# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Ross Forgan' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'James E. Davidson' ; ? # Address 2 ; ; ? # Footnote 2 ; "Francesca P. A. Fabbiani'" '' '' 'Stuart G. Galbraith' '' '' 'David Henderson' '' '' 'Stephen Moggach' '' '' 'Simon Parsons' '' '' 'Peter Tasker' '' '' 'Fraser White' '' '' _publ_contact_author_name 'Ross Forgan' _publ_contact_author_email FORGANROSS@GMAIL.COM _publ_section_title ; Cation and Anion Selectivity of Zwitterionic Salicylaldoxime Metal Salt Extractants ; _publ_requested_coeditor_name S.Moggach@ed.ac.uk _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_name_full ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Nowhere, Nowhere, NO1 4T, UK. ; _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_phone '+44 1865 000000' # Check this file using the IUCr facility at: # http://journals.iucr.org/services/cif/checking/checkfull.html # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures have been sent by mail. ; _publ_requested_category CO # choose from: FI FM FO CI CM CO AD _publ_requested_journal 'Section C' data_dkh13a _database_code_depnum_ccdc_archive 'CCDC 660849' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DKH13A _chemical_melting_point ? _chemical_formula_moiety 'C34 H50 N4 O4 Cu .C1.25 H2.5 Cl2.5' _chemical_formula_sum 'C35.25 H52.50 Cl2.50 Cu N4 O4' _chemical_formula_weight 748.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.0562(7) _cell_length_b 23.6030(12) _cell_length_c 12.4451(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.9300(10) _cell_angle_gamma 90.00 _cell_volume 3949.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7492 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.2 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1582 _exptl_absorpt_coefficient_mu 0.762 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.799432 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35278 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 28.78 _reflns_number_total 9629 _reflns_number_gt 8288 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0483P)^2^+1.6715P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9629 _refine_ls_number_parameters 391 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1091 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.096138(14) 0.031145(9) 0.091405(17) 0.01969(7) Uani 1 1 d . . . O1A O 0.23393(9) 0.02308(5) 0.11505(10) 0.0234(3) Uani 1 1 d . . . C1A C 0.30006(12) -0.00791(7) 0.18740(14) 0.0210(3) Uani 1 1 d . . . C2A C 0.27500(12) -0.04476(7) 0.26529(14) 0.0213(3) Uani 1 1 d . . . C3A C 0.35044(13) -0.07636(7) 0.34156(15) 0.0225(3) Uani 1 1 d . . . H3A H 0.3325 -0.1011 0.3926 0.027 Uiso 1 1 calc R . . C4A C 0.44918(12) -0.07269(7) 0.34484(15) 0.0228(3) Uani 1 1 d . . . C5A C 0.47135(13) -0.03647(7) 0.26601(15) 0.0249(4) Uani 1 1 d . . . H5A H 0.5388 -0.0333 0.2664 0.030 Uiso 1 1 calc R . . C6A C 0.40094(12) -0.00513(7) 0.18781(15) 0.0223(3) Uani 1 1 d . . . C21A C 0.17529(12) -0.04942(7) 0.27366(14) 0.0219(3) Uani 1 1 d . . . H21A H 0.1642 -0.0756 0.3267 0.026 Uiso 1 1 calc R . . N22A N 0.10000(10) -0.02089(6) 0.21496(12) 0.0219(3) Uani 1 1 d . . . O23A O 0.01335(9) -0.03256(6) 0.24456(11) 0.0281(3) Uani 1 1 d . . . H23A H -0.0317 -0.0099 0.2112 0.042 Uiso 1 1 calc R . . C41A C 0.53427(13) -0.10371(8) 0.42969(16) 0.0265(4) Uani 1 1 d D . . C42A C 0.49579(15) -0.14470(9) 0.50248(17) 0.0331(4) Uani 1 1 d D . . H42A H 0.5521 -0.1639 0.5552 0.050 Uiso 1 1 calc R . . H42B H 0.4524 -0.1729 0.4544 0.050 Uiso 1 1 calc R . . H42C H 0.4582 -0.1236 0.5445 0.050 Uiso 1 1 calc R . . C43A C 0.60187(15) -0.06006(9) 0.50663(18) 0.0359(5) Uani 1 1 d D . . H43A H 0.6568 -0.0796 0.5607 0.054 Uiso 1 1 calc R . . H43B H 0.5634 -0.0386 0.5471 0.054 Uiso 1 1 calc R . . H43C H 0.6286 -0.0340 0.4613 0.054 Uiso 1 1 calc R . . C44A C 0.59593(15) -0.13733(9) 0.36784(18) 0.0365(5) Uani 1 1 d D . . H44A H 0.6503 -0.1569 0.4227 0.055 Uiso 1 1 calc R . . H44B H 0.6235 -0.1113 0.3233 0.055 Uiso 1 1 calc R . . H44C H 0.5533 -0.1652 0.3180 0.055 Uiso 1 1 calc R . . C61A C 0.43247(13) 0.02787(8) 0.09985(16) 0.0254(4) Uani 1 1 d . . . H61A H 0.5060 0.0295 0.1230 0.030 Uiso 1 1 calc R . . H61B H 0.4113 0.0064 0.0285 0.030 Uiso 1 1 calc R . . N62A N 0.39444(11) 0.08581(6) 0.07769(13) 0.0248(3) Uani 1 1 d . . . C63A C 0.42419(16) 0.12049(9) 0.17916(17) 0.0351(4) Uani 1 1 d . . . H63A H 0.4977 0.1224 0.2069 0.042 Uiso 1 1 calc R . . H63B H 0.3999 0.1029 0.2384 0.042 Uiso 1 1 calc R . . C64A C 0.3818(2) 0.18003(9) 0.1551(2) 0.0479(6) Uani 1 1 d . . . H64A H 0.4047 0.2034 0.2240 0.058 Uiso 1 1 calc R . . H64B H 0.3083 0.1783 0.1332 0.058 Uiso 1 1 calc R . . C65A C 0.4150(2) 0.20749(10) 0.0610(2) 0.0536(7) Uani 1 1 d . . . H65A H 0.3811 0.2444 0.0410 0.064 Uiso 1 1 calc R . . H65B H 0.4876 0.2144 0.0870 0.064 Uiso 1 1 calc R . . C66A C 0.39035(16) 0.16949(9) -0.04145(19) 0.0400(5) Uani 1 1 d . . . H66A H 0.3173 0.1675 -0.0745 0.048 Uiso 1 1 calc R . . H66B H 0.4190 0.1858 -0.0985 0.048 Uiso 1 1 calc R . . C67A C 0.43113(14) 0.11052(9) -0.01110(17) 0.0325(4) Uani 1 1 d . . . H67A H 0.4112 0.0861 -0.0786 0.039 Uiso 1 1 calc R . . H67B H 0.5047 0.1121 0.0148 0.039 Uiso 1 1 calc R . . O1B O -0.04385(9) 0.04079(5) 0.06384(10) 0.0220(2) Uani 1 1 d . . . C1B C -0.09534(12) 0.08785(7) 0.02966(14) 0.0215(3) Uani 1 1 d . . . C2B C -0.06230(12) 0.13146(7) -0.02923(15) 0.0232(3) Uani 1 1 d . . . C3B C -0.12414(14) 0.17786(8) -0.07206(16) 0.0265(4) Uani 1 1 d . . . H3B H -0.1010 0.2063 -0.1125 0.032 Uiso 1 1 calc R . . C4B C -0.21766(13) 0.18374(8) -0.05755(16) 0.0261(4) Uani 1 1 d . . . C5B C -0.24677(13) 0.14175(8) 0.00485(15) 0.0254(4) Uani 1 1 d . . . H5B H -0.3095 0.1456 0.0185 0.030 Uiso 1 1 calc R . . C6B C -0.18942(12) 0.09460(7) 0.04819(15) 0.0229(3) Uani 1 1 d . . . C21B C 0.03440(13) 0.13147(8) -0.04788(16) 0.0261(4) Uani 1 1 d . . . H21B H 0.0477 0.1600 -0.0955 0.031 Uiso 1 1 calc R . . N22B N 0.10342(10) 0.09578(6) -0.00476(13) 0.0227(3) Uani 1 1 d . . . O23B O 0.18972(9) 0.10653(6) -0.03450(12) 0.0305(3) Uani 1 1 d . . . H23B H 0.2377 0.0894 0.0098 0.046 Uiso 1 1 calc R . . C41B C -0.28238(14) 0.23525(8) -0.10724(17) 0.0303(4) Uani 1 1 d D . . C42B C -0.23955(18) 0.28828(9) -0.0399(2) 0.0446(5) Uani 1 1 d D . . H42D H -0.2810 0.3211 -0.0716 0.067 Uiso 1 1 calc R . . H42E H -0.1716 0.2946 -0.0435 0.067 Uiso 1 1 calc R . . H42F H -0.2386 0.2831 0.0386 0.067 Uiso 1 1 calc R . . C43B C -0.2847(2) 0.24393(12) -0.2300(2) 0.0537(7) Uani 1 1 d D . . H43D H -0.3113 0.2099 -0.2734 0.081 Uiso 1 1 calc R . . H43E H -0.2171 0.2511 -0.2340 0.081 Uiso 1 1 calc R . . H43F H -0.3272 0.2764 -0.2612 0.081 Uiso 1 1 calc R . . C44B C -0.38939(16) 0.22716(10) -0.1036(2) 0.0488(6) Uani 1 1 d D . . H44D H -0.4177 0.1932 -0.1462 0.073 Uiso 1 1 calc R . . H44E H -0.4292 0.2603 -0.1368 0.073 Uiso 1 1 calc R . . H44F H -0.3899 0.2228 -0.0255 0.073 Uiso 1 1 calc R . . C61B C -0.22946(13) 0.04837(8) 0.10645(15) 0.0235(3) Uani 1 1 d . . . H61C H -0.2970 0.0594 0.1081 0.028 Uiso 1 1 calc R . . H61D H -0.2360 0.0134 0.0610 0.028 Uiso 1 1 calc R . . N62B N -0.16947(11) 0.03537(6) 0.22173(13) 0.0241(3) Uani 1 1 d . . . C63B C -0.21537(14) -0.01344(8) 0.26167(16) 0.0291(4) Uani 1 1 d . . . H63C H -0.2176 -0.0461 0.2111 0.035 Uiso 1 1 calc R . . H63D H -0.2846 -0.0038 0.2588 0.035 Uiso 1 1 calc R . . C64B C -0.15829(15) -0.03008(9) 0.38064(17) 0.0341(4) Uani 1 1 d . . . H64C H -0.1933 -0.0615 0.4058 0.041 Uiso 1 1 calc R . . H64D H -0.0912 -0.0436 0.3822 0.041 Uiso 1 1 calc R . . C65B C -0.14858(17) 0.01964(10) 0.46010(18) 0.0401(5) Uani 1 1 d . . . H65C H -0.1050 0.0091 0.5354 0.048 Uiso 1 1 calc R . . H65D H -0.2148 0.0297 0.4674 0.048 Uiso 1 1 calc R . . C66B C -0.10487(17) 0.07007(10) 0.41563(17) 0.0410(5) Uani 1 1 d . . . H66C H -0.0354 0.0616 0.4177 0.049 Uiso 1 1 calc R . . H66D H -0.1041 0.1033 0.4643 0.049 Uiso 1 1 calc R . . C67B C -0.16533(15) 0.08401(9) 0.29543(16) 0.0330(4) Uani 1 1 d . . . H67C H -0.2337 0.0949 0.2941 0.040 Uiso 1 1 calc R . . H67D H -0.1347 0.1165 0.2678 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01483(11) 0.02191(11) 0.02342(12) 0.00194(8) 0.00727(8) -0.00016(7) O1A 0.0158(6) 0.0293(6) 0.0260(6) 0.0048(5) 0.0074(5) -0.0006(5) C1A 0.0159(8) 0.0244(8) 0.0223(8) -0.0031(6) 0.0050(6) 0.0001(6) C2A 0.0177(8) 0.0217(8) 0.0248(8) -0.0038(6) 0.0065(6) -0.0036(6) C3A 0.0216(8) 0.0224(8) 0.0245(8) -0.0005(7) 0.0084(7) -0.0009(6) C4A 0.0188(8) 0.0226(8) 0.0254(9) -0.0012(7) 0.0041(7) 0.0000(6) C5A 0.0169(8) 0.0262(9) 0.0317(9) -0.0012(7) 0.0071(7) -0.0007(6) C6A 0.0184(8) 0.0250(8) 0.0254(9) -0.0003(7) 0.0095(7) -0.0002(6) C21A 0.0204(8) 0.0244(8) 0.0217(8) -0.0008(6) 0.0076(6) -0.0020(6) N22A 0.0159(7) 0.0273(7) 0.0244(7) -0.0009(6) 0.0086(6) -0.0026(6) O23A 0.0172(6) 0.0383(8) 0.0320(7) 0.0088(6) 0.0119(5) 0.0006(5) C41A 0.0216(9) 0.0264(9) 0.0305(9) 0.0031(7) 0.0060(7) 0.0028(7) C42A 0.0268(10) 0.0343(10) 0.0358(11) 0.0085(8) 0.0055(8) 0.0050(8) C43A 0.0278(10) 0.0327(10) 0.0402(11) -0.0013(9) -0.0014(8) 0.0000(8) C44A 0.0317(10) 0.0358(11) 0.0422(12) 0.0042(9) 0.0113(9) 0.0129(9) C61A 0.0176(8) 0.0316(9) 0.0287(9) 0.0019(7) 0.0093(7) -0.0010(7) N62A 0.0236(7) 0.0254(7) 0.0269(8) 0.0026(6) 0.0096(6) -0.0039(6) C63A 0.0402(11) 0.0317(10) 0.0329(10) -0.0045(8) 0.0097(9) -0.0106(9) C64A 0.0611(16) 0.0299(11) 0.0537(14) -0.0074(10) 0.0181(12) -0.0101(10) C65A 0.0600(16) 0.0301(11) 0.0688(17) 0.0058(11) 0.0158(13) -0.0142(11) C66A 0.0322(11) 0.0407(12) 0.0477(13) 0.0154(10) 0.0125(9) -0.0097(9) C67A 0.0245(9) 0.0408(11) 0.0347(10) 0.0076(8) 0.0127(8) -0.0038(8) O1B 0.0170(6) 0.0193(6) 0.0305(7) 0.0019(5) 0.0083(5) 0.0012(4) C1B 0.0182(8) 0.0227(8) 0.0239(8) -0.0023(6) 0.0065(6) -0.0001(6) C2B 0.0185(8) 0.0232(8) 0.0280(9) 0.0009(7) 0.0071(7) 0.0016(6) C3B 0.0245(9) 0.0221(8) 0.0338(10) 0.0021(7) 0.0099(7) 0.0010(7) C4B 0.0221(9) 0.0231(8) 0.0318(9) -0.0021(7) 0.0059(7) 0.0026(7) C5B 0.0199(8) 0.0276(9) 0.0301(9) -0.0041(7) 0.0097(7) 0.0019(7) C6B 0.0185(8) 0.0256(8) 0.0256(8) -0.0029(7) 0.0079(7) -0.0010(6) C21B 0.0230(9) 0.0240(8) 0.0337(10) 0.0035(7) 0.0119(7) -0.0017(7) N22B 0.0173(7) 0.0236(7) 0.0298(8) 0.0008(6) 0.0112(6) -0.0023(5) O23B 0.0173(6) 0.0353(7) 0.0428(8) 0.0131(6) 0.0149(6) 0.0018(5) C41B 0.0261(9) 0.0275(9) 0.0373(10) 0.0027(8) 0.0094(8) 0.0088(7) C42B 0.0448(13) 0.0291(11) 0.0574(15) 0.0019(10) 0.0109(11) 0.0057(9) C43B 0.0546(15) 0.0653(17) 0.0404(13) 0.0120(12) 0.0127(11) 0.0306(13) C44B 0.0252(11) 0.0389(12) 0.0817(18) 0.0111(12) 0.0146(11) 0.0126(9) C61B 0.0171(8) 0.0280(9) 0.0263(9) -0.0005(7) 0.0075(7) -0.0008(7) N62B 0.0226(7) 0.0255(7) 0.0250(8) -0.0019(6) 0.0085(6) -0.0013(6) C63B 0.0243(9) 0.0333(10) 0.0324(10) 0.0020(8) 0.0121(8) -0.0039(8) C64B 0.0295(10) 0.0418(11) 0.0334(10) 0.0074(9) 0.0129(8) 0.0009(8) C65B 0.0365(12) 0.0592(14) 0.0263(10) 0.0005(9) 0.0117(9) 0.0098(10) C66B 0.0437(13) 0.0435(12) 0.0302(11) -0.0090(9) 0.0023(9) 0.0053(10) C67B 0.0326(10) 0.0328(10) 0.0314(10) -0.0056(8) 0.0057(8) 0.0035(8) _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 O1A 1.8820(12) . ? Cu1 O1B 1.9101(12) . ? Cu1 N22A 1.9564(15) . ? Cu1 N22B 1.9599(15) . ? O1A C1A 1.312(2) . ? C1A C6A 1.418(2) . ? C1A C2A 1.421(2) . ? C2A C3A 1.413(2) . ? C2A C21A 1.440(2) . ? C3A C4A 1.379(2) . ? C3A H3A 0.9500 . ? C4A C5A 1.403(2) . ? C4A C41A 1.532(2) . ? C5A C6A 1.383(2) . ? C5A H5A 0.9500 . ? C6A C61A 1.511(2) . ? C21A N22A 1.287(2) . ? C21A H21A 0.9500 . ? N22A O23A 1.3986(17) . ? O23A H23A 0.8400 . ? C41A C42A 1.528(3) . ? C41A C43A 1.533(3) . ? C41A C44A 1.537(3) . ? C42A H42A 0.9800 . ? C42A H42B 0.9800 . ? C42A H42C 0.9800 . ? C43A H43A 0.9800 . ? C43A H43B 0.9800 . ? C43A H43C 0.9800 . ? C44A H44A 0.9800 . ? C44A H44B 0.9800 . ? C44A H44C 0.9800 . ? C61A N62A 1.465(2) . ? C61A H61A 0.9900 . ? C61A H61B 0.9900 . ? N62A C63A 1.460(2) . ? N62A C67A 1.469(2) . ? C63A C64A 1.521(3) . ? C63A H63A 0.9900 . ? C63A H63B 0.9900 . ? C64A C65A 1.525(3) . ? C64A H64A 0.9900 . ? C64A H64B 0.9900 . ? C65A C66A 1.514(3) . ? C65A H65A 0.9900 . ? C65A H65B 0.9900 . ? C66A C67A 1.511(3) . ? C66A H66A 0.9900 . ? C66A H66B 0.9900 . ? C67A H67A 0.9900 . ? C67A H67B 0.9900 . ? O1B C1B 1.326(2) . ? C1B C6B 1.416(2) . ? C1B C2B 1.418(2) . ? C2B C3B 1.403(2) . ? C2B C21B 1.444(2) . ? C3B C4B 1.385(2) . ? C3B H3B 0.9500 . ? C4B C5B 1.392(3) . ? C4B C41B 1.536(2) . ? C5B C6B 1.388(2) . ? C5B H5B 0.9500 . ? C6B C61B 1.507(2) . ? C21B N22B 1.279(2) . ? C21B H21B 0.9500 . ? N22B O23B 1.3908(17) . ? O23B H23B 0.8400 . ? C41B C42B 1.529(3) . ? C41B C44B 1.530(3) . ? C41B C43B 1.532(3) . ? C42B H42D 0.9800 . ? C42B H42E 0.9800 . ? C42B H42F 0.9800 . ? C43B H43D 0.9800 . ? C43B H43E 0.9800 . ? C43B H43F 0.9800 . ? C44B H44D 0.9800 . ? C44B H44E 0.9800 . ? C44B H44F 0.9800 . ? C61B N62B 1.469(2) . ? C61B H61C 0.9900 . ? C61B H61D 0.9900 . ? N62B C67B 1.460(2) . ? N62B C63B 1.476(2) . ? C63B C64B 1.516(3) . ? C63B H63C 0.9900 . ? C63B H63D 0.9900 . ? C64B C65B 1.515(3) . ? C64B H64C 0.9900 . ? C64B H64D 0.9900 . ? C65B C66B 1.516(3) . ? C65B H65C 0.9900 . ? C65B H65D 0.9900 . ? C66B C67B 1.526(3) . ? C66B H66C 0.9900 . ? C66B H66D 0.9900 . ? C67B H67C 0.9900 . ? C67B H67D 0.9900 . ? 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 O1A Cu1 O1B 178.33(5) . . ? O1A Cu1 N22A 91.25(6) . . ? O1B Cu1 N22A 90.42(5) . . ? O1A Cu1 N22B 86.55(6) . . ? O1B Cu1 N22B 91.82(5) . . ? N22A Cu1 N22B 166.95(6) . . ? C1A O1A Cu1 130.89(11) . . ? O1A C1A C6A 118.97(15) . . ? O1A C1A C2A 122.85(15) . . ? C6A C1A C2A 118.18(15) . . ? C3A C2A C1A 119.66(15) . . ? C3A C2A C21A 117.85(15) . . ? C1A C2A C21A 122.43(16) . . ? C4A C3A C2A 122.59(16) . . ? C4A C3A H3A 118.7 . . ? C2A C3A H3A 118.7 . . ? C3A C4A C5A 116.36(16) . . ? C3A C4A C41A 124.57(16) . . ? C5A C4A C41A 119.04(15) . . ? C6A C5A C4A 123.97(16) . . ? C6A C5A H5A 118.0 . . ? C4A C5A H5A 118.0 . . ? C5A C6A C1A 119.19(16) . . ? C5A C6A C61A 118.99(15) . . ? C1A C6A C61A 121.68(16) . . ? N22A C21A C2A 125.16(16) . . ? N22A C21A H21A 117.4 . . ? C2A C21A H21A 117.4 . . ? C21A N22A O23A 112.50(14) . . ? C21A N22A Cu1 127.19(12) . . ? O23A N22A Cu1 120.24(10) . . ? N22A O23A H23A 109.5 . . ? C42A C41A C4A 111.79(15) . . ? C42A C41A C43A 108.50(16) . . ? C4A C41A C43A 109.09(15) . . ? C42A C41A C44A 108.57(16) . . ? C4A C41A C44A 110.03(15) . . ? C43A C41A C44A 108.80(16) . . ? C41A C42A H42A 109.5 . . ? C41A C42A H42B 109.5 . . ? H42A C42A H42B 109.5 . . ? C41A C42A H42C 109.5 . . ? H42A C42A H42C 109.5 . . ? H42B C42A H42C 109.5 . . ? C41A C43A H43A 109.5 . . ? C41A C43A H43B 109.5 . . ? H43A C43A H43B 109.5 . . ? C41A C43A H43C 109.5 . . ? H43A C43A H43C 109.5 . . ? H43B C43A H43C 109.5 . . ? C41A C44A H44A 109.5 . . ? C41A C44A H44B 109.5 . . ? H44A C44A H44B 109.5 . . ? C41A C44A H44C 109.5 . . ? H44A C44A H44C 109.5 . . ? H44B C44A H44C 109.5 . . ? N62A C61A C6A 116.72(14) . . ? N62A C61A H61A 108.1 . . ? C6A C61A H61A 108.1 . . ? N62A C61A H61B 108.1 . . ? C6A C61A H61B 108.1 . . ? H61A C61A H61B 107.3 . . ? C63A N62A C61A 111.32(15) . . ? C63A N62A C67A 110.67(15) . . ? C61A N62A C67A 108.87(14) . . ? N62A C63A C64A 110.52(18) . . ? N62A C63A H63A 109.5 . . ? C64A C63A H63A 109.5 . . ? N62A C63A H63B 109.5 . . ? C64A C63A H63B 109.5 . . ? H63A C63A H63B 108.1 . . ? C63A C64A C65A 110.7(2) . . ? C63A C64A H64A 109.5 . . ? C65A C64A H64A 109.5 . . ? C63A C64A H64B 109.5 . . ? C65A C64A H64B 109.5 . . ? H64A C64A H64B 108.1 . . ? C66A C65A C64A 110.41(18) . . ? C66A C65A H65A 109.6 . . ? C64A C65A H65A 109.6 . . ? C66A C65A H65B 109.6 . . ? C64A C65A H65B 109.6 . . ? H65A C65A H65B 108.1 . . ? C67A C66A C65A 110.98(19) . . ? C67A C66A H66A 109.4 . . ? C65A C66A H66A 109.4 . . ? C67A C66A H66B 109.4 . . ? C65A C66A H66B 109.4 . . ? H66A C66A H66B 108.0 . . ? N62A C67A C66A 111.29(16) . . ? N62A C67A H67A 109.4 . . ? C66A C67A H67A 109.4 . . ? N62A C67A H67B 109.4 . . ? C66A C67A H67B 109.4 . . ? H67A C67A H67B 108.0 . . ? C1B O1B Cu1 126.50(10) . . ? O1B C1B C6B 119.36(15) . . ? O1B C1B C2B 122.92(15) . . ? C6B C1B C2B 117.67(15) . . ? C3B C2B C1B 120.20(16) . . ? C3B C2B C21B 116.53(16) . . ? C1B C2B C21B 123.27(16) . . ? C4B C3B C2B 122.36(17) . . ? C4B C3B H3B 118.8 . . ? C2B C3B H3B 118.8 . . ? C3B C4B C5B 116.47(16) . . ? C3B C4B C41B 120.01(16) . . ? C5B C4B C41B 123.51(16) . . ? C6B C5B C4B 123.77(16) . . ? C6B C5B H5B 118.1 . . ? C4B C5B H5B 118.1 . . ? C5B C6B C1B 119.43(16) . . ? C5B C6B C61B 120.77(15) . . ? C1B C6B C61B 119.61(15) . . ? N22B C21B C2B 124.53(16) . . ? N22B C21B H21B 117.7 . . ? C2B C21B H21B 117.7 . . ? C21B N22B O23B 112.45(14) . . ? C21B N22B Cu1 126.93(12) . . ? O23B N22B Cu1 120.61(10) . . ? N22B O23B H23B 109.5 . . ? C42B C41B C44B 108.64(18) . . ? C42B C41B C43B 109.14(19) . . ? C44B C41B C43B 108.07(19) . . ? C42B C41B C4B 109.55(16) . . ? C44B C41B C4B 111.18(16) . . ? C43B C41B C4B 110.20(16) . . ? C41B C42B H42D 109.5 . . ? C41B C42B H42E 109.5 . . ? H42D C42B H42E 109.5 . . ? C41B C42B H42F 109.5 . . ? H42D C42B H42F 109.5 . . ? H42E C42B H42F 109.5 . . ? C41B C43B H43D 109.5 . . ? C41B C43B H43E 109.5 . . ? H43D C43B H43E 109.5 . . ? C41B C43B H43F 109.5 . . ? H43D C43B H43F 109.5 . . ? H43E C43B H43F 109.5 . . ? C41B C44B H44D 109.5 . . ? C41B C44B H44E 109.5 . . ? H44D C44B H44E 109.5 . . ? C41B C44B H44F 109.5 . . ? H44D C44B H44F 109.5 . . ? H44E C44B H44F 109.5 . . ? N62B C61B C6B 115.62(14) . . ? N62B C61B H61C 108.4 . . ? C6B C61B H61C 108.4 . . ? N62B C61B H61D 108.4 . . ? C6B C61B H61D 108.4 . . ? H61C C61B H61D 107.4 . . ? C67B N62B C61B 110.84(14) . . ? C67B N62B C63B 110.09(15) . . ? C61B N62B C63B 108.00(14) . . ? N62B C63B C64B 111.86(16) . . ? N62B C63B H63C 109.2 . . ? C64B C63B H63C 109.2 . . ? N62B C63B H63D 109.2 . . ? C64B C63B H63D 109.2 . . ? H63C C63B H63D 107.9 . . ? C65B C64B C63B 110.99(17) . . ? C65B C64B H64C 109.4 . . ? C63B C64B H64C 109.4 . . ? C65B C64B H64D 109.4 . . ? C63B C64B H64D 109.4 . . ? H64C C64B H64D 108.0 . . ? C64B C65B C66B 109.81(17) . . ? C64B C65B H65C 109.7 . . ? C66B C65B H65C 109.7 . . ? C64B C65B H65D 109.7 . . ? C66B C65B H65D 109.7 . . ? H65C C65B H65D 108.2 . . ? C65B C66B C67B 110.98(18) . . ? C65B C66B H66C 109.4 . . ? C67B C66B H66C 109.4 . . ? C65B C66B H66D 109.4 . . ? C67B C66B H66D 109.4 . . ? H66C C66B H66D 108.0 . . ? N62B C67B C66B 110.81(17) . . ? N62B C67B H67C 109.5 . . ? C66B C67B H67C 109.5 . . ? N62B C67B H67D 109.5 . . ? C66B C67B H67D 109.5 . . ? H67C C67B H67D 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1A C6A C61A N62A 48.6(2) . . . . ? C6A C61A N62A C63A 58.8(2) . . . . ? C6A C61A N62A C67A -178.89(15) . . . . ? C1B C6B C61B N62B 61.3(2) . . . . ? C6B C61B N62B C63B -175.60(15) . . . . ? C6B C61B N62B C67B 63.72(19) . . . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 28.78 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.465 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.062 # Attachment 'L2.cif' data_RF0007 _database_code_depnum_ccdc_archive 'CCDC 744579' _audit_creation_date 04-12-16 _audit_creation_method CRYSTALS_ver_12.39 _chemical_melting_point ? _cell_length_a 20.1661(7) _cell_length_b 8.5773(3) _cell_length_c 20.6403(7) _cell_angle_alpha 90 _cell_angle_beta 114.661(2) _cell_angle_gamma 90 _cell_volume 3244.5(2) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 _symmetry_space_group_name_Hall '-C 2yc' 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+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C17 H26 N2 O2 # Dc = 1.19 Fooo = 1264.00 Mu = 0.78 M = 290.40 # Found Formula = C17 H26 N2 O2 # Dc = 1.19 FOOO = 1264.00 Mu = 0.78 M = 290.40 _chemical_formula_sum 'C17 H26 N2 O2' _chemical_formula_moiety 'C17 H26 N2 O2' _chemical_formula_weight 290.40 _cell_measurement_reflns_used 7987 _cell_measurement_theta_min 6 _cell_measurement_theta_max 59 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.18 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_max 0.90 _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.078 # Sheldrick geometric approximatio 0.97 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 21572 _reflns_number_total 4287 _diffrn_reflns_av_R_equivalents 0.064 # Number of reflections with Friedels Law is 4287 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4697 _diffrn_reflns_theta_min 2.171 _diffrn_reflns_theta_max 29.918 _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 27.824 _diffrn_measured_fraction_theta_full 0.987 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min -27 _reflns_limit_h_max 25 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.26 _refine_diff_density_max 0.40 _refine_ls_number_reflns 4270 _refine_ls_number_restraints 2 _refine_ls_number_parameters 196 #_refine_ls_R_factor_ref 0.0612 _refine_ls_wR_factor_ref 0.1216 _refine_ls_goodness_of_fit_ref 0.8814 #_reflns_number_all 4270 _refine_ls_R_factor_all 0.0612 _refine_ls_wR_factor_all 0.1216 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 2992 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_gt 0.1182 _refine_ls_shift/su_max 0.000262 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.747E-01 0.00 0.00 0.00 0.00 0.333 ; _publ_section_exptl_refinement ;H atoms placed geometrically after each cycle 063_ALERT_3_B Crystal Probably too Large for Beam Size ..... 0.90 mm 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ........... 0.84 It has been shown (Gorbitz C. H., Acta Cryst. 1999. B55, 1090-1098) that this is not in fact a serious problem. 142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ... 30 Ang. 143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ... 70 Ang. 145_ALERT_4_C su on beta Small or Missing (x 10000) ... 20 Deg. No action taken ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993) SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.16421(5) 0.68105(10) 0.14353(4) 0.0268 1.0000 Uani D . . . . . C1 C 0.15074(6) 0.60614(13) 0.19506(6) 0.0209 1.0000 Uani . . . . . . O2 O 0.07976(5) 1.07853(10) 0.17121(5) 0.0303 1.0000 Uani D . . . . . C2 C 0.11687(6) 0.68163(13) 0.23376(6) 0.0205 1.0000 Uani . . . . . . C3 C 0.10507(6) 0.59862(13) 0.28661(6) 0.0220 1.0000 Uani . . . . . . C4 C 0.12627(6) 0.44391(13) 0.30270(6) 0.0217 1.0000 Uani . . . . . . C5 C 0.15974(6) 0.37360(13) 0.26299(6) 0.0221 1.0000 Uani . . . . . . N6 N 0.14883(5) 0.26074(11) 0.11041(5) 0.0214 1.0000 Uani . . . . . . C6 C 0.17084(6) 0.44967(13) 0.20878(6) 0.0208 1.0000 Uani . . . . . . C21 C 0.09322(6) 0.84384(13) 0.22039(6) 0.0232 1.0000 Uani . . . . . . N22 N 0.10955(5) 0.93003(11) 0.17848(5) 0.0238 1.0000 Uani . . . . . . C41 C 0.11549(7) 0.35549(14) 0.36220(6) 0.0247 1.0000 Uani . . . . . . C42 C 0.18111(8) 0.38641(19) 0.43284(7) 0.0418 1.0000 Uani . . . . . . C43 C 0.10839(10) 0.18003(17) 0.34755(9) 0.0483 1.0000 Uani . . . . . . C44 C 0.04642(8) 0.40871(18) 0.36946(7) 0.0369 1.0000 Uani . . . . . . C61 C 0.20346(6) 0.36132(13) 0.16571(6) 0.0231 1.0000 Uani . . . . . . C63 C 0.09302(6) 0.35670(13) 0.05471(6) 0.0229 1.0000 Uani . . . . . . C64 C 0.03682(6) 0.25391(15) -0.00171(6) 0.0279 1.0000 Uani . . . . . . C65 C 0.07318(7) 0.14631(16) -0.03583(7) 0.0326 1.0000 Uani . . . . . . C66 C 0.13354(8) 0.05342(16) 0.02190(7) 0.0346 1.0000 Uani . . . . . . C67 C 0.18675(7) 0.16094(15) 0.07842(7) 0.0303 1.0000 Uani . . . . . . H31 H 0.0806 0.6528 0.3135 0.0277 1.0000 Uiso . . . . . . H51 H 0.1765 0.2633 0.2742 0.0261 1.0000 Uiso . . . . . . H211 H 0.0638 0.8892 0.2446 0.0290 1.0000 Uiso . . . . . . H421 H 0.1746 0.3293 0.4721 0.0489 1.0000 Uiso . . . . . . H422 H 0.1853 0.5007 0.4433 0.0489 1.0000 Uiso . . . . . . H423 H 0.2266 0.3490 0.4296 0.0489 1.0000 Uiso . . . . . . H431 H 0.1011 0.1258 0.3869 0.0647 1.0000 Uiso . . . . . . H432 H 0.1534 0.1405 0.3445 0.0647 1.0000 Uiso . . . . . . H433 H 0.0651 0.1601 0.3013 0.0647 1.0000 Uiso . . . . . . H441 H 0.0414 0.3491 0.4088 0.0465 1.0000 Uiso . . . . . . H442 H 0.0503 0.5229 0.3811 0.0465 1.0000 Uiso . . . . . . H443 H 0.0029 0.3900 0.3238 0.0465 1.0000 Uiso . . . . . . H611 H 0.2232 0.4380 0.1418 0.0288 1.0000 Uiso . . . . . . H612 H 0.2440 0.2941 0.1987 0.0288 1.0000 Uiso . . . . . . H631 H 0.1173 0.4242 0.0316 0.0287 1.0000 Uiso . . . . . . H632 H 0.0678 0.4235 0.0772 0.0287 1.0000 Uiso . . . . . . H641 H 0.0008 0.3217 -0.0394 0.0331 1.0000 Uiso . . . . . . H642 H 0.0110 0.1897 0.0211 0.0331 1.0000 Uiso . . . . . . H651 H 0.0945 0.2095 -0.0631 0.0386 1.0000 Uiso . . . . . . H652 H 0.0360 0.0726 -0.0690 0.0386 1.0000 Uiso . . . . . . H661 H 0.1604 -0.0082 -0.0004 0.0406 1.0000 Uiso . . . . . . H662 H 0.1110 -0.0190 0.0451 0.0406 1.0000 Uiso . . . . . . H671 H 0.2116 0.2287 0.0558 0.0370 1.0000 Uiso . . . . . . H672 H 0.2240 0.0964 0.1166 0.0370 1.0000 Uiso . . . . . . H1 H 0.1502(8) 0.7706(12) 0.1419(9) 0.0500 1.0000 Uiso D . . . . . H2 H 0.1027(8) 1.1326(18) 0.1527(8) 0.0500 1.0000 Uiso 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 O1 0.0369(5) 0.0181(4) 0.0302(5) 0.0038(3) 0.0187(4) 0.0007(3) C1 0.0215(5) 0.0186(6) 0.0211(5) 0.0008(4) 0.0074(4) -0.0028(4) O2 0.0380(5) 0.0143(4) 0.0412(5) 0.0046(3) 0.0191(4) 0.0031(3) C2 0.0228(5) 0.0149(5) 0.0222(5) -0.0006(4) 0.0078(4) -0.0022(4) C3 0.0243(6) 0.0197(6) 0.0226(5) -0.0020(4) 0.0105(4) -0.0014(4) C4 0.0223(5) 0.0195(6) 0.0209(5) 0.0016(4) 0.0066(4) -0.0026(4) C5 0.0223(6) 0.0163(5) 0.0239(5) 0.0012(4) 0.0057(4) -0.0006(4) N6 0.0239(5) 0.0157(5) 0.0231(5) 0.0000(4) 0.0084(4) 0.0042(4) C6 0.0188(5) 0.0185(6) 0.0230(5) -0.0013(4) 0.0067(4) -0.0006(4) C21 0.0255(6) 0.0174(6) 0.0261(6) -0.0014(4) 0.0102(5) -0.0004(4) N22 0.0267(5) 0.0144(5) 0.0273(5) 0.0009(4) 0.0082(4) 0.0012(4) C41 0.0278(6) 0.0221(6) 0.0239(5) 0.0047(4) 0.0104(5) -0.0013(5) C42 0.0321(7) 0.0602(10) 0.0268(7) 0.0145(6) 0.0060(6) -0.0079(6) C43 0.0828(12) 0.0240(7) 0.0528(9) 0.0058(6) 0.0430(9) -0.0047(7) C44 0.0324(7) 0.0446(8) 0.0366(7) 0.0137(6) 0.0175(6) 0.0018(6) C61 0.0217(5) 0.0208(6) 0.0260(6) -0.0008(4) 0.0093(5) 0.0014(4) C63 0.0249(6) 0.0188(6) 0.0245(5) 0.0034(4) 0.0098(5) 0.0051(4) C64 0.0268(6) 0.0247(6) 0.0273(6) 0.0003(5) 0.0065(5) 0.0047(5) C65 0.0355(7) 0.0319(7) 0.0259(6) -0.0036(5) 0.0083(5) 0.0064(5) C66 0.0375(7) 0.0287(7) 0.0315(7) -0.0072(5) 0.0085(6) 0.0106(5) C67 0.0287(6) 0.0312(7) 0.0291(6) -0.0055(5) 0.0104(5) 0.0095(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2801(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.3635(13) yes O1 . H1 . 0.814(9) no C1 . C2 . 1.4068(16) yes C1 . C6 . 1.3964(16) yes O2 . N22 . 1.3895(12) yes O2 . H2 . 0.850(9) no C2 . C3 . 1.4035(15) yes C2 . C21 . 1.4593(16) yes C3 . C4 . 1.3912(16) yes C3 . H31 . 0.999 no C4 . C5 . 1.3974(16) yes C4 . C41 . 1.5341(15) yes C5 . C6 . 1.3916(16) yes C5 . H51 . 0.999 no N6 . C61 . 1.4872(14) yes N6 . C63 . 1.4785(14) yes N6 . C67 . 1.4747(14) yes C6 . C61 . 1.5119(15) yes C21 . N22 . 1.2811(15) yes C21 . H211 . 1.000 no C41 . C42 . 1.5287(17) yes C41 . C43 . 1.5300(18) yes C41 . C44 . 1.5314(18) yes C42 . H421 . 1.001 no C42 . H422 . 1.000 no C42 . H423 . 1.001 no C43 . H431 . 0.999 no C43 . H432 . 0.995 no C43 . H433 . 1.003 no C44 . H441 . 1.000 no C44 . H442 . 1.004 no C44 . H443 . 0.997 no C61 . H611 . 0.998 no C61 . H612 . 1.000 no C63 . C64 . 1.5220(16) yes C63 . H631 . 0.999 no C63 . H632 . 1.000 no C64 . C65 . 1.5220(17) yes C64 . H641 . 1.000 no C64 . H642 . 0.999 no C65 . C66 . 1.5251(17) yes C65 . H651 . 0.998 no C65 . H652 . 1.001 no C66 . C67 . 1.5225(18) yes C66 . H661 . 0.998 no C66 . H662 . 1.001 no C67 . H671 . 1.001 no C67 . H672 . 0.999 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . H1 . 107.3(12) no O1 . C1 . C2 . 121.87(10) yes O1 . C1 . C6 . 118.40(10) yes C2 . C1 . C6 . 119.73(10) yes N22 . O2 . H2 . 104.9(12) no C1 . C2 . C3 . 119.19(10) yes C1 . C2 . C21 . 121.96(10) yes C3 . C2 . C21 . 118.85(10) yes C2 . C3 . C4 . 122.32(11) yes C2 . C3 . H31 . 118.689 no C4 . C3 . H31 . 118.993 no C3 . C4 . C5 . 116.56(10) yes C3 . C4 . C41 . 122.05(10) yes C5 . C4 . C41 . 121.38(10) yes C4 . C5 . C6 . 123.25(10) yes C4 . C5 . H51 . 118.229 no C6 . C5 . H51 . 118.517 no C61 . N6 . C63 . 110.71(9) yes C61 . N6 . C67 . 108.89(9) yes C63 . N6 . C67 . 110.11(9) yes C1 . C6 . C5 . 118.90(10) yes C1 . C6 . C61 . 121.55(10) yes C5 . C6 . C61 . 119.55(10) yes C2 . C21 . N22 . 121.47(10) yes C2 . C21 . H211 . 119.455 no N22 . C21 . H211 . 119.074 no O2 . N22 . C21 . 112.37(10) yes C4 . C41 . C42 . 108.80(10) yes C4 . C41 . C43 . 111.15(10) yes C42 . C41 . C43 . 109.36(12) yes C4 . C41 . C44 . 111.68(10) yes C42 . C41 . C44 . 108.41(11) yes C43 . C41 . C44 . 107.37(11) yes C41 . C42 . H421 . 109.470 no C41 . C42 . H422 . 109.715 no H421 . C42 . H422 . 109.364 no C41 . C42 . H423 . 109.537 no H421 . C42 . H423 . 109.312 no H422 . C42 . H423 . 109.428 no C41 . C43 . H431 . 109.293 no C41 . C43 . H432 . 109.564 no H431 . C43 . H432 . 109.947 no C41 . C43 . H433 . 109.135 no H431 . C43 . H433 . 109.269 no H432 . C43 . H433 . 109.616 no C41 . C44 . H441 . 109.407 no C41 . C44 . H442 . 109.349 no H441 . C44 . H442 . 109.204 no C41 . C44 . H443 . 109.677 no H441 . C44 . H443 . 109.743 no H442 . C44 . H443 . 109.447 no C6 . C61 . N6 . 112.17(9) yes C6 . C61 . H611 . 108.723 no N6 . C61 . H611 . 108.848 no C6 . C61 . H612 . 108.678 no N6 . C61 . H612 . 108.773 no H611 . C61 . H612 . 109.628 no N6 . C63 . C64 . 110.77(9) yes N6 . C63 . H631 . 109.151 no C64 . C63 . H631 . 109.122 no N6 . C63 . H632 . 109.152 no C64 . C63 . H632 . 109.053 no H631 . C63 . H632 . 109.577 no C63 . C64 . C65 . 110.89(10) yes C63 . C64 . H641 . 108.991 no C65 . C64 . H641 . 109.100 no C63 . C64 . H642 . 109.063 no C65 . C64 . H642 . 109.223 no H641 . C64 . H642 . 109.555 no C64 . C65 . C66 . 109.69(10) yes C64 . C65 . H651 . 109.588 no C66 . C65 . H651 . 109.422 no C64 . C65 . H652 . 109.310 no C66 . C65 . H652 . 109.313 no H651 . C65 . H652 . 109.505 no C65 . C66 . C67 . 111.09(11) yes C65 . C66 . H661 . 109.055 no C67 . C66 . H661 . 109.271 no C65 . C66 . H662 . 108.909 no C67 . C66 . H662 . 108.955 no H661 . C66 . H662 . 109.547 no C66 . C67 . N6 . 111.30(10) yes C66 . C67 . H671 . 108.924 no N6 . C67 . H671 . 109.008 no C66 . C67 . H672 . 109.044 no N6 . C67 . H672 . 109.150 no H671 . C67 . H672 . 109.390 no _exptl_crystal_recrystallization_method 'Slow evaporation from MeOH/CHCL3' # Attachment '[Cu(L2)2(BF4)2].cif' data_pt0541 _database_code_depnum_ccdc_archive 'CCDC 744580' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H52 Cu N4 O4, 2(B F4)' _chemical_formula_sum 'C34 H52 B2 Cu F8 N4 O4' _chemical_formula_weight 817.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4253(3) _cell_length_b 10.7811(4) _cell_length_c 11.2498(4) _cell_angle_alpha 84.524(3) _cell_angle_beta 77.179(2) _cell_angle_gamma 69.818(2) _cell_volume 935.01(6) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4073 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 23.00 _exptl_crystal_description block _exptl_crystal_colour 'light green' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 427 _exptl_absorpt_coefficient_mu 0.667 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.675 _exptl_absorpt_correction_T_max 0.92 _exptl_absorpt_process_details 'SADABS 2004/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'Omega and Phi Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16050 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 30.58 _reflns_number_total 5293 _reflns_number_gt 4241 _reflns_threshold_expression >2sigma(I) _computing_data_collection Smart _computing_cell_refinement Saint _computing_data_reduction Saint _computing_structure_solution 'Dirdif 99.2' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'Platon, Encifer and XCIF' _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. All hydrogen atoms were placed geometrically and allowed to ride on the host atom except for H2 and H62 which were both found on a difference map and fully refined. >>> The Following ALERTS were generated <<< #------------------------------------------ Format: alert-number_ALERT_alert-type_alert-level text 420_ALERT_2_B D-H Without Acceptor O2 - H2 ... ? There is a long range interaction between this donor and the acceptor which is the symmetry equivalent of O1. 912_ALERT_3_B # Missing FCF Reflections Above STH/L=0.6 ...... 429 910_ALERT_3_C # Missing FCF Reflections Below TH(Min) ........ 1 911_ALERT_3_C # Missing FCF Refl Between THmin & STh/l= 0.600 2 The data collection strategy used aimed to achieve a complete data set to 2\q = 53 deg. Some higher angle data were collected in the process and these have been included in the refinement. Please refer to the statistics below. #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 20.82 0.500 0.999 1966 1965 1 23.01 0.550 1.000 2615 2614 1 25.24 0.600 0.999 3377 3374 3 #----------------------------------------------------------- ACTA Min. Res. ---- 27.51 0.650 0.998 4297 4289 8 29.84 0.700 0.957 5370 5140 230 30.58 0.716 0.925 5725 5293 432 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.76 Sadabs corrects for all systematic errors that lead to disparities in the intensities of symmetry-equivalent data. These may include absorption by the mount, crystal decay etc. The crystal was a rather irregular shape, having been cleaved from a larger block; this precluded integration methods for correcting for absorption. 214_ALERT_2_C Atom F2S (Anion/Solvent) ADP max/min Ratio 4.10 prolat 244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for B1S The BF4 slovent molecules are slightly disordered but modelling with ADPs was more suitable. 222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.57 Ratio All of the ADPs for the hydrogen atoms are well within reasonable limits with the largest being 0.05. This is the hydrogen at the end of the piperidine group which would be expected to have the highest thermal motion. ; _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^)+(0.0931P)^2^+0.3490P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary patterson _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5293 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1560 _refine_ls_wR_factor_gt 0.1485 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.0000 0.0000 0.01793(13) Uani 1 2 d S . . C1 C 0.3717(3) -0.1166(2) -0.09390(19) 0.0170(4) Uani 1 1 d . . . C2 C 0.3490(3) -0.1132(2) -0.21575(19) 0.0178(4) Uani 1 1 d . . . C3 C 0.4953(3) -0.1579(2) -0.30998(19) 0.0200(4) Uani 1 1 d . . . H3 H 0.4785 -0.1534 -0.3912 0.024 Uiso 1 1 calc R . . C4 C 0.6623(3) -0.2080(2) -0.2901(2) 0.0205(4) Uani 1 1 d . . . C5 C 0.6824(3) -0.2157(2) -0.1697(2) 0.0190(4) Uani 1 1 d . . . H5 H 0.7951 -0.2521 -0.1525 0.023 Uiso 1 1 calc R . . C6 C 0.5412(3) -0.1715(2) -0.07365(19) 0.0176(4) Uani 1 1 d . . . O1 O 0.2428(2) -0.07009(16) -0.00062(14) 0.0206(3) Uani 1 1 d . . . O2 O -0.1065(2) 0.00684(19) -0.22606(16) 0.0279(4) Uani 1 1 d . . . H2 H -0.186(5) 0.022(4) -0.173(3) 0.045(10) Uiso 1 1 d . . . C21 C 0.1822(3) -0.0688(2) -0.24989(19) 0.0194(4) Uani 1 1 d . . . H21 H 0.1789 -0.0711 -0.3335 0.023 Uiso 1 1 calc R . . N22 N 0.0389(2) -0.02664(19) -0.17388(17) 0.0199(4) Uani 1 1 d . . . C41 C 0.8145(3) -0.2506(2) -0.3991(2) 0.0218(4) Uani 1 1 d . . . C42 C 0.9876(3) -0.3097(3) -0.3584(2) 0.0275(5) Uani 1 1 d . . . H42A H 1.0046 -0.2441 -0.3125 0.041 Uiso 1 1 calc R . . H42B H 1.0813 -0.3349 -0.4302 0.041 Uiso 1 1 calc R . . H42C H 0.9877 -0.3881 -0.3064 0.041 Uiso 1 1 calc R . . C43 C 0.7933(3) -0.3561(3) -0.4712(2) 0.0312(5) Uani 1 1 d . . . H43A H 0.8881 -0.3804 -0.5424 0.047 Uiso 1 1 calc R . . H43B H 0.6829 -0.3206 -0.4982 0.047 Uiso 1 1 calc R . . H43C H 0.7952 -0.4345 -0.4189 0.047 Uiso 1 1 calc R . . C44 C 0.8184(3) -0.1297(3) -0.4826(2) 0.0304(5) Uani 1 1 d . . . H44A H 0.8359 -0.0637 -0.4375 0.046 Uiso 1 1 calc R . . H44B H 0.7086 -0.0914 -0.5100 0.046 Uiso 1 1 calc R . . H44C H 0.9132 -0.1570 -0.5535 0.046 Uiso 1 1 calc R . . C61 C 0.5681(3) -0.1752(2) 0.05476(19) 0.0186(4) Uani 1 1 d . . . H61A H 0.5011 -0.0881 0.0920 0.022 Uiso 1 1 calc R . . H61B H 0.6918 -0.1914 0.0526 0.022 Uiso 1 1 calc R . . N62 N 0.5135(2) -0.28124(19) 0.13318(17) 0.0193(4) Uani 1 1 d . . . C63 C 0.4956(3) -0.2574(3) 0.2656(2) 0.0286(5) Uani 1 1 d . . . H63A H 0.4085 -0.1696 0.2875 0.034 Uiso 1 1 calc R . . H63B H 0.6072 -0.2577 0.2804 0.034 Uiso 1 1 calc R . . C64 C 0.4407(4) -0.3634(3) 0.3450(2) 0.0382(7) Uani 1 1 d . . . H64A H 0.3250 -0.3586 0.3349 0.046 Uiso 1 1 calc R . . H64B H 0.4331 -0.3477 0.4317 0.046 Uiso 1 1 calc R . . C65 C 0.5690(4) -0.5002(3) 0.3109(3) 0.0413(7) Uani 1 1 d . . . H65A H 0.6823 -0.5078 0.3281 0.050 Uiso 1 1 calc R . . H65B H 0.5281 -0.5680 0.3610 0.050 Uiso 1 1 calc R . . C66 C 0.5896(4) -0.5245(3) 0.1768(3) 0.0380(6) Uani 1 1 d . . . H66A H 0.6802 -0.6109 0.1548 0.046 Uiso 1 1 calc R . . H66B H 0.4799 -0.5280 0.1617 0.046 Uiso 1 1 calc R . . C67 C 0.6385(3) -0.4162(2) 0.0974(2) 0.0273(5) Uani 1 1 d . . . H67A H 0.7556 -0.4209 0.1042 0.033 Uiso 1 1 calc R . . H67B H 0.6418 -0.4308 0.0112 0.033 Uiso 1 1 calc R . . B1S B 1.0471(4) 0.6787(3) 0.1295(3) 0.0317(6) Uani 1 1 d . . . F1S F 1.0448(3) 0.55322(19) 0.1246(2) 0.0554(5) Uani 1 1 d . . . F2S F 1.2086(3) 0.6734(3) 0.1316(3) 0.1094(14) Uani 1 1 d . . . F3S F 0.9215(5) 0.7384(3) 0.2252(2) 0.1000(11) Uani 1 1 d . . . F4S F 0.9995(3) 0.7544(2) 0.0285(2) 0.0541(5) Uani 1 1 d . . . H62 H 0.424(4) -0.278(3) 0.120(2) 0.014(6) 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 0.01253(19) 0.0232(2) 0.01691(19) -0.00144(13) -0.00310(13) -0.00418(14) C1 0.0160(10) 0.0154(9) 0.0198(10) 0.0017(7) -0.0037(7) -0.0060(8) C2 0.0157(10) 0.0170(10) 0.0196(10) 0.0006(7) -0.0027(7) -0.0049(8) C3 0.0203(10) 0.0211(10) 0.0180(10) 0.0016(8) -0.0034(8) -0.0071(8) C4 0.0187(10) 0.0180(10) 0.0215(10) 0.0012(8) -0.0005(8) -0.0048(8) C5 0.0132(9) 0.0190(10) 0.0236(10) 0.0032(8) -0.0038(7) -0.0049(8) C6 0.0162(10) 0.0172(10) 0.0200(10) 0.0024(7) -0.0042(7) -0.0067(8) O1 0.0143(7) 0.0269(8) 0.0184(7) -0.0022(6) -0.0022(5) -0.0043(6) O2 0.0141(8) 0.0453(11) 0.0224(8) -0.0037(7) -0.0065(6) -0.0049(7) C21 0.0191(10) 0.0210(10) 0.0175(9) 0.0006(8) -0.0046(8) -0.0056(8) N22 0.0143(8) 0.0247(9) 0.0213(9) -0.0002(7) -0.0065(7) -0.0054(7) C41 0.0146(10) 0.0257(11) 0.0211(10) 0.0001(8) -0.0001(8) -0.0039(8) C42 0.0155(11) 0.0337(13) 0.0285(12) -0.0005(10) -0.0005(8) -0.0044(9) C43 0.0243(12) 0.0328(14) 0.0345(13) -0.0091(10) -0.0011(10) -0.0080(10) C44 0.0254(12) 0.0331(13) 0.0252(12) 0.0049(9) 0.0031(9) -0.0070(10) C61 0.0168(10) 0.0206(10) 0.0205(10) 0.0018(8) -0.0054(7) -0.0085(8) N62 0.0149(9) 0.0262(10) 0.0196(9) 0.0039(7) -0.0064(7) -0.0097(8) C63 0.0276(13) 0.0419(15) 0.0178(10) 0.0016(9) -0.0070(9) -0.0125(11) C64 0.0335(14) 0.065(2) 0.0223(12) 0.0156(12) -0.0106(10) -0.0260(14) C65 0.0397(16) 0.0511(18) 0.0427(16) 0.0273(13) -0.0230(13) -0.0254(14) C66 0.0450(17) 0.0297(14) 0.0455(16) 0.0145(12) -0.0173(13) -0.0193(13) C67 0.0269(12) 0.0212(11) 0.0319(12) 0.0043(9) -0.0062(9) -0.0069(10) B1S 0.0282(15) 0.0328(15) 0.0347(15) 0.0032(12) -0.0040(11) -0.0135(12) F1S 0.0548(13) 0.0357(10) 0.0803(15) 0.0093(9) -0.0188(11) -0.0203(9) F2S 0.0731(17) 0.107(2) 0.196(3) 0.103(2) -0.101(2) -0.0722(17) F3S 0.141(3) 0.0759(18) 0.0613(16) -0.0217(13) 0.0320(16) -0.0366(18) F4S 0.0485(12) 0.0537(12) 0.0744(14) 0.0273(10) -0.0385(10) -0.0264(10) _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 1.9197(15) . ? Cu1 O1 1.9197(15) 2 ? Cu1 N22 1.9426(18) . ? Cu1 N22 1.9426(18) 2 ? C1 O1 1.323(2) . ? C1 C6 1.406(3) . ? C1 C2 1.421(3) . ? C2 C3 1.408(3) . ? C2 C21 1.447(3) . ? C3 C4 1.384(3) . ? C3 H3 0.9500 . ? C4 C5 1.393(3) . ? C4 C41 1.537(3) . ? C5 C6 1.395(3) . ? C5 H5 0.9500 . ? C6 C61 1.506(3) . ? O2 N22 1.396(2) . ? O2 H2 0.78(4) . ? C21 N22 1.278(3) . ? C21 H21 0.9500 . ? C41 C42 1.530(3) . ? C41 C44 1.538(3) . ? C41 C43 1.537(3) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C61 N62 1.512(3) . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? N62 C67 1.501(3) . ? N62 C63 1.502(3) . ? N62 H62 0.79(3) . ? C63 C64 1.518(4) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C64 C65 1.521(5) . ? C64 H64A 0.9900 . ? C64 H64B 0.9900 . ? C65 C66 1.518(4) . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C66 C67 1.517(3) . ? C66 H66A 0.9900 . ? C66 H66B 0.9900 . ? C67 H67A 0.9900 . ? C67 H67B 0.9900 . ? B1S F2S 1.348(4) . ? B1S F3S 1.359(4) . ? B1S F1S 1.366(4) . ? B1S F4S 1.385(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 O1 180.0 . 2 ? O1 Cu1 N22 92.06(7) . . ? O1 Cu1 N22 87.94(7) 2 . ? O1 Cu1 N22 87.94(7) . 2 ? O1 Cu1 N22 92.06(7) 2 2 ? N22 Cu1 N22 180.0 . 2 ? O1 C1 C6 119.28(18) . . ? O1 C1 C2 123.43(19) . . ? C6 C1 C2 117.28(19) . . ? C3 C2 C1 119.21(19) . . ? C3 C2 C21 116.98(19) . . ? C1 C2 C21 123.79(19) . . ? C4 C3 C2 123.3(2) . . ? C4 C3 H3 118.4 . . ? C2 C3 H3 118.4 . . ? C3 C4 C5 117.0(2) . . ? C3 C4 C41 119.60(19) . . ? C5 C4 C41 123.4(2) . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C1 121.53(19) . . ? C5 C6 C61 120.30(19) . . ? C1 C6 C61 118.10(19) . . ? C1 O1 Cu1 128.13(14) . . ? N22 O2 H2 107(3) . . ? N22 C21 C2 123.67(19) . . ? N22 C21 H21 118.2 . . ? C2 C21 H21 118.2 . . ? C21 N22 O2 114.05(18) . . ? C21 N22 Cu1 128.64(15) . . ? O2 N22 Cu1 117.28(14) . . ? C42 C41 C4 111.86(19) . . ? C42 C41 C44 108.6(2) . . ? C4 C41 C44 109.26(19) . . ? C42 C41 C43 107.85(19) . . ? C4 C41 C43 109.77(19) . . ? C44 C41 C43 109.4(2) . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C41 C43 H43A 109.5 . . ? C41 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C41 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C41 C44 H44A 109.5 . . ? C41 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C41 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C6 C61 N62 112.43(17) . . ? C6 C61 H61A 109.1 . . ? N62 C61 H61A 109.1 . . ? C6 C61 H61B 109.1 . . ? N62 C61 H61B 109.1 . . ? H61A C61 H61B 107.9 . . ? C67 N62 C63 111.31(18) . . ? C67 N62 C61 110.84(17) . . ? C63 N62 C61 110.27(17) . . ? C67 N62 H62 106.8(19) . . ? C63 N62 H62 110.3(19) . . ? C61 N62 H62 107.2(18) . . ? N62 C63 C64 110.6(2) . . ? N62 C63 H63A 109.5 . . ? C64 C63 H63A 109.5 . . ? N62 C63 H63B 109.5 . . ? C64 C63 H63B 109.5 . . ? H63A C63 H63B 108.1 . . ? C63 C64 C65 110.8(2) . . ? C63 C64 H64A 109.5 . . ? C65 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? C65 C64 H64B 109.5 . . ? H64A C64 H64B 108.1 . . ? C66 C65 C64 110.6(2) . . ? C66 C65 H65A 109.5 . . ? C64 C65 H65A 109.5 . . ? C66 C65 H65B 109.5 . . ? C64 C65 H65B 109.5 . . ? H65A C65 H65B 108.1 . . ? C67 C66 C65 111.1(2) . . ? C67 C66 H66A 109.4 . . ? C65 C66 H66A 109.4 . . ? C67 C66 H66B 109.4 . . ? C65 C66 H66B 109.4 . . ? H66A C66 H66B 108.0 . . ? N62 C67 C66 112.0(2) . . ? N62 C67 H67A 109.2 . . ? C66 C67 H67A 109.2 . . ? N62 C67 H67B 109.2 . . ? C66 C67 H67B 109.2 . . ? H67A C67 H67B 107.9 . . ? F2S B1S F3S 116.4(3) . . ? F2S B1S F1S 109.2(3) . . ? F3S B1S F1S 107.4(3) . . ? F2S B1S F4S 107.6(2) . . ? F3S B1S F4S 104.6(3) . . ? F1S B1S F4S 111.7(3) . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.380 _refine_diff_density_min -1.129 _refine_diff_density_rms 0.097 # Attachment '[Cu(L2)2(TFA)2].cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 744581' _audit_creation_date 04-10-22 _audit_creation_method CRYSTALS_ver_12.39 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 11.5737(9) _cell_length_b 14.2590(11) _cell_length_c 12.8374(10) _cell_angle_alpha 90 _cell_angle_beta 108.688(3) _cell_angle_gamma 90 _cell_volume 2006.9(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C38 H52 Cu1 F6 N4 O8 # Dc = 1.44 Fooo = 910.00 Mu = 6.28 M = 435.19 # Found Formula = C38 H52 Cu1 F6 N4 O8 # Dc = 1.44 FOOO = 910.00 Mu = 6.28 M = 435.19 _chemical_formula_sum 'C38 H52 Cu1 F6 N4 O8' _chemical_formula_moiety 'C38 H52 Cu1 F6 N4 O8' _chemical_compound_source ? _chemical_formula_weight 870.39 _cell_measurement_reflns_used 7582 _cell_measurement_theta_min 5 _cell_measurement_theta_max 58 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_max 0.52 _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 910 _exptl_absorpt_coefficient_mu 0.628 # Sheldrick geometric approximatio 0.87 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.65 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 14419 _reflns_number_total 4581 _diffrn_reflns_av_R_equivalents 0.050 # Number of reflections with Friedels Law is 4581 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3480 _diffrn_reflns_theta_min 2.064 _diffrn_reflns_theta_max 29.052 _diffrn_measured_fraction_theta_max 0.855 _diffrn_reflns_theta_full 25.276 _diffrn_measured_fraction_theta_full 0.960 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -15 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_diffrn_Wilson_B_factor 1.47 _oxford_diffrn_Wilson_scale 4.41 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.82 _refine_diff_density_max 0.98 _refine_ls_number_reflns 3391 _refine_ls_number_restraints 21 _refine_ls_number_parameters 259 #_refine_ls_R_factor_ref 0.1161 _refine_ls_wR_factor_ref 0.1700 _refine_ls_goodness_of_fit_ref 1.1193 #_reflns_number_all 3391 _refine_ls_R_factor_all 0.1161 _refine_ls_wR_factor_all 0.1700 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 2563 _refine_ls_R_factor_gt 0.0844 _refine_ls_wR_factor_gt 0.1577 _refine_ls_shift/su_max 0.000147 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.00 7.05 0.00 0.00 0.00 0.333 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993) SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C61 C 1.2178(5) 0.2418(4) 1.2228(4) 0.0218 1.0000 Uani . . . . . . C63 C 1.3267(5) 0.2062(5) 1.4201(5) 0.0257 1.0000 Uani . . . . . . C64 C 1.4102(6) 0.1376(5) 1.4981(5) 0.0290 1.0000 Uani . . . . . . C65 C 1.5327(5) 0.1331(5) 1.4784(5) 0.0321 1.0000 Uani . . . . . . C66 C 1.5130(5) 0.1043(5) 1.3584(5) 0.0298 1.0000 Uani . . . . . . C67 C 1.4256(5) 0.1714(5) 1.2794(5) 0.0251 1.0000 Uani . . . . . . C21 C 0.8078(5) 0.0936(4) 1.0639(4) 0.0212 1.0000 Uani . . . . . . C41 C 0.8683(7) 0.3348(5) 1.3567(6) 0.0420 1.0000 Uani . U . . . . C42 C 0.8624(9) 0.4339(7) 1.3129(9) 0.0729 1.0000 Uani . U . . . . C43 C 0.7429(7) 0.3052(6) 1.3569(7) 0.0529 1.0000 Uani . U . . . . C44 C 0.9525(8) 0.3327(10) 1.4758(8) 0.0949 1.0000 Uani . . . . . . O1 O 1.0655(3) 0.1093(3) 1.0863(3) 0.0238 1.0000 Uani . . . . . . C1 C 1.0176(5) 0.1571(4) 1.1488(4) 0.0213 1.0000 Uani . . . . . . C2 C 0.8943(5) 0.1486(4) 1.1454(4) 0.0219 1.0000 Uani . . . . . . C3 C 0.8496(5) 0.2037(5) 1.2156(5) 0.0245 1.0000 Uani . . . . . . C4 C 0.9189(6) 0.2702(5) 1.2857(5) 0.0272 1.0000 Uani . . . . . . C5 C 1.0394(5) 0.2811(4) 1.2855(5) 0.0236 1.0000 Uani . . . . . . C6 C 1.0883(5) 0.2263(4) 1.2207(4) 0.0210 1.0000 Uani . . . . . . Cu1 Cu 1.0000 0.0000 1.0000 0.0214 1.0000 Uani S . . . . . O3 O 1.2226(3) -0.0061(4) 1.2778(3) 0.0302 1.0000 Uani . . . . . . O2 O 1.0482(4) -0.0842(3) 1.1953(4) 0.0349 1.0000 Uani . . . . . . O23 O 0.7298(3) 0.0048(4) 0.9148(3) 0.0311 1.0000 Uani . . . . . . N6 N 1.3058(4) 0.1770(4) 1.3023(4) 0.0231 1.0000 Uani . . . . . . N22 N 0.8346(4) 0.0404(4) 0.9935(4) 0.0219 1.0000 Uani . . . . . . C7 C 1.1201(6) -0.0414(5) 1.2709(5) 0.0282 1.0000 Uani . . . . . . C8 C 1.0864(6) -0.0306(5) 1.3777(5) 0.0348 1.0000 Uani . . . . . . F1 F 1.1087(6) 0.0547(4) 1.4201(4) 0.0857 1.0000 Uani . . . . . . F2 F 0.9747(5) -0.0477(5) 1.3665(4) 0.0957 1.0000 Uani . . . . . . F3 F 1.1549(6) -0.0854(5) 1.4550(4) 0.1051 1.0000 Uani . . . . . . H611 H 1.2420 0.3077 1.2460 0.0270 1.0000 Uiso . . . . . . H612 H 1.2228 0.2309 1.1476 0.0270 1.0000 Uiso . . . . . . H631 H 1.3652 0.2701 1.4310 0.0322 1.0000 Uiso . . . . . . H632 H 1.2469 0.2094 1.4344 0.0322 1.0000 Uiso . . . . . . H641 H 1.4226 0.1584 1.5752 0.0336 1.0000 Uiso . . . . . . H642 H 1.3713 0.0743 1.4860 0.0336 1.0000 Uiso . . . . . . H651 H 1.5859 0.0857 1.5290 0.0369 1.0000 Uiso . . . . . . H652 H 1.5731 0.1959 1.4925 0.0369 1.0000 Uiso . . . . . . H661 H 1.5929 0.1050 1.3443 0.0367 1.0000 Uiso . . . . . . H662 H 1.4780 0.0394 1.3463 0.0367 1.0000 Uiso . . . . . . H671 H 1.4622 0.2355 1.2881 0.0321 1.0000 Uiso . . . . . . H672 H 1.4102 0.1493 1.2021 0.0321 1.0000 Uiso . . . . . . H211 H 0.7205 0.0967 1.0614 0.0270 1.0000 Uiso . . . . . . H421 H 0.9459 0.4531 1.3132 0.0941 1.0000 Uiso . . . . . . H422 H 0.8348 0.4768 1.3618 0.0941 1.0000 Uiso . . . . . . H423 H 0.8045 0.4361 1.2370 0.0941 1.0000 Uiso . . . . . . H431 H 0.7467 0.2395 1.3861 0.0717 1.0000 Uiso . . . . . . H432 H 0.7151 0.3484 1.4056 0.0717 1.0000 Uiso . . . . . . H433 H 0.6848 0.3077 1.2808 0.0717 1.0000 Uiso . . . . . . H441 H 0.9574 0.2672 1.5051 0.1176 1.0000 Uiso . . . . . . H442 H 0.9204 0.3755 1.5212 0.1176 1.0000 Uiso . . . . . . H443 H 1.0364 0.3535 1.4787 0.1176 1.0000 Uiso . . . . . . H31 H 0.7637 0.1940 1.2141 0.0314 1.0000 Uiso . . . . . . H51 H 1.0920 0.3304 1.3333 0.0280 1.0000 Uiso . . . . . . H231 H 0.7525 -0.0131 0.8495 0.0500 1.0000 Uiso . . . . . . H61 H 1.2733 0.1204 1.2935 0.0284 1.0000 Uiso . . . . . . 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 C61 0.018(3) 0.033(4) 0.015(3) 0.001(2) 0.006(2) -0.003(3) C63 0.026(3) 0.032(4) 0.021(3) -0.002(3) 0.009(2) 0.001(3) C64 0.025(3) 0.029(4) 0.028(3) -0.005(3) 0.001(3) 0.000(3) C65 0.019(3) 0.040(4) 0.033(3) 0.000(3) 0.001(3) 0.009(3) C66 0.021(3) 0.030(4) 0.040(4) -0.004(3) 0.012(3) 0.005(3) C67 0.016(3) 0.033(4) 0.028(3) -0.007(3) 0.010(2) -0.003(3) C21 0.019(3) 0.024(3) 0.024(3) 0.001(2) 0.011(2) -0.002(2) C41 0.049(4) 0.037(4) 0.056(4) -0.015(3) 0.040(3) -0.007(3) C42 0.087(5) 0.054(5) 0.101(5) -0.013(4) 0.063(4) 0.006(4) C43 0.050(4) 0.054(5) 0.072(4) -0.022(4) 0.044(4) -0.002(3) C44 0.050(5) 0.186(13) 0.058(6) -0.071(7) 0.031(5) -0.031(7) O1 0.024(2) 0.021(2) 0.032(2) 0.0001(18) 0.0149(18) 0.0013(17) C1 0.021(3) 0.023(3) 0.022(3) 0.003(2) 0.010(2) 0.005(2) C2 0.024(3) 0.024(3) 0.019(3) 0.003(2) 0.009(2) -0.001(3) C3 0.019(3) 0.027(4) 0.029(3) 0.001(3) 0.009(2) 0.000(3) C4 0.031(3) 0.030(4) 0.025(3) 0.002(3) 0.015(3) -0.003(3) C5 0.025(3) 0.024(3) 0.022(3) -0.003(2) 0.007(2) -0.002(3) C6 0.020(3) 0.024(3) 0.019(3) 0.008(2) 0.007(2) 0.003(2) Cu1 0.0173(5) 0.0241(6) 0.0241(5) -0.0044(5) 0.0086(4) 0.0010(5) O3 0.031(2) 0.031(2) 0.030(2) -0.001(2) 0.0124(17) 0.001(2) O2 0.033(2) 0.040(3) 0.032(2) -0.005(2) 0.011(2) -0.012(2) O23 0.025(2) 0.041(3) 0.028(2) -0.011(2) 0.0094(16) -0.002(2) N6 0.020(2) 0.026(3) 0.026(3) -0.002(2) 0.010(2) 0.001(2) N22 0.022(2) 0.024(3) 0.019(2) 0.001(2) 0.0061(19) -0.004(2) C7 0.029(3) 0.031(4) 0.025(3) 0.005(3) 0.010(3) 0.000(3) C8 0.029(3) 0.041(5) 0.035(4) 0.001(3) 0.012(3) -0.004(3) F1 0.129(5) 0.087(5) 0.068(3) -0.043(3) 0.069(4) -0.042(4) F2 0.054(3) 0.187(7) 0.064(3) -0.038(4) 0.042(3) -0.043(4) F3 0.126(5) 0.145(7) 0.063(3) 0.061(4) 0.057(4) 0.065(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.5252(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C61 . C6 . 1.507(7) yes C61 . N6 . 1.505(7) yes C61 . H611 . 0.999 no C61 . H612 . 0.998 no C63 . C64 . 1.507(8) yes C63 . N6 . 1.511(7) yes C63 . H631 . 1.004 no C63 . H632 . 0.999 no C64 . C65 . 1.519(9) yes C64 . H641 . 0.999 no C64 . H642 . 0.999 no C65 . C66 . 1.539(9) yes C65 . H651 . 1.000 no C65 . H652 . 0.999 no C66 . C67 . 1.520(9) yes C66 . H661 . 0.998 no C66 . H662 . 1.002 no C67 . N6 . 1.509(7) yes C67 . H671 . 0.999 no C67 . H672 . 1.001 no C21 . C2 . 1.428(8) yes C21 . N22 . 1.292(7) yes C21 . H211 . 1.001 no C41 . C42 . 1.515(12) yes C41 . C43 . 1.513(10) yes C41 . C44 . 1.527(12) yes C41 . C4 . 1.537(9) yes C42 . H421 . 1.002 no C42 . H422 . 0.999 no C42 . H423 . 0.991 no C43 . H431 . 1.004 no C43 . H432 . 1.001 no C43 . H433 . 0.994 no C44 . H441 . 1.003 no C44 . H442 . 0.993 no C44 . H443 . 1.005 no O1 . C1 . 1.305(7) yes O1 . Cu1 . 1.921(4) yes C1 . C2 . 1.419(8) yes C1 . C6 . 1.418(8) yes C2 . C3 . 1.413(8) yes C3 . C4 . 1.374(9) yes C3 . H31 . 0.997 no C4 . C5 . 1.404(8) yes C5 . C6 . 1.387(8) yes C5 . H51 . 1.002 no Cu1 . O2 2_757 2.673(4) yes Cu1 . N22 2_757 1.975(5) yes Cu1 . O2 . 2.673(4) yes Cu1 . N22 . 1.975(5) yes O3 . C7 . 1.267(7) yes O2 . C7 . 1.220(8) yes O23 . N22 . 1.402(6) yes O23 . H231 . 0.989 no N6 . H61 . 0.882 no C7 . C8 . 1.549(8) yes C8 . F1 . 1.324(9) yes C8 . F2 . 1.277(8) yes C8 . F3 . 1.311(8) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C6 . C61 . N6 . 112.0(5) yes C6 . C61 . H611 . 109.008 no N6 . C61 . H611 . 108.165 no C6 . C61 . H612 . 109.001 no N6 . C61 . H612 . 108.916 no H611 . C61 . H612 . 109.734 no C64 . C63 . N6 . 110.4(5) yes C64 . C63 . H631 . 109.546 no N6 . C63 . H631 . 108.176 no C64 . C63 . H632 . 109.940 no N6 . C63 . H632 . 109.544 no H631 . C63 . H632 . 109.161 no C63 . C64 . C65 . 110.6(5) yes C63 . C64 . H641 . 108.882 no C65 . C64 . H641 . 109.429 no C63 . C64 . H642 . 108.825 no C65 . C64 . H642 . 109.520 no H641 . C64 . H642 . 109.610 no C64 . C65 . C66 . 109.3(5) yes C64 . C65 . H651 . 109.520 no C66 . C65 . H651 . 109.404 no C64 . C65 . H652 . 109.798 no C66 . C65 . H652 . 109.349 no H651 . C65 . H652 . 109.477 no C65 . C66 . C67 . 110.7(5) yes C65 . C66 . H661 . 109.248 no C67 . C66 . H661 . 109.232 no C65 . C66 . H662 . 108.949 no C67 . C66 . H662 . 109.200 no H661 . C66 . H662 . 109.497 no C66 . C67 . N6 . 111.1(5) yes C66 . C67 . H671 . 109.504 no N6 . C67 . H671 . 108.265 no C66 . C67 . H672 . 109.416 no N6 . C67 . H672 . 109.069 no H671 . C67 . H672 . 109.452 no C2 . C21 . N22 . 124.4(5) yes C2 . C21 . H211 . 117.544 no N22 . C21 . H211 . 118.013 no C42 . C41 . C43 . 109.4(7) yes C42 . C41 . C44 . 109.1(8) yes C43 . C41 . C44 . 107.3(6) yes C42 . C41 . C4 . 108.6(6) yes C43 . C41 . C4 . 112.5(6) yes C44 . C41 . C4 . 109.9(7) yes C41 . C42 . H421 . 108.909 no C41 . C42 . H422 . 108.857 no H421 . C42 . H422 . 109.369 no C41 . C42 . H423 . 109.296 no H421 . C42 . H423 . 110.046 no H422 . C42 . H423 . 110.335 no C41 . C43 . H431 . 109.406 no C41 . C43 . H432 . 109.196 no H431 . C43 . H432 . 109.075 no C41 . C43 . H433 . 109.583 no H431 . C43 . H433 . 109.672 no H432 . C43 . H433 . 109.893 no C41 . C44 . H441 . 109.535 no C41 . C44 . H442 . 109.726 no H441 . C44 . H442 . 109.811 no C41 . C44 . H443 . 109.281 no H441 . C44 . H443 . 108.852 no H442 . C44 . H443 . 109.619 no C1 . O1 . Cu1 . 127.7(4) yes O1 . C1 . C2 . 123.9(5) yes O1 . C1 . C6 . 119.6(5) yes C2 . C1 . C6 . 116.4(5) yes C21 . C2 . C1 . 122.1(5) yes C21 . C2 . C3 . 117.3(5) yes C1 . C2 . C3 . 120.2(5) yes C2 . C3 . C4 . 123.0(5) yes C2 . C3 . H31 . 118.414 no C4 . C3 . H31 . 118.559 no C41 . C4 . C3 . 123.2(6) yes C41 . C4 . C5 . 120.1(6) yes C3 . C4 . C5 . 116.5(5) yes C4 . C5 . C6 . 122.3(6) yes C4 . C5 . H51 . 119.053 no C6 . C5 . H51 . 118.603 no C61 . C6 . C1 . 118.5(5) yes C61 . C6 . C5 . 120.1(5) yes C1 . C6 . C5 . 121.4(5) yes O2 2_757 Cu1 . N22 2_757 94.54(16) yes O2 2_757 Cu1 . O1 . 95.82(15) yes N22 2_757 Cu1 . O1 . 90.81(18) yes O2 2_757 Cu1 . O1 2_757 84.18(15) yes N22 2_757 Cu1 . O1 2_757 89.19(18) yes O1 . Cu1 . O1 2_757 179.994 yes O2 2_757 Cu1 . O2 . 179.996 yes N22 2_757 Cu1 . O2 . 85.46(16) yes O1 . Cu1 . O2 . 84.18(15) yes O1 2_757 Cu1 . O2 . 95.82(15) yes O2 2_757 Cu1 . N22 . 85.46(16) yes N22 2_757 Cu1 . N22 . 179.994 yes O1 . Cu1 . N22 . 89.19(18) yes O1 2_757 Cu1 . N22 . 90.81(18) yes O2 . Cu1 . N22 . 94.54(16) yes Cu1 . O2 . C7 . 113.9(4) yes N22 . O23 . H231 . 107.455 no C63 . N6 . C67 . 110.3(4) yes C63 . N6 . C61 . 111.5(4) yes C67 . N6 . C61 . 111.4(4) yes C63 . N6 . H61 . 107.845 no C67 . N6 . H61 . 107.850 no C61 . N6 . H61 . 107.863 no O23 . N22 . C21 . 111.7(4) yes O23 . N22 . Cu1 . 121.9(3) yes C21 . N22 . Cu1 . 126.1(4) yes O3 . C7 . O2 . 129.7(6) yes O3 . C7 . C8 . 113.3(5) yes O2 . C7 . C8 . 116.9(5) yes C7 . C8 . F1 . 112.5(6) yes C7 . C8 . F2 . 114.5(6) yes F1 . C8 . F2 . 106.2(7) yes C7 . C8 . F3 . 110.4(6) yes F1 . C8 . F3 . 104.2(7) yes F2 . C8 . F3 . 108.5(7) yes # Attachment '[Cu(L2)Br2].cif' data_pt6010 _database_code_depnum_ccdc_archive 'CCDC 744582' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H52 Br4 Cu2 N4 O4, 1.75(C H3 OH)' _chemical_formula_sum 'C35.75 H53.75 Br4 Cu2 N5.75 O4' _chemical_formula_weight 1074.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_int_tables_number 60 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.8492(5) _cell_length_b 24.7009(8) _cell_length_c 10.5521(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4391.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8991 _cell_measurement_theta_min 28.71 _cell_measurement_theta_max 2.42 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.99 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2154 _exptl_absorpt_coefficient_mu 4.649 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.11 _exptl_absorpt_correction_T_max 0.55 _exptl_absorpt_process_details 'SADABS version 2006/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32003 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5036 _reflns_number_gt 3888 _reflns_threshold_expression >2sigma(I) _computing_data_collection Smart _computing_cell_refinement Saint _computing_data_reduction Saint _computing_structure_solution 'Shelxs Sheldrick' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Shelxp _computing_publication_material Platon _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. 063_ALERT_3_B Crystal Probably too Large for Beam Size ....... 0.99 mm Gorbitz has shown that use of a large crystal does not appear to matter. See C. H. Gorbitz Acta Cryst. (1999). B55, 1090-1098 601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 125.00 A**3 041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? 043_ALERT_1_C Check Reported Molecular Weight ................ 1074.82 044_ALERT_1_C Calculated and Reported Dx Differ .............. ? 068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? The solvent region was treated by the van der Sluis and Spek method, accounting for approx 121 e/cell. This corresponds to 1.75 molecules of methanol per formula unit and F(000), M, mu, D and the formulae have been calculated on this assumption. 213_ALERT_2_C Atom Br1' has ADP max/min Ratio ............. 3.30 prola 301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. 910_ALERT_3_C # Missing FCF Reflections Below TH(Min) ........ 1 The data collection strategy used aimed to achieve a complete data set to 2\q = 53 deg. Some higher angle data were collected in the process and these have been included in the refinement. Please refer to the completeness statistics below #============================================================================== Resolution & Completeness Statistics (Cumulative) #============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------ 20.82 0.500 1.000 2307 2306 1 23.01 0.550 1.000 3069 3068 1 25.24 0.600 1.000 3974 3973 1 #----------------------------------------------------------- ACTA Min. Res. --- 27.48 0.649 1.000 5037 5036 1 ; _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^)+(0.0456P)^2^+1.2569P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5036 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.04949(2) 0.347634(15) 0.61141(4) 0.02827(11) Uani 1 1 d . . . Br1 Br 0.18745(2) 0.370845(17) 0.59168(5) 0.03570(11) Uani 0.95 1 d P A 1 Br1' Br 0.1817(5) 0.3759(4) 0.5258(7) 0.041(2) Uani 0.05 1 d P A 2 Br2 Br 0.075741(18) 0.253860(13) 0.56210(3) 0.03274(10) Uani 1 1 d . A . O1 O -0.06041(11) 0.33172(8) 0.64279(19) 0.0251(4) Uani 1 1 d . A . C1 C -0.12277(16) 0.35971(11) 0.6015(2) 0.0205(6) Uani 1 1 d . . . C2 C -0.12130(16) 0.41553(12) 0.5767(2) 0.0211(6) Uani 1 1 d . A . C3 C -0.19128(16) 0.44242(12) 0.5413(3) 0.0230(6) Uani 1 1 d . . . H3A H -0.1894 0.4805 0.5287 0.028 Uiso 1 1 calc R A . C4 C -0.26230(16) 0.41613(11) 0.5242(3) 0.0221(6) Uani 1 1 d . A . C5 C -0.26265(17) 0.36005(12) 0.5474(2) 0.0227(6) Uani 1 1 d . . . H5A H -0.3108 0.3406 0.5363 0.027 Uiso 1 1 calc R A . C6 C -0.19569(16) 0.33210(11) 0.5857(2) 0.0203(6) Uani 1 1 d . A . O21 O 0.07651(12) 0.46706(9) 0.6277(2) 0.0316(5) Uani 1 1 d . . . H21A H 0.1204 0.4509 0.6260 0.040(10) Uiso 1 1 d R A . C21 C -0.05000(16) 0.44682(12) 0.5936(3) 0.0230(6) Uani 1 1 d . . . H21B H -0.0546 0.4852 0.5930 0.028 Uiso 1 1 calc R A . N21 N 0.01919(13) 0.42647(10) 0.6093(2) 0.0241(5) Uani 1 1 d . A . C41 C -0.33933(17) 0.44451(12) 0.4837(3) 0.0277(7) Uani 1 1 d . . . C42 C -0.37028(19) 0.41854(14) 0.3603(3) 0.0382(8) Uani 1 1 d . A . H42A H -0.3303 0.4225 0.2935 0.057 Uiso 1 1 calc R . . H42B H -0.4194 0.4366 0.3343 0.057 Uiso 1 1 calc R . . H42C H -0.3808 0.3800 0.3749 0.057 Uiso 1 1 calc R . . C43 C -0.32619(19) 0.50481(13) 0.4583(4) 0.0422(9) Uani 1 1 d . A . H43A H -0.3064 0.5223 0.5354 0.063 Uiso 1 1 calc R . . H43B H -0.3765 0.5215 0.4330 0.063 Uiso 1 1 calc R . . H43C H -0.2872 0.5092 0.3901 0.063 Uiso 1 1 calc R . . C44 C -0.40136(19) 0.43817(15) 0.5878(3) 0.0402(8) Uani 1 1 d . A . H44A H -0.3817 0.4548 0.6661 0.060 Uiso 1 1 calc R . . H44B H -0.4115 0.3996 0.6025 0.060 Uiso 1 1 calc R . . H44C H -0.4507 0.4560 0.5618 0.060 Uiso 1 1 calc R . . C61 C -0.19948(16) 0.27367(11) 0.6220(3) 0.0218(6) Uani 1 1 d . . . H61A H -0.2534 0.2597 0.6040 0.026 Uiso 1 1 calc R A . H61B H -0.1900 0.2702 0.7142 0.026 Uiso 1 1 calc R . . N62 N -0.13930(15) 0.23973(10) 0.5516(2) 0.0218(5) Uani 1 1 d . A . C63 C -0.1546(2) 0.24051(13) 0.4118(3) 0.0285(7) Uani 1 1 d . . . H63A H -0.1522 0.2783 0.3806 0.034 Uiso 1 1 calc R A . H63B H -0.2085 0.2263 0.3947 0.034 Uiso 1 1 calc R . . C64 C -0.09378(19) 0.20636(14) 0.3418(3) 0.0342(7) Uani 1 1 d . A . H64A H -0.0404 0.2224 0.3531 0.041 Uiso 1 1 calc R . . H64B H -0.1062 0.2064 0.2501 0.041 Uiso 1 1 calc R . . C65 C -0.09352(19) 0.14819(14) 0.3907(3) 0.0354(8) Uani 1 1 d . . . H65A H -0.1450 0.1308 0.3711 0.043 Uiso 1 1 calc R A . H65B H -0.0511 0.1274 0.3479 0.043 Uiso 1 1 calc R . . C66 C -0.07979(19) 0.14746(12) 0.5330(3) 0.0332(7) Uani 1 1 d . A . H66A H -0.0848 0.1098 0.5644 0.040 Uiso 1 1 calc R . . H66B H -0.0252 0.1600 0.5512 0.040 Uiso 1 1 calc R . . C67 C -0.13845(18) 0.18326(11) 0.6028(3) 0.0257(6) Uani 1 1 d . . . H67A H -0.1923 0.1675 0.5953 0.031 Uiso 1 1 calc R A . H67B H -0.1243 0.1843 0.6938 0.031 Uiso 1 1 calc R . . H2A H -0.093(2) 0.2539(13) 0.564(3) 0.038(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 0.01370(19) 0.0265(2) 0.0446(2) -0.00015(16) 0.00194(15) -0.00105(15) Br1 0.01562(18) 0.0415(2) 0.0500(3) 0.0023(2) 0.00557(19) -0.00211(14) Br1' 0.030(4) 0.076(6) 0.016(3) 0.023(4) 0.000(3) -0.008(3) Br2 0.02298(17) 0.03122(19) 0.0440(2) -0.01031(14) -0.00198(13) 0.00291(13) O1 0.0132(10) 0.0249(11) 0.0370(11) 0.0054(9) -0.0018(8) 0.0007(8) C1 0.0148(14) 0.0226(15) 0.0240(14) -0.0003(11) 0.0000(11) 0.0011(11) C2 0.0169(14) 0.0239(15) 0.0225(14) 0.0002(12) -0.0005(11) -0.0014(11) C3 0.0218(14) 0.0197(15) 0.0275(15) 0.0036(12) 0.0002(12) -0.0007(12) C4 0.0162(14) 0.0232(15) 0.0269(14) 0.0008(12) -0.0021(11) 0.0004(11) C5 0.0180(14) 0.0230(15) 0.0270(15) -0.0010(12) -0.0025(12) -0.0034(11) C6 0.0190(14) 0.0180(14) 0.0240(14) -0.0016(11) 0.0003(11) -0.0013(11) O21 0.0172(11) 0.0300(12) 0.0477(13) 0.0044(10) -0.0055(9) -0.0091(9) C21 0.0220(15) 0.0226(15) 0.0245(14) 0.0013(12) -0.0014(11) -0.0029(12) N21 0.0151(12) 0.0243(13) 0.0330(13) 0.0026(11) -0.0014(10) -0.0082(10) C41 0.0202(15) 0.0244(16) 0.0386(17) 0.0017(13) -0.0063(13) 0.0019(12) C42 0.0303(18) 0.040(2) 0.0445(19) 0.0000(16) -0.0140(15) 0.0017(15) C43 0.0276(18) 0.0267(18) 0.072(2) 0.0045(17) -0.0126(17) 0.0038(14) C44 0.0237(16) 0.048(2) 0.049(2) 0.0068(16) -0.0032(14) 0.0114(16) C61 0.0168(14) 0.0221(15) 0.0266(15) 0.0009(12) 0.0011(11) -0.0002(11) N62 0.0186(13) 0.0190(13) 0.0278(13) 0.0000(10) -0.0013(10) 0.0006(10) C63 0.0302(17) 0.0301(17) 0.0252(15) -0.0007(12) -0.0015(12) -0.0003(13) C64 0.0278(16) 0.048(2) 0.0268(16) -0.0069(15) 0.0002(13) 0.0016(15) C65 0.0182(15) 0.039(2) 0.049(2) -0.0177(16) 0.0002(14) 0.0037(14) C66 0.0264(17) 0.0225(16) 0.051(2) -0.0056(14) -0.0032(15) 0.0021(13) C67 0.0261(16) 0.0189(15) 0.0322(16) 0.0016(12) -0.0008(13) 0.0001(12) _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 1.9218(18) . ? Cu1 N21 2.013(2) . ? Cu1 Br1 2.4031(5) . ? Cu1 Br2 2.4149(5) . ? Cu1 Br1' 2.504(8) . ? O1 C1 1.331(3) . ? C1 C2 1.404(4) . ? C1 C6 1.415(4) . ? C2 C3 1.404(4) . ? C2 C21 1.440(4) . ? C3 C4 1.373(4) . ? C3 H3A 0.9500 . ? C4 C5 1.407(4) . ? C4 C41 1.536(4) . ? C5 C6 1.383(4) . ? C5 H5A 0.9500 . ? C6 C61 1.495(4) . ? O21 N21 1.405(3) . ? O21 H21A 0.8400 . ? C21 N21 1.280(4) . ? C21 H21B 0.9500 . ? C41 C44 1.525(4) . ? C41 C43 1.529(4) . ? C41 C42 1.542(4) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C61 N62 1.511(4) . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? N62 C67 1.496(4) . ? N62 C63 1.497(4) . ? N62 H2A 0.86(4) . ? C63 C64 1.519(4) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C64 C65 1.527(5) . ? C64 H64A 0.9900 . ? C64 H64B 0.9900 . ? C65 C66 1.519(5) . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C66 C67 1.517(4) . ? C66 H66A 0.9900 . ? C66 H66B 0.9900 . ? C67 H67A 0.9900 . ? C67 H67B 0.9900 . ? 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 N21 87.44(9) . . ? O1 Cu1 Br1 174.71(6) . . ? N21 Cu1 Br1 90.78(7) . . ? O1 Cu1 Br2 91.00(6) . . ? N21 Cu1 Br2 166.38(7) . . ? Br1 Cu1 Br2 91.894(17) . . ? O1 Cu1 Br1' 167.60(19) . . ? N21 Cu1 Br1' 87.2(2) . . ? Br1 Cu1 Br1' 16.55(17) . . ? Br2 Cu1 Br1' 91.6(2) . . ? C1 O1 Cu1 126.73(18) . . ? O1 C1 C2 123.9(2) . . ? O1 C1 C6 118.3(2) . . ? C2 C1 C6 117.8(2) . . ? C1 C2 C3 120.0(2) . . ? C1 C2 C21 121.3(2) . . ? C3 C2 C21 118.7(3) . . ? C4 C3 C2 122.9(3) . . ? C4 C3 H3A 118.6 . . ? C2 C3 H3A 118.6 . . ? C3 C4 C5 116.5(3) . . ? C3 C4 C41 123.9(3) . . ? C5 C4 C41 119.6(2) . . ? C6 C5 C4 122.6(3) . . ? C6 C5 H5A 118.7 . . ? C4 C5 H5A 118.7 . . ? C5 C6 C1 120.2(3) . . ? C5 C6 C61 121.5(2) . . ? C1 C6 C61 118.2(2) . . ? N21 O21 H21A 105.2 . . ? N21 C21 C2 124.4(3) . . ? N21 C21 H21B 117.8 . . ? C2 C21 H21B 117.8 . . ? C21 N21 O21 111.3(2) . . ? C21 N21 Cu1 127.7(2) . . ? O21 N21 Cu1 120.94(17) . . ? C44 C41 C43 109.0(3) . . ? C44 C41 C4 109.4(2) . . ? C43 C41 C4 111.8(2) . . ? C44 C41 C42 109.5(3) . . ? C43 C41 C42 107.8(3) . . ? C4 C41 C42 109.3(2) . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C41 C43 H43A 109.5 . . ? C41 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C41 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C41 C44 H44A 109.5 . . ? C41 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C41 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C6 C61 N62 112.4(2) . . ? C6 C61 H61A 109.1 . . ? N62 C61 H61A 109.1 . . ? C6 C61 H61B 109.1 . . ? N62 C61 H61B 109.1 . . ? H61A C61 H61B 107.9 . . ? C67 N62 C63 111.7(2) . . ? C67 N62 C61 110.3(2) . . ? C63 N62 C61 111.2(2) . . ? C67 N62 H2A 109(2) . . ? C63 N62 H2A 107(2) . . ? C61 N62 H2A 108(2) . . ? N62 C63 C64 110.9(3) . . ? N62 C63 H63A 109.5 . . ? C64 C63 H63A 109.5 . . ? N62 C63 H63B 109.5 . . ? C64 C63 H63B 109.5 . . ? H63A C63 H63B 108.1 . . ? C63 C64 C65 111.1(3) . . ? C63 C64 H64A 109.4 . . ? C65 C64 H64A 109.4 . . ? C63 C64 H64B 109.4 . . ? C65 C64 H64B 109.4 . . ? H64A C64 H64B 108.0 . . ? C66 C65 C64 110.2(3) . . ? C66 C65 H65A 109.6 . . ? C64 C65 H65A 109.6 . . ? C66 C65 H65B 109.6 . . ? C64 C65 H65B 109.6 . . ? H65A C65 H65B 108.1 . . ? C67 C66 C65 111.9(3) . . ? C67 C66 H66A 109.2 . . ? C65 C66 H66A 109.2 . . ? C67 C66 H66B 109.2 . . ? C65 C66 H66B 109.2 . . ? H66A C66 H66B 107.9 . . ? N62 C67 C66 112.0(2) . . ? N62 C67 H67A 109.2 . . ? C66 C67 H67A 109.2 . . ? N62 C67 H67B 109.2 . . ? C66 C67 H67B 109.2 . . ? H67A C67 H67B 107.9 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.304 _refine_diff_density_min -0.873 _refine_diff_density_rms 0.091 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.393 0.250 135.3 30.9 2 0.500 0.893 0.250 135.3 30.6 3 0.000 0.607 0.750 135.3 29.9 4 0.500 0.107 0.750 135.3 29.8 _platon_squeeze_details ; Corresponds to 7 molecules of methanol per unit cell. ; _chemical_compound_source 'Ross Forgan' _exptl_crystal_recrystallization_method 'Diffusion of Et2O / iPr2O into MeOH'