data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Wu, Ming-Jung' _publ_contact_author_email mijuwu@faculty.nsysu.edu.tw _publ_section_title ; The Copper-Mediated Cyclization Reaction of Enediynones with Hydrazine Provides Pyrazolo[1,5-a]pyridines ; _publ_author_name 'Ming-Jung Wu' # Attachment '- 8j.cif' data_a8674 _database_code_depnum_ccdc_archive 'CCDC 792989' #TrackingRef '- 8j.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 N2 O' _chemical_formula_sum 'C20 H16 N2 O' _chemical_formula_weight 300.35 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.0916(13) _cell_length_b 7.3204(4) _cell_length_c 38.0041(18) _cell_angle_alpha 90.00 _cell_angle_beta 97.320(3) _cell_angle_gamma 90.00 _cell_volume 6371.8(6) _cell_formula_units_Z 16 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour 'pale brown' _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9777 _exptl_absorpt_correction_T_max 0.9914 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21286 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5605 _reflns_number_gt 4085 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0894P)^2^+1.2697P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5605 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1535 _refine_ls_wR_factor_gt 0.1279 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 0.38709(15) 0.2802(4) 0.13636(6) 0.0877(9) Uani 1 1 d . . . H1A H 0.3855 0.1519 0.1311 0.132 Uiso 1 1 calc R . . H1B H 0.4076 0.3424 0.1194 0.132 Uiso 1 1 calc R . . H1C H 0.3481 0.3278 0.1351 0.132 Uiso 1 1 calc R . . C2 C 0.42269(9) 0.4844(3) 0.18259(5) 0.0495(5) Uani 1 1 d . . . C3 C 0.43921(11) 0.6264(4) 0.16168(6) 0.0673(7) Uani 1 1 d . . . H3 H 0.4445 0.6054 0.1382 0.081 Uiso 1 1 calc R . . C4 C 0.44772(12) 0.7990(4) 0.17613(7) 0.0764(8) Uani 1 1 d . . . H4 H 0.4587 0.8942 0.1622 0.092 Uiso 1 1 calc R . . C5 C 0.44010(12) 0.8315(3) 0.21081(7) 0.0745(7) Uani 1 1 d . . . H5 H 0.4452 0.9487 0.2201 0.089 Uiso 1 1 calc R . . C6 C 0.42488(10) 0.6902(3) 0.23181(6) 0.0590(6) Uani 1 1 d . . . H6 H 0.4207 0.7123 0.2555 0.071 Uiso 1 1 calc R . . C7 C 0.41564(9) 0.5151(3) 0.21804(5) 0.0450(5) Uani 1 1 d . . . C8 C 0.40164(9) 0.3642(3) 0.24133(5) 0.0424(5) Uani 1 1 d . . . C9 C 0.43635(9) 0.3124(3) 0.27116(5) 0.0508(5) Uani 1 1 d . . . H9 H 0.4712 0.3743 0.2777 0.061 Uiso 1 1 calc R . . C10 C 0.42113(11) 0.1681(3) 0.29244(5) 0.0581(6) Uani 1 1 d . . . H10 H 0.4460 0.1356 0.3127 0.070 Uiso 1 1 calc R . . C11 C 0.37079(11) 0.0763(3) 0.28382(5) 0.0595(6) Uani 1 1 d . . . H11 H 0.3611 -0.0202 0.2979 0.071 Uiso 1 1 calc R . . C12 C 0.33293(10) 0.1272(3) 0.25338(5) 0.0485(5) Uani 1 1 d . . . C13 C 0.27849(10) 0.0758(3) 0.23677(5) 0.0536(6) Uani 1 1 d . . . H13 H 0.2549 -0.0171 0.2437 0.064 Uiso 1 1 calc R . . C14 C 0.26626(9) 0.1905(2) 0.20775(5) 0.0427(5) Uani 1 1 d . . . C15 C 0.21270(9) 0.2002(2) 0.18203(5) 0.0422(5) Uani 1 1 d . . . C16 C 0.16426(10) 0.0958(3) 0.18625(5) 0.0544(5) Uani 1 1 d . . . H16 H 0.1660 0.0126 0.2048 0.065 Uiso 1 1 calc R . . C17 C 0.11329(10) 0.1135(3) 0.16325(6) 0.0614(6) Uani 1 1 d . . . H17 H 0.0810 0.0423 0.1664 0.074 Uiso 1 1 calc R . . C18 C 0.11021(10) 0.2364(3) 0.13569(6) 0.0593(6) Uani 1 1 d . . . H18 H 0.0756 0.2504 0.1205 0.071 Uiso 1 1 calc R . . C19 C 0.15817(10) 0.3379(3) 0.13072(6) 0.0575(6) Uani 1 1 d . . . H19 H 0.1563 0.4195 0.1119 0.069 Uiso 1 1 calc R . . C20 C 0.20937(10) 0.3202(3) 0.15346(5) 0.0514(5) Uani 1 1 d . . . H20 H 0.2419 0.3890 0.1497 0.062 Uiso 1 1 calc R . . C21 C 0.28532(12) 0.7649(3) 0.15408(5) 0.0686(7) Uani 1 1 d . . . H21A H 0.3148 0.7062 0.1703 0.103 Uiso 1 1 calc R . . H21B H 0.2481 0.7521 0.1626 0.103 Uiso 1 1 calc R . . H21C H 0.2945 0.8922 0.1523 0.103 Uiso 1 1 calc R . . C22 C 0.24324(9) 0.7478(2) 0.09347(5) 0.0417(5) Uani 1 1 d . . . C23 C 0.20544(10) 0.8905(3) 0.09734(5) 0.0496(5) Uani 1 1 d . . . H23 H 0.2070 0.9510 0.1190 0.060 Uiso 1 1 calc R . . C24 C 0.16537(10) 0.9432(3) 0.06912(5) 0.0525(5) Uani 1 1 d . . . H24 H 0.1397 1.0383 0.0720 0.063 Uiso 1 1 calc R . . C25 C 0.16277(9) 0.8581(3) 0.03683(5) 0.0511(5) Uani 1 1 d . . . H25 H 0.1360 0.8960 0.0179 0.061 Uiso 1 1 calc R . . C26 C 0.20018(9) 0.7162(3) 0.03291(5) 0.0456(5) Uani 1 1 d . . . H26 H 0.1981 0.6567 0.0112 0.055 Uiso 1 1 calc R . . C27 C 0.24108(9) 0.6596(2) 0.06079(5) 0.0398(4) Uani 1 1 d . . . C28 C 0.27783(9) 0.4984(2) 0.05555(5) 0.0430(5) Uani 1 1 d . . . C29 C 0.25577(11) 0.3268(3) 0.05070(5) 0.0545(5) Uani 1 1 d . . . H29 H 0.2162 0.3075 0.0518 0.065 Uiso 1 1 calc R . . C30 C 0.29133(13) 0.1772(3) 0.04409(5) 0.0617(6) Uani 1 1 d . . . H30 H 0.2752 0.0608 0.0415 0.074 Uiso 1 1 calc R . . C31 C 0.34899(12) 0.2018(3) 0.04143(5) 0.0563(6) Uani 1 1 d . . . H31 H 0.3721 0.1035 0.0365 0.068 Uiso 1 1 calc R . . C32 C 0.37321(10) 0.3775(3) 0.04627(5) 0.0482(5) Uani 1 1 d . . . C33 C 0.42734(10) 0.4544(3) 0.04626(5) 0.0543(6) Uani 1 1 d . . . H33 H 0.4615 0.3952 0.0421 0.065 Uiso 1 1 calc R . . C34 C 0.42094(9) 0.6391(3) 0.05371(5) 0.0479(5) Uani 1 1 d . . . C35 C 0.46606(10) 0.7813(3) 0.05732(5) 0.0549(6) Uani 1 1 d . . . C36 C 0.51380(12) 0.7705(5) 0.03825(7) 0.0825(8) Uani 1 1 d . . . H36 H 0.5170 0.6725 0.0230 0.099 Uiso 1 1 calc R . . C37 C 0.55612(14) 0.9035(6) 0.04175(9) 0.1034(11) Uani 1 1 d . . . H37 H 0.5874 0.8952 0.0286 0.124 Uiso 1 1 calc R . . C38 C 0.55295(14) 1.0469(5) 0.06409(10) 0.0980(11) Uani 1 1 d . . . H38 H 0.5818 1.1365 0.0661 0.118 Uiso 1 1 calc R . . C39 C 0.50673(13) 1.0592(4) 0.08378(8) 0.0837(8) Uani 1 1 d . . . H39 H 0.5047 1.1561 0.0994 0.100 Uiso 1 1 calc R . . C40 C 0.46333(10) 0.9269(3) 0.08027(6) 0.0604(6) Uani 1 1 d . . . H40 H 0.4322 0.9362 0.0934 0.072 Uiso 1 1 calc R . . N1 N 0.35009(7) 0.2710(2) 0.23302(4) 0.0402(4) Uani 1 1 d . . . N2 N 0.30925(7) 0.3114(2) 0.20525(4) 0.0414(4) Uani 1 1 d . . . N3 N 0.33707(7) 0.5205(2) 0.05373(4) 0.0413(4) Uani 1 1 d . . . N4 N 0.36578(7) 0.6821(2) 0.05815(4) 0.0452(4) Uani 1 1 d . . . O1 O 0.41671(7) 0.3075(2) 0.17094(3) 0.0610(4) Uani 1 1 d . . . O2 O 0.28306(7) 0.68215(18) 0.12003(3) 0.0534(4) Uani 1 1 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 0.122(3) 0.0892(18) 0.0493(13) -0.0105(12) 0.0030(14) 0.0120(17) C2 0.0438(13) 0.0600(12) 0.0444(10) 0.0090(9) 0.0043(9) 0.0056(10) C3 0.0666(17) 0.0839(17) 0.0524(12) 0.0209(12) 0.0109(11) 0.0001(14) C4 0.077(2) 0.0743(17) 0.0765(17) 0.0269(13) 0.0033(14) -0.0153(14) C5 0.077(2) 0.0611(14) 0.0824(18) 0.0078(12) -0.0002(14) -0.0163(13) C6 0.0593(16) 0.0616(13) 0.0558(12) 0.0014(10) 0.0063(11) -0.0113(11) C7 0.0351(12) 0.0559(12) 0.0438(10) 0.0078(9) 0.0040(8) -0.0016(9) C8 0.0394(12) 0.0508(10) 0.0382(9) 0.0010(8) 0.0090(8) 0.0003(9) C9 0.0439(13) 0.0680(13) 0.0403(10) 0.0022(9) 0.0055(9) 0.0013(10) C10 0.0586(16) 0.0708(14) 0.0436(11) 0.0106(10) 0.0012(10) 0.0050(12) C11 0.0673(17) 0.0615(13) 0.0491(12) 0.0191(10) 0.0045(11) -0.0023(12) C12 0.0541(14) 0.0470(11) 0.0452(10) 0.0087(8) 0.0099(10) -0.0003(10) C13 0.0548(15) 0.0513(12) 0.0544(12) 0.0103(9) 0.0060(11) -0.0101(10) C14 0.0427(12) 0.0421(10) 0.0441(10) -0.0034(8) 0.0087(9) -0.0007(9) C15 0.0419(12) 0.0421(10) 0.0435(10) -0.0053(8) 0.0083(9) 0.0003(9) C16 0.0510(15) 0.0600(13) 0.0530(12) 0.0050(9) 0.0089(10) -0.0055(11) C17 0.0428(14) 0.0722(14) 0.0690(14) 0.0010(12) 0.0068(11) -0.0095(11) C18 0.0470(15) 0.0736(15) 0.0554(12) -0.0029(11) -0.0011(10) 0.0037(12) C19 0.0565(16) 0.0626(13) 0.0524(12) 0.0042(10) 0.0032(11) 0.0018(12) C20 0.0497(14) 0.0529(12) 0.0514(11) 0.0007(9) 0.0056(10) -0.0051(10) C21 0.0805(19) 0.0719(14) 0.0494(12) -0.0138(10) -0.0071(12) 0.0142(13) C22 0.0430(12) 0.0400(10) 0.0428(10) 0.0007(8) 0.0083(9) -0.0007(9) C23 0.0574(15) 0.0464(11) 0.0455(11) -0.0064(8) 0.0082(10) 0.0042(10) C24 0.0519(14) 0.0477(11) 0.0588(12) 0.0029(9) 0.0102(10) 0.0079(10) C25 0.0470(13) 0.0562(12) 0.0495(11) 0.0075(9) 0.0043(10) -0.0009(10) C26 0.0453(13) 0.0487(11) 0.0433(10) -0.0017(8) 0.0085(9) -0.0058(10) C27 0.0398(12) 0.0381(9) 0.0433(10) -0.0015(7) 0.0123(8) -0.0061(8) C28 0.0482(13) 0.0432(10) 0.0387(10) -0.0030(8) 0.0096(9) -0.0018(9) C29 0.0614(15) 0.0459(11) 0.0578(12) -0.0062(9) 0.0135(11) -0.0061(11) C30 0.088(2) 0.0396(11) 0.0580(13) -0.0059(9) 0.0107(13) -0.0014(12) C31 0.0740(18) 0.0453(11) 0.0497(11) -0.0020(9) 0.0083(11) 0.0149(11) C32 0.0563(15) 0.0512(11) 0.0371(10) 0.0023(8) 0.0068(9) 0.0142(11) C33 0.0504(15) 0.0679(14) 0.0451(11) 0.0030(9) 0.0081(10) 0.0185(12) C34 0.0413(13) 0.0642(13) 0.0382(10) 0.0055(9) 0.0050(9) 0.0040(10) C35 0.0406(13) 0.0746(15) 0.0487(11) 0.0187(10) 0.0027(10) 0.0008(11) C36 0.0556(17) 0.128(2) 0.0657(15) 0.0084(15) 0.0155(13) -0.0133(17) C37 0.057(2) 0.166(4) 0.090(2) 0.035(2) 0.0187(17) -0.024(2) C38 0.060(2) 0.109(3) 0.119(3) 0.060(2) -0.0094(19) -0.0255(18) C39 0.066(2) 0.0637(15) 0.115(2) 0.0239(14) -0.0105(17) -0.0077(14) C40 0.0448(14) 0.0555(13) 0.0794(15) 0.0167(11) 0.0024(11) -0.0011(11) N1 0.0410(10) 0.0452(8) 0.0348(8) 0.0041(6) 0.0064(7) 0.0019(8) N2 0.0396(10) 0.0454(9) 0.0387(8) 0.0021(6) 0.0034(7) 0.0012(8) N3 0.0464(11) 0.0408(8) 0.0371(8) -0.0002(6) 0.0071(7) 0.0019(8) N4 0.0436(11) 0.0479(9) 0.0444(9) 0.0015(7) 0.0067(7) -0.0021(8) O1 0.0774(12) 0.0658(9) 0.0405(7) 0.0031(6) 0.0104(7) 0.0117(8) O2 0.0602(10) 0.0543(8) 0.0446(7) -0.0045(6) 0.0023(7) 0.0138(7) _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 O1 1.416(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 O1 1.370(2) . ? C2 C3 1.391(3) . ? C2 C7 1.395(3) . ? C3 C4 1.382(4) . ? C3 H3 0.9300 . ? C4 C5 1.373(4) . ? C4 H4 0.9300 . ? C5 C6 1.379(3) . ? C5 H5 0.9300 . ? C6 C7 1.391(3) . ? C6 H6 0.9300 . ? C7 C8 1.477(3) . ? C8 C9 1.356(3) . ? C8 N1 1.373(2) . ? C9 C10 1.402(3) . ? C9 H9 0.9300 . ? C10 C11 1.347(3) . ? C10 H10 0.9300 . ? C11 C12 1.408(3) . ? C11 H11 0.9300 . ? C12 C13 1.385(3) . ? C12 N1 1.394(2) . ? C13 C14 1.386(3) . ? C13 H13 0.9300 . ? C14 N2 1.342(2) . ? C14 C15 1.477(3) . ? C15 C16 1.380(3) . ? C15 C20 1.391(3) . ? C16 C17 1.380(3) . ? C16 H16 0.9300 . ? C17 C18 1.376(3) . ? C17 H17 0.9300 . ? C18 C19 1.366(3) . ? C18 H18 0.9300 . ? C19 C20 1.379(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 O2 1.423(2) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 O2 1.363(2) . ? C22 C23 1.381(3) . ? C22 C27 1.395(2) . ? C23 C24 1.379(3) . ? C23 H23 0.9300 . ? C24 C25 1.371(3) . ? C24 H24 0.9300 . ? C25 C26 1.371(3) . ? C25 H25 0.9300 . ? C26 C27 1.390(3) . ? C26 H26 0.9300 . ? C27 C28 1.482(3) . ? C28 C29 1.359(3) . ? C28 N3 1.388(3) . ? C29 C30 1.410(3) . ? C29 H29 0.9300 . ? C30 C31 1.360(3) . ? C30 H30 0.9300 . ? C31 C32 1.405(3) . ? C31 H31 0.9300 . ? C32 C33 1.371(3) . ? C32 N3 1.390(2) . ? C33 C34 1.393(3) . ? C33 H33 0.9300 . ? C34 N4 1.343(3) . ? C34 C35 1.467(3) . ? C35 C40 1.383(3) . ? C35 C36 1.397(3) . ? C36 C37 1.374(4) . ? C36 H36 0.9300 . ? C37 C38 1.358(5) . ? C37 H37 0.9300 . ? C38 C39 1.382(5) . ? C38 H38 0.9300 . ? C39 C40 1.388(3) . ? C39 H39 0.9300 . ? C40 H40 0.9300 . ? N1 N2 1.355(2) . ? N3 N4 1.356(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 O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 123.06(19) . . ? O1 C2 C7 116.43(17) . . ? C3 C2 C7 120.3(2) . . ? C4 C3 C2 119.5(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 120.7(2) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 119.9(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C7 120.8(2) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C6 C7 C2 118.73(18) . . ? C6 C7 C8 119.92(17) . . ? C2 C7 C8 121.28(18) . . ? C9 C8 N1 117.12(17) . . ? C9 C8 C7 123.98(19) . . ? N1 C8 C7 118.90(16) . . ? C8 C9 C10 121.9(2) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C11 C10 C9 120.52(19) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 119.59(19) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C13 C12 N1 104.96(16) . . ? C13 C12 C11 137.3(2) . . ? N1 C12 C11 117.73(19) . . ? C12 C13 C14 106.19(18) . . ? C12 C13 H13 126.9 . . ? C14 C13 H13 126.9 . . ? N2 C14 C13 112.23(18) . . ? N2 C14 C15 119.07(16) . . ? C13 C14 C15 128.60(18) . . ? C16 C15 C20 118.37(19) . . ? C16 C15 C14 121.26(17) . . ? C20 C15 C14 120.33(18) . . ? C17 C16 C15 120.9(2) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C18 C17 C16 120.0(2) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C19 C18 C17 119.8(2) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C20 120.5(2) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C19 C20 C15 120.4(2) . . ? C19 C20 H20 119.8 . . ? C15 C20 H20 119.8 . . ? O2 C21 H21A 109.5 . . ? O2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2 C22 C23 124.31(16) . . ? O2 C22 C27 116.12(16) . . ? C23 C22 C27 119.55(17) . . ? C24 C23 C22 119.98(18) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C25 C24 C23 121.14(19) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C24 C25 C26 119.04(19) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? C25 C26 C27 121.29(17) . . ? C25 C26 H26 119.4 . . ? C27 C26 H26 119.4 . . ? C26 C27 C22 118.99(17) . . ? C26 C27 C28 118.69(16) . . ? C22 C27 C28 122.15(17) . . ? C29 C28 N3 117.11(18) . . ? C29 C28 C27 122.9(2) . . ? N3 C28 C27 119.92(16) . . ? C28 C29 C30 121.7(2) . . ? C28 C29 H29 119.2 . . ? C30 C29 H29 119.2 . . ? C31 C30 C29 120.5(2) . . ? C31 C30 H30 119.7 . . ? C29 C30 H30 119.7 . . ? C30 C31 C32 119.2(2) . . ? C30 C31 H31 120.4 . . ? C32 C31 H31 120.4 . . ? C33 C32 N3 105.19(18) . . ? C33 C32 C31 136.3(2) . . ? N3 C32 C31 118.5(2) . . ? C32 C33 C34 106.14(19) . . ? C32 C33 H33 126.9 . . ? C34 C33 H33 126.9 . . ? N4 C34 C33 112.3(2) . . ? N4 C34 C35 119.69(19) . . ? C33 C34 C35 128.0(2) . . ? C40 C35 C36 118.2(2) . . ? C40 C35 C34 121.1(2) . . ? C36 C35 C34 120.6(2) . . ? C37 C36 C35 120.5(3) . . ? C37 C36 H36 119.7 . . ? C35 C36 H36 119.7 . . ? C38 C37 C36 120.9(3) . . ? C38 C37 H37 119.5 . . ? C36 C37 H37 119.5 . . ? C37 C38 C39 119.7(3) . . ? C37 C38 H38 120.2 . . ? C39 C38 H38 120.1 . . ? C38 C39 C40 120.0(3) . . ? C38 C39 H39 120.0 . . ? C40 C39 H39 120.0 . . ? C35 C40 C39 120.5(3) . . ? C35 C40 H40 119.7 . . ? C39 C40 H40 119.7 . . ? N2 N1 C8 124.58(15) . . ? N2 N1 C12 112.22(16) . . ? C8 N1 C12 123.16(16) . . ? C14 N2 N1 104.39(14) . . ? N4 N3 C28 124.39(15) . . ? N4 N3 C32 112.67(17) . . ? C28 N3 C32 122.93(17) . . ? C34 N4 N3 103.66(16) . . ? C2 O1 C1 116.75(17) . . ? C22 O2 C21 117.78(16) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.174 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.056 # Attachment '- 9a.cif' data_6549 _database_code_depnum_ccdc_archive 'CCDC 792990' #TrackingRef '- 9a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H42 Cu2 N4' _chemical_formula_sum 'C38 H42 Cu2 N4' _chemical_formula_weight 681.84 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 14.2593(3) _cell_length_b 12.1166(3) _cell_length_c 19.4748(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.7380(10) _cell_angle_gamma 90.00 _cell_volume 3294.38(14) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 16070 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.35 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 1.324 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4947 _exptl_absorpt_correction_T_max 0.635 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19908 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5936 _reflns_number_gt 4827 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 19' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0582P)^2^+3.9650P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5936 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1097 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _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 Cu1 Cu 0.33064(3) 0.55979(3) 0.18762(2) 0.02366(13) Uani 1 1 d . . . Cu2 Cu 0.14454(3) 0.62689(3) 0.04177(2) 0.02404(13) Uani 1 1 d . B . N1 N 0.32711(18) 0.5216(2) 0.09014(14) 0.0247(6) Uani 1 1 d . . . N2 N 0.26757(18) 0.5656(2) 0.03192(14) 0.0240(6) Uani 1 1 d . . . N3 N 0.15681(18) 0.6803(2) 0.13757(14) 0.0251(6) Uani 1 1 d . . . N4 N 0.23731(19) 0.6767(2) 0.18991(14) 0.0259(6) Uani 1 1 d . . . C1 C 0.8094(3) 0.3333(6) 0.4476(3) 0.0853(18) Uani 1 1 d . . . H1A H 0.8290 0.2740 0.4210 0.128 Uiso 1 1 calc R . . H1B H 0.8059 0.3073 0.4935 0.128 Uiso 1 1 calc R . . H1C H 0.8551 0.3923 0.4515 0.128 Uiso 1 1 calc R . . C2 C 0.7107(4) 0.3754(5) 0.4103(3) 0.0730(15) Uani 1 1 d . . . H2A H 0.7150 0.4001 0.3636 0.088 Uiso 1 1 calc R . . H2B H 0.6659 0.3143 0.4049 0.088 Uiso 1 1 calc R . . C3 C 0.6714(3) 0.4669(4) 0.4465(2) 0.0592(12) Uani 1 1 d . . . H3A H 0.7196 0.5242 0.4575 0.071 Uiso 1 1 calc R . . H3B H 0.6588 0.4394 0.4905 0.071 Uiso 1 1 calc R . . C4 C 0.5799(3) 0.5181(4) 0.4049(2) 0.0567(12) Uani 1 1 d . . . H4A H 0.5896 0.5347 0.3581 0.068 Uiso 1 1 calc R . . H4B H 0.5691 0.5875 0.4268 0.068 Uiso 1 1 calc R . . C5 C 0.4899(3) 0.4477(3) 0.3982(2) 0.0413(9) Uani 1 1 d . . . H5A H 0.4772 0.4342 0.4446 0.050 Uiso 1 1 calc R . . H5B H 0.5006 0.3769 0.3778 0.050 Uiso 1 1 calc R . . C6 C 0.4023(3) 0.5032(3) 0.35272(18) 0.0371(9) Uani 1 1 d . . . H6A H 0.3446 0.4657 0.3592 0.045 Uiso 1 1 calc R . . H6B H 0.3987 0.5793 0.3674 0.045 Uiso 1 1 calc R . . C7 C 0.4075(2) 0.5001(3) 0.27769(18) 0.0302(8) Uani 1 1 d . . . C8 C 0.4388(2) 0.4649(3) 0.22697(18) 0.0285(8) Uani 1 1 d . . . C9 C 0.4945(2) 0.4087(3) 0.18437(19) 0.0323(8) Uani 1 1 d . . . H9 H 0.5492 0.3715 0.2070 0.039 Uiso 1 1 calc R . . C10 C 0.4732(2) 0.4061(3) 0.11395(19) 0.0316(8) Uani 1 1 d . . . H10 H 0.5143 0.3652 0.0924 0.038 Uiso 1 1 calc R . . C11 C 0.3939(2) 0.4593(3) 0.06755(18) 0.0272(7) Uani 1 1 d . . . C12 C 0.3771(2) 0.4629(3) -0.00502(18) 0.0293(8) Uani 1 1 d . . . H12 H 0.4114 0.4266 -0.0341 0.035 Uiso 1 1 calc R . . C13 C 0.2993(2) 0.5314(3) -0.02532(17) 0.0256(7) Uani 1 1 d . . . C14 C 0.2615(2) 0.5748(3) -0.09624(18) 0.0265(7) Uani 1 1 d . . . C15 C 0.2416(2) 0.6867(3) -0.10625(19) 0.0310(8) Uani 1 1 d . . . H15 H 0.2484 0.7338 -0.0678 0.037 Uiso 1 1 calc R . . C16 C 0.2117(2) 0.7280(3) -0.17352(19) 0.0354(8) Uani 1 1 d . . . H16 H 0.1985 0.8029 -0.1800 0.043 Uiso 1 1 calc R . . C17 C 0.2013(3) 0.6594(3) -0.2308(2) 0.0404(9) Uani 1 1 d . . . H17 H 0.1810 0.6877 -0.2758 0.048 Uiso 1 1 calc R . . C18 C 0.2211(3) 0.5485(3) -0.22131(19) 0.0406(9) Uani 1 1 d . . . H18 H 0.2146 0.5020 -0.2600 0.049 Uiso 1 1 calc R . . C19 C 0.2506(3) 0.5061(3) -0.15443(19) 0.0345(8) Uani 1 1 d . . . H19 H 0.2633 0.4310 -0.1484 0.041 Uiso 1 1 calc R . . C20 C -0.0488(4) 0.5838(5) -0.3836(4) 0.110(3) Uani 1 1 d . . . H20A H -0.0455 0.5541 -0.4288 0.165 Uiso 1 1 calc R . . H20B H 0.0033 0.5555 -0.3490 0.165 Uiso 1 1 calc R . . H20C H -0.0447 0.6628 -0.3850 0.165 Uiso 1 1 calc R . . C21 C -0.1370(4) 0.5529(5) -0.3661(3) 0.0861(18) Uani 1 1 d . . . H21A H -0.1419 0.4731 -0.3659 0.103 Uiso 1 1 calc R A 2 H21B H -0.1896 0.5813 -0.4012 0.103 Uiso 1 1 calc R A 2 C22A C -0.0653(8) 0.6267(9) -0.2752(6) 0.051(3) Uiso 0.40 1 d P B 1 C22 C -0.1448(5) 0.6007(6) -0.2893(4) 0.0489(17) Uiso 0.60 1 d P B 2 C23 C -0.0819(5) 0.5514(4) -0.2308(2) 0.0779(18) Uani 1 1 d . . . C24 C -0.0775(3) 0.5979(3) -0.1556(2) 0.0446(10) Uani 1 1 d . B . H24A H -0.0871 0.6771 -0.1578 0.054 Uiso 1 1 calc R . . H24B H -0.1277 0.5650 -0.1355 0.054 Uiso 1 1 calc R . . C25 C 0.0200(2) 0.5712(3) -0.11016(18) 0.0339(8) Uani 1 1 d . . . H25A H 0.0269 0.4918 -0.1056 0.041 Uiso 1 1 calc R B . H25B H 0.0698 0.5982 -0.1331 0.041 Uiso 1 1 calc R . . C26 C 0.0330(2) 0.6207(3) -0.03961(18) 0.0284(8) Uani 1 1 d . B . C27 C 0.0111(2) 0.6708(3) 0.01017(18) 0.0293(8) Uani 1 1 d . . . C28 C -0.0392(2) 0.7332(3) 0.05344(18) 0.0328(8) Uani 1 1 d . B . H28 H -0.1021 0.7529 0.0342 0.039 Uiso 1 1 calc R . . C29 C -0.0036(2) 0.7656(3) 0.11897(18) 0.0310(8) Uani 1 1 d . . . H29 H -0.0444 0.8066 0.1407 0.037 Uiso 1 1 calc R B . C30 C 0.0913(2) 0.7444(3) 0.16038(17) 0.0262(7) Uani 1 1 d . B . C31 C 0.1301(2) 0.7827(3) 0.22739(17) 0.0283(7) Uani 1 1 d . . . H31 H 0.1004 0.8276 0.2553 0.034 Uiso 1 1 calc R B . C32 C 0.2214(2) 0.7404(3) 0.24381(17) 0.0263(7) Uani 1 1 d . B . C33 C 0.2984(2) 0.7628(3) 0.30526(18) 0.0281(7) Uani 1 1 d . . . C34 C 0.3921(2) 0.7796(3) 0.2970(2) 0.0341(8) Uani 1 1 d . B . H34 H 0.4066 0.7751 0.2526 0.041 Uiso 1 1 calc R . . C35 C 0.4636(3) 0.8027(3) 0.3544(2) 0.0460(10) Uani 1 1 d . . . H35 H 0.5259 0.8141 0.3484 0.055 Uiso 1 1 calc R B . C36 C 0.4435(3) 0.8093(4) 0.4207(2) 0.0488(11) Uani 1 1 d . B . H36 H 0.4922 0.8238 0.4593 0.059 Uiso 1 1 calc R . . C37 C 0.3502(3) 0.7940(4) 0.4296(2) 0.0459(10) Uani 1 1 d . . . H37 H 0.3360 0.7993 0.4740 0.055 Uiso 1 1 calc R B . C38 C 0.2782(3) 0.7709(3) 0.37196(19) 0.0368(9) Uani 1 1 d . B . H38 H 0.2158 0.7607 0.3780 0.044 Uiso 1 1 calc 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 0.0218(2) 0.0253(2) 0.0240(2) -0.00144(16) 0.00491(16) 0.00240(16) Cu2 0.0211(2) 0.0288(2) 0.0227(2) -0.00030(17) 0.00559(16) 0.00346(17) N1 0.0228(13) 0.0256(14) 0.0259(15) 0.0008(12) 0.0050(12) 0.0027(12) N2 0.0228(13) 0.0287(15) 0.0212(14) 0.0020(11) 0.0061(11) 0.0027(12) N3 0.0230(13) 0.0262(14) 0.0261(15) 0.0005(12) 0.0050(11) 0.0042(12) N4 0.0269(14) 0.0270(14) 0.0237(14) -0.0037(12) 0.0046(12) 0.0017(12) C1 0.047(3) 0.126(5) 0.083(4) 0.015(4) 0.015(3) 0.013(3) C2 0.067(3) 0.103(4) 0.048(3) 0.006(3) 0.010(3) 0.017(3) C3 0.053(3) 0.072(3) 0.048(3) 0.009(2) 0.001(2) -0.006(2) C4 0.051(3) 0.063(3) 0.050(3) 0.016(2) -0.004(2) -0.003(2) C5 0.047(2) 0.047(2) 0.028(2) 0.0094(17) 0.0054(17) 0.0047(19) C6 0.039(2) 0.043(2) 0.030(2) 0.0009(17) 0.0091(16) 0.0022(18) C7 0.0269(17) 0.0315(19) 0.030(2) 0.0033(15) 0.0008(15) 0.0009(15) C8 0.0269(17) 0.0293(18) 0.0270(19) 0.0044(15) 0.0003(15) 0.0023(15) C9 0.0284(17) 0.0306(18) 0.037(2) 0.0040(16) 0.0042(15) 0.0106(15) C10 0.0304(18) 0.0293(18) 0.037(2) -0.0012(15) 0.0112(16) 0.0101(15) C11 0.0261(16) 0.0271(17) 0.0305(19) -0.0014(14) 0.0106(14) 0.0044(14) C12 0.0313(18) 0.0287(18) 0.0306(19) -0.0045(15) 0.0122(15) 0.0059(15) C13 0.0257(16) 0.0277(18) 0.0249(18) -0.0006(14) 0.0082(14) 0.0006(14) C14 0.0216(16) 0.0329(19) 0.0263(18) 0.0005(14) 0.0077(14) 0.0037(14) C15 0.0269(17) 0.0337(19) 0.0325(19) -0.0011(16) 0.0065(15) 0.0028(15) C16 0.0341(19) 0.035(2) 0.037(2) 0.0089(17) 0.0065(16) 0.0028(16) C17 0.037(2) 0.056(3) 0.028(2) 0.0114(18) 0.0049(16) -0.0009(19) C18 0.046(2) 0.051(2) 0.025(2) -0.0043(17) 0.0087(17) 0.0014(19) C19 0.041(2) 0.0305(19) 0.033(2) -0.0037(16) 0.0100(16) 0.0037(17) C20 0.066(4) 0.061(4) 0.195(8) 0.026(4) 0.005(4) 0.013(3) C21 0.078(4) 0.070(4) 0.108(5) 0.021(3) 0.013(4) 0.001(3) C23 0.138(5) 0.044(3) 0.034(3) 0.001(2) -0.027(3) -0.010(3) C24 0.049(2) 0.038(2) 0.037(2) 0.0046(17) -0.0140(18) -0.0081(19) C25 0.0302(18) 0.046(2) 0.0256(19) -0.0012(16) 0.0053(15) -0.0052(16) C26 0.0241(16) 0.0325(19) 0.0276(19) 0.0053(15) 0.0032(14) -0.0005(15) C27 0.0218(16) 0.038(2) 0.0270(18) 0.0048(16) 0.0016(14) 0.0011(15) C28 0.0250(17) 0.043(2) 0.031(2) 0.0064(16) 0.0070(15) 0.0089(16) C29 0.0280(17) 0.037(2) 0.0313(19) 0.0023(16) 0.0149(15) 0.0087(16) C30 0.0271(16) 0.0268(17) 0.0270(17) 0.0032(14) 0.0107(14) 0.0048(14) C31 0.0300(17) 0.0301(18) 0.0278(18) -0.0008(14) 0.0128(15) 0.0064(15) C32 0.0319(17) 0.0260(17) 0.0234(17) -0.0011(14) 0.0112(14) 0.0006(15) C33 0.0312(17) 0.0244(17) 0.0287(18) -0.0037(14) 0.0062(15) 0.0023(14) C34 0.0352(19) 0.034(2) 0.035(2) -0.0087(16) 0.0104(16) -0.0018(16) C35 0.034(2) 0.045(2) 0.058(3) -0.010(2) 0.0069(19) -0.0059(19) C36 0.043(2) 0.050(3) 0.047(3) -0.015(2) -0.0084(19) -0.003(2) C37 0.053(2) 0.053(3) 0.028(2) -0.0131(19) 0.0028(18) 0.001(2) C38 0.0353(19) 0.040(2) 0.036(2) -0.0059(17) 0.0088(16) 0.0022(17) _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 Cu1 N1 1.944(3) . ? Cu1 N4 1.950(3) . ? Cu1 C8 1.951(3) . ? Cu1 C7 2.005(3) . ? Cu2 N3 1.949(3) . ? Cu2 N2 1.950(3) . ? Cu2 C27 1.950(3) . ? Cu2 C26 2.005(3) . ? N1 C11 1.358(4) . ? N1 N2 1.378(4) . ? N2 C13 1.351(4) . ? N3 C30 1.356(4) . ? N3 N4 1.372(4) . ? N4 C32 1.358(4) . ? C1 C2 1.534(7) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.484(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.521(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.526(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.532(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.479(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.239(5) . ? C8 C9 1.433(5) . ? C9 C10 1.343(5) . ? C9 H9 0.9300 . ? C10 C11 1.447(5) . ? C10 H10 0.9300 . ? C11 C12 1.385(5) . ? C12 C13 1.378(5) . ? C12 H12 0.9300 . ? C13 C14 1.474(5) . ? C14 C19 1.390(5) . ? C14 C15 1.390(5) . ? C15 C16 1.386(5) . ? C15 H15 0.9300 . ? C16 C17 1.375(5) . ? C16 H16 0.9300 . ? C17 C18 1.378(6) . ? C17 H17 0.9300 . ? C18 C19 1.384(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.418(8) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.629(10) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22A C23 1.313(12) . ? C22 C23 1.430(9) . ? C23 C24 1.557(6) . ? C24 C25 1.523(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.476(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.237(5) . ? C27 C28 1.429(5) . ? C28 C29 1.333(5) . ? C28 H28 0.9300 . ? C29 C30 1.451(4) . ? C29 H29 0.9300 . ? C30 C31 1.389(5) . ? C31 C32 1.375(5) . ? C31 H31 0.9300 . ? C32 C33 1.475(5) . ? C33 C38 1.390(5) . ? C33 C34 1.394(5) . ? C34 C35 1.381(5) . ? C34 H34 0.9300 . ? C35 C36 1.381(6) . ? C35 H35 0.9300 . ? C36 C37 1.388(6) . ? C36 H36 0.9300 . ? C37 C38 1.387(5) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? 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 N1 Cu1 N4 108.23(11) . . ? N1 Cu1 C8 96.02(13) . . ? N4 Cu1 C8 155.16(13) . . ? N1 Cu1 C7 132.01(13) . . ? N4 Cu1 C7 119.75(13) . . ? C8 Cu1 C7 36.46(14) . . ? N3 Cu2 N2 108.26(11) . . ? N3 Cu2 C27 95.93(13) . . ? N2 Cu2 C27 155.79(13) . . ? N3 Cu2 C26 132.18(12) . . ? N2 Cu2 C26 119.51(13) . . ? C27 Cu2 C26 36.41(14) . . ? C11 N1 N2 107.7(3) . . ? C11 N1 Cu1 124.6(2) . . ? N2 N1 Cu1 126.9(2) . . ? C13 N2 N1 107.9(2) . . ? C13 N2 Cu2 131.1(2) . . ? N1 N2 Cu2 118.8(2) . . ? C30 N3 N4 107.6(3) . . ? C30 N3 Cu2 124.7(2) . . ? N4 N3 Cu2 126.8(2) . . ? C32 N4 N3 108.1(3) . . ? C32 N4 Cu1 130.7(2) . . ? N3 N4 Cu1 118.5(2) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 115.0(5) . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2B 108.5 . . ? C1 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 114.6(4) . . ? C2 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? C2 C3 H3B 108.6 . . ? C4 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? C3 C4 C5 115.6(4) . . ? C3 C4 H4A 108.4 . . ? C5 C4 H4A 108.4 . . ? C3 C4 H4B 108.4 . . ? C5 C4 H4B 108.4 . . ? H4A C4 H4B 107.4 . . ? C4 C5 C6 112.1(3) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 111.2(3) . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C6 153.5(3) . . ? C8 C7 Cu1 69.4(2) . . ? C6 C7 Cu1 136.6(3) . . ? C7 C8 C9 163.2(3) . . ? C7 C8 Cu1 74.1(2) . . ? C9 C8 Cu1 122.7(2) . . ? C10 C9 C8 124.4(3) . . ? C10 C9 H9 117.8 . . ? C8 C9 H9 117.8 . . ? C9 C10 C11 127.8(3) . . ? C9 C10 H10 116.1 . . ? C11 C10 H10 116.1 . . ? N1 C11 C12 109.0(3) . . ? N1 C11 C10 123.8(3) . . ? C12 C11 C10 127.0(3) . . ? C13 C12 C11 105.9(3) . . ? C13 C12 H12 127.1 . . ? C11 C12 H12 127.1 . . ? N2 C13 C12 109.5(3) . . ? N2 C13 C14 122.9(3) . . ? C12 C13 C14 127.1(3) . . ? C19 C14 C15 119.0(3) . . ? C19 C14 C13 120.6(3) . . ? C15 C14 C13 120.3(3) . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C17 C16 C15 120.6(4) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 119.7(3) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C19 120.2(4) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C14 120.5(3) . . ? C18 C19 H19 119.8 . . ? C14 C19 H19 119.8 . . ? C21 C20 H20A 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C21 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C20 C21 C22 110.9(6) . . ? C20 C21 H21A 109.4 . . ? C22 C21 H21A 109.4 . . ? C20 C21 H21B 109.4 . . ? C22 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? C23 C22 C21 115.7(6) . . ? C22A C23 C22 49.6(6) . . ? C22A C23 C24 113.0(6) . . ? C22 C23 C24 119.8(5) . . ? C25 C24 C23 109.1(4) . . ? C25 C24 H24A 109.9 . . ? C23 C24 H24A 109.9 . . ? C25 C24 H24B 109.9 . . ? C23 C24 H24B 109.9 . . ? H24A C24 H24B 108.3 . . ? C26 C25 C24 112.5(3) . . ? C26 C25 H25A 109.1 . . ? C24 C25 H25A 109.1 . . ? C26 C25 H25B 109.1 . . ? C24 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? C27 C26 C25 157.7(3) . . ? C27 C26 Cu2 69.4(2) . . ? C25 C26 Cu2 132.9(2) . . ? C26 C27 C28 163.6(3) . . ? C26 C27 Cu2 74.2(2) . . ? C28 C27 Cu2 122.2(2) . . ? C29 C28 C27 125.5(3) . . ? C29 C28 H28 117.2 . . ? C27 C28 H28 117.2 . . ? C28 C29 C30 127.6(3) . . ? C28 C29 H29 116.2 . . ? C30 C29 H29 116.2 . . ? N3 C30 C31 109.3(3) . . ? N3 C30 C29 123.1(3) . . ? C31 C30 C29 127.6(3) . . ? C32 C31 C30 105.7(3) . . ? C32 C31 H31 127.1 . . ? C30 C31 H31 127.1 . . ? N4 C32 C31 109.3(3) . . ? N4 C32 C33 121.2(3) . . ? C31 C32 C33 129.3(3) . . ? C38 C33 C34 118.9(3) . . ? C38 C33 C32 120.7(3) . . ? C34 C33 C32 120.3(3) . . ? C35 C34 C33 120.2(4) . . ? C35 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? C34 C35 C36 120.7(4) . . ? C34 C35 H35 119.6 . . ? C36 C35 H35 119.6 . . ? C35 C36 C37 119.7(4) . . ? C35 C36 H36 120.2 . . ? C37 C36 H36 120.2 . . ? C38 C37 C36 119.8(4) . . ? C38 C37 H37 120.1 . . ? C36 C37 H37 120.1 . . ? C37 C38 C33 120.7(4) . . ? C37 C38 H38 119.6 . . ? C33 C38 H38 119.6 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.733 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.092 # Attachment '- 9e.cif' data_10166 _database_code_depnum_ccdc_archive 'CCDC 792991' #TrackingRef '- 9e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H19 Cl Cu N2 O' _chemical_formula_sum 'C17 H19 Cl Cu N2 O' _chemical_formula_weight 366.33 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' Cu Cu 0.3201 1.2651 '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' Cl Cl 0.1484 0.1585 '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' _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 9.3101(2) _cell_length_b 9.2508(3) _cell_length_c 11.2420(4) _cell_angle_alpha 69.3330(10) _cell_angle_beta 84.4530(10) _cell_angle_gamma 76.7640(10) _cell_volume 881.72(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7097 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 1.392 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5248 _exptl_absorpt_correction_T_max 0.7228 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6959 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3083 _reflns_number_gt 2812 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0796P)^2^+4.7886P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3083 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0866 _refine_ls_R_factor_gt 0.0799 _refine_ls_wR_factor_ref 0.2017 _refine_ls_wR_factor_gt 0.1958 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 Cu1 Cu 0.2257 0.7971 0.1410 0.0473(3) Uani 1 1 d . . . Cl1 Cl 0.44635(19) 0.7297(3) 0.0597(2) 0.0777(6) Uani 1 1 d . . . O1 O 0.6475(6) 0.3645(9) 0.1610(6) 0.0904(19) Uani 1 1 d . . . H1A H 0.5981 0.3281 0.1143 0.109 Uiso 1 1 d R . . H1B H 0.5964 0.4725 0.1192 0.109 Uiso 1 1 d R . . N1 N 0.0665(5) 0.7709(6) 0.0542(5) 0.0448(11) Uani 1 1 d . . . N2 N 0.0734(5) 0.7175(6) -0.0444(5) 0.0438(11) Uani 1 1 d . . . C1 C 0.2278(7) 0.8607(7) 0.2944(6) 0.0497(15) Uani 1 1 d . . . C2 C 0.3550(8) 0.8666(8) 0.3627(7) 0.0562(16) Uani 1 1 d . . . C3 C 0.4447(13) 0.6997(11) 0.4213(12) 0.117(4) Uani 1 1 d . . . H3A H 0.5276 0.7025 0.4644 0.175 Uiso 1 1 calc R . . H3B H 0.4792 0.6557 0.3556 0.175 Uiso 1 1 calc R . . H3C H 0.3840 0.6356 0.4810 0.175 Uiso 1 1 calc R . . C4 C 0.4493(9) 0.9721(11) 0.2712(9) 0.076(2) Uani 1 1 d . . . H4A H 0.5305 0.9757 0.3158 0.114 Uiso 1 1 calc R . . H4B H 0.3909 1.0767 0.2353 0.114 Uiso 1 1 calc R . . H4C H 0.4863 0.9307 0.2044 0.114 Uiso 1 1 calc R . . C5 C 0.2898(11) 0.9371(13) 0.4671(8) 0.086(3) Uani 1 1 d . . . H5A H 0.3687 0.9445 0.5123 0.129 Uiso 1 1 calc R . . H5B H 0.2302 0.8700 0.5252 0.129 Uiso 1 1 calc R . . H5C H 0.2301 1.0405 0.4286 0.129 Uiso 1 1 calc R . . C6 C 0.1010(7) 0.8673(8) 0.2697(6) 0.0496(15) Uani 1 1 d . . . C7 C -0.0563(8) 0.8915(10) 0.2676(7) 0.0649(19) Uani 1 1 d . . . H7 H -0.1101 0.9332 0.3264 0.078 Uiso 1 1 calc R . . C8 C -0.1323(7) 0.8598(10) 0.1894(7) 0.066(2) Uani 1 1 d . . . H8 H -0.2342 0.8795 0.2012 0.079 Uiso 1 1 calc R . . C9 C -0.0770(6) 0.7985(8) 0.0878(6) 0.0478(14) Uani 1 1 d . . . C10 C -0.1605(7) 0.7630(9) 0.0084(6) 0.0535(16) Uani 1 1 d . . . H10 H -0.2623 0.7722 0.0115 0.064 Uiso 1 1 calc R . . C11 C -0.0620(6) 0.7121(7) -0.0751(5) 0.0434(13) Uani 1 1 d . . . C12 C -0.0871(7) 0.6667(7) -0.1828(6) 0.0464(14) Uani 1 1 d . . . C13 C -0.2193(8) 0.6252(8) -0.1901(6) 0.0548(16) Uani 1 1 d . . . H13 H -0.2889 0.6209 -0.1244 0.066 Uiso 1 1 calc R . . C14 C -0.2483(9) 0.5903(9) -0.2936(7) 0.0656(19) Uani 1 1 d . . . H14 H -0.3369 0.5618 -0.2971 0.079 Uiso 1 1 calc R . . C15 C -0.1476(10) 0.5975(10) -0.3912(8) 0.073(2) Uani 1 1 d . . . H15 H -0.1689 0.5771 -0.4621 0.088 Uiso 1 1 calc R . . C16 C -0.0143(10) 0.6351(11) -0.3845(8) 0.077(2) Uani 1 1 d . . . H16 H 0.0551 0.6377 -0.4502 0.093 Uiso 1 1 calc R . . C17 C 0.0168(8) 0.6689(9) -0.2800(7) 0.0624(18) Uani 1 1 d . . . H17 H 0.1072 0.6931 -0.2754 0.075 Uiso 1 1 calc 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 0.0355(4) 0.0609(5) 0.0509(5) -0.0257(4) 0.0007(3) -0.0103(3) Cl1 0.0402(9) 0.1116(17) 0.1033(16) -0.0646(14) 0.0169(9) -0.0215(10) O1 0.055(3) 0.131(6) 0.094(4) -0.057(4) 0.003(3) -0.009(3) N1 0.034(2) 0.058(3) 0.045(3) -0.022(2) 0.002(2) -0.007(2) N2 0.039(3) 0.054(3) 0.040(3) -0.019(2) 0.000(2) -0.009(2) C1 0.055(4) 0.049(3) 0.048(3) -0.018(3) -0.005(3) -0.012(3) C2 0.060(4) 0.055(4) 0.057(4) -0.021(3) -0.016(3) -0.010(3) C3 0.123(9) 0.071(6) 0.151(10) -0.029(6) -0.090(8) 0.011(6) C4 0.056(4) 0.092(6) 0.099(6) -0.052(5) 0.005(4) -0.024(4) C5 0.095(6) 0.117(8) 0.071(5) -0.054(5) -0.001(5) -0.038(6) C6 0.054(4) 0.051(4) 0.046(3) -0.021(3) 0.002(3) -0.009(3) C7 0.047(4) 0.096(6) 0.062(4) -0.047(4) 0.007(3) -0.004(4) C8 0.038(3) 0.106(6) 0.063(4) -0.047(4) 0.008(3) -0.010(4) C9 0.036(3) 0.065(4) 0.043(3) -0.021(3) 0.003(2) -0.008(3) C10 0.033(3) 0.082(5) 0.048(3) -0.025(3) 0.000(3) -0.013(3) C11 0.039(3) 0.050(3) 0.039(3) -0.012(3) -0.002(2) -0.011(3) C12 0.050(3) 0.044(3) 0.043(3) -0.013(3) -0.006(3) -0.006(3) C13 0.056(4) 0.058(4) 0.049(4) -0.013(3) -0.004(3) -0.019(3) C14 0.073(5) 0.062(4) 0.069(5) -0.023(4) -0.013(4) -0.022(4) C15 0.091(6) 0.073(5) 0.069(5) -0.038(4) -0.018(4) -0.013(4) C16 0.084(6) 0.095(6) 0.063(5) -0.043(5) 0.009(4) -0.017(5) C17 0.058(4) 0.083(5) 0.053(4) -0.029(4) 0.003(3) -0.019(4) _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 Cu1 N1 1.954(5) . ? Cu1 C6 1.964(6) . ? Cu1 C1 2.012(6) . ? Cu1 Cl1 2.2130(17) . ? O1 H1A 0.9194 . ? O1 H1B 0.9694 . ? N1 C9 1.344(8) . ? N1 N2 1.355(7) . ? N2 C11 1.355(7) . ? C1 C6 1.222(9) . ? C1 C2 1.493(9) . ? C2 C4 1.513(11) . ? C2 C3 1.521(11) . ? C2 C5 1.547(11) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.431(9) . ? C7 C8 1.325(10) . ? C7 H7 0.9300 . ? C8 C9 1.450(9) . ? C8 H8 0.9300 . ? C9 C10 1.403(9) . ? C10 C11 1.375(9) . ? C10 H10 0.9300 . ? C11 C12 1.468(8) . ? C12 C17 1.386(9) . ? C12 C13 1.388(9) . ? C13 C14 1.378(10) . ? C13 H13 0.9300 . ? C14 C15 1.366(12) . ? C14 H14 0.9300 . ? C15 C16 1.378(12) . ? C15 H15 0.9300 . ? C16 C17 1.389(10) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? 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 N1 Cu1 C6 96.7(2) . . ? N1 Cu1 C1 132.5(2) . . ? C6 Cu1 C1 35.8(3) . . ? N1 Cu1 Cl1 112.77(15) . . ? C6 Cu1 Cl1 150.4(2) . . ? C1 Cu1 Cl1 114.7(2) . . ? H1A O1 H1B 91.4 . . ? C9 N1 N2 105.8(5) . . ? C9 N1 Cu1 124.5(4) . . ? N2 N1 Cu1 129.6(4) . . ? C11 N2 N1 111.8(5) . . ? C6 C1 C2 160.0(7) . . ? C6 C1 Cu1 70.0(4) . . ? C2 C1 Cu1 130.0(5) . . ? C1 C2 C4 110.0(6) . . ? C1 C2 C3 108.9(6) . . ? C4 C2 C3 110.7(8) . . ? C1 C2 C5 107.0(6) . . ? C4 C2 C5 109.5(6) . . ? C3 C2 C5 110.7(8) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C1 C6 C7 164.9(7) . . ? C1 C6 Cu1 74.2(4) . . ? C7 C6 Cu1 120.8(5) . . ? C8 C7 C6 125.9(6) . . ? C8 C7 H7 117.0 . . ? C6 C7 H7 117.0 . . ? C7 C8 C9 128.4(6) . . ? C7 C8 H8 115.8 . . ? C9 C8 H8 115.8 . . ? N1 C9 C10 109.7(5) . . ? N1 C9 C8 123.4(6) . . ? C10 C9 C8 126.9(6) . . ? C11 C10 C9 106.3(5) . . ? C11 C10 H10 126.8 . . ? C9 C10 H10 126.8 . . ? N2 C11 C10 106.4(5) . . ? N2 C11 C12 123.0(5) . . ? C10 C11 C12 130.5(6) . . ? C17 C12 C13 118.9(6) . . ? C17 C12 C11 121.4(6) . . ? C13 C12 C11 119.7(6) . . ? C14 C13 C12 120.6(7) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 120.3(7) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.0(7) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 120.2(8) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C12 C17 C16 119.9(7) . . ? C12 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 2.787 _refine_diff_density_min -3.062 _refine_diff_density_rms 0.124