# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_laphomono _database_code_depnum_ccdc_archive 'CCDC 882769' #TrackingRef '11386_web_deposit_cif_file_0_LuisG.Alves_1337339488.CIF(LuisAlves).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H44 N4 O2 Zr' _chemical_formula_sum 'C36 H44 N4 O2 Zr' _chemical_formula_weight 655.97 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.535(3) _cell_length_b 10.400(4) _cell_length_c 33.062(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.640(18) _cell_angle_gamma 90.00 _cell_volume 3277(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2489 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 21.03 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9637 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29503 _diffrn_reflns_av_R_equivalents 0.2414 _diffrn_reflns_av_sigmaI/netI 0.1736 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5853 _reflns_number_gt 2699 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2\s(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^)+(0.1772P)^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 5853 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1772 _refine_ls_R_factor_gt 0.0846 _refine_ls_wR_factor_ref 0.2990 _refine_ls_wR_factor_gt 0.2141 _refine_ls_goodness_of_fit_ref 0.903 _refine_ls_restrained_S_all 0.903 _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 0.77689(9) 0.27659(8) 0.61232(3) 0.0414(3) Uani 1 1 d . . . N3 N 0.9527(7) 0.4368(6) 0.6360(2) 0.0401(17) Uani 1 1 d . . . O1 O 0.6155(6) 0.1595(6) 0.6281(2) 0.0598(18) Uani 1 1 d . . . N1 N 0.8088(7) 0.0831(7) 0.5689(2) 0.0472(19) Uani 1 1 d . . . C12 C 0.6815(9) -0.0279(9) 0.5084(3) 0.050(2) Uani 1 1 d . . . C5 C 0.9589(10) 0.5575(8) 0.6122(3) 0.051(2) Uani 1 1 d . . . H5A H 1.0376 0.6099 0.6233 0.061 Uiso 1 1 calc R . . H5B H 0.8714 0.6063 0.6165 0.061 Uiso 1 1 calc R . . N2 N 0.8395(7) 0.3394(7) 0.5554(2) 0.0434(18) Uani 1 1 d . . . C11 C 0.6768(9) 0.0697(9) 0.5428(3) 0.051(2) Uani 1 1 d . . . H11A H 0.6541 0.1549 0.5311 0.062 Uiso 1 1 calc R . . H11B H 0.5990 0.0458 0.5605 0.062 Uiso 1 1 calc R . . C24 C 1.1403(9) 0.5124(9) 0.7210(3) 0.047(2) Uani 1 1 d . . . H24 H 1.1611 0.4232 0.7194 0.056 Uiso 1 1 calc R . . C19 C 1.0192(10) 0.5566(8) 0.7024(3) 0.046(2) Uani 1 1 d . . . O2 O 0.6586(6) 0.4351(6) 0.6231(2) 0.0569(17) Uani 1 1 d . . . C10 C 0.8391(9) -0.0405(9) 0.5893(3) 0.046(2) Uani 1 1 d . . . H10A H 0.8651 -0.1037 0.5684 0.055 Uiso 1 1 calc R . . H10B H 0.7513 -0.0714 0.6013 0.055 Uiso 1 1 calc R . . C1 C 0.9311(8) 0.1255(9) 0.5440(3) 0.044(2) Uani 1 1 d . . . H1A H 1.0181 0.1247 0.5611 0.053 Uiso 1 1 calc R . . H1B H 0.9434 0.0645 0.5214 0.053 Uiso 1 1 calc R . . C18 C 0.9171(9) 0.4679(8) 0.6794(2) 0.043(2) Uani 1 1 d . . . H18A H 0.9111 0.3861 0.6946 0.052 Uiso 1 1 calc R . . H18B H 0.8229 0.5080 0.6793 0.052 Uiso 1 1 calc R . . C25 C 0.5295(9) 0.1384(9) 0.6597(3) 0.048(2) Uani 1 1 d . . . C2 C 0.9070(10) 0.2568(9) 0.5276(3) 0.055(3) Uani 1 1 d . . . H2A H 0.9983 0.2950 0.5206 0.066 Uiso 1 1 calc R . . H2B H 0.8487 0.2508 0.5025 0.066 Uiso 1 1 calc R . . C9 C 0.9538(11) -0.0408(9) 0.6223(3) 0.060(3) Uani 1 1 d . . . H9A H 1.0428 -0.0115 0.6107 0.072 Uiso 1 1 calc R . . H9B H 0.9680 -0.1299 0.6322 0.072 Uiso 1 1 calc R . . N4 N 0.9282(8) 0.1855(7) 0.6485(2) 0.051(2) Uani 1 1 d . . . C13 C 0.6992(9) 0.0067(11) 0.4690(3) 0.060(3) Uani 1 1 d . . . H13 H 0.7157 0.0946 0.4629 0.072 Uiso 1 1 calc R . . C21 C 1.0774(11) 0.7688(9) 0.7281(3) 0.056(3) Uani 1 1 d . . . H21 H 1.0556 0.8576 0.7301 0.067 Uiso 1 1 calc R . . C20 C 0.9872(10) 0.6864(9) 0.7068(3) 0.052(2) Uani 1 1 d . . . H20 H 0.9024 0.7192 0.6951 0.063 Uiso 1 1 calc R . . C23 C 1.2335(10) 0.5916(9) 0.7418(3) 0.058(3) Uani 1 1 d . . . H23 H 1.3193 0.5587 0.7529 0.069 Uiso 1 1 calc R . . C30 C 0.4878(10) 0.2351(11) 0.6855(4) 0.062(3) Uani 1 1 d . . . H30 H 0.5167 0.3212 0.6809 0.074 Uiso 1 1 calc R . . C36 C 0.4912(9) 0.5242(10) 0.5767(3) 0.057(3) Uani 1 1 d . . . H36 H 0.5273 0.4731 0.5556 0.069 Uiso 1 1 calc R . . C14 C 0.6941(10) -0.0813(13) 0.4374(3) 0.075(4) Uani 1 1 d . . . H14 H 0.7086 -0.0544 0.4104 0.091 Uiso 1 1 calc R . . C31 C 0.5502(9) 0.5149(8) 0.6147(3) 0.050(2) Uani 1 1 d . . . C16 C 0.6483(13) -0.2452(12) 0.4851(5) 0.089(5) Uani 1 1 d . . . H16 H 0.6327 -0.3334 0.4910 0.107 Uiso 1 1 calc R . . C22 C 1.1989(11) 0.7210(9) 0.7462(3) 0.060(3) Uani 1 1 d . . . H22 H 1.2588 0.7763 0.7617 0.072 Uiso 1 1 calc R . . C26 C 0.4842(12) 0.0122(11) 0.6670(3) 0.072(3) Uani 1 1 d . . . H26 H 0.5114 -0.0555 0.6496 0.087 Uiso 1 1 calc R . . C15 C 0.6672(11) -0.2111(13) 0.4462(4) 0.078(4) Uani 1 1 d . . . H15 H 0.6624 -0.2735 0.4252 0.093 Uiso 1 1 calc R . . C17 C 0.6505(10) -0.1595(10) 0.5166(3) 0.060(3) Uani 1 1 d . . . H17 H 0.6318 -0.1870 0.5433 0.072 Uiso 1 1 calc R . . C3 C 0.8510(10) 0.4764(9) 0.5454(3) 0.052(2) Uani 1 1 d . . . H3A H 0.7638 0.5205 0.5532 0.063 Uiso 1 1 calc R . . H3B H 0.8591 0.4853 0.5157 0.063 Uiso 1 1 calc R . . C32 C 0.4906(11) 0.5869(10) 0.6458(4) 0.064(3) Uani 1 1 d . . . H32 H 0.5264 0.5805 0.6728 0.077 Uiso 1 1 calc R . . C8 C 0.9188(12) 0.0465(9) 0.6585(3) 0.069(3) Uani 1 1 d . . . H8A H 0.8227 0.0270 0.6672 0.083 Uiso 1 1 calc R . . H8B H 0.9845 0.0272 0.6814 0.083 Uiso 1 1 calc R . . C7 C 1.0715(9) 0.2347(8) 0.6555(3) 0.048(2) Uani 1 1 d . . . H7A H 1.1403 0.1730 0.6448 0.058 Uiso 1 1 calc R . . H7B H 1.0911 0.2454 0.6849 0.058 Uiso 1 1 calc R . . C4 C 0.9771(10) 0.5435(9) 0.5664(3) 0.055(2) Uani 1 1 d . . . H4A H 1.0632 0.4933 0.5616 0.066 Uiso 1 1 calc R . . H4B H 0.9891 0.6298 0.5544 0.066 Uiso 1 1 calc R . . C6 C 1.0846(9) 0.3622(9) 0.6343(3) 0.051(2) Uani 1 1 d . . . H6A H 1.1619 0.4123 0.6473 0.061 Uiso 1 1 calc R . . H6B H 1.1082 0.3476 0.6057 0.061 Uiso 1 1 calc R . . C33 C 0.3756(13) 0.6698(11) 0.6361(5) 0.083(4) Uani 1 1 d . . . H33 H 0.3336 0.7199 0.6565 0.099 Uiso 1 1 calc R . . C28 C 0.3601(12) 0.0823(15) 0.7248(4) 0.088(4) Uani 1 1 d . . . H28 H 0.3023 0.0636 0.7470 0.105 Uiso 1 1 calc R . . C35 C 0.3806(12) 0.6058(14) 0.5683(5) 0.087(4) Uani 1 1 d . . . H35 H 0.3438 0.6104 0.5414 0.104 Uiso 1 1 calc R . . C34 C 0.3251(14) 0.6761(13) 0.5956(6) 0.087(4) Uani 1 1 d . . . H34 H 0.2500 0.7325 0.5885 0.105 Uiso 1 1 calc R . . C29 C 0.4032(11) 0.2067(13) 0.7181(4) 0.071(3) Uani 1 1 d . . . H29 H 0.3754 0.2734 0.7358 0.085 Uiso 1 1 calc R . . C27 C 0.3998(15) -0.0145(15) 0.6996(4) 0.105(5) Uani 1 1 d . . . H27 H 0.3698 -0.1001 0.7044 0.126 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 0.0391(5) 0.0423(5) 0.0423(5) 0.0039(4) -0.0058(4) -0.0015(4) N3 0.040(4) 0.045(4) 0.035(4) -0.002(3) -0.007(3) 0.000(3) O1 0.051(4) 0.058(4) 0.071(5) 0.002(4) 0.003(3) -0.016(3) N1 0.043(4) 0.054(5) 0.045(4) -0.002(4) -0.013(3) 0.005(3) C12 0.036(5) 0.054(6) 0.060(6) -0.006(5) -0.013(4) -0.003(4) C5 0.057(6) 0.041(5) 0.054(6) 0.002(4) 0.001(5) -0.015(4) N2 0.041(4) 0.044(4) 0.045(4) 0.011(4) -0.004(3) -0.007(3) C11 0.040(5) 0.052(5) 0.061(6) -0.012(5) -0.008(5) -0.001(4) C24 0.061(6) 0.043(5) 0.036(5) 0.001(4) -0.010(4) -0.001(4) C19 0.065(6) 0.044(5) 0.031(5) 0.004(4) -0.001(4) -0.004(4) O2 0.046(4) 0.057(4) 0.068(4) 0.002(3) 0.000(3) 0.010(3) C10 0.052(5) 0.053(5) 0.033(5) -0.007(4) 0.004(4) 0.001(4) C1 0.025(4) 0.073(6) 0.035(5) 0.005(4) 0.022(4) -0.002(4) C18 0.052(5) 0.047(5) 0.031(4) 0.004(4) -0.003(4) 0.000(4) C25 0.044(5) 0.062(6) 0.038(5) 0.010(5) -0.001(4) -0.009(5) C2 0.046(5) 0.056(6) 0.061(6) -0.007(5) -0.014(5) -0.003(4) C9 0.072(7) 0.041(5) 0.064(7) 0.010(5) -0.026(5) 0.006(5) N4 0.057(5) 0.043(4) 0.052(5) 0.010(4) -0.012(4) -0.004(4) C13 0.036(5) 0.076(7) 0.067(7) -0.018(6) -0.006(5) -0.001(5) C21 0.088(8) 0.041(5) 0.038(5) -0.007(4) -0.003(5) 0.001(5) C20 0.063(6) 0.049(6) 0.044(6) 0.000(4) -0.007(5) 0.007(5) C23 0.056(6) 0.067(7) 0.049(6) -0.002(5) -0.010(5) 0.002(5) C30 0.048(6) 0.067(7) 0.070(7) 0.014(6) 0.003(5) 0.002(5) C36 0.041(5) 0.061(6) 0.070(7) -0.008(5) -0.002(5) 0.000(5) C14 0.047(6) 0.124(11) 0.054(7) -0.017(7) -0.016(5) -0.010(6) C31 0.039(5) 0.038(5) 0.071(7) -0.003(5) -0.010(5) 0.005(4) C16 0.074(8) 0.071(8) 0.118(12) -0.043(8) -0.053(8) 0.020(6) C22 0.072(7) 0.048(5) 0.058(6) 0.003(5) -0.008(5) -0.016(5) C26 0.084(8) 0.074(7) 0.062(7) -0.013(6) 0.029(6) -0.038(6) C15 0.046(6) 0.092(9) 0.094(10) -0.044(8) -0.018(6) -0.002(6) C17 0.053(6) 0.073(7) 0.053(6) 0.006(6) -0.011(5) -0.007(5) C3 0.060(6) 0.051(6) 0.046(5) 0.013(5) -0.010(5) -0.009(5) C32 0.063(7) 0.059(6) 0.071(7) -0.012(6) 0.010(6) 0.003(5) C8 0.083(8) 0.056(6) 0.066(7) 0.027(6) -0.027(6) -0.006(6) C7 0.049(5) 0.051(5) 0.045(5) -0.003(4) -0.015(4) 0.003(4) C4 0.064(6) 0.054(6) 0.046(6) 0.004(5) -0.001(5) -0.013(5) C6 0.040(5) 0.062(6) 0.049(5) -0.011(5) -0.006(4) 0.000(4) C33 0.076(8) 0.056(6) 0.120(12) -0.016(7) 0.064(8) 0.003(6) C28 0.062(8) 0.129(12) 0.072(8) 0.023(9) 0.011(6) -0.014(8) C35 0.050(7) 0.109(11) 0.100(10) 0.028(9) -0.012(7) 0.001(7) C34 0.068(8) 0.069(8) 0.124(13) 0.028(9) -0.009(8) 0.010(7) C29 0.060(7) 0.094(9) 0.060(7) 0.006(7) 0.008(6) 0.016(6) C27 0.119(12) 0.102(11) 0.095(10) -0.012(9) 0.034(9) -0.062(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O2 2.035(6) . ? Zr1 O1 2.042(6) . ? Zr1 N4 2.077(7) . ? Zr1 N2 2.095(7) . ? Zr1 N3 2.474(7) . ? Zr1 N1 2.496(7) . ? N3 C6 1.480(11) . ? N3 C5 1.484(11) . ? N3 C18 1.520(11) . ? O1 C25 1.363(11) . ? N1 C10 1.476(11) . ? N1 C11 1.512(10) . ? N1 C1 1.512(10) . ? C12 C13 1.367(14) . ? C12 C17 1.427(13) . ? C12 C11 1.528(13) . ? C5 C4 1.535(13) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? N2 C2 1.425(12) . ? N2 C3 1.468(11) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C24 C19 1.371(11) . ? C24 C23 1.382(12) . ? C24 H24 0.9500 . ? C19 C20 1.393(12) . ? C19 C18 1.528(12) . ? O2 C31 1.348(10) . ? C10 C9 1.524(11) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C1 C2 1.485(12) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C25 C30 1.385(14) . ? C25 C26 1.405(14) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C9 C8 1.546(15) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N4 C7 1.471(11) . ? N4 C8 1.486(12) . ? C13 C14 1.387(14) . ? C13 H13 0.9500 . ? C21 C22 1.382(14) . ? C21 C20 1.390(13) . ? C21 H21 0.9500 . ? C20 H20 0.9500 . ? C23 C22 1.394(13) . ? C23 H23 0.9500 . ? C30 C29 1.398(16) . ? C30 H30 0.9500 . ? C36 C31 1.366(13) . ? C36 C35 1.375(15) . ? C36 H36 0.9500 . ? C14 C15 1.406(17) . ? C14 H14 0.9500 . ? C31 C32 1.404(14) . ? C16 C15 1.35(2) . ? C16 C17 1.369(16) . ? C16 H16 0.9500 . ? C22 H22 0.9500 . ? C26 C27 1.392(17) . ? C26 H26 0.9500 . ? C15 H15 0.9500 . ? C17 H17 0.9500 . ? C3 C4 1.539(12) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C32 C33 1.424(16) . ? C32 H32 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C7 C6 1.506(13) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C33 C34 1.411(19) . ? C33 H33 0.9500 . ? C28 C27 1.366(18) . ? C28 C29 1.378(17) . ? C28 H28 0.9500 . ? C35 C34 1.287(19) . ? C35 H35 0.9500 . ? C34 H34 0.9500 . ? C29 H29 0.9500 . ? C27 H27 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zr1 O1 90.7(3) . . ? O2 Zr1 N4 130.4(3) . . ? O1 Zr1 N4 95.6(3) . . ? O2 Zr1 N2 94.5(3) . . ? O1 Zr1 N2 130.7(3) . . ? N4 Zr1 N2 116.7(3) . . ? O2 Zr1 N3 76.9(2) . . ? O1 Zr1 N3 146.0(3) . . ? N4 Zr1 N3 70.8(3) . . ? N2 Zr1 N3 82.3(2) . . ? O2 Zr1 N1 146.2(2) . . ? O1 Zr1 N1 76.8(3) . . ? N4 Zr1 N1 82.5(3) . . ? N2 Zr1 N1 72.1(3) . . ? N3 Zr1 N1 129.2(2) . . ? C6 N3 C5 112.1(7) . . ? C6 N3 C18 111.1(6) . . ? C5 N3 C18 109.5(6) . . ? C6 N3 Zr1 101.8(5) . . ? C5 N3 Zr1 116.0(5) . . ? C18 N3 Zr1 106.0(5) . . ? C25 O1 Zr1 140.0(6) . . ? C10 N1 C11 109.2(7) . . ? C10 N1 C1 111.0(7) . . ? C11 N1 C1 111.0(7) . . ? C10 N1 Zr1 117.7(5) . . ? C11 N1 Zr1 106.8(5) . . ? C1 N1 Zr1 100.7(5) . . ? C13 C12 C17 117.8(9) . . ? C13 C12 C11 122.9(9) . . ? C17 C12 C11 119.0(9) . . ? N3 C5 C4 116.8(7) . . ? N3 C5 H5A 108.1 . . ? C4 C5 H5A 108.1 . . ? N3 C5 H5B 108.1 . . ? C4 C5 H5B 108.1 . . ? H5A C5 H5B 107.3 . . ? C2 N2 C3 113.7(8) . . ? C2 N2 Zr1 122.5(6) . . ? C3 N2 Zr1 122.0(6) . . ? N1 C11 C12 116.4(7) . . ? N1 C11 H11A 108.2 . . ? C12 C11 H11A 108.2 . . ? N1 C11 H11B 108.2 . . ? C12 C11 H11B 108.2 . . ? H11A C11 H11B 107.3 . . ? C19 C24 C23 123.0(9) . . ? C19 C24 H24 118.5 . . ? C23 C24 H24 118.5 . . ? C24 C19 C20 117.6(8) . . ? C24 C19 C18 122.4(8) . . ? C20 C19 C18 119.9(8) . . ? C31 O2 Zr1 152.8(6) . . ? N1 C10 C9 117.2(7) . . ? N1 C10 H10A 108.0 . . ? C9 C10 H10A 108.0 . . ? N1 C10 H10B 108.0 . . ? C9 C10 H10B 108.0 . . ? H10A C10 H10B 107.3 . . ? C2 C1 N1 110.7(7) . . ? C2 C1 H1A 109.5 . . ? N1 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? N3 C18 C19 116.3(7) . . ? N3 C18 H18A 108.2 . . ? C19 C18 H18A 108.2 . . ? N3 C18 H18B 108.2 . . ? C19 C18 H18B 108.2 . . ? H18A C18 H18B 107.4 . . ? O1 C25 C30 123.0(9) . . ? O1 C25 C26 118.5(9) . . ? C30 C25 C26 118.5(9) . . ? N2 C2 C1 112.8(9) . . ? N2 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N2 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C10 C9 C8 112.7(8) . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C7 N4 C8 111.5(7) . . ? C7 N4 Zr1 123.9(5) . . ? C8 N4 Zr1 121.7(6) . . ? C12 C13 C14 122.7(11) . . ? C12 C13 H13 118.7 . . ? C14 C13 H13 118.7 . . ? C22 C21 C20 119.8(9) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C20 C19 121.0(9) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C24 C23 C22 118.5(9) . . ? C24 C23 H23 120.8 . . ? C22 C23 H23 120.8 . . ? C25 C30 C29 120.3(10) . . ? C25 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C31 C36 C35 121.4(11) . . ? C31 C36 H36 119.3 . . ? C35 C36 H36 119.3 . . ? C13 C14 C15 118.7(12) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? O2 C31 C36 121.6(9) . . ? O2 C31 C32 120.2(9) . . ? C36 C31 C32 118.1(9) . . ? C15 C16 C17 123.6(13) . . ? C15 C16 H16 118.2 . . ? C17 C16 H16 118.2 . . ? C21 C22 C23 120.0(9) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C27 C26 C25 120.5(12) . . ? C27 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C16 C15 C14 118.6(11) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C16 C17 C12 118.6(11) . . ? C16 C17 H17 120.7 . . ? C12 C17 H17 120.7 . . ? N2 C3 C4 113.6(7) . . ? N2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? N2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C31 C32 C33 118.9(11) . . ? C31 C32 H32 120.5 . . ? C33 C32 H32 120.5 . . ? N4 C8 C9 112.6(9) . . ? N4 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N4 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? N4 C7 C6 108.9(7) . . ? N4 C7 H7A 109.9 . . ? C6 C7 H7A 109.9 . . ? N4 C7 H7B 109.9 . . ? C6 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C5 C4 C3 112.3(8) . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.9 . . ? N3 C6 C7 111.2(7) . . ? N3 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N3 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C34 C33 C32 118.8(11) . . ? C34 C33 H33 120.6 . . ? C32 C33 H33 120.6 . . ? C27 C28 C29 120.4(12) . . ? C27 C28 H28 119.8 . . ? C29 C28 H28 119.8 . . ? C34 C35 C36 122.6(13) . . ? C34 C35 H35 118.7 . . ? C36 C35 H35 118.7 . . ? C35 C34 C33 120.2(12) . . ? C35 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? C28 C29 C30 120.2(12) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C28 C27 C26 120.1(12) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Zr1 N3 C6 179.9(5) . . . . ? O1 Zr1 N3 C6 108.7(6) . . . . ? N4 Zr1 N3 C6 38.1(5) . . . . ? N2 Zr1 N3 C6 -83.7(5) . . . . ? N1 Zr1 N3 C6 -24.4(6) . . . . ? O2 Zr1 N3 C5 -58.1(6) . . . . ? O1 Zr1 N3 C5 -129.3(6) . . . . ? N4 Zr1 N3 C5 160.1(7) . . . . ? N2 Zr1 N3 C5 38.4(6) . . . . ? N1 Zr1 N3 C5 97.7(6) . . . . ? O2 Zr1 N3 C18 63.7(5) . . . . ? O1 Zr1 N3 C18 -7.5(7) . . . . ? N4 Zr1 N3 C18 -78.1(5) . . . . ? N2 Zr1 N3 C18 160.1(5) . . . . ? N1 Zr1 N3 C18 -140.6(5) . . . . ? O2 Zr1 O1 C25 -55.8(9) . . . . ? N4 Zr1 O1 C25 75.0(9) . . . . ? N2 Zr1 O1 C25 -152.3(8) . . . . ? N3 Zr1 O1 C25 11.4(12) . . . . ? N1 Zr1 O1 C25 155.9(9) . . . . ? O2 Zr1 N1 C10 -133.9(6) . . . . ? O1 Zr1 N1 C10 -63.0(6) . . . . ? N4 Zr1 N1 C10 34.5(6) . . . . ? N2 Zr1 N1 C10 155.8(6) . . . . ? N3 Zr1 N1 C10 92.2(6) . . . . ? O2 Zr1 N1 C11 -10.8(8) . . . . ? O1 Zr1 N1 C11 60.1(6) . . . . ? N4 Zr1 N1 C11 157.7(6) . . . . ? N2 Zr1 N1 C11 -81.1(6) . . . . ? N3 Zr1 N1 C11 -144.7(5) . . . . ? O2 Zr1 N1 C1 105.2(6) . . . . ? O1 Zr1 N1 C1 176.1(5) . . . . ? N4 Zr1 N1 C1 -86.3(5) . . . . ? N2 Zr1 N1 C1 34.9(4) . . . . ? N3 Zr1 N1 C1 -28.7(5) . . . . ? C6 N3 C5 C4 63.0(10) . . . . ? C18 N3 C5 C4 -173.3(7) . . . . ? Zr1 N3 C5 C4 -53.4(9) . . . . ? O2 Zr1 N2 C2 -167.9(6) . . . . ? O1 Zr1 N2 C2 -73.1(7) . . . . ? N4 Zr1 N2 C2 52.0(7) . . . . ? N3 Zr1 N2 C2 116.0(6) . . . . ? N1 Zr1 N2 C2 -19.6(6) . . . . ? O2 Zr1 N2 C3 28.5(6) . . . . ? O1 Zr1 N2 C3 123.3(6) . . . . ? N4 Zr1 N2 C3 -111.6(6) . . . . ? N3 Zr1 N2 C3 -47.7(6) . . . . ? N1 Zr1 N2 C3 176.8(6) . . . . ? C10 N1 C11 C12 -62.2(10) . . . . ? C1 N1 C11 C12 60.5(10) . . . . ? Zr1 N1 C11 C12 169.5(7) . . . . ? C13 C12 C11 N1 -101.8(10) . . . . ? C17 C12 C11 N1 85.4(10) . . . . ? C23 C24 C19 C20 -3.2(15) . . . . ? C23 C24 C19 C18 179.9(9) . . . . ? O1 Zr1 O2 C31 -68.1(14) . . . . ? N4 Zr1 O2 C31 -166.0(13) . . . . ? N2 Zr1 O2 C31 62.9(13) . . . . ? N3 Zr1 O2 C31 143.9(14) . . . . ? N1 Zr1 O2 C31 -1.1(16) . . . . ? C11 N1 C10 C9 -170.0(8) . . . . ? C1 N1 C10 C9 67.2(10) . . . . ? Zr1 N1 C10 C9 -48.1(10) . . . . ? C10 N1 C1 C2 -173.2(7) . . . . ? C11 N1 C1 C2 65.1(9) . . . . ? Zr1 N1 C1 C2 -47.7(7) . . . . ? C6 N3 C18 C19 64.9(9) . . . . ? C5 N3 C18 C19 -59.5(9) . . . . ? Zr1 N3 C18 C19 174.7(6) . . . . ? C24 C19 C18 N3 -82.8(11) . . . . ? C20 C19 C18 N3 100.3(10) . . . . ? Zr1 O1 C25 C30 31.4(14) . . . . ? Zr1 O1 C25 C26 -146.9(8) . . . . ? C3 N2 C2 C1 163.1(7) . . . . ? Zr1 N2 C2 C1 -1.8(10) . . . . ? N1 C1 C2 N2 37.7(10) . . . . ? N1 C10 C9 C8 62.5(11) . . . . ? O2 Zr1 N4 C7 -75.9(8) . . . . ? O1 Zr1 N4 C7 -171.6(7) . . . . ? N2 Zr1 N4 C7 47.0(8) . . . . ? N3 Zr1 N4 C7 -23.6(7) . . . . ? N1 Zr1 N4 C7 112.5(7) . . . . ? O2 Zr1 N4 C8 125.0(8) . . . . ? O1 Zr1 N4 C8 29.2(9) . . . . ? N2 Zr1 N4 C8 -112.2(8) . . . . ? N3 Zr1 N4 C8 177.3(9) . . . . ? N1 Zr1 N4 C8 -46.6(8) . . . . ? C17 C12 C13 C14 -2.8(14) . . . . ? C11 C12 C13 C14 -175.6(8) . . . . ? C22 C21 C20 C19 -1.9(16) . . . . ? C24 C19 C20 C21 2.1(15) . . . . ? C18 C19 C20 C21 179.1(9) . . . . ? C19 C24 C23 C22 3.9(16) . . . . ? O1 C25 C30 C29 -177.9(9) . . . . ? C26 C25 C30 C29 0.4(14) . . . . ? C12 C13 C14 C15 1.1(15) . . . . ? Zr1 O2 C31 C36 -24.6(19) . . . . ? Zr1 O2 C31 C32 152.4(10) . . . . ? C35 C36 C31 O2 -180.0(9) . . . . ? C35 C36 C31 C32 3.0(15) . . . . ? C20 C21 C22 C23 2.6(16) . . . . ? C24 C23 C22 C21 -3.5(16) . . . . ? O1 C25 C26 C27 178.1(11) . . . . ? C30 C25 C26 C27 -0.3(16) . . . . ? C17 C16 C15 C14 1.7(18) . . . . ? C13 C14 C15 C16 -0.5(16) . . . . ? C15 C16 C17 C12 -3.4(16) . . . . ? C13 C12 C17 C16 3.8(13) . . . . ? C11 C12 C17 C16 176.9(8) . . . . ? C2 N2 C3 C4 -92.9(9) . . . . ? Zr1 N2 C3 C4 72.1(10) . . . . ? O2 C31 C32 C33 -179.6(9) . . . . ? C36 C31 C32 C33 -2.5(14) . . . . ? C7 N4 C8 C9 -87.6(9) . . . . ? Zr1 N4 C8 C9 73.9(10) . . . . ? C10 C9 C8 N4 -72.0(11) . . . . ? C8 N4 C7 C6 164.3(8) . . . . ? Zr1 N4 C7 C6 3.2(11) . . . . ? N3 C5 C4 C3 64.4(11) . . . . ? N2 C3 C4 C5 -69.7(11) . . . . ? C5 N3 C6 C7 -174.8(7) . . . . ? C18 N3 C6 C7 62.3(9) . . . . ? Zr1 N3 C6 C7 -50.2(7) . . . . ? N4 C7 C6 N3 35.8(10) . . . . ? C31 C32 C33 C34 0.3(16) . . . . ? C31 C36 C35 C34 -1.1(19) . . . . ? C36 C35 C34 C33 -1(2) . . . . ? C32 C33 C34 C35 2(2) . . . . ? C27 C28 C29 C30 0.3(18) . . . . ? C25 C30 C29 C28 -0.4(16) . . . . ? C29 C28 C27 C26 0(2) . . . . ? C25 C26 C27 C28 0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 1.485 _refine_diff_density_min -1.516 _refine_diff_density_rms 0.164 data_lazrclsph _database_code_depnum_ccdc_archive 'CCDC 882770' #TrackingRef '11386_web_deposit_cif_file_0_LuisG.Alves_1337339488.CIF(LuisAlves).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H44 N4 S2 Zr' _chemical_formula_sum 'C36 H44 N4 S2 Zr' _chemical_formula_weight 688.11 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' S S 0.1246 0.1234 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.1188(6) _cell_length_b 14.5903(5) _cell_length_c 20.5693(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.0200(10) _cell_angle_gamma 90.00 _cell_volume 4536.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8704 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 29.32 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.008 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.357 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8702 _exptl_absorpt_correction_T_max 0.9003 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 87286 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 33.62 _reflns_number_total 17901 _reflns_number_gt 11755 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2\s(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^)+(0.0781P)^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 17901 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1310 _refine_ls_wR_factor_gt 0.1234 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.08299(3) 0.27373(3) 0.81374(2) 0.03034(9) Uani 1 1 d . . . S2 S 0.27330(3) 0.14186(3) 0.84925(2) 0.03304(10) Uani 1 1 d . . . N1 N -0.03646(10) 0.09674(10) 0.81592(7) 0.0316(3) Uani 1 1 d . . . N3 N 0.22050(10) -0.00504(10) 0.74277(7) 0.0333(3) Uani 1 1 d . . . C25 C 0.17271(11) 0.33254(11) 0.77920(8) 0.0293(3) Uani 1 1 d . . . N2 N 0.09592(10) -0.01113(10) 0.85459(7) 0.0343(3) Uani 1 1 d . . . C30 C 0.20121(12) 0.31538(13) 0.71616(9) 0.0360(4) Uani 1 1 d . . . H30 H 0.1742 0.2679 0.6913 0.043 Uiso 1 1 calc R . . C5 C 0.26742(14) -0.07591(14) 0.78363(10) 0.0430(4) Uani 1 1 d . . . H5A H 0.3147 -0.0450 0.8094 0.052 Uiso 1 1 calc R . . H5B H 0.2964 -0.1200 0.7543 0.052 Uiso 1 1 calc R . . N4 N 0.08280(10) 0.09567(10) 0.70116(7) 0.0325(3) Uani 1 1 d . . . C31 C 0.25161(11) 0.19602(12) 0.92374(8) 0.0310(3) Uani 1 1 d . . . C10 C -0.09608(12) 0.14497(15) 0.76809(9) 0.0398(4) Uani 1 1 d . . . H10A H -0.0899 0.2118 0.7751 0.048 Uiso 1 1 calc R . . H10B H -0.1580 0.1283 0.7777 0.048 Uiso 1 1 calc R . . C18 C 0.28848(12) 0.04936(13) 0.70700(9) 0.0365(4) Uani 1 1 d . . . H18A H 0.3257 0.0818 0.7397 0.044 Uiso 1 1 calc R . . H18B H 0.2569 0.0967 0.6811 0.044 Uiso 1 1 calc R . . C11 C -0.05268(12) 0.13313(13) 0.88315(9) 0.0348(4) Uani 1 1 d . . . H11A H -0.0312 0.1972 0.8850 0.042 Uiso 1 1 calc R . . H11B H -0.0160 0.0972 0.9143 0.042 Uiso 1 1 calc R . . C36 C 0.30518(14) 0.26889(15) 0.94332(10) 0.0464(5) Uani 1 1 d . . . H36 H 0.3507 0.2896 0.9157 0.056 Uiso 1 1 calc R . . C24 C 0.32730(15) -0.01441(15) 0.59681(9) 0.0454(5) Uani 1 1 d . . . H24 H 0.2706 0.0041 0.5811 0.054 Uiso 1 1 calc R . . C26 C 0.21423(13) 0.40192(12) 0.81477(11) 0.0406(4) Uani 1 1 d . . . H26 H 0.1966 0.4144 0.8580 0.049 Uiso 1 1 calc R . . C19 C 0.34974(13) -0.00126(13) 0.66179(9) 0.0375(4) Uani 1 1 d . . . C8 C 0.01114(12) 0.15261(15) 0.67331(9) 0.0402(4) Uani 1 1 d . . . H8A H 0.0119 0.1476 0.6253 0.048 Uiso 1 1 calc R . . H8B H 0.0223 0.2175 0.6849 0.048 Uiso 1 1 calc R . . C12 C -0.14726(12) 0.13205(15) 0.90665(10) 0.0401(4) Uani 1 1 d . . . C32 C 0.18543(13) 0.16803(13) 0.96547(9) 0.0378(4) Uani 1 1 d . . . H32 H 0.1481 0.1182 0.9534 0.045 Uiso 1 1 calc R . . C6 C 0.15737(14) -0.05086(13) 0.69695(9) 0.0400(4) Uani 1 1 d . . . H6A H 0.1173 -0.0911 0.7217 0.048 Uiso 1 1 calc R . . H6B H 0.1906 -0.0897 0.6664 0.048 Uiso 1 1 calc R . . C2 C 0.00972(14) -0.05453(13) 0.85680(10) 0.0429(4) Uani 1 1 d . . . H2A H -0.0122 -0.0535 0.9019 0.052 Uiso 1 1 calc R . . H2B H 0.0143 -0.1192 0.8428 0.052 Uiso 1 1 calc R . . C1 C -0.05407(13) -0.00361(13) 0.81220(10) 0.0394(4) Uani 1 1 d . . . H1A H -0.0470 -0.0251 0.7669 0.047 Uiso 1 1 calc R . . H1B H -0.1156 -0.0162 0.8252 0.047 Uiso 1 1 calc R . . C13 C -0.18460(15) 0.05516(16) 0.93391(10) 0.0487(5) Uani 1 1 d . . . H13 H -0.1513 0.0000 0.9366 0.058 Uiso 1 1 calc R . . C20 C 0.43186(15) -0.03093(17) 0.68362(11) 0.0501(5) Uani 1 1 d . . . H20 H 0.4485 -0.0227 0.7280 0.060 Uiso 1 1 calc R . . C22 C 0.46842(17) -0.08363(18) 0.57768(13) 0.0578(6) Uani 1 1 d . . . H22 H 0.5089 -0.1114 0.5489 0.069 Uiso 1 1 calc R . . C4 C 0.20958(16) -0.12928(14) 0.82998(11) 0.0499(5) Uani 1 1 d . . . H4A H 0.2460 -0.1770 0.8518 0.060 Uiso 1 1 calc R . . H4B H 0.1624 -0.1607 0.8045 0.060 Uiso 1 1 calc R . . C7 C 0.10309(14) 0.01866(14) 0.65888(9) 0.0402(4) Uani 1 1 d . . . H7A H 0.1367 0.0403 0.6210 0.048 Uiso 1 1 calc R . . H7B H 0.0476 -0.0100 0.6427 0.048 Uiso 1 1 calc R . . C29 C 0.26837(13) 0.36676(16) 0.68958(11) 0.0472(5) Uani 1 1 d . . . H29 H 0.2872 0.3541 0.6467 0.057 Uiso 1 1 calc R . . C21 C 0.49069(16) -0.07278(19) 0.64134(13) 0.0582(6) Uani 1 1 d . . . H21 H 0.5465 -0.0937 0.6572 0.070 Uiso 1 1 calc R . . C9 C -0.08019(13) 0.12514(16) 0.69698(10) 0.0454(5) Uani 1 1 d . . . H9A H -0.1255 0.1579 0.6705 0.054 Uiso 1 1 calc R . . H9B H -0.0884 0.0587 0.6893 0.054 Uiso 1 1 calc R . . C33 C 0.17315(16) 0.21139(15) 1.02407(10) 0.0471(5) Uani 1 1 d . . . H33 H 0.1273 0.1915 1.0517 0.057 Uiso 1 1 calc R . . C27 C 0.28147(14) 0.45293(15) 0.78717(13) 0.0530(6) Uani 1 1 d . . . H27 H 0.3096 0.5002 0.8116 0.064 Uiso 1 1 calc R . . C17 C -0.19494(16) 0.21210(19) 0.90613(14) 0.0657(7) Uani 1 1 d . . . H17 H -0.1694 0.2665 0.8893 0.079 Uiso 1 1 calc R . . C3 C 0.16670(14) -0.06983(14) 0.88186(10) 0.0424(4) Uani 1 1 d . . . H3A H 0.1418 -0.1099 0.9158 0.051 Uiso 1 1 calc R . . H3B H 0.2125 -0.0307 0.9028 0.051 Uiso 1 1 calc R . . C35 C 0.29294(18) 0.31145(17) 1.00251(12) 0.0608(6) Uani 1 1 d . . . H35 H 0.3306 0.3606 1.0153 0.073 Uiso 1 1 calc R . . C23 C 0.38606(17) -0.05399(18) 0.55454(11) 0.0568(6) Uani 1 1 d . . . H23 H 0.3704 -0.0610 0.5099 0.068 Uiso 1 1 calc R . . C28 C 0.30782(14) 0.43538(17) 0.72431(13) 0.0552(6) Uani 1 1 d . . . H28 H 0.3533 0.4711 0.7055 0.066 Uiso 1 1 calc R . . C14 C -0.27011(17) 0.0569(2) 0.95757(12) 0.0625(7) Uani 1 1 d . . . H14 H -0.2954 0.0026 0.9746 0.075 Uiso 1 1 calc R . . C34 C 0.22677(18) 0.28347(17) 1.04306(11) 0.0572(6) Uani 1 1 d . . . H34 H 0.2181 0.3133 1.0835 0.069 Uiso 1 1 calc R . . C16 C -0.2807(2) 0.2141(3) 0.93019(19) 0.0920(11) Uani 1 1 d . . . H16 H -0.3144 0.2691 0.9287 0.110 Uiso 1 1 calc R . . C15 C -0.31663(17) 0.1341(3) 0.95650(15) 0.0766(9) Uani 1 1 d . . . H15 H -0.3745 0.1351 0.9737 0.092 Uiso 1 1 calc R . . Zr1 Zr 0.121565(10) 0.102464(10) 0.797775(7) 0.02480(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0336(2) 0.02270(19) 0.0348(2) -0.00099(15) 0.00286(16) -0.00044(15) S2 0.0320(2) 0.0363(2) 0.0306(2) -0.00739(17) -0.00482(15) 0.00275(17) N1 0.0340(7) 0.0280(7) 0.0326(7) -0.0013(6) -0.0006(6) -0.0069(6) N3 0.0437(8) 0.0265(7) 0.0298(7) -0.0045(6) 0.0005(6) 0.0032(6) C25 0.0297(7) 0.0219(7) 0.0364(8) 0.0041(6) -0.0008(6) 0.0023(6) N2 0.0439(8) 0.0258(7) 0.0331(7) 0.0030(6) 0.0017(6) -0.0009(6) C30 0.0346(8) 0.0344(9) 0.0391(9) 0.0034(7) 0.0012(7) 0.0047(7) C5 0.0571(12) 0.0308(9) 0.0411(10) 0.0000(8) 0.0029(9) 0.0143(9) N4 0.0389(8) 0.0338(8) 0.0244(6) -0.0050(6) -0.0051(5) -0.0026(6) C31 0.0360(8) 0.0291(8) 0.0276(7) -0.0018(6) -0.0069(6) 0.0011(6) C10 0.0300(8) 0.0471(11) 0.0422(10) 0.0021(9) -0.0053(7) -0.0030(7) C18 0.0444(10) 0.0325(9) 0.0326(8) -0.0048(7) 0.0041(7) 0.0031(7) C11 0.0369(9) 0.0329(9) 0.0348(9) -0.0047(7) 0.0046(7) -0.0060(7) C36 0.0524(12) 0.0462(12) 0.0405(10) -0.0075(9) 0.0003(9) -0.0144(9) C24 0.0526(12) 0.0482(12) 0.0355(10) -0.0006(9) 0.0060(8) 0.0133(9) C26 0.0432(10) 0.0297(9) 0.0487(11) 0.0007(8) -0.0066(8) -0.0019(7) C19 0.0422(10) 0.0347(9) 0.0358(9) -0.0037(7) 0.0051(7) 0.0051(7) C8 0.0418(10) 0.0502(12) 0.0281(8) 0.0022(8) -0.0101(7) 0.0004(8) C12 0.0369(9) 0.0428(10) 0.0408(10) -0.0015(8) 0.0068(8) -0.0056(8) C32 0.0470(10) 0.0360(9) 0.0302(8) 0.0006(7) -0.0044(7) -0.0053(8) C6 0.0530(11) 0.0301(9) 0.0369(9) -0.0135(7) 0.0032(8) -0.0032(8) C2 0.0544(11) 0.0266(9) 0.0480(11) -0.0001(8) 0.0081(9) -0.0085(8) C1 0.0431(10) 0.0322(9) 0.0429(10) -0.0080(8) 0.0026(8) -0.0139(7) C13 0.0531(12) 0.0493(12) 0.0441(11) 0.0008(9) 0.0131(9) -0.0125(10) C20 0.0467(11) 0.0569(14) 0.0467(11) -0.0097(10) 0.0003(9) 0.0054(10) C22 0.0601(14) 0.0571(14) 0.0570(14) -0.0066(11) 0.0188(11) 0.0155(11) C4 0.0714(15) 0.0302(9) 0.0481(12) 0.0076(9) 0.0049(10) 0.0151(10) C7 0.0490(11) 0.0436(11) 0.0279(8) -0.0115(8) -0.0019(7) -0.0057(8) C29 0.0379(10) 0.0503(12) 0.0538(12) 0.0148(10) 0.0101(9) 0.0051(9) C21 0.0454(12) 0.0634(15) 0.0660(15) -0.0076(13) 0.0048(11) 0.0120(11) C9 0.0377(10) 0.0555(12) 0.0423(10) 0.0016(9) -0.0145(8) -0.0044(9) C33 0.0639(13) 0.0461(12) 0.0314(9) 0.0047(8) 0.0028(9) -0.0038(10) C27 0.0432(11) 0.0363(11) 0.0790(16) 0.0015(11) -0.0084(10) -0.0096(9) C17 0.0524(13) 0.0559(15) 0.0896(19) 0.0151(14) 0.0228(13) 0.0080(11) C3 0.0573(12) 0.0316(9) 0.0385(10) 0.0101(8) 0.0039(8) 0.0074(9) C35 0.0758(16) 0.0514(14) 0.0551(13) -0.0209(11) 0.0011(12) -0.0209(12) C23 0.0695(15) 0.0636(16) 0.0377(11) -0.0060(10) 0.0112(10) 0.0156(12) C28 0.0336(10) 0.0479(13) 0.0843(18) 0.0187(12) 0.0053(10) -0.0039(9) C14 0.0550(14) 0.0803(19) 0.0527(13) -0.0023(13) 0.0164(11) -0.0249(13) C34 0.0842(17) 0.0536(14) 0.0338(10) -0.0127(10) 0.0022(10) -0.0082(12) C16 0.0592(17) 0.091(2) 0.127(3) 0.011(2) 0.0337(18) 0.0227(16) C15 0.0408(12) 0.113(3) 0.0766(19) -0.0017(18) 0.0189(12) -0.0100(15) Zr1 0.03125(8) 0.02108(8) 0.02197(7) -0.00182(5) -0.00240(5) -0.00140(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 S1 C25 1.7651(17) . ? S1 Zr1 2.5882(4) . ? S2 C31 1.7599(17) . ? S2 Zr1 2.5745(4) . ? N1 C1 1.490(2) . ? N1 C10 1.498(2) . ? N1 C11 1.506(2) . ? N1 Zr1 2.4260(15) . ? N3 C6 1.488(2) . ? N3 C18 1.501(2) . ? N3 C5 1.502(2) . ? N3 Zr1 2.4573(15) . ? C25 C26 1.392(2) . ? C25 C30 1.396(2) . ? N2 C2 1.450(2) . ? N2 C3 1.474(2) . ? N2 Zr1 2.0686(14) . ? C30 C29 1.383(3) . ? C30 H30 0.9500 . ? C5 C4 1.520(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? N4 C7 1.457(2) . ? N4 C8 1.473(2) . ? N4 Zr1 2.0642(14) . ? C31 C32 1.391(3) . ? C31 C36 1.392(3) . ? C10 C9 1.514(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C18 C19 1.516(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C11 C12 1.518(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C36 C35 1.382(3) . ? C36 H36 0.9500 . ? C24 C23 1.381(3) . ? C24 C19 1.386(3) . ? C24 H24 0.9500 . ? C26 C27 1.389(3) . ? C26 H26 0.9500 . ? C19 C20 1.382(3) . ? C8 C9 1.526(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C12 C17 1.372(3) . ? C12 C13 1.379(3) . ? C32 C33 1.377(3) . ? C32 H32 0.9500 . ? C6 C7 1.514(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C2 C1 1.514(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C13 C14 1.390(3) . ? C13 H13 0.9500 . ? C20 C21 1.396(3) . ? C20 H20 0.9500 . ? C22 C21 1.355(4) . ? C22 C23 1.394(3) . ? C22 H22 0.9500 . ? C4 C3 1.528(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C29 C28 1.361(4) . ? C29 H29 0.9500 . ? C21 H21 0.9500 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C33 C34 1.380(3) . ? C33 H33 0.9500 . ? C27 C28 1.384(4) . ? C27 H27 0.9500 . ? C17 C16 1.397(4) . ? C17 H17 0.9500 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C35 C34 1.376(3) . ? C35 H35 0.9500 . ? C23 H23 0.9500 . ? C28 H28 0.9500 . ? C14 C15 1.328(4) . ? C14 H14 0.9500 . ? C34 H34 0.9500 . ? C16 C15 1.399(5) . ? C16 H16 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 S1 Zr1 103.99(6) . . ? C31 S2 Zr1 106.25(6) . . ? C1 N1 C10 108.85(14) . . ? C1 N1 C11 111.21(14) . . ? C10 N1 C11 109.37(14) . . ? C1 N1 Zr1 101.63(11) . . ? C10 N1 Zr1 117.74(11) . . ? C11 N1 Zr1 107.82(10) . . ? C6 N3 C18 111.35(14) . . ? C6 N3 C5 109.65(15) . . ? C18 N3 C5 108.51(15) . . ? C6 N3 Zr1 100.93(11) . . ? C18 N3 Zr1 108.41(10) . . ? C5 N3 Zr1 117.83(11) . . ? C26 C25 C30 118.35(17) . . ? C26 C25 S1 118.98(14) . . ? C30 C25 S1 122.59(14) . . ? C2 N2 C3 112.41(15) . . ? C2 N2 Zr1 123.03(12) . . ? C3 N2 Zr1 122.58(12) . . ? C29 C30 C25 120.72(19) . . ? C29 C30 H30 119.6 . . ? C25 C30 H30 119.6 . . ? N3 C5 C4 115.62(17) . . ? N3 C5 H5A 108.4 . . ? C4 C5 H5A 108.4 . . ? N3 C5 H5B 108.4 . . ? C4 C5 H5B 108.4 . . ? H5A C5 H5B 107.4 . . ? C7 N4 C8 111.34(14) . . ? C7 N4 Zr1 123.54(12) . . ? C8 N4 Zr1 122.79(11) . . ? C32 C31 C36 117.84(17) . . ? C32 C31 S2 123.54(14) . . ? C36 C31 S2 118.58(14) . . ? N1 C10 C9 116.14(17) . . ? N1 C10 H10A 108.3 . . ? C9 C10 H10A 108.3 . . ? N1 C10 H10B 108.3 . . ? C9 C10 H10B 108.3 . . ? H10A C10 H10B 107.4 . . ? N3 C18 C19 118.30(15) . . ? N3 C18 H18A 107.7 . . ? C19 C18 H18A 107.7 . . ? N3 C18 H18B 107.7 . . ? C19 C18 H18B 107.7 . . ? H18A C18 H18B 107.1 . . ? N1 C11 C12 117.30(15) . . ? N1 C11 H11A 108.0 . . ? C12 C11 H11A 108.0 . . ? N1 C11 H11B 108.0 . . ? C12 C11 H11B 108.0 . . ? H11A C11 H11B 107.2 . . ? C35 C36 C31 120.8(2) . . ? C35 C36 H36 119.6 . . ? C31 C36 H36 119.6 . . ? C23 C24 C19 121.1(2) . . ? C23 C24 H24 119.5 . . ? C19 C24 H24 119.5 . . ? C27 C26 C25 120.1(2) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C20 C19 C24 118.21(18) . . ? C20 C19 C18 120.55(18) . . ? C24 C19 C18 121.14(17) . . ? N4 C8 C9 113.03(17) . . ? N4 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? N4 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C17 C12 C13 118.5(2) . . ? C17 C12 C11 119.11(19) . . ? C13 C12 C11 122.2(2) . . ? C33 C32 C31 121.00(18) . . ? C33 C32 H32 119.5 . . ? C31 C32 H32 119.5 . . ? N3 C6 C7 111.23(15) . . ? N3 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N3 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N2 C2 C1 109.26(15) . . ? N2 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? N2 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? N1 C1 C2 109.87(14) . . ? N1 C1 H1A 109.7 . . ? C2 C1 H1A 109.7 . . ? N1 C1 H1B 109.7 . . ? C2 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? C12 C13 C14 121.1(2) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C19 C20 C21 120.9(2) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C21 C22 C23 119.9(2) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C5 C4 C3 113.77(18) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? N4 C7 C6 109.02(14) . . ? N4 C7 H7A 109.9 . . ? C6 C7 H7A 109.9 . . ? N4 C7 H7B 109.9 . . ? C6 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C28 C29 C30 120.6(2) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C22 C21 C20 120.2(2) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C10 C9 C8 114.71(16) . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? C8 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C32 C33 C34 120.7(2) . . ? C32 C33 H33 119.7 . . ? C34 C33 H33 119.7 . . ? C28 C27 C26 120.5(2) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C12 C17 C16 120.4(3) . . ? C12 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? N2 C3 C4 112.22(17) . . ? N2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C34 C35 C36 120.7(2) . . ? C34 C35 H35 119.6 . . ? C36 C35 H35 119.6 . . ? C24 C23 C22 119.7(2) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C29 C28 C27 119.7(2) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C15 C14 C13 120.4(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C35 C34 C33 119.0(2) . . ? C35 C34 H34 120.5 . . ? C33 C34 H34 120.5 . . ? C17 C16 C15 119.3(3) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C14 C15 C16 120.3(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? N4 Zr1 N2 116.91(6) . . ? N4 Zr1 N1 83.28(5) . . ? N2 Zr1 N1 71.97(6) . . ? N4 Zr1 N3 71.99(5) . . ? N2 Zr1 N3 82.55(6) . . ? N1 Zr1 N3 131.15(5) . . ? N4 Zr1 S2 129.96(4) . . ? N2 Zr1 S2 96.96(4) . . ? N1 Zr1 S2 144.80(4) . . ? N3 Zr1 S2 77.68(4) . . ? N4 Zr1 S1 96.19(4) . . ? N2 Zr1 S1 131.07(4) . . ? N1 Zr1 S1 77.82(3) . . ? N3 Zr1 S1 144.60(4) . . ? S2 Zr1 S1 86.182(15) . . ? 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 Zr1 S1 C25 C26 -130.49(13) . . . . ? Zr1 S1 C25 C30 52.72(15) . . . . ? C26 C25 C30 C29 -0.7(3) . . . . ? S1 C25 C30 C29 176.13(14) . . . . ? C6 N3 C5 C4 -65.8(2) . . . . ? C18 N3 C5 C4 172.38(17) . . . . ? Zr1 N3 C5 C4 48.8(2) . . . . ? Zr1 S2 C31 C32 40.13(16) . . . . ? Zr1 S2 C31 C36 -142.12(15) . . . . ? C1 N1 C10 C9 -65.8(2) . . . . ? C11 N1 C10 C9 172.53(16) . . . . ? Zr1 N1 C10 C9 49.1(2) . . . . ? C6 N3 C18 C19 -61.8(2) . . . . ? C5 N3 C18 C19 59.0(2) . . . . ? Zr1 N3 C18 C19 -171.92(13) . . . . ? C1 N1 C11 C12 -66.7(2) . . . . ? C10 N1 C11 C12 53.6(2) . . . . ? Zr1 N1 C11 C12 -177.25(14) . . . . ? C32 C31 C36 C35 0.3(3) . . . . ? S2 C31 C36 C35 -177.6(2) . . . . ? C30 C25 C26 C27 0.8(3) . . . . ? S1 C25 C26 C27 -176.12(15) . . . . ? C23 C24 C19 C20 -1.6(3) . . . . ? C23 C24 C19 C18 174.8(2) . . . . ? N3 C18 C19 C20 -94.0(2) . . . . ? N3 C18 C19 C24 89.7(2) . . . . ? C7 N4 C8 C9 93.13(19) . . . . ? Zr1 N4 C8 C9 -70.09(19) . . . . ? N1 C11 C12 C17 -102.2(2) . . . . ? N1 C11 C12 C13 83.6(2) . . . . ? C36 C31 C32 C33 0.3(3) . . . . ? S2 C31 C32 C33 178.08(16) . . . . ? C18 N3 C6 C7 -64.77(19) . . . . ? C5 N3 C6 C7 175.13(16) . . . . ? Zr1 N3 C6 C7 50.11(16) . . . . ? C3 N2 C2 C1 -164.36(16) . . . . ? Zr1 N2 C2 C1 0.0(2) . . . . ? C10 N1 C1 C2 176.15(15) . . . . ? C11 N1 C1 C2 -63.3(2) . . . . ? Zr1 N1 C1 C2 51.23(16) . . . . ? N2 C2 C1 N1 -38.0(2) . . . . ? C17 C12 C13 C14 3.1(3) . . . . ? C11 C12 C13 C14 177.3(2) . . . . ? C24 C19 C20 C21 0.2(3) . . . . ? C18 C19 C20 C21 -176.2(2) . . . . ? N3 C5 C4 C3 -62.9(3) . . . . ? C8 N4 C7 C6 -164.46(16) . . . . ? Zr1 N4 C7 C6 -1.4(2) . . . . ? N3 C6 C7 N4 -37.1(2) . . . . ? C25 C30 C29 C28 -0.2(3) . . . . ? C23 C22 C21 C20 -0.8(4) . . . . ? C19 C20 C21 C22 1.0(4) . . . . ? N1 C10 C9 C8 -61.5(2) . . . . ? N4 C8 C9 C10 68.7(2) . . . . ? C31 C32 C33 C34 -0.5(3) . . . . ? C25 C26 C27 C28 0.0(3) . . . . ? C13 C12 C17 C16 -2.7(4) . . . . ? C11 C12 C17 C16 -177.1(3) . . . . ? C2 N2 C3 C4 91.5(2) . . . . ? Zr1 N2 C3 C4 -72.9(2) . . . . ? C5 C4 C3 N2 71.6(2) . . . . ? C31 C36 C35 C34 -0.8(4) . . . . ? C19 C24 C23 C22 1.8(4) . . . . ? C21 C22 C23 C24 -0.6(4) . . . . ? C30 C29 C28 C27 1.0(3) . . . . ? C26 C27 C28 C29 -0.9(3) . . . . ? C12 C13 C14 C15 -2.5(4) . . . . ? C36 C35 C34 C33 0.7(4) . . . . ? C32 C33 C34 C35 -0.1(4) . . . . ? C12 C17 C16 C15 1.8(5) . . . . ? C13 C14 C15 C16 1.4(5) . . . . ? C17 C16 C15 C14 -1.1(5) . . . . ? C7 N4 Zr1 N2 -49.04(16) . . . . ? C8 N4 Zr1 N2 112.14(14) . . . . ? C7 N4 Zr1 N1 -114.89(14) . . . . ? C8 N4 Zr1 N1 46.30(14) . . . . ? C7 N4 Zr1 N3 22.42(13) . . . . ? C8 N4 Zr1 N3 -176.39(15) . . . . ? C7 N4 Zr1 S2 78.00(15) . . . . ? C8 N4 Zr1 S2 -120.81(13) . . . . ? C7 N4 Zr1 S1 168.20(13) . . . . ? C8 N4 Zr1 S1 -30.61(14) . . . . ? C2 N2 Zr1 N4 -50.33(16) . . . . ? C3 N2 Zr1 N4 112.42(14) . . . . ? C2 N2 Zr1 N1 22.02(13) . . . . ? C3 N2 Zr1 N1 -175.23(15) . . . . ? C2 N2 Zr1 N3 -115.74(14) . . . . ? C3 N2 Zr1 N3 47.01(14) . . . . ? C2 N2 Zr1 S2 167.71(13) . . . . ? C3 N2 Zr1 S2 -29.53(14) . . . . ? C2 N2 Zr1 S1 76.72(15) . . . . ? C3 N2 Zr1 S1 -120.53(13) . . . . ? C1 N1 Zr1 N4 82.89(11) . . . . ? C10 N1 Zr1 N4 -35.85(12) . . . . ? C11 N1 Zr1 N4 -160.10(12) . . . . ? C1 N1 Zr1 N2 -38.28(11) . . . . ? C10 N1 Zr1 N2 -157.02(13) . . . . ? C11 N1 Zr1 N2 78.73(11) . . . . ? C1 N1 Zr1 N3 23.99(13) . . . . ? C10 N1 Zr1 N3 -94.75(13) . . . . ? C11 N1 Zr1 N3 141.00(10) . . . . ? C1 N1 Zr1 S2 -114.37(10) . . . . ? C10 N1 Zr1 S2 126.89(12) . . . . ? C11 N1 Zr1 S2 2.64(14) . . . . ? C1 N1 Zr1 S1 -179.27(11) . . . . ? C10 N1 Zr1 S1 61.99(12) . . . . ? C11 N1 Zr1 S1 -62.26(10) . . . . ? C6 N3 Zr1 N4 -37.52(11) . . . . ? C18 N3 Zr1 N4 79.55(11) . . . . ? C5 N3 Zr1 N4 -156.81(15) . . . . ? C6 N3 Zr1 N2 83.98(11) . . . . ? C18 N3 Zr1 N2 -158.95(12) . . . . ? C5 N3 Zr1 N2 -35.32(14) . . . . ? C6 N3 Zr1 N1 25.89(13) . . . . ? C18 N3 Zr1 N1 142.96(10) . . . . ? C5 N3 Zr1 N1 -93.40(14) . . . . ? C6 N3 Zr1 S2 -177.19(11) . . . . ? C18 N3 Zr1 S2 -60.12(10) . . . . ? C5 N3 Zr1 S2 63.52(13) . . . . ? C6 N3 Zr1 S1 -112.33(11) . . . . ? C18 N3 Zr1 S1 4.74(14) . . . . ? C5 N3 Zr1 S1 128.38(12) . . . . ? C31 S2 Zr1 N4 148.27(8) . . . . ? C31 S2 Zr1 N2 -77.54(7) . . . . ? C31 S2 Zr1 N1 -9.12(9) . . . . ? C31 S2 Zr1 N3 -158.31(7) . . . . ? C31 S2 Zr1 S1 53.39(6) . . . . ? C25 S1 Zr1 N4 -79.05(7) . . . . ? C25 S1 Zr1 N2 146.66(8) . . . . ? C25 S1 Zr1 N1 -160.78(7) . . . . ? C25 S1 Zr1 N3 -11.66(9) . . . . ? C25 S1 Zr1 S2 50.76(6) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 33.62 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.740 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.088 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.125 -0.055 0.431 1541 407 ' ' _platon_squeeze_details ; ; data_lacloipr _database_code_depnum_ccdc_archive 'CCDC 882771' #TrackingRef '11386_web_deposit_cif_file_0_LuisG.Alves_ #1337339488.CIF(LuisAlves).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H41 Cl N4 O Zr' _chemical_formula_sum 'C27 H41 Cl N4 O Zr' _chemical_formula_weight 564.31 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 12.1845(18) _cell_length_b 19.475(4) _cell_length_c 14.086(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.659(5) _cell_angle_gamma 90.00 _cell_volume 3304.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 638 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 19.22 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.134 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.435 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9660 _exptl_absorpt_correction_T_max 0.9828 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21133 _diffrn_reflns_av_R_equivalents 0.1551 _diffrn_reflns_av_sigmaI/netI 0.2365 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 25.68 _reflns_number_total 6244 _reflns_number_gt 2732 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2\s(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^)+(0.0861P)^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 6244 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1528 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.1901 _refine_ls_wR_factor_gt 0.1649 _refine_ls_goodness_of_fit_ref 0.839 _refine_ls_restrained_S_all 0.839 _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 0.70706(6) 0.19014(4) 0.32339(5) 0.0208(2) Uani 1 1 d . . . Cl1 Cl 0.53269(16) 0.22031(12) 0.21115(14) 0.0371(5) Uani 1 1 d . . . N1 N 0.5723(5) 0.1964(3) 0.4418(4) 0.0247(14) Uani 1 1 d . . . O1 O 0.7497(4) 0.1418(3) 0.2127(3) 0.0287(13) Uani 1 1 d . . . N3 N 0.9083(4) 0.2068(3) 0.3525(4) 0.0189(14) Uani 1 1 d . . . C19 C 1.0586(6) 0.2614(4) 0.2667(5) 0.0248(18) Uani 1 1 d . . . C5 C 0.9773(6) 0.1435(4) 0.3714(6) 0.0298(19) Uani 1 1 d . . . H5A H 1.0552 0.1579 0.3917 0.036 Uiso 1 1 calc R . . H5B H 0.9748 0.1185 0.3099 0.036 Uiso 1 1 calc R . . N2 N 0.7433(5) 0.1118(3) 0.4219(4) 0.0241(15) Uani 1 1 d . . . N4 N 0.7401(5) 0.2912(3) 0.3697(4) 0.0257(15) Uani 1 1 d . . . C10 C 0.5192(6) 0.2645(4) 0.4541(5) 0.0246(18) Uani 1 1 d . . . H10A H 0.4823 0.2620 0.5119 0.030 Uiso 1 1 calc R . . H10B H 0.4604 0.2718 0.3983 0.030 Uiso 1 1 calc R . . C13 C 0.4345(6) 0.0827(4) 0.5659(6) 0.036(2) Uani 1 1 d . . . H13 H 0.4997 0.0558 0.5670 0.043 Uiso 1 1 calc R . . C7 C 0.8467(6) 0.3143(4) 0.4193(6) 0.036(2) Uani 1 1 d . . . H7A H 0.8371 0.3355 0.4814 0.043 Uiso 1 1 calc R . . H7B H 0.8781 0.3494 0.3801 0.043 Uiso 1 1 calc R . . C11 C 0.4837(6) 0.1428(4) 0.4181(5) 0.0265(19) Uani 1 1 d . . . H11A H 0.5198 0.0987 0.4068 0.032 Uiso 1 1 calc R . . H11B H 0.4365 0.1560 0.3573 0.032 Uiso 1 1 calc R . . C16 C 0.2465(7) 0.1620(5) 0.5641(6) 0.038(2) Uani 1 1 d . . . H16 H 0.1817 0.1894 0.5633 0.046 Uiso 1 1 calc R . . C23 C 1.2065(7) 0.3456(4) 0.2893(5) 0.032(2) Uani 1 1 d . . . H23 H 1.2315 0.3905 0.3078 0.038 Uiso 1 1 calc R . . C18 C 0.9374(5) 0.2419(4) 0.2649(5) 0.0226(17) Uani 1 1 d . . . H18A H 0.8922 0.2842 0.2541 0.027 Uiso 1 1 calc R . . H18B H 0.9152 0.2114 0.2090 0.027 Uiso 1 1 calc R . . C2 C 0.7119(6) 0.1130(4) 0.5185(5) 0.0274(19) Uani 1 1 d . . . H2A H 0.7791 0.1109 0.5676 0.033 Uiso 1 1 calc R . . H2B H 0.6647 0.0728 0.5274 0.033 Uiso 1 1 calc R . . C9 C 0.5940(6) 0.3275(4) 0.4636(6) 0.031(2) Uani 1 1 d . . . H9A H 0.5485 0.3684 0.4725 0.037 Uiso 1 1 calc R . . H9B H 0.6498 0.3224 0.5220 0.037 Uiso 1 1 calc R . . C4 C 0.9469(6) 0.0933(4) 0.4454(6) 0.0288(19) Uani 1 1 d . . . H4A H 0.9480 0.1176 0.5073 0.035 Uiso 1 1 calc R . . H4B H 1.0037 0.0566 0.4554 0.035 Uiso 1 1 calc R . . C22 C 1.2783(6) 0.2998(5) 0.2585(5) 0.034(2) Uani 1 1 d . . . H22 H 1.3527 0.3128 0.2553 0.041 Uiso 1 1 calc R . . C12 C 0.4090(6) 0.1316(4) 0.4943(5) 0.0239(18) Uani 1 1 d . . . C24 C 1.0977(6) 0.3272(4) 0.2937(5) 0.030(2) Uani 1 1 d . . . H24 H 1.0488 0.3597 0.3153 0.036 Uiso 1 1 calc R . . C1 C 0.6483(6) 0.1792(4) 0.5298(5) 0.0233(18) Uani 1 1 d . . . H1A H 0.6052 0.1741 0.5837 0.028 Uiso 1 1 calc R . . H1B H 0.7017 0.2173 0.5458 0.028 Uiso 1 1 calc R . . C17 C 0.3134(6) 0.1710(4) 0.4925(6) 0.033(2) Uani 1 1 d . . . H17 H 0.2937 0.2038 0.4430 0.039 Uiso 1 1 calc R . . C21 C 1.2427(6) 0.2352(5) 0.2325(6) 0.034(2) Uani 1 1 d . . . H21 H 1.2935 0.2036 0.2116 0.041 Uiso 1 1 calc R . . C20 C 1.1339(6) 0.2141(4) 0.2355(5) 0.0289(19) Uani 1 1 d . . . H20 H 1.1108 0.1688 0.2170 0.035 Uiso 1 1 calc R . . C6 C 0.9267(6) 0.2524(4) 0.4367(5) 0.032(2) Uani 1 1 d . . . H6A H 1.0045 0.2687 0.4472 0.038 Uiso 1 1 calc R . . H6B H 0.9130 0.2270 0.4947 0.038 Uiso 1 1 calc R . . C15 C 0.2733(7) 0.1142(5) 0.6354(6) 0.044(3) Uani 1 1 d . . . H15 H 0.2284 0.1094 0.6846 0.053 Uiso 1 1 calc R . . C3 C 0.8312(6) 0.0600(4) 0.4163(6) 0.030(2) Uani 1 1 d . . . H3A H 0.8248 0.0419 0.3500 0.036 Uiso 1 1 calc R . . H3B H 0.8221 0.0212 0.4598 0.036 Uiso 1 1 calc R . . C14 C 0.3676(7) 0.0721(4) 0.6355(6) 0.043(2) Uani 1 1 d . . . H14 H 0.3847 0.0372 0.6826 0.051 Uiso 1 1 calc R . . C8 C 0.6538(6) 0.3396(4) 0.3789(6) 0.0294(19) Uani 1 1 d . . . H8A H 0.5988 0.3383 0.3196 0.035 Uiso 1 1 calc R . . H8B H 0.6864 0.3863 0.3844 0.035 Uiso 1 1 calc R . . C25 C 0.7177(8) 0.1142(5) 0.1220(7) 0.051(3) Uani 1 1 d . . . H25 H 0.6462 0.1368 0.0944 0.061 Uiso 1 1 calc R . . C26 C 0.7994(9) 0.1298(5) 0.0566(7) 0.073(4) Uani 1 1 d . . . H26A H 0.8107 0.1796 0.0543 0.109 Uiso 1 1 calc R . . H26B H 0.7712 0.1129 -0.0080 0.109 Uiso 1 1 calc R . . H26C H 0.8701 0.1073 0.0803 0.109 Uiso 1 1 calc R . . C27 C 0.6935(10) 0.0363(5) 0.1302(8) 0.081(4) Uani 1 1 d . . . H27A H 0.7637 0.0112 0.1448 0.122 Uiso 1 1 calc R . . H27B H 0.6525 0.0197 0.0693 0.122 Uiso 1 1 calc R . . H27C H 0.6490 0.0287 0.1817 0.122 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 0.0206(4) 0.0224(4) 0.0206(4) 0.0005(4) 0.0066(3) 0.0009(4) Cl1 0.0256(11) 0.0554(14) 0.0302(12) 0.0045(10) 0.0036(9) 0.0088(10) N1 0.023(3) 0.029(4) 0.023(3) -0.001(3) 0.007(3) -0.006(3) O1 0.023(3) 0.037(3) 0.025(3) -0.011(3) -0.001(2) -0.002(2) N3 0.024(3) 0.012(3) 0.023(3) 0.002(3) 0.011(3) 0.001(2) C19 0.022(4) 0.030(5) 0.024(4) 0.002(4) 0.004(3) 0.003(4) C5 0.027(4) 0.023(5) 0.040(5) 0.002(4) 0.008(4) -0.005(4) N2 0.033(4) 0.017(3) 0.023(4) 0.005(3) 0.006(3) 0.003(3) N4 0.021(3) 0.019(4) 0.039(4) 0.000(3) 0.012(3) 0.002(3) C10 0.021(4) 0.028(5) 0.028(5) -0.002(4) 0.015(3) 0.011(3) C13 0.029(5) 0.029(5) 0.056(6) -0.002(4) 0.021(4) -0.013(4) C7 0.039(5) 0.034(5) 0.035(5) -0.008(4) 0.009(4) 0.001(4) C11 0.032(5) 0.028(5) 0.020(4) -0.007(4) 0.007(4) -0.008(4) C16 0.024(5) 0.052(6) 0.041(5) -0.010(5) 0.012(4) -0.010(4) C23 0.040(5) 0.024(5) 0.031(5) 0.002(4) 0.008(4) -0.003(4) C18 0.021(4) 0.019(4) 0.029(5) 0.001(3) 0.007(3) 0.009(3) C2 0.028(5) 0.028(5) 0.026(5) 0.006(4) 0.005(4) 0.003(4) C9 0.037(5) 0.017(5) 0.042(5) -0.002(4) 0.019(4) 0.002(3) C4 0.017(4) 0.031(5) 0.037(5) 0.007(4) 0.001(4) 0.003(4) C22 0.014(4) 0.059(6) 0.026(4) 0.010(4) -0.007(3) -0.011(4) C12 0.030(5) 0.021(4) 0.022(4) -0.008(3) 0.007(3) -0.008(4) C24 0.026(4) 0.040(6) 0.026(4) 0.000(4) 0.011(3) -0.001(4) C1 0.023(4) 0.026(5) 0.022(4) 0.001(3) 0.008(3) -0.001(3) C17 0.029(5) 0.041(6) 0.031(5) 0.001(4) 0.015(4) -0.008(4) C21 0.027(5) 0.049(6) 0.030(5) 0.016(4) 0.014(4) 0.004(4) C20 0.026(5) 0.030(5) 0.032(5) -0.005(4) 0.006(4) 0.009(4) C6 0.031(5) 0.040(5) 0.025(5) -0.014(4) 0.008(4) -0.010(4) C15 0.053(6) 0.050(6) 0.037(5) -0.011(5) 0.026(5) -0.035(5) C3 0.028(5) 0.028(5) 0.037(5) 0.003(4) 0.014(4) 0.004(4) C14 0.041(5) 0.033(5) 0.059(6) 0.004(5) 0.023(5) -0.003(4) C8 0.034(5) 0.010(4) 0.047(5) 0.003(4) 0.017(4) 0.004(4) C25 0.057(6) 0.050(7) 0.049(6) -0.015(5) 0.017(5) -0.006(5) C26 0.112(9) 0.061(8) 0.054(7) -0.030(6) 0.041(7) -0.035(7) C27 0.137(11) 0.052(7) 0.065(8) -0.019(6) 0.049(8) -0.024(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.957(5) . ? Zr1 N2 2.065(6) . ? Zr1 N4 2.094(6) . ? Zr1 N3 2.446(5) . ? Zr1 N1 2.513(5) . ? Zr1 Cl1 2.519(2) . ? N1 C1 1.470(9) . ? N1 C10 1.498(9) . ? N1 C11 1.502(9) . ? O1 C25 1.387(9) . ? N3 C6 1.473(9) . ? N3 C5 1.493(9) . ? N3 C18 1.499(8) . ? C19 C24 1.400(10) . ? C19 C20 1.417(10) . ? C19 C18 1.521(9) . ? C5 C4 1.516(10) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? N2 C2 1.469(9) . ? N2 C3 1.482(9) . ? N4 C8 1.433(8) . ? N4 C7 1.450(9) . ? C10 C9 1.522(10) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C13 C14 1.383(10) . ? C13 C12 1.388(10) . ? C13 H13 0.9500 . ? C7 C6 1.547(11) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C11 C12 1.523(9) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C16 C15 1.373(12) . ? C16 C17 1.400(10) . ? C16 H16 0.9500 . ? C23 C22 1.365(11) . ? C23 C24 1.384(10) . ? C23 H23 0.9500 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C2 C1 1.526(9) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C9 C8 1.507(10) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C4 C3 1.550(10) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C22 C21 1.362(11) . ? C22 H22 0.9500 . ? C12 C17 1.392(10) . ? C24 H24 0.9500 . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C17 H17 0.9500 . ? C21 C20 1.394(10) . ? C21 H21 0.9500 . ? C20 H20 0.9500 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C15 C14 1.411(12) . ? C15 H15 0.9500 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C14 H14 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C25 C26 1.486(12) . ? C25 C27 1.555(12) . ? C25 H25 1.0000 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 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 O1 Zr1 N2 97.2(2) . . ? O1 Zr1 N4 129.7(2) . . ? N2 Zr1 N4 118.3(2) . . ? O1 Zr1 N3 79.49(18) . . ? N2 Zr1 N3 83.0(2) . . ? N4 Zr1 N3 71.5(2) . . ? O1 Zr1 N1 146.1(2) . . ? N2 Zr1 N1 71.6(2) . . ? N4 Zr1 N1 82.1(2) . . ? N3 Zr1 N1 128.39(18) . . ? O1 Zr1 Cl1 84.95(15) . . ? N2 Zr1 Cl1 131.99(17) . . ? N4 Zr1 Cl1 94.63(18) . . ? N3 Zr1 Cl1 143.48(14) . . ? N1 Zr1 Cl1 80.31(14) . . ? C1 N1 C10 109.4(5) . . ? C1 N1 C11 111.7(6) . . ? C10 N1 C11 109.4(5) . . ? C1 N1 Zr1 99.1(4) . . ? C10 N1 Zr1 117.1(4) . . ? C11 N1 Zr1 109.8(4) . . ? C25 O1 Zr1 148.1(5) . . ? C6 N3 C5 110.0(6) . . ? C6 N3 C18 111.2(5) . . ? C5 N3 C18 109.1(5) . . ? C6 N3 Zr1 104.0(4) . . ? C5 N3 Zr1 116.4(4) . . ? C18 N3 Zr1 106.1(4) . . ? C24 C19 C20 118.0(7) . . ? C24 C19 C18 121.5(6) . . ? C20 C19 C18 120.4(7) . . ? N3 C5 C4 117.7(6) . . ? N3 C5 H5A 107.9 . . ? C4 C5 H5A 107.9 . . ? N3 C5 H5B 107.9 . . ? C4 C5 H5B 107.9 . . ? H5A C5 H5B 107.2 . . ? C2 N2 C3 110.6(6) . . ? C2 N2 Zr1 123.5(4) . . ? C3 N2 Zr1 123.4(4) . . ? C8 N4 C7 111.6(6) . . ? C8 N4 Zr1 122.5(5) . . ? C7 N4 Zr1 123.9(5) . . ? N1 C10 C9 117.4(6) . . ? N1 C10 H10A 107.9 . . ? C9 C10 H10A 107.9 . . ? N1 C10 H10B 107.9 . . ? C9 C10 H10B 107.9 . . ? H10A C10 H10B 107.2 . . ? C14 C13 C12 121.8(8) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? N4 C7 C6 109.4(6) . . ? N4 C7 H7A 109.8 . . ? C6 C7 H7A 109.8 . . ? N4 C7 H7B 109.8 . . ? C6 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? N1 C11 C12 115.4(6) . . ? N1 C11 H11A 108.4 . . ? C12 C11 H11A 108.4 . . ? N1 C11 H11B 108.4 . . ? C12 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C15 C16 C17 120.7(8) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C22 C23 C24 120.6(8) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? N3 C18 C19 116.7(6) . . ? N3 C18 H18A 108.1 . . ? C19 C18 H18A 108.1 . . ? N3 C18 H18B 108.1 . . ? C19 C18 H18B 108.1 . . ? H18A C18 H18B 107.3 . . ? N2 C2 C1 108.5(6) . . ? N2 C2 H2A 110.0 . . ? C1 C2 H2A 110.0 . . ? N2 C2 H2B 110.0 . . ? C1 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? C8 C9 C10 114.2(6) . . ? C8 C9 H9A 108.7 . . ? C10 C9 H9A 108.7 . . ? C8 C9 H9B 108.7 . . ? C10 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C5 C4 C3 113.2(6) . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C21 C22 C23 119.7(7) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C13 C12 C17 119.1(7) . . ? C13 C12 C11 121.2(7) . . ? C17 C12 C11 119.7(7) . . ? C23 C24 C19 120.9(7) . . ? C23 C24 H24 119.5 . . ? C19 C24 H24 119.5 . . ? N1 C1 C2 111.7(6) . . ? N1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? N1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? C12 C17 C16 119.7(8) . . ? C12 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C22 C21 C20 122.0(8) . . ? C22 C21 H21 119.0 . . ? C20 C21 H21 119.0 . . ? C21 C20 C19 118.8(7) . . ? C21 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? N3 C6 C7 109.1(6) . . ? N3 C6 H6A 109.9 . . ? C7 C6 H6A 109.9 . . ? N3 C6 H6B 109.9 . . ? C7 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? C16 C15 C14 120.0(8) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? N2 C3 C4 109.6(6) . . ? N2 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? N2 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C13 C14 C15 118.6(8) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? N4 C8 C9 114.7(6) . . ? N4 C8 H8A 108.6 . . ? C9 C8 H8A 108.6 . . ? N4 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? O1 C25 C26 111.8(8) . . ? O1 C25 C27 109.9(8) . . ? C26 C25 C27 113.4(8) . . ? O1 C25 H25 107.1 . . ? C26 C25 H25 107.1 . . ? C27 C25 H25 107.1 . . ? 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 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 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 O1 Zr1 N1 C1 113.9(5) . . . . ? N2 Zr1 N1 C1 38.9(4) . . . . ? N4 Zr1 N1 C1 -84.4(4) . . . . ? N3 Zr1 N1 C1 -25.7(5) . . . . ? Cl1 Zr1 N1 C1 179.5(4) . . . . ? O1 Zr1 N1 C10 -128.7(5) . . . . ? N2 Zr1 N1 C10 156.3(5) . . . . ? N4 Zr1 N1 C10 32.9(5) . . . . ? N3 Zr1 N1 C10 91.6(5) . . . . ? Cl1 Zr1 N1 C10 -63.2(5) . . . . ? O1 Zr1 N1 C11 -3.2(7) . . . . ? N2 Zr1 N1 C11 -78.2(5) . . . . ? N4 Zr1 N1 C11 158.4(5) . . . . ? N3 Zr1 N1 C11 -142.9(4) . . . . ? Cl1 Zr1 N1 C11 62.3(4) . . . . ? N2 Zr1 O1 C25 115.9(10) . . . . ? N4 Zr1 O1 C25 -107.6(10) . . . . ? N3 Zr1 O1 C25 -162.6(10) . . . . ? N1 Zr1 O1 C25 48.4(11) . . . . ? Cl1 Zr1 O1 C25 -15.8(10) . . . . ? O1 Zr1 N3 C6 174.8(5) . . . . ? N2 Zr1 N3 C6 -86.6(5) . . . . ? N4 Zr1 N3 C6 36.4(4) . . . . ? N1 Zr1 N3 C6 -26.8(5) . . . . ? Cl1 Zr1 N3 C6 108.4(4) . . . . ? O1 Zr1 N3 C5 -64.2(5) . . . . ? N2 Zr1 N3 C5 34.5(5) . . . . ? N4 Zr1 N3 C5 157.5(5) . . . . ? N1 Zr1 N3 C5 94.3(5) . . . . ? Cl1 Zr1 N3 C5 -130.5(4) . . . . ? O1 Zr1 N3 C18 57.3(4) . . . . ? N2 Zr1 N3 C18 156.0(4) . . . . ? N4 Zr1 N3 C18 -81.0(4) . . . . ? N1 Zr1 N3 C18 -144.2(4) . . . . ? Cl1 Zr1 N3 C18 -9.0(5) . . . . ? C6 N3 C5 C4 68.8(8) . . . . ? C18 N3 C5 C4 -169.0(6) . . . . ? Zr1 N3 C5 C4 -49.1(8) . . . . ? O1 Zr1 N2 C2 -169.9(5) . . . . ? N4 Zr1 N2 C2 47.1(6) . . . . ? N3 Zr1 N2 C2 111.6(6) . . . . ? N1 Zr1 N2 C2 -22.8(5) . . . . ? Cl1 Zr1 N2 C2 -80.3(6) . . . . ? O1 Zr1 N2 C3 29.8(6) . . . . ? N4 Zr1 N2 C3 -113.2(5) . . . . ? N3 Zr1 N2 C3 -48.7(5) . . . . ? N1 Zr1 N2 C3 176.9(6) . . . . ? Cl1 Zr1 N2 C3 119.4(5) . . . . ? O1 Zr1 N4 C8 120.8(5) . . . . ? N2 Zr1 N4 C8 -110.1(6) . . . . ? N3 Zr1 N4 C8 178.9(6) . . . . ? N1 Zr1 N4 C8 -46.0(5) . . . . ? Cl1 Zr1 N4 C8 33.5(5) . . . . ? O1 Zr1 N4 C7 -76.5(6) . . . . ? N2 Zr1 N4 C7 52.5(6) . . . . ? N3 Zr1 N4 C7 -18.4(5) . . . . ? N1 Zr1 N4 C7 116.7(6) . . . . ? Cl1 Zr1 N4 C7 -163.8(5) . . . . ? C1 N1 C10 C9 66.2(8) . . . . ? C11 N1 C10 C9 -171.1(6) . . . . ? Zr1 N1 C10 C9 -45.4(8) . . . . ? C8 N4 C7 C6 161.1(6) . . . . ? Zr1 N4 C7 C6 -3.2(8) . . . . ? C1 N1 C11 C12 60.1(8) . . . . ? C10 N1 C11 C12 -61.2(8) . . . . ? Zr1 N1 C11 C12 169.0(5) . . . . ? C6 N3 C18 C19 64.7(8) . . . . ? C5 N3 C18 C19 -56.8(8) . . . . ? Zr1 N3 C18 C19 177.2(5) . . . . ? C24 C19 C18 N3 -95.5(8) . . . . ? C20 C19 C18 N3 88.3(8) . . . . ? C3 N2 C2 C1 163.7(6) . . . . ? Zr1 N2 C2 C1 1.2(8) . . . . ? N1 C10 C9 C8 59.6(9) . . . . ? N3 C5 C4 C3 64.5(9) . . . . ? C24 C23 C22 C21 -0.4(12) . . . . ? C14 C13 C12 C17 -0.1(12) . . . . ? C14 C13 C12 C11 179.9(7) . . . . ? N1 C11 C12 C13 -91.4(9) . . . . ? N1 C11 C12 C17 88.6(9) . . . . ? C22 C23 C24 C19 -0.1(11) . . . . ? C20 C19 C24 C23 0.5(11) . . . . ? C18 C19 C24 C23 -175.9(7) . . . . ? C10 N1 C1 C2 -175.4(5) . . . . ? C11 N1 C1 C2 63.4(7) . . . . ? Zr1 N1 C1 C2 -52.3(6) . . . . ? N2 C2 C1 N1 39.9(8) . . . . ? C13 C12 C17 C16 1.8(11) . . . . ? C11 C12 C17 C16 -178.2(7) . . . . ? C15 C16 C17 C12 -0.9(12) . . . . ? C23 C22 C21 C20 0.5(12) . . . . ? C22 C21 C20 C19 -0.1(11) . . . . ? C24 C19 C20 C21 -0.4(11) . . . . ? C18 C19 C20 C21 176.0(7) . . . . ? C5 N3 C6 C7 -174.9(6) . . . . ? C18 N3 C6 C7 64.2(7) . . . . ? Zr1 N3 C6 C7 -49.6(6) . . . . ? N4 C7 C6 N3 38.2(8) . . . . ? C17 C16 C15 C14 -1.7(12) . . . . ? C2 N2 C3 C4 -88.9(7) . . . . ? Zr1 N2 C3 C4 73.6(7) . . . . ? C5 C4 C3 N2 -71.0(8) . . . . ? C12 C13 C14 C15 -2.4(12) . . . . ? C16 C15 C14 C13 3.3(13) . . . . ? C7 N4 C8 C9 -91.2(8) . . . . ? Zr1 N4 C8 C9 73.4(8) . . . . ? C10 C9 C8 N4 -70.9(9) . . . . ? Zr1 O1 C25 C26 137.9(9) . . . . ? Zr1 O1 C25 C27 -95.3(12) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.484 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.122 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.004 0.000 0.000 398 241 ' ' 2 0.008 0.500 0.500 398 240 ' ' _platon_squeeze_details ; ;