# Electronic Supplementary Material for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name J.Zaleski _publ_contact_author_address ; Department of Chemistry Indiana University 800 E. Kirkwood Avenue Bloomington IN 47405-4001 UNITED STATES OF AMERICA ; _publ_contact_author_email ZALESKI@INDIANA.EDU _publ_section_title ;Elucidation of the extraordinary 4-membered pyrrole ring-contracted azeteoporphyrinoid as an intermediate in chlorin oxidation ; loop_ _publ_author_name J.Zaleski 'Tillmann Kopke' 'Maren Pink' # Attachment '4Cu' data_05230 _database_code_depnum_ccdc_archive 'CCDC 615719' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H26 Cu N4 O2, C H2 Cl2' _chemical_formula_sum 'C44 H28 Cl2 Cu N4 O2' _chemical_formula_weight 779.14 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' Cl Cl 0.1484 0.1585 '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 monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8343(10) _cell_length_b 15.1780(17) _cell_length_c 25.437(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.284(3) _cell_angle_gamma 90.00 _cell_volume 3410.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 4144 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1596 _exptl_absorpt_coefficient_mu 0.845 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8492 _exptl_absorpt_correction_T_max 0.9203 _exptl_absorpt_process_details 'SADABS, R. Blessing; 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_details '0.30 degree frames measured for 30 seconds each' _diffrn_measurement_method \w-scans _diffrn_measurement_device 'three-circle goniometer with fixed chi' _diffrn_measurement_device_type 'Bruker Platform goniometer' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker SMART 6000' _diffrn_detector_area_resol_mean 44.52 _diffrn_standards_number 123 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1070 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 29978 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 26.46 _reflns_number_total 7001 _reflns_number_gt 5095 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SIR-92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2003), XTEL (loc. libr.)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0332P)^2^+5.9866P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7001 _refine_ls_number_parameters 551 _refine_ls_number_restraints 142 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.048 _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 0.24701(4) 0.07868(3) 0.507549(16) 0.02958(12) Uani 1 1 d . A . N1 N 0.1802(3) 0.19483(17) 0.47884(10) 0.0283(6) Uani 1 1 d D A . C2 C 0.1137(16) 0.3049(7) 0.4188(5) 0.025(3) Uani 0.528(12) 1 d PD A 1 H2 H 0.0840 0.3327 0.3869 0.030 Uiso 0.528(12) 1 calc PR A 1 C3 C 0.1656(17) 0.3437(7) 0.4637(4) 0.027(3) Uani 0.528(12) 1 d PD A 1 H3 H 0.1710 0.4053 0.4700 0.032 Uiso 0.528(12) 1 calc PR A 1 C1 C 0.1144(4) 0.2095(2) 0.43084(13) 0.0318(7) Uani 1 1 d D . . O2A O 0.091(3) 0.2875(10) 0.4215(8) 0.025(3) Uani 0.317(8) 1 d PD A 2 C3A C 0.177(4) 0.3474(17) 0.4539(10) 0.027(3) Uani 0.317(8) 1 d PD A 2 O3A O 0.1615(9) 0.4156(4) 0.4592(3) 0.039(3) Uani 0.317(8) 1 d PD A 2 C4 C 0.2105(4) 0.2763(2) 0.49981(13) 0.0309(7) Uani 1 1 d D . . C2B C 0.134(5) 0.3139(18) 0.4195(14) 0.025(3) Uani 0.155(9) 1 d PD A 3 O2B O 0.092(2) 0.3555(10) 0.3898(6) 0.068(8) Uani 0.155(9) 1 d PD A 3 O3B O 0.165(5) 0.3381(14) 0.4734(9) 0.027(3) Uani 0.155(9) 1 d PD A 3 C5 C 0.2672(4) 0.2943(2) 0.54942(13) 0.0308(7) Uani 1 1 d . A . N2 N 0.3275(3) 0.14032(17) 0.57110(11) 0.0301(6) Uani 1 1 d D A . C7 C 0.363(2) 0.2458(7) 0.6366(4) 0.032(3) Uani 0.472(12) 1 d PD A 1 H7 H 0.3740 0.3014 0.6534 0.038 Uiso 0.472(12) 1 calc PR A 1 C8 C 0.389(4) 0.1632(9) 0.6576(6) 0.035(3) Uani 0.472(12) 1 d PD A 1 H8 H 0.4031 0.1498 0.6937 0.043 Uiso 0.472(12) 1 calc PR A 1 C6 C 0.3134(4) 0.2280(2) 0.58292(12) 0.0322(7) Uani 1 1 d D . . C7A C 0.344(3) 0.2359(18) 0.6454(9) 0.032(3) Uani 0.299(8) 1 d PD A 2 O7A O 0.3674(12) 0.2939(5) 0.6658(3) 0.053(3) Uani 0.299(8) 1 d PD A 2 O8A O 0.420(3) 0.1521(13) 0.6504(7) 0.035(3) Uani 0.299(8) 1 d PD A 2 C9 C 0.3897(4) 0.1013(2) 0.61474(14) 0.0359(8) Uani 1 1 d D . . C10 C 0.4387(4) 0.0146(2) 0.61903(13) 0.0314(7) Uani 1 1 d . A . O7B O 0.363(4) 0.2497(14) 0.6264(8) 0.032(3) Uani 0.229(8) 1 d PD A 3 C8B C 0.412(5) 0.177(2) 0.6591(12) 0.035(3) Uani 0.229(8) 1 d PD A 3 O8B O 0.4553(13) 0.1817(6) 0.6979(3) 0.041(4) Uani 0.229(8) 1 d PD A 3 N3 N 0.3257(3) -0.03494(17) 0.53520(10) 0.0294(6) Uani 1 1 d D A . C11 C 0.4148(4) -0.0471(2) 0.57877(13) 0.0320(7) Uani 1 1 d D . . C12 C 0.4762(4) -0.1353(2) 0.57905(13) 0.0342(8) Uani 1 1 d D A . H12 H 0.5434 -0.1596 0.6044 0.041 Uiso 1 1 calc R . . C13 C 0.4191(4) -0.1765(2) 0.53606(13) 0.0339(8) Uani 1 1 d D . . H13 H 0.4399 -0.2352 0.5254 0.041 Uiso 1 1 calc R A . C14 C 0.3215(4) -0.1150(2) 0.50950(13) 0.0306(7) Uani 1 1 d D A . C15 C 0.2301(4) -0.1350(2) 0.46625(13) 0.0297(7) Uani 1 1 d . . . N4 N 0.1544(3) 0.01810(17) 0.44644(10) 0.0287(6) Uani 1 1 d D . . C16 C 0.1448(4) -0.0720(2) 0.43894(12) 0.0295(7) Uani 1 1 d D A . C17 C 0.0426(4) -0.0907(2) 0.39648(13) 0.0330(7) Uani 1 1 d D . . H17 H 0.0131 -0.1475 0.3846 0.040 Uiso 1 1 calc R A . C18 C -0.0046(4) -0.0120(2) 0.37621(13) 0.0325(7) Uani 1 1 d D A . H18 H -0.0719 -0.0034 0.3474 0.039 Uiso 1 1 calc R . . C19 C 0.0681(4) 0.0553(2) 0.40719(13) 0.0297(7) Uani 1 1 d D A . C20 C 0.0552(4) 0.1464(2) 0.39706(13) 0.0296(7) Uani 1 1 d . A . C21 C 0.2851(4) 0.3883(2) 0.56683(13) 0.0319(7) Uani 1 1 d . . . C22 C 0.4162(5) 0.4333(3) 0.55554(18) 0.0514(11) Uani 1 1 d . A . H22 H 0.4940 0.4048 0.5363 0.062 Uiso 1 1 calc R . . C23 C 0.4362(5) 0.5196(3) 0.57175(19) 0.0578(12) Uani 1 1 d . . . H23 H 0.5281 0.5494 0.5641 0.069 Uiso 1 1 calc R A . C24 C 0.3242(5) 0.5624(2) 0.59880(16) 0.0476(10) Uani 1 1 d . A . H24 H 0.3373 0.6220 0.6093 0.057 Uiso 1 1 calc R . . C25 C 0.1934(5) 0.5184(3) 0.61050(16) 0.0483(10) Uani 1 1 d . . . H25 H 0.1156 0.5476 0.6293 0.058 Uiso 1 1 calc R A . C26 C 0.1737(4) 0.4313(2) 0.59497(15) 0.0421(9) Uani 1 1 d . A . H26 H 0.0832 0.4011 0.6038 0.051 Uiso 1 1 calc R . . C27 C 0.5108(4) -0.0133(2) 0.66923(13) 0.0310(7) Uani 1 1 d . . . C28 C 0.6401(4) 0.0289(2) 0.68868(14) 0.0343(8) Uani 1 1 d . A . H28 H 0.6888 0.0724 0.6679 0.041 Uiso 1 1 calc R . . C29 C 0.6977(4) 0.0084(2) 0.73753(15) 0.0385(8) Uani 1 1 d . . . H29 H 0.7845 0.0384 0.7505 0.046 Uiso 1 1 calc R A . C30 C 0.6292(4) -0.0562(2) 0.76782(14) 0.0407(9) Uani 1 1 d . A . H30 H 0.6675 -0.0693 0.8019 0.049 Uiso 1 1 calc R . . C31 C 0.5054(4) -0.1012(2) 0.74838(14) 0.0410(9) Uani 1 1 d . . . H31 H 0.4611 -0.1472 0.7684 0.049 Uiso 1 1 calc R A . C32 C 0.4455(4) -0.0795(2) 0.69965(13) 0.0377(8) Uani 1 1 d . A . H32 H 0.3589 -0.1099 0.6868 0.045 Uiso 1 1 calc R . . C33 C 0.2227(4) -0.2295(2) 0.44862(13) 0.0302(7) Uani 1 1 d . A . C34 C 0.1786(4) -0.2952(2) 0.48319(13) 0.0315(7) Uani 1 1 d . . . H34 H 0.1521 -0.2803 0.5182 0.038 Uiso 1 1 calc R A . C35 C 0.1729(4) -0.3832(2) 0.46699(14) 0.0362(8) Uani 1 1 d . A . H35 H 0.1425 -0.4278 0.4909 0.043 Uiso 1 1 calc R . . C36 C 0.2116(4) -0.4053(2) 0.41593(15) 0.0406(9) Uani 1 1 d . . . H36 H 0.2076 -0.4650 0.4048 0.049 Uiso 1 1 calc R A . C37 C 0.2558(4) -0.3404(2) 0.38137(14) 0.0409(9) Uani 1 1 d . A . H37 H 0.2822 -0.3554 0.3463 0.049 Uiso 1 1 calc R . . C38 C 0.2620(4) -0.2532(2) 0.39760(13) 0.0355(8) Uani 1 1 d . . . H38 H 0.2935 -0.2091 0.3735 0.043 Uiso 1 1 calc R A . C39 C -0.0171(4) 0.1772(2) 0.34734(13) 0.0305(7) Uani 1 1 d . . . C40 C 0.0461(5) 0.1565(3) 0.29914(15) 0.0515(11) Uani 1 1 d . A . H40 H 0.1325 0.1193 0.2979 0.062 Uiso 1 1 calc R . . C41 C -0.0146(6) 0.1891(3) 0.25275(16) 0.0574(12) Uani 1 1 d . . . H41 H 0.0293 0.1737 0.2200 0.069 Uiso 1 1 calc R A . C42 C -0.1390(5) 0.2440(2) 0.25415(15) 0.0453(10) Uani 1 1 d . A . H42 H -0.1799 0.2673 0.2225 0.054 Uiso 1 1 calc R . . C43 C -0.2035(4) 0.2649(2) 0.30169(14) 0.0392(8) Uani 1 1 d . . . H43 H -0.2895 0.3025 0.3028 0.047 Uiso 1 1 calc R A . C44 C -0.1437(4) 0.2316(2) 0.34785(14) 0.0334(7) Uani 1 1 d . A . H44 H -0.1897 0.2460 0.3804 0.040 Uiso 1 1 calc R . . Cl1 Cl 0.3739(2) 0.31332(19) 0.31670(12) 0.0979(8) Uani 0.679(3) 1 d PDU B 1 Cl2 Cl 0.1536(4) 0.4424(3) 0.2825(2) 0.0945(9) Uani 0.679(3) 1 d PDU B 1 C1S C 0.3304(12) 0.4094(9) 0.2948(8) 0.211(10) Uani 0.679(3) 1 d PDU B 1 H1S1 H 0.3871 0.4170 0.2616 0.253 Uiso 0.679(3) 1 calc PR B 1 H1S2 H 0.3735 0.4522 0.3201 0.253 Uiso 0.679(3) 1 calc PR B 1 Cl1D Cl 0.3715(6) 0.3710(5) 0.3223(3) 0.0979(8) Uani 0.321(3) 1 d PDU B 2 Cl2D Cl 0.1267(11) 0.4729(7) 0.2776(5) 0.0945(9) Uani 0.321(3) 1 d PDU B 2 C1D C 0.205(2) 0.3686(9) 0.2856(10) 0.121(9) Uani 0.321(3) 1 d PDU B 2 H1D1 H 0.2257 0.3430 0.2506 0.145 Uiso 0.321(3) 1 calc PR B 2 H1D2 H 0.1304 0.3300 0.3033 0.145 Uiso 0.321(3) 1 calc PR B 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 0.0257(2) 0.0312(2) 0.0318(2) -0.00003(17) -0.00064(16) 0.00236(18) N1 0.0253(14) 0.0297(14) 0.0299(15) -0.0035(11) -0.0003(12) 0.0012(11) C2 0.021(6) 0.023(5) 0.032(2) 0.008(3) 0.001(3) -0.006(4) C3 0.035(3) 0.033(3) 0.012(7) 0.010(4) 0.011(5) 0.005(2) C1 0.0291(17) 0.0331(18) 0.0332(18) 0.0001(14) 0.0003(15) 0.0062(14) O2A 0.021(6) 0.023(5) 0.032(2) 0.008(3) 0.001(3) -0.006(4) C3A 0.035(3) 0.033(3) 0.012(7) 0.010(4) 0.011(5) 0.005(2) O3A 0.038(5) 0.021(4) 0.057(5) -0.004(3) -0.007(4) -0.002(3) C4 0.0276(17) 0.0291(17) 0.0362(19) -0.0040(14) -0.0007(14) 0.0052(13) C2B 0.021(6) 0.023(5) 0.032(2) 0.008(3) 0.001(3) -0.006(4) O2B 0.072(15) 0.064(15) 0.066(15) -0.021(11) -0.016(12) 0.000(11) O3B 0.035(3) 0.033(3) 0.012(7) 0.010(4) 0.011(5) 0.005(2) C5 0.0236(16) 0.0325(17) 0.0363(19) -0.0035(14) -0.0013(14) 0.0021(14) N2 0.0250(14) 0.0311(14) 0.0340(16) -0.0003(11) -0.0022(12) -0.0001(11) C7 0.038(3) 0.050(4) 0.007(7) 0.001(4) 0.001(6) -0.002(3) C8 0.028(8) 0.045(6) 0.034(4) -0.001(3) -0.005(4) 0.009(4) C6 0.0301(18) 0.0344(18) 0.0319(18) -0.0062(14) -0.0050(14) 0.0021(14) C7A 0.038(3) 0.050(4) 0.007(7) 0.001(4) 0.001(6) -0.002(3) O7A 0.082(8) 0.033(5) 0.043(6) -0.014(4) -0.024(5) 0.016(5) O8A 0.028(8) 0.045(6) 0.034(4) -0.001(3) -0.005(4) 0.009(4) C9 0.0291(18) 0.039(2) 0.039(2) 0.0028(15) -0.0036(15) -0.0010(15) C10 0.0244(16) 0.0359(18) 0.0338(18) 0.0068(14) 0.0013(14) -0.0004(14) O7B 0.038(3) 0.050(4) 0.007(7) 0.001(4) 0.001(6) -0.002(3) C8B 0.028(8) 0.045(6) 0.034(4) -0.001(3) -0.005(4) 0.009(4) O8B 0.059(8) 0.033(6) 0.031(7) -0.001(4) -0.010(5) 0.004(5) N3 0.0254(14) 0.0318(15) 0.0311(15) -0.0004(11) 0.0012(12) 0.0007(11) C11 0.0270(17) 0.0366(18) 0.0325(18) 0.0037(14) 0.0030(14) 0.0001(14) C12 0.0274(17) 0.042(2) 0.0338(19) 0.0055(15) 0.0013(15) 0.0081(15) C13 0.0334(19) 0.0351(19) 0.0333(19) 0.0042(14) 0.0042(15) 0.0059(15) C14 0.0287(17) 0.0336(17) 0.0297(18) 0.0026(14) 0.0047(14) 0.0016(14) C15 0.0270(17) 0.0305(17) 0.0315(18) 0.0020(13) 0.0070(14) -0.0008(14) N4 0.0263(14) 0.0297(14) 0.0302(15) 0.0028(11) 0.0015(12) 0.0022(11) C16 0.0268(16) 0.0292(17) 0.0325(17) 0.0006(14) 0.0038(14) 0.0003(14) C17 0.0297(17) 0.0316(18) 0.0378(19) -0.0009(14) 0.0015(15) -0.0033(14) C18 0.0300(18) 0.0356(18) 0.0319(18) -0.0010(14) -0.0036(15) 0.0021(14) C19 0.0261(17) 0.0318(18) 0.0311(18) -0.0004(13) 0.0020(14) 0.0017(13) C20 0.0268(17) 0.0302(17) 0.0319(18) 0.0000(13) 0.0026(14) 0.0072(13) C21 0.0297(18) 0.0326(17) 0.0333(19) -0.0033(14) -0.0110(15) 0.0070(14) C22 0.038(2) 0.041(2) 0.075(3) -0.015(2) 0.005(2) -0.0016(18) C23 0.047(2) 0.045(2) 0.081(3) -0.013(2) -0.006(2) -0.007(2) C24 0.060(3) 0.033(2) 0.050(2) -0.0059(16) -0.022(2) 0.0102(19) C25 0.054(3) 0.044(2) 0.047(2) -0.0127(17) -0.012(2) 0.025(2) C26 0.036(2) 0.041(2) 0.049(2) -0.0082(17) -0.0054(17) 0.0111(16) C27 0.0317(18) 0.0316(17) 0.0297(18) -0.0005(13) -0.0010(14) 0.0012(14) C28 0.0323(18) 0.0282(18) 0.042(2) 0.0015(14) -0.0026(16) -0.0018(14) C29 0.039(2) 0.0291(18) 0.047(2) -0.0074(15) -0.0104(17) 0.0012(15) C30 0.050(2) 0.045(2) 0.0278(18) -0.0041(15) -0.0093(16) 0.0057(17) C31 0.044(2) 0.043(2) 0.036(2) 0.0038(15) 0.0047(17) -0.0040(17) C32 0.0351(19) 0.041(2) 0.0366(19) 0.0024(16) -0.0008(15) -0.0069(17) C33 0.0277(17) 0.0301(17) 0.0330(18) 0.0023(13) 0.0007(14) 0.0028(14) C34 0.0320(18) 0.0346(18) 0.0279(17) -0.0005(13) 0.0008(14) 0.0029(15) C35 0.0351(19) 0.0343(19) 0.039(2) 0.0042(15) -0.0003(16) 0.0012(15) C36 0.044(2) 0.033(2) 0.045(2) -0.0052(15) -0.0012(17) 0.0053(16) C37 0.047(2) 0.043(2) 0.0327(19) -0.0012(15) 0.0042(17) 0.0072(17) C38 0.038(2) 0.0363(19) 0.0323(19) 0.0027(14) 0.0037(15) 0.0019(15) C39 0.0376(19) 0.0237(16) 0.0301(17) -0.0007(13) -0.0059(15) -0.0009(14) C40 0.071(3) 0.045(2) 0.038(2) -0.0019(17) 0.003(2) 0.019(2) C41 0.091(4) 0.048(3) 0.034(2) -0.0036(18) 0.003(2) 0.012(2) C42 0.068(3) 0.033(2) 0.034(2) 0.0020(15) -0.0179(19) -0.0066(19) C43 0.043(2) 0.0318(18) 0.043(2) 0.0059(15) -0.0141(17) -0.0003(16) C44 0.0350(19) 0.0310(18) 0.0341(19) 0.0003(14) -0.0052(15) -0.0015(15) Cl1 0.0509(9) 0.0808(17) 0.162(2) 0.0365(18) 0.0035(11) 0.0032(13) Cl2 0.0575(18) 0.096(3) 0.1302(19) 0.024(2) -0.0089(14) 0.0129(16) C1S 0.099(8) 0.156(12) 0.38(2) 0.178(15) 0.068(12) 0.042(9) Cl1D 0.0509(9) 0.0808(17) 0.162(2) 0.0365(18) 0.0035(11) 0.0032(13) Cl2D 0.0575(18) 0.096(3) 0.1302(19) 0.024(2) -0.0089(14) 0.0129(16) C1D 0.073(13) 0.056(9) 0.23(3) -0.057(13) -0.036(13) -0.003(9) _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 N4 1.980(3) . ? Cu1 N3 1.987(3) . ? Cu1 N2 1.996(3) . ? Cu1 N1 1.996(3) . ? N1 C1 1.368(4) . ? N1 C4 1.373(4) . ? C2 C3 1.363(13) . ? C2 C1 1.480(10) . ? C2 H2 0.9500 . ? C3 C4 1.429(10) . ? C3 H3 0.9500 . ? C1 O2A 1.227(17) . ? C1 C20 1.386(5) . ? C1 C2B 1.62(2) . ? O2A C3A 1.44(2) . ? C3A O3A 1.05(3) . ? C3A C4 1.62(2) . ? C4 O3B 1.220(18) . ? C4 C5 1.383(5) . ? C2B O2B 1.05(3) . ? C2B O3B 1.44(2) . ? C5 C6 1.379(5) . ? C5 C21 1.502(5) . ? N2 C6 1.370(4) . ? N2 C9 1.371(4) . ? C7 C8 1.381(14) . ? C7 C6 1.457(11) . ? C7 H7 0.9500 . ? C8 C9 1.440(12) . ? C8 H8 0.9500 . ? C6 O7B 1.231(17) . ? C6 C7A 1.62(2) . ? C7A O7A 1.04(3) . ? C7A O8A 1.44(2) . ? O8A C9 1.220(17) . ? C9 C10 1.389(5) . ? C9 C8B 1.62(2) . ? C10 C11 1.403(5) . ? C10 C27 1.486(5) . ? O7B C8B 1.44(2) . ? C8B O8B 1.06(3) . ? N3 C11 1.369(4) . ? N3 C14 1.380(4) . ? C11 C12 1.443(5) . ? C12 C13 1.355(5) . ? C12 H12 0.9500 . ? C13 C14 1.437(4) . ? C13 H13 0.9500 . ? C14 C15 1.395(5) . ? C15 C16 1.400(5) . ? C15 C33 1.503(5) . ? N4 C19 1.374(4) . ? N4 C16 1.383(4) . ? C16 C17 1.433(5) . ? C17 C18 1.365(5) . ? C17 H17 0.9500 . ? C18 C19 1.440(4) . ? C18 H18 0.9500 . ? C19 C20 1.412(4) . ? C20 C39 1.489(5) . ? C21 C22 1.376(5) . ? C21 C26 1.383(5) . ? C22 C23 1.384(5) . ? C22 H22 0.9500 . ? C23 C24 1.372(6) . ? C23 H23 0.9500 . ? C24 C25 1.368(6) . ? C24 H24 0.9500 . ? C25 C26 1.391(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C32 1.394(5) . ? C27 C28 1.397(5) . ? C28 C29 1.376(5) . ? C28 H28 0.9500 . ? C29 C30 1.387(5) . ? C29 H29 0.9500 . ? C30 C31 1.379(5) . ? C30 H30 0.9500 . ? C31 C32 1.385(5) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C34 1.387(5) . ? C33 C38 1.393(5) . ? C34 C35 1.399(5) . ? C34 H34 0.9500 . ? C35 C36 1.386(5) . ? C35 H35 0.9500 . ? C36 C37 1.379(5) . ? C36 H36 0.9500 . ? C37 C38 1.386(5) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C39 C40 1.386(5) . ? C39 C44 1.390(5) . ? C40 C41 1.385(6) . ? C40 H40 0.9500 . ? C41 C42 1.379(6) . ? C41 H41 0.9500 . ? C42 C43 1.376(5) . ? C42 H42 0.9500 . ? C43 C44 1.381(5) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? Cl1 C1S 1.606(9) . ? Cl2 C1S 1.669(10) . ? C1S H1S1 0.9900 . ? C1S H1S2 0.9900 . ? Cl1D C1D 1.742(12) . ? Cl2D C1D 1.737(12) . ? C1D H1D1 0.9900 . ? C1D H1D2 0.9900 . ? 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 N4 Cu1 N3 91.00(11) . . ? N4 Cu1 N2 176.42(11) . . ? N3 Cu1 N2 89.86(11) . . ? N4 Cu1 N1 90.14(11) . . ? N3 Cu1 N1 176.70(11) . . ? N2 Cu1 N1 89.19(11) . . ? C1 N1 C4 106.4(3) . . ? C1 N1 Cu1 126.4(2) . . ? C4 N1 Cu1 126.6(2) . . ? C3 C2 C1 104.3(8) . . ? C3 C2 H2 127.8 . . ? C1 C2 H2 127.8 . . ? C2 C3 C4 108.7(8) . . ? C2 C3 H3 125.6 . . ? C4 C3 H3 125.6 . . ? O2A C1 N1 113.7(9) . . ? O2A C1 C20 118.8(9) . . ? N1 C1 C20 126.8(3) . . ? O2A C1 C2 9.6(15) . . ? N1 C1 C2 110.2(5) . . ? C20 C1 C2 123.0(5) . . ? O2A C1 C2B 16(2) . . ? N1 C1 C2B 105.8(11) . . ? C20 C1 C2B 127.3(12) . . ? C2 C1 C2B 6.6(15) . . ? C1 O2A C3A 114.2(19) . . ? O3A C3A O2A 129(3) . . ? O3A C3A C4 126(2) . . ? O2A C3A C4 95(2) . . ? O3B C4 N1 114.6(11) . . ? O3B C4 C5 117.8(11) . . ? N1 C4 C5 127.0(3) . . ? O3B C4 C3 6.8(17) . . ? N1 C4 C3 110.0(5) . . ? C5 C4 C3 122.9(5) . . ? O3B C4 C3A 14(3) . . ? N1 C4 C3A 106.6(10) . . ? C5 C4 C3A 126.3(11) . . ? C3 C4 C3A 7.5(14) . . ? O2B C2B O3B 126(3) . . ? O2B C2B C1 133(3) . . ? O3B C2B C1 96(2) . . ? C4 O3B C2B 113(2) . . ? C6 C5 C4 121.6(3) . . ? C6 C5 C21 118.7(3) . . ? C4 C5 C21 119.6(3) . . ? C6 N2 C9 106.2(3) . . ? C6 N2 Cu1 126.9(2) . . ? C9 N2 Cu1 126.4(2) . . ? C8 C7 C6 104.0(8) . . ? C8 C7 H7 128.0 . . ? C6 C7 H7 128.0 . . ? C7 C8 C9 107.6(9) . . ? C7 C8 H8 126.2 . . ? C9 C8 H8 126.2 . . ? O7B C6 N2 115.1(10) . . ? O7B C6 C5 117.5(10) . . ? N2 C6 C5 126.9(3) . . ? O7B C6 C7 6(2) . . ? N2 C6 C7 111.1(5) . . ? C5 C6 C7 122.0(5) . . ? O7B C6 C7A 16(2) . . ? N2 C6 C7A 105.8(10) . . ? C5 C6 C7A 127.0(11) . . ? C7 C6 C7A 10.1(11) . . ? O7A C7A O8A 128(3) . . ? O7A C7A C6 126(2) . . ? O8A C7A C6 96(2) . . ? C9 O8A C7A 113(2) . . ? O8A C9 N2 114.6(9) . . ? O8A C9 C10 118.2(9) . . ? N2 C9 C10 126.6(3) . . ? O8A C9 C8 13(2) . . ? N2 C9 C8 109.1(6) . . ? C10 C9 C8 124.2(6) . . ? O8A C9 C8B 7.8(18) . . ? N2 C9 C8B 107.6(11) . . ? C10 C9 C8B 125.5(12) . . ? C8 C9 C8B 9(3) . . ? C9 C10 C11 122.0(3) . . ? C9 C10 C27 118.0(3) . . ? C11 C10 C27 120.0(3) . . ? C6 O7B C8B 115(2) . . ? O8B C8B O7B 126(3) . . ? O8B C8B C9 137(3) . . ? O7B C8B C9 96(2) . . ? C11 N3 C14 106.2(3) . . ? C11 N3 Cu1 127.1(2) . . ? C14 N3 Cu1 126.0(2) . . ? N3 C11 C10 125.8(3) . . ? N3 C11 C12 110.1(3) . . ? C10 C11 C12 124.1(3) . . ? C13 C12 C11 106.6(3) . . ? C13 C12 H12 126.7 . . ? C11 C12 H12 126.7 . . ? C12 C13 C14 107.4(3) . . ? C12 C13 H13 126.3 . . ? C14 C13 H13 126.3 . . ? N3 C14 C15 125.4(3) . . ? N3 C14 C13 109.5(3) . . ? C15 C14 C13 124.9(3) . . ? C14 C15 C16 123.4(3) . . ? C14 C15 C33 117.9(3) . . ? C16 C15 C33 118.8(3) . . ? C19 N4 C16 105.8(3) . . ? C19 N4 Cu1 127.2(2) . . ? C16 N4 Cu1 126.3(2) . . ? N4 C16 C15 125.1(3) . . ? N4 C16 C17 109.8(3) . . ? C15 C16 C17 125.0(3) . . ? C18 C17 C16 107.5(3) . . ? C18 C17 H17 126.2 . . ? C16 C17 H17 126.2 . . ? C17 C18 C19 106.2(3) . . ? C17 C18 H18 126.9 . . ? C19 C18 H18 126.9 . . ? N4 C19 C20 125.4(3) . . ? N4 C19 C18 110.5(3) . . ? C20 C19 C18 124.0(3) . . ? C1 C20 C19 122.2(3) . . ? C1 C20 C39 118.0(3) . . ? C19 C20 C39 119.8(3) . . ? C22 C21 C26 118.4(3) . . ? C22 C21 C5 119.8(3) . . ? C26 C21 C5 121.8(3) . . ? C21 C22 C23 121.0(4) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C22 120.4(4) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 119.4(4) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 120.4(4) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C21 C26 C25 120.5(4) . . ? C21 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C32 C27 C28 118.3(3) . . ? C32 C27 C10 120.3(3) . . ? C28 C27 C10 121.3(3) . . ? C29 C28 C27 120.9(3) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C28 C29 C30 120.1(3) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C31 C30 C29 119.9(3) . . ? C31 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C30 C31 C32 120.1(3) . . ? C30 C31 H31 119.9 . . ? C32 C31 H31 119.9 . . ? C31 C32 C27 120.7(3) . . ? C31 C32 H32 119.7 . . ? C27 C32 H32 119.7 . . ? C34 C33 C38 118.5(3) . . ? C34 C33 C15 120.6(3) . . ? C38 C33 C15 121.0(3) . . ? C33 C34 C35 120.7(3) . . ? C33 C34 H34 119.7 . . ? C35 C34 H34 119.7 . . ? C36 C35 C34 119.9(3) . . ? C36 C35 H35 120.1 . . ? C34 C35 H35 120.1 . . ? C37 C36 C35 119.8(3) . . ? C37 C36 H36 120.1 . . ? C35 C36 H36 120.1 . . ? C36 C37 C38 120.2(3) . . ? C36 C37 H37 119.9 . . ? C38 C37 H37 119.9 . . ? C37 C38 C33 121.0(3) . . ? C37 C38 H38 119.5 . . ? C33 C38 H38 119.5 . . ? C40 C39 C44 118.1(3) . . ? C40 C39 C20 120.5(3) . . ? C44 C39 C20 121.3(3) . . ? C41 C40 C39 121.1(4) . . ? C41 C40 H40 119.4 . . ? C39 C40 H40 119.4 . . ? C42 C41 C40 119.9(4) . . ? C42 C41 H41 120.0 . . ? C40 C41 H41 120.0 . . ? C43 C42 C41 119.7(4) . . ? C43 C42 H42 120.2 . . ? C41 C42 H42 120.2 . . ? C42 C43 C44 120.3(4) . . ? C42 C43 H43 119.9 . . ? C44 C43 H43 119.9 . . ? C43 C44 C39 120.9(3) . . ? C43 C44 H44 119.5 . . ? C39 C44 H44 119.5 . . ? Cl1 C1S Cl2 124.0(8) . . ? Cl1 C1S H1S1 106.3 . . ? Cl2 C1S H1S1 106.3 . . ? Cl1 C1S H1S2 106.3 . . ? Cl2 C1S H1S2 106.3 . . ? H1S1 C1S H1S2 106.4 . . ? Cl2D C1D Cl1D 112.1(9) . . ? Cl2D C1D H1D1 109.2 . . ? Cl1D C1D H1D1 109.2 . . ? Cl2D C1D H1D2 109.2 . . ? Cl1D C1D H1D2 109.2 . . ? H1D1 C1D H1D2 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Cu1 N1 C1 -6.8(3) . . . . ? N3 Cu1 N1 C1 103.5(19) . . . . ? N2 Cu1 N1 C1 176.8(3) . . . . ? N4 Cu1 N1 C4 -176.7(3) . . . . ? N3 Cu1 N1 C4 -66(2) . . . . ? N2 Cu1 N1 C4 6.8(3) . . . . ? C1 C2 C3 C4 5.5(14) . . . . ? C4 N1 C1 O2A -4.9(13) . . . . ? Cu1 N1 C1 O2A -176.6(12) . . . . ? C4 N1 C1 C20 -175.2(3) . . . . ? Cu1 N1 C1 C20 13.2(5) . . . . ? C4 N1 C1 C2 4.7(7) . . . . ? Cu1 N1 C1 C2 -166.9(7) . . . . ? C4 N1 C1 C2B 9.9(18) . . . . ? Cu1 N1 C1 C2B -161.7(18) . . . . ? C3 C2 C1 O2A 107(9) . . . . ? C3 C2 C1 N1 -6.5(12) . . . . ? C3 C2 C1 C20 173.5(8) . . . . ? C3 C2 C1 C2B -55(12) . . . . ? N1 C1 O2A C3A 18(2) . . . . ? C20 C1 O2A C3A -170.6(17) . . . . ? C2 C1 O2A C3A -52(7) . . . . ? C2B C1 O2A C3A -45(7) . . . . ? C1 O2A C3A O3A -166(3) . . . . ? C1 O2A C3A C4 -20(3) . . . . ? C1 N1 C4 O3B 4(2) . . . . ? Cu1 N1 C4 O3B 176(2) . . . . ? C1 N1 C4 C5 175.1(3) . . . . ? Cu1 N1 C4 C5 -13.3(5) . . . . ? C1 N1 C4 C3 -1.2(7) . . . . ? Cu1 N1 C4 C3 170.4(6) . . . . ? C1 N1 C4 C3A -8.3(13) . . . . ? Cu1 N1 C4 C3A 163.3(13) . . . . ? C2 C3 C4 O3B -136(18) . . . . ? C2 C3 C4 N1 -3.0(12) . . . . ? C2 C3 C4 C5 -179.5(8) . . . . ? C2 C3 C4 C3A 61(11) . . . . ? O3A C3A C4 O3B 37(8) . . . . ? O2A C3A C4 O3B -110(12) . . . . ? O3A C3A C4 N1 163(3) . . . . ? O2A C3A C4 N1 16(2) . . . . ? O3A C3A C4 C5 -20(4) . . . . ? O2A C3A C4 C5 -167.2(12) . . . . ? O3A C3A C4 C3 46(9) . . . . ? O2A C3A C4 C3 -102(12) . . . . ? O2A C1 C2B O2B -51(6) . . . . ? N1 C1 C2B O2B -173(5) . . . . ? C20 C1 C2B O2B 12(6) . . . . ? C2 C1 C2B O2B -40(9) . . . . ? O2A C1 C2B O3B 104(9) . . . . ? N1 C1 C2B O3B -18(3) . . . . ? C20 C1 C2B O3B 167(2) . . . . ? C2 C1 C2B O3B 115(14) . . . . ? N1 C4 O3B C2B -19(4) . . . . ? C5 C4 O3B C2B 170(3) . . . . ? C3 C4 O3B C2B 30(15) . . . . ? C3A C4 O3B C2B 39(8) . . . . ? O2B C2B O3B C4 179(4) . . . . ? C1 C2B O3B C4 22(4) . . . . ? O3B C4 C5 C6 177(3) . . . . ? N1 C4 C5 C6 5.9(5) . . . . ? C3 C4 C5 C6 -178.2(7) . . . . ? C3A C4 C5 C6 -170.1(15) . . . . ? O3B C4 C5 C21 -6(3) . . . . ? N1 C4 C5 C21 -176.6(3) . . . . ? C3 C4 C5 C21 -0.7(8) . . . . ? C3A C4 C5 C21 7.5(16) . . . . ? N4 Cu1 N2 C6 -74.0(18) . . . . ? N3 Cu1 N2 C6 -177.8(3) . . . . ? N1 Cu1 N2 C6 5.3(3) . . . . ? N4 Cu1 N2 C9 96.5(17) . . . . ? N3 Cu1 N2 C9 -7.4(3) . . . . ? N1 Cu1 N2 C9 175.8(3) . . . . ? C6 C7 C8 C9 13(3) . . . . ? C9 N2 C6 O7B 3(2) . . . . ? Cu1 N2 C6 O7B 175(2) . . . . ? C9 N2 C6 C5 174.5(3) . . . . ? Cu1 N2 C6 C5 -13.4(5) . . . . ? C9 N2 C6 C7 -2.3(9) . . . . ? Cu1 N2 C6 C7 169.8(9) . . . . ? C9 N2 C6 C7A -11.4(11) . . . . ? Cu1 N2 C6 C7A 160.6(11) . . . . ? C4 C5 C6 O7B 180(2) . . . . ? C21 C5 C6 O7B 2(2) . . . . ? C4 C5 C6 N2 8.2(5) . . . . ? C21 C5 C6 N2 -169.3(3) . . . . ? C4 C5 C6 C7 -175.3(10) . . . . ? C21 C5 C6 C7 7.2(11) . . . . ? C4 C5 C6 C7A -164.6(13) . . . . ? C21 C5 C6 C7A 17.9(14) . . . . ? C8 C7 C6 O7B -140(21) . . . . ? C8 C7 C6 N2 -7(2) . . . . ? C8 C7 C6 C5 176.0(16) . . . . ? C8 C7 C6 C7A 53(7) . . . . ? O7B C6 C7A O7A 37(6) . . . . ? N2 C6 C7A O7A 165(3) . . . . ? C5 C6 C7A O7A -21(4) . . . . ? C7 C6 C7A O7A 42(6) . . . . ? O7B C6 C7A O8A -109(9) . . . . ? N2 C6 C7A O8A 19(2) . . . . ? C5 C6 C7A O8A -167.1(13) . . . . ? C7 C6 C7A O8A -104(8) . . . . ? O7A C7A O8A C9 -166(3) . . . . ? C6 C7A O8A C9 -22(3) . . . . ? C7A O8A C9 N2 17(3) . . . . ? C7A O8A C9 C10 -171.1(16) . . . . ? C7A O8A C9 C8 -50(6) . . . . ? C7A O8A C9 C8B -10(16) . . . . ? C6 N2 C9 O8A -2.4(15) . . . . ? Cu1 N2 C9 O8A -174.5(14) . . . . ? C6 N2 C9 C10 -173.0(3) . . . . ? Cu1 N2 C9 C10 14.9(5) . . . . ? C6 N2 C9 C8 10.5(15) . . . . ? Cu1 N2 C9 C8 -161.6(14) . . . . ? C6 N2 C9 C8B 1.4(19) . . . . ? Cu1 N2 C9 C8B -170.7(19) . . . . ? C7 C8 C9 O8A 102(8) . . . . ? C7 C8 C9 N2 -15(3) . . . . ? C7 C8 C9 C10 168.1(14) . . . . ? C7 C8 C9 C8B 66(9) . . . . ? O8A C9 C10 C11 -176.9(15) . . . . ? N2 C9 C10 C11 -6.6(5) . . . . ? C8 C9 C10 C11 169.4(17) . . . . ? C8B C9 C10 C11 180(2) . . . . ? O8A C9 C10 C27 6.4(15) . . . . ? N2 C9 C10 C27 176.7(3) . . . . ? C8 C9 C10 C27 -7.3(17) . . . . ? C8B C9 C10 C27 3(2) . . . . ? N2 C6 O7B C8B -6(4) . . . . ? C5 C6 O7B C8B -179(3) . . . . ? C7 C6 O7B C8B 43(17) . . . . ? C7A C6 O7B C8B 51(7) . . . . ? C6 O7B C8B O8B -179(4) . . . . ? C6 O7B C8B C9 6(4) . . . . ? O8A C9 C8B O8B -25(14) . . . . ? N2 C9 C8B O8B -179(5) . . . . ? C10 C9 C8B O8B -4(7) . . . . ? C8 C9 C8B O8B 80(9) . . . . ? O8A C9 C8B O7B 149(19) . . . . ? N2 C9 C8B O7B -4(3) . . . . ? C10 C9 C8B O7B 170(2) . . . . ? C8 C9 C8B O7B -105(11) . . . . ? N4 Cu1 N3 C11 176.6(3) . . . . ? N2 Cu1 N3 C11 -6.9(3) . . . . ? N1 Cu1 N3 C11 66(2) . . . . ? N4 Cu1 N3 C14 7.9(3) . . . . ? N2 Cu1 N3 C14 -175.6(3) . . . . ? N1 Cu1 N3 C14 -102.3(19) . . . . ? C14 N3 C11 C10 -173.5(3) . . . . ? Cu1 N3 C11 C10 16.0(5) . . . . ? C14 N3 C11 C12 3.6(3) . . . . ? Cu1 N3 C11 C12 -166.9(2) . . . . ? C9 C10 C11 N3 -9.7(5) . . . . ? C27 C10 C11 N3 167.0(3) . . . . ? C9 C10 C11 C12 173.6(3) . . . . ? C27 C10 C11 C12 -9.7(5) . . . . ? N3 C11 C12 C13 -1.8(4) . . . . ? C10 C11 C12 C13 175.3(3) . . . . ? C11 C12 C13 C14 -0.7(4) . . . . ? C11 N3 C14 C15 172.5(3) . . . . ? Cu1 N3 C14 C15 -16.8(5) . . . . ? C11 N3 C14 C13 -4.0(3) . . . . ? Cu1 N3 C14 C13 166.6(2) . . . . ? C12 C13 C14 N3 3.0(4) . . . . ? C12 C13 C14 C15 -173.6(3) . . . . ? N3 C14 C15 C16 8.8(5) . . . . ? C13 C14 C15 C16 -175.1(3) . . . . ? N3 C14 C15 C33 -170.7(3) . . . . ? C13 C14 C15 C33 5.3(5) . . . . ? N3 Cu1 N4 C19 177.3(3) . . . . ? N2 Cu1 N4 C19 73.5(18) . . . . ? N1 Cu1 N4 C19 -5.8(3) . . . . ? N3 Cu1 N4 C16 7.6(3) . . . . ? N2 Cu1 N4 C16 -96.2(17) . . . . ? N1 Cu1 N4 C16 -175.5(3) . . . . ? C19 N4 C16 C15 171.9(3) . . . . ? Cu1 N4 C16 C15 -16.6(4) . . . . ? C19 N4 C16 C17 -3.9(3) . . . . ? Cu1 N4 C16 C17 167.5(2) . . . . ? C14 C15 C16 N4 8.8(5) . . . . ? C33 C15 C16 N4 -171.7(3) . . . . ? C14 C15 C16 C17 -176.0(3) . . . . ? C33 C15 C16 C17 3.6(5) . . . . ? N4 C16 C17 C18 3.0(4) . . . . ? C15 C16 C17 C18 -172.9(3) . . . . ? C16 C17 C18 C19 -0.8(4) . . . . ? C16 N4 C19 C20 -174.6(3) . . . . ? Cu1 N4 C19 C20 14.0(5) . . . . ? C16 N4 C19 C18 3.5(3) . . . . ? Cu1 N4 C19 C18 -167.9(2) . . . . ? C17 C18 C19 N4 -1.7(4) . . . . ? C17 C18 C19 C20 176.5(3) . . . . ? O2A C1 C20 C19 -175.3(13) . . . . ? N1 C1 C20 C19 -5.5(5) . . . . ? C2 C1 C20 C19 174.6(8) . . . . ? C2B C1 C20 C19 168(2) . . . . ? O2A C1 C20 C39 7.8(14) . . . . ? N1 C1 C20 C39 177.6(3) . . . . ? C2 C1 C20 C39 -2.3(8) . . . . ? C2B C1 C20 C39 -9(2) . . . . ? N4 C19 C20 C1 -8.8(5) . . . . ? C18 C19 C20 C1 173.4(3) . . . . ? N4 C19 C20 C39 168.0(3) . . . . ? C18 C19 C20 C39 -9.8(5) . . . . ? C6 C5 C21 C22 90.4(4) . . . . ? C4 C5 C21 C22 -87.2(4) . . . . ? C6 C5 C21 C26 -88.5(4) . . . . ? C4 C5 C21 C26 93.9(4) . . . . ? C26 C21 C22 C23 -0.2(6) . . . . ? C5 C21 C22 C23 -179.1(4) . . . . ? C21 C22 C23 C24 -1.0(7) . . . . ? C22 C23 C24 C25 1.2(7) . . . . ? C23 C24 C25 C26 -0.3(6) . . . . ? C22 C21 C26 C25 1.2(6) . . . . ? C5 C21 C26 C25 -179.9(3) . . . . ? C24 C25 C26 C21 -1.0(6) . . . . ? C9 C10 C27 C32 118.1(4) . . . . ? C11 C10 C27 C32 -58.7(5) . . . . ? C9 C10 C27 C28 -58.2(4) . . . . ? C11 C10 C27 C28 125.0(4) . . . . ? C32 C27 C28 C29 -2.7(5) . . . . ? C10 C27 C28 C29 173.7(3) . . . . ? C27 C28 C29 C30 1.2(5) . . . . ? C28 C29 C30 C31 1.6(5) . . . . ? C29 C30 C31 C32 -2.8(6) . . . . ? C30 C31 C32 C27 1.3(6) . . . . ? C28 C27 C32 C31 1.4(5) . . . . ? C10 C27 C32 C31 -175.0(3) . . . . ? C14 C15 C33 C34 56.8(4) . . . . ? C16 C15 C33 C34 -122.8(4) . . . . ? C14 C15 C33 C38 -122.3(4) . . . . ? C16 C15 C33 C38 58.1(4) . . . . ? C38 C33 C34 C35 -0.4(5) . . . . ? C15 C33 C34 C35 -179.5(3) . . . . ? C33 C34 C35 C36 0.0(5) . . . . ? C34 C35 C36 C37 0.1(6) . . . . ? C35 C36 C37 C38 0.1(6) . . . . ? C36 C37 C38 C33 -0.5(6) . . . . ? C34 C33 C38 C37 0.7(5) . . . . ? C15 C33 C38 C37 179.7(3) . . . . ? C1 C20 C39 C40 114.4(4) . . . . ? C19 C20 C39 C40 -62.5(5) . . . . ? C1 C20 C39 C44 -61.6(4) . . . . ? C19 C20 C39 C44 121.4(4) . . . . ? C44 C39 C40 C41 0.1(6) . . . . ? C20 C39 C40 C41 -176.0(4) . . . . ? C39 C40 C41 C42 0.8(7) . . . . ? C40 C41 C42 C43 -1.0(7) . . . . ? C41 C42 C43 C44 0.4(6) . . . . ? C42 C43 C44 C39 0.6(5) . . . . ? C40 C39 C44 C43 -0.8(5) . . . . ? C20 C39 C44 C43 175.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.736 _refine_diff_density_min -0.719 _refine_diff_density_rms 0.066 data_05273 _database_code_depnum_ccdc_archive 'CCDC 615720' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H24 Cu N4 O' _chemical_formula_sum 'C43 H26 Cu N4 O' _chemical_formula_weight 678.22 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 monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.680(2) _cell_length_b 16.236(2) _cell_length_c 14.8470(19) _cell_angle_alpha 90.00 _cell_angle_beta 119.522(3) _cell_angle_gamma 90.00 _cell_volume 3079.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2599 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1396 _exptl_absorpt_coefficient_mu 0.754 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8340 _exptl_absorpt_correction_T_max 0.9284 _exptl_absorpt_process_details 'SADABS, R. Blessing; 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_details '0.30 degree frames measured for 5 seconds each' _diffrn_measurement_method \w-scans _diffrn_measurement_device 'three-circle goniometer with fixed chi' _diffrn_measurement_device_type 'Bruker Platform goniometer' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker SMART 6000' _diffrn_detector_area_resol_mean 44.52 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15876 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0669 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.07 _reflns_number_total 5462 _reflns_number_gt 3882 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SIR-92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2003), XTEL (loc. libr.)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0654P)^2^+3.9018P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5462 _refine_ls_number_parameters 455 _refine_ls_number_restraints 92 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1488 _refine_ls_wR_factor_gt 0.1301 _refine_ls_goodness_of_fit_ref 1.021 _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 0.69423(4) 0.11785(3) 0.62720(4) 0.02854(17) Uani 1 1 d . . . N1 N 0.6079(2) 0.10259(17) 0.4765(2) 0.0284(7) Uani 0.711(4) 1 d PDU A 1 C1 C 0.5012(3) 0.0994(2) 0.4161(3) 0.0256(8) Uani 0.711(4) 1 d PDU A 1 C2 C 0.4679(4) 0.0808(3) 0.3067(4) 0.0220(11) Uani 0.711(4) 1 d PDU A 1 H2 H 0.3984 0.0732 0.2518 0.026 Uiso 0.711(4) 1 calc PR A 1 C3 C 0.5584(4) 0.0766(3) 0.3008(4) 0.0251(10) Uani 0.711(4) 1 d PDU A 1 H3 H 0.5646 0.0669 0.2409 0.030 Uiso 0.711(4) 1 calc PR A 1 C4 C 0.6434(3) 0.0904(2) 0.4071(3) 0.0280(8) Uani 0.711(4) 1 d PDU A 1 N1D N 0.6079(2) 0.10259(17) 0.4765(2) 0.0284(7) Uani 0.289(4) 1 d PDU A 2 C1D C 0.5012(3) 0.0994(2) 0.4161(3) 0.0256(8) Uani 0.289(4) 1 d PDU A 2 C2D C 0.5317(8) 0.0849(8) 0.3410(8) 0.0220(11) Uani 0.289(4) 1 d PDU A 2 O3D O 0.4836(7) 0.0725(5) 0.2523(7) 0.0251(10) Uani 0.289(4) 1 d PDU A 2 C4D C 0.6434(3) 0.0904(2) 0.4071(3) 0.0280(8) Uani 0.289(4) 1 d PDU A 2 C5 C 0.7477(3) 0.0915(2) 0.4305(3) 0.0250(8) Uani 1 1 d . . . N2 N 0.8229(2) 0.11766(16) 0.6182(2) 0.0246(7) Uani 1 1 d D A . C6 C 0.8320(3) 0.1033(2) 0.5318(3) 0.0254(8) Uani 1 1 d D A . C7 C 0.9414(3) 0.0972(2) 0.5602(3) 0.0302(9) Uani 1 1 d D . . H7 H 0.9684 0.0870 0.5148 0.036 Uiso 1 1 calc R A . C8 C 0.9975(3) 0.1087(2) 0.6631(3) 0.0293(9) Uani 1 1 d D A . H8 H 1.0717 0.1087 0.7039 0.035 Uiso 1 1 calc R . . C9 C 0.9238(3) 0.12107(19) 0.7003(3) 0.0227(8) Uani 1 1 d D . . C10 C 0.9514(3) 0.13033(19) 0.8047(3) 0.0238(8) Uani 1 1 d . A . N3 N 0.7723(2) 0.13347(17) 0.7787(2) 0.0257(7) Uani 1 1 d . A . C11 C 0.8793(3) 0.1375(2) 0.8395(3) 0.0249(8) Uani 1 1 d . . . C12 C 0.9079(3) 0.1548(2) 0.9457(3) 0.0362(10) Uani 1 1 d . A . H12 H 0.9769 0.1613 1.0022 0.043 Uiso 1 1 calc R . . C13 C 0.8203(3) 0.1597(2) 0.9493(3) 0.0364(10) Uani 1 1 d . . . H13 H 0.8147 0.1700 1.0094 0.044 Uiso 1 1 calc R A . C14 C 0.7337(3) 0.1468(2) 0.8454(3) 0.0257(8) Uani 1 1 d . A . C15 C 0.6269(3) 0.1484(2) 0.8174(3) 0.0261(8) Uani 1 1 d . . . N4 N 0.5653(2) 0.12156(17) 0.6335(2) 0.0309(7) Uani 0.711(4) 1 d PDU A 2 C16 C 0.5503(3) 0.1378(2) 0.7160(3) 0.0293(8) Uani 0.711(4) 1 d PDU A 2 C17 C 0.4331(5) 0.1392(3) 0.6339(5) 0.0333(12) Uani 0.711(4) 1 d PDU A 2 O18 O 0.3573(3) 0.1529(3) 0.6367(4) 0.0443(11) Uani 0.711(4) 1 d PDU A 2 C19 C 0.4630(3) 0.1230(2) 0.5545(3) 0.0265(8) Uani 0.711(4) 1 d PDU A 2 N4D N 0.5653(2) 0.12156(17) 0.6335(2) 0.0309(7) Uani 0.289(4) 1 d PDU A 1 C16D C 0.5503(3) 0.1378(2) 0.7160(3) 0.0293(8) Uani 0.289(4) 1 d PDU A 1 C17D C 0.4431(7) 0.1552(8) 0.6942(9) 0.0333(12) Uani 0.289(4) 1 d PDU A 1 H17D H 0.4189 0.1684 0.7411 0.040 Uiso 0.289(4) 1 calc PR A 1 C18D C 0.3868(8) 0.1475(11) 0.5879(9) 0.0443(11) Uani 0.289(4) 1 d PDU A 1 H18D H 0.3137 0.1562 0.5446 0.053 Uiso 0.289(4) 1 calc PR A 1 C19D C 0.4630(3) 0.1230(2) 0.5545(3) 0.0265(8) Uani 0.289(4) 1 d PDU A 1 C20 C 0.4280(3) 0.11275(19) 0.4502(3) 0.0217(8) Uani 1 1 d . . . C21 C 0.7709(3) 0.0818(2) 0.3442(3) 0.0262(8) Uani 1 1 d . A . C22 C 0.7425(4) 0.0109(2) 0.2834(3) 0.0393(11) Uani 1 1 d . . . H22 H 0.7100 -0.0332 0.2989 0.047 Uiso 1 1 calc R A . C23 C 0.7606(4) 0.0038(3) 0.2006(3) 0.0472(12) Uani 1 1 d . A . H23 H 0.7407 -0.0450 0.1600 0.057 Uiso 1 1 calc R . . C24 C 0.8077(4) 0.0674(3) 0.1769(3) 0.0435(11) Uani 1 1 d . . . H24 H 0.8193 0.0630 0.1196 0.052 Uiso 1 1 calc R A . C25 C 0.8375(4) 0.1369(2) 0.2371(4) 0.0411(11) Uani 1 1 d . A . H25 H 0.8703 0.1806 0.2212 0.049 Uiso 1 1 calc R . . C26 C 0.8208(3) 0.1444(2) 0.3203(3) 0.0351(10) Uani 1 1 d . . . H26 H 0.8434 0.1927 0.3618 0.042 Uiso 1 1 calc R A . C27 C 1.0648(3) 0.1298(2) 0.8839(3) 0.0228(8) Uani 1 1 d . . . C28 C 1.1054(3) 0.0661(2) 0.9566(3) 0.0253(8) Uani 1 1 d . A . H28 H 1.0605 0.0233 0.9550 0.030 Uiso 1 1 calc R . . C29 C 1.2099(3) 0.0648(2) 1.0305(3) 0.0298(9) Uani 1 1 d . . . H29 H 1.2365 0.0208 1.0789 0.036 Uiso 1 1 calc R A . C30 C 1.2765(3) 0.1268(2) 1.0350(3) 0.0301(9) Uani 1 1 d . A . H30 H 1.3484 0.1258 1.0863 0.036 Uiso 1 1 calc R . . C31 C 1.2369(3) 0.1906(2) 0.9634(3) 0.0304(9) Uani 1 1 d . . . H31 H 1.2821 0.2334 0.9658 0.036 Uiso 1 1 calc R A . C32 C 1.1325(3) 0.1921(2) 0.8891(3) 0.0270(8) Uani 1 1 d . A . H32 H 1.1064 0.2362 0.8408 0.032 Uiso 1 1 calc R . . C33 C 0.5964(3) 0.1634(2) 0.8980(3) 0.0307(9) Uani 1 1 d . A . C34 C 0.6282(3) 0.2343(2) 0.9588(3) 0.0347(10) Uani 1 1 d . . . H34 H 0.6699 0.2740 0.9487 0.042 Uiso 1 1 calc R A . C35 C 0.6000(3) 0.2477(2) 1.0335(4) 0.0399(11) Uani 1 1 d . A . H35 H 0.6226 0.2962 1.0745 0.048 Uiso 1 1 calc R . . C36 C 0.5388(4) 0.1909(3) 1.0488(4) 0.0506(13) Uani 1 1 d . . . H36 H 0.5192 0.2001 1.1002 0.061 Uiso 1 1 calc R A . C37 C 0.5064(5) 0.1206(3) 0.9887(5) 0.0618(16) Uani 1 1 d . A . H37 H 0.4646 0.0811 0.9989 0.074 Uiso 1 1 calc R . . C38 C 0.5346(4) 0.1075(3) 0.9139(4) 0.0501(13) Uani 1 1 d . . . H38 H 0.5113 0.0591 0.8726 0.060 Uiso 1 1 calc R A . C39 C 0.3145(3) 0.11729(19) 0.3746(3) 0.0229(8) Uani 1 1 d . A . C40 C 0.2404(3) 0.0765(2) 0.3924(3) 0.0295(9) Uani 1 1 d . . . H40 H 0.2637 0.0446 0.4535 0.035 Uiso 1 1 calc R A . C41 C 0.1349(3) 0.0818(2) 0.3231(3) 0.0370(10) Uani 1 1 d . A . H41 H 0.0862 0.0542 0.3372 0.044 Uiso 1 1 calc R . . C42 C 0.0991(3) 0.1273(2) 0.2325(3) 0.0368(10) Uani 1 1 d . . . H42 H 0.0265 0.1300 0.1837 0.044 Uiso 1 1 calc R A . C43 C 0.1708(3) 0.1685(2) 0.2145(3) 0.0321(9) Uani 1 1 d . A . H43 H 0.1468 0.2006 0.1535 0.038 Uiso 1 1 calc R . . C44 C 0.2771(3) 0.1638(2) 0.2839(3) 0.0276(9) Uani 1 1 d . . . H44 H 0.3251 0.1925 0.2697 0.033 Uiso 1 1 calc R A . 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 0.0300(3) 0.0175(2) 0.0342(3) 0.00220(18) 0.0128(2) -0.00047(18) N1 0.0263(17) 0.0175(15) 0.0417(19) 0.0012(13) 0.0170(15) 0.0010(12) C1 0.034(2) 0.0133(16) 0.031(2) 0.0038(14) 0.0171(18) 0.0040(14) C2 0.027(3) 0.016(2) 0.022(3) 0.001(2) 0.011(2) 0.004(2) C3 0.025(3) 0.022(2) 0.025(3) 0.001(2) 0.010(2) 0.003(2) C4 0.029(2) 0.0136(16) 0.036(2) 0.0026(15) 0.0124(17) 0.0014(14) N1D 0.0263(17) 0.0175(15) 0.0417(19) 0.0012(13) 0.0170(15) 0.0010(12) C1D 0.034(2) 0.0133(16) 0.031(2) 0.0038(14) 0.0171(18) 0.0040(14) C2D 0.027(3) 0.016(2) 0.022(3) 0.001(2) 0.011(2) 0.004(2) O3D 0.025(3) 0.022(2) 0.025(3) 0.001(2) 0.010(2) 0.003(2) C4D 0.029(2) 0.0136(16) 0.036(2) 0.0026(15) 0.0124(17) 0.0014(14) C5 0.032(2) 0.0141(16) 0.027(2) 0.0033(14) 0.0132(18) -0.0007(14) N2 0.0329(19) 0.0163(14) 0.0240(17) 0.0009(12) 0.0135(15) -0.0016(12) C6 0.029(2) 0.0189(17) 0.028(2) 0.0030(14) 0.0133(18) -0.0026(14) C7 0.035(2) 0.028(2) 0.033(2) 0.0006(16) 0.021(2) -0.0038(16) C8 0.027(2) 0.0278(19) 0.032(2) 0.0002(16) 0.0132(19) -0.0047(16) C9 0.028(2) 0.0156(16) 0.0219(19) 0.0006(13) 0.0108(17) -0.0030(14) C10 0.029(2) 0.0129(16) 0.028(2) 0.0005(13) 0.0130(17) -0.0008(14) N3 0.0272(18) 0.0188(15) 0.0346(19) 0.0030(12) 0.0180(16) 0.0018(12) C11 0.031(2) 0.0166(17) 0.027(2) 0.0027(14) 0.0145(18) 0.0009(14) C12 0.039(3) 0.0214(19) 0.043(3) 0.0003(17) 0.016(2) 0.0017(17) C13 0.045(3) 0.024(2) 0.040(3) 0.0042(17) 0.021(2) 0.0008(17) C14 0.029(2) 0.0158(16) 0.030(2) 0.0040(14) 0.0128(18) 0.0020(15) C15 0.031(2) 0.0145(16) 0.035(2) 0.0037(15) 0.0189(19) 0.0002(15) N4 0.0347(18) 0.0208(15) 0.0272(17) 0.0039(13) 0.0077(15) -0.0063(13) C16 0.027(2) 0.0202(17) 0.035(2) 0.0076(15) 0.0106(18) -0.0017(15) C17 0.049(3) 0.014(2) 0.046(4) -0.002(3) 0.030(3) -0.008(2) O18 0.039(2) 0.037(2) 0.053(3) 0.002(2) 0.020(2) -0.0005(19) C19 0.030(2) 0.0177(17) 0.0256(19) 0.0043(14) 0.0093(16) -0.0046(14) N4D 0.0347(18) 0.0208(15) 0.0272(17) 0.0039(13) 0.0077(15) -0.0063(13) C16D 0.027(2) 0.0202(17) 0.035(2) 0.0076(15) 0.0106(18) -0.0017(15) C17D 0.049(3) 0.014(2) 0.046(4) -0.002(3) 0.030(3) -0.008(2) C18D 0.039(2) 0.037(2) 0.053(3) 0.002(2) 0.020(2) -0.0005(19) C19D 0.030(2) 0.0177(17) 0.0256(19) 0.0043(14) 0.0093(16) -0.0046(14) C20 0.026(2) 0.0127(16) 0.0244(19) 0.0014(13) 0.0108(17) -0.0009(13) C21 0.029(2) 0.0219(18) 0.025(2) 0.0009(14) 0.0110(17) -0.0001(15) C22 0.059(3) 0.027(2) 0.031(2) -0.0013(16) 0.021(2) -0.0095(19) C23 0.077(4) 0.032(2) 0.033(3) -0.0058(18) 0.027(3) -0.004(2) C24 0.069(3) 0.034(2) 0.037(3) 0.0041(18) 0.034(3) 0.012(2) C25 0.060(3) 0.030(2) 0.047(3) 0.0019(19) 0.036(3) -0.001(2) C26 0.048(3) 0.0253(19) 0.040(2) -0.0029(17) 0.028(2) -0.0015(18) C27 0.028(2) 0.0193(17) 0.0198(19) -0.0018(13) 0.0111(17) -0.0011(14) C28 0.030(2) 0.0200(17) 0.025(2) -0.0015(14) 0.0127(18) -0.0055(15) C29 0.039(2) 0.0217(18) 0.026(2) 0.0042(15) 0.0138(19) 0.0029(16) C30 0.028(2) 0.032(2) 0.024(2) -0.0008(16) 0.0082(18) -0.0001(16) C31 0.034(2) 0.0237(19) 0.032(2) -0.0027(16) 0.016(2) -0.0081(16) C32 0.032(2) 0.0201(18) 0.026(2) 0.0013(15) 0.0122(18) -0.0022(15) C33 0.033(2) 0.0226(19) 0.042(2) -0.0002(16) 0.023(2) 0.0008(16) C34 0.042(3) 0.0226(19) 0.049(3) -0.0008(17) 0.029(2) -0.0052(17) C35 0.048(3) 0.028(2) 0.050(3) -0.0089(18) 0.030(2) -0.0015(18) C36 0.075(4) 0.036(2) 0.072(4) -0.005(2) 0.060(3) 0.000(2) C37 0.094(4) 0.036(3) 0.101(5) -0.014(3) 0.083(4) -0.018(3) C38 0.075(4) 0.026(2) 0.081(4) -0.017(2) 0.063(3) -0.017(2) C39 0.029(2) 0.0122(15) 0.0239(19) -0.0030(13) 0.0102(17) -0.0002(14) C40 0.031(2) 0.0169(17) 0.038(2) 0.0065(15) 0.016(2) 0.0032(15) C41 0.032(2) 0.023(2) 0.051(3) 0.0003(18) 0.017(2) -0.0021(17) C42 0.026(2) 0.0227(19) 0.042(3) -0.0030(17) 0.002(2) 0.0019(16) C43 0.038(3) 0.0197(18) 0.025(2) -0.0009(15) 0.0050(19) 0.0012(16) C44 0.034(2) 0.0181(17) 0.025(2) -0.0022(14) 0.0102(19) -0.0020(15) _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 N4 1.942(3) . ? Cu1 N2 1.959(3) . ? Cu1 N1 1.970(3) . ? Cu1 N3 1.974(3) . ? N1 C1 1.370(4) . ? N1 C4 1.379(4) . ? C1 C20 1.413(5) . ? C1 C2 1.478(6) . ? C2 C3 1.376(6) . ? C2 H2 0.9500 . ? C3 C4 1.469(6) . ? C3 H3 0.9500 . ? C4 C5 1.392(5) . ? C2D O3D 1.164(9) . ? C5 C6 1.413(5) . ? C5 C21 1.488(5) . ? N2 C6 1.373(4) . ? N2 C9 1.380(4) . ? C6 C7 1.449(5) . ? C7 C8 1.344(5) . ? C7 H7 0.9500 . ? C8 C9 1.450(5) . ? C8 H8 0.9500 . ? C9 C10 1.404(5) . ? C10 C11 1.394(5) . ? C10 C27 1.491(5) . ? N3 C11 1.375(5) . ? N3 C14 1.379(5) . ? C11 C12 1.445(6) . ? C12 C13 1.316(6) . ? C12 H12 0.9500 . ? C13 C14 1.451(6) . ? C13 H13 0.9500 . ? C14 C15 1.411(5) . ? C15 C16 1.375(5) . ? C15 C33 1.490(5) . ? N4 C16 1.372(4) . ? N4 C19 1.376(4) . ? N4 C17 1.965(6) . ? C16 C17 1.543(7) . ? C17 O18 1.155(6) . ? C17 C19 1.470(6) . ? C19 C20 1.380(5) . ? C17D C18D 1.380(9) . ? C17D H17D 0.9500 . ? C18D H18D 0.9500 . ? C20 C39 1.483(5) . ? C21 C22 1.394(5) . ? C21 C26 1.397(5) . ? C22 C23 1.385(6) . ? C22 H22 0.9500 . ? C23 C24 1.381(6) . ? C23 H23 0.9500 . ? C24 C25 1.370(6) . ? C24 H24 0.9500 . ? C25 C26 1.379(6) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C32 1.393(5) . ? C27 C28 1.399(5) . ? C28 C29 1.378(5) . ? C28 H28 0.9500 . ? C29 C30 1.381(5) . ? C29 H29 0.9500 . ? C30 C31 1.389(5) . ? C30 H30 0.9500 . ? C31 C32 1.379(5) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C38 1.383(6) . ? C33 C34 1.394(5) . ? C34 C35 1.379(6) . ? C34 H34 0.9500 . ? C35 C36 1.383(6) . ? C35 H35 0.9500 . ? C36 C37 1.381(6) . ? C36 H36 0.9500 . ? C37 C38 1.380(6) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C39 C44 1.399(5) . ? C39 C40 1.405(5) . ? C40 C41 1.377(6) . ? C40 H40 0.9500 . ? C41 C42 1.392(6) . ? C41 H41 0.9500 . ? C42 C43 1.378(6) . ? C42 H42 0.9500 . ? C43 C44 1.385(5) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? 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 N4 Cu1 N2 178.03(12) . . ? N4 Cu1 N1 87.82(12) . . ? N2 Cu1 N1 91.39(12) . . ? N4 Cu1 N3 88.47(13) . . ? N2 Cu1 N3 92.32(12) . . ? N1 Cu1 N3 176.29(12) . . ? C1 N1 C4 103.7(3) . . ? C1 N1 Cu1 129.5(2) . . ? C4 N1 Cu1 126.7(2) . . ? N1 C1 C20 125.9(3) . . ? N1 C1 C2 112.2(3) . . ? C20 C1 C2 121.9(3) . . ? C3 C2 C1 105.9(4) . . ? C3 C2 H2 127.0 . . ? C1 C2 H2 127.0 . . ? C2 C3 C4 105.0(4) . . ? C2 C3 H3 127.5 . . ? C4 C3 H3 127.5 . . ? N1 C4 C5 125.8(3) . . ? N1 C4 C3 113.0(3) . . ? C5 C4 C3 121.2(4) . . ? C4 C5 C6 123.1(3) . . ? C4 C5 C21 118.3(3) . . ? C6 C5 C21 118.6(3) . . ? C6 N2 C9 106.0(3) . . ? C6 N2 Cu1 127.2(2) . . ? C9 N2 Cu1 126.2(2) . . ? N2 C6 C5 125.4(3) . . ? N2 C6 C7 110.1(3) . . ? C5 C6 C7 124.4(3) . . ? C8 C7 C6 107.0(3) . . ? C8 C7 H7 126.5 . . ? C6 C7 H7 126.5 . . ? C7 C8 C9 107.3(3) . . ? C7 C8 H8 126.3 . . ? C9 C8 H8 126.3 . . ? N2 C9 C10 125.4(3) . . ? N2 C9 C8 109.6(3) . . ? C10 C9 C8 124.9(3) . . ? C11 C10 C9 124.1(3) . . ? C11 C10 C27 117.6(3) . . ? C9 C10 C27 118.2(3) . . ? C11 N3 C14 105.1(3) . . ? C11 N3 Cu1 126.1(2) . . ? C14 N3 Cu1 128.7(3) . . ? N3 C11 C10 125.7(3) . . ? N3 C11 C12 110.5(3) . . ? C10 C11 C12 123.8(4) . . ? C13 C12 C11 107.0(4) . . ? C13 C12 H12 126.5 . . ? C11 C12 H12 126.5 . . ? C12 C13 C14 108.0(4) . . ? C12 C13 H13 126.0 . . ? C14 C13 H13 126.0 . . ? N3 C14 C15 125.5(3) . . ? N3 C14 C13 109.4(3) . . ? C15 C14 C13 125.1(4) . . ? C16 C15 C14 120.7(4) . . ? C16 C15 C33 119.5(3) . . ? C14 C15 C33 119.8(4) . . ? C16 N4 C19 99.8(3) . . ? C16 N4 Cu1 129.6(3) . . ? C19 N4 Cu1 129.8(3) . . ? C16 N4 C17 51.4(2) . . ? C19 N4 C17 48.4(2) . . ? Cu1 N4 C17 173.0(2) . . ? N4 C16 C15 126.7(3) . . ? N4 C16 C17 84.5(3) . . ? C15 C16 C17 148.7(4) . . ? O18 C17 C19 137.5(6) . . ? O18 C17 C16 133.9(5) . . ? C19 C17 C16 88.5(4) . . ? O18 C17 N4 176.8(5) . . ? C19 C17 N4 44.4(2) . . ? C16 C17 N4 44.0(2) . . ? N4 C19 C20 126.9(3) . . ? N4 C19 C17 87.2(3) . . ? C20 C19 C17 145.9(4) . . ? C18D C17D H17D 129.0 . . ? C17D C18D H18D 126.9 . . ? C19 C20 C1 119.5(3) . . ? C19 C20 C39 120.1(3) . . ? C1 C20 C39 120.3(3) . . ? C22 C21 C26 117.6(4) . . ? C22 C21 C5 121.5(3) . . ? C26 C21 C5 120.9(3) . . ? C23 C22 C21 121.1(4) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C24 C23 C22 120.1(4) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 C24 C23 119.3(4) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 121.1(4) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C25 C26 C21 120.7(4) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? C32 C27 C28 118.2(3) . . ? C32 C27 C10 121.9(3) . . ? C28 C27 C10 119.9(3) . . ? C29 C28 C27 120.6(3) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C30 120.7(3) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C29 C30 C31 119.2(4) . . ? C29 C30 H30 120.4 . . ? C31 C30 H30 120.4 . . ? C32 C31 C30 120.4(3) . . ? C32 C31 H31 119.8 . . ? C30 C31 H31 119.8 . . ? C31 C32 C27 120.8(3) . . ? C31 C32 H32 119.6 . . ? C27 C32 H32 119.6 . . ? C38 C33 C34 118.1(4) . . ? C38 C33 C15 120.7(4) . . ? C34 C33 C15 121.2(3) . . ? C35 C34 C33 120.9(4) . . ? C35 C34 H34 119.6 . . ? C33 C34 H34 119.6 . . ? C34 C35 C36 120.3(4) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C37 C36 C35 119.3(4) . . ? C37 C36 H36 120.4 . . ? C35 C36 H36 120.4 . . ? C38 C37 C36 120.2(4) . . ? C38 C37 H37 119.9 . . ? C36 C37 H37 119.9 . . ? C37 C38 C33 121.2(4) . . ? C37 C38 H38 119.4 . . ? C33 C38 H38 119.4 . . ? C44 C39 C40 117.6(3) . . ? C44 C39 C20 121.1(3) . . ? C40 C39 C20 121.2(3) . . ? C41 C40 C39 121.3(4) . . ? C41 C40 H40 119.3 . . ? C39 C40 H40 119.3 . . ? C40 C41 C42 120.3(4) . . ? C40 C41 H41 119.8 . . ? C42 C41 H41 119.8 . . ? C43 C42 C41 119.0(4) . . ? C43 C42 H42 120.5 . . ? C41 C42 H42 120.5 . . ? C42 C43 C44 121.2(4) . . ? C42 C43 H43 119.4 . . ? C44 C43 H43 119.4 . . ? C43 C44 C39 120.6(4) . . ? C43 C44 H44 119.7 . . ? C39 C44 H44 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Cu1 N1 C1 1.1(3) . . . . ? N2 Cu1 N1 C1 -177.1(3) . . . . ? N3 Cu1 N1 C1 0.6(19) . . . . ? N4 Cu1 N1 C4 -177.2(3) . . . . ? N2 Cu1 N1 C4 4.7(3) . . . . ? N3 Cu1 N1 C4 -178(37) . . . . ? C4 N1 C1 C20 -176.5(3) . . . . ? Cu1 N1 C1 C20 4.9(5) . . . . ? C4 N1 C1 C2 2.9(4) . . . . ? Cu1 N1 C1 C2 -175.7(3) . . . . ? N1 C1 C2 C3 -3.0(5) . . . . ? C20 C1 C2 C3 176.5(3) . . . . ? C1 C2 C3 C4 1.6(5) . . . . ? C1 N1 C4 C5 177.4(3) . . . . ? Cu1 N1 C4 C5 -4.0(5) . . . . ? C1 N1 C4 C3 -1.8(4) . . . . ? Cu1 N1 C4 C3 176.8(3) . . . . ? C2 C3 C4 N1 0.1(5) . . . . ? C2 C3 C4 C5 -179.2(4) . . . . ? N1 C4 C5 C6 1.8(5) . . . . ? C3 C4 C5 C6 -179.1(3) . . . . ? N1 C4 C5 C21 -176.5(3) . . . . ? C3 C4 C5 C21 2.6(5) . . . . ? N4 Cu1 N2 C6 -71(4) . . . . ? N1 Cu1 N2 C6 -5.0(3) . . . . ? N3 Cu1 N2 C6 175.2(3) . . . . ? N4 Cu1 N2 C9 118(4) . . . . ? N1 Cu1 N2 C9 -175.7(3) . . . . ? N3 Cu1 N2 C9 4.5(3) . . . . ? C9 N2 C6 C5 176.9(3) . . . . ? Cu1 N2 C6 C5 4.7(5) . . . . ? C9 N2 C6 C7 0.3(4) . . . . ? Cu1 N2 C6 C7 -171.9(2) . . . . ? C4 C5 C6 N2 -2.1(5) . . . . ? C21 C5 C6 N2 176.2(3) . . . . ? C4 C5 C6 C7 174.0(3) . . . . ? C21 C5 C6 C7 -7.7(5) . . . . ? N2 C6 C7 C8 -0.6(4) . . . . ? C5 C6 C7 C8 -177.3(3) . . . . ? C6 C7 C8 C9 0.7(4) . . . . ? C6 N2 C9 C10 -176.4(3) . . . . ? Cu1 N2 C9 C10 -4.1(5) . . . . ? C6 N2 C9 C8 0.2(4) . . . . ? Cu1 N2 C9 C8 172.5(2) . . . . ? C7 C8 C9 N2 -0.6(4) . . . . ? C7 C8 C9 C10 176.0(3) . . . . ? N2 C9 C10 C11 -0.1(5) . . . . ? C8 C9 C10 C11 -176.2(3) . . . . ? N2 C9 C10 C27 177.9(3) . . . . ? C8 C9 C10 C27 1.8(5) . . . . ? N4 Cu1 N3 C11 179.6(3) . . . . ? N2 Cu1 N3 C11 -2.2(3) . . . . ? N1 Cu1 N3 C11 -180(100) . . . . ? N4 Cu1 N3 C14 -4.0(3) . . . . ? N2 Cu1 N3 C14 174.2(3) . . . . ? N1 Cu1 N3 C14 -3.5(19) . . . . ? C14 N3 C11 C10 -177.8(3) . . . . ? Cu1 N3 C11 C10 -0.7(5) . . . . ? C14 N3 C11 C12 -0.9(4) . . . . ? Cu1 N3 C11 C12 176.2(2) . . . . ? C9 C10 C11 N3 2.6(5) . . . . ? C27 C10 C11 N3 -175.3(3) . . . . ? C9 C10 C11 C12 -173.9(3) . . . . ? C27 C10 C11 C12 8.2(5) . . . . ? N3 C11 C12 C13 1.0(4) . . . . ? C10 C11 C12 C13 178.0(3) . . . . ? C11 C12 C13 C14 -0.7(4) . . . . ? C11 N3 C14 C15 179.9(3) . . . . ? Cu1 N3 C14 C15 2.9(5) . . . . ? C11 N3 C14 C13 0.5(4) . . . . ? Cu1 N3 C14 C13 -176.5(2) . . . . ? C12 C13 C14 N3 0.2(4) . . . . ? C12 C13 C14 C15 -179.2(3) . . . . ? N3 C14 C15 C16 -1.3(5) . . . . ? C13 C14 C15 C16 178.0(3) . . . . ? N3 C14 C15 C33 180.0(3) . . . . ? C13 C14 C15 C33 -0.7(5) . . . . ? N2 Cu1 N4 C16 -108(4) . . . . ? N1 Cu1 N4 C16 -174.4(3) . . . . ? N3 Cu1 N4 C16 5.6(3) . . . . ? N2 Cu1 N4 C19 59(4) . . . . ? N1 Cu1 N4 C19 -7.1(3) . . . . ? N3 Cu1 N4 C19 172.9(3) . . . . ? N2 Cu1 N4 C17 -12(5) . . . . ? N1 Cu1 N4 C17 -79(2) . . . . ? N3 Cu1 N4 C17 101(2) . . . . ? C19 N4 C16 C15 -176.4(3) . . . . ? Cu1 N4 C16 C15 -6.3(5) . . . . ? C17 N4 C16 C15 -177.4(5) . . . . ? C19 N4 C16 C17 1.0(3) . . . . ? Cu1 N4 C16 C17 171.1(3) . . . . ? C14 C15 C16 N4 3.0(5) . . . . ? C33 C15 C16 N4 -178.3(3) . . . . ? C14 C15 C16 C17 -172.0(6) . . . . ? C33 C15 C16 C17 6.7(8) . . . . ? N4 C16 C17 O18 -176.6(7) . . . . ? C15 C16 C17 O18 -0.6(11) . . . . ? N4 C16 C17 C19 -0.9(3) . . . . ? C15 C16 C17 C19 175.0(6) . . . . ? C15 C16 C17 N4 175.9(7) . . . . ? C16 N4 C17 O18 51(10) . . . . ? C19 N4 C17 O18 -128(10) . . . . ? Cu1 N4 C17 O18 -51(11) . . . . ? C16 N4 C17 C19 178.7(4) . . . . ? Cu1 N4 C17 C19 77(2) . . . . ? C19 N4 C17 C16 -178.7(4) . . . . ? Cu1 N4 C17 C16 -101(2) . . . . ? C16 N4 C19 C20 178.0(3) . . . . ? Cu1 N4 C19 C20 7.9(5) . . . . ? C17 N4 C19 C20 179.0(5) . . . . ? C16 N4 C19 C17 -1.1(3) . . . . ? Cu1 N4 C19 C17 -171.1(3) . . . . ? O18 C17 C19 N4 176.3(7) . . . . ? C16 C17 C19 N4 0.9(3) . . . . ? O18 C17 C19 C20 -2.3(11) . . . . ? C16 C17 C19 C20 -177.7(5) . . . . ? N4 C17 C19 C20 -178.6(7) . . . . ? N4 C19 C20 C1 -0.2(5) . . . . ? C17 C19 C20 C1 178.1(5) . . . . ? N4 C19 C20 C39 -179.1(3) . . . . ? C17 C19 C20 C39 -0.8(8) . . . . ? N1 C1 C20 C19 -6.2(5) . . . . ? C2 C1 C20 C19 174.5(3) . . . . ? N1 C1 C20 C39 172.7(3) . . . . ? C2 C1 C20 C39 -6.6(5) . . . . ? C4 C5 C21 C22 -61.3(5) . . . . ? C6 C5 C21 C22 120.3(4) . . . . ? C4 C5 C21 C26 117.7(4) . . . . ? C6 C5 C21 C26 -60.7(5) . . . . ? C26 C21 C22 C23 -1.6(6) . . . . ? C5 C21 C22 C23 177.4(4) . . . . ? C21 C22 C23 C24 0.0(7) . . . . ? C22 C23 C24 C25 1.0(7) . . . . ? C23 C24 C25 C26 -0.3(7) . . . . ? C24 C25 C26 C21 -1.3(7) . . . . ? C22 C21 C26 C25 2.2(6) . . . . ? C5 C21 C26 C25 -176.8(4) . . . . ? C11 C10 C27 C32 -115.7(4) . . . . ? C9 C10 C27 C32 66.3(4) . . . . ? C11 C10 C27 C28 63.4(4) . . . . ? C9 C10 C27 C28 -114.6(4) . . . . ? C32 C27 C28 C29 -0.7(5) . . . . ? C10 C27 C28 C29 -179.8(3) . . . . ? C27 C28 C29 C30 0.6(6) . . . . ? C28 C29 C30 C31 -0.4(6) . . . . ? C29 C30 C31 C32 0.2(6) . . . . ? C30 C31 C32 C27 -0.2(6) . . . . ? C28 C27 C32 C31 0.5(5) . . . . ? C10 C27 C32 C31 179.6(3) . . . . ? C16 C15 C33 C38 57.9(5) . . . . ? C14 C15 C33 C38 -123.4(5) . . . . ? C16 C15 C33 C34 -121.5(4) . . . . ? C14 C15 C33 C34 57.2(5) . . . . ? C38 C33 C34 C35 0.7(7) . . . . ? C15 C33 C34 C35 -179.8(4) . . . . ? C33 C34 C35 C36 -0.3(7) . . . . ? C34 C35 C36 C37 0.1(8) . . . . ? C35 C36 C37 C38 -0.2(9) . . . . ? C36 C37 C38 C33 0.6(9) . . . . ? C34 C33 C38 C37 -0.9(8) . . . . ? C15 C33 C38 C37 179.6(5) . . . . ? C19 C20 C39 C44 133.3(4) . . . . ? C1 C20 C39 C44 -45.5(5) . . . . ? C19 C20 C39 C40 -45.3(5) . . . . ? C1 C20 C39 C40 135.8(3) . . . . ? C44 C39 C40 C41 0.2(5) . . . . ? C20 C39 C40 C41 178.9(3) . . . . ? C39 C40 C41 C42 0.8(6) . . . . ? C40 C41 C42 C43 -1.5(6) . . . . ? C41 C42 C43 C44 1.3(6) . . . . ? C42 C43 C44 C39 -0.3(5) . . . . ? C40 C39 C44 C43 -0.4(5) . . . . ? C20 C39 C44 C43 -179.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.144 _refine_diff_density_min -0.536 _refine_diff_density_rms 0.088 # Attachment '3Ni' data_05310 _database_code_depnum_ccdc_archive 'CCDC 617061' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H26 N4 Ni O' _chemical_formula_weight 673.39 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.6193(14) _cell_length_b 16.3787(15) _cell_length_c 14.8341(14) _cell_angle_alpha 90.00 _cell_angle_beta 119.585(2) _cell_angle_gamma 90.00 _cell_volume 3088.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 8991 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 26.3 _exptl_crystal_description plate _exptl_crystal_colour dark _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.672 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8773 _exptl_absorpt_correction_T_max 0.9001 _exptl_absorpt_process_details 'SADABS, R. Blessing; 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_details '0.30 degree frames measured for 20 seconds each' _diffrn_measurement_method \w-scans _diffrn_measurement_device 'three-circle goniometer with fixed chi' _diffrn_measurement_device_type 'Bruker Platform goniometer' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker SMART 6000' _diffrn_detector_area_resol_mean 44.52 _diffrn_standards_number 160 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 808 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 42768 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 26.46 _reflns_number_total 6345 _reflns_number_gt 5431 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SIR-92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2003), XTEL (loc. libr.)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0340P)^2^+3.0846P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6345 _refine_ls_number_parameters 487 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 Ni1 Ni 0.93810(2) 0.619278(16) 0.62630(2) 0.02657(9) Uani 1 1 d . A . N1 N 1.00911(14) 0.63413(11) 0.77471(15) 0.0277(4) Uani 1 1 d . . . N2 N 0.80291(14) 0.61676(10) 0.61872(13) 0.0259(4) Uani 1 1 d . . . N3 N 0.87420(15) 0.60251(11) 0.47929(16) 0.0302(4) Uani 1 1 d . . . N4 N 1.06924(16) 0.62573(11) 0.63241(14) 0.0305(4) Uani 1 1 d . . . C1 C 1.11468(17) 0.64672(13) 0.84317(17) 0.0279(5) Uani 1 1 d . A . C2 C 1.1349(3) 0.65874(16) 0.9482(2) 0.0274(6) Uani 0.850(5) 1 d P A 1 H2 H 1.2011 0.6688 1.0079 0.033 Uiso 0.850(5) 1 calc PR A 1 C3 C 1.0401(3) 0.65270(16) 0.9444(2) 0.0274(6) Uani 0.850(5) 1 d P A 1 H3 H 1.0270 0.6578 1.0008 0.033 Uiso 0.850(5) 1 calc PR A 1 O3D O 1.1121(11) 0.6537(8) 1.0016(11) 0.044(4) Uani 0.150(5) 1 d P A 2 C2D C 1.0788(16) 0.6451(10) 0.9194(14) 0.0274(6) Uani 0.150(5) 1 d P A 2 C4 C 0.96351(17) 0.63690(13) 0.83712(16) 0.0270(4) Uani 1 1 d . A . C5 C 0.85740(17) 0.63009(12) 0.80405(16) 0.0248(4) Uani 1 1 d . . . C6 C 0.78163(17) 0.62141(13) 0.69950(16) 0.0266(4) Uani 1 1 d . A . C7 C 0.67120(18) 0.61130(15) 0.66265(19) 0.0350(5) Uani 1 1 d . . . H7 H 0.6376 0.6124 0.7034 0.042 Uiso 1 1 calc R A . C8 C 0.62437(19) 0.59997(15) 0.55964(19) 0.0355(5) Uani 1 1 d . A . H8 H 0.5515 0.5913 0.5139 0.043 Uiso 1 1 calc R . . C9 C 0.70518(17) 0.60352(13) 0.53171(16) 0.0273(4) Uani 1 1 d . A . C10 C 0.68755(17) 0.59065(13) 0.43118(16) 0.0263(4) Uani 1 1 d . . . C11 C 0.76860(18) 0.58871(13) 0.40903(17) 0.0290(5) Uani 1 1 d . A . C12 C 0.7483(4) 0.57305(19) 0.3032(3) 0.0251(8) Uani 0.739(7) 1 d P A 1 H12 H 0.6825 0.5621 0.2433 0.030 Uiso 0.739(7) 1 calc PR A 1 C13 C 0.8454(3) 0.57780(19) 0.3099(3) 0.0246(8) Uani 0.739(7) 1 d P A 1 H13 H 0.8607 0.5691 0.2555 0.029 Uiso 0.739(7) 1 calc PR A 1 O13D O 0.7740(7) 0.5708(5) 0.2544(7) 0.047(3) Uani 0.261(7) 1 d P A 2 C12D C 0.8113(13) 0.5841(6) 0.3385(10) 0.033(3) Uani 0.261(7) 1 d P A 2 C14 C 0.92065(17) 0.59908(13) 0.41806(17) 0.0276(5) Uani 1 1 d . A . C15 C 1.02636(16) 0.61423(12) 0.44976(16) 0.0240(4) Uani 1 1 d . . . C16 C 1.09432(17) 0.62650(13) 0.55345(17) 0.0277(5) Uani 1 1 d . A . C17 C 1.2103(6) 0.6507(4) 0.5913(6) 0.0261(16) Uani 0.411(6) 1 d P A 1 H17 H 1.2416 0.6593 0.5492 0.031 Uiso 0.411(6) 1 calc PR A 1 C18 C 1.2586(5) 0.6574(3) 0.6962(5) 0.0255(15) Uani 0.411(6) 1 d P A 1 H18 H 1.3300 0.6694 0.7443 0.031 Uiso 0.411(6) 1 calc PR A 1 C17D C 1.2024(4) 0.6420(3) 0.6344(5) 0.0273(11) Uani 0.589(6) 1 d P A 2 O18D O 1.2830(3) 0.65584(17) 0.6362(2) 0.0335(10) Uani 0.589(6) 1 d P A 2 C19 C 1.16826(18) 0.64064(13) 0.71543(18) 0.0299(5) Uani 1 1 d . A . C20 C 1.19446(17) 0.64975(13) 0.81708(17) 0.0271(4) Uani 1 1 d . . . C21 C 0.82354(16) 0.62977(13) 0.88404(16) 0.0254(4) Uani 1 1 d . A . C22 C 0.85283(17) 0.56518(13) 0.95439(16) 0.0286(5) Uani 1 1 d . . . H22 H 0.8939 0.5217 0.9508 0.034 Uiso 1 1 calc R A . C23 C 0.82253(18) 0.56387(14) 1.02951(17) 0.0325(5) Uani 1 1 d . A . H23 H 0.8428 0.5196 1.0769 0.039 Uiso 1 1 calc R . . C24 C 0.76304(18) 0.62686(15) 1.03528(17) 0.0327(5) Uani 1 1 d . . . H24 H 0.7421 0.6259 1.0866 0.039 Uiso 1 1 calc R A . C25 C 0.73396(19) 0.69121(14) 0.96656(18) 0.0337(5) Uani 1 1 d . A . H25 H 0.6931 0.7346 0.9709 0.040 Uiso 1 1 calc R . . C26 C 0.76386(18) 0.69311(14) 0.89126(17) 0.0312(5) Uani 1 1 d . . . H26 H 0.7436 0.7378 0.8444 0.037 Uiso 1 1 calc R A . C27 C 0.57720(17) 0.58070(14) 0.34454(16) 0.0286(5) Uani 1 1 d . A . C28 C 0.5438(2) 0.50865(16) 0.28811(19) 0.0409(6) Uani 1 1 d . . . H28 H 0.5910 0.4639 0.3062 0.049 Uiso 1 1 calc R A . C29 C 0.4417(2) 0.50145(17) 0.2052(2) 0.0472(7) Uani 1 1 d . A . H29 H 0.4197 0.4519 0.1670 0.057 Uiso 1 1 calc R . . C30 C 0.3731(2) 0.56566(17) 0.1786(2) 0.0460(7) Uani 1 1 d . . . H30 H 0.3039 0.5610 0.1213 0.055 Uiso 1 1 calc R A . C31 C 0.4041(2) 0.63670(17) 0.2349(2) 0.0454(6) Uani 1 1 d . A . H31 H 0.3561 0.6809 0.2169 0.055 Uiso 1 1 calc R . . C32 C 0.50536(18) 0.64432(15) 0.3178(2) 0.0375(5) Uani 1 1 d . . . H32 H 0.5259 0.6935 0.3567 0.045 Uiso 1 1 calc R A . C33 C 1.06446(17) 0.61829(12) 0.37315(16) 0.0259(4) Uani 1 1 d . A . C34 C 1.01051(19) 0.66452(13) 0.28280(16) 0.0298(5) Uani 1 1 d . . . H34 H 0.9485 0.6932 0.2693 0.036 Uiso 1 1 calc R A . C35 C 1.0474(2) 0.66880(14) 0.21231(18) 0.0350(5) Uani 1 1 d . A . H35 H 1.0100 0.7000 0.1507 0.042 Uiso 1 1 calc R . . C36 C 1.1378(2) 0.62814(14) 0.2314(2) 0.0398(6) Uani 1 1 d . . . H36 H 1.1626 0.6312 0.1832 0.048 Uiso 1 1 calc R A . C37 C 1.1925(2) 0.58253(15) 0.3218(2) 0.0408(6) Uani 1 1 d . A . H37 H 1.2552 0.5548 0.3357 0.049 Uiso 1 1 calc R . . C38 C 1.15567(19) 0.57763(14) 0.39149(19) 0.0336(5) Uani 1 1 d . . . H38 H 1.1932 0.5460 0.4528 0.040 Uiso 1 1 calc R A . C39 C 1.30615(18) 0.66394(14) 0.89814(19) 0.0335(5) Uani 1 1 d . A . C40 C 1.3832(2) 0.60730(18) 0.9146(3) 0.0585(9) Uani 1 1 d . . . H40 H 1.3652 0.5593 0.8734 0.070 Uiso 1 1 calc R A . C41 C 1.4869(2) 0.62038(19) 0.9913(3) 0.0721(11) Uani 1 1 d . A . H41 H 1.5390 0.5807 1.0028 0.087 Uiso 1 1 calc R . . C42 C 1.5147(2) 0.68976(18) 1.0504(3) 0.0558(8) Uani 1 1 d . . . H42 H 1.5858 0.6985 1.1023 0.067 Uiso 1 1 calc R A . C43 C 1.4389(2) 0.74689(17) 1.0342(2) 0.0459(6) Uani 1 1 d . A . H43 H 1.4576 0.7951 1.0752 0.055 Uiso 1 1 calc R . . C44 C 1.33531(19) 0.73415(15) 0.9583(2) 0.0385(6) Uani 1 1 d . . . H44 H 1.2836 0.7740 0.9472 0.046 Uiso 1 1 calc R A . 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 Ni1 0.02930(16) 0.02290(15) 0.02792(16) 0.00226(11) 0.01443(12) 0.00212(11) N1 0.0233(9) 0.0257(9) 0.0342(10) 0.0045(8) 0.0143(8) 0.0013(7) N2 0.0280(9) 0.0251(9) 0.0219(9) 0.0010(7) 0.0103(7) 0.0030(7) N3 0.0300(10) 0.0234(9) 0.0416(11) 0.0034(8) 0.0211(9) 0.0014(7) N4 0.0426(11) 0.0252(9) 0.0232(9) 0.0035(7) 0.0157(8) 0.0072(8) C1 0.0277(11) 0.0239(10) 0.0313(11) 0.0044(9) 0.0139(9) 0.0027(8) C2 0.0237(14) 0.0302(10) 0.0244(10) -0.0001(7) 0.0089(10) -0.0032(8) C3 0.0237(14) 0.0302(10) 0.0244(10) -0.0001(7) 0.0089(10) -0.0032(8) O3D 0.037(8) 0.051(8) 0.047(9) 0.007(6) 0.025(8) -0.001(6) C2D 0.0237(14) 0.0302(10) 0.0244(10) -0.0001(7) 0.0089(10) -0.0032(8) C4 0.0286(11) 0.0246(10) 0.0254(11) 0.0031(8) 0.0115(9) 0.0008(8) C5 0.0280(11) 0.0211(10) 0.0246(10) 0.0014(8) 0.0124(9) 0.0022(8) C6 0.0267(11) 0.0261(11) 0.0253(10) 0.0001(8) 0.0114(9) 0.0038(8) C7 0.0305(12) 0.0402(13) 0.0333(12) -0.0026(10) 0.0148(10) 0.0042(10) C8 0.0264(12) 0.0412(13) 0.0331(12) -0.0006(10) 0.0102(10) 0.0045(10) C9 0.0267(11) 0.0275(11) 0.0243(10) 0.0014(8) 0.0100(9) 0.0042(8) C10 0.0271(11) 0.0245(10) 0.0233(10) 0.0019(8) 0.0094(9) 0.0028(8) C11 0.0321(12) 0.0228(10) 0.0318(12) 0.0036(9) 0.0156(10) 0.0031(9) C12 0.025(2) 0.0283(16) 0.0199(17) -0.0001(12) 0.0094(16) -0.0033(14) C13 0.026(2) 0.0274(16) 0.0193(17) -0.0008(12) 0.0100(18) -0.0035(13) O13D 0.041(6) 0.057(5) 0.042(5) -0.004(4) 0.020(5) -0.010(4) C12D 0.034(7) 0.031(5) 0.038(7) 0.004(4) 0.020(7) 0.001(5) C14 0.0295(11) 0.0208(10) 0.0308(11) 0.0024(8) 0.0136(10) 0.0015(8) C15 0.0274(11) 0.0208(10) 0.0222(10) 0.0020(8) 0.0110(9) 0.0015(8) C16 0.0317(11) 0.0252(11) 0.0255(11) 0.0030(8) 0.0136(9) 0.0074(9) C17 0.019(4) 0.034(3) 0.022(4) 0.002(3) 0.009(3) 0.001(2) C18 0.021(3) 0.031(3) 0.020(3) 0.001(2) 0.006(3) 0.000(2) C17D 0.028(3) 0.026(2) 0.030(3) 0.002(2) 0.016(3) 0.0030(17) O18D 0.029(2) 0.0411(17) 0.0310(18) -0.0016(12) 0.0152(16) -0.0024(12) C19 0.0340(12) 0.0265(11) 0.0339(12) 0.0063(9) 0.0204(10) 0.0080(9) C20 0.0237(10) 0.0239(10) 0.0317(11) 0.0002(9) 0.0121(9) 0.0008(8) C21 0.0247(10) 0.0261(10) 0.0218(10) -0.0026(8) 0.0089(8) -0.0015(8) C22 0.0313(11) 0.0272(11) 0.0244(11) -0.0003(8) 0.0116(9) 0.0038(9) C23 0.0370(13) 0.0326(12) 0.0247(11) 0.0032(9) 0.0129(10) 0.0013(10) C24 0.0325(12) 0.0408(13) 0.0263(11) -0.0040(10) 0.0157(10) -0.0010(10) C25 0.0363(13) 0.0340(12) 0.0312(12) -0.0034(10) 0.0169(10) 0.0058(10) C26 0.0361(12) 0.0278(11) 0.0279(11) 0.0025(9) 0.0144(10) 0.0061(9) C27 0.0282(11) 0.0317(12) 0.0220(10) 0.0020(9) 0.0093(9) 0.0012(9) C28 0.0432(14) 0.0353(13) 0.0313(13) -0.0022(10) 0.0084(11) 0.0068(11) C29 0.0476(15) 0.0426(15) 0.0338(14) -0.0080(11) 0.0066(12) -0.0061(12) C30 0.0325(13) 0.0498(16) 0.0359(14) 0.0043(12) 0.0018(11) -0.0049(11) C31 0.0284(13) 0.0428(15) 0.0500(16) 0.0047(12) 0.0079(12) 0.0045(11) C32 0.0292(12) 0.0332(12) 0.0400(13) -0.0031(10) 0.0094(11) 0.0006(10) C33 0.0319(11) 0.0214(10) 0.0250(10) -0.0030(8) 0.0144(9) -0.0023(8) C34 0.0382(12) 0.0253(11) 0.0234(11) -0.0022(8) 0.0134(10) 0.0017(9) C35 0.0523(15) 0.0285(11) 0.0248(11) 0.0003(9) 0.0195(11) -0.0018(10) C36 0.0625(17) 0.0303(12) 0.0435(14) -0.0044(10) 0.0392(14) -0.0050(11) C37 0.0507(15) 0.0324(13) 0.0549(16) 0.0050(11) 0.0380(14) 0.0077(11) C38 0.0403(13) 0.0259(11) 0.0387(13) 0.0072(9) 0.0227(11) 0.0057(10) C39 0.0236(11) 0.0316(12) 0.0410(13) -0.0017(10) 0.0125(10) 0.0004(9) C40 0.0289(14) 0.0405(15) 0.088(2) -0.0247(15) 0.0148(15) 0.0013(11) C41 0.0251(14) 0.0503(18) 0.113(3) -0.0226(18) 0.0125(16) 0.0067(12) C42 0.0241(13) 0.0511(17) 0.071(2) -0.0106(15) 0.0074(13) -0.0051(12) C43 0.0363(14) 0.0402(14) 0.0538(17) -0.0119(12) 0.0166(13) -0.0075(11) C44 0.0301(12) 0.0346(13) 0.0473(15) -0.0053(11) 0.0164(11) 0.0013(10) _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 Ni1 N4 1.877(2) . ? Ni1 N3 1.922(2) . ? Ni1 N2 1.9239(18) . ? Ni1 N1 1.9305(19) . ? N1 C1 1.381(3) . ? N1 C4 1.383(3) . ? N1 C2D 1.876(18) . ? N2 C6 1.381(3) . ? N2 C9 1.390(3) . ? N3 C14 1.378(3) . ? N3 C11 1.390(3) . ? N3 C12D 1.844(13) . ? N4 C19 1.383(3) . ? N4 C16 1.389(3) . ? N4 C17D 1.950(5) . ? C1 C20 1.399(3) . ? C1 C2 1.448(4) . ? C1 C2D 1.46(2) . ? C2 C3 1.362(5) . ? C2 H2 0.9500 . ? C3 C4 1.447(4) . ? C3 H3 0.9500 . ? O3D C2D 1.08(2) . ? C2D C4 1.52(2) . ? C4 C5 1.381(3) . ? C5 C6 1.399(3) . ? C5 C21 1.494(3) . ? C6 C7 1.436(3) . ? C7 C8 1.344(3) . ? C7 H7 0.9500 . ? C8 C9 1.433(3) . ? C8 H8 0.9500 . ? C9 C10 1.398(3) . ? C10 C11 1.377(3) . ? C10 C27 1.495(3) . ? C11 C12D 1.460(16) . ? C11 C12 1.469(4) . ? C12 C13 1.375(6) . ? C12 H12 0.9500 . ? C13 C14 1.471(4) . ? C13 H13 0.9500 . ? O13D C12D 1.109(16) . ? C12D C14 1.465(15) . ? C14 C15 1.398(3) . ? C15 C16 1.373(3) . ? C15 C33 1.494(3) . ? C16 C17D 1.459(6) . ? C16 C17 1.552(8) . ? C17 C18 1.358(10) . ? C17 H17 0.9500 . ? C18 C19 1.508(6) . ? C18 H18 0.9500 . ? C17D O18D 1.188(6) . ? C17D C19 1.512(6) . ? C19 C20 1.368(3) . ? C20 C39 1.492(3) . ? C21 C26 1.393(3) . ? C21 C22 1.397(3) . ? C22 C23 1.388(3) . ? C22 H22 0.9500 . ? C23 C24 1.379(3) . ? C23 H23 0.9500 . ? C24 C25 1.380(3) . ? C24 H24 0.9500 . ? C25 C26 1.386(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.388(3) . ? C27 C32 1.391(3) . ? C28 C29 1.393(4) . ? C28 H28 0.9500 . ? C29 C30 1.371(4) . ? C29 H29 0.9500 . ? C30 C31 1.372(4) . ? C30 H30 0.9500 . ? C31 C32 1.386(3) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C38 1.392(3) . ? C33 C34 1.396(3) . ? C34 C35 1.395(3) . ? C34 H34 0.9500 . ? C35 C36 1.378(4) . ? C35 H35 0.9500 . ? C36 C37 1.392(4) . ? C36 H36 0.9500 . ? C37 C38 1.383(3) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C39 C40 1.385(3) . ? C39 C44 1.387(3) . ? C40 C41 1.391(4) . ? C40 H40 0.9500 . ? C41 C42 1.369(4) . ? C41 H41 0.9500 . ? C42 C43 1.378(4) . ? C42 H42 0.9500 . ? C43 C44 1.386(4) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? 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 N4 Ni1 N3 88.60(8) . . ? N4 Ni1 N2 177.94(8) . . ? N3 Ni1 N2 91.19(8) . . ? N4 Ni1 N1 88.66(8) . . ? N3 Ni1 N1 177.03(8) . . ? N2 Ni1 N1 91.59(7) . . ? C1 N1 C4 103.64(18) . . ? C1 N1 C2D 50.6(7) . . ? C4 N1 C2D 53.1(7) . . ? C1 N1 Ni1 129.32(15) . . ? C4 N1 Ni1 127.01(14) . . ? C2D N1 Ni1 178.2(5) . . ? C6 N2 C9 104.22(18) . . ? C6 N2 Ni1 127.82(14) . . ? C9 N2 Ni1 127.79(15) . . ? C14 N3 C11 103.03(19) . . ? C14 N3 C12D 51.7(5) . . ? C11 N3 C12D 51.4(5) . . ? C14 N3 Ni1 129.22(15) . . ? C11 N3 Ni1 127.73(15) . . ? C12D N3 Ni1 178.6(4) . . ? C19 N4 C16 98.81(18) . . ? C19 N4 Ni1 130.41(15) . . ? C16 N4 Ni1 130.40(15) . . ? C19 N4 C17D 50.5(2) . . ? C16 N4 C17D 48.3(2) . . ? Ni1 N4 C17D 175.11(17) . . ? N1 C1 C20 125.7(2) . . ? N1 C1 C2 111.8(2) . . ? C20 C1 C2 122.5(2) . . ? N1 C1 C2D 82.5(8) . . ? C20 C1 C2D 151.7(8) . . ? C2 C1 C2D 29.7(7) . . ? C3 C2 C1 106.4(3) . . ? C3 C2 H2 126.8 . . ? C1 C2 H2 126.8 . . ? C2 C3 C4 106.1(3) . . ? C2 C3 H3 126.9 . . ? C4 C3 H3 126.9 . . ? O3D C2D C1 138(2) . . ? O3D C2D C4 128(2) . . ? C1 C2D C4 93.4(10) . . ? O3D C2D N1 175(2) . . ? C1 C2D N1 46.9(5) . . ? C4 C2D N1 46.6(5) . . ? C5 C4 N1 126.0(2) . . ? C5 C4 C3 121.9(2) . . ? N1 C4 C3 112.0(2) . . ? C5 C4 C2D 153.7(8) . . ? N1 C4 C2D 80.2(8) . . ? C3 C4 C2D 32.1(7) . . ? C4 C5 C6 122.5(2) . . ? C4 C5 C21 118.19(19) . . ? C6 C5 C21 119.26(19) . . ? N2 C6 C5 125.0(2) . . ? N2 C6 C7 110.85(19) . . ? C5 C6 C7 124.1(2) . . ? C8 C7 C6 107.1(2) . . ? C8 C7 H7 126.4 . . ? C6 C7 H7 126.4 . . ? C7 C8 C9 107.1(2) . . ? C7 C8 H8 126.5 . . ? C9 C8 H8 126.5 . . ? N2 C9 C10 125.3(2) . . ? N2 C9 C8 110.73(19) . . ? C10 C9 C8 123.9(2) . . ? C11 C10 C9 122.0(2) . . ? C11 C10 C27 118.9(2) . . ? C9 C10 C27 119.1(2) . . ? C10 C11 N3 125.8(2) . . ? C10 C11 C12D 153.4(6) . . ? N3 C11 C12D 80.6(6) . . ? C10 C11 C12 121.0(3) . . ? N3 C11 C12 113.2(2) . . ? C12D C11 C12 32.7(5) . . ? C13 C12 C11 104.8(4) . . ? C13 C12 H12 127.6 . . ? C11 C12 H12 127.6 . . ? C12 C13 C14 106.4(4) . . ? C12 C13 H13 126.8 . . ? C14 C13 H13 126.8 . . ? O13D C12D C11 132.0(17) . . ? O13D C12D C14 132.4(17) . . ? C11 C12D C14 95.6(7) . . ? O13D C12D N3 178.0(9) . . ? C11 C12D N3 48.0(4) . . ? C14 C12D N3 47.5(4) . . ? N3 C14 C15 126.4(2) . . ? N3 C14 C12D 80.8(6) . . ? C15 C14 C12D 152.4(6) . . ? N3 C14 C13 112.4(2) . . ? C15 C14 C13 121.1(3) . . ? C12D C14 C13 31.8(5) . . ? C16 C15 C14 118.1(2) . . ? C16 C15 C33 120.69(19) . . ? C14 C15 C33 121.17(19) . . ? C15 C16 N4 126.7(2) . . ? C15 C16 C17D 147.0(3) . . ? N4 C16 C17D 86.4(3) . . ? C15 C16 C17 120.0(3) . . ? N4 C16 C17 113.1(3) . . ? C17D C16 C17 27.4(2) . . ? C18 C17 C16 107.0(7) . . ? C18 C17 H17 126.5 . . ? C16 C17 H17 126.5 . . ? C17 C18 C19 101.1(6) . . ? C17 C18 H18 129.4 . . ? C19 C18 H18 129.4 . . ? O18D C17D C16 135.3(6) . . ? O18D C17D C19 134.3(6) . . ? C16 C17D C19 90.2(3) . . ? O18D C17D N4 176.8(4) . . ? C16 C17D N4 45.32(17) . . ? C19 C17D N4 44.89(17) . . ? C20 C19 N4 126.9(2) . . ? C20 C19 C18 113.2(3) . . ? N4 C19 C18 119.6(3) . . ? C20 C19 C17D 148.4(3) . . ? N4 C19 C17D 84.6(3) . . ? C18 C19 C17D 35.2(3) . . ? C19 C20 C1 118.9(2) . . ? C19 C20 C39 120.3(2) . . ? C1 C20 C39 120.8(2) . . ? C26 C21 C22 118.6(2) . . ? C26 C21 C5 121.60(19) . . ? C22 C21 C5 119.76(19) . . ? C23 C22 C21 120.7(2) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C24 C23 C22 120.0(2) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.0(2) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C25 C26 120.5(2) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C21 120.2(2) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? C28 C27 C32 118.3(2) . . ? C28 C27 C10 121.3(2) . . ? C32 C27 C10 120.4(2) . . ? C27 C28 C29 120.6(2) . . ? C27 C28 H28 119.7 . . ? C29 C28 H28 119.7 . . ? C30 C29 C28 120.1(2) . . ? C30 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? C29 C30 C31 120.0(2) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 120.0 . . ? C30 C31 C32 120.3(2) . . ? C30 C31 H31 119.9 . . ? C32 C31 H31 119.9 . . ? C31 C32 C27 120.7(2) . . ? C31 C32 H32 119.6 . . ? C27 C32 H32 119.6 . . ? C38 C33 C34 118.7(2) . . ? C38 C33 C15 120.73(19) . . ? C34 C33 C15 120.57(19) . . ? C35 C34 C33 120.2(2) . . ? C35 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? C36 C35 C34 120.5(2) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C35 C36 C37 119.6(2) . . ? C35 C36 H36 120.2 . . ? C37 C36 H36 120.2 . . ? C38 C37 C36 120.0(2) . . ? C38 C37 H37 120.0 . . ? C36 C37 H37 120.0 . . ? C37 C38 C33 121.0(2) . . ? C37 C38 H38 119.5 . . ? C33 C38 H38 119.5 . . ? C40 C39 C44 118.5(2) . . ? C40 C39 C20 120.6(2) . . ? C44 C39 C20 120.9(2) . . ? C39 C40 C41 120.3(3) . . ? C39 C40 H40 119.9 . . ? C41 C40 H40 119.9 . . ? C42 C41 C40 120.7(3) . . ? C42 C41 H41 119.7 . . ? C40 C41 H41 119.7 . . ? C41 C42 C43 119.6(3) . . ? C41 C42 H42 120.2 . . ? C43 C42 H42 120.2 . . ? C42 C43 C44 120.1(3) . . ? C42 C43 H43 120.0 . . ? C44 C43 H43 120.0 . . ? C43 C44 C39 120.9(2) . . ? C43 C44 H44 119.6 . . ? C39 C44 H44 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Ni1 N1 C1 2.11(19) . . . . ? N3 Ni1 N1 C1 24.6(16) . . . . ? N2 Ni1 N1 C1 -175.84(18) . . . . ? N4 Ni1 N1 C4 -179.97(18) . . . . ? N3 Ni1 N1 C4 -157.5(14) . . . . ? N2 Ni1 N1 C4 2.08(18) . . . . ? N4 Ni1 N1 C2D -86(22) . . . . ? N3 Ni1 N1 C2D -63(22) . . . . ? N2 Ni1 N1 C2D 96(22) . . . . ? N4 Ni1 N2 C6 -99(2) . . . . ? N3 Ni1 N2 C6 176.71(18) . . . . ? N1 Ni1 N2 C6 -2.25(18) . . . . ? N4 Ni1 N2 C9 86(2) . . . . ? N3 Ni1 N2 C9 2.17(18) . . . . ? N1 Ni1 N2 C9 -176.79(18) . . . . ? N4 Ni1 N3 C14 -0.25(18) . . . . ? N2 Ni1 N3 C14 177.70(18) . . . . ? N1 Ni1 N3 C14 -22.7(16) . . . . ? N4 Ni1 N3 C11 177.96(18) . . . . ? N2 Ni1 N3 C11 -4.09(18) . . . . ? N1 Ni1 N3 C11 155.5(14) . . . . ? N4 Ni1 N3 C12D 127(20) . . . . ? N2 Ni1 N3 C12D -55(20) . . . . ? N1 Ni1 N3 C12D 105(20) . . . . ? N3 Ni1 N4 C19 177.69(19) . . . . ? N2 Ni1 N4 C19 94(2) . . . . ? N1 Ni1 N4 C19 -3.45(19) . . . . ? N3 Ni1 N4 C16 6.25(19) . . . . ? N2 Ni1 N4 C16 -78(2) . . . . ? N1 Ni1 N4 C16 -174.89(19) . . . . ? N3 Ni1 N4 C17D 79(3) . . . . ? N2 Ni1 N4 C17D -5(4) . . . . ? N1 Ni1 N4 C17D -102(3) . . . . ? C4 N1 C1 C20 -179.6(2) . . . . ? C2D N1 C1 C20 176.4(7) . . . . ? Ni1 N1 C1 C20 -1.3(3) . . . . ? C4 N1 C1 C2 -1.0(2) . . . . ? C2D N1 C1 C2 -4.9(7) . . . . ? Ni1 N1 C1 C2 177.33(16) . . . . ? C4 N1 C1 C2D 4.0(7) . . . . ? Ni1 N1 C1 C2D -177.7(6) . . . . ? N1 C1 C2 C3 0.5(3) . . . . ? C20 C1 C2 C3 179.3(2) . . . . ? C2D C1 C2 C3 -9.4(13) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? N1 C1 C2D O3D -176(2) . . . . ? C20 C1 C2D O3D 10(3) . . . . ? C2 C1 C2D O3D -5.5(14) . . . . ? N1 C1 C2D C4 -3.5(6) . . . . ? C20 C1 C2D C4 -177.3(7) . . . . ? C2 C1 C2D C4 167.2(18) . . . . ? C20 C1 C2D N1 -173.8(12) . . . . ? C2 C1 C2D N1 170.7(12) . . . . ? C1 N1 C2D O3D 151(18) . . . . ? C4 N1 C2D O3D -24(18) . . . . ? Ni1 N1 C2D O3D -120(19) . . . . ? C4 N1 C2D C1 -175.2(8) . . . . ? Ni1 N1 C2D C1 89(22) . . . . ? C1 N1 C2D C4 175.2(8) . . . . ? Ni1 N1 C2D C4 -96(22) . . . . ? C1 N1 C4 C5 177.8(2) . . . . ? C2D N1 C4 C5 -178.4(7) . . . . ? Ni1 N1 C4 C5 -0.5(3) . . . . ? C1 N1 C4 C3 1.1(2) . . . . ? C2D N1 C4 C3 4.9(6) . . . . ? Ni1 N1 C4 C3 -177.30(16) . . . . ? C1 N1 C4 C2D -3.8(6) . . . . ? Ni1 N1 C4 C2D 177.8(6) . . . . ? C2 C3 C4 C5 -177.7(2) . . . . ? C2 C3 C4 N1 -0.8(3) . . . . ? C2 C3 C4 C2D 8.3(11) . . . . ? O3D C2D C4 C5 -6(3) . . . . ? C1 C2D C4 C5 -179.5(7) . . . . ? N1 C2D C4 C5 177.0(12) . . . . ? O3D C2D C4 N1 177.2(19) . . . . ? C1 C2D C4 N1 3.5(6) . . . . ? O3D C2D C4 C3 5.8(11) . . . . ? C1 C2D C4 C3 -167.9(16) . . . . ? N1 C2D C4 C3 -171.4(11) . . . . ? N1 C4 C5 C6 -1.7(3) . . . . ? C3 C4 C5 C6 174.7(2) . . . . ? C2D C4 C5 C6 -178.1(14) . . . . ? N1 C4 C5 C21 176.55(19) . . . . ? C3 C4 C5 C21 -7.0(3) . . . . ? C2D C4 C5 C21 0.2(15) . . . . ? C9 N2 C6 C5 176.5(2) . . . . ? Ni1 N2 C6 C5 0.9(3) . . . . ? C9 N2 C6 C7 -0.1(2) . . . . ? Ni1 N2 C6 C7 -175.70(15) . . . . ? C4 C5 C6 N2 1.6(3) . . . . ? C21 C5 C6 N2 -176.71(19) . . . . ? C4 C5 C6 C7 177.7(2) . . . . ? C21 C5 C6 C7 -0.6(3) . . . . ? N2 C6 C7 C8 0.3(3) . . . . ? C5 C6 C7 C8 -176.3(2) . . . . ? C6 C7 C8 C9 -0.4(3) . . . . ? C6 N2 C9 C10 -176.7(2) . . . . ? Ni1 N2 C9 C10 -1.1(3) . . . . ? C6 N2 C9 C8 -0.1(2) . . . . ? Ni1 N2 C9 C8 175.46(15) . . . . ? C7 C8 C9 N2 0.3(3) . . . . ? C7 C8 C9 C10 177.0(2) . . . . ? N2 C9 C10 C11 1.0(3) . . . . ? C8 C9 C10 C11 -175.2(2) . . . . ? N2 C9 C10 C27 -177.48(19) . . . . ? C8 C9 C10 C27 6.4(3) . . . . ? C9 C10 C11 N3 -3.1(3) . . . . ? C27 C10 C11 N3 175.3(2) . . . . ? C9 C10 C11 C12D -174.5(9) . . . . ? C27 C10 C11 C12D 4.0(10) . . . . ? C9 C10 C11 C12 178.5(2) . . . . ? C27 C10 C11 C12 -3.1(3) . . . . ? C14 N3 C11 C10 -176.1(2) . . . . ? C12D N3 C11 C10 -176.1(5) . . . . ? Ni1 N3 C11 C10 5.3(3) . . . . ? C14 N3 C11 C12D 0.0(4) . . . . ? Ni1 N3 C11 C12D -178.6(4) . . . . ? C14 N3 C11 C12 2.4(2) . . . . ? C12D N3 C11 C12 2.4(4) . . . . ? Ni1 N3 C11 C12 -176.19(17) . . . . ? C10 C11 C12 C13 178.4(2) . . . . ? N3 C11 C12 C13 -0.2(3) . . . . ? C12D C11 C12 C13 4.3(7) . . . . ? C11 C12 C13 C14 -2.0(3) . . . . ? C10 C11 C12D O13D -10(2) . . . . ? N3 C11 C12D O13D 177.3(12) . . . . ? C12 C11 C12D O13D 1.4(7) . . . . ? C10 C11 C12D C14 173.0(6) . . . . ? N3 C11 C12D C14 0.0(4) . . . . ? C12 C11 C12D C14 -175.9(11) . . . . ? C10 C11 C12D N3 172.9(9) . . . . ? C12 C11 C12D N3 -175.9(7) . . . . ? C14 N3 C12D O13D 88(49) . . . . ? C11 N3 C12D O13D -92(49) . . . . ? Ni1 N3 C12D O13D -41(67) . . . . ? C14 N3 C12D C11 180.0(5) . . . . ? Ni1 N3 C12D C11 51(20) . . . . ? C11 N3 C12D C14 -180.0(5) . . . . ? Ni1 N3 C12D C14 -129(20) . . . . ? C11 N3 C14 C15 175.6(2) . . . . ? C12D N3 C14 C15 175.6(5) . . . . ? Ni1 N3 C14 C15 -5.8(3) . . . . ? C11 N3 C14 C12D 0.0(4) . . . . ? Ni1 N3 C14 C12D 178.6(4) . . . . ? C11 N3 C14 C13 -3.7(2) . . . . ? C12D N3 C14 C13 -3.7(4) . . . . ? Ni1 N3 C14 C13 174.84(17) . . . . ? O13D C12D C14 N3 -177.3(12) . . . . ? C11 C12D C14 N3 0.0(4) . . . . ? O13D C12D C14 C15 10.4(19) . . . . ? C11 C12D C14 C15 -172.4(5) . . . . ? N3 C12D C14 C15 -172.3(8) . . . . ? O13D C12D C14 C13 -3.8(7) . . . . ? C11 C12D C14 C13 173.4(11) . . . . ? N3 C12D C14 C13 173.4(8) . . . . ? C12 C13 C14 N3 3.8(3) . . . . ? C12 C13 C14 C15 -175.6(2) . . . . ? C12 C13 C14 C12D -3.2(8) . . . . ? N3 C14 C15 C16 6.5(3) . . . . ? C12D C14 C15 C16 177.1(9) . . . . ? C13 C14 C15 C16 -174.2(2) . . . . ? N3 C14 C15 C33 -172.58(19) . . . . ? C12D C14 C15 C33 -2.0(10) . . . . ? C13 C14 C15 C33 6.7(3) . . . . ? C14 C15 C16 N4 -0.2(3) . . . . ? C33 C15 C16 N4 178.92(19) . . . . ? C14 C15 C16 C17D 178.3(4) . . . . ? C33 C15 C16 C17D -2.7(5) . . . . ? C14 C15 C16 C17 -174.8(3) . . . . ? C33 C15 C16 C17 4.2(4) . . . . ? C19 N4 C16 C15 179.5(2) . . . . ? Ni1 N4 C16 C15 -7.1(3) . . . . ? C17D N4 C16 C15 179.1(3) . . . . ? C19 N4 C16 C17D 0.3(2) . . . . ? Ni1 N4 C16 C17D 173.7(2) . . . . ? C19 N4 C16 C17 -5.5(3) . . . . ? Ni1 N4 C16 C17 167.9(3) . . . . ? C17D N4 C16 C17 -5.9(3) . . . . ? C15 C16 C17 C18 -179.1(4) . . . . ? N4 C16 C17 C18 5.6(5) . . . . ? C17D C16 C17 C18 -7.3(5) . . . . ? C16 C17 C18 C19 -2.5(5) . . . . ? C15 C16 C17D O18D 5.7(8) . . . . ? N4 C16 C17D O18D -175.5(5) . . . . ? C17 C16 C17D O18D -7.3(5) . . . . ? C15 C16 C17D C19 -179.0(3) . . . . ? N4 C16 C17D C19 -0.3(2) . . . . ? C17 C16 C17D C19 167.9(8) . . . . ? C15 C16 C17D N4 -178.7(5) . . . . ? C17 C16 C17D N4 168.2(7) . . . . ? C19 N4 C17D O18D -76(10) . . . . ? C16 N4 C17D O18D 103(10) . . . . ? Ni1 N4 C17D O18D 26(12) . . . . ? C19 N4 C17D C16 -179.6(3) . . . . ? Ni1 N4 C17D C16 -77(3) . . . . ? C16 N4 C17D C19 179.6(3) . . . . ? Ni1 N4 C17D C19 103(3) . . . . ? C16 N4 C19 C20 177.7(2) . . . . ? Ni1 N4 C19 C20 4.3(3) . . . . ? C17D N4 C19 C20 178.0(3) . . . . ? C16 N4 C19 C18 4.2(3) . . . . ? Ni1 N4 C19 C18 -169.2(3) . . . . ? C17D N4 C19 C18 4.5(3) . . . . ? C16 N4 C19 C17D -0.3(2) . . . . ? Ni1 N4 C19 C17D -173.7(2) . . . . ? C17 C18 C19 C20 -175.3(4) . . . . ? C17 C18 C19 N4 -1.0(5) . . . . ? C17 C18 C19 C17D 6.8(4) . . . . ? O18D C17D C19 C20 -1.3(8) . . . . ? C16 C17D C19 C20 -176.6(4) . . . . ? N4 C17D C19 C20 -176.9(5) . . . . ? O18D C17D C19 N4 175.6(5) . . . . ? C16 C17D C19 N4 0.3(2) . . . . ? O18D C17D C19 C18 2.5(5) . . . . ? C16 C17D C19 C18 -172.8(5) . . . . ? N4 C17D C19 C18 -173.1(4) . . . . ? N4 C19 C20 C1 -2.2(3) . . . . ? C18 C19 C20 C1 171.6(3) . . . . ? C17D C19 C20 C1 173.9(4) . . . . ? N4 C19 C20 C39 178.7(2) . . . . ? C18 C19 C20 C39 -7.5(4) . . . . ? C17D C19 C20 C39 -5.1(6) . . . . ? N1 C1 C20 C19 0.8(3) . . . . ? C2 C1 C20 C19 -177.7(2) . . . . ? C2D C1 C20 C19 173.3(14) . . . . ? N1 C1 C20 C39 179.9(2) . . . . ? C2 C1 C20 C39 1.4(3) . . . . ? C2D C1 C20 C39 -7.7(14) . . . . ? C4 C5 C21 C26 113.6(2) . . . . ? C6 C5 C21 C26 -68.0(3) . . . . ? C4 C5 C21 C22 -65.7(3) . . . . ? C6 C5 C21 C22 112.7(2) . . . . ? C26 C21 C22 C23 0.4(3) . . . . ? C5 C21 C22 C23 179.8(2) . . . . ? C21 C22 C23 C24 -0.1(3) . . . . ? C22 C23 C24 C25 -0.2(4) . . . . ? C23 C24 C25 C26 0.2(4) . . . . ? C24 C25 C26 C21 0.2(4) . . . . ? C22 C21 C26 C25 -0.4(3) . . . . ? C5 C21 C26 C25 -179.8(2) . . . . ? C11 C10 C27 C28 64.1(3) . . . . ? C9 C10 C27 C28 -117.4(3) . . . . ? C11 C10 C27 C32 -115.2(3) . . . . ? C9 C10 C27 C32 63.3(3) . . . . ? C32 C27 C28 C29 1.6(4) . . . . ? C10 C27 C28 C29 -177.7(2) . . . . ? C27 C28 C29 C30 -0.1(4) . . . . ? C28 C29 C30 C31 -1.2(5) . . . . ? C29 C30 C31 C32 0.9(5) . . . . ? C30 C31 C32 C27 0.7(4) . . . . ? C28 C27 C32 C31 -2.0(4) . . . . ? C10 C27 C32 C31 177.4(2) . . . . ? C16 C15 C33 C38 47.1(3) . . . . ? C14 C15 C33 C38 -133.9(2) . . . . ? C16 C15 C33 C34 -131.5(2) . . . . ? C14 C15 C33 C34 47.6(3) . . . . ? C38 C33 C34 C35 0.6(3) . . . . ? C15 C33 C34 C35 179.2(2) . . . . ? C33 C34 C35 C36 -0.6(3) . . . . ? C34 C35 C36 C37 0.0(4) . . . . ? C35 C36 C37 C38 0.5(4) . . . . ? C36 C37 C38 C33 -0.5(4) . . . . ? C34 C33 C38 C37 -0.1(3) . . . . ? C15 C33 C38 C37 -178.7(2) . . . . ? C19 C20 C39 C40 -59.7(4) . . . . ? C1 C20 C39 C40 121.2(3) . . . . ? C19 C20 C39 C44 119.9(3) . . . . ? C1 C20 C39 C44 -59.1(3) . . . . ? C44 C39 C40 C41 1.2(5) . . . . ? C20 C39 C40 C41 -179.1(3) . . . . ? C39 C40 C41 C42 -1.0(6) . . . . ? C40 C41 C42 C43 0.5(6) . . . . ? C41 C42 C43 C44 -0.2(5) . . . . ? C42 C43 C44 C39 0.5(4) . . . . ? C40 C39 C44 C43 -1.0(4) . . . . ? C20 C39 C44 C43 179.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.46 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.512 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.058 # Attachment '4Ni' data_06021 _database_code_depnum_ccdc_archive 'CCDC 617062' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H26 N4 Ni O2' _chemical_formula_sum 'C43 H26 N4 Ni O2' _chemical_formula_weight 689.39 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I-42d _symmetry_space_group_name_Hall 'I -4 2bw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x, -y+1/2, -z+1/4' '-x, y+1/2, -z+1/4' 'y, x+1/2, z+1/4' '-y, -x+1/2, z+1/4' '-y, x, -z' 'y, -x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1, -z+3/4' '-x+1/2, y+1, -z+3/4' 'y+1/2, x+1, z+3/4' '-y+1/2, -x+1, z+3/4' '-y+1/2, x+1/2, -z+1/2' 'y+1/2, -x+1/2, -z+1/2' _cell_length_a 15.117(4) _cell_length_b 15.117(4) _cell_length_c 13.535(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3093.0(15) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2022 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 22.3 _exptl_crystal_description block _exptl_crystal_colour red-violet _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.676 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9054 _exptl_absorpt_correction_T_max 0.9355 _exptl_absorpt_process_details 'SADABS, R. Blessing; 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_details '0.30 degree frames measured for 60 seconds each' _diffrn_measurement_method \w-scans _diffrn_measurement_device 'three-circle goniometer with fixed chi' _diffrn_measurement_device_type 'Bruker Platform goniometer' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker SMART 6000' _diffrn_detector_area_resol_mean 44.52 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12824 _diffrn_reflns_av_R_equivalents 0.0806 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.12 _reflns_number_total 1382 _reflns_number_gt 1196 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SIR-2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2003), XTEL (loc. libr.)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0600P)^2^+0.8624P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(3) _refine_ls_number_reflns 1382 _refine_ls_number_parameters 124 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.035 _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 Ni1 Ni 1.0000 0.0000 0.5000 0.0300(2) Uani 1 4 d S . . N1 N 0.88963(15) 0.06457(16) 0.4975(3) 0.0325(6) Uani 1 1 d D A . C1 C 0.8790(2) 0.1536(2) 0.4822(3) 0.0378(9) Uani 1 1 d D . . C2 C 0.78855(19) 0.17791(19) 0.4937(3) 0.0458(9) Uani 0.75 1 d P A 1 H2 H 0.7642 0.2353 0.4847 0.055 Uiso 0.75 1 calc PR A 1 C3 C 0.7433(2) 0.1029(2) 0.5200(3) 0.0465(10) Uani 0.75 1 d P A 1 H3 H 0.6821 0.0986 0.5348 0.056 Uiso 0.75 1 calc PR A 1 O2A O 0.78855(19) 0.17791(19) 0.4937(3) 0.0458(9) Uani 0.167(4) 1 d PD A 2 C3A C 0.7433(2) 0.1029(2) 0.5200(3) 0.0465(10) Uani 0.167(4) 1 d PD A 2 O1A O 0.6727(8) 0.1167(10) 0.5376(14) 0.062(5) Uani 0.167(4) 1 d PD A 2 O3B O 0.7433(2) 0.1029(2) 0.5200(3) 0.0465(10) Uani 0.083(4) 1 d PD A 3 C2B C 0.78855(19) 0.17791(19) 0.4937(3) 0.0458(9) Uani 0.083(4) 1 d PD A 3 O1B O 0.7430(15) 0.2345(13) 0.498(2) 0.062(5) Uani 0.083(4) 1 d PD A 3 C4 C 0.80644(19) 0.0324(2) 0.5209(3) 0.0358(9) Uani 1 1 d D . . C5 C 0.7844(2) -0.0561(2) 0.5333(3) 0.0340(9) Uani 1 1 d . A . C6 C 0.6920(2) -0.08085(19) 0.5595(3) 0.0348(8) Uani 1 1 d . . . C7 C 0.6254(2) -0.0805(2) 0.4903(4) 0.0464(9) Uani 1 1 d . A . H7 H 0.6381 -0.0625 0.4246 0.056 Uiso 1 1 calc R . . C8 C 0.5400(2) -0.1058(3) 0.5146(4) 0.0499(10) Uani 1 1 d . . . H8 H 0.4946 -0.1046 0.4661 0.060 Uiso 1 1 calc R A . C9 C 0.5212(2) -0.1326(2) 0.6093(3) 0.0459(9) Uani 1 1 d . A . H9 H 0.4631 -0.1509 0.6263 0.055 Uiso 1 1 calc R . . C10 C 0.5870(3) -0.1329(3) 0.6792(4) 0.0533(11) Uani 1 1 d . . . H10 H 0.5740 -0.1504 0.7450 0.064 Uiso 1 1 calc R A . C11 C 0.6722(2) -0.1077(3) 0.6545(3) 0.0458(9) Uani 1 1 d . A . H11 H 0.7174 -0.1089 0.7032 0.055 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 Ni1 0.0191(2) 0.0191(2) 0.0518(5) 0.000 0.000 0.000 N1 0.0250(12) 0.0208(11) 0.0518(18) 0.0012(16) 0.0037(15) -0.0002(8) C1 0.0317(17) 0.0263(15) 0.055(3) 0.0008(16) 0.0020(17) 0.0060(13) C2 0.0323(15) 0.0234(14) 0.082(3) 0.005(2) 0.001(2) 0.0041(12) C3 0.0247(17) 0.0366(18) 0.078(3) -0.0065(19) 0.0033(17) 0.0054(14) O2A 0.0323(15) 0.0234(14) 0.082(3) 0.005(2) 0.001(2) 0.0041(12) C3A 0.0247(17) 0.0366(18) 0.078(3) -0.0065(19) 0.0033(17) 0.0054(14) O1A 0.017(7) 0.028(7) 0.140(16) -0.005(9) 0.000(8) 0.003(5) O3B 0.0247(17) 0.0366(18) 0.078(3) -0.0065(19) 0.0033(17) 0.0054(14) C2B 0.0323(15) 0.0234(14) 0.082(3) 0.005(2) 0.001(2) 0.0041(12) O1B 0.017(7) 0.028(7) 0.140(16) -0.005(9) 0.000(8) 0.003(5) C4 0.0226(16) 0.0251(14) 0.060(3) 0.0002(15) 0.0038(16) 0.0004(12) C5 0.0197(15) 0.0266(16) 0.056(3) -0.0016(14) 0.0014(15) -0.0046(13) C6 0.0238(17) 0.0228(17) 0.058(2) -0.0024(15) 0.0061(16) -0.0042(13) C7 0.0299(17) 0.052(2) 0.057(3) 0.006(2) 0.0000(18) -0.0065(16) C8 0.0304(17) 0.052(2) 0.067(3) 0.000(2) -0.0039(19) -0.0062(15) C9 0.030(2) 0.039(2) 0.068(3) -0.0011(18) 0.0090(17) -0.0086(14) C10 0.041(2) 0.060(3) 0.059(3) 0.011(2) 0.0045(19) -0.012(2) C11 0.0320(19) 0.047(2) 0.058(3) 0.0002(19) -0.0027(18) -0.0054(15) _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 Ni1 N1 1.933(2) 7_646 ? Ni1 N1 1.933(2) 2_755 ? Ni1 N1 1.933(2) 8_666 ? Ni1 N1 1.933(2) . ? N1 C1 1.371(4) . ? N1 C4 1.385(4) . ? C1 C5 1.373(5) 8_666 ? C1 C2 1.425(4) . ? C2 C3 1.371(4) . ? C2 H2 0.9500 . ? C3 C4 1.431(4) . ? C3 H3 0.9500 . ? C4 C5 1.388(4) . ? C5 C1 1.373(5) 7_646 ? C5 C6 1.489(4) . ? C6 C7 1.374(5) . ? C6 C11 1.382(6) . ? C7 C8 1.386(5) . ? C7 H7 0.9500 . ? C8 C9 1.374(6) . ? C8 H8 0.9500 . ? C9 C10 1.372(6) . ? C9 H9 0.9500 . ? C10 C11 1.384(5) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? 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 Ni1 N1 90.017(4) 7_646 2_755 ? N1 Ni1 N1 178.0(2) 7_646 8_666 ? N1 Ni1 N1 90.017(4) 2_755 8_666 ? N1 Ni1 N1 90.017(4) 7_646 . ? N1 Ni1 N1 178.0(2) 2_755 . ? N1 Ni1 N1 90.017(4) 8_666 . ? C1 N1 C4 105.9(2) . . ? C1 N1 Ni1 126.8(2) . . ? C4 N1 Ni1 127.0(2) . . ? N1 C1 C5 127.6(3) . 8_666 ? N1 C1 C2 110.4(3) . . ? C5 C1 C2 121.7(3) 8_666 . ? C3 C2 C1 107.1(3) . . ? C3 C2 H2 126.5 . . ? C1 C2 H2 126.5 . . ? C2 C3 C4 106.6(3) . . ? C2 C3 H3 126.7 . . ? C4 C3 H3 126.7 . . ? N1 C4 C5 125.8(3) . . ? N1 C4 C3 110.0(3) . . ? C5 C4 C3 124.0(3) . . ? C1 C5 C4 120.4(3) 7_646 . ? C1 C5 C6 119.8(3) 7_646 . ? C4 C5 C6 119.8(3) . . ? C7 C6 C11 118.4(3) . . ? C7 C6 C5 121.6(3) . . ? C11 C6 C5 119.9(3) . . ? C6 C7 C8 121.3(4) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C9 C8 C7 119.7(4) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C10 C9 C8 119.6(3) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 120.5(4) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C6 C11 C10 120.5(4) . . ? C6 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Ni1 N1 C1 -170.9(4) 7_646 . . . ? N1 Ni1 N1 C1 -79.9(4) 2_755 . . . ? N1 Ni1 N1 C1 11.1(3) 8_666 . . . ? N1 Ni1 N1 C4 16.4(3) 7_646 . . . ? N1 Ni1 N1 C4 107.4(4) 2_755 . . . ? N1 Ni1 N1 C4 -161.6(4) 8_666 . . . ? C4 N1 C1 C5 173.1(4) . . . 8_666 ? Ni1 N1 C1 C5 -0.9(6) . . . 8_666 ? C4 N1 C1 C2 -1.3(5) . . . . ? Ni1 N1 C1 C2 -175.3(3) . . . . ? N1 C1 C2 C3 2.2(5) . . . . ? C5 C1 C2 C3 -172.6(4) 8_666 . . . ? C1 C2 C3 C4 -2.1(5) . . . . ? C1 N1 C4 C5 173.6(4) . . . . ? Ni1 N1 C4 C5 -12.4(7) . . . . ? C1 N1 C4 C3 0.0(5) . . . . ? Ni1 N1 C4 C3 173.9(3) . . . . ? C2 C3 C4 N1 1.4(5) . . . . ? C2 C3 C4 C5 -172.4(4) . . . . ? N1 C4 C5 C1 -3.1(7) . . . 7_646 ? C3 C4 C5 C1 169.7(4) . . . 7_646 ? N1 C4 C5 C6 179.4(4) . . . . ? C3 C4 C5 C6 -7.8(7) . . . . ? C1 C5 C6 C7 -100.8(4) 7_646 . . . ? C4 C5 C6 C7 76.7(5) . . . . ? C1 C5 C6 C11 77.1(5) 7_646 . . . ? C4 C5 C6 C11 -105.4(4) . . . . ? C11 C6 C7 C8 0.3(6) . . . . ? C5 C6 C7 C8 178.3(3) . . . . ? C6 C7 C8 C9 -0.6(6) . . . . ? C7 C8 C9 C10 0.9(6) . . . . ? C8 C9 C10 C11 -1.1(6) . . . . ? C7 C6 C11 C10 -0.5(6) . . . . ? C5 C6 C11 C10 -178.5(4) . . . . ? C9 C10 C11 C6 0.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.12 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.192 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.057