# Electronic Supplementary Material (ESI) for Chemical Communications # 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_001 _database_code_depnum_ccdc_archive 'CCDC 912051' #TrackingRef '15601_web_deposit_cif_file_0_LiangZhang_1353570714.001.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common IPrCu(COOH) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H37 Cu N2 O2' _chemical_formula_weight 497.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.798(3) _cell_length_b 10.814(3) _cell_length_c 16.337(6) _cell_angle_alpha 70.744(5) _cell_angle_beta 86.134(7) _cell_angle_gamma 85.896(5) _cell_volume 1628.1(9) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Fragment _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.014 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.691 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8194 _exptl_absorpt_correction_T_max 0.8572 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8138 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0577 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5523 _reflns_number_gt 4174 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0732P)^2^+0.1203P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5523 _refine_ls_number_parameters 301 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1296 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2244(4) 0.7122(4) 0.2501(2) 0.0568(10) Uani 1 1 d DU . . C2 C -0.2282(3) 0.7562(3) 0.24287(18) 0.0335(7) Uani 1 1 d . . . C3 C -0.4473(3) 0.7627(3) 0.2966(2) 0.0440(8) Uani 1 1 d . . . H3 H -0.5239 0.7533 0.3367 0.053 Uiso 1 1 calc R . . C4 C -0.4482(3) 0.8144(3) 0.2103(2) 0.0454(8) Uani 1 1 d . . . H4 H -0.5267 0.8478 0.1772 0.054 Uiso 1 1 calc R . . C5 C -0.2738(3) 0.8565(3) 0.08706(19) 0.0391(7) Uani 1 1 d . . . C6 C -0.2654(4) 0.9913(3) 0.0474(2) 0.0521(9) Uani 1 1 d . . . C7 C -0.2971(5) 1.0880(3) 0.0957(3) 0.0621(10) Uani 1 1 d . . . H7 H -0.3430 1.0394 0.1527 0.074 Uiso 1 1 calc R . . C8 C -0.1700(7) 1.1355(6) 0.1148(5) 0.126(2) Uani 1 1 d . . . H8A H -0.1924 1.1977 0.1464 0.189 Uiso 1 1 calc R . . H8B H -0.1192 1.1794 0.0603 0.189 Uiso 1 1 calc R . . H8C H -0.1136 1.0611 0.1503 0.189 Uiso 1 1 calc R . . C9 C -0.3977(7) 1.1966(5) 0.0477(4) 0.110(2) Uani 1 1 d . . . H9A H -0.4801 1.1582 0.0378 0.164 Uiso 1 1 calc R . . H9B H -0.3554 1.2477 -0.0082 0.164 Uiso 1 1 calc R . . H9C H -0.4226 1.2540 0.0824 0.164 Uiso 1 1 calc R . . C10 C -0.2269(4) 1.0335(4) -0.0406(2) 0.0636(11) Uani 1 1 d . . . H10 H -0.2180 1.1245 -0.0702 0.076 Uiso 1 1 calc R . . C11 C -0.2015(5) 0.9471(5) -0.0850(3) 0.0762(13) Uani 1 1 d . . . H11 H -0.1784 0.9796 -0.1455 0.091 Uiso 1 1 calc R . . C12 C -0.2085(5) 0.8128(5) -0.0445(2) 0.0721(12) Uani 1 1 d . . . H12 H -0.1893 0.7541 -0.0767 0.087 Uiso 1 1 calc R . . C13 C -0.2444(4) 0.7646(4) 0.0447(2) 0.0529(9) Uani 1 1 d . . . C14 C -0.2496(4) 0.6162(4) 0.0895(2) 0.0603(10) Uani 1 1 d . . . H14 H -0.2794 0.6016 0.1516 0.072 Uiso 1 1 calc R . . C15 C -0.1089(6) 0.5492(5) 0.0888(4) 0.1053(18) Uani 1 1 d . . . H15A H -0.1143 0.4549 0.1190 0.158 Uiso 1 1 calc R . . H15B H -0.0461 0.5854 0.1183 0.158 Uiso 1 1 calc R . . H15C H -0.0749 0.5641 0.0287 0.158 Uiso 1 1 calc R . . C16 C -0.3504(8) 0.5562(6) 0.0526(5) 0.135(3) Uani 1 1 d . . . H16A H -0.3503 0.4618 0.0840 0.203 Uiso 1 1 calc R . . H16B H -0.3258 0.5706 -0.0089 0.203 Uiso 1 1 calc R . . H16C H -0.4419 0.5963 0.0582 0.203 Uiso 1 1 calc R . . C17 C -0.2623(3) 0.6644(3) 0.40185(18) 0.0356(7) Uani 1 1 d . . . C18 C -0.2193(3) 0.7436(3) 0.4449(2) 0.0439(8) Uani 1 1 d . . . C19 C -0.2242(4) 0.8929(3) 0.4071(2) 0.0538(9) Uani 1 1 d . . . H19 H -0.2605 0.9167 0.3478 0.065 Uiso 1 1 calc R . . C20 C -0.3225(6) 0.9552(5) 0.4585(3) 0.0954(17) Uani 1 1 d . . . H20A H -0.4127 0.9191 0.4631 0.143 Uiso 1 1 calc R . . H20B H -0.3299 1.0502 0.4291 0.143 Uiso 1 1 calc R . . H20C H -0.2889 0.9369 0.5167 0.143 Uiso 1 1 calc R . . C21 C -0.0819(6) 0.9420(5) 0.3954(4) 0.109(2) Uani 1 1 d . . . H21A H -0.0242 0.8985 0.3605 0.164 Uiso 1 1 calc R . . H21B H -0.0431 0.9225 0.4523 0.164 Uiso 1 1 calc R . . H21C H -0.0858 1.0370 0.3656 0.164 Uiso 1 1 calc R . . C22 C -0.1702(4) 0.6809(4) 0.5281(2) 0.0547(9) Uani 1 1 d . . . H22 H -0.1408 0.7316 0.5607 0.066 Uiso 1 1 calc R . . C23 C -0.1647(4) 0.5469(4) 0.5623(2) 0.0580(10) Uani 1 1 d . . . H23 H -0.1299 0.5061 0.6184 0.070 Uiso 1 1 calc R . . C24 C -0.2078(4) 0.4696(3) 0.5182(2) 0.0505(9) Uani 1 1 d . . . H24 H -0.2025 0.3768 0.5438 0.061 Uiso 1 1 calc R . . C25 C -0.2591(3) 0.5267(3) 0.43618(19) 0.0387(7) Uani 1 1 d . . . C26 C -0.3082(4) 0.4421(3) 0.3876(2) 0.0463(8) Uani 1 1 d . . . H26 H -0.3539 0.5016 0.3349 0.056 Uiso 1 1 calc R . . C27 C -0.4135(4) 0.3488(4) 0.4422(3) 0.0697(12) Uani 1 1 d . . . H27A H -0.4443 0.2962 0.4089 0.105 Uiso 1 1 calc R . . H27B H -0.4921 0.3994 0.4577 0.105 Uiso 1 1 calc R . . H27C H -0.3722 0.2907 0.4952 0.105 Uiso 1 1 calc R . . C28 C -0.1884(4) 0.3671(4) 0.3570(3) 0.0689(11) Uani 1 1 d . . . H28A H -0.2231 0.3142 0.3252 0.103 Uiso 1 1 calc R . . H28B H -0.1403 0.3094 0.4074 0.103 Uiso 1 1 calc R . . H28C H -0.1249 0.4295 0.3189 0.103 Uiso 1 1 calc R . . N1 N -0.3160(2) 0.8105(2) 0.17813(15) 0.0362(6) Uani 1 1 d . . . N2 N -0.3120(2) 0.7257(2) 0.31596(15) 0.0340(6) Uani 1 1 d . . . O1 O 0.1390(2) 0.6704(2) 0.21601(16) 0.0561(6) Uani 1 1 d . . . O2 O 0.2265(3) 0.7858(3) 0.2863(2) 0.0698(8) Uani 1 1 d U . . Cu1 Cu -0.04097(4) 0.72461(4) 0.23234(2) 0.04119(16) Uani 1 1 d . . . H1 H 0.312(2) 0.665(3) 0.240(2) 0.050 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.058(2) 0.053(2) 0.047(2) 0.0077(14) -0.0016(19) -0.038(2) C2 0.0428(18) 0.0296(15) 0.0283(15) -0.0080(12) -0.0053(13) -0.0075(13) C3 0.0341(18) 0.053(2) 0.0410(17) -0.0107(15) 0.0015(14) 0.0000(15) C4 0.0353(19) 0.050(2) 0.0432(18) -0.0051(15) -0.0082(14) 0.0007(15) C5 0.0398(18) 0.0449(18) 0.0285(15) -0.0062(13) -0.0036(13) -0.0020(14) C6 0.058(2) 0.047(2) 0.0400(18) 0.0001(16) -0.0058(16) -0.0001(16) C7 0.084(3) 0.039(2) 0.060(2) -0.0113(18) -0.005(2) -0.0098(19) C8 0.115(5) 0.126(5) 0.168(7) -0.084(5) -0.037(4) -0.006(4) C9 0.129(5) 0.084(4) 0.109(4) -0.031(3) -0.014(4) 0.043(3) C10 0.081(3) 0.050(2) 0.043(2) 0.0072(18) 0.0010(19) -0.0072(19) C11 0.099(4) 0.077(3) 0.036(2) 0.004(2) 0.005(2) -0.011(2) C12 0.096(3) 0.082(3) 0.039(2) -0.022(2) 0.003(2) -0.005(2) C13 0.061(2) 0.055(2) 0.0391(18) -0.0106(16) -0.0006(16) -0.0046(17) C14 0.084(3) 0.049(2) 0.049(2) -0.0184(17) -0.0069(19) -0.001(2) C15 0.113(5) 0.079(3) 0.122(5) -0.037(3) -0.004(3) 0.027(3) C16 0.163(6) 0.075(4) 0.151(6) 0.003(4) -0.070(5) -0.028(4) C17 0.0349(17) 0.0407(17) 0.0260(14) -0.0045(13) 0.0010(12) -0.0022(13) C18 0.049(2) 0.049(2) 0.0324(16) -0.0098(15) 0.0008(14) -0.0108(15) C19 0.077(3) 0.047(2) 0.0399(19) -0.0148(16) -0.0038(17) -0.0135(18) C20 0.146(5) 0.058(3) 0.074(3) -0.019(2) 0.017(3) 0.013(3) C21 0.099(4) 0.049(3) 0.171(6) -0.021(3) 0.000(4) -0.030(3) C22 0.067(3) 0.064(2) 0.0341(18) -0.0137(17) -0.0066(16) -0.0172(19) C23 0.069(3) 0.064(2) 0.0315(17) -0.0003(17) -0.0112(17) -0.0072(19) C24 0.057(2) 0.045(2) 0.0398(18) -0.0006(16) -0.0039(16) -0.0032(16) C25 0.0373(18) 0.0443(18) 0.0323(16) -0.0096(14) 0.0014(13) -0.0042(14) C26 0.058(2) 0.0401(18) 0.0391(18) -0.0105(15) 0.0008(15) -0.0058(15) C27 0.068(3) 0.072(3) 0.074(3) -0.030(2) 0.013(2) -0.026(2) C28 0.071(3) 0.068(3) 0.076(3) -0.036(2) 0.006(2) -0.006(2) N1 0.0366(15) 0.0369(14) 0.0300(13) -0.0037(11) -0.0031(11) -0.0028(11) N2 0.0344(14) 0.0380(14) 0.0276(12) -0.0077(10) -0.0016(10) -0.0030(11) O1 0.0440(15) 0.0565(15) 0.0627(16) -0.0119(13) -0.0021(12) -0.0074(12) O2 0.0583(18) 0.0623(18) 0.084(2) -0.0166(14) -0.0038(14) -0.0068(14) Cu1 0.0338(2) 0.0442(3) 0.0353(2) 0.00054(16) -0.00089(15) -0.00106(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.139(5) . ? C1 O1 1.224(4) . ? C1 H1 0.999(10) . ? C2 N1 1.358(4) . ? C2 N2 1.363(4) . ? C2 Cu1 1.848(3) . ? C3 C4 1.335(5) . ? C3 N2 1.383(4) . ? C3 H3 0.9500 . ? C4 N1 1.368(4) . ? C4 H4 0.9500 . ? C5 C13 1.391(5) . ? C5 C6 1.392(5) . ? C5 N1 1.446(4) . ? C6 C10 1.392(5) . ? C6 C7 1.509(5) . ? C7 C8 1.469(7) . ? C7 C9 1.515(6) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.361(6) . ? C10 H10 0.9500 . ? C11 C12 1.388(6) . ? C11 H11 0.9500 . ? C12 C13 1.406(5) . ? C12 H12 0.9500 . ? C13 C14 1.531(5) . ? C14 C16 1.480(7) . ? C14 C15 1.512(6) . ? C14 H14 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.376(5) . ? C17 C25 1.406(4) . ? C17 N2 1.442(4) . ? C18 C22 1.405(5) . ? C18 C19 1.525(5) . ? C19 C20 1.502(6) . ? C19 C21 1.505(6) . ? C19 H19 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.369(5) . ? C22 H22 0.9500 . ? C23 C24 1.373(5) . ? C23 H23 0.9500 . ? C24 C25 1.390(4) . ? C24 H24 0.9500 . ? C25 C26 1.514(5) . ? C26 C27 1.519(5) . ? C26 C28 1.530(5) . ? C26 H26 1.0000 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? O1 Cu1 1.848(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 137.3(5) . . ? O2 C1 H1 119(2) . . ? O1 C1 H1 104(2) . . ? N1 C2 N2 103.4(3) . . ? N1 C2 Cu1 127.7(2) . . ? N2 C2 Cu1 128.9(2) . . ? C4 C3 N2 106.0(3) . . ? C4 C3 H3 127.0 . . ? N2 C3 H3 127.0 . . ? C3 C4 N1 107.8(3) . . ? C3 C4 H4 126.1 . . ? N1 C4 H4 126.1 . . ? C13 C5 C6 124.2(3) . . ? C13 C5 N1 118.5(3) . . ? C6 C5 N1 117.2(3) . . ? C5 C6 C10 116.2(3) . . ? C5 C6 C7 122.7(3) . . ? C10 C6 C7 121.0(3) . . ? C8 C7 C6 110.6(4) . . ? C8 C7 C9 113.8(5) . . ? C6 C7 C9 110.9(4) . . ? C8 C7 H7 107.1 . . ? C6 C7 H7 107.1 . . ? C9 C7 H7 107.1 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C6 121.3(4) . . ? C11 C10 H10 119.3 . . ? C6 C10 H10 119.3 . . ? C10 C11 C12 121.9(4) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C11 C12 C13 119.1(4) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C5 C13 C12 117.1(3) . . ? C5 C13 C14 123.9(3) . . ? C12 C13 C14 119.0(3) . . ? C16 C14 C15 111.1(5) . . ? C16 C14 C13 113.0(4) . . ? C15 C14 C13 110.9(4) . . ? C16 C14 H14 107.2 . . ? C15 C14 H14 107.2 . . ? C13 C14 H14 107.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C25 123.9(3) . . ? C18 C17 N2 118.3(3) . . ? C25 C17 N2 117.8(3) . . ? C17 C18 C22 116.9(3) . . ? C17 C18 C19 123.4(3) . . ? C22 C18 C19 119.7(3) . . ? C20 C19 C21 114.0(4) . . ? C20 C19 C18 111.8(3) . . ? C21 C19 C18 110.4(3) . . ? C20 C19 H19 106.7 . . ? C21 C19 H19 106.7 . . ? C18 C19 H19 106.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C18 120.1(3) . . ? C23 C22 H22 119.9 . . ? C18 C22 H22 119.9 . . ? C22 C23 C24 122.0(3) . . ? C22 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C23 C24 C25 120.2(3) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C24 C25 C17 116.8(3) . . ? C24 C25 C26 120.4(3) . . ? C17 C25 C26 122.7(3) . . ? C25 C26 C27 111.3(3) . . ? C25 C26 C28 111.3(3) . . ? C27 C26 C28 110.9(3) . . ? C25 C26 H26 107.7 . . ? C27 C26 H26 107.7 . . ? C28 C26 H26 107.7 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C2 N1 C4 111.3(2) . . ? C2 N1 C5 123.8(2) . . ? C4 N1 C5 124.9(2) . . ? C2 N2 C3 111.5(2) . . ? C2 N2 C17 123.0(2) . . ? C3 N2 C17 125.5(2) . . ? C1 O1 Cu1 115.8(3) . . ? O1 Cu1 C2 170.54(12) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 1.054 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.061 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.318 0.247 0.255 193 49 ' ' 2 -0.318 0.753 0.745 193 49 ' ' _platon_squeeze_details ; One disordered Benzene molecule per formual unit of IPrCu(COOH) were not modelled and the disordered density was taken into accountusing the SQUEEZE/PLATON procedure. (Sluis, P. van der; Spek, A. L. Acta Crystallogr.1990, A46, 194?01) as implemented in PLATON (Spek, A.L. ActaCrystallogr. 1990, A46, C34; Spek, A.L. J. Appl. Cryst. 2003, 36, 7?3.PLATON - a multipurpose crystallographic tool. Utrecht University, Utrecht, The Netherlands). ;