# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'David Amabilino' _publ_contact_author_address ; Institut de Ciencia de Materials de CSIC Campus Universitari Bellaterra 08193 SPAIN ; _publ_contact_author_email AMABILINO@ICMAB.ES _publ_section_title ; Polymorphs of a Pyrazole Nitronyl Nitroxide and its complexes with metal (II) hexafluoroacetylacetonates ; loop_ _publ_author_name 'David Amabilino' 'Laure Catala' 'Jaume Veciana' 'Klaus Wurst' # Attachment 'CO.CIF' data_co _database_code_depnum_ccdc_archive 'CCDC 603117' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H34 Co2 F24 N8 O12' _chemical_formula_weight 1392.61 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 32.361(1) _cell_length_b 8.8752(4) _cell_length_c 21.1416(5) _cell_angle_alpha 90.00 _cell_angle_beta 118.260(2) _cell_angle_gamma 90.00 _cell_volume 5348.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 218(2) _cell_measurement_reflns_used 13350 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 23.0 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.729 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2784 _exptl_absorpt_coefficient_mu 0.769 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 218(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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11193 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 22.94 _reflns_number_total 3665 _reflns_number_gt 3020 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Disorder of two CF3-groups; 2:1 F1-F3:F1a-F3a and 1:1 F4-F6:F4a-F6a ; _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^)+(0.0433P)^2^+8.5373P] 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, refined at N4' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3665 _refine_ls_number_parameters 450 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0928 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 Co1 Co 0.653074(13) 0.57584(5) 0.472631(19) 0.03255(15) Uani 1 1 d . . . O1 O 0.78753(9) 1.0344(3) 0.75854(11) 0.0543(6) Uani 1 1 d . . . O2 O 0.80159(7) 1.0471(2) 0.55140(10) 0.0366(5) Uani 1 1 d . . . O3 O 0.58947(7) 0.4722(2) 0.40608(10) 0.0433(5) Uani 1 1 d . . . O4 O 0.66203(7) 0.4211(2) 0.55073(10) 0.0400(5) Uani 1 1 d . . . O5 O 0.61135(8) 0.7125(3) 0.49871(11) 0.0468(6) Uani 1 1 d . . . O6 O 0.63761(8) 0.7133(2) 0.38696(10) 0.0416(5) Uani 1 1 d . . . N1 N 0.80069(9) 1.0758(3) 0.71300(12) 0.0381(6) Uani 1 1 d . . . N2 N 0.80750(8) 1.0814(3) 0.61544(12) 0.0341(6) Uani 1 1 d . . . N3 N 0.71074(8) 0.6951(3) 0.55397(11) 0.0328(6) Uani 1 1 d . . . N4 N 0.72411(9) 0.6643(3) 0.62371(12) 0.0360(6) Uani 1 1 d . . . H4 H 0.7122(12) 0.593(4) 0.6342(17) 0.040(10) Uiso 1 1 d . . . C1 C 0.78982(10) 1.0032(3) 0.65073(14) 0.0311(7) Uani 1 1 d . . . C2 C 0.83374(11) 1.2050(4) 0.72592(17) 0.0467(8) Uani 1 1 d . . . C3 C 0.82436(12) 1.2356(4) 0.64816(17) 0.0467(8) Uani 1 1 d . . . C4 C 0.76158(10) 0.8691(3) 0.62641(13) 0.0309(7) Uani 1 1 d . . . C5 C 0.73343(10) 0.8202(3) 0.55543(14) 0.0310(7) Uani 1 1 d . . . H5 H 0.7310 0.8697 0.5145 0.037 Uiso 1 1 calc . . . C6 C 0.75397(11) 0.7651(4) 0.66798(14) 0.0375(7) Uani 1 1 d . . . H6 H 0.7674 0.7655 0.7183 0.045 Uiso 1 1 calc . . . C7 C 0.56867(11) 0.3828(4) 0.42646(16) 0.0434(8) Uani 1 1 d . . . C8 C 0.58638(12) 0.3064(4) 0.49178(17) 0.0498(9) Uani 1 1 d . . . H8 H 0.5668 0.2380 0.4990 0.060 Uiso 1 1 calc . . . C9 C 0.63160(12) 0.3275(4) 0.54631(15) 0.0430(8) Uani 1 1 d . . . C10 C 0.57835(12) 0.7894(4) 0.45250(19) 0.0493(9) Uani 1 1 d . . . C11 C 0.57022(12) 0.8283(4) 0.38392(18) 0.0517(9) Uani 1 1 d . . . H11 H 0.5436 0.8863 0.3549 0.062 Uiso 1 1 calc . . . C12 C 0.59980(12) 0.7852(4) 0.35668(16) 0.0424(8) Uani 1 1 d . . . C21 C 0.88299(14) 1.1450(6) 0.7754(2) 0.0840(14) Uani 1 1 d . . . H21A H 0.9057 1.2249 0.7857 0.126 Uiso 1 1 calc R . . H21B H 0.8899 1.0622 0.7520 0.126 Uiso 1 1 calc R . . H21C H 0.8845 1.1099 0.8199 0.126 Uiso 1 1 calc R . . C22 C 0.82249(16) 1.3355(4) 0.7619(2) 0.0687(12) Uani 1 1 d . . . H22A H 0.8421 1.4212 0.7655 0.103 Uiso 1 1 calc R . . H22B H 0.8285 1.3054 0.8097 0.103 Uiso 1 1 calc R . . H22C H 0.7897 1.3630 0.7336 0.103 Uiso 1 1 calc R . . C31 C 0.86616(17) 1.2837(5) 0.6402(3) 0.0854(15) Uani 1 1 d . . . H31A H 0.8771 1.3809 0.6631 0.128 Uiso 1 1 calc R . . H31B H 0.8574 1.2914 0.5897 0.128 Uiso 1 1 calc R . . H31C H 0.8910 1.2098 0.6628 0.128 Uiso 1 1 calc R . . C32 C 0.78316(16) 1.3416(4) 0.6061(2) 0.0675(11) Uani 1 1 d . . . H32A H 0.7569 1.3127 0.6136 0.101 Uiso 1 1 calc R . . H32B H 0.7740 1.3352 0.5554 0.101 Uiso 1 1 calc R . . H32C H 0.7924 1.4441 0.6227 0.101 Uiso 1 1 calc R . . C71 C 0.51799(15) 0.3496(6) 0.3706(2) 0.0705(13) Uani 1 1 d . . . C91 C 0.64839(18) 0.2189(6) 0.6108(2) 0.0792(15) Uani 1 1 d . . . C101 C 0.54224(15) 0.8368(5) 0.4756(3) 0.0701(11) Uani 1 1 d . . . C121 C 0.58465(14) 0.8210(4) 0.27785(18) 0.0563(10) Uani 1 1 d . . . F1 F 0.5207(2) 0.2334(9) 0.3267(4) 0.106(2) Uani 0.67 1 d P . . F2 F 0.4932(2) 0.2889(14) 0.3961(3) 0.116(3) Uani 0.67 1 d P . . F3 F 0.4983(4) 0.4572(12) 0.3269(6) 0.105(4) Uani 0.67 1 d P . . F4 F 0.6210(5) 0.174(2) 0.6276(9) 0.153(6) Uani 0.50 1 d P . . F6 F 0.6848(6) 0.251(2) 0.6583(7) 0.204(10) Uani 0.50 1 d P . . F5 F 0.6597(5) 0.0820(12) 0.5854(5) 0.154(4) Uani 0.50 1 d P . . F7 F 0.51759(16) 0.9535(5) 0.4415(2) 0.178(2) Uani 1 1 d . . . F8 F 0.51316(12) 0.7303(4) 0.4661(2) 0.1401(14) Uani 1 1 d . . . F9 F 0.56081(11) 0.8711(4) 0.54357(18) 0.1224(12) Uani 1 1 d . . . F10 F 0.56589(13) 0.7044(3) 0.23728(12) 0.1149(12) Uani 1 1 d . . . F11 F 0.62074(10) 0.8637(3) 0.26928(11) 0.0837(7) Uani 1 1 d . . . F12 F 0.55410(10) 0.9342(3) 0.25192(12) 0.0882(8) Uani 1 1 d . . . F4A F 0.6235(5) 0.1082(16) 0.6025(6) 0.174(9) Uani 0.50 1 d P . . F6A F 0.6412(4) 0.3062(13) 0.6647(4) 0.114(3) Uani 0.50 1 d P . . F5A F 0.6932(4) 0.2036(14) 0.6480(6) 0.082(4) Uani 0.50 1 d P . . F1A F 0.5036(5) 0.2274(14) 0.3627(12) 0.127(7) Uani 0.33 1 d P . . F2A F 0.4879(3) 0.430(2) 0.3955(8) 0.126(5) Uani 0.33 1 d P . . F3A F 0.5040(8) 0.418(3) 0.3153(10) 0.151(13) Uani 0.33 1 d P . . 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 Co1 0.0337(2) 0.0382(3) 0.0285(2) -0.00210(17) 0.01707(18) -0.00561(18) O1 0.0761(17) 0.0596(16) 0.0384(12) -0.0152(11) 0.0362(12) -0.0173(13) O2 0.0387(12) 0.0454(13) 0.0305(11) -0.0076(9) 0.0204(9) -0.0045(10) O3 0.0419(12) 0.0498(14) 0.0351(11) 0.0017(10) 0.0158(10) -0.0097(11) O4 0.0397(12) 0.0482(13) 0.0308(11) 0.0013(9) 0.0156(9) -0.0096(11) O5 0.0453(13) 0.0583(15) 0.0447(12) -0.0020(11) 0.0277(11) 0.0022(12) O6 0.0417(13) 0.0464(13) 0.0421(12) 0.0061(10) 0.0243(10) -0.0015(11) N1 0.0420(15) 0.0403(15) 0.0335(14) -0.0107(11) 0.0191(12) -0.0076(12) N2 0.0332(14) 0.0388(15) 0.0318(13) -0.0104(11) 0.0167(11) -0.0075(11) N3 0.0371(14) 0.0393(15) 0.0258(13) -0.0036(10) 0.0180(11) -0.0043(12) N4 0.0459(16) 0.0368(16) 0.0295(14) -0.0006(12) 0.0213(12) -0.0085(13) C1 0.0297(16) 0.0371(17) 0.0284(15) -0.0060(13) 0.0152(12) -0.0030(14) C2 0.0440(19) 0.052(2) 0.0488(19) -0.0214(16) 0.0255(16) -0.0153(17) C3 0.057(2) 0.043(2) 0.0535(19) -0.0197(16) 0.0370(17) -0.0191(17) C4 0.0313(16) 0.0377(17) 0.0257(15) -0.0037(13) 0.0150(12) -0.0021(14) C5 0.0336(16) 0.0346(18) 0.0289(15) -0.0017(12) 0.0181(13) -0.0032(14) C6 0.0429(18) 0.0426(19) 0.0236(14) -0.0038(14) 0.0130(13) -0.0022(15) C7 0.0363(18) 0.052(2) 0.0388(18) -0.0034(16) 0.0153(15) -0.0091(16) C8 0.044(2) 0.062(2) 0.0424(19) 0.0049(16) 0.0196(16) -0.0180(17) C9 0.050(2) 0.046(2) 0.0326(16) 0.0019(14) 0.0189(15) -0.0105(17) C10 0.046(2) 0.047(2) 0.063(2) -0.0047(18) 0.0322(18) -0.0017(18) C11 0.046(2) 0.051(2) 0.057(2) 0.0093(17) 0.0238(17) 0.0078(17) C12 0.048(2) 0.0351(19) 0.0408(17) 0.0002(14) 0.0182(16) -0.0088(16) C21 0.047(2) 0.105(4) 0.074(3) -0.021(3) 0.007(2) -0.013(2) C22 0.096(3) 0.054(2) 0.082(3) -0.038(2) 0.064(2) -0.034(2) C31 0.101(3) 0.083(3) 0.116(4) -0.057(3) 0.087(3) -0.059(3) C32 0.090(3) 0.041(2) 0.070(2) -0.0053(19) 0.037(2) 0.001(2) C71 0.053(3) 0.090(4) 0.050(3) 0.011(3) 0.009(2) -0.026(3) C91 0.072(3) 0.090(4) 0.048(3) 0.015(2) 0.006(3) -0.042(3) C101 0.059(3) 0.080(3) 0.088(3) 0.003(3) 0.048(2) 0.012(3) C121 0.068(3) 0.047(2) 0.047(2) 0.0015(18) 0.0212(19) -0.010(2) F1 0.064(4) 0.123(6) 0.089(4) -0.039(4) 0.001(3) -0.027(3) F2 0.041(3) 0.217(10) 0.075(4) 0.040(6) 0.015(2) -0.043(6) F3 0.046(3) 0.084(4) 0.132(10) 0.038(4) -0.001(4) 0.009(3) F4 0.151(11) 0.207(16) 0.156(12) 0.114(11) 0.117(11) 0.026(10) F6 0.205(17) 0.197(15) 0.066(6) 0.074(8) -0.055(9) -0.132(13) F5 0.233(11) 0.089(6) 0.136(8) 0.052(5) 0.086(8) 0.070(7) F7 0.201(4) 0.190(4) 0.241(4) 0.113(4) 0.183(4) 0.140(4) F8 0.108(2) 0.156(3) 0.221(4) -0.068(3) 0.131(3) -0.054(2) F9 0.097(2) 0.177(3) 0.124(2) -0.058(2) 0.0777(19) -0.001(2) F10 0.184(3) 0.0708(17) 0.0510(13) -0.0147(12) 0.0239(16) -0.0452(19) F11 0.104(2) 0.1014(19) 0.0571(13) 0.0174(13) 0.0476(13) -0.0079(16) F12 0.0921(18) 0.0881(18) 0.0619(14) 0.0281(13) 0.0182(13) 0.0204(15) F4A 0.181(13) 0.129(10) 0.068(6) 0.057(5) -0.058(7) -0.128(10) F6A 0.129(7) 0.175(8) 0.049(3) 0.016(4) 0.050(4) -0.023(6) F5A 0.070(5) 0.098(6) 0.075(6) 0.048(5) 0.033(5) 0.036(6) F1A 0.064(10) 0.066(7) 0.17(2) -0.024(10) -0.007(9) -0.022(6) F2A 0.040(5) 0.194(13) 0.135(10) -0.050(10) 0.033(5) 0.002(8) F3A 0.072(13) 0.28(4) 0.045(6) 0.064(13) -0.020(7) -0.068(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O6 2.040(2) . ? Co1 O4 2.060(2) . ? Co1 O5 2.074(2) . ? Co1 O2 2.075(2) 7_666 ? Co1 O3 2.078(2) . ? Co1 N3 2.126(2) . ? O1 N1 1.277(3) . ? O2 N2 1.311(3) . ? O2 Co1 2.075(2) 7_666 ? O3 C7 1.242(4) . ? O4 C9 1.258(4) . ? O5 C10 1.254(4) . ? O6 C12 1.254(4) . ? N1 C1 1.354(4) . ? N1 C2 1.502(4) . ? N2 C1 1.330(4) . ? N2 C3 1.513(4) . ? N3 C5 1.323(4) . ? N3 N4 1.353(3) . ? N4 C6 1.324(4) . ? N4 H4 0.82(3) . ? C1 C4 1.439(4) . ? C2 C22 1.522(5) . ? C2 C21 1.529(5) . ? C2 C3 1.548(5) . ? C3 C31 1.502(5) . ? C3 C32 1.527(5) . ? C4 C6 1.375(4) . ? C4 C5 1.406(4) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? C7 C8 1.395(5) . ? C7 C71 1.528(5) . ? C8 C9 1.381(5) . ? C8 H8 0.9400 . ? C9 C91 1.543(5) . ? C10 C11 1.389(5) . ? C10 C101 1.524(5) . ? C11 C12 1.384(5) . ? C11 H11 0.9400 . ? C12 C121 1.531(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 H22C 0.9700 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 H31C 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 H32C 0.9700 . ? C71 F1A 1.161(13) . ? C71 F3A 1.199(18) . ? C71 F3 1.270(10) . ? C71 F2 1.276(7) . ? C71 F1 1.417(9) . ? C71 F2A 1.490(11) . ? C91 F6 1.165(12) . ? C91 F4 1.172(10) . ? C91 F4A 1.229(9) . ? C91 F5A 1.289(11) . ? C91 F5 1.443(10) . ? C91 F6A 1.485(10) . ? C101 F8 1.281(5) . ? C101 F7 1.298(5) . ? C101 F9 1.304(5) . ? C121 F10 1.297(4) . ? C121 F11 1.319(5) . ? C121 F12 1.331(4) . ? F1 F1A 1.13(2) . ? F1 F3A 1.70(3) . ? F2 F1A 1.063(19) . ? F2 F2A 1.264(13) . ? F3 F3A 0.51(4) . ? F3 F2A 1.65(2) . ? F4 F4A 0.82(2) . ? F4 F6A 1.393(16) . ? F6 F5A 0.59(3) . ? F6 F6A 1.56(2) . ? F5 F4A 1.397(17) . ? F5 F5A 1.655(18) . ? 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 O6 Co1 O4 173.08(8) . . ? O6 Co1 O5 88.25(9) . . ? O4 Co1 O5 92.24(9) . . ? O6 Co1 O2 90.11(8) . 7_666 ? O4 Co1 O2 89.89(8) . 7_666 ? O5 Co1 O2 175.59(8) . 7_666 ? O6 Co1 O3 85.15(8) . . ? O4 Co1 O3 88.05(8) . . ? O5 Co1 O3 83.00(9) . . ? O2 Co1 O3 100.94(8) 7_666 . ? O6 Co1 N3 99.95(9) . . ? O4 Co1 N3 86.97(8) . . ? O5 Co1 N3 85.78(9) . . ? O2 Co1 N3 90.47(8) 7_666 . ? O3 Co1 N3 167.53(9) . . ? N2 O2 Co1 126.92(16) . 7_666 ? C7 O3 Co1 124.99(19) . . ? C9 O4 Co1 124.95(19) . . ? C10 O5 Co1 122.2(2) . . ? C12 O6 Co1 121.8(2) . . ? O1 N1 C1 124.7(2) . . ? O1 N1 C2 123.1(2) . . ? C1 N1 C2 112.0(2) . . ? O2 N2 C1 124.6(2) . . ? O2 N2 C3 121.8(2) . . ? C1 N2 C3 111.9(2) . . ? C5 N3 N4 104.8(2) . . ? C5 N3 Co1 134.53(18) . . ? N4 N3 Co1 119.08(19) . . ? C6 N4 N3 112.6(3) . . ? C6 N4 H4 127(2) . . ? N3 N4 H4 120(2) . . ? N2 C1 N1 108.3(2) . . ? N2 C1 C4 126.9(2) . . ? N1 C1 C4 124.7(2) . . ? N1 C2 C22 110.7(3) . . ? N1 C2 C21 106.3(3) . . ? C22 C2 C21 110.0(3) . . ? N1 C2 C3 100.1(2) . . ? C22 C2 C3 115.2(3) . . ? C21 C2 C3 113.8(3) . . ? C31 C3 N2 110.8(3) . . ? C31 C3 C32 110.1(3) . . ? N2 C3 C32 105.3(3) . . ? C31 C3 C2 115.7(3) . . ? N2 C3 C2 100.0(2) . . ? C32 C3 C2 113.8(3) . . ? C6 C4 C5 104.7(2) . . ? C6 C4 C1 127.1(2) . . ? C5 C4 C1 128.2(3) . . ? N3 C5 C4 110.9(2) . . ? N3 C5 H5 124.6 . . ? C4 C5 H5 124.6 . . ? N4 C6 C4 107.1(2) . . ? N4 C6 H6 126.5 . . ? C4 C6 H6 126.5 . . ? O3 C7 C8 128.2(3) . . ? O3 C7 C71 114.5(3) . . ? C8 C7 C71 117.3(3) . . ? C9 C8 C7 122.5(3) . . ? C9 C8 H8 118.8 . . ? C7 C8 H8 118.8 . . ? O4 C9 C8 129.4(3) . . ? O4 C9 C91 114.3(3) . . ? C8 C9 C91 116.3(3) . . ? O5 C10 C11 128.2(3) . . ? O5 C10 C101 113.6(3) . . ? C11 C10 C101 118.1(3) . . ? C12 C11 C10 122.6(3) . . ? C12 C11 H11 118.7 . . ? C10 C11 H11 118.7 . . ? O6 C12 C11 128.9(3) . . ? O6 C12 C121 113.2(3) . . ? C11 C12 C121 117.8(3) . . ? C2 C21 H21A 109.5 . . ? C2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2 C22 H22A 109.5 . . ? C2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C3 C31 H31A 109.5 . . ? C3 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C3 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C3 C32 H32A 109.5 . . ? C3 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C3 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? F1A C71 F3A 113.0(16) . . ? F1A C71 F3 124.6(10) . . ? F3A C71 F3 23.6(19) . . ? F1A C71 F2 51.4(11) . . ? F3A C71 F2 127.0(13) . . ? F3 C71 F2 115.1(8) . . ? F1A C71 F1 51.0(13) . . ? F3A C71 F1 80.8(16) . . ? F3 C71 F1 103.7(7) . . ? F2 C71 F1 102.3(7) . . ? F1A C71 F2A 102.3(12) . . ? F3A C71 F2A 95.4(16) . . ? F3 C71 F2A 73.1(10) . . ? F2 C71 F2A 53.7(6) . . ? F1 C71 F2A 146.3(6) . . ? F1A C71 C7 120.2(7) . . ? F3A C71 C7 115.3(12) . . ? F3 C71 C7 113.7(7) . . ? F2 C71 C7 114.5(4) . . ? F1 C71 C7 105.7(4) . . ? F2A C71 C7 106.1(5) . . ? F6 C91 F4 115.0(11) . . ? F6 C91 F4A 130.0(8) . . ? F4 C91 F4A 39.7(10) . . ? F6 C91 F5A 27.4(15) . . ? F4 C91 F5A 125.0(9) . . ? F4A C91 F5A 118.3(10) . . ? F6 C91 F5 101.2(13) . . ? F4 C91 F5 100.7(9) . . ? F4A C91 F5 62.5(9) . . ? F5A C91 F5 74.3(8) . . ? F6 C91 F6A 70.9(12) . . ? F4 C91 F6A 61.9(9) . . ? F4A C91 F6A 101.3(10) . . ? F5A C91 F6A 97.2(7) . . ? F5 C91 F6A 152.1(5) . . ? F6 C91 C9 113.6(7) . . ? F4 C91 C9 118.7(8) . . ? F4A C91 C9 116.2(5) . . ? F5A C91 C9 115.4(6) . . ? F5 C91 C9 104.1(5) . . ? F6A C91 C9 103.6(5) . . ? F8 C101 F7 106.8(4) . . ? F8 C101 F9 105.4(4) . . ? F7 C101 F9 105.5(4) . . ? F8 C101 C10 111.4(4) . . ? F7 C101 C10 113.9(4) . . ? F9 C101 C10 113.2(4) . . ? F10 C121 F11 107.8(4) . . ? F10 C121 F12 107.8(3) . . ? F11 C121 F12 105.1(3) . . ? F10 C121 C12 111.2(3) . . ? F11 C121 C12 111.2(3) . . ? F12 C121 C12 113.4(3) . . ? F1A F1 C71 52.8(7) . . ? F1A F1 F3A 85.3(12) . . ? C71 F1 F3A 44.0(8) . . ? F1A F2 F2A 126.0(14) . . ? F1A F2 C71 58.7(9) . . ? F2A F2 C71 71.8(7) . . ? F3A F3 C71 70(3) . . ? F3A F3 F2A 126(4) . . ? C71 F3 F2A 59.6(7) . . ? F4A F4 C91 73.9(11) . . ? F4A F4 F6A 143.2(18) . . ? C91 F4 F6A 70.2(9) . . ? F5A F6 C91 88(2) . . ? F5A F6 F6A 148(3) . . ? C91 F6 F6A 64.2(10) . . ? F4A F5 C91 51.2(5) . . ? F4A F5 F5A 89.8(7) . . ? C91 F5 F5A 48.6(5) . . ? F4 F4A C91 66.4(10) . . ? F4 F4A F5 129.9(15) . . ? C91 F4A F5 66.3(7) . . ? F4 F6A C91 47.9(5) . . ? F4 F6A F6 83.6(9) . . ? C91 F6A F6 44.9(6) . . ? F6 F5A C91 64.5(18) . . ? F6 F5A F5 121(2) . . ? C91 F5A F5 57.1(7) . . ? F2 F1A F1 145.8(18) . . ? F2 F1A C71 69.8(9) . . ? F1 F1A C71 76.2(15) . . ? F2 F2A C71 54.5(5) . . ? F2 F2A F3 94.0(8) . . ? C71 F2A F3 47.3(5) . . ? F3 F3A C71 86(3) . . ? F3 F3A F1 139(4) . . ? C71 F3A F1 55.2(11) . . ? 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 H4 O1 0.82(3) 2.32(3) 2.926(3) 131(3) 4_646 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 22.94 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.437 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.050 # Attachment 'NI.CIF' data_ni _database_code_depnum_ccdc_archive 'CCDC 603118' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30.50 H32.50 Cl1.50 F12 N8 Ni O8' _chemical_formula_weight 979.03 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 '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 13.111(3) _cell_length_b 13.153(4) _cell_length_c 13.664(4) _cell_angle_alpha 95.901(8) _cell_angle_beta 110.85(1) _cell_angle_gamma 103.85(1) _cell_volume 2091.6(10) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4413 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 19.0 _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.015 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 994 _exptl_absorpt_coefficient_mu 0.669 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'Nonius KappaCCD' _diffrn_measurement_method 'phi-and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5862 _diffrn_reflns_av_R_equivalents 0.1717 _diffrn_reflns_av_sigmaI/netI 0.2349 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 19.00 _reflns_number_total 3347 _reflns_number_gt 1500 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement ? _computing_data_reduction 'DENZO and SCALEPACK' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; small crystal with low diffraction and poor data, some carbon atoms must be refined with isotropic displacement parameter (C1, C13 and C19). Disorder of solvent CHCl3 nearby a symmetry centre (hydrogen atoms was not calculated) and a slighly disorder of one PzNN-group (not solved). ; _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^)+(0.0762P)^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 SHELXL _refine_ls_extinction_coef 0.0031(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3347 _refine_ls_number_parameters 545 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2209 _refine_ls_R_factor_gt 0.0922 _refine_ls_wR_factor_ref 0.2124 _refine_ls_wR_factor_gt 0.1718 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _refine_ls_shift/su_max 0.002 _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 0.32862(18) 0.05687(19) 0.69670(18) 0.0543(9) Uani 1 1 d . . . O1 O 0.1764(14) -0.4445(13) 0.3739(18) 0.229(12) Uani 1 1 d . . . O2 O -0.0744(9) -0.2755(10) 0.4005(11) 0.106(6) Uani 1 1 d . . . O3 O 0.4488(11) 0.1611(12) 0.3467(11) 0.100(5) Uani 1 1 d . . . O4 O 0.1289(13) 0.2694(12) 0.2450(11) 0.121(6) Uani 1 1 d . . . O5 O 0.3979(8) 0.1999(8) 0.8076(8) 0.053(3) Uani 1 1 d . . . O6 O 0.4875(10) 0.0656(10) 0.7024(9) 0.059(4) Uani 1 1 d . . . O7 O 0.3508(10) -0.0242(9) 0.8183(8) 0.060(3) Uani 1 1 d . . . O8 O 0.1767(10) 0.0593(8) 0.6942(9) 0.057(4) Uani 1 1 d . . . N1 N 0.0854(15) -0.4252(14) 0.3630(15) 0.113(7) Uani 1 1 d . . . N2 N -0.0385(11) -0.3452(12) 0.3687(10) 0.046(4) Uani 1 1 d . . . N3 N 0.2659(13) -0.0922(10) 0.5952(10) 0.045(4) Uani 1 1 d . . . N4 N 0.3381(11) -0.1490(14) 0.5931(12) 0.065(4) Uani 1 1 d . . . H4 H 0.4119 -0.1256 0.6284 0.078 Uiso 1 1 calc . . . N5 N 0.3668(14) 0.1933(11) 0.2880(11) 0.057(4) Uani 1 1 d . . . N6 N 0.2154(17) 0.2454(13) 0.2434(15) 0.081(5) Uani 1 1 d . . . N7 N 0.2989(12) 0.1391(10) 0.5712(11) 0.051(4) Uani 1 1 d . . . N8 N 0.2217(12) 0.1925(12) 0.5502(13) 0.061(4) Uani 1 1 d . . . H8 H 0.1856 0.2026 0.5910 0.073 Uiso 1 1 calc . . . C1 C 0.0699(17) -0.3397(15) 0.4086(15) 0.052(5) Uiso 1 1 d . . . C2 C -0.0306(17) -0.5032(16) 0.2837(18) 0.084(6) Uani 1 1 d . . . C3 C -0.1112(15) -0.4439(15) 0.2855(16) 0.065(6) Uani 1 1 d . . . C4 C 0.1657(17) -0.2560(13) 0.4836(14) 0.057(5) Uani 1 1 d . . . C5 C 0.1641(13) -0.1560(18) 0.5291(15) 0.059(5) Uani 1 1 d . . . H5 H 0.0967 -0.1361 0.5140 0.071 Uiso 1 1 calc . . . C6 C 0.2825(18) -0.2454(17) 0.5301(17) 0.072(6) Uani 1 1 d . . . H6A H 0.3164 -0.2984 0.5186 0.087 Uiso 1 1 calc . . . C7 C 0.2878(16) 0.2108(14) 0.322(2) 0.057(5) Uani 1 1 d . . . C8 C 0.3597(19) 0.2273(14) 0.1838(15) 0.066(6) Uani 1 1 d . . . C9 C 0.2432(17) 0.2399(16) 0.1461(19) 0.074(6) Uani 1 1 d . . . C10 C 0.2767(14) 0.1936(13) 0.4208(16) 0.046(5) Uani 1 1 d . . . C11 C 0.3344(13) 0.1386(14) 0.4916(17) 0.051(5) Uani 1 1 d . . . H11 H 0.3890 0.1066 0.4846 0.061 Uiso 1 1 calc . . . C12 C 0.2062(15) 0.2280(15) 0.4614(18) 0.073(6) Uani 1 1 d . . . H12 H 0.1571 0.2685 0.4319 0.088 Uiso 1 1 calc . . . C13 C 0.4958(16) 0.2615(15) 0.8318(14) 0.055(5) Uiso 1 1 d . . . C14 C 0.5791(15) 0.2425(15) 0.8054(16) 0.073(6) Uani 1 1 d . . . H14 H 0.6472 0.2989 0.8274 0.087 Uiso 1 1 calc . . . C15 C 0.5739(15) 0.1467(18) 0.7481(15) 0.052(5) Uani 1 1 d . . . C16 C 0.2754(18) -0.0615(16) 0.8488(13) 0.058(5) Uani 1 1 d . . . C17 C 0.1640(17) -0.0481(15) 0.8178(17) 0.061(5) Uani 1 1 d . . . H17 H 0.1133 -0.0836 0.8461 0.073 Uiso 1 1 calc . . . C18 C 0.1296(16) 0.0172(15) 0.7457(16) 0.051(5) Uani 1 1 d . . . C21 C -0.017(2) -0.533(2) 0.183(2) 0.154(11) Uani 1 1 d . . . H21A H 0.0388 -0.5728 0.1948 0.230 Uiso 1 1 calc . . . H21B H 0.0092 -0.4692 0.1582 0.230 Uiso 1 1 calc . . . H21C H -0.0897 -0.5779 0.1286 0.230 Uiso 1 1 calc . . . C22 C -0.0410(17) -0.6035(19) 0.3335(18) 0.117(8) Uani 1 1 d . . . H22A H -0.0464 -0.5859 0.4019 0.176 Uiso 1 1 calc . . . H22B H 0.0258 -0.6276 0.3441 0.176 Uiso 1 1 calc . . . H22C H -0.1091 -0.6599 0.2858 0.176 Uiso 1 1 calc . . . C31 C -0.1625(18) -0.401(2) 0.1837(19) 0.142(10) Uani 1 1 d . . . H31A H -0.1015 -0.3634 0.1646 0.214 Uiso 1 1 calc . . . H31B H -0.2037 -0.3530 0.1970 0.214 Uiso 1 1 calc . . . H31C H -0.2145 -0.4609 0.1255 0.214 Uiso 1 1 calc . . . C32 C -0.2077(18) -0.4987(18) 0.313(2) 0.160(12) Uani 1 1 d . . . H32A H -0.2580 -0.4544 0.3085 0.241 Uiso 1 1 calc . . . H32B H -0.1776 -0.5105 0.3858 0.241 Uiso 1 1 calc . . . H32C H -0.2501 -0.5670 0.2639 0.241 Uiso 1 1 calc . . . C81 C 0.4600(19) 0.3285(18) 0.2177(19) 0.135(10) Uani 1 1 d . . . H81A H 0.5311 0.3103 0.2442 0.202 Uiso 1 1 calc . . . H81B H 0.4573 0.3779 0.2739 0.202 Uiso 1 1 calc . . . H81C H 0.4556 0.3617 0.1568 0.202 Uiso 1 1 calc . . . C82 C 0.3857(17) 0.1440(16) 0.1184(16) 0.102(7) Uani 1 1 d . . . H82A H 0.4649 0.1460 0.1539 0.153 Uiso 1 1 calc . . . H82B H 0.3724 0.1594 0.0477 0.153 Uiso 1 1 calc . . . H82C H 0.3363 0.0735 0.1118 0.153 Uiso 1 1 calc . . . C91 C 0.234(2) 0.339(2) 0.1041(17) 0.134(9) Uani 1 1 d . . . H91A H 0.1556 0.3409 0.0796 0.201 Uiso 1 1 calc . . . H91B H 0.2587 0.3403 0.0450 0.201 Uiso 1 1 calc . . . H91C H 0.2827 0.4016 0.1606 0.201 Uiso 1 1 calc . . . C92 C 0.153(2) 0.145(2) 0.0626(19) 0.134(10) Uani 1 1 d . . . H92A H 0.0791 0.1582 0.0405 0.201 Uiso 1 1 calc . . . H92B H 0.1490 0.0811 0.0929 0.201 Uiso 1 1 calc . . . H92C H 0.1724 0.1341 0.0010 0.201 Uiso 1 1 calc . . . C131 C 0.521(2) 0.365(2) 0.907(2) 0.084(7) Uani 1 1 d . . . C151 C 0.6743(18) 0.138(2) 0.721(2) 0.089(7) Uani 1 1 d . . . C161 C 0.3055(17) -0.1364(17) 0.927(2) 0.067(6) Uani 1 1 d . . . C181 C 0.011(2) 0.033(2) 0.7319(19) 0.080(7) Uani 1 1 d . . . F1 F 0.4699(14) 0.4263(11) 0.8557(13) 0.164(6) Uani 1 1 d . . . F2 F 0.6240(12) 0.4202(12) 0.9477(14) 0.188(9) Uani 1 1 d . . . F3 F 0.479(2) 0.3541(11) 0.9717(14) 0.239(12) Uani 1 1 d . . . F4 F 0.7575(11) 0.2260(10) 0.7472(12) 0.142(6) Uani 1 1 d . . . F5 F 0.7240(10) 0.0716(12) 0.7789(12) 0.140(6) Uani 1 1 d . . . F6 F 0.6483(10) 0.0971(10) 0.6227(11) 0.111(4) Uani 1 1 d . . . F7 F 0.2324(11) -0.1721(11) 0.9689(10) 0.137(5) Uani 1 1 d . . . F8 F 0.4058(11) -0.0962(10) 1.0050(10) 0.118(5) Uani 1 1 d . . . F9 F 0.3133(11) -0.2252(10) 0.8794(10) 0.120(4) Uani 1 1 d . . . F10 F -0.0426(8) -0.0202(10) 0.7834(9) 0.105(4) Uani 1 1 d . . . F11 F 0.0319(9) 0.1354(11) 0.7733(11) 0.113(4) Uani 1 1 d . . . F12 F -0.0542(8) 0.0156(10) 0.6314(10) 0.099(4) Uani 1 1 d . . . C19 C 0.510(3) -0.559(2) 0.521(3) 0.043(8) Uiso 0.50 1 d P . . Cl1 Cl 0.3910(9) -0.5143(9) 0.4757(11) 0.287(6) Uani 1 1 d . . . Cl2 Cl 0.5236(18) -0.5974(13) 0.6194(15) 0.238(9) Uani 0.50 1 d P . . 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 0.0560(15) 0.0579(17) 0.0445(17) 0.0093(13) 0.0161(13) 0.0154(12) O1 0.087(12) 0.128(16) 0.36(3) -0.123(17) -0.004(15) 0.051(11) O2 0.057(8) 0.088(11) 0.125(13) -0.069(9) -0.003(8) 0.035(8) O3 0.071(10) 0.161(14) 0.086(12) 0.042(10) 0.032(9) 0.055(10) O4 0.143(13) 0.188(16) 0.100(13) 0.058(11) 0.069(11) 0.128(13) O5 0.060(7) 0.044(7) 0.048(8) -0.005(6) 0.024(6) 0.007(6) O6 0.041(8) 0.080(10) 0.044(9) 0.005(8) 0.003(7) 0.020(7) O7 0.073(8) 0.062(9) 0.046(9) 0.020(7) 0.023(7) 0.020(7) O8 0.085(9) 0.038(8) 0.062(10) 0.025(7) 0.044(8) 0.015(7) N1 0.073(13) 0.105(16) 0.150(18) -0.025(14) 0.022(13) 0.063(13) N2 0.046(10) 0.043(10) 0.032(10) -0.009(8) -0.002(8) 0.016(9) N3 0.053(10) 0.043(10) 0.033(10) -0.002(8) 0.010(9) 0.016(10) N4 0.042(10) 0.063(13) 0.070(12) -0.006(10) -0.003(9) 0.026(10) N5 0.056(11) 0.063(11) 0.047(13) 0.014(9) 0.009(10) 0.024(9) N6 0.117(16) 0.101(14) 0.061(14) 0.023(11) 0.059(14) 0.055(12) N7 0.042(9) 0.040(10) 0.064(12) -0.002(8) 0.022(9) 0.002(8) N8 0.052(10) 0.078(12) 0.056(13) 0.006(10) 0.019(9) 0.033(9) C2 0.064(15) 0.059(16) 0.089(19) 0.007(15) 0.003(14) -0.007(14) C3 0.041(12) 0.066(15) 0.067(16) -0.015(14) -0.007(12) 0.038(13) C4 0.078(16) 0.023(13) 0.060(14) -0.009(11) 0.017(12) 0.021(11) C5 0.017(11) 0.081(16) 0.050(13) -0.003(12) -0.008(10) 0.002(11) C6 0.060(15) 0.065(17) 0.091(18) 0.002(14) 0.035(14) 0.015(13) C7 0.041(13) 0.052(14) 0.076(19) 0.013(13) 0.018(15) 0.021(10) C8 0.14(2) 0.048(14) 0.048(15) 0.028(12) 0.063(14) 0.038(14) C9 0.066(15) 0.072(16) 0.10(2) 0.054(16) 0.025(15) 0.049(13) C10 0.056(12) 0.039(12) 0.058(15) 0.023(11) 0.027(12) 0.029(10) C11 0.047(11) 0.051(13) 0.066(15) 0.001(12) 0.032(12) 0.023(10) C12 0.086(15) 0.104(18) 0.059(16) 0.028(14) 0.031(13) 0.071(13) C14 0.085(14) 0.047(14) 0.111(18) 0.031(13) 0.064(14) 0.017(11) C15 0.031(13) 0.070(17) 0.055(15) 0.033(13) -0.001(12) 0.031(13) C16 0.080(18) 0.068(16) 0.019(12) 0.011(12) 0.013(12) 0.019(14) C17 0.035(12) 0.054(13) 0.090(16) 0.017(13) 0.031(11) -0.006(10) C18 0.058(16) 0.047(14) 0.044(15) 0.008(12) 0.010(12) 0.027(12) C21 0.15(2) 0.23(3) 0.12(2) 0.03(2) 0.07(2) 0.10(2) C22 0.111(18) 0.11(2) 0.11(2) 0.030(17) 0.016(16) 0.053(16) C31 0.098(17) 0.18(3) 0.09(2) -0.020(19) -0.042(15) 0.075(18) C32 0.094(16) 0.11(2) 0.28(4) 0.00(2) 0.11(2) -0.002(15) C81 0.16(2) 0.101(19) 0.15(2) 0.010(17) 0.111(19) -0.029(17) C82 0.134(18) 0.096(17) 0.077(17) 0.000(14) 0.051(15) 0.029(14) C91 0.20(2) 0.17(3) 0.11(2) 0.11(2) 0.078(19) 0.14(2) C92 0.13(2) 0.17(3) 0.09(2) 0.00(2) 0.060(17) 0.01(2) C131 0.11(2) 0.08(2) 0.08(2) 0.014(17) 0.036(18) 0.055(17) C151 0.040(16) 0.10(2) 0.061(18) -0.031(16) -0.017(15) -0.008(15) C161 0.054(15) 0.039(14) 0.10(2) 0.015(15) 0.018(15) 0.012(12) C181 0.11(2) 0.070(18) 0.046(17) 0.037(15) 0.031(16) 0.001(17) F1 0.201(16) 0.076(11) 0.173(16) -0.002(10) 0.025(13) 0.056(11) F2 0.085(10) 0.153(15) 0.220(19) -0.104(13) -0.009(11) 0.013(10) F3 0.46(3) 0.100(12) 0.196(19) -0.040(12) 0.25(2) -0.012(15) F4 0.096(9) 0.109(11) 0.205(15) -0.020(11) 0.081(10) -0.011(9) F5 0.077(9) 0.197(16) 0.175(15) 0.090(13) 0.048(9) 0.073(10) F6 0.104(9) 0.130(11) 0.107(11) 0.007(9) 0.060(9) 0.027(8) F7 0.110(9) 0.196(14) 0.144(13) 0.118(11) 0.064(10) 0.058(10) F8 0.101(9) 0.125(12) 0.090(10) 0.048(9) -0.004(8) 0.019(8) F9 0.174(12) 0.069(9) 0.124(12) 0.034(8) 0.050(10) 0.059(9) F10 0.074(8) 0.154(11) 0.121(11) 0.076(10) 0.054(8) 0.049(7) F11 0.101(9) 0.104(11) 0.161(13) 0.042(10) 0.070(9) 0.047(9) F12 0.066(8) 0.151(12) 0.077(10) 0.051(9) 0.019(7) 0.027(8) Cl1 0.229(10) 0.209(11) 0.420(19) 0.033(12) 0.115(12) 0.093(10) Cl2 0.35(3) 0.125(14) 0.146(16) -0.006(13) 0.018(17) 0.034(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O8 1.989(11) . ? Ni1 O6 2.031(10) . ? Ni1 O7 2.038(12) . ? Ni1 O5 2.068(9) . ? Ni1 N3 2.073(12) . ? Ni1 N7 2.090(14) . ? O1 N1 1.241(16) . ? O2 N2 1.233(13) . ? O3 N5 1.285(15) . ? O4 N6 1.254(17) . ? O5 C13 1.248(17) . ? O6 C15 1.262(19) . ? O7 C16 1.222(18) . ? O8 C18 1.186(19) . ? N1 C1 1.32(2) . ? N1 C2 1.55(2) . ? N2 C1 1.308(18) . ? N2 C3 1.490(19) . ? N3 C5 1.323(17) . ? N3 N4 1.346(15) . ? N4 C6 1.330(19) . ? N4 H4 0.8700 . ? N5 C7 1.333(19) . ? N5 C8 1.514(19) . ? N6 C7 1.36(2) . ? N6 C9 1.50(2) . ? N7 C11 1.327(17) . ? N7 N8 1.331(15) . ? N8 C12 1.311(19) . ? N8 H8 0.8700 . ? C1 C4 1.42(2) . ? C2 C3 1.46(2) . ? C2 C21 1.48(2) . ? C2 C22 1.54(3) . ? C3 C32 1.49(2) . ? C3 C31 1.54(3) . ? C4 C6 1.40(2) . ? C4 C5 1.40(2) . ? C5 H5 0.9400 . ? C6 H6A 0.9400 . ? C7 C10 1.44(2) . ? C8 C9 1.48(2) . ? C8 C82 1.52(2) . ? C8 C81 1.52(2) . ? C9 C91 1.50(3) . ? C9 C92 1.52(3) . ? C10 C12 1.37(2) . ? C10 C11 1.38(2) . ? C11 H11 0.9400 . ? C12 H12 0.9400 . ? C13 C14 1.33(2) . ? C13 C131 1.50(3) . ? C14 C15 1.39(2) . ? C14 H14 0.9400 . ? C15 C151 1.51(2) . ? C16 C17 1.43(2) . ? C16 C161 1.54(2) . ? C17 C18 1.40(2) . ? C17 H17 0.9400 . ? C18 C181 1.56(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 H22C 0.9700 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 H31C 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 H32C 0.9700 . ? C81 H81A 0.9700 . ? C81 H81B 0.9700 . ? C81 H81C 0.9700 . ? C82 H82A 0.9700 . ? C82 H82B 0.9700 . ? C82 H82C 0.9700 . ? C91 H91A 0.9700 . ? C91 H91B 0.9700 . ? C91 H91C 0.9700 . ? C92 H92A 0.9700 . ? C92 H92B 0.9700 . ? C92 H92C 0.9700 . ? C131 F3 1.21(2) . ? C131 F2 1.25(2) . ? C131 F1 1.28(2) . ? C151 F6 1.28(2) . ? C151 F4 1.30(2) . ? C151 F5 1.36(2) . ? C161 F7 1.302(19) . ? C161 F8 1.302(19) . ? C161 F9 1.322(19) . ? C181 F12 1.30(2) . ? C181 F10 1.303(18) . ? C181 F11 1.33(2) . ? C19 Cl1 1.41(3) 2_646 ? C19 Cl2 1.45(3) . ? C19 Cl1 1.73(3) . ? C19 C19 1.76(7) 2_646 ? Cl1 C19 1.41(3) 2_646 ? Cl1 Cl2 2.40(2) 2_646 ? Cl2 Cl1 2.40(2) 2_646 ? 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 O8 Ni1 O6 176.0(5) . . ? O8 Ni1 O7 90.1(5) . . ? O6 Ni1 O7 91.6(5) . . ? O8 Ni1 O5 87.5(4) . . ? O6 Ni1 O5 88.9(4) . . ? O7 Ni1 O5 89.6(4) . . ? O8 Ni1 N3 94.2(5) . . ? O6 Ni1 N3 89.5(5) . . ? O7 Ni1 N3 86.1(5) . . ? O5 Ni1 N3 175.4(5) . . ? O8 Ni1 N7 87.6(6) . . ? O6 Ni1 N7 90.8(5) . . ? O7 Ni1 N7 177.6(6) . . ? O5 Ni1 N7 90.7(5) . . ? N3 Ni1 N7 93.7(5) . . ? C13 O5 Ni1 124.1(11) . . ? C15 O6 Ni1 124.6(11) . . ? C16 O7 Ni1 123.7(12) . . ? C18 O8 Ni1 126.9(12) . . ? O1 N1 C1 128.6(18) . . ? O1 N1 C2 120.9(16) . . ? C1 N1 C2 110.4(17) . . ? O2 N2 C1 121.9(15) . . ? O2 N2 C3 124.8(12) . . ? C1 N2 C3 113.2(14) . . ? C5 N3 N4 104.3(13) . . ? C5 N3 Ni1 136.2(14) . . ? N4 N3 Ni1 119.4(12) . . ? C6 N4 N3 111.4(13) . . ? C6 N4 H4 124.3 . . ? N3 N4 H4 124.3 . . ? O3 N5 C7 121.1(18) . . ? O3 N5 C8 123.8(16) . . ? C7 N5 C8 114.7(17) . . ? O4 N6 C7 126.0(17) . . ? O4 N6 C9 122(2) . . ? C7 N6 C9 111.2(17) . . ? C11 N7 N8 106.7(14) . . ? C11 N7 Ni1 130.7(15) . . ? N8 N7 Ni1 121.9(13) . . ? C12 N8 N7 112.8(13) . . ? C12 N8 H8 123.6 . . ? N7 N8 H8 123.6 . . ? N2 C1 N1 109.9(18) . . ? N2 C1 C4 129.9(18) . . ? N1 C1 C4 120.0(18) . . ? C3 C2 C21 120(2) . . ? C3 C2 C22 115.4(17) . . ? C21 C2 C22 107.0(19) . . ? C3 C2 N1 102.7(16) . . ? C21 C2 N1 106.8(18) . . ? C22 C2 N1 103.4(17) . . ? C2 C3 N2 103.5(14) . . ? C2 C3 C32 116.2(18) . . ? N2 C3 C32 109.3(16) . . ? C2 C3 C31 115.6(18) . . ? N2 C3 C31 103.9(16) . . ? C32 C3 C31 107.5(18) . . ? C6 C4 C5 100.7(15) . . ? C6 C4 C1 132.8(18) . . ? C5 C4 C1 126.5(18) . . ? N3 C5 C4 114.1(15) . . ? N3 C5 H5 123.0 . . ? C4 C5 H5 123.0 . . ? N4 C6 C4 109.5(15) . . ? N4 C6 H6A 125.2 . . ? C4 C6 H6A 125.2 . . ? N5 C7 N6 107(2) . . ? N5 C7 C10 128(2) . . ? N6 C7 C10 125.5(18) . . ? C9 C8 N5 99.6(14) . . ? C9 C8 C82 119.9(19) . . ? N5 C8 C82 108.1(15) . . ? C9 C8 C81 117.3(17) . . ? N5 C8 C81 104.0(16) . . ? C82 C8 C81 106.3(16) . . ? C8 C9 C91 114.5(17) . . ? C8 C9 N6 104.7(16) . . ? C91 C9 N6 108.3(18) . . ? C8 C9 C92 113.4(18) . . ? C91 C9 C92 108.4(19) . . ? N6 C9 C92 107.1(16) . . ? C12 C10 C11 107.3(17) . . ? C12 C10 C7 126(2) . . ? C11 C10 C7 126.4(18) . . ? N7 C11 C10 107.8(14) . . ? N7 C11 H11 126.1 . . ? C10 C11 H11 126.1 . . ? N8 C12 C10 105.3(16) . . ? N8 C12 H12 127.3 . . ? C10 C12 H12 127.3 . . ? O5 C13 C14 127.8(18) . . ? O5 C13 C131 113.5(18) . . ? C14 C13 C131 118.6(19) . . ? C13 C14 C15 125.6(17) . . ? C13 C14 H14 117.2 . . ? C15 C14 H14 117.2 . . ? O6 C15 C14 127.0(16) . . ? O6 C15 C151 112.6(18) . . ? C14 C15 C151 119.8(19) . . ? O7 C16 C17 128.6(19) . . ? O7 C16 C161 114.0(18) . . ? C17 C16 C161 117.4(19) . . ? C18 C17 C16 120.8(15) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? O8 C18 C17 129.0(17) . . ? O8 C18 C181 117.6(19) . . ? C17 C18 C181 113.3(19) . . ? C2 C21 H21A 109.5 . . ? C2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2 C22 H22A 109.5 . . ? C2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C3 C31 H31A 109.5 . . ? C3 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C3 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C3 C32 H32A 109.5 . . ? C3 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C3 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C8 C81 H81A 109.5 . . ? C8 C81 H81B 109.5 . . ? H81A C81 H81B 109.5 . . ? C8 C81 H81C 109.5 . . ? H81A C81 H81C 109.5 . . ? H81B C81 H81C 109.5 . . ? C8 C82 H82A 109.5 . . ? C8 C82 H82B 109.5 . . ? H82A C82 H82B 109.5 . . ? C8 C82 H82C 109.5 . . ? H82A C82 H82C 109.5 . . ? H82B C82 H82C 109.5 . . ? C9 C91 H91A 109.5 . . ? C9 C91 H91B 109.5 . . ? H91A C91 H91B 109.5 . . ? C9 C91 H91C 109.5 . . ? H91A C91 H91C 109.5 . . ? H91B C91 H91C 109.5 . . ? C9 C92 H92A 109.5 . . ? C9 C92 H92B 109.5 . . ? H92A C92 H92B 109.5 . . ? C9 C92 H92C 109.5 . . ? H92A C92 H92C 109.5 . . ? H92B C92 H92C 109.5 . . ? F3 C131 F2 113(2) . . ? F3 C131 F1 100(2) . . ? F2 C131 F1 104(2) . . ? F3 C131 C13 113(2) . . ? F2 C131 C13 115.4(19) . . ? F1 C131 C13 110(2) . . ? F6 C151 F4 107(2) . . ? F6 C151 F5 106(2) . . ? F4 C151 F5 103.7(18) . . ? F6 C151 C15 114.9(17) . . ? F4 C151 C15 116(2) . . ? F5 C151 C15 108(2) . . ? F7 C161 F8 108(2) . . ? F7 C161 F9 102.9(17) . . ? F8 C161 F9 103.2(17) . . ? F7 C161 C16 116.9(17) . . ? F8 C161 C16 113.4(17) . . ? F9 C161 C16 111.4(19) . . ? F12 C181 F10 110.6(19) . . ? F12 C181 F11 107(2) . . ? F10 C181 F11 104.7(19) . . ? F12 C181 C18 110.7(18) . . ? F10 C181 C18 117(2) . . ? F11 C181 C18 106.3(17) . . ? Cl1 C19 Cl2 114(2) 2_646 . ? Cl1 C19 Cl1 113(2) 2_646 . ? Cl2 C19 Cl1 112(2) . . ? Cl1 C19 C19 65.1(19) 2_646 2_646 ? Cl2 C19 C19 135(3) . 2_646 ? Cl1 C19 C19 47.6(15) . 2_646 ? C19 Cl1 C19 67(2) 2_646 . ? C19 Cl1 Cl2 33.5(15) 2_646 2_646 ? C19 Cl1 Cl2 90.2(14) . 2_646 ? C19 Cl2 Cl1 32.4(13) . 2_646 ? 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 H4 O3 0.87 1.92 2.666(19) 143.6 2_656 N8 H8 O2 0.87 1.96 2.676(18) 139.4 2_556 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 19.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.356 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.072 data_4pznn _database_code_depnum_ccdc_archive 'CCDC 603119' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H15 N4 O2' _chemical_formula_weight 223.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 13.8867(4) _cell_length_b 13.1057(3) _cell_length_c 13.4309(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.917(1) _cell_angle_gamma 90.00 _cell_volume 2350.64(11) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 12832 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 24.0 _exptl_crystal_description block _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11308 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 23.00 _reflns_number_total 3267 _reflns_number_gt 2775 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement ? _computing_data_reduction 'DENZO and SCALEPACK' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0482P)^2^+0.5204P] 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, refined at N4 and N8' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0162(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3267 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0908 _refine_ls_wR_factor_gt 0.0866 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.45939(8) -0.07247(9) 0.86979(11) 0.0552(4) Uani 1 1 d . . . O2 O 0.26406(8) 0.21699(8) 0.81613(9) 0.0456(3) Uani 1 1 d . . . N1 N 0.38547(9) -0.01118(10) 0.86681(10) 0.0367(3) Uani 1 1 d . . . N2 N 0.29443(9) 0.12602(9) 0.84307(9) 0.0336(3) Uani 1 1 d . . . N3 N 0.56792(11) 0.14956(12) 0.69818(12) 0.0561(4) Uani 1 1 d . . . N4 N 0.51903(12) 0.23788(13) 0.70047(14) 0.0587(5) Uani 1 1 d . . . H4 H 0.5348(15) 0.2955(17) 0.6729(16) 0.073(7) Uiso 1 1 d . . . C1 C 0.37722(11) 0.08275(11) 0.82742(11) 0.0323(4) Uani 1 1 d . . . C2 C 0.29453(11) -0.04444(12) 0.89752(13) 0.0384(4) Uani 1 1 d . . . C3 C 0.24820(11) 0.06166(12) 0.90948(12) 0.0378(4) Uani 1 1 d . . . C4 C 0.44455(11) 0.12913(12) 0.77687(12) 0.0362(4) Uani 1 1 d . . . C5 C 0.52261(13) 0.08392(13) 0.74443(14) 0.0467(4) Uani 1 1 d . . . H5 H 0.5405 0.0147 0.7546 0.056 Uiso 1 1 calc . . . C6 C 0.44531(13) 0.22900(13) 0.74616(15) 0.0515(5) Uani 1 1 d . . . H6 H 0.4022 0.2812 0.7555 0.062 Uiso 1 1 calc . . . C21 C 0.32480(15) -0.10778(15) 0.99552(16) 0.0611(5) Uani 1 1 d . . . H21A H 0.2659 -0.1238 1.0181 0.092 Uiso 1 1 calc R . . H21B H 0.3719 -0.0695 1.0493 0.092 Uiso 1 1 calc R . . H21C H 0.3560 -0.1705 0.9820 0.092 Uiso 1 1 calc R . . C22 C 0.23215(13) -0.10769(14) 0.80752(15) 0.0522(5) Uani 1 1 d . . . H22A H 0.1722 -0.1318 0.8239 0.078 Uiso 1 1 calc R . . H22B H 0.2711 -0.1657 0.7958 0.078 Uiso 1 1 calc R . . H22C H 0.2134 -0.0659 0.7456 0.078 Uiso 1 1 calc R . . C31 C 0.28461(14) 0.10689(15) 1.01814(13) 0.0557(5) Uani 1 1 d . . . H31A H 0.2553 0.0694 1.0648 0.084 Uiso 1 1 calc R . . H31B H 0.2647 0.1779 1.0165 0.084 Uiso 1 1 calc R . . H31C H 0.3570 0.1021 1.0421 0.084 Uiso 1 1 calc R . . C32 C 0.13502(12) 0.06684(15) 0.87036(17) 0.0588(5) Uani 1 1 d . . . H32A H 0.1056 0.0229 0.9122 0.088 Uiso 1 1 calc R . . H32B H 0.1139 0.0444 0.7988 0.088 Uiso 1 1 calc R . . H32C H 0.1131 0.1365 0.8750 0.088 Uiso 1 1 calc R . . O3 O 0.03126(8) 0.10746(9) 0.28659(8) 0.0438(3) Uani 1 1 d . . . O4 O 0.23644(10) 0.06944(11) 0.61762(9) 0.0622(4) Uani 1 1 d . . . N5 N 0.10559(9) 0.07875(9) 0.36242(9) 0.0328(3) Uani 1 1 d . . . N6 N 0.20217(10) 0.05987(10) 0.51933(10) 0.0398(3) Uani 1 1 d . . . N7 N -0.05184(10) 0.30384(11) 0.50498(11) 0.0478(4) Uani 1 1 d . . . N8 N 0.02086(10) 0.29815(11) 0.59592(12) 0.0434(4) Uani 1 1 d . . . H8 H 0.0185(14) 0.3393(14) 0.6501(16) 0.060(6) Uiso 1 1 d . . . C7 C 0.12104(11) 0.10963(11) 0.46056(11) 0.0332(4) Uani 1 1 d . . . C8 C 0.17600(11) -0.00458(11) 0.35086(12) 0.0358(4) Uani 1 1 d . . . C9 C 0.25810(11) 0.00292(12) 0.45644(12) 0.0387(4) Uani 1 1 d . . . C10 C 0.06414(11) 0.18439(11) 0.49803(11) 0.0339(4) Uani 1 1 d . . . C11 C -0.02499(12) 0.23471(13) 0.44578(13) 0.0411(4) Uani 1 1 d . . . H11 H -0.0612 0.2209 0.3770 0.049 Uiso 1 1 calc . . . C12 C 0.09035(12) 0.22864(12) 0.59521(12) 0.0396(4) Uani 1 1 d . . . H12 H 0.1466 0.2126 0.6503 0.047 Uiso 1 1 calc . . . C81 C 0.21214(13) 0.01690(15) 0.25573(13) 0.0501(5) Uani 1 1 d . . . H81A H 0.1565 0.0103 0.1939 0.075 Uiso 1 1 calc R . . H81B H 0.2641 -0.0315 0.2528 0.075 Uiso 1 1 calc R . . H81C H 0.2388 0.0857 0.2598 0.075 Uiso 1 1 calc R . . C82 C 0.11617(14) -0.10338(13) 0.33669(15) 0.0542(5) Uani 1 1 d . . . H82A H 0.0900 -0.1140 0.3959 0.081 Uiso 1 1 calc R . . H82B H 0.1593 -0.1600 0.3310 0.081 Uiso 1 1 calc R . . H82C H 0.0610 -0.0991 0.2742 0.081 Uiso 1 1 calc R . . C91 C 0.34775(13) 0.06925(15) 0.45403(15) 0.0539(5) Uani 1 1 d . . . H91A H 0.3243 0.1339 0.4211 0.081 Uiso 1 1 calc R . . H91B H 0.3875 0.0347 0.4152 0.081 Uiso 1 1 calc R . . H91C H 0.3884 0.0813 0.5242 0.081 Uiso 1 1 calc R . . C92 C 0.29462(15) -0.09808(14) 0.50860(15) 0.0568(5) Uani 1 1 d . . . H92A H 0.3408 -0.0854 0.5761 0.085 Uiso 1 1 calc R . . H92B H 0.3285 -0.1362 0.4663 0.085 Uiso 1 1 calc R . . H92C H 0.2379 -0.1371 0.5168 0.085 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 0.0422(7) 0.0378(7) 0.0903(10) 0.0051(6) 0.0259(7) 0.0133(6) O2 0.0476(7) 0.0341(7) 0.0536(7) 0.0017(5) 0.0116(6) 0.0115(5) N1 0.0306(7) 0.0326(7) 0.0483(8) -0.0005(6) 0.0131(6) 0.0047(6) N2 0.0332(7) 0.0316(7) 0.0350(7) -0.0015(6) 0.0079(6) 0.0045(6) N3 0.0489(9) 0.0616(10) 0.0639(10) 0.0095(8) 0.0259(8) 0.0024(8) N4 0.0569(10) 0.0502(10) 0.0763(12) 0.0145(9) 0.0304(9) -0.0052(8) C1 0.0303(8) 0.0309(8) 0.0349(9) -0.0014(7) 0.0079(7) 0.0021(7) C2 0.0324(8) 0.0381(9) 0.0463(10) 0.0027(7) 0.0136(7) -0.0017(7) C3 0.0320(8) 0.0413(9) 0.0427(10) -0.0016(7) 0.0146(7) -0.0002(7) C4 0.0333(8) 0.0373(9) 0.0381(9) 0.0010(7) 0.0101(7) -0.0002(7) C5 0.0448(10) 0.0487(10) 0.0515(11) 0.0062(8) 0.0216(9) 0.0026(8) C6 0.0477(10) 0.0437(11) 0.0703(13) 0.0056(9) 0.0284(9) -0.0005(8) C21 0.0638(12) 0.0569(12) 0.0655(13) 0.0202(10) 0.0229(10) 0.0063(10) C22 0.0466(10) 0.0431(10) 0.0669(12) -0.0090(9) 0.0156(9) -0.0060(8) C31 0.0610(12) 0.0679(12) 0.0434(11) -0.0074(9) 0.0229(9) 0.0028(10) C32 0.0339(9) 0.0602(12) 0.0835(15) -0.0065(10) 0.0182(10) 0.0037(8) O3 0.0399(6) 0.0582(7) 0.0309(6) 0.0027(5) 0.0056(5) 0.0076(5) O4 0.0664(8) 0.0821(9) 0.0307(7) -0.0029(6) 0.0012(6) 0.0223(7) N5 0.0326(7) 0.0379(7) 0.0280(7) 0.0029(6) 0.0085(6) 0.0012(6) N6 0.0441(8) 0.0461(8) 0.0278(8) 0.0002(6) 0.0074(6) 0.0061(7) N7 0.0437(8) 0.0515(9) 0.0486(9) -0.0052(7) 0.0132(7) 0.0051(7) N8 0.0450(8) 0.0449(9) 0.0437(9) -0.0086(7) 0.0181(7) -0.0025(7) C7 0.0339(8) 0.0365(8) 0.0294(9) 0.0036(7) 0.0092(7) -0.0008(7) C8 0.0370(8) 0.0361(9) 0.0365(9) -0.0003(7) 0.0136(7) 0.0021(7) C9 0.0398(9) 0.0393(9) 0.0377(9) 0.0022(7) 0.0117(7) 0.0066(7) C10 0.0347(8) 0.0363(8) 0.0325(9) -0.0001(7) 0.0124(7) -0.0027(7) C11 0.0400(9) 0.0471(10) 0.0373(9) -0.0022(8) 0.0123(8) 0.0017(8) C12 0.0377(9) 0.0436(10) 0.0384(10) -0.0018(8) 0.0121(7) -0.0020(8) C81 0.0485(10) 0.0662(12) 0.0398(10) 0.0012(9) 0.0193(8) 0.0097(9) C82 0.0558(11) 0.0407(10) 0.0629(12) -0.0069(9) 0.0109(9) -0.0038(9) C91 0.0410(10) 0.0604(12) 0.0578(12) -0.0010(9) 0.0093(9) -0.0016(9) C92 0.0648(12) 0.0500(11) 0.0544(12) 0.0095(9) 0.0143(10) 0.0160(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 O1 N1 1.2954(16) . ? O2 N2 1.2832(16) . ? N1 C1 1.3324(19) . ? N1 C2 1.4968(19) . ? N2 C1 1.3491(19) . ? N2 C3 1.494(2) . ? N3 C5 1.318(2) . ? N3 N4 1.346(2) . ? N4 C6 1.335(2) . ? N4 H4 0.89(2) . ? C1 C4 1.433(2) . ? C2 C21 1.515(2) . ? C2 C22 1.525(2) . ? C2 C3 1.559(2) . ? C3 C32 1.516(2) . ? C3 C31 1.527(2) . ? C4 C6 1.373(2) . ? C4 C5 1.405(2) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 H22C 0.9700 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 H31C 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 H32C 0.9700 . ? O3 N5 1.2914(16) . ? O4 N6 1.2807(17) . ? N5 C7 1.3387(19) . ? N5 C8 1.5019(19) . ? N6 C7 1.3527(19) . ? N6 C9 1.495(2) . ? N7 C11 1.325(2) . ? N7 N8 1.357(2) . ? N8 C12 1.329(2) . ? N8 H8 0.91(2) . ? C7 C10 1.434(2) . ? C8 C81 1.522(2) . ? C8 C82 1.522(2) . ? C8 C9 1.560(2) . ? C9 C92 1.518(2) . ? C9 C91 1.526(2) . ? C10 C12 1.383(2) . ? C10 C11 1.408(2) . ? C11 H11 0.9400 . ? C12 H12 0.9400 . ? C81 H81A 0.9700 . ? C81 H81B 0.9700 . ? C81 H81C 0.9700 . ? C82 H82A 0.9700 . ? C82 H82B 0.9700 . ? C82 H82C 0.9700 . ? C91 H91A 0.9700 . ? C91 H91B 0.9700 . ? C91 H91C 0.9700 . ? C92 H92A 0.9700 . ? C92 H92B 0.9700 . ? C92 H92C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 N1 C1 124.49(12) . . ? O1 N1 C2 122.16(12) . . ? C1 N1 C2 113.03(12) . . ? O2 N2 C1 125.08(13) . . ? O2 N2 C3 122.07(12) . . ? C1 N2 C3 112.31(12) . . ? C5 N3 N4 103.98(14) . . ? C6 N4 N3 112.99(15) . . ? C6 N4 H4 124.7(13) . . ? N3 N4 H4 122.3(13) . . ? N1 C1 N2 108.10(13) . . ? N1 C1 C4 125.73(13) . . ? N2 C1 C4 126.18(13) . . ? N1 C2 C21 110.18(13) . . ? N1 C2 C22 106.18(13) . . ? C21 C2 C22 110.66(15) . . ? N1 C2 C3 99.90(12) . . ? C21 C2 C3 115.04(14) . . ? C22 C2 C3 113.95(13) . . ? N2 C3 C32 110.01(14) . . ? N2 C3 C31 105.51(13) . . ? C32 C3 C31 110.73(14) . . ? N2 C3 C2 100.66(11) . . ? C32 C3 C2 114.97(14) . . ? C31 C3 C2 114.01(14) . . ? C6 C4 C5 103.81(14) . . ? C6 C4 C1 127.34(14) . . ? C5 C4 C1 128.83(14) . . ? N3 C5 C4 112.30(15) . . ? N3 C5 H5 123.9 . . ? C4 C5 H5 123.9 . . ? N4 C6 C4 106.93(15) . . ? N4 C6 H6 126.5 . . ? C4 C6 H6 126.5 . . ? C2 C21 H21A 109.5 . . ? C2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2 C22 H22A 109.5 . . ? C2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C3 C31 H31A 109.5 . . ? C3 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C3 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C3 C32 H32A 109.5 . . ? C3 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C3 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O3 N5 C7 124.47(12) . . ? O3 N5 C8 122.18(12) . . ? C7 N5 C8 112.86(12) . . ? O4 N6 C7 124.67(13) . . ? O4 N6 C9 121.85(12) . . ? C7 N6 C9 112.94(12) . . ? C11 N7 N8 103.90(13) . . ? C12 N8 N7 113.20(14) . . ? C12 N8 H8 126.5(12) . . ? N7 N8 H8 120.3(12) . . ? N5 C7 N6 108.17(13) . . ? N5 C7 C10 126.67(13) . . ? N6 C7 C10 125.14(13) . . ? N5 C8 C81 109.04(12) . . ? N5 C8 C82 106.45(12) . . ? C81 C8 C82 110.29(14) . . ? N5 C8 C9 101.22(11) . . ? C81 C8 C9 115.11(13) . . ? C82 C8 C9 113.89(13) . . ? N6 C9 C92 109.52(13) . . ? N6 C9 C91 106.31(13) . . ? C92 C9 C91 109.59(14) . . ? N6 C9 C8 100.46(11) . . ? C92 C9 C8 115.65(14) . . ? C91 C9 C8 114.44(13) . . ? C12 C10 C11 103.99(14) . . ? C12 C10 C7 126.17(14) . . ? C11 C10 C7 129.70(14) . . ? N7 C11 C10 112.01(14) . . ? N7 C11 H11 124.0 . . ? C10 C11 H11 124.0 . . ? N8 C12 C10 106.89(14) . . ? N8 C12 H12 126.6 . . ? C10 C12 H12 126.6 . . ? C8 C81 H81A 109.5 . . ? C8 C81 H81B 109.5 . . ? H81A C81 H81B 109.5 . . ? C8 C81 H81C 109.5 . . ? H81A C81 H81C 109.5 . . ? H81B C81 H81C 109.5 . . ? C8 C82 H82A 109.5 . . ? C8 C82 H82B 109.5 . . ? H82A C82 H82B 109.5 . . ? C8 C82 H82C 109.5 . . ? H82A C82 H82C 109.5 . . ? H82B C82 H82C 109.5 . . ? C9 C91 H91A 109.5 . . ? C9 C91 H91B 109.5 . . ? H91A C91 H91B 109.5 . . ? C9 C91 H91C 109.5 . . ? H91A C91 H91C 109.5 . . ? H91B C91 H91C 109.5 . . ? C9 C92 H92A 109.5 . . ? C9 C92 H92B 109.5 . . ? H92A C92 H92B 109.5 . . ? C9 C92 H92C 109.5 . . ? H92A C92 H92C 109.5 . . ? H92B C92 H92C 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 N1 C1 C4 C5 10.2(3) . . . . ? N5 C7 C10 C11 7.2(3) . . . . ? 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 H4 O1 0.89(2) 1.83(2) 2.704(2) 164.6(19) 2_656 N8 H8 O3 0.91(2) 1.92(2) 2.8119(18) 163.5(17) 4_566 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.150 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.030