# Supplementary Material (ESI) for PCCP # This journal is (c) the Owner Societies 2009 data_global _journal_coden_Cambridge 1326 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Van Doorslaer, Sabine' 'Vimalkumar Balasubramanian' 'Carol Cristescu' 'Maria Ezhevskaya' 'Hans Moons' 'Markus Neuburger' 'Cornelia Palivan' _publ_contact_author_name 'Sabine Van Doorslaer' _publ_contact_author_email SABINE.VANDOORSLAER@UA.AC.BE _publ_section_title ; Structural characterization of a highly active superoxide-dismutase mimic ; # Attachment 'Cu-l11.cif' data_cul1_123k _database_code_depnum_ccdc_archive 'CCDC 724629' _audit_creation_date 09-02-10 _audit_creation_method CRYSTALS_ver_12.86 _chemical_name_systematic ? _chemical_melting_point ? _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 8.2044(5) _cell_length_b 10.5939(6) _cell_length_c 12.6014(7) _cell_angle_alpha 111.339(2) _cell_angle_beta 97.147(2) _cell_angle_gamma 99.073(2) _cell_volume 987.54(10) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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' 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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C28 H40 Cl2 Cu2 N10 O10 S4 # Dc = 1.69 Fooo = 514.00 Mu = 14.90 M = 501.47 # Found Formula = C28 H40 Cl2 Cu2 N10 O10 S4 # Dc = 1.69 FOOO = 514.00 Mu = 14.90 M = 501.47 _chemical_formula_sum 'C28 H40 Cl2 Cu2 N10 O10 S4' _chemical_formula_moiety 'C20 H16 Cl2 Cu2 N10 O6, 4(C2 H6 O S)' _chemical_compound_source ? _chemical_formula_weight 1002.95 _cell_measurement_reflns_used 1516 _cell_measurement_theta_min 4 _cell_measurement_theta_max 26 _cell_measurement_temperature 123 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_min 0.01 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.12 _exptl_crystal_density_diffrn 1.686 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 514 _exptl_absorpt_coefficient_mu 1.490 # Sheldrick geometric approximatio 0.89 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.99 # 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 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # 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 123 _diffrn_reflns_number 6570 _reflns_number_total 3974 _diffrn_reflns_av_R_equivalents 0.033 # Number of reflections with Friedels Law is 3974 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4136 _diffrn_reflns_theta_min 2.163 _diffrn_reflns_theta_max 26.597 _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 25.001 _diffrn_measured_fraction_theta_full 0.961 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min -13 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 1.31 _oxford_diffrn_Wilson_scale 55.47 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.47 _refine_diff_density_max 0.77 # 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>2.5\s(I) _refine_ls_number_reflns 2607 _refine_ls_number_restraints 59 _refine_ls_number_parameters 253 _oxford_refine_ls_R_factor_ref 0.0387 _refine_ls_wR_factor_ref 0.0365 _refine_ls_goodness_of_fit_ref 1.1069 _refine_ls_shift/su_max 0.000269 # The values computed from all data _oxford_reflns_number_all 3950 _refine_ls_R_factor_all 0.0788 _refine_ls_wR_factor_all 0.0623 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2725 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_gt 0.0377 # 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: 0.262 0.108 0.139 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., 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 0.69298(6) 0.45585(5) 0.48457(4) 0.0156 1.0000 Uani . . . . . . . Cl1 Cl 0.60580(11) 0.65523(9) 0.49221(8) 0.0175 1.0000 Uani . . . . . . . S1 S 0.43496(14) 0.16161(12) -0.22550(9) 0.0291 1.0000 Uani D . . . . . . S2 S 1.10638(13) -0.02127(11) 0.24537(9) 0.0241 1.0000 Uani D . . . . . . O1 O 0.7730(3) 0.5233(3) 0.6476(2) 0.0188 1.0000 Uani . . . . . . . O2 O 0.7733(3) 0.1048(3) 0.0978(2) 0.0228 1.0000 Uani . . . . . . . O3 O 0.3692(3) 0.3414(3) 0.0568(2) 0.0260 1.0000 Uani . . . . . . . O4 O 0.5215(4) 0.0901(3) -0.1581(3) 0.0334 1.0000 Uani . . . . . . . O5 O 0.9792(4) 0.0352(3) 0.3169(2) 0.0259 1.0000 Uani . . . . . . . N1 N 0.8464(4) 0.3277(3) 0.4535(3) 0.0160 1.0000 Uani D . . . . . . N2 N 0.8299(4) 0.2459(3) 0.3366(3) 0.0180 1.0000 Uani D . . . . . . N3 N 0.5659(4) 0.2173(3) 0.0764(3) 0.0199 1.0000 Uani D . . . . . . N4 N 0.5036(4) 0.3817(3) 0.2381(3) 0.0181 1.0000 Uani D . . . . . . N5 N 0.6220(4) 0.3571(3) 0.3120(3) 0.0163 1.0000 Uani D . . . . . . C1 C 0.9001(4) 0.4948(4) 0.7028(3) 0.0161 1.0000 Uani D . . . . . . C2 C 0.9488(4) 0.5683(4) 0.8249(3) 0.0162 1.0000 Uani D . . . . . . C3 C 1.0773(4) 0.5423(3) 0.8894(3) 0.0172 1.0000 Uani D . . . . . . C4 C 1.1658(4) 0.4416(4) 0.8368(3) 0.0190 1.0000 Uani D . . . . . . C5 C 1.1217(4) 0.3679(4) 0.7184(3) 0.0212 1.0000 Uani D . . . . . . C6 C 0.9904(4) 0.3925(4) 0.6496(3) 0.0160 1.0000 Uani D . . . . . . C7 C 0.9588(4) 0.3130(4) 0.5269(3) 0.0163 1.0000 Uani D . . . . . . C8 C 0.7095(5) 0.2665(4) 0.2666(3) 0.0170 1.0000 Uani D . . . . . . C9 C 0.6879(4) 0.1857(4) 0.1390(3) 0.0166 1.0000 Uani D . . . . . . C10 C 0.4719(5) 0.3169(4) 0.1207(3) 0.0196 1.0000 Uani D . . . . . . C11 C 0.5938(7) 0.3001(6) -0.2175(5) 0.0474 1.0000 Uani D . . . . . . C12 C 0.4176(7) 0.0567(6) -0.3713(4) 0.0403 1.0000 Uani D . . . . . . C13 C 0.9889(6) -0.1351(4) 0.1049(4) 0.0299 1.0000 Uani D . . . . . . C14 C 1.1997(5) 0.1130(5) 0.2051(4) 0.0269 1.0000 Uani D . . . . . . H2 H 0.8782 0.1759 0.3137 0.0244 1.0000 Uiso DR . . . . . . H3 H 0.5476 0.1737 0.0008 0.0214 1.0000 Uiso DR . . . . . . H4 H 0.4328 0.4284 0.2693 0.0212 1.0000 Uiso DR . . . . . . H21 H 0.8918 0.6362 0.8621 0.0194 1.0000 Uiso DR . . . . . . H31 H 1.1060 0.5931 0.9703 0.0194 1.0000 Uiso DR . . . . . . H41 H 1.2538 0.4254 0.8810 0.0243 1.0000 Uiso DR . . . . . . H51 H 1.1792 0.2975 0.6817 0.0259 1.0000 Uiso DR . . . . . . H71 H 1.0228 0.2459 0.4976 0.0205 1.0000 Uiso DR . . . . . . H111 H 0.6913 0.2638 -0.2376 0.0691 1.0000 Uiso DR . . . . . . H112 H 0.5507 0.3371 -0.2724 0.0691 1.0000 Uiso DR . . . . . . H113 H 0.6182 0.3701 -0.1396 0.0691 1.0000 Uiso DR . . . . . . H121 H 0.3319 -0.0250 -0.3900 0.0632 1.0000 Uiso DR . . . . . . H122 H 0.3889 0.1064 -0.4189 0.0630 1.0000 Uiso DR . . . . . . H123 H 0.5234 0.0317 -0.3826 0.0625 1.0000 Uiso DR . . . . . . H131 H 0.9109 -0.0891 0.0796 0.0411 1.0000 Uiso DR . . . . . . H132 H 0.9305 -0.2172 0.1096 0.0410 1.0000 Uiso DR . . . . . . H133 H 1.0667 -0.1565 0.0533 0.0407 1.0000 Uiso DR . . . . . . H141 H 1.2754 0.0787 0.1543 0.0434 1.0000 Uiso DR . . . . . . H142 H 1.2593 0.1916 0.2744 0.0430 1.0000 Uiso DR . . . . . . H143 H 1.1132 0.1400 0.1659 0.0427 1.0000 Uiso DR . . . . . . 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 0.0155(2) 0.0174(3) 0.0122(2) 0.00269(19) 0.00027(17) 0.00882(19) Cl1 0.0166(4) 0.0171(5) 0.0186(4) 0.0064(4) 0.0023(3) 0.0057(4) S1 0.0321(6) 0.0336(6) 0.0205(5) 0.0083(5) 0.0030(4) 0.0114(5) S2 0.0310(5) 0.0232(6) 0.0220(5) 0.0082(4) 0.0089(4) 0.0156(5) O1 0.0184(13) 0.0214(15) 0.0150(13) 0.0033(11) 0.0001(10) 0.0119(11) O2 0.0221(14) 0.0291(17) 0.0165(13) 0.0044(12) 0.0069(11) 0.0124(12) O3 0.0257(15) 0.0373(18) 0.0152(13) 0.0080(13) 0.0005(11) 0.0159(13) O4 0.0489(19) 0.0346(19) 0.0205(15) 0.0115(14) 0.0073(13) 0.0182(15) O5 0.0357(16) 0.0276(17) 0.0200(14) 0.0080(13) 0.0127(12) 0.0198(13) N1 0.0165(15) 0.0146(17) 0.0125(14) 0.0006(13) 0.0013(12) 0.0035(13) N2 0.0198(16) 0.0215(18) 0.0101(14) 0.0013(13) 0.0016(12) 0.0104(14) N3 0.0187(15) 0.0266(19) 0.0093(14) 0.0010(14) 0.0026(12) 0.0062(14) N4 0.0164(15) 0.0254(19) 0.0138(15) 0.0069(14) 0.0015(12) 0.0113(14) N5 0.0146(15) 0.0198(17) 0.0135(15) 0.0042(13) 0.0035(12) 0.0066(13) C1 0.0139(16) 0.015(2) 0.0188(18) 0.0058(16) 0.0046(14) 0.0036(15) C2 0.0192(18) 0.014(2) 0.0144(17) 0.0042(15) 0.0019(14) 0.0073(15) C3 0.0224(19) 0.014(2) 0.0107(17) 0.0023(15) 0.0007(14) 0.0015(15) C4 0.0160(17) 0.025(2) 0.0173(18) 0.0113(17) -0.0018(14) 0.0056(16) C5 0.0220(19) 0.022(2) 0.0208(19) 0.0067(17) 0.0059(16) 0.0108(17) C6 0.0125(17) 0.017(2) 0.0177(18) 0.0054(16) 0.0017(14) 0.0064(15) C7 0.0157(17) 0.017(2) 0.0141(17) 0.0033(15) 0.0024(14) 0.0055(15) C8 0.0177(18) 0.016(2) 0.0167(18) 0.0057(16) 0.0038(14) 0.0028(15) C9 0.0149(17) 0.018(2) 0.0118(16) 0.0024(15) 0.0009(14) 0.0010(15) C10 0.0176(18) 0.026(2) 0.0148(18) 0.0078(17) 0.0052(15) 0.0040(16) C11 0.049(3) 0.035(3) 0.053(3) 0.022(3) -0.011(3) 0.003(2) C12 0.055(3) 0.038(3) 0.028(2) 0.016(2) 0.004(2) 0.009(2) C13 0.040(2) 0.018(2) 0.024(2) -0.0006(18) 0.0133(19) 0.0017(19) C14 0.025(2) 0.025(2) 0.030(2) 0.0085(19) 0.0061(17) 0.0055(18) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.1365(2) 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 . Cl1 2_666 2.6454(10) yes Cu1 . Cl1 . 2.3083(10) yes Cu1 . O1 . 1.901(3) yes Cu1 . N1 . 1.963(3) yes Cu1 . N5 . 2.000(3) yes S1 . O4 . 1.512(3) yes S1 . C11 . 1.765(5) yes S1 . C12 . 1.741(5) yes S2 . O5 . 1.516(3) yes S2 . C13 . 1.781(4) yes S2 . C14 . 1.774(4) yes O1 . C1 . 1.317(4) yes O2 . C9 . 1.205(4) yes O3 . C10 . 1.216(4) yes N1 . N2 . 1.386(4) yes N1 . C7 . 1.292(5) yes N2 . C8 . 1.339(5) yes N2 . H2 . 0.869 no N3 . C9 . 1.356(5) yes N3 . C10 . 1.398(5) yes N3 . H3 . 0.876 no N4 . N5 . 1.382(4) yes N4 . C10 . 1.355(5) yes N4 . H4 . 0.862 no N5 . C8 . 1.298(5) yes C1 . C2 . 1.418(5) yes C1 . C6 . 1.421(5) yes C2 . C3 . 1.375(5) yes C2 . H21 . 0.933 no C3 . C4 . 1.397(5) yes C3 . H31 . 0.942 no C4 . C5 . 1.377(5) yes C4 . H41 . 0.932 no C5 . C6 . 1.415(5) yes C5 . H51 . 0.951 no C6 . C7 . 1.433(5) yes C7 . H71 . 0.944 no C8 . C9 . 1.492(5) yes C11 . H111 . 0.963 no C11 . H112 . 0.969 no C11 . H113 . 0.964 no C12 . H121 . 0.958 no C12 . H122 . 0.963 no C12 . H123 . 0.959 no C13 . H131 . 0.954 no C13 . H132 . 0.950 no C13 . H133 . 0.961 no C14 . H141 . 0.963 no C14 . H142 . 0.965 no C14 . H143 . 0.953 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 Cl1 2_666 Cu1 . Cl1 . 91.40(3) yes Cl1 2_666 Cu1 . O1 . 90.49(8) yes Cl1 . Cu1 . O1 . 94.31(8) yes Cl1 2_666 Cu1 . N1 . 113.64(9) yes Cl1 . Cu1 . N1 . 154.16(9) yes O1 . Cu1 . N1 . 91.90(11) yes Cl1 2_666 Cu1 . N5 . 89.48(9) yes Cl1 . Cu1 . N5 . 95.03(9) yes O1 . Cu1 . N5 . 170.66(12) yes N1 . Cu1 . N5 . 79.57(12) yes Cu1 2_666 Cl1 . Cu1 . 88.60(3) yes O4 . S1 . C11 . 104.8(2) yes O4 . S1 . C12 . 105.4(2) yes C11 . S1 . C12 . 97.8(3) yes O5 . S2 . C13 . 106.33(19) yes O5 . S2 . C14 . 106.21(18) yes C13 . S2 . C14 . 97.1(2) yes Cu1 . O1 . C1 . 127.7(2) yes Cu1 . N1 . N2 . 113.8(2) yes Cu1 . N1 . C7 . 128.4(2) yes N2 . N1 . C7 . 117.8(3) yes N1 . N2 . C8 . 114.1(3) yes N1 . N2 . H2 . 121.7 no C8 . N2 . H2 . 123.0 no C9 . N3 . C10 . 126.3(3) yes C9 . N3 . H3 . 116.6 no C10 . N3 . H3 . 117.1 no N5 . N4 . C10 . 124.3(3) yes N5 . N4 . H4 . 116.8 no C10 . N4 . H4 . 117.7 no N4 . N5 . Cu1 . 128.0(2) yes N4 . N5 . C8 . 118.2(3) yes Cu1 . N5 . C8 . 113.5(2) yes O1 . C1 . C2 . 118.1(3) yes O1 . C1 . C6 . 124.9(3) yes C2 . C1 . C6 . 117.0(3) yes C1 . C2 . C3 . 121.7(3) yes C1 . C2 . H21 . 118.8 no C3 . C2 . H21 . 119.4 no C2 . C3 . C4 . 121.1(3) yes C2 . C3 . H31 . 119.4 no C4 . C3 . H31 . 119.5 no C3 . C4 . C5 . 118.7(3) yes C3 . C4 . H41 . 120.6 no C5 . C4 . H41 . 120.6 no C4 . C5 . C6 . 121.5(3) yes C4 . C5 . H51 . 119.6 no C6 . C5 . H51 . 118.9 no C1 . C6 . C5 . 119.9(3) yes C1 . C6 . C7 . 123.3(3) yes C5 . C6 . C7 . 116.7(3) yes C6 . C7 . N1 . 123.4(3) yes C6 . C7 . H71 . 118.7 no N1 . C7 . H71 . 117.9 no N2 . C8 . N5 . 119.0(3) yes N2 . C8 . C9 . 117.3(3) yes N5 . C8 . C9 . 123.7(3) yes C8 . C9 . N3 . 112.2(3) yes C8 . C9 . O2 . 123.0(3) yes N3 . C9 . O2 . 124.7(3) yes N3 . C10 . N4 . 115.2(3) yes N3 . C10 . O3 . 121.3(3) yes N4 . C10 . O3 . 123.5(3) yes S1 . C11 . H111 . 108.1 no S1 . C11 . H112 . 107.6 no H111 . C11 . H112 . 110.8 no S1 . C11 . H113 . 108.4 no H111 . C11 . H113 . 111.5 no H112 . C11 . H113 . 110.2 no S1 . C12 . H121 . 107.9 no S1 . C12 . H122 . 109.8 no H121 . C12 . H122 . 110.7 no S1 . C12 . H123 . 108.9 no H121 . C12 . H123 . 109.9 no H122 . C12 . H123 . 109.7 no S2 . C13 . H131 . 108.6 no S2 . C13 . H132 . 109.0 no H131 . C13 . H132 . 110.2 no S2 . C13 . H133 . 107.9 no H131 . C13 . H133 . 110.5 no H132 . C13 . H133 . 110.6 no S2 . C14 . H141 . 108.8 no S2 . C14 . H142 . 108.9 no H141 . C14 . H142 . 110.9 no S2 . C14 . H143 . 108.9 no H141 . C14 . H143 . 110.1 no H142 . C14 . H143 . 109.2 no 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 N2 . H2 . O5 . 160 0.87 1.83 2.660(6) yes N3 . H3 . O4 . 176 0.88 1.84 2.714(6) yes N4 . H4 . O1 2_666 160 0.86 2.13 2.952(6) yes C2 . H21 . O3 2_666 140 0.93 2.49 3.265(6) yes C7 . H71 . O5 . 134 0.94 2.48 3.207(6) yes C13 . H131 . O2 . 155 0.95 2.45 3.338(6) yes