# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Guillaume Pilet' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Fabrice Fenain' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Rita Matrak' '' '' M.Medebielle '' '' 'Jean-Bernard Tommasino' '' '' _publ_contact_author_name 'Dr Guillaume Pilet' _publ_contact_author_email GUILLAUME.PILET@UNIV-LYON1.FR _publ_section_title ; Trifluoromethylated enaminones and their explorative coordination chemistry with Cu(II): synthesis, redox properties and structural characterization of the complexes ; _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_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _publ_contact_author_address ; Groupe de Cristallographie et Ing\'enierie Mol\'eculaire Laboratoire des Multimat\'eriaux et Interfaces UMR 5615 CNRS-Universit\'e Claude Bernard Lyon 1 B\^at. Jules Raulin 43 bd du 11 Novembre 1918 69622 Villeurbanne cedex FRANCE ; _publ_contact_author_fax '(+33)4 72 43 11 60' _publ_contact_author_phone '(+33)4 72 44 82 20' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # 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 will be sent by e-mail. ; _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Guillaume Chastanet' # Attachment 'new_[Cu_L1_2].cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 682201' _audit_creation_date 07-03-20 _audit_creation_method CRYSTALS_ver_12.84 #_oxford_structure_analysis_title 'import in P 21/c' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 4.9303(3) _cell_length_b 9.2242(4) _cell_length_c 23.976(1) _cell_angle_alpha 90 _cell_angle_beta 92.432(2) _cell_angle_gamma 90 _cell_volume 1089.4(1) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-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 = C22 H18 Cu1 F6 N2 O2 # Dc = 1.58 Fooo = 497.01 Mu = 10.75 M = 259.97 # Found Formula = C22 H18 Cu0.50 F6.00 N2 O2 # Dc = 1.58 FOOO = 497.01 Mu = 10.75 M = 259.97 _chemical_formula_sum 'C22 H18 Cu1 F6 N2 O2' _chemical_formula_moiety 'C22 H18 Cu1 F6 N2 O2' _chemical_compound_source ? _chemical_formula_weight 519.93 _cell_measurement_reflns_used 2552 _cell_measurement_theta_min 0 _cell_measurement_theta_max 28 _cell_measurement_temperature 290 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.82 _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 497.007 _exptl_absorpt_coefficient_mu 1.075 # Sheldrick geometric approximatio 0.85 0.86 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8456 _exptl_absorpt_correction_T_max 0.8602 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 290 _diffrn_reflns_number 5070 _reflns_number_total 2581 _diffrn_reflns_av_R_equivalents 0.051 # Number of reflections with Friedels Law is 2581 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2420 _diffrn_reflns_theta_min 2.366 _diffrn_reflns_theta_max 27.887 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.050 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _reflns_limit_h_min -6 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 31 #_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 -0.25 _refine_diff_density_max 0.32 _refine_ls_number_reflns 1108 _refine_ls_number_restraints 13 _refine_ls_number_parameters 180 #_refine_ls_R_factor_ref 0.0382 _refine_ls_wR_factor_ref 0.0444 _refine_ls_goodness_of_fit_ref 1.1837 #_reflns_number_all 2576 _refine_ls_R_factor_all 0.1120 _refine_ls_wR_factor_all 0.0949 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 1108 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_gt 0.0444 _refine_ls_shift/su_max 0.000676 # 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 F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.397 0.294 0.264 0.772E-01 0.642E-01 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # 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). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. 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 atomsattached 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 Cu1 Cu 1.0000 0.0000 1.0000 0.0491 1.0000 Uani S . . . . . C1 C 0.9820(10) -0.2104(5) 0.85038(18) 0.0602 1.0000 Uani . . . . . . C2 C 0.7945(12) -0.2603(6) 0.8105(2) 0.0745 1.0000 Uani . . . . . . C3 C 0.6950(13) -0.1684(7) 0.7695(2) 0.0804 1.0000 Uani . . . . . . C4 C 0.7845(13) -0.0295(6) 0.7677(2) 0.0794 1.0000 Uani . . . . . . C5 C 0.9754(11) 0.0200(6) 0.80790(18) 0.0695 1.0000 Uani . . . . . . C6 C 1.0760(9) -0.0701(5) 0.84995(16) 0.0510 1.0000 Uani . . . . . . C7 C 1.2902(9) -0.0140(5) 0.89109(16) 0.0555 1.0000 Uani . . . . . . N8 N 1.2661(8) -0.0783(4) 0.94735(13) 0.0499 1.0000 Uani . . . . . . C9 C 1.4226(11) -0.1864(6) 0.95868(19) 0.0612 1.0000 Uani . . . . . . C10 C 1.4255(11) -0.2753(5) 1.0064(2) 0.0658 1.0000 Uani . . . . . . C11 C 1.2468(11) -0.2580(5) 1.04688(18) 0.0566 1.0000 Uani . . . . . . O12 O 1.0706(8) -0.1573(4) 1.05057(13) 0.0690 1.0000 Uani . . . . . . C13 C 1.2423(11) -0.3721(5) 1.09601(17) 0.0816 1.0000 Uani D . . . . . F14 F 1.320(5) -0.4987(16) 1.0838(7) 0.1594 0.35(2) Uani D . P . . . F15 F 1.404(4) -0.319(2) 1.1360(6) 0.1174 0.35(2) Uani D . P . . . F16 F 0.997(3) -0.377(2) 1.1127(8) 0.1160 0.35(2) Uani D . P . . . F17 F 1.016(2) -0.4363(17) 1.0921(8) 0.2285 0.65(2) Uani D . P . . . F18 F 1.268(4) -0.3101(13) 1.1424(4) 0.1833 0.65(2) Uani D . P . . . F19 F 1.430(3) -0.4634(12) 1.0917(5) 0.1109 0.65(2) Uani D . P . . . H11 H 1.0498 -0.2748 0.8777 0.0710 1.0000 Uiso . . . . . . H21 H 0.7358 -0.3557 0.8114 0.0870 1.0000 Uiso . . . . . . H31 H 0.5610 -0.2013 0.7438 0.0971 1.0000 Uiso . . . . . . H41 H 0.7210 0.0332 0.7395 0.0951 1.0000 Uiso . . . . . . H51 H 1.0340 0.1151 0.8067 0.0830 1.0000 Uiso . . . . . . H71 H 1.2697 0.0905 0.8941 0.0668 1.0000 Uiso . . . . . . H72 H 1.4677 -0.0359 0.8777 0.0669 1.0000 Uiso . . . . . . H91 H 1.5499 -0.2086 0.9322 0.0750 1.0000 Uiso . . . . . . H101 H 1.5554 -0.3476 1.0101 0.0780 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 Cu1 0.0619(5) 0.0465(4) 0.0389(3) -0.0013(4) 0.0016(3) 0.0012(5) C1 0.077(4) 0.058(3) 0.045(2) 0.004(2) -0.003(2) -0.003(3) C2 0.100(4) 0.065(3) 0.059(3) -0.008(3) -0.001(3) -0.009(3) C3 0.089(4) 0.099(5) 0.051(3) -0.010(3) -0.009(3) 0.000(4) C4 0.102(4) 0.086(5) 0.049(2) 0.012(3) -0.005(3) 0.016(3) C5 0.093(4) 0.064(3) 0.052(2) 0.006(2) 0.005(2) 0.005(3) C6 0.064(3) 0.053(2) 0.036(2) -0.0034(18) 0.0096(19) 0.004(2) C7 0.066(3) 0.057(3) 0.0436(19) 0.002(2) 0.0105(18) -0.001(3) N8 0.060(2) 0.049(2) 0.0412(18) -0.0035(16) 0.0026(16) -0.002(2) C9 0.067(3) 0.063(3) 0.054(3) -0.008(2) 0.009(2) 0.005(3) C10 0.084(5) 0.057(3) 0.055(3) -0.003(2) -0.006(3) 0.017(3) C11 0.073(3) 0.047(3) 0.049(2) -0.001(2) -0.007(2) 0.000(3) O12 0.092(3) 0.062(2) 0.0543(18) 0.0159(15) 0.0183(18) 0.019(2) C13 0.092(5) 0.077(4) 0.076(4) 0.015(3) 0.004(4) 0.010(4) F14 0.37(4) 0.025(5) 0.092(10) -0.004(6) 0.096(17) -0.014(12) F15 0.143(13) 0.137(17) 0.067(11) 0.042(10) -0.058(9) -0.052(11) F16 0.119(14) 0.121(14) 0.112(12) 0.059(10) 0.051(9) 0.015(10) F17 0.113(9) 0.216(14) 0.35(2) 0.216(14) -0.044(11) -0.038(9) F18 0.39(2) 0.110(8) 0.053(5) 0.019(4) 0.050(10) 0.092(12) F19 0.144(7) 0.080(7) 0.109(6) 0.033(5) 0.009(5) 0.052(6) _refine_ls_extinction_method None #_oxford_refine_ls_scale 0.2775(8) 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 Cu1 . N8 2_757 1.994(4) yes Cu1 . O12 2_757 1.913(3) yes Cu1 . N8 . 1.994(4) yes Cu1 . O12 . 1.913(3) yes C1 . C2 . 1.380(7) yes C1 . C6 . 1.375(6) yes C1 . H11 . 0.936 no C2 . C3 . 1.374(7) yes C2 . H21 . 0.927 no C3 . C4 . 1.357(8) yes C3 . H31 . 0.934 no C4 . C5 . 1.396(7) yes C4 . H41 . 0.933 no C5 . C6 . 1.382(6) yes C5 . H51 . 0.924 no C6 . C7 . 1.506(6) yes C7 . N8 . 1.483(5) yes C7 . H71 . 0.972 no C7 . H72 . 0.967 no N8 . C9 . 1.283(6) yes C9 . C10 . 1.406(6) yes C9 . H91 . 0.934 no C10 . C11 . 1.349(6) yes C10 . H101 . 0.927 no C11 . O12 . 1.277(6) yes C11 . C13 . 1.580(5) yes C13 . F14 . 1.267(14) yes C13 . F15 . 1.316(12) yes C13 . F16 . 1.291(15) yes C13 . F17 . 1.265(11) yes C13 . F18 . 1.253(10) yes C13 . F19 . 1.260(9) 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 N8 2_757 Cu1 . O12 2_757 91.12(14) yes N8 2_757 Cu1 . N8 . 179.994 yes O12 2_757 Cu1 . N8 . 88.88(14) yes N8 2_757 Cu1 . O12 . 88.88(14) yes O12 2_757 Cu1 . O12 . 179.994 yes N8 . Cu1 . O12 . 91.12(14) yes C2 . C1 . C6 . 121.7(4) yes C2 . C1 . H11 . 118.8 no C6 . C1 . H11 . 119.5 no C1 . C2 . C3 . 119.9(5) yes C1 . C2 . H21 . 120.1 no C3 . C2 . H21 . 119.9 no C2 . C3 . C4 . 119.9(5) yes C2 . C3 . H31 . 119.5 no C4 . C3 . H31 . 120.5 no C3 . C4 . C5 . 119.9(5) yes C3 . C4 . H41 . 120.5 no C5 . C4 . H41 . 119.6 no C4 . C5 . C6 . 121.2(5) yes C4 . C5 . H51 . 119.4 no C6 . C5 . H51 . 119.4 no C5 . C6 . C1 . 117.4(4) yes C5 . C6 . C7 . 119.4(4) yes C1 . C6 . C7 . 123.1(4) yes C6 . C7 . N8 . 112.2(4) yes C6 . C7 . H71 . 108.5 no N8 . C7 . H71 . 108.5 no C6 . C7 . H72 . 109.3 no N8 . C7 . H72 . 109.1 no H71 . C7 . H72 . 109.3 no C7 . N8 . Cu1 . 120.7(3) yes C7 . N8 . C9 . 115.7(4) yes Cu1 . N8 . C9 . 123.6(3) yes N8 . C9 . C10 . 127.6(4) yes N8 . C9 . H91 . 116.2 no C10 . C9 . H91 . 116.1 no C9 . C10 . C11 . 122.2(4) yes C9 . C10 . H101 . 118.7 no C11 . C10 . H101 . 119.1 no C10 . C11 . O12 . 127.1(4) yes C10 . C11 . C13 . 119.2(4) yes O12 . C11 . C13 . 113.7(4) yes C11 . O12 . Cu1 . 127.9(3) yes C11 . C13 . F14 . 115.4(9) yes C11 . C13 . F15 . 105.4(9) yes F14 . C13 . F15 . 109.6(2) yes C11 . C13 . F16 . 107.4(9) yes F14 . C13 . F16 . 109.5(2) yes F15 . C13 . F16 . 109.5(2) yes C11 . C13 . F17 . 107.3(7) yes F14 . C13 . F17 . 79.9(10) yes F15 . C13 . F17 . 137.3(11) yes F16 . C13 . F17 . 33.9(9) yes C11 . C13 . F18 . 110.8(7) yes F14 . C13 . F18 . 127.2(11) yes F15 . C13 . F18 . 31.4(9) yes F16 . C13 . F18 . 78.5(9) yes F17 . C13 . F18 . 109.5(2) yes C11 . C13 . F19 . 110.5(6) yes F14 . C13 . F19 . 30.0(10) yes F15 . C13 . F19 . 83.5(9) yes F16 . C13 . F19 . 134.7(11) yes F17 . C13 . F19 . 109.3(2) yes F18 . C13 . F19 . 109.4(2) yes # Attachment 'new_[Cu2_L2_4].cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 682202' _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 10.2689(4) _cell_length_b 10.2371(4) _cell_length_c 21.4894(10) _cell_angle_alpha 90 _cell_angle_beta 92.757(2) _cell_angle_gamma 90 _cell_volume 2256.43(16) _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 8 # Given Formula = C11 H7 Cu1 F3 N2 O1 # Dc = 1.79 Fooo = 1084.00 Mu = 19.63 M = 607.46 # Found Formula = C11 H6 Cu0.50 F3 N2 O1 # Dc = 1.60 FOOO = 1084.00 Mu = 10.45 M = 541.90 _chemical_formula_sum 'C11 H6 Cu0.50 F3 N2 O1' _chemical_formula_moiety 'C11 H6 Cu0.50 F3 N2 O1' _chemical_compound_source ? _chemical_formula_weight 270.95 _cell_measurement_reflns_used 4327 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 290 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.31 _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 1.045 # Sheldrick geometric approximatio 0.73 0.81 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7340 _exptl_absorpt_correction_T_max 0.8123 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 290 _diffrn_reflns_number 8447 _reflns_number_total 5027 _diffrn_reflns_av_R_equivalents 0.044 # Number of reflections with Friedels Law is 5027 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5165 _diffrn_reflns_theta_min 1.898 _diffrn_reflns_theta_max 27.534 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.056 _diffrn_measured_fraction_theta_full 0.982 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 27 #_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 -0.44 _refine_diff_density_max 0.27 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement #_oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 2282 _refine_ls_number_restraints 84 _refine_ls_number_parameters 352 #_oxford_refine_ls_R_factor_ref 0.0400 _refine_ls_wR_factor_ref 0.0459 _refine_ls_goodness_of_fit_ref 1.1652 _refine_ls_shift/su_max 0.004280 # The values computed from all data #_oxford_reflns_number_all 5010 _refine_ls_R_factor_all 0.1045 _refine_ls_wR_factor_all 0.0810 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2628 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_gt 0.0493 # 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 F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refxyz # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.537 0.339 0.354 ; # 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). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. 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 atomsattached 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cu1 Cu 0.26684(5) 0.22862(5) 0.51042(2) 0.0488 1.0000 Uani . . . . . . . N1 N 0.6925(4) 0.0158(4) 0.4694(2) 0.0714 1.0000 Uani . . . . . . . C2 C 0.6434(4) 0.1025(4) 0.4437(2) 0.0560 1.0000 Uani . . . . . . . C3 C 0.5868(4) 0.2135(4) 0.41166(18) 0.0537 1.0000 Uani D . . . . . . C4 C 0.6220(4) 0.2398(5) 0.3515(2) 0.0737 1.0000 Uani D . . . . . . C5 C 0.5694(5) 0.3450(5) 0.3201(2) 0.0865 1.0000 Uani D . . . . . . C6 C 0.4822(5) 0.4243(5) 0.3485(2) 0.0789 1.0000 Uani D . . . . . . C7 C 0.4448(4) 0.3993(4) 0.4083(2) 0.0661 1.0000 Uani D . . . . . . C8 C 0.4971(4) 0.2932(4) 0.44079(18) 0.0481 1.0000 Uani D . . . . . . N9 N 0.4547(3) 0.2659(3) 0.50116(14) 0.0478 1.0000 Uani D . . . . . . C10 C 0.5411(4) 0.2574(3) 0.54701(18) 0.0507 1.0000 Uani D . . . . . . C11 C 0.5143(4) 0.2290(4) 0.60948(19) 0.0579 1.0000 Uani D . . . . . . C12 C 0.3917(4) 0.2226(4) 0.63069(17) 0.0517 1.0000 Uani D . . . . . . O13 O 0.2843(3) 0.2361(3) 0.59941(12) 0.0571 1.0000 Uani . . . . . . . C14 C 0.3708(5) 0.1988(6) 0.6989(2) 0.0761 1.0000 Uani . . . . . . . F15 F 0.2990(4) 0.0943(4) 0.70722(15) 0.1181 1.0000 Uani . . . . . . . F16 F 0.3106(4) 0.2959(4) 0.72481(15) 0.1241 1.0000 Uani . . . . . . . F17 F 0.4812(4) 0.1820(5) 0.73254(14) 0.1271 1.0000 Uani . . . . . . . N21 N 0.2213(4) 0.5497(4) 0.5172(2) 0.0743 1.0000 Uani . . . . . . . C22 C 0.1517(4) 0.4966(4) 0.5482(2) 0.0559 1.0000 Uani . . . . . . . C23 C 0.0627(4) 0.4291(4) 0.58598(19) 0.0562 1.0000 Uani D . . . . . . C24 C 0.0131(4) 0.4908(5) 0.6373(2) 0.0731 1.0000 Uani D . . . . . . C25 C -0.0741(4) 0.4268(5) 0.6736(2) 0.0859 1.0000 Uani D . . . . . . C26 C -0.1130(4) 0.3015(5) 0.6572(2) 0.0834 1.0000 Uani D . . . . . . C27 C -0.0654(4) 0.2404(4) 0.6062(2) 0.0651 1.0000 Uani D . . . . . . C28 C 0.0223(4) 0.3023(4) 0.56998(17) 0.0485 1.0000 Uani D . . . . . . N29 N 0.0748(3) 0.2431(3) 0.51647(15) 0.0476 1.0000 Uani D . . . . . . C30 C -0.0072(4) 0.1904(4) 0.4761(2) 0.0606 1.0000 Uani D . . . . . . C31 C 0.0245(4) 0.1345(4) 0.4186(2) 0.0650 1.0000 Uani D . . . . . . C32 C 0.1455(4) 0.1434(4) 0.39614(19) 0.0558 1.0000 Uani D . . . . . . O33 O 0.2479(3) 0.1891(3) 0.42323(13) 0.0620 1.0000 Uani . . . . . . . C34 C 0.1707(5) 0.0974(5) 0.3308(2) 0.0726 1.0000 Uani . . . . . . . F35 F 0.2621(4) 0.0068(4) 0.32977(15) 0.1077 1.0000 Uani . . . . . . . F36 F 0.2090(4) 0.1951(4) 0.29539(13) 0.1034 1.0000 Uani . . . . . . . F37 F 0.0663(3) 0.0458(4) 0.30103(14) 0.1051 1.0000 Uani . . . . . . . H161 H 0.0391(15) 0.5754(18) 0.6468(8) 0.0867 1.0000 Uiso D . . . . . . H162 H -0.1060(15) 0.468(2) 0.7083(8) 0.1039 1.0000 Uiso D . . . . . . H163 H -0.1723(15) 0.2583(19) 0.6806(8) 0.0991 1.0000 Uiso D . . . . . . H164 H -0.0918(15) 0.1554(18) 0.5960(8) 0.0767 1.0000 Uiso D . . . . . . H142 H 0.3844(14) 0.4521(17) 0.4269(9) 0.0782 1.0000 Uiso D . . . . . . H143 H 0.4462(15) 0.4959(17) 0.3270(9) 0.0939 1.0000 Uiso D . . . . . . H144 H 0.5939(16) 0.3623(18) 0.2791(9) 0.1029 1.0000 Uiso D . . . . . . H145 H 0.6819(14) 0.1848(17) 0.3329(9) 0.0870 1.0000 Uiso D . . . . . . H1 H 0.5841(19) 0.2150(10) 0.6378(9) 0.0666 1.0000 Uiso D . . . . . . H4 H -0.0398(19) 0.0915(13) 0.3943(9) 0.0748 1.0000 Uiso D . . . . . . H301 H -0.0950(18) 0.1904(12) 0.4857(9) 0.0722 1.0000 Uiso D . . . . . . H101 H 0.6286(18) 0.2747(10) 0.5378(9) 0.0599 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 Cu1 0.0439(3) 0.0608(3) 0.0420(2) -0.0004(2) 0.00499(17) 0.0007(2) N1 0.070(2) 0.062(2) 0.082(3) 0.003(2) 0.010(2) 0.006(2) C2 0.052(2) 0.057(3) 0.060(3) -0.004(2) 0.013(2) -0.006(2) C3 0.057(2) 0.051(2) 0.055(2) 0.0024(19) 0.0174(19) -0.002(2) C4 0.077(3) 0.078(3) 0.069(3) 0.004(3) 0.028(2) 0.004(3) C5 0.101(4) 0.100(4) 0.062(3) 0.017(3) 0.036(3) 0.003(3) C6 0.097(4) 0.072(3) 0.069(3) 0.027(3) 0.019(3) 0.009(3) C7 0.077(3) 0.061(3) 0.063(3) 0.012(2) 0.020(2) 0.004(2) C8 0.048(2) 0.050(2) 0.048(2) -0.0004(18) 0.0084(17) -0.0057(18) N9 0.0516(17) 0.0472(18) 0.0453(17) 0.0031(14) 0.0098(15) -0.0019(15) C10 0.0432(19) 0.057(3) 0.052(2) 0.0016(18) 0.0055(17) -0.0060(17) C11 0.049(2) 0.072(3) 0.051(2) 0.007(2) -0.0044(18) -0.002(2) C12 0.055(2) 0.056(2) 0.045(2) 0.0046(18) 0.0002(18) -0.0001(19) O13 0.0502(15) 0.076(2) 0.0455(14) 0.0005(13) 0.0064(12) 0.0040(14) C14 0.077(3) 0.096(4) 0.055(3) 0.009(3) -0.001(3) -0.006(3) F15 0.146(3) 0.136(3) 0.074(2) 0.0263(19) 0.019(2) -0.041(3) F16 0.173(4) 0.145(3) 0.0573(18) -0.0161(19) 0.033(2) 0.029(3) F17 0.105(3) 0.219(4) 0.0563(19) 0.035(2) -0.0085(19) 0.001(3) N21 0.077(3) 0.064(2) 0.083(3) 0.002(2) 0.007(2) -0.011(2) C22 0.060(3) 0.046(2) 0.061(3) -0.0058(19) 0.002(2) -0.006(2) C23 0.057(2) 0.050(2) 0.061(3) -0.006(2) 0.006(2) 0.002(2) C24 0.081(3) 0.062(3) 0.077(3) -0.024(2) 0.017(3) -0.009(2) C25 0.087(4) 0.090(4) 0.083(4) -0.026(3) 0.032(3) -0.007(3) C26 0.075(3) 0.093(4) 0.085(4) -0.013(3) 0.033(3) -0.011(3) C27 0.062(2) 0.061(3) 0.073(3) -0.006(2) 0.020(2) -0.009(2) C28 0.045(2) 0.053(3) 0.048(2) -0.0061(17) 0.0090(18) 0.0024(17) N29 0.0481(16) 0.0433(19) 0.0516(18) -0.0057(14) 0.0052(15) 0.0001(14) C30 0.045(2) 0.062(3) 0.075(3) -0.016(2) 0.003(2) -0.0024(19) C31 0.058(3) 0.070(3) 0.065(3) -0.022(2) -0.004(2) -0.004(2) C32 0.061(3) 0.053(3) 0.053(2) -0.0026(19) -0.002(2) 0.002(2) O33 0.0543(17) 0.086(2) 0.0459(15) -0.0039(14) 0.0071(14) -0.0051(14) C34 0.082(3) 0.080(3) 0.056(3) -0.004(3) 0.000(3) 0.003(3) F35 0.123(3) 0.121(3) 0.079(2) -0.0282(18) 0.0104(18) 0.042(2) F36 0.142(3) 0.114(3) 0.0558(17) 0.0099(16) 0.0122(17) -0.021(2) F37 0.116(3) 0.129(3) 0.0687(19) -0.0315(18) -0.0096(18) -0.015(2) _refine_ls_extinction_method None #_oxford_refine_ls_scale 0.2188(5) 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 Cu1 . N1 2_656 2.570(4) yes Cu1 . N9 . 1.986(3) yes Cu1 . O13 . 1.914(3) yes Cu1 . N29 . 1.988(3) yes Cu1 . O33 . 1.918(3) yes N1 . C2 . 1.149(6) yes C2 . C3 . 1.437(6) yes C3 . C4 . 1.385(6) yes C3 . C8 . 1.401(6) yes C4 . C5 . 1.369(7) yes C4 . H145 . 0.936(18) no C5 . C6 . 1.375(7) yes C5 . H144 . 0.944(19) no C6 . C7 . 1.382(6) yes C6 . H143 . 0.933(19) no C7 . C8 . 1.385(6) yes C7 . H142 . 0.927(18) no C8 . N9 . 1.416(5) yes N9 . C10 . 1.297(5) yes C10 . C11 . 1.413(5) yes C10 . H101 . 0.946(18) no C11 . C12 . 1.361(6) yes C11 . H1 . 0.929(18) no C12 . O13 . 1.272(5) yes C12 . C14 . 1.511(6) yes C14 . F15 . 1.316(6) yes C14 . F16 . 1.309(6) yes C14 . F17 . 1.326(6) yes N21 . C22 . 1.139(5) yes C22 . C23 . 1.429(6) yes C23 . C24 . 1.389(6) yes C23 . C28 . 1.400(6) yes C24 . C25 . 1.380(7) yes C24 . H161 . 0.926(18) no C25 . C26 . 1.383(7) yes C25 . H162 . 0.931(19) no C26 . C27 . 1.373(6) yes C26 . H163 . 0.921(19) no C27 . C28 . 1.373(6) yes C27 . H164 . 0.934(18) no C28 . N29 . 1.429(5) yes N29 . C30 . 1.297(5) yes C30 . C31 . 1.415(6) yes C30 . H301 . 0.935(18) no C31 . C32 . 1.357(6) yes C31 . H4 . 0.932(18) no C32 . O33 . 1.267(5) yes C32 . C34 . 1.516(6) yes C34 . F35 . 1.321(6) yes C34 . F36 . 1.328(6) yes C34 . F37 . 1.330(6) 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 N1 2_656 Cu1 . N9 . 93.06(13) yes N1 2_656 Cu1 . O13 . 82.18(13) yes N9 . Cu1 . O13 . 92.74(12) yes N1 2_656 Cu1 . N29 . 102.41(12) yes N9 . Cu1 . N29 . 164.51(12) yes O13 . Cu1 . N29 . 88.70(12) yes N1 2_656 Cu1 . O33 . 88.12(14) yes N9 . Cu1 . O33 . 89.76(12) yes O13 . Cu1 . O33 . 170.10(13) yes N29 . Cu1 . O33 . 91.44(13) yes Cu1 2_656 N1 . C2 . 153.7(4) yes N1 . C2 . C3 . 177.8(5) yes C2 . C3 . C4 . 118.9(4) yes C2 . C3 . C8 . 120.4(4) yes C4 . C3 . C8 . 120.7(4) yes C3 . C4 . C5 . 119.9(4) yes C3 . C4 . H145 . 119.2(13) no C5 . C4 . H145 . 120.9(13) no C4 . C5 . C6 . 119.7(4) yes C4 . C5 . H144 . 119.5(13) no C6 . C5 . H144 . 120.8(13) no C5 . C6 . C7 . 121.4(4) yes C5 . C6 . H143 . 119.7(13) no C7 . C6 . H143 . 119.0(13) no C6 . C7 . C8 . 119.7(4) yes C6 . C7 . H142 . 120.9(13) no C8 . C7 . H142 . 119.5(13) no C3 . C8 . C7 . 118.6(4) yes C3 . C8 . N9 . 122.2(3) yes C7 . C8 . N9 . 119.2(3) yes C8 . N9 . Cu1 . 118.2(2) yes C8 . N9 . C10 . 118.7(3) yes Cu1 . N9 . C10 . 122.9(2) yes N9 . C10 . C11 . 125.3(3) yes N9 . C10 . H101 . 116.8(12) no C11 . C10 . H101 . 117.9(12) no C10 . C11 . C12 . 123.6(4) yes C10 . C11 . H1 . 118.4(12) no C12 . C11 . H1 . 118.0(13) no C11 . C12 . O13 . 127.6(4) yes C11 . C12 . C14 . 120.6(4) yes O13 . C12 . C14 . 111.7(4) yes C12 . O13 . Cu1 . 124.1(2) yes C12 . C14 . F15 . 111.7(4) yes C12 . C14 . F16 . 112.5(4) yes F15 . C14 . F16 . 106.3(5) yes C12 . C14 . F17 . 113.1(4) yes F15 . C14 . F17 . 106.9(5) yes F16 . C14 . F17 . 106.0(5) yes N21 . C22 . C23 . 178.8(5) yes C22 . C23 . C24 . 120.0(4) yes C22 . C23 . C28 . 119.9(4) yes C24 . C23 . C28 . 120.0(4) yes C23 . C24 . C25 . 120.3(4) yes C23 . C24 . H161 . 119.1(13) no C25 . C24 . H161 . 120.6(13) no C24 . C25 . C26 . 119.0(4) yes C24 . C25 . H162 . 120.0(13) no C26 . C25 . H162 . 121.0(13) no C25 . C26 . C27 . 121.0(5) yes C25 . C26 . H163 . 119.8(13) no C27 . C26 . H163 . 119.2(13) no C26 . C27 . C28 . 120.7(4) yes C26 . C27 . H164 . 120.1(13) no C28 . C27 . H164 . 119.2(13) no C23 . C28 . C27 . 118.9(4) yes C23 . C28 . N29 . 118.2(3) yes C27 . C28 . N29 . 122.9(3) yes C28 . N29 . Cu1 . 119.9(2) yes C28 . N29 . C30 . 117.2(3) yes Cu1 . N29 . C30 . 122.7(3) yes N29 . C30 . C31 . 125.7(4) yes N29 . C30 . H301 . 117.1(13) no C31 . C30 . H301 . 117.2(13) no C30 . C31 . C32 . 122.4(4) yes C30 . C31 . H4 . 119.6(13) no C32 . C31 . H4 . 118.0(13) no C31 . C32 . O33 . 128.0(4) yes C31 . C32 . C34 . 120.5(4) yes O33 . C32 . C34 . 111.5(4) yes C32 . O33 . Cu1 . 124.7(3) yes C32 . C34 . F35 . 112.7(4) yes C32 . C34 . F36 . 111.4(4) yes F35 . C34 . F36 . 106.8(4) yes C32 . C34 . F37 . 113.5(4) yes F35 . C34 . F37 . 105.7(4) yes F36 . C34 . F37 . 106.2(4) yes # Attachment 'new_[Cu_L3_2].cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 682203' _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 12.0582(7) _cell_length_b 16.326(1) _cell_length_c 20.279(1) _cell_angle_alpha 68.198(4) _cell_angle_beta 80.075(3) _cell_angle_gamma 78.876(4) _cell_volume 3614.7(4) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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 6 # Given Formula = C26 H16 Cu1 F6 N4 O2 # Dc = 1.64 Fooo = 1794.00 Mu = 9.86 M = 1781.92 # Found Formula = C26 H16 Cu1 F6 N4 O2 # Dc = 1.64 FOOO = 1794.00 Mu = 9.86 M = 1781.92 _chemical_formula_sum 'C26 H16 Cu1 F6 N4 O2' _chemical_formula_moiety 'C26 H16 Cu1 F6 N4 O2' _chemical_compound_source ? _chemical_formula_weight 593.97 _cell_measurement_reflns_used 12576 _cell_measurement_theta_min 0 _cell_measurement_theta_max 26 _cell_measurement_temperature 293 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.637 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1794 _exptl_absorpt_coefficient_mu 0.986 # Sheldrick geometric approximatio 0.84 0.92 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8423 _exptl_absorpt_correction_T_max 0.9151 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _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 293 _diffrn_reflns_number 22876 _reflns_number_total 13648 _diffrn_reflns_av_R_equivalents 0.092 # Number of reflections with Friedels Law is 13648 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 13714 _diffrn_reflns_theta_min 1.088 _diffrn_reflns_theta_max 25.670 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.670 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -14 _reflns_limit_h_max 14 _reflns_limit_k_min -18 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 24 #_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 -0.50 _refine_diff_density_max 0.49 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement #_oxford_reflns_threshold_expression_ref I>1.0\s(I) _refine_ls_number_reflns 5871 _refine_ls_number_restraints 0 _refine_ls_number_parameters 1054 #_oxford_refine_ls_R_factor_ref 0.0683 _refine_ls_wR_factor_ref 0.0556 _refine_ls_goodness_of_fit_ref 1.1551 _refine_ls_shift/su_max 0.000024 # The values computed from all data #_oxford_reflns_number_all 13590 _refine_ls_R_factor_all 0.1759 _refine_ls_wR_factor_all 0.1206 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4618 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_gt 0.0480 # 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 F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.419 0.355 0.259 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Grazia, A., Moliterni, G., Polidori, G. & Spagna, R. (1999). J. App. Cryst. 32, 115-119. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. 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 atomsattached 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cu1 Cu 0.16451(8) 0.60291(7) 0.58661(5) 0.0444 1.0000 Uani . . . . . . . N111 N 0.1644(5) 0.5951(4) 0.6983(4) 0.0420 1.0000 Uani . . . . . . . C112 C 0.0916(7) 0.5669(5) 0.7562(5) 0.0481 1.0000 Uani . . . . . . . C113 C 0.1003(8) 0.5764(6) 0.8213(5) 0.0552 1.0000 Uani . . . . . . . C114 C 0.1855(8) 0.6159(6) 0.8256(5) 0.0531 1.0000 Uani . . . . . . . C115 C 0.2656(7) 0.6471(5) 0.7655(4) 0.0452 1.0000 Uani . . . . . . . C116 C 0.3555(8) 0.6898(6) 0.7657(5) 0.0575 1.0000 Uani . . . . . . . C117 C 0.4276(7) 0.7204(7) 0.7043(5) 0.0612 1.0000 Uani . . . . . . . C118 C 0.4157(7) 0.7071(6) 0.6421(5) 0.0574 1.0000 Uani . . . . . . . C119 C 0.3294(7) 0.6625(6) 0.6399(5) 0.0522 1.0000 Uani . . . . . . . C120 C 0.2506(7) 0.6351(5) 0.7025(4) 0.0430 1.0000 Uani . . . . . . . N121 N 0.3105(5) 0.6422(4) 0.5821(4) 0.0432 1.0000 Uani . . . . . . . C122 C 0.3971(8) 0.6344(8) 0.5344(6) 0.0789 1.0000 Uani . . . . . . . C123 C 0.3961(7) 0.6219(8) 0.4696(5) 0.0744 1.0000 Uani . . . . . . . C124 C 0.2991(8) 0.6224(6) 0.4419(5) 0.0535 1.0000 Uani . . . . . . . C125 C 0.3198(10) 0.6113(7) 0.3691(5) 0.0672 1.0000 Uani . . . . . . . F126 F 0.3887(5) 0.6620(4) 0.3217(3) 0.0930 1.0000 Uani . . . . . . . F127 F 0.3663(10) 0.5301(5) 0.3721(3) 0.1589 1.0000 Uani . . . . . . . F128 F 0.2280(7) 0.6256(7) 0.3395(4) 0.1540 1.0000 Uani . . . . . . . O129 O 0.1988(5) 0.6267(4) 0.4684(3) 0.0508 1.0000 Uani . . . . . . . N130 N 0.0658(6) 0.7277(5) 0.5686(3) 0.0504 1.0000 Uani . . . . . . . C131 C 0.0966(9) 0.8070(7) 0.5511(5) 0.0628 1.0000 Uani . . . . . . . C132 C 0.0167(14) 0.8830(7) 0.5527(6) 0.0880 1.0000 Uani . . . . . . . C133 C -0.0954(13) 0.8743(9) 0.5733(7) 0.0921 1.0000 Uani . . . . . . . C134 C -0.1320(10) 0.7912(8) 0.5910(5) 0.0714 1.0000 Uani . . . . . . . C135 C -0.2468(11) 0.7738(10) 0.6154(7) 0.0941 1.0000 Uani . . . . . . . C136 C -0.2698(9) 0.6904(11) 0.6330(7) 0.0952 1.0000 Uani . . . . . . . C137 C -0.1890(8) 0.6196(8) 0.6277(5) 0.0745 1.0000 Uani . . . . . . . C138 C -0.0776(7) 0.6332(7) 0.6045(4) 0.0543 1.0000 Uani . . . . . . . C139 C -0.0459(8) 0.7189(6) 0.5869(4) 0.0519 1.0000 Uani . . . . . . . N140 N 0.0158(5) 0.5671(5) 0.5974(3) 0.0450 1.0000 Uani . . . . . . . C141 C -0.0067(7) 0.4964(7) 0.5888(5) 0.0577 1.0000 Uani . . . . . . . C142 C 0.0747(8) 0.4255(7) 0.5845(5) 0.0628 1.0000 Uani . . . . . . . C143 C 0.1905(8) 0.4196(6) 0.5908(4) 0.0511 1.0000 Uani . . . . . . . C144 C 0.2721(8) 0.3401(6) 0.5806(5) 0.0550 1.0000 Uani . . . . . . . F145 F 0.3357(4) 0.3642(4) 0.5181(3) 0.0715 1.0000 Uani . . . . . . . F146 F 0.3414(5) 0.3049(3) 0.6308(3) 0.0822 1.0000 Uani . . . . . . . F147 F 0.2202(5) 0.2741(4) 0.5821(4) 0.0945 1.0000 Uani . . . . . . . O148 O 0.2403(4) 0.4745(4) 0.5995(3) 0.0462 1.0000 Uani . . . . . . . Cu2 Cu 0.09311(8) 0.29248(7) 0.91028(5) 0.0432 1.0000 Uani . . . . . . . N211 N 0.2039(5) 0.1596(4) 0.9361(3) 0.0425 1.0000 Uani . . . . . . . C212 C 0.2713(7) 0.1167(6) 0.9869(4) 0.0530 1.0000 Uani . . . . . . . C213 C 0.3550(7) 0.0420(6) 0.9852(4) 0.0534 1.0000 Uani . . . . . . . C214 C 0.3674(7) 0.0159(6) 0.9276(5) 0.0569 1.0000 Uani . . . . . . . C215 C 0.3001(7) 0.0593(6) 0.8725(4) 0.0491 1.0000 Uani . . . . . . . C216 C 0.3069(8) 0.0365(6) 0.8111(5) 0.0593 1.0000 Uani . . . . . . . C217 C 0.2362(8) 0.0841(7) 0.7592(5) 0.0615 1.0000 Uani . . . . . . . C218 C 0.1550(7) 0.1551(6) 0.7666(4) 0.0505 1.0000 Uani . . . . . . . C219 C 0.1416(7) 0.1794(5) 0.8256(4) 0.0416 1.0000 Uani . . . . . . . C220 C 0.2166(7) 0.1305(5) 0.8800(4) 0.0444 1.0000 Uani . . . . . . . N221 N 0.0611(5) 0.2501(4) 0.8367(3) 0.0417 1.0000 Uani . . . . . . . C222 C -0.0301(8) 0.2752(6) 0.8045(4) 0.0526 1.0000 Uani . . . . . . . C223 C -0.1179(7) 0.3459(6) 0.8067(4) 0.0486 1.0000 Uani . . . . . . . C224 C -0.1153(7) 0.4053(6) 0.8391(4) 0.0477 1.0000 Uani . . . . . . . C225 C -0.2220(8) 0.4731(7) 0.8390(5) 0.0616 1.0000 Uani . . . . . . . F226 F -0.2962(4) 0.4816(4) 0.7956(3) 0.0745 1.0000 Uani . . . . . . . F227 F -0.2789(5) 0.4560(4) 0.9047(3) 0.0855 1.0000 Uani . . . . . . . F228 F -0.1944(5) 0.5554(4) 0.8225(4) 0.0928 1.0000 Uani . . . . . . . O229 O -0.0392(5) 0.4123(4) 0.8716(3) 0.0509 1.0000 Uani . . . . . . . N230 N 0.2302(5) 0.3546(4) 0.8491(4) 0.0422 1.0000 Uani . . . . . . . C231 C 0.2684(8) 0.3682(5) 0.7808(5) 0.0509 1.0000 Uani . . . . . . . C232 C 0.3646(7) 0.4106(5) 0.7461(4) 0.0470 1.0000 Uani . . . . . . . C233 C 0.4188(7) 0.4414(6) 0.7832(5) 0.0492 1.0000 Uani . . . . . . . C234 C 0.3794(6) 0.4326(5) 0.8551(4) 0.0398 1.0000 Uani . . . . . . . C235 C 0.4256(7) 0.4665(6) 0.8963(5) 0.0603 1.0000 Uani . . . . . . . C236 C 0.3765(9) 0.4592(7) 0.9639(5) 0.0684 1.0000 Uani . . . . . . . C237 C 0.2801(8) 0.4127(6) 0.9949(5) 0.0589 1.0000 Uani . . . . . . . C238 C 0.2356(6) 0.3769(6) 0.9568(4) 0.0427 1.0000 Uani . . . . . . . C239 C 0.2828(7) 0.3877(5) 0.8854(4) 0.0416 1.0000 Uani . . . . . . . N240 N 0.1413(5) 0.3290(4) 0.9814(3) 0.0406 1.0000 Uani . . . . . . . C241 C 0.0973(7) 0.3068(6) 1.0485(5) 0.0511 1.0000 Uani . . . . . . . C242 C 0.0029(7) 0.2621(6) 1.0795(4) 0.0495 1.0000 Uani . . . . . . . C243 C -0.0607(7) 0.2361(5) 1.0426(4) 0.0397 1.0000 Uani . . . . . . . C244 C -0.1720(8) 0.2025(6) 1.0815(5) 0.0517 1.0000 Uani . . . . . . . F245 F -0.2595(4) 0.2653(3) 1.0587(3) 0.0662 1.0000 Uani . . . . . . . F246 F -0.1889(4) 0.1320(3) 1.0692(3) 0.0639 1.0000 Uani . . . . . . . F247 F -0.1806(4) 0.1802(4) 1.1521(2) 0.0718 1.0000 Uani . . . . . . . O248 O -0.0419(5) 0.2390(4) 0.9789(3) 0.0492 1.0000 Uani . . . . . . . Cu3 Cu 0.26342(8) 0.00175(7) 1.24715(5) 0.0439 1.0000 Uani . . . . . . . N311 N 0.1271(6) -0.0701(5) 1.3304(4) 0.0475 1.0000 Uani . . . . . . . C312 C 0.1202(8) -0.1551(7) 1.3662(5) 0.0552 1.0000 Uani . . . . . . . C313 C 0.0209(9) -0.1875(6) 1.4008(5) 0.0578 1.0000 Uani . . . . . . . C314 C -0.0786(9) -0.1307(7) 1.4024(5) 0.0599 1.0000 Uani . . . . . . . C315 C -0.0764(8) -0.0381(6) 1.3648(4) 0.0476 1.0000 Uani . . . . . . . C316 C -0.1726(7) 0.0271(7) 1.3627(5) 0.0535 1.0000 Uani . . . . . . . C317 C -0.1644(8) 0.1138(7) 1.3233(5) 0.0589 1.0000 Uani . . . . . . . C318 C -0.0614(7) 0.1428(6) 1.2859(4) 0.0488 1.0000 Uani . . . . . . . C319 C 0.0371(8) 0.0815(6) 1.2889(4) 0.0481 1.0000 Uani . . . . . . . C320 C 0.0280(7) -0.0112(6) 1.3294(4) 0.0431 1.0000 Uani . . . . . . . N321 N 0.1450(5) 0.1045(4) 1.2523(3) 0.0418 1.0000 Uani . . . . . . . C322 C 0.1684(7) 0.1847(6) 1.2377(4) 0.0474 1.0000 Uani . . . . . . . C323 C 0.2671(7) 0.2201(5) 1.1994(5) 0.0471 1.0000 Uani . . . . . . . C324 C 0.3517(7) 0.1769(6) 1.1637(4) 0.0445 1.0000 Uani . . . . . . . C325 C 0.4559(8) 0.2241(6) 1.1265(5) 0.0560 1.0000 Uani . . . . . . . F326 F 0.4469(4) 0.3074(3) 1.1254(3) 0.0649 1.0000 Uani . . . . . . . F327 F 0.5462(4) 0.1795(4) 1.1607(3) 0.0828 1.0000 Uani . . . . . . . F328 F 0.4810(5) 0.2266(4) 1.0595(3) 0.0908 1.0000 Uani . . . . . . . O329 O 0.3576(5) 0.1036(4) 1.1567(3) 0.0522 1.0000 Uani . . . . . . . N330 N 0.1941(6) -0.0294(4) 1.1743(3) 0.0429 1.0000 Uani . . . . . . . C331 C 0.0953(7) 0.0037(5) 1.1478(4) 0.0442 1.0000 Uani . . . . . . . C332 C 0.0582(7) -0.0269(6) 1.1000(4) 0.0497 1.0000 Uani . . . . . . . C333 C 0.1248(8) -0.0930(6) 1.0800(4) 0.0546 1.0000 Uani . . . . . . . C334 C 0.2322(7) -0.1282(5) 1.1063(4) 0.0460 1.0000 Uani . . . . . . . C335 C 0.3114(8) -0.1923(6) 1.0848(5) 0.0548 1.0000 Uani . . . . . . . C336 C 0.4135(9) -0.2196(6) 1.1102(5) 0.0630 1.0000 Uani . . . . . . . C337 C 0.4424(8) -0.1904(6) 1.1614(5) 0.0600 1.0000 Uani . . . . . . . C338 C 0.3680(7) -0.1313(5) 1.1861(4) 0.0431 1.0000 Uani . . . . . . . C339 C 0.2634(7) -0.0957(5) 1.1549(4) 0.0431 1.0000 Uani . . . . . . . N340 N 0.3793(6) -0.0984(4) 1.2400(4) 0.0460 1.0000 Uani . . . . . . . C341 C 0.4554(7) -0.1397(5) 1.2830(5) 0.0501 1.0000 Uani . . . . . . . C342 C 0.4774(8) -0.1144(6) 1.3381(5) 0.0554 1.0000 Uani . . . . . . . C343 C 0.4193(8) -0.0405(7) 1.3531(5) 0.0587 1.0000 Uani . . . . . . . C344 C 0.4502(10) -0.0227(8) 1.4153(6) 0.0751 1.0000 Uani . . . . . . . F345 F 0.4859(6) 0.0564(5) 1.3948(4) 0.1018 1.0000 Uani . . . . . . . F346 F 0.5319(6) -0.0823(4) 1.4500(3) 0.1044 1.0000 Uani . . . . . . . F347 F 0.3625(6) -0.0202(5) 1.4643(3) 0.1068 1.0000 Uani . . . . . . . O348 O 0.3395(5) 0.0153(4) 1.3226(3) 0.0524 1.0000 Uani . . . . . . . H1121 H 0.0276 0.5364 0.7526 0.0579 1.0000 Uiso . . . . . . . H1131 H 0.0415 0.5533 0.8650 0.0677 1.0000 Uiso . . . . . . . H1141 H 0.1920 0.6241 0.8722 0.0654 1.0000 Uiso . . . . . . . H1161 H 0.3672 0.6976 0.8117 0.0709 1.0000 Uiso . . . . . . . H1171 H 0.4917 0.7533 0.7038 0.0774 1.0000 Uiso . . . . . . . H1181 H 0.4700 0.7303 0.5967 0.0737 1.0000 Uiso . . . . . . . H1221 H 0.4741 0.6397 0.5452 0.0980 1.0000 Uiso . . . . . . . H1231 H 0.4730 0.6123 0.4412 0.0921 1.0000 Uiso . . . . . . . H1311 H 0.1823 0.8111 0.5361 0.0821 1.0000 Uiso . . . . . . . H1321 H 0.0470 0.9450 0.5372 0.1122 1.0000 Uiso . . . . . . . H1331 H -0.1515 0.9298 0.5753 0.1141 1.0000 Uiso . . . . . . . H1351 H -0.3096 0.8242 0.6213 0.1143 1.0000 Uiso . . . . . . . H1361 H -0.3544 0.6794 0.6495 0.1141 1.0000 Uiso . . . . . . . H1371 H -0.2117 0.5564 0.6421 0.0956 1.0000 Uiso . . . . . . . H1411 H -0.0899 0.4937 0.5867 0.0721 1.0000 Uiso . . . . . . . H1421 H 0.0513 0.3736 0.5751 0.0774 1.0000 Uiso . . . . . . . H2121 H 0.2640 0.1367 1.0298 0.0596 1.0000 Uiso . . . . . . . H2131 H 0.4044 0.0083 1.0258 0.0614 1.0000 Uiso . . . . . . . H2141 H 0.4283 -0.0361 0.9246 0.0675 1.0000 Uiso . . . . . . . H2161 H 0.3671 -0.0137 0.8051 0.0746 1.0000 Uiso . . . . . . . H2171 H 0.2416 0.0660 0.7154 0.0746 1.0000 Uiso . . . . . . . H2181 H 0.1035 0.1909 0.7269 0.0600 1.0000 Uiso . . . . . . . H2221 H -0.0382 0.2405 0.7742 0.0655 1.0000 Uiso . . . . . . . H2231 H -0.1887 0.3532 0.7826 0.0588 1.0000 Uiso . . . . . . . H2311 H 0.2261 0.3463 0.7529 0.0595 1.0000 Uiso . . . . . . . H2321 H 0.3916 0.4184 0.6932 0.0548 1.0000 Uiso . . . . . . . H2331 H 0.4893 0.4718 0.7590 0.0545 1.0000 Uiso . . . . . . . H2351 H 0.4949 0.5002 0.8749 0.0701 1.0000 Uiso . . . . . . . H2361 H 0.4090 0.4862 0.9927 0.0903 1.0000 Uiso . . . . . . . H2371 H 0.2432 0.4066 1.0466 0.0757 1.0000 Uiso . . . . . . . H2411 H 0.1387 0.3238 1.0806 0.0572 1.0000 Uiso . . . . . . . H2421 H -0.0205 0.2478 1.1332 0.0627 1.0000 Uiso . . . . . . . H3121 H 0.1945 -0.1998 1.3675 0.0695 1.0000 Uiso . . . . . . . H3131 H 0.0202 -0.2550 1.4270 0.0775 1.0000 Uiso . . . . . . . H3141 H -0.1530 -0.1537 1.4295 0.0746 1.0000 Uiso . . . . . . . H3161 H -0.2494 0.0105 1.3904 0.0704 1.0000 Uiso . . . . . . . H3171 H -0.2347 0.1604 1.3205 0.0676 1.0000 Uiso . . . . . . . H3181 H -0.0590 0.2094 1.2559 0.0591 1.0000 Uiso . . . . . . . H3221 H 0.1066 0.2250 1.2580 0.0614 1.0000 Uiso . . . . . . . H3231 H 0.2764 0.2826 1.1974 0.0560 1.0000 Uiso . . . . . . . H3311 H 0.0436 0.0532 1.1619 0.0534 1.0000 Uiso . . . . . . . H3321 H -0.0184 0.0007 1.0806 0.0660 1.0000 Uiso . . . . . . . H3331 H 0.0974 -0.1176 1.0475 0.0649 1.0000 Uiso . . . . . . . H3351 H 0.2918 -0.2173 1.0498 0.0642 1.0000 Uiso . . . . . . . H3361 H 0.4712 -0.2627 1.0917 0.0746 1.0000 Uiso . . . . . . . H3371 H 0.5205 -0.2153 1.1819 0.0737 1.0000 Uiso . . . . . . . H3411 H 0.5030 -0.1954 1.2767 0.0605 1.0000 Uiso . . . . . . . H3421 H 0.5411 -0.1524 1.3695 0.0763 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 Cu1 0.0407(6) 0.0491(7) 0.0472(6) -0.0222(5) -0.0069(5) -0.0019(5) N111 0.039(4) 0.037(4) 0.049(4) -0.016(3) -0.011(3) 0.003(3) C112 0.042(5) 0.033(5) 0.072(7) -0.018(5) -0.007(5) -0.012(4) C113 0.057(6) 0.052(6) 0.056(6) -0.022(5) -0.004(5) -0.001(5) C114 0.057(6) 0.052(6) 0.053(6) -0.023(5) -0.005(5) -0.006(5) C115 0.043(5) 0.048(5) 0.053(5) -0.028(4) -0.009(4) -0.001(4) C116 0.057(6) 0.066(7) 0.062(6) -0.035(5) -0.021(5) 0.002(5) C117 0.042(5) 0.083(7) 0.073(7) -0.045(6) -0.008(5) -0.005(5) C118 0.034(5) 0.077(7) 0.063(6) -0.032(5) -0.006(4) 0.004(5) C119 0.034(5) 0.075(7) 0.064(6) -0.037(5) -0.023(5) -0.007(5) C120 0.039(5) 0.037(5) 0.055(6) -0.017(4) -0.008(4) -0.004(4) N121 0.026(4) 0.059(5) 0.054(4) -0.036(4) 0.002(3) 0.000(3) C122 0.051(6) 0.120(10) 0.093(8) -0.063(7) 0.002(6) -0.032(6) C123 0.043(6) 0.133(10) 0.082(7) -0.075(7) 0.014(5) -0.035(6) C124 0.058(6) 0.059(6) 0.054(6) -0.029(5) 0.003(5) -0.021(5) C125 0.089(8) 0.076(8) 0.053(6) -0.040(6) 0.004(6) -0.025(6) F126 0.115(5) 0.112(5) 0.057(4) -0.029(3) 0.026(3) -0.061(4) F127 0.343(13) 0.074(5) 0.070(5) -0.041(4) -0.018(6) -0.026(6) F128 0.120(6) 0.320(13) 0.075(5) -0.105(6) 0.004(4) -0.093(7) O129 0.043(4) 0.052(4) 0.056(4) -0.017(3) -0.004(3) -0.006(3) N130 0.043(5) 0.071(6) 0.044(4) -0.029(4) -0.006(3) -0.003(4) C131 0.089(8) 0.064(7) 0.046(6) -0.021(5) -0.025(5) -0.017(6) C132 0.152(13) 0.056(7) 0.068(8) -0.031(6) -0.050(8) 0.008(8) C133 0.121(11) 0.090(10) 0.081(9) -0.056(8) -0.052(8) 0.038(9) C134 0.086(9) 0.075(8) 0.051(6) -0.036(6) -0.017(6) 0.031(7) C135 0.071(9) 0.120(11) 0.090(9) -0.061(9) -0.029(7) 0.056(8) C136 0.054(7) 0.138(12) 0.102(10) -0.071(10) 0.004(6) 0.015(8) C137 0.050(6) 0.117(9) 0.073(7) -0.053(7) 0.007(5) -0.023(6) C138 0.042(6) 0.077(7) 0.041(5) -0.019(5) -0.003(4) -0.004(5) C139 0.055(6) 0.065(7) 0.039(5) -0.030(5) -0.017(4) 0.019(5) N140 0.041(4) 0.056(5) 0.042(4) -0.023(4) -0.003(3) -0.009(4) C141 0.038(5) 0.081(8) 0.057(6) -0.024(6) -0.007(4) -0.012(5) C142 0.052(6) 0.075(7) 0.069(7) -0.031(6) 0.003(5) -0.022(6) C143 0.065(6) 0.046(6) 0.042(5) -0.015(4) 0.009(4) -0.019(5) C144 0.054(6) 0.049(6) 0.066(7) -0.024(5) 0.000(5) -0.012(5) F145 0.064(3) 0.077(4) 0.075(4) -0.037(3) 0.016(3) -0.015(3) F146 0.098(4) 0.052(4) 0.095(4) -0.029(3) -0.028(4) 0.015(3) F147 0.075(4) 0.081(4) 0.153(6) -0.074(4) 0.021(4) -0.031(3) O148 0.048(3) 0.053(4) 0.043(3) -0.021(3) -0.006(3) -0.010(3) Cu2 0.0422(6) 0.0516(7) 0.0403(6) -0.0201(5) -0.0038(5) -0.0096(5) N211 0.035(4) 0.056(5) 0.040(4) -0.019(4) -0.005(3) -0.007(3) C212 0.053(6) 0.060(6) 0.044(5) -0.012(5) -0.004(4) -0.016(5) C213 0.048(5) 0.057(6) 0.043(5) -0.008(5) -0.008(4) 0.003(5) C214 0.054(6) 0.049(6) 0.058(6) -0.009(5) -0.005(5) -0.007(5) C215 0.049(5) 0.045(5) 0.052(6) -0.019(5) 0.000(5) -0.005(4) C216 0.068(6) 0.040(5) 0.069(7) -0.025(5) 0.006(5) -0.006(5) C217 0.074(7) 0.068(7) 0.054(6) -0.036(5) -0.002(5) -0.010(6) C218 0.054(6) 0.051(6) 0.051(5) -0.028(5) 0.000(4) -0.001(4) C219 0.040(5) 0.048(5) 0.043(5) -0.020(4) 0.000(4) -0.014(4) C220 0.043(5) 0.048(5) 0.046(5) -0.018(4) 0.003(4) -0.018(4) N221 0.040(4) 0.050(4) 0.036(4) -0.014(3) -0.009(3) -0.008(3) C222 0.065(6) 0.060(6) 0.044(5) -0.027(5) 0.003(5) -0.026(5) C223 0.052(5) 0.054(6) 0.044(5) -0.023(4) -0.015(4) 0.003(5) C224 0.038(5) 0.065(6) 0.040(5) -0.015(5) -0.003(4) -0.015(5) C225 0.050(6) 0.076(8) 0.061(7) -0.023(5) -0.005(5) -0.016(5) F226 0.053(3) 0.091(4) 0.086(4) -0.040(3) -0.026(3) 0.011(3) F227 0.061(4) 0.117(5) 0.079(4) -0.045(4) 0.007(3) -0.002(3) F228 0.071(4) 0.059(4) 0.147(6) -0.041(4) -0.017(4) 0.009(3) O229 0.050(4) 0.057(4) 0.053(4) -0.026(3) -0.009(3) -0.007(3) N230 0.044(4) 0.036(4) 0.042(4) -0.010(3) -0.010(3) -0.001(3) C231 0.065(6) 0.034(5) 0.049(6) -0.011(4) -0.020(5) 0.011(5) C232 0.050(5) 0.038(5) 0.042(5) -0.007(4) -0.003(4) 0.001(4) C233 0.035(5) 0.053(6) 0.057(6) -0.019(5) -0.004(4) -0.002(4) C234 0.030(4) 0.037(5) 0.054(5) -0.017(4) -0.011(4) 0.000(4) C235 0.045(5) 0.064(7) 0.071(7) -0.017(5) -0.014(5) -0.013(5) C236 0.068(7) 0.096(8) 0.058(6) -0.036(6) -0.005(5) -0.035(6) C237 0.056(6) 0.077(7) 0.051(6) -0.030(5) 0.002(5) -0.019(5) C238 0.033(5) 0.060(6) 0.044(5) -0.029(4) -0.004(4) -0.005(4) C239 0.040(5) 0.050(5) 0.041(5) -0.021(4) -0.009(4) -0.009(4) N240 0.036(4) 0.050(4) 0.041(4) -0.020(3) -0.006(3) -0.008(3) C241 0.053(6) 0.060(6) 0.045(6) -0.022(5) -0.011(4) -0.005(5) C242 0.042(5) 0.072(6) 0.042(5) -0.024(5) -0.001(4) -0.019(5) C243 0.042(5) 0.037(5) 0.037(5) -0.014(4) -0.001(4) -0.001(4) C244 0.057(6) 0.062(6) 0.043(6) -0.023(5) -0.008(5) -0.013(5) F245 0.042(3) 0.067(4) 0.080(4) -0.018(3) -0.002(3) -0.005(3) F246 0.072(4) 0.063(3) 0.068(3) -0.031(3) 0.008(3) -0.032(3) F247 0.075(4) 0.107(4) 0.041(3) -0.025(3) 0.005(3) -0.043(3) O248 0.053(4) 0.061(4) 0.040(3) -0.024(3) -0.003(3) -0.015(3) Cu3 0.0475(7) 0.0415(6) 0.0473(6) -0.0206(5) -0.0111(5) -0.0013(5) N311 0.051(5) 0.051(5) 0.040(4) -0.017(4) -0.010(3) -0.001(4) C312 0.065(6) 0.057(7) 0.044(5) -0.015(5) -0.019(5) -0.005(5) C313 0.074(7) 0.058(6) 0.046(6) -0.015(5) -0.009(5) -0.023(6) C314 0.066(7) 0.084(8) 0.043(5) -0.027(5) -0.001(5) -0.033(6) C315 0.054(6) 0.053(6) 0.041(5) -0.018(5) -0.011(4) -0.009(5) C316 0.050(6) 0.069(7) 0.049(5) -0.030(5) 0.000(4) -0.014(5) C317 0.048(6) 0.077(7) 0.051(6) -0.029(5) -0.003(5) 0.003(5) C318 0.052(6) 0.046(5) 0.041(5) -0.011(4) -0.007(4) 0.002(5) C319 0.060(6) 0.050(6) 0.037(5) -0.019(4) -0.014(4) 0.002(5) C320 0.054(6) 0.046(6) 0.029(4) -0.011(4) -0.006(4) -0.008(5) N321 0.038(4) 0.045(5) 0.047(4) -0.023(4) -0.012(3) 0.002(3) C322 0.061(6) 0.043(6) 0.043(5) -0.022(4) -0.012(4) 0.002(5) C323 0.045(5) 0.042(5) 0.058(6) -0.021(5) -0.013(4) -0.001(4) C324 0.048(5) 0.040(5) 0.051(5) -0.017(4) -0.020(4) -0.005(4) C325 0.061(6) 0.054(6) 0.064(6) -0.029(5) -0.007(5) -0.015(5) F326 0.073(4) 0.046(3) 0.078(4) -0.021(3) -0.008(3) -0.015(3) F327 0.051(3) 0.059(4) 0.134(5) -0.024(3) -0.027(3) -0.005(3) F328 0.110(5) 0.093(5) 0.084(4) -0.048(4) 0.026(4) -0.045(4) O329 0.054(4) 0.049(4) 0.064(4) -0.032(3) -0.006(3) -0.007(3) N330 0.053(5) 0.035(4) 0.038(4) -0.011(3) -0.005(3) -0.002(4) C331 0.045(5) 0.041(5) 0.046(5) -0.017(4) -0.001(4) -0.007(4) C332 0.054(6) 0.052(6) 0.049(5) -0.020(5) -0.014(4) -0.011(5) C333 0.076(7) 0.046(6) 0.049(5) -0.024(5) -0.005(5) -0.012(5) C334 0.051(5) 0.046(5) 0.034(5) -0.004(4) -0.011(4) -0.004(4) C335 0.076(7) 0.048(6) 0.053(6) -0.033(5) -0.010(5) -0.004(5) C336 0.086(8) 0.051(6) 0.055(6) -0.031(5) -0.005(5) 0.009(5) C337 0.065(6) 0.054(6) 0.057(6) -0.024(5) -0.001(5) 0.004(5) C338 0.054(5) 0.032(5) 0.038(5) -0.003(4) -0.007(4) -0.011(4) C339 0.059(6) 0.038(5) 0.034(5) -0.014(4) -0.004(4) -0.008(4) N340 0.052(4) 0.038(4) 0.049(4) -0.020(3) -0.013(4) 0.007(3) C341 0.047(5) 0.037(5) 0.067(6) -0.022(5) -0.012(5) 0.004(4) C342 0.066(6) 0.054(6) 0.060(6) -0.032(5) -0.020(5) -0.002(5) C343 0.063(6) 0.068(7) 0.054(6) -0.025(5) -0.021(5) -0.009(6) C344 0.067(7) 0.087(9) 0.081(8) -0.040(7) -0.037(7) 0.015(7) F345 0.121(6) 0.087(5) 0.130(6) -0.062(4) -0.055(4) -0.004(4) F346 0.110(5) 0.121(5) 0.111(5) -0.075(4) -0.071(4) 0.042(4) F347 0.096(5) 0.165(7) 0.075(4) -0.070(5) -0.030(4) 0.024(5) O348 0.059(4) 0.049(4) 0.060(4) -0.029(3) -0.021(3) -0.002(3) _refine_ls_extinction_method None #_oxford_refine_ls_scale 0.06580(11) 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 Cu1 . N111 . 2.221(6) yes Cu1 . N121 . 1.964(6) yes Cu1 . O129 . 2.258(6) yes Cu1 . N130 . 2.089(7) yes Cu1 . N140 . 1.945(7) yes Cu1 . O148 . 2.058(6) yes N111 . C112 . 1.326(10) yes N111 . C120 . 1.360(9) yes C112 . C113 . 1.410(12) yes C112 . H1121 . 1.022 no C113 . C114 . 1.344(12) yes C113 . H1131 . 1.033 no C114 . C115 . 1.415(11) yes C114 . H1141 . 1.019 no C115 . C116 . 1.398(12) yes C115 . C120 . 1.408(11) yes C116 . C117 . 1.374(13) yes C116 . H1161 . 1.023 no C117 . C118 . 1.392(12) yes C117 . H1171 . 1.020 no C118 . C119 . 1.395(11) yes C118 . H1181 . 1.024 no C119 . C120 . 1.429(11) yes C119 . N121 . 1.394(9) yes N121 . C122 . 1.317(11) yes C122 . C123 . 1.405(13) yes C122 . H1221 . 1.017 no C123 . C124 . 1.378(12) yes C123 . H1231 . 1.022 no C124 . C125 . 1.526(12) yes C124 . O129 . 1.236(9) yes C125 . F126 . 1.304(11) yes C125 . F127 . 1.320(11) yes C125 . F128 . 1.291(12) yes N130 . C131 . 1.318(11) yes N130 . C139 . 1.355(11) yes C131 . C132 . 1.423(15) yes C131 . H1311 . 1.034 no C132 . C133 . 1.363(16) yes C132 . H1321 . 1.059 no C133 . C134 . 1.407(16) yes C133 . H1331 . 1.031 no C134 . C135 . 1.433(16) yes C134 . C139 . 1.431(12) yes C135 . C136 . 1.345(17) yes C135 . H1351 . 1.031 no C136 . C137 . 1.385(15) yes C136 . H1361 . 1.045 no C137 . C138 . 1.376(12) yes C137 . H1371 . 1.041 no C138 . C139 . 1.420(12) yes C138 . N140 . 1.430(10) yes N140 . C141 . 1.312(11) yes C141 . C142 . 1.385(12) yes C141 . H1411 . 1.022 no C142 . C143 . 1.405(12) yes C142 . H1421 . 1.031 no C143 . C144 . 1.526(12) yes C143 . O148 . 1.248(9) yes C144 . F145 . 1.328(10) yes C144 . F146 . 1.319(10) yes C144 . F147 . 1.336(9) yes Cu2 . N211 . 2.246(7) yes Cu2 . N221 . 1.980(6) yes Cu2 . O229 . 2.253(6) yes Cu2 . N230 . 2.075(7) yes Cu2 . N240 . 1.959(6) yes Cu2 . O248 . 2.053(5) yes N211 . C212 . 1.321(10) yes N211 . C220 . 1.363(9) yes C212 . C213 . 1.433(12) yes C212 . H2121 . 1.023 no C213 . C214 . 1.362(12) yes C213 . H2131 . 1.020 no C214 . C215 . 1.382(12) yes C214 . H2141 . 1.022 no C215 . C216 . 1.413(12) yes C215 . C220 . 1.418(11) yes C216 . C217 . 1.373(13) yes C216 . H2161 . 1.014 no C217 . C218 . 1.403(12) yes C217 . H2171 . 1.023 no C218 . C219 . 1.369(10) yes C218 . H2181 . 1.029 no C219 . C220 . 1.444(11) yes C219 . N221 . 1.418(10) yes N221 . C222 . 1.295(10) yes C222 . C223 . 1.416(11) yes C222 . H2221 . 1.005 no C223 . C224 . 1.366(11) yes C223 . H2231 . 1.020 no C224 . C225 . 1.528(12) yes C224 . O229 . 1.262(9) yes C225 . F226 . 1.314(10) yes C225 . F227 . 1.345(10) yes C225 . F228 . 1.352(11) yes N230 . C231 . 1.330(10) yes N230 . C239 . 1.351(9) yes C231 . C232 . 1.410(11) yes C231 . H2311 . 1.015 no C232 . C233 . 1.350(11) yes C232 . H2321 . 1.032 no C233 . C234 . 1.417(11) yes C233 . H2331 . 1.024 no C234 . C235 . 1.391(11) yes C234 . C239 . 1.421(10) yes C235 . C236 . 1.368(12) yes C235 . H2351 . 1.032 no C236 . C237 . 1.434(12) yes C236 . H2361 . 1.013 no C237 . C238 . 1.353(11) yes C237 . H2371 . 1.042 no C238 . C239 . 1.420(10) yes C238 . N240 . 1.417(10) yes N240 . C241 . 1.312(10) yes C241 . C242 . 1.399(11) yes C241 . H2411 . 1.024 no C242 . C243 . 1.373(11) yes C242 . H2421 . 1.025 no C243 . C244 . 1.524(11) yes C243 . O248 . 1.256(8) yes C244 . F245 . 1.333(10) yes C244 . F246 . 1.323(9) yes C244 . F247 . 1.330(9) yes Cu3 . N311 . 2.289(7) yes Cu3 . N321 . 2.004(6) yes Cu3 . O329 . 2.273(6) yes Cu3 . N330 . 2.070(7) yes Cu3 . N340 . 1.968(6) yes Cu3 . O348 . 2.012(5) yes N311 . C312 . 1.318(11) yes N311 . C320 . 1.379(10) yes C312 . C313 . 1.373(12) yes C312 . H3121 . 1.038 no C313 . C314 . 1.371(13) yes C313 . H3131 . 1.031 no C314 . C315 . 1.421(12) yes C314 . H3141 . 1.027 no C315 . C316 . 1.410(12) yes C315 . C320 . 1.400(11) yes C316 . C317 . 1.356(12) yes C316 . H3161 . 1.025 no C317 . C318 . 1.407(12) yes C317 . H3171 . 1.017 no C318 . C319 . 1.392(11) yes C318 . H3181 . 1.033 no C319 . C320 . 1.444(11) yes C319 . N321 . 1.426(10) yes N321 . C322 . 1.307(10) yes C322 . C323 . 1.403(11) yes C322 . H3221 . 1.031 no C323 . C324 . 1.381(11) yes C323 . H3231 . 1.033 no C324 . C325 . 1.535(12) yes C324 . O329 . 1.243(9) yes C325 . F326 . 1.336(9) yes C325 . F327 . 1.333(10) yes C325 . F328 . 1.326(10) yes N330 . C331 . 1.325(10) yes N330 . C339 . 1.372(9) yes C331 . C332 . 1.408(11) yes C331 . H3311 . 1.020 no C332 . C333 . 1.361(11) yes C332 . H3321 . 1.023 no C333 . C334 . 1.420(11) yes C333 . H3331 . 1.013 no C334 . C335 . 1.416(11) yes C334 . C339 . 1.410(11) yes C335 . C336 . 1.347(12) yes C335 . H3351 . 1.019 no C336 . C337 . 1.409(12) yes C336 . H3361 . 1.019 no C337 . C338 . 1.362(11) yes C337 . H3371 . 1.042 no C338 . C339 . 1.431(11) yes C338 . N340 . 1.422(10) yes N340 . C341 . 1.287(10) yes C341 . C342 . 1.406(11) yes C341 . H3411 . 1.016 no C342 . C343 . 1.384(12) yes C342 . H3421 . 1.036 no C343 . C344 . 1.514(13) yes C343 . O348 . 1.259(10) yes C344 . F345 . 1.334(12) yes C344 . F346 . 1.332(11) yes C344 . F347 . 1.325(12) 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 N111 . Cu1 . N121 . 78.1(3) yes N111 . Cu1 . O129 . 167.2(2) yes N121 . Cu1 . O129 . 89.2(2) yes N111 . Cu1 . N130 . 87.4(2) yes N121 . Cu1 . N130 . 96.4(3) yes O129 . Cu1 . N130 . 91.9(2) yes N111 . Cu1 . N140 . 97.8(3) yes N121 . Cu1 . N140 . 175.5(3) yes O129 . Cu1 . N140 . 94.8(2) yes N130 . Cu1 . N140 . 81.4(3) yes N111 . Cu1 . O148 . 97.3(2) yes N121 . Cu1 . O148 . 92.3(2) yes O129 . Cu1 . O148 . 85.3(2) yes N130 . Cu1 . O148 . 170.8(3) yes N140 . Cu1 . O148 . 90.1(3) yes Cu1 . N111 . C112 . 131.6(5) yes Cu1 . N111 . C120 . 110.0(5) yes C112 . N111 . C120 . 118.1(7) yes N111 . C112 . C113 . 122.8(7) yes N111 . C112 . H1121 . 117.4 no C113 . C112 . H1121 . 119.8 no C112 . C113 . C114 . 119.2(8) yes C112 . C113 . H1131 . 120.0 no C114 . C113 . H1131 . 120.8 no C113 . C114 . C115 . 120.3(8) yes C113 . C114 . H1141 . 120.0 no C115 . C114 . H1141 . 119.8 no C114 . C115 . C116 . 123.5(8) yes C114 . C115 . C120 . 116.9(7) yes C116 . C115 . C120 . 119.6(8) yes C115 . C116 . C117 . 119.8(8) yes C115 . C116 . H1161 . 119.6 no C117 . C116 . H1161 . 120.6 no C116 . C117 . C118 . 121.4(8) yes C116 . C117 . H1171 . 120.0 no C118 . C117 . H1171 . 118.7 no C117 . C118 . C119 . 121.0(8) yes C117 . C118 . H1181 . 120.6 no C119 . C118 . H1181 . 118.5 no C118 . C119 . C120 . 117.6(7) yes C118 . C119 . N121 . 126.7(8) yes C120 . C119 . N121 . 115.7(7) yes C119 . C120 . C115 . 120.6(7) yes C119 . C120 . N111 . 116.7(7) yes C115 . C120 . N111 . 122.7(7) yes C119 . N121 . Cu1 . 117.6(5) yes C119 . N121 . C122 . 118.6(7) yes Cu1 . N121 . C122 . 122.6(6) yes N121 . C122 . C123 . 128.3(8) yes N121 . C122 . H1221 . 115.8 no C123 . C122 . H1221 . 115.9 no C122 . C123 . C124 . 124.6(8) yes C122 . C123 . H1231 . 117.0 no C124 . C123 . H1231 . 118.4 no C123 . C124 . C125 . 114.8(8) yes C123 . C124 . O129 . 129.8(8) yes C125 . C124 . O129 . 115.3(8) yes C124 . C125 . F126 . 115.2(8) yes C124 . C125 . F127 . 113.1(9) yes F126 . C125 . F127 . 103.6(9) yes C124 . C125 . F128 . 113.6(9) yes F126 . C125 . F128 . 105.8(9) yes F127 . C125 . F128 . 104.5(9) yes Cu1 . O129 . C124 . 117.6(5) yes Cu1 . N130 . C131 . 130.2(7) yes Cu1 . N130 . C139 . 110.4(6) yes C131 . N130 . C139 . 118.9(8) yes N130 . C131 . C132 . 122.2(10) yes N130 . C131 . H1311 . 116.3 no C132 . C131 . H1311 . 121.5 no C131 . C132 . C133 . 119.5(11) yes C131 . C132 . H1321 . 118.3 no C133 . C132 . H1321 . 122.2 no C132 . C133 . C134 . 120.0(11) yes C132 . C133 . H1331 . 118.3 no C134 . C133 . H1331 . 121.7 no C133 . C134 . C135 . 124.7(11) yes C133 . C134 . C139 . 116.5(11) yes C135 . C134 . C139 . 118.7(11) yes C134 . C135 . C136 . 118.8(10) yes C134 . C135 . H1351 . 120.1 no C136 . C135 . H1351 . 121.0 no C135 . C136 . C137 . 123.8(11) yes C135 . C136 . H1361 . 117.7 no C137 . C136 . H1361 . 118.4 no C136 . C137 . C138 . 119.4(11) yes C136 . C137 . H1371 . 120.4 no C138 . C137 . H1371 . 120.2 no C137 . C138 . C139 . 120.2(9) yes C137 . C138 . N140 . 126.1(9) yes C139 . C138 . N140 . 113.6(8) yes C134 . C139 . C138 . 119.1(10) yes C134 . C139 . N130 . 122.9(10) yes C138 . C139 . N130 . 118.0(8) yes C138 . N140 . Cu1 . 114.2(6) yes C138 . N140 . C141 . 117.9(7) yes Cu1 . N140 . C141 . 127.2(6) yes N140 . C141 . C142 . 124.0(8) yes N140 . C141 . H1411 . 117.0 no C142 . C141 . H1411 . 119.0 no C141 . C142 . C143 . 124.0(8) yes C141 . C142 . H1421 . 119.6 no C143 . C142 . H1421 . 116.4 no C142 . C143 . C144 . 118.4(8) yes C142 . C143 . O148 . 128.8(8) yes C144 . C143 . O148 . 112.6(8) yes C143 . C144 . F145 . 111.1(7) yes C143 . C144 . F146 . 111.5(8) yes F145 . C144 . F146 . 107.5(8) yes C143 . C144 . F147 . 113.9(8) yes F145 . C144 . F147 . 106.2(7) yes F146 . C144 . F147 . 106.4(8) yes C143 . O148 . Cu1 . 122.1(5) yes N211 . Cu2 . N221 . 78.6(3) yes N211 . Cu2 . O229 . 166.8(2) yes N221 . Cu2 . O229 . 89.0(2) yes N211 . Cu2 . N230 . 90.1(2) yes N221 . Cu2 . N230 . 95.2(3) yes O229 . Cu2 . N230 . 95.5(2) yes N211 . Cu2 . N240 . 96.7(2) yes N221 . Cu2 . N240 . 174.0(3) yes O229 . Cu2 . N240 . 95.9(2) yes N230 . Cu2 . N240 . 81.0(3) yes N211 . Cu2 . O248 . 92.7(2) yes N221 . Cu2 . O248 . 91.6(2) yes O229 . Cu2 . O248 . 83.1(2) yes N230 . Cu2 . O248 . 173.1(2) yes N240 . Cu2 . O248 . 92.4(2) yes Cu2 . N211 . C212 . 131.6(6) yes Cu2 . N211 . C220 . 109.7(5) yes C212 . N211 . C220 . 117.3(7) yes N211 . C212 . C213 . 123.0(8) yes N211 . C212 . H2121 . 119.4 no C213 . C212 . H2121 . 117.6 no C212 . C213 . C214 . 118.2(8) yes C212 . C213 . H2131 . 121.9 no C214 . C213 . H2131 . 120.0 no C213 . C214 . C215 . 121.1(8) yes C213 . C214 . H2141 . 119.5 no C215 . C214 . H2141 . 119.3 no C214 . C215 . C216 . 124.8(8) yes C214 . C215 . C220 . 116.7(8) yes C216 . C215 . C220 . 118.4(8) yes C215 . C216 . C217 . 120.3(8) yes C215 . C216 . H2161 . 118.8 no C217 . C216 . H2161 . 120.8 no C216 . C217 . C218 . 120.8(8) yes C216 . C217 . H2171 . 119.3 no C218 . C217 . H2171 . 119.9 no C217 . C218 . C219 . 122.0(8) yes C217 . C218 . H2181 . 119.9 no C219 . C218 . H2181 . 118.0 no C218 . C219 . C220 . 117.5(8) yes C218 . C219 . N221 . 125.0(7) yes C220 . C219 . N221 . 117.4(7) yes C219 . C220 . C215 . 120.9(8) yes C219 . C220 . N211 . 115.5(7) yes C215 . C220 . N211 . 123.6(8) yes C219 . N221 . Cu2 . 114.9(5) yes C219 . N221 . C222 . 119.0(7) yes Cu2 . N221 . C222 . 125.7(6) yes N221 . C222 . C223 . 127.5(7) yes N221 . C222 . H2221 . 115.5 no C223 . C222 . H2221 . 116.9 no C222 . C223 . C224 . 124.7(8) yes C222 . C223 . H2231 . 118.2 no C224 . C223 . H2231 . 117.1 no C223 . C224 . C225 . 116.2(8) yes C223 . C224 . O229 . 130.4(8) yes C225 . C224 . O229 . 113.3(8) yes C224 . C225 . F226 . 117.1(8) yes C224 . C225 . F227 . 111.3(8) yes F226 . C225 . F227 . 106.8(7) yes C224 . C225 . F228 . 110.8(8) yes F226 . C225 . F228 . 106.3(8) yes F227 . C225 . F228 . 103.6(8) yes Cu2 . O229 . C224 . 117.3(5) yes Cu2 . N230 . C231 . 129.3(6) yes Cu2 . N230 . C239 . 112.7(5) yes C231 . N230 . C239 . 117.9(7) yes N230 . C231 . C232 . 123.3(8) yes N230 . C231 . H2311 . 117.8 no C232 . C231 . H2311 . 118.9 no C231 . C232 . C233 . 118.5(8) yes C231 . C232 . H2321 . 120.1 no C233 . C232 . H2321 . 121.4 no C232 . C233 . C234 . 121.0(8) yes C232 . C233 . H2331 . 119.6 no C234 . C233 . H2331 . 119.3 no C233 . C234 . C235 . 125.1(8) yes C233 . C234 . C239 . 115.9(7) yes C235 . C234 . C239 . 118.9(8) yes C234 . C235 . C236 . 120.4(8) yes C234 . C235 . H2351 . 120.0 no C236 . C235 . H2351 . 119.5 no C235 . C236 . C237 . 120.7(8) yes C235 . C236 . H2361 . 119.8 no C237 . C236 . H2361 . 119.5 no C236 . C237 . C238 . 120.0(8) yes C236 . C237 . H2371 . 120.6 no C238 . C237 . H2371 . 119.4 no C237 . C238 . C239 . 119.6(8) yes C237 . C238 . N240 . 125.4(7) yes C239 . C238 . N240 . 115.0(6) yes C234 . C239 . C238 . 120.3(7) yes C234 . C239 . N230 . 123.2(7) yes C238 . C239 . N230 . 116.5(7) yes C238 . N240 . Cu2 . 114.8(5) yes C238 . N240 . C241 . 120.8(7) yes Cu2 . N240 . C241 . 124.2(6) yes N240 . C241 . C242 . 126.8(7) yes N240 . C241 . H2411 . 114.9 no C242 . C241 . H2411 . 118.3 no C241 . C242 . C243 . 124.3(7) yes C241 . C242 . H2421 . 118.1 no C243 . C242 . H2421 . 117.7 no C242 . C243 . C244 . 117.3(7) yes C242 . C243 . O248 . 128.7(7) yes C244 . C243 . O248 . 113.9(7) yes C243 . C244 . F245 . 110.0(7) yes C243 . C244 . F246 . 112.5(7) yes F245 . C244 . F246 . 106.2(7) yes C243 . C244 . F247 . 114.1(7) yes F245 . C244 . F247 . 107.0(7) yes F246 . C244 . F247 . 106.6(7) yes C243 . O248 . Cu2 . 122.9(5) yes N311 . Cu3 . N321 . 78.6(3) yes N311 . Cu3 . O329 . 164.1(2) yes N321 . Cu3 . O329 . 86.5(2) yes N311 . Cu3 . N330 . 86.0(2) yes N321 . Cu3 . N330 . 97.4(3) yes O329 . Cu3 . N330 . 90.7(2) yes N311 . Cu3 . N340 . 102.0(3) yes N321 . Cu3 . N340 . 178.8(3) yes O329 . Cu3 . N340 . 92.8(2) yes N330 . Cu3 . N340 . 81.6(3) yes N311 . Cu3 . O348 . 91.9(2) yes N321 . Cu3 . O348 . 89.2(2) yes O329 . Cu3 . O348 . 93.2(2) yes N330 . Cu3 . O348 . 172.6(3) yes N340 . Cu3 . O348 . 91.8(3) yes Cu3 . N311 . C312 . 132.4(6) yes Cu3 . N311 . C320 . 109.2(5) yes C312 . N311 . C320 . 117.0(8) yes N311 . C312 . C313 . 123.9(9) yes N311 . C312 . H3121 . 117.5 no C313 . C312 . H3121 . 118.7 no C312 . C313 . C314 . 120.7(9) yes C312 . C313 . H3131 . 120.5 no C314 . C313 . H3131 . 118.8 no C313 . C314 . C315 . 118.0(8) yes C313 . C314 . H3141 . 121.6 no C315 . C314 . H3141 . 120.5 no C314 . C315 . C316 . 123.4(9) yes C314 . C315 . C320 . 117.5(8) yes C316 . C315 . C320 . 119.1(8) yes C315 . C316 . C317 . 119.8(8) yes C315 . C316 . H3161 . 121.4 no C317 . C316 . H3161 . 118.8 no C316 . C317 . C318 . 122.5(8) yes C316 . C317 . H3171 . 119.7 no C318 . C317 . H3171 . 117.9 no C317 . C318 . C319 . 119.8(8) yes C317 . C318 . H3181 . 120.1 no C319 . C318 . H3181 . 120.1 no C318 . C319 . C320 . 117.8(8) yes C318 . C319 . N321 . 123.8(8) yes C320 . C319 . N321 . 118.3(7) yes C319 . C320 . C315 . 120.9(8) yes C319 . C320 . N311 . 116.1(8) yes C315 . C320 . N311 . 123.0(8) yes C319 . N321 . Cu3 . 115.5(5) yes C319 . N321 . C322 . 119.7(7) yes Cu3 . N321 . C322 . 123.3(6) yes N321 . C322 . C323 . 127.5(7) yes N321 . C322 . H3221 . 114.7 no C323 . C322 . H3221 . 117.8 no C322 . C323 . C324 . 124.0(7) yes C322 . C323 . H3231 . 117.8 no C324 . C323 . H3231 . 118.2 no C323 . C324 . C325 . 117.1(8) yes C323 . C324 . O329 . 129.8(8) yes C325 . C324 . O329 . 113.1(7) yes C324 . C325 . F326 . 114.9(8) yes C324 . C325 . F327 . 109.4(7) yes F326 . C325 . F327 . 105.7(7) yes C324 . C325 . F328 . 111.8(7) yes F326 . C325 . F328 . 107.5(7) yes F327 . C325 . F328 . 107.1(8) yes Cu3 . O329 . C324 . 115.4(5) yes Cu3 . N330 . C331 . 129.2(5) yes Cu3 . N330 . C339 . 111.5(5) yes C331 . N330 . C339 . 119.3(7) yes N330 . C331 . C332 . 122.4(8) yes N330 . C331 . H3311 . 119.6 no C332 . C331 . H3311 . 118.0 no C331 . C332 . C333 . 119.7(8) yes C331 . C332 . H3321 . 119.8 no C333 . C332 . H3321 . 120.5 no C332 . C333 . C334 . 119.2(8) yes C332 . C333 . H3331 . 120.4 no C334 . C333 . H3331 . 120.4 no C333 . C334 . C335 . 123.7(8) yes C333 . C334 . C339 . 118.2(8) yes C335 . C334 . C339 . 118.0(8) yes C334 . C335 . C336 . 119.9(8) yes C334 . C335 . H3351 . 120.3 no C336 . C335 . H3351 . 119.8 no C335 . C336 . C337 . 122.0(8) yes C335 . C336 . H3361 . 118.7 no C337 . C336 . H3361 . 119.3 no C336 . C337 . C338 . 120.7(9) yes C336 . C337 . H3371 . 120.0 no C338 . C337 . H3371 . 119.3 no C337 . C338 . C339 . 117.9(8) yes C337 . C338 . N340 . 128.7(8) yes C339 . C338 . N340 . 113.5(7) yes C338 . C339 . C334 . 121.1(8) yes C338 . C339 . N330 . 117.7(7) yes C334 . C339 . N330 . 121.1(8) yes C338 . N340 . Cu3 . 114.9(5) yes C338 . N340 . C341 . 119.0(7) yes Cu3 . N340 . C341 . 125.8(6) yes N340 . C341 . C342 . 125.3(8) yes N340 . C341 . H3411 . 117.1 no C342 . C341 . H3411 . 117.5 no C341 . C342 . C343 . 124.0(8) yes C341 . C342 . H3421 . 119.0 no C343 . C342 . H3421 . 117.0 no C342 . C343 . C344 . 118.1(8) yes C342 . C343 . O348 . 128.6(8) yes C344 . C343 . O348 . 113.2(8) yes C343 . C344 . F345 . 111.9(9) yes C343 . C344 . F346 . 114.6(9) yes F345 . C344 . F346 . 106.0(9) yes C343 . C344 . F347 . 112.7(9) yes F345 . C344 . F347 . 104.9(9) yes F346 . C344 . F347 . 106.0(9) yes C343 . O348 . Cu3 . 123.3(5) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C333 . H3331 . O248 2_557 153 1.01 2.47 3.400(14) yes