# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author_name # Name of author for correspondence 'Andrea Bencini' _publ_contact_author_address # Address of author for correspondence ; Department of Chemistry University of Florence via della Lastruccia 3 I-50019 Sesto F.no Florence Italy ; _publ_contact_author_email andrea.bencini@unifi.it _publ_contact_author_phone +390554573371 _publ_section_title ; Proton and metal binding by cyclen-based highly rigid cryptands ; loop_ _publ_author_name _publ_author_address _publ_author_footnote A.Benicini ; Department of Chemistry University of Florence via della Lastruccia 3 I-50019 Sesto F.no Florence Italy ; ; . ; C.Bazzicalupi ; Department of Chemistry University of Florence Via della Lastruccia 3 50019 Sesto Fiorentino Florence Italy ; ; . ; I.Matera ; Department of Chemistry University of Florence Via della Lastruccia 3 50019 Sesto Fiorentino Florence Italy ; ; . ; S.Ciattini ; Department of Chemistry University of Florence Via della Lastruccia 3 50019 Sesto Fiorentino Florence Italy ; ; . ; B.Valtancoli ; Department of Chemistry University of Florence Via della Lastruccia 3 50019 Sesto Fiorentino Florence Italy ; ; . ; data_[HL1]L1.ClO4.3.5H2O _database_code_depnum_ccdc_archive 'CCDC 787304' #TrackingRef '- revised CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H64 Cl N8 O9.50' _chemical_formula_weight 892.48 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5000(2) _cell_length_b 23.3006(7) _cell_length_c 19.3576(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.935(3) _cell_angle_gamma 90.00 _cell_volume 4664.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 2150 _cell_measurement_theta_min 3.7899 _cell_measurement_theta_max 70.1221 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1908 _exptl_absorpt_coefficient_mu 1.244 _exptl_absorpt_correction_T_min 0.70139 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.1241 _diffrn_standards_number 0 _diffrn_standards_interval_count infinity _diffrn_standards_interval_time infinity _diffrn_standards_decay_% ? _diffrn_reflns_number 15733 _diffrn_reflns_av_R_equivalents 0.0892 _diffrn_reflns_av_sigmaI/netI 0.1561 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.45 _diffrn_reflns_theta_max 58.93 _reflns_number_total 6624 _reflns_number_gt 2906 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SIR97 (Altomare 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 Ver. 1.01\b (Farrugia, 1997)' _computing_publication_material 'PARST93 (Nardelli, 1993)' _refine_special_details ; H5 and H1 hydrogen atoms, involved in dense H-bond networks, feature long N-H bond lenghts. So for the N4-H5 and the N6-H1 bond lengths, dfix restrains were used ; _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^)+(0.1356P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6624 _refine_ls_number_parameters 587 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1841 _refine_ls_R_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.2568 _refine_ls_wR_factor_gt 0.2102 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.935 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.58947(17) -0.04263(9) 0.15662(11) 0.0492(6) Uani 1 1 d . . . O11 O 0.7200(4) -0.0490(2) 0.1448(3) 0.0683(17) Uani 1 1 d . . . O12 O 0.5205(5) -0.0090(2) 0.0996(3) 0.084(2) Uani 1 1 d . . . O13 O 0.5859(9) -0.0131(4) 0.2176(4) 0.146(3) Uani 1 1 d . . . O14 O 0.5329(5) -0.0969(2) 0.1577(3) 0.0739(18) Uani 1 1 d . . . N1 N 0.7074(5) 0.3137(2) 0.2296(3) 0.0373(15) Uani 1 1 d . . . C1 C 0.5889(6) 0.2914(3) 0.2503(3) 0.0373(18) Uani 1 1 d . . . H1A H 0.5730 0.3114 0.2919 0.045 Uiso 1 1 calc R . . H1B H 0.5999 0.2509 0.2616 0.045 Uiso 1 1 calc R . . C2 C 0.4732(6) 0.2991(3) 0.1918(3) 0.0398(19) Uani 1 1 d . . . H2A H 0.3964 0.2838 0.2068 0.048 Uiso 1 1 calc R . . H2B H 0.4593 0.3397 0.1822 0.048 Uiso 1 1 calc R . . N2 N 0.4943(5) 0.2693(2) 0.1270(3) 0.0300(14) Uani 1 1 d . . . H4 H 0.576(7) 0.273(3) 0.130(3) 0.053(11) Uiso 1 1 d . . . C3 C 0.4252(6) 0.2941(3) 0.0621(3) 0.0364(18) Uani 1 1 d . . . H3A H 0.4222 0.3356 0.0667 0.044 Uiso 1 1 calc R . . H3B H 0.3371 0.2799 0.0530 0.044 Uiso 1 1 calc R . . C4 C 0.4936(6) 0.2783(3) 0.0009(3) 0.0365(18) Uani 1 1 d . . . H4A H 0.4918 0.2370 -0.0054 0.044 Uiso 1 1 calc R . . H4B H 0.4481 0.2956 -0.0420 0.044 Uiso 1 1 calc R . . N3 N 0.6278(5) 0.2982(2) 0.0139(3) 0.0328(14) Uani 1 1 d . . . C5 C 0.6362(7) 0.3594(3) -0.0041(4) 0.0436(19) Uani 1 1 d . . . H5A H 0.5599 0.3792 0.0053 0.052 Uiso 1 1 calc R . . H5B H 0.6385 0.3629 -0.0538 0.052 Uiso 1 1 calc R . . C6 C 0.7585(7) 0.3879(3) 0.0385(4) 0.051(2) Uani 1 1 d . . . H6A H 0.8327 0.3755 0.0187 0.062 Uiso 1 1 calc R . . H6B H 0.7507 0.4291 0.0318 0.062 Uiso 1 1 calc R . . N4 N 0.7852(7) 0.3765(3) 0.1133(4) 0.0587(19) Uani 1 1 d D . . H5 H 0.814(9) 0.3315(16) 0.126(5) 0.14(4) Uiso 1 1 d D . . C7 C 0.6903(8) 0.3979(4) 0.1509(5) 0.072(3) Uani 1 1 d . . . H7A H 0.6053 0.3854 0.1281 0.086 Uiso 1 1 calc R . . H7B H 0.6917 0.4395 0.1505 0.086 Uiso 1 1 calc R . . C8 C 0.7162(7) 0.3761(3) 0.2286(4) 0.055(2) Uani 1 1 d . . . H8A H 0.8015 0.3881 0.2515 0.066 Uiso 1 1 calc R . . H8B H 0.6530 0.3926 0.2540 0.066 Uiso 1 1 calc R . . C9 C 0.8258(6) 0.2867(3) 0.2701(3) 0.044(2) Uani 1 1 d . . . H9A H 0.9016 0.3044 0.2567 0.053 Uiso 1 1 calc R . . H9B H 0.8286 0.2938 0.3197 0.053 Uiso 1 1 calc R . . C10 C 0.8303(6) 0.2240(3) 0.2581(3) 0.0357(18) Uani 1 1 d . . . C11 C 0.8478(6) 0.1855(4) 0.3128(4) 0.049(2) Uani 1 1 d . . . H11 H 0.8588 0.1996 0.3584 0.058 Uiso 1 1 calc R . . C12 C 0.8498(7) 0.1259(4) 0.3029(4) 0.049(2) Uani 1 1 d . . . H12 H 0.8619 0.1017 0.3417 0.059 Uiso 1 1 calc R . . C13 C 0.8337(6) 0.1025(3) 0.2356(4) 0.042(2) Uani 1 1 d . . . H13 H 0.8349 0.0630 0.2287 0.050 Uiso 1 1 calc R . . C14 C 0.8158(5) 0.1408(3) 0.1787(3) 0.0306(17) Uani 1 1 d . . . C15 C 0.8185(6) 0.1992(3) 0.1918(3) 0.0315(17) Uani 1 1 d . . . O1 O 0.7961(4) 0.23101(19) 0.1297(2) 0.0325(11) Uani 1 1 d . . . C16 C 0.7715(6) 0.1896(3) 0.0768(3) 0.0289(16) Uani 1 1 d . . . C17 C 0.7843(6) 0.1344(3) 0.1034(3) 0.0295(16) Uani 1 1 d . . . C18 C 0.7564(6) 0.0877(3) 0.0588(4) 0.0349(18) Uani 1 1 d . . . H18 H 0.7643 0.0503 0.0758 0.042 Uiso 1 1 calc R . . C19 C 0.7167(6) 0.0986(3) -0.0113(4) 0.0363(18) Uani 1 1 d . . . H19 H 0.6981 0.0681 -0.0424 0.044 Uiso 1 1 calc R . . C20 C 0.7036(6) 0.1558(3) -0.0371(3) 0.0341(18) Uani 1 1 d . . . H20 H 0.6758 0.1615 -0.0849 0.041 Uiso 1 1 calc R . . C21 C 0.7305(6) 0.2031(3) 0.0059(3) 0.0307(17) Uani 1 1 d . . . C22 C 0.7138(6) 0.2635(3) -0.0214(3) 0.0348(18) Uani 1 1 d . . . H22A H 0.7978 0.2819 -0.0155 0.042 Uiso 1 1 calc R . . H22B H 0.6792 0.2624 -0.0712 0.042 Uiso 1 1 calc R . . N5 N 0.1975(5) 0.1182(2) 0.0359(3) 0.0303(14) Uani 1 1 d . . . C23 C 0.1855(6) 0.0565(3) 0.0269(4) 0.0371(18) Uani 1 1 d . . . H23A H 0.2706 0.0391 0.0378 0.045 Uiso 1 1 calc R . . H23B H 0.1507 0.0480 -0.0218 0.045 Uiso 1 1 calc R . . C24 C 0.0973(6) 0.0298(3) 0.0739(4) 0.042(2) Uani 1 1 d . . . H24A H 0.0086 0.0401 0.0550 0.050 Uiso 1 1 calc R . . H24B H 0.1041 -0.0116 0.0713 0.050 Uiso 1 1 calc R . . N6 N 0.1250(5) 0.0470(3) 0.1482(3) 0.0396(15) Uani 1 1 d D . . H1 H 0.132(6) 0.0940(10) 0.142(3) 0.053(11) Uiso 1 1 d D . . C25 C 0.2526(6) 0.0293(3) 0.1834(4) 0.045(2) Uani 1 1 d . . . H25A H 0.3167 0.0403 0.1553 0.054 Uiso 1 1 calc R . . H25B H 0.2551 -0.0121 0.1885 0.054 Uiso 1 1 calc R . . C26 C 0.2839(7) 0.0571(3) 0.2545(4) 0.047(2) Uani 1 1 d . . . H26A H 0.2187 0.0465 0.2821 0.057 Uiso 1 1 calc R . . H26B H 0.3666 0.0430 0.2786 0.057 Uiso 1 1 calc R . . N7 N 0.2892(5) 0.1206(2) 0.2492(3) 0.0363(15) Uani 1 1 d . . . C27 C 0.4223(6) 0.1435(3) 0.2638(3) 0.0381(18) Uani 1 1 d . . . H27A H 0.4703 0.1249 0.3051 0.046 Uiso 1 1 calc R . . H27B H 0.4200 0.1843 0.2731 0.046 Uiso 1 1 calc R . . C28 C 0.4904(6) 0.1328(3) 0.2007(3) 0.0366(18) Uani 1 1 d . . . H28A H 0.5749 0.1509 0.2089 0.044 Uiso 1 1 calc R . . H28B H 0.5024 0.0919 0.1949 0.044 Uiso 1 1 calc R . . N8 N 0.4121(5) 0.1566(3) 0.1363(3) 0.0298(14) Uani 1 1 d . . . H2 H 0.332(7) 0.146(3) 0.141(3) 0.053(11) Uiso 1 1 d . . . H3 H 0.431(6) 0.194(3) 0.134(4) 0.053(11) Uiso 1 1 d . . . C29 C 0.4338(5) 0.1296(3) 0.0695(3) 0.0325(17) Uani 1 1 d . . . H29A H 0.4479 0.0887 0.0763 0.039 Uiso 1 1 calc R . . H29B H 0.5101 0.1461 0.0552 0.039 Uiso 1 1 calc R . . C30 C 0.3154(6) 0.1401(3) 0.0126(3) 0.0336(17) Uani 1 1 d . . . H30A H 0.3062 0.1809 0.0029 0.040 Uiso 1 1 calc R . . H30B H 0.3270 0.1208 -0.0303 0.040 Uiso 1 1 calc R . . C31 C 0.0815(6) 0.1474(3) 0.0011(3) 0.0325(17) Uani 1 1 d . . . H31A H 0.0063 0.1290 0.0143 0.039 Uiso 1 1 calc R . . H31B H 0.0753 0.1435 -0.0492 0.039 Uiso 1 1 calc R . . C32 C 0.0797(6) 0.2096(3) 0.0191(3) 0.0291(16) Uani 1 1 d . . . C33 C 0.0611(6) 0.2536(3) -0.0313(3) 0.0341(17) Uani 1 1 d . . . H33 H 0.0453 0.2433 -0.0784 0.041 Uiso 1 1 calc R . . C34 C 0.0651(6) 0.3114(3) -0.0147(3) 0.0383(19) Uani 1 1 d . . . H34 H 0.0549 0.3384 -0.0506 0.046 Uiso 1 1 calc R . . C35 C 0.0841(6) 0.3300(3) 0.0550(3) 0.0336(17) Uani 1 1 d . . . H35 H 0.0871 0.3688 0.0663 0.040 Uiso 1 1 calc R . . C36 C 0.0983(6) 0.2879(3) 0.1067(4) 0.0319(17) Uani 1 1 d . . . C37 C 0.0960(5) 0.2300(3) 0.0877(3) 0.0269(16) Uani 1 1 d . . . O2 O 0.1203(4) 0.19409(18) 0.1460(2) 0.0299(11) Uani 1 1 d . . . C38 C 0.1458(6) 0.2306(3) 0.2037(3) 0.0282(16) Uani 1 1 d . . . C39 C 0.1308(6) 0.2881(3) 0.1839(3) 0.0305(17) Uani 1 1 d . . . C40 C 0.1587(6) 0.3318(3) 0.2347(4) 0.0360(18) Uani 1 1 d . . . H40 H 0.1500 0.3704 0.2227 0.043 Uiso 1 1 calc R . . C41 C 0.1997(6) 0.3143(3) 0.3031(4) 0.0401(19) Uani 1 1 d . . . H41 H 0.2182 0.3419 0.3381 0.048 Uiso 1 1 calc R . . C42 C 0.2141(6) 0.2564(4) 0.3209(4) 0.042(2) Uani 1 1 d . . . H42 H 0.2438 0.2467 0.3675 0.051 Uiso 1 1 calc R . . C43 C 0.1857(6) 0.2122(3) 0.2715(4) 0.0349(18) Uani 1 1 d . . . C44 C 0.2042(6) 0.1497(3) 0.2911(3) 0.0404(19) Uani 1 1 d . . . H44A H 0.2414 0.1467 0.3404 0.048 Uiso 1 1 calc R . . H44B H 0.1207 0.1308 0.2839 0.048 Uiso 1 1 calc R . . OW1 O -0.0153(5) -0.0357(2) 0.2060(3) 0.0604(16) Uani 1 1 d . . . OW2 O 0.0240(6) -0.0422(3) 0.3470(3) 0.092(2) Uani 1 1 d . . . OW3 O -0.1333(12) -0.0081(6) 0.4328(7) 0.068(4) Uiso 0.40 1 d P . . OW4 O 0.421(2) 0.4681(10) -0.0624(12) 0.045(6) Uiso 0.20 1 d P . . OW5 O 0.085(2) 0.4530(10) -0.0581(11) 0.037(6) Uiso 0.20 1 d P . . OW6 O 0.1691(13) 0.4498(6) -0.0707(7) 0.060(4) Uiso 0.40 1 d P . . OW7 O 0.6394(17) 0.4865(8) -0.1314(10) 0.073(6) Uiso 0.30 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0448(11) 0.0428(13) 0.0602(13) -0.0079(11) 0.0092(9) -0.0012(10) O11 0.031(3) 0.071(4) 0.101(5) 0.004(4) 0.008(3) -0.001(3) O12 0.067(4) 0.050(4) 0.123(6) 0.035(4) -0.015(4) 0.009(3) O13 0.174(8) 0.180(9) 0.082(5) -0.079(6) 0.016(5) 0.025(7) O14 0.066(4) 0.047(4) 0.108(5) 0.026(4) 0.013(3) -0.019(3) N1 0.035(3) 0.035(4) 0.043(4) -0.017(3) 0.010(3) -0.010(3) C1 0.032(4) 0.040(5) 0.041(4) -0.019(4) 0.011(3) -0.007(3) C2 0.030(4) 0.048(5) 0.043(4) -0.014(4) 0.010(3) 0.000(4) N2 0.029(3) 0.029(4) 0.033(3) -0.004(3) 0.007(3) 0.005(3) C3 0.038(4) 0.027(5) 0.045(5) -0.005(4) 0.012(3) 0.001(3) C4 0.036(4) 0.034(5) 0.038(4) 0.004(4) 0.003(3) -0.006(3) N3 0.031(3) 0.024(4) 0.043(4) -0.005(3) 0.007(3) -0.007(3) C5 0.046(4) 0.032(5) 0.054(5) 0.001(4) 0.013(4) -0.004(4) C6 0.052(5) 0.039(5) 0.063(6) -0.001(5) 0.010(4) -0.008(4) N4 0.076(5) 0.043(5) 0.061(5) -0.008(4) 0.025(4) -0.006(4) C7 0.062(6) 0.043(6) 0.118(8) -0.011(6) 0.036(6) -0.011(5) C8 0.057(5) 0.049(6) 0.066(6) -0.014(5) 0.032(5) -0.013(4) C9 0.025(4) 0.072(6) 0.033(4) -0.015(4) 0.002(3) -0.013(4) C10 0.021(4) 0.055(6) 0.030(4) -0.007(4) 0.000(3) 0.009(3) C11 0.021(4) 0.089(7) 0.033(4) -0.004(5) -0.003(3) 0.001(4) C12 0.043(4) 0.068(7) 0.038(5) 0.010(5) 0.009(4) 0.015(4) C13 0.025(4) 0.053(6) 0.046(5) 0.001(4) 0.003(3) 0.006(4) C14 0.016(3) 0.038(5) 0.037(4) 0.004(4) 0.005(3) 0.001(3) C15 0.020(3) 0.048(5) 0.027(4) 0.001(4) 0.007(3) -0.003(3) O1 0.030(2) 0.036(3) 0.031(3) -0.009(2) 0.005(2) -0.005(2) C16 0.019(3) 0.034(5) 0.036(4) -0.013(4) 0.009(3) -0.005(3) C17 0.022(3) 0.034(5) 0.032(4) -0.002(4) 0.004(3) 0.004(3) C18 0.030(4) 0.030(5) 0.048(5) 0.000(4) 0.015(3) 0.000(3) C19 0.035(4) 0.034(5) 0.042(4) -0.008(4) 0.011(3) 0.001(3) C20 0.029(4) 0.045(5) 0.029(4) -0.008(4) 0.008(3) -0.003(4) C21 0.032(4) 0.033(5) 0.028(4) -0.006(4) 0.009(3) -0.006(3) C22 0.041(4) 0.040(5) 0.025(4) -0.006(4) 0.008(3) -0.005(4) N5 0.023(3) 0.029(4) 0.040(3) -0.005(3) 0.008(3) -0.002(3) C23 0.034(4) 0.030(5) 0.048(5) -0.012(4) 0.009(3) -0.008(3) C24 0.036(4) 0.040(5) 0.052(5) -0.010(4) 0.017(4) 0.000(4) N6 0.030(3) 0.037(4) 0.054(4) -0.001(4) 0.014(3) -0.005(3) C25 0.043(4) 0.030(5) 0.064(5) 0.001(4) 0.015(4) -0.007(4) C26 0.049(5) 0.039(5) 0.053(5) 0.012(4) 0.007(4) -0.006(4) N7 0.030(3) 0.037(4) 0.043(3) 0.003(3) 0.009(3) -0.004(3) C27 0.037(4) 0.039(5) 0.036(4) 0.004(4) 0.000(3) -0.004(4) C28 0.030(4) 0.036(5) 0.043(4) 0.010(4) 0.006(3) 0.006(3) N8 0.031(3) 0.022(4) 0.037(3) 0.006(3) 0.007(3) 0.002(3) C29 0.018(3) 0.042(5) 0.038(4) 0.004(4) 0.006(3) 0.002(3) C30 0.035(4) 0.038(5) 0.030(4) -0.002(4) 0.013(3) -0.001(3) C31 0.025(4) 0.041(5) 0.032(4) -0.011(4) 0.005(3) -0.005(3) C32 0.024(3) 0.031(5) 0.031(4) -0.004(4) 0.001(3) 0.000(3) C33 0.031(4) 0.041(5) 0.032(4) -0.007(4) 0.007(3) 0.004(4) C34 0.036(4) 0.046(5) 0.033(4) 0.011(4) 0.005(3) 0.004(4) C35 0.032(4) 0.029(5) 0.040(4) 0.004(4) 0.006(3) 0.007(3) C36 0.025(4) 0.030(5) 0.043(4) -0.003(4) 0.013(3) 0.002(3) C37 0.019(3) 0.030(4) 0.033(4) 0.006(4) 0.006(3) 0.003(3) O2 0.031(2) 0.033(3) 0.025(2) 0.000(2) 0.003(2) -0.001(2) C38 0.033(4) 0.026(4) 0.026(4) -0.006(3) 0.007(3) -0.004(3) C39 0.021(3) 0.041(5) 0.033(4) -0.001(4) 0.012(3) -0.001(3) C40 0.036(4) 0.029(5) 0.046(5) -0.011(4) 0.013(4) -0.004(3) C41 0.038(4) 0.045(5) 0.040(5) -0.020(4) 0.014(4) -0.009(4) C42 0.037(4) 0.062(6) 0.029(4) -0.009(4) 0.008(3) -0.006(4) C43 0.026(4) 0.041(5) 0.040(4) 0.000(4) 0.012(3) -0.001(3) C44 0.037(4) 0.055(6) 0.032(4) 0.000(4) 0.012(3) 0.002(4) OW1 0.054(3) 0.060(4) 0.067(4) 0.021(3) 0.011(3) -0.001(3) OW2 0.106(5) 0.102(6) 0.069(4) 0.001(4) 0.016(4) 0.032(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 O13 1.373(6) . ? Cl1 O14 1.398(5) . ? Cl1 O11 1.435(5) . ? Cl1 O12 1.442(6) . ? N1 C8 1.457(9) . ? N1 C1 1.467(7) . ? N1 C9 1.490(8) . ? C1 C2 1.521(8) . ? C2 N2 1.485(7) . ? N2 C3 1.457(8) . ? C3 C4 1.533(8) . ? C4 N3 1.463(7) . ? N3 C22 1.465(7) . ? N3 C5 1.473(8) . ? C5 C6 1.551(9) . ? C6 N4 1.451(9) . ? N4 C7 1.421(9) . ? C7 C8 1.566(11) . ? C9 C10 1.481(9) . ? C10 C11 1.376(10) . ? C10 C15 1.394(9) . ? C11 C12 1.402(10) . ? C12 C13 1.396(9) . ? C13 C14 1.405(9) . ? C14 C15 1.384(9) . ? C14 C17 1.445(8) . ? C15 O1 1.397(7) . ? O1 C16 1.399(7) . ? C16 C17 1.382(9) . ? C16 C21 1.403(9) . ? C17 C18 1.389(9) . ? C18 C19 1.372(9) . ? C19 C20 1.422(9) . ? C20 C21 1.382(9) . ? C21 C22 1.502(9) . ? N5 C23 1.451(8) . ? N5 C31 1.456(7) . ? N5 C30 1.480(7) . ? C23 C24 1.536(8) . ? C24 N6 1.475(8) . ? N6 C25 1.454(8) . ? C25 C26 1.506(9) . ? C26 N7 1.485(8) . ? N7 C44 1.472(7) . ? N7 C27 1.477(8) . ? C27 C28 1.540(8) . ? C28 N8 1.476(8) . ? N8 C29 1.491(8) . ? C29 C30 1.532(8) . ? C31 C32 1.492(8) . ? C32 C37 1.391(8) . ? C32 C33 1.405(9) . ? C33 C34 1.383(9) . ? C34 C35 1.398(8) . ? C35 C36 1.391(9) . ? C36 C37 1.396(9) . ? C36 C39 1.475(8) . ? C37 O2 1.393(7) . ? O2 C38 1.394(7) . ? C38 C43 1.375(9) . ? C38 C39 1.395(9) . ? C39 C40 1.410(9) . ? C40 C41 1.380(9) . ? C41 C42 1.396(10) . ? C42 C43 1.401(9) . ? C43 C44 1.509(9) . ? OW5 OW6 0.96(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O13 Cl1 O14 111.4(5) . . ? O13 Cl1 O11 111.0(5) . . ? O14 Cl1 O11 109.2(4) . . ? O13 Cl1 O12 107.6(5) . . ? O14 Cl1 O12 110.1(4) . . ? O11 Cl1 O12 107.5(4) . . ? C8 N1 C1 114.6(5) . . ? C8 N1 C9 112.3(6) . . ? C1 N1 C9 112.1(5) . . ? N1 C1 C2 111.2(6) . . ? N2 C2 C1 110.9(5) . . ? C3 N2 C2 114.7(5) . . ? N2 C3 C4 109.9(5) . . ? N3 C4 C3 110.8(5) . . ? C4 N3 C22 113.4(5) . . ? C4 N3 C5 111.2(5) . . ? C22 N3 C5 110.8(5) . . ? N3 C5 C6 111.5(6) . . ? N4 C6 C5 116.9(6) . . ? C7 N4 C6 114.6(7) . . ? N4 C7 C8 110.9(7) . . ? N1 C8 C7 109.6(6) . . ? C10 C9 N1 112.4(5) . . ? C11 C10 C15 114.7(7) . . ? C11 C10 C9 121.8(7) . . ? C15 C10 C9 123.6(7) . . ? C10 C11 C12 122.9(7) . . ? C13 C12 C11 120.9(7) . . ? C12 C13 C14 117.5(7) . . ? C15 C14 C13 119.0(7) . . ? C15 C14 C17 106.3(6) . . ? C13 C14 C17 134.6(7) . . ? C14 C15 C10 124.9(7) . . ? C14 C15 O1 111.7(6) . . ? C10 C15 O1 123.2(7) . . ? C15 O1 C16 104.2(5) . . ? C17 C16 O1 112.1(6) . . ? C17 C16 C21 124.6(6) . . ? O1 C16 C21 123.2(6) . . ? C16 C17 C18 120.0(6) . . ? C16 C17 C14 105.7(6) . . ? C18 C17 C14 134.0(7) . . ? C19 C18 C17 117.8(7) . . ? C18 C19 C20 121.0(7) . . ? C21 C20 C19 122.7(6) . . ? C20 C21 C16 113.9(6) . . ? C20 C21 C22 122.5(6) . . ? C16 C21 C22 123.5(6) . . ? N3 C22 C21 113.4(5) . . ? C23 N5 C31 111.1(5) . . ? C23 N5 C30 111.4(5) . . ? C31 N5 C30 112.0(5) . . ? N5 C23 C24 112.2(5) . . ? N6 C24 C23 115.6(5) . . ? C25 N6 C24 113.0(5) . . ? N6 C25 C26 110.1(6) . . ? N7 C26 C25 111.7(6) . . ? C44 N7 C27 111.8(5) . . ? C44 N7 C26 112.8(5) . . ? C27 N7 C26 113.1(5) . . ? N7 C27 C28 110.1(5) . . ? N8 C28 C27 110.0(5) . . ? C28 N8 C29 115.3(5) . . ? N8 C29 C30 109.3(5) . . ? N5 C30 C29 110.1(5) . . ? N5 C31 C32 113.0(5) . . ? C37 C32 C33 113.2(6) . . ? C37 C32 C31 123.4(6) . . ? C33 C32 C31 123.5(6) . . ? C34 C33 C32 123.6(6) . . ? C33 C34 C35 121.3(7) . . ? C36 C35 C34 117.1(7) . . ? C35 C36 C37 119.8(6) . . ? C35 C36 C39 134.8(7) . . ? C37 C36 C39 105.1(6) . . ? C32 C37 O2 122.9(6) . . ? C32 C37 C36 125.1(6) . . ? O2 C37 C36 112.0(6) . . ? C37 O2 C38 105.4(5) . . ? C43 C38 O2 124.0(6) . . ? C43 C38 C39 124.3(6) . . ? O2 C38 C39 111.6(6) . . ? C38 C39 C40 120.0(6) . . ? C38 C39 C36 105.7(6) . . ? C40 C39 C36 133.9(7) . . ? C41 C40 C39 116.7(7) . . ? C40 C41 C42 121.6(7) . . ? C41 C42 C43 122.7(7) . . ? C38 C43 C42 114.6(7) . . ? C38 C43 C44 123.1(7) . . ? C42 C43 C44 122.3(6) . . ? N7 C44 C43 111.8(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 C8 N1 C1 C2 74.0(7) . . . . ? C9 N1 C1 C2 -156.5(6) . . . . ? N1 C1 C2 N2 58.8(8) . . . . ? C1 C2 N2 C3 -152.6(6) . . . . ? C2 N2 C3 C4 156.3(5) . . . . ? N2 C3 C4 N3 -58.1(7) . . . . ? C3 C4 N3 C22 152.4(6) . . . . ? C3 C4 N3 C5 -81.9(7) . . . . ? C4 N3 C5 C6 154.0(6) . . . . ? C22 N3 C5 C6 -79.0(7) . . . . ? N3 C5 C6 N4 -46.7(9) . . . . ? C5 C6 N4 C7 -64.1(9) . . . . ? C6 N4 C7 C8 171.7(6) . . . . ? C1 N1 C8 C7 -105.1(6) . . . . ? C9 N1 C8 C7 125.5(6) . . . . ? N4 C7 C8 N1 -62.1(8) . . . . ? C8 N1 C9 C10 -167.1(5) . . . . ? C1 N1 C9 C10 62.2(7) . . . . ? N1 C9 C10 C11 -126.6(6) . . . . ? N1 C9 C10 C15 53.9(8) . . . . ? C15 C10 C11 C12 -1.8(9) . . . . ? C9 C10 C11 C12 178.7(6) . . . . ? C10 C11 C12 C13 0.0(10) . . . . ? C11 C12 C13 C14 0.0(10) . . . . ? C12 C13 C14 C15 1.8(9) . . . . ? C12 C13 C14 C17 -173.0(6) . . . . ? C13 C14 C15 C10 -4.0(9) . . . . ? C17 C14 C15 C10 172.1(6) . . . . ? C13 C14 C15 O1 -178.6(5) . . . . ? C17 C14 C15 O1 -2.5(7) . . . . ? C11 C10 C15 C14 3.9(9) . . . . ? C9 C10 C15 C14 -176.6(6) . . . . ? C11 C10 C15 O1 177.9(5) . . . . ? C9 C10 C15 O1 -2.6(9) . . . . ? C14 C15 O1 C16 3.4(6) . . . . ? C10 C15 O1 C16 -171.3(5) . . . . ? C15 O1 C16 C17 -3.1(6) . . . . ? C15 O1 C16 C21 173.0(5) . . . . ? O1 C16 C17 C18 176.4(5) . . . . ? C21 C16 C17 C18 0.3(9) . . . . ? O1 C16 C17 C14 1.7(6) . . . . ? C21 C16 C17 C14 -174.4(5) . . . . ? C15 C14 C17 C16 0.5(6) . . . . ? C13 C14 C17 C16 175.7(7) . . . . ? C15 C14 C17 C18 -173.1(6) . . . . ? C13 C14 C17 C18 2.1(12) . . . . ? C16 C17 C18 C19 0.2(9) . . . . ? C14 C17 C18 C19 173.1(6) . . . . ? C17 C18 C19 C20 -0.6(9) . . . . ? C18 C19 C20 C21 0.5(9) . . . . ? C19 C20 C21 C16 -0.1(9) . . . . ? C19 C20 C21 C22 -178.6(6) . . . . ? C17 C16 C21 C20 -0.3(9) . . . . ? O1 C16 C21 C20 -176.0(5) . . . . ? C17 C16 C21 C22 178.2(6) . . . . ? O1 C16 C21 C22 2.5(9) . . . . ? C4 N3 C22 C21 -66.0(7) . . . . ? C5 N3 C22 C21 168.2(5) . . . . ? C20 C21 C22 N3 123.7(6) . . . . ? C16 C21 C22 N3 -54.7(8) . . . . ? C31 N5 C23 C24 -75.6(7) . . . . ? C30 N5 C23 C24 158.8(5) . . . . ? N5 C23 C24 N6 -49.0(8) . . . . ? C23 C24 N6 C25 -62.9(8) . . . . ? C24 N6 C25 C26 169.8(6) . . . . ? N6 C25 C26 N7 -62.7(7) . . . . ? C25 C26 N7 C44 125.8(6) . . . . ? C25 C26 N7 C27 -106.0(6) . . . . ? C44 N7 C27 C28 -155.5(5) . . . . ? C26 N7 C27 C28 75.8(7) . . . . ? N7 C27 C28 N8 54.3(7) . . . . ? C27 C28 N8 C29 -155.5(5) . . . . ? C28 N8 C29 C30 157.8(5) . . . . ? C23 N5 C30 C29 -79.9(7) . . . . ? C31 N5 C30 C29 154.9(5) . . . . ? N8 C29 C30 N5 -56.1(7) . . . . ? C23 N5 C31 C32 170.1(5) . . . . ? C30 N5 C31 C32 -64.6(7) . . . . ? N5 C31 C32 C37 -54.1(8) . . . . ? N5 C31 C32 C33 126.0(6) . . . . ? C37 C32 C33 C34 3.1(9) . . . . ? C31 C32 C33 C34 -177.0(6) . . . . ? C32 C33 C34 C35 -2.2(10) . . . . ? C33 C34 C35 C36 -0.2(9) . . . . ? C34 C35 C36 C37 1.3(9) . . . . ? C34 C35 C36 C39 173.5(6) . . . . ? C33 C32 C37 O2 -177.7(5) . . . . ? C31 C32 C37 O2 2.4(9) . . . . ? C33 C32 C37 C36 -1.9(9) . . . . ? C31 C32 C37 C36 178.2(5) . . . . ? C35 C36 C37 C32 -0.2(9) . . . . ? C39 C36 C37 C32 -174.4(5) . . . . ? C35 C36 C37 O2 176.0(5) . . . . ? C39 C36 C37 O2 1.7(6) . . . . ? C32 C37 O2 C38 173.1(5) . . . . ? C36 C37 O2 C38 -3.2(6) . . . . ? C37 O2 C38 C43 -174.1(6) . . . . ? C37 O2 C38 C39 3.5(6) . . . . ? C43 C38 C39 C40 0.8(9) . . . . ? O2 C38 C39 C40 -176.8(5) . . . . ? C43 C38 C39 C36 175.1(6) . . . . ? O2 C38 C39 C36 -2.5(7) . . . . ? C35 C36 C39 C38 -172.5(7) . . . . ? C37 C36 C39 C38 0.5(6) . . . . ? C35 C36 C39 C40 0.6(12) . . . . ? C37 C36 C39 C40 173.6(6) . . . . ? C38 C39 C40 C41 -0.4(9) . . . . ? C36 C39 C40 C41 -172.7(6) . . . . ? C39 C40 C41 C42 0.7(9) . . . . ? C40 C41 C42 C43 -1.4(10) . . . . ? O2 C38 C43 C42 175.9(5) . . . . ? C39 C38 C43 C42 -1.4(9) . . . . ? O2 C38 C43 C44 -1.1(9) . . . . ? C39 C38 C43 C44 -178.4(6) . . . . ? C41 C42 C43 C38 1.7(9) . . . . ? C41 C42 C43 C44 178.7(6) . . . . ? C27 N7 C44 C43 65.2(7) . . . . ? C26 N7 C44 C43 -165.9(6) . . . . ? C38 C43 C44 N7 52.8(8) . . . . ? C42 C43 C44 N7 -124.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 58.93 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.781 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.088 #===END data_[H2L2](ClO4)2 _database_code_depnum_ccdc_archive 'CCDC 787305' #TrackingRef '- revised CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H32 Cl2 N4 O9' _chemical_formula_weight 567.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.2267(9) _cell_length_b 13.5562(9) _cell_length_c 15.5440(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.713(7) _cell_angle_gamma 90.00 _cell_volume 2563.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used 2591 _cell_measurement_theta_min 3.6698 _cell_measurement_theta_max 27.5421 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_T_min 0.49590 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number 0 _diffrn_standards_interval_count infinity _diffrn_standards_interval_time infinity _diffrn_standards_decay_% ? _diffrn_reflns_number 9348 _diffrn_reflns_av_R_equivalents 0.0773 _diffrn_reflns_av_sigmaI/netI 0.1146 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 23.25 _reflns_number_total 3442 _reflns_number_gt 1708 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SIR97 (Altomare 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 Ver. 1.01\b (Farrugia, 1997)' _computing_publication_material 'PARST93 (Nardelli, 1993)' _refine_special_details ; ISOR restrains were used for the adp parameters of oxygens O11 and O12 belonging to a perchlorate anion, most likely affected by rotational disorder ; _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^)+(0.1409P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3442 _refine_ls_number_parameters 334 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1585 _refine_ls_R_factor_gt 0.0815 _refine_ls_wR_factor_ref 0.2329 _refine_ls_wR_factor_gt 0.1941 _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_restrained_S_all 0.928 _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 Cl1 Cl 0.25346(16) 0.29716(16) -0.31282(14) 0.0703(7) Uani 1 1 d . . . O11 O 0.2169(8) 0.3905(7) -0.3341(6) 0.172(3) Uani 1 1 d U . . O12 O 0.3498(5) 0.2960(6) -0.2579(5) 0.141(3) Uani 1 1 d U . . O13 O 0.1749(5) 0.2492(6) -0.2678(4) 0.117(2) Uani 1 1 d . . . O14 O 0.2686(6) 0.2438(5) -0.3885(4) 0.121(2) Uani 1 1 d . . . Cl2 Cl 0.23553(14) 0.36184(14) 0.35865(13) 0.0620(6) Uani 1 1 d . . . O21 O 0.2472(5) 0.3972(5) 0.2741(4) 0.108(2) Uani 1 1 d . . . O22 O 0.2901(4) 0.4282(4) 0.4191(4) 0.096(2) Uani 1 1 d . . . O23 O 0.2824(5) 0.2679(4) 0.3667(5) 0.103(2) Uani 1 1 d . . . O24 O 0.1229(5) 0.3596(6) 0.3694(5) 0.130(3) Uani 1 1 d . . . N1 N 0.3886(4) 0.2008(4) 0.0522(4) 0.0496(15) Uani 1 1 d . . . C1 C 0.4085(5) 0.1102(5) 0.0029(4) 0.0559(19) Uani 1 1 d . . . H1A H 0.3724 0.0550 0.0279 0.067 Uiso 1 1 calc R . . H1B H 0.4867 0.0967 0.0078 0.067 Uiso 1 1 calc R . . C2 C 0.3667(5) 0.1190(5) -0.0913(4) 0.060(2) Uani 1 1 d . . . H2C H 0.4181 0.1575 -0.1212 0.072 Uiso 1 1 calc R . . H2D H 0.3612 0.0539 -0.1173 0.072 Uiso 1 1 calc R . . N2 N 0.2574(4) 0.1672(4) -0.1009(4) 0.0565(16) Uani 1 1 d . . . H2A H 0.2562 0.2136 -0.0596 0.068 Uiso 1 1 calc R . . H2B H 0.2492 0.1981 -0.1523 0.068 Uiso 1 1 calc R . . C3 C 0.1622(5) 0.1007(5) -0.0954(5) 0.060(2) Uani 1 1 d . . . H3A H 0.1784 0.0542 -0.0484 0.072 Uiso 1 1 calc R . . H3B H 0.1485 0.0636 -0.1488 0.072 Uiso 1 1 calc R . . C4 C 0.0616(5) 0.1598(5) -0.0802(5) 0.060(2) Uani 1 1 d . . . H4C H 0.0449 0.2055 -0.1276 0.072 Uiso 1 1 calc R . . H4D H -0.0006 0.1158 -0.0783 0.072 Uiso 1 1 calc R . . N3 N 0.0793(4) 0.2151(4) 0.0018(3) 0.0479(14) Uani 1 1 d . . . C5 C 0.0488(6) 0.1537(6) 0.0744(5) 0.067(2) Uani 1 1 d . . . H5A H 0.0778 0.0876 0.0692 0.080 Uiso 1 1 calc R . . H5B H -0.0307 0.1490 0.0719 0.080 Uiso 1 1 calc R . . C6 C 0.0933(6) 0.1974(7) 0.1594(5) 0.078(2) Uani 1 1 d . . . H6A H 0.0492 0.2539 0.1725 0.094 Uiso 1 1 calc R . . H6B H 0.0893 0.1490 0.2050 0.094 Uiso 1 1 calc R . . N4 N 0.2101(4) 0.2288(4) 0.1561(3) 0.0574(16) Uani 1 1 d . . . H4A H 0.2169 0.2536 0.1031 0.069 Uiso 1 1 calc R . . H4B H 0.2245 0.2780 0.1944 0.069 Uiso 1 1 calc R . . C7 C 0.2947(6) 0.1509(5) 0.1744(5) 0.063(2) Uani 1 1 d . . . H7A H 0.2709 0.0906 0.1446 0.075 Uiso 1 1 calc R . . H7B H 0.3044 0.1373 0.2359 0.075 Uiso 1 1 calc R . . C8 C 0.4020(5) 0.1845(5) 0.1444(4) 0.0557(19) Uani 1 1 d . . . H8A H 0.4256 0.2451 0.1739 0.067 Uiso 1 1 calc R . . H8B H 0.4580 0.1348 0.1585 0.067 Uiso 1 1 calc R . . C9 C 0.4566(5) 0.2839(5) 0.0261(5) 0.0526(18) Uani 1 1 d . . . H9A H 0.4487 0.2885 -0.0365 0.063 Uiso 1 1 calc R . . H9B H 0.5332 0.2697 0.0443 0.063 Uiso 1 1 calc R . . C10 C 0.4280(5) 0.3815(5) 0.0626(4) 0.0494(18) Uani 1 1 d . . . C11 C 0.5047(5) 0.4334(5) 0.1152(5) 0.0547(19) Uani 1 1 d . . . H11 H 0.5723 0.4040 0.1318 0.066 Uiso 1 1 calc R . . C12 C 0.4855(6) 0.5268(6) 0.1444(5) 0.067(2) Uani 1 1 d . . . H12 H 0.5388 0.5593 0.1807 0.080 Uiso 1 1 calc R . . C13 C 0.3865(7) 0.5719(5) 0.1192(5) 0.065(2) Uani 1 1 d . . . H13 H 0.3736 0.6357 0.1378 0.078 Uiso 1 1 calc R . . C14 C 0.3067(6) 0.5234(5) 0.0669(5) 0.0590(19) Uani 1 1 d . . . H14 H 0.2404 0.5542 0.0488 0.071 Uiso 1 1 calc R . . C15 C 0.3273(5) 0.4259(5) 0.0413(4) 0.0530(19) Uani 1 1 d . . . O1 O 0.2459(3) 0.3701(3) -0.0062(3) 0.0646(15) Uani 1 1 d . . . C16 C 0.1655(5) 0.4166(5) -0.0637(5) 0.0548(19) Uani 1 1 d . . . C17 C 0.1931(6) 0.4889(6) -0.1203(5) 0.067(2) Uani 1 1 d . . . H17 H 0.2657 0.5094 -0.1199 0.080 Uiso 1 1 calc R . . C18 C 0.1130(8) 0.5305(6) -0.1773(5) 0.079(2) Uani 1 1 d . . . H18 H 0.1305 0.5822 -0.2128 0.095 Uiso 1 1 calc R . . C19 C 0.0090(8) 0.4963(7) -0.1817(6) 0.080(3) Uani 1 1 d . . . H19 H -0.0444 0.5223 -0.2222 0.096 Uiso 1 1 calc R . . C20 C -0.0186(5) 0.4230(6) -0.1262(5) 0.062(2) Uani 1 1 d . . . H20 H -0.0905 0.3999 -0.1298 0.074 Uiso 1 1 calc R . . C21 C 0.0584(5) 0.3838(5) -0.0659(4) 0.0479(17) Uani 1 1 d . . . C22 C 0.0216(5) 0.3110(5) -0.0008(5) 0.057(2) Uani 1 1 d . . . H22A H 0.0322 0.3407 0.0562 0.068 Uiso 1 1 calc R . . H22B H -0.0566 0.2992 -0.0140 0.068 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0787(14) 0.0471(13) 0.0860(16) 0.0041(12) 0.0133(11) -0.0063(11) O11 0.240(7) 0.106(5) 0.181(7) 0.031(5) 0.068(6) 0.037(6) O12 0.104(4) 0.154(6) 0.162(6) -0.036(5) -0.009(4) -0.025(4) O13 0.107(4) 0.136(6) 0.107(5) 0.045(5) 0.009(4) -0.043(4) O14 0.167(6) 0.101(5) 0.096(5) -0.023(5) 0.019(4) 0.036(5) Cl2 0.0634(12) 0.0430(12) 0.0787(15) -0.0059(11) 0.0023(9) 0.0018(10) O21 0.168(6) 0.087(5) 0.074(4) 0.004(4) 0.031(4) -0.002(4) O22 0.117(4) 0.061(4) 0.104(4) -0.030(4) -0.024(3) 0.010(3) O23 0.106(4) 0.039(3) 0.160(6) -0.009(4) -0.010(4) 0.013(3) O24 0.070(4) 0.138(6) 0.184(7) 0.009(6) 0.021(4) -0.003(4) N1 0.060(3) 0.029(3) 0.060(4) 0.000(3) 0.004(3) 0.005(3) C1 0.066(4) 0.027(4) 0.076(5) -0.003(4) 0.009(4) 0.007(4) C2 0.067(5) 0.040(5) 0.073(5) -0.022(4) 0.012(4) 0.008(4) N2 0.053(3) 0.052(4) 0.063(4) -0.010(3) 0.005(3) 0.002(3) C3 0.066(5) 0.043(4) 0.068(5) -0.006(4) -0.003(3) -0.004(4) C4 0.056(4) 0.047(5) 0.075(5) -0.002(4) -0.001(3) -0.005(4) N3 0.048(3) 0.034(3) 0.062(4) -0.003(3) 0.007(3) -0.007(3) C5 0.067(5) 0.044(5) 0.089(6) 0.011(5) 0.011(4) -0.018(4) C6 0.071(5) 0.103(7) 0.064(5) 0.009(5) 0.020(4) 0.002(5) N4 0.077(4) 0.044(4) 0.051(4) 0.004(3) 0.005(3) 0.002(3) C7 0.085(5) 0.042(5) 0.061(5) 0.011(4) 0.002(4) 0.001(4) C8 0.065(4) 0.037(4) 0.064(5) 0.015(4) 0.002(3) 0.003(4) C9 0.046(4) 0.034(4) 0.078(5) 0.004(4) 0.005(3) -0.002(4) C10 0.051(4) 0.030(4) 0.066(5) -0.001(4) 0.001(3) 0.002(3) C11 0.057(4) 0.026(4) 0.080(5) 0.010(4) 0.002(4) -0.007(4) C12 0.079(5) 0.056(6) 0.064(5) 0.001(5) -0.004(4) -0.014(5) C13 0.102(6) 0.021(4) 0.075(5) -0.008(4) 0.022(4) -0.001(4) C14 0.062(4) 0.040(5) 0.077(5) 0.011(4) 0.018(4) 0.009(4) C15 0.059(4) 0.036(4) 0.063(5) -0.009(4) 0.003(3) -0.003(4) O1 0.045(3) 0.035(3) 0.109(4) 0.009(3) -0.017(3) 0.001(2) C16 0.059(4) 0.037(4) 0.068(5) -0.016(4) 0.003(4) -0.012(4) C17 0.063(5) 0.043(5) 0.097(6) -0.003(5) 0.021(4) -0.023(4) C18 0.117(7) 0.053(5) 0.065(6) 0.026(5) -0.002(5) 0.003(6) C19 0.090(6) 0.072(6) 0.071(6) -0.012(5) -0.024(5) 0.015(5) C20 0.053(4) 0.055(5) 0.077(5) -0.013(5) -0.002(4) 0.008(4) C21 0.046(4) 0.034(4) 0.065(5) -0.008(4) 0.014(3) -0.001(4) C22 0.053(4) 0.047(5) 0.072(5) -0.010(4) 0.009(3) 0.006(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 O11 1.371(8) . ? Cl1 O12 1.385(6) . ? Cl1 O13 1.403(6) . ? Cl1 O14 1.409(6) . ? Cl2 O23 1.397(5) . ? Cl2 O24 1.404(6) . ? Cl2 O22 1.419(5) . ? Cl2 O21 1.419(6) . ? N1 C8 1.444(8) . ? N1 C9 1.481(8) . ? N1 C1 1.481(8) . ? C1 C2 1.506(8) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N2 1.481(7) . ? C2 H2C 0.9700 . ? C2 H2D 0.9700 . ? N2 C3 1.481(8) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? C3 C4 1.506(9) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N3 1.476(8) . ? C4 H4C 0.9700 . ? C4 H4D 0.9700 . ? N3 C22 1.479(8) . ? N3 C5 1.480(8) . ? C5 C6 1.501(10) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N4 1.495(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N4 C7 1.487(8) . ? N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? C7 C8 1.506(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.495(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.374(8) . ? C10 C15 1.381(8) . ? C11 C12 1.373(9) . ? C11 H11 0.9300 . ? C12 C13 1.377(9) . ? C12 H12 0.9300 . ? C13 C14 1.374(9) . ? C13 H13 0.9300 . ? C14 C15 1.410(9) . ? C14 H14 0.9300 . ? C15 O1 1.400(7) . ? O1 C16 1.411(7) . ? C16 C21 1.380(8) . ? C16 C17 1.382(10) . ? C17 C18 1.374(9) . ? C17 H17 0.9300 . ? C18 C19 1.349(10) . ? C18 H18 0.9300 . ? C19 C20 1.380(11) . ? C19 H19 0.9300 . ? C20 C21 1.368(9) . ? C20 H20 0.9300 . ? C21 C22 1.513(9) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? 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 O11 Cl1 O12 113.3(5) . . ? O11 Cl1 O13 109.0(5) . . ? O12 Cl1 O13 105.6(4) . . ? O11 Cl1 O14 109.8(5) . . ? O12 Cl1 O14 109.6(5) . . ? O13 Cl1 O14 109.4(4) . . ? O23 Cl2 O24 111.6(4) . . ? O23 Cl2 O22 110.9(3) . . ? O24 Cl2 O22 109.7(4) . . ? O23 Cl2 O21 108.2(4) . . ? O24 Cl2 O21 107.9(4) . . ? O22 Cl2 O21 108.3(4) . . ? C8 N1 C9 112.2(5) . . ? C8 N1 C1 112.3(5) . . ? C9 N1 C1 111.3(5) . . ? N1 C1 C2 112.4(5) . . ? N1 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? N1 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.9 . . ? N2 C2 C1 110.3(5) . . ? N2 C2 H2C 109.6 . . ? C1 C2 H2C 109.6 . . ? N2 C2 H2D 109.6 . . ? C1 C2 H2D 109.6 . . ? H2C C2 H2D 108.1 . . ? C3 N2 C2 115.6(6) . . ? C3 N2 H2A 108.4 . . ? C2 N2 H2A 108.4 . . ? C3 N2 H2B 108.4 . . ? C2 N2 H2B 108.4 . . ? H2A N2 H2B 107.4 . . ? N2 C3 C4 110.1(6) . . ? N2 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? N2 C3 H3B 109.6 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? N3 C4 C3 110.7(5) . . ? N3 C4 H4C 109.5 . . ? C3 C4 H4C 109.5 . . ? N3 C4 H4D 109.5 . . ? C3 C4 H4D 109.5 . . ? H4C C4 H4D 108.1 . . ? C4 N3 C22 113.2(5) . . ? C4 N3 C5 110.2(5) . . ? C22 N3 C5 111.1(5) . . ? N3 C5 C6 110.6(6) . . ? N3 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? N3 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N4 C6 C5 110.3(6) . . ? N4 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N4 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C7 N4 C6 116.1(6) . . ? C7 N4 H4A 108.3 . . ? C6 N4 H4A 108.3 . . ? C7 N4 H4B 108.3 . . ? C6 N4 H4B 108.3 . . ? H4A N4 H4B 107.4 . . ? N4 C7 C8 109.7(6) . . ? N4 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? N4 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? N1 C8 C7 109.7(5) . . ? N1 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? N1 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N1 C9 C10 114.3(5) . . ? N1 C9 H9A 108.7 . . ? C10 C9 H9A 108.7 . . ? N1 C9 H9B 108.7 . . ? C10 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C11 C10 C15 117.3(6) . . ? C11 C10 C9 120.5(6) . . ? C15 C10 C9 122.1(6) . . ? C12 C11 C10 122.6(6) . . ? C12 C11 H11 118.7 . . ? C10 C11 H11 118.7 . . ? C11 C12 C13 119.3(6) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 120.5(7) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 118.6(6) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? C10 C15 O1 117.4(6) . . ? C10 C15 C14 121.4(6) . . ? O1 C15 C14 121.2(6) . . ? C15 O1 C16 120.4(5) . . ? C21 C16 C17 120.3(6) . . ? C21 C16 O1 118.1(7) . . ? C17 C16 O1 121.4(6) . . ? C18 C17 C16 119.8(7) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 120.0(8) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.2(7) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C21 C20 C19 120.9(7) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C16 118.6(7) . . ? C20 C21 C22 118.7(6) . . ? C16 C21 C22 122.6(6) . . ? N3 C22 C21 114.7(5) . . ? N3 C22 H22A 108.6 . . ? C21 C22 H22A 108.6 . . ? N3 C22 H22B 108.6 . . ? C21 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? 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 C8 N1 C1 C2 165.1(5) . . . . ? C9 N1 C1 C2 -68.2(7) . . . . ? N1 C1 C2 N2 -42.6(8) . . . . ? C1 C2 N2 C3 -85.8(7) . . . . ? C2 N2 C3 C4 163.7(6) . . . . ? N2 C3 C4 N3 -60.7(7) . . . . ? C3 C4 N3 C22 146.8(6) . . . . ? C3 C4 N3 C5 -88.1(7) . . . . ? C4 N3 C5 C6 165.1(6) . . . . ? C22 N3 C5 C6 -68.6(7) . . . . ? N3 C5 C6 N4 -44.8(8) . . . . ? C5 C6 N4 C7 -84.6(8) . . . . ? C6 N4 C7 C8 164.0(6) . . . . ? C9 N1 C8 C7 145.5(5) . . . . ? C1 N1 C8 C7 -88.3(6) . . . . ? N4 C7 C8 N1 -61.7(7) . . . . ? C8 N1 C9 C10 -62.6(7) . . . . ? C1 N1 C9 C10 170.6(5) . . . . ? N1 C9 C10 C11 119.5(7) . . . . ? N1 C9 C10 C15 -64.6(9) . . . . ? C15 C10 C11 C12 -1.8(11) . . . . ? C9 C10 C11 C12 174.3(7) . . . . ? C10 C11 C12 C13 -1.1(11) . . . . ? C11 C12 C13 C14 1.3(11) . . . . ? C12 C13 C14 C15 1.4(11) . . . . ? C11 C10 C15 O1 -174.7(6) . . . . ? C9 C10 C15 O1 9.2(10) . . . . ? C11 C10 C15 C14 4.7(10) . . . . ? C9 C10 C15 C14 -171.4(7) . . . . ? C13 C14 C15 C10 -4.5(11) . . . . ? C13 C14 C15 O1 174.8(6) . . . . ? C10 C15 O1 C16 -150.0(6) . . . . ? C14 C15 O1 C16 30.6(10) . . . . ? C15 O1 C16 C21 -138.7(6) . . . . ? C15 O1 C16 C17 45.1(9) . . . . ? C21 C16 C17 C18 2.0(10) . . . . ? O1 C16 C17 C18 178.1(7) . . . . ? C16 C17 C18 C19 -4.2(12) . . . . ? C17 C18 C19 C20 3.2(12) . . . . ? C18 C19 C20 C21 0.1(11) . . . . ? C19 C20 C21 C16 -2.3(10) . . . . ? C19 C20 C21 C22 173.9(6) . . . . ? C17 C16 C21 C20 1.3(10) . . . . ? O1 C16 C21 C20 -175.0(6) . . . . ? C17 C16 C21 C22 -174.8(6) . . . . ? O1 C16 C21 C22 9.0(9) . . . . ? C4 N3 C22 C21 -62.7(7) . . . . ? C5 N3 C22 C21 172.7(5) . . . . ? C20 C21 C22 N3 124.8(6) . . . . ? C16 C21 C22 N3 -59.2(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4B O21 0.90 2.04 2.935(9) 174.7 . N2 H2B O13 0.90 2.05 2.909(8) 159.5 . N4 H4A N3 0.90 2.25 2.752(7) 115.0 . N2 H2A N1 0.90 2.26 2.772(7) 115.7 . N4 H4A N1 0.90 2.42 2.867(8) 110.5 . N2 H2A N3 0.90 2.45 2.899(7) 111.2 . _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.527 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.077 #===END data_[H2L2](ZnCl4)H2O _database_code_depnum_ccdc_archive 'CCDC 787306' #TrackingRef '- revised CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H34 Cl4 N4 O2 Zn' _chemical_formula_weight 593.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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 9.9245(3) _cell_length_b 15.6324(5) _cell_length_c 17.8004(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.571(4) _cell_angle_gamma 90.00 _cell_volume 2714.75(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used 4036 _cell_measurement_theta_min 3.7198 _cell_measurement_theta_max 28.9786 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 1.325 _exptl_absorpt_correction_T_min 0.64093 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number 0 _diffrn_standards_interval_count infinity _diffrn_standards_interval_time infinity _diffrn_standards_decay_% ? _diffrn_reflns_number 10271 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 23.26 _reflns_number_total 3703 _reflns_number_gt 2367 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SIR97 (Altomare 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 Ver. 1.01\b (Farrugia, 1997)' _computing_publication_material 'PARST93 (Nardelli, 1993)' _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^)+(0.1880P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3703 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1200 _refine_ls_R_factor_gt 0.0855 _refine_ls_wR_factor_ref 0.2583 _refine_ls_wR_factor_gt 0.2322 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.33356(12) 0.14287(8) 0.19063(7) 0.0696(5) Uani 1 1 d . . . Cl4 Cl 0.18829(19) 0.07405(12) 0.26354(11) 0.0446(5) Uani 1 1 d . . . Cl2 Cl 0.3986(2) 0.28096(11) 0.23636(10) 0.0480(6) Uani 1 1 d . . . Cl3 Cl 0.52900(18) 0.05916(14) 0.19007(12) 0.0531(6) Uani 1 1 d . . . Cl1 Cl 0.2083(2) 0.15232(19) 0.06716(13) 0.0719(8) Uani 1 1 d . . . N1 N 0.7594(8) 0.1688(5) 0.5980(4) 0.066(2) Uani 1 1 d . . . C1 C 0.6126(10) 0.1367(7) 0.5876(8) 0.078(3) Uani 1 1 d . . . H1A H 0.6002 0.0886 0.5526 0.094 Uiso 1 1 calc R . . H1B H 0.5925 0.1178 0.6362 0.094 Uiso 1 1 calc R . . C2 C 0.5168(11) 0.2087(7) 0.5560(6) 0.073(3) Uani 1 1 d . . . H2C H 0.4225 0.1898 0.5512 0.088 Uiso 1 1 calc R . . H2D H 0.5305 0.2570 0.5907 0.088 Uiso 1 1 calc R . . N2 N 0.5435(8) 0.2348(6) 0.4808(5) 0.078(3) Uani 1 1 d . . . H2A H 0.5108 0.1938 0.4468 0.093 Uiso 1 1 calc R . . H2B H 0.6349 0.2370 0.4834 0.093 Uiso 1 1 calc R . . C3 C 0.4834(11) 0.3196(8) 0.4503(7) 0.081(3) Uani 1 1 d . . . H3A H 0.4723 0.3200 0.3951 0.097 Uiso 1 1 calc R . . H3B H 0.3936 0.3267 0.4637 0.097 Uiso 1 1 calc R . . C4 C 0.5712(10) 0.3899(7) 0.4816(6) 0.073(3) Uani 1 1 d . . . H4C H 0.5603 0.4002 0.5339 0.087 Uiso 1 1 calc R . . H4D H 0.5434 0.4413 0.4523 0.087 Uiso 1 1 calc R . . N3 N 0.7171(8) 0.3722(5) 0.4803(4) 0.0602(19) Uani 1 1 d . . . C5 C 0.8085(13) 0.4299(6) 0.5286(7) 0.081(3) Uani 1 1 d . . . H5A H 0.7650 0.4854 0.5295 0.097 Uiso 1 1 calc R . . H5B H 0.8917 0.4374 0.5080 0.097 Uiso 1 1 calc R . . C6 C 0.8431(11) 0.3959(7) 0.6069(6) 0.073(3) Uani 1 1 d . . . H6C H 0.7602 0.3877 0.6277 0.088 Uiso 1 1 calc R . . H6D H 0.9018 0.4358 0.6394 0.088 Uiso 1 1 calc R . . N4 N 0.9144(8) 0.3133(6) 0.6043(5) 0.069(2) Uani 1 1 d . . . H4A H 0.9990 0.3236 0.5951 0.083 Uiso 1 1 calc R . . H4B H 0.8691 0.2825 0.5649 0.083 Uiso 1 1 calc R . . C7 C 0.9271(12) 0.2590(8) 0.6785(7) 0.087(3) Uani 1 1 d . . . H7A H 1.0069 0.2221 0.6837 0.105 Uiso 1 1 calc R . . H7B H 0.9373 0.2961 0.7228 0.105 Uiso 1 1 calc R . . C8 C 0.8042(12) 0.2082(8) 0.6731(7) 0.090(4) Uani 1 1 d . . . H8A H 0.7310 0.2443 0.6845 0.108 Uiso 1 1 calc R . . H8B H 0.8202 0.1635 0.7114 0.108 Uiso 1 1 calc R . . C9 C 0.8518(11) 0.1037(8) 0.5822(6) 0.078(3) Uani 1 1 d . . . H9A H 0.8484 0.0564 0.6170 0.093 Uiso 1 1 calc R . . H9B H 0.9442 0.1266 0.5926 0.093 Uiso 1 1 calc R . . C10 C 0.8227(11) 0.0691(6) 0.5001(7) 0.071(3) Uani 1 1 d . . . C11 C 0.7971(13) -0.0207(7) 0.4846(10) 0.100(4) Uani 1 1 d . . . H11 H 0.7949 -0.0574 0.5255 0.120 Uiso 1 1 calc R . . C12 C 0.7761(14) -0.0538(8) 0.4130(11) 0.102(4) Uani 1 1 d . . . H12 H 0.7610 -0.1121 0.4052 0.123 Uiso 1 1 calc R . . C13 C 0.7774(13) -0.0025(9) 0.3552(9) 0.096(4) Uani 1 1 d . . . H13 H 0.7607 -0.0249 0.3059 0.115 Uiso 1 1 calc R . . C14 C 0.8036(12) 0.0868(7) 0.3655(7) 0.084(3) Uani 1 1 d . . . H14 H 0.8073 0.1222 0.3239 0.101 Uiso 1 1 calc R . . C15 C 0.8232(11) 0.1187(6) 0.4376(7) 0.067(3) Uani 1 1 d . . . O1 O 0.8361(8) 0.2069(4) 0.4503(4) 0.077(2) Uani 1 1 d . . . C16 C 0.9224(10) 0.2555(6) 0.4114(5) 0.058(2) Uani 1 1 d . . . C17 C 1.0408(11) 0.2227(6) 0.3947(6) 0.068(3) Uani 1 1 d . . . H17 H 1.0643 0.1660 0.4061 0.081 Uiso 1 1 calc R . . C18 C 1.1234(11) 0.2728(8) 0.3618(6) 0.079(3) Uani 1 1 d . . . H18 H 1.2046 0.2501 0.3514 0.095 Uiso 1 1 calc R . . C19 C 1.0917(12) 0.3562(7) 0.3432(7) 0.075(3) Uani 1 1 d . . . H19 H 1.1500 0.3905 0.3208 0.090 Uiso 1 1 calc R . . C20 C 0.9694(11) 0.3875(7) 0.3589(6) 0.071(3) Uani 1 1 d . . . H20 H 0.9466 0.4442 0.3466 0.085 Uiso 1 1 calc R . . C21 C 0.8812(10) 0.3398(5) 0.3912(5) 0.058(2) Uani 1 1 d . . . C22 C 0.7427(10) 0.3722(7) 0.3983(6) 0.068(3) Uani 1 1 d . . . H22A H 0.6737 0.3370 0.3671 0.082 Uiso 1 1 calc R . . H22B H 0.7324 0.4301 0.3784 0.082 Uiso 1 1 calc R . . OW O 0.4644(9) 0.0872(6) 0.3928(5) 0.106(3) 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 Zn1 0.0653(8) 0.0845(9) 0.0598(8) -0.0021(6) 0.0137(6) -0.0066(6) Cl4 0.0461(11) 0.0477(11) 0.0422(11) -0.0002(9) 0.0135(9) -0.0121(8) Cl2 0.0855(14) 0.0363(10) 0.0310(10) -0.0120(8) 0.0342(10) -0.0274(9) Cl3 0.0305(10) 0.0789(14) 0.0508(13) 0.0039(10) 0.0101(9) 0.0107(9) Cl1 0.0405(12) 0.132(2) 0.0432(13) 0.0029(13) 0.0068(10) 0.0016(12) N1 0.072(5) 0.087(5) 0.042(4) 0.001(4) 0.016(4) 0.009(4) C1 0.058(6) 0.080(7) 0.104(9) 0.018(6) 0.035(6) -0.012(5) C2 0.068(6) 0.093(8) 0.064(6) -0.005(6) 0.025(5) -0.016(6) N2 0.053(5) 0.106(7) 0.076(6) -0.021(5) 0.014(4) -0.011(5) C3 0.068(7) 0.114(9) 0.061(7) 0.001(7) 0.015(6) 0.025(7) C4 0.075(7) 0.080(7) 0.064(6) -0.006(6) 0.012(6) 0.011(6) N3 0.056(4) 0.068(5) 0.057(5) 0.003(4) 0.011(4) 0.002(4) C5 0.096(8) 0.060(6) 0.091(9) -0.016(6) 0.027(7) -0.011(6) C6 0.070(6) 0.087(7) 0.061(7) -0.014(6) 0.011(5) -0.006(6) N4 0.056(5) 0.093(6) 0.058(5) -0.001(5) 0.006(4) -0.010(4) C7 0.076(7) 0.105(8) 0.077(8) -0.004(7) 0.005(6) -0.006(6) C8 0.074(7) 0.109(9) 0.087(9) 0.029(7) 0.021(7) 0.009(7) C9 0.067(6) 0.094(7) 0.075(7) 0.032(6) 0.019(6) 0.012(6) C10 0.069(6) 0.060(6) 0.090(8) 0.008(6) 0.029(6) -0.007(5) C11 0.104(9) 0.059(7) 0.149(14) 0.017(8) 0.057(10) 0.008(6) C12 0.102(9) 0.065(8) 0.149(14) -0.005(9) 0.049(10) -0.010(7) C13 0.084(8) 0.094(10) 0.106(10) -0.035(9) 0.010(8) -0.013(7) C14 0.091(8) 0.081(8) 0.086(8) -0.003(6) 0.032(7) 0.010(6) C15 0.076(6) 0.048(5) 0.086(8) 0.003(5) 0.040(6) 0.000(5) O1 0.099(5) 0.059(4) 0.085(5) 0.012(3) 0.048(4) 0.006(3) C16 0.067(6) 0.062(5) 0.048(5) 0.005(4) 0.017(5) -0.008(5) C17 0.072(6) 0.067(6) 0.070(7) -0.001(5) 0.027(6) 0.008(5) C18 0.064(6) 0.101(9) 0.067(7) -0.023(6) -0.001(6) 0.003(6) C19 0.076(7) 0.078(7) 0.079(7) -0.015(6) 0.034(6) -0.023(6) C20 0.085(7) 0.063(6) 0.068(7) -0.006(5) 0.024(6) -0.009(5) C21 0.071(6) 0.054(5) 0.050(5) 0.004(4) 0.012(5) 0.005(4) C22 0.068(6) 0.078(6) 0.058(6) 0.004(5) 0.011(5) 0.011(5) OW 0.106(6) 0.105(6) 0.099(6) -0.013(5) -0.002(5) -0.019(5) _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 Zn1 Cl1 2.323(3) . ? Zn1 Cl3 2.341(2) . ? Zn1 Cl2 2.355(2) . ? Zn1 Cl4 2.368(2) . ? N1 C9 1.432(13) . ? N1 C8 1.464(15) . ? N1 C1 1.520(13) . ? C1 C2 1.513(15) . ? C2 N2 1.469(13) . ? N2 C3 1.513(15) . ? C3 C4 1.449(16) . ? C4 N3 1.478(12) . ? N3 C5 1.446(13) . ? N3 C22 1.526(12) . ? C5 C6 1.473(15) . ? C6 N4 1.476(14) . ? N4 C7 1.555(15) . ? C7 C8 1.444(16) . ? C9 C10 1.534(16) . ? C10 C15 1.358(14) . ? C10 C11 1.444(16) . ? C11 C12 1.36(2) . ? C12 C13 1.306(19) . ? C13 C14 1.427(17) . ? C14 C15 1.357(16) . ? C15 O1 1.399(12) . ? O1 C16 1.416(11) . ? C16 C17 1.363(13) . ? C16 C21 1.408(13) . ? C17 C18 1.343(15) . ? C18 C19 1.368(15) . ? C19 C20 1.385(15) . ? C20 C21 1.355(13) . ? C21 C22 1.492(14) . ? 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 Cl1 Zn1 Cl3 109.36(9) . . ? Cl1 Zn1 Cl2 109.51(10) . . ? Cl3 Zn1 Cl2 109.82(9) . . ? Cl1 Zn1 Cl4 105.87(9) . . ? Cl3 Zn1 Cl4 109.67(9) . . ? Cl2 Zn1 Cl4 112.50(8) . . ? C9 N1 C8 112.4(9) . . ? C9 N1 C1 112.0(9) . . ? C8 N1 C1 112.0(8) . . ? C2 C1 N1 108.9(8) . . ? N2 C2 C1 109.8(8) . . ? C2 N2 C3 116.4(8) . . ? C4 C3 N2 110.9(9) . . ? C3 C4 N3 111.9(8) . . ? C5 N3 C4 112.5(8) . . ? C5 N3 C22 111.8(8) . . ? C4 N3 C22 110.6(8) . . ? N3 C5 C6 110.4(9) . . ? C5 C6 N4 108.4(8) . . ? C6 N4 C7 114.5(8) . . ? C8 C7 N4 107.9(9) . . ? C7 C8 N1 113.8(10) . . ? N1 C9 C10 115.0(9) . . ? C15 C10 C11 115.2(12) . . ? C15 C10 C9 123.4(9) . . ? C11 C10 C9 121.3(11) . . ? C12 C11 C10 122.8(13) . . ? C13 C12 C11 119.1(12) . . ? C12 C13 C14 121.8(13) . . ? C15 C14 C13 118.2(12) . . ? C14 C15 C10 123.0(10) . . ? C14 C15 O1 120.5(10) . . ? C10 C15 O1 116.4(9) . . ? C15 O1 C16 119.7(7) . . ? C17 C16 C21 121.1(8) . . ? C17 C16 O1 121.8(8) . . ? C21 C16 O1 117.0(8) . . ? C18 C17 C16 119.7(10) . . ? C17 C18 C19 122.0(10) . . ? C18 C19 C20 117.3(10) . . ? C21 C20 C19 123.3(10) . . ? C20 C21 C16 116.4(9) . . ? C20 C21 C22 121.7(9) . . ? C16 C21 C22 121.7(9) . . ? C21 C22 N3 113.5(8) . . ? 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 C9 N1 C1 C2 -144.6(9) . . . . ? C8 N1 C1 C2 88.1(11) . . . . ? N1 C1 C2 N2 61.9(12) . . . . ? C1 C2 N2 C3 -164.9(9) . . . . ? C2 N2 C3 C4 83.0(10) . . . . ? N2 C3 C4 N3 44.8(11) . . . . ? C3 C4 N3 C5 -164.7(9) . . . . ? C3 C4 N3 C22 69.5(11) . . . . ? C4 N3 C5 C6 88.5(11) . . . . ? C22 N3 C5 C6 -146.4(9) . . . . ? N3 C5 C6 N4 61.6(11) . . . . ? C5 C6 N4 C7 -166.2(9) . . . . ? C6 N4 C7 C8 86.7(12) . . . . ? N4 C7 C8 N1 43.4(13) . . . . ? C9 N1 C8 C7 68.3(12) . . . . ? C1 N1 C8 C7 -164.6(10) . . . . ? C8 N1 C9 C10 -171.4(9) . . . . ? C1 N1 C9 C10 61.5(11) . . . . ? N1 C9 C10 C15 60.0(14) . . . . ? N1 C9 C10 C11 -122.2(11) . . . . ? C15 C10 C11 C12 0.5(18) . . . . ? C9 C10 C11 C12 -177.5(12) . . . . ? C10 C11 C12 C13 -1(2) . . . . ? C11 C12 C13 C14 2(2) . . . . ? C12 C13 C14 C15 -2.1(19) . . . . ? C13 C14 C15 C10 1.9(17) . . . . ? C13 C14 C15 O1 -173.8(10) . . . . ? C11 C10 C15 C14 -1.1(16) . . . . ? C9 C10 C15 C14 176.8(11) . . . . ? C11 C10 C15 O1 174.8(9) . . . . ? C9 C10 C15 O1 -7.3(15) . . . . ? C14 C15 O1 C16 -45.8(14) . . . . ? C10 C15 O1 C16 138.2(9) . . . . ? C15 O1 C16 C17 -34.4(14) . . . . ? C15 O1 C16 C21 146.2(9) . . . . ? C21 C16 C17 C18 3.3(16) . . . . ? O1 C16 C17 C18 -176.1(10) . . . . ? C16 C17 C18 C19 -1.0(17) . . . . ? C17 C18 C19 C20 -0.6(17) . . . . ? C18 C19 C20 C21 -0.2(17) . . . . ? C19 C20 C21 C16 2.4(15) . . . . ? C19 C20 C21 C22 -172.2(10) . . . . ? C17 C16 C21 C20 -4.0(14) . . . . ? O1 C16 C21 C20 175.5(9) . . . . ? C17 C16 C21 C22 170.6(10) . . . . ? O1 C16 C21 C22 -9.9(13) . . . . ? C20 C21 C22 N3 -123.5(10) . . . . ? C16 C21 C22 N3 62.3(12) . . . . ? C5 N3 C22 C21 64.0(11) . . . . ? C4 N3 C22 C21 -169.8(8) . . . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 1.643 _refine_diff_density_min -1.084 _refine_diff_density_rms 0.148 #===END data_[HL2ZnCl3] _database_code_depnum_ccdc_archive 'CCDC 787307' #TrackingRef '- revised CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H31 Cl3 N4 O Zn' _chemical_formula_weight 539.23 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' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.7838(2) _cell_length_b 14.7915(3) _cell_length_c 18.3776(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2387.72(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used 3166 _cell_measurement_theta_min 3.8351 _cell_measurement_theta_max 72.1126 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 4.691 _exptl_absorpt_correction_T_min 0.72014 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.1241 _diffrn_standards_number 0 _diffrn_standards_interval_count infinity _diffrn_standards_interval_time infinity _diffrn_standards_decay_% ? _diffrn_reflns_number 9509 _diffrn_reflns_av_R_equivalents 0.0691 _diffrn_reflns_av_sigmaI/netI 0.0696 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 72.37 _reflns_number_total 4358 _reflns_number_gt 3430 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SIR97 (Altomare 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 Ver. 1.01\b (Farrugia, 1997)' _computing_publication_material 'PARST93 (Nardelli, 1993)' _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^)+(0.0282P)^2^+5.1450P] 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 ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(3) _refine_ls_number_reflns 4358 _refine_ls_number_parameters 288 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 Zn Zn 0.93221(8) 0.95690(5) 0.43959(4) 0.02095(17) Uani 1 1 d . . . Cl1 Cl 1.15710(15) 0.93805(10) 0.49643(7) 0.0264(3) Uani 1 1 d . . . Cl2 Cl 0.88682(17) 0.86726(9) 0.34103(7) 0.0264(3) Uani 1 1 d . . . Cl3 Cl 0.8833(2) 1.09999(9) 0.40385(7) 0.0313(3) Uani 1 1 d . . . N1 N 0.5768(5) 1.0190(3) 0.6026(2) 0.0200(10) Uani 1 1 d . . . C1 C 0.5729(7) 1.0119(4) 0.5225(3) 0.0233(12) Uani 1 1 d . . . H1A H 0.6411 1.0565 0.5016 0.028 Uiso 1 1 calc R . . H1B H 0.4708 1.0247 0.5053 0.028 Uiso 1 1 calc R . . C2 C 0.6205(6) 0.9177(4) 0.4979(3) 0.0227(12) Uani 1 1 d . . . H2A H 0.5580 0.8727 0.5221 0.027 Uiso 1 1 calc R . . H2B H 0.6051 0.9119 0.4458 0.027 Uiso 1 1 calc R . . N2 N 0.7817(5) 0.9022(3) 0.5155(2) 0.0190(10) Uani 1 1 d . . . H2C H 0.8007 0.9292 0.5590 0.023 Uiso 1 1 calc R . . C3 C 0.8220(7) 0.8050(4) 0.5227(3) 0.0253(13) Uani 1 1 d . . . H3A H 0.9316 0.7986 0.5190 0.030 Uiso 1 1 calc R . . H3B H 0.7767 0.7718 0.4827 0.030 Uiso 1 1 calc R . . C4 C 0.7691(7) 0.7631(4) 0.5944(3) 0.0237(13) Uani 1 1 d . . . H4A H 0.6595 0.7550 0.5926 0.028 Uiso 1 1 calc R . . H4B H 0.8150 0.7038 0.5995 0.028 Uiso 1 1 calc R . . N3 N 0.8075(5) 0.8176(3) 0.6586(2) 0.0210(10) Uani 1 1 d . . . C5 C 0.7313(7) 0.7831(4) 0.7240(3) 0.0294(14) Uani 1 1 d . . . H5A H 0.7890 0.8000 0.7670 0.035 Uiso 1 1 calc R . . H5B H 0.7258 0.7177 0.7221 0.035 Uiso 1 1 calc R . . C6 C 0.5735(8) 0.8222(4) 0.7284(3) 0.0310(14) Uani 1 1 d . . . H6A H 0.5155 0.8056 0.6855 0.037 Uiso 1 1 calc R . . H6B H 0.5212 0.7988 0.7710 0.037 Uiso 1 1 calc R . . N4 N 0.5870(6) 0.9225(3) 0.7334(3) 0.0265(11) Uani 1 1 d . . . H2 H 0.658(7) 0.945(4) 0.697(3) 0.027(16) Uiso 1 1 d . . . H5 H 0.608(7) 0.931(4) 0.775(3) 0.027(17) Uiso 1 1 d . . . C7 C 0.4440(7) 0.9732(4) 0.7158(3) 0.0317(14) Uani 1 1 d . . . H7A H 0.4450 1.0316 0.7398 0.038 Uiso 1 1 calc R . . H7B H 0.3562 0.9397 0.7330 0.038 Uiso 1 1 calc R . . C8 C 0.4340(7) 0.9860(4) 0.6334(3) 0.0290(13) Uani 1 1 d . . . H8A H 0.4079 0.9288 0.6108 0.035 Uiso 1 1 calc R . . H8B H 0.3534 1.0288 0.6224 0.035 Uiso 1 1 calc R . . C9 C 0.6121(6) 1.1116(4) 0.6275(3) 0.0219(12) Uani 1 1 d . . . H9A H 0.5959 1.1151 0.6797 0.026 Uiso 1 1 calc R . . H9B H 0.5423 1.1535 0.6045 0.026 Uiso 1 1 calc R . . C10 C 0.7730(7) 1.1401(4) 0.6108(3) 0.0207(12) Uani 1 1 d . . . C11 C 0.8016(7) 1.2190(4) 0.5713(3) 0.0262(13) Uani 1 1 d . . . H11 H 0.7197 1.2518 0.5531 0.031 Uiso 1 1 calc R . . C12 C 0.9466(7) 1.2498(4) 0.5585(3) 0.0289(13) Uani 1 1 d . . . H12 H 0.9622 1.3020 0.5313 0.035 Uiso 1 1 calc R . . C13 C 1.0693(8) 1.2025(4) 0.5864(3) 0.0333(14) Uani 1 1 d . . . H13 H 1.1679 1.2236 0.5792 0.040 Uiso 1 1 calc R . . C14 C 1.0446(7) 1.1241(4) 0.6248(3) 0.0268(13) Uani 1 1 d . . . H14 H 1.1269 1.0914 0.6428 0.032 Uiso 1 1 calc R . . C15 C 0.8983(7) 1.0937(4) 0.6369(3) 0.0229(12) Uani 1 1 d . . . O1 O 0.8722(4) 1.0121(2) 0.6725(2) 0.0248(9) Uani 1 1 d . . . C16 C 0.9725(6) 0.9846(4) 0.7277(3) 0.0205(12) Uani 1 1 d . . . C17 C 1.0154(6) 1.0428(4) 0.7822(3) 0.0255(12) Uani 1 1 d . . . H17 H 0.9807 1.1022 0.7822 0.031 Uiso 1 1 calc R . . C18 C 1.1104(6) 1.0126(4) 0.8372(3) 0.0238(12) Uani 1 1 d . . . H18 H 1.1439 1.0526 0.8728 0.029 Uiso 1 1 calc R . . C19 C 1.1554(6) 0.9235(4) 0.8392(3) 0.0224(12) Uani 1 1 d . . . H19 H 1.2178 0.9029 0.8766 0.027 Uiso 1 1 calc R . . C20 C 1.1071(6) 0.8644(4) 0.7852(3) 0.0216(12) Uani 1 1 d . . . H20 H 1.1364 0.8041 0.7873 0.026 Uiso 1 1 calc R . . C21 C 1.0162(6) 0.8936(4) 0.7282(3) 0.0206(12) Uani 1 1 d . . . C22 C 0.9740(6) 0.8282(4) 0.6666(3) 0.0225(13) Uani 1 1 d . . . H22A H 1.0161 0.8505 0.6212 0.027 Uiso 1 1 calc R . . H22B H 1.0192 0.7696 0.6764 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn 0.0209(4) 0.0235(3) 0.0184(3) 0.0003(3) 0.0014(3) 0.0014(3) Cl1 0.0186(6) 0.0361(8) 0.0246(7) -0.0031(6) 0.0005(5) -0.0001(6) Cl2 0.0329(8) 0.0272(6) 0.0192(6) -0.0056(5) -0.0004(6) 0.0032(6) Cl3 0.0504(10) 0.0232(7) 0.0204(6) 0.0018(5) 0.0022(7) 0.0046(7) N1 0.019(2) 0.024(2) 0.018(2) -0.0077(17) -0.001(2) -0.002(2) C1 0.016(3) 0.033(3) 0.020(3) -0.003(2) -0.006(3) 0.004(3) C2 0.021(3) 0.031(3) 0.016(2) -0.004(2) 0.000(2) 0.000(2) N2 0.021(2) 0.020(2) 0.016(2) -0.0023(19) 0.0010(19) 0.000(2) C3 0.023(3) 0.022(3) 0.031(3) -0.006(2) -0.005(3) -0.002(3) C4 0.033(3) 0.017(3) 0.022(3) -0.002(2) -0.004(3) -0.006(3) N3 0.028(3) 0.022(2) 0.013(2) -0.0014(19) 0.002(2) -0.008(2) C5 0.049(4) 0.021(3) 0.018(3) 0.005(2) 0.000(3) -0.013(3) C6 0.040(4) 0.035(3) 0.019(3) 0.000(2) 0.001(3) -0.016(3) N4 0.025(3) 0.042(3) 0.012(2) 0.000(2) 0.003(2) -0.007(2) C7 0.020(3) 0.049(4) 0.026(3) -0.010(3) 0.010(3) -0.007(3) C8 0.015(3) 0.045(4) 0.027(3) -0.007(3) -0.003(3) -0.006(3) C9 0.019(3) 0.032(3) 0.015(2) -0.004(2) -0.003(2) 0.005(3) C10 0.027(3) 0.017(3) 0.018(3) -0.006(2) -0.004(2) 0.005(2) C11 0.040(4) 0.019(3) 0.019(3) 0.001(2) -0.006(3) 0.009(3) C12 0.047(4) 0.024(3) 0.016(2) 0.000(2) 0.002(3) -0.004(3) C13 0.031(3) 0.034(3) 0.035(3) -0.007(3) 0.012(3) -0.006(3) C14 0.025(3) 0.021(3) 0.034(3) 0.003(2) 0.006(3) -0.002(3) C15 0.022(3) 0.019(3) 0.028(3) -0.005(2) 0.002(3) -0.002(2) O1 0.021(2) 0.0211(19) 0.032(2) 0.0080(16) -0.0087(18) 0.0002(17) C16 0.012(3) 0.024(3) 0.026(3) 0.000(2) -0.001(2) -0.001(2) C17 0.023(3) 0.020(3) 0.034(3) -0.001(3) 0.002(2) -0.004(3) C18 0.021(3) 0.033(3) 0.017(2) -0.003(2) -0.001(2) -0.009(3) C19 0.022(3) 0.028(3) 0.018(3) 0.005(2) -0.002(2) -0.006(2) C20 0.023(3) 0.019(3) 0.022(3) 0.003(2) -0.001(2) 0.003(3) C21 0.019(3) 0.020(3) 0.023(3) 0.002(2) 0.003(2) -0.007(2) C22 0.032(3) 0.014(3) 0.021(3) 0.003(2) -0.003(3) 0.002(2) _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 Zn N2 2.085(4) . ? Zn Cl1 2.2519(15) . ? Zn Cl3 2.2573(15) . ? Zn Cl2 2.2799(14) . ? N1 C8 1.460(7) . ? N1 C1 1.476(6) . ? N1 C9 1.478(7) . ? C1 C2 1.524(7) . ? C2 N2 1.470(7) . ? N2 C3 1.486(7) . ? C3 C4 1.528(8) . ? C4 N3 1.469(7) . ? N3 C5 1.467(7) . ? N3 C22 1.478(7) . ? C5 C6 1.504(9) . ? C6 N4 1.492(7) . ? N4 C7 1.498(8) . ? C7 C8 1.529(7) . ? C9 C10 1.507(8) . ? C10 C15 1.383(8) . ? C10 C11 1.397(8) . ? C11 C12 1.373(9) . ? C12 C13 1.383(9) . ? C13 C14 1.376(8) . ? C14 C15 1.380(8) . ? C15 O1 1.393(6) . ? O1 C16 1.403(6) . ? C16 C17 1.374(8) . ? C16 C21 1.399(7) . ? C17 C18 1.384(8) . ? C18 C19 1.376(7) . ? C19 C20 1.389(7) . ? C20 C21 1.386(7) . ? C21 C22 1.533(7) . ? 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 Zn Cl1 101.42(13) . . ? N2 Zn Cl3 115.98(13) . . ? Cl1 Zn Cl3 114.70(6) . . ? N2 Zn Cl2 101.22(13) . . ? Cl1 Zn Cl2 116.74(6) . . ? Cl3 Zn Cl2 106.31(6) . . ? C8 N1 C1 110.1(5) . . ? C8 N1 C9 111.7(4) . . ? C1 N1 C9 112.3(4) . . ? N1 C1 C2 110.8(4) . . ? N2 C2 C1 110.0(4) . . ? C2 N2 C3 113.6(4) . . ? C2 N2 Zn 113.8(3) . . ? C3 N2 Zn 106.5(3) . . ? N2 C3 C4 113.4(5) . . ? N3 C4 C3 113.6(4) . . ? C4 N3 C5 111.3(4) . . ? C4 N3 C22 111.5(5) . . ? C5 N3 C22 114.0(5) . . ? N3 C5 C6 109.4(5) . . ? N4 C6 C5 108.2(5) . . ? C6 N4 C7 114.7(5) . . ? N4 C7 C8 108.9(5) . . ? N1 C8 C7 112.0(5) . . ? N1 C9 C10 113.2(5) . . ? C15 C10 C11 116.9(6) . . ? C15 C10 C9 122.4(5) . . ? C11 C10 C9 120.6(5) . . ? C12 C11 C10 122.1(6) . . ? C11 C12 C13 119.5(5) . . ? C14 C13 C12 119.6(6) . . ? C13 C14 C15 120.3(6) . . ? C14 C15 C10 121.6(5) . . ? C14 C15 O1 120.8(5) . . ? C10 C15 O1 117.6(5) . . ? C15 O1 C16 119.2(4) . . ? C17 C16 C21 121.5(5) . . ? C17 C16 O1 121.1(5) . . ? C21 C16 O1 117.1(5) . . ? C16 C17 C18 119.7(5) . . ? C19 C18 C17 120.1(5) . . ? C18 C19 C20 119.7(5) . . ? C21 C20 C19 121.4(5) . . ? C20 C21 C16 117.5(5) . . ? C20 C21 C22 120.0(5) . . ? C16 C21 C22 122.4(5) . . ? N3 C22 C21 112.3(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 C8 N1 C1 C2 -85.0(6) . . . . ? C9 N1 C1 C2 149.8(5) . . . . ? N1 C1 C2 N2 -66.4(6) . . . . ? C1 C2 N2 C3 155.9(4) . . . . ? C1 C2 N2 Zn -82.0(5) . . . . ? Cl1 Zn N2 C2 171.1(3) . . . . ? Cl3 Zn N2 C2 46.1(4) . . . . ? Cl2 Zn N2 C2 -68.4(3) . . . . ? Cl1 Zn N2 C3 -63.0(3) . . . . ? Cl3 Zn N2 C3 172.1(3) . . . . ? Cl2 Zn N2 C3 57.5(3) . . . . ? C2 N2 C3 C4 -76.3(6) . . . . ? Zn N2 C3 C4 157.7(4) . . . . ? N2 C3 C4 N3 -48.0(7) . . . . ? C3 C4 N3 C5 169.9(5) . . . . ? C3 C4 N3 C22 -61.6(6) . . . . ? C4 N3 C5 C6 -84.9(6) . . . . ? C22 N3 C5 C6 148.0(5) . . . . ? N3 C5 C6 N4 -61.0(6) . . . . ? C5 C6 N4 C7 162.4(5) . . . . ? C6 N4 C7 C8 -84.8(6) . . . . ? C1 N1 C8 C7 168.0(5) . . . . ? C9 N1 C8 C7 -66.5(6) . . . . ? N4 C7 C8 N1 -47.6(7) . . . . ? C8 N1 C9 C10 167.3(5) . . . . ? C1 N1 C9 C10 -68.5(6) . . . . ? N1 C9 C10 C15 -59.3(6) . . . . ? N1 C9 C10 C11 124.8(5) . . . . ? C15 C10 C11 C12 0.1(8) . . . . ? C9 C10 C11 C12 176.3(5) . . . . ? C10 C11 C12 C13 -1.1(9) . . . . ? C11 C12 C13 C14 1.7(9) . . . . ? C12 C13 C14 C15 -1.3(9) . . . . ? C13 C14 C15 C10 0.3(9) . . . . ? C13 C14 C15 O1 176.7(5) . . . . ? C11 C10 C15 C14 0.3(8) . . . . ? C9 C10 C15 C14 -175.8(5) . . . . ? C11 C10 C15 O1 -176.2(5) . . . . ? C9 C10 C15 O1 7.7(8) . . . . ? C14 C15 O1 C16 33.7(7) . . . . ? C10 C15 O1 C16 -149.8(5) . . . . ? C15 O1 C16 C17 48.3(7) . . . . ? C15 O1 C16 C21 -137.1(5) . . . . ? C21 C16 C17 C18 3.4(8) . . . . ? O1 C16 C17 C18 177.8(5) . . . . ? C16 C17 C18 C19 -3.3(8) . . . . ? C17 C18 C19 C20 1.1(8) . . . . ? C18 C19 C20 C21 1.1(8) . . . . ? C19 C20 C21 C16 -1.1(8) . . . . ? C19 C20 C21 C22 175.8(5) . . . . ? C17 C16 C21 C20 -1.2(8) . . . . ? O1 C16 C21 C20 -175.8(5) . . . . ? C17 C16 C21 C22 -178.0(5) . . . . ? O1 C16 C21 C22 7.5(8) . . . . ? C4 N3 C22 C21 173.5(4) . . . . ? C5 N3 C22 C21 -59.4(6) . . . . ? C20 C21 C22 N3 121.8(5) . . . . ? C16 C21 C22 N3 -61.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.561 _refine_diff_density_min -0.634 _refine_diff_density_rms 0.115 #===END data_[CuL1](PF6)2CH3CN _database_code_depnum_ccdc_archive 'CCDC 787308' #TrackingRef '- revised CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H31 Cu F12 N5 O P2' _chemical_formula_weight 759.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.3780(9) _cell_length_b 19.190(2) _cell_length_c 13.4790(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.338(7) _cell_angle_gamma 90.00 _cell_volume 2940.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 3000 _cell_measurement_theta_min 4.00 _cell_measurement_theta_max 22.00 _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.714 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1540 _exptl_absorpt_coefficient_mu 0.958 _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number 0 _diffrn_standards_interval_count infinity _diffrn_standards_interval_time infinity _diffrn_standards_decay_% ? _diffrn_reflns_number 16899 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0668 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5147 _reflns_number_gt 3533 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SIR97 (Altomare 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 Ver. 1.01\b (Farrugia, 1997)' _computing_publication_material 'PARST93 (Nardelli, 1993)' _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^)+(0.1279P)^2^+14.5520P] 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 5147 _refine_ls_number_parameters 407 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1136 _refine_ls_R_factor_gt 0.0807 _refine_ls_wR_factor_ref 0.2401 _refine_ls_wR_factor_gt 0.2220 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.002 _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 0.28267(7) 0.19630(4) 0.95925(6) 0.0225(3) Uani 1 1 d . . . P1 P 0.72900(17) 0.26960(11) 0.96209(14) 0.0295(5) Uani 1 1 d . . . F11 F 0.7928(5) 0.2009(3) 0.9317(6) 0.081(2) Uani 1 1 d . . . F12 F 0.8311(6) 0.2858(4) 1.0411(5) 0.095(3) Uani 1 1 d . . . F13 F 0.6547(8) 0.2300(4) 1.0396(6) 0.101(3) Uani 1 1 d . . . F14 F 0.6639(5) 0.3371(3) 0.9958(6) 0.090(2) Uani 1 1 d . . . F15 F 0.8031(7) 0.3105(4) 0.8854(6) 0.100(3) Uani 1 1 d . . . F16 F 0.6274(5) 0.2521(5) 0.8834(5) 0.104(3) Uani 1 1 d . . . P2 P 0.0039(2) 0.00699(13) 0.76901(18) 0.0433(6) Uani 1 1 d . . . F21 F 0.1093(5) 0.0316(3) 0.8438(5) 0.0715(18) Uani 1 1 d . . . F22 F 0.0470(6) -0.0716(3) 0.7821(5) 0.0718(17) Uani 1 1 d . . . F23 F 0.0833(9) 0.0180(5) 0.6805(6) 0.131(3) Uani 1 1 d . . . F24 F -0.0728(5) -0.0030(3) 0.8642(5) 0.0745(19) Uani 1 1 d . . . F25 F -0.0391(6) 0.0862(3) 0.7611(5) 0.083(2) Uani 1 1 d . . . F26 F -0.1066(8) -0.0152(5) 0.7040(6) 0.123(3) Uani 1 1 d . . . N1 N 0.2742(4) 0.1974(3) 1.1076(4) 0.0207(12) Uani 1 1 d . . . C1 C 0.1421(7) 0.2145(5) 1.1167(6) 0.0386(19) Uani 1 1 d . . . H1A H 0.1195 0.2056 1.1842 0.046 Uiso 1 1 calc R . . H1B H 0.1290 0.2636 1.1028 0.046 Uiso 1 1 calc R . . C2 C 0.0668(7) 0.1715(5) 1.0460(6) 0.039(2) Uani 1 1 d . . . H2A H 0.0636 0.1240 1.0703 0.047 Uiso 1 1 calc R . . H2B H -0.0127 0.1899 1.0434 0.047 Uiso 1 1 calc R . . N2 N 0.1122(5) 0.1714(4) 0.9454(5) 0.0335(15) Uani 1 1 d . . . H2 H 0.1023 0.1290 0.9162 0.040 Uiso 1 1 calc R . . C3 C 0.0753(7) 0.2281(4) 0.8763(6) 0.0359(18) Uani 1 1 d . . . H3A H 0.0845 0.2728 0.9093 0.043 Uiso 1 1 calc R . . H3B H -0.0070 0.2223 0.8562 0.043 Uiso 1 1 calc R . . C4 C 0.1507(6) 0.2260(5) 0.7849(6) 0.0351(18) Uani 1 1 d . . . H4A H 0.1189 0.1914 0.7388 0.042 Uiso 1 1 calc R . . H4B H 0.1467 0.2709 0.7520 0.042 Uiso 1 1 calc R . . N3 N 0.2770(5) 0.2088(3) 0.8112(4) 0.0245(13) Uani 1 1 d . . . C5 C 0.3584(7) 0.2692(4) 0.7922(5) 0.0308(17) Uani 1 1 d . . . H5A H 0.3315 0.2935 0.7324 0.037 Uiso 1 1 calc R . . H5B H 0.4370 0.2517 0.7821 0.037 Uiso 1 1 calc R . . C6 C 0.3615(7) 0.3191(4) 0.8790(5) 0.0316(17) Uani 1 1 d . . . H6A H 0.4212 0.3544 0.8702 0.038 Uiso 1 1 calc R . . H6B H 0.2860 0.3421 0.8834 0.038 Uiso 1 1 calc R . . N4 N 0.3891(5) 0.2783(3) 0.9712(4) 0.0289(14) Uani 1 1 d . . . H4 H 0.4656 0.2643 0.9733 0.035 Uiso 1 1 calc R . . C7 C 0.3600(7) 0.3116(4) 1.0663(5) 0.0324(17) Uani 1 1 d . . . H7A H 0.2858 0.3363 1.0584 0.039 Uiso 1 1 calc R . . H7B H 0.4207 0.3449 1.0861 0.039 Uiso 1 1 calc R . . C8 C 0.3510(7) 0.2554(4) 1.1453(5) 0.0348(18) Uani 1 1 d . . . H8A H 0.4288 0.2375 1.1630 0.042 Uiso 1 1 calc R . . H8B H 0.3186 0.2752 1.2045 0.042 Uiso 1 1 calc R . . C9 C 0.3002(6) 0.1296(4) 1.1579(5) 0.0299(17) Uani 1 1 d . . . H9A H 0.2446 0.0947 1.1332 0.036 Uiso 1 1 calc R . . H9B H 0.2907 0.1347 1.2287 0.036 Uiso 1 1 calc R . . C10 C 0.4242(6) 0.1053(3) 1.1399(5) 0.0266(16) Uani 1 1 d . . . C11 C 0.5087(7) 0.0908(4) 1.2157(5) 0.0350(18) Uani 1 1 d . . . H11 H 0.4882 0.0954 1.2815 0.042 Uiso 1 1 calc R . . C12 C 0.6230(8) 0.0696(4) 1.1955(6) 0.0381(19) Uani 1 1 d . . . H12 H 0.6760 0.0601 1.2481 0.046 Uiso 1 1 calc R . . C13 C 0.6588(7) 0.0626(4) 1.1002(6) 0.0358(18) Uani 1 1 d . . . H13 H 0.7357 0.0496 1.0880 0.043 Uiso 1 1 calc R . . C14 C 0.5771(6) 0.0753(3) 1.0208(6) 0.0276(16) Uani 1 1 d . . . C15 C 0.4632(6) 0.0941(4) 1.0456(5) 0.0262(15) Uani 1 1 d . . . O1 O 0.3932(4) 0.1067(2) 0.9594(3) 0.0242(11) Uani 1 1 d . . . C16 C 0.4687(6) 0.1004(4) 0.8795(5) 0.0264(15) Uani 1 1 d . . . C17 C 0.5791(6) 0.0792(3) 0.9132(5) 0.0261(15) Uani 1 1 d . . . C18 C 0.6643(7) 0.0721(4) 0.8416(6) 0.0350(18) Uani 1 1 d . . . H18A H 0.7407 0.0585 0.8596 0.042 Uiso 1 1 calc R . . C19 C 0.6318(7) 0.0860(4) 0.7434(6) 0.039(2) Uani 1 1 d . . . H19 H 0.6864 0.0789 0.6949 0.047 Uiso 1 1 calc R . . C20 C 0.5199(7) 0.1104(4) 0.7149(6) 0.0328(17) Uani 1 1 d . . . H20 H 0.5030 0.1214 0.6486 0.039 Uiso 1 1 calc R . . C21 C 0.4331(6) 0.1187(4) 0.7839(5) 0.0269(16) Uani 1 1 d . . . C22 C 0.3120(6) 0.1443(4) 0.7556(5) 0.0293(16) Uani 1 1 d . . . H22A H 0.3077 0.1542 0.6849 0.035 Uiso 1 1 calc R . . H22B H 0.2559 0.1076 0.7679 0.035 Uiso 1 1 calc R . . N35 N 0.6024(7) 0.0898(4) 0.4693(5) 0.0470(18) Uani 1 1 d . . . C36 C 0.6476(8) 0.0375(5) 0.4829(6) 0.0390(19) Uani 1 1 d . . . C37 C 0.7081(9) -0.0275(5) 0.4996(8) 0.060(3) Uani 1 1 d . . . H37A H 0.7551 -0.0377 0.4439 0.090 Uiso 1 1 calc R . . H37B H 0.6516 -0.0641 0.5074 0.090 Uiso 1 1 calc R . . H37C H 0.7578 -0.0241 0.5587 0.090 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0196(4) 0.0226(5) 0.0251(5) 0.0010(3) -0.0004(3) 0.0002(4) P1 0.0264(10) 0.0335(12) 0.0287(10) -0.0032(8) 0.0014(8) -0.0033(8) F11 0.044(3) 0.068(4) 0.129(5) -0.051(4) -0.002(3) 0.005(3) F12 0.061(4) 0.130(6) 0.091(5) -0.058(4) -0.033(3) 0.024(4) F13 0.139(7) 0.065(5) 0.103(6) 0.015(4) 0.058(5) -0.022(4) F14 0.042(3) 0.054(4) 0.173(7) -0.041(4) 0.005(4) 0.010(3) F15 0.089(5) 0.119(7) 0.095(5) 0.044(4) 0.030(4) -0.005(5) F16 0.047(4) 0.162(8) 0.100(5) -0.065(5) -0.033(3) 0.024(4) P2 0.0364(12) 0.0423(14) 0.0510(13) 0.0024(10) -0.0012(10) -0.0042(10) F21 0.055(4) 0.048(4) 0.109(5) -0.011(3) -0.028(3) 0.004(3) F22 0.085(4) 0.037(3) 0.094(4) -0.017(3) 0.019(3) 0.006(3) F23 0.162(9) 0.144(8) 0.093(6) 0.025(5) 0.073(6) 0.016(7) F24 0.067(4) 0.070(4) 0.089(4) 0.016(3) 0.030(3) 0.025(3) F25 0.068(4) 0.053(4) 0.125(6) 0.035(4) -0.023(4) 0.009(3) F26 0.109(7) 0.120(7) 0.135(7) -0.024(5) -0.066(5) -0.025(5) N1 0.012(3) 0.017(3) 0.033(3) 0.000(2) 0.000(2) 0.003(2) C1 0.038(5) 0.042(5) 0.037(4) 0.003(4) 0.013(4) 0.012(4) C2 0.023(4) 0.052(5) 0.042(5) 0.012(4) 0.005(3) 0.005(4) N2 0.028(3) 0.035(4) 0.038(4) 0.001(3) 0.000(3) -0.001(3) C3 0.030(4) 0.040(5) 0.038(4) 0.006(4) -0.001(3) 0.010(4) C4 0.023(4) 0.042(5) 0.040(4) 0.003(4) -0.009(3) 0.006(3) N3 0.024(3) 0.024(3) 0.025(3) 0.000(2) -0.004(2) -0.001(2) C5 0.034(4) 0.025(4) 0.033(4) 0.004(3) 0.003(3) -0.008(3) C6 0.033(4) 0.028(4) 0.035(4) 0.005(3) 0.004(3) -0.001(3) N4 0.025(3) 0.029(3) 0.032(3) 0.001(3) -0.002(3) -0.001(3) C7 0.039(4) 0.022(4) 0.036(4) -0.004(3) -0.002(3) 0.000(3) C8 0.042(5) 0.032(4) 0.030(4) -0.004(3) -0.007(3) 0.010(4) C9 0.034(4) 0.031(4) 0.025(4) 0.005(3) 0.002(3) -0.002(3) C10 0.037(4) 0.008(3) 0.034(4) 0.002(3) -0.002(3) -0.001(3) C11 0.049(5) 0.030(4) 0.025(4) 0.007(3) -0.011(3) -0.004(4) C12 0.048(5) 0.029(5) 0.036(4) 0.006(3) -0.017(4) 0.003(4) C13 0.028(4) 0.024(4) 0.055(5) 0.003(4) -0.007(3) 0.003(3) C14 0.024(4) 0.010(4) 0.048(4) 0.003(3) -0.005(3) -0.001(3) C15 0.029(4) 0.015(4) 0.033(4) 0.003(3) -0.009(3) -0.004(3) O1 0.022(2) 0.024(3) 0.027(2) 0.002(2) 0.0008(19) 0.000(2) C16 0.027(4) 0.023(4) 0.030(4) -0.001(3) 0.006(3) 0.002(3) C17 0.026(4) 0.014(4) 0.039(4) -0.002(3) 0.001(3) -0.003(3) C18 0.028(4) 0.020(4) 0.057(5) 0.000(4) 0.009(4) 0.007(3) C19 0.041(5) 0.026(4) 0.053(5) -0.001(4) 0.023(4) -0.004(4) C20 0.040(4) 0.029(4) 0.030(4) -0.003(3) 0.007(3) -0.002(3) C21 0.029(4) 0.023(4) 0.028(4) -0.004(3) 0.003(3) -0.006(3) C22 0.032(4) 0.032(4) 0.024(4) -0.006(3) 0.001(3) 0.002(3) N35 0.052(5) 0.041(5) 0.048(4) -0.001(4) 0.003(3) -0.001(4) C36 0.041(5) 0.044(6) 0.032(4) -0.005(4) 0.001(3) -0.008(4) C37 0.062(7) 0.043(6) 0.075(7) -0.004(5) -0.009(5) 0.006(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.988(6) . ? Cu1 N2 1.998(6) . ? Cu1 N1 2.005(6) . ? Cu1 N3 2.008(5) . ? Cu1 O1 2.131(5) . ? P1 F11 1.567(6) . ? P1 F14 1.569(6) . ? P1 F13 1.567(6) . ? P1 F16 1.573(6) . ? P1 F12 1.574(6) . ? P1 F15 1.570(7) . ? P2 F23 1.540(7) . ? P2 F26 1.562(7) . ? P2 F22 1.593(6) . ? P2 F24 1.593(6) . ? P2 F25 1.598(6) . ? P2 F21 1.607(6) . ? N1 C9 1.492(9) . ? N1 C8 1.491(10) . ? N1 C1 1.549(9) . ? C1 C2 1.503(12) . ? C2 N2 1.470(10) . ? N2 C3 1.481(10) . ? C3 C4 1.530(11) . ? C4 N3 1.504(9) . ? N3 C22 1.510(9) . ? N3 C5 1.510(9) . ? C5 C6 1.511(10) . ? C6 N4 1.492(9) . ? N4 C7 1.481(9) . ? C7 C8 1.523(11) . ? C9 C10 1.514(10) . ? C10 C15 1.379(10) . ? C10 C11 1.403(10) . ? C11 C12 1.400(12) . ? C12 C13 1.370(11) . ? C13 C14 1.410(10) . ? C14 C15 1.399(10) . ? C14 C17 1.453(10) . ? C15 O1 1.402(8) . ? O1 C16 1.409(8) . ? C16 C21 1.380(10) . ? C16 C17 1.380(10) . ? C17 C18 1.402(10) . ? C18 C19 1.386(12) . ? C19 C20 1.396(12) . ? C20 C21 1.393(10) . ? C21 C22 1.498(10) . ? N35 C36 1.138(11) . ? C36 C37 1.438(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N2 141.5(3) . . ? N4 Cu1 N1 88.0(2) . . ? N2 Cu1 N1 90.5(2) . . ? N4 Cu1 N3 88.9(2) . . ? N2 Cu1 N3 86.8(2) . . ? N1 Cu1 N3 171.2(2) . . ? N4 Cu1 O1 106.3(2) . . ? N2 Cu1 O1 112.2(2) . . ? N1 Cu1 O1 93.43(19) . . ? N3 Cu1 O1 95.3(2) . . ? F11 P1 F14 178.1(4) . . ? F11 P1 F13 92.0(4) . . ? F14 P1 F13 86.2(4) . . ? F11 P1 F16 88.8(4) . . ? F14 P1 F16 91.7(4) . . ? F13 P1 F16 86.8(5) . . ? F11 P1 F12 90.3(4) . . ? F14 P1 F12 89.1(4) . . ? F13 P1 F12 92.7(5) . . ? F16 P1 F12 179.0(5) . . ? F11 P1 F15 89.0(4) . . ? F14 P1 F15 92.9(4) . . ? F13 P1 F15 179.0(5) . . ? F16 P1 F15 93.6(5) . . ? F12 P1 F15 86.9(5) . . ? F23 P2 F26 95.0(6) . . ? F23 P2 F22 91.6(4) . . ? F26 P2 F22 92.3(4) . . ? F23 P2 F24 177.0(5) . . ? F26 P2 F24 88.0(5) . . ? F22 P2 F24 88.5(3) . . ? F23 P2 F25 90.3(5) . . ? F26 P2 F25 89.2(4) . . ? F22 P2 F25 177.5(4) . . ? F24 P2 F25 89.5(4) . . ? F23 P2 F21 90.0(5) . . ? F26 P2 F21 174.7(5) . . ? F22 P2 F21 89.5(3) . . ? F24 P2 F21 87.1(4) . . ? F25 P2 F21 88.9(3) . . ? C9 N1 C8 113.1(5) . . ? C9 N1 C1 108.9(5) . . ? C8 N1 C1 111.8(6) . . ? C9 N1 Cu1 115.3(4) . . ? C8 N1 Cu1 107.3(4) . . ? C1 N1 Cu1 99.7(4) . . ? C2 C1 N1 111.3(6) . . ? N2 C2 C1 111.9(6) . . ? C2 N2 C3 118.5(6) . . ? C2 N2 Cu1 106.9(5) . . ? C3 N2 Cu1 97.6(5) . . ? N2 C3 C4 109.5(6) . . ? N3 C4 C3 112.2(6) . . ? C22 N3 C5 111.6(5) . . ? C22 N3 C4 109.3(5) . . ? C5 N3 C4 112.3(6) . . ? C22 N3 Cu1 113.4(4) . . ? C5 N3 Cu1 105.4(4) . . ? C4 N3 Cu1 104.6(4) . . ? N3 C5 C6 110.5(6) . . ? N4 C6 C5 108.0(6) . . ? C7 N4 C6 116.6(6) . . ? C7 N4 Cu1 104.7(4) . . ? C6 N4 Cu1 104.0(4) . . ? N4 C7 C8 108.9(6) . . ? N1 C8 C7 110.2(6) . . ? N1 C9 C10 111.4(6) . . ? C15 C10 C11 113.8(7) . . ? C15 C10 C9 122.2(6) . . ? C11 C10 C9 124.0(7) . . ? C10 C11 C12 122.1(7) . . ? C13 C12 C11 121.7(7) . . ? C12 C13 C14 118.8(7) . . ? C15 C14 C13 116.9(7) . . ? C15 C14 C17 106.1(6) . . ? C13 C14 C17 136.8(7) . . ? C10 C15 C14 126.6(7) . . ? C10 C15 O1 122.9(6) . . ? C14 C15 O1 110.2(6) . . ? C15 O1 C16 106.0(5) . . ? C15 O1 Cu1 117.0(4) . . ? C16 O1 Cu1 116.5(4) . . ? C21 C16 C17 127.7(7) . . ? C21 C16 O1 121.8(6) . . ? C17 C16 O1 110.4(6) . . ? C16 C17 C18 116.6(7) . . ? C16 C17 C14 107.0(6) . . ? C18 C17 C14 136.2(7) . . ? C19 C18 C17 118.3(7) . . ? C18 C19 C20 122.2(7) . . ? C21 C20 C19 121.2(7) . . ? C16 C21 C20 114.0(7) . . ? C16 C21 C22 123.6(6) . . ? C20 C21 C22 122.4(6) . . ? N3 C22 C21 113.6(6) . . ? N35 C36 C37 178.2(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Cu1 N1 C9 -128.3(5) . . . . ? N2 Cu1 N1 C9 90.2(5) . . . . ? N3 Cu1 N1 C9 162.7(13) . . . . ? O1 Cu1 N1 C9 -22.0(5) . . . . ? N4 Cu1 N1 C8 -1.3(4) . . . . ? N2 Cu1 N1 C8 -142.8(4) . . . . ? N3 Cu1 N1 C8 -70.3(16) . . . . ? O1 Cu1 N1 C8 105.0(4) . . . . ? N4 Cu1 N1 C1 115.3(4) . . . . ? N2 Cu1 N1 C1 -26.2(5) . . . . ? N3 Cu1 N1 C1 46.3(16) . . . . ? O1 Cu1 N1 C1 -138.4(4) . . . . ? C9 N1 C1 C2 -76.2(7) . . . . ? C8 N1 C1 C2 158.1(6) . . . . ? Cu1 N1 C1 C2 45.0(7) . . . . ? N1 C1 C2 N2 -47.1(9) . . . . ? C1 C2 N2 C3 -87.0(8) . . . . ? C1 C2 N2 Cu1 21.8(8) . . . . ? N4 Cu1 N2 C2 -83.6(6) . . . . ? N1 Cu1 N2 C2 3.9(5) . . . . ? N3 Cu1 N2 C2 -167.8(5) . . . . ? O1 Cu1 N2 C2 97.8(5) . . . . ? N4 Cu1 N2 C3 39.4(6) . . . . ? N1 Cu1 N2 C3 126.8(5) . . . . ? N3 Cu1 N2 C3 -44.8(5) . . . . ? O1 Cu1 N2 C3 -139.3(4) . . . . ? C2 N2 C3 C4 168.9(7) . . . . ? Cu1 N2 C3 C4 55.0(7) . . . . ? N2 C3 C4 N3 -38.9(9) . . . . ? C3 C4 N3 C22 122.1(7) . . . . ? C3 C4 N3 C5 -113.5(7) . . . . ? C3 C4 N3 Cu1 0.3(7) . . . . ? N4 Cu1 N3 C22 124.9(5) . . . . ? N2 Cu1 N3 C22 -93.4(5) . . . . ? N1 Cu1 N3 C22 -166.1(13) . . . . ? O1 Cu1 N3 C22 18.6(5) . . . . ? N4 Cu1 N3 C5 2.5(4) . . . . ? N2 Cu1 N3 C5 144.2(5) . . . . ? N1 Cu1 N3 C5 71.5(16) . . . . ? O1 Cu1 N3 C5 -103.8(4) . . . . ? N4 Cu1 N3 C4 -116.0(5) . . . . ? N2 Cu1 N3 C4 25.7(5) . . . . ? N1 Cu1 N3 C4 -47.0(17) . . . . ? O1 Cu1 N3 C4 137.7(5) . . . . ? C22 N3 C5 C6 -153.2(6) . . . . ? C4 N3 C5 C6 83.6(7) . . . . ? Cu1 N3 C5 C6 -29.7(7) . . . . ? N3 C5 C6 N4 52.5(8) . . . . ? C5 C6 N4 C7 -161.2(6) . . . . ? C5 C6 N4 Cu1 -46.6(6) . . . . ? N2 Cu1 N4 C7 63.8(6) . . . . ? N1 Cu1 N4 C7 -24.5(4) . . . . ? N3 Cu1 N4 C7 147.3(5) . . . . ? O1 Cu1 N4 C7 -117.5(4) . . . . ? N2 Cu1 N4 C6 -59.0(6) . . . . ? N1 Cu1 N4 C6 -147.4(5) . . . . ? N3 Cu1 N4 C6 24.4(5) . . . . ? O1 Cu1 N4 C6 119.6(4) . . . . ? C6 N4 C7 C8 159.5(6) . . . . ? Cu1 N4 C7 C8 45.3(7) . . . . ? C9 N1 C8 C7 155.1(6) . . . . ? C1 N1 C8 C7 -81.4(7) . . . . ? Cu1 N1 C8 C7 26.9(7) . . . . ? N4 C7 C8 N1 -49.3(8) . . . . ? C8 N1 C9 C10 -62.5(8) . . . . ? C1 N1 C9 C10 172.5(6) . . . . ? Cu1 N1 C9 C10 61.5(7) . . . . ? N1 C9 C10 C15 -58.4(9) . . . . ? N1 C9 C10 C11 122.8(7) . . . . ? C15 C10 C11 C12 2.3(11) . . . . ? C9 C10 C11 C12 -178.8(7) . . . . ? C10 C11 C12 C13 0.7(12) . . . . ? C11 C12 C13 C14 -1.7(12) . . . . ? C12 C13 C14 C15 -0.4(10) . . . . ? C12 C13 C14 C17 174.1(8) . . . . ? C11 C10 C15 C14 -4.6(10) . . . . ? C9 C10 C15 C14 176.4(7) . . . . ? C11 C10 C15 O1 -178.8(6) . . . . ? C9 C10 C15 O1 2.3(10) . . . . ? C13 C14 C15 C10 3.8(11) . . . . ? C17 C14 C15 C10 -172.3(7) . . . . ? C13 C14 C15 O1 178.6(6) . . . . ? C17 C14 C15 O1 2.5(7) . . . . ? C10 C15 O1 C16 170.6(6) . . . . ? C14 C15 O1 C16 -4.4(7) . . . . ? C10 C15 O1 Cu1 38.8(8) . . . . ? C14 C15 O1 Cu1 -136.3(5) . . . . ? N4 Cu1 O1 C15 63.4(5) . . . . ? N2 Cu1 O1 C15 -117.5(5) . . . . ? N1 Cu1 O1 C15 -25.5(5) . . . . ? N3 Cu1 O1 C15 153.8(4) . . . . ? N4 Cu1 O1 C16 -63.4(5) . . . . ? N2 Cu1 O1 C16 115.7(5) . . . . ? N1 Cu1 O1 C16 -152.3(4) . . . . ? N3 Cu1 O1 C16 26.9(5) . . . . ? C15 O1 C16 C21 -171.0(6) . . . . ? Cu1 O1 C16 C21 -38.9(8) . . . . ? C15 O1 C16 C17 4.7(7) . . . . ? Cu1 O1 C16 C17 136.9(5) . . . . ? C21 C16 C17 C18 -3.3(11) . . . . ? O1 C16 C17 C18 -178.8(6) . . . . ? C21 C16 C17 C14 172.2(7) . . . . ? O1 C16 C17 C14 -3.3(8) . . . . ? C15 C14 C17 C16 0.5(8) . . . . ? C13 C14 C17 C16 -174.4(8) . . . . ? C15 C14 C17 C18 174.7(8) . . . . ? C13 C14 C17 C18 -0.2(14) . . . . ? C16 C17 C18 C19 -0.6(10) . . . . ? C14 C17 C18 C19 -174.4(8) . . . . ? C17 C18 C19 C20 3.7(11) . . . . ? C18 C19 C20 C21 -3.3(12) . . . . ? C17 C16 C21 C20 3.8(11) . . . . ? O1 C16 C21 C20 178.8(6) . . . . ? C17 C16 C21 C22 -177.1(7) . . . . ? O1 C16 C21 C22 -2.1(11) . . . . ? C19 C20 C21 C16 -0.4(11) . . . . ? C19 C20 C21 C22 -179.5(7) . . . . ? C5 N3 C22 C21 60.7(8) . . . . ? C4 N3 C22 C21 -174.5(6) . . . . ? Cu1 N3 C22 C21 -58.2(7) . . . . ? C16 C21 C22 N3 58.1(9) . . . . ? C20 C21 C22 N3 -122.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 2.403 _refine_diff_density_min -0.637 _refine_diff_density_rms 0.145 #===END