# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_cvd347 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H48 N4 O4 Zr' _chemical_formula_weight 547.88 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' Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.0054(4) _cell_length_b 11.3687(4) _cell_length_c 27.7723(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.035(4) _cell_angle_gamma 90.00 _cell_volume 2842.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 6179 _cell_measurement_theta_min 2.880 _cell_measurement_theta_max 28.495 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.420 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.945 _exptl_absorpt_correction_T_max 0.950 _exptl_absorpt_process_details abspack _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '255 images at 1.0 deg. in \w and 25 sec.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10977 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5266 _reflns_number_gt 4706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro Version 1.171.34.40' _computing_cell_refinement 'CrysAlisPro Version 1.171.34.40' _computing_data_reduction 'CrysAlisPro Version 1.171.34.40' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0269P)^2^+1.7081P] 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 5266 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0764 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _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 Zr1 Zr 0.30545(2) 0.775112(18) 0.128541(7) 0.01294(8) Uani 1 1 d . . . N1 N 0.5272(2) 0.88005(16) 0.15205(6) 0.0143(4) Uani 1 1 d . . . C2 C 0.6406(2) 0.80172(19) 0.17391(8) 0.0175(5) Uani 1 1 d . . . H2A H 0.7389 0.8407 0.1729 0.021 Uiso 1 1 calc R . . H2B H 0.6462 0.7283 0.1549 0.021 Uiso 1 1 calc R . . C3 C 0.6056(3) 0.7718(2) 0.22544(9) 0.0215(5) Uani 1 1 d . . . H3A H 0.5004 0.7476 0.2278 0.026 Uiso 1 1 calc R . . H3B H 0.6689 0.7058 0.2367 0.026 Uiso 1 1 calc R . . O4 O 0.6324(2) 0.87277(16) 0.25452(6) 0.0293(4) Uani 1 1 d . . . C5 C 0.5774(3) 0.8597(3) 0.30147(9) 0.0398(7) Uani 1 1 d . . . H5A H 0.4696 0.8485 0.2998 0.060 Uiso 1 1 calc R . . H5B H 0.6006 0.9304 0.3203 0.060 Uiso 1 1 calc R . . H5C H 0.6240 0.7911 0.3169 0.060 Uiso 1 1 calc R . . C7 C 0.7030(3) 1.0447(2) 0.16536(9) 0.0233(5) Uani 1 1 d . . . H7A H 0.7228 1.0223 0.1989 0.035 Uiso 1 1 calc R . . H7B H 0.6975 1.1306 0.1629 0.035 Uiso 1 1 calc R . . H7C H 0.7831 1.0155 0.1452 0.035 Uiso 1 1 calc R . . C8 C 0.4526(3) 1.07544(19) 0.12825(9) 0.0203(5) Uani 1 1 d . . . H8 H 0.4837 1.1553 0.1275 0.024 Uiso 1 1 calc R . . C9 C 0.3140(3) 1.05158(19) 0.11004(8) 0.0189(5) Uani 1 1 d . . . C10 C 0.2138(3) 1.1476(2) 0.09143(10) 0.0312(6) Uani 1 1 d . . . H10A H 0.1822 1.1296 0.0583 0.047 Uiso 1 1 calc R . . H10B H 0.2674 1.2226 0.0921 0.047 Uiso 1 1 calc R . . H10C H 0.1263 1.1533 0.1118 0.047 Uiso 1 1 calc R . . O11 O 0.25801(17) 0.94573(13) 0.10752(6) 0.0177(3) Uani 1 1 d . . . N12 N 0.4658(2) 0.74161(16) 0.06073(7) 0.0172(4) Uani 1 1 d . . . C13 C 0.4699(3) 0.8425(2) 0.02765(8) 0.0204(5) Uani 1 1 d . . . H13A H 0.5580 0.8355 0.0070 0.024 Uiso 1 1 calc R . . H13B H 0.4803 0.9159 0.0466 0.024 Uiso 1 1 calc R . . C14 C 0.3316(3) 0.8504(2) -0.00401(9) 0.0230(5) Uani 1 1 d . . . H14A H 0.2421 0.8467 0.0161 0.028 Uiso 1 1 calc R . . H14B H 0.3304 0.9262 -0.0215 0.028 Uiso 1 1 calc R . . O15 O 0.33016(19) 0.75553(15) -0.03746(6) 0.0264(4) Uani 1 1 d . . . C16 C 0.1944(3) 0.7523(3) -0.06380(10) 0.0335(7) Uani 1 1 d . . . H16A H 0.1125 0.7389 -0.0417 0.050 Uiso 1 1 calc R . . H16B H 0.1972 0.6884 -0.0875 0.050 Uiso 1 1 calc R . . H16C H 0.1793 0.8274 -0.0805 0.050 Uiso 1 1 calc R . . C6 C 0.5565(2) 0.9916(2) 0.14847(8) 0.0163(5) Uani 1 1 d . . . C17 C 0.5449(3) 0.6490(2) 0.05079(9) 0.0199(5) Uani 1 1 d . . . C18 C 0.6388(3) 0.6392(2) 0.00630(9) 0.0270(6) Uani 1 1 d . . . H18A H 0.5790 0.6607 -0.0222 0.040 Uiso 1 1 calc R . . H18B H 0.6743 0.5582 0.0030 0.040 Uiso 1 1 calc R . . H18C H 0.7241 0.6925 0.0093 0.040 Uiso 1 1 calc R . . C19 C 0.5516(3) 0.5471(2) 0.08173(9) 0.0220(5) Uani 1 1 d . . . H19 H 0.6082 0.4823 0.0706 0.026 Uiso 1 1 calc R . . C20 C 0.4860(3) 0.53380(19) 0.12480(9) 0.0195(5) Uani 1 1 d . . . C21 C 0.5042(3) 0.4234(2) 0.15413(10) 0.0310(6) Uani 1 1 d . . . H21A H 0.5562 0.4418 0.1845 0.047 Uiso 1 1 calc R . . H21B H 0.5622 0.3659 0.1361 0.047 Uiso 1 1 calc R . . H21C H 0.4063 0.3904 0.1609 0.047 Uiso 1 1 calc R . . O22 O 0.40160(17) 0.61463(13) 0.14430(6) 0.0186(3) Uani 1 1 d . . . N23 N 0.1219(2) 0.70801(16) 0.09119(7) 0.0175(4) Uani 1 1 d . . . C24 C 0.1229(3) 0.6075(2) 0.05850(9) 0.0220(5) Uani 1 1 d . . . H24A H 0.2241 0.5981 0.0457 0.026 Uiso 1 1 calc R . . H24B H 0.0545 0.6235 0.0310 0.026 Uiso 1 1 calc R . . C25 C 0.0768(3) 0.4930(2) 0.08258(10) 0.0339(7) Uani 1 1 d . . . H25A H 0.1439 0.4767 0.1099 0.051 Uiso 1 1 calc R . . H25B H 0.0820 0.4285 0.0593 0.051 Uiso 1 1 calc R . . H25C H -0.0251 0.5004 0.0940 0.051 Uiso 1 1 calc R . . C26 C -0.0264(3) 0.7587(2) 0.09672(9) 0.0225(5) Uani 1 1 d . . . H26A H -0.0305 0.7981 0.1285 0.027 Uiso 1 1 calc R . . H26B H -0.1002 0.6942 0.0966 0.027 Uiso 1 1 calc R . . C27 C -0.0705(3) 0.8475(2) 0.05755(10) 0.0317(6) Uani 1 1 d . . . H27A H -0.0025 0.9148 0.0589 0.048 Uiso 1 1 calc R . . H27B H -0.1722 0.8747 0.0628 0.048 Uiso 1 1 calc R . . H27C H -0.0650 0.8100 0.0259 0.048 Uiso 1 1 calc R . . N28 N 0.2185(2) 0.79539(15) 0.19651(7) 0.0146(4) Uani 1 1 d . . . C29 C 0.1728(3) 0.6943(2) 0.22529(9) 0.0192(5) Uani 1 1 d . . . H29A H 0.2218 0.7003 0.2574 0.023 Uiso 1 1 calc R . . H29B H 0.2103 0.6220 0.2098 0.023 Uiso 1 1 calc R . . C30 C 0.0065(3) 0.6800(2) 0.23247(10) 0.0288(6) Uani 1 1 d . . . H30A H -0.0311 0.7473 0.2506 0.043 Uiso 1 1 calc R . . H30B H -0.0121 0.6074 0.2504 0.043 Uiso 1 1 calc R . . H30C H -0.0444 0.6761 0.2010 0.043 Uiso 1 1 calc R . . C31 C 0.2092(2) 0.9079(2) 0.22167(8) 0.0181(5) Uani 1 1 d . . . H31A H 0.2937 0.9578 0.2119 0.022 Uiso 1 1 calc R . . H31B H 0.2201 0.8935 0.2567 0.022 Uiso 1 1 calc R . . C32 C 0.0651(3) 0.9756(2) 0.21229(9) 0.0243(6) Uani 1 1 d . . . H32A H 0.0543 0.9923 0.1778 0.037 Uiso 1 1 calc R . . H32B H 0.0677 1.0497 0.2303 0.037 Uiso 1 1 calc R . . H32C H -0.0193 0.9281 0.2228 0.037 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 Zr1 0.01109(12) 0.01297(11) 0.01479(12) -0.00179(8) 0.00088(8) -0.00110(9) N1 0.0116(9) 0.0171(9) 0.0142(10) -0.0012(7) 0.0019(8) 0.0009(8) C2 0.0104(11) 0.0176(11) 0.0245(13) -0.0029(9) -0.0010(9) 0.0021(9) C3 0.0152(12) 0.0228(11) 0.0264(13) 0.0032(10) -0.0040(10) 0.0025(10) O4 0.0362(11) 0.0333(10) 0.0185(9) -0.0027(8) 0.0015(8) 0.0008(8) C5 0.0433(18) 0.0561(19) 0.0201(14) 0.0039(13) 0.0010(13) 0.0149(15) C7 0.0184(12) 0.0192(12) 0.0324(14) -0.0022(10) 0.0011(11) -0.0059(10) C8 0.0236(13) 0.0121(11) 0.0254(13) 0.0010(9) -0.0002(11) -0.0054(10) C9 0.0239(13) 0.0153(11) 0.0176(12) 0.0017(9) 0.0011(10) 0.0000(10) C10 0.0333(15) 0.0212(13) 0.0387(16) 0.0081(11) -0.0094(13) 0.0028(11) O11 0.0170(8) 0.0148(8) 0.0211(9) 0.0017(6) -0.0035(7) -0.0023(7) N12 0.0162(10) 0.0189(10) 0.0166(10) -0.0045(8) 0.0005(8) -0.0051(8) C13 0.0231(13) 0.0194(12) 0.0187(12) -0.0033(10) 0.0052(10) -0.0071(10) C14 0.0262(13) 0.0216(12) 0.0213(13) 0.0021(10) 0.0027(11) -0.0052(10) O15 0.0263(9) 0.0318(10) 0.0211(9) -0.0058(7) -0.0021(7) -0.0065(8) C16 0.0325(15) 0.0464(17) 0.0213(14) 0.0015(12) -0.0043(12) -0.0100(13) C6 0.0153(11) 0.0181(11) 0.0154(12) -0.0018(9) 0.0015(9) -0.0005(9) C17 0.0152(12) 0.0241(12) 0.0204(13) -0.0107(10) 0.0009(10) -0.0063(10) C18 0.0269(14) 0.0290(13) 0.0253(14) -0.0104(11) 0.0100(11) -0.0046(11) C19 0.0193(12) 0.0174(11) 0.0295(14) -0.0103(10) 0.0025(11) 0.0022(10) C20 0.0184(12) 0.0114(11) 0.0289(14) -0.0051(10) -0.0003(11) 0.0012(9) C21 0.0367(16) 0.0158(12) 0.0409(17) 0.0011(11) 0.0098(13) 0.0047(11) O22 0.0190(8) 0.0150(8) 0.0218(9) -0.0018(7) 0.0043(7) 0.0009(7) N23 0.0147(10) 0.0200(10) 0.0178(10) -0.0044(8) 0.0013(8) -0.0026(8) C24 0.0200(12) 0.0245(12) 0.0215(13) -0.0054(10) 0.0030(10) -0.0072(10) C25 0.0396(17) 0.0244(13) 0.0380(16) -0.0082(12) 0.0059(13) -0.0125(12) C26 0.0128(11) 0.0295(13) 0.0251(13) -0.0059(10) -0.0018(10) -0.0014(10) C27 0.0198(13) 0.0359(15) 0.0392(16) -0.0018(13) -0.0077(12) 0.0032(12) N28 0.0119(9) 0.0153(9) 0.0167(10) -0.0006(7) 0.0009(8) 0.0011(7) C29 0.0184(12) 0.0195(12) 0.0199(12) 0.0028(9) 0.0013(10) 0.0029(9) C30 0.0218(13) 0.0269(13) 0.0379(16) 0.0072(12) 0.0057(12) -0.0017(11) C31 0.0135(11) 0.0221(12) 0.0187(12) -0.0060(10) 0.0001(9) -0.0020(10) C32 0.0194(13) 0.0210(12) 0.0326(15) -0.0080(10) -0.0002(11) 0.0043(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zr1 O22 2.0631(15) . ? Zr1 O11 2.0680(15) . ? Zr1 N28 2.0696(19) . ? Zr1 N23 2.0808(18) . ? Zr1 N1 2.4062(18) . ? Zr1 N12 2.4240(19) . ? N1 C6 1.299(3) . ? N1 C2 1.477(3) . ? C2 C3 1.510(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O4 1.421(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? O4 C5 1.411(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C7 C6 1.517(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.365(3) . ? C8 C6 1.443(3) . ? C8 H8 0.9500 . ? C9 O11 1.306(3) . ? C9 C10 1.502(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? N12 C17 1.303(3) . ? N12 C13 1.470(3) . ? C13 C14 1.514(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O15 1.423(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? O15 C16 1.414(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C19 1.444(3) . ? C17 C18 1.514(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.352(3) . ? C19 H19 0.9500 . ? C20 O22 1.315(3) . ? C20 C21 1.504(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? N23 C24 1.460(3) . ? N23 C26 1.465(3) . ? C24 C25 1.524(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.531(4) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? N28 C31 1.461(3) . ? N28 C29 1.463(3) . ? C29 C30 1.523(3) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.527(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 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 O22 Zr1 O11 166.69(6) . . ? O22 Zr1 N28 93.97(7) . . ? O11 Zr1 N28 94.20(7) . . ? O22 Zr1 N23 96.21(7) . . ? O11 Zr1 N23 92.57(7) . . ? N28 Zr1 N23 100.67(7) . . ? O22 Zr1 N1 92.17(6) . . ? O11 Zr1 N1 77.16(6) . . ? N28 Zr1 N1 91.33(7) . . ? N23 Zr1 N1 164.82(7) . . ? O22 Zr1 N12 76.84(6) . . ? O11 Zr1 N12 92.92(6) . . ? N28 Zr1 N12 165.18(7) . . ? N23 Zr1 N12 91.96(7) . . ? N1 Zr1 N12 77.62(6) . . ? C6 N1 C2 118.65(18) . . ? C6 N1 Zr1 129.20(15) . . ? C2 N1 Zr1 112.15(13) . . ? N1 C2 C3 111.72(18) . . ? N1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? O4 C3 C2 108.70(19) . . ? O4 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? O4 C3 H3B 109.9 . . ? C2 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C5 O4 C3 112.4(2) . . ? O4 C5 H5A 109.5 . . ? O4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C6 126.5(2) . . ? C9 C8 H8 116.7 . . ? C6 C8 H8 116.7 . . ? O11 C9 C8 123.5(2) . . ? O11 C9 C10 115.0(2) . . ? C8 C9 C10 121.5(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 O11 Zr1 140.49(14) . . ? C17 N12 C13 118.6(2) . . ? C17 N12 Zr1 128.82(16) . . ? C13 N12 Zr1 112.63(14) . . ? N12 C13 C14 112.30(19) . . ? N12 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? N12 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? O15 C14 C13 109.4(2) . . ? O15 C14 H14A 109.8 . . ? C13 C14 H14A 109.8 . . ? O15 C14 H14B 109.8 . . ? C13 C14 H14B 109.8 . . ? H14A C14 H14B 108.2 . . ? C16 O15 C14 110.79(19) . . ? O15 C16 H16A 109.5 . . ? O15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1 C6 C8 122.9(2) . . ? N1 C6 C7 122.8(2) . . ? C8 C6 C7 114.28(19) . . ? N12 C17 C19 122.7(2) . . ? N12 C17 C18 123.2(2) . . ? C19 C17 C18 114.1(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C17 127.0(2) . . ? C20 C19 H19 116.5 . . ? C17 C19 H19 116.5 . . ? O22 C20 C19 123.5(2) . . ? O22 C20 C21 114.7(2) . . ? C19 C20 C21 121.8(2) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 O22 Zr1 140.70(15) . . ? C24 N23 C26 112.93(18) . . ? C24 N23 Zr1 125.66(15) . . ? C26 N23 Zr1 121.40(14) . . ? N23 C24 C25 113.0(2) . . ? N23 C24 H24A 109.0 . . ? C25 C24 H24A 109.0 . . ? N23 C24 H24B 109.0 . . ? C25 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N23 C26 C27 114.2(2) . . ? N23 C26 H26A 108.7 . . ? C27 C26 H26A 108.7 . . ? N23 C26 H26B 108.7 . . ? C27 C26 H26B 108.7 . . ? H26A C26 H26B 107.6 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C31 N28 C29 114.06(18) . . ? C31 N28 Zr1 124.03(14) . . ? C29 N28 Zr1 121.70(14) . . ? N28 C29 C30 116.25(19) . . ? N28 C29 H29A 108.2 . . ? C30 C29 H29A 108.2 . . ? N28 C29 H29B 108.2 . . ? C30 C29 H29B 108.2 . . ? H29A C29 H29B 107.4 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N28 C31 C32 114.51(18) . . ? N28 C31 H31A 108.6 . . ? C32 C31 H31A 108.6 . . ? N28 C31 H31B 108.6 . . ? C32 C31 H31B 108.6 . . ? H31A C31 H31B 107.6 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 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 O22 Zr1 N1 C6 174.0(2) . . . . ? O11 Zr1 N1 C6 2.00(19) . . . . ? N28 Zr1 N1 C6 -92.0(2) . . . . ? N23 Zr1 N1 C6 50.4(4) . . . . ? N12 Zr1 N1 C6 97.9(2) . . . . ? O22 Zr1 N1 C2 -6.88(14) . . . . ? O11 Zr1 N1 C2 -178.84(15) . . . . ? N28 Zr1 N1 C2 87.15(14) . . . . ? N23 Zr1 N1 C2 -130.4(3) . . . . ? N12 Zr1 N1 C2 -82.90(14) . . . . ? C6 N1 C2 C3 101.4(2) . . . . ? Zr1 N1 C2 C3 -77.88(19) . . . . ? N1 C2 C3 O4 -72.6(2) . . . . ? C2 C3 O4 C5 169.3(2) . . . . ? C6 C8 C9 O11 -1.8(4) . . . . ? C6 C8 C9 C10 177.9(2) . . . . ? C8 C9 O11 Zr1 6.4(4) . . . . ? C10 C9 O11 Zr1 -173.28(18) . . . . ? O22 Zr1 O11 C9 -42.8(4) . . . . ? N28 Zr1 O11 C9 84.9(2) . . . . ? N23 Zr1 O11 C9 -174.1(2) . . . . ? N1 Zr1 O11 C9 -5.5(2) . . . . ? N12 Zr1 O11 C9 -82.0(2) . . . . ? O22 Zr1 N12 C17 5.24(18) . . . . ? O11 Zr1 N12 C17 176.64(19) . . . . ? N28 Zr1 N12 C17 58.0(3) . . . . ? N23 Zr1 N12 C17 -90.68(19) . . . . ? N1 Zr1 N12 C17 100.47(19) . . . . ? O22 Zr1 N12 C13 -174.71(15) . . . . ? O11 Zr1 N12 C13 -3.31(14) . . . . ? N28 Zr1 N12 C13 -122.0(3) . . . . ? N23 Zr1 N12 C13 89.37(14) . . . . ? N1 Zr1 N12 C13 -79.48(14) . . . . ? C17 N12 C13 C14 103.6(2) . . . . ? Zr1 N12 C13 C14 -76.5(2) . . . . ? N12 C13 C14 O15 -69.3(2) . . . . ? C13 C14 O15 C16 173.16(19) . . . . ? C2 N1 C6 C8 -179.2(2) . . . . ? Zr1 N1 C6 C8 -0.1(3) . . . . ? C2 N1 C6 C7 0.6(3) . . . . ? Zr1 N1 C6 C7 179.71(16) . . . . ? C9 C8 C6 N1 -0.8(4) . . . . ? C9 C8 C6 C7 179.4(2) . . . . ? C13 N12 C17 C19 178.2(2) . . . . ? Zr1 N12 C17 C19 -1.8(3) . . . . ? C13 N12 C17 C18 -1.2(3) . . . . ? Zr1 N12 C17 C18 178.90(16) . . . . ? N12 C17 C19 C20 -3.1(4) . . . . ? C18 C17 C19 C20 176.2(2) . . . . ? C17 C19 C20 O22 1.6(4) . . . . ? C17 C19 C20 C21 -178.7(2) . . . . ? C19 C20 O22 Zr1 6.9(4) . . . . ? C21 C20 O22 Zr1 -172.75(17) . . . . ? O11 Zr1 O22 C20 -48.8(4) . . . . ? N28 Zr1 O22 C20 -176.6(2) . . . . ? N23 Zr1 O22 C20 82.2(2) . . . . ? N1 Zr1 O22 C20 -85.1(2) . . . . ? N12 Zr1 O22 C20 -8.3(2) . . . . ? O22 Zr1 N23 C24 -38.65(19) . . . . ? O11 Zr1 N23 C24 131.34(18) . . . . ? N28 Zr1 N23 C24 -133.89(18) . . . . ? N1 Zr1 N23 C24 84.5(3) . . . . ? N12 Zr1 N23 C24 38.32(18) . . . . ? O22 Zr1 N23 C26 139.93(17) . . . . ? O11 Zr1 N23 C26 -50.09(18) . . . . ? N28 Zr1 N23 C26 44.68(18) . . . . ? N1 Zr1 N23 C26 -97.0(3) . . . . ? N12 Zr1 N23 C26 -143.11(18) . . . . ? C26 N23 C24 C25 -82.0(3) . . . . ? Zr1 N23 C24 C25 96.7(2) . . . . ? C24 N23 C26 C27 -84.5(2) . . . . ? Zr1 N23 C26 C27 96.8(2) . . . . ? O22 Zr1 N28 C31 143.15(16) . . . . ? O11 Zr1 N28 C31 -26.34(17) . . . . ? N23 Zr1 N28 C31 -119.76(16) . . . . ? N1 Zr1 N28 C31 50.88(16) . . . . ? N12 Zr1 N28 C31 92.2(3) . . . . ? O22 Zr1 N28 C29 -31.22(16) . . . . ? O11 Zr1 N28 C29 159.29(16) . . . . ? N23 Zr1 N28 C29 65.87(16) . . . . ? N1 Zr1 N28 C29 -123.49(16) . . . . ? N12 Zr1 N28 C29 -82.2(3) . . . . ? C31 N28 C29 C30 74.8(3) . . . . ? Zr1 N28 C29 C30 -110.3(2) . . . . ? C29 N28 C31 C32 -95.0(2) . . . . ? Zr1 N28 C31 C32 90.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.532 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 957076' ####################################################################### # # 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_cvd359 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H52 N4 O4 Zr' _chemical_formula_weight 575.94 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' Zr Zr -2.9673 0.5597 '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 20.5933(13) _cell_length_b 9.7100(5) _cell_length_c 17.6258(12) _cell_angle_alpha 90.00 _cell_angle_beta 117.329(8) _cell_angle_gamma 90.00 _cell_volume 3131.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 104(2) _cell_measurement_reflns_used 3890 _cell_measurement_theta_min 2.937 _cell_measurement_theta_max 27.424 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.385 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.960 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details abspack _exptl_special_details ; ? ; _diffrn_ambient_temperature 104(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '526 images at 1.0 deg. in \w and 40 sec.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12209 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2769 _reflns_number_gt 2427 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro Version 1.171.34.44' _computing_cell_refinement 'CrysAlisPro Version 1.171.34.44' _computing_data_reduction 'CrysAlisPro Version 1.171.34.44' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0331P)^2^+0.4768P] 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 2769 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0782 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.126 _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 Zr1 Zr 0.0000 0.30674(3) 0.2500 0.01457(11) Uani 1 2 d S . . N1 N -0.01036(10) 0.50345(19) 0.32685(11) 0.0168(4) Uani 1 1 d . . . C2 C 0.06039(12) 0.5682(2) 0.38165(13) 0.0204(5) Uani 1 1 d . . . H2A H 0.0531 0.6673 0.3887 0.024 Uiso 1 1 calc R . . H2B H 0.0929 0.5604 0.3544 0.024 Uiso 1 1 calc R . . C3 C 0.09603(12) 0.4985(3) 0.46891(14) 0.0241(5) Uani 1 1 d . . . H3A H 0.0676 0.5215 0.4998 0.029 Uiso 1 1 calc R . . H3B H 0.0936 0.3975 0.4606 0.029 Uiso 1 1 calc R . . C4 C 0.17482(13) 0.5395(3) 0.52363(15) 0.0282(6) Uani 1 1 d . . . H4A H 0.1960 0.4845 0.5769 0.034 Uiso 1 1 calc R . . H4B H 0.2036 0.5212 0.4925 0.034 Uiso 1 1 calc R . . O5 O 0.17822(9) 0.68159(17) 0.54366(10) 0.0307(4) Uani 1 1 d . . . C6 C 0.24978(14) 0.7217(3) 0.60290(17) 0.0402(7) Uani 1 1 d . . . H6A H 0.2658 0.6672 0.6552 0.060 Uiso 1 1 calc R . . H6B H 0.2500 0.8196 0.6164 0.060 Uiso 1 1 calc R . . H6C H 0.2831 0.7060 0.5781 0.060 Uiso 1 1 calc R . . C7 C -0.06803(14) 0.6909(2) 0.36945(16) 0.0295(6) Uani 1 1 d . . . H7A H -0.0292 0.6851 0.4284 0.044 Uiso 1 1 calc R . . H7B H -0.1152 0.7037 0.3695 0.044 Uiso 1 1 calc R . . H7C H -0.0586 0.7690 0.3407 0.044 Uiso 1 1 calc R . . C8 C -0.06970(12) 0.5591(2) 0.32265(14) 0.0201(5) Uani 1 1 d . . . C9 C -0.14155(12) 0.5025(2) 0.27220(14) 0.0211(5) Uani 1 1 d . . . H9 H -0.1805 0.5445 0.2785 0.025 Uiso 1 1 calc R . . C10 C -0.15964(12) 0.3954(2) 0.21653(14) 0.0197(5) Uani 1 1 d . . . O11 O -0.11214(8) 0.32887(15) 0.20027(9) 0.0184(4) Uani 1 1 d . . . C11 C -0.23675(12) 0.3446(3) 0.16806(16) 0.0299(6) Uani 1 1 d . . . H11A H -0.2518 0.3482 0.1067 0.045 Uiso 1 1 calc R . . H11B H -0.2692 0.4031 0.1811 0.045 Uiso 1 1 calc R . . H11C H -0.2397 0.2495 0.1848 0.045 Uiso 1 1 calc R . . N13 N 0.00547(10) 0.17087(18) 0.34296(11) 0.0167(4) Uani 1 1 d . . . C14 C 0.05447(12) 0.0515(2) 0.36860(14) 0.0233(5) Uani 1 1 d . . . H14A H 0.0672 0.0294 0.3222 0.028 Uiso 1 1 calc R . . H14B H 0.0282 -0.0288 0.3759 0.028 Uiso 1 1 calc R . . C15 C 0.12434(13) 0.0737(3) 0.45068(15) 0.0359(7) Uani 1 1 d . . . H15A H 0.1535 0.1460 0.4420 0.054 Uiso 1 1 calc R . . H15B H 0.1525 -0.0121 0.4670 0.054 Uiso 1 1 calc R . . H15C H 0.1122 0.1016 0.4961 0.054 Uiso 1 1 calc R . . C16 C -0.03778(13) 0.1810(2) 0.38919(15) 0.0223(5) Uani 1 1 d . . . H16A H -0.0538 0.2776 0.3872 0.027 Uiso 1 1 calc R . . H16B H -0.0063 0.1570 0.4498 0.027 Uiso 1 1 calc R . . C17 C -0.10469(13) 0.0883(3) 0.35412(18) 0.0343(6) Uani 1 1 d . . . H17A H -0.1354 0.1088 0.2935 0.051 Uiso 1 1 calc R . . H17B H -0.1326 0.1045 0.3857 0.051 Uiso 1 1 calc R . . H17C H -0.0892 -0.0083 0.3605 0.051 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 Zr1 0.01306(17) 0.01345(18) 0.01617(17) 0.000 0.00582(13) 0.000 N1 0.0177(10) 0.0161(10) 0.0163(9) -0.0004(8) 0.0076(8) -0.0023(8) C2 0.0238(13) 0.0171(12) 0.0218(12) -0.0048(10) 0.0116(10) -0.0027(10) C3 0.0250(13) 0.0247(13) 0.0201(12) -0.0020(10) 0.0081(11) -0.0025(10) C4 0.0275(14) 0.0280(14) 0.0250(13) -0.0043(11) 0.0086(11) -0.0002(11) O5 0.0236(9) 0.0327(11) 0.0320(10) -0.0130(8) 0.0093(8) -0.0062(8) C6 0.0284(15) 0.053(2) 0.0351(15) -0.0183(14) 0.0109(12) -0.0160(13) C7 0.0313(14) 0.0204(13) 0.0409(15) -0.0045(12) 0.0201(12) 0.0016(11) C8 0.0273(13) 0.0156(12) 0.0196(12) 0.0030(9) 0.0125(10) 0.0028(10) C9 0.0181(12) 0.0192(12) 0.0283(13) 0.0042(10) 0.0126(10) 0.0061(10) C10 0.0156(12) 0.0194(12) 0.0222(12) 0.0073(10) 0.0072(10) 0.0035(10) O11 0.0140(8) 0.0187(9) 0.0203(8) -0.0008(6) 0.0060(7) 0.0014(6) C11 0.0154(13) 0.0342(15) 0.0366(15) 0.0005(11) 0.0089(11) 0.0030(11) N13 0.0155(9) 0.0170(10) 0.0169(9) 0.0013(8) 0.0069(8) 0.0004(8) C14 0.0250(13) 0.0209(13) 0.0258(12) 0.0019(10) 0.0132(11) 0.0019(10) C15 0.0293(15) 0.0414(17) 0.0302(14) 0.0124(12) 0.0078(12) 0.0123(13) C16 0.0284(13) 0.0174(12) 0.0247(12) 0.0008(10) 0.0153(11) 0.0010(10) C17 0.0354(15) 0.0237(14) 0.0566(18) 0.0042(13) 0.0322(14) -0.0019(12) _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 Zr1 N13 2.0660(18) 2 ? Zr1 N13 2.0660(18) . ? Zr1 O11 2.0710(14) . ? Zr1 O11 2.0710(14) 2 ? Zr1 N1 2.4070(18) . ? Zr1 N1 2.4070(18) 2 ? N1 C8 1.307(3) . ? N1 C2 1.469(3) . ? C2 C3 1.525(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.511(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O5 1.418(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? O5 C6 1.414(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.514(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.440(3) . ? C9 C10 1.360(3) . ? C9 H9 0.9500 . ? C10 O11 1.309(3) . ? C10 C11 1.499(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? N13 C16 1.460(3) . ? N13 C14 1.465(3) . ? C14 C15 1.516(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.520(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 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 N13 Zr1 N13 100.63(10) 2 . ? N13 Zr1 O11 94.96(6) 2 . ? N13 Zr1 O11 92.64(6) . . ? N13 Zr1 O11 92.64(6) 2 2 ? N13 Zr1 O11 94.96(6) . 2 ? O11 Zr1 O11 168.09(8) . 2 ? N13 Zr1 N1 165.10(6) 2 . ? N13 Zr1 N1 92.70(7) . . ? O11 Zr1 N1 77.65(6) . . ? O11 Zr1 N1 92.82(6) 2 . ? N13 Zr1 N1 92.70(7) 2 2 ? N13 Zr1 N1 165.10(6) . 2 ? O11 Zr1 N1 92.82(6) . 2 ? O11 Zr1 N1 77.65(6) 2 2 ? N1 Zr1 N1 74.97(8) . 2 ? C8 N1 C2 118.65(19) . . ? C8 N1 Zr1 128.21(15) . . ? C2 N1 Zr1 113.09(13) . . ? N1 C2 C3 110.23(18) . . ? N1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C4 C3 C2 113.9(2) . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3B 108.8 . . ? C2 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? O5 C4 C3 109.33(19) . . ? O5 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? O5 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? C6 O5 C4 111.55(19) . . ? O5 C6 H6A 109.5 . . ? O5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C9 123.1(2) . . ? N1 C8 C7 122.1(2) . . ? C9 C8 C7 114.8(2) . . ? C10 C9 C8 127.0(2) . . ? C10 C9 H9 116.5 . . ? C8 C9 H9 116.5 . . ? O11 C10 C9 123.4(2) . . ? O11 C10 C11 114.6(2) . . ? C9 C10 C11 122.0(2) . . ? C10 O11 Zr1 139.35(14) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C16 N13 C14 113.01(18) . . ? C16 N13 Zr1 125.06(14) . . ? C14 N13 Zr1 121.92(14) . . ? N13 C14 C15 113.5(2) . . ? N13 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? N13 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N13 C16 C17 113.88(19) . . ? N13 C16 H16A 108.8 . . ? C17 C16 H16A 108.8 . . ? N13 C16 H16B 108.8 . . ? C17 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.563 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 957077' ####################################################################### # # 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_cvd396 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H58 N6 O2 Zr' _chemical_formula_weight 602.02 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' Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 22.7484(11) _cell_length_b 9.6640(3) _cell_length_c 30.8841(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.737(4) _cell_angle_gamma 90.00 _cell_volume 6670.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 112(2) _cell_measurement_reflns_used 6969 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 28.34 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2592 _exptl_absorpt_coefficient_mu 0.361 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.950 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details abspack _exptl_special_details ; ? ; _diffrn_ambient_temperature 112(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '509 images at 1.0 deg. in \w and 50sec' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 50110 _diffrn_reflns_av_R_equivalents 0.0780 _diffrn_reflns_av_sigmaI/netI 0.0932 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 28.38 _reflns_number_total 14891 _reflns_number_gt 9258 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro 1.171.35.11, Oxford Diffraction' _computing_cell_refinement 'CrysAlisPro 1.171.35.11, Oxford Diffraction' _computing_data_reduction 'CrysAlisPro 1.171.35.11, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0323P)^2^+1.3593P] 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 14891 _refine_ls_number_parameters 717 _refine_ls_number_restraints 116 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1058 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.009 _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 Zr1 Zr 0.591745(13) 0.75410(3) 0.343117(10) 0.01726(8) Uani 1 1 d . . . Zr2 Zr 0.348041(13) 0.98989(3) 0.089971(10) 0.01706(8) Uani 1 1 d . . . O1 O 0.51665(9) 0.7590(2) 0.37247(7) 0.0198(5) Uani 1 1 d . . . O2 O 0.67664(9) 0.7495(2) 0.32789(7) 0.0211(5) Uani 1 1 d . . . O3 O 0.27269(9) 0.9883(2) 0.11873(7) 0.0205(5) Uani 1 1 d . . . O4 O 0.43353(9) 0.9956(2) 0.07564(7) 0.0205(5) Uani 1 1 d . . . N1 N 0.61888(11) 0.6010(3) 0.40463(9) 0.0193(6) Uani 1 1 d . . . N2 N 0.64861(11) 0.8998(3) 0.39868(8) 0.0186(6) Uani 1 1 d . . . N3 N 0.56057(11) 0.5901(3) 0.30222(8) 0.0198(6) Uani 1 1 d . . . N4 N 0.56471(11) 0.9188(3) 0.30156(9) 0.0211(6) Uani 1 1 d . . . N5 N 0.7785(2) 0.3052(7) 0.3639(2) 0.0289(19) Uani 0.620(11) 1 d PDU A 1 C8 C 0.76203(15) 0.4328(4) 0.38283(12) 0.0284(8) Uani 0.50 1 d PD A 1 H8A H 0.7749 0.5115 0.3663 0.034 Uiso 0.620(11) 1 calc PR A 1 H8B H 0.7838 0.4393 0.4136 0.034 Uiso 0.620(11) 1 calc PR A 1 C9 C 0.8431(3) 0.3096(10) 0.3637(3) 0.042(2) Uani 0.620(11) 1 d PDU A 1 H9A H 0.8552 0.2239 0.3509 0.063 Uiso 0.620(11) 1 calc PR A 1 H9B H 0.8651 0.3191 0.3940 0.063 Uiso 0.620(11) 1 calc PR A 1 H9C H 0.8520 0.3888 0.3462 0.063 Uiso 0.620(11) 1 calc PR A 1 C10 C 0.7464(5) 0.2860(11) 0.3191(3) 0.042(3) Uani 0.620(11) 1 d PDU A 1 H10A H 0.7588 0.1987 0.3074 0.063 Uiso 0.620(11) 1 calc PR A 1 H10B H 0.7554 0.3629 0.3007 0.063 Uiso 0.620(11) 1 calc PR A 1 H10C H 0.7033 0.2834 0.3189 0.063 Uiso 0.620(11) 1 calc PR A 1 N5' N 0.7805(3) 0.3768(10) 0.3423(3) 0.025(3) Uani 0.380(11) 1 d PDU A 2 C8' C 0.76203(15) 0.4328(4) 0.38283(12) 0.0284(8) Uani 0.50 1 d PD A 2 H8'1 H 0.7803 0.5255 0.3887 0.034 Uiso 0.380(11) 1 calc PR A 2 H8'2 H 0.7794 0.3726 0.4079 0.034 Uiso 0.380(11) 1 calc PR A 2 C9' C 0.8457(4) 0.3704(15) 0.3470(4) 0.042(3) Uani 0.380(11) 1 d PDU A 2 H9'1 H 0.8627 0.4623 0.3546 0.063 Uiso 0.380(11) 1 calc PR A 2 H9'2 H 0.8561 0.3400 0.3191 0.063 Uiso 0.380(11) 1 calc PR A 2 H9'3 H 0.8618 0.3046 0.3703 0.063 Uiso 0.380(11) 1 calc PR A 2 C10' C 0.7551(9) 0.2410(12) 0.3314(6) 0.043(5) Uani 0.380(11) 1 d PDU A 2 H10D H 0.7114 0.2460 0.3279 0.065 Uiso 0.380(11) 1 calc PR A 2 H10E H 0.7707 0.1760 0.3551 0.065 Uiso 0.380(11) 1 calc PR A 2 H10F H 0.7660 0.2092 0.3038 0.065 Uiso 0.380(11) 1 calc PR A 2 N6 N 0.49415(12) 1.2173(3) 0.43826(9) 0.0246(6) Uani 1 1 d . . . N7 N 0.37661(11) 0.8324(2) 0.15008(8) 0.0178(6) Uani 1 1 d . . . N8 N 0.40095(11) 1.1367(3) 0.14754(8) 0.0187(6) Uani 1 1 d . . . N9 N 0.31766(11) 0.8291(3) 0.04721(8) 0.0189(6) Uani 1 1 d . . . N10 N 0.31830(11) 1.1555(3) 0.04925(8) 0.0180(6) Uani 1 1 d . . . N11 N 0.52265(11) 0.4975(3) 0.10823(9) 0.0242(6) Uani 1 1 d . . . N12 N 0.25118(12) 1.4703(3) 0.18611(9) 0.0245(6) Uani 1 1 d . . . C1 C 0.60876(15) 0.4511(3) 0.46789(11) 0.0276(8) Uani 1 1 d . . . H1A H 0.6361 0.3848 0.4580 0.041 Uiso 1 1 calc R . . H1B H 0.5752 0.4012 0.4765 0.041 Uiso 1 1 calc R . . H1C H 0.6302 0.5032 0.4932 0.041 Uiso 1 1 calc R . . C2 C 0.58517(15) 0.5503(3) 0.43063(10) 0.0203(7) Uani 1 1 d . . . C3 C 0.52282(14) 0.5868(3) 0.42697(11) 0.0229(8) Uani 1 1 d . . . H3 H 0.5006 0.5365 0.4449 0.027 Uiso 1 1 calc R . . C4 C 0.49283(14) 0.6857(3) 0.40051(10) 0.0209(7) Uani 1 1 d . . . C5 C 0.42880(14) 0.7210(4) 0.40187(12) 0.0301(8) Uani 1 1 d . . . H5A H 0.4263 0.8174 0.4112 0.045 Uiso 1 1 calc R . . H5B H 0.4141 0.6599 0.4228 0.045 Uiso 1 1 calc R . . H5C H 0.4043 0.7087 0.3725 0.045 Uiso 1 1 calc R . . C6 C 0.68331(14) 0.5631(3) 0.41232(11) 0.0216(8) Uani 1 1 d . A . H6A H 0.6963 0.5348 0.4434 0.026 Uiso 1 1 calc R . . H6B H 0.7071 0.6451 0.4070 0.026 Uiso 1 1 calc R . . C7 C 0.69529(14) 0.4463(4) 0.38248(12) 0.0281(8) Uani 1 1 d . . . H7A H 0.6739 0.4644 0.3520 0.034 Uiso 1 1 calc R A 1 H7B H 0.6799 0.3585 0.3926 0.034 Uiso 1 1 calc R A 1 C11 C 0.73325(15) 1.0393(4) 0.43872(12) 0.0354(9) Uani 1 1 d . . . H11A H 0.7045 1.1103 0.4437 0.053 Uiso 1 1 calc R . . H11B H 0.7680 1.0836 0.4299 0.053 Uiso 1 1 calc R . . H11C H 0.7463 0.9867 0.4660 0.053 Uiso 1 1 calc R . . C12 C 0.70382(15) 0.9419(3) 0.40242(11) 0.0255(8) Uani 1 1 d . . . C13 C 0.74223(15) 0.8999(4) 0.37283(12) 0.0303(9) Uani 1 1 d . . . H13 H 0.7812 0.9392 0.3777 0.036 Uiso 1 1 calc R . . C14 C 0.72873(15) 0.8098(4) 0.33860(11) 0.0262(8) Uani 1 1 d . . . C15 C 0.77269(16) 0.7728(4) 0.30967(13) 0.0399(10) Uani 1 1 d . . . H15A H 0.7766 0.6719 0.3085 0.060 Uiso 1 1 calc R . . H15B H 0.8117 0.8136 0.3218 0.060 Uiso 1 1 calc R . . H15C H 0.7584 0.8087 0.2799 0.060 Uiso 1 1 calc R . . C16 C 0.61354(14) 0.9438(3) 0.43182(10) 0.0190(7) Uani 1 1 d . . . H16A H 0.6412 0.9697 0.4593 0.023 Uiso 1 1 calc R . . H16B H 0.5888 0.8653 0.4386 0.023 Uiso 1 1 calc R . . C17 C 0.57303(14) 1.0659(3) 0.41602(11) 0.0217(8) Uani 1 1 d . . . H17A H 0.5975 1.1504 0.4157 0.026 Uiso 1 1 calc R . . H17B H 0.5516 1.0484 0.3856 0.026 Uiso 1 1 calc R . . C18 C 0.52803(15) 1.0881(3) 0.44605(11) 0.0244(8) Uani 1 1 d . . . H18A H 0.4995 1.0097 0.4422 0.029 Uiso 1 1 calc R . . H18B H 0.5496 1.0869 0.4770 0.029 Uiso 1 1 calc R . . C19 C 0.45427(16) 1.2296(4) 0.46968(12) 0.0394(10) Uani 1 1 d . . . H19A H 0.4319 1.3166 0.4646 0.059 Uiso 1 1 calc R . . H19B H 0.4778 1.2288 0.4997 0.059 Uiso 1 1 calc R . . H19C H 0.4262 1.1516 0.4660 0.059 Uiso 1 1 calc R . . C20 C 0.46003(17) 1.2260(4) 0.39374(12) 0.0427(11) Uani 1 1 d . . . H20A H 0.4326 1.1472 0.3881 0.064 Uiso 1 1 calc R . . H20B H 0.4874 1.2245 0.3727 0.064 Uiso 1 1 calc R . . H20C H 0.4370 1.3124 0.3903 0.064 Uiso 1 1 calc R . . C21 C 0.52969(14) 0.4656(3) 0.31348(11) 0.0246(8) Uani 1 1 d . . . H21A H 0.5380 0.4537 0.3459 0.029 Uiso 1 1 calc R . . H21B H 0.5459 0.3839 0.3004 0.029 Uiso 1 1 calc R . . C22 C 0.46202(14) 0.4711(3) 0.29736(11) 0.0281(8) Uani 1 1 d . . . H22A H 0.4451 0.5475 0.3120 0.042 Uiso 1 1 calc R . . H22B H 0.4441 0.3836 0.3044 0.042 Uiso 1 1 calc R . . H22C H 0.4534 0.4857 0.2654 0.042 Uiso 1 1 calc R . . C23 C 0.57119(15) 0.5884(3) 0.25681(11) 0.0260(8) Uani 1 1 d . . . H23A H 0.5783 0.6844 0.2479 0.031 Uiso 1 1 calc R . . H23B H 0.5345 0.5547 0.2372 0.031 Uiso 1 1 calc R . . C24 C 0.62353(16) 0.4992(4) 0.24981(11) 0.0366(9) Uani 1 1 d . . . H24A H 0.6604 0.5334 0.2683 0.055 Uiso 1 1 calc R . . H24B H 0.6274 0.5032 0.2188 0.055 Uiso 1 1 calc R . . H24C H 0.6166 0.4032 0.2578 0.055 Uiso 1 1 calc R . . C25 C 0.60064(15) 1.0387(3) 0.29406(11) 0.0289(8) Uani 1 1 d . . . H25A H 0.6344 1.0481 0.3193 0.035 Uiso 1 1 calc R . . H25B H 0.5757 1.1230 0.2931 0.035 Uiso 1 1 calc R . . C26 C 0.62563(18) 1.0300(4) 0.25152(13) 0.0427(11) Uani 1 1 d . . . H26A H 0.6510 0.9477 0.2524 0.064 Uiso 1 1 calc R . . H26B H 0.6494 1.1129 0.2486 0.064 Uiso 1 1 calc R . . H26C H 0.5925 1.0237 0.2263 0.064 Uiso 1 1 calc R . . C27 C 0.50427(15) 0.9216(3) 0.27442(11) 0.0261(8) Uani 1 1 d . . . H27A H 0.4880 0.8263 0.2722 0.031 Uiso 1 1 calc R . . H27B H 0.5073 0.9520 0.2443 0.031 Uiso 1 1 calc R . . C28 C 0.46025(15) 1.0157(4) 0.29177(12) 0.0329(9) Uani 1 1 d . . . H28A H 0.4542 0.9820 0.3205 0.049 Uiso 1 1 calc R . . H28B H 0.4219 1.0157 0.2711 0.049 Uiso 1 1 calc R . . H28C H 0.4763 1.1101 0.2949 0.049 Uiso 1 1 calc R . . C29 C 0.36911(14) 0.6871(3) 0.21494(11) 0.0253(8) Uani 1 1 d . . . H29A H 0.3970 0.6222 0.2051 0.038 Uiso 1 1 calc R . . H29B H 0.3361 0.6355 0.2237 0.038 Uiso 1 1 calc R . . H29C H 0.3901 0.7403 0.2402 0.038 Uiso 1 1 calc R . . C30 C 0.34451(14) 0.7849(3) 0.17769(10) 0.0191(7) Uani 1 1 d . . . C31 C 0.28251(14) 0.8230(3) 0.17552(11) 0.0221(8) Uani 1 1 d . . . H31 H 0.2618 0.7767 0.1953 0.027 Uiso 1 1 calc R . . C32 C 0.25098(14) 0.9176(3) 0.14841(11) 0.0217(7) Uani 1 1 d . . . C33 C 0.18658(15) 0.9505(4) 0.15023(12) 0.0330(9) Uani 1 1 d . . . H33A H 0.1834 1.0472 0.1591 0.049 Uiso 1 1 calc R . . H33B H 0.1728 0.8898 0.1717 0.049 Uiso 1 1 calc R . . H33C H 0.1617 0.9358 0.1211 0.049 Uiso 1 1 calc R . . C34 C 0.43972(13) 0.7879(3) 0.15525(10) 0.0192(7) Uani 1 1 d . . . H34A H 0.4551 0.7648 0.1865 0.023 Uiso 1 1 calc R . . H34B H 0.4640 0.8652 0.1470 0.023 Uiso 1 1 calc R . . C35 C 0.44640(14) 0.6625(3) 0.12669(11) 0.0214(7) Uani 1 1 d . . . H35A H 0.4288 0.5803 0.1386 0.026 Uiso 1 1 calc R . . H35B H 0.4242 0.6788 0.0964 0.026 Uiso 1 1 calc R . . C36 C 0.51166(14) 0.6347(3) 0.12537(11) 0.0236(8) Uani 1 1 d . . . H36A H 0.5260 0.7059 0.1068 0.028 Uiso 1 1 calc R . . H36B H 0.5353 0.6439 0.1556 0.028 Uiso 1 1 calc R . . C37 C 0.58666(15) 0.4720(4) 0.11222(12) 0.0377(10) Uani 1 1 d . . . H37A H 0.5930 0.3775 0.1025 0.057 Uiso 1 1 calc R . . H37B H 0.6064 0.4831 0.1430 0.057 Uiso 1 1 calc R . . H37C H 0.6035 0.5381 0.0938 0.057 Uiso 1 1 calc R . . C38 C 0.49341(15) 0.4816(4) 0.06237(11) 0.0301(8) Uani 1 1 d . . . H38A H 0.5088 0.5514 0.0443 0.045 Uiso 1 1 calc R . . H38B H 0.4501 0.4938 0.0599 0.045 Uiso 1 1 calc R . . H38C H 0.5016 0.3890 0.0520 0.045 Uiso 1 1 calc R . . C39 C 0.48365(15) 1.2751(3) 0.19073(11) 0.0284(8) Uani 1 1 d . . . H39A H 0.4545 1.3465 0.1946 0.043 Uiso 1 1 calc R . . H39B H 0.5196 1.3189 0.1837 0.043 Uiso 1 1 calc R . . H39C H 0.4944 1.2216 0.2180 0.043 Uiso 1 1 calc R . . C40 C 0.45657(15) 1.1795(3) 0.15347(11) 0.0208(7) Uani 1 1 d . . . C41 C 0.49720(15) 1.1400(3) 0.12514(11) 0.0236(8) Uani 1 1 d . . . H41 H 0.5365 1.1773 0.1322 0.028 Uiso 1 1 calc R . . C42 C 0.48585(14) 1.0552(3) 0.08923(11) 0.0215(7) Uani 1 1 d . . . C43 C 0.53231(15) 1.0240(4) 0.06204(11) 0.0308(9) Uani 1 1 d . . . H43A H 0.5355 0.9236 0.0586 0.046 Uiso 1 1 calc R . . H43B H 0.5710 1.0609 0.0768 0.046 Uiso 1 1 calc R . . H43C H 0.5209 1.0671 0.0330 0.046 Uiso 1 1 calc R . . C44 C 0.36395(14) 1.1807(3) 0.17958(10) 0.0206(7) Uani 1 1 d . . . H44A H 0.3904 1.2031 0.2079 0.025 Uiso 1 1 calc R . . H44B H 0.3377 1.1031 0.1848 0.025 Uiso 1 1 calc R . . C45 C 0.32533(14) 1.3067(3) 0.16364(11) 0.0215(8) Uani 1 1 d . . . H45A H 0.3514 1.3882 0.1625 0.026 Uiso 1 1 calc R . . H45B H 0.3028 1.2893 0.1335 0.026 Uiso 1 1 calc R . . C46 C 0.28174(15) 1.3367(3) 0.19422(11) 0.0267(8) Uani 1 1 d . . . H46A H 0.2513 1.2623 0.1909 0.032 Uiso 1 1 calc R . . H46B H 0.3038 1.3346 0.2250 0.032 Uiso 1 1 calc R . . C47 C 0.21421(18) 1.4948(4) 0.21917(13) 0.0429(10) Uani 1 1 d . . . H47A H 0.1942 1.5846 0.2137 0.064 Uiso 1 1 calc R . . H47B H 0.2395 1.4950 0.2486 0.064 Uiso 1 1 calc R . . H47C H 0.1841 1.4215 0.2175 0.064 Uiso 1 1 calc R . . C48 C 0.21498(16) 1.4799(4) 0.14225(12) 0.0370(9) Uani 1 1 d . . . H48A H 0.1846 1.4068 0.1384 0.056 Uiso 1 1 calc R . . H48B H 0.2406 1.4688 0.1202 0.056 Uiso 1 1 calc R . . H48C H 0.1953 1.5705 0.1385 0.056 Uiso 1 1 calc R . . C49 C 0.28295(14) 0.7101(3) 0.05753(11) 0.0246(8) Uani 1 1 d . . . H49A H 0.2893 0.6987 0.0899 0.030 Uiso 1 1 calc R . . H49B H 0.2979 0.6256 0.0451 0.030 Uiso 1 1 calc R . . C50 C 0.21576(15) 0.7241(4) 0.03952(12) 0.0339(9) Uani 1 1 d . . . H50A H 0.2002 0.8052 0.0528 0.051 Uiso 1 1 calc R . . H50B H 0.1951 0.6409 0.0468 0.051 Uiso 1 1 calc R . . H50C H 0.2091 0.7353 0.0074 0.051 Uiso 1 1 calc R . . C51 C 0.32837(15) 0.8259(3) 0.00183(10) 0.0258(8) Uani 1 1 d . . . H51A H 0.3394 0.9200 -0.0064 0.031 Uiso 1 1 calc R . . H51B H 0.2907 0.7999 -0.0181 0.031 Uiso 1 1 calc R . . C52 C 0.37751(17) 0.7253(4) -0.00516(12) 0.0363(10) Uani 1 1 d . . . H52A H 0.4154 0.7525 0.0135 0.054 Uiso 1 1 calc R . . H52B H 0.3818 0.7274 -0.0361 0.054 Uiso 1 1 calc R . . H52C H 0.3669 0.6315 0.0027 0.054 Uiso 1 1 calc R . . C53 C 0.35517(14) 1.2730(3) 0.04076(10) 0.0223(7) Uani 1 1 d . . . H53A H 0.3898 1.2813 0.0653 0.027 Uiso 1 1 calc R . . H53B H 0.3313 1.3590 0.0400 0.027 Uiso 1 1 calc R . . C54 C 0.37802(15) 1.2590(4) -0.00260(11) 0.0302(9) Uani 1 1 d . . . H54A H 0.4042 1.1780 -0.0011 0.045 Uiso 1 1 calc R . . H54B H 0.4005 1.3424 -0.0075 0.045 Uiso 1 1 calc R . . H54C H 0.3440 1.2478 -0.0270 0.045 Uiso 1 1 calc R . . C55 C 0.25702(14) 1.1608(3) 0.02440(10) 0.0209(7) Uani 1 1 d . . . H55A H 0.2394 1.0670 0.0238 0.025 Uiso 1 1 calc R . . H55B H 0.2581 1.1876 -0.0064 0.025 Uiso 1 1 calc R . . C56 C 0.21657(14) 1.2614(3) 0.04309(11) 0.0276(8) Uani 1 1 d . . . H56A H 0.2122 1.2309 0.0726 0.041 Uiso 1 1 calc R . . H56B H 0.1772 1.2640 0.0238 0.041 Uiso 1 1 calc R . . H56C H 0.2344 1.3541 0.0450 0.041 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 Zr1 0.01698(15) 0.01775(17) 0.01586(16) -0.00196(14) 0.00000(12) -0.00099(13) Zr2 0.01818(16) 0.01543(17) 0.01587(16) 0.00014(14) -0.00122(12) 0.00052(13) O1 0.0184(11) 0.0214(13) 0.0182(11) 0.0005(10) 0.0002(9) -0.0001(9) O2 0.0180(11) 0.0241(13) 0.0210(12) -0.0059(11) 0.0029(9) -0.0012(10) O3 0.0200(11) 0.0168(12) 0.0241(12) 0.0042(10) 0.0024(10) 0.0015(9) O4 0.0179(11) 0.0220(12) 0.0207(12) -0.0006(11) 0.0011(9) -0.0007(9) N1 0.0158(14) 0.0187(15) 0.0212(15) -0.0024(12) -0.0020(12) 0.0016(11) N2 0.0222(15) 0.0186(15) 0.0153(15) -0.0045(12) 0.0042(12) 0.0013(11) N3 0.0215(15) 0.0208(15) 0.0154(14) -0.0001(12) -0.0007(12) -0.0009(11) N4 0.0207(15) 0.0215(15) 0.0203(15) -0.0025(13) 0.0018(12) -0.0038(11) N5 0.021(3) 0.033(4) 0.031(3) 0.000(3) 0.003(2) 0.012(2) C8 0.0232(19) 0.032(2) 0.029(2) 0.0002(17) 0.0005(16) 0.0057(15) C9 0.029(3) 0.056(6) 0.042(5) -0.002(4) 0.009(3) 0.014(4) C10 0.037(4) 0.044(7) 0.044(6) -0.015(5) 0.007(4) 0.018(5) N5' 0.025(4) 0.023(5) 0.027(6) -0.003(4) 0.006(4) 0.006(3) C8' 0.0232(19) 0.032(2) 0.029(2) 0.0002(17) 0.0005(16) 0.0057(15) C9' 0.028(5) 0.057(9) 0.039(8) 0.008(7) 0.003(5) 0.017(5) C10' 0.050(10) 0.021(7) 0.060(13) -0.006(8) 0.015(8) 0.001(7) N6 0.0244(15) 0.0268(16) 0.0226(15) 0.0008(13) 0.0040(12) 0.0066(12) N7 0.0174(14) 0.0139(14) 0.0198(15) -0.0005(12) -0.0026(12) 0.0013(11) N8 0.0255(16) 0.0127(14) 0.0172(15) 0.0010(12) 0.0017(12) 0.0010(11) N9 0.0230(15) 0.0150(15) 0.0176(15) 0.0002(12) 0.0004(12) -0.0014(11) N10 0.0167(14) 0.0162(14) 0.0190(15) 0.0023(12) -0.0017(11) -0.0010(11) N11 0.0243(15) 0.0270(16) 0.0219(15) 0.0002(14) 0.0059(12) 0.0086(12) N12 0.0267(16) 0.0208(16) 0.0272(16) -0.0026(13) 0.0084(13) 0.0029(12) C1 0.0250(19) 0.030(2) 0.0260(19) 0.0054(16) 0.0015(15) -0.0019(15) C2 0.0256(19) 0.0198(18) 0.0144(17) -0.0017(14) 0.0012(15) 0.0009(14) C3 0.0218(18) 0.028(2) 0.0198(18) 0.0012(16) 0.0062(15) -0.0042(14) C4 0.0191(17) 0.0254(19) 0.0173(17) -0.0052(15) 0.0015(14) -0.0033(14) C5 0.0220(18) 0.030(2) 0.038(2) -0.0010(18) 0.0061(16) -0.0013(15) C6 0.0187(18) 0.0238(19) 0.0193(18) -0.0006(15) -0.0045(14) 0.0026(14) C7 0.0238(19) 0.030(2) 0.028(2) -0.0066(17) -0.0021(16) 0.0052(15) C11 0.025(2) 0.043(2) 0.037(2) -0.0172(19) 0.0036(17) -0.0105(16) C12 0.0234(19) 0.025(2) 0.027(2) -0.0021(16) -0.0001(16) -0.0036(14) C13 0.0183(18) 0.040(2) 0.034(2) -0.0136(18) 0.0081(16) -0.0097(16) C14 0.0206(18) 0.031(2) 0.028(2) -0.0034(17) 0.0072(15) -0.0031(15) C15 0.029(2) 0.050(3) 0.045(2) -0.019(2) 0.0197(19) -0.0106(18) C16 0.0201(17) 0.0191(18) 0.0167(17) -0.0037(14) 0.0003(14) -0.0030(13) C17 0.0242(19) 0.0205(18) 0.0197(18) -0.0006(15) 0.0024(15) 0.0029(14) C18 0.0269(19) 0.025(2) 0.0213(19) -0.0005(16) 0.0053(15) 0.0029(15) C19 0.040(2) 0.042(2) 0.040(2) -0.002(2) 0.0150(19) 0.0144(18) C20 0.037(2) 0.055(3) 0.034(2) 0.000(2) 0.0015(18) 0.024(2) C21 0.0286(19) 0.0214(19) 0.0208(18) 0.0002(15) -0.0027(15) -0.0040(14) C22 0.0276(19) 0.024(2) 0.030(2) 0.0000(17) -0.0008(16) -0.0033(15) C23 0.033(2) 0.024(2) 0.0191(19) -0.0015(16) -0.0013(15) -0.0034(15) C24 0.044(2) 0.044(2) 0.022(2) -0.0073(19) 0.0072(18) 0.0061(19) C25 0.028(2) 0.028(2) 0.028(2) 0.0015(17) -0.0006(16) -0.0065(15) C26 0.044(2) 0.047(3) 0.040(2) 0.013(2) 0.016(2) -0.007(2) C27 0.033(2) 0.0224(19) 0.0197(18) 0.0021(16) -0.0037(16) -0.0048(15) C28 0.0266(19) 0.035(2) 0.034(2) 0.0070(19) -0.0030(16) 0.0010(16) C29 0.0234(19) 0.027(2) 0.0240(19) 0.0069(16) 0.0008(15) -0.0012(14) C30 0.0257(18) 0.0118(17) 0.0177(17) -0.0019(14) -0.0010(14) -0.0024(13) C31 0.0257(19) 0.0214(19) 0.0202(18) 0.0032(15) 0.0068(15) -0.0012(14) C32 0.0219(18) 0.0188(18) 0.0240(19) -0.0018(15) 0.0034(15) -0.0011(14) C33 0.0240(19) 0.036(2) 0.040(2) 0.0090(19) 0.0091(17) 0.0049(16) C34 0.0179(17) 0.0211(18) 0.0169(17) 0.0018(15) -0.0013(13) 0.0023(13) C35 0.0204(18) 0.0240(19) 0.0186(18) -0.0007(15) 0.0007(14) 0.0001(14) C36 0.0223(18) 0.030(2) 0.0158(18) -0.0001(16) -0.0025(14) 0.0035(14) C37 0.031(2) 0.052(3) 0.028(2) -0.0038(19) -0.0005(17) 0.0168(18) C38 0.0285(19) 0.035(2) 0.027(2) -0.0045(18) 0.0048(16) 0.0004(16) C39 0.0299(19) 0.031(2) 0.0218(18) -0.0038(17) -0.0020(15) -0.0071(15) C40 0.0265(19) 0.0157(18) 0.0175(17) -0.0002(15) -0.0032(15) -0.0002(14) C41 0.0194(18) 0.027(2) 0.0222(19) 0.0001(16) -0.0019(15) -0.0040(14) C42 0.0204(18) 0.0198(18) 0.0232(18) 0.0065(15) 0.0012(15) 0.0029(13) C43 0.0267(19) 0.038(2) 0.028(2) 0.0004(18) 0.0061(16) -0.0023(16) C44 0.0278(19) 0.0178(18) 0.0154(17) 0.0003(15) 0.0021(14) -0.0010(14) C45 0.0239(18) 0.0178(18) 0.0220(19) -0.0015(15) 0.0026(15) -0.0002(14) C46 0.033(2) 0.0215(19) 0.028(2) 0.0013(16) 0.0112(16) 0.0018(15) C47 0.050(3) 0.035(2) 0.052(3) 0.005(2) 0.031(2) 0.0074(19) C48 0.029(2) 0.037(2) 0.040(2) -0.007(2) -0.0052(18) 0.0061(17) C49 0.0259(19) 0.0208(18) 0.0244(19) -0.0016(16) -0.0024(15) -0.0048(14) C50 0.027(2) 0.031(2) 0.040(2) -0.0023(19) -0.0032(17) -0.0076(16) C51 0.036(2) 0.0197(19) 0.0189(18) 0.0005(15) -0.0011(16) -0.0008(15) C52 0.053(3) 0.030(2) 0.029(2) -0.0036(18) 0.0153(19) 0.0001(18) C53 0.0231(17) 0.0202(18) 0.0210(18) 0.0017(15) -0.0022(14) -0.0043(14) C54 0.0288(19) 0.035(2) 0.027(2) 0.0061(18) 0.0064(16) -0.0019(16) C55 0.0252(18) 0.0179(18) 0.0169(17) 0.0014(15) -0.0036(14) 0.0010(14) C56 0.0238(18) 0.029(2) 0.028(2) 0.0008(17) 0.0001(15) 0.0019(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zr1 N4 2.065(3) . ? Zr1 N3 2.068(3) . ? Zr1 O2 2.072(2) . ? Zr1 O1 2.078(2) . ? Zr1 N1 2.396(3) . ? Zr1 N2 2.403(2) . ? Zr2 N10 2.070(2) . ? Zr2 O3 2.072(2) . ? Zr2 N9 2.073(2) . ? Zr2 O4 2.074(2) . ? Zr2 N7 2.395(3) . ? Zr2 N8 2.414(3) . ? O1 C4 1.312(4) . ? O2 C14 1.306(4) . ? O3 C32 1.311(4) . ? O4 C42 1.318(4) . ? N1 C2 1.305(4) . ? N1 C6 1.486(4) . ? N2 C12 1.305(4) . ? N2 C16 1.473(4) . ? N3 C23 1.467(4) . ? N3 C21 1.467(4) . ? N4 C25 1.462(4) . ? N4 C27 1.471(4) . ? N5 C8 1.444(6) . ? N5 C10 1.451(9) . ? N5 C9 1.470(7) . ? C8 C7 1.522(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? N5' C10' 1.448(12) . ? N5' C9' 1.464(10) . ? C9' H9'1 0.9800 . ? C9' H9'2 0.9800 . ? C9' H9'3 0.9800 . ? C10' H10D 0.9800 . ? C10' H10E 0.9800 . ? C10' H10F 0.9800 . ? N6 C20 1.450(4) . ? N6 C19 1.452(4) . ? N6 C18 1.464(4) . ? N7 C30 1.305(4) . ? N7 C34 1.478(4) . ? N8 C40 1.311(4) . ? N8 C44 1.476(4) . ? N9 C49 1.463(4) . ? N9 C51 1.467(4) . ? N10 C55 1.462(4) . ? N10 C53 1.464(4) . ? N11 C38 1.457(4) . ? N11 C37 1.459(4) . ? N11 C36 1.466(4) . ? N12 C48 1.451(4) . ? N12 C47 1.458(4) . ? N12 C46 1.465(4) . ? C1 C2 1.517(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.445(4) . ? C3 C4 1.356(4) . ? C3 H3 0.9500 . ? C4 C5 1.504(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.514(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C11 C12 1.520(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.436(5) . ? C13 C14 1.360(4) . ? C13 H13 0.9500 . ? C14 C15 1.503(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.520(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.519(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.528(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.518(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.528(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.522(4) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C30 1.513(4) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 C31 1.447(4) . ? C31 C32 1.352(4) . ? C31 H31 0.9500 . ? C32 C33 1.510(4) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C35 1.523(4) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.517(4) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 C40 1.514(4) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 C41 1.438(5) . ? C41 C42 1.365(4) . ? C41 H41 0.9500 . ? C42 C43 1.498(4) . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 C45 1.529(4) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 C46 1.519(4) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 C50 1.532(4) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C51 C52 1.527(4) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 C54 1.530(4) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 C56 1.525(4) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 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 N4 Zr1 N3 100.52(10) . . ? N4 Zr1 O2 93.31(9) . . ? N3 Zr1 O2 94.20(9) . . ? N4 Zr1 O1 94.57(9) . . ? N3 Zr1 O1 93.88(9) . . ? O2 Zr1 O1 167.51(8) . . ? N4 Zr1 N1 166.28(9) . . ? N3 Zr1 N1 91.12(9) . . ? O2 Zr1 N1 93.06(9) . . ? O1 Zr1 N1 77.26(8) . . ? N4 Zr1 N2 92.91(9) . . ? N3 Zr1 N2 164.37(9) . . ? O2 Zr1 N2 76.93(8) . . ? O1 Zr1 N2 92.99(8) . . ? N1 Zr1 N2 76.73(9) . . ? N10 Zr2 O3 93.64(9) . . ? N10 Zr2 N9 99.22(10) . . ? O3 Zr2 N9 93.63(9) . . ? N10 Zr2 O4 93.61(9) . . ? O3 Zr2 O4 167.15(8) . . ? N9 Zr2 O4 95.67(9) . . ? N10 Zr2 N7 166.70(9) . . ? O3 Zr2 N7 77.86(8) . . ? N9 Zr2 N7 91.58(9) . . ? O4 Zr2 N7 93.01(8) . . ? N10 Zr2 N8 93.13(9) . . ? O3 Zr2 N8 91.57(9) . . ? N9 Zr2 N8 166.26(9) . . ? O4 Zr2 N8 77.44(8) . . ? N7 Zr2 N8 77.09(8) . . ? C4 O1 Zr1 138.6(2) . . ? C14 O2 Zr1 140.6(2) . . ? C32 O3 Zr2 138.85(19) . . ? C42 O4 Zr2 140.4(2) . . ? C2 N1 C6 118.9(3) . . ? C2 N1 Zr1 128.7(2) . . ? C6 N1 Zr1 112.31(19) . . ? C12 N2 C16 119.0(3) . . ? C12 N2 Zr1 128.9(2) . . ? C16 N2 Zr1 112.10(19) . . ? C23 N3 C21 112.9(3) . . ? C23 N3 Zr1 119.6(2) . . ? C21 N3 Zr1 127.5(2) . . ? C25 N4 C27 112.7(3) . . ? C25 N4 Zr1 126.8(2) . . ? C27 N4 Zr1 120.5(2) . . ? C8 N5 C10 111.9(6) . . ? C8 N5 C9 108.2(5) . . ? C10 N5 C9 109.1(7) . . ? N5 C8 C7 113.9(3) . . ? N5 C8 H8A 108.8 . . ? C7 C8 H8A 108.8 . . ? N5 C8 H8B 108.8 . . ? C7 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? N5 C9 H9A 109.5 . . ? N5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N5 C10 H10A 109.5 . . ? N5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C10' N5' C9' 109.7(10) . . ? N5' C9' H9'1 109.5 . . ? N5' C9' H9'2 109.5 . . ? H9'1 C9' H9'2 109.5 . . ? N5' C9' H9'3 109.5 . . ? H9'1 C9' H9'3 109.5 . . ? H9'2 C9' H9'3 109.5 . . ? N5' C10' H10D 109.5 . . ? N5' C10' H10E 109.5 . . ? H10D C10' H10E 109.5 . . ? N5' C10' H10F 109.5 . . ? H10D C10' H10F 109.5 . . ? H10E C10' H10F 109.5 . . ? C20 N6 C19 109.8(3) . . ? C20 N6 C18 112.2(3) . . ? C19 N6 C18 109.6(3) . . ? C30 N7 C34 118.5(3) . . ? C30 N7 Zr2 128.8(2) . . ? C34 N7 Zr2 112.73(19) . . ? C40 N8 C44 118.1(3) . . ? C40 N8 Zr2 128.6(2) . . ? C44 N8 Zr2 113.24(19) . . ? C49 N9 C51 112.6(3) . . ? C49 N9 Zr2 125.4(2) . . ? C51 N9 Zr2 122.0(2) . . ? C55 N10 C53 113.6(2) . . ? C55 N10 Zr2 121.2(2) . . ? C53 N10 Zr2 125.12(19) . . ? C38 N11 C37 109.4(3) . . ? C38 N11 C36 111.6(3) . . ? C37 N11 C36 110.9(3) . . ? C48 N12 C47 110.0(3) . . ? C48 N12 C46 112.6(3) . . ? C47 N12 C46 109.9(3) . . ? 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 . . ? N1 C2 C3 122.7(3) . . ? N1 C2 C1 122.6(3) . . ? C3 C2 C1 114.7(3) . . ? C4 C3 C2 126.5(3) . . ? C4 C3 H3 116.7 . . ? C2 C3 H3 116.7 . . ? O1 C4 C3 123.7(3) . . ? O1 C4 C5 114.7(3) . . ? C3 C4 C5 121.6(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 111.8(2) . . ? N1 C6 H6A 109.3 . . ? C7 C6 H6A 109.3 . . ? N1 C6 H6B 109.3 . . ? C7 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C6 C7 C8 110.6(3) . . ? C6 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 C13 123.0(3) . . ? N2 C12 C11 122.9(3) . . ? C13 C12 C11 114.1(3) . . ? C14 C13 C12 126.9(3) . . ? C14 C13 H13 116.6 . . ? C12 C13 H13 116.6 . . ? O2 C14 C13 123.0(3) . . ? O2 C14 C15 114.6(3) . . ? C13 C14 C15 122.4(3) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 C16 C17 112.1(3) . . ? N2 C16 H16A 109.2 . . ? C17 C16 H16A 109.2 . . ? N2 C16 H16B 109.2 . . ? C17 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C16 110.5(3) . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? N6 C18 C17 114.5(3) . . ? N6 C18 H18A 108.6 . . ? C17 C18 H18A 108.6 . . ? N6 C18 H18B 108.6 . . ? C17 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? N6 C19 H19A 109.5 . . ? N6 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N6 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N6 C20 H20A 109.5 . . ? N6 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N6 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N3 C21 C22 113.1(3) . . ? N3 C21 H21A 109.0 . . ? C22 C21 H21A 109.0 . . ? N3 C21 H21B 109.0 . . ? C22 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N3 C23 C24 114.6(3) . . ? N3 C23 H23A 108.6 . . ? C24 C23 H23A 108.6 . . ? N3 C23 H23B 108.6 . . ? C24 C23 H23B 108.6 . . ? H23A C23 H23B 107.6 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N4 C25 C26 113.6(3) . . ? N4 C25 H25A 108.8 . . ? C26 C25 H25A 108.8 . . ? N4 C25 H25B 108.8 . . ? C26 C25 H25B 108.8 . . ? H25A C25 H25B 107.7 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N4 C27 C28 114.6(3) . . ? N4 C27 H27A 108.6 . . ? C28 C27 H27A 108.6 . . ? N4 C27 H27B 108.6 . . ? C28 C27 H27B 108.6 . . ? H27A C27 H27B 107.6 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 H29A 109.5 . . ? C30 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C30 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N7 C30 C31 122.6(3) . . ? N7 C30 C29 123.0(3) . . ? C31 C30 C29 114.4(3) . . ? C32 C31 C30 126.9(3) . . ? C32 C31 H31 116.5 . . ? C30 C31 H31 116.5 . . ? O3 C32 C31 124.0(3) . . ? O3 C32 C33 114.3(3) . . ? C31 C32 C33 121.7(3) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N7 C34 C35 111.6(2) . . ? N7 C34 H34A 109.3 . . ? C35 C34 H34A 109.3 . . ? N7 C34 H34B 109.3 . . ? C35 C34 H34B 109.3 . . ? H34A C34 H34B 108.0 . . ? C36 C35 C34 111.1(3) . . ? C36 C35 H35A 109.4 . . ? C34 C35 H35A 109.4 . . ? C36 C35 H35B 109.4 . . ? C34 C35 H35B 109.4 . . ? H35A C35 H35B 108.0 . . ? N11 C36 C35 113.8(3) . . ? N11 C36 H36A 108.8 . . ? C35 C36 H36A 108.8 . . ? N11 C36 H36B 108.8 . . ? C35 C36 H36B 108.8 . . ? H36A C36 H36B 107.7 . . ? N11 C37 H37A 109.5 . . ? N11 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? N11 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N11 C38 H38A 109.5 . . ? N11 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? N11 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C40 C39 H39A 109.5 . . ? C40 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C40 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? N8 C40 C41 123.0(3) . . ? N8 C40 C39 123.0(3) . . ? C41 C40 C39 114.1(3) . . ? C42 C41 C40 127.5(3) . . ? C42 C41 H41 116.3 . . ? C40 C41 H41 116.3 . . ? O4 C42 C41 122.9(3) . . ? O4 C42 C43 115.0(3) . . ? C41 C42 C43 122.0(3) . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? N8 C44 C45 112.2(3) . . ? N8 C44 H44A 109.2 . . ? C45 C44 H44A 109.2 . . ? N8 C44 H44B 109.2 . . ? C45 C44 H44B 109.2 . . ? H44A C44 H44B 107.9 . . ? C46 C45 C44 110.8(3) . . ? C46 C45 H45A 109.5 . . ? C44 C45 H45A 109.5 . . ? C46 C45 H45B 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 108.1 . . ? N12 C46 C45 113.9(3) . . ? N12 C46 H46A 108.8 . . ? C45 C46 H46A 108.8 . . ? N12 C46 H46B 108.8 . . ? C45 C46 H46B 108.8 . . ? H46A C46 H46B 107.7 . . ? N12 C47 H47A 109.5 . . ? N12 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? N12 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? N12 C48 H48A 109.5 . . ? N12 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? N12 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? N9 C49 C50 113.2(3) . . ? N9 C49 H49A 108.9 . . ? C50 C49 H49A 108.9 . . ? N9 C49 H49B 108.9 . . ? C50 C49 H49B 108.9 . . ? H49A C49 H49B 107.8 . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? N9 C51 C52 113.9(3) . . ? N9 C51 H51A 108.8 . . ? C52 C51 H51A 108.8 . . ? N9 C51 H51B 108.8 . . ? C52 C51 H51B 108.8 . . ? H51A C51 H51B 107.7 . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? N10 C53 C54 112.8(3) . . ? N10 C53 H53A 109.0 . . ? C54 C53 H53A 109.0 . . ? N10 C53 H53B 109.0 . . ? C54 C53 H53B 109.0 . . ? H53A C53 H53B 107.8 . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? N10 C55 C56 114.0(3) . . ? N10 C55 H55A 108.7 . . ? C56 C55 H55A 108.7 . . ? N10 C55 H55B 108.7 . . ? C56 C55 H55B 108.7 . . ? H55A C55 H55B 107.6 . . ? C55 C56 H56A 109.5 . . ? C55 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C55 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.961 _refine_diff_density_min -0.612 _refine_diff_density_rms 0.088 _database_code_depnum_ccdc_archive 'CCDC 957078' ####################################################################### # # 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_cvd340 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H56 N4 O8 Zr' _chemical_formula_weight 716.03 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' Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 19.2359(18) _cell_length_b 18.1915(15) _cell_length_c 10.2582(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3589.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 1165 _cell_measurement_theta_min 2.897 _cell_measurement_theta_max 24.992 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.358 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details abspack _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12467 _diffrn_reflns_av_R_equivalents 0.1225 _diffrn_reflns_av_sigmaI/netI 0.1177 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3182 _reflns_number_gt 1830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro Version 1.171.34.44' _computing_cell_refinement 'CrysAlisPro Version 1.171.34.44' _computing_data_reduction 'CrysAlisPro Version 1.171.34.44' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0564P)^2^+4.0255P] 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 3182 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1294 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1550 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 Zr1 Zr 0.57039(4) 0.7500 0.7500 0.0156(2) Uani 1 2 d S . . O3 O 0.5079(2) 0.77441(19) 0.9127(4) 0.0220(9) Uani 1 1 d . . . C10 C 0.4897(3) 0.8337(3) 0.9740(6) 0.0222(14) Uani 1 1 d . . . C11 C 0.4838(3) 0.8991(3) 0.9145(6) 0.0254(15) Uani 1 1 d . . . H13 H 0.4779 0.9408 0.9690 0.031 Uiso 1 1 calc R . . C12 C 0.4854(3) 0.9119(3) 0.7767(6) 0.0221(15) Uani 1 1 d . . . N2 N 0.5037(2) 0.8603(2) 0.6940(4) 0.0177(11) Uani 1 1 d . . . C9 C 0.4752(4) 0.8235(3) 1.1159(5) 0.0344(17) Uani 1 1 d . . . H12A H 0.4396 0.7855 1.1272 0.052 Uiso 1 1 calc R . . H12B H 0.4586 0.8699 1.1532 0.052 Uiso 1 1 calc R . . H12C H 0.5180 0.8083 1.1605 0.052 Uiso 1 1 calc R . . C13 C 0.4640(3) 0.9885(3) 0.7341(6) 0.0301(15) Uani 1 1 d . . . H14A H 0.5048 1.0151 0.7020 0.045 Uiso 1 1 calc R . . H14B H 0.4440 1.0149 0.8084 0.045 Uiso 1 1 calc R . . H14C H 0.4293 0.9849 0.6644 0.045 Uiso 1 1 calc R . . C14 C 0.4890(3) 0.8773(3) 0.5537(5) 0.0223(14) Uani 1 1 d . . . H15A H 0.5196 0.8470 0.4975 0.027 Uiso 1 1 calc R . . H15B H 0.4994 0.9296 0.5363 0.027 Uiso 1 1 calc R . . C15 C 0.4143(3) 0.8618(3) 0.5210(5) 0.0245(14) Uani 1 1 d . . . H15C H 0.4028 0.8100 0.5413 0.029 Uiso 1 1 calc R . . H15D H 0.3833 0.8940 0.5727 0.029 Uiso 1 1 calc R . . O4 O 0.4052(2) 0.8754(2) 0.3864(4) 0.0298(10) Uani 1 1 d . . . C16 C 0.3375(3) 0.8573(4) 0.3437(6) 0.0375(17) Uani 1 1 d . . . H15E H 0.3300 0.8043 0.3536 0.056 Uiso 1 1 calc R . . H15F H 0.3323 0.8709 0.2518 0.056 Uiso 1 1 calc R . . H15G H 0.3032 0.8841 0.3961 0.056 Uiso 1 1 calc R . . O1 O 0.6322(2) 0.8374(2) 0.8305(4) 0.0308(11) Uani 1 1 d . . . C2 C 0.6489(3) 0.9044(3) 0.7927(6) 0.0286(16) Uani 1 1 d . . . C3 C 0.6569(3) 0.9217(3) 0.6633(6) 0.0281(15) Uani 1 1 d . . . H23 H 0.6637 0.9719 0.6416 0.034 Uiso 1 1 calc R . . C4 C 0.6558(3) 0.8707(3) 0.5605(6) 0.0298(16) Uani 1 1 d . . . N1 N 0.6359(3) 0.8016(2) 0.5771(5) 0.0262(12) Uani 1 1 d . . . C1 C 0.6608(4) 0.9579(4) 0.8988(6) 0.0453(19) Uani 1 1 d . . . H22A H 0.6172 0.9663 0.9459 0.068 Uiso 1 1 calc R . . H22B H 0.6773 1.0045 0.8618 0.068 Uiso 1 1 calc R . . H22C H 0.6958 0.9385 0.9591 0.068 Uiso 1 1 calc R . . C5 C 0.6786(4) 0.9002(4) 0.4288(6) 0.050(2) Uani 1 1 d . . . H24A H 0.7199 0.8734 0.3993 0.075 Uiso 1 1 calc R . . H24B H 0.6896 0.9526 0.4367 0.075 Uiso 1 1 calc R . . H24C H 0.6409 0.8936 0.3655 0.075 Uiso 1 1 calc R . . C6 C 0.6507(3) 0.7536(4) 0.4553(6) 0.0409(16) Uani 1 1 d . . . H25A H 0.6178 0.7118 0.4531 0.049 Uiso 1 1 calc R . . H25B H 0.6435 0.7833 0.3756 0.049 Uiso 1 1 calc R . . C7 C 0.7257(4) 0.7243(5) 0.4575(7) 0.059(2) Uani 1 1 d . . . H25C H 0.7587 0.7652 0.4418 0.070 Uiso 1 1 calc R . . H25D H 0.7360 0.7029 0.5441 0.070 Uiso 1 1 calc R . . O2 O 0.7338(2) 0.6706(2) 0.3610(4) 0.0440(13) Uani 1 1 d . . . C8 C 0.8029(4) 0.6465(4) 0.3607(7) 0.059(2) Uani 1 1 d . . . H25E H 0.8333 0.6869 0.3336 0.088 Uiso 1 1 calc R . . H25F H 0.8079 0.6054 0.2997 0.088 Uiso 1 1 calc R . . H25G H 0.8158 0.6304 0.4486 0.088 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 Zr1 0.0196(4) 0.0143(4) 0.0130(3) -0.0012(4) 0.000 0.000 O3 0.026(2) 0.016(2) 0.024(2) -0.0004(16) 0.0017(19) -0.0012(17) C10 0.025(4) 0.015(3) 0.027(3) -0.002(3) -0.001(3) -0.002(3) C11 0.027(4) 0.024(3) 0.025(4) -0.012(3) 0.003(3) -0.004(3) C12 0.018(3) 0.016(3) 0.032(4) 0.000(3) 0.007(3) -0.002(2) N2 0.020(3) 0.018(3) 0.015(2) 0.000(2) 0.000(2) -0.004(2) C9 0.048(5) 0.034(4) 0.022(3) -0.004(3) 0.010(3) -0.005(3) C13 0.040(4) 0.018(3) 0.032(4) 0.004(3) -0.003(4) 0.001(3) C14 0.023(3) 0.022(3) 0.022(3) 0.009(3) 0.003(3) 0.002(3) C15 0.029(4) 0.026(3) 0.019(3) 0.001(3) -0.001(3) 0.003(3) O4 0.025(2) 0.046(3) 0.019(2) 0.005(2) -0.0038(19) -0.002(2) C16 0.030(4) 0.055(5) 0.027(4) 0.002(3) -0.013(3) 0.001(3) O1 0.024(2) 0.028(2) 0.041(3) 0.007(2) -0.001(2) -0.004(2) C2 0.014(3) 0.028(4) 0.044(4) 0.001(3) -0.001(3) -0.004(3) C3 0.024(4) 0.021(3) 0.040(4) -0.001(3) 0.008(3) -0.001(3) C4 0.021(3) 0.038(4) 0.031(4) 0.002(3) 0.002(3) 0.012(3) N1 0.024(3) 0.016(3) 0.038(3) -0.006(2) -0.009(3) 0.007(2) C1 0.032(4) 0.057(5) 0.047(4) -0.015(4) 0.001(4) -0.006(4) C5 0.047(5) 0.066(5) 0.038(4) 0.007(4) 0.007(4) 0.025(4) C6 0.039(4) 0.057(4) 0.027(3) -0.005(4) 0.001(3) -0.004(4) C7 0.028(4) 0.119(7) 0.029(4) -0.021(4) 0.007(3) 0.021(4) O2 0.038(3) 0.056(3) 0.038(3) -0.017(2) 0.003(2) 0.015(2) C8 0.043(5) 0.079(6) 0.053(5) -0.016(5) 0.007(4) 0.021(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 Zr1 O3 2.105(4) 4_566 ? Zr1 O3 2.105(4) . ? Zr1 O1 2.150(4) . ? Zr1 O1 2.150(4) 4_566 ? Zr1 N1 2.369(5) . ? Zr1 N1 2.369(5) 4_566 ? Zr1 N2 2.450(4) . ? Zr1 N2 2.450(4) 4_566 ? O3 C10 1.297(6) . ? C10 C11 1.341(8) . ? C10 C9 1.494(7) . ? C11 C12 1.433(7) . ? C11 H13 0.9500 . ? C12 N2 1.314(7) . ? C12 C13 1.517(7) . ? N2 C14 1.498(7) . ? C9 H12A 0.9800 . ? C9 H12B 0.9800 . ? C9 H12C 0.9800 . ? C13 H14A 0.9800 . ? C13 H14B 0.9800 . ? C13 H14C 0.9800 . ? C14 C15 1.503(8) . ? C14 H15A 0.9900 . ? C14 H15B 0.9900 . ? C15 O4 1.414(6) . ? C15 H15C 0.9900 . ? C15 H15D 0.9900 . ? O4 C16 1.413(7) . ? C16 H15E 0.9800 . ? C16 H15F 0.9800 . ? C16 H15G 0.9800 . ? O1 C2 1.319(7) . ? C2 C3 1.373(9) . ? C2 C1 1.478(8) . ? C3 C4 1.405(8) . ? C3 H23 0.9500 . ? C4 N1 1.325(7) . ? C4 C5 1.518(8) . ? N1 C6 1.550(7) . ? C1 H22A 0.9800 . ? C1 H22B 0.9800 . ? C1 H22C 0.9800 . ? C5 H24A 0.9800 . ? C5 H24B 0.9800 . ? C5 H24C 0.9800 . ? C6 C7 1.538(9) . ? C6 H25A 0.9900 . ? C6 H25B 0.9900 . ? C7 O2 1.399(7) . ? C7 H25C 0.9900 . ? C7 H25D 0.9900 . ? O2 C8 1.400(8) . ? C8 H25E 0.9800 . ? C8 H25F 0.9800 . ? C8 H25G 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 O3 Zr1 O3 110.3(2) 4_566 . ? O3 Zr1 O1 140.94(14) 4_566 . ? O3 Zr1 O1 81.69(15) . . ? O3 Zr1 O1 81.69(15) 4_566 4_566 ? O3 Zr1 O1 140.94(14) . 4_566 ? O1 Zr1 O1 112.9(2) . 4_566 ? O3 Zr1 N1 78.10(15) 4_566 . ? O3 Zr1 N1 144.49(14) . . ? O1 Zr1 N1 72.58(16) . . ? O1 Zr1 N1 73.23(15) 4_566 . ? O3 Zr1 N1 144.49(14) 4_566 4_566 ? O3 Zr1 N1 78.10(15) . 4_566 ? O1 Zr1 N1 73.23(15) . 4_566 ? O1 Zr1 N1 72.58(16) 4_566 4_566 ? N1 Zr1 N1 115.8(2) . 4_566 ? O3 Zr1 N2 71.80(14) 4_566 . ? O3 Zr1 N2 73.39(14) . . ? O1 Zr1 N2 76.91(15) . . ? O1 Zr1 N2 143.62(15) 4_566 . ? N1 Zr1 N2 77.19(15) . . ? N1 Zr1 N2 141.10(15) 4_566 . ? O3 Zr1 N2 73.39(14) 4_566 4_566 ? O3 Zr1 N2 71.80(14) . 4_566 ? O1 Zr1 N2 143.62(15) . 4_566 ? O1 Zr1 N2 76.91(15) 4_566 4_566 ? N1 Zr1 N2 141.10(15) . 4_566 ? N1 Zr1 N2 77.19(15) 4_566 4_566 ? N2 Zr1 N2 116.9(2) . 4_566 ? C10 O3 Zr1 135.6(3) . . ? O3 C10 C11 122.7(5) . . ? O3 C10 C9 114.8(5) . . ? C11 C10 C9 122.6(5) . . ? C10 C11 C12 126.3(5) . . ? C10 C11 H13 116.9 . . ? C12 C11 H13 116.9 . . ? N2 C12 C11 121.8(5) . . ? N2 C12 C13 122.9(5) . . ? C11 C12 C13 115.4(5) . . ? C12 N2 C14 115.0(5) . . ? C12 N2 Zr1 125.1(4) . . ? C14 N2 Zr1 119.5(3) . . ? C10 C9 H12A 109.5 . . ? C10 C9 H12B 109.5 . . ? H12A C9 H12B 109.5 . . ? C10 C9 H12C 109.5 . . ? H12A C9 H12C 109.5 . . ? H12B C9 H12C 109.5 . . ? C12 C13 H14A 109.5 . . ? C12 C13 H14B 109.5 . . ? H14A C13 H14B 109.5 . . ? C12 C13 H14C 109.5 . . ? H14A C13 H14C 109.5 . . ? H14B C13 H14C 109.5 . . ? N2 C14 C15 110.9(5) . . ? N2 C14 H15A 109.5 . . ? C15 C14 H15A 109.5 . . ? N2 C14 H15B 109.5 . . ? C15 C14 H15B 109.5 . . ? H15A C14 H15B 108.0 . . ? O4 C15 C14 107.7(5) . . ? O4 C15 H15C 110.2 . . ? C14 C15 H15C 110.2 . . ? O4 C15 H15D 110.2 . . ? C14 C15 H15D 110.2 . . ? H15C C15 H15D 108.5 . . ? C16 O4 C15 112.1(5) . . ? O4 C16 H15E 109.5 . . ? O4 C16 H15F 109.5 . . ? H15E C16 H15F 109.5 . . ? O4 C16 H15G 109.5 . . ? H15E C16 H15G 109.5 . . ? H15F C16 H15G 109.5 . . ? C2 O1 Zr1 134.9(4) . . ? O1 C2 C3 121.5(6) . . ? O1 C2 C1 115.5(6) . . ? C3 C2 C1 123.0(6) . . ? C2 C3 C4 125.0(6) . . ? C2 C3 H23 117.5 . . ? C4 C3 H23 117.5 . . ? N1 C4 C3 122.3(6) . . ? N1 C4 C5 122.2(6) . . ? C3 C4 C5 115.5(6) . . ? C4 N1 C6 112.1(5) . . ? C4 N1 Zr1 128.7(4) . . ? C6 N1 Zr1 118.6(4) . . ? C2 C1 H22A 109.5 . . ? C2 C1 H22B 109.5 . . ? H22A C1 H22B 109.5 . . ? C2 C1 H22C 109.5 . . ? H22A C1 H22C 109.5 . . ? H22B C1 H22C 109.5 . . ? C4 C5 H24A 109.5 . . ? C4 C5 H24B 109.5 . . ? H24A C5 H24B 109.5 . . ? C4 C5 H24C 109.5 . . ? H24A C5 H24C 109.5 . . ? H24B C5 H24C 109.5 . . ? C7 C6 N1 110.9(5) . . ? C7 C6 H25A 109.5 . . ? N1 C6 H25A 109.5 . . ? C7 C6 H25B 109.5 . . ? N1 C6 H25B 109.5 . . ? H25A C6 H25B 108.0 . . ? O2 C7 C6 109.6(6) . . ? O2 C7 H25C 109.7 . . ? C6 C7 H25C 109.7 . . ? O2 C7 H25D 109.7 . . ? C6 C7 H25D 109.7 . . ? H25C C7 H25D 108.2 . . ? C7 O2 C8 109.0(5) . . ? O2 C8 H25E 109.5 . . ? O2 C8 H25F 109.5 . . ? H25E C8 H25F 109.5 . . ? O2 C8 H25G 109.5 . . ? H25E C8 H25G 109.5 . . ? H25F C8 H25G 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 O3 Zr1 O3 C10 -104.0(5) 4_566 . . . ? O1 Zr1 O3 C10 37.5(5) . . . . ? O1 Zr1 O3 C10 153.8(5) 4_566 . . . ? N1 Zr1 O3 C10 -6.0(7) . . . . ? N1 Zr1 O3 C10 112.0(5) 4_566 . . . ? N2 Zr1 O3 C10 -41.2(5) . . . . ? N2 Zr1 O3 C10 -167.7(5) 4_566 . . . ? Zr1 O3 C10 C11 30.0(9) . . . . ? Zr1 O3 C10 C9 -150.6(4) . . . . ? O3 C10 C11 C12 10.2(10) . . . . ? C9 C10 C11 C12 -169.1(6) . . . . ? C10 C11 C12 N2 -10.6(10) . . . . ? C10 C11 C12 C13 168.9(6) . . . . ? C11 C12 N2 C14 168.1(5) . . . . ? C13 C12 N2 C14 -11.4(8) . . . . ? C11 C12 N2 Zr1 -19.5(8) . . . . ? C13 C12 N2 Zr1 161.0(4) . . . . ? O3 Zr1 N2 C12 152.3(5) 4_566 . . . ? O3 Zr1 N2 C12 33.7(4) . . . . ? O1 Zr1 N2 C12 -51.4(4) . . . . ? O1 Zr1 N2 C12 -162.3(4) 4_566 . . . ? N1 Zr1 N2 C12 -126.2(4) . . . . ? N1 Zr1 N2 C12 -10.8(6) 4_566 . . . ? N2 Zr1 N2 C12 92.6(4) 4_566 . . . ? O3 Zr1 N2 C14 -35.6(4) 4_566 . . . ? O3 Zr1 N2 C14 -154.2(4) . . . . ? O1 Zr1 N2 C14 120.7(4) . . . . ? O1 Zr1 N2 C14 9.8(5) 4_566 . . . ? N1 Zr1 N2 C14 45.9(4) . . . . ? N1 Zr1 N2 C14 161.2(3) 4_566 . . . ? N2 Zr1 N2 C14 -95.3(4) 4_566 . . . ? C12 N2 C14 C15 -81.2(6) . . . . ? Zr1 N2 C14 C15 106.0(5) . . . . ? N2 C14 C15 O4 -177.1(4) . . . . ? C14 C15 O4 C16 175.7(5) . . . . ? O3 Zr1 O1 C2 -1.4(6) 4_566 . . . ? O3 Zr1 O1 C2 -113.5(5) . . . . ? O1 Zr1 O1 C2 104.3(5) 4_566 . . . ? N1 Zr1 O1 C2 41.7(5) . . . . ? N1 Zr1 O1 C2 166.5(6) 4_566 . . . ? N2 Zr1 O1 C2 -38.7(5) . . . . ? N2 Zr1 O1 C2 -156.6(5) 4_566 . . . ? Zr1 O1 C2 C3 -32.5(9) . . . . ? Zr1 O1 C2 C1 149.6(5) . . . . ? O1 C2 C3 C4 -7.1(10) . . . . ? C1 C2 C3 C4 170.6(6) . . . . ? C2 C3 C4 N1 11.0(10) . . . . ? C2 C3 C4 C5 -169.3(6) . . . . ? C3 C4 N1 C6 -170.6(5) . . . . ? C5 C4 N1 C6 9.8(8) . . . . ? C3 C4 N1 Zr1 18.1(8) . . . . ? C5 C4 N1 Zr1 -161.5(4) . . . . ? O3 Zr1 N1 C4 120.9(5) 4_566 . . . ? O3 Zr1 N1 C4 12.6(6) . . . . ? O1 Zr1 N1 C4 -32.9(5) . . . . ? O1 Zr1 N1 C4 -154.3(5) 4_566 . . . ? N1 Zr1 N1 C4 -93.8(5) 4_566 . . . ? N2 Zr1 N1 C4 47.2(5) . . . . ? N2 Zr1 N1 C4 164.3(4) 4_566 . . . ? O3 Zr1 N1 C6 -49.9(4) 4_566 . . . ? O3 Zr1 N1 C6 -158.2(3) . . . . ? O1 Zr1 N1 C6 156.3(4) . . . . ? O1 Zr1 N1 C6 34.9(4) 4_566 . . . ? N1 Zr1 N1 C6 95.4(4) 4_566 . . . ? N2 Zr1 N1 C6 -123.7(4) . . . . ? N2 Zr1 N1 C6 -6.5(5) 4_566 . . . ? C4 N1 C6 C7 85.1(7) . . . . ? Zr1 N1 C6 C7 -102.7(6) . . . . ? N1 C6 C7 O2 168.9(5) . . . . ? C6 C7 O2 C8 177.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.050 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.105 _database_code_depnum_ccdc_archive 'CCDC 957075' ####################################################################### # # 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_cvd422 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H70 N2 O10 Zr2' _chemical_formula_weight 849.36 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' Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9999(8) _cell_length_b 10.4571(8) _cell_length_c 12.1982(12) _cell_angle_alpha 110.312(8) _cell_angle_beta 96.841(7) _cell_angle_gamma 113.111(7) _cell_volume 1050.92(16) _cell_formula_units_Z 1 _cell_measurement_temperature 111(2) _cell_measurement_reflns_used 1059 _cell_measurement_theta_min 3.235 _cell_measurement_theta_max 26.306 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.546 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.950 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details abspack _exptl_special_details ; ? ; _diffrn_ambient_temperature 111(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Sapphire2-CCD, Oxford Diffraction' _diffrn_measurement_method '501 images at 1.0 deg. in \w and 60 sec.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8218 _diffrn_reflns_av_R_equivalents 0.0816 _diffrn_reflns_av_sigmaI/netI 0.1348 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3908 _reflns_number_gt 2775 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro 1.171.35.11, Agilent Techn.' _computing_cell_refinement 'CrysAlisPro 1.171.35.11, Agilent Techn.' _computing_data_reduction 'CrysAlisPro 1.171.35.11, Agilent Techn.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0439P)^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 3908 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1107 _refine_ls_R_factor_gt 0.0691 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1231 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 Zr1 Zr -0.03159(7) 0.92985(7) 0.33820(5) 0.0233(2) Uani 1 1 d . . . O1 O -0.1802(5) 0.7193(4) 0.2970(4) 0.0402(12) Uani 1 1 d . . . N1 N 0.1962(6) 1.1381(6) 0.3618(5) 0.0388(14) Uani 1 1 d . . . C1 C -0.2571(11) 0.5668(8) 0.2096(8) 0.085(3) Uani 1 1 d . . . H1A H -0.2099 0.5740 0.1428 0.102 Uiso 1 1 calc R . . O2 O 0.1058(4) 0.9653(4) 0.5123(3) 0.0264(9) Uani 1 1 d . . . C2 C -0.2043(9) 0.4680(8) 0.2454(7) 0.061(2) Uani 1 1 d . . . H2A H -0.0946 0.5080 0.2569 0.092 Uiso 1 1 calc R . . H2B H -0.2583 0.3622 0.1808 0.092 Uiso 1 1 calc R . . H2C H -0.2253 0.4688 0.3220 0.092 Uiso 1 1 calc R . . O3 O -0.1337(4) 0.9728(4) 0.2214(3) 0.0294(10) Uani 1 1 d . . . C3 C -0.4047(11) 0.5109(10) 0.1512(10) 0.120(4) Uani 1 1 d . . . H3A H -0.4644 0.5039 0.2090 0.180 Uiso 1 1 calc R . . H3B H -0.4416 0.4083 0.0846 0.180 Uiso 1 1 calc R . . H3C H -0.4157 0.5799 0.1174 0.180 Uiso 1 1 calc R . . O4 O 0.0725(5) 0.8265(5) 0.2267(4) 0.0394(11) Uani 1 1 d . . . C4 C 0.2388(7) 0.9399(8) 0.5164(6) 0.0352(16) Uani 1 1 d . . . H4 H 0.2539 0.9164 0.4334 0.042 Uiso 1 1 calc R . . O5 O 0.2620(6) 1.4234(6) 0.3188(5) 0.0571(14) Uani 1 1 d . . . C5 C 0.2062(8) 0.7987(8) 0.5389(7) 0.052(2) Uani 1 1 d . . . H5A H 0.1938 0.8187 0.6207 0.078 Uiso 1 1 calc R . . H5B H 0.2912 0.7746 0.5332 0.078 Uiso 1 1 calc R . . H5C H 0.1126 0.7112 0.4774 0.078 Uiso 1 1 calc R . . C6 C 0.3787(7) 1.0824(8) 0.6054(6) 0.0452(18) Uani 1 1 d . . . H6A H 0.3913 1.1680 0.5845 0.068 Uiso 1 1 calc R . . H6B H 0.4677 1.0648 0.6018 0.068 Uiso 1 1 calc R . . H6C H 0.3688 1.1077 0.6883 0.068 Uiso 1 1 calc R . . C7 C -0.1802(7) 0.9803(7) 0.1100(5) 0.0347(16) Uani 1 1 d . . . H7 H -0.1063 1.0816 0.1153 0.042 Uiso 1 1 calc R . . C8 C -0.3335(8) 0.9713(9) 0.0909(6) 0.050(2) Uani 1 1 d . . . H8A H -0.4078 0.8727 0.0856 0.075 Uiso 1 1 calc R . . H8B H -0.3621 0.9792 0.0147 0.075 Uiso 1 1 calc R . . H8C H -0.3320 1.0561 0.1597 0.075 Uiso 1 1 calc R . . C9 C -0.1739(8) 0.8540(8) 0.0062(6) 0.0454(18) Uani 1 1 d . . . H9A H -0.0702 0.8660 0.0216 0.068 Uiso 1 1 calc R . . H9B H -0.2028 0.8603 -0.0707 0.068 Uiso 1 1 calc R . . H9C H -0.2446 0.7535 0.0003 0.068 Uiso 1 1 calc R . . C10 C 0.1907(10) 0.7250(9) 0.0912(6) 0.070(3) Uani 1 1 d . . . H10A H 0.1730 0.6424 0.1172 0.105 Uiso 1 1 calc R . . H10B H 0.2888 0.7575 0.0739 0.105 Uiso 1 1 calc R . . H10C H 0.1091 0.6871 0.0171 0.105 Uiso 1 1 calc R . . C11 C 0.1922(8) 0.8560(8) 0.1887(6) 0.0418(17) Uani 1 1 d . . . C12 C 0.3115(8) 1.0019(8) 0.2351(7) 0.0488(19) Uani 1 1 d . . . H12 H 0.3978 1.0138 0.2064 0.059 Uiso 1 1 calc R . . C13 C 0.3164(8) 1.1391(9) 0.3245(7) 0.0458(19) Uani 1 1 d . . . C14 C 0.4662(8) 1.2851(8) 0.3706(8) 0.063(2) Uani 1 1 d . . . H14A H 0.4484 1.3646 0.3567 0.094 Uiso 1 1 calc R . . H14B H 0.5364 1.2637 0.3265 0.094 Uiso 1 1 calc R . . H14C H 0.5107 1.3212 0.4583 0.094 Uiso 1 1 calc R . . C15 C 0.2072(8) 1.2844(7) 0.4417(6) 0.050(2) Uani 1 1 d . . . H15A H 0.3144 1.3549 0.4925 0.060 Uiso 1 1 calc R . . H15B H 0.1450 1.2672 0.4975 0.060 Uiso 1 1 calc R . . C16 C 0.1550(7) 1.3616(7) 0.3740(6) 0.0394(17) Uani 1 1 d . . . H16A H 0.0563 1.2853 0.3107 0.047 Uiso 1 1 calc R . . H16B H 0.1400 1.4447 0.4321 0.047 Uiso 1 1 calc R . . C17 C 0.2117(9) 1.4860(9) 0.2452(7) 0.063(2) Uani 1 1 d . . . H17A H 0.1164 1.4053 0.1815 0.095 Uiso 1 1 calc R . . H17B H 0.2894 1.5251 0.2069 0.095 Uiso 1 1 calc R . . H17C H 0.1948 1.5704 0.2967 0.095 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 Zr1 0.0262(3) 0.0189(3) 0.0187(3) 0.0028(2) 0.0068(2) 0.0093(2) O1 0.036(3) 0.022(2) 0.044(3) 0.007(2) 0.006(2) 0.003(2) N1 0.035(3) 0.030(3) 0.043(3) 0.015(3) 0.000(3) 0.010(3) C1 0.097(8) 0.016(4) 0.080(6) -0.004(4) -0.028(6) 0.004(4) O2 0.027(2) 0.029(2) 0.022(2) 0.0041(18) 0.0083(18) 0.0173(19) C2 0.087(6) 0.036(4) 0.054(5) 0.011(4) 0.025(5) 0.029(4) O3 0.028(2) 0.038(2) 0.018(2) 0.0087(19) 0.0060(18) 0.014(2) C3 0.086(8) 0.040(5) 0.142(10) -0.008(6) -0.051(7) 0.008(5) O4 0.044(3) 0.050(3) 0.039(3) 0.021(2) 0.022(2) 0.031(2) C4 0.035(4) 0.058(4) 0.022(3) 0.014(3) 0.010(3) 0.032(4) O5 0.068(4) 0.058(3) 0.059(3) 0.035(3) 0.020(3) 0.033(3) C5 0.058(5) 0.056(5) 0.049(5) 0.013(4) 0.013(4) 0.043(4) C6 0.031(4) 0.065(5) 0.039(4) 0.020(4) 0.012(3) 0.024(4) C7 0.041(4) 0.036(4) 0.026(4) 0.010(3) 0.010(3) 0.020(3) C8 0.057(5) 0.075(5) 0.029(4) 0.017(4) 0.011(4) 0.046(4) C9 0.051(5) 0.052(4) 0.027(4) 0.008(3) 0.007(3) 0.027(4) C10 0.122(8) 0.081(6) 0.040(5) 0.023(5) 0.037(5) 0.076(6) C11 0.053(5) 0.053(5) 0.033(4) 0.021(4) 0.016(4) 0.035(4) C12 0.054(5) 0.050(5) 0.061(5) 0.033(4) 0.026(4) 0.032(4) C13 0.032(4) 0.061(5) 0.064(5) 0.044(4) 0.017(4) 0.024(4) C14 0.045(5) 0.049(5) 0.094(7) 0.043(5) 0.009(4) 0.014(4) C15 0.051(5) 0.032(4) 0.046(5) 0.006(3) -0.006(4) 0.016(4) C16 0.046(4) 0.033(4) 0.032(4) 0.006(3) 0.013(3) 0.018(3) C17 0.097(7) 0.064(5) 0.057(5) 0.033(5) 0.025(5) 0.057(5) _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 Zr1 O3 1.932(4) . ? Zr1 O1 1.948(4) . ? Zr1 O4 2.074(4) . ? Zr1 O2 2.157(4) 2_576 ? Zr1 O2 2.212(4) . ? Zr1 N1 2.351(5) . ? Zr1 Zr1 3.5764(12) 2_576 ? O1 C1 1.390(7) . ? N1 C13 1.333(8) . ? N1 C15 1.453(8) . ? C1 C3 1.346(11) . ? C1 C2 1.491(10) . ? C1 H1A 1.0000 . ? O2 C4 1.453(7) . ? O2 Zr1 2.157(4) 2_576 ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? O3 C7 1.421(7) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? O4 C11 1.299(7) . ? C4 C6 1.495(8) . ? C4 C5 1.513(9) . ? C4 H4 1.0000 . ? O5 C16 1.394(7) . ? O5 C17 1.431(8) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.483(8) . ? C7 C9 1.509(8) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.463(9) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.372(9) . ? C12 C13 1.447(10) . ? C12 H12 0.9500 . ? C13 C14 1.516(9) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.515(9) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 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 O3 Zr1 O1 100.73(17) . . ? O3 Zr1 O4 97.72(17) . . ? O1 Zr1 O4 84.59(18) . . ? O3 Zr1 O2 95.86(15) . 2_576 ? O1 Zr1 O2 95.00(16) . 2_576 ? O4 Zr1 O2 166.25(16) . 2_576 ? O3 Zr1 O2 159.85(15) . . ? O1 Zr1 O2 95.01(16) . . ? O4 Zr1 O2 96.20(15) . . ? O2 Zr1 O2 70.12(16) 2_576 . ? O3 Zr1 N1 87.87(17) . . ? O1 Zr1 N1 159.80(19) . . ? O4 Zr1 N1 76.10(18) . . ? O2 Zr1 N1 102.33(17) 2_576 . ? O2 Zr1 N1 81.41(16) . . ? O3 Zr1 Zr1 129.96(12) . 2_576 ? O1 Zr1 Zr1 96.12(13) . 2_576 ? O4 Zr1 Zr1 130.74(12) . 2_576 ? O2 Zr1 Zr1 35.57(10) 2_576 2_576 ? O2 Zr1 Zr1 34.55(9) . 2_576 ? N1 Zr1 Zr1 92.09(13) . 2_576 ? C1 O1 Zr1 146.9(5) . . ? C13 N1 C15 118.1(6) . . ? C13 N1 Zr1 130.1(5) . . ? C15 N1 Zr1 111.3(4) . . ? C3 C1 O1 117.5(8) . . ? C3 C1 C2 120.2(8) . . ? O1 C1 C2 111.6(7) . . ? C3 C1 H1A 101.0 . . ? O1 C1 H1A 101.0 . . ? C2 C1 H1A 101.0 . . ? C4 O2 Zr1 129.0(3) . 2_576 ? C4 O2 Zr1 120.5(3) . . ? Zr1 O2 Zr1 109.88(16) 2_576 . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C7 O3 Zr1 159.2(4) . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C11 O4 Zr1 142.9(4) . . ? O2 C4 C6 111.1(5) . . ? O2 C4 C5 109.1(5) . . ? C6 C4 C5 114.7(5) . . ? O2 C4 H4 107.2 . . ? C6 C4 H4 107.2 . . ? C5 C4 H4 107.2 . . ? C16 O5 C17 112.7(6) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O3 C7 C8 111.0(5) . . ? O3 C7 C9 108.9(5) . . ? C8 C7 C9 112.3(5) . . ? O3 C7 H7 108.2 . . ? C8 C7 H7 108.2 . . ? C9 C7 H7 108.2 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O4 C11 C12 122.0(7) . . ? O4 C11 C10 116.0(7) . . ? C12 C11 C10 122.0(7) . . ? C11 C12 C13 125.3(7) . . ? C11 C12 H12 117.4 . . ? C13 C12 H12 117.4 . . ? N1 C13 C12 122.2(6) . . ? N1 C13 C14 122.1(7) . . ? C12 C13 C14 115.6(6) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 C16 113.8(6) . . ? N1 C15 H15A 108.8 . . ? C16 C15 H15A 108.8 . . ? N1 C15 H15B 108.8 . . ? C16 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? O5 C16 C15 110.8(6) . . ? O5 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? O5 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? O5 C17 H17A 109.5 . . ? O5 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O5 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 O3 Zr1 O1 C1 64.5(9) . . . . ? O4 Zr1 O1 C1 -32.3(9) . . . . ? O2 Zr1 O1 C1 161.5(9) 2_576 . . . ? O2 Zr1 O1 C1 -128.1(9) . . . . ? N1 Zr1 O1 C1 -49.4(11) . . . . ? Zr1 Zr1 O1 C1 -162.8(9) 2_576 . . . ? O3 Zr1 N1 C13 -108.3(6) . . . . ? O1 Zr1 N1 C13 7.7(9) . . . . ? O4 Zr1 N1 C13 -9.8(6) . . . . ? O2 Zr1 N1 C13 156.1(6) 2_576 . . . ? O2 Zr1 N1 C13 88.8(6) . . . . ? Zr1 Zr1 N1 C13 121.7(6) 2_576 . . . ? O3 Zr1 N1 C15 79.3(4) . . . . ? O1 Zr1 N1 C15 -164.7(5) . . . . ? O4 Zr1 N1 C15 177.8(4) . . . . ? O2 Zr1 N1 C15 -16.2(4) 2_576 . . . ? O2 Zr1 N1 C15 -83.5(4) . . . . ? Zr1 Zr1 N1 C15 -50.6(4) 2_576 . . . ? Zr1 O1 C1 C3 -105.9(12) . . . . ? Zr1 O1 C1 C2 109.5(9) . . . . ? O3 Zr1 O2 C4 -123.5(5) . . . . ? O1 Zr1 O2 C4 95.1(4) . . . . ? O4 Zr1 O2 C4 10.0(4) . . . . ? O2 Zr1 O2 C4 -171.4(5) 2_576 . . . ? N1 Zr1 O2 C4 -64.9(4) . . . . ? Zr1 Zr1 O2 C4 -171.4(5) 2_576 . . . ? O3 Zr1 O2 Zr1 47.9(5) . . . 2_576 ? O1 Zr1 O2 Zr1 -93.51(19) . . . 2_576 ? O4 Zr1 O2 Zr1 -178.60(18) . . . 2_576 ? O2 Zr1 O2 Zr1 0.0 2_576 . . 2_576 ? N1 Zr1 O2 Zr1 106.5(2) . . . 2_576 ? O1 Zr1 O3 C7 -87.9(10) . . . . ? O4 Zr1 O3 C7 -2.0(10) . . . . ? O2 Zr1 O3 C7 175.8(10) 2_576 . . . ? O2 Zr1 O3 C7 131.3(10) . . . . ? N1 Zr1 O3 C7 73.7(10) . . . . ? Zr1 Zr1 O3 C7 164.6(10) 2_576 . . . ? O3 Zr1 O4 C11 85.0(7) . . . . ? O1 Zr1 O4 C11 -174.9(7) . . . . ? O2 Zr1 O4 C11 -86.0(10) 2_576 . . . ? O2 Zr1 O4 C11 -80.4(7) . . . . ? N1 Zr1 O4 C11 -0.9(7) . . . . ? Zr1 Zr1 O4 C11 -81.5(7) 2_576 . . . ? Zr1 O2 C4 C6 -47.8(7) 2_576 . . . ? Zr1 O2 C4 C6 121.8(4) . . . . ? Zr1 O2 C4 C5 79.6(6) 2_576 . . . ? Zr1 O2 C4 C5 -110.8(5) . . . . ? Zr1 O3 C7 C8 150.7(8) . . . . ? Zr1 O3 C7 C9 26.6(13) . . . . ? Zr1 O4 C11 C12 6.7(11) . . . . ? Zr1 O4 C11 C10 -171.9(5) . . . . ? O4 C11 C12 C13 -3.6(11) . . . . ? C10 C11 C12 C13 174.9(7) . . . . ? C15 N1 C13 C12 -173.6(6) . . . . ? Zr1 N1 C13 C12 14.5(10) . . . . ? C15 N1 C13 C14 4.9(9) . . . . ? Zr1 N1 C13 C14 -167.0(5) . . . . ? C11 C12 C13 N1 -6.8(11) . . . . ? C11 C12 C13 C14 174.6(6) . . . . ? C13 N1 C15 C16 90.6(7) . . . . ? Zr1 N1 C15 C16 -96.0(6) . . . . ? C17 O5 C16 C15 175.0(5) . . . . ? N1 C15 C16 O5 -73.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.910 _refine_diff_density_min -0.766 _refine_diff_density_rms 0.115 #=================================END _database_code_depnum_ccdc_archive 'CCDC 957079'