) -0.016(4) 0.031(4) 0.008(3) Cl2 0.0661(10) 0.0526(9) 0.0498(8) 0.0069(6) 0.0214(7) 0.0025(7) O21 0.149(6) 0.086(4) 0.138(5) 0.047(4) 0.100(5) 0.013(4) O22 0.201(8) 0.119(5) 0.058(3) -0.013(3) 0.015(4) 0.030(6) O23 0.141(6) 0.054(3) 0.128(5) 0.002(3) 0.023(4) 0.021(3) O24 0.074(4) 0.162(7) 0.180(7) 0.064(6) -0.012(4) -0.010(4) Cl1 0.0555(9) 0.0719(10) 0.0399(8) -0.0060(6) 0.0176(6) -0.0024(7) O11 0.062(3) 0.096(4) 0.066(3) -0.009(3) 0.016(2) -0.003(3) O12 0.095(3) 0.071(3) 0.071(3) -0.017(3) 0.028(3) -0.015(3) O13 0.093(4) 0.164(6) 0.075(3) -0.041(4) 0.054(3) -0.056(4) O14 0.121(5) 0.094(4) 0.066(3) 0.004(3) 0.010(3) 0.036(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric.Sci.(1965),15(II-A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d Plane 1 m1 = .58486( .00146) m2 = .78002( .00104) m3 = -.22251( .00186) D = 5.06664( .01308) Atom d s d/s (d/s)**2 N1 * .0728 .0046 15.899 252.771 N2 * -.0610 .0042 -14.667 215.127 N3 * .0644 .0051 12.583 158.338 N5 * -.0809 .0058 -13.962 194.932 Cu1 .0772 .0008 100.027 10005.430 #=========== Sum((d/s)**2) for starred atoms 821.168 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarity Plane 2 m1 = .61038( .00110) m2 = .77287( .00092) m3 = -.17350( .00128) D = 5.39980( .00818) Atom d s d/s (d/s)**2 N1 * -.0181 .0046 -3.924 15.398 N2 * -.1339 .0042 -32.259 1040.618 C4 * .1319 .0067 19.835 393.433 C7 * .0665 .0067 9.901 98.030 N3 * .1351 .0051 26.364 695.061 N5 * -.0324 .0058 -5.627 31.665 #=========== Sum((d/s)**2) for starred atoms 2274.205 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity Plane 3 m1 = -.63475( .00170) m2 = .05432( .00258) m3 = -.77080( .00137) D = -8.32551( .01341) Atom d s d/s (d/s)**2 N3 * .0000 .0044 .000 .000 N4 * .0000 .0044 .000 .000 N5 * .0000 .0057 .000 .000 #=========== Sum((d/s)**2) for starred atoms .000 Plane 4 m1 = -.66255( .00315) m2 = -.73694( .00277) m3 = .13400( .00331) D = -5.82773( .02524) Atom d s d/s (d/s)**2 N1 * .0000 .0046 .000 .000 C4 * .0000 .0067 .000 .000 C2 * .0000 .0072 .000 .000 #=========== Sum((d/s)**2) for starred atoms .000 Plane 5 m1 = .61748( .00254) m2 = .78441( .00204) m3 = -.05850( .00346) D = 5.56832( .01283) Atom d s d/s (d/s)**2 N2 * .0000 .0042 .000 .000 C7 * .0000 .0067 .000 .000 C9 * .0000 .0062 .000 .000 #=========== Sum((d/s)**2) for starred atoms .000 Weighted least-squares lines through the starred atoms (Schoemaker,Waser,Marsh & Bergman,Acta Cryst.(1959).12,600) m1,m2,m3 are the direction cosines referred to the X,Y,Z orthogonal axes. X0,Y0,Z0 are the coordinates of the centroid of the set of atoms. Equation of the line: (X-X0)/m1=(Y-Y0)/m2=(Z-Z0)/m3 Line 1 m1 = -.76534( .00149) X0 = 9.33237( .00249) m2 = -.64330( .00178) Y0 = 1.67546( .00268) m3 = -.02053( .00185) Z0 = 2.56021( .00205) Atom d s d/s (d/s)**2 N4 * .0000 .0066 .000 .000 Cu1 * .0000 .0010 .002 .000 #=========== Sum((d/s)**2) for starred atoms .000 Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 3.19( .12) 176.81( .12) 1 3 80.95( .16) 99.05( .16) 1 4 7.19( .21) 172.81( .21) 1 5 9.60( .22) 170.40( .22) 2 3 77.78( .15) 102.22( .15) 2 4 4.28( .19) 175.72( .19) 2 5 6.64( .22) 173.36( .22) 3 4 73.90( .23) 106.10( .23) 3 5 72.29( .24) 107.71( .24) 4 5 5.73( .26) 174.27( .26) Angles formed by lines and normals to planes Line - plane angle (s.u.) angle (s.u.) 1 1 19.12( .13) 160.88( .13) 1 2 16.10( .12) 163.90( .12) 1 3 62.18( .17) 117.82( .17) 1 4 11.93( .19) 168.07( .19) 1 5 12.58( .18) 167.42( .18) ; 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 N2 1.945(4) . ? Cu1 N1 1.956(4) . ? Cu1 N3 2.053(4) . ? Cu1 N5 2.122(5) . ? Cu1 N4 2.226(5) . ? N1 C1 1.330(7) . ? N1 C5 1.344(7) . ? N2 C10 1.348(7) . ? N2 C6 1.351(6) . ? C1 C2 1.419(9) . ? C1 C17 1.482(10) . ? C2 C3 1.355(11) . ? C2 H2 0.9300 . ? C3 C4 1.377(10) . ? C3 H3 0.9300 . ? C4 C5 1.387(8) . ? C4 H4 0.9300 . ? C5 C6 1.492(8) . ? C6 C7 1.382(8) . ? C7 C8 1.396(9) . ? C7 H7 0.9300 . ? C8 C9 1.381(9) . ? C8 H8 0.9300 . ? C9 C10 1.377(8) . ? C9 H9 0.9300 . ? C10 C11 1.499(8) . ? C11 N3 1.486(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? N3 C12 1.483(7) . ? N3 H1N3 0.92(7) . ? C12 C13 1.526(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N4 1.481(7) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? N4 C15 1.467(7) . ? N4 C14 1.492(7) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.520(9) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N5 1.474(9) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? N5 C17 1.505(9) . ? N5 H1N5 0.75(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? Cl2 O24 1.377(6) . ? Cl2 O21 1.390(5) . ? Cl2 O23 1.408(6) . ? Cl2 O22 1.426(6) . ? Cl1 O12 1.421(5) . ? Cl1 O11 1.431(5) . ? Cl1 O13 1.433(5) . ? Cl1 O14 1.440(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 79.57(18) . . ? N2 Cu1 N3 80.92(18) . . ? N1 Cu1 N3 160.5(2) . . ? N2 Cu1 N5 158.9(2) . . ? N1 Cu1 N5 81.1(2) . . ? N3 Cu1 N5 118.4(2) . . ? N2 Cu1 N4 110.60(18) . . ? N1 Cu1 N4 102.27(17) . . ? N3 Cu1 N4 83.78(17) . . ? N5 Cu1 N4 81.7(2) . . ? C1 N1 C5 122.4(5) . . ? C1 N1 Cu1 120.2(4) . . ? C5 N1 Cu1 117.3(4) . . ? C10 N2 C6 122.2(5) . . ? C10 N2 Cu1 119.6(3) . . ? C6 N2 Cu1 117.5(3) . . ? N1 C1 C2 118.0(6) . . ? N1 C1 C17 115.4(5) . . ? C2 C1 C17 126.5(6) . . ? C3 C2 C1 119.9(6) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.9(6) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 117.7(6) . . ? C3 C4 H4 121.1 . . ? C5 C4 H4 121.1 . . ? N1 C5 C4 121.0(5) . . ? N1 C5 C6 112.2(4) . . ? C4 C5 C6 126.8(6) . . ? N2 C6 C7 120.1(5) . . ? N2 C6 C5 111.5(5) . . ? C7 C6 C5 128.3(5) . . ? C6 C7 C8 118.1(5) . . ? C6 C7 H7 120.9 . . ? C8 C7 H7 120.9 . . ? C9 C8 C7 120.7(6) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C10 C9 C8 119.1(5) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? N2 C10 C9 119.8(5) . . ? N2 C10 C11 111.9(5) . . ? C9 C10 C11 128.3(5) . . ? N3 C11 C10 110.0(4) . . ? N3 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? N3 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C12 N3 C11 109.0(5) . . ? C12 N3 Cu1 108.0(3) . . ? C11 N3 Cu1 109.0(3) . . ? C12 N3 H1N3 108(4) . . ? C11 N3 H1N3 110(4) . . ? Cu1 N3 H1N3 113(4) . . ? N3 C12 C13 111.3(5) . . ? N3 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? N3 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? N4 C13 C12 108.9(4) . . ? N4 C13 H13A 109.9 . . ? C12 C13 H13A 109.9 . . ? N4 C13 H13B 109.9 . . ? C12 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C15 N4 C13 111.9(5) . . ? C15 N4 C14 110.8(4) . . ? C13 N4 C14 110.1(5) . . ? C15 N4 Cu1 106.4(4) . . ? C13 N4 Cu1 104.4(3) . . ? C14 N4 Cu1 113.2(4) . . ? N4 C14 H14A 109.5 . . ? N4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N4 C15 C16 110.2(5) . . ? N4 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? N4 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? N5 C16 C15 110.7(5) . . ? N5 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? N5 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? C16 N5 C17 114.3(5) . . ? C16 N5 Cu1 108.5(4) . . ? C17 N5 Cu1 109.3(4) . . ? C16 N5 H1N5 116(6) . . ? C17 N5 H1N5 99(5) . . ? Cu1 N5 H1N5 109(6) . . ? C1 C17 N5 112.4(5) . . ? C1 C17 H17A 109.1 . . ? N5 C17 H17A 109.1 . . ? C1 C17 H17B 109.1 . . ? N5 C17 H17B 109.1 . . ? H17A C17 H17B 107.8 . . ? O24 Cl2 O21 109.5(5) . . ? O24 Cl2 O23 113.3(5) . . ? O21 Cl2 O23 112.5(4) . . ? O24 Cl2 O22 104.3(6) . . ? O21 Cl2 O22 109.5(5) . . ? O23 Cl2 O22 107.4(4) . . ? O12 Cl1 O11 109.5(3) . . ? O12 Cl1 O13 111.7(3) . . ? O11 Cl1 O13 109.5(3) . . ? O12 Cl1 O14 109.6(3) . . ? O11 Cl1 O14 106.7(4) . . ? O13 Cl1 O14 109.7(4) . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 59.99 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.674 _refine_diff_density_min -0.776 _refine_diff_density_rms 0.097 #===END