# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Catherine E Housecroft' 'Edwin Constable' 'Markus Neuburger' 'Silvia Schaffner' 'Guoqi Zhang' _publ_contact_author_name 'Catherine E Housecroft' _publ_contact_author_email CATHERINE.HOUSECROFT@UNIBAS.CH _publ_section_title ; In search of enantioselective selective catalysts for the Henry reaction: Are two metal centres better than one? ; # Attachment 'GQ7_complex_1new.cif' data_gq7_173k _database_code_depnum_ccdc_archive 'CCDC 717570' _audit_creation_date 08-11-12 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'gq7_173k_0m in P2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.9835(3) _cell_length_b 20.8163(7) _cell_length_c 11.0230(4) _cell_angle_alpha 90 _cell_angle_beta 101.777(2) _cell_angle_gamma 90 _cell_volume 1793.32(11) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-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' _cell_formula_units_Z 4 # Given Formula = C20 H22 Cu1 N2 O5 # Dc = 1.61 Fooo = 900.00 Mu = 12.55 M = 867.90 # Found Formula = C20 H22 Cu1 N2 O5 # Dc = 1.61 FOOO = 900.00 Mu = 12.55 M = 867.90 _chemical_formula_sum 'C20 H22 Cu1 N2 O5' _chemical_formula_moiety 'C20 H20 Cu N2 O4, H2 O' _chemical_compound_source ? _chemical_formula_weight 433.95 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_max 0.43 _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 1.255 # Sheldrick geometric approximatio 0.79 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 0.98 # 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 173 _diffrn_reflns_number 55033 _reflns_number_total 12420 _diffrn_reflns_av_R_equivalents 0.033 # Number of reflections with Friedels Law is 6504 # Number of reflections without Friedels Law is 12420 # Theoretical number of reflections is about 6388 _diffrn_reflns_theta_min 1.957 _diffrn_reflns_theta_max 32.317 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 31.024 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -12 _reflns_limit_h_max 11 _reflns_limit_k_min -30 _reflns_limit_k_max 30 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _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 -0.55 _refine_diff_density_max 0.40 _refine_ls_number_reflns 8548 _refine_ls_number_restraints 1 _refine_ls_number_parameters 506 #_refine_ls_R_factor_ref 0.0235 _refine_ls_wR_factor_ref 0.0262 _refine_ls_goodness_of_fit_ref 1.0676 #_reflns_number_all 12395 _refine_ls_R_factor_all 0.0411 _refine_ls_wR_factor_all 0.0370 # 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 8548 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_gt 0.0262 _refine_ls_shift/su_max 0.015963 _refine_ls_abs_structure_Flack 0.004(7) _refine_ls_abs_structure_details 'Flack (1983), 5916 Friedel-pairs' # 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 ad _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: 0.427 0.370 0.253 ; 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 0.36510(3) 0.53060(3) 0.39004(2) 0.0187 1.0000 Uani . . . . . . Cu2 Cu 0.11153(3) 0.58139(3) 0.61865(2) 0.0177 1.0000 Uani . . . . . . N1 N 0.4240(2) 0.62083(10) 0.39795(16) 0.0194 1.0000 Uani . . . . . . N2 N 0.1922(2) 0.55536(8) 0.24688(15) 0.0200 1.0000 Uani . . . . . . N3 N 0.2510(2) 0.55964(8) 0.77815(15) 0.0207 1.0000 Uani . . . . . . N4 N 0.0852(2) 0.4890(1) 0.59624(16) 0.0183 1.0000 Uani . . . . . . C1 C 0.6145(2) 0.54976(12) 0.61516(19) 0.0194 1.0000 Uani . . . . . . C2 C 0.7217(2) 0.52431(12) 0.72316(19) 0.0230 1.0000 Uani . . . . . . C3 C 0.8237(3) 0.56386(11) 0.8085(2) 0.0271 1.0000 Uani . . . . . . C4 C 0.8267(3) 0.63012(13) 0.7891(2) 0.0285 1.0000 Uani . . . . . . C5 C 0.7275(3) 0.65634(11) 0.6854(2) 0.0239 1.0000 Uani . . . . . . C6 C 0.6200(3) 0.61698(11) 0.5976(2) 0.0193 1.0000 Uani . . . . . . C7 C 0.5244(3) 0.64879(11) 0.4888(2) 0.0208 1.0000 Uani . . . . . . C8 C 0.3451(2) 0.65589(9) 0.28459(17) 0.0206 1.0000 Uani . . . . . . C9 C 0.3309(3) 0.72853(12) 0.2946(2) 0.0284 1.0000 Uani . . . . . . C10 C 0.2407(3) 0.75689(11) 0.1707(2) 0.0321 1.0000 Uani . . . . . . C11 C 0.0659(3) 0.72661(11) 0.1264(2) 0.0330 1.0000 Uani . . . . . . C12 C 0.0798(3) 0.65322(12) 0.1147(2) 0.0274 1.0000 Uani . . . . . . C13 C 0.1680(2) 0.62579(9) 0.23976(17) 0.0208 1.0000 Uani . . . . . . C14 C 0.0946(2) 0.51663(10) 0.17313(18) 0.0233 1.0000 Uani . . . . . . C15 C 0.0912(3) 0.44780(11) 0.1861(2) 0.0244 1.0000 Uani . . . . . . C16 C -0.0329(3) 0.41342(13) 0.0999(2) 0.0314 1.0000 Uani . . . . . . C17 C -0.0620(3) 0.34922(13) 0.1176(3) 0.0342 1.0000 Uani . . . . . . C18 C 0.0315(3) 0.31721(12) 0.2198(2) 0.0313 1.0000 Uani . . . . . . C19 C 0.1545(3) 0.34926(11) 0.3046(2) 0.0258 1.0000 Uani . . . . . . C20 C 0.1886(2) 0.41581(11) 0.2892(2) 0.0232 1.0000 Uani . . . . . . C21 C 0.2935(2) 0.69551(10) 0.71504(19) 0.0194 1.0000 Uani . . . . . . C22 C 0.3420(2) 0.75960(11) 0.6961(2) 0.0229 1.0000 Uani . . . . . . C23 C 0.4698(3) 0.79032(11) 0.7774(2) 0.0279 1.0000 Uani . . . . . . C24 C 0.5560(3) 0.75848(12) 0.8843(2) 0.0308 1.0000 Uani . . . . . . C25 C 0.5117(3) 0.69670(11) 0.9074(2) 0.0270 1.0000 Uani . . . . . . C26 C 0.3817(3) 0.66421(10) 0.8235(2) 0.0225 1.0000 Uani . . . . . . C27 C 0.3544(3) 0.59765(9) 0.84887(19) 0.0231 1.0000 Uani . . . . . . C28 C 0.2328(2) 0.49158(8) 0.81037(16) 0.0201 1.0000 Uani . . . . . . C29 C 0.3763(3) 0.46385(11) 0.9089(2) 0.0287 1.0000 Uani . . . . . . C30 C 0.3474(3) 0.39224(10) 0.9273(2) 0.0320 1.0000 Uani . . . . . . C31 C 0.3212(3) 0.35495(10) 0.8062(2) 0.0296 1.0000 Uani . . . . . . C32 C 0.1731(3) 0.38313(11) 0.7092(2) 0.0261 1.0000 Uani . . . . . . C33 C 0.2121(2) 0.45362(9) 0.68929(17) 0.0202 1.0000 Uani . . . . . . C34 C -0.0216(3) 0.46072(10) 0.5108(2) 0.0182 1.0000 Uani . . . . . . C35 C -0.1369(3) 0.49258(11) 0.4118(2) 0.0188 1.0000 Uani . . . . . . C36 C -0.2462(3) 0.45325(11) 0.3262(2) 0.0228 1.0000 Uani . . . . . . C37 C -0.3542(3) 0.47899(11) 0.2250(2) 0.0267 1.0000 Uani . . . . . . C38 C -0.3539(3) 0.54569(11) 0.2059(2) 0.0262 1.0000 Uani . . . . . . C39 C -0.2503(2) 0.58507(12) 0.28833(18) 0.0209 1.0000 Uani . . . . . . C40 C -0.1381(2) 0.55992(12) 0.39487(18) 0.0177 1.0000 Uani . . . . . . O1 O 0.5183(2) 0.50919(8) 0.54018(15) 0.0230 1.0000 Uani . . . . . . O2 O 0.7255(2) 0.45954(9) 0.74444(17) 0.0324 1.0000 Uani . . . . . . O3 O 0.30636(19) 0.44210(8) 0.37578(15) 0.0249 1.0000 Uani . . . . . . O4 O 0.2419(2) 0.31793(9) 0.40655(17) 0.0320 1.0000 Uani . . . . . . O5 O 0.1734(2) 0.67013(8) 0.63064(15) 0.0242 1.0000 Uani . . . . . . O6 O 0.2597(2) 0.79101(8) 0.59049(16) 0.0286 1.0000 Uani . . . . . . O7 O -0.04121(19) 0.60125(8) 0.46758(14) 0.0199 1.0000 Uani . . . . . . O8 O -0.25447(19) 0.64982(8) 0.26695(16) 0.0261 1.0000 Uani . . . . . . O21 O 0.5528(2) 0.37185(9) 0.55001(17) 0.0346 1.0000 Uani . . . . . . O22 O -0.0637(2) 0.73806(9) 0.44976(16) 0.0322 1.0000 Uani . . . . . . H2 H 0.6783 0.4405 0.6841 0.0463 1.0000 Uiso R . . . . . H4 H 0.3180 0.3415 0.4398 0.0479 1.0000 Uiso R . . . . . H6 H 0.1786 0.7708 0.5575 0.0421 1.0000 Uiso R . . . . . H8 H -0.1948 0.6663 0.3248 0.0386 1.0000 Uiso R . . . . . H11 H 0.6028 0.3506 0.5080 0.0511 1.0000 Uiso R . . . . . H12 H 0.5327 0.4035 0.5112 0.0524 1.0000 Uiso R . . . . . H13 H -0.0339 0.7073 0.4891 0.0482 1.0000 Uiso R . . . . . H14 H -0.1276 0.7552 0.4881 0.0475 1.0000 Uiso R . . . . . H31 H 0.8888 0.5459 0.8805 0.0313 1.0000 Uiso R . . . . . H41 H 0.8999 0.6568 0.8479 0.0328 1.0000 Uiso R . . . . . H51 H 0.7280 0.7019 0.6705 0.0290 1.0000 Uiso R . . . . . H71 H 0.5384 0.6929 0.4836 0.0250 1.0000 Uiso R . . . . . H81 H 0.4146 0.6468 0.2213 0.0237 1.0000 Uiso R . . . . . H91 H 0.2672 0.7399 0.3586 0.0334 1.0000 Uiso R . . . . . H92 H 0.4435 0.7472 0.3155 0.0329 1.0000 Uiso R . . . . . H101 H 0.3113 0.7517 0.1089 0.0376 1.0000 Uiso R . . . . . H102 H 0.2267 0.8035 0.1816 0.0375 1.0000 Uiso R . . . . . H111 H 0.0148 0.7428 0.0464 0.0383 1.0000 Uiso R . . . . . H112 H -0.0094 0.7357 0.1827 0.0394 1.0000 Uiso R . . . . . H121 H -0.0367 0.6362 0.0910 0.0322 1.0000 Uiso R . . . . . H122 H 0.1427 0.6418 0.0510 0.0326 1.0000 Uiso R . . . . . H131 H 0.1001 0.6370 0.3010 0.0250 1.0000 Uiso R . . . . . H141 H 0.0143 0.5341 0.1062 0.0288 1.0000 Uiso R . . . . . H161 H -0.0973 0.4345 0.0297 0.0378 1.0000 Uiso R . . . . . H171 H -0.1435 0.3284 0.0630 0.0415 1.0000 Uiso R . . . . . H181 H 0.0120 0.2740 0.2343 0.0388 1.0000 Uiso R . . . . . H231 H 0.4995 0.8331 0.7593 0.0339 1.0000 Uiso R . . . . . H241 H 0.6456 0.7782 0.9409 0.0372 1.0000 Uiso R . . . . . H251 H 0.5715 0.6747 0.9775 0.0308 1.0000 Uiso R . . . . . H271 H 0.4186 0.5805 0.9233 0.0273 1.0000 Uiso R . . . . . H281 H 0.1251 0.4884 0.8407 0.0230 1.0000 Uiso R . . . . . H291 H 0.3822 0.4864 0.9873 0.0322 1.0000 Uiso R . . . . . H292 H 0.4819 0.4710 0.8839 0.0319 1.0000 Uiso R . . . . . H301 H 0.4451 0.3751 0.9812 0.0371 1.0000 Uiso R . . . . . H302 H 0.2481 0.3865 0.9657 0.0370 1.0000 Uiso R . . . . . H311 H 0.2946 0.3110 0.8218 0.0362 1.0000 Uiso R . . . . . H312 H 0.4265 0.3550 0.7748 0.0358 1.0000 Uiso R . . . . . H321 H 0.0687 0.3796 0.7401 0.0297 1.0000 Uiso R . . . . . H322 H 0.1595 0.3595 0.6328 0.0303 1.0000 Uiso R . . . . . H331 H 0.3188 0.4569 0.6612 0.0236 1.0000 Uiso R . . . . . H341 H -0.0254 0.4155 0.5088 0.0228 1.0000 Uiso R . . . . . H361 H -0.2403 0.4080 0.3418 0.0269 1.0000 Uiso R . . . . . H371 H -0.4239 0.4520 0.1697 0.0299 1.0000 Uiso R . . . . . H381 H -0.4276 0.5629 0.1366 0.0305 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02003(9) 0.01443(11) 0.02007(12) 0.00083(9) 0.00077(8) -0.00190(9) Cu2 0.02084(9) 0.01193(10) 0.01842(11) 0.00067(9) -0.00076(8) -0.00137(9) N1 0.0210(7) 0.0176(9) 0.0184(8) 0.0035(6) 0.0014(7) 0.0003(6) N2 0.0206(7) 0.0179(7) 0.0210(7) 0.0005(5) 0.0028(6) -0.0007(5) N3 0.0243(7) 0.0153(6) 0.0218(7) 0.0014(5) 0.0030(6) 0.0012(5) N4 0.0224(8) 0.0138(8) 0.0179(8) 0.0009(6) 0.0020(6) 0.0002(6) C1 0.0182(9) 0.0191(11) 0.0213(10) 0.0015(6) 0.0052(8) 0.0011(6) C2 0.0234(8) 0.0218(10) 0.0229(9) 0.0014(8) 0.0028(7) 0.0036(8) C3 0.0281(9) 0.0283(11) 0.0218(9) -0.0009(8) -0.0025(7) 0.0058(7) C4 0.0282(10) 0.0296(12) 0.0249(10) -0.0065(9) -0.0011(9) 0.0007(8) C5 0.0271(9) 0.0212(10) 0.0221(10) -0.0058(8) 0.0022(8) -0.0016(7) C6 0.0204(9) 0.0184(10) 0.0184(9) -0.0001(8) 0.0021(8) -0.0003(6) C7 0.0238(9) 0.0146(10) 0.0245(11) -0.0009(8) 0.0060(8) -0.0008(7) C8 0.0219(8) 0.0186(8) 0.0205(8) 0.0047(6) 0.0023(6) 0.0000(6) C9 0.0372(10) 0.0193(11) 0.0265(11) 0.0054(9) 0.0013(9) 0.0008(8) C10 0.0377(10) 0.0233(9) 0.0330(11) 0.0115(8) 0.0017(9) 0.0007(8) C11 0.0322(10) 0.0304(10) 0.0340(11) 0.0144(8) 0.0006(8) 0.0049(8) C12 0.0252(9) 0.0307(11) 0.0237(10) 0.0056(8) -0.0010(7) -0.0011(8) C13 0.0223(8) 0.0180(7) 0.0215(8) 0.0021(6) 0.0030(6) 0.0022(6) C14 0.0235(8) 0.0254(10) 0.0198(8) -0.0008(6) 0.0020(7) -0.0001(6) C15 0.0234(8) 0.0266(10) 0.0231(9) -0.0052(8) 0.0043(8) -0.0031(7) C16 0.0296(10) 0.0343(13) 0.0301(12) -0.0111(9) 0.0054(9) -0.0040(8) C17 0.0333(10) 0.0281(12) 0.0409(14) -0.0186(10) 0.0067(10) -0.0083(9) C18 0.0295(10) 0.0245(11) 0.0412(13) -0.0136(9) 0.0099(10) -0.0059(8) C19 0.0277(9) 0.0176(10) 0.0338(11) -0.0077(8) 0.0100(9) -0.0033(7) C20 0.0221(8) 0.0214(10) 0.0275(10) -0.0065(8) 0.0082(8) -0.0043(7) C21 0.0213(8) 0.0133(9) 0.0233(9) -0.0023(7) 0.0036(7) -0.0010(6) C22 0.0233(8) 0.0189(10) 0.0271(10) -0.0024(8) 0.0064(8) -0.0014(7) C23 0.0288(9) 0.0160(9) 0.0391(13) -0.0093(8) 0.0071(9) -0.0037(7) C24 0.0283(9) 0.0260(11) 0.0349(12) -0.0122(9) -0.0011(9) -0.0034(8) C25 0.0293(9) 0.0232(11) 0.0246(10) -0.0078(8) -0.0034(8) -0.0004(8) C26 0.0252(8) 0.0162(9) 0.0252(10) -0.0037(7) 0.0027(7) -0.0013(7) C27 0.0283(8) 0.0177(8) 0.0217(8) 0.0001(6) 0.0015(7) 0.0007(6) C28 0.0254(8) 0.0151(7) 0.0187(7) 0.0021(6) 0.0017(6) 0.0008(6) C29 0.0353(11) 0.0210(9) 0.0249(10) 0.0041(7) -0.0048(8) 0.0010(7) C30 0.0437(11) 0.0214(9) 0.0272(10) 0.0087(7) -0.0018(8) 0.0029(8) C31 0.0367(10) 0.0183(9) 0.0315(10) 0.0065(7) 0.0019(8) 0.0062(7) C32 0.0351(10) 0.0131(10) 0.0277(11) -0.0002(8) 0.0003(9) -0.0014(7) C33 0.0229(8) 0.0163(7) 0.0201(8) 0.0036(6) 0.0015(6) 0.0018(6) C34 0.0236(8) 0.0148(9) 0.0159(9) 0.0012(7) 0.0028(7) -0.0009(7) C35 0.0213(9) 0.0168(9) 0.0181(8) -0.0019(8) 0.0032(8) -0.0019(6) C36 0.0243(8) 0.0189(10) 0.0238(10) -0.0024(7) 0.0020(8) -0.0008(7) C37 0.0247(9) 0.0239(10) 0.0275(10) -0.0074(8) -0.0039(8) -0.0007(7) C38 0.0250(8) 0.0285(12) 0.0218(9) -0.0007(7) -0.0027(7) 0.0038(7) C39 0.0193(7) 0.0206(9) 0.0226(8) 0.0009(8) 0.0039(6) 0.0022(8) C40 0.0161(9) 0.0198(11) 0.0174(9) 0.0009(6) 0.0038(7) 0.0002(6) O1 0.0252(6) 0.0167(7) 0.0249(8) 0.0025(6) 0.0000(6) -0.0026(5) O2 0.0393(8) 0.0224(8) 0.0313(8) 0.0062(6) -0.0026(7) 0.0044(6) O3 0.0277(7) 0.0159(7) 0.0292(8) -0.0011(6) 0.0009(6) -0.0038(5) O4 0.0381(8) 0.0182(8) 0.0386(10) -0.0010(7) 0.0055(8) -0.0073(6) O5 0.0281(7) 0.0154(7) 0.0254(8) 0.0011(6) -0.0032(6) -0.0060(5) O6 0.0362(8) 0.0161(8) 0.0321(9) -0.0006(6) 0.0033(7) -0.0069(6) O7 0.0245(6) 0.0143(7) 0.0184(7) 0.0015(5) -0.0019(6) -0.0021(5) O8 0.0262(6) 0.0200(7) 0.0295(8) 0.0035(6) -0.0007(6) 0.0012(5) O21 0.0446(9) 0.0227(9) 0.0372(10) 0.0054(7) 0.0102(8) 0.0081(7) O22 0.0427(8) 0.0190(8) 0.0343(10) 0.0042(7) 0.0063(8) 0.0072(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.23296(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . Cu2 . 3.6944(4) yes Cu1 . N1 . 1.934(2) yes Cu1 . N2 . 1.9420(16) yes Cu1 . O1 . 1.8993(17) yes Cu1 . O3 . 1.8997(16) yes Cu2 . N3 . 1.9331(17) yes Cu2 . N4 . 1.9450(19) yes Cu2 . O5 . 1.9097(16) yes Cu2 . O7 . 1.8979(16) yes N1 . C7 . 1.287(3) yes N1 . C8 . 1.473(3) yes N2 . C13 . 1.479(2) yes N2 . C14 . 1.288(2) yes N3 . C27 . 1.286(3) yes N3 . C28 . 1.475(2) yes N4 . C33 . 1.482(3) yes N4 . C34 . 1.278(3) yes C1 . C2 . 1.420(3) yes C1 . C6 . 1.414(3) yes C1 . O1 . 1.314(3) yes C2 . C3 . 1.383(3) yes C2 . O2 . 1.368(3) yes C3 . C4 . 1.397(4) yes C3 . H31 . 0.934 no C4 . C5 . 1.364(3) yes C4 . H41 . 0.957 no C5 . C6 . 1.416(3) yes C5 . H51 . 0.962 no C6 . C7 . 1.444(3) yes C7 . H71 . 0.927 no C8 . C9 . 1.522(3) yes C8 . C13 . 1.533(3) yes C8 . H81 . 0.994 no C9 . C10 . 1.527(3) yes C9 . H91 . 0.979 no C9 . H92 . 0.964 no C10 . C11 . 1.518(3) yes C10 . H101 . 0.975 no C10 . H102 . 0.986 no C11 . C12 . 1.539(3) yes C11 . H111 . 0.954 no C11 . H112 . 0.967 no C12 . C13 . 1.525(3) yes C12 . H121 . 0.980 no C12 . H122 . 0.973 no C13 . H131 . 0.976 no C14 . C15 . 1.441(3) yes C14 . H141 . 0.946 no C15 . C16 . 1.419(3) yes C15 . C20 . 1.407(3) yes C16 . C17 . 1.377(4) yes C16 . H161 . 0.945 no C17 . C18 . 1.388(4) yes C17 . H171 . 0.903 no C18 . C19 . 1.382(3) yes C18 . H181 . 0.933 no C19 . C20 . 1.429(3) yes C19 . O4 . 1.362(3) yes C20 . O3 . 1.314(3) yes C21 . C22 . 1.417(3) yes C21 . C26 . 1.416(3) yes C21 . O5 . 1.304(3) yes C22 . C23 . 1.371(3) yes C22 . O6 . 1.379(3) yes C23 . C24 . 1.403(4) yes C23 . H231 . 0.954 no C24 . C25 . 1.371(3) yes C24 . H241 . 0.942 no C25 . C26 . 1.414(3) yes C25 . H251 . 0.940 no C26 . C27 . 1.439(3) yes C27 . H271 . 0.944 no C28 . C29 . 1.522(3) yes C28 . C33 . 1.531(3) yes C28 . H281 . 0.986 no C29 . C30 . 1.528(3) yes C29 . H291 . 0.975 no C29 . H292 . 0.951 no C30 . C31 . 1.522(3) yes C30 . H301 . 0.948 no C30 . H302 . 0.979 no C31 . C32 . 1.538(3) yes C31 . H311 . 0.962 no C31 . H312 . 0.972 no C32 . C33 . 1.525(3) yes C32 . H321 . 0.965 no C32 . H322 . 0.962 no C33 . H331 . 0.966 no C34 . C35 . 1.438(3) yes C34 . H341 . 0.942 no C35 . C36 . 1.409(3) yes C35 . C40 . 1.414(3) yes C36 . C37 . 1.372(3) yes C36 . H361 . 0.957 no C37 . C38 . 1.404(3) yes C37 . H371 . 0.926 no C38 . C39 . 1.369(3) yes C38 . H381 . 0.935 no C39 . C40 . 1.423(3) yes C39 . O8 . 1.368(3) yes C40 . O7 . 1.315(3) yes O2 . H2 . 0.799 no O4 . H4 . 0.809 no O6 . H6 . 0.796 no O8 . H8 . 0.792 no O21 . H11 . 0.803 no O21 . H12 . 0.784 no O22 . H13 . 0.783 no O22 . H14 . 0.808 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 Cu2 . Cu1 . N1 . 81.57(5) yes Cu2 . Cu1 . N2 . 94.64(5) yes N1 . Cu1 . N2 . 84.54(8) yes Cu2 . Cu1 . O1 . 79.51(5) yes N1 . Cu1 . O1 . 94.65(7) yes N2 . Cu1 . O1 . 174.14(7) yes Cu2 . Cu1 . O3 . 100.00(5) yes N1 . Cu1 . O3 . 177.87(7) yes N2 . Cu1 . O3 . 93.87(7) yes O1 . Cu1 . O3 . 87.06(7) yes Cu1 . Cu2 . N3 . 105.02(5) yes Cu1 . Cu2 . N4 . 71.96(5) yes N3 . Cu2 . N4 . 84.90(8) yes Cu1 . Cu2 . O5 . 98.86(5) yes N3 . Cu2 . O5 . 94.06(7) yes N4 . Cu2 . O5 . 170.05(7) yes Cu1 . Cu2 . O7 . 78.89(5) yes N3 . Cu2 . O7 . 175.35(7) yes N4 . Cu2 . O7 . 94.05(7) yes O5 . Cu2 . O7 . 87.75(7) yes Cu1 . N1 . C7 . 125.54(16) yes Cu1 . N1 . C8 . 112.65(13) yes C7 . N1 . C8 . 121.79(19) yes Cu1 . N2 . C13 . 111.70(12) yes Cu1 . N2 . C14 . 125.80(14) yes C13 . N2 . C14 . 122.08(17) yes Cu2 . N3 . C27 . 125.93(14) yes Cu2 . N3 . C28 . 112.16(12) yes C27 . N3 . C28 . 121.85(17) yes Cu2 . N4 . C33 . 111.27(13) yes Cu2 . N4 . C34 . 125.98(16) yes C33 . N4 . C34 . 122.70(19) yes C2 . C1 . C6 . 117.0(2) yes C2 . C1 . O1 . 117.6(2) yes C6 . C1 . O1 . 125.5(2) yes C1 . C2 . C3 . 121.2(2) yes C1 . C2 . O2 . 120.0(2) yes C3 . C2 . O2 . 118.8(2) yes C2 . C3 . C4 . 120.7(2) yes C2 . C3 . H31 . 119.3 no C4 . C3 . H31 . 120.0 no C3 . C4 . C5 . 119.9(2) yes C3 . C4 . H41 . 119.8 no C5 . C4 . H41 . 120.3 no C4 . C5 . C6 . 120.5(2) yes C4 . C5 . H51 . 121.0 no C6 . C5 . H51 . 118.4 no C5 . C6 . C1 . 120.7(2) yes C5 . C6 . C7 . 116.5(2) yes C1 . C6 . C7 . 122.8(2) yes C6 . C7 . N1 . 125.3(2) yes C6 . C7 . H71 . 117.1 no N1 . C7 . H71 . 117.5 no N1 . C8 . C9 . 117.13(17) yes N1 . C8 . C13 . 106.11(15) yes C9 . C8 . C13 . 110.58(16) yes N1 . C8 . H81 . 107.4 no C9 . C8 . H81 . 107.5 no C13 . C8 . H81 . 107.8 no C8 . C9 . C10 . 110.4(2) yes C8 . C9 . H91 . 110.4 no C10 . C9 . H91 . 109.4 no C8 . C9 . H92 . 109.8 no C10 . C9 . H92 . 107.7 no H91 . C9 . H92 . 109.1 no C9 . C10 . C11 . 111.24(18) yes C9 . C10 . H101 . 110.3 no C11 . C10 . H101 . 110.7 no C9 . C10 . H102 . 108.4 no C11 . C10 . H102 . 109.2 no H101 . C10 . H102 . 106.9 no C10 . C11 . C12 . 111.22(18) yes C10 . C11 . H111 . 110.0 no C12 . C11 . H111 . 107.4 no C10 . C11 . H112 . 111.3 no C12 . C11 . H112 . 108.2 no H111 . C11 . H112 . 108.6 no C11 . C12 . C13 . 108.92(18) yes C11 . C12 . H121 . 107.5 no C13 . C12 . H121 . 110.1 no C11 . C12 . H122 . 111.1 no C13 . C12 . H122 . 110.5 no H121 . C12 . H122 . 108.6 no C8 . C13 . C12 . 111.32(15) yes C8 . C13 . N2 . 106.62(14) yes C12 . C13 . N2 . 116.78(17) yes C8 . C13 . H131 . 106.6 no C12 . C13 . H131 . 108.4 no N2 . C13 . H131 . 106.6 no N2 . C14 . C15 . 125.50(18) yes N2 . C14 . H141 . 118.6 no C15 . C14 . H141 . 115.8 no C14 . C15 . C16 . 117.4(2) yes C14 . C15 . C20 . 122.17(19) yes C16 . C15 . C20 . 119.9(2) yes C15 . C16 . C17 . 120.6(3) yes C15 . C16 . H161 . 120.2 no C17 . C16 . H161 . 119.2 no C16 . C17 . C18 . 120.2(2) yes C16 . C17 . H171 . 119.4 no C18 . C17 . H171 . 120.4 no C17 . C18 . C19 . 120.5(2) yes C17 . C18 . H181 . 121.4 no C19 . C18 . H181 . 118.0 no C18 . C19 . C20 . 120.9(2) yes C18 . C19 . O4 . 120.1(2) yes C20 . C19 . O4 . 119.0(2) yes C19 . C20 . C15 . 117.9(2) yes C19 . C20 . O3 . 116.3(2) yes C15 . C20 . O3 . 125.8(2) yes C22 . C21 . C26 . 117.00(18) yes C22 . C21 . O5 . 117.36(19) yes C26 . C21 . O5 . 125.63(18) yes C21 . C22 . C23 . 122.1(2) yes C21 . C22 . O6 . 118.28(19) yes C23 . C22 . O6 . 119.6(2) yes C22 . C23 . C24 . 120.0(2) yes C22 . C23 . H231 . 118.9 no C24 . C23 . H231 . 121.1 no C23 . C24 . C25 . 119.9(2) yes C23 . C24 . H241 . 121.7 no C25 . C24 . H241 . 118.4 no C24 . C25 . C26 . 120.7(2) yes C24 . C25 . H251 . 120.1 no C26 . C25 . H251 . 119.2 no C21 . C26 . C25 . 120.30(19) yes C21 . C26 . C27 . 122.57(19) yes C25 . C26 . C27 . 117.0(2) yes C26 . C27 . N3 . 125.35(19) yes C26 . C27 . H271 . 117.2 no N3 . C27 . H271 . 117.5 no N3 . C28 . C29 . 116.07(16) yes N3 . C28 . C33 . 106.52(14) yes C29 . C28 . C33 . 111.01(16) yes N3 . C28 . H281 . 106.3 no C29 . C28 . H281 . 108.3 no C33 . C28 . H281 . 108.3 no C28 . C29 . C30 . 110.64(18) yes C28 . C29 . H291 . 110.1 no C30 . C29 . H291 . 109.5 no C28 . C29 . H292 . 108.4 no C30 . C29 . H292 . 110.9 no H291 . C29 . H292 . 107.2 no C29 . C30 . C31 . 112.27(17) yes C29 . C30 . H301 . 108.8 no C31 . C30 . H301 . 107.9 no C29 . C30 . H302 . 109.5 no C31 . C30 . H302 . 109.8 no H301 . C30 . H302 . 108.6 no C30 . C31 . C32 . 111.31(17) yes C30 . C31 . H311 . 108.8 no C32 . C31 . H311 . 108.7 no C30 . C31 . H312 . 109.7 no C32 . C31 . H312 . 110.5 no H311 . C31 . H312 . 107.7 no C31 . C32 . C33 . 108.47(17) yes C31 . C32 . H321 . 108.8 no C33 . C32 . H321 . 109.9 no C31 . C32 . H322 . 110.3 no C33 . C32 . H322 . 110.8 no H321 . C32 . H322 . 108.6 no C28 . C33 . C32 . 111.09(16) yes C28 . C33 . N4 . 106.51(15) yes C32 . C33 . N4 . 116.58(16) yes C28 . C33 . H331 . 107.3 no C32 . C33 . H331 . 109.4 no N4 . C33 . H331 . 105.4 no N4 . C34 . C35 . 125.1(2) yes N4 . C34 . H341 . 119.4 no C35 . C34 . H341 . 115.5 no C34 . C35 . C36 . 116.9(2) yes C34 . C35 . C40 . 122.9(2) yes C36 . C35 . C40 . 120.0(2) yes C35 . C36 . C37 . 121.2(2) yes C35 . C36 . H361 . 116.8 no C37 . C36 . H361 . 122.0 no C36 . C37 . C38 . 119.2(2) yes C36 . C37 . H371 . 119.4 no C38 . C37 . H371 . 121.3 no C37 . C38 . C39 . 120.8(2) yes C37 . C38 . H381 . 118.7 no C39 . C38 . H381 . 120.5 no C38 . C39 . C40 . 121.4(2) yes C38 . C39 . O8 . 119.05(19) yes C40 . C39 . O8 . 119.6(2) yes C39 . C40 . C35 . 117.4(2) yes C39 . C40 . O7 . 117.1(2) yes C35 . C40 . O7 . 125.5(2) yes C1 . O1 . Cu1 . 125.94(15) yes C2 . O2 . H2 . 110.8 no C20 . O3 . Cu1 . 126.29(15) yes C19 . O4 . H4 . 107.1 no C21 . O5 . Cu2 . 125.69(14) yes C22 . O6 . H6 . 109.7 no C40 . O7 . Cu2 . 125.82(14) yes C39 . O8 . H8 . 107.4 no H11 . O21 . H12 . 102.7 no H13 . O22 . H14 . 103.0 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 O2 . H2 . O21 . 167 0.80 2.15 2.936(2) yes O4 . H4 . O21 . 160 0.81 2.11 2.884(2) yes O6 . H6 . O22 . 166 0.80 2.16 2.942(2) yes O8 . H8 . O22 . 162 0.79 2.15 2.916(2) yes O21 . H11 . O6 2_646 176 0.80 2.10 2.901(2) yes O22 . H13 . O5 . 142 0.78 2.17 2.832(2) yes O22 . H14 . O4 2_556 165 0.81 2.08 2.867(2) yes # Attachment 'GQ16_2_complex_3.cif' data_gq16_2_123k _database_code_depnum_ccdc_archive 'CCDC 717571' _audit_creation_date 08-08-11 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'gq16_2_123k_0m in P1' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.8481(3) _cell_length_b 11.8842(4) _cell_length_c 11.9786(4) _cell_angle_alpha 96.919(2) _cell_angle_beta 106.430(2) _cell_angle_gamma 109.055(2) _cell_volume 1110.04(7) _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 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' _cell_formula_units_Z 2 # Given Formula = C24 H24 Cu1 N2 O12 # Dc = 1.78 Fooo = 502.00 Mu = 10.63 M = 1192.01 # Found Formula = C24 H32 Cu1 N2 O4 # Dc = 1.42 FOOO = 502.00 Mu = 10.17 M = 952.15 _chemical_formula_sum 'C24 H32 Cu1 N2 O4' _chemical_formula_moiety 'C24 H32 Cu N2 O4' _chemical_compound_source ? _chemical_formula_weight 476.08 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 123 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_max 0.12 _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 502 _exptl_absorpt_coefficient_mu 1.017 # Sheldrick geometric approximatio 0.96 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.98 # 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 '\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 25366 _reflns_number_total 13379 _diffrn_reflns_av_R_equivalents 0.041 # Number of reflections with Friedels Law is 7256 # Number of reflections without Friedels Law is 13379 # Theoretical number of reflections is about 7745 _diffrn_reflns_theta_min 2.282 _diffrn_reflns_theta_max 32.055 _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 25.003 _diffrn_measured_fraction_theta_full 0.973 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -12 _reflns_limit_h_max 13 _reflns_limit_k_min -17 _reflns_limit_k_max 17 _reflns_limit_l_min -17 _reflns_limit_l_max 17 _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 0.68 _refine_ls_number_reflns 7017 _refine_ls_number_restraints 791 _refine_ls_number_parameters 560 #_refine_ls_R_factor_ref 0.0452 _refine_ls_wR_factor_ref 0.0470 _refine_ls_goodness_of_fit_ref 1.1747 #_reflns_number_all 13351 _refine_ls_R_factor_all 0.1012 _refine_ls_wR_factor_all 0.0877 # 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 7017 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_gt 0.0470 _refine_ls_shift/su_max 0.001488 _refine_ls_abs_structure_Flack 0.035(17) _refine_ls_abs_structure_details 'Flack (1983), 6123 Friedel-pairs' # 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 ad _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: 1.07 -0.434E-01 0.688 ; 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 0.18562(15) 0.55740(11) 0.56274(11) 0.0126 1.0000 Uani . U . . . . Cu2 Cu 0.70038(15) 0.57301(12) 0.57941(12) 0.0153 1.0000 Uani . U . . . . N1 N 0.1746(6) 0.5213(5) 0.3920(5) 0.0145 1.0000 Uani . U . . . . N2 N 0.0216(7) 0.3825(5) 0.5239(5) 0.0148 1.0000 Uani . U . . . . N51 N 0.6672(7) 0.6204(5) 0.7337(5) 0.0165 1.0000 Uani . U . . . . N52 N 0.9056(7) 0.7292(5) 0.6328(5) 0.0172 1.0000 Uani . U . . . . O1 O 0.3915(6) 0.6997(4) 0.6144(4) 0.0163 1.0000 Uani . U . . . . O2 O 0.1374(6) 0.6043(4) 0.7034(4) 0.0180 1.0000 Uani . U . . . . O3 O 0.5875(6) 0.9537(5) 0.6987(5) 0.0218 1.0000 Uani . U . . . . O4 O 0.2341(7) 0.6854(5) 0.9499(6) 0.0266 1.0000 Uani . U . . . . O51 O 0.5351(6) 0.4102(5) 0.5393(5) 0.0222 1.0000 Uani . U . . . . O52 O 0.7014(6) 0.5384(5) 0.4199(5) 0.0210 1.0000 Uani . U . . . . O53 O 0.2728(6) 0.1826(5) 0.4293(5) 0.0169 1.0000 Uani . U . . . . O54 O 0.6817(5) 0.4348(5) 0.1945(5) 0.0158 1.0000 Uani . U . . . . C1 C 0.4550(10) 0.7617(7) 0.5420(8) 0.0165 1.0000 Uani . U . . . . C2 C 0.5524(9) 0.8913(7) 0.5812(7) 0.0177 1.0000 Uani . U . . . . C3 C 0.6271(8) 0.9574(6) 0.5115(6) 0.0200 1.0000 Uani . U . . . . C4 C 0.6033(8) 0.9005(6) 0.3945(6) 0.0246 1.0000 Uani . U . . . . C5 C 0.4998(9) 0.7777(7) 0.3521(7) 0.0232 1.0000 Uani . U . . . . C6 C 0.4315(9) 0.7084(7) 0.4230(7) 0.0158 1.0000 Uani . U . . . . C7 C 0.3395(6) 0.5726(4) 0.3743(4) 0.0133 1.0000 Uani . U . . . . C8 C 0.0933(8) 0.3855(5) 0.3451(5) 0.0159 1.0000 Uani . U . . . . C9 C 0.0321(8) 0.3459(6) 0.2078(6) 0.0187 1.0000 Uani . U . . . . C10 C -0.0508(8) 0.2051(6) 0.1683(6) 0.0214 1.0000 Uani . U . . . . C11 C -0.2005(9) 0.1599(7) 0.2145(6) 0.0246 1.0000 Uani . U . . . . C12 C -0.1405(8) 0.1993(5) 0.3500(6) 0.0193 1.0000 Uani . U . . . . C13 C -0.0493(8) 0.3391(5) 0.3924(6) 0.0138 1.0000 Uani . U . . . . C14 C -0.1085(7) 0.3613(5) 0.5795(5) 0.0180 1.0000 Uani . U . . . . C15 C -0.0432(9) 0.4082(7) 0.7116(7) 0.0140 1.0000 Uani . U . . . . C16 C -0.1099(9) 0.3343(7) 0.7803(7) 0.0251 1.0000 Uani . U . . . . C17 C -0.0576(7) 0.3732(5) 0.9045(5) 0.0264 1.0000 Uani . U . . . . C18 C 0.0606(7) 0.4928(5) 0.9584(5) 0.0236 1.0000 Uani . U . . . . C19 C 0.1261(8) 0.5658(6) 0.8929(6) 0.0169 1.0000 Uani . U . . . . C20 C 0.0814(9) 0.5278(7) 0.7660(7) 0.0128 1.0000 Uani . U . . . . C21 C 0.4474(9) 0.9591(7) 0.7296(7) 0.0236 1.0000 Uani . U . . . . C22 C 0.5169(10) 1.0683(8) 0.8339(7) 0.0306 1.0000 Uani . U . . . . C23 C 0.3997(9) 0.7235(8) 0.9584(8) 0.0343 1.0000 Uani . U . . . . C24 C 0.4968(11) 0.8484(8) 1.0393(8) 0.0343 1.0000 Uani . U . . . . C51 C 0.4459(10) 0.3548(7) 0.6021(8) 0.0173 1.0000 Uani . U . . . . C52 C 0.3093(9) 0.2388(7) 0.5466(7) 0.0178 1.0000 Uani . U . . . . C53 C 0.2044(8) 0.1804(6) 0.6042(6) 0.0213 1.0000 Uani . U . . . . C54 C 0.2234(8) 0.2357(6) 0.7191(6) 0.0249 1.0000 Uani . U . . . . C55 C 0.3490(9) 0.3508(7) 0.7743(7) 0.0196 1.0000 Uani . U . . . . C56 C 0.4654(10) 0.4081(7) 0.7196(8) 0.0196 1.0000 Uani . U . . . . C57 C 0.6243(7) 0.5177(5) 0.7940(5) 0.0194 1.0000 Uani . U . . . . C58 C 0.8270(8) 0.7239(6) 0.8131(6) 0.0184 1.0000 Uani . U . . . . C59 C 0.8047(9) 0.7963(7) 0.9169(6) 0.0230 1.0000 Uani . U . . . . C60 C 0.9744(9) 0.9022(6) 0.9912(6) 0.0292 1.0000 Uani . U . . . . C61 C 1.0423(10) 0.9834(7) 0.9169(7) 0.0292 1.0000 Uani . U . . . . C62 C 1.0640(9) 0.9091(6) 0.8124(6) 0.0233 1.0000 Uani . U . . . . C63 C 0.8943(7) 0.8049(6) 0.7377(6) 0.0169 1.0000 Uani . U . . . . C64 C 0.9328(8) 0.7933(6) 0.5416(6) 0.0246 1.0000 Uani . U . . . . C65 C 0.9292(10) 0.7247(8) 0.4262(8) 0.0241 1.0000 Uani . U . . . . C66 C 1.0370(10) 0.7850(8) 0.3690(8) 0.0323 1.0000 Uani . U . . . . C67 C 1.0263(7) 0.7308(5) 0.2581(5) 0.0262 1.0000 Uani . U . . . . C68 C 0.9036(7) 0.6166(5) 0.1992(5) 0.0222 1.0000 Uani . U . . . . C69 C 0.7964(8) 0.5529(6) 0.2553(6) 0.0147 1.0000 Uani . U . . . . C70 C 0.8081(9) 0.6043(8) 0.3710(7) 0.0162 1.0000 Uani . U . . . . C71 C 0.4124(10) 0.1667(9) 0.3953(8) 0.0327 1.0000 Uani . U . . . . C72 C 0.3381(11) 0.0677(8) 0.2848(8) 0.0300 1.0000 Uani . U . . . . C73 C 0.5068(8) 0.4267(7) 0.1526(8) 0.0369 1.0000 Uani . U . . . . C74 C 0.3997(10) 0.2965(8) 0.0828(9) 0.0370 1.0000 Uani . U . . . . H1 H 0.1042 0.5540 0.3516 0.0250 1.0000 Uiso R . . . . . H2 H 0.0823 0.3396 0.5510 0.0213 1.0000 Uiso R . . . . . H3 H 0.5901 0.6531 0.7156 0.0204 1.0000 Uiso R . . . . . H4 H 0.9940 0.7097 0.6627 0.0248 1.0000 Uiso R . . . . . H31 H 0.6963 1.0430 0.5428 0.0227 1.0000 Uiso R . . . . . H41 H 0.6570 0.9455 0.3456 0.0274 1.0000 Uiso R . . . . . H51 H 0.4747 0.7393 0.2703 0.0214 1.0000 Uiso R . . . . . H71 H 0.4114 0.5331 0.4132 0.0156 1.0000 Uiso R . . . . . H72 H 0.3197 0.5548 0.2899 0.0156 1.0000 Uiso R . . . . . H81 H 0.1761 0.3514 0.3772 0.0179 1.0000 Uiso R . . . . . H91 H -0.0498 0.3801 0.1737 0.0208 1.0000 Uiso R . . . . . H92 H 0.1274 0.3747 0.1810 0.0208 1.0000 Uiso R . . . . . H101 H 0.0317 0.1710 0.2010 0.0234 1.0000 Uiso R . . . . . H102 H -0.0918 0.1801 0.0825 0.0234 1.0000 Uiso R . . . . . H111 H -0.2833 0.1935 0.1806 0.0237 1.0000 Uiso R . . . . . H112 H -0.2516 0.0721 0.1904 0.0237 1.0000 Uiso R . . . . . H121 H -0.2370 0.1737 0.3760 0.0195 1.0000 Uiso R . . . . . H122 H -0.0632 0.1616 0.3841 0.0195 1.0000 Uiso R . . . . . H131 H -0.1305 0.3751 0.3622 0.0146 1.0000 Uiso R . . . . . H141 H -0.1838 0.4002 0.5449 0.0200 1.0000 Uiso R . . . . . H142 H -0.1707 0.2746 0.5618 0.0200 1.0000 Uiso R . . . . . H161 H -0.1946 0.2537 0.7414 0.0297 1.0000 Uiso R . . . . . H171 H -0.1013 0.3196 0.9516 0.0316 1.0000 Uiso R . . . . . H181 H 0.0949 0.5231 1.0433 0.0268 1.0000 Uiso R . . . . . H211 H 0.3659 0.9693 0.6633 0.0256 1.0000 Uiso R . . . . . H212 H 0.3940 0.8856 0.7524 0.0256 1.0000 Uiso R . . . . . H221 H 0.4254 1.0757 0.8582 0.0328 1.0000 Uiso R . . . . . H222 H 0.5707 1.1412 0.8104 0.0328 1.0000 Uiso R . . . . . H223 H 0.5987 1.0575 0.8995 0.0328 1.0000 Uiso R . . . . . H231 H 0.4475 0.6673 0.9900 0.0357 1.0000 Uiso R . . . . . H232 H 0.4075 0.7260 0.8803 0.0357 1.0000 Uiso R . . . . . H241 H 0.6140 0.8746 1.0448 0.0362 1.0000 Uiso R . . . . . H242 H 0.4894 0.8461 1.1175 0.0362 1.0000 Uiso R . . . . . H243 H 0.4495 0.9048 1.0077 0.0362 1.0000 Uiso R . . . . . H531 H 0.1172 0.1008 0.5650 0.0242 1.0000 Uiso R . . . . . H541 H 0.1505 0.1947 0.7598 0.0297 1.0000 Uiso R . . . . . H551 H 0.3568 0.3922 0.8508 0.0244 1.0000 Uiso R . . . . . H571 H 0.6092 0.5476 0.8666 0.0218 1.0000 Uiso R . . . . . H572 H 0.7181 0.4911 0.8131 0.0218 1.0000 Uiso R . . . . . H581 H 0.9093 0.6897 0.8462 0.0197 1.0000 Uiso R . . . . . H591 H 0.7695 0.7433 0.9669 0.0256 1.0000 Uiso R . . . . . H592 H 0.7197 0.8291 0.8862 0.0256 1.0000 Uiso R . . . . . H601 H 0.9567 0.9499 1.0533 0.0303 1.0000 Uiso R . . . . . H602 H 1.0563 0.8685 1.0265 0.0303 1.0000 Uiso R . . . . . H611 H 1.1507 1.0453 0.9659 0.0300 1.0000 Uiso R . . . . . H612 H 0.9644 1.0215 0.8855 0.0300 1.0000 Uiso R . . . . . H621 H 1.1476 0.8754 0.8436 0.0237 1.0000 Uiso R . . . . . H622 H 1.1011 0.9620 0.7628 0.0237 1.0000 Uiso R . . . . . H631 H 0.8137 0.8412 0.7068 0.0186 1.0000 Uiso R . . . . . H641 H 1.0425 0.8588 0.5764 0.0275 1.0000 Uiso R . . . . . H642 H 0.8462 0.8268 0.5211 0.0275 1.0000 Uiso R . . . . . H661 H 1.1203 0.8660 0.4079 0.0355 1.0000 Uiso R . . . . . H671 H 1.1047 0.7725 0.2214 0.0340 1.0000 Uiso R . . . . . H681 H 0.8921 0.5807 0.1195 0.0283 1.0000 Uiso R . . . . . H711 H 0.4838 0.1450 0.4585 0.0350 1.0000 Uiso R . . . . . H712 H 0.4787 0.2416 0.3806 0.0350 1.0000 Uiso R . . . . . H721 H 0.4279 0.0560 0.2611 0.0335 1.0000 Uiso R . . . . . H722 H 0.2717 -0.0069 0.2999 0.0335 1.0000 Uiso R . . . . . H723 H 0.2666 0.0897 0.2220 0.0335 1.0000 Uiso R . . . . . H731 H 0.4956 0.4821 0.1016 0.0390 1.0000 Uiso R . . . . . H732 H 0.4725 0.4463 0.2192 0.0390 1.0000 Uiso R . . . . . H741 H 0.2823 0.2868 0.0529 0.0347 1.0000 Uiso R . . . . . H742 H 0.4357 0.2777 0.0168 0.0347 1.0000 Uiso R . . . . . H743 H 0.4126 0.2419 0.1344 0.0347 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0134(4) 0.0071(5) 0.0128(5) 0.0003(4) 0.0039(4) -0.0004(4) Cu2 0.0149(4) 0.0098(5) 0.0149(5) -0.0025(4) 0.0044(4) -0.0006(4) N1 0.013(2) 0.0114(16) 0.0157(17) 0.0029(16) 0.0057(19) -0.0002(16) N2 0.015(2) 0.0107(17) 0.0132(16) -0.0016(16) 0.0042(17) -0.0006(16) N51 0.020(2) 0.0095(19) 0.017(2) 0.0008(14) 0.0061(18) 0.0029(16) N52 0.018(2) 0.0100(19) 0.020(2) 0.0011(14) 0.008(2) 0.0022(14) O1 0.0164(19) 0.0104(18) 0.0177(19) 0.0006(14) 0.0073(16) -0.0005(12) O2 0.021(2) 0.0104(17) 0.0168(19) -0.0003(13) 0.0073(17) -0.0002(16) O3 0.015(2) 0.023(2) 0.021(2) -0.0018(18) 0.0015(17) 0.0053(18) O4 0.028(2) 0.0151(18) 0.030(3) 0.0001(17) 0.007(2) 0.0049(16) O51 0.025(3) 0.0117(17) 0.022(2) -0.0001(15) 0.0090(18) -0.0023(15) O52 0.018(2) 0.018(2) 0.0197(18) -0.0023(16) 0.0082(18) -0.0023(16) O53 0.0117(18) 0.0097(19) 0.024(2) 0.0021(16) 0.0017(16) 0.0014(16) O54 0.0130(17) 0.0168(18) 0.015(2) -0.0016(15) 0.0043(15) 0.0053(14) C1 0.016(3) 0.011(2) 0.019(2) 0.0012(17) 0.007(2) 0.002(2) C2 0.014(3) 0.013(2) 0.022(2) 0.0005(18) 0.004(2) 0.0028(19) C3 0.020(3) 0.011(2) 0.027(3) 0.0059(18) 0.004(2) 0.005(2) C4 0.026(3) 0.017(2) 0.026(3) 0.008(2) 0.009(3) -0.001(2) C5 0.017(3) 0.021(2) 0.016(3) 0.000(2) 0.003(2) -0.008(2) C6 0.016(3) 0.013(2) 0.017(2) 0.0031(18) 0.006(2) 0.0038(19) C7 0.010(2) 0.0143(18) 0.015(2) 0.0018(17) 0.0046(17) 0.0041(16) C8 0.022(2) 0.0101(17) 0.0130(18) 0.0022(14) 0.0064(18) 0.0020(17) C9 0.023(3) 0.0150(19) 0.0136(18) 0.0016(18) 0.004(2) 0.003(2) C10 0.027(3) 0.016(2) 0.016(2) -0.0023(19) 0.003(2) 0.007(2) C11 0.027(3) 0.015(2) 0.018(2) -0.003(2) 0.003(2) -0.003(2) C12 0.022(3) 0.0081(18) 0.019(2) -0.0002(18) 0.005(2) -0.0021(18) C13 0.015(2) 0.0073(17) 0.0139(17) -0.0002(14) 0.0020(16) 0.0017(15) C14 0.013(2) 0.017(2) 0.021(2) 0.0025(19) 0.0062(19) 0.0013(19) C15 0.010(3) 0.014(3) 0.018(2) 0.0030(19) 0.006(2) 0.003(2) C16 0.033(4) 0.019(3) 0.021(2) 0.002(2) 0.017(3) 0.002(3) C17 0.033(3) 0.025(2) 0.020(2) 0.008(2) 0.013(2) 0.006(2) C18 0.022(3) 0.029(2) 0.016(2) 0.0019(18) 0.007(2) 0.006(2) C19 0.017(3) 0.016(2) 0.0176(19) -0.0003(16) 0.006(2) 0.0079(18) C20 0.016(3) 0.011(2) 0.0162(19) 0.0042(16) 0.006(2) 0.010(2) C21 0.018(3) 0.020(3) 0.026(3) -0.001(2) 0.009(2) -0.001(2) C22 0.025(3) 0.027(3) 0.030(4) -0.007(3) 0.014(3) -0.002(3) C23 0.029(2) 0.026(3) 0.036(4) -0.005(3) 0.009(3) 0.000(2) C24 0.035(4) 0.023(3) 0.031(4) -0.002(3) 0.008(3) 0.001(3) C51 0.015(3) 0.011(2) 0.022(3) 0.0036(19) 0.004(2) 0.0017(18) C52 0.017(3) 0.010(2) 0.023(2) 0.0063(18) 0.003(2) 0.0029(17) C53 0.017(3) 0.012(2) 0.031(3) 0.009(2) 0.006(2) 0.002(2) C54 0.021(3) 0.021(2) 0.032(3) 0.011(2) 0.011(3) 0.004(2) C55 0.020(3) 0.019(3) 0.021(3) 0.005(2) 0.008(2) 0.009(2) C56 0.021(3) 0.011(3) 0.024(3) 0.005(2) 0.007(2) 0.0041(19) C57 0.021(3) 0.016(2) 0.017(2) 0.0067(16) 0.002(2) 0.0051(17) C58 0.018(2) 0.014(2) 0.0167(19) -0.0017(14) 0.0020(17) 0.0039(16) C59 0.027(3) 0.022(3) 0.014(2) 0.0002(18) 0.006(2) 0.0050(19) C60 0.032(3) 0.023(3) 0.021(3) -0.004(2) 0.004(2) 0.003(2) C61 0.034(3) 0.014(3) 0.027(3) -0.0045(19) 0.006(2) 0.001(2) C62 0.024(3) 0.012(2) 0.023(3) -0.0004(18) 0.002(2) 0.0002(17) C63 0.015(2) 0.0125(19) 0.019(2) -0.0012(13) 0.0022(18) 0.0054(15) C64 0.033(4) 0.014(2) 0.021(2) 0.0035(17) 0.009(3) 0.003(2) C65 0.029(4) 0.016(3) 0.020(3) 0.002(2) 0.008(3) 0.000(2) C66 0.030(4) 0.021(3) 0.037(4) 0.003(3) 0.016(3) -0.004(3) C67 0.029(3) 0.023(2) 0.033(3) 0.016(2) 0.016(2) 0.0092(19) C68 0.020(3) 0.028(2) 0.023(3) 0.0090(19) 0.010(2) 0.0109(18) C69 0.017(2) 0.0096(19) 0.019(2) 0.0060(16) 0.0050(19) 0.0079(16) C70 0.009(3) 0.019(3) 0.017(2) 0.0044(19) 0.001(2) 0.004(2) C71 0.018(3) 0.033(4) 0.037(4) -0.011(3) 0.000(3) 0.011(3) C72 0.033(4) 0.019(3) 0.032(4) -0.003(2) 0.008(3) 0.007(3) C73 0.016(2) 0.032(3) 0.048(5) -0.012(3) 0.000(3) 0.008(2) C74 0.029(3) 0.030(3) 0.028(4) 0.001(3) -0.004(3) -0.007(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4237(6) 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 . 2.006(6) yes Cu1 . N2 . 2.014(5) yes Cu1 . O1 . 1.913(5) yes Cu1 . O2 . 1.915(5) yes Cu2 . N51 . 1.995(6) yes Cu2 . N52 . 2.002(5) yes Cu2 . O51 . 1.909(5) yes Cu2 . O52 . 1.909(5) yes N1 . C7 . 1.473(7) yes N1 . C8 . 1.494(8) yes N1 . H1 . 0.898 no N2 . C13 . 1.475(8) yes N2 . C14 . 1.454(8) yes N2 . H2 . 0.880 no N51 . C57 . 1.491(8) yes N51 . C58 . 1.496(8) yes N51 . H3 . 0.880 no N52 . C63 . 1.501(9) yes N52 . C64 . 1.436(9) yes N52 . H4 . 0.880 no O1 . C1 . 1.330(10) yes O2 . C20 . 1.310(9) yes O3 . C2 . 1.406(9) yes O3 . C21 . 1.409(9) yes O4 . C19 . 1.382(9) yes O4 . C23 . 1.354(9) yes O51 . C51 . 1.318(10) yes O52 . C70 . 1.337(10) yes O53 . C52 . 1.38(1) yes O53 . C71 . 1.465(9) yes O54 . C69 . 1.391(8) yes O54 . C73 . 1.451(7) yes C1 . C2 . 1.437(10) yes C1 . C6 . 1.416(11) yes C2 . C3 . 1.372(11) yes C3 . C4 . 1.406(9) yes C3 . H31 . 0.960 no C4 . C5 . 1.382(9) yes C4 . H41 . 0.960 no C5 . C6 . 1.377(12) yes C5 . H51 . 0.960 no C6 . C7 . 1.502(9) yes C7 . H71 . 0.960 no C7 . H72 . 0.960 no C8 . C9 . 1.537(9) yes C8 . C13 . 1.497(9) yes C8 . H81 . 0.960 no C9 . C10 . 1.541(9) yes C9 . H91 . 0.960 no C9 . H92 . 0.960 no C10 . C11 . 1.540(11) yes C10 . H101 . 0.960 no C10 . H102 . 0.960 no C11 . C12 . 1.517(10) yes C11 . H111 . 0.960 no C11 . H112 . 0.960 no C12 . C13 . 1.536(8) yes C12 . H121 . 0.960 no C12 . H122 . 0.960 no C13 . H131 . 0.960 no C14 . C15 . 1.487(10) yes C14 . H141 . 0.960 no C14 . H142 . 0.960 no C15 . C16 . 1.381(11) yes C15 . C20 . 1.417(11) yes C16 . C17 . 1.395(10) yes C16 . H161 . 0.960 no C17 . C18 . 1.399(8) yes C17 . H171 . 0.960 no C18 . C19 . 1.340(9) yes C18 . H181 . 0.960 no C19 . C20 . 1.430(10) yes C21 . C22 . 1.509(10) yes C21 . H211 . 0.960 no C21 . H212 . 0.960 no C22 . H221 . 0.960 no C22 . H222 . 0.960 no C22 . H223 . 0.960 no C23 . C24 . 1.494(11) yes C23 . H231 . 0.960 no C23 . H232 . 0.960 no C24 . H241 . 0.960 no C24 . H242 . 0.960 no C24 . H243 . 0.960 no C51 . C52 . 1.428(10) yes C51 . C56 . 1.410(12) yes C52 . C53 . 1.370(11) yes C53 . C54 . 1.391(10) yes C53 . H531 . 0.960 no C54 . C55 . 1.384(10) yes C54 . H541 . 0.960 no C55 . C56 . 1.409(12) yes C55 . H551 . 0.960 no C56 . C57 . 1.511(9) yes C57 . H571 . 0.960 no C57 . H572 . 0.960 no C58 . C59 . 1.523(10) yes C58 . C63 . 1.495(10) yes C58 . H581 . 0.960 no C59 . C60 . 1.539(9) yes C59 . H591 . 0.960 no C59 . H592 . 0.960 no C60 . C61 . 1.488(12) yes C60 . H601 . 0.960 no C60 . H602 . 0.960 no C61 . C62 . 1.537(11) yes C61 . H611 . 0.960 no C61 . H612 . 0.960 no C62 . C63 . 1.532(9) yes C62 . H621 . 0.960 no C62 . H622 . 0.960 no C63 . H631 . 0.960 no C64 . C65 . 1.505(11) yes C64 . H641 . 0.960 no C64 . H642 . 0.960 no C65 . C66 . 1.390(13) yes C65 . C70 . 1.415(12) yes C66 . C67 . 1.368(11) yes C66 . H661 . 0.960 no C67 . C68 . 1.376(8) yes C67 . H671 . 0.960 no C68 . C69 . 1.393(9) yes C68 . H681 . 0.960 no C69 . C70 . 1.406(11) yes C71 . C72 . 1.482(11) yes C71 . H711 . 0.960 no C71 . H712 . 0.960 no C72 . H721 . 0.960 no C72 . H722 . 0.960 no C72 . H723 . 0.960 no C73 . C74 . 1.508(11) yes C73 . H731 . 0.960 no C73 . H732 . 0.960 no C74 . H741 . 0.960 no C74 . H742 . 0.960 no C74 . H743 . 0.960 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 N1 . Cu1 . N2 . 85.4(2) yes N1 . Cu1 . O1 . 95.1(2) yes N2 . Cu1 . O1 . 162.0(2) yes N1 . Cu1 . O2 . 162.4(2) yes N2 . Cu1 . O2 . 93.9(2) yes O1 . Cu1 . O2 . 91.0(2) yes N51 . Cu2 . N52 . 87.3(2) yes N51 . Cu2 . O51 . 94.2(2) yes N52 . Cu2 . O51 . 169.2(2) yes N51 . Cu2 . O52 . 169.8(2) yes N52 . Cu2 . O52 . 94.4(2) yes O51 . Cu2 . O52 . 86.1(2) yes Cu1 . N1 . C7 . 114.6(4) yes Cu1 . N1 . C8 . 107.5(4) yes C7 . N1 . C8 . 111.7(5) yes Cu1 . N1 . H1 . 106.3 no C7 . N1 . H1 . 108.7 no C8 . N1 . H1 . 107.8 no Cu1 . N2 . C13 . 107.5(4) yes Cu1 . N2 . C14 . 115.5(4) yes C13 . N2 . C14 . 113.2(5) yes Cu1 . N2 . H2 . 106.7 no C13 . N2 . H2 . 107.0 no C14 . N2 . H2 . 106.6 no Cu2 . N51 . C57 . 113.7(4) yes Cu2 . N51 . C58 . 107.5(4) yes C57 . N51 . C58 . 110.7(5) yes Cu2 . N51 . H3 . 104.8 no C57 . N51 . H3 . 114.6 no C58 . N51 . H3 . 104.9 no Cu2 . N52 . C63 . 106.3(4) yes Cu2 . N52 . C64 . 115.9(4) yes C63 . N52 . C64 . 113.8(5) yes Cu2 . N52 . H4 . 106.3 no C63 . N52 . H4 . 105.2 no C64 . N52 . H4 . 108.5 no Cu1 . O1 . C1 . 124.9(5) yes Cu1 . O2 . C20 . 123.7(5) yes C2 . O3 . C21 . 116.8(5) yes C19 . O4 . C23 . 119.7(6) yes Cu2 . O51 . C51 . 129.4(5) yes Cu2 . O52 . C70 . 128.6(5) yes C52 . O53 . C71 . 117.7(5) yes C69 . O54 . C73 . 112.6(5) yes O1 . C1 . C2 . 120.8(7) yes O1 . C1 . C6 . 124.0(7) yes C2 . C1 . C6 . 115.1(8) yes C1 . C2 . O3 . 120.2(8) yes C1 . C2 . C3 . 122.5(7) yes O3 . C2 . C3 . 117.0(6) yes C2 . C3 . C4 . 120.4(6) yes C2 . C3 . H31 . 119.8 no C4 . C3 . H31 . 119.8 no C3 . C4 . C5 . 117.8(7) yes C3 . C4 . H41 . 121.0 no C5 . C4 . H41 . 121.2 no C4 . C5 . C6 . 122.5(8) yes C4 . C5 . H51 . 118.7 no C6 . C5 . H51 . 118.8 no C1 . C6 . C5 . 121.3(7) yes C1 . C6 . C7 . 119.9(7) yes C5 . C6 . C7 . 118.7(7) yes C6 . C7 . N1 . 114.7(5) yes C6 . C7 . H71 . 108.1 no N1 . C7 . H71 . 108.1 no C6 . C7 . H72 . 108.2 no N1 . C7 . H72 . 108.2 no H71 . C7 . H72 . 109.5 no N1 . C8 . C9 . 113.2(5) yes N1 . C8 . C13 . 107.5(5) yes C9 . C8 . C13 . 111.9(5) yes N1 . C8 . H81 . 108.0 no C9 . C8 . H81 . 108.0 no C13 . C8 . H81 . 108.0 no C8 . C9 . C10 . 109.3(5) yes C8 . C9 . H91 . 109.5 no C10 . C9 . H91 . 109.5 no C8 . C9 . H92 . 109.5 no C10 . C9 . H92 . 109.6 no H91 . C9 . H92 . 109.5 no C9 . C10 . C11 . 109.1(5) yes C9 . C10 . H101 . 109.5 no C11 . C10 . H101 . 109.6 no C9 . C10 . H102 . 109.6 no C11 . C10 . H102 . 109.6 no H101 . C10 . H102 . 109.5 no C10 . C11 . C12 . 111.0(5) yes C10 . C11 . H111 . 109.1 no C12 . C11 . H111 . 109.1 no C10 . C11 . H112 . 109.1 no C12 . C11 . H112 . 109.0 no H111 . C11 . H112 . 109.5 no C11 . C12 . C13 . 110.5(5) yes C11 . C12 . H121 . 109.3 no C13 . C12 . H121 . 109.2 no C11 . C12 . H122 . 109.2 no C13 . C12 . H122 . 109.1 no H121 . C12 . H122 . 109.5 no C12 . C13 . C8 . 111.6(5) yes C12 . C13 . N2 . 113.1(5) yes C8 . C13 . N2 . 107.8(5) yes C12 . C13 . H131 . 108.0 no C8 . C13 . H131 . 108.1 no N2 . C13 . H131 . 108.1 no N2 . C14 . C15 . 115.0(5) yes N2 . C14 . H141 . 108.1 no C15 . C14 . H141 . 108.1 no N2 . C14 . H142 . 108.0 no C15 . C14 . H142 . 108.0 no H141 . C14 . H142 . 109.5 no C14 . C15 . C16 . 118.7(7) yes C14 . C15 . C20 . 120.8(7) yes C16 . C15 . C20 . 120.5(8) yes C15 . C16 . C17 . 121.9(7) yes C15 . C16 . H161 . 119.0 no C17 . C16 . H161 . 119.1 no C16 . C17 . C18 . 117.9(6) yes C16 . C17 . H171 . 121.1 no C18 . C17 . H171 . 121.0 no C17 . C18 . C19 . 120.8(6) yes C17 . C18 . H181 . 119.6 no C19 . C18 . H181 . 119.6 no O4 . C19 . C18 . 118.2(6) yes O4 . C19 . C20 . 118.7(7) yes C18 . C19 . C20 . 123.1(6) yes C19 . C20 . C15 . 115.7(7) yes C19 . C20 . O2 . 121.5(7) yes C15 . C20 . O2 . 122.3(7) yes O3 . C21 . C22 . 106.5(6) yes O3 . C21 . H211 . 110.2 no C22 . C21 . H211 . 110.2 no O3 . C21 . H212 . 110.2 no C22 . C21 . H212 . 110.2 no H211 . C21 . H212 . 109.5 no C21 . C22 . H221 . 109.4 no C21 . C22 . H222 . 109.5 no H221 . C22 . H222 . 109.5 no C21 . C22 . H223 . 109.5 no H221 . C22 . H223 . 109.5 no H222 . C22 . H223 . 109.5 no O4 . C23 . C24 . 110.1(7) yes O4 . C23 . H231 . 109.3 no C24 . C23 . H231 . 109.4 no O4 . C23 . H232 . 109.4 no C24 . C23 . H232 . 109.2 no H231 . C23 . H232 . 109.5 no C23 . C24 . H241 . 109.5 no C23 . C24 . H242 . 109.4 no H241 . C24 . H242 . 109.5 no C23 . C24 . H243 . 109.5 no H241 . C24 . H243 . 109.5 no H242 . C24 . H243 . 109.5 no O51 . C51 . C52 . 119.6(8) yes O51 . C51 . C56 . 123.9(7) yes C52 . C51 . C56 . 116.3(8) yes C51 . C52 . O53 . 120.8(8) yes C51 . C52 . C53 . 122.4(8) yes O53 . C52 . C53 . 116.7(6) yes C52 . C53 . C54 . 120.4(6) yes C52 . C53 . H531 . 119.8 no C54 . C53 . H531 . 119.8 no C53 . C54 . C55 . 119.2(7) yes C53 . C54 . H541 . 120.5 no C55 . C54 . H541 . 120.3 no C54 . C55 . C56 . 121.0(8) yes C54 . C55 . H551 . 119.5 no C56 . C55 . H551 . 119.5 no C51 . C56 . C55 . 120.5(7) yes C51 . C56 . C57 . 120.1(8) yes C55 . C56 . C57 . 118.9(7) yes C56 . C57 . N51 . 114.4(5) yes C56 . C57 . H571 . 108.4 no N51 . C57 . H571 . 108.4 no C56 . C57 . H572 . 108.0 no N51 . C57 . H572 . 108.0 no H571 . C57 . H572 . 109.5 no N51 . C58 . C59 . 113.8(5) yes N51 . C58 . C63 . 108.5(5) yes C59 . C58 . C63 . 111.3(5) yes N51 . C58 . H581 . 107.6 no C59 . C58 . H581 . 107.7 no C63 . C58 . H581 . 107.7 no C58 . C59 . C60 . 109.8(6) yes C58 . C59 . H591 . 109.4 no C60 . C59 . H591 . 109.4 no C58 . C59 . H592 . 109.4 no C60 . C59 . H592 . 109.4 no H591 . C59 . H592 . 109.5 no C59 . C60 . C61 . 112.1(6) yes C59 . C60 . H601 . 108.8 no C61 . C60 . H601 . 108.9 no C59 . C60 . H602 . 108.8 no C61 . C60 . H602 . 108.7 no H601 . C60 . H602 . 109.5 no C60 . C61 . C62 . 110.5(6) yes C60 . C61 . H611 . 109.2 no C62 . C61 . H611 . 109.3 no C60 . C61 . H612 . 109.1 no C62 . C61 . H612 . 109.2 no H611 . C61 . H612 . 109.5 no C61 . C62 . C63 . 110.0(6) yes C61 . C62 . H621 . 109.3 no C63 . C62 . H621 . 109.4 no C61 . C62 . H622 . 109.3 no C63 . C62 . H622 . 109.4 no H621 . C62 . H622 . 109.5 no C62 . C63 . N52 . 112.9(5) yes C62 . C63 . C58 . 111.2(5) yes N52 . C63 . C58 . 109.7(5) yes C62 . C63 . H631 . 107.6 no N52 . C63 . H631 . 107.6 no C58 . C63 . H631 . 107.6 no N52 . C64 . C65 . 119.3(6) yes N52 . C64 . H641 . 107.0 no C65 . C64 . H641 . 107.0 no N52 . C64 . H642 . 106.9 no C65 . C64 . H642 . 106.9 no H641 . C64 . H642 . 109.5 no C64 . C65 . C66 . 118.9(8) yes C64 . C65 . C70 . 120.6(8) yes C66 . C65 . C70 . 120.2(8) yes C65 . C66 . C67 . 121.1(8) yes C65 . C66 . H661 . 119.5 no C67 . C66 . H661 . 119.4 no C66 . C67 . C68 . 120.2(6) yes C66 . C67 . H671 . 119.9 no C68 . C67 . H671 . 119.9 no C67 . C68 . C69 . 119.9(6) yes C67 . C68 . H681 . 120.0 no C69 . C68 . H681 . 120.0 no C68 . C69 . O54 . 117.5(6) yes C68 . C69 . C70 . 121.2(6) yes O54 . C69 . C70 . 121.3(7) yes C65 . C70 . C69 . 117.3(8) yes C65 . C70 . O52 . 124.5(8) yes C69 . C70 . O52 . 118.3(7) yes O53 . C71 . C72 . 108.3(6) yes O53 . C71 . H711 . 109.8 no C72 . C71 . H711 . 109.8 no O53 . C71 . H712 . 109.7 no C72 . C71 . H712 . 109.7 no H711 . C71 . H712 . 109.5 no C71 . C72 . H721 . 109.5 no C71 . C72 . H722 . 109.4 no H721 . C72 . H722 . 109.5 no C71 . C72 . H723 . 109.5 no H721 . C72 . H723 . 109.5 no H722 . C72 . H723 . 109.5 no O54 . C73 . C74 . 106.5(6) yes O54 . C73 . H731 . 110.0 no C74 . C73 . H731 . 110.0 no O54 . C73 . H732 . 110.3 no C74 . C73 . H732 . 110.5 no H731 . C73 . H732 . 109.5 no C73 . C74 . H741 . 109.4 no C73 . C74 . H742 . 109.7 no H741 . C74 . H742 . 109.5 no C73 . C74 . H743 . 109.3 no H741 . C74 . H743 . 109.5 no H742 . C74 . H743 . 109.5 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 N51 . H3 . O1 . 161 0.88 2.11 2.956(2) yes N52 . H4 . O2 1_655 160 0.88 2.06 2.904(2) yes