data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year 2012 _journal_volume 14 _journal_page_first 7493 #TrackingRef 'Cu(dkt)(morph)2X.cif' #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2012-05-23 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? #============================================================================== # # SUBMISSION DETAILS _publ_contact_author_name 'Stilinovicc, Vladimir' # Name of author for correspondence _publ_contact_author_address ;Department of Chemistry University of Zagreb Zagreb Croatia ; # Address of author for correspondence _publ_contact_author_email vstilinovic@chem.pmf.hr _publ_contact_author_fax '+385 1 4606341' _publ_contact_author_phone '+385 1 4606371' _publ_contact_letter ; Submission dated :2012-05-23 Dear Madam/Dear Sir, This CIF file contains the results of the collection, reduction, and X-ray structural data of fout organic compounds. The structures have been described in the manuscript under the title: Keto-enol tautomerism in asymmetric Schiff bases derived from p-phenylenediamine by the authors: K. Uzarevic, M. Rubcic, V. Stilinovic, B. Kaitner and M. Cindric. The manuscript will be sent to the Journal of Molecular Structure for publication upon the deposition data with CCDC and the deposition numbers are available. The data have been checked using checkCIF/PLATON. We ask you kindly that the structural data be deposited with CCDC. Sincerely yours, V. Stilinovic ; #============================================================================== # # TITLE AND AUTHOR LIST _publ_section_title ; Bis(morpholine) hydrogen bond pincer -- a novel series of heteroleptic Cu(II) coordination compounds as receptors for electron rich guests ; _publ_section_title_footnote ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_footnote _publ_author_address 'V. Stilinovic' ; ? ; ;Department of Chemistry University of Zagreb Zagreb Croatia ; K.Uarevic ; ? ; ;Department of Chemistry University of Zagreb Zagreb Croatia ; I.Cvrtila ; ? ; ;Department of Chemistry University of Zagreb Zagreb Croatia ; 'B. Kaitner' ; ? ; ;Department of Chemistry University of Zagreb Zagreb Croatia ; #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_acac_Cl _database_code_depnum_ccdc_archive 'CCDC 883439' #TrackingRef 'Cu(dkt)(morph)2X.cif' _audit_creation_date 2011-11-23T13:55:26-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; acetylacetonatochlorobis(morpholine)copper(II) ; _chemical_formula_sum 'C13 H25 Cl Cu N2 O4' _chemical_formula_moiety 'C13 H25 Cl Cu N2 O4' _chemical_formula_weight 372.35 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall 'P -2yn' 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 18.7558(11) _cell_length_b 10.1597(4) _cell_length_c 18.8355(12) _cell_angle_alpha 90 _cell_angle_beta 104.734(6) _cell_angle_gamma 90 _cell_volume 3471.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 275 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 52.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_special_details ; ? ; _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.427 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.61596 _exptl_absorpt_correction_T_max 0.79111 _exptl_absorpt_process_details 'N.W. Alcock (1970). Cryst. Computing, p271' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 27 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_unetI/netI 0.047 _diffrn_reflns_number 31363 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.81 _diffrn_reflns_theta_max 27 _diffrn_reflns_theta_full 27 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 7519 _reflns_number_gt 5073 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0214P)^2^+39.0725P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 7519 _refine_ls_number_parameters 399 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1103 _refine_ls_R_factor_gt 0.0821 _refine_ls_wR_factor_ref 0.2296 _refine_ls_wR_factor_gt 0.2234 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.151 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.69 _refine_diff_density_min -0.661 _refine_diff_density_rms 0.126 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.77052(6) 0.05285(10) 0.34376(6) 0.0461(3) Uani 1 1 d . . . Cl1 Cl 0.76086(14) -0.0296(2) 0.21454(14) 0.0556(6) Uani 1 1 d . . . N2 N 0.8412(4) 0.2011(7) 0.3399(4) 0.0434(17) Uani 1 1 d D . . N1 N 0.6859(4) 0.1830(7) 0.3285(4) 0.0427(16) Uani 1 1 d D . . O1 O 0.8556(4) -0.0467(7) 0.3981(4) 0.067(2) Uani 1 1 d . . . O2 O 0.7030(4) -0.0768(6) 0.3649(4) 0.0647(19) Uani 1 1 d . . . O4 O 0.9777(4) 0.3420(8) 0.3767(4) 0.072(2) Uani 1 1 d . . . C14 C 0.9036(5) 0.1682(10) 0.3089(6) 0.056(2) Uani 1 1 d D . . H14A H 0.8852 0.1329 0.2598 0.067 Uiso 1 1 calc R . . H14B H 0.9339 0.1014 0.3389 0.067 Uiso 1 1 calc R . . C4 C 0.7210(7) -0.1908(9) 0.3931(5) 0.061(3) Uani 1 1 d . . . O3 O 0.5374(4) 0.2612(8) 0.3255(6) 0.084(3) Uani 1 1 d . . . C11 C 0.8688(5) 0.2663(10) 0.4121(5) 0.057(2) Uani 1 1 d D . . H11A H 0.8956 0.2029 0.4474 0.069 Uiso 1 1 calc R . . H11B H 0.8273 0.2979 0.4293 0.069 Uiso 1 1 calc R . . C2 C 0.8561(7) -0.1624(11) 0.4212(5) 0.066(3) Uani 1 1 d . . . C3 C 0.7924(7) -0.2374(11) 0.4176(6) 0.073(3) Uani 1 1 d . . . H3 H 0.7986 -0.3247 0.4327 0.087 Uiso 1 1 calc R . . C13 C 0.9489(6) 0.2876(10) 0.3060(6) 0.060(3) Uani 1 1 d . . . H13A H 0.9893 0.2645 0.2849 0.072 Uiso 1 1 calc R . . H13B H 0.9189 0.3529 0.2745 0.072 Uiso 1 1 calc R . . C5 C 0.6548(8) -0.2766(10) 0.3956(7) 0.082(4) Uani 1 1 d . . . H5A H 0.6456 -0.2707 0.4433 0.123 Uiso 1 1 calc R . . H5B H 0.6649 -0.3664 0.3857 0.123 Uiso 1 1 calc R . . H5C H 0.6122 -0.2466 0.3592 0.123 Uiso 1 1 calc R . . C10 C 0.6593(6) 0.2016(10) 0.3950(6) 0.062(3) Uani 1 1 d D . . H10A H 0.7 0.2316 0.4345 0.075 Uiso 1 1 calc R . . H10B H 0.643 0.1174 0.4094 0.075 Uiso 1 1 calc R . . C9 C 0.5968(6) 0.2991(11) 0.3850(7) 0.073(3) Uani 1 1 d . . . H9A H 0.58 0.3034 0.4296 0.088 Uiso 1 1 calc R . . H9B H 0.614 0.3859 0.3758 0.088 Uiso 1 1 calc R . . C8 C 0.5598(6) 0.2513(11) 0.2595(7) 0.074(3) Uani 1 1 d . . . H8A H 0.5762 0.3368 0.2472 0.088 Uiso 1 1 calc R . . H8B H 0.5179 0.225 0.2201 0.088 Uiso 1 1 calc R . . C7 C 0.6214(5) 0.1524(10) 0.2658(6) 0.059(3) Uani 1 1 d D . . H7A H 0.6031 0.0651 0.2724 0.071 Uiso 1 1 calc R . . H7B H 0.6371 0.1523 0.2205 0.071 Uiso 1 1 calc R . . C12 C 0.9190(6) 0.3809(12) 0.4069(7) 0.073(3) Uani 1 1 d . . . H12A H 0.8905 0.4493 0.3766 0.088 Uiso 1 1 calc R . . H12B H 0.9391 0.4172 0.4556 0.088 Uiso 1 1 calc R . . C1 C 0.9270(7) -0.2262(14) 0.4522(8) 0.103(5) Uani 1 1 d . . . H1A H 0.9643 -0.1603 0.4685 0.155 Uiso 1 1 calc R . . H1B H 0.9398 -0.2801 0.4154 0.155 Uiso 1 1 calc R . . H1C H 0.9236 -0.2801 0.493 0.155 Uiso 1 1 calc R . . H2N H 0.8142(8) 0.2631(16) 0.3098(5) 0.05(3) Uiso 1 1 d D . . H1N H 0.7021(10) 0.2630(13) 0.3175(6) 0.08(3) Uiso 1 1 d D . . Cu2 Cu 0.66036(6) 0.17387(10) 0.74559(6) 0.0473(3) Uani 1 1 d . . . Cl2 Cl 0.78992(14) 0.2534(2) 0.75106(14) 0.0575(6) Uani 1 1 d . . . N3 N 0.6879(4) 0.0357(6) 0.8254(4) 0.0423(16) Uani 1 1 d D . . N4 N 0.6487(4) 0.0316(7) 0.6666(4) 0.0475(18) Uani 1 1 d D . . O6 O 0.6420(4) 0.2929(6) 0.8201(4) 0.0631(18) Uani 1 1 d . . . O5 O 0.6086(4) 0.2864(7) 0.6662(4) 0.073(2) Uani 1 1 d . . . O7 O 0.6980(6) -0.0755(9) 0.9680(4) 0.091(3) Uani 1 1 d U . . C24 C 0.6887(6) 0.0609(10) 0.6104(5) 0.056(2) Uani 1 1 d D . . H24A H 0.7407 0.0723 0.634 0.068 Uiso 1 1 calc R . . H24B H 0.6704 0.1429 0.586 0.068 Uiso 1 1 calc R . . C18 C 0.6121(5) 0.4056(9) 0.8077(7) 0.065(3) Uani 1 1 d . . . C23 C 0.7452(6) 0.0724(10) 0.8916(5) 0.061(3) Uani 1 1 d D . . H23A H 0.7287 0.1484 0.9144 0.073 Uiso 1 1 calc R . . H23B H 0.7898 0.0968 0.8778 0.073 Uiso 1 1 calc R . . C16 C 0.5841(6) 0.4003(10) 0.6743(7) 0.064(3) Uani 1 1 d . . . O8 O 0.6037(5) -0.0661(9) 0.5188(4) 0.077(2) Uani 1 1 d . . . C20 C 0.6227(6) -0.0101(12) 0.8488(6) 0.072(3) Uani 1 1 d D . . H20A H 0.586 -0.0427 0.8064 0.087 Uiso 1 1 calc R . . H20B H 0.6014 0.0634 0.869 0.087 Uiso 1 1 calc R . . C22 C 0.7616(8) -0.0381(11) 0.9455(6) 0.079(4) Uani 1 1 d . . . H22A H 0.7798 -0.113 0.9234 0.095 Uiso 1 1 calc R . . H22B H 0.7999 -0.0112 0.9881 0.095 Uiso 1 1 calc R . . C25 C 0.6796(7) -0.0467(11) 0.5545(5) 0.069(3) Uani 1 1 d . . . H25A H 0.7063 -0.0239 0.5183 0.082 Uiso 1 1 calc R . . H25B H 0.7003 -0.1277 0.5783 0.082 Uiso 1 1 calc R . . C27 C 0.5721(6) -0.0005(12) 0.6295(6) 0.068(3) Uani 1 1 d D . . H27A H 0.5475 0.0788 0.6073 0.081 Uiso 1 1 calc R . . H27B H 0.5472 -0.0307 0.6658 0.081 Uiso 1 1 calc R . . C19 C 0.6088(7) 0.4806(11) 0.8756(7) 0.083(4) Uani 1 1 d . . . H19A H 0.5583 0.4902 0.8772 0.125 Uiso 1 1 calc R . . H19B H 0.6304 0.566 0.8747 0.125 Uiso 1 1 calc R . . H19C H 0.6356 0.4334 0.9182 0.125 Uiso 1 1 calc R . . C17 C 0.5853(6) 0.4600(10) 0.7384(8) 0.072(3) Uani 1 1 d . . . H17 H 0.5665 0.5451 0.7361 0.086 Uiso 1 1 calc R . . C21 C 0.6427(8) -0.1179(13) 0.9056(7) 0.093(4) Uani 1 1 d U . . H21A H 0.5991 -0.1439 0.9208 0.111 Uiso 1 1 calc R . . H21B H 0.6603 -0.1941 0.8841 0.111 Uiso 1 1 calc R . . C26 C 0.5650(8) -0.1045(14) 0.5711(7) 0.089(4) Uani 1 1 d . . . H26A H 0.5847 -0.1871 0.5936 0.107 Uiso 1 1 calc R . . H26B H 0.5134 -0.1177 0.5467 0.107 Uiso 1 1 calc R . . C15 C 0.5463(8) 0.4674(13) 0.6029(8) 0.104(5) Uani 1 1 d . . . H15A H 0.5723 0.4477 0.5664 0.156 Uiso 1 1 calc R . . H15B H 0.546 0.5608 0.6105 0.156 Uiso 1 1 calc R . . H15C H 0.4964 0.4361 0.5867 0.156 Uiso 1 1 calc R . . H3N H 0.7053(6) -0.0356(15) 0.8059(9) 0.03(2) Uiso 1 1 d D . . H4N H 0.6695(7) -0.0428(15) 0.6899(10) 0.04(2) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0489(6) 0.0340(5) 0.0534(7) 0.0068(5) 0.0095(5) 0.0063(5) Cl1 0.0588(14) 0.0410(12) 0.0651(15) -0.0128(11) 0.0123(11) -0.0011(10) N2 0.041(4) 0.041(4) 0.044(4) -0.003(3) 0.002(3) 0.008(3) N1 0.042(4) 0.034(4) 0.052(4) 0.002(3) 0.011(3) 0.001(3) O1 0.067(4) 0.048(4) 0.074(5) 0.018(4) -0.002(4) 0.012(3) O2 0.085(5) 0.035(3) 0.078(5) 0.013(3) 0.029(4) 0.006(3) O4 0.049(4) 0.083(5) 0.080(5) -0.003(4) 0.009(4) -0.018(4) C14 0.054(6) 0.050(5) 0.061(6) 0.000(5) 0.011(5) 0.007(5) C4 0.109(9) 0.042(5) 0.040(5) -0.002(4) 0.030(6) -0.003(6) O3 0.047(4) 0.077(5) 0.135(8) -0.009(5) 0.034(5) 0.006(4) C11 0.055(6) 0.065(6) 0.053(6) -0.005(5) 0.017(5) -0.004(5) C2 0.092(8) 0.053(6) 0.047(6) 0.010(5) 0.006(5) 0.027(6) C3 0.109(10) 0.045(6) 0.061(7) 0.018(5) 0.016(6) 0.017(6) C13 0.053(6) 0.059(6) 0.072(7) 0.002(5) 0.020(5) -0.005(5) C5 0.136(11) 0.043(6) 0.080(8) -0.003(6) 0.052(8) -0.022(7) C10 0.057(6) 0.057(6) 0.077(7) -0.001(5) 0.024(5) 0.004(5) C9 0.065(7) 0.064(7) 0.098(9) 0.000(6) 0.034(7) 0.012(6) C8 0.047(6) 0.060(7) 0.102(9) 0.012(6) -0.002(6) 0.010(5) C7 0.057(6) 0.048(5) 0.065(6) 0.000(5) 0.001(5) 0.009(5) C12 0.058(7) 0.075(8) 0.079(8) -0.028(6) 0.003(6) -0.023(6) C1 0.101(10) 0.087(10) 0.103(11) 0.019(8) -0.008(8) 0.033(8) Cu2 0.0601(7) 0.0323(5) 0.0505(6) 0.0038(5) 0.0158(5) 0.0107(5) Cl2 0.0724(16) 0.0404(12) 0.0622(15) -0.0004(11) 0.0219(12) -0.0137(11) N3 0.059(4) 0.031(3) 0.043(4) -0.003(3) 0.023(3) 0.001(3) N4 0.063(5) 0.034(4) 0.041(4) 0.005(3) 0.004(3) 0.007(3) O6 0.073(5) 0.045(4) 0.075(5) -0.005(3) 0.026(4) 0.012(3) O5 0.094(6) 0.054(4) 0.067(5) 0.016(4) 0.013(4) 0.032(4) O7 0.147(8) 0.081(6) 0.053(4) 0.016(4) 0.039(4) -0.006(6) C24 0.069(6) 0.054(6) 0.051(6) 0.002(5) 0.025(5) 0.011(5) C18 0.050(6) 0.035(5) 0.117(10) -0.007(6) 0.037(6) 0.005(4) C23 0.075(7) 0.048(6) 0.054(6) 0.001(5) 0.007(5) -0.003(5) C16 0.052(6) 0.043(5) 0.099(9) 0.021(6) 0.026(6) 0.013(5) O8 0.085(5) 0.097(6) 0.042(4) -0.006(4) 0.001(4) 0.003(5) C20 0.074(7) 0.086(8) 0.062(7) 0.012(6) 0.027(6) -0.002(6) C22 0.118(10) 0.056(7) 0.051(6) 0.007(5) -0.002(7) -0.013(7) C25 0.101(9) 0.062(7) 0.044(6) -0.006(5) 0.021(6) -0.009(6) C27 0.064(7) 0.077(7) 0.063(7) -0.010(6) 0.016(5) -0.019(6) C19 0.084(8) 0.048(6) 0.125(11) -0.027(7) 0.039(8) -0.002(6) C17 0.064(7) 0.035(5) 0.123(11) 0.009(6) 0.034(7) 0.014(5) C21 0.129(11) 0.089(9) 0.073(7) 0.012(7) 0.051(6) -0.041(8) C26 0.099(10) 0.095(10) 0.069(8) -0.008(7) 0.014(7) -0.042(8) C15 0.105(10) 0.089(10) 0.123(12) 0.059(9) 0.040(9) 0.052(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O2 1.937(7) . ? Cu1 O1 1.946(6) . ? Cu1 N2 2.020(7) . ? Cu1 N1 2.029(7) . ? Cu1 Cl1 2.537(3) . ? N2 C14 1.473(11) . ? N2 C11 1.483(11) . ? N2 H2N 0.9100(10) . ? N1 C10 1.473(12) . ? N1 C7 1.494(11) . ? N1 H1N 0.9099(10) . ? O1 C2 1.252(12) . ? O2 C4 1.283(11) . ? O4 C13 1.416(12) . ? O4 C12 1.418(13) . ? C14 C13 1.490(13) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C4 C3 1.384(15) . ? C4 C5 1.528(15) . ? O3 C8 1.412(14) . ? O3 C9 1.418(14) . ? C11 C12 1.516(14) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C2 C3 1.405(16) . ? C2 C1 1.461(15) . ? C3 H3 0.93 . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C10 C9 1.510(13) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C8 C7 1.513(13) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? Cu2 O5 1.936(7) . ? Cu2 O6 1.948(7) . ? Cu2 N3 2.025(7) . ? Cu2 N4 2.046(7) . ? Cu2 Cl2 2.538(3) . ? N3 C23 1.471(12) . ? N3 C20 1.476(12) . ? N3 H3N 0.9100(10) . ? N4 C27 1.465(12) . ? N4 C24 1.476(12) . ? N4 H4N 0.9100(10) . ? O6 C18 1.271(11) . ? O5 C16 1.268(12) . ? O7 C22 1.415(15) . ? O7 C21 1.422(15) . ? C24 C25 1.497(13) . ? C24 H24A 0.97 . ? C24 H24B 0.97 . ? C18 C17 1.388(16) . ? C18 C19 1.504(15) . ? C23 C22 1.494(14) . ? C23 H23A 0.97 . ? C23 H23B 0.97 . ? C16 C17 1.346(16) . ? C16 C15 1.513(15) . ? O8 C26 1.418(13) . ? O8 C25 1.426(13) . ? C20 C21 1.511(16) . ? C20 H20A 0.97 . ? C20 H20B 0.97 . ? C22 H22A 0.97 . ? C22 H22B 0.97 . ? C25 H25A 0.97 . ? C25 H25B 0.97 . ? C27 C26 1.506(16) . ? C27 H27A 0.97 . ? C27 H27B 0.97 . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? C17 H17 0.93 . ? C21 H21A 0.97 . ? C21 H21B 0.97 . ? C26 H26A 0.97 . ? C26 H26B 0.97 . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? 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 O2 Cu1 O1 91.7(3) . . ? O2 Cu1 N2 169.6(3) . . ? O1 Cu1 N2 87.1(3) . . ? O2 Cu1 N1 86.8(3) . . ? O1 Cu1 N1 157.0(3) . . ? N2 Cu1 N1 90.3(3) . . ? O2 Cu1 Cl1 94.7(2) . . ? O1 Cu1 Cl1 100.5(2) . . ? N2 Cu1 Cl1 95.7(2) . . ? N1 Cu1 Cl1 102.5(2) . . ? C14 N2 C11 109.7(7) . . ? C14 N2 Cu1 116.1(6) . . ? C11 N2 Cu1 112.3(6) . . ? C14 N2 H2N 106.4(9) . . ? C11 N2 H2N 105.7(9) . . ? Cu1 N2 H2N 105.9(15) . . ? C10 N1 C7 108.5(7) . . ? C10 N1 Cu1 112.6(6) . . ? C7 N1 Cu1 115.1(5) . . ? C10 N1 H1N 106.4(9) . . ? C7 N1 H1N 104.9(9) . . ? Cu1 N1 H1N 108.7(16) . . ? C2 O1 Cu1 127.1(8) . . ? C4 O2 Cu1 125.6(8) . . ? C13 O4 C12 109.7(7) . . ? N2 C14 C13 110.4(8) . . ? N2 C14 H14A 109.6 . . ? C13 C14 H14A 109.6 . . ? N2 C14 H14B 109.6 . . ? C13 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? O2 C4 C3 125.3(10) . . ? O2 C4 C5 113.4(11) . . ? C3 C4 C5 121.3(10) . . ? C8 O3 C9 111.5(8) . . ? N2 C11 C12 111.2(8) . . ? N2 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? N2 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108 . . ? O1 C2 C3 124.2(10) . . ? O1 C2 C1 118.7(12) . . ? C3 C2 C1 117.1(11) . . ? C4 C3 C2 124.7(10) . . ? C4 C3 H3 117.6 . . ? C2 C3 H3 117.6 . . ? O4 C13 C14 111.6(9) . . ? O4 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? O4 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 108 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C10 C9 113.5(9) . . ? N1 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? N1 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? O3 C9 C10 110.4(9) . . ? O3 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? O3 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? O3 C8 C7 111.8(9) . . ? O3 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? O3 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? N1 C7 C8 111.9(8) . . ? N1 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? N1 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? O4 C12 C11 111.7(9) . . ? O4 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? O4 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O5 Cu2 O6 92.5(3) . . ? O5 Cu2 N3 165.0(3) . . ? O6 Cu2 N3 87.4(3) . . ? O5 Cu2 N4 85.2(3) . . ? O6 Cu2 N4 163.0(3) . . ? N3 Cu2 N4 90.6(3) . . ? O5 Cu2 Cl2 97.5(3) . . ? O6 Cu2 Cl2 96.7(2) . . ? N3 Cu2 Cl2 97.4(2) . . ? N4 Cu2 Cl2 100.3(2) . . ? C23 N3 C20 108.0(8) . . ? C23 N3 Cu2 116.5(5) . . ? C20 N3 Cu2 111.4(6) . . ? C23 N3 H3N 106.6(9) . . ? C20 N3 H3N 106.2(10) . . ? Cu2 N3 H3N 107.6(15) . . ? C27 N4 C24 108.5(8) . . ? C27 N4 Cu2 114.5(6) . . ? C24 N4 Cu2 113.5(6) . . ? C27 N4 H4N 107.1(10) . . ? C24 N4 H4N 106.2(9) . . ? Cu2 N4 H4N 106.5(16) . . ? C18 O6 Cu2 125.3(8) . . ? C16 O5 Cu2 124.9(8) . . ? C22 O7 C21 109.2(8) . . ? N4 C24 C25 111.7(8) . . ? N4 C24 H24A 109.3 . . ? C25 C24 H24A 109.3 . . ? N4 C24 H24B 109.3 . . ? C25 C24 H24B 109.3 . . ? H24A C24 H24B 107.9 . . ? O6 C18 C17 124.7(11) . . ? O6 C18 C19 114.3(11) . . ? C17 C18 C19 121.0(10) . . ? N3 C23 C22 111.5(8) . . ? N3 C23 H23A 109.3 . . ? C22 C23 H23A 109.3 . . ? N3 C23 H23B 109.3 . . ? C22 C23 H23B 109.3 . . ? H23A C23 H23B 108 . . ? O5 C16 C17 126.5(10) . . ? O5 C16 C15 114.0(11) . . ? C17 C16 C15 119.4(10) . . ? C26 O8 C25 109.7(8) . . ? N3 C20 C21 111.4(9) . . ? N3 C20 H20A 109.3 . . ? C21 C20 H20A 109.4 . . ? N3 C20 H20B 109.3 . . ? C21 C20 H20B 109.3 . . ? H20A C20 H20B 108 . . ? O7 C22 C23 111.2(10) . . ? O7 C22 H22A 109.4 . . ? C23 C22 H22A 109.4 . . ? O7 C22 H22B 109.4 . . ? C23 C22 H22B 109.4 . . ? H22A C22 H22B 108 . . ? O8 C25 C24 110.7(9) . . ? O8 C25 H25A 109.5 . . ? C24 C25 H25A 109.5 . . ? O8 C25 H25B 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 108.1 . . ? N4 C27 C26 113.5(10) . . ? N4 C27 H27A 108.9 . . ? C26 C27 H27A 108.9 . . ? N4 C27 H27B 108.9 . . ? C26 C27 H27B 108.9 . . ? H27A C27 H27B 107.7 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C16 C17 C18 125.6(10) . . ? C16 C17 H17 117.2 . . ? C18 C17 H17 117.2 . . ? O7 C21 C20 111.3(10) . . ? O7 C21 H21A 109.4 . . ? C20 C21 H21A 109.4 . . ? O7 C21 H21B 109.4 . . ? C20 C21 H21B 109.4 . . ? H21A C21 H21B 108 . . ? O8 C26 C27 110.4(10) . . ? O8 C26 H26A 109.6 . . ? C27 C26 H26A 109.6 . . ? O8 C26 H26B 109.6 . . ? C27 C26 H26B 109.6 . . ? H26A C26 H26B 108.1 . . ? C16 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? data_bzac _database_code_depnum_ccdc_archive 'CCDC 883440' #TrackingRef 'Cu(dkt)(morph)2X.cif' _audit_creation_date 2011-11-23T15:18:09-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; benzoylacetonatochlorobis(morpholine)copper(II) ; _chemical_formula_sum 'C18 H29 Cl Cu N2 O5' _chemical_formula_moiety 'C18 H27 Cl Cu N2 O4, H2 O' _chemical_formula_weight 452.42 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8963(2) _cell_length_b 11.7384(3) _cell_length_c 13.5638(3) _cell_angle_alpha 82.211(2) _cell_angle_beta 84.292(5) _cell_angle_gamma 73.527(3) _cell_volume 1041.07(5) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 275 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 52.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 474 _exptl_special_details ; ? ; _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.54 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.207 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.59872 _exptl_absorpt_correction_T_max 0.73194 _exptl_absorpt_process_details 'N.W. Alcock (1970). Cryst. Computing, p271' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 27 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_unetI/netI 0.0301 _diffrn_reflns_number 6784 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.99 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.974 _diffrn_measured_fraction_theta_max 0.974 _reflns_number_total 3563 _reflns_number_gt 2910 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0559P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3563 _refine_ls_number_parameters 261 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0847 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.293 _refine_diff_density_min -0.565 _refine_diff_density_rms 0.08 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.54850(4) 0.75479(3) 0.717116(19) 0.03361(12) Uani 1 1 d . . . Cl2 Cl 0.22318(10) 0.88915(7) 0.63698(5) 0.0541(2) Uani 1 1 d . . . O2 O 0.4220(3) 0.71905(14) 0.84828(11) 0.0383(4) Uani 1 1 d . . . N1 N 0.6158(3) 0.89155(18) 0.77004(14) 0.0347(4) Uani 1 1 d D . . O1 O 0.5313(3) 0.60826(15) 0.67328(12) 0.0414(4) Uani 1 1 d . . . N2 N 0.7615(3) 0.75906(18) 0.59833(14) 0.0370(5) Uani 1 1 d D . . O4 O 0.9768(3) 0.66158(16) 0.42232(12) 0.0506(5) Uani 1 1 d . . . O5 O 0.7784(4) 1.0289(3) 0.59627(19) 0.0695(7) Uani 1 1 d . . . O3 O 0.6918(3) 1.02454(19) 0.91784(14) 0.0605(5) Uani 1 1 d . . . C11 C 0.4511(4) 0.9706(2) 0.82863(19) 0.0444(6) Uani 1 1 d . . . H11A H 0.4087 0.9239 0.887 0.053 Uiso 1 1 calc R . . H11B H 0.3354 1.0049 0.7884 0.053 Uiso 1 1 calc R . . C2 C 0.4496(3) 0.5320(2) 0.72278(17) 0.0353(5) Uani 1 1 d . . . C17 C 0.8269(4) 0.7722(3) 0.41469(18) 0.0495(7) Uani 1 1 d . . . H17A H 0.7606 0.7825 0.353 0.059 Uiso 1 1 calc R . . H17B H 0.8903 0.8365 0.4127 0.059 Uiso 1 1 calc R . . C4 C 0.3502(3) 0.6301(2) 0.87672(16) 0.0330(5) Uani 1 1 d . . . C18 C 0.6715(4) 0.7792(3) 0.50117(18) 0.0474(7) Uani 1 1 d . . . H18A H 0.5742 0.8574 0.4949 0.057 Uiso 1 1 calc R . . H18B H 0.599 0.72 0.4989 0.057 Uiso 1 1 calc R . . C10 C 0.2200(4) 0.7229(2) 1.03314(19) 0.0466(6) Uani 1 1 d . . . H10 H 0.2505 0.7921 1.0024 0.056 Uiso 1 1 calc R . . C14 C 0.7966(4) 0.8508(2) 0.8281(2) 0.0469(6) Uani 1 1 d . . . H14A H 0.9088 0.8054 0.7879 0.056 Uiso 1 1 calc R . . H14B H 0.7708 0.798 0.8863 0.056 Uiso 1 1 calc R . . C5 C 0.2597(3) 0.6241(2) 0.98174(16) 0.0337(5) Uani 1 1 d . . . C15 C 0.9341(4) 0.6500(2) 0.60234(18) 0.0440(6) Uani 1 1 d . . . H15A H 0.8826 0.5804 0.6091 0.053 Uiso 1 1 calc R . . H15B H 1.0075 0.6456 0.6608 0.053 Uiso 1 1 calc R . . C3 C 0.3539(4) 0.5421(2) 0.81743(18) 0.0398(6) Uani 1 1 d . . . H3 H 0.2868 0.485 0.8432 0.048 Uiso 1 1 calc R . . C9 C 0.1351(5) 0.7198(3) 1.1300(2) 0.0583(8) Uani 1 1 d . . . H9 H 0.1072 0.7872 1.1636 0.07 Uiso 1 1 calc R . . C16 C 1.0777(4) 0.6476(3) 0.51074(19) 0.0547(7) Uani 1 1 d . . . H16A H 1.1427 0.7112 0.5085 0.066 Uiso 1 1 calc R . . H16B H 1.1824 0.5721 0.5149 0.066 Uiso 1 1 calc R . . C12 C 0.5216(5) 1.0698(3) 0.8608(2) 0.0569(8) Uani 1 1 d . . . H12A H 0.5551 1.1196 0.8023 0.068 Uiso 1 1 calc R . . H12B H 0.4123 1.1193 0.8998 0.068 Uiso 1 1 calc R . . C13 C 0.8547(5) 0.9531(3) 0.8612(2) 0.0600(8) Uani 1 1 d . . . H13A H 0.9712 0.9221 0.9012 0.072 Uiso 1 1 calc R . . H13B H 0.8925 1.0022 0.8031 0.072 Uiso 1 1 calc R . . C6 C 0.2165(4) 0.5216(2) 1.03053(18) 0.0394(6) Uani 1 1 d . . . H6 H 0.2433 0.4538 0.9975 0.047 Uiso 1 1 calc R . . C7 C 0.1337(4) 0.5190(2) 1.12788(18) 0.0431(6) Uani 1 1 d . . . H7 H 0.1067 0.4493 1.1598 0.052 Uiso 1 1 calc R . . C1 C 0.4622(4) 0.4235(3) 0.6727(2) 0.0514(7) Uani 1 1 d . . . H1A H 0.4806 0.4417 0.6018 0.077 Uiso 1 1 calc R . . H1B H 0.3392 0.4 0.6884 0.077 Uiso 1 1 calc R . . H1C H 0.5748 0.3593 0.6958 0.077 Uiso 1 1 calc R . . C8 C 0.0917(4) 0.6175(3) 1.17695(19) 0.0500(7) Uani 1 1 d . . . H8 H 0.034 0.6159 1.2419 0.06 Uiso 1 1 calc R . . H1N H 0.643(3) 0.9400(17) 0.7154(11) 0.037(7) Uiso 1 1 d D . . H2N H 0.811(4) 0.8224(14) 0.6014(19) 0.046(8) Uiso 1 1 d D . . H2W H 0.778(6) 1.051(4) 0.544(3) 0.084(14) Uiso 1 1 d . . . H1W H 0.894(5) 1.010(3) 0.608(2) 0.067(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.04474(19) 0.03465(18) 0.02415(16) -0.00829(11) 0.00531(12) -0.01549(13) Cl2 0.0497(4) 0.0650(5) 0.0400(4) -0.0064(3) -0.0063(3) -0.0020(3) O2 0.0603(11) 0.0350(9) 0.0244(8) -0.0077(7) 0.0073(7) -0.0223(8) N1 0.0470(12) 0.0354(11) 0.0247(10) -0.0084(8) 0.0079(8) -0.0176(9) O1 0.0599(11) 0.0383(10) 0.0315(9) -0.0104(7) 0.0079(8) -0.0226(8) N2 0.0485(12) 0.0357(12) 0.0289(10) -0.0118(9) 0.0067(9) -0.0140(10) O4 0.0664(12) 0.0492(11) 0.0340(9) -0.0188(8) 0.0099(8) -0.0102(9) O5 0.0493(14) 0.104(2) 0.0518(15) 0.0240(14) -0.0042(11) -0.0299(13) O3 0.0829(15) 0.0675(14) 0.0453(11) -0.0285(10) 0.0034(10) -0.0360(12) C11 0.0490(15) 0.0432(15) 0.0435(14) -0.0195(12) 0.0104(12) -0.0145(12) C2 0.0372(13) 0.0367(14) 0.0353(13) -0.0084(10) -0.0040(10) -0.0129(10) C17 0.0712(18) 0.0469(16) 0.0274(13) -0.0048(11) 0.0051(12) -0.0139(14) C4 0.0335(12) 0.0356(13) 0.0299(12) -0.0016(10) -0.0021(9) -0.0104(10) C18 0.0536(16) 0.0501(16) 0.0307(13) -0.0034(11) 0.0042(11) -0.0044(13) C10 0.0648(17) 0.0424(15) 0.0370(14) -0.0075(12) 0.0091(12) -0.0243(13) C14 0.0528(16) 0.0470(16) 0.0449(15) -0.0137(12) -0.0032(12) -0.0159(13) C5 0.0323(12) 0.0418(14) 0.0285(12) -0.0058(10) 0.0006(9) -0.0124(10) C15 0.0451(14) 0.0523(16) 0.0314(13) -0.0102(11) 0.0024(11) -0.0072(12) C3 0.0468(14) 0.0467(15) 0.0347(13) -0.0103(11) 0.0046(11) -0.0267(12) C9 0.079(2) 0.0599(19) 0.0410(16) -0.0218(14) 0.0145(14) -0.0261(16) C16 0.0483(16) 0.068(2) 0.0426(16) -0.0164(14) 0.0093(13) -0.0074(14) C12 0.077(2) 0.0442(16) 0.0531(17) -0.0233(13) 0.0119(15) -0.0204(15) C13 0.0605(19) 0.069(2) 0.0616(19) -0.0239(16) -0.0062(15) -0.0270(16) C6 0.0413(14) 0.0448(15) 0.0349(13) -0.0065(11) 0.0004(10) -0.0165(11) C7 0.0451(15) 0.0498(16) 0.0352(13) 0.0045(12) 0.0006(11) -0.0198(12) C1 0.0645(18) 0.0512(17) 0.0482(16) -0.0191(13) 0.0033(13) -0.0276(14) C8 0.0536(16) 0.068(2) 0.0292(13) -0.0062(13) 0.0089(11) -0.0222(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 1.9321(16) . ? Cu1 O2 1.9491(15) . ? Cu1 N1 2.027(2) . ? Cu1 N2 2.0751(19) . ? Cu1 Cl2 2.5916(7) . ? O2 C4 1.277(3) . ? N1 C14 1.470(3) . ? N1 C11 1.485(3) . ? N1 H1N 0.909(2) . ? O1 C2 1.272(3) . ? N2 C18 1.474(3) . ? N2 C15 1.479(3) . ? N2 H2N 0.909(2) . ? O4 C17 1.411(3) . ? O4 C16 1.413(3) . ? O5 H2W 0.72(4) . ? O5 H1W 0.79(3) . ? O3 C12 1.405(4) . ? O3 C13 1.423(4) . ? C11 C12 1.510(4) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C2 C3 1.388(3) . ? C2 C1 1.501(3) . ? C17 C18 1.502(3) . ? C17 H17A 0.97 . ? C17 H17B 0.97 . ? C4 C3 1.386(3) . ? C4 C5 1.498(3) . ? C18 H18A 0.97 . ? C18 H18B 0.97 . ? C10 C5 1.380(3) . ? C10 C9 1.384(4) . ? C10 H10 0.93 . ? C14 C13 1.503(4) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C5 C6 1.387(3) . ? C15 C16 1.508(3) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C3 H3 0.93 . ? C9 C8 1.376(4) . ? C9 H9 0.93 . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C6 C7 1.385(3) . ? C6 H6 0.93 . ? C7 C8 1.358(4) . ? C7 H7 0.93 . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? C8 H8 0.93 . ? 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 O1 Cu1 O2 92.18(7) . . ? O1 Cu1 N1 169.94(8) . . ? O2 Cu1 N1 88.37(7) . . ? O1 Cu1 N2 85.96(7) . . ? O2 Cu1 N2 162.30(8) . . ? N1 Cu1 N2 90.47(8) . . ? O1 Cu1 Cl2 95.58(6) . . ? O2 Cu1 Cl2 97.07(5) . . ? N1 Cu1 Cl2 94.32(6) . . ? N2 Cu1 Cl2 100.63(6) . . ? C4 O2 Cu1 126.46(15) . . ? C14 N1 C11 108.56(19) . . ? C14 N1 Cu1 112.30(15) . . ? C11 N1 Cu1 116.83(15) . . ? C14 N1 H1N 108.1(15) . . ? C11 N1 H1N 104.6(15) . . ? Cu1 N1 H1N 105.8(15) . . ? C2 O1 Cu1 126.25(15) . . ? C18 N2 C15 109.77(19) . . ? C18 N2 Cu1 112.26(15) . . ? C15 N2 Cu1 112.56(15) . . ? C18 N2 H2N 106.4(16) . . ? C15 N2 H2N 107.8(17) . . ? Cu1 N2 H2N 107.7(16) . . ? C17 O4 C16 109.6(2) . . ? H2W O5 H1W 105(4) . . ? C12 O3 C13 110.1(2) . . ? N1 C11 C12 110.9(2) . . ? N1 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? O1 C2 C3 125.1(2) . . ? O1 C2 C1 115.7(2) . . ? C3 C2 C1 119.2(2) . . ? O4 C17 C18 111.3(2) . . ? O4 C17 H17A 109.4 . . ? C18 C17 H17A 109.4 . . ? O4 C17 H17B 109.4 . . ? C18 C17 H17B 109.4 . . ? H17A C17 H17B 108 . . ? O2 C4 C3 124.2(2) . . ? O2 C4 C5 115.6(2) . . ? C3 C4 C5 120.2(2) . . ? N2 C18 C17 112.8(2) . . ? N2 C18 H18A 109 . . ? C17 C18 H18A 109 . . ? N2 C18 H18B 109 . . ? C17 C18 H18B 109 . . ? H18A C18 H18B 107.8 . . ? C5 C10 C9 120.5(2) . . ? C5 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? N1 C14 C13 112.2(2) . . ? N1 C14 H14A 109.2 . . ? C13 C14 H14A 109.2 . . ? N1 C14 H14B 109.2 . . ? C13 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C10 C5 C6 118.2(2) . . ? C10 C5 C4 119.5(2) . . ? C6 C5 C4 122.3(2) . . ? N2 C15 C16 112.5(2) . . ? N2 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? N2 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? C4 C3 C2 125.4(2) . . ? C4 C3 H3 117.3 . . ? C2 C3 H3 117.3 . . ? C8 C9 C10 120.4(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? O4 C16 C15 111.8(2) . . ? O4 C16 H16A 109.2 . . ? C15 C16 H16A 109.2 . . ? O4 C16 H16B 109.2 . . ? C15 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? O3 C12 C11 111.7(2) . . ? O3 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? O3 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 108 . . ? O3 C13 C14 111.1(2) . . ? O3 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? O3 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108 . . ? C7 C6 C5 120.8(2) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C8 C7 C6 120.4(2) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C8 C9 119.6(2) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? data_bzac_NO3 _database_code_depnum_ccdc_archive 'CCDC 883441' #TrackingRef 'Cu(dkt)(morph)2X.cif' _audit_creation_date 2011-11-23T15:52:43-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; benzoylacetonatonitratobis(morpholine)copper(II) ; _chemical_formula_sum 'C18 H27 Cu N3 O7' _chemical_formula_moiety 'C18 H27 Cu N3 O7' _chemical_formula_weight 460.97 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn ' 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 13.5493(6) _cell_length_b 11.3606(4) _cell_length_c 13.7432(6) _cell_angle_alpha 90 _cell_angle_beta 92.171(4) _cell_angle_gamma 90 _cell_volume 2113.95(15) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 126 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 52.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_special_details ; ? ; _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.077 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 27 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_unetI/netI 0.062 _diffrn_reflns_number 7690 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.14 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 3670 _reflns_number_gt 2268 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0370P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3670 _refine_ls_number_parameters 271 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0657 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0789 _refine_ls_wR_factor_gt 0.0761 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.933 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.288 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.041 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 0.61614(3) 0.33086(3) 0.81105(3) 0.04798(14) Uani 1 1 d . . . O2 O 0.63433(16) 0.43174(15) 0.92235(14) 0.0557(6) Uani 1 1 d . . . N2 N 0.58132(18) 0.21604(19) 0.70126(17) 0.0457(6) Uani 1 1 d D . . O5 O 0.78092(16) 0.33067(17) 0.74212(17) 0.0740(7) Uani 1 1 d . . . O1 O 0.54760(15) 0.45140(16) 0.73677(15) 0.0580(6) Uani 1 1 d . . . N1 N 0.65794(19) 0.19606(18) 0.90189(18) 0.0468(6) Uani 1 1 d D . . C12 C 0.7847(3) 0.1044(3) 1.0098(3) 0.0787(11) Uani 1 1 d . . . H12A H 0.7839 0.0319 0.9725 0.094 Uiso 1 1 calc R . . H12B H 0.851 0.1154 1.0374 0.094 Uiso 1 1 calc R . . C11 C 0.7590(2) 0.2063(3) 0.9424(2) 0.0674(10) Uani 1 1 d . . . H11A H 0.7659 0.2797 0.9781 0.081 Uiso 1 1 calc R . . H11B H 0.8047 0.2079 0.8898 0.081 Uiso 1 1 calc R . . N3 N 0.8201(2) 0.4263(2) 0.72781(19) 0.0559(7) Uani 1 1 d U . . O7 O 0.89735(18) 0.4342(2) 0.6836(2) 0.0884(8) Uani 1 1 d U . . C14 C 0.5904(2) 0.1797(2) 0.9811(2) 0.0582(8) Uani 1 1 d . . . H14A H 0.5246 0.164 0.9539 0.07 Uiso 1 1 calc R . . H14B H 0.5876 0.2518 1.0187 0.07 Uiso 1 1 calc R . . C18 C 0.4777(2) 0.1788(3) 0.7030(2) 0.0721(10) Uani 1 1 d . . . H18A H 0.4354 0.2476 0.6975 0.086 Uiso 1 1 calc R . . H18B H 0.466 0.1412 0.7648 0.086 Uiso 1 1 calc R . . O4 O 0.7190(2) 0.0945(2) 1.08487(17) 0.0814(7) Uani 1 1 d . . . O3 O 0.47230(19) 0.1404(2) 0.52986(18) 0.0805(7) Uani 1 1 d . . . C5 C 0.6546(2) 0.6014(2) 1.0172(2) 0.0430(7) Uani 1 1 d . . . O6 O 0.78109(18) 0.5165(2) 0.7551(2) 0.0910(8) Uani 1 1 d . . . C16 C 0.5729(3) 0.1653(3) 0.5269(2) 0.0688(9) Uani 1 1 d . . . H16A H 0.5879 0.1944 0.4628 0.083 Uiso 1 1 calc R . . H16B H 0.6106 0.0938 0.5388 0.083 Uiso 1 1 calc R . . C6 C 0.6758(2) 0.5340(3) 1.0992(2) 0.0573(9) Uani 1 1 d . . . H6 H 0.6644 0.4533 1.0971 0.069 Uiso 1 1 calc R . . C4 C 0.6187(2) 0.5430(2) 0.9249(2) 0.0460(7) Uani 1 1 d U . . C1 C 0.4857(3) 0.6365(3) 0.6900(3) 0.0747(10) Uani 1 1 d . . . H1A H 0.5155 0.6294 0.628 0.112 Uiso 1 1 calc R . . H1B H 0.4902 0.7167 0.7118 0.112 Uiso 1 1 calc R . . H1C H 0.4175 0.6138 0.6837 0.112 Uiso 1 1 calc R . . C15 C 0.6022(3) 0.2563(3) 0.6026(2) 0.0688(10) Uani 1 1 d . . . H15A H 0.6721 0.273 0.599 0.083 Uiso 1 1 calc R . . H15B H 0.5663 0.3287 0.589 0.083 Uiso 1 1 calc R . . C3 C 0.5721(2) 0.6050(2) 0.8509(2) 0.0510(8) Uani 1 1 d U . . H3 H 0.5622 0.685 0.8607 0.061 Uiso 1 1 calc R . . C2 C 0.5388(2) 0.5577(3) 0.7629(2) 0.0516(8) Uani 1 1 d . . . C13 C 0.6213(3) 0.0801(3) 1.0476(3) 0.0751(10) Uani 1 1 d . . . H13A H 0.5769 0.0761 1.1012 0.09 Uiso 1 1 calc R . . H13B H 0.6163 0.0065 1.012 0.09 Uiso 1 1 calc R . . C17 C 0.4507(3) 0.0942(3) 0.6212(3) 0.0883(12) Uani 1 1 d . . . H17A H 0.4867 0.0212 0.6314 0.106 Uiso 1 1 calc R . . H17B H 0.3807 0.0765 0.6223 0.106 Uiso 1 1 calc R . . C10 C 0.6719(2) 0.7214(2) 1.0231(2) 0.0534(8) Uani 1 1 d . . . H10 H 0.6575 0.7689 0.9693 0.064 Uiso 1 1 calc R . . C9 C 0.7102(2) 0.7709(3) 1.1080(2) 0.0603(9) Uani 1 1 d . . . H9 H 0.7217 0.8516 1.1109 0.072 Uiso 1 1 calc R . . C7 C 0.7133(2) 0.5842(3) 1.1838(2) 0.0615(9) Uani 1 1 d . . . H7 H 0.7264 0.5377 1.2385 0.074 Uiso 1 1 calc R . . C8 C 0.7313(2) 0.7027(3) 1.1875(3) 0.0617(9) Uani 1 1 d . . . H8 H 0.7578 0.7366 1.2442 0.074 Uiso 1 1 calc R . . H1N H 0.656(2) 0.1251(12) 0.8713(18) 0.062(9) Uiso 1 1 d D . . H2N H 0.6185(16) 0.1514(13) 0.716(2) 0.054(9) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0610(3) 0.03815(19) 0.0444(2) -0.00152(19) -0.00233(17) 0.00410(19) O2 0.0838(16) 0.0346(10) 0.0485(13) -0.0014(9) -0.0024(11) 0.0083(10) N2 0.0505(17) 0.0427(13) 0.0436(16) -0.0006(12) -0.0029(13) 0.0046(13) O5 0.0852(17) 0.0459(12) 0.0915(18) 0.0059(12) 0.0105(14) -0.0224(12) O1 0.0713(15) 0.0459(11) 0.0556(14) -0.0045(10) -0.0128(11) 0.0096(10) N1 0.0568(17) 0.0390(14) 0.0441(15) -0.0035(12) -0.0041(13) 0.0045(12) C12 0.071(3) 0.080(2) 0.083(3) 0.016(2) -0.021(2) 0.005(2) C11 0.061(2) 0.072(2) 0.069(2) 0.0169(19) -0.0036(19) 0.0055(18) N3 0.0637(18) 0.0510(15) 0.0529(17) 0.0067(14) 0.0022(13) -0.0127(16) O7 0.0822(18) 0.0770(15) 0.108(2) 0.0093(15) 0.0354(15) -0.0144(14) C14 0.060(2) 0.0543(18) 0.061(2) 0.0070(17) 0.0043(17) -0.0056(17) C18 0.061(2) 0.087(2) 0.069(2) -0.014(2) 0.0124(18) -0.011(2) O4 0.110(2) 0.0820(16) 0.0511(16) 0.0137(13) -0.0162(16) -0.0059(16) O3 0.0745(19) 0.1042(18) 0.0614(17) -0.0172(14) -0.0170(14) 0.0024(15) C5 0.0421(18) 0.0409(16) 0.0461(19) -0.0042(15) 0.0048(15) 0.0031(14) O6 0.0880(19) 0.0544(14) 0.132(2) -0.0039(15) 0.0299(17) -0.0017(14) C16 0.080(3) 0.082(2) 0.044(2) -0.0056(19) -0.0015(18) -0.005(2) C6 0.074(2) 0.0470(16) 0.051(2) -0.0040(17) 0.0049(18) -0.0049(16) C4 0.0460(19) 0.0422(16) 0.0501(18) -0.0007(13) 0.0077(14) 0.0047(13) C1 0.081(3) 0.070(2) 0.071(2) 0.0051(19) -0.017(2) 0.0217(19) C15 0.083(3) 0.074(2) 0.050(2) -0.0035(19) 0.0075(19) -0.0130(19) C3 0.055(2) 0.0407(15) 0.057(2) -0.0030(14) -0.0025(15) 0.0075(14) C2 0.0476(19) 0.0491(18) 0.058(2) 0.0015(17) 0.0012(16) 0.0053(15) C13 0.090(3) 0.069(2) 0.067(2) 0.015(2) 0.008(2) -0.007(2) C17 0.071(3) 0.107(3) 0.087(3) -0.035(3) 0.008(2) -0.037(2) C10 0.059(2) 0.0452(16) 0.056(2) -0.0015(17) -0.0002(17) 0.0046(16) C9 0.068(2) 0.0478(17) 0.065(2) -0.0075(19) 0.0027(19) -0.0042(17) C7 0.078(2) 0.065(2) 0.042(2) -0.0011(17) 0.0006(17) 0.0000(18) C8 0.064(2) 0.066(2) 0.055(2) -0.0153(18) 0.0028(18) -0.0043(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O2 1.9198(18) . ? Cu1 O1 1.9256(19) . ? Cu1 N2 2.036(2) . ? Cu1 N1 2.042(2) . ? Cu1 O5 2.458(2) . ? O2 C4 1.283(3) . ? N2 C18 1.468(4) . ? N2 C15 1.468(4) . ? N2 H2N 0.909(2) . ? O5 N3 1.229(3) . ? O1 C2 1.267(3) . ? N1 C14 1.461(4) . ? N1 C11 1.463(4) . ? N1 H1N 0.909(2) . ? C12 O4 1.393(4) . ? C12 C11 1.515(4) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? N3 O6 1.219(3) . ? N3 O7 1.233(3) . ? C14 C13 1.503(4) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C18 C17 1.513(4) . ? C18 H18A 0.97 . ? C18 H18B 0.97 . ? O4 C13 1.411(4) . ? O3 C16 1.394(4) . ? O3 C17 1.402(4) . ? C5 C6 1.383(4) . ? C5 C10 1.385(4) . ? C5 C4 1.497(4) . ? C16 C15 1.509(4) . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? C6 C7 1.375(4) . ? C6 H6 0.93 . ? C4 C3 1.370(4) . ? C1 C2 1.506(4) . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C3 C2 1.384(4) . ? C3 H3 0.93 . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C17 H17A 0.97 . ? C17 H17B 0.97 . ? C10 C9 1.379(4) . ? C10 H10 0.93 . ? C9 C8 1.361(4) . ? C9 H9 0.93 . ? C7 C8 1.369(4) . ? C7 H7 0.93 . ? C8 H8 0.93 . ? 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 O2 Cu1 O1 92.44(8) . . ? O2 Cu1 N2 172.72(10) . . ? O1 Cu1 N2 88.24(9) . . ? O2 Cu1 N1 86.35(9) . . ? O1 Cu1 N1 166.99(10) . . ? N2 Cu1 N1 91.36(9) . . ? O2 Cu1 O5 102.50(8) . . ? O1 Cu1 O5 102.90(8) . . ? N2 Cu1 O5 84.39(9) . . ? N1 Cu1 O5 90.00(9) . . ? C4 O2 Cu1 126.44(19) . . ? C18 N2 C15 108.8(2) . . ? C18 N2 Cu1 111.58(19) . . ? C15 N2 Cu1 115.93(18) . . ? C18 N2 H2N 106.7(17) . . ? C15 N2 H2N 109.4(18) . . ? Cu1 N2 H2N 104.0(17) . . ? N3 O5 Cu1 117.73(19) . . ? C2 O1 Cu1 125.2(2) . . ? C14 N1 C11 109.3(2) . . ? C14 N1 Cu1 112.59(18) . . ? C11 N1 Cu1 114.01(18) . . ? C14 N1 H1N 103.0(18) . . ? C11 N1 H1N 104.8(18) . . ? Cu1 N1 H1N 112.4(18) . . ? O4 C12 C11 112.1(3) . . ? O4 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? O4 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? N1 C11 C12 111.2(3) . . ? N1 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? N1 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108 . . ? O6 N3 O5 119.9(3) . . ? O6 N3 O7 118.5(3) . . ? O5 N3 O7 121.5(3) . . ? N1 C14 C13 112.4(3) . . ? N1 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? N1 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? N2 C18 C17 112.1(3) . . ? N2 C18 H18A 109.2 . . ? C17 C18 H18A 109.2 . . ? N2 C18 H18B 109.2 . . ? C17 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C12 O4 C13 110.9(3) . . ? C16 O3 C17 109.9(3) . . ? C6 C5 C10 117.9(3) . . ? C6 C5 C4 119.7(2) . . ? C10 C5 C4 122.3(3) . . ? O3 C16 C15 110.5(3) . . ? O3 C16 H16A 109.6 . . ? C15 C16 H16A 109.6 . . ? O3 C16 H16B 109.6 . . ? C15 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C7 C6 C5 121.2(3) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? O2 C4 C3 123.9(3) . . ? O2 C4 C5 114.3(2) . . ? C3 C4 C5 121.8(2) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 C15 C16 111.6(2) . . ? N2 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? N2 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 108 . . ? C4 C3 C2 125.1(3) . . ? C4 C3 H3 117.4 . . ? C2 C3 H3 117.4 . . ? O1 C2 C3 125.9(3) . . ? O1 C2 C1 115.2(3) . . ? C3 C2 C1 118.9(3) . . ? O4 C13 C14 111.7(3) . . ? O4 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? O4 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 107.9 . . ? O3 C17 C18 112.0(3) . . ? O3 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? O3 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C9 C10 C5 120.5(3) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.7 . . ? C8 C9 C10 120.5(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C8 C7 C6 119.9(3) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 119.9(3) . . ? C9 C8 H8 120 . . ? C7 C8 H8 120 . . ? data_dbm_Cl _database_code_depnum_ccdc_archive 'CCDC 883442' #TrackingRef 'Cu(dkt)(morph)2X.cif' _audit_creation_date 2011-11-24T16:01:51-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (1,3-diphenyl-1,3-propanedionato)aquabis(morpholine)copper(II) chloride - morpholinium chloride ; _chemical_formula_sum 'C27 H41 Cl2 Cu N3 O6' _chemical_formula_moiety 'C23 H31 Cu N2 O5, C4 H10 N O, 2Cl' _chemical_formula_weight 638.07 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C m' _symmetry_space_group_name_Hall 'C -2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z' _cell_length_a 11.1998(10) _cell_length_b 17.0668(10) _cell_length_c 8.4726(6) _cell_angle_alpha 90 _cell_angle_beta 102.461(8) _cell_angle_gamma 90 _cell_volume 1581.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 174 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 52.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.34 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 670 _exptl_special_details ; ? ; _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.11 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.901 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 27 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_unetI/netI 0.0577 _diffrn_reflns_number 3713 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_theta_max 26.99 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _reflns_number_total 2644 _reflns_number_gt 2060 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0809P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2644 _refine_ls_number_parameters 193 _refine_ls_number_restraints 37 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.133 _refine_ls_wR_factor_gt 0.13 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(2) _refine_diff_density_max 0.867 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.078 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O4 O 0.8702(7) 0.5 0.3932(10) 0.47(2) Uani 1 2 d SDU . . C14 C 0.9277(5) 0.571600(12) 0.3661(5) 0.47(3) Uani 1 1 d DU . . H14A H 0.9953 0.582 0.4566 0.567 Uiso 1 1 calc R . . H14B H 0.8696 0.6142 0.3593 0.567 Uiso 1 1 calc R . . C13 C 0.9746(4) 0.568262(12) 0.2123(3) 0.51(2) Uani 1 1 d DU . . H13A H 0.9058 0.5672 0.1205 0.61 Uiso 1 1 calc R . . H13B H 1.0218 0.6152 0.2039 0.61 Uiso 1 1 calc R . . N2 N 1.0504(5) 0.5 0.2070(9) 0.43(2) Uani 1 2 d SDU . . H2A H 1.079 0.5 0.1155 0.52 Uiso 1 2 calc SR . . H2B H 1.1145 0.5 0.2919 0.52 Uiso 1 2 calc SR . . Cl2 Cl 1.0840(18) 0.5 -0.087(2) 0.1053(11) Uani 1 2 d S . . Cu1 Cu 0.5242(18) 0.5 1.107(2) 0.0391(3) Uani 1 2 d SD . . Cl1 Cl 0.3370(18) 0.5 0.512(2) 0.0941(11) Uani 1 2 d S . . O1 O 0.6059(19) 0.5816(2) 1.010(2) 0.0513(12) Uani 1 1 d . . . N1 N 0.4688(18) 0.4153(2) 1.246(2) 0.0349(11) Uani 1 1 d . . . H1N H 0.4289 0.439 1.3156 0.042 Uiso 1 1 calc R . . C8 C 0.7086(19) 0.5 0.853(3) 0.0454(18) Uani 1 2 d S . . H8 H 0.7577 0.5 0.777 0.054 Uiso 1 2 calc SR . . O3 O 0.4573(19) 0.2553(2) 1.345(2) 0.0739(15) Uani 1 1 d . . . C1 C 0.7178(18) 0.6471(3) 0.846(2) 0.0373(11) Uani 1 1 d . . . C7 C 0.6732(18) 0.5729(3) 0.907(2) 0.0341(11) Uani 1 1 d . . . C3 C 0.6952(19) 0.7869(3) 0.813(2) 0.0504(14) Uani 1 1 d . . . H3 H 0.6559 0.8333 0.8287 0.06 Uiso 1 1 calc R . . C4 C 0.7930(19) 0.7887(3) 0.734(2) 0.0534(15) Uani 1 1 d . . . H4 H 0.8181 0.8357 0.6966 0.064 Uiso 1 1 calc R . . C6 C 0.8172(19) 0.6505(3) 0.769(2) 0.0501(14) Uani 1 1 d . . . H6 H 0.859 0.6046 0.7563 0.06 Uiso 1 1 calc R . . C11 C 0.3538(19) 0.2934(4) 1.262(3) 0.072(2) Uani 1 1 d . . . H11A H 0.3113 0.3166 1.339 0.086 Uiso 1 1 calc R . . H11B H 0.2993 0.2559 1.1973 0.086 Uiso 1 1 calc R . . C12 C 0.3868(19) 0.3578(3) 1.152(2) 0.0528(15) Uani 1 1 d . . . H12A H 0.4259 0.3343 1.072 0.063 Uiso 1 1 calc R . . H12B H 0.3128 0.3837 1.0956 0.063 Uiso 1 1 calc R . . O2 O 0.3565(19) 0.5 0.895(2) 0.0607(16) Uani 1 2 d SD . . C5 C 0.8529(19) 0.7180(3) 0.714(3) 0.0553(15) Uani 1 1 d . . . H5 H 0.9178 0.7184 0.6616 0.066 Uiso 1 1 calc R . . C2 C 0.6561(19) 0.7168(3) 0.866(2) 0.0415(13) Uani 1 1 d . . . H2 H 0.5893 0.7158 0.9149 0.05 Uiso 1 1 calc R . . C9 C 0.5788(19) 0.3742(3) 1.342(2) 0.0530(15) Uani 1 1 d . . . H9A H 0.6294 0.4111 1.4145 0.064 Uiso 1 1 calc R . . H9B H 0.6271 0.3524 1.2707 0.064 Uiso 1 1 calc R . . C10 C 0.5365(19) 0.3084(4) 1.441(2) 0.0689(19) Uani 1 1 d . . . H10A H 0.6075 0.2804 1.4997 0.083 Uiso 1 1 calc R . . H10B H 0.4953 0.3314 1.5193 0.083 Uiso 1 1 calc R . . H1W H 0.283(4) 0.5 0.919(8) 0.07(3) Uiso 1 2 d SD . . H2W H 0.342(5) 0.5 0.787(3) 0.030(17) Uiso 1 2 d SD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O4 0.47(3) 0.46(3) 0.47(3) 0 0.096(11) 0 C14 0.48(3) 0.46(3) 0.48(3) 0.004(10) 0.113(12) 0.011(10) C13 0.51(2) 0.51(2) 0.51(2) 0.0001(10) 0.110(5) 0.0000(10) N2 0.43(2) 0.43(2) 0.43(2) 0 0.093(5) 0 Cl2 0.076(2) 0.0801(19) 0.166(3) 0 0.0401(19) 0 Cu1 0.0534(6) 0.0304(4) 0.0418(4) 0 0.0286(4) 0 Cl1 0.155(3) 0.0744(15) 0.0779(15) 0 0.0809(19) 0 O1 0.083(3) 0.0320(19) 0.051(2) -0.0010(16) 0.041(2) -0.005(2) N1 0.048(3) 0.032(2) 0.028(2) 0.0008(16) 0.016(2) -0.001(2) C8 0.052(5) 0.044(4) 0.048(4) 0 0.029(4) 0 O3 0.117(5) 0.034(2) 0.069(3) 0.0116(19) 0.016(3) 0.000(3) C1 0.039(3) 0.039(3) 0.035(2) 0.0024(19) 0.010(2) -0.002(2) C7 0.037(3) 0.033(2) 0.032(2) -0.0003(17) 0.007(2) -0.004(2) C3 0.061(4) 0.041(3) 0.051(3) -0.005(2) 0.016(3) -0.004(3) C4 0.058(4) 0.045(3) 0.055(3) 0.004(2) 0.008(3) -0.022(3) C6 0.047(4) 0.046(3) 0.063(3) 0.008(2) 0.025(3) 0.005(3) C11 0.088(6) 0.060(4) 0.066(4) 0.006(3) 0.011(4) -0.031(4) C12 0.064(4) 0.040(3) 0.051(3) 0.009(2) 0.005(3) -0.012(3) O2 0.061(4) 0.081(4) 0.041(3) 0 0.012(3) 0 C5 0.051(4) 0.052(3) 0.071(4) 0.003(3) 0.030(3) -0.013(3) C2 0.055(4) 0.029(2) 0.042(3) 0.000(2) 0.013(3) -0.001(3) C9 0.050(4) 0.057(3) 0.051(3) 0.012(3) 0.010(3) 0.000(3) C10 0.080(5) 0.065(4) 0.057(3) 0.025(3) 0.004(3) -0.001(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O4 C14 1.4230(2) . ? O4 C14 1.4230(2) 2_565 ? C14 C13 1.507(2) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C13 N2 1.4480(2) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? N2 C13 1.4480(2) 2_565 ? N2 H2A 0.9 . ? N2 H2B 0.9 . ? Cu1 O1 1.943(4) . ? Cu1 O1 1.943(4) 2_565 ? Cu1 N1 2.044(4) 2_565 ? Cu1 N1 2.044(4) . ? Cu1 O2 2.301(6) . ? O1 C7 1.28(3) . ? N1 C12 1.46(2) . ? N1 C9 1.50(2) . ? N1 H1N 0.91 . ? C8 C7 1.412(15) . ? C8 C7 1.412(15) 2_565 ? C8 H8 0.93 . ? O3 C11 1.38(3) . ? O3 C10 1.40(2) . ? C1 C2 1.404(17) . ? C1 C6 1.41(3) . ? C1 C7 1.494(16) . ? C3 C2 1.382(15) . ? C3 C4 1.40(3) . ? C3 H3 0.93 . ? C4 C5 1.409(9) . ? C4 H4 0.93 . ? C6 C5 1.336(17) . ? C6 H6 0.93 . ? C11 C12 1.54(2) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? O2 H1W 0.89(2) . ? O2 H2W 0.891(18) . ? C5 H5 0.93 . ? C2 H2 0.93 . ? C9 C10 1.536(19) . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O4 C14 118.35(4) . 2_565 ? O4 C14 C13 111.2(4) . . ? O4 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? O4 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108 . . ? N2 C13 C14 111.9(3) . . ? N2 C13 H13A 109.2 . . ? C14 C13 H13A 109.2 . . ? N2 C13 H13B 109.2 . . ? C14 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C13 N2 C13 107.14(4) 2_565 . ? C13 N2 H2A 110.3 2_565 . ? C13 N2 H2A 110.3 . . ? C13 N2 H2B 110.3 2_565 . ? C13 N2 H2B 110.3 . . ? H2A N2 H2B 108.5 . . ? O1 Cu1 O1 91.6(2) . 2_565 ? O1 Cu1 N1 88.03(14) . 2_565 ? O1 Cu1 N1 168.5(13) 2_565 2_565 ? O1 Cu1 N1 168.5(13) . . ? O1 Cu1 N1 88.03(14) 2_565 . ? N1 Cu1 N1 90.0(3) 2_565 . ? O1 Cu1 O2 92.8(9) . . ? O1 Cu1 O2 92.8(9) 2_565 . ? N1 Cu1 O2 98.7(9) 2_565 . ? N1 Cu1 O2 98.7(9) . . ? C7 O1 Cu1 127.2(3) . . ? C12 N1 C9 109.2(4) . . ? C12 N1 Cu1 113.3(12) . . ? C9 N1 Cu1 109.2(14) . . ? C12 N1 H1N 108.3 . . ? C9 N1 H1N 108.3 . . ? Cu1 N1 H1N 108.3 . . ? C7 C8 C7 123.4(7) . 2_565 ? C7 C8 H8 118.3 . . ? C7 C8 H8 118.3 2_565 . ? C11 O3 C10 110.3(5) . . ? C2 C1 C6 118.7(5) . . ? C2 C1 C7 117.8(17) . . ? C6 C1 C7 123.5(11) . . ? O1 C7 C8 124.9(12) . . ? O1 C7 C1 115.3(9) . . ? C8 C7 C1 119.8(17) . . ? C2 C3 C4 120.6(12) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 118.7(11) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C5 C6 C1 121.6(13) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? O3 C11 C12 111.1(17) . . ? O3 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? O3 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108 . . ? N1 C12 C11 110.8(14) . . ? N1 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108 . . ? Cu1 O2 H1W 118(4) . . ? Cu1 O2 H2W 137(3) . . ? H1W O2 H2W 105(4) . . ? C6 C5 C4 121(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C3 C2 C1 119.7(18) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? N1 C9 C10 109.0(16) . . ? N1 C9 H9A 109.9 . . ? C10 C9 H9A 109.9 . . ? N1 C9 H9B 109.9 . . ? C10 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? O3 C10 C9 112.8(14) . . ? O3 C10 H10A 109 . . ? C9 C10 H10A 109 . . ? O3 C10 H10B 109 . . ? C9 C10 H10B 109 . . ? H10A C10 H10B 107.8 . . ? data_dpm _database_code_depnum_ccdc_archive 'CCDC 883443' #TrackingRef 'Cu(dkt)(morph)2X.cif' _audit_creation_date 2011-11-23T17:53:47-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (2,2,6,6-tetramethyl-3,5-heptanedionato)chloroobis(morpholine)copper(II) monohydrate ; _chemical_formula_sum 'C19 H39 Cl Cu N2 O5' _chemical_formula_moiety 'C19 H37 Cl Cu N2 O4, H2 O' _chemical_formula_weight 474.51 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0852(3) _cell_length_b 9.7689(2) _cell_length_c 20.8357(4) _cell_angle_alpha 90 _cell_angle_beta 91.745(2) _cell_angle_gamma 90 _cell_volume 2458.70(9) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 324 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 52.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1012 _exptl_special_details ; ? ; _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.025 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 27 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_unetI/netI 0.0461 _diffrn_reflns_number 11059 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 27 _diffrn_reflns_theta_full 27 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _reflns_number_total 5280 _reflns_number_gt 3768 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0804P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5280 _refine_ls_number_parameters 275 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.91 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.075 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O5 O 0.1685(4) 0.0795(5) 0.2278(3) 0.0975(12) Uani 1 1 d D . . C10 C 0.3732(9) 0.9503(7) 0.0737(3) 0.171(4) Uani 1 1 d U . . H10A H 0.3774 0.9785 0.0297 0.256 Uiso 1 1 calc R . . H10B H 0.446 0.9508 0.0934 0.256 Uiso 1 1 calc R . . H10C H 0.3264 1.0122 0.0962 0.256 Uiso 1 1 calc R . . C9 C 0.4121(9) 0.7235(10) 0.0456(4) 0.198(4) Uani 1 1 d U . . H9A H 0.4006 0.6302 0.0583 0.296 Uiso 1 1 calc R . . H9B H 0.4851 0.752 0.0592 0.296 Uiso 1 1 calc R . . H9C H 0.4042 0.7307 -0.0002 0.296 Uiso 1 1 calc R . . H1N H 0.081(3) 0.369(3) 0.1846(16) 0.055(11) Uiso 1 1 d D . . H2N H 0.122(3) 0.382(3) 0.2877(17) 0.053(11) Uiso 1 1 d D . . H1W H 0.148(6) 0.002(4) 0.220(3) 0.13(3) Uiso 1 1 d D . . H2W H 0.103(3) 0.098(8) 0.232(4) 0.15(3) Uiso 1 1 d D . . Cu1 Cu 0.19965(3) 0.56389(4) 0.222315(16) 0.03150(14) Uani 1 1 d . . . Cl2 Cl 0.04799(8) 0.75663(9) 0.23948(4) 0.0487(2) Uani 1 1 d . . . O1 O 0.30586(18) 0.6635(2) 0.27551(10) 0.0358(5) Uani 1 1 d . . . N1 N 0.1128(2) 0.4353(3) 0.16173(12) 0.0351(6) Uani 1 1 d D . . N2 N 0.1710(2) 0.4444(3) 0.30057(12) 0.0349(6) Uani 1 1 d D . . O2 O 0.2554(2) 0.6482(2) 0.14595(10) 0.0395(5) Uani 1 1 d . . . C5 C 0.3563(3) 0.7725(3) 0.25945(15) 0.0336(7) Uani 1 1 d . . . C7 C 0.3128(3) 0.7576(3) 0.14390(15) 0.0368(7) Uani 1 1 d . . . O3 O 0.0473(3) 0.3371(3) 0.03600(12) 0.0623(8) Uani 1 1 d . . . C6 C 0.3602(3) 0.8201(3) 0.19708(15) 0.0416(8) Uani 1 1 d . . . H6 H 0.3981 0.9014 0.1905 0.05 Uiso 1 1 calc R . . O4 O 0.2155(3) 0.3599(3) 0.43095(12) 0.0686(8) Uani 1 1 d . . . C4 C 0.4136(3) 0.8481(3) 0.31588(16) 0.0414(8) Uani 1 1 d . . . C15 C 0.0280(3) 0.5045(4) 0.12070(16) 0.0452(8) Uani 1 1 d . . . H15A H 0.0628 0.5758 0.0959 0.054 Uiso 1 1 calc R . . H15B H -0.0263 0.5473 0.1476 0.054 Uiso 1 1 calc R . . C12 C 0.1875(3) 0.3547(3) 0.12154(17) 0.0446(8) Uani 1 1 d . . . H12A H 0.2353 0.2985 0.149 0.054 Uiso 1 1 calc R . . H12B H 0.234 0.4165 0.0978 0.054 Uiso 1 1 calc R . . C18 C 0.1167(4) 0.4277(4) 0.41383(18) 0.0632(12) Uani 1 1 d . . . H18A H 0.0927 0.4814 0.45 0.076 Uiso 1 1 calc R . . H18B H 0.0597 0.3605 0.4037 0.076 Uiso 1 1 calc R . . C14 C -0.0293(3) 0.4047(4) 0.07571(19) 0.0583(10) Uani 1 1 d . . . H14A H -0.0684 0.3371 0.1005 0.07 Uiso 1 1 calc R . . H14B H -0.0833 0.4532 0.0489 0.07 Uiso 1 1 calc R . . C13 C 0.1231(4) 0.2633(4) 0.07454(18) 0.0561(10) Uani 1 1 d . . . H13A H 0.1746 0.2165 0.0473 0.067 Uiso 1 1 calc R . . H13B H 0.0836 0.1944 0.0984 0.067 Uiso 1 1 calc R . . C16 C 0.2687(3) 0.3624(4) 0.31993(18) 0.0508(9) Uani 1 1 d . . . H16A H 0.3313 0.4229 0.3279 0.061 Uiso 1 1 calc R . . H16B H 0.287 0.3013 0.2852 0.061 Uiso 1 1 calc R . . C19 C 0.1308(3) 0.5206(4) 0.35664(16) 0.0499(9) Uani 1 1 d . . . H19A H 0.0604 0.5632 0.3453 0.06 Uiso 1 1 calc R . . H19B H 0.1831 0.5925 0.368 0.06 Uiso 1 1 calc R . . C8 C 0.3278(4) 0.8137(4) 0.07636(17) 0.0574(10) Uani 1 1 d U . . C2 C 0.3228(4) 0.8926(4) 0.36096(19) 0.0638(11) Uani 1 1 d . . . H2A H 0.285 0.8132 0.3764 0.096 Uiso 1 1 calc R . . H2B H 0.271 0.9507 0.3381 0.096 Uiso 1 1 calc R . . H2C H 0.3553 0.9418 0.3967 0.096 Uiso 1 1 calc R . . C17 C 0.2487(4) 0.2792(4) 0.3797(2) 0.0685(12) Uani 1 1 d . . . H17A H 0.1921 0.2112 0.3701 0.082 Uiso 1 1 calc R . . H17B H 0.3163 0.2312 0.3923 0.082 Uiso 1 1 calc R . . C3 C 0.4754(5) 0.9753(5) 0.2968(2) 0.0872(18) Uani 1 1 d . . . H3A H 0.5105 1.0156 0.3342 0.131 Uiso 1 1 calc R . . H3B H 0.4244 1.0397 0.2775 0.131 Uiso 1 1 calc R . . H3C H 0.5306 0.9516 0.2665 0.131 Uiso 1 1 calc R . . C1 C 0.4903(4) 0.7499(5) 0.3506(2) 0.0757(14) Uani 1 1 d . . . H1A H 0.5508 0.7274 0.3237 0.114 Uiso 1 1 calc R . . H1B H 0.4506 0.668 0.3608 0.114 Uiso 1 1 calc R . . H1C H 0.5185 0.7916 0.3895 0.114 Uiso 1 1 calc R . . C11 C 0.2298(7) 0.7953(9) 0.0362(3) 0.163(3) Uani 1 1 d U . . H11A H 0.1756 0.8627 0.0469 0.244 Uiso 1 1 calc R . . H11B H 0.2001 0.7054 0.0429 0.244 Uiso 1 1 calc R . . H11C H 0.2483 0.8054 -0.008 0.244 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 O5 0.095(3) 0.070(3) 0.127(4) 0.011(2) 0.000(3) 0.005(2) C10 0.304(9) 0.129(5) 0.078(4) 0.041(4) -0.022(5) -0.114(6) C9 0.230(8) 0.271(8) 0.097(5) 0.045(5) 0.093(5) 0.092(6) Cu1 0.0352(2) 0.0335(2) 0.0255(2) 0.00014(15) -0.00327(14) -0.00538(17) Cl2 0.0487(5) 0.0462(5) 0.0510(5) -0.0031(4) -0.0019(4) 0.0154(4) O1 0.0383(12) 0.0387(12) 0.0301(11) 0.0023(9) -0.0054(9) -0.0102(10) N1 0.0395(15) 0.0388(14) 0.0267(13) -0.0005(11) -0.0019(11) -0.0058(13) N2 0.0405(16) 0.0349(14) 0.0290(13) 0.0000(11) -0.0055(11) -0.0084(13) O2 0.0484(14) 0.0442(13) 0.0258(11) 0.0006(9) -0.0014(9) -0.0124(11) C5 0.0311(17) 0.0338(17) 0.0358(17) -0.0027(13) 0.0003(13) -0.0012(14) C7 0.0411(19) 0.0393(18) 0.0298(16) 0.0042(13) 0.0006(13) -0.0024(15) O3 0.080(2) 0.0722(18) 0.0346(14) -0.0120(12) -0.0108(13) -0.0051(16) C6 0.047(2) 0.0424(18) 0.0357(17) 0.0025(14) 0.0010(15) -0.0115(16) O4 0.089(2) 0.080(2) 0.0365(15) 0.0166(14) -0.0150(14) -0.0131(18) C4 0.043(2) 0.0462(19) 0.0354(17) -0.0050(14) -0.0024(14) -0.0104(16) C15 0.043(2) 0.054(2) 0.0380(18) -0.0081(16) -0.0075(15) 0.0030(18) C12 0.051(2) 0.0424(19) 0.0400(18) -0.0062(14) -0.0013(15) 0.0034(17) C18 0.075(3) 0.079(3) 0.036(2) 0.0058(19) 0.0097(19) -0.018(3) C14 0.052(2) 0.076(3) 0.046(2) -0.0029(19) -0.0172(18) -0.011(2) C13 0.077(3) 0.046(2) 0.045(2) -0.0158(17) -0.001(2) -0.003(2) C16 0.058(2) 0.046(2) 0.048(2) 0.0061(16) -0.0026(18) 0.0084(19) C19 0.058(2) 0.056(2) 0.0365(18) 0.0030(16) 0.0064(16) 0.0053(19) C8 0.071(3) 0.071(2) 0.0292(18) 0.0094(17) -0.0032(16) -0.026(2) C2 0.074(3) 0.070(3) 0.048(2) -0.019(2) 0.005(2) -0.003(2) C17 0.083(3) 0.052(2) 0.069(3) 0.023(2) -0.015(2) 0.003(2) C3 0.121(4) 0.085(3) 0.056(3) -0.008(2) 0.001(3) -0.069(3) C1 0.067(3) 0.085(3) 0.073(3) -0.020(2) -0.037(2) 0.011(3) C11 0.138(6) 0.251(7) 0.096(4) 0.097(5) -0.058(4) -0.072(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O5 H1W 0.82(2) . ? O5 H2W 0.82(2) . ? C10 C8 1.444(7) . ? C10 H10A 0.96 . ? C10 H10B 0.96 . ? C10 H10C 0.96 . ? C9 C8 1.505(8) . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? Cu1 O2 1.931(2) . ? Cu1 O1 1.933(2) . ? Cu1 N2 2.043(2) . ? Cu1 N1 2.048(3) . ? Cu1 Cl2 2.6594(9) . ? O1 C5 1.277(4) . ? N1 C12 1.477(4) . ? N1 C15 1.478(4) . ? N1 H1N 0.90(2) . ? N2 C16 1.473(5) . ? N2 C19 1.479(4) . ? N2 H2N 0.88(2) . ? O2 C7 1.276(4) . ? C5 C6 1.382(4) . ? C5 C4 1.535(4) . ? C7 C6 1.374(5) . ? C7 C8 1.526(4) . ? O3 C13 1.399(5) . ? O3 C14 1.422(5) . ? C6 H6 0.93 . ? O4 C17 1.395(5) . ? O4 C18 1.402(5) . ? C4 C1 1.504(5) . ? C4 C3 1.510(5) . ? C4 C2 1.530(5) . ? C15 C14 1.507(5) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C12 C13 1.522(5) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C18 C19 1.511(5) . ? C18 H18A 0.97 . ? C18 H18B 0.97 . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C16 C17 1.513(5) . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? C19 H19A 0.97 . ? C19 H19B 0.97 . ? C8 C11 1.441(7) . ? C2 H2A 0.96 . ? C2 H2B 0.96 . ? C2 H2C 0.96 . ? C17 H17A 0.97 . ? C17 H17B 0.97 . ? C3 H3A 0.96 . ? C3 H3B 0.96 . ? C3 H3C 0.96 . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? 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 H1W O5 H2W 86(7) . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 Cu1 O1 90.90(9) . . ? O2 Cu1 N2 166.64(11) . . ? O1 Cu1 N2 87.45(10) . . ? O2 Cu1 N1 86.49(10) . . ? O1 Cu1 N1 168.90(10) . . ? N2 Cu1 N1 92.59(10) . . ? O2 Cu1 Cl2 93.91(7) . . ? O1 Cu1 Cl2 90.86(7) . . ? N2 Cu1 Cl2 99.37(8) . . ? N1 Cu1 Cl2 100.08(8) . . ? C5 O1 Cu1 125.7(2) . . ? C12 N1 C15 109.9(3) . . ? C12 N1 Cu1 111.4(2) . . ? C15 N1 Cu1 114.1(2) . . ? C12 N1 H1N 101(2) . . ? C15 N1 H1N 109(3) . . ? Cu1 N1 H1N 110(3) . . ? C16 N2 C19 109.7(3) . . ? C16 N2 Cu1 112.0(2) . . ? C19 N2 Cu1 114.3(2) . . ? C16 N2 H2N 103(2) . . ? C19 N2 H2N 111(2) . . ? Cu1 N2 H2N 106(2) . . ? C7 O2 Cu1 126.05(19) . . ? O1 C5 C6 123.8(3) . . ? O1 C5 C4 114.1(3) . . ? C6 C5 C4 122.1(3) . . ? O2 C7 C6 123.9(3) . . ? O2 C7 C8 114.3(3) . . ? C6 C7 C8 121.7(3) . . ? C13 O3 C14 109.3(3) . . ? C7 C6 C5 125.7(3) . . ? C7 C6 H6 117.1 . . ? C5 C6 H6 117.1 . . ? C17 O4 C18 109.6(3) . . ? C1 C4 C3 110.4(4) . . ? C1 C4 C2 109.2(3) . . ? C3 C4 C2 107.3(3) . . ? C1 C4 C5 108.6(3) . . ? C3 C4 C5 114.2(3) . . ? C2 C4 C5 106.9(3) . . ? N1 C15 C14 111.2(3) . . ? N1 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? N1 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108 . . ? N1 C12 C13 111.6(3) . . ? N1 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? N1 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 108 . . ? O4 C18 C19 111.6(3) . . ? O4 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? O4 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 108 . . ? O3 C14 C15 111.6(3) . . ? O3 C14 H14A 109.3 . . ? C15 C14 H14A 109.3 . . ? O3 C14 H14B 109.3 . . ? C15 C14 H14B 109.3 . . ? H14A C14 H14B 108 . . ? O3 C13 C12 112.3(3) . . ? O3 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? O3 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? N2 C16 C17 111.8(3) . . ? N2 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? N2 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? N2 C19 C18 111.6(3) . . ? N2 C19 H19A 109.3 . . ? C18 C19 H19A 109.3 . . ? N2 C19 H19B 109.3 . . ? C18 C19 H19B 109.3 . . ? H19A C19 H19B 108 . . ? C11 C8 C10 113.6(6) . . ? C11 C8 C9 103.6(6) . . ? C10 C8 C9 105.2(6) . . ? C11 C8 C7 111.9(4) . . ? C10 C8 C7 115.0(4) . . ? C9 C8 C7 106.4(4) . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O4 C17 C16 112.5(3) . . ? O4 C17 H17A 109.1 . . ? C16 C17 H17A 109.1 . . ? O4 C17 H17B 109.1 . . ? C16 C17 H17B 109.1 . . ? H17A C17 H17B 107.8 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? data_dpm_SCN _database_code_depnum_ccdc_archive 'CCDC 883444' #TrackingRef 'Cu(dkt)(morph)2X.cif' _vrf_RFACG01_ALERT_3_A ; PROBLEM: The value of the R factor is > 0.20 R factor given 0.216 RESPONSE: All obtained crystals of the compound were of extremely poor quality. The material is soft and the crystals easily deformed under even the most subtle strains. In addition, they grew as long thin needles (almost fibers), due to which they wery weakly diffracted. Therefore the data thus obtained were of quite low quality which naturally led to low quality of the structure demonstrated by a high R and a number of aditional problems (aee below). In spite of this, however, all the non-H atoms could easily be located in the electron difference map, and the overall shape of the molecule as well as the packing of molecules can be considered to be reasonably determined. ; _vrf_RFACR01_ALERT_3_A ; PROBLEM: The value of the weighted R factor is > 0.45 Weighted R factor given 0.535 RESPONSE: See above ; _vrf_PLAT082_ALERT_2_A ; PROBLEM: High R1 Value ..... 0.22 RESPONSE: See above ; _vrf_PLAT084_ALERT_2_A ; PROBLEM: High wR2 Value ..... 0.53 RESPONSE: See above ; _vrf_RINTA01_ALERT_3_B ; PROBLEM: The value of Rint is greater than 0.18 Rint given 0.184 RESPONSE: See above ; _vrf_PLAT020_ALERT_3_B ; PROBLEM: The value of Rint is greater than 0.12 ......... 0.184 RESPONSE: See above ; _vrf_PLAT341_ALERT_3_B ; PROBLEM: Low Bond Precision on C-C Bonds ........0.0300 Ang RESPONSE: See above ; _vrf_PLAT097_ALERT_2_C ; PROBLEM: Large Reported Max. (Positive) Residual Density 2.70 eA-3 RESPONSE: Due to the low quality of the data, the residual difference map is extremely uneaven, with high maxima and equally low minima (see below). The highest peak of 2.70 eA-3 at 0.4164 0.1498 0.4121 is at a distance of 1.46 A from N3 and cannot ba attributed to a missed atom but is obviously an artifact due to the low crystal quality. ; _vrf_PLAT098_ALERT_2_C ; PROBLEM: Large Reported Min. (Negative) Residual Density -2.65 eA-3 RESPONSE: As described above, the residual difference map is extremely uneaven. The deepest hole of -2.65 eA-3 at 0.7642 0.1484 0.9870 is 1.18 A from H19B, and can therefore not be accounted by erroneous atom type assignation. ; _vrf_PLAT242_ALERT_2_B ; PROBLEM: Check Low Ueq as Compared to Neighbors for C8 RESPONSE: C8 is a quaternary atom of a t-butyl group ; _audit_creation_date 2012-01-11T12:40:01-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (2,2,6,6-tetramethyl-3,5-heptanedionato)thiocyanatobis(morpholine)copper(II) ; _chemical_formula_sum 'C20 H37 Cu N3 O4 S' _chemical_formula_moiety 'C20 H37 Cu N3 O4 S' _chemical_formula_weight 479.13 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc ' 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 10.458(2) _cell_length_b 37.201(6) _cell_length_c 7.053(2) _cell_angle_alpha 90 _cell_angle_beta 108.72(2) _cell_angle_gamma 90 _cell_volume 2598.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 102 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 52.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020 _exptl_special_details ; ? ; _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.98 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.947 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 27 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1839 _diffrn_reflns_av_unetI/netI 0.1229 _diffrn_reflns_number 19725 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -47 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.1 _diffrn_reflns_theta_max 27 _diffrn_reflns_theta_full 27 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 5629 _reflns_number_gt 4155 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5629 _refine_ls_number_parameters 262 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.2423 _refine_ls_R_factor_gt 0.2156 _refine_ls_wR_factor_ref 0.5347 _refine_ls_wR_factor_gt 0.5189 _refine_ls_goodness_of_fit_ref 1.843 _refine_ls_restrained_S_all 1.841 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.697 _refine_diff_density_min -2.652 _refine_diff_density_rms 0.191 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' 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 C1 C 0.7852(19) 0.0890(7) 0.379(4) 0.158(13) Uani 1 1 d D . . H1A H 0.789 0.1075 0.4755 0.237 Uiso 1 1 calc R . . H1B H 0.7842 0.0997 0.255 0.237 Uiso 1 1 calc R . . H1C H 0.863 0.0737 0.4283 0.237 Uiso 1 1 calc R . . C2 C 0.673(4) 0.0368(10) 0.220(6) 0.240(19) Uani 1 1 d DU . . H2A H 0.5895 0.0238 0.1756 0.36 Uiso 1 1 calc R . . H2B H 0.744 0.0211 0.2953 0.36 Uiso 1 1 calc R . . H2C H 0.6942 0.0458 0.1057 0.36 Uiso 1 1 calc R . . Cu1 Cu 0.41081(16) 0.14950(3) 0.0000(2) 0.0504(6) Uani 1 1 d . . . S1 S 0.4171(4) 0.23557(9) 0.5279(5) 0.0660(9) Uani 1 1 d . . . C3 C 0.651(3) 0.0554(10) 0.547(3) 0.175(15) Uani 1 1 d D . . H3A H 0.5704 0.0415 0.5263 0.262 Uiso 1 1 calc R . . H3B H 0.6487 0.0761 0.6265 0.262 Uiso 1 1 calc R . . H3C H 0.7284 0.0409 0.6146 0.262 Uiso 1 1 calc R . . C16 C 0.6702(11) 0.1906(4) 0.1225(16) 0.056(3) Uani 1 1 d . . . H16A H 0.7105 0.17 0.2046 0.068 Uiso 1 1 calc R . . H16B H 0.6305 0.2057 0.2004 0.068 Uiso 1 1 calc R . . O2 O 0.2666(9) 0.1161(3) -0.0053(16) 0.075(3) Uani 1 1 d . . . C15 C 0.1566(12) 0.1928(4) -0.1341(19) 0.059(3) Uani 1 1 d . . . H15A H 0.197 0.208 -0.0187 0.07 Uiso 1 1 calc R . . H15B H 0.1131 0.1728 -0.0909 0.07 Uiso 1 1 calc R . . N2 N 0.5618(8) 0.1777(3) -0.0569(13) 0.049(2) Uani 1 1 d U . . H2 H 0.5238 0.1974 -0.13 0.059 Uiso 1 1 calc R . . O1 O 0.5465(9) 0.1147(3) 0.1379(15) 0.071(2) Uani 1 1 d . . . N1 N 0.2645(9) 0.1787(3) -0.2069(14) 0.052(2) Uani 1 1 d . . . H1 H 0.3062 0.198 -0.2403 0.063 Uiso 1 1 calc R . . N3 N 0.4111(13) 0.1785(4) 0.2691(16) 0.070(3) Uani 1 1 d . . . C20 C 0.4117(13) 0.2026(4) 0.3769(15) 0.057(3) Uani 1 1 d . . . O4 O 0.8400(10) 0.1890(3) -0.0328(18) 0.084(3) Uani 1 1 d U . . C19 C 0.6275(15) 0.1564(5) -0.179(2) 0.078(4) Uani 1 1 d U . . H19A H 0.5604 0.15 -0.3056 0.094 Uiso 1 1 calc R . . H19B H 0.6631 0.1343 -0.1093 0.094 Uiso 1 1 calc R . . O3 O -0.0117(10) 0.1910(4) -0.4635(16) 0.090(3) Uani 1 1 d U . . C17 C 0.7790(15) 0.2112(5) 0.075(2) 0.077(4) Uani 1 1 d . . . H17A H 0.7407 0.2323 -0.004 0.092 Uiso 1 1 calc R . . H17B H 0.846 0.2192 0.1979 0.092 Uiso 1 1 calc R . . C12 C 0.1989(15) 0.1587(5) -0.3935(18) 0.070(4) Uani 1 1 d . . . H12A H 0.1586 0.137 -0.3618 0.084 Uiso 1 1 calc R . . H12B H 0.2667 0.1517 -0.4531 0.084 Uiso 1 1 calc R . . C14 C 0.0521(14) 0.2139(6) -0.288(2) 0.084(4) Uani 1 1 d U . . H14A H -0.0158 0.2225 -0.2322 0.101 Uiso 1 1 calc R . . H14B H 0.0936 0.2346 -0.3284 0.101 Uiso 1 1 calc R . . C5 C 0.5295(18) 0.0857(4) 0.222(2) 0.074(4) Uani 1 1 d . . . C6 C 0.4019(17) 0.0742(4) 0.217(2) 0.079(4) Uani 1 1 d . . . H6 H 0.3977 0.0558 0.3042 0.095 Uiso 1 1 calc R . . C7 C 0.2784(16) 0.0881(4) 0.091(2) 0.075(4) Uani 1 1 d . . . C8 C 0.1456(18) 0.0689(5) 0.088(3) 0.096(4) Uani 1 1 d DU . . C4 C 0.6603(19) 0.0672(6) 0.347(4) 0.133(8) Uani 1 1 d DU . . C13 C 0.0898(16) 0.1808(5) -0.5452(19) 0.081(4) Uani 1 1 d U . . H13A H 0.13 0.2021 -0.5818 0.097 Uiso 1 1 calc R . . H13B H 0.05 0.1666 -0.6653 0.097 Uiso 1 1 calc R . . C18 C 0.7401(19) 0.1768(7) -0.219(3) 0.103(6) Uani 1 1 d U . . H18A H 0.7839 0.1615 -0.2913 0.124 Uiso 1 1 calc R . . H18B H 0.7031 0.1974 -0.3034 0.124 Uiso 1 1 calc R . . C11 C 0.031(2) 0.0945(6) 0.033(5) 0.149(10) Uani 1 1 d U . . H11A H 0.0338 0.1086 -0.0797 0.223 Uiso 1 1 calc R . . H11B H 0.0378 0.11 0.1443 0.223 Uiso 1 1 calc R . . H11C H -0.0523 0.0814 -0.0017 0.223 Uiso 1 1 calc R . . C9 C 0.154(3) 0.0495(11) 0.275(4) 0.210(15) Uani 1 1 d DU . . H9A H 0.2323 0.0343 0.3123 0.315 Uiso 1 1 calc R . . H9B H 0.0745 0.035 0.2537 0.315 Uiso 1 1 calc R . . H9C H 0.1605 0.0665 0.3797 0.315 Uiso 1 1 calc R . . C10 C 0.114(3) 0.0474(8) -0.122(5) 0.178(12) Uani 1 1 d U . . H10A H 0.1799 0.0288 -0.1085 0.266 Uiso 1 1 calc R . . H10B H 0.1173 0.0639 -0.2254 0.266 Uiso 1 1 calc R . . H10C H 0.0255 0.0369 -0.1569 0.266 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 C1 0.083(13) 0.16(2) 0.23(3) 0.10(2) 0.049(16) 0.047(15) C2 0.24(2) 0.24(2) 0.24(2) -0.012(10) 0.074(11) 0.010(10) Cu1 0.0557(8) 0.0446(9) 0.0510(9) 0.0037(6) 0.0175(6) -0.0021(6) S1 0.099(2) 0.0519(19) 0.0546(17) 0.0003(14) 0.0350(15) 0.0008(16) C3 0.17(2) 0.25(4) 0.097(15) 0.08(2) 0.031(15) 0.07(3) C16 0.050(6) 0.064(8) 0.046(5) -0.008(5) 0.001(4) -0.012(5) O2 0.060(5) 0.062(6) 0.096(7) 0.014(5) 0.017(5) -0.010(4) C15 0.058(6) 0.061(8) 0.067(7) -0.001(6) 0.034(5) -0.008(5) N2 0.040(4) 0.055(6) 0.044(4) 0.008(4) 0.003(3) -0.002(3) O1 0.065(5) 0.060(6) 0.088(6) 0.019(5) 0.025(4) 0.008(4) N1 0.048(5) 0.050(6) 0.065(5) 0.009(4) 0.027(4) 0.003(4) N3 0.090(8) 0.071(8) 0.054(5) -0.005(6) 0.029(5) 0.006(6) C20 0.065(7) 0.081(9) 0.026(4) 0.001(5) 0.015(4) 0.009(6) O4 0.055(5) 0.088(8) 0.113(7) 0.029(6) 0.033(4) 0.001(4) C19 0.075(8) 0.118(13) 0.046(6) -0.018(6) 0.025(5) -0.013(6) O3 0.052(5) 0.130(10) 0.081(6) 0.016(6) 0.010(4) 0.014(5) C17 0.068(8) 0.100(12) 0.053(7) 0.003(7) 0.004(6) -0.007(7) C12 0.078(9) 0.093(11) 0.039(6) 0.006(6) 0.019(5) 0.006(7) C14 0.056(7) 0.124(14) 0.081(8) 0.007(6) 0.034(6) 0.026(7) C5 0.111(11) 0.040(7) 0.079(8) 0.009(7) 0.040(8) 0.020(7) C6 0.102(11) 0.049(8) 0.092(11) 0.027(7) 0.040(9) 0.010(7) C7 0.094(10) 0.053(8) 0.082(9) 0.003(7) 0.032(7) -0.018(7) C8 0.083(9) 0.071(10) 0.133(11) 0.034(8) 0.031(10) -0.015(6) C4 0.090(13) 0.153(19) 0.161(18) 0.090(13) 0.047(13) 0.046(14) C13 0.085(8) 0.107(12) 0.050(6) 0.012(6) 0.020(6) 0.011(8) C18 0.088(9) 0.145(18) 0.094(8) 0.000(11) 0.053(6) -0.009(9) C11 0.097(12) 0.070(12) 0.28(3) 0.025(13) 0.061(17) -0.007(8) C9 0.15(2) 0.28(4) 0.211(17) 0.14(2) 0.08(2) -0.02(2) C10 0.22(3) 0.112(19) 0.23(2) -0.063(18) 0.11(3) -0.096(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C4 1.491(17) . ? C2 C4 1.476(18) . ? Cu1 O1 1.937(9) . ? Cu1 O2 1.945(9) . ? Cu1 N2 2.041(9) . ? Cu1 N1 2.054(9) . ? Cu1 N3 2.182(11) . ? S1 C20 1.614(13) . ? C3 C4 1.51(3) . ? C16 N2 1.481(12) . ? C16 C17 1.50(2) . ? O2 C7 1.229(17) . ? C15 N1 1.478(14) . ? C15 C14 1.49(2) . ? N2 C19 1.492(17) . ? O1 C5 1.271(17) . ? N1 C12 1.475(17) . ? N3 C20 1.174(16) . ? O4 C17 1.41(2) . ? O4 C18 1.47(2) . ? C19 C18 1.50(2) . ? O3 C13 1.412(19) . ? O3 C14 1.47(2) . ? C12 C13 1.53(2) . ? C5 C6 1.39(2) . ? C5 C4 1.53(2) . ? C6 C7 1.41(2) . ? C7 C8 1.56(2) . ? C8 C9 1.482(17) . ? C8 C11 1.48(3) . ? C8 C10 1.62(4) . ? 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 O1 Cu1 O2 91.2(4) . . ? O1 Cu1 N2 87.4(4) . . ? O2 Cu1 N2 165.7(4) . . ? O1 Cu1 N1 165.7(4) . . ? O2 Cu1 N1 85.9(4) . . ? N2 Cu1 N1 92.0(4) . . ? O1 Cu1 N3 95.6(5) . . ? O2 Cu1 N3 96.7(5) . . ? N2 Cu1 N3 97.6(4) . . ? N1 Cu1 N3 98.6(4) . . ? N2 C16 C17 113.7(10) . . ? C7 O2 Cu1 126.3(10) . . ? N1 C15 C14 113.4(10) . . ? C16 N2 C19 107.3(9) . . ? C16 N2 Cu1 115.2(7) . . ? C19 N2 Cu1 111.7(9) . . ? C5 O1 Cu1 127.7(10) . . ? C12 N1 C15 107.5(10) . . ? C12 N1 Cu1 113.2(8) . . ? C15 N1 Cu1 114.8(7) . . ? C20 N3 Cu1 159.9(10) . . ? N3 C20 S1 178.4(12) . . ? C17 O4 C18 110.6(12) . . ? N2 C19 C18 112.0(15) . . ? C13 O3 C14 107.6(11) . . ? O4 C17 C16 109.2(13) . . ? N1 C12 C13 112.5(13) . . ? O3 C14 C15 109.5(14) . . ? O1 C5 C6 121.8(13) . . ? O1 C5 C4 114.6(15) . . ? C6 C5 C4 123.3(14) . . ? C5 C6 C7 125.5(14) . . ? O2 C7 C6 124.6(14) . . ? O2 C7 C8 116.8(14) . . ? C6 C7 C8 118.3(14) . . ? C9 C8 C11 111(2) . . ? C9 C8 C7 114.4(18) . . ? C11 C8 C7 110.5(15) . . ? C9 C8 C10 121(2) . . ? C11 C8 C10 100(2) . . ? C7 C8 C10 99.3(15) . . ? C2 C4 C1 105.2(19) . . ? C2 C4 C3 113(2) . . ? C1 C4 C3 109(2) . . ? C2 C4 C5 103(2) . . ? C1 C4 C5 114.9(16) . . ? C3 C4 C5 110.8(17) . . ? O3 C13 C12 110.4(11) . . ? O4 C18 C19 111.3(13) . . ? data_dbm_Cl_solv _database_code_depnum_ccdc_archive 'CCDC 883445' #TrackingRef 'Cu(dkt)(morph)2X.cif' _vrf_PLAT223_ALERT_4_A ; PROBLEM: Large Solvent/Anion H Ueq(max)/Ueq(min) ... 10.0 Ratio RESPONSE: The structure contains a number of morpholine molecules (4 independant molecules; 14 per unit cell) which are severely disordered. The disorder was only partially resolvable in spite of the low temperature data collection. This led to a number of problems with the structural model. However, these problems were restrained to the solvent molecules. ; _vrf_PLAT430_ALERT_2_A ; PROBLEM: Short Inter D...A Contact N2 .. N2 .. 2.12 Ang. RESPONSE: The morpholine molecule is an average of several conformations disordered about the twofold axis. See above. ; _vrf_PLAT245_ALERT_2_B ; PROBLEM: U(iso) H1W Smaller than U(eq) O7 by ... 0.053 AngSq. RESPONSE: The hydrogen atoms on the water molecule could not be located from the difference map, so the water molecule was modeled so that hydrogen atoms are in correct positions relative to neighboring acceptors, namely two chloride ions. ; _vrf_FORMU01_ALERT_2_G ; PROBLEM: There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. RESPONSE: The hydrogen atoms bonded to nitrogen in tne disordered solvent could not be located from the difference map. Since there is some ambiguity concerning their correct placement (one of the morpholine molecules is protonated, all severely disordered) they were omitted from the structural model. ; _audit_creation_date 2012-01-18T18:44:38-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (1,3-diphenyl-1,3-propanedionato)chlorobis(morpholine)copper(II) - morpholinium chloride morpholine solvate hydrate ; _chemical_formula_sum 'C74 H126 Cl3 Cu2 N11 O17' _chemical_formula_moiety '2(C23 H29 Cl Cu N2 O4), 6(C4 H9 N O), C4 H10 N O, Cl, 2(H2 O)' _chemical_formula_weight 1675.30 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/m ' _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 15.888(5) _cell_length_b 16.700(3) _cell_length_c 17.261(13) _cell_angle_alpha 90 _cell_angle_beta 113.85(6) _cell_angle_gamma 90 _cell_volume 4189(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150.0(2) _cell_measurement_reflns_used 142 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 52.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1782 _exptl_special_details ; ? ; _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.674 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150.0(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 27 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_unetI/netI 0.1504 _diffrn_reflns_number 8084 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.966 _diffrn_measured_fraction_theta_max 0.966 _reflns_number_total 3714 _reflns_number_gt 1778 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1267P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3714 _refine_ls_number_parameters 289 _refine_ls_number_restraints 53 _refine_ls_R_factor_all 0.1456 _refine_ls_R_factor_gt 0.0837 _refine_ls_wR_factor_ref 0.2405 _refine_ls_wR_factor_gt 0.2246 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.969 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.84 _refine_diff_density_min -0.686 _refine_diff_density_rms 0.094 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.65117(8) 0 0.33535(8) 0.0391(4) Uani 1 2 d S . . Cl1 Cl 0.4923(2) 0 0.20174(18) 0.0624(8) Uani 1 2 d S . . Cl2 Cl 0.5 0 0.5 0.0878(18) Uani 1 4 d SD . . O1 O 0.7103(3) 0.0836(2) 0.2963(3) 0.0445(12) Uani 1 1 d . . . O2 O 0.6260(3) 0.2458(3) 0.4690(3) 0.0527(14) Uani 1 1 d . . . N3 N 0.9012(14) 0 0.475(3) 0.08(2) Uani 0.5 2 d SPD . 1 O8 O 0.9029(13) 0 0.473(2) 0.062(14) Uiso 0.5 2 d SPD . 2 C8 C 0.7892(7) 0 0.2384(6) 0.041(2) Uani 1 2 d S . . H8 H 0.8273 0 0.2092 0.049 Uiso 1 2 calc SR . . N1 N 0.6180(4) 0.0866(3) 0.4003(3) 0.0349(13) Uani 1 1 d D . . C7 C 0.7628(4) 0.0744(4) 0.2587(4) 0.0324(15) Uani 1 1 d . . . C1 C 0.7976(4) 0.1500(4) 0.2350(4) 0.0385(16) Uani 1 1 d D . . C10 C 0.5438(5) 0.2171(4) 0.4013(5) 0.052(2) Uani 1 1 d . . . H10A H 0.512 0.2616 0.3652 0.063 Uiso 1 1 calc R . . H10B H 0.5031 0.1941 0.4247 0.063 Uiso 1 1 calc R . . C4 C 0.8552(5) 0.2930(4) 0.1890(5) 0.055(2) Uani 1 1 d . . . H4 H 0.8745 0.3406 0.1735 0.066 Uiso 1 1 calc R . . C9 C 0.5659(5) 0.1552(3) 0.3495(4) 0.0412(17) Uani 1 1 d . . . H9A H 0.5089 0.1358 0.3058 0.049 Uiso 1 1 calc R . . H9B H 0.6015 0.18 0.3217 0.049 Uiso 1 1 calc R . . C2 C 0.7825(5) 0.2216(4) 0.2649(5) 0.051(2) Uani 1 1 d . . . H2 H 0.7526 0.223 0.3013 0.061 Uiso 1 1 calc R . . C11 C 0.6740(5) 0.1811(4) 0.5214(5) 0.054(2) Uani 1 1 d . . . H11A H 0.6357 0.1572 0.5469 0.065 Uiso 1 1 calc R . . H11B H 0.7293 0.2013 0.5667 0.065 Uiso 1 1 calc R . . C12 C 0.7006(5) 0.1172(4) 0.4724(4) 0.0459(18) Uani 1 1 d . . . H12A H 0.7434 0.1397 0.4512 0.055 Uiso 1 1 calc R . . H12B H 0.731 0.0733 0.5101 0.055 Uiso 1 1 calc R . . C3 C 0.8116(6) 0.2932(4) 0.2414(5) 0.061(2) Uani 1 1 d . . . H3 H 0.8005 0.3416 0.2623 0.073 Uiso 1 1 calc R . . C19 C 0.9500(5) 0.07088(12) 0.4675(5) 0.068(2) Uani 1 1 d D . . H19A H 0.9191 0.1181 0.4758 0.082 Uiso 1 1 calc R . 1 H19B H 0.9488 0.0734 0.4109 0.082 Uiso 1 1 calc R . 1 C6 C 0.8422(6) 0.1510(4) 0.1802(5) 0.065(2) Uani 1 1 d D . . H6 H 0.8526 0.1032 0.1579 0.078 Uiso 1 1 calc R . . N4 N 0.8710(10) 0 0.6304(9) 0.135(5) Uani 1 2 d S . . O4 O 0.9567(11) 0 0.8032(10) 0.183(7) Uani 1 2 d S . . C5 C 0.8707(7) 0.2209(5) 0.1590(6) 0.080(3) Uani 1 1 d . . . H5 H 0.9016 0.22 0.1233 0.096 Uiso 1 1 calc R . . C18 C 0.8688(18) 0.0688(10) 0.9832(12) 0.209(12) Uani 1 1 d D . . H18A H 0.8804 0.116 0.9562 0.251 Uiso 1 1 calc R . . H18B H 0.9078 0.0725 1.0431 0.251 Uiso 1 1 calc R . . C15 C 0.9164(9) 0.0711(6) 0.6784(7) 0.123(4) Uani 1 1 d D . . H15A H 0.8885 0.119 0.6467 0.147 Uiso 1 1 calc R . . H15B H 0.9811 0.0707 0.6887 0.147 Uiso 1 1 calc R . . C16 C 0.9055(10) 0.0702(6) 0.7630(8) 0.131(5) Uani 1 1 d D . . H16A H 0.9315 0.1179 0.796 0.158 Uiso 1 1 calc R . . H16B H 0.8414 0.0655 0.7541 0.158 Uiso 1 1 calc R . . O5 O 0.7626(12) 0 1.0058(15) 0.234(10) Uani 1 2 d S . . C17 C 0.7680(15) 0.0719(13) 0.9729(12) 0.258(15) Uani 1 1 d D . . H17A H 0.7573 0.1155 1.0049 0.31 Uiso 1 1 calc R . . H17B H 0.7255 0.0762 0.9139 0.31 Uiso 1 1 calc R . . N5 N 0.897(2) 0 0.9500(16) 0.36(2) Uani 1 2 d S . . O3 O 0 0.2689(6) 0 0.165(6) Uani 1 2 d SDU . . N2 N 0 0.4366(11) 0 0.179(5) Uani 1 2 d SDU . . C13 C -0.064(2) 0.3884(13) -0.0682(10) 0.178(6) Uani 0.5 1 d PDU A 1 H13A H -0.0376 0.3759 -0.1086 0.213 Uiso 0.5 1 calc PR A 1 H13B H -0.1206 0.4181 -0.0976 0.213 Uiso 0.5 1 calc PR A 1 C14 C -0.0843(7) 0.3122(10) -0.0323(13) 0.083(4) Uani 0.5 1 d PDU A 1 H14A H -0.1045 0.3239 0.0125 0.1 Uiso 0.5 1 calc PR A 1 H14B H -0.1319 0.2817 -0.0761 0.1 Uiso 0.5 1 calc PR A 1 C14A C -0.0606(13) 0.3132(10) -0.0712(8) 0.088(4) Uani 0.5 1 d PDU A 2 H14C H -0.1161 0.2828 -0.1021 0.105 Uiso 0.5 1 calc PR A 2 H14D H -0.031 0.3254 -0.1091 0.105 Uiso 0.5 1 calc PR A 2 C13A C -0.0832(11) 0.3891(13) -0.036(2) 0.178(6) Uani 0.5 1 d PDU A 2 H13C H -0.1305 0.4188 -0.0813 0.214 Uiso 0.5 1 calc PR A 2 H13D H -0.1058 0.3765 0.0066 0.214 Uiso 0.5 1 calc PR A 2 O7 O 0.6576(4) 0 0.7174(3) 0.163(6) Uani 1 2 d SD . . H1N H 0.577(3) 0.069(3) 0.422(3) 0.023(16) Uiso 1 1 d D . . H1W H 0.63292(4) 0 0.7522(3) 0.11(5) Uiso 1 2 d SD . . H2W H 0.6164(7) 0 0.6680(2) 0.1(8) Uiso 1 2 d SD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0362(8) 0.0310(6) 0.0467(8) 0 0.0133(6) 0 Cl1 0.060(2) 0.0583(16) 0.0557(18) 0 0.0099(15) 0 Cl2 0.104(4) 0.043(2) 0.166(5) 0 0.107(4) 0 O1 0.042(3) 0.029(2) 0.066(3) 0.002(2) 0.027(3) -0.002(2) O2 0.038(3) 0.039(3) 0.076(4) -0.013(3) 0.018(3) -0.003(2) N3 0.035(16) 0.010(10) 0.14(4) 0 -0.032(12) 0 C8 0.035(6) 0.043(6) 0.046(6) 0 0.018(5) 0 N1 0.030(3) 0.027(3) 0.048(4) 0.000(3) 0.016(3) -0.004(2) C7 0.022(4) 0.037(4) 0.031(4) 0.007(3) 0.002(3) 0.000(3) C1 0.029(4) 0.038(4) 0.040(4) -0.003(3) 0.005(3) -0.001(3) C10 0.035(4) 0.035(4) 0.081(6) 0.003(4) 0.017(4) 0.004(3) C4 0.050(5) 0.050(5) 0.052(5) 0.004(4) 0.009(4) -0.014(4) C9 0.036(4) 0.032(3) 0.052(4) 0.006(3) 0.014(4) 0.006(3) C2 0.055(5) 0.045(4) 0.055(5) 0.006(4) 0.023(4) -0.005(4) C11 0.040(5) 0.061(5) 0.051(5) -0.005(4) 0.007(4) -0.004(4) C12 0.036(4) 0.044(4) 0.046(4) -0.006(3) 0.004(4) 0.002(3) C3 0.058(6) 0.041(4) 0.066(6) -0.004(4) 0.008(5) 0.002(4) C19 0.057(6) 0.045(4) 0.077(6) -0.002(4) -0.001(4) 0.006(4) C6 0.080(7) 0.043(4) 0.086(7) -0.009(4) 0.047(6) -0.011(4) N4 0.122(12) 0.085(9) 0.123(11) 0 -0.028(9) 0 O4 0.176(14) 0.110(10) 0.169(13) 0 -0.029(11) 0 C5 0.089(8) 0.070(6) 0.098(8) -0.014(5) 0.054(7) -0.019(5) C18 0.45(4) 0.106(11) 0.178(17) 0.003(11) 0.24(2) 0.025(17) C15 0.140(12) 0.075(7) 0.128(11) -0.004(7) 0.028(9) -0.016(7) C16 0.170(14) 0.088(8) 0.169(14) -0.041(9) 0.102(13) -0.017(9) O5 0.121(13) 0.199(19) 0.28(3) 0 -0.027(14) 0 C17 0.42(4) 0.20(2) 0.074(11) 0.045(13) 0.024(17) 0.10(3) N5 0.85(7) 0.108(13) 0.39(4) 0 0.55(5) 0 O3 0.087(6) 0.086(7) 0.202(11) 0 -0.065(8) 0 N2 0.179(6) 0.179(6) 0.179(6) 0 0.071(2) 0 C13 0.178(6) 0.178(6) 0.178(6) 0.0004(10) 0.072(2) 0.0000(10) C14 0.083(4) 0.083(4) 0.083(4) 0.0004(10) 0.0336(18) -0.0009(10) C14A 0.087(4) 0.088(4) 0.088(4) -0.0004(10) 0.0352(19) 0.0002(10) C13A 0.178(6) 0.178(6) 0.178(6) 0.0001(10) 0.072(2) 0.0003(10) O7 0.154(12) 0.085(8) 0.312(18) 0 0.159(14) 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 1.949(4) . ? Cu1 O1 1.949(4) 6 ? Cu1 N1 2.026(5) 6 ? Cu1 N1 2.026(5) . ? Cu1 Cl1 2.643(4) . ? O1 C7 1.257(7) . ? O2 C11 1.417(8) . ? O2 C10 1.438(8) . ? N3 C19 1.4484(15) . ? N3 C19 1.4484(15) 6 ? O8 C19 1.4236(15) . ? O8 C19 1.4236(15) 6 ? C8 C7 1.401(7) . ? C8 C7 1.401(7) 6 ? C8 H8 0.93 . ? N1 C9 1.477(8) . ? N1 C12 1.487(8) . ? N1 H1N 0.917(19) . ? C7 C1 1.499(8) . ? C1 C2 1.361(9) . ? C1 C6 1.394(2) . ? C10 C9 1.498(9) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C4 C3 1.344(10) . ? C4 C5 1.371(10) . ? C4 H4 0.93 . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C2 C3 1.399(10) . ? C2 H2 0.93 . ? C11 C12 1.523(9) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C3 H3 0.93 . ? C19 C19 1.529(14) 2_756 ? C19 H19A 0.97 . ? C19 H19B 0.97 . ? C6 C5 1.355(10) . ? C6 H6 0.93 . ? N4 C15 1.460(12) 6 ? N4 C15 1.460(12) . ? O4 C16 1.435(14) . ? O4 C16 1.435(14) 6 ? C5 H5 0.93 . ? C18 N5 1.435(17) . ? C18 C17 1.539(2) . ? C18 H18A 0.97 . ? C18 H18B 0.97 . ? C15 C16 1.537(2) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? O5 C17 1.35(2) 6 ? O5 C17 1.35(2) . ? C17 H17A 0.97 . ? C17 H17B 0.97 . ? N5 C18 1.435(17) 6 ? O3 C14 1.423(2) . ? O3 C14 1.423(2) 2 ? O3 C14A 1.424(2) 2 ? O3 C14A 1.424(2) . ? N2 C13A 1.448(2) 2 ? N2 C13A 1.449(2) . ? N2 C13 1.449(2) . ? N2 C13 1.449(2) 2 ? C13 C14 1.507(2) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C14A C13A 1.507(2) . ? C14A H14C 0.97 . ? C14A H14D 0.97 . ? C13A H13C 0.97 . ? C13A H13D 0.97 . ? O7 H1W 0.8400(5) . ? O7 H2W 0.8400(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 91.5(3) . 6 ? O1 Cu1 N1 166.5(2) . 6 ? O1 Cu1 N1 87.1(2) 6 6 ? O1 Cu1 N1 87.1(2) . . ? O1 Cu1 N1 166.5(2) 6 . ? N1 Cu1 N1 91.1(3) 6 . ? O1 Cu1 Cl1 97.04(15) . . ? O1 Cu1 Cl1 97.04(15) 6 . ? N1 Cu1 Cl1 96.46(17) 6 . ? N1 Cu1 Cl1 96.46(17) . . ? C7 O1 Cu1 127.2(4) . . ? C11 O2 C10 110.1(5) . . ? C19 N3 C19 109.6(3) . 6 ? C19 O8 C19 112.5(3) . 6 ? C7 C8 C7 125.0(9) . 6 ? C7 C8 H8 117.5 . . ? C7 C8 H8 117.5 6 . ? C9 N1 C12 108.9(5) . . ? C9 N1 Cu1 115.8(4) . . ? C12 N1 Cu1 111.7(4) . . ? C9 N1 H1N 100(3) . . ? C12 N1 H1N 107(3) . . ? Cu1 N1 H1N 113(3) . . ? O1 C7 C8 124.5(6) . . ? O1 C7 C1 115.6(5) . . ? C8 C7 C1 119.9(6) . . ? C2 C1 C6 117.5(6) . . ? C2 C1 C7 119.8(6) . . ? C6 C1 C7 122.7(6) . . ? O2 C10 C9 111.1(5) . . ? O2 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? O2 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108 . . ? C3 C4 C5 118.5(7) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? N1 C9 C10 113.1(6) . . ? N1 C9 H9A 109 . . ? C10 C9 H9A 109 . . ? N1 C9 H9B 109 . . ? C10 C9 H9B 109 . . ? H9A C9 H9B 107.8 . . ? C1 C2 C3 120.8(7) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? O2 C11 C12 112.2(6) . . ? O2 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? O2 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? N1 C12 C11 110.9(5) . . ? N1 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108 . . ? C4 C3 C2 120.8(7) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? O8 C19 C19 111.7(13) . 2_756 ? N3 C19 C19 111.7(14) . 2_756 ? O8 C19 H19A 110.8 . . ? N3 C19 H19A 109.3 . . ? C19 C19 H19A 109.3 2_756 . ? O8 C19 H19B 107.8 . . ? N3 C19 H19B 109.3 . . ? C19 C19 H19B 109.3 2_756 . ? H19A C19 H19B 107.9 . . ? C5 C6 C1 120.8(7) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? C15 N4 C15 108.7(13) 6 . ? C16 O4 C16 109.5(14) . 6 ? C6 C5 C4 121.6(8) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? N5 C18 C17 117(2) . . ? N5 C18 H18A 107.9 . . ? C17 C18 H18A 107.9 . . ? N5 C18 H18B 107.9 . . ? C17 C18 H18B 107.9 . . ? H18A C18 H18B 107.2 . . ? N4 C15 C16 108.2(11) . . ? N4 C15 H15A 110.1 . . ? C16 C15 H15A 110.1 . . ? N4 C15 H15B 110.1 . . ? C16 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? O4 C16 C15 102.0(11) . . ? O4 C16 H16A 111.4 . . ? C15 C16 H16A 111.4 . . ? O4 C16 H16B 111.4 . . ? C15 C16 H16B 111.4 . . ? H16A C16 H16B 109.2 . . ? C17 O5 C17 126(3) 6 . ? O5 C17 C18 99.3(17) . . ? O5 C17 H17A 111.9 . . ? C18 C17 H17A 111.9 . . ? O5 C17 H17B 111.9 . . ? C18 C17 H17B 111.9 . . ? H17A C17 H17B 109.6 . . ? C18 N5 C18 106.4(16) . 6 ? C14 O3 C14 118.8(17) . 2 ? C14 O3 C14A 105.9(12) . 2 ? C14 O3 C14A 105.9(12) 2 . ? C14A O3 C14A 117.4(17) 2 . ? C13A N2 C13A 114(3) 2 . ? C13A N2 C13 105(2) 2 . ? C13A N2 C13 105(2) . 2 ? C13 N2 C13 113(2) . 2 ? N2 C13 C14 109.4(16) . . ? N2 C13 H13A 109.8 . . ? C14 C13 H13A 109.8 . . ? N2 C13 H13B 109.8 . . ? C14 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? O3 C14 C13 105.5(17) . . ? O3 C14 H14A 110.6 . . ? C13 C14 H14A 110.6 . . ? O3 C14 H14B 110.6 . . ? C13 C14 H14B 110.6 . . ? H14A C14 H14B 108.8 . . ? O3 C14A C13A 106.3(18) . . ? O3 C14A H14C 110.5 . . ? C13A C14A H14C 110.5 . . ? O3 C14A H14D 110.5 . . ? C13A C14A H14D 110.5 . . ? H14C C14A H14D 108.7 . . ? N2 C13A C14A 108.1(16) . . ? N2 C13A H13C 110.1 . . ? C14A C13A H13C 110.1 . . ? N2 C13A H13D 110.1 . . ? C14A C13A H13D 110.1 . . ? H13C C13A H13D 108.4 . . ? H1W O7 H2W 109.2(11) . . ? data_dbm_SCN _database_code_depnum_ccdc_archive 'CCDC 883446' #TrackingRef 'Cu(dkt)(morph)2X.cif' _audit_creation_date 2011-11-23T18:08:39-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (1,3-diphenyl-1,3-propanedionato)thiocyanatobis(morpholine)copper(II) ; _chemical_formula_sum 'C24 H29 Cu N3 O4 S' _chemical_formula_moiety 'C24 H29 Cu N3 O4 S' _chemical_formula_weight 519.1 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/m' _symmetry_space_group_name_Hall '-P 2yb ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 6.4957(2) _cell_length_b 23.0280(10) _cell_length_c 8.5679(3) _cell_angle_alpha 90 _cell_angle_beta 102.451(4) _cell_angle_gamma 90 _cell_volume 1251.47(8) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 96 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 52.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 542 _exptl_special_details ; ? ; _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.99 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 27 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_unetI/netI 0.0429 _diffrn_reflns_number 11965 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 27 _diffrn_reflns_theta_full 27 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _reflns_number_total 2758 _reflns_number_gt 1875 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0504P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2758 _refine_ls_number_parameters 161 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.24 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.24490(6) 0.25 0.72231(5) 0.04512(16) Uani 1 2 d S . . S2 S 0.92329(14) 0.25 1.13747(11) 0.0578(3) Uani 1 2 d SU . . N1 N 0.0957(3) 0.18574(9) 0.8215(2) 0.0446(5) Uani 1 1 d D . . O1 O 0.3187(3) 0.19025(7) 0.58338(18) 0.0546(4) Uani 1 1 d . . . C13 C 0.6932(6) 0.25 1.0079(4) 0.0474(8) Uani 1 2 d SU . . C8 C 0.4436(5) 0.25 0.3999(4) 0.0473(8) Uani 1 2 d S . . H8 H 0.5075 0.25 0.3127 0.057 Uiso 1 2 calc SR . . C7 C 0.3983(3) 0.19668(10) 0.4616(3) 0.0435(6) Uani 1 1 d . . . O2 O -0.0739(3) 0.07056(8) 0.8311(2) 0.0714(5) Uani 1 1 d U . . N2 N 0.5380(5) 0.25 0.9176(4) 0.0609(8) Uani 1 2 d S . . C1 C 0.4430(4) 0.14142(11) 0.3845(3) 0.0464(6) Uani 1 1 d . . . C9 C -0.0976(4) 0.16548(12) 0.7099(3) 0.0566(7) Uani 1 1 d . . . H9A H -0.0604 0.1509 0.6134 0.068 Uiso 1 1 calc R . . H9B H -0.1926 0.1981 0.6804 0.068 Uiso 1 1 calc R . . C11 C 0.1023(4) 0.08838(13) 0.9451(3) 0.0682(8) Uani 1 1 d U . . H11A H 0.1923 0.0551 0.9793 0.082 Uiso 1 1 calc R . . H11B H 0.0567 0.1035 1.0377 0.082 Uiso 1 1 calc R . . C2 C 0.3208(4) 0.09267(12) 0.3979(3) 0.0592(7) Uani 1 1 d . . . H2 H 0.2096 0.0958 0.45 0.071 Uiso 1 1 calc R . . C12 C 0.2278(4) 0.13461(12) 0.8805(3) 0.0589(7) Uani 1 1 d . . . H12A H 0.3455 0.1467 0.9643 0.071 Uiso 1 1 calc R . . H12B H 0.2842 0.1184 0.7939 0.071 Uiso 1 1 calc R . . C6 C 0.6084(4) 0.13598(12) 0.3073(3) 0.0570(7) Uani 1 1 d . . . H6 H 0.6897 0.1683 0.2956 0.068 Uiso 1 1 calc R . . C10 C -0.2092(4) 0.11847(13) 0.7812(4) 0.0694(8) Uani 1 1 d . . . H10A H -0.258 0.1339 0.8722 0.083 Uiso 1 1 calc R . . H10B H -0.3314 0.1056 0.7027 0.083 Uiso 1 1 calc R . . C5 C 0.6539(5) 0.08253(15) 0.2471(3) 0.0761(9) Uani 1 1 d . . . H5 H 0.7673 0.0789 0.1975 0.091 Uiso 1 1 calc R . . C3 C 0.3616(5) 0.04016(13) 0.3357(4) 0.0758(9) Uani 1 1 d . . . H3 H 0.2769 0.0082 0.3433 0.091 Uiso 1 1 calc R . . C4 C 0.5312(6) 0.03511(14) 0.2610(3) 0.0822(10) Uani 1 1 d . . . H4 H 0.5614 -0.0006 0.2203 0.099 Uiso 1 1 calc R . . H1N H 0.069(4) 0.2020(10) 0.9116(16) 0.054(7) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0404(2) 0.0533(3) 0.0451(2) 0 0.01681(17) 0 S2 0.0430(5) 0.0852(7) 0.0466(5) 0 0.0126(4) 0 N1 0.0390(10) 0.0538(13) 0.0436(11) -0.0013(10) 0.0144(9) -0.0009(9) O1 0.0676(11) 0.0537(11) 0.0511(10) 0.0003(8) 0.0315(9) -0.0012(9) C13 0.0428(19) 0.050(2) 0.055(2) 0 0.0230(17) 0 C8 0.051(2) 0.052(2) 0.0419(18) 0 0.0168(15) 0 C7 0.0391(12) 0.0524(15) 0.0393(12) -0.0008(11) 0.0092(10) 0.0016(11) O2 0.0630(12) 0.0549(12) 0.0914(13) 0.0083(11) 0.0057(11) -0.0043(10) N2 0.0393(17) 0.072(2) 0.069(2) 0 0.0078(16) 0 C1 0.0536(14) 0.0493(15) 0.0361(12) 0.0031(11) 0.0093(11) 0.0027(12) C9 0.0417(13) 0.0581(17) 0.0663(16) 0.0074(13) 0.0032(12) -0.0007(12) C11 0.0636(18) 0.070(2) 0.0715(18) 0.0224(16) 0.0151(15) 0.0027(15) C2 0.0677(17) 0.0557(17) 0.0555(15) -0.0030(13) 0.0162(13) -0.0018(14) C12 0.0427(14) 0.0707(19) 0.0610(16) 0.0151(14) 0.0063(12) 0.0044(13) C6 0.0704(17) 0.0548(17) 0.0510(14) 0.0028(13) 0.0245(13) 0.0037(14) C10 0.0466(16) 0.0634(19) 0.095(2) 0.0079(17) 0.0079(15) -0.0101(14) C5 0.097(2) 0.072(2) 0.0685(18) 0.0034(17) 0.0392(17) 0.0221(19) C3 0.103(2) 0.0507(18) 0.0742(19) -0.0029(15) 0.0201(18) -0.0062(17) C4 0.128(3) 0.054(2) 0.069(2) -0.0032(16) 0.030(2) 0.019(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 1.9456(16) 4_565 ? Cu1 O1 1.9456(16) . ? Cu1 N1 2.0510(19) 4_565 ? Cu1 N1 2.0510(19) . ? Cu1 N2 2.247(3) . ? S2 C13 1.659(4) . ? N1 C9 1.480(3) . ? N1 C12 1.480(3) . ? N1 H1N 0.909(2) . ? O1 C7 1.269(2) . ? C13 N2 1.131(4) . ? C8 C7 1.393(3) . ? C8 C7 1.393(3) 4_565 ? C8 H8 0.93 . ? C7 C1 1.491(3) . ? O2 C11 1.396(3) . ? O2 C10 1.418(3) . ? C1 C6 1.384(3) . ? C1 C2 1.394(3) . ? C9 C10 1.504(3) . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C11 C12 1.516(4) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C2 C3 1.370(4) . ? C2 H2 0.93 . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C6 C5 1.391(4) . ? C6 H6 0.93 . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C5 C4 1.372(4) . ? C5 H5 0.93 . ? C3 C4 1.394(4) . ? C3 H3 0.93 . ? C4 H4 0.93 . ? 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 O1 Cu1 O1 90.01(9) 4_565 . ? O1 Cu1 N1 86.79(7) 4_565 4_565 ? O1 Cu1 N1 164.67(8) . 4_565 ? O1 Cu1 N1 164.67(8) 4_565 . ? O1 Cu1 N1 86.79(7) . . ? N1 Cu1 N1 92.36(11) 4_565 . ? O1 Cu1 N2 100.06(7) 4_565 . ? O1 Cu1 N2 100.06(7) . . ? N1 Cu1 N2 95.26(7) 4_565 . ? N1 Cu1 N2 95.26(7) . . ? C9 N1 C12 108.6(2) . . ? C9 N1 Cu1 111.76(14) . . ? C12 N1 Cu1 115.11(14) . . ? C9 N1 H1N 112.8(15) . . ? C12 N1 H1N 104.0(15) . . ? Cu1 N1 H1N 104.4(16) . . ? C7 O1 Cu1 128.19(15) . . ? N2 C13 S2 178.9(3) . . ? C7 C8 C7 123.6(3) . 4_565 ? C7 C8 H8 118.2 . . ? C7 C8 H8 118.2 4_565 . ? O1 C7 C8 124.9(2) . . ? O1 C7 C1 114.7(2) . . ? C8 C7 C1 120.5(2) . . ? C11 O2 C10 110.1(2) . . ? C13 N2 Cu1 175.3(3) . . ? C6 C1 C2 118.8(2) . . ? C6 C1 C7 122.3(2) . . ? C2 C1 C7 118.8(2) . . ? N1 C9 C10 112.4(2) . . ? N1 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N1 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? O2 C11 C12 112.0(2) . . ? O2 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? O2 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C3 C2 C1 121.1(3) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? N1 C12 C11 111.4(2) . . ? N1 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? N1 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 108 . . ? C1 C6 C5 120.4(3) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? O2 C10 C9 111.2(2) . . ? O2 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? O2 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108 . . ? C4 C5 C6 119.9(3) . . ? C4 C5 H5 120 . . ? C6 C5 H5 120 . . ? C2 C3 C4 119.4(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? data_tfacac _database_code_depnum_ccdc_archive 'CCDC 883447' #TrackingRef 'Cu(dkt)(morph)2X.cif' _audit_creation_date 2011-12-08T13:43:13-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1,1,1-trifluoroacetylacetonatochlorobis(morpholine)copper(II) - morpholine solvate ; _chemical_formula_sum 'C17 H31 Cl Cu F3 N3 O5' _chemical_formula_moiety 'C13 H22 Cl Cu F3 N2 O4, C4 H9 N O' _chemical_formula_weight 513.44 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 10.2419(7) _cell_length_b 13.1084(11) _cell_length_c 16.9868(12) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2280.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(1) _cell_measurement_reflns_used 289 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 52.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1068 _exptl_special_details ; ? ; _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.131 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150.0(1) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 27 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0712 _diffrn_reflns_av_unetI/netI 0.1354 _diffrn_reflns_number 18163 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.88 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 4454 _reflns_number_gt 2633 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0512P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4454 _refine_ls_number_parameters 284 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.085 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 0.839 _refine_ls_restrained_S_all 0.842 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.49(2) _refine_diff_density_max 0.637 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.073 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Cl Cl 0.1484 0.1585 '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' 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 0.88937(6) 0.12466(5) 0.48897(3) 0.02869(18) Uani 1 1 d . . . Cl1 Cl 0.97691(11) 0.30437(11) 0.49110(8) 0.0362(4) Uani 1 1 d . . . O3 O 0.6829(4) 0.1033(3) 0.7418(2) 0.0365(11) Uani 1 1 d . . . O4 O 0.6330(3) 0.1305(3) 0.25293(18) 0.0360(10) Uani 1 1 d . . . F2 F 1.1104(3) -0.0852(3) 0.30435(18) 0.0545(10) Uani 1 1 d . . . F1 F 1.2896(3) -0.0201(4) 0.3328(2) 0.0822(17) Uani 1 1 d . . . N2 N 0.7476(5) 0.1471(4) 0.4072(3) 0.0253(13) Uani 1 1 d . . . F3 F 1.1415(4) 0.0664(3) 0.2739(2) 0.0773(14) Uani 1 1 d . . . N1 N 0.7603(4) 0.1338(4) 0.5803(2) 0.0259(12) Uani 1 1 d . . . O1 O 0.9929(4) 0.0668(4) 0.4018(2) 0.0387(11) Uani 1 1 d . . . O2 O 1.0166(4) 0.0734(4) 0.5660(2) 0.0393(11) Uani 1 1 d . . . C10 C 0.6930(6) 0.0495(5) 0.3766(3) 0.0317(15) Uani 1 1 d . . . H10A H 0.6569 0.0104 0.42 0.038 Uiso 1 1 calc R . . H10B H 0.7623 0.0096 0.3528 0.038 Uiso 1 1 calc R . . C1 C 1.1653(5) -0.0018(5) 0.3306(3) 0.0320(15) Uani 1 1 d . . . C11 C 0.5870(5) 0.0697(5) 0.3160(3) 0.0389(17) Uani 1 1 d . . . H11A H 0.5555 0.0052 0.2955 0.047 Uiso 1 1 calc R . . H11B H 0.5143 0.104 0.3413 0.047 Uiso 1 1 calc R . . C13 C 0.7890(6) 0.2116(5) 0.3402(3) 0.0283(15) Uani 1 1 d . . . H13A H 0.8628 0.1801 0.3139 0.034 Uiso 1 1 calc R . . H13B H 0.8165 0.2778 0.3595 0.034 Uiso 1 1 calc R . . C12 C 0.6777(6) 0.2249(5) 0.2821(3) 0.0350(16) Uani 1 1 d . . . H12A H 0.6061 0.26 0.3078 0.042 Uiso 1 1 calc R . . H12B H 0.707 0.2669 0.2385 0.042 Uiso 1 1 calc R . . C3 C 1.1779(5) 0.0177(4) 0.4762(3) 0.0322(14) Uani 1 1 d . . . H3 H 1.2632 -0.0055 0.4709 0.039 Uiso 1 1 calc R . . C8 C 0.6356(6) 0.0389(5) 0.6814(3) 0.0385(16) Uani 1 1 d . . . H8A H 0.5534 0.0656 0.6618 0.046 Uiso 1 1 calc R . . H8B H 0.6195 -0.0285 0.7028 0.046 Uiso 1 1 calc R . . C9 C 0.7318(6) 0.0310(5) 0.6141(3) 0.0366(16) Uani 1 1 d . . . H9A H 0.8123 0.0004 0.6328 0.044 Uiso 1 1 calc R . . H9B H 0.6961 -0.0128 0.5734 0.044 Uiso 1 1 calc R . . C2 C 1.1055(6) 0.0324(4) 0.4101(3) 0.0260(13) Uani 1 1 d . . . C4 C 1.1297(6) 0.0360(5) 0.5519(3) 0.0332(15) Uani 1 1 d . . . C6 C 0.7994(6) 0.2027(5) 0.6444(3) 0.0292(15) Uani 1 1 d . . . H6A H 0.808 0.2715 0.6241 0.035 Uiso 1 1 calc R . . H6B H 0.8837 0.1817 0.6648 0.035 Uiso 1 1 calc R . . N3 N 0.8757(6) -0.1621(4) 0.4954(3) 0.0682(16) Uani 1 1 d D . . C7 C 0.6994(7) 0.2016(6) 0.7106(3) 0.0392(17) Uani 1 1 d . . . H7A H 0.7277 0.2474 0.7521 0.047 Uiso 1 1 calc R . . H7B H 0.6164 0.2261 0.6908 0.047 Uiso 1 1 calc R . . C15 C 0.8864(10) -0.2125(7) 0.4267(4) 0.099(3) Uani 1 1 d D . . H15A H 0.91 -0.164 0.386 0.119 Uiso 1 1 calc R . . H15B H 0.8016 -0.2403 0.4132 0.119 Uiso 1 1 calc R . . C16 C 0.8845(10) -0.2243(7) 0.5650(4) 0.114(4) Uani 1 1 d D . . H16A H 0.8106 -0.2704 0.5674 0.136 Uiso 1 1 calc R . . H16B H 0.8828 -0.1813 0.6115 0.136 Uiso 1 1 calc R . . O5 O 1.0109(8) -0.3481(5) 0.4950(5) 0.146(3) Uani 1 1 d . . . C5 C 1.2093(6) 0.0040(6) 0.6226(3) 0.0490(18) Uani 1 1 d . . . H5A H 1.1771 0.0382 0.6687 0.073 Uiso 1 1 calc R . . H5B H 1.2991 0.022 0.6144 0.073 Uiso 1 1 calc R . . H5C H 1.2022 -0.0684 0.6297 0.073 Uiso 1 1 calc R . . C14 C 0.9864(13) -0.2994(10) 0.4262(5) 0.166(7) Uani 1 1 d D . . H14A H 0.9572 -0.35 0.3884 0.199 Uiso 1 1 calc R . . H14B H 1.0684 -0.2721 0.4069 0.199 Uiso 1 1 calc R . . C17 C 1.0119(9) -0.2855(9) 0.5629(6) 0.110(4) Uani 1 1 d D . . H17A H 1.086 -0.2395 0.5612 0.132 Uiso 1 1 calc R . . H17B H 1.0192 -0.3273 0.6098 0.132 Uiso 1 1 calc R . . H2N H 0.687(6) 0.179(5) 0.424(3) 0.04(2) Uiso 1 1 d . . . H3N H 0.815(3) -0.1133(15) 0.5008(7) 0.24(6) Uiso 1 1 d D . . H1N H 0.678(6) 0.159(5) 0.561(4) 0.07(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0270(3) 0.0431(4) 0.0159(3) 0.0002(4) 0.0008(3) 0.0094(3) Cl1 0.0272(6) 0.0558(9) 0.0256(8) 0.0033(8) -0.0018(7) -0.0140(6) O3 0.052(2) 0.037(3) 0.021(2) 0.0071(19) 0.0104(18) 0.004(2) O4 0.042(2) 0.045(3) 0.0207(18) 0.000(2) -0.0076(17) -0.001(2) F2 0.059(2) 0.057(3) 0.047(2) -0.0237(17) 0.015(2) -0.011(2) F1 0.028(2) 0.158(5) 0.061(3) -0.053(3) 0.0104(18) -0.001(3) N2 0.026(3) 0.035(4) 0.015(2) -0.005(2) 0.004(2) 0.002(3) F3 0.142(4) 0.050(3) 0.040(2) 0.009(2) 0.047(2) 0.022(3) N1 0.028(3) 0.033(3) 0.017(2) 0.006(2) 0.0013(19) 0.004(3) O1 0.036(2) 0.058(3) 0.022(2) -0.004(2) 0.0030(18) 0.022(2) O2 0.035(2) 0.061(3) 0.021(2) 0.000(2) 0.0001(18) 0.025(2) C10 0.044(4) 0.030(4) 0.021(3) -0.005(3) 0.000(3) -0.005(3) C1 0.026(3) 0.039(4) 0.031(3) -0.005(3) 0.002(3) -0.004(3) C11 0.041(4) 0.047(4) 0.029(3) -0.009(3) 0.000(3) -0.008(3) C13 0.034(3) 0.034(4) 0.017(3) 0.000(3) 0.001(3) 0.001(3) C12 0.041(4) 0.042(5) 0.022(3) 0.009(3) -0.009(3) -0.003(3) C3 0.028(3) 0.032(3) 0.036(4) -0.007(3) 0.003(3) 0.008(3) C8 0.046(4) 0.045(4) 0.024(3) 0.004(3) 0.003(3) -0.010(4) C9 0.049(4) 0.038(4) 0.023(3) 0.007(3) 0.002(3) 0.004(3) C2 0.025(3) 0.026(3) 0.026(3) -0.002(2) 0.007(3) -0.010(3) C4 0.036(4) 0.032(4) 0.032(3) -0.003(3) -0.007(3) 0.012(3) C6 0.033(4) 0.034(4) 0.020(3) 0.001(3) 0.004(3) -0.008(3) N3 0.128(5) 0.047(3) 0.030(3) 0.001(3) 0.008(4) 0.012(4) C7 0.053(4) 0.047(5) 0.018(3) 0.001(3) 0.005(3) 0.007(4) C15 0.160(10) 0.092(8) 0.044(5) 0.015(5) 0.020(6) -0.041(8) C16 0.235(13) 0.063(7) 0.042(5) 0.012(4) 0.053(7) 0.073(8) O5 0.233(8) 0.104(5) 0.101(6) 0.010(5) -0.001(7) 0.067(5) C5 0.056(4) 0.059(5) 0.032(3) -0.002(3) -0.010(3) 0.014(4) C14 0.240(14) 0.211(15) 0.047(6) -0.039(8) -0.063(7) 0.155(13) C17 0.117(9) 0.135(11) 0.079(7) 0.013(7) -0.055(7) 0.043(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O2 1.965(4) . ? Cu1 O1 1.973(4) . ? Cu1 N2 2.031(5) . ? Cu1 N1 2.041(4) . ? Cu1 Cl1 2.5208(15) . ? O3 C7 1.403(8) . ? O3 C8 1.414(7) . ? O4 C12 1.409(7) . ? O4 C11 1.417(7) . ? F2 C1 1.307(7) . ? F1 C1 1.295(6) . ? N2 C13 1.479(7) . ? N2 C10 1.489(7) . ? N2 H2N 0.80(6) . ? F3 C1 1.337(7) . ? N1 C6 1.471(7) . ? N1 C9 1.493(8) . ? N1 H1N 0.96(6) . ? O1 C2 1.246(6) . ? O2 C4 1.280(7) . ? C10 C11 1.519(7) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C1 C2 1.548(7) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C13 C12 1.518(7) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C3 C2 1.360(7) . ? C3 C4 1.398(7) . ? C3 H3 0.93 . ? C8 C9 1.513(7) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C4 C5 1.511(7) . ? C6 C7 1.521(8) . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? N3 C15 1.345(9) . ? N3 C16 1.439(8) . ? N3 H3N 0.900(2) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C15 C14 1.532(2) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C16 C17 1.531(2) . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? O5 C14 1.354(10) . ? O5 C17 1.415(10) . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C17 H17A 0.97 . ? C17 H17B 0.97 . ? 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 O2 Cu1 O1 90.68(15) . . ? O2 Cu1 N2 168.3(2) . . ? O1 Cu1 N2 85.79(18) . . ? O2 Cu1 N1 86.76(17) . . ? O1 Cu1 N1 160.2(2) . . ? N2 Cu1 N1 92.77(17) . . ? O2 Cu1 Cl1 94.25(14) . . ? O1 Cu1 Cl1 100.32(14) . . ? N2 Cu1 Cl1 97.39(17) . . ? N1 Cu1 Cl1 99.49(17) . . ? C7 O3 C8 108.4(4) . . ? C12 O4 C11 109.6(4) . . ? C13 N2 C10 109.3(4) . . ? C13 N2 Cu1 113.8(4) . . ? C10 N2 Cu1 112.5(4) . . ? C13 N2 H2N 101(5) . . ? C10 N2 H2N 107(5) . . ? Cu1 N2 H2N 113(4) . . ? C6 N1 C9 108.8(4) . . ? C6 N1 Cu1 115.0(3) . . ? C9 N1 Cu1 111.5(4) . . ? C6 N1 H1N 106(4) . . ? C9 N1 H1N 106(4) . . ? Cu1 N1 H1N 109(4) . . ? C2 O1 Cu1 123.5(3) . . ? C4 O2 Cu1 127.3(3) . . ? N2 C10 C11 110.8(5) . . ? N2 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? F1 C1 F2 106.2(5) . . ? F1 C1 F3 108.9(5) . . ? F2 C1 F3 103.6(5) . . ? F1 C1 C2 114.7(5) . . ? F2 C1 C2 111.7(5) . . ? F3 C1 C2 111.2(5) . . ? O4 C11 C10 111.9(4) . . ? O4 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? O4 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? N2 C13 C12 110.5(5) . . ? N2 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? O4 C12 C13 111.8(5) . . ? O4 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? O4 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? C2 C3 C4 122.9(4) . . ? C2 C3 H3 118.5 . . ? C4 C3 H3 118.5 . . ? O3 C8 C9 111.5(5) . . ? O3 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? O3 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108 . . ? N1 C9 C8 110.8(5) . . ? N1 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? O1 C2 C3 130.4(5) . . ? O1 C2 C1 111.9(4) . . ? C3 C2 C1 117.6(5) . . ? O2 C4 C3 123.9(5) . . ? O2 C4 C5 116.5(5) . . ? C3 C4 C5 119.5(5) . . ? N1 C6 C7 111.0(5) . . ? N1 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108 . . ? C15 N3 C16 115.5(6) . . ? C15 N3 H3N 119.6(10) . . ? C16 N3 H3N 111.2(8) . . ? O3 C7 C6 111.7(5) . . ? O3 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? O3 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? N3 C15 C14 115.0(7) . . ? N3 C15 H15A 108.5 . . ? C14 C15 H15A 108.5 . . ? N3 C15 H15B 108.5 . . ? C14 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? N3 C16 C17 109.3(7) . . ? N3 C16 H16A 109.8 . . ? C17 C16 H16A 109.8 . . ? N3 C16 H16B 109.8 . . ? C17 C16 H16B 109.8 . . ? H16A C16 H16B 108.3 . . ? C14 O5 C17 115.5(7) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O5 C14 C15 118.0(8) . . ? O5 C14 H14A 107.8 . . ? C15 C14 H14A 107.8 . . ? O5 C14 H14B 107.8 . . ? C15 C14 H14B 107.8 . . ? H14A C14 H14B 107.1 . . ? O5 C17 C16 108.5(7) . . ? O5 C17 H17A 110 . . ? C16 C17 H17A 110 . . ? O5 C17 H17B 110 . . ? C16 C17 H17B 110 . . ? H17A C17 H17B 108.4 . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF