# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_z:\xraydata\gareth\cddito~1\work\datase~1\ctpm _audit_creation_method SHELXL-97 _chemical_name_systematic ; mer-[Cd(k-O,N,N-3.11a)2] ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C40 H40 Cd N10 O4, 2(C H4 O), 2(O) ; _chemical_formula_sum 'C42 H48 Cd N10 O8' _chemical_formula_weight 933.30 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.329(7) _cell_length_b 12.877(7) _cell_length_c 14.883(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.625(18) _cell_angle_gamma 90.00 _cell_volume 2362(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 0.521 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9449 _exptl_absorpt_correction_T_max 0.9795 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Smart 6K' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13397 _diffrn_reflns_av_R_equivalents 0.0583 _diffrn_reflns_av_sigmaI/netI 0.1202 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8279 _reflns_number_gt 6016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Smart - Bruker' _computing_cell_refinement 'Saint- Bruker' _computing_data_reduction 'Saint - Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Xseed _computing_publication_material Xseed _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. There are two very disordered solvent molecules within the structure. We have modelled these as two isolated water molecules (2 isolated oyxgen atoms) rather than squeezing the structure. More complicated disordered models did not result in an improved refinement. ; _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^)+(0.0856P)^2^+3.6957P] 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 constr _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 0.02(5) _refine_ls_number_reflns 8279 _refine_ls_number_parameters 561 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1096 _refine_ls_R_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1631 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd -0.01277(4) 0.94668(7) 0.75056(5) 0.02629(18) Uani 1 1 d . . . O1 O 0.1334(7) 1.0690(7) 0.7487(6) 0.040(2) Uani 1 1 d . . . O1W O 0.360(3) 0.9777(19) 0.849(3) 0.43(3) Uani 1 1 d . . . N1 N -0.0435(6) 0.9339(8) 0.5434(5) 0.0285(19) Uani 1 1 d . . . C1 C -0.0729(9) 0.9277(10) 0.3741(7) 0.048(3) Uani 1 1 d . . . H1A H -0.0592 0.8530 0.3693 0.072 Uiso 1 1 calc R . . H1B H -0.0424 0.9634 0.3224 0.072 Uiso 1 1 calc R . . H1C H -0.1513 0.9402 0.3748 0.072 Uiso 1 1 calc R . . O2 O -0.1677(5) 0.8033(5) 0.5123(5) 0.0349(16) Uani 1 1 d . . . O2W O 0.352(2) 0.9222(17) 0.6573(18) 0.302(16) Uani 1 1 d . . . N2 N 0.0150(6) 0.9883(5) 0.6073(5) 0.0212(17) Uani 1 1 d . . . C2 C -0.0206(7) 0.9685(8) 0.4592(7) 0.032(3) Uani 1 1 d . . . O3 O 0.1338(7) 0.8242(7) 0.7584(6) 0.040(2) Uani 1 1 d . . . N3 N 0.1431(6) 1.1289(6) 0.6035(6) 0.0315(19) Uani 1 1 d . . . H3N H 0.1743 1.1754 0.5695 0.038 Uiso 1 1 calc R . . C3 C 0.0548(8) 1.0471(8) 0.4680(7) 0.035(2) Uani 1 1 d . . . H3 H 0.0868 1.0859 0.4214 0.042 Uiso 1 1 calc R . . O4 O -0.1685(5) 1.0885(5) 0.9825(5) 0.0313(15) Uani 1 1 d . . . N4 N 0.2350(8) 1.2133(7) 0.7197(7) 0.034(2) Uani 1 1 d . . . H4N H 0.2650 1.2500 0.6772 0.041 Uiso 1 1 calc R . . C4 C 0.0737(7) 1.0573(7) 0.5611(7) 0.031(2) Uani 1 1 d . . . O5 O 0.3650(6) 1.2816(6) 0.5719(6) 0.049(2) Uani 1 1 d . . . H5 H 0.3149 1.2980 0.5352 0.059 Uiso 1 1 calc R . . N5 N -0.1139(6) 0.8365(5) 0.6592(6) 0.0293(19) Uani 1 1 d . . . C5 C 0.1664(7) 1.1323(7) 0.6943(7) 0.028(2) Uani 1 1 d . . . O6 O 0.3664(6) 0.6074(6) 0.9406(5) 0.0457(19) Uani 1 1 d . . . H6 H 0.3105 0.5974 0.9703 0.055 Uiso 1 1 calc R . . N6 N -0.0448(5) 0.9570(9) 0.9560(5) 0.0269(17) Uani 1 1 d . . . C6 C 0.2594(10) 1.2400(9) 0.8096(8) 0.035(3) Uani 1 1 d . . . N7 N 0.0152(6) 0.9038(6) 0.8962(6) 0.028(2) Uani 1 1 d . . . C7 C 0.3482(8) 1.3127(8) 0.8213(8) 0.038(3) Uani 1 1 d . . . H7 H 0.3886 1.3340 0.7711 0.045 Uiso 1 1 calc R . . N8 N 0.1444(6) 0.7639(6) 0.9045(6) 0.0297(19) Uani 1 1 d . . . H8N H 0.1769 0.7181 0.9400 0.036 Uiso 1 1 calc R . . C8 C 0.3744(9) 1.3516(8) 0.9082(8) 0.042(3) Uani 1 1 d . . . H8 H 0.4338 1.3981 0.9152 0.050 Uiso 1 1 calc R . . N9 N 0.2349(9) 0.6802(8) 0.7911(8) 0.042(3) Uani 1 1 d . . . H9N H 0.2663 0.6449 0.8353 0.050 Uiso 1 1 calc R . . C9 C 0.3172(9) 1.3250(8) 0.9828(8) 0.040(3) Uani 1 1 d . . . N10 N -0.1144(6) 1.0557(6) 0.8380(6) 0.0306(19) Uani 1 1 d . . . C10 C 0.2290(10) 1.2521(8) 0.9679(8) 0.044(3) Uani 1 1 d . . . H10 H 0.1889 1.2288 1.0176 0.053 Uiso 1 1 calc R . . C11 C 0.2022(9) 1.2160(8) 0.8831(8) 0.045(3) Uani 1 1 d . . . H11 H 0.1406 1.1722 0.8758 0.054 Uiso 1 1 calc R . . C12 C 0.3439(9) 1.3638(9) 1.0739(9) 0.052(3) Uani 1 1 d . . . H12A H 0.4077 1.4091 1.0720 0.078 Uiso 1 1 calc R . . H12B H 0.3594 1.3050 1.1141 0.078 Uiso 1 1 calc R . . H12C H 0.2822 1.4032 1.0963 0.078 Uiso 1 1 calc R . . C13 C -0.1167(7) 0.8498(6) 0.5732(7) 0.024(2) Uani 1 1 d . . . C14 C -0.1784(8) 0.7565(7) 0.6974(7) 0.033(2) Uani 1 1 d . . . C15 C -0.2899(8) 0.7483(8) 0.6849(8) 0.039(3) Uani 1 1 d . . . H15 H -0.3273 0.7936 0.6442 0.047 Uiso 1 1 calc R . . C16 C -0.3483(11) 0.6723(11) 0.7327(11) 0.049(4) Uani 1 1 d . . . H16 H -0.4250 0.6697 0.7247 0.059 Uiso 1 1 calc R . . C17 C -0.2990(9) 0.6026(8) 0.7897(9) 0.049(3) Uani 1 1 d . . . C18 C -0.1884(9) 0.6100(8) 0.8043(8) 0.046(3) Uani 1 1 d . . . H17 H -0.1523 0.5642 0.8452 0.055 Uiso 1 1 calc R . . C19 C -0.1289(13) 0.6863(9) 0.7579(10) 0.046(4) Uani 1 1 d . . . H18 H -0.0526 0.6901 0.7681 0.055 Uiso 1 1 calc R . . C20 C -0.3637(10) 0.5229(9) 0.8406(10) 0.063(4) Uani 1 1 d . . . H20B H -0.3709 0.5457 0.9030 0.095 Uiso 1 1 calc R . . H20A H -0.3261 0.4559 0.8397 0.095 Uiso 1 1 calc R . . H20C H -0.4360 0.5156 0.8121 0.095 Uiso 1 1 calc R . . C21 C -0.0732(8) 0.9648(9) 1.1251(7) 0.043(3) Uani 1 1 d . . . H21A H -0.0485 0.9243 1.1775 0.064 Uiso 1 1 calc R . . H21B H -0.1522 0.9593 1.1179 0.064 Uiso 1 1 calc R . . H21C H -0.0529 1.0378 1.1338 0.064 Uiso 1 1 calc R . . C22 C -0.0213(7) 0.9240(8) 1.0430(7) 0.032(3) Uani 1 1 d . . . C23 C 0.0552(7) 0.8463(8) 1.0355(7) 0.032(2) Uani 1 1 d . . . H23 H 0.0890 0.8079 1.0831 0.039 Uiso 1 1 calc R . . C24 C 0.0727(7) 0.8358(7) 0.9435(7) 0.029(2) Uani 1 1 d . . . C25 C 0.1659(7) 0.7614(7) 0.8149(7) 0.026(2) Uani 1 1 d . . . C26 C 0.2585(9) 0.6500(8) 0.7032(8) 0.032(3) Uani 1 1 d . . . C27 C 0.3444(8) 0.5789(7) 0.6940(8) 0.038(3) Uani 1 1 d . . . H27 H 0.3847 0.5565 0.7458 0.046 Uiso 1 1 calc R . . C28 C 0.3706(9) 0.5412(9) 0.6093(9) 0.048(3) Uani 1 1 d . . . H28 H 0.4297 0.4945 0.6043 0.057 Uiso 1 1 calc R . . C29 C 0.3119(10) 0.5707(8) 0.5320(8) 0.044(3) Uani 1 1 d . . . C30 C 0.2280(10) 0.6435(8) 0.5421(9) 0.049(3) Uani 1 1 d . . . H30 H 0.1893 0.6673 0.4900 0.059 Uiso 1 1 calc R . . C31 C 0.2001(9) 0.6814(8) 0.6245(8) 0.046(3) Uani 1 1 d . . . H31 H 0.1415 0.7289 0.6287 0.055 Uiso 1 1 calc R . . C32 C 0.3385(9) 0.5293(9) 0.4387(8) 0.050(3) Uani 1 1 d . . . H32A H 0.3095 0.4588 0.4316 0.075 Uiso 1 1 calc R . . H32B H 0.4173 0.5280 0.4322 0.075 Uiso 1 1 calc R . . H32C H 0.3055 0.5746 0.3925 0.075 Uiso 1 1 calc R . . C33 C -0.1164(7) 1.0418(7) 0.9240(7) 0.028(2) Uani 1 1 d . . . C34 C -0.1785(7) 1.1366(7) 0.7947(7) 0.031(2) Uani 1 1 d . . . C35 C -0.2893(8) 1.1434(8) 0.8037(8) 0.038(2) Uani 1 1 d . . . H35 H -0.3252 1.0962 0.8419 0.046 Uiso 1 1 calc R . . C36 C -0.3495(13) 1.2198(11) 0.7564(12) 0.058(4) Uani 1 1 d . . . H36 H -0.4256 1.2249 0.7642 0.069 Uiso 1 1 calc R . . C37 C -0.2980(9) 1.2885(9) 0.6977(9) 0.052(3) Uani 1 1 d . . . C38 C -0.1871(8) 1.2813(8) 0.6888(8) 0.039(3) Uani 1 1 d . . . H38 H -0.1503 1.3264 0.6494 0.047 Uiso 1 1 calc R . . C39 C -0.1290(11) 1.2051(9) 0.7399(9) 0.036(3) Uani 1 1 d . . . H39 H -0.0523 1.2020 0.7355 0.044 Uiso 1 1 calc R . . C40 C -0.3629(11) 1.3679(10) 0.6423(11) 0.068(4) Uani 1 1 d . . . H40A H -0.3312 1.4371 0.6513 0.103 Uiso 1 1 calc R . . H40B H -0.4383 1.3683 0.6615 0.103 Uiso 1 1 calc R . . H40C H -0.3609 1.3494 0.5785 0.103 Uiso 1 1 calc R . . C41 C 0.4249(13) 1.1975(13) 0.5368(13) 0.099(6) Uani 1 1 d . . . H41A H 0.4681 1.2221 0.4867 0.148 Uiso 1 1 calc R . . H41B H 0.3748 1.1433 0.5153 0.148 Uiso 1 1 calc R . . H41C H 0.4733 1.1691 0.5840 0.148 Uiso 1 1 calc R . . C42 C 0.4279(12) 0.6886(11) 0.9802(11) 0.079(5) Uani 1 1 d . . . H42C H 0.3793 0.7371 1.0100 0.119 Uiso 1 1 calc R . . H42B H 0.4673 0.7254 0.9336 0.119 Uiso 1 1 calc R . . H42A H 0.4798 0.6597 1.0246 0.119 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 Cd1 0.0318(3) 0.0167(2) 0.0304(3) 0.0010(4) 0.0023(2) 0.0001(5) O1 0.031(5) 0.034(5) 0.055(6) 0.003(4) -0.011(5) -0.004(4) O1W 0.44(4) 0.18(3) 0.66(7) 0.07(3) -0.21(4) 0.18(3) N1 0.035(4) 0.017(5) 0.033(4) 0.005(4) 0.003(3) -0.004(4) C1 0.064(6) 0.051(9) 0.031(6) -0.004(5) 0.008(5) -0.013(6) O2 0.031(4) 0.023(3) 0.051(5) -0.007(3) -0.003(3) 0.001(3) O2W 0.43(4) 0.20(2) 0.28(3) 0.10(2) -0.05(2) -0.23(3) N2 0.042(4) 0.014(3) 0.008(4) -0.001(3) -0.001(3) -0.005(3) C2 0.033(5) 0.032(9) 0.031(6) 0.004(4) 0.004(4) 0.009(4) O3 0.046(6) 0.032(5) 0.042(6) 0.011(4) 0.019(5) 0.014(4) N3 0.026(4) 0.025(4) 0.043(6) 0.009(4) -0.001(4) -0.004(3) C3 0.030(5) 0.035(6) 0.042(7) 0.010(5) 0.006(5) -0.005(4) O4 0.032(4) 0.026(3) 0.036(4) -0.002(3) 0.004(3) -0.001(3) N4 0.034(5) 0.025(5) 0.044(7) 0.004(4) -0.002(5) -0.008(4) C4 0.014(4) 0.030(5) 0.048(7) 0.005(5) 0.004(4) 0.005(4) O5 0.035(4) 0.052(5) 0.059(6) 0.006(4) 0.013(4) 0.004(4) N5 0.029(4) 0.013(4) 0.046(6) -0.003(4) 0.005(4) -0.004(3) C5 0.021(4) 0.019(5) 0.045(7) 0.006(5) 0.008(4) -0.003(4) O6 0.045(5) 0.044(5) 0.048(5) 0.006(4) -0.002(4) -0.007(4) N6 0.027(3) 0.027(5) 0.027(4) 0.003(5) 0.001(3) -0.002(5) C6 0.037(7) 0.035(6) 0.033(7) 0.009(5) 0.006(5) 0.014(5) N7 0.024(4) 0.019(4) 0.042(6) -0.003(3) 0.005(4) 0.006(3) C7 0.031(5) 0.036(6) 0.047(7) 0.008(5) 0.002(5) 0.008(4) N8 0.037(4) 0.012(4) 0.040(6) 0.003(3) 0.004(4) 0.005(3) C8 0.040(6) 0.023(5) 0.061(9) -0.004(5) -0.004(5) -0.002(4) N9 0.043(6) 0.033(6) 0.050(8) 0.001(5) 0.003(5) -0.001(4) C9 0.039(6) 0.032(6) 0.049(7) 0.001(5) 0.004(5) 0.012(5) N10 0.032(4) 0.021(4) 0.039(6) -0.006(4) -0.002(4) 0.008(3) C10 0.061(7) 0.028(6) 0.044(8) 0.010(5) 0.002(6) -0.004(5) C11 0.045(6) 0.034(6) 0.057(8) 0.001(5) 0.005(6) -0.015(5) C12 0.054(7) 0.037(6) 0.064(9) -0.014(6) -0.013(6) 0.015(5) C13 0.022(5) 0.013(4) 0.039(7) 0.005(4) 0.007(4) 0.010(3) C14 0.034(5) 0.021(5) 0.045(7) -0.003(4) 0.012(5) -0.001(4) C15 0.034(6) 0.028(5) 0.055(8) 0.003(5) 0.000(5) -0.005(4) C16 0.023(7) 0.041(8) 0.085(11) 0.003(7) 0.009(6) -0.010(6) C17 0.053(7) 0.027(6) 0.068(9) 0.003(6) 0.023(6) -0.011(5) C18 0.044(6) 0.027(6) 0.068(9) 0.017(5) 0.013(6) 0.002(5) C19 0.045(9) 0.026(7) 0.068(10) 0.018(6) -0.005(7) -0.006(6) C20 0.058(8) 0.038(7) 0.095(12) 0.014(7) 0.027(7) -0.019(6) C21 0.057(6) 0.036(8) 0.036(6) 0.003(5) 0.005(5) 0.011(5) C22 0.022(4) 0.037(9) 0.038(6) 0.005(5) 0.002(4) -0.011(4) C23 0.032(5) 0.036(6) 0.028(6) 0.002(4) 0.000(4) 0.004(4) C24 0.023(5) 0.020(5) 0.044(7) -0.003(4) 0.001(4) -0.002(4) C25 0.028(5) 0.016(5) 0.035(6) 0.007(4) -0.004(4) 0.011(4) C26 0.035(6) 0.022(6) 0.038(7) -0.004(5) 0.004(5) -0.002(5) C27 0.027(5) 0.025(5) 0.063(8) 0.006(5) 0.004(5) 0.004(4) C28 0.044(6) 0.038(6) 0.061(9) -0.010(6) 0.013(6) -0.012(5) C29 0.049(7) 0.030(6) 0.053(8) -0.005(5) 0.000(6) -0.017(5) C30 0.071(8) 0.024(5) 0.054(8) 0.007(5) 0.003(6) 0.010(5) C31 0.052(7) 0.043(6) 0.043(7) 0.008(5) 0.010(5) 0.026(5) C32 0.053(7) 0.044(6) 0.053(8) -0.005(6) 0.011(6) -0.012(5) C33 0.022(5) 0.016(5) 0.044(7) -0.005(4) 0.001(4) -0.002(3) C34 0.029(5) 0.018(5) 0.045(7) -0.005(4) -0.005(4) 0.009(4) C35 0.039(6) 0.026(5) 0.048(7) -0.002(5) -0.003(5) 0.000(4) C36 0.037(8) 0.035(8) 0.101(13) 0.009(7) 0.005(8) 0.009(6) C37 0.041(6) 0.040(7) 0.074(10) -0.012(6) -0.007(6) 0.013(5) C38 0.040(6) 0.023(5) 0.054(7) 0.006(5) -0.005(5) 0.000(4) C39 0.031(7) 0.031(7) 0.047(8) 0.004(5) 0.003(6) -0.001(5) C40 0.063(8) 0.047(8) 0.093(12) 0.020(7) -0.021(8) 0.020(6) C41 0.089(12) 0.082(12) 0.124(16) -0.034(11) -0.016(11) 0.047(9) C42 0.067(9) 0.068(10) 0.104(13) -0.018(9) 0.019(9) -0.031(8) _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 Cd1 N2 2.234(7) . ? Cd1 N7 2.254(9) . ? Cd1 N5 2.307(8) . ? Cd1 N10 2.308(8) . ? Cd1 O1 2.394(9) . ? Cd1 O3 2.399(9) . ? O1 C5 1.227(12) . ? N1 C2 1.367(12) . ? N1 N2 1.370(11) . ? N1 C13 1.486(12) . ? C1 C2 1.500(15) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 C13 1.243(12) . ? N2 C4 1.347(12) . ? C2 C3 1.378(14) . ? O3 C25 1.224(12) . ? N3 C5 1.374(13) . ? N3 C4 1.397(12) . ? N3 H3N 0.8800 . ? C3 C4 1.405(15) . ? C3 H3 0.9500 . ? O4 C33 1.250(11) . ? N4 C5 1.388(13) . ? N4 C6 1.405(15) . ? N4 H4N 0.8800 . ? O5 C41 1.419(15) . ? O5 H5 0.8400 . ? N5 C13 1.290(12) . ? N5 C14 1.430(12) . ? O6 C42 1.411(15) . ? O6 H6 0.8400 . ? N6 N7 1.359(11) . ? N6 C22 1.385(12) . ? N6 C33 1.474(13) . ? C6 C11 1.353(16) . ? C6 C7 1.448(16) . ? N7 C24 1.317(12) . ? C7 C8 1.416(16) . ? C7 H7 0.9500 . ? N8 C25 1.368(12) . ? N8 C24 1.416(12) . ? N8 H8N 0.8800 . ? C8 C9 1.376(16) . ? C8 H8 0.9500 . ? N9 C25 1.400(13) . ? N9 C26 1.404(15) . ? N9 H9N 0.8800 . ? C9 C10 1.449(16) . ? C9 C12 1.474(17) . ? N10 C33 1.293(13) . ? N10 C34 1.448(12) . ? C10 C11 1.376(16) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C14 C15 1.386(14) . ? C14 C19 1.403(17) . ? C15 C16 1.418(17) . ? C15 H15 0.9500 . ? C16 C17 1.365(19) . ? C16 H16 0.9500 . ? C17 C18 1.378(16) . ? C17 C20 1.516(14) . ? C18 C19 1.418(16) . ? C18 H17 0.9500 . ? C19 H18 0.9500 . ? C20 H20B 0.9800 . ? C20 H20A 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.491(14) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.382(13) . ? C23 C24 1.399(14) . ? C23 H23 0.9500 . ? C26 C27 1.409(14) . ? C26 C31 1.417(16) . ? C27 C28 1.397(16) . ? C27 H27 0.9500 . ? C28 C29 1.394(17) . ? C28 H28 0.9500 . ? C29 C30 1.408(17) . ? C29 C32 1.533(17) . ? C30 C31 1.372(16) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C34 C39 1.358(16) . ? C34 C35 1.379(13) . ? C35 C36 1.409(18) . ? C35 H35 0.9500 . ? C36 C37 1.41(2) . ? C36 H36 0.9500 . ? C37 C38 1.380(15) . ? C37 C40 1.526(16) . ? C38 C39 1.423(16) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 H42C 0.9800 . ? C42 H42B 0.9800 . ? C42 H42A 0.9800 . ? 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 N2 Cd1 N7 162.4(3) . . ? N2 Cd1 N5 71.3(3) . . ? N7 Cd1 N5 118.8(3) . . ? N2 Cd1 N10 119.5(3) . . ? N7 Cd1 N10 71.2(3) . . ? N5 Cd1 N10 114.4(3) . . ? N2 Cd1 O1 72.3(3) . . ? N7 Cd1 O1 94.4(3) . . ? N5 Cd1 O1 142.4(3) . . ? N10 Cd1 O1 91.6(3) . . ? N2 Cd1 O3 93.9(3) . . ? N7 Cd1 O3 72.4(3) . . ? N5 Cd1 O3 91.0(3) . . ? N10 Cd1 O3 142.4(3) . . ? O1 Cd1 O3 82.4(2) . . ? C5 O1 Cd1 135.1(7) . . ? C2 N1 N2 110.6(8) . . ? C2 N1 C13 130.9(8) . . ? N2 N1 C13 118.5(7) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 N2 N1 105.2(8) . . ? C4 N2 Cd1 138.1(7) . . ? N1 N2 Cd1 116.6(5) . . ? N1 C2 C3 107.9(9) . . ? N1 C2 C1 124.4(9) . . ? C3 C2 C1 127.6(10) . . ? C25 O3 Cd1 134.1(7) . . ? C5 N3 C4 125.0(8) . . ? C5 N3 H3N 117.5 . . ? C4 N3 H3N 117.5 . . ? C2 C3 C4 104.8(9) . . ? C2 C3 H3 127.6 . . ? C4 C3 H3 127.6 . . ? C5 N4 C6 123.7(10) . . ? C5 N4 H4N 118.1 . . ? C6 N4 H4N 118.1 . . ? N2 C4 N3 122.4(9) . . ? N2 C4 C3 111.5(9) . . ? N3 C4 C3 126.1(9) . . ? C41 O5 H5 109.5 . . ? C13 N5 C14 119.4(8) . . ? C13 N5 Cd1 120.1(6) . . ? C14 N5 Cd1 120.4(7) . . ? O1 C5 N3 124.3(9) . . ? O1 C5 N4 122.0(10) . . ? N3 C5 N4 113.6(9) . . ? C42 O6 H6 109.5 . . ? N7 N6 C22 110.7(8) . . ? N7 N6 C33 119.6(8) . . ? C22 N6 C33 129.5(8) . . ? C11 C6 N4 127.7(12) . . ? C11 C6 C7 117.4(11) . . ? N4 C6 C7 114.4(10) . . ? C24 N7 N6 106.3(8) . . ? C24 N7 Cd1 137.9(7) . . ? N6 N7 Cd1 115.8(6) . . ? C8 C7 C6 119.4(10) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C25 N8 C24 123.7(8) . . ? C25 N8 H8N 118.1 . . ? C24 N8 H8N 118.1 . . ? C9 C8 C7 122.8(10) . . ? C9 C8 H8 118.6 . . ? C7 C8 H8 118.6 . . ? C25 N9 C26 125.9(10) . . ? C25 N9 H9N 117.1 . . ? C26 N9 H9N 117.1 . . ? C8 C9 C10 115.9(11) . . ? C8 C9 C12 123.6(11) . . ? C10 C9 C12 120.5(11) . . ? C33 N10 C34 121.0(8) . . ? C33 N10 Cd1 120.0(6) . . ? C34 N10 Cd1 119.0(6) . . ? C11 C10 C9 121.3(11) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C6 C11 C10 123.1(11) . . ? C6 C11 H11 118.4 . . ? C10 C11 H11 118.4 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C13 N5 131.2(8) . . ? O2 C13 N1 115.6(9) . . ? N5 C13 N1 113.2(8) . . ? C15 C14 C19 116.7(10) . . ? C15 C14 N5 124.3(9) . . ? C19 C14 N5 118.8(10) . . ? C14 C15 C16 120.0(11) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C17 C16 C15 122.9(12) . . ? C17 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? C16 C17 C18 118.2(10) . . ? C16 C17 C20 121.6(11) . . ? C18 C17 C20 120.1(11) . . ? C17 C18 C19 119.7(11) . . ? C17 C18 H17 120.2 . . ? C19 C18 H17 120.2 . . ? C14 C19 C18 122.5(13) . . ? C14 C19 H18 118.8 . . ? C18 C19 H18 118.8 . . ? C17 C20 H20B 109.5 . . ? C17 C20 H20A 109.5 . . ? H20B C20 H20A 109.5 . . ? C17 C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 N6 105.8(9) . . ? C23 C22 C21 129.1(10) . . ? N6 C22 C21 125.1(9) . . ? C22 C23 C24 105.9(9) . . ? C22 C23 H23 127.1 . . ? C24 C23 H23 127.1 . . ? N7 C24 C23 111.3(8) . . ? N7 C24 N8 123.3(9) . . ? C23 C24 N8 125.4(9) . . ? O3 C25 N8 125.9(8) . . ? O3 C25 N9 120.5(10) . . ? N8 C25 N9 113.6(8) . . ? N9 C26 C27 116.5(11) . . ? N9 C26 C31 125.3(10) . . ? C27 C26 C31 118.1(10) . . ? C28 C27 C26 120.5(11) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C29 C28 C27 121.5(12) . . ? C29 C28 H28 119.3 . . ? C27 C28 H28 119.3 . . ? C28 C29 C30 117.3(12) . . ? C28 C29 C32 122.3(11) . . ? C30 C29 C32 120.3(11) . . ? C31 C30 C29 122.4(12) . . ? C31 C30 H30 118.8 . . ? C29 C30 H30 118.8 . . ? C30 C31 C26 120.2(10) . . ? C30 C31 H31 119.9 . . ? C26 C31 H31 119.9 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O4 C33 N10 130.3(9) . . ? O4 C33 N6 116.4(9) . . ? N10 C33 N6 113.2(8) . . ? C39 C34 C35 118.7(10) . . ? C39 C34 N10 119.1(9) . . ? C35 C34 N10 122.1(9) . . ? C34 C35 C36 120.3(11) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C35 C36 C37 120.5(13) . . ? C35 C36 H36 119.7 . . ? C37 C36 H36 119.7 . . ? C38 C37 C36 118.9(12) . . ? C38 C37 C40 120.0(12) . . ? C36 C37 C40 121.2(12) . . ? C37 C38 C39 118.7(11) . . ? C37 C38 H38 120.6 . . ? C39 C38 H38 120.6 . . ? C34 C39 C38 122.7(11) . . ? C34 C39 H39 118.6 . . ? C38 C39 H39 118.6 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? O5 C41 H41A 109.5 . . ? O5 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? O5 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? O6 C42 H42C 109.5 . . ? O6 C42 H42B 109.5 . . ? H42C C42 H42B 109.5 . . ? O6 C42 H42A 109.5 . . ? H42C C42 H42A 109.5 . . ? H42B C42 H42A 109.5 . . ? 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 N2 Cd1 O1 C5 18.8(10) . . . . ? N7 Cd1 O1 C5 -173.1(10) . . . . ? N5 Cd1 O1 C5 33.7(13) . . . . ? N10 Cd1 O1 C5 -101.8(11) . . . . ? O3 Cd1 O1 C5 115.4(11) . . . . ? C2 N1 N2 C4 0.4(10) . . . . ? C13 N1 N2 C4 179.4(7) . . . . ? C2 N1 N2 Cd1 178.7(6) . . . . ? C13 N1 N2 Cd1 -2.3(10) . . . . ? N7 Cd1 N2 C4 -51.1(16) . . . . ? N5 Cd1 N2 C4 -179.1(9) . . . . ? N10 Cd1 N2 C4 72.8(9) . . . . ? O1 Cd1 N2 C4 -8.7(9) . . . . ? O3 Cd1 N2 C4 -89.4(9) . . . . ? N7 Cd1 N2 N1 131.3(10) . . . . ? N5 Cd1 N2 N1 3.3(6) . . . . ? N10 Cd1 N2 N1 -104.8(6) . . . . ? O1 Cd1 N2 N1 173.7(7) . . . . ? O3 Cd1 N2 N1 93.1(7) . . . . ? N2 N1 C2 C3 0.1(11) . . . . ? C13 N1 C2 C3 -178.8(9) . . . . ? N2 N1 C2 C1 -178.2(9) . . . . ? C13 N1 C2 C1 2.9(16) . . . . ? N2 Cd1 O3 C25 -173.0(11) . . . . ? N7 Cd1 O3 C25 18.3(10) . . . . ? N5 Cd1 O3 C25 -101.7(11) . . . . ? N10 Cd1 O3 C25 32.9(13) . . . . ? O1 Cd1 O3 C25 115.4(11) . . . . ? N1 C2 C3 C4 -0.6(10) . . . . ? C1 C2 C3 C4 177.7(10) . . . . ? N1 N2 C4 N3 178.9(8) . . . . ? Cd1 N2 C4 N3 1.1(14) . . . . ? N1 N2 C4 C3 -0.7(10) . . . . ? Cd1 N2 C4 C3 -178.5(7) . . . . ? C5 N3 C4 N2 5.5(13) . . . . ? C5 N3 C4 C3 -174.9(9) . . . . ? C2 C3 C4 N2 0.8(11) . . . . ? C2 C3 C4 N3 -178.8(8) . . . . ? N2 Cd1 N5 C13 -4.6(6) . . . . ? N7 Cd1 N5 C13 -168.8(6) . . . . ? N10 Cd1 N5 C13 110.1(6) . . . . ? O1 Cd1 N5 C13 -19.6(9) . . . . ? O3 Cd1 N5 C13 -98.4(6) . . . . ? N2 Cd1 N5 C14 178.8(7) . . . . ? N7 Cd1 N5 C14 14.6(7) . . . . ? N10 Cd1 N5 C14 -66.5(7) . . . . ? O1 Cd1 N5 C14 163.8(6) . . . . ? O3 Cd1 N5 C14 85.0(6) . . . . ? Cd1 O1 C5 N3 -20.5(16) . . . . ? Cd1 O1 C5 N4 161.8(7) . . . . ? C4 N3 C5 O1 4.1(14) . . . . ? C4 N3 C5 N4 -178.0(8) . . . . ? C6 N4 C5 O1 -10.1(15) . . . . ? C6 N4 C5 N3 171.9(9) . . . . ? C5 N4 C6 C11 -20.3(17) . . . . ? C5 N4 C6 C7 168.5(9) . . . . ? C22 N6 N7 C24 2.3(10) . . . . ? C33 N6 N7 C24 178.3(8) . . . . ? C22 N6 N7 Cd1 179.7(6) . . . . ? C33 N6 N7 Cd1 -4.3(10) . . . . ? N2 Cd1 N7 C24 -49.2(16) . . . . ? N5 Cd1 N7 C24 72.3(9) . . . . ? N10 Cd1 N7 C24 -179.5(10) . . . . ? O1 Cd1 N7 C24 -89.4(9) . . . . ? O3 Cd1 N7 C24 -8.8(9) . . . . ? N2 Cd1 N7 N6 134.4(9) . . . . ? N5 Cd1 N7 N6 -104.0(7) . . . . ? N10 Cd1 N7 N6 4.1(6) . . . . ? O1 Cd1 N7 N6 94.2(7) . . . . ? O3 Cd1 N7 N6 174.8(7) . . . . ? C11 C6 C7 C8 2.7(15) . . . . ? N4 C6 C7 C8 174.9(9) . . . . ? C6 C7 C8 C9 -1.3(15) . . . . ? C7 C8 C9 C10 1.3(15) . . . . ? C7 C8 C9 C12 179.3(10) . . . . ? N2 Cd1 N10 C33 -168.7(6) . . . . ? N7 Cd1 N10 C33 -4.1(7) . . . . ? N5 Cd1 N10 C33 109.8(7) . . . . ? O1 Cd1 N10 C33 -98.2(7) . . . . ? O3 Cd1 N10 C33 -18.7(9) . . . . ? N2 Cd1 N10 C34 13.6(7) . . . . ? N7 Cd1 N10 C34 178.2(7) . . . . ? N5 Cd1 N10 C34 -68.0(7) . . . . ? O1 Cd1 N10 C34 84.0(7) . . . . ? O3 Cd1 N10 C34 163.5(6) . . . . ? C8 C9 C10 C11 -2.7(15) . . . . ? C12 C9 C10 C11 179.2(10) . . . . ? N4 C6 C11 C10 -175.3(11) . . . . ? C7 C6 C11 C10 -4.3(17) . . . . ? C9 C10 C11 C6 4.4(18) . . . . ? C14 N5 C13 O2 -0.5(14) . . . . ? Cd1 N5 C13 O2 -177.2(7) . . . . ? C14 N5 C13 N1 -178.6(7) . . . . ? Cd1 N5 C13 N1 4.8(9) . . . . ? C2 N1 C13 O2 -1.2(13) . . . . ? N2 N1 C13 O2 180.0(7) . . . . ? C2 N1 C13 N5 177.2(9) . . . . ? N2 N1 C13 N5 -1.7(11) . . . . ? C13 N5 C14 C15 -56.4(13) . . . . ? Cd1 N5 C14 C15 120.2(10) . . . . ? C13 N5 C14 C19 129.4(11) . . . . ? Cd1 N5 C14 C19 -54.0(12) . . . . ? C19 C14 C15 C16 0.6(16) . . . . ? N5 C14 C15 C16 -173.8(11) . . . . ? C14 C15 C16 C17 -2(2) . . . . ? C15 C16 C17 C18 3(2) . . . . ? C15 C16 C17 C20 179.4(12) . . . . ? C16 C17 C18 C19 -2.2(19) . . . . ? C20 C17 C18 C19 -178.6(12) . . . . ? C15 C14 C19 C18 0.2(18) . . . . ? N5 C14 C19 C18 174.8(11) . . . . ? C17 C18 C19 C14 1(2) . . . . ? N7 N6 C22 C23 -0.9(10) . . . . ? C33 N6 C22 C23 -176.4(9) . . . . ? N7 N6 C22 C21 -179.2(9) . . . . ? C33 N6 C22 C21 5.3(16) . . . . ? N6 C22 C23 C24 -0.7(10) . . . . ? C21 C22 C23 C24 177.5(9) . . . . ? N6 N7 C24 C23 -2.8(10) . . . . ? Cd1 N7 C24 C23 -179.4(7) . . . . ? N6 N7 C24 N8 178.7(8) . . . . ? Cd1 N7 C24 N8 2.1(15) . . . . ? C22 C23 C24 N7 2.2(11) . . . . ? C22 C23 C24 N8 -179.3(8) . . . . ? C25 N8 C24 N7 3.8(14) . . . . ? C25 N8 C24 C23 -174.5(9) . . . . ? Cd1 O3 C25 N8 -20.9(17) . . . . ? Cd1 O3 C25 N9 162.0(8) . . . . ? C24 N8 C25 O3 5.8(15) . . . . ? C24 N8 C25 N9 -176.9(8) . . . . ? C26 N9 C25 O3 -12.1(16) . . . . ? C26 N9 C25 N8 170.5(9) . . . . ? C25 N9 C26 C27 169.0(10) . . . . ? C25 N9 C26 C31 -14.0(17) . . . . ? N9 C26 C27 C28 177.3(9) . . . . ? C31 C26 C27 C28 0.1(15) . . . . ? C26 C27 C28 C29 -1.3(16) . . . . ? C27 C28 C29 C30 2.7(16) . . . . ? C27 C28 C29 C32 -179.3(9) . . . . ? C28 C29 C30 C31 -3.1(17) . . . . ? C32 C29 C30 C31 178.9(11) . . . . ? C29 C30 C31 C26 2.0(18) . . . . ? N9 C26 C31 C30 -177.4(11) . . . . ? C27 C26 C31 C30 -0.5(17) . . . . ? C34 N10 C33 O4 0.8(15) . . . . ? Cd1 N10 C33 O4 -176.9(7) . . . . ? C34 N10 C33 N6 -179.1(8) . . . . ? Cd1 N10 C33 N6 3.2(10) . . . . ? N7 N6 C33 O4 -179.2(8) . . . . ? C22 N6 C33 O4 -4.0(14) . . . . ? N7 N6 C33 N10 0.7(12) . . . . ? C22 N6 C33 N10 175.9(9) . . . . ? C33 N10 C34 C39 127.4(11) . . . . ? Cd1 N10 C34 C39 -54.8(12) . . . . ? C33 N10 C34 C35 -56.0(13) . . . . ? Cd1 N10 C34 C35 121.8(9) . . . . ? C39 C34 C35 C36 0.2(17) . . . . ? N10 C34 C35 C36 -176.4(11) . . . . ? C34 C35 C36 C37 2(2) . . . . ? C35 C36 C37 C38 -1(2) . . . . ? C35 C36 C37 C40 176.7(13) . . . . ? C36 C37 C38 C39 -0.5(18) . . . . ? C40 C37 C38 C39 -178.7(12) . . . . ? C35 C34 C39 C38 -2.2(18) . . . . ? N10 C34 C39 C38 174.5(10) . . . . ? C37 C38 C39 C34 2.4(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.063 _refine_diff_density_min -1.548 _refine_diff_density_rms 0.127 _database_code_depnum_ccdc_archive 'CCDC 971041' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_c:cu311aacetate _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C126 H144 Cu6 N30 O18, 6(C2 H3 O2), 6(C H4 O) ; _chemical_formula_sum 'C144 H186 Cu6 N30 O36 ' _chemical_formula_weight 3294.53 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 Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 31.7325(8) _cell_length_b 31.7325(8) _cell_length_c 13.6585(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 11910.8(10) _cell_formula_units_Z 3 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1432 _cell_measurement_theta_min 2.464 _cell_measurement_theta_max 18.595 _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5166 _exptl_absorpt_coefficient_mu 0.872 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8951 _exptl_absorpt_correction_T_max 0.9577 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMart - 6K' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22616 _diffrn_reflns_av_R_equivalents 0.1729 _diffrn_reflns_av_sigmaI/netI 0.1710 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4635 _reflns_number_gt 1988 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Smart- Bruker' _computing_cell_refinement 'Saint- Bruker' _computing_data_reduction 'Saint- Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Xseed _computing_publication_material Xseed _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. The crystals produced were all found to poorly diffract resulting in poor data correlation. The connectivity of the structure is not in question. The hydrogen positions of the two methanol hydroxide groups were DFIX restrained to give more ideal hydrogen bonding positions. ; _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^)+(0.0610P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4635 _refine_ls_number_parameters 331 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1489 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1434 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 0.811 _refine_ls_restrained_S_all 0.842 _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 0.14138(2) 0.53885(2) 0.64865(6) 0.0385(3) Uani 1 1 d . . . O1 O 0.09188(13) 0.55229(13) 0.5878(3) 0.0378(11) Uani 1 1 d . . . N1 N 0.17447(16) 0.49587(16) 0.5153(4) 0.0393(13) Uani 1 1 d . . . C1 C 0.2126(2) 0.4727(2) 0.3781(6) 0.060(2) Uani 1 1 d . . . H1A H 0.2314 0.4696 0.4318 0.090 Uiso 1 1 calc R . . H1B H 0.2349 0.4967 0.3308 0.090 Uiso 1 1 calc R . . H1C H 0.1935 0.4411 0.3457 0.090 Uiso 1 1 calc R . . O2 O 0.23698(12) 0.49219(13) 0.5856(3) 0.0406(11) Uani 1 1 d . . . N2 N 0.14081(15) 0.51054(16) 0.5273(4) 0.0379(13) Uani 1 1 d . . . C2 C 0.17946(19) 0.4889(2) 0.4179(6) 0.0407(17) Uani 1 1 d . . . O3 O 0.07355(14) 0.53403(16) 0.2327(3) 0.0541(13) Uani 1 1 d D . . N3 N 0.09295(15) 0.52931(15) 0.4270(4) 0.0414(14) Uani 1 1 d . . . H3N H 0.0811 0.5280 0.3681 0.050 Uiso 1 1 calc R . . C3 C 0.1480(2) 0.49867(19) 0.3673(5) 0.0424(17) Uani 1 1 d . . . H3 H 0.1422 0.4960 0.2988 0.051 Uiso 1 1 calc R . . O4 O 0.00953(14) 0.54043(14) 0.2819(3) 0.0455(11) Uani 1 1 d . . . N4 N 0.04310(15) 0.55825(15) 0.4728(4) 0.0351(13) Uani 1 1 d . . . H4N H 0.0361 0.5552 0.4099 0.042 Uiso 1 1 calc R . . C4 C 0.12619(19) 0.51352(19) 0.4382(6) 0.0386(17) Uani 1 1 d . . . O5 O 0.1257(2) 0.5029(3) 0.1254(4) 0.107(2) Uani 1 1 d D . . N5 N 0.19335(16) 0.52206(16) 0.6743(4) 0.0395(14) Uani 1 1 d . . . C5 C 0.07730(19) 0.54682(19) 0.5013(5) 0.0334(15) Uani 1 1 d . . . O6 O 0.08320(13) 0.48221(13) 0.7414(3) 0.0397(11) Uani 1 1 d D . . C6 C 0.01767(19) 0.57432(19) 0.5322(5) 0.0354(16) Uani 1 1 d . . . H6 H 0.0546(8) 0.4777(18) 0.730(4) 0.029(16) Uiso 1 1 d D . . C7 C -0.0069(2) 0.5941(2) 0.4843(5) 0.0428(17) Uani 1 1 d . . . H7 H -0.0052 0.5970 0.4149 0.051 Uiso 1 1 calc R . . C8 C -0.0340(2) 0.6097(2) 0.5370(6) 0.0472(18) Uani 1 1 d . . . H8 H -0.0510 0.6227 0.5027 0.057 Uiso 1 1 calc R . . C9 C -0.0370(2) 0.6068(2) 0.6376(6) 0.0444(17) Uani 1 1 d . . . C10 C -0.01253(19) 0.5866(2) 0.6855(5) 0.0401(16) Uani 1 1 d . . . H10 H -0.0146 0.5834 0.7548 0.048 Uiso 1 1 calc R . . C11 C 0.01497(19) 0.57103(19) 0.6334(5) 0.0405(17) Uani 1 1 d . . . H11 H 0.0320 0.5581 0.6676 0.049 Uiso 1 1 calc R . . C12 C -0.0663(2) 0.6244(2) 0.6959(6) 0.063(2) Uani 1 1 d . . . H12A H -0.0797 0.6389 0.6512 0.095 Uiso 1 1 calc R . . H12C H -0.0451 0.6489 0.7437 0.095 Uiso 1 1 calc R . . H12B H -0.0930 0.5968 0.7302 0.095 Uiso 1 1 calc R . . C13 C 0.20434(19) 0.50359(19) 0.5987(5) 0.0376(16) Uani 1 1 d . . . C14 C 0.2230(2) 0.53653(19) 0.7600(6) 0.0421(18) Uani 1 1 d . . . C15 C 0.2739(2) 0.56838(19) 0.7557(6) 0.0470(19) Uani 1 1 d . . . H15 H 0.2899 0.5792 0.6944 0.056 Uiso 1 1 calc R . . C16 C 0.3000(2) 0.5836(2) 0.8424(7) 0.053(2) Uani 1 1 d . . . H16 H 0.3341 0.6053 0.8386 0.064 Uiso 1 1 calc R . . C17 C 0.2794(2) 0.5691(2) 0.9339(7) 0.057(2) Uani 1 1 d . . . C18 C 0.2289(2) 0.5381(2) 0.9369(6) 0.054(2) Uani 1 1 d . . . H18 H 0.2131 0.5274 0.9984 0.065 Uiso 1 1 calc R . . C19 C 0.2014(2) 0.5226(2) 0.8511(6) 0.0460(18) Uani 1 1 d . . . H19 H 0.1672 0.5021 0.8554 0.055 Uiso 1 1 calc R . . C20 C 0.3088(3) 0.5859(3) 1.0257(6) 0.083(3) Uani 1 1 d . . . H20A H 0.3431 0.6075 1.0092 0.125 Uiso 1 1 calc R . . H20B H 0.3053 0.5577 1.0620 0.125 Uiso 1 1 calc R . . H20C H 0.2973 0.6036 1.0663 0.125 Uiso 1 1 calc R . . C21 C 0.0102(2) 0.5160(3) 0.1176(5) 0.058(2) Uani 1 1 d . . . H21C H 0.0318 0.5101 0.0758 0.088 Uiso 1 1 calc R . . H21B H 0.0057 0.5417 0.0887 0.088 Uiso 1 1 calc R . . H21A H -0.0214 0.4861 0.1233 0.088 Uiso 1 1 calc R . . C22 C 0.0330(2) 0.5319(2) 0.2193(5) 0.0435(17) Uani 1 1 d . . . C23 C 0.0978(3) 0.4628(3) 0.0528(7) 0.102(3) Uani 1 1 d . . . H23C H 0.0965 0.4769 -0.0102 0.152 Uiso 1 1 calc R . . H23B H 0.0646 0.4416 0.0769 0.152 Uiso 1 1 calc R . . H23A H 0.1140 0.4437 0.0443 0.152 Uiso 1 1 calc R . . C24 C 0.0785(2) 0.43482(18) 0.7565(5) 0.054(2) Uani 1 1 d . . . H24A H 0.0503 0.4151 0.7986 0.081 Uiso 1 1 calc R . . H24B H 0.1080 0.4388 0.7880 0.081 Uiso 1 1 calc R . . H24C H 0.0739 0.4185 0.6933 0.081 Uiso 1 1 calc R . . H5 H 0.1230 0.5333 0.1379 1.9(10) Uiso 1 1 d RD . . 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 0.0189(4) 0.0219(4) 0.0758(6) -0.0006(4) -0.0042(4) 0.0112(3) O1 0.022(2) 0.026(2) 0.066(3) -0.001(2) -0.007(2) 0.0128(18) N1 0.024(3) 0.025(3) 0.072(4) 0.000(3) -0.002(3) 0.014(2) C1 0.035(4) 0.048(4) 0.106(6) -0.005(4) 0.002(4) 0.028(3) O2 0.021(2) 0.028(2) 0.075(3) 0.012(2) 0.006(2) 0.0143(18) N2 0.019(2) 0.030(3) 0.071(4) 0.002(3) 0.005(3) 0.017(2) C2 0.020(3) 0.022(3) 0.079(6) -0.008(3) -0.004(3) 0.010(3) O3 0.034(3) 0.065(3) 0.067(4) 0.003(3) 0.001(2) 0.027(2) N3 0.022(3) 0.027(3) 0.073(4) -0.012(3) -0.011(3) 0.012(2) C3 0.026(3) 0.025(3) 0.073(5) -0.009(3) -0.003(3) 0.011(3) O4 0.030(2) 0.045(3) 0.064(3) -0.006(2) -0.009(2) 0.020(2) N4 0.025(3) 0.031(3) 0.055(4) 0.000(3) -0.007(2) 0.018(2) C4 0.018(3) 0.015(3) 0.079(6) -0.005(3) -0.008(3) 0.006(3) O5 0.097(5) 0.167(6) 0.085(5) 0.000(5) -0.006(4) 0.086(5) N5 0.023(3) 0.020(2) 0.074(4) -0.007(3) -0.001(3) 0.010(2) C5 0.019(3) 0.018(3) 0.058(5) -0.001(3) -0.002(3) 0.005(2) O6 0.024(2) 0.022(2) 0.073(3) -0.002(2) -0.007(2) 0.0115(19) C6 0.023(3) 0.020(3) 0.060(5) -0.003(3) -0.007(3) 0.008(3) C7 0.033(3) 0.038(4) 0.064(5) -0.004(3) -0.009(3) 0.023(3) C8 0.031(4) 0.037(4) 0.081(6) 0.000(4) -0.007(4) 0.023(3) C9 0.025(3) 0.030(3) 0.078(6) -0.005(4) -0.004(4) 0.013(3) C10 0.030(3) 0.029(3) 0.057(5) -0.005(3) -0.002(3) 0.012(3) C11 0.023(3) 0.020(3) 0.076(6) -0.003(3) -0.009(3) 0.009(3) C12 0.045(4) 0.048(4) 0.110(7) -0.020(4) -0.004(4) 0.032(4) C13 0.017(3) 0.020(3) 0.070(5) 0.009(3) 0.001(3) 0.005(3) C14 0.023(3) 0.019(3) 0.088(6) -0.010(4) -0.017(4) 0.013(3) C15 0.023(3) 0.019(3) 0.103(6) -0.006(4) -0.008(4) 0.013(3) C16 0.023(4) 0.021(3) 0.118(7) -0.019(4) -0.024(4) 0.013(3) C17 0.042(4) 0.038(4) 0.101(7) -0.017(4) -0.028(5) 0.027(4) C18 0.044(4) 0.038(4) 0.086(6) 0.000(4) -0.016(4) 0.024(3) C19 0.028(3) 0.030(3) 0.079(6) 0.000(4) -0.015(4) 0.014(3) C20 0.074(5) 0.064(5) 0.125(8) -0.036(5) -0.055(5) 0.045(5) C21 0.055(5) 0.069(5) 0.056(5) 0.004(4) -0.001(4) 0.034(4) C22 0.039(4) 0.029(3) 0.061(5) 0.003(3) 0.006(4) 0.016(3) C23 0.100(8) 0.101(8) 0.102(8) -0.004(6) 0.008(6) 0.049(6) C24 0.035(4) 0.018(3) 0.106(6) -0.003(4) -0.022(4) 0.010(3) _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 N2 1.880(5) . ? Cu1 O2 1.936(4) 14_456 ? Cu1 N5 2.001(5) . ? Cu1 O1 2.003(4) . ? Cu1 O6 2.219(4) . ? O1 C5 1.248(7) . ? N1 C2 1.371(8) . ? N1 N2 1.372(6) . ? N1 C13 1.423(8) . ? C1 C2 1.487(8) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 C13 1.269(6) . ? O2 Cu1 1.936(4) 15_556 ? N2 C4 1.323(7) . ? C2 C3 1.371(8) . ? O3 C22 1.269(7) . ? N3 C5 1.364(7) . ? N3 C4 1.384(7) . ? N3 H3N 0.8800 . ? C3 C4 1.402(8) . ? C3 H3 0.9500 . ? O4 C22 1.248(7) . ? N4 C5 1.362(7) . ? N4 C6 1.408(7) . ? N4 H4N 0.8800 . ? O5 C23 1.505(9) . ? O5 H5 1.0233 . ? N5 C13 1.318(8) . ? N5 C14 1.426(8) . ? O6 C24 1.450(6) . ? O6 H6 0.860(11) . ? C6 C7 1.386(8) . ? C6 C11 1.385(8) . ? C7 C8 1.389(8) . ? C7 H7 0.9500 . ? C8 C9 1.377(9) . ? C8 H8 0.9500 . ? C9 C10 1.394(8) . ? C9 C12 1.527(8) . ? C10 C11 1.394(8) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12C 0.9800 . ? C12 H12B 0.9800 . ? C14 C19 1.381(9) . ? C14 C15 1.415(7) . ? C15 C16 1.387(9) . ? C15 H15 0.9500 . ? C16 C17 1.378(10) . ? C16 H16 0.9500 . ? C17 C18 1.401(9) . ? C17 C20 1.494(9) . ? C18 C19 1.395(9) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.530(9) . ? C21 H21C 0.9800 . ? C21 H21B 0.9800 . ? C21 H21A 0.9800 . ? C23 H23C 0.9800 . ? C23 H23B 0.9800 . ? C23 H23A 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 N2 Cu1 O2 159.23(19) . 14_456 ? N2 Cu1 N5 80.8(2) . . ? O2 Cu1 N5 98.98(19) 14_456 . ? N2 Cu1 O1 85.11(19) . . ? O2 Cu1 O1 92.99(16) 14_456 . ? N5 Cu1 O1 165.5(2) . . ? N2 Cu1 O6 108.09(18) . . ? O2 Cu1 O6 92.54(16) 14_456 . ? N5 Cu1 O6 98.46(17) . . ? O1 Cu1 O6 89.19(15) . . ? C5 O1 Cu1 129.7(4) . . ? C2 N1 N2 110.1(5) . . ? C2 N1 C13 133.2(5) . . ? N2 N1 C13 114.2(5) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C13 O2 Cu1 127.3(4) . 15_556 ? C4 N2 N1 105.9(5) . . ? C4 N2 Cu1 134.2(4) . . ? N1 N2 Cu1 116.4(4) . . ? C3 C2 N1 107.3(5) . . ? C3 C2 C1 128.0(7) . . ? N1 C2 C1 124.7(6) . . ? C5 N3 C4 124.3(6) . . ? C5 N3 H3N 117.8 . . ? C4 N3 H3N 117.8 . . ? C2 C3 C4 105.4(6) . . ? C2 C3 H3 127.3 . . ? C4 C3 H3 127.3 . . ? C5 N4 C6 127.5(6) . . ? C5 N4 H4N 116.2 . . ? C6 N4 H4N 116.2 . . ? N2 C4 N3 119.1(6) . . ? N2 C4 C3 111.2(5) . . ? N3 C4 C3 129.7(7) . . ? C23 O5 H5 128.1 . . ? C13 N5 C14 120.6(5) . . ? C13 N5 Cu1 114.7(4) . . ? C14 N5 Cu1 123.8(4) . . ? O1 C5 N3 125.1(5) . . ? O1 C5 N4 121.5(6) . . ? N3 C5 N4 113.4(6) . . ? C24 O6 Cu1 122.3(3) . . ? C24 O6 H6 108(3) . . ? Cu1 O6 H6 114(3) . . ? C7 C6 C11 118.6(6) . . ? C7 C6 N4 116.5(6) . . ? C11 C6 N4 125.0(5) . . ? C6 C7 C8 120.4(7) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 121.9(6) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C10 117.6(6) . . ? C8 C9 C12 122.0(6) . . ? C10 C9 C12 120.3(7) . . ? C9 C10 C11 121.0(7) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C6 C11 C10 120.6(6) . . ? C6 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? O2 C13 N5 132.2(6) . . ? O2 C13 N1 114.0(6) . . ? N5 C13 N1 113.7(5) . . ? C19 C14 C15 118.2(6) . . ? C19 C14 N5 119.7(5) . . ? C15 C14 N5 121.9(7) . . ? C16 C15 C14 118.9(7) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C17 C16 C15 123.9(6) . . ? C17 C16 H16 118.1 . . ? C15 C16 H16 118.1 . . ? C16 C17 C18 116.5(7) . . ? C16 C17 C20 122.3(7) . . ? C18 C17 C20 121.1(8) . . ? C19 C18 C17 121.1(7) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C14 C19 C18 121.5(6) . . ? C14 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 H21C 109.5 . . ? C22 C21 H21B 109.5 . . ? H21C C21 H21B 109.5 . . ? C22 C21 H21A 109.5 . . ? H21C C21 H21A 109.5 . . ? H21B C21 H21A 109.5 . . ? O4 C22 O3 126.1(7) . . ? O4 C22 C21 117.3(6) . . ? O3 C22 C21 116.5(6) . . ? O5 C23 H23C 109.5 . . ? O5 C23 H23B 109.5 . . ? H23C C23 H23B 109.5 . . ? O5 C23 H23A 109.5 . . ? H23C C23 H23A 109.5 . . ? H23B C23 H23A 109.5 . . ? O6 C24 H24A 109.5 . . ? O6 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O6 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 N2 Cu1 O1 C5 -7.7(5) . . . . ? O2 Cu1 O1 C5 151.6(5) 14_456 . . . ? N5 Cu1 O1 C5 6.2(9) . . . . ? O6 Cu1 O1 C5 -115.9(5) . . . . ? C2 N1 N2 C4 -1.3(6) . . . . ? C13 N1 N2 C4 163.1(4) . . . . ? C2 N1 N2 Cu1 -163.2(4) . . . . ? C13 N1 N2 Cu1 1.3(6) . . . . ? O2 Cu1 N2 C4 -67.1(8) 14_456 . . . ? N5 Cu1 N2 C4 -158.1(5) . . . . ? O1 Cu1 N2 C4 18.4(5) . . . . ? O6 Cu1 N2 C4 105.9(5) . . . . ? O2 Cu1 N2 N1 88.2(6) 14_456 . . . ? N5 Cu1 N2 N1 -2.8(4) . . . . ? O1 Cu1 N2 N1 173.7(4) . . . . ? O6 Cu1 N2 N1 -98.7(4) . . . . ? N2 N1 C2 C3 -0.8(6) . . . . ? C13 N1 C2 C3 -161.2(5) . . . . ? N2 N1 C2 C1 -179.6(5) . . . . ? C13 N1 C2 C1 20.0(9) . . . . ? N1 C2 C3 C4 2.5(6) . . . . ? C1 C2 C3 C4 -178.8(5) . . . . ? N1 N2 C4 N3 -177.8(4) . . . . ? Cu1 N2 C4 N3 -20.7(8) . . . . ? N1 N2 C4 C3 2.9(6) . . . . ? Cu1 N2 C4 C3 160.0(4) . . . . ? C5 N3 C4 N2 6.7(8) . . . . ? C5 N3 C4 C3 -174.2(5) . . . . ? C2 C3 C4 N2 -3.4(6) . . . . ? C2 C3 C4 N3 177.4(5) . . . . ? N2 Cu1 N5 C13 4.0(4) . . . . ? O2 Cu1 N5 C13 -154.9(4) 14_456 . . . ? O1 Cu1 N5 C13 -9.9(9) . . . . ? O6 Cu1 N5 C13 111.1(4) . . . . ? N2 Cu1 N5 C14 172.9(5) . . . . ? O2 Cu1 N5 C14 13.9(5) 14_456 . . . ? O1 Cu1 N5 C14 158.9(6) . . . . ? O6 Cu1 N5 C14 -80.0(5) . . . . ? Cu1 O1 C5 N3 0.4(8) . . . . ? Cu1 O1 C5 N4 -179.7(3) . . . . ? C4 N3 C5 O1 2.3(8) . . . . ? C4 N3 C5 N4 -177.5(5) . . . . ? C6 N4 C5 O1 -3.9(8) . . . . ? C6 N4 C5 N3 176.0(5) . . . . ? N2 Cu1 O6 C24 50.9(4) . . . . ? O2 Cu1 O6 C24 -131.6(4) 14_456 . . . ? N5 Cu1 O6 C24 -32.1(4) . . . . ? O1 Cu1 O6 C24 135.4(4) . . . . ? C5 N4 C6 C7 165.7(5) . . . . ? C5 N4 C6 C11 -15.4(8) . . . . ? C11 C6 C7 C8 -0.7(8) . . . . ? N4 C6 C7 C8 178.3(5) . . . . ? C6 C7 C8 C9 0.9(9) . . . . ? C7 C8 C9 C10 -1.2(9) . . . . ? C7 C8 C9 C12 179.3(5) . . . . ? C8 C9 C10 C11 1.5(8) . . . . ? C12 C9 C10 C11 -179.0(5) . . . . ? C7 C6 C11 C10 1.0(8) . . . . ? N4 C6 C11 C10 -177.9(5) . . . . ? C9 C10 C11 C6 -1.4(8) . . . . ? Cu1 O2 C13 N5 25.1(8) 15_556 . . . ? Cu1 O2 C13 N1 -156.3(3) 15_556 . . . ? C14 N5 C13 O2 5.0(9) . . . . ? Cu1 N5 C13 O2 174.2(5) . . . . ? C14 N5 C13 N1 -173.6(5) . . . . ? Cu1 N5 C13 N1 -4.4(6) . . . . ? C2 N1 C13 O2 -16.9(8) . . . . ? N2 N1 C13 O2 -176.7(4) . . . . ? C2 N1 C13 N5 161.9(6) . . . . ? N2 N1 C13 N5 2.1(6) . . . . ? C13 N5 C14 C19 -133.1(6) . . . . ? Cu1 N5 C14 C19 58.7(6) . . . . ? C13 N5 C14 C15 52.4(7) . . . . ? Cu1 N5 C14 C15 -115.8(5) . . . . ? C19 C14 C15 C16 1.0(8) . . . . ? N5 C14 C15 C16 175.6(5) . . . . ? C14 C15 C16 C17 0.7(9) . . . . ? C15 C16 C17 C18 -1.5(9) . . . . ? C15 C16 C17 C20 179.4(5) . . . . ? C16 C17 C18 C19 0.6(9) . . . . ? C20 C17 C18 C19 179.7(6) . . . . ? C15 C14 C19 C18 -1.9(8) . . . . ? N5 C14 C19 C18 -176.6(5) . . . . ? C17 C18 C19 C14 1.1(9) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.492 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 971034' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_c:\users\gol\desktop\steed\compou~1\311ai _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 N5 O2' _chemical_formula_sum 'C20 H21 N5 O2' _chemical_formula_weight 363.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8615(2) _cell_length_b 11.0671(4) _cell_length_c 14.0882(5) _cell_angle_alpha 91.1250(10) _cell_angle_beta 98.7050(10) _cell_angle_gamma 97.0080(10) _cell_volume 895.95(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9724 _exptl_absorpt_correction_T_max 0.9946 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Smart 6K' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16676 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 30.52 _reflns_number_total 5478 _reflns_number_gt 3835 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Smart - Bruker' _computing_cell_refinement 'Saint - Bruker' _computing_data_reduction 'Saint - Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Xseed _computing_publication_material Xseed _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^)+(0.0836P)^2^+0.1955P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5478 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1549 _refine_ls_wR_factor_gt 0.1364 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 O1 O 0.03657(17) 0.03248(9) 0.12447(8) 0.0250(2) Uani 1 1 d . . . N1 N 0.79335(19) 0.26884(10) -0.01580(8) 0.0204(2) Uani 1 1 d . . . C1 C 0.8549(2) 0.24537(13) -0.18901(10) 0.0244(3) Uani 1 1 d . . . H1A H 0.7907 0.1866 -0.2421 0.037 Uiso 1 1 calc R . . H1B H 1.0183 0.2356 -0.1673 0.037 Uiso 1 1 calc R . . H1C H 0.8443 0.3283 -0.2109 0.037 Uiso 1 1 calc R . . O2 O 1.13534(17) 0.38676(9) -0.03139(7) 0.0245(2) Uani 1 1 d . . . N2 N 0.63718(19) 0.22984(10) 0.04457(9) 0.0207(2) Uani 1 1 d . . . C2 C 0.7208(2) 0.22359(12) -0.10833(10) 0.0202(3) Uani 1 1 d . . . N3 N 0.2707(2) 0.10425(11) 0.01963(9) 0.0221(2) Uani 1 1 d . . . H3N H 0.1601 0.0714 -0.0261 0.027 Uiso 1 1 calc R . . C3 C 0.5104(2) 0.15490(12) -0.10795(10) 0.0219(3) Uani 1 1 d . . . H3 H 0.4132 0.1117 -0.1610 0.026 Uiso 1 1 calc R . . N4 N 0.3864(2) 0.14409(11) 0.18308(9) 0.0224(3) Uani 1 1 d . . . H4N H 0.5119 0.1836 0.1656 0.027 Uiso 1 1 calc R . . C4 C 0.4679(2) 0.16176(12) -0.01169(10) 0.0202(3) Uani 1 1 d . . . N5 N 1.0301(2) 0.35919(11) 0.11799(9) 0.0221(2) Uani 1 1 d . . . H5N H 0.9135 0.3263 0.1455 0.027 Uiso 1 1 calc R . . C5 C 0.2223(2) 0.09090(12) 0.11139(10) 0.0207(3) Uani 1 1 d . . . C6 C 0.3784(2) 0.14326(12) 0.28241(10) 0.0219(3) Uani 1 1 d . . . C7 C 0.5822(3) 0.18870(14) 0.34385(11) 0.0279(3) Uani 1 1 d . . . H7 H 0.7176 0.2181 0.3176 0.034 Uiso 1 1 calc R . . C8 C 0.5888(3) 0.19129(14) 0.44265(12) 0.0307(3) Uani 1 1 d . . . H8 H 0.7292 0.2225 0.4831 0.037 Uiso 1 1 calc R . . C9 C 0.3948(3) 0.14925(14) 0.48374(11) 0.0298(3) Uani 1 1 d . . . C10 C 0.1922(3) 0.10653(15) 0.42164(11) 0.0298(3) Uani 1 1 d . . . H10 H 0.0562 0.0789 0.4481 0.036 Uiso 1 1 calc R . . C11 C 0.1810(3) 0.10276(14) 0.32223(11) 0.0269(3) Uani 1 1 d . . . H11 H 0.0397 0.0728 0.2819 0.032 Uiso 1 1 calc R . . C12 C 0.4055(4) 0.14555(16) 0.59133(12) 0.0385(4) Uani 1 1 d . . . H12D H 0.5614 0.1795 0.6229 0.058 Uiso 0.50 1 calc PR . . H12F H 0.3718 0.0610 0.6096 0.058 Uiso 0.50 1 calc PR . . H12E H 0.2902 0.1937 0.6114 0.058 Uiso 0.50 1 calc PR . . H12C H 0.2543 0.1100 0.6063 0.058 Uiso 0.50 1 calc PR . . H12B H 0.4438 0.2285 0.6196 0.058 Uiso 0.50 1 calc PR . . H12A H 0.5254 0.0958 0.6179 0.058 Uiso 0.50 1 calc PR . . C13 C 1.0037(2) 0.34470(12) 0.02130(10) 0.0198(3) Uani 1 1 d . . . C14 C 1.2219(2) 0.42064(12) 0.18002(10) 0.0199(3) Uani 1 1 d . . . C15 C 1.4273(2) 0.47171(13) 0.15047(10) 0.0214(3) Uani 1 1 d . . . H15 H 1.4416 0.4709 0.0842 0.026 Uiso 1 1 calc R . . C16 C 1.6115(2) 0.52394(13) 0.21874(10) 0.0226(3) Uani 1 1 d . . . H16 H 1.7512 0.5583 0.1980 0.027 Uiso 1 1 calc R . . C17 C 1.5975(2) 0.52741(13) 0.31652(10) 0.0230(3) Uani 1 1 d . . . C18 C 1.3880(3) 0.47868(13) 0.34417(10) 0.0243(3) Uani 1 1 d . . . H18 H 1.3716 0.4820 0.4102 0.029 Uiso 1 1 calc R . . C19 C 1.2037(2) 0.42578(13) 0.27770(10) 0.0227(3) Uani 1 1 d . . . H19 H 1.0633 0.3926 0.2986 0.027 Uiso 1 1 calc R . . C20 C 1.8035(3) 0.57640(16) 0.39035(11) 0.0304(3) Uani 1 1 d . . . H20C H 1.7594 0.5713 0.4547 0.046 Uiso 0.50 1 calc PR . . H20A H 1.8534 0.6616 0.3779 0.046 Uiso 0.50 1 calc PR . . H20B H 1.9315 0.5281 0.3865 0.046 Uiso 0.50 1 calc PR . . H20D H 1.9368 0.6027 0.3580 0.046 Uiso 0.50 1 calc PR . . H20F H 1.8428 0.5124 0.4348 0.046 Uiso 0.50 1 calc PR . . H20E H 1.7647 0.6459 0.4262 0.046 Uiso 0.50 1 calc PR . . 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 O1 0.0192(5) 0.0280(5) 0.0255(5) 0.0011(4) 0.0026(4) -0.0052(4) N1 0.0163(5) 0.0219(6) 0.0220(6) 0.0011(4) 0.0030(4) -0.0024(4) C1 0.0234(7) 0.0257(7) 0.0230(7) 0.0007(5) 0.0038(5) -0.0018(5) O2 0.0213(5) 0.0282(5) 0.0227(5) 0.0021(4) 0.0045(4) -0.0035(4) N2 0.0160(5) 0.0213(5) 0.0238(6) 0.0008(4) 0.0040(4) -0.0026(4) C2 0.0193(6) 0.0196(6) 0.0211(6) 0.0011(5) 0.0012(5) 0.0022(5) N3 0.0169(5) 0.0247(6) 0.0227(6) 0.0007(4) 0.0014(4) -0.0031(4) C3 0.0206(6) 0.0214(6) 0.0220(7) -0.0005(5) 0.0008(5) -0.0008(5) N4 0.0181(5) 0.0241(6) 0.0231(6) 0.0010(5) 0.0010(4) -0.0025(4) C4 0.0172(6) 0.0186(6) 0.0246(7) 0.0025(5) 0.0031(5) 0.0014(5) N5 0.0174(5) 0.0255(6) 0.0217(6) 0.0001(4) 0.0035(4) -0.0047(4) C5 0.0187(6) 0.0191(6) 0.0236(7) 0.0021(5) 0.0019(5) 0.0015(5) C6 0.0225(6) 0.0192(6) 0.0232(7) 0.0014(5) 0.0013(5) 0.0020(5) C7 0.0230(7) 0.0283(7) 0.0301(8) -0.0006(6) -0.0005(6) -0.0002(6) C8 0.0298(8) 0.0282(8) 0.0300(8) -0.0035(6) -0.0054(6) 0.0012(6) C9 0.0390(9) 0.0240(7) 0.0258(7) -0.0003(6) 0.0000(6) 0.0077(6) C10 0.0321(8) 0.0327(8) 0.0241(7) 0.0020(6) 0.0058(6) 0.0007(6) C11 0.0224(7) 0.0292(7) 0.0272(7) 0.0015(6) 0.0013(6) -0.0010(6) C12 0.0559(11) 0.0344(9) 0.0239(8) -0.0006(6) -0.0001(7) 0.0088(8) C13 0.0179(6) 0.0182(6) 0.0226(6) 0.0002(5) 0.0018(5) 0.0007(5) C14 0.0185(6) 0.0186(6) 0.0215(6) 0.0005(5) 0.0015(5) 0.0002(5) C15 0.0202(6) 0.0240(6) 0.0195(6) 0.0000(5) 0.0044(5) -0.0009(5) C16 0.0178(6) 0.0240(7) 0.0253(7) 0.0004(5) 0.0035(5) -0.0005(5) C17 0.0200(6) 0.0249(7) 0.0232(7) -0.0017(5) 0.0007(5) 0.0031(5) C18 0.0252(7) 0.0287(7) 0.0193(6) 0.0012(5) 0.0047(5) 0.0032(5) C19 0.0200(6) 0.0255(7) 0.0226(7) 0.0012(5) 0.0056(5) -0.0002(5) C20 0.0233(7) 0.0421(9) 0.0240(7) -0.0061(6) -0.0002(6) 0.0026(6) _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 O1 C5 1.2374(16) . ? N1 C2 1.3731(18) . ? N1 N2 1.3789(16) . ? N1 C13 1.4259(17) . ? C1 C2 1.484(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 C13 1.2093(16) . ? N2 C4 1.3179(17) . ? C2 C3 1.3686(19) . ? N3 C5 1.3717(19) . ? N3 C4 1.3862(17) . ? N3 H3N 0.8800 . ? C3 C4 1.418(2) . ? C3 H3 0.9500 . ? N4 C5 1.3548(18) . ? N4 C6 1.4075(19) . ? N4 H4N 0.8800 . ? N5 C13 1.3515(18) . ? N5 C14 1.4081(17) . ? N5 H5N 0.8800 . ? C6 C11 1.391(2) . ? C6 C7 1.397(2) . ? C7 C8 1.386(2) . ? C7 H7 0.9500 . ? C8 C9 1.387(2) . ? C8 H8 0.9500 . ? C9 C10 1.390(2) . ? C9 C12 1.509(2) . ? C10 C11 1.392(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12D 0.9800 . ? C12 H12F 0.9800 . ? C12 H12E 0.9800 . ? C12 H12C 0.9800 . ? C12 H12B 0.9800 . ? C12 H12A 0.9800 . ? C14 C15 1.3918(18) . ? C14 C19 1.397(2) . ? C15 C16 1.3916(19) . ? C15 H15 0.9500 . ? C16 C17 1.392(2) . ? C16 H16 0.9500 . ? C17 C18 1.394(2) . ? C17 C20 1.507(2) . ? C18 C19 1.380(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20D 0.9800 . ? C20 H20F 0.9800 . ? C20 H20E 0.9800 . ? 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 C2 N1 N2 112.03(11) . . ? C2 N1 C13 127.93(12) . . ? N2 N1 C13 120.02(11) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 N2 N1 104.24(11) . . ? C3 C2 N1 106.09(12) . . ? C3 C2 C1 129.05(13) . . ? N1 C2 C1 124.84(12) . . ? C5 N3 C4 129.59(12) . . ? C5 N3 H3N 115.2 . . ? C4 N3 H3N 115.2 . . ? C2 C3 C4 105.52(12) . . ? C2 C3 H3 127.2 . . ? C4 C3 H3 127.2 . . ? C5 N4 C6 127.28(12) . . ? C5 N4 H4N 116.4 . . ? C6 N4 H4N 116.4 . . ? N2 C4 N3 123.86(13) . . ? N2 C4 C3 112.11(12) . . ? N3 C4 C3 124.03(13) . . ? C13 N5 C14 127.76(12) . . ? C13 N5 H5N 116.1 . . ? C14 N5 H5N 116.1 . . ? O1 C5 N4 123.99(13) . . ? O1 C5 N3 119.59(12) . . ? N4 C5 N3 116.42(12) . . ? C11 C6 C7 118.72(13) . . ? C11 C6 N4 124.22(13) . . ? C7 C6 N4 117.05(13) . . ? C8 C7 C6 120.64(14) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 121.45(14) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C10 117.21(14) . . ? C8 C9 C12 121.46(15) . . ? C10 C9 C12 121.29(16) . . ? C9 C10 C11 122.49(15) . . ? C9 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? C6 C11 C10 119.47(14) . . ? C6 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C9 C12 H12D 109.5 . . ? C9 C12 H12F 109.5 . . ? H12D C12 H12F 109.5 . . ? C9 C12 H12E 109.5 . . ? H12D C12 H12E 109.5 . . ? H12F C12 H12E 109.5 . . ? C9 C12 H12C 109.5 . . ? H12D C12 H12C 141.1 . . ? H12F C12 H12C 56.3 . . ? H12E C12 H12C 56.3 . . ? C9 C12 H12B 109.5 . . ? H12D C12 H12B 56.3 . . ? H12F C12 H12B 141.1 . . ? H12E C12 H12B 56.3 . . ? H12C C12 H12B 109.5 . . ? C9 C12 H12A 109.5 . . ? H12D C12 H12A 56.3 . . ? H12F C12 H12A 56.3 . . ? H12E C12 H12A 141.1 . . ? H12C C12 H12A 109.5 . . ? H12B C12 H12A 109.5 . . ? O2 C13 N5 127.40(13) . . ? O2 C13 N1 121.07(12) . . ? N5 C13 N1 111.52(11) . . ? C15 C14 C19 118.98(12) . . ? C15 C14 N5 124.29(12) . . ? C19 C14 N5 116.69(12) . . ? C16 C15 C14 119.50(13) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 122.10(13) . . ? C15 C16 H16 118.9 . . ? C17 C16 H16 118.9 . . ? C16 C17 C18 117.37(13) . . ? C16 C17 C20 121.61(13) . . ? C18 C17 C20 120.95(13) . . ? C19 C18 C17 121.42(13) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C14 120.58(13) . . ? C18 C19 H19 119.7 . . ? C14 C19 H19 119.7 . . ? C17 C20 H20C 109.5 . . ? C17 C20 H20A 109.5 . . ? H20C C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20C C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20D 109.5 . . ? H20C C20 H20D 141.1 . . ? H20A C20 H20D 56.3 . . ? H20B C20 H20D 56.3 . . ? C17 C20 H20F 109.5 . . ? H20C C20 H20F 56.3 . . ? H20A C20 H20F 141.1 . . ? H20B C20 H20F 56.3 . . ? H20D C20 H20F 109.5 . . ? C17 C20 H20E 109.5 . . ? H20C C20 H20E 56.3 . . ? H20A C20 H20E 56.3 . . ? H20B C20 H20E 141.1 . . ? H20D C20 H20E 109.5 . . ? H20F C20 H20E 109.5 . . ? 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 C2 N1 N2 C4 -0.69(15) . . . . ? C13 N1 N2 C4 -179.21(11) . . . . ? N2 N1 C2 C3 0.88(15) . . . . ? C13 N1 C2 C3 179.25(12) . . . . ? N2 N1 C2 C1 -177.64(12) . . . . ? C13 N1 C2 C1 0.7(2) . . . . ? N1 C2 C3 C4 -0.68(15) . . . . ? C1 C2 C3 C4 177.76(14) . . . . ? N1 N2 C4 N3 -179.40(12) . . . . ? N1 N2 C4 C3 0.24(15) . . . . ? C5 N3 C4 N2 -9.6(2) . . . . ? C5 N3 C4 C3 170.84(14) . . . . ? C2 C3 C4 N2 0.28(16) . . . . ? C2 C3 C4 N3 179.91(12) . . . . ? C6 N4 C5 O1 0.1(2) . . . . ? C6 N4 C5 N3 -179.81(12) . . . . ? C4 N3 C5 O1 -177.79(13) . . . . ? C4 N3 C5 N4 2.1(2) . . . . ? C5 N4 C6 C11 -10.7(2) . . . . ? C5 N4 C6 C7 170.71(13) . . . . ? C11 C6 C7 C8 1.2(2) . . . . ? N4 C6 C7 C8 179.89(13) . . . . ? C6 C7 C8 C9 0.0(2) . . . . ? C7 C8 C9 C10 -1.2(2) . . . . ? C7 C8 C9 C12 176.55(15) . . . . ? C8 C9 C10 C11 1.3(2) . . . . ? C12 C9 C10 C11 -176.44(15) . . . . ? C7 C6 C11 C10 -1.1(2) . . . . ? N4 C6 C11 C10 -179.68(14) . . . . ? C9 C10 C11 C6 -0.2(2) . . . . ? C14 N5 C13 O2 -3.8(2) . . . . ? C14 N5 C13 N1 175.39(12) . . . . ? C2 N1 C13 O2 6.9(2) . . . . ? N2 N1 C13 O2 -174.86(12) . . . . ? C2 N1 C13 N5 -172.41(13) . . . . ? N2 N1 C13 N5 5.85(17) . . . . ? C13 N5 C14 C15 -4.1(2) . . . . ? C13 N5 C14 C19 178.20(13) . . . . ? C19 C14 C15 C16 1.6(2) . . . . ? N5 C14 C15 C16 -176.08(13) . . . . ? C14 C15 C16 C17 -0.2(2) . . . . ? C15 C16 C17 C18 -1.5(2) . . . . ? C15 C16 C17 C20 175.73(14) . . . . ? C16 C17 C18 C19 1.9(2) . . . . ? C20 C17 C18 C19 -175.35(14) . . . . ? C17 C18 C19 C14 -0.6(2) . . . . ? C15 C14 C19 C18 -1.2(2) . . . . ? N5 C14 C19 C18 176.65(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4N N2 0.88 2.01 2.7332(17) 139.0 . N5 H5N N2 0.88 2.15 2.6152(16) 112.8 . N3 H3N O1 0.88 1.92 2.7861(15) 166.1 2 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.462 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 971043' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_c:\users\gol\desktop\steed\compou~2\gol1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 N5 O2' _chemical_formula_sum 'C20 H21 N5 O2' _chemical_formula_weight 363.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.594(4) _cell_length_b 7.122(6) _cell_length_c 28.06(3) _cell_angle_alpha 93.46(2) _cell_angle_beta 92.554(15) _cell_angle_gamma 104.922(15) _cell_volume 883.7(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 799 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 21.36 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.566 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details TwinAbs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Smart-6K _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1788 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0653 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 0.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1780 _reflns_number_gt 1359 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Smart - Bruker' _computing_cell_refinement 'Apex2 -Bruker' _computing_data_reduction 'Apex2 - Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Xseed _computing_publication_material Xseed _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. Crystal was twinned with two domains resulting in low two theta full value, low bond precision, and large su on c axis value. Connectivity of structure is clearly defined and therefore it is felt the crystal refinement is of good quality. BASF Shelx command was utilised to improve refinement statistics due to twinning of crystal. This resulted in a number of restraints. ; _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^)+(0.1850P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1789 _refine_ls_number_parameters 250 _refine_ls_number_restraints 69 _refine_ls_R_factor_all 0.1001 _refine_ls_R_factor_gt 0.0698 _refine_ls_wR_factor_ref 0.2483 _refine_ls_wR_factor_gt 0.2140 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.053 _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 O1 O 0.5108(13) 0.9743(7) 0.3245(2) 0.0231(14) Uani 1 1 d U . . N1 N 0.3405(16) 0.5238(8) 0.2163(3) 0.0195(16) Uani 1 1 d U . . C1 C 0.380(2) 0.1755(11) 0.2183(3) 0.027(2) Uani 1 1 d U . . H1A H 0.4333 0.1584 0.1859 0.041 Uiso 1 1 calc R . . H1B H 0.1669 0.1234 0.2201 0.041 Uiso 1 1 calc R . . H1C H 0.4865 0.1085 0.2387 0.041 Uiso 1 1 calc R . . O2 O -0.0114(14) 0.3300(7) 0.1613(2) 0.0251(15) Uani 1 1 d U . . N2 N 0.4656(17) 0.7105(8) 0.2363(3) 0.0204(16) Uani 1 1 d U . . C2 C 0.467(2) 0.3914(10) 0.2344(3) 0.0203(19) Uani 1 1 d U . . N3 N 0.8726(16) 0.8408(8) 0.2956(3) 0.0211(16) Uani 1 1 d U . . H3N H 1.0631 0.8505 0.2959 0.025 Uiso 1 1 calc R . . C3 C 0.685(2) 0.4881(11) 0.2673(3) 0.024(2) Uani 1 1 d U . . H3 H 0.8140 0.4370 0.2859 0.029 Uiso 1 1 calc R . . N4 N 1.0078(16) 1.1180(9) 0.3462(3) 0.0234(17) Uani 1 1 d U . . H4N H 1.1887 1.1073 0.3436 0.028 Uiso 1 1 calc R . . C4 C 0.6731(18) 0.6832(10) 0.2673(3) 0.0155(17) Uani 1 1 d U . . N5 N 0.0447(16) 0.6614(9) 0.1668(2) 0.0196(16) Uani 1 1 d U . . H5N H 0.1505 0.7669 0.1821 0.024 Uiso 1 1 calc R . . C5 C 0.7767(18) 0.9771(10) 0.3222(3) 0.0143(16) Uani 1 1 d U . . C6 C 0.970(2) 1.2793(11) 0.3751(3) 0.0228(19) Uani 1 1 d U . . C7 C 1.158(2) 1.4600(11) 0.3693(3) 0.027(2) Uani 1 1 d U . . H7 H 1.3040 1.4731 0.3469 0.032 Uiso 1 1 calc R . . C8 C 1.132(2) 1.6218(11) 0.3967(4) 0.031(2) Uani 1 1 d U . . H8 H 1.2565 1.7435 0.3916 0.037 Uiso 1 1 calc R . . C9 C 0.926(2) 1.6074(12) 0.4311(4) 0.030(2) Uani 1 1 d U . . C10 C 0.740(2) 1.4226(12) 0.4369(4) 0.034(2) Uani 1 1 d U . . H10 H 0.5981 1.4088 0.4600 0.040 Uiso 1 1 calc R . . C11 C 0.760(2) 1.2595(11) 0.4091(3) 0.026(2) Uani 1 1 d U . . H11 H 0.6323 1.1379 0.4134 0.031 Uiso 1 1 calc R . . C12 C 0.898(3) 1.7809(13) 0.4619(4) 0.047(3) Uani 1 1 d U . . H12B H 1.0132 1.8980 0.4494 0.070 Uiso 1 1 calc R . . H12A H 0.9735 1.7731 0.4940 0.070 Uiso 1 1 calc R . . H12C H 0.6899 1.7826 0.4619 0.070 Uiso 1 1 calc R . . C13 C 0.1022(19) 0.4943(10) 0.1786(3) 0.0201(19) Uani 1 1 d U . . C14 C -0.172(2) 0.6802(11) 0.1317(3) 0.0218(18) Uani 1 1 d U . . C15 C -0.353(2) 0.5274(11) 0.1016(3) 0.025(2) Uani 1 1 d U . . H15 H -0.3410 0.4006 0.1050 0.030 Uiso 1 1 calc R . . C16 C -0.550(2) 0.5624(12) 0.0669(4) 0.028(2) Uani 1 1 d U . . H16 H -0.6680 0.4581 0.0473 0.033 Uiso 1 1 calc R . . C17 C -0.577(2) 0.7506(11) 0.0603(3) 0.0230(19) Uani 1 1 d U . . C18 C -0.394(2) 0.9022(12) 0.0900(3) 0.028(2) Uani 1 1 d U . . H18 H -0.4039 1.0292 0.0861 0.034 Uiso 1 1 calc R . . C19 C -0.1990(19) 0.8697(11) 0.1249(3) 0.0211(19) Uani 1 1 d U . . H19 H -0.0819 0.9745 0.1444 0.025 Uiso 1 1 calc R . . C20 C -0.789(2) 0.7863(12) 0.0218(3) 0.031(2) Uani 1 1 d U . . H20C H -0.7569 0.9240 0.0196 0.047 Uiso 1 1 calc R . . H20A H -0.9934 0.7306 0.0295 0.047 Uiso 1 1 calc R . . H20B H -0.7527 0.7271 -0.0082 0.047 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 O1 0.017(3) 0.021(3) 0.029(4) -0.005(2) 0.001(2) 0.002(2) N1 0.023(4) 0.012(3) 0.022(4) -0.006(3) -0.001(3) 0.004(3) C1 0.035(6) 0.016(3) 0.030(6) 0.000(3) 0.001(4) 0.005(4) O2 0.030(4) 0.013(3) 0.029(4) -0.004(2) -0.004(3) 0.001(2) N2 0.027(4) 0.015(3) 0.017(4) -0.004(3) -0.002(3) 0.002(3) C2 0.024(5) 0.017(3) 0.023(5) -0.002(3) 0.001(3) 0.012(3) N3 0.012(4) 0.020(3) 0.030(5) -0.008(3) -0.004(3) 0.005(3) C3 0.023(5) 0.019(3) 0.029(6) 0.004(3) -0.001(4) 0.004(3) N4 0.017(4) 0.021(3) 0.031(5) -0.009(3) 0.000(3) 0.005(3) C4 0.013(4) 0.014(3) 0.019(5) -0.002(3) 0.000(3) 0.003(3) N5 0.016(4) 0.013(3) 0.031(5) -0.001(3) -0.003(3) 0.006(3) C5 0.010(4) 0.021(4) 0.013(4) 0.000(3) -0.001(3) 0.007(3) C6 0.025(5) 0.017(3) 0.028(6) -0.002(3) -0.008(4) 0.010(3) C7 0.033(6) 0.021(4) 0.024(6) 0.000(3) -0.002(4) 0.003(3) C8 0.035(6) 0.019(4) 0.034(7) 0.006(4) -0.006(4) 0.000(4) C9 0.039(6) 0.020(4) 0.029(6) -0.010(4) -0.010(4) 0.011(4) C10 0.024(6) 0.029(4) 0.047(7) -0.004(4) 0.009(4) 0.006(4) C11 0.017(5) 0.024(4) 0.035(6) 0.003(4) -0.002(4) 0.001(4) C12 0.052(8) 0.033(5) 0.055(8) -0.012(5) -0.004(6) 0.017(5) C13 0.023(5) 0.018(4) 0.017(5) 0.000(3) -0.004(3) 0.002(3) C14 0.019(5) 0.021(4) 0.027(5) 0.002(3) 0.003(3) 0.008(3) C15 0.024(5) 0.020(4) 0.032(6) -0.001(4) -0.003(4) 0.008(3) C16 0.019(5) 0.026(4) 0.034(6) -0.002(4) -0.005(4) 0.001(3) C17 0.026(5) 0.026(4) 0.019(5) 0.010(3) 0.005(3) 0.008(3) C18 0.039(6) 0.019(4) 0.028(6) 0.003(3) 0.001(4) 0.008(4) C19 0.017(5) 0.018(3) 0.029(6) -0.002(3) -0.002(3) 0.006(3) C20 0.021(5) 0.035(5) 0.038(6) 0.005(4) -0.002(4) 0.008(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.221(9) . ? N1 C2 1.340(10) . ? N1 N2 1.379(8) . ? N1 C13 1.455(11) . ? C1 C2 1.520(10) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? O2 C13 1.212(9) . ? N2 C4 1.322(10) . ? C2 C3 1.347(12) . ? N3 C5 1.361(10) . ? N3 C4 1.424(10) . ? N3 H3N 0.8600 . ? C3 C4 1.404(10) . ? C3 H3 0.9300 . ? N4 C5 1.377(10) . ? N4 C6 1.417(10) . ? N4 H4N 0.8600 . ? N5 C13 1.341(10) . ? N5 C14 1.406(11) . ? N5 H5N 0.8600 . ? C6 C7 1.377(12) . ? C6 C11 1.376(13) . ? C7 C8 1.381(13) . ? C7 H7 0.9300 . ? C8 C9 1.370(14) . ? C8 H8 0.9300 . ? C9 C10 1.397(12) . ? C9 C12 1.501(13) . ? C10 C11 1.384(12) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12B 0.9600 . ? C12 H12A 0.9600 . ? C12 H12C 0.9600 . ? C14 C15 1.397(12) . ? C14 C19 1.410(11) . ? C15 C16 1.375(13) . ? C15 H15 0.9300 . ? C16 C17 1.401(11) . ? C16 H16 0.9300 . ? C17 C18 1.391(12) . ? C17 C20 1.496(12) . ? C18 C19 1.366(12) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? 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 C2 N1 N2 113.4(7) . . ? C2 N1 C13 128.4(6) . . ? N2 N1 C13 118.2(6) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 N2 N1 101.7(6) . . ? N1 C2 C3 106.9(7) . . ? N1 C2 C1 124.9(8) . . ? C3 C2 C1 128.2(7) . . ? C5 N3 C4 123.3(7) . . ? C5 N3 H3N 118.4 . . ? C4 N3 H3N 118.4 . . ? C2 C3 C4 104.7(7) . . ? C2 C3 H3 127.6 . . ? C4 C3 H3 127.6 . . ? C5 N4 C6 124.9(7) . . ? C5 N4 H4N 117.5 . . ? C6 N4 H4N 117.5 . . ? N2 C4 C3 113.3(7) . . ? N2 C4 N3 122.0(6) . . ? C3 C4 N3 124.6(7) . . ? C13 N5 C14 126.1(7) . . ? C13 N5 H5N 117.0 . . ? C14 N5 H5N 117.0 . . ? O1 C5 N3 123.2(7) . . ? O1 C5 N4 123.2(7) . . ? N3 C5 N4 113.7(7) . . ? C7 C6 C11 119.8(8) . . ? C7 C6 N4 118.0(9) . . ? C11 C6 N4 122.3(7) . . ? C6 C7 C8 120.3(9) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C9 C8 C7 121.5(8) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 117.4(8) . . ? C8 C9 C12 122.4(8) . . ? C10 C9 C12 120.2(10) . . ? C11 C10 C9 121.7(10) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C6 C11 C10 119.3(8) . . ? C6 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C9 C12 H12B 109.5 . . ? C9 C12 H12A 109.5 . . ? H12B C12 H12A 109.5 . . ? C9 C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? O2 C13 N5 128.7(8) . . ? O2 C13 N1 118.5(7) . . ? N5 C13 N1 112.8(6) . . ? C15 C14 N5 125.2(7) . . ? C15 C14 C19 117.3(8) . . ? N5 C14 C19 117.3(7) . . ? C16 C15 C14 120.8(8) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 121.9(8) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C18 C17 C16 117.1(9) . . ? C18 C17 C20 121.8(7) . . ? C16 C17 C20 121.1(8) . . ? C19 C18 C17 121.8(8) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C18 C19 C14 121.2(8) . . ? C18 C19 H19 119.4 . . ? C14 C19 H19 119.4 . . ? C17 C20 H20C 109.5 . . ? C17 C20 H20A 109.5 . . ? H20C C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20C C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? 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 C2 N1 N2 C4 -0.2(10) . . . . ? C13 N1 N2 C4 -178.4(7) . . . . ? N2 N1 C2 C3 -0.3(11) . . . . ? C13 N1 C2 C3 177.7(9) . . . . ? N2 N1 C2 C1 -178.3(8) . . . . ? C13 N1 C2 C1 -0.3(15) . . . . ? N1 C2 C3 C4 0.6(10) . . . . ? C1 C2 C3 C4 178.6(8) . . . . ? N1 N2 C4 C3 0.6(10) . . . . ? N1 N2 C4 N3 177.3(7) . . . . ? C2 C3 C4 N2 -0.7(11) . . . . ? C2 C3 C4 N3 -177.4(8) . . . . ? C5 N3 C4 N2 51.2(12) . . . . ? C5 N3 C4 C3 -132.4(9) . . . . ? C4 N3 C5 O1 0.9(12) . . . . ? C4 N3 C5 N4 -179.2(7) . . . . ? C6 N4 C5 O1 -2.3(12) . . . . ? C6 N4 C5 N3 177.9(7) . . . . ? C5 N4 C6 C7 -134.1(9) . . . . ? C5 N4 C6 C11 47.8(12) . . . . ? C11 C6 C7 C8 -1.6(13) . . . . ? N4 C6 C7 C8 -179.7(7) . . . . ? C6 C7 C8 C9 2.0(13) . . . . ? C7 C8 C9 C10 -1.1(13) . . . . ? C7 C8 C9 C12 178.7(9) . . . . ? C8 C9 C10 C11 -0.1(14) . . . . ? C12 C9 C10 C11 -179.9(9) . . . . ? C7 C6 C11 C10 0.4(13) . . . . ? N4 C6 C11 C10 178.4(8) . . . . ? C9 C10 C11 C6 0.4(14) . . . . ? C14 N5 C13 O2 2.0(15) . . . . ? C14 N5 C13 N1 -179.9(7) . . . . ? C2 N1 C13 O2 3.1(14) . . . . ? N2 N1 C13 O2 -179.0(8) . . . . ? C2 N1 C13 N5 -175.3(9) . . . . ? N2 N1 C13 N5 2.7(11) . . . . ? C13 N5 C14 C15 -3.6(15) . . . . ? C13 N5 C14 C19 179.7(8) . . . . ? N5 C14 C15 C16 -177.0(8) . . . . ? C19 C14 C15 C16 -0.3(14) . . . . ? C14 C15 C16 C17 0.0(15) . . . . ? C15 C16 C17 C18 0.7(15) . . . . ? C15 C16 C17 C20 179.1(9) . . . . ? C16 C17 C18 C19 -1.2(14) . . . . ? C20 C17 C18 C19 -179.6(9) . . . . ? C17 C18 C19 C14 0.9(14) . . . . ? C15 C14 C19 C18 -0.2(14) . . . . ? N5 C14 C19 C18 176.8(8) . . . . ? _diffrn_measured_fraction_theta_max 0.562 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.562 _refine_diff_density_max 0.330 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.087 _database_code_depnum_ccdc_archive 'CCDC 971042'