# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_LBSQCuCl _database_code_depnum_ccdc_archive 'CCDC 899392' #TrackingRef 'web_deposit_cif_file_0_TimStorr_1360779887.LBSQCu_submission.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_formula_sum 'C35 H44 Cl1 Cu1 N2 O2' _chemical_formula_moiety 'C35 H44 Cl1 Cu1 N2 O2' _chemical_formula_weight 623.74 #============================================================= # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' 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 #------------------------------------------------ _cell_length_a 16.4069(18) _cell_length_b 12.3090(14) _cell_length_c 17.1757(19) _cell_angle_alpha 90 _cell_angle_beta 110.1470(10) _cell_angle_gamma 90 _cell_volume 3256.4(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9773 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 28.62 _cell_measurement_temperature 150(2) _exptl_crystal_description plate _exptl_crystal_colour 'dark blue' _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_max 0.37 _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_meas ? _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 0.785 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6899 _exptl_absorpt_correction_T_max 0.7457 #============================================================================= # 7. EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 150(2) _diffrn_reflns_number 35679 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_theta_min 2.081 _diffrn_reflns_theta_max 28.618 _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 25.184 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 #========================================================================== # 8. REFINEMENT DATA # The values actually used during refinement # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _oxford_reflns_threshold_expression_ref I>2.5\s(I) _refine_ls_number_reflns 7055 _refine_ls_number_restraints 0 _refine_ls_number_parameters 372 _oxford_refine_ls_R_factor_ref 0.0413 _refine_ls_wR_factor_ref 0.0624 _refine_ls_goodness_of_fit_ref 1.1308 # The values computed from all data _oxford_reflns_number_all 13145 _refine_ls_R_factor_all 0.1114 _refine_ls_wR_factor_all 0.0714 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 7237 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_gt 0.0642 _reflns_number_total 7775 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F) + ( 0.00P)^2^ + 0.07P] ,where P=(max(Fo,0) + 2Fc)/3 ; _refine_ls_shift/su_max 0.0013258 _refine_diff_density_min -0.41 _refine_diff_density_max 1.48 _reflns_limit_h_min -21 _reflns_limit_h_max 20 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _oxford_refine_ls_scale 0.08218(12) _oxford_diffrn_Wilson_B_factor 1.82 _oxford_diffrn_Wilson_scale 154.66 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 7775 # Theoretical number of reflections is about 16700 #--------------------------------------------------------- _chemical_name_systematic ; ; # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment constr # none if no extinction, _refine_ls_extinction_method None #========================================================== # 9. General computing _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _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 ORTEP/PovRay/XXXX #=================================================================== # 10. ATOMIC COORDINATES AND THERMAL PARAMETERS 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' 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' 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' #============================================================================== # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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 0.331037(15) 0.692127(18) 0.050085(13) 0.0218 1.0000 Uani . . . . . . Cl1 Cl 0.27100(4) 0.76698(4) -0.07293(3) 0.0356 1.0000 Uani . . . . . . O1 O 0.28415(9) 0.77659(12) 0.12527(8) 0.0236 1.0000 Uani . . . . . . O2 O 0.39752(9) 0.37299(11) 0.03630(8) 0.0243 1.0000 Uani . . . . . . N1 N 0.43094(11) 0.67935(12) 0.15201(10) 0.0210 1.0000 Uani . . . . . . N2 N 0.33902(10) 0.53885(13) 0.02201(9) 0.0211 1.0000 Uani . . . . . . C1 C 0.33688(12) 0.77974(16) 0.19968(11) 0.0206 1.0000 Uani . . . . . . C2 C 0.32286(12) 0.84119(15) 0.26591(11) 0.0205 1.0000 Uani . . . . . . C3 C 0.37689(13) 0.81844(15) 0.34477(12) 0.0229 1.0000 Uani . . . . . . C4 C 0.44593(12) 0.73914(15) 0.36562(11) 0.0214 1.0000 Uani . . . . . . C5 C 0.46324(13) 0.68603(15) 0.30355(12) 0.0222 1.0000 Uani . . . . . . C6 C 0.41460(12) 0.71232(15) 0.21953(11) 0.0194 1.0000 Uani . . . . . . C7 C 0.50289(12) 0.61020(15) 0.16145(11) 0.0207 1.0000 Uani . . . . . . C8 C 0.58648(13) 0.63950(17) 0.21187(12) 0.0254 1.0000 Uani . . . . . . C9 C 0.65635(13) 0.57203(18) 0.22044(12) 0.0278 1.0000 Uani . . . . . . C10 C 0.64458(13) 0.47267(18) 0.17918(13) 0.0298 1.0000 Uani . . . . . . C11 C 0.56271(13) 0.44274(17) 0.12768(12) 0.0253 1.0000 Uani . . . . . . C12 C 0.49087(13) 0.51106(16) 0.11768(11) 0.0225 1.0000 Uani . . . . . . C13 C 0.40678(13) 0.47876(15) 0.05938(11) 0.0217 1.0000 Uani . . . . . . C14 C 0.31535(13) 0.36620(16) -0.02387(11) 0.0229 1.0000 Uani . . . . . . C15 C 0.27550(14) 0.27398(16) -0.06804(12) 0.0262 1.0000 Uani . . . . . . C16 C 0.19601(15) 0.29756(16) -0.12912(13) 0.0268 1.0000 Uani . . . . . . C17 C 0.15832(13) 0.40287(17) -0.14564(12) 0.0249 1.0000 Uani . . . . . . C18 C 0.19889(13) 0.48951(16) -0.09550(12) 0.0234 1.0000 Uani . . . . . . C19 C 0.27879(13) 0.46904(15) -0.03439(11) 0.0221 1.0000 Uani . . . . . . C20 C 0.24623(13) 0.91939(17) 0.24885(12) 0.0255 1.0000 Uani . . . . . . C21 C 0.49823(13) 0.71950(17) 0.45748(12) 0.0247 1.0000 Uani . . . . . . C22 C 0.31581(16) 0.16065(17) -0.04712(13) 0.0328 1.0000 Uani . . . . . . C23 C 0.07343(13) 0.41799(17) -0.21985(13) 0.0288 1.0000 Uani . . . . . . C24 C 0.16121(14) 0.8527(2) 0.22152(15) 0.0371 1.0000 Uani . . . . . . C25 C 0.24508(15) 1.00036(18) 0.18067(13) 0.0316 1.0000 Uani . . . . . . C26 C 0.25089(17) 0.9846(2) 0.32645(14) 0.0422 1.0000 Uani . . . . . . C27 C 0.54945(17) 0.8225(2) 0.49471(14) 0.0370 1.0000 Uani . . . . . . C28 C 0.43607(16) 0.69082(18) 0.50385(14) 0.0331 1.0000 Uani . . . . . . C29 C 0.56295(15) 0.6255(2) 0.46840(14) 0.0366 1.0000 Uani . . . . . . C30 C 0.40402(19) 0.1567(2) -0.05873(18) 0.0476 1.0000 Uani . . . . . . C31 C 0.32767(16) 0.1359(2) 0.04348(14) 0.0385 1.0000 Uani . . . . . . C32 C 0.2560(2) 0.0754(2) -0.10180(19) 0.0650 1.0000 Uani . . . . . . C33 C 0.0870(2) 0.3796(3) -0.29940(15) 0.0537 1.0000 Uani . . . . . . C34 C 0.0461(2) 0.5376(2) -0.23429(19) 0.0568 1.0000 Uani . . . . . . C35 C 0.00081(19) 0.3519(4) -0.2075(2) 0.0822 1.0000 Uani . . . . . . H31 H 0.3682 0.8558 0.3890 0.022(2) 1.0000 Uiso R . . . . . H51 H 0.5069 0.6327 0.3147 0.021(2) 1.0000 Uiso R . . . . . H81 H 0.5939 0.7069 0.2403 0.025(2) 1.0000 Uiso R . . . . . H91 H 0.7126 0.5942 0.2546 0.030(2) 1.0000 Uiso R . . . . . H101 H 0.6917 0.4264 0.1856 0.030(2) 1.0000 Uiso R . . . . . H111 H 0.5547 0.3767 0.0978 0.026(2) 1.0000 Uiso R . . . . . H161 H 0.1661 0.2399 -0.1614 0.026(2) 1.0000 Uiso R . . . . . H181 H 0.1756 0.5606 -0.1022 0.023(2) 1.0000 Uiso R . . . . . H242 H 0.1133 0.9017 0.2112 0.0468(15) 1.0000 Uiso R . . . . . H241 H 0.1622 0.8058 0.2670 0.0466(15) 1.0000 Uiso R . . . . . H243 H 0.1563 0.8088 0.1733 0.0464(15) 1.0000 Uiso R . . . . . H251 H 0.1971 1.0484 0.1728 0.0382(15) 1.0000 Uiso R . . . . . H253 H 0.2982 1.0422 0.1995 0.0385(15) 1.0000 Uiso R . . . . . H252 H 0.2395 0.9637 0.1296 0.0378(15) 1.0000 Uiso R . . . . . H262 H 0.2016 1.0326 0.3110 0.0533(15) 1.0000 Uiso R . . . . . H261 H 0.3035 1.0263 0.3446 0.0532(15) 1.0000 Uiso R . . . . . H263 H 0.2482 0.9357 0.3699 0.0533(15) 1.0000 Uiso R . . . . . H273 H 0.5811 0.8103 0.5522 0.0441(15) 1.0000 Uiso R . . . . . H271 H 0.5896 0.8383 0.4658 0.0442(15) 1.0000 Uiso R . . . . . H272 H 0.5105 0.8833 0.4891 0.0438(15) 1.0000 Uiso R . . . . . H281 H 0.4693 0.6752 0.5603 0.0378(15) 1.0000 Uiso R . . . . . H282 H 0.3976 0.7515 0.5023 0.0385(15) 1.0000 Uiso R . . . . . H283 H 0.4024 0.6276 0.4796 0.0383(15) 1.0000 Uiso R . . . . . H293 H 0.5925 0.6133 0.5265 0.0434(15) 1.0000 Uiso R . . . . . H291 H 0.6040 0.6432 0.4424 0.0425(15) 1.0000 Uiso R . . . . . H292 H 0.5319 0.5600 0.4437 0.0432(15) 1.0000 Uiso R . . . . . H301 H 0.4282 0.0842 -0.0449 0.0603(15) 1.0000 Uiso R . . . . . H302 H 0.4442 0.2112 -0.0234 0.0608(15) 1.0000 Uiso R . . . . . H303 H 0.3951 0.1718 -0.1162 0.0603(15) 1.0000 Uiso R . . . . . H312 H 0.3519 0.0633 0.0542 0.0470(15) 1.0000 Uiso R . . . . . H313 H 0.3682 0.1873 0.0801 0.0476(15) 1.0000 Uiso R . . . . . H311 H 0.2725 0.1385 0.0522 0.0480(15) 1.0000 Uiso R . . . . . H321 H 0.2847 0.0069 -0.0834 0.0871(15) 1.0000 Uiso R . . . . . H322 H 0.2515 0.0894 -0.1580 0.0872(15) 1.0000 Uiso R . . . . . H323 H 0.2005 0.0758 -0.0934 0.0875(15) 1.0000 Uiso R . . . . . H332 H 0.0319 0.3895 -0.3455 0.0711(15) 1.0000 Uiso R . . . . . H333 H 0.1345 0.4244 -0.3077 0.0726(15) 1.0000 Uiso R . . . . . H331 H 0.1012 0.3018 -0.2926 0.0718(15) 1.0000 Uiso R . . . . . H341 H -0.0050 0.5412 -0.2844 0.0774(15) 1.0000 Uiso R . . . . . H343 H 0.0953 0.5767 -0.2401 0.0777(15) 1.0000 Uiso R . . . . . H342 H 0.0320 0.5597 -0.1849 0.0779(15) 1.0000 Uiso R . . . . . H352 H -0.0515 0.3602 -0.2553 0.1132(15) 1.0000 Uiso R . . . . . H351 H -0.0078 0.3848 -0.1583 0.1128(15) 1.0000 Uiso R . . . . . H353 H 0.0194 0.2760 -0.1989 0.1137(15) 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 0.02569(15) 0.02009(15) 0.01779(14) -0.00110(7) 0.00528(11) 0.00288(8) Cl1 0.0507(3) 0.0277(3) 0.0243(3) 0.00475(19) 0.0077(2) 0.0062(2) O1 0.0246(7) 0.0256(7) 0.0178(6) -0.0011(5) 0.0036(5) 0.0028(5) O2 0.0290(7) 0.0199(7) 0.0215(6) -0.0023(5) 0.0056(5) 0.0026(5) N1 0.0225(8) 0.0187(7) 0.0200(8) -0.0029(6) 0.0052(6) -0.0017(6) N2 0.0245(8) 0.0213(8) 0.0179(7) -0.0014(6) 0.0077(6) 0.0003(6) C1 0.0233(9) 0.0200(8) 0.0179(8) -0.0026(7) 0.0065(7) -0.0028(7) C2 0.0211(9) 0.0204(9) 0.0199(8) -0.0011(7) 0.0071(7) -0.0011(7) C3 0.0244(10) 0.0248(10) 0.0190(9) -0.0026(7) 0.0067(8) -0.0017(7) C4 0.0221(9) 0.0230(9) 0.0176(8) 0.0010(7) 0.0049(7) -0.0027(7) C5 0.0225(9) 0.0220(10) 0.0210(9) 0.0016(7) 0.0061(8) -0.0001(7) C6 0.0229(9) 0.0167(8) 0.0191(8) -0.0020(7) 0.0080(7) -0.0028(7) C7 0.0226(9) 0.0227(9) 0.0180(8) 0.0019(7) 0.0083(7) 0.0020(7) C8 0.0247(10) 0.0275(10) 0.0241(9) 0.0008(8) 0.0088(8) -0.0020(7) C9 0.0196(9) 0.0379(12) 0.0262(9) 0.0020(8) 0.0082(8) -0.0022(8) C10 0.0236(10) 0.0385(12) 0.0294(10) 0.0072(9) 0.0118(8) 0.0083(8) C11 0.0297(10) 0.0246(9) 0.0246(9) 0.0013(8) 0.0131(8) 0.0045(8) C12 0.0245(9) 0.0229(9) 0.0207(8) 0.0024(7) 0.0087(7) 0.0025(7) C13 0.0285(10) 0.0195(9) 0.0198(8) -0.0022(7) 0.0120(8) 0.0002(7) C14 0.0252(9) 0.0244(9) 0.0186(8) 0.0009(7) 0.0066(7) 0.0001(7) C15 0.0367(11) 0.0210(9) 0.0199(9) -0.0005(7) 0.0086(8) 0.0009(8) C16 0.0352(11) 0.0209(10) 0.0222(9) -0.0034(7) 0.0071(8) -0.0060(7) C17 0.0248(10) 0.0295(10) 0.0225(9) -0.0005(7) 0.0107(8) -0.0004(8) C18 0.0263(10) 0.0209(9) 0.0238(9) -0.0027(7) 0.0097(8) 0.0014(7) C19 0.0270(10) 0.0210(9) 0.0197(8) -0.0011(7) 0.0098(7) -0.0009(7) C20 0.0241(10) 0.0293(10) 0.0230(9) -0.0014(7) 0.0077(8) 0.0052(7) C21 0.0271(10) 0.0276(10) 0.0183(9) 0.0003(7) 0.0063(7) 0.0012(8) C22 0.0457(13) 0.0195(9) 0.0266(10) 0.0013(8) 0.0039(9) 0.0033(9) C23 0.0238(10) 0.0317(11) 0.0275(10) 0.0002(8) 0.0044(8) 0.0004(8) C24 0.0247(10) 0.0456(14) 0.0407(12) 0.0050(10) 0.0107(9) 0.0030(10) C25 0.0359(12) 0.0272(10) 0.0293(10) 0.0021(8) 0.0082(9) 0.0066(8) C26 0.0477(14) 0.0469(14) 0.0298(11) -0.0052(10) 0.0105(10) 0.0216(11) C27 0.0385(13) 0.0403(13) 0.0250(10) -0.0002(9) 0.0016(9) -0.0088(10) C28 0.0352(12) 0.0397(13) 0.0249(10) 0.0046(8) 0.0112(9) -0.0015(9) C29 0.0348(12) 0.0451(14) 0.0268(10) 0.0069(9) 0.0069(9) 0.0131(10) C30 0.0699(18) 0.0283(12) 0.0528(15) 0.0053(11) 0.0316(14) 0.0156(12) C31 0.0446(14) 0.0330(13) 0.0347(12) 0.0112(9) 0.0096(11) 0.0053(9) C32 0.086(2) 0.0205(12) 0.0552(17) -0.0057(11) -0.0186(16) 0.0013(13) C33 0.0507(16) 0.072(2) 0.0268(11) -0.0072(12) -0.0018(11) 0.0190(14) C34 0.0516(17) 0.0476(16) 0.0482(15) -0.0086(12) -0.0125(13) 0.0135(13) C35 0.0321(15) 0.134(3) 0.066(2) 0.051(2) -0.0018(14) -0.0209(18) 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 . 2.2021(6) yes Cu1 . O1 . 2.0062(14) yes Cu1 . N1 . 1.9492(16) yes Cu1 . N2 . 1.9628(16) yes O1 . C1 . 1.273(2) yes O2 . C13 . 1.354(2) yes O2 . C14 . 1.390(2) yes N1 . C6 . 1.340(2) yes N1 . C7 . 1.419(2) yes N2 . C13 . 1.305(2) yes N2 . C19 . 1.412(2) yes C1 . C2 . 1.449(3) yes C1 . C6 . 1.460(3) yes C2 . C3 . 1.368(3) yes C2 . C20 . 1.529(3) yes C3 . C4 . 1.444(3) yes C3 . H31 . 0.939 no C4 . C5 . 1.361(3) yes C4 . C21 . 1.533(3) yes C5 . C6 . 1.425(3) yes C5 . H51 . 0.942 no C7 . C8 . 1.394(3) yes C7 . C12 . 1.411(3) yes C8 . C9 . 1.382(3) yes C8 . H81 . 0.949 no C9 . C10 . 1.393(3) yes C9 . H91 . 0.947 no C10 . C11 . 1.380(3) yes C10 . H101 . 0.936 no C11 . C12 . 1.409(3) yes C11 . H111 . 0.946 no C12 . C13 . 1.453(3) yes C14 . C15 . 1.396(3) yes C14 . C19 . 1.386(3) yes C15 . C16 . 1.394(3) yes C15 . C22 . 1.533(3) yes C16 . C17 . 1.422(3) yes C16 . H161 . 0.930 no C17 . C18 . 1.388(3) yes C17 . C23 . 1.542(3) yes C18 . C19 . 1.391(3) yes C18 . H181 . 0.945 no C20 . C24 . 1.545(3) yes C20 . C25 . 1.533(3) yes C20 . C26 . 1.535(3) yes C21 . C27 . 1.534(3) yes C21 . C28 . 1.536(3) yes C21 . C29 . 1.537(3) yes C22 . C30 . 1.528(4) yes C22 . C31 . 1.531(3) yes C22 . C32 . 1.521(3) yes C23 . C33 . 1.532(3) yes C23 . C34 . 1.534(3) yes C23 . C35 . 1.516(4) yes C24 . H242 . 0.957 no C24 . H241 . 0.967 no C24 . H243 . 0.969 no C25 . H251 . 0.956 no C25 . H253 . 0.967 no C25 . H252 . 0.963 no C26 . H262 . 0.961 no C26 . H261 . 0.959 no C26 . H263 . 0.972 no C27 . H273 . 0.957 no C27 . H271 . 0.971 no C27 . H272 . 0.967 no C28 . H281 . 0.954 no C28 . H282 . 0.971 no C28 . H283 . 0.962 no C29 . H293 . 0.959 no C29 . H291 . 0.953 no C29 . H292 . 0.971 no C30 . H301 . 0.972 no C30 . H302 . 0.988 no C30 . H303 . 0.965 no C31 . H312 . 0.969 no C31 . H313 . 0.975 no C31 . H311 . 0.967 no C32 . H321 . 0.965 no C32 . H322 . 0.958 no C32 . H323 . 0.969 no C33 . H332 . 0.983 no C33 . H333 . 1.005 no C33 . H331 . 0.983 no C34 . H341 . 0.973 no C34 . H343 . 0.974 no C34 . H342 . 0.991 no C35 . H352 . 0.966 no C35 . H351 . 0.991 no C35 . H353 . 0.978 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 . Cu1 . O1 . 104.88(4) yes Cl1 . Cu1 . N1 . 148.79(5) yes O1 . Cu1 . N1 . 81.60(6) yes Cl1 . Cu1 . N2 . 102.24(5) yes O1 . Cu1 . N2 . 136.81(6) yes N1 . Cu1 . N2 . 92.09(6) yes Cu1 . O1 . C1 . 112.53(12) yes C13 . O2 . C14 . 104.94(15) yes Cu1 . N1 . C6 . 113.32(13) yes Cu1 . N1 . C7 . 124.08(12) yes C6 . N1 . C7 . 119.30(16) yes Cu1 . N2 . C13 . 122.79(13) yes Cu1 . N2 . C19 . 131.55(13) yes C13 . N2 . C19 . 105.59(15) yes O1 . C1 . C2 . 124.55(17) yes O1 . C1 . C6 . 116.99(16) yes C2 . C1 . C6 . 118.39(16) yes C1 . C2 . C3 . 116.52(17) yes C1 . C2 . C20 . 121.35(16) yes C3 . C2 . C20 . 121.88(17) yes C2 . C3 . C4 . 124.71(18) yes C2 . C3 . H31 . 118.2 no C4 . C3 . H31 . 117.0 no C3 . C4 . C5 . 119.20(17) yes C3 . C4 . C21 . 118.36(17) yes C5 . C4 . C21 . 122.43(17) yes C4 . C5 . C6 . 119.27(18) yes C4 . C5 . H51 . 121.6 no C6 . C5 . H51 . 119.1 no C1 . C6 . C5 . 120.33(17) yes C1 . C6 . N1 . 112.89(16) yes C5 . C6 . N1 . 126.76(18) yes N1 . C7 . C8 . 121.18(17) yes N1 . C7 . C12 . 119.99(17) yes C8 . C7 . C12 . 118.81(18) yes C7 . C8 . C9 . 120.89(19) yes C7 . C8 . H81 . 118.1 no C9 . C8 . H81 . 121.0 no C8 . C9 . C10 . 120.59(19) yes C8 . C9 . H91 . 119.3 no C10 . C9 . H91 . 120.1 no C9 . C10 . C11 . 119.62(19) yes C9 . C10 . H101 . 120.7 no C11 . C10 . H101 . 119.7 no C10 . C11 . C12 . 120.49(19) yes C10 . C11 . H111 . 120.0 no C12 . C11 . H111 . 119.5 no C7 . C12 . C11 . 119.57(18) yes C7 . C12 . C13 . 121.94(17) yes C11 . C12 . C13 . 118.44(17) yes C12 . C13 . O2 . 116.68(16) yes C12 . C13 . N2 . 129.00(17) yes O2 . C13 . N2 . 114.21(17) yes O2 . C14 . C15 . 127.26(17) yes O2 . C14 . C19 . 107.90(16) yes C15 . C14 . C19 . 124.83(18) yes C14 . C15 . C16 . 112.41(18) yes C14 . C15 . C22 . 121.94(18) yes C16 . C15 . C22 . 125.61(18) yes C15 . C16 . C17 . 124.73(18) yes C15 . C16 . H161 . 117.0 no C17 . C16 . H161 . 118.2 no C16 . C17 . C18 . 119.59(18) yes C16 . C17 . C23 . 118.81(18) yes C18 . C17 . C23 . 121.59(18) yes C17 . C18 . C19 . 117.06(18) yes C17 . C18 . H181 . 123.2 no C19 . C18 . H181 . 119.7 no N2 . C19 . C18 . 131.47(17) yes N2 . C19 . C14 . 107.29(16) yes C18 . C19 . C14 . 121.12(18) yes C2 . C20 . C24 . 108.70(17) yes C2 . C20 . C25 . 110.40(16) yes C24 . C20 . C25 . 109.93(17) yes C2 . C20 . C26 . 111.78(16) yes C24 . C20 . C26 . 108.12(19) yes C25 . C20 . C26 . 107.87(19) yes C4 . C21 . C27 . 109.30(17) yes C4 . C21 . C28 . 109.49(17) yes C27 . C21 . C28 . 109.89(18) yes C4 . C21 . C29 . 111.25(16) yes C27 . C21 . C29 . 108.35(19) yes C28 . C21 . C29 . 108.54(18) yes C15 . C22 . C30 . 110.48(19) yes C15 . C22 . C31 . 108.23(18) yes C30 . C22 . C31 . 109.4(2) yes C15 . C22 . C32 . 110.41(19) yes C30 . C22 . C32 . 109.7(2) yes C31 . C22 . C32 . 108.6(2) yes C17 . C23 . C33 . 109.44(18) yes C17 . C23 . C34 . 112.34(18) yes C33 . C23 . C34 . 106.0(2) yes C17 . C23 . C35 . 110.45(19) yes C33 . C23 . C35 . 108.7(3) yes C34 . C23 . C35 . 109.7(3) yes C20 . C24 . H242 . 108.7 no C20 . C24 . H241 . 108.0 no H242 . C24 . H241 . 108.1 no C20 . C24 . H243 . 110.8 no H242 . C24 . H243 . 111.8 no H241 . C24 . H243 . 109.3 no C20 . C25 . H251 . 107.6 no C20 . C25 . H253 . 108.6 no H251 . C25 . H253 . 108.7 no C20 . C25 . H252 . 111.3 no H251 . C25 . H252 . 110.2 no H253 . C25 . H252 . 110.3 no C20 . C26 . H262 . 107.2 no C20 . C26 . H261 . 109.5 no H262 . C26 . H261 . 109.8 no C20 . C26 . H263 . 109.9 no H262 . C26 . H263 . 109.6 no H261 . C26 . H263 . 110.8 no C21 . C27 . H273 . 108.9 no C21 . C27 . H271 . 108.9 no H273 . C27 . H271 . 109.7 no C21 . C27 . H272 . 110.5 no H273 . C27 . H272 . 109.3 no H271 . C27 . H272 . 109.6 no C21 . C28 . H281 . 108.9 no C21 . C28 . H282 . 110.5 no H281 . C28 . H282 . 108.7 no C21 . C28 . H283 . 110.3 no H281 . C28 . H283 . 108.6 no H282 . C28 . H283 . 109.9 no C21 . C29 . H293 . 109.0 no C21 . C29 . H291 . 110.0 no H293 . C29 . H291 . 109.7 no C21 . C29 . H292 . 109.6 no H293 . C29 . H292 . 109.1 no H291 . C29 . H292 . 109.5 no C22 . C30 . H301 . 108.8 no C22 . C30 . H302 . 111.1 no H301 . C30 . H302 . 110.1 no C22 . C30 . H303 . 108.1 no H301 . C30 . H303 . 109.4 no H302 . C30 . H303 . 109.4 no C22 . C31 . H312 . 106.0 no C22 . C31 . H313 . 110.3 no H312 . C31 . H313 . 109.4 no C22 . C31 . H311 . 110.6 no H312 . C31 . H311 . 110.2 no H313 . C31 . H311 . 110.2 no C22 . C32 . H321 . 105.2 no C22 . C32 . H322 . 107.8 no H321 . C32 . H322 . 110.3 no C22 . C32 . H323 . 110.1 no H321 . C32 . H323 . 109.5 no H322 . C32 . H323 . 113.5 no C23 . C33 . H332 . 107.7 no C23 . C33 . H333 . 108.4 no H332 . C33 . H333 . 111.2 no C23 . C33 . H331 . 107.2 no H332 . C33 . H331 . 109.3 no H333 . C33 . H331 . 112.8 no C23 . C34 . H341 . 107.5 no C23 . C34 . H343 . 106.5 no H341 . C34 . H343 . 112.2 no C23 . C34 . H342 . 105.4 no H341 . C34 . H342 . 111.2 no H343 . C34 . H342 . 113.5 no C23 . C35 . H352 . 109.6 no C23 . C35 . H351 . 104.4 no H352 . C35 . H351 . 109.6 no C23 . C35 . H353 . 108.3 no H352 . C35 . H353 . 111.7 no H351 . C35 . H353 . 113.0 no data_LBSQCuOAc _database_code_depnum_ccdc_archive 'CCDC 899393' #TrackingRef 'web_deposit_cif_file_0_TimStorr_1360779887.LBSQCu_submission.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_formula_sum 'C39 H50 Cu1 N3 O4' _chemical_formula_moiety 'C39 H50 Cu1 N3 O4' _chemical_formula_weight 688.39 #============================================================= # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' 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 #------------------------------------------------ _cell_length_a 12.5963(12) _cell_length_b 16.3407(16) _cell_length_c 18.3053(18) _cell_angle_alpha 90 _cell_angle_beta 98.1790(10) _cell_angle_gamma 90 _cell_volume 3729.5(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9856 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 27.86 _cell_measurement_temperature 298 _exptl_crystal_description plate _exptl_crystal_colour 'dark blue' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_max 0.32 _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_meas ? _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 0.627 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6170 _exptl_absorpt_correction_T_max 0.7458 #============================================================================= # 7. EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 298 _diffrn_reflns_number 44491 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_theta_min 2.055 _diffrn_reflns_theta_max 28.826 _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 25.655 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 #========================================================================== # 8. REFINEMENT DATA # The values actually used during refinement # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _oxford_reflns_threshold_expression_ref I>2.5\s(I) _refine_ls_number_reflns 6148 _refine_ls_number_restraints 48 _refine_ls_number_parameters 454 _oxford_refine_ls_R_factor_ref 0.0417 _refine_ls_wR_factor_ref 0.0440 _refine_ls_goodness_of_fit_ref 1.0332 # The values computed from all data _oxford_reflns_number_all 9153 _refine_ls_R_factor_all 0.0659 _refine_ls_wR_factor_all 0.0874 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6638 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_gt 0.0458 _reflns_number_total 9153 _refine_ls_structure_factor_coef F _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: 0.217 0.194 0.900E-01 0.135E-01 ; _refine_ls_shift/su_max 0.0019360 _refine_diff_density_min -0.32 _refine_diff_density_max 0.55 _reflns_limit_h_min -17 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 21 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _oxford_refine_ls_scale 0.10252(12) _oxford_diffrn_Wilson_B_factor 3.19 _oxford_diffrn_Wilson_scale 100.76 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 9153 # Theoretical number of reflections is about 19508 #--------------------------------------------------------- _chemical_name_systematic ; ; # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment constr # none if no extinction, _refine_ls_extinction_method None #========================================================== # 9. General computing _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _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 ORTEP/PovRay/XXXX #=================================================================== # 10. ATOMIC COORDINATES AND THERMAL PARAMETERS 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' #============================================================================== # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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 0.60070(2) 0.139585(18) 0.711113(15) 0.0411 1.0000 Uani . . . . . . O1 O 0.73396(13) 0.10418(10) 0.77206(8) 0.0449 1.0000 Uani . . . . . . O2 O 0.43201(13) 0.16404(10) 0.50402(8) 0.0445 1.0000 Uani . . . . . . O100 O 0.4393(2) 0.21549(16) 0.76604(18) 0.1032 1.0000 Uani . . . . . . O101 O 0.50842(14) 0.09314(12) 0.77422(10) 0.0554 1.0000 Uani . . . . . . N1 N 0.69571(14) 0.21319(11) 0.66942(10) 0.0392 1.0000 Uani . . . . . . N2 N 0.51075(15) 0.12641(12) 0.61548(10) 0.0418 1.0000 Uani . . . . . . N200 N 0.2996(3) 0.3986(3) 0.5374(2) 0.1204 1.0000 Uani . . . . . . C1 C 0.66447(17) 0.26790(14) 0.61090(12) 0.0396 1.0000 Uani . . . . . . C2 C 0.71825(19) 0.34221(14) 0.60574(14) 0.0465 1.0000 Uani . . . . . . C3 C 0.6857(2) 0.39718(16) 0.55009(15) 0.0551 1.0000 Uani . . . . . . C4 C 0.5999(2) 0.37991(17) 0.49713(17) 0.0634 1.0000 Uani . . . . . . C5 C 0.5437(2) 0.30856(17) 0.50160(15) 0.0560 1.0000 Uani . . . . . . C6 C 0.57348(18) 0.25216(15) 0.55875(13) 0.0432 1.0000 Uani . . . . . . C7 C 0.50891(17) 0.17949(15) 0.56229(12) 0.0416 1.0000 Uani . . . . . . C8 C 0.38023(18) 0.09403(14) 0.52318(12) 0.0414 1.0000 Uani . . . . . . C9 C 0.29425(18) 0.05376(14) 0.48296(12) 0.0415 1.0000 Uani . . . . . . C10 C 0.26135(19) -0.01394(15) 0.51915(13) 0.0451 1.0000 Uani . . . . . . C11 C 0.30680(19) -0.04036(14) 0.59012(13) 0.0443 1.0000 Uani . . . . . . C12 C 0.39241(18) 0.00280(15) 0.62730(12) 0.0437 1.0000 Uani . . . . . . C13 C 0.42789(18) 0.07031(14) 0.59256(12) 0.0407 1.0000 Uani . . . . . . C14 C 0.2406(2) 0.08378(16) 0.40727(12) 0.0464 1.0000 Uani . . . . . . C15 C 0.2621(2) -0.11525(13) 0.62544(14) 0.0575 1.0000 Uani D U . . . . C16 C 0.1973(3) 0.17016(19) 0.41535(15) 0.0658 1.0000 Uani . . . . . . C17 C 0.3219(3) 0.0845(2) 0.35296(15) 0.0706 1.0000 Uani . . . . . . C18 C 0.1468(3) 0.0288(2) 0.37663(16) 0.0765 1.0000 Uani . . . . . . C19 C 0.1750(5) -0.1592(3) 0.5743(3) 0.1112 0.623(6) Uani D U P . 1 . C20 C 0.3487(4) -0.1759(3) 0.6508(4) 0.0982 0.623(6) Uani D U P . 1 . C21 C 0.2140(5) -0.0867(3) 0.6927(3) 0.0943 0.623(6) Uani D U P . 1 . C22 C 0.81589(17) 0.13993(14) 0.75330(11) 0.0367 1.0000 Uani . . . . . . C23 C 0.92393(18) 0.12784(14) 0.78980(11) 0.0399 1.0000 Uani . . . . . . C24 C 1.00402(18) 0.15509(14) 0.75329(12) 0.0421 1.0000 Uani . . . . . . C25 C 0.98878(17) 0.19597(14) 0.68320(12) 0.0384 1.0000 Uani . . . . . . C26 C 0.88695(17) 0.21390(14) 0.65211(12) 0.0385 1.0000 Uani . . . . . . C27 C 0.79912(17) 0.19250(13) 0.68844(11) 0.0367 1.0000 Uani . . . . . . C28 C 0.9460(2) 0.07908(15) 0.86199(13) 0.0468 1.0000 Uani . . . . . . C29 C 1.08660(19) 0.21774(15) 0.64693(13) 0.0450 1.0000 Uani . . . . . . C30 C 0.9152(3) -0.01041(18) 0.84644(17) 0.0713 1.0000 Uani . . . . . . C31 C 0.8798(3) 0.1125(2) 0.91880(15) 0.0708 1.0000 Uani . . . . . . C32 C 1.0639(3) 0.0827(2) 0.89532(18) 0.0835 1.0000 Uani . . . . . . C33 C 1.1444(3) 0.1386(2) 0.63148(19) 0.0738 1.0000 Uani . . . . . . C34 C 1.1622(2) 0.2719(2) 0.69892(16) 0.0654 1.0000 Uani . . . . . . C35 C 1.0567(2) 0.26367(18) 0.57438(14) 0.0552 1.0000 Uani . . . . . . C100 C 0.4392(2) 0.1453(2) 0.78841(15) 0.0558 1.0000 Uani . . . . . . C101 C 0.3566(2) 0.1139(2) 0.83234(18) 0.0781 1.0000 Uani . . . . . . C200 C 0.3519(3) 0.4006(3) 0.5896(3) 0.0932 1.0000 Uani . . . . . . C201 C 0.4220(3) 0.4013(3) 0.6615(2) 0.1136 1.0000 Uani . . . . . . C319 C 0.1425(6) -0.1144(5) 0.6178(5) 0.0891 0.377(6) Uani D U P . 2 . C320 C 0.2956(8) -0.1902(4) 0.5855(5) 0.0904 0.377(6) Uani D U P . 2 . C321 C 0.3052(7) -0.1243(5) 0.7067(4) 0.0939 0.377(6) Uani D U P . 2 . H21 H 0.7781 0.3552 0.6413 0.050(2) 1.0000 Uiso R . . . . . H31 H 0.7243 0.4457 0.5478 0.059(2) 1.0000 Uiso R . . . . . H41 H 0.5801 0.4167 0.4579 0.068(2) 1.0000 Uiso R . . . . . H51 H 0.4820 0.2975 0.4666 0.061(2) 1.0000 Uiso R . . . . . H101 H 0.2026 -0.0455 0.4949 0.048(2) 1.0000 Uiso R . . . . . H121 H 0.4252 -0.0126 0.6758 0.045(2) 1.0000 Uiso R . . . . . H161 H 0.1607 0.1871 0.3679 0.0847(19) 1.0000 Uiso R . . . . . H162 H 0.2572 0.2061 0.4314 0.0845(19) 1.0000 Uiso R . . . . . H163 H 0.1458 0.1696 0.4508 0.0850(19) 1.0000 Uiso R . . . . . H171 H 0.3782 0.1223 0.3703 0.0920(19) 1.0000 Uiso R . . . . . H172 H 0.2846 0.1015 0.3062 0.0915(19) 1.0000 Uiso R . . . . . H173 H 0.3489 0.0299 0.3505 0.0919(19) 1.0000 Uiso R . . . . . H181 H 0.0926 0.0306 0.4101 0.1025(19) 1.0000 Uiso R . . . . . H182 H 0.1159 0.0509 0.3298 0.1024(19) 1.0000 Uiso R . . . . . H183 H 0.1731 -0.0267 0.3713 0.1029(19) 1.0000 Uiso R . . . . . H191 H 0.2089 -0.1814 0.5342 0.1314(19) 0.623(6) Uiso R . P . 1 . H192 H 0.1192 -0.1206 0.5564 0.1317(19) 0.623(6) Uiso R . P . 1 . H193 H 0.1465 -0.2025 0.6016 0.1319(19) 0.623(6) Uiso R . P . 1 . H201 H 0.3871 -0.1887 0.6110 0.1189(19) 0.623(6) Uiso R . P . 1 . H202 H 0.3963 -0.1506 0.6902 0.1182(19) 0.623(6) Uiso R . P . 1 . H203 H 0.3179 -0.2240 0.6692 0.1187(19) 0.623(6) Uiso R . P . 1 . H211 H 0.1856 -0.1330 0.7157 0.1136(19) 0.623(6) Uiso R . P . 1 . H212 H 0.1556 -0.0511 0.6764 0.1134(19) 0.623(6) Uiso R . P . 1 . H213 H 0.2660 -0.0589 0.7274 0.1138(19) 0.623(6) Uiso R . P . 1 . H241 H 1.0763 0.1455 0.7745 0.043(2) 1.0000 Uiso R . . . . . H261 H 0.8754 0.2415 0.6059 0.039(2) 1.0000 Uiso R . . . . . H301 H 0.9642 -0.0321 0.8142 0.0939(19) 1.0000 Uiso R . . . . . H302 H 0.9268 -0.0401 0.8931 0.0937(19) 1.0000 Uiso R . . . . . H303 H 0.8405 -0.0142 0.8239 0.0938(19) 1.0000 Uiso R . . . . . H311 H 0.8039 0.1125 0.9001 0.0910(19) 1.0000 Uiso R . . . . . H312 H 0.9053 0.1671 0.9307 0.0910(19) 1.0000 Uiso R . . . . . H313 H 0.8934 0.0789 0.9625 0.0905(19) 1.0000 Uiso R . . . . . H321 H 1.1032 0.0548 0.8608 0.1157(19) 1.0000 Uiso R . . . . . H322 H 1.0827 0.1391 0.9019 0.1157(19) 1.0000 Uiso R . . . . . H323 H 1.0697 0.0553 0.9408 0.1153(19) 1.0000 Uiso R . . . . . H331 H 1.2070 0.1526 0.6096 0.0963(19) 1.0000 Uiso R . . . . . H332 H 1.0955 0.1062 0.5977 0.0963(19) 1.0000 Uiso R . . . . . H333 H 1.1646 0.1103 0.6775 0.0966(19) 1.0000 Uiso R . . . . . H341 H 1.2244 0.2859 0.6760 0.0858(19) 1.0000 Uiso R . . . . . H342 H 1.1238 0.3200 0.7114 0.0858(19) 1.0000 Uiso R . . . . . H343 H 1.1856 0.2414 0.7431 0.0854(19) 1.0000 Uiso R . . . . . H351 H 1.1223 0.2773 0.5540 0.0704(19) 1.0000 Uiso R . . . . . H352 H 1.0154 0.3126 0.5837 0.0704(19) 1.0000 Uiso R . . . . . H353 H 1.0115 0.2285 0.5408 0.0702(19) 1.0000 Uiso R . . . . . H1011 H 0.3196 0.1582 0.8500 0.1030(19) 1.0000 Uiso R . . . . . H1012 H 0.3914 0.0820 0.8718 0.1030(19) 1.0000 Uiso R . . . . . H1013 H 0.3073 0.0808 0.8011 0.1030(19) 1.0000 Uiso R . . . . . H2011 H 0.4707 0.4467 0.6637 0.1145(19) 1.0000 Uiso R . . . . . H2012 H 0.3791 0.4059 0.7007 0.1145(19) 1.0000 Uiso R . . . . . H2013 H 0.4620 0.3511 0.6669 0.1145(19) 1.0000 Uiso R . . . . . H3191 H 0.1180 -0.1650 0.6366 0.1057(19) 0.377(6) Uiso R . P . 2 . H3192 H 0.1208 -0.0700 0.6464 0.1056(19) 0.377(6) Uiso R . P . 2 . H3193 H 0.1128 -0.1073 0.5671 0.1056(19) 0.377(6) Uiso R . P . 2 . H3201 H 0.3718 -0.1888 0.5872 0.1108(19) 0.377(6) Uiso R . P . 2 . H3202 H 0.2747 -0.2382 0.6100 0.1108(19) 0.377(6) Uiso R . P . 2 . H3203 H 0.2620 -0.1902 0.5350 0.1103(19) 0.377(6) Uiso R . P . 2 . H3211 H 0.3046 -0.0718 0.7299 0.1177(19) 0.377(6) Uiso R . P . 2 . H3212 H 0.2615 -0.1627 0.7289 0.1178(19) 0.377(6) Uiso R . P . 2 . H3213 H 0.3773 -0.1442 0.7107 0.1172(19) 0.377(6) Uiso R . P . 2 . 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 0.03792(14) 0.04719(16) 0.03649(14) 0.00773(13) -0.00061(10) -0.00341(13) O1 0.0425(9) 0.0507(9) 0.0395(8) 0.0103(7) -0.0009(7) -0.0027(7) O2 0.0445(9) 0.0499(9) 0.0361(8) 0.0087(7) -0.0042(6) -0.0051(7) O100 0.1000(19) 0.0703(17) 0.146(3) 0.0073(16) 0.0396(18) 0.0079(14) O101 0.0487(10) 0.0681(12) 0.0499(10) 0.0146(9) 0.0092(8) 0.0002(9) N1 0.0391(10) 0.0387(10) 0.0377(9) 0.0050(8) -0.0016(8) -0.0020(8) N2 0.0395(10) 0.0448(11) 0.0392(10) 0.0082(8) -0.0006(8) -0.0039(8) N200 0.084(2) 0.177(4) 0.097(3) 0.018(3) 0.004(2) 0.002(3) C1 0.0370(11) 0.0405(12) 0.0405(11) 0.0069(9) 0.0028(9) 0.0021(9) C2 0.0437(12) 0.0435(14) 0.0510(13) 0.0045(10) 0.0025(10) -0.0013(10) C3 0.0534(15) 0.0421(14) 0.0687(17) 0.0160(12) 0.0053(13) -0.0044(11) C4 0.0595(16) 0.0567(17) 0.0699(18) 0.0326(14) -0.0051(14) -0.0011(13) C5 0.0513(14) 0.0583(16) 0.0542(15) 0.0194(13) -0.0071(12) -0.0034(12) C6 0.0413(12) 0.0439(13) 0.0429(12) 0.0095(10) 0.0010(9) -0.0009(10) C7 0.0379(11) 0.0474(13) 0.0372(11) 0.0062(10) -0.0026(9) -0.0006(10) C8 0.0420(12) 0.0436(13) 0.0376(11) 0.0045(10) 0.0020(9) 0.0003(10) C9 0.0414(12) 0.0460(13) 0.0352(11) -0.0025(9) -0.0011(9) 0.0013(10) C10 0.0471(13) 0.0432(13) 0.0428(12) -0.0037(10) -0.0009(10) -0.0046(10) C11 0.0473(13) 0.0407(13) 0.0437(12) 0.0012(10) 0.0027(10) -0.0020(10) C12 0.0463(13) 0.0453(13) 0.0375(11) 0.0070(10) -0.0009(9) 0.0007(10) C13 0.0386(11) 0.0455(13) 0.0360(11) 0.0028(9) -0.0021(9) -0.0005(10) C14 0.0498(13) 0.0543(14) 0.0325(11) -0.0011(10) -0.0035(10) 0.0015(11) C15 0.0694(16) 0.0439(13) 0.0574(15) 0.0064(11) 0.0035(13) -0.0126(12) C16 0.0764(19) 0.0702(19) 0.0461(14) 0.0010(13) -0.0074(13) 0.0193(16) C17 0.075(2) 0.096(2) 0.0410(14) 0.0050(15) 0.0068(13) 0.0157(17) C18 0.080(2) 0.087(2) 0.0532(16) 0.0028(16) -0.0231(15) -0.0153(18) C19 0.143(6) 0.089(4) 0.089(4) 0.028(3) -0.029(4) -0.070(4) C20 0.101(4) 0.062(3) 0.131(5) 0.041(4) 0.016(4) 0.006(3) C21 0.130(5) 0.064(3) 0.099(4) 0.009(3) 0.052(4) -0.022(3) C22 0.0400(11) 0.0381(11) 0.0308(9) -0.0001(9) 0.0012(8) -0.0013(10) C23 0.0440(12) 0.0400(12) 0.0331(10) 0.0017(9) -0.0031(9) -0.0014(9) C24 0.0370(11) 0.0462(14) 0.0404(11) 0.0030(10) -0.0041(9) 0.0014(9) C25 0.0400(11) 0.0377(11) 0.0368(11) -0.0013(9) 0.0023(9) -0.0001(9) C26 0.0430(12) 0.0390(12) 0.0324(10) 0.0021(9) 0.0012(9) -0.0004(9) C27 0.0385(11) 0.0370(11) 0.0325(10) -0.0006(9) -0.0022(8) -0.0015(9) C28 0.0501(13) 0.0498(14) 0.0376(12) 0.0098(10) -0.0040(10) -0.0005(11) C29 0.0409(12) 0.0497(14) 0.0446(13) 0.0023(11) 0.0068(10) 0.0008(10) C30 0.100(2) 0.0496(16) 0.0607(17) 0.0140(14) -0.0021(16) 0.0021(16) C31 0.090(2) 0.083(2) 0.0379(13) 0.0071(14) 0.0027(14) 0.0101(17) C32 0.0646(19) 0.117(3) 0.0611(18) 0.0395(19) -0.0170(15) -0.0054(19) C33 0.075(2) 0.076(2) 0.075(2) 0.0065(17) 0.0298(16) 0.0221(17) C34 0.0568(16) 0.078(2) 0.0582(16) 0.0079(15) -0.0027(13) -0.0210(15) C35 0.0529(15) 0.0683(17) 0.0451(13) 0.0057(12) 0.0093(11) -0.0089(13) C100 0.0448(13) 0.0695(19) 0.0516(14) -0.0003(14) 0.0014(11) -0.0065(14) C101 0.0539(17) 0.119(3) 0.0637(18) -0.0085(18) 0.0148(14) -0.0083(18) C200 0.078(3) 0.096(3) 0.112(3) 0.001(3) 0.036(3) -0.008(2) C201 0.090(3) 0.146(4) 0.107(3) -0.055(3) 0.025(2) -0.034(3) C319 0.070(5) 0.086(6) 0.114(7) 0.034(5) 0.026(5) -0.010(5) C320 0.118(7) 0.049(4) 0.110(7) 0.003(5) 0.035(6) -0.013(5) C321 0.126(7) 0.081(6) 0.068(5) 0.027(4) -0.007(5) -0.047(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 . O1 . 1.9658(15) yes Cu1 . O100 . 2.695(3) yes Cu1 . O101 . 1.9088(17) yes Cu1 . N1 . 1.9290(18) yes Cu1 . N2 . 1.9571(18) yes Cu1 . C7 . 2.879(2) yes Cu1 . C22 . 2.711(2) yes Cu1 . C27 . 2.732(2) yes Cu1 . C100 . 2.640(3) yes O1 . C22 . 1.275(3) yes O2 . C7 . 1.359(3) yes O2 . C8 . 1.387(3) yes O100 . C100 . 1.218(4) yes O101 . C100 . 1.272(3) yes N1 . C1 . 1.408(3) yes N1 . C27 . 1.343(3) yes N2 . C7 . 1.302(3) yes N2 . C13 . 1.408(3) yes N200 . C200 . 1.080(5) yes C1 . C2 . 1.400(3) yes C1 . C6 . 1.407(3) yes C2 . C3 . 1.376(3) yes C2 . H21 . 0.947 no C3 . C4 . 1.375(4) yes C3 . H31 . 0.935 no C4 . C5 . 1.372(4) yes C4 . H41 . 0.943 no C5 . C6 . 1.405(3) yes C5 . H51 . 0.952 no C6 . C7 . 1.446(3) yes C8 . C9 . 1.386(3) yes C8 . C13 . 1.381(3) yes C9 . C10 . 1.383(3) yes C9 . C14 . 1.533(3) yes C10 . C11 . 1.411(3) yes C10 . H101 . 0.957 no C11 . C12 . 1.384(3) yes C11 . C15 . 1.528(3) yes C12 . C13 . 1.379(3) yes C12 . H121 . 0.958 no C14 . C16 . 1.528(4) yes C14 . C17 . 1.525(4) yes C14 . C18 . 1.526(4) yes C15 . C19 . 1.518(5) yes C15 . C20 . 1.498(5) yes C15 . C21 . 1.521(5) yes C16 . H161 . 0.965 no C16 . H162 . 0.969 no C16 . H163 . 0.979 no C17 . H171 . 0.960 no C17 . H172 . 0.958 no C17 . H173 . 0.959 no C18 . H181 . 0.981 no C18 . H182 . 0.960 no C18 . H183 . 0.976 no C19 . H191 . 0.971 no C19 . H192 . 0.966 no C19 . H193 . 0.964 no C20 . H201 . 0.953 no C20 . H202 . 0.963 no C20 . H203 . 0.959 no C21 . H211 . 0.959 no C21 . H212 . 0.953 no C21 . H213 . 0.959 no C22 . C23 . 1.442(3) yes C22 . C27 . 1.456(3) yes C23 . C24 . 1.362(3) yes C23 . C28 . 1.534(3) yes C24 . C25 . 1.435(3) yes C24 . H241 . 0.950 no C25 . C26 . 1.359(3) yes C25 . C29 . 1.523(3) yes C26 . C27 . 1.414(3) yes C26 . H261 . 0.951 no C28 . C30 . 1.529(4) yes C28 . C31 . 1.524(4) yes C28 . C32 . 1.524(4) yes C29 . C33 . 1.530(4) yes C29 . C34 . 1.529(4) yes C29 . C35 . 1.525(3) yes C30 . H301 . 0.979 no C30 . H302 . 0.976 no C30 . H303 . 0.974 no C31 . H311 . 0.969 no C31 . H312 . 0.963 no C31 . H313 . 0.966 no C32 . H321 . 0.969 no C32 . H322 . 0.954 no C32 . H323 . 0.938 no C33 . H331 . 0.962 no C33 . H332 . 0.966 no C33 . H333 . 0.963 no C34 . H341 . 0.968 no C34 . H342 . 0.967 no C34 . H343 . 0.960 no C35 . H351 . 0.979 no C35 . H352 . 0.982 no C35 . H353 . 0.966 no C100 . C101 . 1.494(4) yes C101 . H1011 . 0.943 no C101 . H1012 . 0.946 no C101 . H1013 . 0.951 no C200 . C201 . 1.478(6) yes C201 . H2011 . 0.960 no C201 . H2012 . 0.960 no C201 . H2013 . 0.960 no C319 . H3191 . 0.963 no C319 . H3192 . 0.957 no C319 . H3193 . 0.957 no C320 . H3201 . 0.955 no C320 . H3202 . 0.959 no C320 . H3203 . 0.960 no C321 . H3211 . 0.958 no C321 . H3212 . 0.961 no C321 . H3213 . 0.957 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 O1 . Cu1 . O100 . 123.52(9) yes O1 . Cu1 . O101 . 94.81(7) yes O100 . Cu1 . O101 . 53.17(8) yes O1 . Cu1 . N1 . 83.12(7) yes O100 . Cu1 . N1 . 113.83(8) yes O101 . Cu1 . N1 . 162.33(8) yes O1 . Cu1 . N2 . 144.51(8) yes O100 . Cu1 . N2 . 90.74(9) yes O101 . Cu1 . N2 . 99.94(8) yes N1 . Cu1 . N2 . 91.58(8) yes O1 . Cu1 . C7 . 143.07(7) yes O100 . Cu1 . C7 . 91.49(8) yes O101 . Cu1 . C7 . 117.74(7) yes N1 . Cu1 . C7 . 70.89(7) yes N2 . Cu1 . C7 . 22.33(7) yes O1 . Cu1 . C22 . 25.90(6) yes O100 . Cu1 . C22 . 132.03(8) yes O101 . Cu1 . C22 . 119.92(7) yes N1 . Cu1 . C22 . 57.31(7) yes N2 . Cu1 . C22 . 133.10(7) yes O1 . Cu1 . C27 . 56.87(6) yes O100 . Cu1 . C27 . 131.76(8) yes O101 . Cu1 . C27 . 150.10(7) yes N1 . Cu1 . C27 . 27.12(7) yes N2 . Cu1 . C27 . 108.95(7) yes O1 . Cu1 . C100 . 111.54(8) yes O100 . Cu1 . C100 . 26.37(8) yes O101 . Cu1 . C100 . 26.82(9) yes N1 . Cu1 . C100 . 139.36(9) yes N2 . Cu1 . C100 . 95.23(8) yes C7 . Cu1 . C22 . 121.32(6) yes C7 . Cu1 . C27 . 92.15(6) yes C22 . Cu1 . C27 . 31.04(6) yes C7 . Cu1 . C100 . 105.24(7) yes C22 . Cu1 . C100 . 131.52(7) yes C27 . Cu1 . C100 . 149.52(8) yes Cu1 . O1 . C22 . 111.77(13) yes C7 . O2 . C8 . 105.25(16) yes Cu1 . O100 . C100 . 74.27(18) yes Cu1 . O101 . C100 . 110.57(18) yes Cu1 . N1 . C1 . 125.10(14) yes Cu1 . N1 . C27 . 111.96(14) yes C1 . N1 . C27 . 120.86(19) yes Cu1 . N2 . C7 . 122.84(16) yes Cu1 . N2 . C13 . 130.44(15) yes C7 . N2 . C13 . 106.10(18) yes N1 . C1 . C2 . 121.1(2) yes N1 . C1 . C6 . 120.8(2) yes C2 . C1 . C6 . 117.9(2) yes C1 . C2 . C3 . 121.3(2) yes C1 . C2 . H21 . 119.6 no C3 . C2 . H21 . 119.1 no C2 . C3 . C4 . 120.6(2) yes C2 . C3 . H31 . 119.1 no C4 . C3 . H31 . 120.3 no C3 . C4 . C5 . 119.5(2) yes C3 . C4 . H41 . 120.2 no C5 . C4 . H41 . 120.3 no C4 . C5 . C6 . 121.1(2) yes C4 . C5 . H51 . 120.0 no C6 . C5 . H51 . 118.9 no C1 . C6 . C5 . 119.4(2) yes C1 . C6 . C7 . 121.9(2) yes C5 . C6 . C7 . 118.7(2) yes C6 . C7 . O2 . 117.39(19) yes C6 . C7 . N2 . 129.1(2) yes O2 . C7 . N2 . 113.5(2) yes C6 . C7 . Cu1 . 94.34(13) yes O2 . C7 . Cu1 . 147.83(15) yes N2 . C7 . Cu1 . 34.84(10) yes O2 . C8 . C9 . 128.1(2) yes O2 . C8 . C13 . 107.80(19) yes C9 . C8 . C13 . 124.1(2) yes C8 . C9 . C10 . 113.0(2) yes C8 . C9 . C14 . 122.6(2) yes C10 . C9 . C14 . 124.4(2) yes C9 . C10 . C11 . 125.2(2) yes C9 . C10 . H101 . 118.2 no C11 . C10 . H101 . 116.6 no C10 . C11 . C12 . 118.9(2) yes C10 . C11 . C15 . 120.6(2) yes C12 . C11 . C15 . 120.6(2) yes C11 . C12 . C13 . 117.5(2) yes C11 . C12 . H121 . 121.6 no C13 . C12 . H121 . 120.8 no N2 . C13 . C8 . 107.36(19) yes N2 . C13 . C12 . 131.2(2) yes C8 . C13 . C12 . 121.4(2) yes C9 . C14 . C16 . 109.01(19) yes C9 . C14 . C17 . 109.9(2) yes C16 . C14 . C17 . 109.7(2) yes C9 . C14 . C18 . 111.3(2) yes C16 . C14 . C18 . 108.1(2) yes C17 . C14 . C18 . 108.8(2) yes C11 . C15 . C19 . 113.3(2) yes C11 . C15 . C20 . 111.4(2) yes C19 . C15 . C20 . 107.975(12) yes C11 . C15 . C21 . 108.1(2) yes C19 . C15 . C21 . 107.974(13) yes C20 . C15 . C21 . 107.975(11) yes C14 . C16 . H161 . 108.0 no C14 . C16 . H162 . 108.4 no H161 . C16 . H162 . 110.6 no C14 . C16 . H163 . 109.5 no H161 . C16 . H163 . 108.8 no H162 . C16 . H163 . 111.4 no C14 . C17 . H171 . 108.9 no C14 . C17 . H172 . 107.2 no H171 . C17 . H172 . 110.8 no C14 . C17 . H173 . 107.4 no H171 . C17 . H173 . 111.3 no H172 . C17 . H173 . 111.0 no C14 . C18 . H181 . 108.9 no C14 . C18 . H182 . 107.5 no H181 . C18 . H182 . 108.5 no C14 . C18 . H183 . 109.1 no H181 . C18 . H183 . 111.6 no H182 . C18 . H183 . 111.0 no C15 . C19 . H191 . 106.6 no C15 . C19 . H192 . 109.1 no H191 . C19 . H192 . 111.4 no C15 . C19 . H193 . 108.5 no H191 . C19 . H193 . 110.7 no H192 . C19 . H193 . 110.4 no C15 . C20 . H201 . 109.6 no C15 . C20 . H202 . 107.3 no H201 . C20 . H202 . 109.8 no C15 . C20 . H203 . 109.7 no H201 . C20 . H203 . 111.3 no H202 . C20 . H203 . 109.1 no C15 . C21 . H211 . 109.2 no C15 . C21 . H212 . 108.1 no H211 . C21 . H212 . 107.5 no C15 . C21 . H213 . 111.6 no H211 . C21 . H213 . 110.2 no H212 . C21 . H213 . 110.1 no O1 . C22 . Cu1 . 42.34(10) yes O1 . C22 . C23 . 124.00(19) yes Cu1 . C22 . C23 . 166.25(16) yes O1 . C22 . C27 . 117.44(18) yes Cu1 . C22 . C27 . 75.27(12) yes C23 . C22 . C27 . 118.47(19) yes C22 . C23 . C24 . 116.36(19) yes C22 . C23 . C28 . 120.9(2) yes C24 . C23 . C28 . 122.4(2) yes C23 . C24 . C25 . 125.2(2) yes C23 . C24 . H241 . 118.6 no C25 . C24 . H241 . 116.1 no C24 . C25 . C26 . 118.2(2) yes C24 . C25 . C29 . 119.02(19) yes C26 . C25 . C29 . 122.8(2) yes C25 . C26 . C27 . 120.3(2) yes C25 . C26 . H261 . 119.4 no C27 . C26 . H261 . 120.3 no C22 . C27 . C26 . 119.80(19) yes C22 . C27 . N1 . 112.51(19) yes C26 . C27 . N1 . 127.67(19) yes C22 . C27 . Cu1 . 73.69(12) yes C26 . C27 . Cu1 . 160.76(15) yes N1 . C27 . Cu1 . 40.92(10) yes C23 . C28 . C30 . 109.0(2) yes C23 . C28 . C31 . 110.6(2) yes C30 . C28 . C31 . 108.7(2) yes C23 . C28 . C32 . 111.8(2) yes C30 . C28 . C32 . 108.6(3) yes C31 . C28 . C32 . 108.0(2) yes C25 . C29 . C33 . 108.6(2) yes C25 . C29 . C34 . 109.5(2) yes C33 . C29 . C34 . 109.5(2) yes C25 . C29 . C35 . 112.34(19) yes C33 . C29 . C35 . 108.7(2) yes C34 . C29 . C35 . 108.2(2) yes C28 . C30 . H301 . 107.1 no C28 . C30 . H302 . 108.0 no H301 . C30 . H302 . 108.6 no C28 . C30 . H303 . 110.1 no H301 . C30 . H303 . 112.1 no H302 . C30 . H303 . 110.8 no C28 . C31 . H311 . 111.5 no C28 . C31 . H312 . 106.8 no H311 . C31 . H312 . 111.2 no C28 . C31 . H313 . 108.1 no H311 . C31 . H313 . 110.0 no H312 . C31 . H313 . 109.0 no C28 . C32 . H321 . 106.2 no C28 . C32 . H322 . 107.3 no H321 . C32 . H322 . 113.3 no C28 . C32 . H323 . 106.5 no H321 . C32 . H323 . 111.8 no H322 . C32 . H323 . 111.2 no C29 . C33 . H331 . 108.4 no C29 . C33 . H332 . 107.7 no H331 . C33 . H332 . 110.5 no C29 . C33 . H333 . 108.5 no H331 . C33 . H333 . 110.4 no H332 . C33 . H333 . 111.2 no C29 . C34 . H341 . 109.8 no C29 . C34 . H342 . 109.3 no H341 . C34 . H342 . 111.8 no C29 . C34 . H343 . 108.3 no H341 . C34 . H343 . 108.5 no H342 . C34 . H343 . 109.1 no C29 . C35 . H351 . 109.1 no C29 . C35 . H352 . 108.7 no H351 . C35 . H352 . 112.2 no C29 . C35 . H353 . 108.1 no H351 . C35 . H353 . 110.2 no H352 . C35 . H353 . 108.3 no Cu1 . C100 . O101 . 42.61(12) yes Cu1 . C100 . O100 . 79.36(19) yes O101 . C100 . O100 . 121.9(3) yes Cu1 . C100 . C101 . 157.8(2) yes O101 . C100 . C101 . 115.5(3) yes O100 . C100 . C101 . 122.6(3) yes C100 . C101 . H1011 . 109.7 no C100 . C101 . H1012 . 108.5 no H1011 . C101 . H1012 . 111.1 no C100 . C101 . H1013 . 108.5 no H1011 . C101 . H1013 . 109.4 no H1012 . C101 . H1013 . 109.6 no N200 . C200 . C201 . 178.4(5) yes C200 . C201 . H2011 . 109.9 no C200 . C201 . H2012 . 109.7 no H2011 . C201 . H2012 . 109.5 no C200 . C201 . H2013 . 108.8 no H2011 . C201 . H2013 . 109.5 no H2012 . C201 . H2013 . 109.5 no C15 . C319 . H3191 . 109.2 no C15 . C319 . H3192 . 108.6 no H3191 . C319 . H3192 . 108.9 no C15 . C319 . H3193 . 110.0 no H3191 . C319 . H3193 . 110.5 no H3192 . C319 . H3193 . 109.5 no C15 . C320 . H3201 . 108.3 no C15 . C320 . H3202 . 108.8 no H3201 . C320 . H3202 . 110.2 no C15 . C320 . H3203 . 110.4 no H3201 . C320 . H3203 . 109.5 no H3202 . C320 . H3203 . 109.7 no C15 . C321 . H3211 . 108.9 no C15 . C321 . H3212 . 109.3 no H3211 . C321 . H3212 . 110.8 no C15 . C321 . H3213 . 108.1 no H3211 . C321 . H3213 . 109.8 no H3212 . C321 . H3213 . 109.9 no