# 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_mk73 _database_code_depnum_ccdc_archive 'CCDC 902358' #TrackingRef 'combined_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H25 N' _chemical_formula_weight 207.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.5358(2) _cell_length_b 10.7021(2) _cell_length_c 16.7625(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1351.88(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 38748 _cell_measurement_theta_min 4.1274 _cell_measurement_theta_max 75.7279 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.019 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.428 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.62675 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46839 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0053 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.90 _diffrn_reflns_theta_max 75.92 _reflns_number_total 1646 _reflns_number_gt 1638 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _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. The N-H proton was refined freely. The methyl groups were refined as idealised rigid groups allowed to rotate but not tip. The anomalous scattering was not sufficient to determine the absolute structure. For this reason the Friedel opposite reflections were averaged and the Flack parameter is thus indeterminate. ; _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^)+(0.0520P)^2^+0.2076P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.3(6) _chemical_absolute_configuration . _refine_ls_number_reflns 1646 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0833 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 N N 0.52489(15) 0.34592(10) 0.37911(6) 0.0184(2) Uani 1 1 d . . . H1 H 0.628(3) 0.3040(17) 0.3804(10) 0.028(4) Uiso 1 1 d . . . C1 C 0.40265(17) 0.33318(11) 0.31849(7) 0.0183(3) Uani 1 1 d . . . C2 C 0.25775(17) 0.40423(11) 0.33948(7) 0.0187(3) Uani 1 1 d . . . C3 C 0.29592(17) 0.46249(11) 0.41480(7) 0.0185(3) Uani 1 1 d . . . C4 C 0.46311(17) 0.42389(11) 0.43821(7) 0.0178(3) Uani 1 1 d . . . C5 C 0.44480(18) 0.25524(11) 0.24468(7) 0.0202(3) Uani 1 1 d . . . C6 C 0.6330(2) 0.20216(16) 0.24934(9) 0.0346(4) Uani 1 1 d . . . H6A H 0.7184 0.2709 0.2536 0.052 Uiso 1 1 calc R . . H6B H 0.6580 0.1535 0.2011 0.052 Uiso 1 1 calc R . . H6C H 0.6433 0.1481 0.2963 0.052 Uiso 1 1 calc R . . C7 C 0.3153(2) 0.14520(13) 0.23675(9) 0.0288(3) Uani 1 1 d . . . H7A H 0.3488 0.0941 0.1906 0.043 Uiso 1 1 calc R . . H7B H 0.1946 0.1772 0.2293 0.043 Uiso 1 1 calc R . . H7C H 0.3200 0.0941 0.2852 0.043 Uiso 1 1 calc R . . C8 C 0.4327(2) 0.33673(13) 0.16937(8) 0.0299(3) Uani 1 1 d . . . H8A H 0.5171 0.4061 0.1735 0.045 Uiso 1 1 calc R . . H8B H 0.3120 0.3700 0.1642 0.045 Uiso 1 1 calc R . . H8C H 0.4611 0.2861 0.1224 0.045 Uiso 1 1 calc R . . C9 C 0.08672(18) 0.42205(13) 0.29507(8) 0.0246(3) Uani 1 1 d . . . H9A H 0.0831 0.3652 0.2493 0.037 Uiso 1 1 calc R . . H9B H 0.0786 0.5086 0.2763 0.037 Uiso 1 1 calc R . . H9C H -0.0133 0.4041 0.3307 0.037 Uiso 1 1 calc R . . C10 C 0.17297(19) 0.55121(13) 0.45675(8) 0.0263(3) Uani 1 1 d . . . H10A H 0.2424 0.6170 0.4828 0.039 Uiso 1 1 calc R . . H10B H 0.1042 0.5056 0.4969 0.039 Uiso 1 1 calc R . . H10C H 0.0920 0.5890 0.4179 0.039 Uiso 1 1 calc R . . C11 C 0.57152(18) 0.44978(12) 0.51284(7) 0.0212(3) Uani 1 1 d . . . C12 C 0.4647(2) 0.41391(15) 0.58731(7) 0.0294(3) Uani 1 1 d . . . H12A H 0.4421 0.3237 0.5870 0.044 Uiso 1 1 calc R . . H12B H 0.3516 0.4590 0.5873 0.044 Uiso 1 1 calc R . . H12C H 0.5324 0.4361 0.6352 0.044 Uiso 1 1 calc R . . C13 C 0.6223(2) 0.58932(13) 0.51683(10) 0.0352(4) Uani 1 1 d . . . H13A H 0.5143 0.6402 0.5185 0.053 Uiso 1 1 calc R . . H13B H 0.6921 0.6116 0.4696 0.053 Uiso 1 1 calc R . . H13C H 0.6928 0.6048 0.5650 0.053 Uiso 1 1 calc R . . C14 C 0.74292(19) 0.37318(14) 0.51317(8) 0.0261(3) Uani 1 1 d . . . H14A H 0.8141 0.3947 0.4662 0.039 Uiso 1 1 calc R . . H14B H 0.7139 0.2839 0.5119 0.039 Uiso 1 1 calc R . . H14C H 0.8106 0.3918 0.5616 0.039 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 N 0.0216(5) 0.0176(5) 0.0159(5) -0.0010(4) -0.0014(4) 0.0027(5) C1 0.0237(6) 0.0168(5) 0.0145(5) 0.0008(4) -0.0015(5) -0.0015(5) C2 0.0222(6) 0.0174(5) 0.0165(5) 0.0014(5) -0.0009(5) -0.0012(5) C3 0.0226(6) 0.0162(5) 0.0166(5) 0.0011(4) 0.0017(5) -0.0001(5) C4 0.0233(6) 0.0153(5) 0.0146(5) 0.0001(4) 0.0006(5) -0.0008(5) C5 0.0266(6) 0.0181(6) 0.0160(5) -0.0031(5) 0.0001(5) -0.0004(5) C6 0.0333(8) 0.0412(8) 0.0294(8) -0.0176(7) -0.0024(7) 0.0104(7) C7 0.0419(8) 0.0211(6) 0.0236(6) -0.0039(5) 0.0016(6) -0.0068(6) C8 0.0486(9) 0.0236(6) 0.0175(6) -0.0005(5) 0.0045(6) -0.0036(7) C9 0.0232(6) 0.0280(6) 0.0227(6) 0.0003(5) -0.0025(5) 0.0001(6) C10 0.0265(6) 0.0268(6) 0.0255(6) -0.0061(6) 0.0024(6) 0.0034(6) C11 0.0273(6) 0.0198(6) 0.0166(5) -0.0007(5) -0.0035(5) -0.0005(5) C12 0.0328(7) 0.0396(8) 0.0157(6) -0.0013(6) 0.0008(5) 0.0031(7) C13 0.0498(9) 0.0226(7) 0.0330(7) -0.0025(6) -0.0164(7) -0.0046(7) C14 0.0258(6) 0.0324(7) 0.0202(6) 0.0008(5) -0.0034(5) 0.0015(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N C4 1.3764(16) . ? N C1 1.3784(16) . ? C1 C2 1.3763(18) . ? C1 C5 1.5256(16) . ? C2 C3 1.4372(16) . ? C2 C9 1.5006(18) . ? C3 C4 1.3827(17) . ? C3 C10 1.5015(18) . ? C4 C11 1.5196(17) . ? C5 C6 1.530(2) . ? C5 C7 1.5351(19) . ? C5 C8 1.5369(18) . ? C11 C14 1.5299(19) . ? C11 C12 1.5339(18) . ? C11 C13 1.5431(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N C1 111.38(11) . . ? C2 C1 N 106.68(10) . . ? C2 C1 C5 132.42(11) . . ? N C1 C5 120.85(11) . . ? C1 C2 C3 107.79(11) . . ? C1 C2 C9 128.66(11) . . ? C3 C2 C9 123.55(12) . . ? C4 C3 C2 107.58(11) . . ? C4 C3 C10 128.19(12) . . ? C2 C3 C10 124.21(12) . . ? N C4 C3 106.56(11) . . ? N C4 C11 121.41(11) . . ? C3 C4 C11 131.99(11) . . ? C1 C5 C6 110.77(11) . . ? C1 C5 C7 110.94(11) . . ? C6 C5 C7 107.98(11) . . ? C1 C5 C8 110.09(10) . . ? C6 C5 C8 107.92(12) . . ? C7 C5 C8 109.05(11) . . ? C4 C11 C14 111.05(10) . . ? C4 C11 C12 110.02(11) . . ? C14 C11 C12 107.81(11) . . ? C4 C11 C13 110.20(11) . . ? C14 C11 C13 108.00(12) . . ? C12 C11 C13 109.70(12) . . ? 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 C4 N C1 C2 -0.44(14) . . . . ? C4 N C1 C5 177.52(10) . . . . ? N C1 C2 C3 0.70(13) . . . . ? C5 C1 C2 C3 -176.92(12) . . . . ? N C1 C2 C9 -179.24(12) . . . . ? C5 C1 C2 C9 3.1(2) . . . . ? C1 C2 C3 C4 -0.72(13) . . . . ? C9 C2 C3 C4 179.22(11) . . . . ? C1 C2 C3 C10 177.89(12) . . . . ? C9 C2 C3 C10 -2.17(19) . . . . ? C1 N C4 C3 -0.02(13) . . . . ? C1 N C4 C11 178.13(11) . . . . ? C2 C3 C4 N 0.45(13) . . . . ? C10 C3 C4 N -178.09(12) . . . . ? C2 C3 C4 C11 -177.43(12) . . . . ? C10 C3 C4 C11 4.0(2) . . . . ? C2 C1 C5 C6 175.82(14) . . . . ? N C1 C5 C6 -1.53(16) . . . . ? C2 C1 C5 C7 -64.27(17) . . . . ? N C1 C5 C7 118.38(13) . . . . ? C2 C1 C5 C8 56.53(18) . . . . ? N C1 C5 C8 -120.82(13) . . . . ? N C4 C11 C14 -3.41(16) . . . . ? C3 C4 C11 C14 174.20(12) . . . . ? N C4 C11 C12 -122.68(13) . . . . ? C3 C4 C11 C12 54.93(17) . . . . ? N C4 C11 C13 116.23(14) . . . . ? C3 C4 C11 C13 -66.16(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 75.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.163 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.037 _iucr_refine_instructions_details ; TITL MK73 in P2(1)2(1)2(1) CELL 1.54184 7.535813 10.702097 16.762482 90.0000 90.0000 90.0000 ZERR 4.00 0.000200 0.000200 0.000300 0.0000 0.0000 0.0000 LATT -1 SYMM -x+1/2,-y, z+1/2 SYMM -x, y+1/2,-z+1/2 SYMM x+1/2,-y+1/2,-z SFAC C H N UNIT 56 100 4 TEMP -173 SIZE 0.25 0.2 0.2 rem ACTA 150 CONF MERG 3 FMAP 2 PLAN 10 L.S. 4 WGHT 0.052000 0.207600 FVAR 11.32220 N 3 0.524893 0.345920 0.379113 11.00000 0.02155 0.01759 = 0.01592 -0.00104 -0.00143 0.00268 H1 2 0.627528 0.304022 0.380426 11.00000 0.02850 C1 1 0.402650 0.333184 0.318487 11.00000 0.02367 0.01683 = 0.01452 0.00077 -0.00149 -0.00153 C2 1 0.257754 0.404229 0.339484 11.00000 0.02224 0.01737 = 0.01652 0.00138 -0.00092 -0.00118 C3 1 0.295924 0.462492 0.414801 11.00000 0.02260 0.01616 = 0.01660 0.00108 0.00165 -0.00013 C4 1 0.463110 0.423894 0.438210 11.00000 0.02330 0.01534 = 0.01464 0.00008 0.00060 -0.00080 C5 1 0.444799 0.255245 0.244676 11.00000 0.02660 0.01809 = 0.01603 -0.00311 0.00007 -0.00038 C6 1 0.633030 0.202161 0.249336 11.00000 0.03327 0.04116 = 0.02942 -0.01758 -0.00236 0.01038 AFIX 137 H6A 2 0.718380 0.270928 0.253591 11.00000 -1.50000 H6B 2 0.657999 0.153471 0.201111 11.00000 -1.50000 H6C 2 0.643276 0.148082 0.296290 11.00000 -1.50000 AFIX 0 C7 1 0.315339 0.145201 0.236751 11.00000 0.04187 0.02110 = 0.02355 -0.00392 0.00162 -0.00678 AFIX 137 H7A 2 0.348769 0.094063 0.190640 11.00000 -1.50000 H7B 2 0.194596 0.177158 0.229321 11.00000 -1.50000 H7C 2 0.320005 0.094128 0.285231 11.00000 -1.50000 AFIX 0 C8 1 0.432667 0.336725 0.169373 11.00000 0.04859 0.02361 = 0.01748 -0.00046 0.00446 -0.00356 AFIX 137 H8A 2 0.517090 0.406079 0.173485 11.00000 -1.50000 H8B 2 0.312037 0.369976 0.164238 11.00000 -1.50000 H8C 2 0.461139 0.286076 0.122378 11.00000 -1.50000 AFIX 0 C9 1 0.086719 0.422050 0.295068 11.00000 0.02322 0.02795 = 0.02267 0.00034 -0.00246 0.00010 AFIX 137 H9A 2 0.083120 0.365158 0.249285 11.00000 -1.50000 H9B 2 0.078595 0.508564 0.276261 11.00000 -1.50000 H9C 2 -0.013254 0.404065 0.330652 11.00000 -1.50000 AFIX 0 C10 1 0.172969 0.551207 0.456755 11.00000 0.02652 0.02680 = 0.02552 -0.00610 0.00240 0.00344 AFIX 137 H10A 2 0.242441 0.616960 0.482836 11.00000 -1.50000 H10B 2 0.104215 0.505609 0.496943 11.00000 -1.50000 H10C 2 0.092002 0.588955 0.417867 11.00000 -1.50000 AFIX 0 C11 1 0.571519 0.449781 0.512844 11.00000 0.02727 0.01976 = 0.01656 -0.00066 -0.00349 -0.00050 C12 1 0.464743 0.413912 0.587309 11.00000 0.03282 0.03957 = 0.01573 -0.00131 0.00081 0.00312 AFIX 137 H12A 2 0.442104 0.323741 0.586992 11.00000 -1.50000 H12B 2 0.351553 0.459000 0.587307 11.00000 -1.50000 H12C 2 0.532353 0.436080 0.635204 11.00000 -1.50000 AFIX 0 C13 1 0.622297 0.589321 0.516827 11.00000 0.04979 0.02265 = 0.03302 -0.00250 -0.01644 -0.00463 AFIX 137 H13A 2 0.514269 0.640236 0.518471 11.00000 -1.50000 H13B 2 0.692079 0.611578 0.469584 11.00000 -1.50000 H13C 2 0.692792 0.604771 0.564955 11.00000 -1.50000 AFIX 0 C14 1 0.742925 0.373176 0.513171 11.00000 0.02580 0.03241 = 0.02016 0.00083 -0.00336 0.00151 AFIX 137 H14A 2 0.814098 0.394685 0.466207 11.00000 -1.50000 H14B 2 0.713850 0.283946 0.511867 11.00000 -1.50000 H14C 2 0.810622 0.391826 0.561648 11.00000 -1.50000 HKLF 4 ; data_mk69 _database_code_depnum_ccdc_archive 'CCDC 902359' #TrackingRef 'combined_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H48 K N O6' _chemical_formula_weight 509.75 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' K K 0.2009 0.2494 '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' 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 9.8304(2) _cell_length_b 17.5251(4) _cell_length_c 16.5980(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.083(2) _cell_angle_gamma 90.00 _cell_volume 2859.47(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 22263 _cell_measurement_theta_min 2.3196 _cell_measurement_theta_max 30.8312 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97204 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 155683 _diffrn_reflns_av_R_equivalents 0.0631 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7090 _reflns_number_gt 5974 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _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^)+(0.0324P)^2^+1.1686P] 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 7090 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0793 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 K K 0.44137(2) 0.199213(13) 0.241614(14) 0.01428(6) Uani 1 1 d . . . N N 0.33007(9) 0.35005(5) 0.18283(6) 0.01353(19) Uani 1 1 d . . . O1 O 0.21276(8) 0.14430(5) 0.15812(5) 0.01693(17) Uani 1 1 d . . . O2 O 0.46545(8) 0.13875(5) 0.07747(5) 0.01930(18) Uani 1 1 d . . . O3 O 0.68050(8) 0.11406(5) 0.18205(5) 0.01973(18) Uani 1 1 d . . . O4 O 0.69263(8) 0.20041(5) 0.32387(5) 0.01863(17) Uani 1 1 d . . . O5 O 0.46753(9) 0.13803(5) 0.40597(5) 0.02245(19) Uani 1 1 d . . . O6 O 0.28989(8) 0.06877(5) 0.29756(5) 0.01749(17) Uani 1 1 d . . . C1 C 0.46642(11) 0.36609(6) 0.18763(7) 0.0128(2) Uani 1 1 d . . . C2 C 0.50776(11) 0.37519(6) 0.26815(7) 0.0143(2) Uani 1 1 d . . . C3 C 0.38830(12) 0.36403(6) 0.31554(7) 0.0151(2) Uani 1 1 d . . . C4 C 0.28240(11) 0.34931(6) 0.26052(7) 0.0141(2) Uani 1 1 d . . . C5 C 0.55049(11) 0.37476(6) 0.11071(7) 0.0146(2) Uani 1 1 d . . . C6 C 0.46653(13) 0.35156(8) 0.03680(7) 0.0224(3) Uani 1 1 d . . . H6A H 0.4434 0.2973 0.0404 0.034 Uiso 1 1 calc R . . H6B H 0.5197 0.3607 -0.0122 0.034 Uiso 1 1 calc R . . H6C H 0.3828 0.3819 0.0349 0.034 Uiso 1 1 calc R . . C7 C 0.59533(14) 0.45808(7) 0.09951(8) 0.0237(3) Uani 1 1 d . . . H7A H 0.5148 0.4906 0.0938 0.036 Uiso 1 1 calc R . . H7B H 0.6517 0.4623 0.0510 0.036 Uiso 1 1 calc R . . H7C H 0.6481 0.4745 0.1466 0.036 Uiso 1 1 calc R . . C8 C 0.67749(13) 0.32384(8) 0.11335(8) 0.0270(3) Uani 1 1 d . . . H8A H 0.7361 0.3397 0.1581 0.041 Uiso 1 1 calc R . . H8B H 0.7275 0.3287 0.0626 0.041 Uiso 1 1 calc R . . H8C H 0.6500 0.2706 0.1210 0.041 Uiso 1 1 calc R . . C9 C 0.64626(12) 0.39594(7) 0.30104(7) 0.0198(2) Uani 1 1 d . . . H9A H 0.7042 0.3505 0.3019 0.030 Uiso 1 1 calc R . . H9B H 0.6366 0.4159 0.3559 0.030 Uiso 1 1 calc R . . H9C H 0.6878 0.4349 0.2666 0.030 Uiso 1 1 calc R . . C10 C 0.38174(13) 0.36961(7) 0.40624(7) 0.0216(3) Uani 1 1 d . . . H10A H 0.2978 0.3958 0.4220 0.032 Uiso 1 1 calc R . . H10B H 0.4603 0.3985 0.4261 0.032 Uiso 1 1 calc R . . H10C H 0.3829 0.3182 0.4295 0.032 Uiso 1 1 calc R . . C11 C 0.13110(12) 0.33678(7) 0.27686(7) 0.0166(2) Uani 1 1 d . . . C12 C 0.05443(12) 0.31899(8) 0.19873(8) 0.0243(3) Uani 1 1 d . . . H12A H 0.0674 0.3609 0.1604 0.036 Uiso 1 1 calc R . . H12B H -0.0427 0.3132 0.2103 0.036 Uiso 1 1 calc R . . H12C H 0.0895 0.2715 0.1755 0.036 Uiso 1 1 calc R . . C13 C 0.06608(12) 0.40906(7) 0.31280(8) 0.0203(2) Uani 1 1 d . . . H13A H 0.1117 0.4220 0.3635 0.030 Uiso 1 1 calc R . . H13B H -0.0307 0.3997 0.3230 0.030 Uiso 1 1 calc R . . H13C H 0.0759 0.4515 0.2748 0.030 Uiso 1 1 calc R . . C14 C 0.10847(14) 0.26990(8) 0.33583(9) 0.0277(3) Uani 1 1 d . . . H14A H 0.1449 0.2229 0.3123 0.041 Uiso 1 1 calc R . . H14B H 0.0109 0.2638 0.3459 0.041 Uiso 1 1 calc R . . H14C H 0.1553 0.2806 0.3867 0.041 Uiso 1 1 calc R . . C15 C 0.22787(12) 0.16634(7) 0.07611(7) 0.0201(2) Uani 1 1 d . . . H15A H 0.2443 0.2220 0.0737 0.024 Uiso 1 1 calc R . . H15B H 0.1419 0.1557 0.0471 0.024 Uiso 1 1 calc R . . C16 C 0.34303(13) 0.12555(7) 0.03368(7) 0.0212(3) Uani 1 1 d . . . H16A H 0.3239 0.0701 0.0311 0.025 Uiso 1 1 calc R . . H16B H 0.3523 0.1450 -0.0220 0.025 Uiso 1 1 calc R . . C17 C 0.56605(12) 0.08258(7) 0.06073(7) 0.0194(2) Uani 1 1 d . . . H17A H 0.5768 0.0769 0.0017 0.023 Uiso 1 1 calc R . . H17B H 0.5374 0.0328 0.0831 0.023 Uiso 1 1 calc R . . C18 C 0.69890(12) 0.10627(7) 0.09771(7) 0.0208(2) Uani 1 1 d . . . H18A H 0.7694 0.0674 0.0865 0.025 Uiso 1 1 calc R . . H18B H 0.7291 0.1554 0.0743 0.025 Uiso 1 1 calc R . . C19 C 0.80515(12) 0.13025(8) 0.22209(8) 0.0245(3) Uani 1 1 d . . . H19A H 0.8434 0.1790 0.2023 0.029 Uiso 1 1 calc R . . H19B H 0.8720 0.0892 0.2115 0.029 Uiso 1 1 calc R . . C20 C 0.77648(13) 0.13556(7) 0.31060(8) 0.0232(3) Uani 1 1 d . . . H20A H 0.7296 0.0888 0.3292 0.028 Uiso 1 1 calc R . . H20B H 0.8627 0.1408 0.3410 0.028 Uiso 1 1 calc R . . C21 C 0.66727(13) 0.21508(7) 0.40693(7) 0.0223(3) Uani 1 1 d . . . H21A H 0.6140 0.2628 0.4117 0.027 Uiso 1 1 calc R . . H21B H 0.7552 0.2231 0.4348 0.027 Uiso 1 1 calc R . . C22 C 0.59107(14) 0.15157(8) 0.44881(8) 0.0258(3) Uani 1 1 d . . . H22A H 0.6471 0.1046 0.4497 0.031 Uiso 1 1 calc R . . H22B H 0.5709 0.1663 0.5051 0.031 Uiso 1 1 calc R . . C23 C 0.41637(13) 0.06335(8) 0.42016(8) 0.0244(3) Uani 1 1 d . . . H23A H 0.4091 0.0543 0.4789 0.029 Uiso 1 1 calc R . . H23B H 0.4797 0.0251 0.3974 0.029 Uiso 1 1 calc R . . C24 C 0.27911(13) 0.05491(8) 0.38167(7) 0.0232(3) Uani 1 1 d . . . H24A H 0.2440 0.0027 0.3910 0.028 Uiso 1 1 calc R . . H24B H 0.2146 0.0916 0.4060 0.028 Uiso 1 1 calc R . . C25 C 0.16339(12) 0.05229(7) 0.25865(7) 0.0184(2) Uani 1 1 d . . . H25A H 0.0909 0.0857 0.2803 0.022 Uiso 1 1 calc R . . H25B H 0.1373 -0.0015 0.2685 0.022 Uiso 1 1 calc R . . C26 C 0.18021(12) 0.06591(7) 0.17002(7) 0.0189(2) Uani 1 1 d . . . H26A H 0.2540 0.0333 0.1486 0.023 Uiso 1 1 calc R . . H26B H 0.0949 0.0531 0.1413 0.023 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 K 0.01523(12) 0.01270(11) 0.01491(11) -0.00004(9) -0.00150(8) -0.00005(9) N 0.0124(4) 0.0119(4) 0.0162(5) 0.0000(3) 0.0006(3) 0.0003(3) O1 0.0211(4) 0.0138(4) 0.0159(4) 0.0009(3) -0.0006(3) -0.0005(3) O2 0.0188(4) 0.0183(4) 0.0207(4) -0.0046(3) -0.0017(3) 0.0020(3) O3 0.0149(4) 0.0249(5) 0.0194(4) -0.0045(3) -0.0002(3) -0.0002(3) O4 0.0211(4) 0.0160(4) 0.0188(4) -0.0016(3) -0.0036(3) 0.0036(3) O5 0.0234(5) 0.0233(5) 0.0207(4) 0.0050(3) -0.0061(3) -0.0010(4) O6 0.0165(4) 0.0189(4) 0.0170(4) 0.0034(3) 0.0003(3) -0.0021(3) C1 0.0117(5) 0.0096(5) 0.0170(5) 0.0007(4) 0.0002(4) 0.0011(4) C2 0.0144(5) 0.0111(5) 0.0173(5) 0.0004(4) -0.0016(4) 0.0010(4) C3 0.0167(5) 0.0126(5) 0.0159(5) 0.0005(4) 0.0005(4) 0.0021(4) C4 0.0144(5) 0.0111(5) 0.0169(5) 0.0000(4) 0.0017(4) 0.0008(4) C5 0.0139(5) 0.0127(5) 0.0173(5) -0.0001(4) 0.0017(4) -0.0007(4) C6 0.0227(6) 0.0289(7) 0.0154(6) -0.0018(5) 0.0026(5) -0.0063(5) C7 0.0308(7) 0.0175(6) 0.0228(6) 0.0003(5) 0.0087(5) -0.0069(5) C8 0.0216(6) 0.0299(7) 0.0295(7) 0.0033(5) 0.0071(5) 0.0098(5) C9 0.0165(6) 0.0207(6) 0.0223(6) 0.0012(5) -0.0047(4) -0.0013(5) C10 0.0242(6) 0.0248(6) 0.0157(6) -0.0004(5) 0.0004(5) 0.0032(5) C11 0.0142(5) 0.0152(5) 0.0206(6) -0.0014(4) 0.0036(4) 0.0000(4) C12 0.0126(6) 0.0305(7) 0.0298(7) -0.0094(5) 0.0010(5) -0.0012(5) C13 0.0160(6) 0.0197(6) 0.0251(6) -0.0029(5) 0.0042(5) 0.0004(5) C14 0.0233(6) 0.0218(6) 0.0378(8) 0.0065(6) 0.0102(6) -0.0024(5) C15 0.0206(6) 0.0228(6) 0.0170(6) 0.0036(5) -0.0037(4) 0.0015(5) C16 0.0240(6) 0.0249(6) 0.0147(6) -0.0010(5) -0.0030(5) -0.0001(5) C17 0.0220(6) 0.0177(6) 0.0185(6) -0.0044(4) 0.0023(5) 0.0015(5) C18 0.0198(6) 0.0219(6) 0.0207(6) -0.0048(5) 0.0051(5) 0.0015(5) C19 0.0133(6) 0.0286(7) 0.0315(7) -0.0088(5) -0.0025(5) 0.0030(5) C20 0.0205(6) 0.0210(6) 0.0282(7) -0.0042(5) -0.0083(5) 0.0072(5) C21 0.0254(6) 0.0230(6) 0.0186(6) -0.0047(5) -0.0067(5) 0.0002(5) C22 0.0291(7) 0.0313(7) 0.0170(6) 0.0019(5) -0.0079(5) -0.0014(5) C23 0.0248(6) 0.0263(7) 0.0220(6) 0.0112(5) -0.0018(5) -0.0007(5) C24 0.0217(6) 0.0287(7) 0.0193(6) 0.0088(5) 0.0023(5) -0.0012(5) C25 0.0162(6) 0.0152(6) 0.0238(6) 0.0003(5) 0.0005(5) -0.0035(4) C26 0.0201(6) 0.0140(5) 0.0226(6) -0.0027(4) -0.0019(5) -0.0025(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 K O1 2.8085(8) . ? K O4 2.8206(8) . ? K O6 2.8825(8) . ? K O2 2.9331(8) . ? K O5 2.9420(9) . ? K O3 2.9559(9) . ? K N 3.0223(10) . ? K C1 3.0687(11) . ? K C4 3.0759(11) . ? K C3 3.1816(11) . ? K C2 3.1828(11) . ? K C15 3.5023(12) . ? N C1 1.3717(14) . ? N C4 1.3727(14) . ? O1 C15 1.4230(14) . ? O1 C26 1.4244(14) . ? O2 C17 1.4230(14) . ? O2 C16 1.4239(14) . ? O3 C18 1.4184(14) . ? O3 C19 1.4217(14) . ? O4 C20 1.4213(14) . ? O4 C21 1.4247(14) . ? O5 C23 1.4218(15) . ? O5 C22 1.4263(15) . ? O6 C24 1.4212(14) . ? O6 C25 1.4299(14) . ? C1 C2 1.4054(15) . ? C1 C5 1.5294(15) . ? C2 C3 1.4277(16) . ? C2 C9 1.5106(15) . ? C3 C4 1.4076(16) . ? C3 C10 1.5102(16) . ? C4 C11 1.5282(16) . ? C5 C6 1.5325(16) . ? C5 C8 1.5352(16) . ? C5 C7 1.5366(16) . ? C11 C12 1.5310(17) . ? C11 C13 1.5395(16) . ? C11 C14 1.5433(17) . ? C15 C16 1.5134(17) . ? C17 C18 1.5008(17) . ? C19 C20 1.4991(18) . ? C21 C22 1.5114(18) . ? C23 C24 1.4994(17) . ? C25 C26 1.4997(17) . ? 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 K O4 160.21(3) . . ? O1 K O6 58.26(2) . . ? O4 K O6 107.60(2) . . ? O1 K O2 58.90(2) . . ? O4 K O2 112.36(2) . . ? O6 K O2 93.16(2) . . ? O1 K O5 113.67(2) . . ? O4 K O5 58.57(2) . . ? O6 K O5 57.10(2) . . ? O2 K O5 136.26(3) . . ? O1 K O3 107.35(2) . . ? O4 K O3 57.95(2) . . ? O6 K O3 96.82(2) . . ? O2 K O3 56.06(2) . . ? O5 K O3 93.30(3) . . ? O1 K N 81.45(2) . . ? O4 K N 117.78(3) . . ? O6 K N 127.64(3) . . ? O2 K N 92.62(3) . . ? O5 K N 130.49(3) . . ? O3 K N 128.41(3) . . ? O1 K C1 104.30(3) . . ? O4 K C1 93.65(3) . . ? O6 K C1 153.07(3) . . ? O2 K C1 93.81(3) . . ? O5 K C1 127.67(3) . . ? O3 K C1 108.62(3) . . ? N K C1 26.02(3) . . ? O1 K C4 86.39(3) . . ? O4 K C4 112.89(3) . . ? O6 K C4 112.49(3) . . ? O2 K C4 116.45(3) . . ? O5 K C4 105.12(3) . . ? O3 K C4 150.49(3) . . ? N K C4 26.00(3) . . ? C1 K C4 41.91(3) . . ? O1 K C3 111.71(3) . . ? O4 K C3 87.17(3) . . ? O6 K C3 120.71(3) . . ? O2 K C3 134.40(3) . . ? O5 K C3 89.28(3) . . ? O3 K C3 135.91(3) . . ? N K C3 43.19(3) . . ? C1 K C3 42.33(3) . . ? C4 K C3 25.93(3) . . ? O1 K C2 124.34(3) . . ? O4 K C2 75.32(3) . . ? O6 K C2 146.07(3) . . ? O2 K C2 117.50(3) . . ? O5 K C2 101.96(3) . . ? O3 K C2 111.87(3) . . ? N K C2 43.22(3) . . ? C1 K C2 25.90(3) . . ? C4 K C2 42.38(3) . . ? C3 K C2 25.93(3) . . ? O1 K C15 22.85(3) . . ? O4 K C15 154.72(3) . . ? O6 K C15 79.22(3) . . ? O2 K C15 42.36(3) . . ? O5 K C15 135.96(3) . . ? O3 K C15 97.50(3) . . ? N K C15 71.00(3) . . ? C1 K C15 88.63(3) . . ? C4 K C15 85.23(3) . . ? C3 K C15 110.70(3) . . ? C2 K C15 112.98(3) . . ? C1 N C4 106.39(9) . . ? C1 N K 78.88(6) . . ? C4 N K 79.18(6) . . ? C15 O1 C26 114.72(9) . . ? C15 O1 K 107.13(6) . . ? C26 O1 K 116.22(6) . . ? C17 O2 C16 112.02(9) . . ? C17 O2 K 119.23(7) . . ? C16 O2 K 117.62(7) . . ? C18 O3 C19 111.69(9) . . ? C18 O3 K 118.77(7) . . ? C19 O3 K 115.36(7) . . ? C20 O4 C21 113.36(9) . . ? C20 O4 K 115.26(7) . . ? C21 O4 K 108.38(7) . . ? C23 O5 C22 111.82(9) . . ? C23 O5 K 117.30(7) . . ? C22 O5 K 118.35(7) . . ? C24 O6 C25 110.06(9) . . ? C24 O6 K 119.43(7) . . ? C25 O6 K 117.65(6) . . ? N C1 C2 111.08(10) . . ? N C1 C5 120.06(10) . . ? C2 C1 C5 128.81(10) . . ? N C1 K 75.10(6) . . ? C2 C1 K 81.59(6) . . ? C5 C1 K 112.47(7) . . ? C1 C2 C3 105.75(9) . . ? C1 C2 C9 129.06(10) . . ? C3 C2 C9 125.14(10) . . ? C1 C2 K 72.51(6) . . ? C3 C2 K 76.99(6) . . ? C9 C2 K 117.89(7) . . ? C4 C3 C2 106.01(10) . . ? C4 C3 C10 128.75(10) . . ? C2 C3 C10 125.21(10) . . ? C4 C3 K 72.84(6) . . ? C2 C3 K 77.09(6) . . ? C10 C3 K 116.77(7) . . ? N C4 C3 110.76(10) . . ? N C4 C11 120.11(10) . . ? C3 C4 C11 129.07(10) . . ? N C4 K 74.82(6) . . ? C3 C4 K 81.23(6) . . ? C11 C4 K 112.95(7) . . ? C1 C5 C6 110.54(9) . . ? C1 C5 C8 111.03(10) . . ? C6 C5 C8 107.79(10) . . ? C1 C5 C7 110.54(9) . . ? C6 C5 C7 108.03(10) . . ? C8 C5 C7 108.81(10) . . ? C4 C11 C12 110.92(10) . . ? C4 C11 C13 110.80(9) . . ? C12 C11 C13 106.96(10) . . ? C4 C11 C14 111.28(10) . . ? C12 C11 C14 108.14(10) . . ? C13 C11 C14 108.59(10) . . ? O1 C15 C16 113.34(10) . . ? O1 C15 K 50.03(5) . . ? C16 C15 K 89.71(7) . . ? O2 C16 C15 108.54(9) . . ? O2 C17 C18 109.47(9) . . ? O3 C18 C17 108.55(9) . . ? O3 C19 C20 107.90(10) . . ? O4 C20 C19 108.14(10) . . ? O4 C21 C22 113.56(10) . . ? O4 C21 K 49.15(5) . . ? C22 C21 K 89.31(7) . . ? O5 C22 C21 108.39(10) . . ? O5 C23 C24 109.79(10) . . ? O6 C24 C23 109.47(10) . . ? O6 C25 C26 108.29(9) . . ? O1 C26 C25 108.34(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 O1 K N C1 -151.32(6) . . . . ? O4 K N C1 23.73(7) . . . . ? O6 K N C1 170.66(6) . . . . ? O2 K N C1 -93.31(6) . . . . ? O5 K N C1 94.76(7) . . . . ? O3 K N C1 -45.92(7) . . . . ? C4 K N C1 109.29(9) . . . . ? C3 K N C1 73.72(7) . . . . ? C2 K N C1 35.47(6) . . . . ? C15 K N C1 -130.37(7) . . . . ? O1 K N C4 99.39(6) . . . . ? O4 K N C4 -85.56(6) . . . . ? O6 K N C4 61.37(7) . . . . ? O2 K N C4 157.40(6) . . . . ? O5 K N C4 -14.53(7) . . . . ? O3 K N C4 -155.21(6) . . . . ? C1 K N C4 -109.29(9) . . . . ? C3 K N C4 -35.57(6) . . . . ? C2 K N C4 -73.82(7) . . . . ? C15 K N C4 120.34(6) . . . . ? O4 K O1 C15 -106.40(9) . . . . ? O6 K O1 C15 -154.41(7) . . . . ? O2 K O1 C15 -37.74(6) . . . . ? O5 K O1 C15 -168.80(7) . . . . ? O3 K O1 C15 -67.10(7) . . . . ? N K O1 C15 60.58(7) . . . . ? C1 K O1 C15 48.04(7) . . . . ? C4 K O1 C15 86.26(7) . . . . ? C3 K O1 C15 92.00(7) . . . . ? C2 K O1 C15 66.21(7) . . . . ? O4 K O1 C26 23.36(12) . . . . ? O6 K O1 C26 -24.66(7) . . . . ? O2 K O1 C26 92.02(7) . . . . ? O5 K O1 C26 -39.05(8) . . . . ? O3 K O1 C26 62.66(7) . . . . ? N K O1 C26 -169.66(7) . . . . ? C1 K O1 C26 177.79(7) . . . . ? C4 K O1 C26 -143.98(7) . . . . ? C3 K O1 C26 -138.24(7) . . . . ? C2 K O1 C26 -164.03(7) . . . . ? C15 K O1 C26 129.76(11) . . . . ? O1 K O2 C17 -129.44(8) . . . . ? O4 K O2 C17 30.62(8) . . . . ? O6 K O2 C17 -79.88(8) . . . . ? O5 K O2 C17 -36.70(9) . . . . ? O3 K O2 C17 16.22(7) . . . . ? N K O2 C17 152.18(8) . . . . ? C1 K O2 C17 126.15(8) . . . . ? C4 K O2 C17 163.03(7) . . . . ? C3 K O2 C17 139.77(8) . . . . ? C2 K O2 C17 115.18(8) . . . . ? C15 K O2 C17 -150.09(9) . . . . ? O1 K O2 C16 11.62(7) . . . . ? O4 K O2 C16 171.67(7) . . . . ? O6 K O2 C16 61.17(8) . . . . ? O5 K O2 C16 104.35(8) . . . . ? O3 K O2 C16 157.27(9) . . . . ? N K O2 C16 -66.76(8) . . . . ? C1 K O2 C16 -92.79(8) . . . . ? C4 K O2 C16 -55.92(8) . . . . ? C3 K O2 C16 -79.17(9) . . . . ? C2 K O2 C16 -103.76(8) . . . . ? C15 K O2 C16 -9.03(7) . . . . ? O1 K O3 C18 47.95(8) . . . . ? O4 K O3 C18 -146.71(9) . . . . ? O6 K O3 C18 106.77(8) . . . . ? O2 K O3 C18 17.54(7) . . . . ? O5 K O3 C18 164.01(8) . . . . ? N K O3 C18 -44.86(9) . . . . ? C1 K O3 C18 -64.28(8) . . . . ? C4 K O3 C18 -66.77(10) . . . . ? C3 K O3 C18 -103.61(8) . . . . ? C2 K O3 C18 -91.71(8) . . . . ? C15 K O3 C18 26.80(8) . . . . ? O1 K O3 C19 -175.44(8) . . . . ? O4 K O3 C19 -10.10(8) . . . . ? O6 K O3 C19 -116.62(8) . . . . ? O2 K O3 C19 154.15(9) . . . . ? O5 K O3 C19 -59.38(8) . . . . ? N K O3 C19 91.75(8) . . . . ? C1 K O3 C19 72.33(8) . . . . ? C4 K O3 C19 69.84(10) . . . . ? C3 K O3 C19 33.00(10) . . . . ? C2 K O3 C19 44.91(9) . . . . ? C15 K O3 C19 163.41(8) . . . . ? O1 K O4 C20 19.81(12) . . . . ? O6 K O4 C20 61.35(8) . . . . ? O2 K O4 C20 -39.78(8) . . . . ? O5 K O4 C20 91.84(8) . . . . ? O3 K O4 C20 -25.69(8) . . . . ? N K O4 C20 -145.61(8) . . . . ? C1 K O4 C20 -135.42(8) . . . . ? C4 K O4 C20 -173.92(8) . . . . ? C3 K O4 C20 -177.27(8) . . . . ? C2 K O4 C20 -153.89(8) . . . . ? C15 K O4 C20 -40.90(11) . . . . ? O1 K O4 C21 -108.42(9) . . . . ? O6 K O4 C21 -66.88(7) . . . . ? O2 K O4 C21 -168.01(7) . . . . ? O5 K O4 C21 -36.39(7) . . . . ? O3 K O4 C21 -153.92(8) . . . . ? N K O4 C21 86.16(7) . . . . ? C1 K O4 C21 96.35(7) . . . . ? C4 K O4 C21 57.84(8) . . . . ? C3 K O4 C21 54.50(7) . . . . ? C2 K O4 C21 77.88(7) . . . . ? C15 K O4 C21 -169.13(8) . . . . ? O1 K O5 C23 30.57(9) . . . . ? O4 K O5 C23 -128.84(9) . . . . ? O6 K O5 C23 15.99(7) . . . . ? O2 K O5 C23 -38.47(9) . . . . ? O3 K O5 C23 -80.00(8) . . . . ? N K O5 C23 129.83(8) . . . . ? C1 K O5 C23 163.35(8) . . . . ? C4 K O5 C23 123.28(8) . . . . ? C3 K O5 C23 144.05(8) . . . . ? C2 K O5 C23 166.82(8) . . . . ? C15 K O5 C23 24.35(10) . . . . ? O1 K O5 C22 169.49(8) . . . . ? O4 K O5 C22 10.08(8) . . . . ? O6 K O5 C22 154.91(9) . . . . ? O2 K O5 C22 100.44(9) . . . . ? O3 K O5 C22 58.91(9) . . . . ? N K O5 C22 -91.26(9) . . . . ? C1 K O5 C22 -57.74(9) . . . . ? C4 K O5 C22 -97.80(9) . . . . ? C3 K O5 C22 -77.04(9) . . . . ? C2 K O5 C22 -54.26(9) . . . . ? C15 K O5 C22 163.26(8) . . . . ? O1 K O6 C24 -147.38(8) . . . . ? O4 K O6 C24 47.93(8) . . . . ? O2 K O6 C24 162.59(8) . . . . ? O5 K O6 C24 16.89(7) . . . . ? O3 K O6 C24 106.41(8) . . . . ? N K O6 C24 -101.64(8) . . . . ? C1 K O6 C24 -92.59(10) . . . . ? C4 K O6 C24 -77.03(8) . . . . ? C3 K O6 C24 -49.43(8) . . . . ? C2 K O6 C24 -41.80(10) . . . . ? C15 K O6 C24 -157.21(8) . . . . ? O1 K O6 C25 -9.64(7) . . . . ? O4 K O6 C25 -174.33(7) . . . . ? O2 K O6 C25 -59.66(7) . . . . ? O5 K O6 C25 154.63(8) . . . . ? O3 K O6 C25 -115.84(7) . . . . ? N K O6 C25 36.11(8) . . . . ? C1 K O6 C25 45.15(10) . . . . ? C4 K O6 C25 60.71(8) . . . . ? C3 K O6 C25 88.32(8) . . . . ? C2 K O6 C25 95.95(8) . . . . ? C15 K O6 C25 -19.47(7) . . . . ? C4 N C1 C2 0.45(12) . . . . ? K N C1 C2 -74.65(8) . . . . ? C4 N C1 C5 -177.27(9) . . . . ? K N C1 C5 107.63(9) . . . . ? C4 N C1 K 75.10(7) . . . . ? O1 K C1 N 29.32(6) . . . . ? O4 K C1 N -159.10(6) . . . . ? O6 K C1 N -16.49(10) . . . . ? O2 K C1 N 88.17(6) . . . . ? O5 K C1 N -106.75(6) . . . . ? O3 K C1 N 143.56(6) . . . . ? C4 K C1 N -38.27(6) . . . . ? C3 K C1 N -77.36(7) . . . . ? C2 K C1 N -114.56(9) . . . . ? C15 K C1 N 46.11(6) . . . . ? O1 K C1 C2 143.88(6) . . . . ? O4 K C1 C2 -44.54(6) . . . . ? O6 K C1 C2 98.07(8) . . . . ? O2 K C1 C2 -157.27(6) . . . . ? O5 K C1 C2 7.81(8) . . . . ? O3 K C1 C2 -101.88(6) . . . . ? N K C1 C2 114.56(9) . . . . ? C4 K C1 C2 76.28(7) . . . . ? C3 K C1 C2 37.20(6) . . . . ? C15 K C1 C2 160.66(7) . . . . ? O1 K C1 C5 -87.49(7) . . . . ? O4 K C1 C5 84.10(7) . . . . ? O6 K C1 C5 -133.29(7) . . . . ? O2 K C1 C5 -28.63(7) . . . . ? O5 K C1 C5 136.45(7) . . . . ? O3 K C1 C5 26.75(8) . . . . ? N K C1 C5 -116.81(10) . . . . ? C4 K C1 C5 -155.08(9) . . . . ? C3 K C1 C5 165.84(9) . . . . ? C2 K C1 C5 128.64(11) . . . . ? C15 K C1 C5 -70.70(7) . . . . ? N C1 C2 C3 -0.09(12) . . . . ? C5 C1 C2 C3 177.38(10) . . . . ? K C1 C2 C3 -70.48(8) . . . . ? N C1 C2 C9 -177.52(11) . . . . ? C5 C1 C2 C9 -0.05(19) . . . . ? K C1 C2 C9 112.09(12) . . . . ? N C1 C2 K 70.40(8) . . . . ? C5 C1 C2 K -112.13(11) . . . . ? O1 K C2 C1 -43.78(7) . . . . ? O4 K C2 C1 133.64(7) . . . . ? O6 K C2 C1 -126.54(7) . . . . ? O2 K C2 C1 25.76(7) . . . . ? O5 K C2 C1 -173.69(6) . . . . ? O3 K C2 C1 87.77(6) . . . . ? N K C2 C1 -35.63(6) . . . . ? C4 K C2 C1 -74.28(7) . . . . ? C3 K C2 C1 -111.40(9) . . . . ? C15 K C2 C1 -21.08(7) . . . . ? O1 K C2 C3 67.62(7) . . . . ? O4 K C2 C3 -114.96(7) . . . . ? O6 K C2 C3 -15.14(9) . . . . ? O2 K C2 C3 137.16(6) . . . . ? O5 K C2 C3 -62.29(7) . . . . ? O3 K C2 C3 -160.83(6) . . . . ? N K C2 C3 75.76(7) . . . . ? C1 K C2 C3 111.40(9) . . . . ? C4 K C2 C3 37.11(6) . . . . ? C15 K C2 C3 90.32(7) . . . . ? O1 K C2 C9 -169.28(7) . . . . ? O4 K C2 C9 8.14(8) . . . . ? O6 K C2 C9 107.96(9) . . . . ? O2 K C2 C9 -99.74(8) . . . . ? O5 K C2 C9 60.81(8) . . . . ? O3 K C2 C9 -37.73(9) . . . . ? N K C2 C9 -161.14(10) . . . . ? C1 K C2 C9 -125.50(11) . . . . ? C4 K C2 C9 160.22(10) . . . . ? C3 K C2 C9 123.10(11) . . . . ? C15 K C2 C9 -146.58(8) . . . . ? C1 C2 C3 C4 -0.31(12) . . . . ? C9 C2 C3 C4 177.26(10) . . . . ? K C2 C3 C4 -67.62(8) . . . . ? C1 C2 C3 C10 -178.86(11) . . . . ? C9 C2 C3 C10 -1.30(18) . . . . ? K C2 C3 C10 113.82(11) . . . . ? C1 C2 C3 K 67.32(7) . . . . ? C9 C2 C3 K -115.12(11) . . . . ? O1 K C3 C4 -13.20(7) . . . . ? O4 K C3 C4 172.94(7) . . . . ? O6 K C3 C4 -78.23(7) . . . . ? O2 K C3 C4 53.95(8) . . . . ? O5 K C3 C4 -128.49(7) . . . . ? O3 K C3 C4 137.50(6) . . . . ? N K C3 C4 35.67(6) . . . . ? C1 K C3 C4 74.37(7) . . . . ? C2 K C3 C4 111.53(9) . . . . ? C15 K C3 C4 11.30(7) . . . . ? O1 K C3 C2 -124.73(6) . . . . ? O4 K C3 C2 61.41(6) . . . . ? O6 K C3 C2 170.24(6) . . . . ? O2 K C3 C2 -57.58(8) . . . . ? O5 K C3 C2 119.98(6) . . . . ? O3 K C3 C2 25.97(8) . . . . ? N K C3 C2 -75.86(7) . . . . ? C1 K C3 C2 -37.16(6) . . . . ? C4 K C3 C2 -111.53(9) . . . . ? C15 K C3 C2 -100.23(6) . . . . ? O1 K C3 C10 112.11(8) . . . . ? O4 K C3 C10 -61.75(8) . . . . ? O6 K C3 C10 47.08(9) . . . . ? O2 K C3 C10 179.26(7) . . . . ? O5 K C3 C10 -3.18(8) . . . . ? O3 K C3 C10 -97.18(9) . . . . ? N K C3 C10 160.98(10) . . . . ? C1 K C3 C10 -160.32(10) . . . . ? C4 K C3 C10 125.31(12) . . . . ? C2 K C3 C10 -123.16(11) . . . . ? C15 K C3 C10 136.62(8) . . . . ? C1 N C4 C3 -0.66(12) . . . . ? K N C4 C3 74.22(8) . . . . ? C1 N C4 C11 177.08(10) . . . . ? K N C4 C11 -108.04(10) . . . . ? C1 N C4 K -74.88(7) . . . . ? C2 C3 C4 N 0.61(13) . . . . ? C10 C3 C4 N 179.09(11) . . . . ? K C3 C4 N -70.01(8) . . . . ? C2 C3 C4 C11 -176.87(11) . . . . ? C10 C3 C4 C11 1.6(2) . . . . ? K C3 C4 C11 112.51(12) . . . . ? C2 C3 C4 K 70.61(8) . . . . ? C10 C3 C4 K -110.90(12) . . . . ? O1 K C4 N -77.85(6) . . . . ? O4 K C4 N 106.77(6) . . . . ? O6 K C4 N -131.22(6) . . . . ? O2 K C4 N -25.39(7) . . . . ? O5 K C4 N 168.60(6) . . . . ? O3 K C4 N 41.83(9) . . . . ? C1 K C4 N 38.30(6) . . . . ? C3 K C4 N 114.43(9) . . . . ? C2 K C4 N 77.32(7) . . . . ? C15 K C4 N -54.97(6) . . . . ? O1 K C4 C3 167.72(7) . . . . ? O4 K C4 C3 -7.65(7) . . . . ? O6 K C4 C3 114.36(6) . . . . ? O2 K C4 C3 -139.82(6) . . . . ? O5 K C4 C3 54.17(7) . . . . ? O3 K C4 C3 -72.60(9) . . . . ? N K C4 C3 -114.43(9) . . . . ? C1 K C4 C3 -76.13(7) . . . . ? C2 K C4 C3 -37.11(6) . . . . ? C15 K C4 C3 -169.40(7) . . . . ? O1 K C4 C11 38.87(7) . . . . ? O4 K C4 C11 -136.50(7) . . . . ? O6 K C4 C11 -14.49(8) . . . . ? O2 K C4 C11 91.33(8) . . . . ? O5 K C4 C11 -74.68(8) . . . . ? O3 K C4 C11 158.56(7) . . . . ? N K C4 C11 116.72(10) . . . . ? C1 K C4 C11 155.02(10) . . . . ? C3 K C4 C11 -128.85(11) . . . . ? C2 K C4 C11 -165.96(10) . . . . ? C15 K C4 C11 61.75(8) . . . . ? N C1 C5 C6 -8.42(14) . . . . ? C2 C1 C5 C6 174.31(11) . . . . ? K C1 C5 C6 76.87(10) . . . . ? N C1 C5 C8 -128.00(11) . . . . ? C2 C1 C5 C8 54.73(15) . . . . ? K C1 C5 C8 -42.71(11) . . . . ? N C1 C5 C7 111.14(12) . . . . ? C2 C1 C5 C7 -66.13(15) . . . . ? K C1 C5 C7 -163.57(8) . . . . ? N C4 C11 C12 5.28(15) . . . . ? C3 C4 C11 C12 -177.44(11) . . . . ? K C4 C11 C12 -79.94(10) . . . . ? N C4 C11 C13 -113.35(12) . . . . ? C3 C4 C11 C13 63.92(15) . . . . ? K C4 C11 C13 161.42(7) . . . . ? N C4 C11 C14 125.72(11) . . . . ? C3 C4 C11 C14 -57.00(16) . . . . ? K C4 C11 C14 40.50(11) . . . . ? C26 O1 C15 C16 -62.26(13) . . . . ? K O1 C15 C16 68.35(10) . . . . ? C26 O1 C15 K -130.60(10) . . . . ? O4 K C15 O1 130.48(7) . . . . ? O6 K C15 O1 21.96(6) . . . . ? O2 K C15 O1 128.94(8) . . . . ? O5 K C15 O1 14.82(9) . . . . ? O3 K C15 O1 117.52(7) . . . . ? N K C15 O1 -114.35(7) . . . . ? C1 K C15 O1 -133.88(7) . . . . ? C4 K C15 O1 -92.04(7) . . . . ? C3 K C15 O1 -96.98(7) . . . . ? C2 K C15 O1 -124.84(7) . . . . ? O1 K C15 C16 -121.42(11) . . . . ? O4 K C15 C16 9.06(11) . . . . ? O6 K C15 C16 -99.46(7) . . . . ? O2 K C15 C16 7.52(6) . . . . ? O5 K C15 C16 -106.60(7) . . . . ? O3 K C15 C16 -3.90(7) . . . . ? N K C15 C16 124.23(7) . . . . ? C1 K C15 C16 104.70(7) . . . . ? C4 K C15 C16 146.54(7) . . . . ? C3 K C15 C16 141.60(7) . . . . ? C2 K C15 C16 113.74(7) . . . . ? C17 O2 C16 C15 158.69(10) . . . . ? K O2 C16 C15 14.97(12) . . . . ? O1 C15 C16 O2 -56.47(13) . . . . ? K C15 C16 O2 -11.05(9) . . . . ? C16 O2 C17 C18 170.91(10) . . . . ? K O2 C17 C18 -46.02(11) . . . . ? C19 O3 C18 C17 175.11(10) . . . . ? K O3 C18 C17 -46.81(12) . . . . ? O2 C17 C18 O3 59.39(13) . . . . ? C18 O3 C19 C20 -178.62(10) . . . . ? K O3 C19 C20 41.77(12) . . . . ? C21 O4 C20 C19 -175.23(10) . . . . ? K O4 C20 C19 59.06(11) . . . . ? O3 C19 C20 O4 -66.32(13) . . . . ? C20 O4 C21 C22 -62.53(13) . . . . ? K O4 C21 C22 66.77(11) . . . . ? C20 O4 C21 K -129.30(10) . . . . ? O1 K C21 O4 129.05(8) . . . . ? O6 K C21 O4 117.76(7) . . . . ? O2 K C21 O4 15.54(9) . . . . ? O5 K C21 O4 130.71(9) . . . . ? O3 K C21 O4 22.35(7) . . . . ? N K C21 O4 -104.78(7) . . . . ? C1 K C21 O4 -85.52(7) . . . . ? C4 K C21 O4 -127.65(7) . . . . ? C3 K C21 O4 -122.45(7) . . . . ? C2 K C21 O4 -95.48(7) . . . . ? C15 K C21 O4 62.4(3) . . . . ? O1 K C21 C22 6.44(12) . . . . ? O4 K C21 C22 -122.61(11) . . . . ? O6 K C21 C22 -4.85(8) . . . . ? O2 K C21 C22 -107.07(8) . . . . ? O5 K C21 C22 8.10(7) . . . . ? O3 K C21 C22 -100.26(8) . . . . ? N K C21 C22 132.62(7) . . . . ? C1 K C21 C22 151.87(8) . . . . ? C4 K C21 C22 109.74(8) . . . . ? C3 K C21 C22 114.94(8) . . . . ? C2 K C21 C22 141.91(8) . . . . ? C15 K C21 C22 -60.2(3) . . . . ? C23 O5 C22 C21 157.25(11) . . . . ? K O5 C22 C21 16.23(13) . . . . ? O4 C21 C22 O5 -55.84(14) . . . . ? K C21 C22 O5 -11.80(10) . . . . ? C22 O5 C23 C24 173.59(11) . . . . ? K O5 C23 C24 -44.95(12) . . . . ? C25 O6 C24 C23 173.29(10) . . . . ? K O6 C24 C23 -46.06(12) . . . . ? O5 C23 C24 O6 58.77(14) . . . . ? C24 O6 C25 C26 -178.71(10) . . . . ? K O6 C25 C26 39.86(11) . . . . ? C15 O1 C26 C25 -178.22(9) . . . . ? K O1 C26 C25 55.75(10) . . . . ? O6 C25 C26 O1 -61.77(12) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.336 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.041 _iucr_refine_instructions_details ; TITL MK69 in P2(1)/n CELL 0.71073 9.830420 17.525062 16.597971 90.0000 90.0833 90.0000 ZERR 4.00 0.000200 0.000400 0.000300 0.0000 0.0020 0.0000 LATT 1 SYMM -x+1/2, y+1/2,-z+1/2 SFAC C H N O K UNIT 104.00 192.00 4.00 24.00 4.00 MERG 2 FMAP 2 PLAN 10 TEMP -173 SIZE 0.25 0.2 0.1 SHEL 999 0.75 ACTA CONF L.S. 10 WGHT 0.032400 1.168600 FVAR 2.88712 K 5 0.441366 0.199213 0.241614 11.00000 0.01523 0.01270 = 0.01491 -0.00004 -0.00150 -0.00005 N 3 0.330073 0.350055 0.182829 11.00000 0.01243 0.01192 = 0.01624 -0.00003 0.00063 0.00027 O1 4 0.212763 0.144304 0.158121 11.00000 0.02109 0.01378 = 0.01593 0.00089 -0.00061 -0.00055 O2 4 0.465447 0.138753 0.077474 11.00000 0.01883 0.01833 = 0.02075 -0.00463 -0.00167 0.00201 O3 4 0.680502 0.114061 0.182054 11.00000 0.01494 0.02490 = 0.01936 -0.00449 -0.00016 -0.00020 O4 4 0.692630 0.200407 0.323869 11.00000 0.02108 0.01598 = 0.01882 -0.00162 -0.00359 0.00355 O5 4 0.467526 0.138028 0.405966 11.00000 0.02341 0.02326 = 0.02067 0.00503 -0.00610 -0.00100 O6 4 0.289893 0.068775 0.297557 11.00000 0.01648 0.01893 = 0.01704 0.00335 0.00032 -0.00210 C1 1 0.466421 0.366089 0.187632 11.00000 0.01168 0.00960 = 0.01703 0.00070 0.00022 0.00110 C2 1 0.507757 0.375190 0.268154 11.00000 0.01443 0.01106 = 0.01727 0.00038 -0.00159 0.00102 C3 1 0.388303 0.364029 0.315535 11.00000 0.01670 0.01260 = 0.01589 0.00051 0.00055 0.00208 C4 1 0.282405 0.349314 0.260519 11.00000 0.01435 0.01108 = 0.01692 0.00000 0.00166 0.00077 C5 1 0.550488 0.374761 0.110713 11.00000 0.01390 0.01272 = 0.01726 -0.00008 0.00168 -0.00070 C6 1 0.466534 0.351562 0.036797 11.00000 0.02272 0.02890 = 0.01544 -0.00183 0.00262 -0.00634 AFIX 137 H6A 2 0.443448 0.297270 0.040390 11.00000 -1.50000 H6B 2 0.519673 0.360725 -0.012168 11.00000 -1.50000 H6C 2 0.382796 0.381856 0.034901 11.00000 -1.50000 AFIX 0 C7 1 0.595331 0.458077 0.099506 11.00000 0.03081 0.01746 = 0.02279 0.00031 0.00869 -0.00686 AFIX 137 H7A 2 0.514849 0.490635 0.093757 11.00000 -1.50000 H7B 2 0.651657 0.462281 0.051041 11.00000 -1.50000 H7C 2 0.648086 0.474452 0.146572 11.00000 -1.50000 AFIX 0 C8 1 0.677492 0.323837 0.113353 11.00000 0.02165 0.02993 = 0.02945 0.00327 0.00713 0.00979 AFIX 137 H8A 2 0.736052 0.339719 0.158147 11.00000 -1.50000 H8B 2 0.727450 0.328709 0.062561 11.00000 -1.50000 H8C 2 0.650044 0.270576 0.121035 11.00000 -1.50000 AFIX 0 C9 1 0.646265 0.395942 0.301036 11.00000 0.01645 0.02073 = 0.02228 0.00116 -0.00466 -0.00135 AFIX 137 H9A 2 0.704227 0.350452 0.301924 11.00000 -1.50000 H9B 2 0.636635 0.415903 0.355885 11.00000 -1.50000 H9C 2 0.687790 0.434934 0.266629 11.00000 -1.50000 AFIX 0 C10 1 0.381743 0.369606 0.406244 11.00000 0.02424 0.02481 = 0.01570 -0.00040 0.00038 0.00322 AFIX 137 H10A 2 0.297763 0.395750 0.421990 11.00000 -1.50000 H10B 2 0.460349 0.398463 0.426069 11.00000 -1.50000 H10C 2 0.382860 0.318225 0.429536 11.00000 -1.50000 AFIX 0 C11 1 0.131097 0.336777 0.276857 11.00000 0.01415 0.01523 = 0.02056 -0.00139 0.00363 0.00000 C12 1 0.054427 0.318987 0.198728 11.00000 0.01256 0.03050 = 0.02982 -0.00945 0.00104 -0.00118 AFIX 137 H12A 2 0.067398 0.360866 0.160374 11.00000 -1.50000 H12B 2 -0.042738 0.313177 0.210339 11.00000 -1.50000 H12C 2 0.089545 0.271530 0.175460 11.00000 -1.50000 AFIX 0 C13 1 0.066081 0.409059 0.312802 11.00000 0.01602 0.01969 = 0.02515 -0.00293 0.00422 0.00039 AFIX 137 H13A 2 0.111677 0.421964 0.363548 11.00000 -1.50000 H13B 2 -0.030684 0.399750 0.322964 11.00000 -1.50000 H13C 2 0.075866 0.451475 0.274773 11.00000 -1.50000 AFIX 0 C14 1 0.108472 0.269903 0.335830 11.00000 0.02333 0.02184 = 0.03782 0.00653 0.01019 -0.00239 AFIX 137 H14A 2 0.144880 0.222859 0.312327 11.00000 -1.50000 H14B 2 0.010869 0.263753 0.345863 11.00000 -1.50000 H14C 2 0.155298 0.280632 0.386749 11.00000 -1.50000 AFIX 0 C15 1 0.227875 0.166336 0.076106 11.00000 0.02056 0.02275 = 0.01700 0.00363 -0.00370 0.00155 AFIX 23 H15A 2 0.244335 0.222018 0.073660 11.00000 -1.20000 H15B 2 0.141859 0.155734 0.047101 11.00000 -1.20000 AFIX 0 C16 1 0.343026 0.125554 0.033682 11.00000 0.02402 0.02490 = 0.01475 -0.00102 -0.00301 -0.00014 AFIX 23 H16A 2 0.323934 0.070142 0.031065 11.00000 -1.20000 H16B 2 0.352309 0.145032 -0.022028 11.00000 -1.20000 AFIX 0 C17 1 0.566049 0.082585 0.060726 11.00000 0.02199 0.01774 = 0.01851 -0.00439 0.00231 0.00147 AFIX 23 H17A 2 0.576801 0.076871 0.001738 11.00000 -1.20000 H17B 2 0.537378 0.032767 0.083116 11.00000 -1.20000 AFIX 0 C18 1 0.698902 0.106268 0.097709 11.00000 0.01975 0.02194 = 0.02067 -0.00477 0.00512 0.00152 AFIX 23 H18A 2 0.769394 0.067356 0.086523 11.00000 -1.20000 H18B 2 0.729127 0.155389 0.074342 11.00000 -1.20000 AFIX 0 C19 1 0.805148 0.130251 0.222093 11.00000 0.01334 0.02862 = 0.03147 -0.00881 -0.00245 0.00305 AFIX 23 H19A 2 0.843353 0.179019 0.202272 11.00000 -1.20000 H19B 2 0.871980 0.089203 0.211548 11.00000 -1.20000 AFIX 0 C20 1 0.776476 0.135556 0.310600 11.00000 0.02051 0.02101 = 0.02815 -0.00421 -0.00825 0.00715 AFIX 23 H20A 2 0.729600 0.088793 0.329242 11.00000 -1.20000 H20B 2 0.862690 0.140785 0.341004 11.00000 -1.20000 AFIX 0 C21 1 0.667267 0.215076 0.406928 11.00000 0.02543 0.02297 = 0.01855 -0.00466 -0.00666 0.00019 AFIX 23 H21A 2 0.614044 0.262816 0.411701 11.00000 -1.20000 H21B 2 0.755250 0.223098 0.434762 11.00000 -1.20000 AFIX 0 C22 1 0.591071 0.151570 0.448808 11.00000 0.02907 0.03126 = 0.01698 0.00188 -0.00794 -0.00144 AFIX 23 H22A 2 0.647104 0.104637 0.449670 11.00000 -1.20000 H22B 2 0.570882 0.166301 0.505117 11.00000 -1.20000 AFIX 0 C23 1 0.416369 0.063353 0.420159 11.00000 0.02479 0.02631 = 0.02199 0.01122 -0.00175 -0.00074 AFIX 23 H23A 2 0.409094 0.054265 0.478864 11.00000 -1.20000 H23B 2 0.479733 0.025105 0.397447 11.00000 -1.20000 AFIX 0 C24 1 0.279112 0.054909 0.381667 11.00000 0.02166 0.02872 = 0.01927 0.00880 0.00230 -0.00123 AFIX 23 H24A 2 0.243975 0.002719 0.391011 11.00000 -1.20000 H24B 2 0.214620 0.091635 0.406005 11.00000 -1.20000 AFIX 0 C25 1 0.163386 0.052291 0.258650 11.00000 0.01625 0.01520 = 0.02376 0.00027 0.00051 -0.00349 AFIX 23 H25A 2 0.090888 0.085668 0.280313 11.00000 -1.20000 H25B 2 0.137319 -0.001465 0.268517 11.00000 -1.20000 AFIX 0 C26 1 0.180208 0.065913 0.170022 11.00000 0.02008 0.01398 = 0.02255 -0.00270 -0.00194 -0.00248 AFIX 23 H26A 2 0.253962 0.033280 0.148582 11.00000 -1.20000 H26B 2 0.094938 0.053078 0.141251 11.00000 -1.20000 HKLF 4 ; data_mwal21 _database_code_depnum_ccdc_archive 'CCDC 902360' #TrackingRef 'mwal21.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H27 N Zr' _chemical_formula_weight 360.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zr Zr -0.1862 2.2449 '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' 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 6.4001(2) _cell_length_b 29.9375(12) _cell_length_c 9.3920(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.842(4) _cell_angle_gamma 90.00 _cell_volume 1747.28(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9084 _cell_measurement_theta_min 4.4270 _cell_measurement_theta_max 75.8948 _exptl_crystal_description plate _exptl_crystal_colour violet _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 5.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.16026 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23478 _diffrn_reflns_av_R_equivalents 0.0705 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.07 _diffrn_reflns_theta_max 76.09 _reflns_number_total 3589 _reflns_number_gt 3014 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER XP' _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. The hydrogens of the seven-membered ring and of the C9 and C10 atoms were refined freely. For the freely refined H atoms, CH distances were restrained equal. The methyls were refined using a rigid model. ; _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^)+(0.0221P)^2^+1.5742P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3589 _refine_ls_number_parameters 232 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0718 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.039 _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 Zr Zr 0.34048(4) 0.156514(8) 0.35673(3) 0.01743(7) Uani 1 1 d . . . N N 0.5922(4) 0.09870(8) 0.4577(2) 0.0176(5) Uani 1 1 d . . . C1 C 0.4143(5) 0.20479(11) 0.1768(3) 0.0259(7) Uani 1 1 d D . . H1 H 0.527(4) 0.2026(12) 0.128(4) 0.033(10) Uiso 1 1 d D . . C2 C 0.2257(5) 0.18007(11) 0.1128(3) 0.0258(7) Uani 1 1 d D . . H2 H 0.228(6) 0.1652(11) 0.025(3) 0.037(11) Uiso 1 1 d D . . C3 C 0.0413(5) 0.17247(11) 0.1686(3) 0.0250(7) Uani 1 1 d D . . H3 H -0.058(5) 0.1520(10) 0.115(3) 0.029(10) Uiso 1 1 d D . . C4 C 0.0002(5) 0.18824(11) 0.3022(3) 0.0243(6) Uani 1 1 d D . . H4 H -0.127(4) 0.1772(10) 0.323(3) 0.018(8) Uiso 1 1 d D . . C5 C 0.1331(5) 0.21479(10) 0.4128(3) 0.0252(7) Uani 1 1 d D . . H5 H 0.081(5) 0.2184(12) 0.497(3) 0.032(10) Uiso 1 1 d D . . C6 C 0.3405(6) 0.23243(10) 0.4178(4) 0.0260(7) Uani 1 1 d D . . H6 H 0.414(5) 0.2453(11) 0.506(2) 0.025(9) Uiso 1 1 d D . . C7 C 0.4655(5) 0.22789(10) 0.3131(4) 0.0258(7) Uani 1 1 d D . . H7 H 0.606(3) 0.2387(12) 0.344(4) 0.035(11) Uiso 1 1 d D . . C8 C 0.4244(5) 0.07589(9) 0.3663(3) 0.0180(6) Uani 1 1 d . . . C9 C 0.2411(5) 0.07799(10) 0.4229(3) 0.0226(6) Uani 1 1 d D . . H9 H 0.108(4) 0.0653(12) 0.379(4) 0.032(10) Uiso 1 1 d D . . C10 C 0.3006(5) 0.10192(10) 0.5564(3) 0.0203(6) Uani 1 1 d D . . H10 H 0.212(5) 0.1072(11) 0.620(3) 0.026(9) Uiso 1 1 d D . . C11 C 0.5172(5) 0.11333(9) 0.5761(3) 0.0187(6) Uani 1 1 d . . . C12 C 0.4627(5) 0.04922(10) 0.2368(3) 0.0236(6) Uani 1 1 d . . . C13 C 0.2475(6) 0.03701(12) 0.1326(4) 0.0360(8) Uani 1 1 d . . . H13A H 0.1598 0.0201 0.1862 0.054 Uiso 1 1 calc R . . H13B H 0.2736 0.0188 0.0520 0.054 Uiso 1 1 calc R . . H13C H 0.1713 0.0644 0.0929 0.054 Uiso 1 1 calc R . . C14 C 0.5835(6) 0.00648(11) 0.2996(4) 0.0299(7) Uani 1 1 d . . . H14A H 0.7187 0.0145 0.3689 0.045 Uiso 1 1 calc R . . H14B H 0.6148 -0.0113 0.2195 0.045 Uiso 1 1 calc R . . H14C H 0.4942 -0.0110 0.3504 0.045 Uiso 1 1 calc R . . C15 C 0.6039(6) 0.07592(11) 0.1556(3) 0.0297(8) Uani 1 1 d . . . H15A H 0.5260 0.1026 0.1115 0.045 Uiso 1 1 calc R . . H15B H 0.6383 0.0573 0.0784 0.045 Uiso 1 1 calc R . . H15C H 0.7374 0.0848 0.2250 0.045 Uiso 1 1 calc R . . C16 C 0.6689(5) 0.13426(10) 0.7084(3) 0.0220(6) Uani 1 1 d . . . C17 C 0.8206(5) 0.16750(10) 0.6605(3) 0.0250(7) Uani 1 1 d . . . H17A H 0.8901 0.1531 0.5902 0.038 Uiso 1 1 calc R . . H17B H 0.9307 0.1772 0.7464 0.038 Uiso 1 1 calc R . . H17C H 0.7383 0.1934 0.6143 0.038 Uiso 1 1 calc R . . C18 C 0.8053(5) 0.09646(11) 0.7953(3) 0.0266(7) Uani 1 1 d . . . H18A H 0.7110 0.0753 0.8292 0.040 Uiso 1 1 calc R . . H18B H 0.9084 0.1091 0.8800 0.040 Uiso 1 1 calc R . . H18C H 0.8833 0.0809 0.7319 0.040 Uiso 1 1 calc R . . C19 C 0.5417(6) 0.15796(12) 0.8053(3) 0.0294(7) Uani 1 1 d . . . H19A H 0.4510 0.1812 0.7482 0.044 Uiso 1 1 calc R . . H19B H 0.6420 0.1716 0.8895 0.044 Uiso 1 1 calc R . . H19C H 0.4509 0.1362 0.8403 0.044 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 Zr 0.01959(13) 0.01740(12) 0.01474(12) 0.00209(10) 0.00299(8) 0.00133(10) N 0.0204(13) 0.0187(12) 0.0127(11) 0.0010(9) 0.0019(9) 0.0013(9) C1 0.0311(18) 0.0255(16) 0.0251(16) 0.0108(12) 0.0146(13) 0.0057(13) C2 0.0308(18) 0.0304(17) 0.0148(15) 0.0075(12) 0.0030(12) 0.0077(13) C3 0.0255(17) 0.0285(16) 0.0180(15) 0.0048(12) -0.0006(13) 0.0045(13) C4 0.0192(16) 0.0291(16) 0.0254(16) 0.0034(12) 0.0067(13) 0.0036(12) C5 0.0301(18) 0.0225(15) 0.0252(16) 0.0004(12) 0.0111(13) 0.0095(13) C6 0.0322(18) 0.0176(14) 0.0269(16) -0.0059(12) 0.0043(14) 0.0015(13) C7 0.0256(17) 0.0183(14) 0.0346(18) 0.0066(13) 0.0092(14) -0.0029(12) C8 0.0228(15) 0.0147(13) 0.0147(13) 0.0028(10) 0.0011(11) 0.0025(11) C9 0.0226(17) 0.0211(15) 0.0212(15) 0.0032(11) -0.0008(12) -0.0017(12) C10 0.0214(15) 0.0212(14) 0.0193(14) 0.0047(11) 0.0069(12) 0.0015(11) C11 0.0235(16) 0.0180(13) 0.0142(13) 0.0016(11) 0.0038(11) 0.0010(11) C12 0.0306(18) 0.0200(15) 0.0176(14) -0.0009(11) 0.0009(12) 0.0020(12) C13 0.047(2) 0.0327(19) 0.0225(17) -0.0087(14) -0.0040(15) 0.0035(16) C14 0.042(2) 0.0229(16) 0.0247(16) -0.0022(13) 0.0078(15) 0.0069(14) C15 0.047(2) 0.0288(17) 0.0165(15) -0.0008(12) 0.0132(14) 0.0074(14) C16 0.0272(17) 0.0213(15) 0.0162(14) -0.0022(11) 0.0027(12) -0.0024(12) C17 0.0243(16) 0.0246(16) 0.0239(16) -0.0036(12) 0.0012(12) -0.0029(12) C18 0.0312(18) 0.0271(16) 0.0186(15) 0.0023(12) 0.0001(12) 0.0020(13) C19 0.0372(19) 0.0335(17) 0.0167(14) -0.0057(13) 0.0052(13) 0.0037(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 Zr C4 2.318(3) . ? Zr C3 2.324(3) . ? Zr C5 2.328(3) . ? Zr C2 2.341(3) . ? Zr C6 2.344(3) . ? Zr C7 2.352(3) . ? Zr C1 2.356(3) . ? Zr N 2.400(2) . ? Zr C11 2.466(3) . ? Zr C8 2.470(3) . ? Zr C10 2.546(3) . ? Zr C9 2.551(3) . ? N C11 1.383(4) . ? N C8 1.384(4) . ? C1 C2 1.421(5) . ? C1 C7 1.423(5) . ? C2 C3 1.420(5) . ? C3 C4 1.423(4) . ? C4 C5 1.418(5) . ? C5 C6 1.419(5) . ? C6 C7 1.415(5) . ? C8 C9 1.400(4) . ? C8 C12 1.523(4) . ? C9 C10 1.415(4) . ? C10 C11 1.397(4) . ? C11 C16 1.517(4) . ? C12 C13 1.531(4) . ? C12 C14 1.538(4) . ? C12 C15 1.539(4) . ? C16 C17 1.531(4) . ? C16 C19 1.533(4) . ? C16 C18 1.539(4) . ? 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 C4 Zr C3 35.71(11) . . ? C4 Zr C5 35.55(11) . . ? C3 Zr C5 66.87(12) . . ? C4 Zr C2 66.56(11) . . ? C3 Zr C2 35.44(11) . . ? C5 Zr C2 86.18(11) . . ? C4 Zr C6 66.54(12) . . ? C3 Zr C6 86.47(12) . . ? C5 Zr C6 35.38(12) . . ? C2 Zr C6 85.92(12) . . ? C4 Zr C7 85.99(11) . . ? C3 Zr C7 86.18(12) . . ? C5 Zr C7 66.10(12) . . ? C2 Zr C7 66.16(12) . . ? C6 Zr C7 35.07(12) . . ? C4 Zr C1 85.94(11) . . ? C3 Zr C1 66.33(12) . . ? C5 Zr C1 85.74(11) . . ? C2 Zr C1 35.21(12) . . ? C6 Zr C1 65.94(12) . . ? C7 Zr C1 35.17(12) . . ? C4 Zr N 152.77(10) . . ? C3 Zr N 143.33(10) . . ? C5 Zr N 144.72(10) . . ? C2 Zr N 128.89(10) . . ? C6 Zr N 129.93(10) . . ? C7 Zr N 119.99(10) . . ? C1 Zr N 119.67(10) . . ? C4 Zr C11 128.19(10) . . ? C3 Zr C11 150.82(11) . . ? C5 Zr C11 112.10(10) . . ? C2 Zr C11 161.70(10) . . ? C6 Zr C11 109.32(10) . . ? C7 Zr C11 120.99(11) . . ? C1 Zr C11 142.22(11) . . ? N Zr C11 33.00(8) . . ? C4 Zr C8 126.37(11) . . ? C3 Zr C8 111.16(11) . . ? C5 Zr C8 148.77(11) . . ? C2 Zr C8 110.15(10) . . ? C6 Zr C8 162.08(11) . . ? C7 Zr C8 144.51(11) . . ? C1 Zr C8 123.12(10) . . ? N Zr C8 33.00(9) . . ? C11 Zr C8 53.49(9) . . ? C4 Zr C10 99.85(10) . . ? C3 Zr C10 118.85(11) . . ? C5 Zr C10 98.69(10) . . ? C2 Zr C10 148.31(11) . . ? C6 Zr C10 115.88(11) . . ? C7 Zr C10 144.09(11) . . ? C1 Zr C10 174.19(10) . . ? N Zr C10 54.70(9) . . ? C11 Zr C10 32.32(10) . . ? C8 Zr C10 53.50(9) . . ? C4 Zr C9 98.95(11) . . ? C3 Zr C9 99.60(11) . . ? C5 Zr C9 116.52(11) . . ? C2 Zr C9 118.56(11) . . ? C6 Zr C9 145.03(11) . . ? C7 Zr C9 174.20(11) . . ? C1 Zr C9 147.64(11) . . ? N Zr C9 54.69(9) . . ? C11 Zr C9 53.45(10) . . ? C8 Zr C9 32.35(10) . . ? C10 Zr C9 32.23(9) . . ? C11 N C8 106.7(2) . . ? C11 N Zr 76.12(16) . . ? C8 N Zr 76.27(15) . . ? C2 C1 C7 128.6(3) . . ? C2 C1 Zr 71.82(17) . . ? C7 C1 Zr 72.26(17) . . ? C3 C2 C1 128.7(3) . . ? C3 C2 Zr 71.61(17) . . ? C1 C2 Zr 72.97(17) . . ? C2 C3 C4 128.1(3) . . ? C2 C3 Zr 72.95(18) . . ? C4 C3 Zr 71.94(18) . . ? C5 C4 C3 128.8(3) . . ? C5 C4 Zr 72.59(18) . . ? C3 C4 Zr 72.35(18) . . ? C4 C5 C6 128.6(3) . . ? C4 C5 Zr 71.86(17) . . ? C6 C5 Zr 72.93(17) . . ? C7 C6 C5 128.4(3) . . ? C7 C6 Zr 72.78(17) . . ? C5 C6 Zr 71.70(17) . . ? C6 C7 C1 128.7(3) . . ? C6 C7 Zr 72.15(18) . . ? C1 C7 Zr 72.57(17) . . ? N C8 C9 109.8(2) . . ? N C8 C12 120.3(3) . . ? C9 C8 C12 129.5(3) . . ? N C8 Zr 70.74(15) . . ? C9 C8 Zr 77.02(17) . . ? C12 C8 Zr 123.97(19) . . ? C8 C9 C10 106.7(3) . . ? C8 C9 Zr 70.64(16) . . ? C10 C9 Zr 73.71(17) . . ? C11 C10 C9 106.8(3) . . ? C11 C10 Zr 70.68(16) . . ? C9 C10 Zr 74.06(17) . . ? N C11 C10 109.9(3) . . ? N C11 C16 120.8(3) . . ? C10 C11 C16 129.0(3) . . ? N C11 Zr 70.88(15) . . ? C10 C11 Zr 77.01(17) . . ? C16 C11 Zr 122.92(19) . . ? C8 C12 C13 110.1(3) . . ? C8 C12 C14 107.0(2) . . ? C13 C12 C14 109.9(3) . . ? C8 C12 C15 110.4(2) . . ? C13 C12 C15 110.6(3) . . ? C14 C12 C15 108.7(3) . . ? C11 C16 C17 110.8(2) . . ? C11 C16 C19 110.5(3) . . ? C17 C16 C19 109.7(3) . . ? C11 C16 C18 107.5(2) . . ? C17 C16 C18 108.3(3) . . ? C19 C16 C18 109.9(3) . . ? 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 C4 Zr N C11 -59.2(3) . . . . ? C3 Zr N C11 -128.0(2) . . . . ? C5 Zr N C11 11.4(3) . . . . ? C2 Zr N C11 -176.01(18) . . . . ? C6 Zr N C11 60.2(2) . . . . ? C7 Zr N C11 101.69(19) . . . . ? C1 Zr N C11 142.46(18) . . . . ? C8 Zr N C11 -111.4(2) . . . . ? C10 Zr N C11 -35.80(17) . . . . ? C9 Zr N C11 -75.56(18) . . . . ? C4 Zr N C8 52.2(3) . . . . ? C3 Zr N C8 -16.6(2) . . . . ? C5 Zr N C8 122.8(2) . . . . ? C2 Zr N C8 -64.6(2) . . . . ? C6 Zr N C8 171.66(17) . . . . ? C7 Zr N C8 -146.86(17) . . . . ? C1 Zr N C8 -106.10(18) . . . . ? C11 Zr N C8 111.4(2) . . . . ? C10 Zr N C8 75.65(17) . . . . ? C9 Zr N C8 35.88(16) . . . . ? C4 Zr C1 C2 -53.76(19) . . . . ? C3 Zr C1 C2 -22.83(18) . . . . ? C5 Zr C1 C2 -89.4(2) . . . . ? C6 Zr C1 C2 -119.8(2) . . . . ? C7 Zr C1 C2 -142.6(3) . . . . ? N Zr C1 C2 116.47(18) . . . . ? C11 Zr C1 C2 149.27(19) . . . . ? C8 Zr C1 C2 77.8(2) . . . . ? C10 Zr C1 C2 130.7(10) . . . . ? C9 Zr C1 C2 46.6(3) . . . . ? C4 Zr C1 C7 88.8(2) . . . . ? C3 Zr C1 C7 119.7(2) . . . . ? C5 Zr C1 C7 53.2(2) . . . . ? C2 Zr C1 C7 142.6(3) . . . . ? C6 Zr C1 C7 22.72(19) . . . . ? N Zr C1 C7 -100.97(19) . . . . ? C11 Zr C1 C7 -68.2(2) . . . . ? C8 Zr C1 C7 -139.63(18) . . . . ? C10 Zr C1 C7 -86.8(11) . . . . ? C9 Zr C1 C7 -170.87(19) . . . . ? C7 C1 C2 C3 0.3(6) . . . . ? Zr C1 C2 C3 48.1(3) . . . . ? C7 C1 C2 Zr -47.8(3) . . . . ? C4 Zr C2 C3 -23.48(19) . . . . ? C5 Zr C2 C3 -54.2(2) . . . . ? C6 Zr C2 C3 -89.6(2) . . . . ? C7 Zr C2 C3 -119.7(2) . . . . ? C1 Zr C2 C3 -142.2(3) . . . . ? N Zr C2 C3 130.08(18) . . . . ? C11 Zr C2 C3 123.1(3) . . . . ? C8 Zr C2 C3 98.5(2) . . . . ? C10 Zr C2 C3 46.2(3) . . . . ? C9 Zr C2 C3 64.1(2) . . . . ? C4 Zr C2 C1 118.7(2) . . . . ? C3 Zr C2 C1 142.2(3) . . . . ? C5 Zr C2 C1 88.0(2) . . . . ? C6 Zr C2 C1 52.6(2) . . . . ? C7 Zr C2 C1 22.51(18) . . . . ? N Zr C2 C1 -87.7(2) . . . . ? C11 Zr C2 C1 -94.6(4) . . . . ? C8 Zr C2 C1 -119.31(19) . . . . ? C10 Zr C2 C1 -171.59(18) . . . . ? C9 Zr C2 C1 -153.73(18) . . . . ? C1 C2 C3 C4 0.6(6) . . . . ? Zr C2 C3 C4 49.2(3) . . . . ? C1 C2 C3 Zr -48.6(3) . . . . ? C4 Zr C3 C2 141.2(3) . . . . ? C5 Zr C3 C2 118.4(2) . . . . ? C6 Zr C3 C2 87.9(2) . . . . ? C7 Zr C3 C2 52.8(2) . . . . ? C1 Zr C3 C2 22.69(19) . . . . ? N Zr C3 C2 -85.8(2) . . . . ? C11 Zr C3 C2 -147.4(2) . . . . ? C8 Zr C3 C2 -95.3(2) . . . . ? C10 Zr C3 C2 -154.35(18) . . . . ? C9 Zr C3 C2 -126.8(2) . . . . ? C5 Zr C3 C4 -22.84(19) . . . . ? C2 Zr C3 C4 -141.2(3) . . . . ? C6 Zr C3 C4 -53.3(2) . . . . ? C7 Zr C3 C4 -88.4(2) . . . . ? C1 Zr C3 C4 -118.5(2) . . . . ? N Zr C3 C4 133.03(19) . . . . ? C11 Zr C3 C4 71.4(3) . . . . ? C8 Zr C3 C4 123.44(19) . . . . ? C10 Zr C3 C4 64.4(2) . . . . ? C9 Zr C3 C4 92.0(2) . . . . ? C2 C3 C4 C5 -0.8(6) . . . . ? Zr C3 C4 C5 48.8(3) . . . . ? C2 C3 C4 Zr -49.6(3) . . . . ? C3 Zr C4 C5 -142.1(3) . . . . ? C2 Zr C4 C5 -118.8(2) . . . . ? C6 Zr C4 C5 -22.86(18) . . . . ? C7 Zr C4 C5 -53.09(19) . . . . ? C1 Zr C4 C5 -88.35(19) . . . . ? N Zr C4 C5 110.4(2) . . . . ? C11 Zr C4 C5 73.9(2) . . . . ? C8 Zr C4 C5 142.74(17) . . . . ? C10 Zr C4 C5 91.19(19) . . . . ? C9 Zr C4 C5 123.86(18) . . . . ? C5 Zr C4 C3 142.1(3) . . . . ? C2 Zr C4 C3 23.32(19) . . . . ? C6 Zr C4 C3 119.3(2) . . . . ? C7 Zr C4 C3 89.0(2) . . . . ? C1 Zr C4 C3 53.8(2) . . . . ? N Zr C4 C3 -107.4(2) . . . . ? C11 Zr C4 C3 -143.98(18) . . . . ? C8 Zr C4 C3 -75.1(2) . . . . ? C10 Zr C4 C3 -126.68(19) . . . . ? C9 Zr C4 C3 -94.0(2) . . . . ? C3 C4 C5 C6 0.2(6) . . . . ? Zr C4 C5 C6 48.9(3) . . . . ? C3 C4 C5 Zr -48.7(3) . . . . ? C3 Zr C5 C4 22.93(18) . . . . ? C2 Zr C5 C4 53.68(19) . . . . ? C6 Zr C5 C4 142.0(3) . . . . ? C7 Zr C5 C4 119.3(2) . . . . ? C1 Zr C5 C4 88.98(19) . . . . ? N Zr C5 C4 -132.06(19) . . . . ? C11 Zr C5 C4 -125.41(18) . . . . ? C8 Zr C5 C4 -70.1(3) . . . . ? C10 Zr C5 C4 -94.80(18) . . . . ? C9 Zr C5 C4 -66.5(2) . . . . ? C4 Zr C5 C6 -142.0(3) . . . . ? C3 Zr C5 C6 -119.1(2) . . . . ? C2 Zr C5 C6 -88.3(2) . . . . ? C7 Zr C5 C6 -22.75(19) . . . . ? C1 Zr C5 C6 -53.0(2) . . . . ? N Zr C5 C6 85.9(2) . . . . ? C11 Zr C5 C6 92.57(19) . . . . ? C8 Zr C5 C6 147.9(2) . . . . ? C10 Zr C5 C6 123.18(19) . . . . ? C9 Zr C5 C6 151.53(18) . . . . ? C4 C5 C6 C7 0.1(6) . . . . ? Zr C5 C6 C7 48.6(3) . . . . ? C4 C5 C6 Zr -48.5(3) . . . . ? C4 Zr C6 C7 -119.1(2) . . . . ? C3 Zr C6 C7 -88.4(2) . . . . ? C5 Zr C6 C7 -142.0(3) . . . . ? C2 Zr C6 C7 -52.9(2) . . . . ? C1 Zr C6 C7 -22.78(19) . . . . ? N Zr C6 C7 86.7(2) . . . . ? C11 Zr C6 C7 116.7(2) . . . . ? C8 Zr C6 C7 101.6(4) . . . . ? C10 Zr C6 C7 151.13(19) . . . . ? C9 Zr C6 C7 169.89(19) . . . . ? C4 Zr C6 C5 22.96(18) . . . . ? C3 Zr C6 C5 53.63(19) . . . . ? C2 Zr C6 C5 89.1(2) . . . . ? C7 Zr C6 C5 142.0(3) . . . . ? C1 Zr C6 C5 119.2(2) . . . . ? N Zr C6 C5 -131.29(18) . . . . ? C11 Zr C6 C5 -101.24(19) . . . . ? C8 Zr C6 C5 -116.4(4) . . . . ? C10 Zr C6 C5 -66.9(2) . . . . ? C9 Zr C6 C5 -48.1(3) . . . . ? C5 C6 C7 C1 0.4(6) . . . . ? Zr C6 C7 C1 48.6(3) . . . . ? C5 C6 C7 Zr -48.3(3) . . . . ? C2 C1 C7 C6 -0.8(6) . . . . ? Zr C1 C7 C6 -48.5(3) . . . . ? C2 C1 C7 Zr 47.6(3) . . . . ? C4 Zr C7 C6 53.5(2) . . . . ? C3 Zr C7 C6 89.3(2) . . . . ? C5 Zr C7 C6 22.94(19) . . . . ? C2 Zr C7 C6 119.6(2) . . . . ? C1 Zr C7 C6 142.1(3) . . . . ? N Zr C7 C6 -117.9(2) . . . . ? C11 Zr C7 C6 -79.4(2) . . . . ? C8 Zr C7 C6 -148.7(2) . . . . ? C10 Zr C7 C6 -47.8(3) . . . . ? C9 Zr C7 C6 -95.1(11) . . . . ? C4 Zr C7 C1 -88.6(2) . . . . ? C3 Zr C7 C1 -52.8(2) . . . . ? C5 Zr C7 C1 -119.2(2) . . . . ? C2 Zr C7 C1 -22.53(18) . . . . ? C6 Zr C7 C1 -142.1(3) . . . . ? N Zr C7 C1 99.98(19) . . . . ? C11 Zr C7 C1 138.45(18) . . . . ? C8 Zr C7 C1 69.1(3) . . . . ? C10 Zr C7 C1 170.07(18) . . . . ? C9 Zr C7 C1 122.8(10) . . . . ? C11 N C8 C9 2.9(3) . . . . ? Zr N C8 C9 -67.8(2) . . . . ? C11 N C8 C12 -170.6(2) . . . . ? Zr N C8 C12 118.8(2) . . . . ? C11 N C8 Zr 70.65(18) . . . . ? C4 Zr C8 N -153.31(15) . . . . ? C3 Zr C8 N 169.47(15) . . . . ? C5 Zr C8 N -110.6(2) . . . . ? C2 Zr C8 N 131.52(16) . . . . ? C6 Zr C8 N -21.2(4) . . . . ? C7 Zr C8 N 54.6(2) . . . . ? C1 Zr C8 N 94.63(18) . . . . ? C11 Zr C8 N -39.10(15) . . . . ? C10 Zr C8 N -79.61(17) . . . . ? C9 Zr C8 N -116.6(2) . . . . ? C4 Zr C8 C9 -36.7(2) . . . . ? C3 Zr C8 C9 -73.91(19) . . . . ? C5 Zr C8 C9 6.1(3) . . . . ? C2 Zr C8 C9 -111.86(18) . . . . ? C6 Zr C8 C9 95.4(4) . . . . ? C7 Zr C8 C9 171.26(19) . . . . ? C1 Zr C8 C9 -148.75(18) . . . . ? N Zr C8 C9 116.6(2) . . . . ? C11 Zr C8 C9 77.53(19) . . . . ? C10 Zr C8 C9 37.01(17) . . . . ? C4 Zr C8 C12 92.5(3) . . . . ? C3 Zr C8 C12 55.3(3) . . . . ? C5 Zr C8 C12 135.3(3) . . . . ? C2 Zr C8 C12 17.4(3) . . . . ? C6 Zr C8 C12 -135.4(3) . . . . ? C7 Zr C8 C12 -59.5(3) . . . . ? C1 Zr C8 C12 -19.5(3) . . . . ? N Zr C8 C12 -114.2(3) . . . . ? C11 Zr C8 C12 -153.3(3) . . . . ? C10 Zr C8 C12 166.2(3) . . . . ? C9 Zr C8 C12 129.2(3) . . . . ? N C8 C9 C10 -1.7(3) . . . . ? C12 C8 C9 C10 171.0(3) . . . . ? Zr C8 C9 C10 -65.4(2) . . . . ? N C8 C9 Zr 63.73(19) . . . . ? C12 C8 C9 Zr -123.6(3) . . . . ? C4 Zr C9 C8 150.86(18) . . . . ? C3 Zr C9 C8 114.66(18) . . . . ? C5 Zr C9 C8 -176.49(17) . . . . ? C2 Zr C9 C8 82.7(2) . . . . ? C6 Zr C9 C8 -147.7(2) . . . . ? C7 Zr C9 C8 -60.9(11) . . . . ? C1 Zr C9 C8 54.3(3) . . . . ? N Zr C9 C8 -36.63(16) . . . . ? C11 Zr C9 C8 -77.66(19) . . . . ? C10 Zr C9 C8 -114.8(3) . . . . ? C4 Zr C9 C10 -94.30(19) . . . . ? C3 Zr C9 C10 -130.49(19) . . . . ? C5 Zr C9 C10 -61.6(2) . . . . ? C2 Zr C9 C10 -162.42(18) . . . . ? C6 Zr C9 C10 -32.9(3) . . . . ? C7 Zr C9 C10 54.0(11) . . . . ? C1 Zr C9 C10 169.1(2) . . . . ? N Zr C9 C10 78.22(18) . . . . ? C11 Zr C9 C10 37.18(17) . . . . ? C8 Zr C9 C10 114.8(3) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? Zr C9 C10 C11 -63.5(2) . . . . ? C8 C9 C10 Zr 63.4(2) . . . . ? C4 Zr C10 C11 -154.07(18) . . . . ? C3 Zr C10 C11 173.63(17) . . . . ? C5 Zr C10 C11 -118.05(18) . . . . ? C2 Zr C10 C11 145.1(2) . . . . ? C6 Zr C10 C11 -85.47(19) . . . . ? C7 Zr C10 C11 -57.2(3) . . . . ? C1 Zr C10 C11 21.4(11) . . . . ? N Zr C10 C11 36.58(16) . . . . ? C8 Zr C10 C11 77.59(18) . . . . ? C9 Zr C10 C11 114.7(3) . . . . ? C4 Zr C10 C9 91.18(19) . . . . ? C3 Zr C10 C9 58.9(2) . . . . ? C5 Zr C10 C9 127.20(19) . . . . ? C2 Zr C10 C9 30.3(3) . . . . ? C6 Zr C10 C9 159.78(19) . . . . ? C7 Zr C10 C9 -171.99(19) . . . . ? C1 Zr C10 C9 -93.3(11) . . . . ? N Zr C10 C9 -78.17(19) . . . . ? C11 Zr C10 C9 -114.7(3) . . . . ? C8 Zr C10 C9 -37.15(17) . . . . ? C8 N C11 C10 -3.0(3) . . . . ? Zr N C11 C10 67.7(2) . . . . ? C8 N C11 C16 171.7(2) . . . . ? Zr N C11 C16 -117.6(3) . . . . ? C8 N C11 Zr -70.76(18) . . . . ? C9 C10 C11 N 2.0(3) . . . . ? Zr C10 C11 N -63.83(19) . . . . ? C9 C10 C11 C16 -172.1(3) . . . . ? Zr C10 C11 C16 122.1(3) . . . . ? C9 C10 C11 Zr 65.8(2) . . . . ? C4 Zr C11 N 149.98(17) . . . . ? C3 Zr C11 N 105.2(2) . . . . ? C5 Zr C11 N -172.95(16) . . . . ? C2 Zr C11 N 9.9(4) . . . . ? C6 Zr C11 N -135.15(17) . . . . ? C7 Zr C11 N -98.39(18) . . . . ? C1 Zr C11 N -59.8(2) . . . . ? C8 Zr C11 N 39.10(16) . . . . ? C10 Zr C11 N 116.7(2) . . . . ? C9 Zr C11 N 79.66(18) . . . . ? C4 Zr C11 C10 33.2(2) . . . . ? C3 Zr C11 C10 -11.5(3) . . . . ? C5 Zr C11 C10 70.3(2) . . . . ? C2 Zr C11 C10 -106.8(4) . . . . ? C6 Zr C11 C10 108.11(19) . . . . ? C7 Zr C11 C10 144.87(18) . . . . ? C1 Zr C11 C10 -176.54(18) . . . . ? N Zr C11 C10 -116.7(2) . . . . ? C8 Zr C11 C10 -77.64(18) . . . . ? C9 Zr C11 C10 -37.08(17) . . . . ? C4 Zr C11 C16 -95.1(3) . . . . ? C3 Zr C11 C16 -139.9(2) . . . . ? C5 Zr C11 C16 -58.0(3) . . . . ? C2 Zr C11 C16 124.8(4) . . . . ? C6 Zr C11 C16 -20.2(3) . . . . ? C7 Zr C11 C16 16.5(3) . . . . ? C1 Zr C11 C16 55.1(3) . . . . ? N Zr C11 C16 114.9(3) . . . . ? C8 Zr C11 C16 154.0(3) . . . . ? C10 Zr C11 C16 -128.4(3) . . . . ? C9 Zr C11 C16 -165.4(3) . . . . ? N C8 C12 C13 -166.1(3) . . . . ? C9 C8 C12 C13 21.9(4) . . . . ? Zr C8 C12 C13 -79.9(3) . . . . ? N C8 C12 C14 74.6(3) . . . . ? C9 C8 C12 C14 -97.5(4) . . . . ? Zr C8 C12 C14 160.7(2) . . . . ? N C8 C12 C15 -43.6(4) . . . . ? C9 C8 C12 C15 144.4(3) . . . . ? Zr C8 C12 C15 42.5(3) . . . . ? N C11 C16 C17 44.0(4) . . . . ? C10 C11 C16 C17 -142.5(3) . . . . ? Zr C11 C16 C17 -42.1(3) . . . . ? N C11 C16 C19 165.8(3) . . . . ? C10 C11 C16 C19 -20.6(4) . . . . ? Zr C11 C16 C19 79.8(3) . . . . ? N C11 C16 C18 -74.2(3) . . . . ? C10 C11 C16 C18 99.3(4) . . . . ? Zr C11 C16 C18 -160.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 72.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.343 _refine_diff_density_min -0.636 _refine_diff_density_rms 0.077 _iucr_refine_instructions_details ; TITL mwal21 in P2(1)/n CELL 1.54184 6.4001 29.9375 9.3920 90.000 103.842 90.000 ZERR 4.00 0.0002 0.0012 0.0004 0.000 0.004 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N ZR UNIT 76 108 4 4 SIZE 0.08 0.06 0.02 TEMP -173 ACTA 145 CONF FMAP 2 PLAN 10 L.S. 8 SADI C1 H1 C2 H2 C3 H3 C4 H4 C5 H5 C6 H6 C7 H7 C9 H9 C10 H10 OMIT -8 0 2 OMIT 5 0 7 OMIT -8 2 3 OMIT 5 2 7 OMIT -8 2 2 OMIT 2 7 10 OMIT -8 1 3 OMIT -8 3 3 OMIT -7 18 2 OMIT 7 3 3 OMIT -7 3 8 OMIT 2 9 10 OMIT -6 8 9 OMIT -8 1 4 OMIT -4 2 10 OMIT -2 30 7 OMIT 4 17 7 OMIT 3 18 8 OMIT -6 15 8 OMIT 3 22 7 OMIT 6 1 5 OMIT 6 3 5 OMIT 7 5 1 OMIT -3 23 9 OMIT -6 19 7 OMIT 2 5 0 OMIT 4 3 7 OMIT 7 3 2 OMIT -5 24 6 OMIT -4 32 2 OMIT -1 4 11 OMIT 7 1 3 WGHT 0.022100 1.574200 FVAR 1.50038 ZR 4 0.340479 0.156514 0.356725 11.00000 0.01959 0.01740 = 0.01474 0.00209 0.00299 0.00133 N 3 0.592218 0.098704 0.457706 11.00000 0.02039 0.01866 = 0.01272 0.00096 0.00187 0.00135 C1 1 0.414259 0.204789 0.176767 11.00000 0.03106 0.02551 = 0.02511 0.01078 0.01465 0.00565 H1 2 0.527025 0.202571 0.128226 11.00000 0.03278 C2 1 0.225710 0.180071 0.112794 11.00000 0.03083 0.03042 = 0.01478 0.00752 0.00305 0.00769 H2 2 0.227978 0.165223 0.024587 11.00000 0.03721 C3 1 0.041252 0.172471 0.168579 11.00000 0.02548 0.02852 = 0.01799 0.00475 -0.00055 0.00446 H3 2 -0.058065 0.152005 0.115200 11.00000 0.02866 C4 1 0.000169 0.188240 0.302221 11.00000 0.01916 0.02906 = 0.02540 0.00340 0.00672 0.00365 H4 2 -0.127402 0.177157 0.322625 11.00000 0.01788 C5 1 0.133051 0.214789 0.412847 11.00000 0.03007 0.02251 = 0.02516 0.00044 0.01113 0.00949 H5 2 0.081137 0.218353 0.497138 11.00000 0.03164 C6 1 0.340520 0.232428 0.417752 11.00000 0.03223 0.01761 = 0.02685 -0.00587 0.00428 0.00149 H6 2 0.414383 0.245280 0.505992 11.00000 0.02478 C7 1 0.465492 0.227891 0.313058 11.00000 0.02565 0.01828 = 0.03465 0.00660 0.00925 -0.00294 H7 2 0.606050 0.238742 0.343569 11.00000 0.03493 C8 1 0.424365 0.075892 0.366256 11.00000 0.02285 0.01472 = 0.01470 0.00276 0.00107 0.00253 C9 1 0.241126 0.077993 0.422933 11.00000 0.02257 0.02106 = 0.02120 0.00324 -0.00082 -0.00167 H9 2 0.108353 0.065297 0.379124 11.00000 0.03210 C10 1 0.300566 0.101921 0.556406 11.00000 0.02139 0.02119 = 0.01929 0.00471 0.00689 0.00148 H10 2 0.211776 0.107150 0.620064 11.00000 0.02553 C11 1 0.517242 0.113329 0.576081 11.00000 0.02349 0.01803 = 0.01417 0.00158 0.00383 0.00101 C12 1 0.462673 0.049215 0.236802 11.00000 0.03063 0.01995 = 0.01762 -0.00090 0.00093 0.00198 C13 1 0.247470 0.037005 0.132592 11.00000 0.04669 0.03270 = 0.02246 -0.00868 -0.00398 0.00351 AFIX 137 H13A 2 0.159772 0.020078 0.186187 11.00000 -1.50000 H13B 2 0.273606 0.018761 0.051960 11.00000 -1.50000 H13C 2 0.171267 0.064360 0.092919 11.00000 -1.50000 AFIX 0 C14 1 0.583549 0.006481 0.299577 11.00000 0.04191 0.02289 = 0.02468 -0.00225 0.00777 0.00693 AFIX 137 H14A 2 0.718706 0.014526 0.368868 11.00000 -1.50000 H14B 2 0.614777 -0.011278 0.219484 11.00000 -1.50000 H14C 2 0.494200 -0.011039 0.350386 11.00000 -1.50000 AFIX 0 C15 1 0.603900 0.075922 0.155560 11.00000 0.04651 0.02883 = 0.01652 -0.00081 0.01315 0.00741 AFIX 137 H15A 2 0.525972 0.102625 0.111481 11.00000 -1.50000 H15B 2 0.638276 0.057300 0.078420 11.00000 -1.50000 H15C 2 0.737384 0.084850 0.225047 11.00000 -1.50000 AFIX 0 C16 1 0.668940 0.134265 0.708386 11.00000 0.02721 0.02131 = 0.01623 -0.00217 0.00273 -0.00242 C17 1 0.820647 0.167496 0.660532 11.00000 0.02426 0.02460 = 0.02388 -0.00362 0.00122 -0.00289 AFIX 137 H17A 2 0.890073 0.153079 0.590208 11.00000 -1.50000 H17B 2 0.930734 0.177240 0.746432 11.00000 -1.50000 H17C 2 0.738256 0.193445 0.614320 11.00000 -1.50000 AFIX 0 C18 1 0.805282 0.096455 0.795254 11.00000 0.03122 0.02713 = 0.01861 0.00230 0.00013 0.00204 AFIX 137 H18A 2 0.710967 0.075264 0.829180 11.00000 -1.50000 H18B 2 0.908445 0.109075 0.879971 11.00000 -1.50000 H18C 2 0.883268 0.080946 0.731934 11.00000 -1.50000 AFIX 0 C19 1 0.541736 0.157964 0.805329 11.00000 0.03717 0.03353 = 0.01672 -0.00571 0.00518 0.00365 AFIX 137 H19A 2 0.450960 0.181213 0.748242 11.00000 -1.50000 H19B 2 0.642019 0.171605 0.889460 11.00000 -1.50000 H19C 2 0.450908 0.136224 0.840262 11.00000 -1.50000 HKLF 4 ; data_mk71 _database_code_depnum_ccdc_archive 'CCDC 902361' #TrackingRef 'combined_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H31 N Zr' _chemical_formula_weight 388.69 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' 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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.5908(3) _cell_length_b 13.9470(4) _cell_length_c 14.3385(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1917.96(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 21369 _cell_measurement_theta_min 2.5498 _cell_measurement_theta_max 30.8253 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.574 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93908 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 98371 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 30.89 _reflns_number_total 5864 _reflns_number_gt 5449 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _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. The hydrogens at the seven-membered ring were refined freely. The methyls were refined as idealised rigid groups allowed to rotate but not tip. ; _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^)+(0.0172P)^2^+0.5970P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(2) _chemical_absolute_configuration . _refine_ls_number_reflns 5864 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0461 _refine_ls_wR_factor_gt 0.0446 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.003 _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 Zr Zr 0.444860(15) 0.565954(10) 0.845922(9) 0.01321(3) Uani 1 1 d . . . N N 0.37904(13) 0.64777(9) 0.70908(9) 0.0119(3) Uani 1 1 d . . . C1 C 0.5354(2) 0.65436(13) 0.97235(11) 0.0294(4) Uani 1 1 d . . . H1 H 0.537(2) 0.7229(14) 0.9787(14) 0.027(5) Uiso 1 1 d . . . C2 C 0.4054(2) 0.61453(14) 1.00090(12) 0.0249(4) Uani 1 1 d . . . H2 H 0.336(2) 0.6571(13) 1.0219(13) 0.017(5) Uiso 1 1 d . . . C3 C 0.3586(2) 0.51747(14) 0.99123(12) 0.0235(4) Uani 1 1 d . . . H3 H 0.266(2) 0.5050(16) 1.0082(14) 0.031(6) Uiso 1 1 d . . . C4 C 0.43012(19) 0.43868(13) 0.95139(10) 0.0231(3) Uani 1 1 d . . . H4 H 0.376(2) 0.3786(15) 0.9450(14) 0.029(6) Uiso 1 1 d . . . C5 C 0.5650(2) 0.43602(14) 0.90913(10) 0.0254(3) Uani 1 1 d . . . H5 H 0.590(2) 0.3786(13) 0.8781(13) 0.023(5) Uiso 1 1 d . . . C6 C 0.6617(2) 0.51242(16) 0.89756(12) 0.0286(4) Uani 1 1 d . . . H6 H 0.740(2) 0.4944(15) 0.8633(14) 0.029(6) Uiso 1 1 d . . . C7 C 0.6483(2) 0.60944(17) 0.92687(12) 0.0307(5) Uani 1 1 d . . . H7 H 0.718(3) 0.6494(17) 0.9101(17) 0.045(7) Uiso 1 1 d . . . C8 C 0.25377(15) 0.61035(11) 0.74101(10) 0.0121(3) Uani 1 1 d . . . C9 C 0.25466(16) 0.50944(11) 0.73090(10) 0.0129(3) Uani 1 1 d . . . C10 C 0.38508(17) 0.48505(11) 0.68857(10) 0.0123(3) Uani 1 1 d . . . C11 C 0.45738(15) 0.57221(11) 0.67473(8) 0.0121(2) Uani 1 1 d . . . C12 C 0.13731(16) 0.68025(11) 0.76574(11) 0.0160(3) Uani 1 1 d . . . C13 C 0.0590(2) 0.70095(13) 0.67443(12) 0.0299(4) Uani 1 1 d . . . H13A H -0.0149 0.7480 0.6861 0.045 Uiso 1 1 calc R . . H13B H 0.0176 0.6415 0.6508 0.045 Uiso 1 1 calc R . . H13C H 0.1243 0.7266 0.6281 0.045 Uiso 1 1 calc R . . C14 C 0.03550(18) 0.64120(12) 0.83848(15) 0.0308(4) Uani 1 1 d . . . H14A H 0.0874 0.6202 0.8937 0.046 Uiso 1 1 calc R . . H14B H -0.0157 0.5867 0.8122 0.046 Uiso 1 1 calc R . . H14C H -0.0305 0.6917 0.8562 0.046 Uiso 1 1 calc R . . C15 C 0.19856(17) 0.77438(12) 0.80282(12) 0.0206(3) Uani 1 1 d . . . H15A H 0.2529 0.7615 0.8593 0.031 Uiso 1 1 calc R . . H15B H 0.1227 0.8190 0.8175 0.031 Uiso 1 1 calc R . . H15C H 0.2593 0.8028 0.7553 0.031 Uiso 1 1 calc R . . C16 C 0.14023(17) 0.43884(13) 0.75305(11) 0.0218(3) Uani 1 1 d . . . H16A H 0.0619 0.4488 0.7102 0.033 Uiso 1 1 calc R . . H16B H 0.1086 0.4485 0.8174 0.033 Uiso 1 1 calc R . . H16C H 0.1758 0.3734 0.7460 0.033 Uiso 1 1 calc R . . C17 C 0.42602(17) 0.38544(10) 0.65779(12) 0.0193(3) Uani 1 1 d . . . H17A H 0.5112 0.3659 0.6904 0.029 Uiso 1 1 calc R . . H17B H 0.4428 0.3853 0.5904 0.029 Uiso 1 1 calc R . . H17C H 0.3507 0.3405 0.6726 0.029 Uiso 1 1 calc R . . C18 C 0.59041(16) 0.59469(11) 0.62025(10) 0.0150(3) Uani 1 1 d . . . C19 C 0.5464(2) 0.60801(13) 0.51759(10) 0.0261(4) Uani 1 1 d . . . H19A H 0.4771 0.6594 0.5133 0.039 Uiso 1 1 calc R . . H19B H 0.5061 0.5482 0.4941 0.039 Uiso 1 1 calc R . . H19C H 0.6283 0.6249 0.4801 0.039 Uiso 1 1 calc R . . C20 C 0.65556(16) 0.68817(11) 0.65541(14) 0.0234(3) Uani 1 1 d . . . H20A H 0.6881 0.6794 0.7196 0.035 Uiso 1 1 calc R . . H20B H 0.5857 0.7394 0.6536 0.035 Uiso 1 1 calc R . . H20C H 0.7346 0.7055 0.6155 0.035 Uiso 1 1 calc R . . C21 C 0.70102(18) 0.51546(12) 0.62652(11) 0.0203(3) Uani 1 1 d . . . H21A H 0.6665 0.4575 0.5955 0.030 Uiso 1 1 calc R . . H21B H 0.7204 0.5012 0.6922 0.030 Uiso 1 1 calc R . . H21C H 0.7868 0.5370 0.5959 0.030 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 Zr 0.01346(6) 0.01772(6) 0.00844(5) 0.00039(6) -0.00104(6) -0.00207(6) N 0.0108(6) 0.0133(6) 0.0116(6) 0.0006(5) 0.0010(5) 0.0012(5) C1 0.0479(13) 0.0252(9) 0.0152(7) 0.0013(6) -0.0076(8) -0.0132(9) C2 0.0389(12) 0.0243(9) 0.0115(7) -0.0020(6) 0.0019(7) 0.0003(8) C3 0.0264(10) 0.0295(10) 0.0145(7) 0.0012(7) 0.0042(7) -0.0051(8) C4 0.0337(9) 0.0205(7) 0.0152(6) 0.0033(7) -0.0015(6) -0.0066(9) C5 0.0314(9) 0.0291(8) 0.0156(6) 0.0023(7) -0.0041(7) 0.0085(11) C6 0.0164(8) 0.0524(13) 0.0170(8) 0.0084(8) -0.0040(7) 0.0032(9) C7 0.0254(10) 0.0484(12) 0.0184(8) 0.0114(8) -0.0093(7) -0.0163(9) C8 0.0106(7) 0.0156(7) 0.0100(6) -0.0015(5) 0.0002(5) -0.0007(6) C9 0.0144(7) 0.0133(7) 0.0109(6) -0.0002(6) -0.0027(6) -0.0021(6) C10 0.0150(7) 0.0118(7) 0.0100(6) -0.0009(5) -0.0035(5) 0.0010(6) C11 0.0140(6) 0.0140(6) 0.0081(5) 0.0013(5) -0.0004(5) 0.0015(7) C12 0.0113(7) 0.0178(8) 0.0190(7) -0.0043(6) 0.0016(6) 0.0011(6) C13 0.0231(8) 0.0348(9) 0.0317(9) -0.0090(7) -0.0099(8) 0.0153(8) C14 0.0231(9) 0.0262(8) 0.0432(10) -0.0095(8) 0.0180(9) -0.0042(7) C15 0.0155(8) 0.0190(8) 0.0274(8) -0.0072(6) 0.0013(7) 0.0009(6) C16 0.0213(8) 0.0181(7) 0.0259(7) -0.0027(8) 0.0032(6) -0.0070(8) C17 0.0237(8) 0.0141(6) 0.0202(7) -0.0011(6) -0.0027(8) 0.0028(6) C18 0.0147(8) 0.0171(7) 0.0133(6) 0.0026(5) 0.0040(5) 0.0030(5) C19 0.0236(9) 0.0399(9) 0.0146(7) 0.0093(6) 0.0054(7) 0.0057(9) C20 0.0174(7) 0.0201(7) 0.0327(8) 0.0026(8) 0.0098(8) -0.0020(6) C21 0.0184(8) 0.0225(8) 0.0199(7) 0.0032(6) 0.0064(6) 0.0067(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zr C6 2.3306(19) . ? Zr C5 2.3307(18) . ? Zr C4 2.3362(16) . ? Zr C3 2.3413(17) . ? Zr C7 2.3503(19) . ? Zr C2 2.3537(17) . ? Zr N 2.3560(13) . ? Zr C1 2.3581(17) . ? Zr C8 2.4506(15) . ? Zr C11 2.4592(11) . ? Zr C9 2.5825(15) . ? Zr C10 2.5869(15) . ? N C11 1.3848(19) . ? N C8 1.3876(19) . ? C1 C7 1.411(3) . ? C1 C2 1.425(3) . ? C2 C3 1.433(2) . ? C3 C4 1.416(3) . ? C4 C5 1.429(3) . ? C5 C6 1.423(3) . ? C6 C7 1.423(3) . ? C8 C9 1.415(2) . ? C8 C12 1.524(2) . ? C9 C10 1.431(2) . ? C9 C16 1.508(2) . ? C10 C11 1.413(2) . ? C10 C17 1.510(2) . ? C11 C18 1.528(2) . ? C12 C14 1.529(2) . ? C12 C15 1.533(2) . ? C12 C13 1.537(2) . ? C18 C20 1.531(2) . ? C18 C21 1.534(2) . ? C18 C19 1.543(2) . ? 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 C6 Zr C5 35.54(7) . . ? C6 Zr C4 66.73(7) . . ? C5 Zr C4 35.65(6) . . ? C6 Zr C3 86.56(7) . . ? C5 Zr C3 66.67(7) . . ? C4 Zr C3 35.23(6) . . ? C6 Zr C7 35.39(7) . . ? C5 Zr C7 66.31(7) . . ? C4 Zr C7 85.79(6) . . ? C3 Zr C7 85.89(7) . . ? C6 Zr C2 86.31(7) . . ? C5 Zr C2 86.34(6) . . ? C4 Zr C2 66.29(6) . . ? C3 Zr C2 35.54(6) . . ? C7 Zr C2 65.98(7) . . ? C6 Zr N 131.21(6) . . ? C5 Zr N 146.39(5) . . ? C4 Zr N 152.99(5) . . ? C3 Zr N 141.85(6) . . ? C7 Zr N 120.59(6) . . ? C2 Zr N 127.14(6) . . ? C6 Zr C1 66.08(8) . . ? C5 Zr C1 85.73(7) . . ? C4 Zr C1 85.52(6) . . ? C3 Zr C1 66.23(7) . . ? C7 Zr C1 34.87(8) . . ? C2 Zr C1 35.21(7) . . ? N Zr C1 119.06(6) . . ? C6 Zr C8 160.63(6) . . ? C5 Zr C8 143.59(6) . . ? C4 Zr C8 122.96(6) . . ? C3 Zr C8 110.80(6) . . ? C7 Zr C8 149.20(7) . . ? C2 Zr C8 112.75(6) . . ? N Zr C8 33.49(5) . . ? C1 Zr C8 127.97(6) . . ? C6 Zr C11 106.55(6) . . ? C5 Zr C11 113.05(5) . . ? C4 Zr C11 132.54(5) . . ? C3 Zr C11 156.31(6) . . ? C7 Zr C11 116.31(6) . . ? C2 Zr C11 160.05(6) . . ? N Zr C11 33.34(4) . . ? C1 Zr C11 136.95(6) . . ? C8 Zr C11 54.18(5) . . ? C6 Zr C9 137.35(6) . . ? C5 Zr C9 111.11(6) . . ? C4 Zr C9 97.97(5) . . ? C3 Zr C9 103.34(6) . . ? C7 Zr C9 168.73(6) . . ? C2 Zr C9 125.26(6) . . ? N Zr C9 55.02(5) . . ? C1 Zr C9 155.61(7) . . ? C8 Zr C9 32.52(4) . . ? C11 Zr C9 53.69(5) . . ? C6 Zr C10 109.58(6) . . ? C5 Zr C10 96.29(5) . . ? C4 Zr C10 102.69(5) . . ? C3 Zr C10 124.88(6) . . ? C7 Zr C10 136.66(7) . . ? C2 Zr C10 155.97(6) . . ? N Zr C10 54.93(4) . . ? C1 Zr C10 168.56(6) . . ? C8 Zr C10 53.78(5) . . ? C11 Zr C10 32.41(5) . . ? C9 Zr C10 32.15(5) . . ? C11 N C8 107.52(12) . . ? C11 N Zr 77.42(7) . . ? C8 N Zr 77.00(8) . . ? C7 C1 C2 129.15(17) . . ? C7 C1 Zr 72.26(10) . . ? C2 C1 Zr 72.23(10) . . ? C1 C2 C3 127.91(18) . . ? C1 C2 Zr 72.57(10) . . ? C3 C2 Zr 71.76(10) . . ? C4 C3 C2 128.38(18) . . ? C4 C3 Zr 72.19(9) . . ? C2 C3 Zr 72.70(10) . . ? C3 C4 C5 129.02(17) . . ? C3 C4 Zr 72.58(10) . . ? C5 C4 Zr 71.96(10) . . ? C6 C5 C4 128.36(18) . . ? C6 C5 Zr 72.22(11) . . ? C4 C5 Zr 72.38(10) . . ? C5 C6 C7 128.25(18) . . ? C5 C6 Zr 72.24(11) . . ? C7 C6 Zr 73.06(12) . . ? C1 C7 C6 128.91(18) . . ? C1 C7 Zr 72.87(11) . . ? C6 C7 Zr 71.55(11) . . ? N C8 C9 109.58(14) . . ? N C8 C12 118.07(13) . . ? C9 C8 C12 131.64(14) . . ? N C8 Zr 69.51(8) . . ? C9 C8 Zr 78.87(9) . . ? C12 C8 Zr 124.53(10) . . ? C8 C9 C10 106.56(14) . . ? C8 C9 C16 128.56(15) . . ? C10 C9 C16 124.76(14) . . ? C8 C9 Zr 68.61(9) . . ? C10 C9 Zr 74.10(8) . . ? C16 C9 Zr 125.36(10) . . ? C11 C10 C9 106.50(13) . . ? C11 C10 C17 128.52(14) . . ? C9 C10 C17 124.74(14) . . ? C11 C10 Zr 68.82(8) . . ? C9 C10 Zr 73.75(8) . . ? C17 C10 Zr 126.78(10) . . ? N C11 C10 109.77(12) . . ? N C11 C18 118.60(13) . . ? C10 C11 C18 131.12(13) . . ? N C11 Zr 69.24(7) . . ? C10 C11 Zr 78.78(8) . . ? C18 C11 Zr 123.93(9) . . ? C8 C12 C14 113.50(14) . . ? C8 C12 C15 110.33(13) . . ? C14 C12 C15 108.24(13) . . ? C8 C12 C13 106.26(13) . . ? C14 C12 C13 109.63(15) . . ? C15 C12 C13 108.78(14) . . ? C11 C18 C20 110.31(12) . . ? C11 C18 C21 113.55(12) . . ? C20 C18 C21 108.17(13) . . ? C11 C18 C19 106.51(13) . . ? C20 C18 C19 108.85(14) . . ? C21 C18 C19 109.37(13) . . ? 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 C6 Zr N C11 50.03(12) . . . . ? C5 Zr N C11 -0.44(15) . . . . ? C4 Zr N C11 -74.14(15) . . . . ? C3 Zr N C11 -139.66(10) . . . . ? C7 Zr N C11 92.20(11) . . . . ? C2 Zr N C11 173.83(9) . . . . ? C1 Zr N C11 132.57(10) . . . . ? C8 Zr N C11 -111.59(12) . . . . ? C9 Zr N C11 -75.44(9) . . . . ? C10 Zr N C11 -35.92(8) . . . . ? C6 Zr N C8 161.62(10) . . . . ? C5 Zr N C8 111.15(12) . . . . ? C4 Zr N C8 37.45(16) . . . . ? C3 Zr N C8 -28.07(13) . . . . ? C7 Zr N C8 -156.21(10) . . . . ? C2 Zr N C8 -74.58(10) . . . . ? C1 Zr N C8 -115.84(10) . . . . ? C11 Zr N C8 111.59(12) . . . . ? C9 Zr N C8 36.15(8) . . . . ? C10 Zr N C8 75.67(9) . . . . ? C6 Zr C1 C7 22.56(11) . . . . ? C5 Zr C1 C7 53.30(11) . . . . ? C4 Zr C1 C7 89.06(11) . . . . ? C3 Zr C1 C7 119.66(12) . . . . ? C2 Zr C1 C7 143.00(17) . . . . ? N Zr C1 C7 -102.76(11) . . . . ? C8 Zr C1 C7 -141.80(11) . . . . ? C11 Zr C1 C7 -66.39(14) . . . . ? C9 Zr C1 C7 -171.48(13) . . . . ? C10 Zr C1 C7 -47.4(4) . . . . ? C6 Zr C1 C2 -120.43(12) . . . . ? C5 Zr C1 C2 -89.69(12) . . . . ? C4 Zr C1 C2 -53.93(12) . . . . ? C3 Zr C1 C2 -23.34(10) . . . . ? C7 Zr C1 C2 -143.00(17) . . . . ? N Zr C1 C2 114.25(11) . . . . ? C8 Zr C1 C2 75.20(12) . . . . ? C11 Zr C1 C2 150.61(10) . . . . ? C9 Zr C1 C2 45.52(19) . . . . ? C10 Zr C1 C2 169.6(3) . . . . ? C7 C1 C2 C3 1.0(3) . . . . ? Zr C1 C2 C3 48.67(17) . . . . ? C7 C1 C2 Zr -47.66(18) . . . . ? C6 Zr C2 C1 52.17(12) . . . . ? C5 Zr C2 C1 87.78(12) . . . . ? C4 Zr C2 C1 118.34(13) . . . . ? C3 Zr C2 C1 141.41(17) . . . . ? C7 Zr C2 C1 22.13(11) . . . . ? N Zr C2 C1 -89.04(12) . . . . ? C8 Zr C2 C1 -124.26(11) . . . . ? C11 Zr C2 C1 -79.1(2) . . . . ? C9 Zr C2 C1 -158.84(10) . . . . ? C10 Zr C2 C1 -174.98(13) . . . . ? C6 Zr C2 C3 -89.24(12) . . . . ? C5 Zr C2 C3 -53.62(12) . . . . ? C4 Zr C2 C3 -23.07(11) . . . . ? C7 Zr C2 C3 -119.27(13) . . . . ? N Zr C2 C3 129.55(11) . . . . ? C1 Zr C2 C3 -141.41(17) . . . . ? C8 Zr C2 C3 94.33(11) . . . . ? C11 Zr C2 C3 139.52(16) . . . . ? C9 Zr C2 C3 59.75(13) . . . . ? C10 Zr C2 C3 43.6(2) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? Zr C2 C3 C4 49.06(17) . . . . ? C1 C2 C3 Zr -48.97(17) . . . . ? C6 Zr C3 C4 -53.07(11) . . . . ? C5 Zr C3 C4 -22.59(10) . . . . ? C7 Zr C3 C4 -88.53(12) . . . . ? C2 Zr C3 C4 -141.54(17) . . . . ? N Zr C3 C4 134.23(11) . . . . ? C1 Zr C3 C4 -118.40(13) . . . . ? C8 Zr C3 C4 118.10(10) . . . . ? C11 Zr C3 C4 71.91(19) . . . . ? C9 Zr C3 C4 84.92(11) . . . . ? C10 Zr C3 C4 58.48(13) . . . . ? C6 Zr C3 C2 88.47(12) . . . . ? C5 Zr C3 C2 118.95(13) . . . . ? C4 Zr C3 C2 141.54(17) . . . . ? C7 Zr C3 C2 53.01(12) . . . . ? N Zr C3 C2 -84.23(14) . . . . ? C1 Zr C3 C2 23.14(11) . . . . ? C8 Zr C3 C2 -100.36(11) . . . . ? C11 Zr C3 C2 -146.55(14) . . . . ? C9 Zr C3 C2 -133.54(11) . . . . ? C10 Zr C3 C2 -159.98(10) . . . . ? C2 C3 C4 C5 -1.5(3) . . . . ? Zr C3 C4 C5 47.78(16) . . . . ? C2 C3 C4 Zr -49.25(17) . . . . ? C6 Zr C4 C3 119.71(12) . . . . ? C5 Zr C4 C3 142.76(16) . . . . ? C7 Zr C4 C3 88.83(12) . . . . ? C2 Zr C4 C3 23.25(11) . . . . ? N Zr C4 C3 -102.94(14) . . . . ? C1 Zr C4 C3 53.85(12) . . . . ? C8 Zr C4 C3 -79.37(12) . . . . ? C11 Zr C4 C3 -148.78(10) . . . . ? C9 Zr C4 C3 -101.86(11) . . . . ? C10 Zr C4 C3 -134.21(10) . . . . ? C6 Zr C4 C5 -23.05(10) . . . . ? C3 Zr C4 C5 -142.76(16) . . . . ? C7 Zr C4 C5 -53.93(11) . . . . ? C2 Zr C4 C5 -119.51(12) . . . . ? N Zr C4 C5 114.30(13) . . . . ? C1 Zr C4 C5 -88.91(11) . . . . ? C8 Zr C4 C5 137.87(10) . . . . ? C11 Zr C4 C5 68.45(12) . . . . ? C9 Zr C4 C5 115.38(10) . . . . ? C10 Zr C4 C5 83.03(10) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? Zr C4 C5 C6 48.72(16) . . . . ? C3 C4 C5 Zr -48.00(16) . . . . ? C4 Zr C5 C6 -141.77(15) . . . . ? C3 Zr C5 C6 -119.42(12) . . . . ? C7 Zr C5 C6 -23.46(10) . . . . ? C2 Zr C5 C6 -88.79(11) . . . . ? N Zr C5 C6 86.64(14) . . . . ? C1 Zr C5 C6 -53.50(11) . . . . ? C8 Zr C5 C6 146.75(11) . . . . ? C11 Zr C5 C6 86.38(11) . . . . ? C9 Zr C5 C6 144.67(10) . . . . ? C10 Zr C5 C6 115.19(10) . . . . ? C6 Zr C5 C4 141.77(15) . . . . ? C3 Zr C5 C4 22.35(10) . . . . ? C7 Zr C5 C4 118.31(11) . . . . ? C2 Zr C5 C4 52.98(10) . . . . ? N Zr C5 C4 -131.59(10) . . . . ? C1 Zr C5 C4 88.27(11) . . . . ? C8 Zr C5 C4 -71.48(13) . . . . ? C11 Zr C5 C4 -131.85(9) . . . . ? C9 Zr C5 C4 -73.56(10) . . . . ? C10 Zr C5 C4 -103.04(10) . . . . ? C4 C5 C6 C7 1.3(3) . . . . ? Zr C5 C6 C7 50.06(17) . . . . ? C4 C5 C6 Zr -48.78(16) . . . . ? C4 Zr C6 C5 23.12(9) . . . . ? C3 Zr C6 C5 53.25(10) . . . . ? C7 Zr C6 C5 140.99(15) . . . . ? C2 Zr C6 C5 88.85(11) . . . . ? N Zr C6 C5 -132.74(9) . . . . ? C1 Zr C6 C5 118.73(11) . . . . ? C8 Zr C6 C5 -101.1(2) . . . . ? C11 Zr C6 C5 -106.67(10) . . . . ? C9 Zr C6 C5 -52.76(13) . . . . ? C10 Zr C6 C5 -72.67(10) . . . . ? C5 Zr C6 C7 -140.99(15) . . . . ? C4 Zr C6 C7 -117.87(11) . . . . ? C3 Zr C6 C7 -87.74(11) . . . . ? C2 Zr C6 C7 -52.14(11) . . . . ? N Zr C6 C7 86.27(12) . . . . ? C1 Zr C6 C7 -22.26(10) . . . . ? C8 Zr C6 C7 117.90(19) . . . . ? C11 Zr C6 C7 112.34(10) . . . . ? C9 Zr C6 C7 166.24(10) . . . . ? C10 Zr C6 C7 146.33(10) . . . . ? C2 C1 C7 C6 0.1(3) . . . . ? Zr C1 C7 C6 -47.59(18) . . . . ? C2 C1 C7 Zr 47.65(18) . . . . ? C5 C6 C7 C1 -1.7(3) . . . . ? Zr C6 C7 C1 48.06(18) . . . . ? C5 C6 C7 Zr -49.75(17) . . . . ? C6 Zr C7 C1 -142.72(16) . . . . ? C5 Zr C7 C1 -119.17(12) . . . . ? C4 Zr C7 C1 -88.21(11) . . . . ? C3 Zr C7 C1 -52.88(11) . . . . ? C2 Zr C7 C1 -22.33(10) . . . . ? N Zr C7 C1 97.97(11) . . . . ? C8 Zr C7 C1 72.21(15) . . . . ? C11 Zr C7 C1 135.75(10) . . . . ? C9 Zr C7 C1 161.8(3) . . . . ? C10 Zr C7 C1 167.73(9) . . . . ? C5 Zr C7 C6 23.55(10) . . . . ? C4 Zr C7 C6 54.51(11) . . . . ? C3 Zr C7 C6 89.84(11) . . . . ? C2 Zr C7 C6 120.39(12) . . . . ? N Zr C7 C6 -119.31(10) . . . . ? C1 Zr C7 C6 142.72(16) . . . . ? C8 Zr C7 C6 -145.07(12) . . . . ? C11 Zr C7 C6 -81.53(11) . . . . ? C9 Zr C7 C6 -55.5(4) . . . . ? C10 Zr C7 C6 -49.55(13) . . . . ? C11 N C8 C9 2.69(17) . . . . ? Zr N C8 C9 -69.42(12) . . . . ? C11 N C8 C12 -168.78(13) . . . . ? Zr N C8 C12 119.11(13) . . . . ? C11 N C8 Zr 72.11(9) . . . . ? C6 Zr C8 N -45.6(2) . . . . ? C5 Zr C8 N -119.58(10) . . . . ? C4 Zr C8 N -160.78(8) . . . . ? C3 Zr C8 N 161.88(9) . . . . ? C7 Zr C8 N 42.71(16) . . . . ? C2 Zr C8 N 123.57(9) . . . . ? C1 Zr C8 N 86.38(10) . . . . ? C11 Zr C8 N -39.06(8) . . . . ? C9 Zr C8 N -115.98(13) . . . . ? C10 Zr C8 N -79.43(9) . . . . ? C6 Zr C8 C9 70.3(2) . . . . ? C5 Zr C8 C9 -3.60(15) . . . . ? C4 Zr C8 C9 -44.80(12) . . . . ? C3 Zr C8 C9 -82.14(11) . . . . ? C7 Zr C8 C9 158.68(12) . . . . ? C2 Zr C8 C9 -120.45(10) . . . . ? N Zr C8 C9 115.98(13) . . . . ? C1 Zr C8 C9 -157.64(10) . . . . ? C11 Zr C8 C9 76.91(10) . . . . ? C10 Zr C8 C9 36.55(9) . . . . ? C6 Zr C8 C12 -156.30(18) . . . . ? C5 Zr C8 C12 129.77(12) . . . . ? C4 Zr C8 C12 88.57(13) . . . . ? C3 Zr C8 C12 51.23(14) . . . . ? C7 Zr C8 C12 -67.95(18) . . . . ? C2 Zr C8 C12 12.91(14) . . . . ? N Zr C8 C12 -110.66(15) . . . . ? C1 Zr C8 C12 -24.27(15) . . . . ? C11 Zr C8 C12 -149.72(15) . . . . ? C9 Zr C8 C12 133.37(18) . . . . ? C10 Zr C8 C12 169.92(15) . . . . ? N C8 C9 C10 -1.59(18) . . . . ? C12 C8 C9 C10 168.33(15) . . . . ? Zr C8 C9 C10 -64.94(11) . . . . ? N C8 C9 C16 -177.80(14) . . . . ? C12 C8 C9 C16 -7.9(3) . . . . ? Zr C8 C9 C16 118.85(16) . . . . ? N C8 C9 Zr 63.35(10) . . . . ? C12 C8 C9 Zr -126.73(18) . . . . ? C6 Zr C9 C8 -152.55(10) . . . . ? C5 Zr C9 C8 177.71(10) . . . . ? C4 Zr C9 C8 143.34(10) . . . . ? C3 Zr C9 C8 107.88(10) . . . . ? C7 Zr C9 C8 -107.8(3) . . . . ? C2 Zr C9 C8 76.81(11) . . . . ? N Zr C9 C8 -37.26(9) . . . . ? C1 Zr C9 C8 46.56(18) . . . . ? C11 Zr C9 C8 -78.57(10) . . . . ? C10 Zr C9 C8 -115.47(14) . . . . ? C6 Zr C9 C10 -37.08(13) . . . . ? C5 Zr C9 C10 -66.82(10) . . . . ? C4 Zr C9 C10 -101.19(10) . . . . ? C3 Zr C9 C10 -136.66(10) . . . . ? C7 Zr C9 C10 7.7(4) . . . . ? C2 Zr C9 C10 -167.72(9) . . . . ? N Zr C9 C10 78.21(9) . . . . ? C1 Zr C9 C10 162.03(13) . . . . ? C8 Zr C9 C10 115.47(14) . . . . ? C11 Zr C9 C10 36.90(8) . . . . ? C6 Zr C9 C16 84.57(16) . . . . ? C5 Zr C9 C16 54.83(15) . . . . ? C4 Zr C9 C16 20.46(14) . . . . ? C3 Zr C9 C16 -15.01(15) . . . . ? C7 Zr C9 C16 129.4(3) . . . . ? C2 Zr C9 C16 -46.07(16) . . . . ? N Zr C9 C16 -160.14(15) . . . . ? C1 Zr C9 C16 -76.3(2) . . . . ? C8 Zr C9 C16 -122.89(18) . . . . ? C11 Zr C9 C16 158.55(16) . . . . ? C10 Zr C9 C16 121.65(17) . . . . ? C8 C9 C10 C11 -0.10(17) . . . . ? C16 C9 C10 C11 176.29(14) . . . . ? Zr C9 C10 C11 -61.39(10) . . . . ? C8 C9 C10 C17 -174.88(15) . . . . ? C16 C9 C10 C17 1.5(2) . . . . ? Zr C9 C10 C17 123.83(15) . . . . ? C8 C9 C10 Zr 61.29(11) . . . . ? C16 C9 C10 Zr -122.33(15) . . . . ? C6 Zr C10 C11 -90.22(10) . . . . ? C5 Zr C10 C11 -124.16(9) . . . . ? C4 Zr C10 C11 -159.75(9) . . . . ? C3 Zr C10 C11 169.97(9) . . . . ? C7 Zr C10 C11 -62.33(12) . . . . ? C2 Zr C10 C11 140.72(14) . . . . ? N Zr C10 C11 36.99(8) . . . . ? C1 Zr C10 C11 -24.5(4) . . . . ? C8 Zr C10 C11 78.49(9) . . . . ? C9 Zr C10 C11 115.48(13) . . . . ? C6 Zr C10 C9 154.30(10) . . . . ? C5 Zr C10 C9 120.37(10) . . . . ? C4 Zr C10 C9 84.77(10) . . . . ? C3 Zr C10 C9 54.50(12) . . . . ? C7 Zr C10 C9 -177.81(10) . . . . ? C2 Zr C10 C9 25.24(18) . . . . ? N Zr C10 C9 -78.49(9) . . . . ? C1 Zr C10 C9 -140.0(3) . . . . ? C8 Zr C10 C9 -36.99(8) . . . . ? C11 Zr C10 C9 -115.48(13) . . . . ? C6 Zr C10 C17 32.75(14) . . . . ? C5 Zr C10 C17 -1.19(14) . . . . ? C4 Zr C10 C17 -36.78(14) . . . . ? C3 Zr C10 C17 -67.05(15) . . . . ? C7 Zr C10 C17 60.64(16) . . . . ? C2 Zr C10 C17 -96.31(19) . . . . ? N Zr C10 C17 159.96(15) . . . . ? C1 Zr C10 C17 98.4(3) . . . . ? C8 Zr C10 C17 -158.54(15) . . . . ? C11 Zr C10 C17 122.97(17) . . . . ? C9 Zr C10 C17 -121.55(17) . . . . ? C8 N C11 C10 -2.76(15) . . . . ? Zr N C11 C10 69.05(10) . . . . ? C8 N C11 C18 169.95(12) . . . . ? Zr N C11 C18 -118.24(11) . . . . ? C8 N C11 Zr -71.81(10) . . . . ? C9 C10 C11 N 1.77(15) . . . . ? C17 C10 C11 N 176.28(15) . . . . ? Zr C10 C11 N -62.91(9) . . . . ? C9 C10 C11 C18 -169.72(14) . . . . ? C17 C10 C11 C18 4.8(3) . . . . ? Zr C10 C11 C18 125.60(15) . . . . ? C9 C10 C11 Zr 64.68(10) . . . . ? C17 C10 C11 Zr -120.81(16) . . . . ? C6 Zr C11 N -143.03(9) . . . . ? C5 Zr C11 N 179.73(9) . . . . ? C4 Zr C11 N 143.63(9) . . . . ? C3 Zr C11 N 95.54(16) . . . . ? C7 Zr C11 N -106.33(10) . . . . ? C2 Zr C11 N -14.5(2) . . . . ? C1 Zr C11 N -70.57(13) . . . . ? C8 Zr C11 N 39.25(8) . . . . ? C9 Zr C11 N 79.77(9) . . . . ? C10 Zr C11 N 116.36(12) . . . . ? C6 Zr C11 C10 100.61(10) . . . . ? C5 Zr C11 C10 63.37(10) . . . . ? C4 Zr C11 C10 27.27(12) . . . . ? C3 Zr C11 C10 -20.82(19) . . . . ? C7 Zr C11 C10 137.30(10) . . . . ? C2 Zr C11 C10 -130.91(18) . . . . ? N Zr C11 C10 -116.36(12) . . . . ? C1 Zr C11 C10 173.07(11) . . . . ? C8 Zr C11 C10 -77.12(10) . . . . ? C9 Zr C11 C10 -36.59(9) . . . . ? C6 Zr C11 C18 -31.81(13) . . . . ? C5 Zr C11 C18 -69.05(13) . . . . ? C4 Zr C11 C18 -105.15(13) . . . . ? C3 Zr C11 C18 -153.24(15) . . . . ? C7 Zr C11 C18 4.88(14) . . . . ? C2 Zr C11 C18 96.7(2) . . . . ? N Zr C11 C18 111.22(15) . . . . ? C1 Zr C11 C18 40.65(16) . . . . ? C8 Zr C11 C18 150.46(14) . . . . ? C9 Zr C11 C18 -169.01(14) . . . . ? C10 Zr C11 C18 -132.42(16) . . . . ? N C8 C12 C14 -153.52(14) . . . . ? C9 C8 C12 C14 37.3(2) . . . . ? Zr C8 C12 C14 -70.10(17) . . . . ? N C8 C12 C15 -31.84(19) . . . . ? C9 C8 C12 C15 158.93(17) . . . . ? Zr C8 C12 C15 51.58(17) . . . . ? N C8 C12 C13 85.91(17) . . . . ? C9 C8 C12 C13 -83.3(2) . . . . ? Zr C8 C12 C13 169.34(11) . . . . ? N C11 C18 C20 30.47(18) . . . . ? C10 C11 C18 C20 -158.66(15) . . . . ? Zr C11 C18 C20 -52.65(16) . . . . ? N C11 C18 C21 152.06(13) . . . . ? C10 C11 C18 C21 -37.1(2) . . . . ? Zr C11 C18 C21 68.95(16) . . . . ? N C11 C18 C19 -87.51(15) . . . . ? C10 C11 C18 C19 83.37(18) . . . . ? Zr C11 C18 C19 -170.62(10) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.304 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.062 _iucr_refine_instructions_details ; TITL MK71 in P2(1)2(1)2(1) CELL 0.71073 9.590760 13.947041 14.338490 90.0000 90.0000 90.0000 ZERR 4.00 0.000300 0.000400 0.000300 0.0000 0.0000 0.0000 LATT -1 SYMM -x+1/2,-y, z+1/2 SYMM -x, y+1/2,-z+1/2 SYMM x+1/2,-y+1/2,-z SFAC C H N Zr UNIT 84 124 4 4 TEMP -173 SIZE 0.2 0.15 0.05 ACTA 61 CONF MERG 2 FMAP 2 PLAN 10 L.S. 4 WGHT 0.017200 0.597000 FVAR 3.12289 ZR 4 0.444860 0.565954 0.845922 11.00000 0.01346 0.01772 = 0.00844 0.00039 -0.00104 -0.00207 N 3 0.379037 0.647767 0.709076 11.00000 0.01079 0.01333 = 0.01162 0.00065 0.00103 0.00121 C1 1 0.535422 0.654357 0.972348 11.00000 0.04792 0.02518 = 0.01520 0.00132 -0.00759 -0.01325 H1 2 0.536747 0.722855 0.978662 11.00000 0.02743 C2 1 0.405431 0.614530 1.000896 11.00000 0.03886 0.02429 = 0.01149 -0.00197 0.00193 0.00025 H2 2 0.336231 0.657138 1.021898 11.00000 0.01728 C3 1 0.358649 0.517475 0.991226 11.00000 0.02642 0.02946 = 0.01452 0.00121 0.00421 -0.00512 H3 2 0.266434 0.504961 1.008243 11.00000 0.03107 C4 1 0.430123 0.438676 0.951389 11.00000 0.03366 0.02045 = 0.01518 0.00327 -0.00146 -0.00660 H4 2 0.375872 0.378568 0.945038 11.00000 0.02865 C5 1 0.564974 0.436025 0.909132 11.00000 0.03144 0.02914 = 0.01563 0.00226 -0.00412 0.00847 H5 2 0.589793 0.378550 0.878059 11.00000 0.02259 C6 1 0.661726 0.512418 0.897555 11.00000 0.01639 0.05238 = 0.01703 0.00835 -0.00402 0.00319 H6 2 0.740342 0.494370 0.863265 11.00000 0.02937 C7 1 0.648350 0.609442 0.926874 11.00000 0.02543 0.04838 = 0.01840 0.01144 -0.00927 -0.01629 H7 2 0.718149 0.649407 0.910137 11.00000 0.04485 C8 1 0.253765 0.610348 0.741007 11.00000 0.01065 0.01563 = 0.01002 -0.00148 0.00016 -0.00066 C9 1 0.254660 0.509435 0.730895 11.00000 0.01444 0.01326 = 0.01088 -0.00020 -0.00275 -0.00212 C10 1 0.385082 0.485054 0.688568 11.00000 0.01498 0.01184 = 0.00999 -0.00093 -0.00354 0.00103 C11 1 0.457385 0.572213 0.674727 11.00000 0.01405 0.01401 = 0.00815 0.00133 -0.00041 0.00148 C12 1 0.137307 0.680252 0.765738 11.00000 0.01130 0.01782 = 0.01898 -0.00434 0.00159 0.00114 C13 1 0.059000 0.700950 0.674432 11.00000 0.02312 0.03482 = 0.03167 -0.00900 -0.00988 0.01534 AFIX 137 H13A 2 -0.014857 0.747997 0.686121 11.00000 -1.50000 H13B 2 0.017636 0.641467 0.650805 11.00000 -1.50000 H13C 2 0.124281 0.726585 0.628140 11.00000 -1.50000 AFIX 0 C14 1 0.035501 0.641197 0.838484 11.00000 0.02305 0.02620 = 0.04323 -0.00946 0.01801 -0.00424 AFIX 137 H14A 2 0.087394 0.620187 0.893701 11.00000 -1.50000 H14B 2 -0.015653 0.586712 0.812178 11.00000 -1.50000 H14C 2 -0.030488 0.691660 0.856198 11.00000 -1.50000 AFIX 0 C15 1 0.198564 0.774376 0.802823 11.00000 0.01547 0.01901 = 0.02735 -0.00724 0.00132 0.00086 AFIX 137 H15A 2 0.252885 0.761482 0.859338 11.00000 -1.50000 H15B 2 0.122705 0.818961 0.817516 11.00000 -1.50000 H15C 2 0.259255 0.802840 0.755316 11.00000 -1.50000 AFIX 0 C16 1 0.140232 0.438836 0.753054 11.00000 0.02135 0.01806 = 0.02590 -0.00273 0.00323 -0.00700 AFIX 137 H16A 2 0.061922 0.448769 0.710224 11.00000 -1.50000 H16B 2 0.108645 0.448502 0.817370 11.00000 -1.50000 H16C 2 0.175778 0.373363 0.745964 11.00000 -1.50000 AFIX 0 C17 1 0.426024 0.385436 0.657789 11.00000 0.02367 0.01412 = 0.02018 -0.00108 -0.00265 0.00282 AFIX 137 H17A 2 0.511188 0.365881 0.690418 11.00000 -1.50000 H17B 2 0.442807 0.385263 0.590370 11.00000 -1.50000 H17C 2 0.350654 0.340500 0.672600 11.00000 -1.50000 AFIX 0 C18 1 0.590412 0.594689 0.620254 11.00000 0.01472 0.01708 = 0.01331 0.00256 0.00395 0.00297 C19 1 0.546447 0.608012 0.517589 11.00000 0.02362 0.03995 = 0.01463 0.00935 0.00543 0.00572 AFIX 137 H19A 2 0.477062 0.659407 0.513321 11.00000 -1.50000 H19B 2 0.506067 0.548151 0.494103 11.00000 -1.50000 H19C 2 0.628279 0.624941 0.480116 11.00000 -1.50000 AFIX 0 C20 1 0.655562 0.688172 0.655405 11.00000 0.01739 0.02015 = 0.03269 0.00256 0.00978 -0.00200 AFIX 137 H20A 2 0.688097 0.679430 0.719635 11.00000 -1.50000 H20B 2 0.585706 0.739419 0.653593 11.00000 -1.50000 H20C 2 0.734583 0.705501 0.615486 11.00000 -1.50000 AFIX 0 C21 1 0.701024 0.515459 0.626520 11.00000 0.01837 0.02255 = 0.01994 0.00322 0.00635 0.00674 AFIX 137 H21A 2 0.666483 0.457538 0.595480 11.00000 -1.50000 H21B 2 0.720405 0.501218 0.692181 11.00000 -1.50000 H21C 2 0.786827 0.537021 0.595899 11.00000 -1.50000 HKLF 4 ; data_mk60 _database_code_depnum_ccdc_archive 'CCDC 902362' #TrackingRef 'combined_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H34 N2 Zr' _chemical_formula_weight 417.73 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' 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/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 9.3606(2) _cell_length_b 25.4410(4) _cell_length_c 9.9949(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.929(3) _cell_angle_gamma 90.00 _cell_volume 2122.12(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 40727 _cell_measurement_theta_min 2.2809 _cell_measurement_theta_max 30.8569 _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.525 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96399 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 124284 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 30.93 _reflns_number_total 6426 _reflns_number_gt 5885 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _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. The hydrogens at the seven-membered ring were refined freely. The methyl groups were refined as idealised rigid groups allowed to rotate but not tip. ; _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^)+(0.0170P)^2^+1.0999P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6426 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0274 _refine_ls_R_factor_gt 0.0229 _refine_ls_wR_factor_ref 0.0507 _refine_ls_wR_factor_gt 0.0491 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.004 _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 Zr Zr 0.416828(12) 0.361904(4) 0.465547(11) 0.01228(3) Uani 1 1 d . . . N1 N 0.25430(11) 0.42702(3) 0.52069(10) 0.01195(16) Uani 1 1 d . . . N2 N 0.24074(11) 0.34172(4) 0.58184(10) 0.01256(17) Uani 1 1 d . . . C1 C 0.69240(14) 0.37889(5) 0.58541(14) 0.0181(2) Uani 1 1 d . . . H1 H 0.7534(19) 0.3976(6) 0.6734(18) 0.025(4) Uiso 1 1 d . . . C2 C 0.62372(14) 0.40905(5) 0.45057(14) 0.0187(2) Uani 1 1 d . . . H2 H 0.6432(19) 0.4455(6) 0.4617(18) 0.025(4) Uiso 1 1 d . . . C3 C 0.51619(14) 0.39225(5) 0.30245(14) 0.0186(2) Uani 1 1 d . . . H3 H 0.4769(19) 0.4193(6) 0.2307(18) 0.025(4) Uiso 1 1 d . . . C4 C 0.44986(14) 0.34127(5) 0.25288(13) 0.0180(2) Uani 1 1 d . . . H4 H 0.3714(18) 0.3389(6) 0.1495(17) 0.018(4) Uiso 1 1 d . . . C5 C 0.47558(14) 0.29427(5) 0.33848(14) 0.0180(2) Uani 1 1 d . . . H5 H 0.4135(18) 0.2651(6) 0.2885(17) 0.022(4) Uiso 1 1 d . . . C6 C 0.57310(14) 0.28686(5) 0.49526(14) 0.0183(2) Uani 1 1 d . . . H6 H 0.5630(18) 0.2539(6) 0.5348(17) 0.022(4) Uiso 1 1 d . . . C7 C 0.66931(14) 0.32459(5) 0.60537(14) 0.0183(2) Uani 1 1 d . . . H7 H 0.7152(19) 0.3134(6) 0.7032(18) 0.027(4) Uiso 1 1 d . . . C8 C 0.30335(13) 0.39026(4) 0.63126(12) 0.01213(19) Uani 1 1 d . . . C9 C 0.14322(12) 0.40153(4) 0.39196(12) 0.01143(18) Uani 1 1 d . . . C10 C 0.13487(12) 0.34802(4) 0.43036(12) 0.01152(18) Uani 1 1 d . . . C11 C 0.39576(14) 0.40412(4) 0.79621(12) 0.0151(2) Uani 1 1 d . . . C12 C 0.48974(16) 0.45512(5) 0.81619(14) 0.0246(3) Uani 1 1 d . . . H12A H 0.5703 0.4501 0.7803 0.037 Uiso 1 1 calc R . . H12B H 0.5430 0.4647 0.9227 0.037 Uiso 1 1 calc R . . H12C H 0.4161 0.4833 0.7585 0.037 Uiso 1 1 calc R . . C13 C 0.50705(17) 0.35948(5) 0.88611(14) 0.0250(3) Uani 1 1 d . . . H13A H 0.5925 0.3553 0.8559 0.037 Uiso 1 1 calc R . . H13B H 0.4457 0.3267 0.8667 0.037 Uiso 1 1 calc R . . H13C H 0.5543 0.3678 0.9934 0.037 Uiso 1 1 calc R . . C14 C 0.26788(16) 0.41229(5) 0.85110(14) 0.0236(2) Uani 1 1 d . . . H14A H 0.3197 0.4240 0.9559 0.035 Uiso 1 1 calc R . . H14B H 0.2115 0.3791 0.8434 0.035 Uiso 1 1 calc R . . H14C H 0.1911 0.4390 0.7889 0.035 Uiso 1 1 calc R . . C15 C 0.04789(13) 0.43618(4) 0.25420(12) 0.0147(2) Uani 1 1 d . . . C16 C 0.11369(15) 0.49266(5) 0.28777(14) 0.0212(2) Uani 1 1 d . . . H16A H 0.1035 0.5063 0.3748 0.032 Uiso 1 1 calc R . . H16B H 0.0526 0.5150 0.2004 0.032 Uiso 1 1 calc R . . H16C H 0.2268 0.4926 0.3095 0.032 Uiso 1 1 calc R . . C17 C -0.12713(14) 0.43814(5) 0.22843(14) 0.0208(2) Uani 1 1 d . . . H17A H -0.1304 0.4511 0.3193 0.031 Uiso 1 1 calc R . . H17B H -0.1735 0.4028 0.2051 0.031 Uiso 1 1 calc R . . H17C H -0.1889 0.4618 0.1445 0.031 Uiso 1 1 calc R . . C18 C 0.05661(16) 0.41853(5) 0.11105(13) 0.0231(2) Uani 1 1 d . . . H18A H -0.0120 0.4412 0.0272 0.035 Uiso 1 1 calc R . . H18B H 0.0199 0.3821 0.0881 0.035 Uiso 1 1 calc R . . H18C H 0.1675 0.4211 0.1265 0.035 Uiso 1 1 calc R . . C19 C 0.02589(13) 0.30097(4) 0.35555(13) 0.0141(2) Uani 1 1 d . . . C20 C -0.04866(15) 0.29980(5) 0.18445(13) 0.0208(2) Uani 1 1 d . . . H20A H -0.1132 0.2679 0.1471 0.031 Uiso 1 1 calc R . . H20B H 0.0365 0.3000 0.1530 0.031 Uiso 1 1 calc R . . H20C H -0.1171 0.3307 0.1434 0.031 Uiso 1 1 calc R . . C21 C 0.12067(14) 0.24949(4) 0.41381(15) 0.0195(2) Uani 1 1 d . . . H21A H 0.1695 0.2489 0.5237 0.029 Uiso 1 1 calc R . . H21B H 0.2048 0.2474 0.3813 0.029 Uiso 1 1 calc R . . H21C H 0.0480 0.2195 0.3735 0.029 Uiso 1 1 calc R . . C22 C -0.10852(14) 0.30320(5) 0.40383(15) 0.0199(2) Uani 1 1 d . . . H22A H -0.1779 0.2724 0.3647 0.030 Uiso 1 1 calc R . . H22B H -0.1720 0.3352 0.3639 0.030 Uiso 1 1 calc R . . H22C H -0.0613 0.3035 0.5136 0.030 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 Zr 0.01022(5) 0.01403(5) 0.01338(5) 0.00005(4) 0.00603(4) 0.00106(4) N1 0.0118(4) 0.0126(4) 0.0112(4) 0.0007(3) 0.0051(3) 0.0016(3) N2 0.0133(4) 0.0132(4) 0.0127(4) 0.0006(3) 0.0073(3) 0.0006(3) C1 0.0124(5) 0.0210(5) 0.0197(5) -0.0046(4) 0.0062(4) -0.0012(4) C2 0.0167(5) 0.0184(5) 0.0231(6) -0.0033(4) 0.0108(5) -0.0042(4) C3 0.0196(5) 0.0209(5) 0.0179(5) 0.0007(4) 0.0109(5) -0.0023(4) C4 0.0177(5) 0.0220(5) 0.0164(5) -0.0033(4) 0.0093(4) -0.0023(4) C5 0.0170(5) 0.0173(5) 0.0221(6) -0.0047(4) 0.0110(5) -0.0017(4) C6 0.0170(5) 0.0156(5) 0.0238(6) 0.0005(4) 0.0105(5) 0.0029(4) C7 0.0131(5) 0.0218(5) 0.0186(5) 0.0010(4) 0.0060(4) 0.0046(4) C8 0.0129(4) 0.0126(5) 0.0117(5) 0.0004(4) 0.0063(4) 0.0023(4) C9 0.0103(4) 0.0127(4) 0.0115(4) 0.0001(4) 0.0051(4) 0.0008(3) C10 0.0110(4) 0.0128(4) 0.0125(5) 0.0000(4) 0.0069(4) 0.0007(4) C11 0.0174(5) 0.0157(5) 0.0104(5) -0.0006(4) 0.0046(4) 0.0027(4) C12 0.0273(6) 0.0245(6) 0.0164(6) -0.0055(5) 0.0051(5) -0.0073(5) C13 0.0298(6) 0.0250(6) 0.0131(5) 0.0016(4) 0.0035(5) 0.0118(5) C14 0.0269(6) 0.0296(6) 0.0167(5) -0.0013(5) 0.0120(5) 0.0050(5) C15 0.0143(5) 0.0147(5) 0.0125(5) 0.0023(4) 0.0038(4) 0.0015(4) C16 0.0225(6) 0.0150(5) 0.0201(6) 0.0057(4) 0.0044(5) -0.0002(4) C17 0.0139(5) 0.0213(6) 0.0216(6) 0.0024(4) 0.0031(4) 0.0042(4) C18 0.0290(6) 0.0262(6) 0.0136(5) 0.0044(4) 0.0093(5) 0.0032(5) C19 0.0134(5) 0.0131(5) 0.0175(5) -0.0024(4) 0.0085(4) -0.0018(4) C20 0.0219(6) 0.0196(5) 0.0192(6) -0.0068(4) 0.0080(5) -0.0041(4) C21 0.0189(5) 0.0120(5) 0.0299(6) -0.0010(4) 0.0131(5) -0.0011(4) C22 0.0169(5) 0.0178(5) 0.0299(6) -0.0026(5) 0.0149(5) -0.0028(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 Zr C7 2.3341(11) . ? Zr C2 2.3397(12) . ? Zr C1 2.3402(12) . ? Zr C6 2.3409(11) . ? Zr C4 2.3419(12) . ? Zr C3 2.3435(12) . ? Zr C5 2.3471(11) . ? Zr C8 2.4465(10) . ? Zr N2 2.4631(9) . ? Zr N1 2.4743(9) . ? Zr C10 2.5246(10) . ? Zr C9 2.5318(10) . ? N1 C8 1.3591(13) . ? N1 C9 1.3948(13) . ? N2 C8 1.3601(14) . ? N2 C10 1.3932(13) . ? C1 C2 1.4259(17) . ? C1 C7 1.4262(17) . ? C2 C3 1.4275(17) . ? C3 C4 1.4265(16) . ? C4 C5 1.4259(17) . ? C5 C6 1.4243(17) . ? C6 C7 1.4304(17) . ? C8 C11 1.5163(15) . ? C9 C10 1.4261(14) . ? C9 C15 1.5351(14) . ? C10 C19 1.5302(15) . ? C11 C13 1.5279(16) . ? C11 C12 1.5292(17) . ? C11 C14 1.5401(17) . ? C15 C18 1.5365(16) . ? C15 C16 1.5394(16) . ? C15 C17 1.5398(16) . ? C19 C20 1.5269(16) . ? C19 C22 1.5391(15) . ? C19 C21 1.5407(15) . ? 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 C7 Zr C2 66.66(4) . . ? C7 Zr C1 35.53(4) . . ? C2 Zr C1 35.48(4) . . ? C7 Zr C6 35.63(4) . . ? C2 Zr C6 86.47(4) . . ? C1 Zr C6 66.74(4) . . ? C7 Zr C4 86.45(4) . . ? C2 Zr C4 66.64(4) . . ? C1 Zr C4 86.45(4) . . ? C6 Zr C4 66.45(4) . . ? C7 Zr C3 86.40(4) . . ? C2 Zr C3 35.49(4) . . ? C1 Zr C3 66.58(4) . . ? C6 Zr C3 86.27(4) . . ? C4 Zr C3 35.45(4) . . ? C7 Zr C5 66.67(4) . . ? C2 Zr C5 86.42(4) . . ? C1 Zr C5 86.46(4) . . ? C6 Zr C5 35.37(4) . . ? C4 Zr C5 35.41(4) . . ? C3 Zr C5 66.49(4) . . ? C7 Zr C8 110.30(4) . . ? C2 Zr C8 121.19(4) . . ? C1 Zr C8 108.35(4) . . ? C6 Zr C8 126.34(4) . . ? C4 Zr C8 163.10(4) . . ? C3 Zr C8 143.57(4) . . ? C5 Zr C8 149.59(4) . . ? C7 Zr N2 110.20(4) . . ? C2 Zr N2 152.53(4) . . ? C1 Zr N2 127.95(4) . . ? C6 Zr N2 106.46(4) . . ? C4 Zr N2 140.64(4) . . ? C3 Zr N2 163.37(4) . . ? C5 Zr N2 118.26(4) . . ? C8 Zr N2 32.16(3) . . ? C7 Zr N1 134.18(4) . . ? C2 Zr N1 106.34(4) . . ? C1 Zr N1 114.12(4) . . ? C6 Zr N1 158.40(4) . . ? C4 Zr N1 134.39(4) . . ? C3 Zr N1 114.34(4) . . ? C5 Zr N1 158.40(4) . . ? C8 Zr N1 32.06(3) . . ? N2 Zr N1 54.84(3) . . ? C7 Zr C10 137.53(4) . . ? C2 Zr C10 154.99(4) . . ? C1 Zr C10 159.65(4) . . ? C6 Zr C10 117.22(4) . . ? C4 Zr C10 113.68(4) . . ? C3 Zr C10 131.94(4) . . ? C5 Zr C10 107.96(4) . . ? C8 Zr C10 52.30(3) . . ? N2 Zr C10 32.41(3) . . ? N1 Zr C10 54.22(3) . . ? C7 Zr C9 162.29(4) . . ? C2 Zr C9 122.35(4) . . ? C1 Zr C9 144.16(4) . . ? C6 Zr C9 148.58(4) . . ? C4 Zr C9 110.95(4) . . ? C3 Zr C9 109.55(4) . . ? C5 Zr C9 126.07(4) . . ? C8 Zr C9 52.20(3) . . ? N2 Zr C9 54.20(3) . . ? N1 Zr C9 32.33(3) . . ? C10 Zr C9 32.76(3) . . ? C8 N1 C9 105.44(9) . . ? C8 N1 Zr 72.84(6) . . ? C9 N1 Zr 76.11(6) . . ? C8 N2 C10 105.53(9) . . ? C8 N2 Zr 73.24(6) . . ? C10 N2 Zr 76.22(6) . . ? C2 C1 C7 128.42(11) . . ? C2 C1 Zr 72.24(7) . . ? C7 C1 Zr 72.00(6) . . ? C1 C2 C3 128.57(11) . . ? C1 C2 Zr 72.28(7) . . ? C3 C2 Zr 72.40(7) . . ? C4 C3 C2 128.60(11) . . ? C4 C3 Zr 72.21(7) . . ? C2 C3 Zr 72.11(7) . . ? C5 C4 C3 128.72(11) . . ? C5 C4 Zr 72.50(7) . . ? C3 C4 Zr 72.34(7) . . ? C6 C5 C4 128.39(11) . . ? C6 C5 Zr 72.07(7) . . ? C4 C5 Zr 72.10(7) . . ? C5 C6 C7 128.62(11) . . ? C5 C6 Zr 72.55(7) . . ? C7 C6 Zr 71.93(6) . . ? C1 C7 C6 128.67(11) . . ? C1 C7 Zr 72.47(7) . . ? C6 C7 Zr 72.44(6) . . ? N1 C8 N2 113.46(9) . . ? N1 C8 C11 122.71(9) . . ? N2 C8 C11 123.08(9) . . ? N1 C8 Zr 75.10(6) . . ? N2 C8 Zr 74.59(6) . . ? C11 C8 Zr 126.58(7) . . ? N1 C9 C10 107.73(9) . . ? N1 C9 C15 116.62(9) . . ? C10 C9 C15 135.17(9) . . ? N1 C9 Zr 71.56(5) . . ? C10 C9 Zr 73.34(6) . . ? C15 C9 Zr 126.15(7) . . ? N2 C10 C9 107.66(9) . . ? N2 C10 C19 115.45(9) . . ? C9 C10 C19 136.13(10) . . ? N2 C10 Zr 71.37(6) . . ? C9 C10 Zr 73.90(6) . . ? C19 C10 Zr 126.95(7) . . ? C8 C11 C13 111.59(9) . . ? C8 C11 C12 110.52(9) . . ? C13 C11 C12 110.81(10) . . ? C8 C11 C14 105.43(9) . . ? C13 C11 C14 108.90(10) . . ? C12 C11 C14 109.44(10) . . ? C9 C15 C18 114.39(9) . . ? C9 C15 C16 109.14(9) . . ? C18 C15 C16 106.92(10) . . ? C9 C15 C17 108.11(9) . . ? C18 C15 C17 110.79(10) . . ? C16 C15 C17 107.25(9) . . ? C20 C19 C10 115.34(9) . . ? C20 C19 C22 109.15(10) . . ? C10 C19 C22 106.06(9) . . ? C20 C19 C21 107.43(9) . . ? C10 C19 C21 109.75(9) . . ? C22 C19 C21 109.00(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 C7 Zr N1 C8 -50.20(8) . . . . ? C2 Zr N1 C8 -123.28(6) . . . . ? C1 Zr N1 C8 -86.27(7) . . . . ? C6 Zr N1 C8 1.18(13) . . . . ? C4 Zr N1 C8 163.65(6) . . . . ? C3 Zr N1 C8 -160.29(6) . . . . ? C5 Zr N1 C8 112.41(11) . . . . ? N2 Zr N1 C8 34.31(6) . . . . ? C10 Zr N1 C8 74.38(6) . . . . ? C9 Zr N1 C8 111.31(8) . . . . ? C7 Zr N1 C9 -161.50(6) . . . . ? C2 Zr N1 C9 125.41(6) . . . . ? C1 Zr N1 C9 162.42(6) . . . . ? C6 Zr N1 C9 -110.13(11) . . . . ? C4 Zr N1 C9 52.34(8) . . . . ? C3 Zr N1 C9 88.41(6) . . . . ? C5 Zr N1 C9 1.10(13) . . . . ? C8 Zr N1 C9 -111.31(8) . . . . ? N2 Zr N1 C9 -77.00(6) . . . . ? C10 Zr N1 C9 -36.92(6) . . . . ? C7 Zr N2 C8 96.28(7) . . . . ? C2 Zr N2 C8 18.27(11) . . . . ? C1 Zr N2 C8 60.65(7) . . . . ? C6 Zr N2 C8 133.69(6) . . . . ? C4 Zr N2 C8 -153.56(7) . . . . ? C3 Zr N2 C8 -87.53(14) . . . . ? C5 Zr N2 C8 169.94(6) . . . . ? N1 Zr N2 C8 -34.20(6) . . . . ? C10 Zr N2 C8 -111.21(8) . . . . ? C9 Zr N2 C8 -74.18(6) . . . . ? C7 Zr N2 C10 -152.51(6) . . . . ? C2 Zr N2 C10 129.48(9) . . . . ? C1 Zr N2 C10 171.86(6) . . . . ? C6 Zr N2 C10 -115.10(6) . . . . ? C4 Zr N2 C10 -42.35(9) . . . . ? C3 Zr N2 C10 23.67(15) . . . . ? C5 Zr N2 C10 -78.85(7) . . . . ? C8 Zr N2 C10 111.21(8) . . . . ? N1 Zr N2 C10 77.01(6) . . . . ? C9 Zr N2 C10 37.03(6) . . . . ? C7 Zr C1 C2 142.19(11) . . . . ? C6 Zr C1 C2 119.18(8) . . . . ? C4 Zr C1 C2 53.32(7) . . . . ? C3 Zr C1 C2 22.93(7) . . . . ? C5 Zr C1 C2 88.80(7) . . . . ? C8 Zr C1 C2 -118.34(7) . . . . ? N2 Zr C1 C2 -147.61(6) . . . . ? N1 Zr C1 C2 -84.42(7) . . . . ? C10 Zr C1 C2 -135.00(11) . . . . ? C9 Zr C1 C2 -68.41(9) . . . . ? C2 Zr C1 C7 -142.19(11) . . . . ? C6 Zr C1 C7 -23.01(7) . . . . ? C4 Zr C1 C7 -88.87(7) . . . . ? C3 Zr C1 C7 -119.27(8) . . . . ? C5 Zr C1 C7 -53.40(7) . . . . ? C8 Zr C1 C7 99.46(7) . . . . ? N2 Zr C1 C7 70.20(8) . . . . ? N1 Zr C1 C7 133.39(7) . . . . ? C10 Zr C1 C7 82.80(13) . . . . ? C9 Zr C1 C7 149.40(7) . . . . ? C7 C1 C2 C3 -0.6(2) . . . . ? Zr C1 C2 C3 -48.64(12) . . . . ? C7 C1 C2 Zr 48.08(12) . . . . ? C7 Zr C2 C1 -22.83(7) . . . . ? C6 Zr C2 C1 -53.48(7) . . . . ? C4 Zr C2 C1 -119.32(8) . . . . ? C3 Zr C2 C1 -142.00(11) . . . . ? C5 Zr C2 C1 -88.92(7) . . . . ? C8 Zr C2 C1 77.57(8) . . . . ? N2 Zr C2 C1 66.31(11) . . . . ? N1 Zr C2 C1 108.81(7) . . . . ? C10 Zr C2 C1 144.43(9) . . . . ? C9 Zr C2 C1 139.87(7) . . . . ? C7 Zr C2 C3 119.17(8) . . . . ? C1 Zr C2 C3 142.00(11) . . . . ? C6 Zr C2 C3 88.52(7) . . . . ? C4 Zr C2 C3 22.68(7) . . . . ? C5 Zr C2 C3 53.08(7) . . . . ? C8 Zr C2 C3 -140.43(7) . . . . ? N2 Zr C2 C3 -151.68(8) . . . . ? N1 Zr C2 C3 -109.18(7) . . . . ? C10 Zr C2 C3 -73.57(11) . . . . ? C9 Zr C2 C3 -78.12(8) . . . . ? C1 C2 C3 C4 0.5(2) . . . . ? Zr C2 C3 C4 -48.05(12) . . . . ? C1 C2 C3 Zr 48.60(12) . . . . ? C7 Zr C3 C4 88.94(7) . . . . ? C2 Zr C3 C4 142.38(11) . . . . ? C1 Zr C3 C4 119.46(8) . . . . ? C6 Zr C3 C4 53.23(7) . . . . ? C5 Zr C3 C4 22.85(7) . . . . ? C8 Zr C3 C4 -151.05(7) . . . . ? N2 Zr C3 C4 -87.47(14) . . . . ? N1 Zr C3 C4 -133.51(7) . . . . ? C10 Zr C3 C4 -70.66(8) . . . . ? C9 Zr C3 C4 -98.94(7) . . . . ? C7 Zr C3 C2 -53.44(7) . . . . ? C1 Zr C3 C2 -22.92(7) . . . . ? C6 Zr C3 C2 -89.15(7) . . . . ? C4 Zr C3 C2 -142.38(11) . . . . ? C5 Zr C3 C2 -119.53(8) . . . . ? C8 Zr C3 C2 66.57(10) . . . . ? N2 Zr C3 C2 130.14(12) . . . . ? N1 Zr C3 C2 84.11(7) . . . . ? C10 Zr C3 C2 146.96(7) . . . . ? C9 Zr C3 C2 118.68(7) . . . . ? C2 C3 C4 C5 -0.7(2) . . . . ? Zr C3 C4 C5 -48.71(12) . . . . ? C2 C3 C4 Zr 48.01(12) . . . . ? C7 Zr C4 C5 53.30(7) . . . . ? C2 Zr C4 C5 119.36(8) . . . . ? C1 Zr C4 C5 88.90(7) . . . . ? C6 Zr C4 C5 22.76(7) . . . . ? C3 Zr C4 C5 142.07(11) . . . . ? C8 Zr C4 C5 -119.36(13) . . . . ? N2 Zr C4 C5 -64.73(9) . . . . ? N1 Zr C4 C5 -150.30(6) . . . . ? C10 Zr C4 C5 -87.95(7) . . . . ? C9 Zr C4 C5 -123.34(7) . . . . ? C7 Zr C4 C3 -88.78(7) . . . . ? C2 Zr C4 C3 -22.71(7) . . . . ? C1 Zr C4 C3 -53.18(7) . . . . ? C6 Zr C4 C3 -119.31(8) . . . . ? C5 Zr C4 C3 -142.07(11) . . . . ? C8 Zr C4 C3 98.56(14) . . . . ? N2 Zr C4 C3 153.20(6) . . . . ? N1 Zr C4 C3 67.63(8) . . . . ? C10 Zr C4 C3 129.97(7) . . . . ? C9 Zr C4 C3 94.59(7) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? Zr C4 C5 C6 -48.04(12) . . . . ? C3 C4 C5 Zr 48.65(12) . . . . ? C7 Zr C5 C6 22.85(7) . . . . ? C2 Zr C5 C6 88.94(7) . . . . ? C1 Zr C5 C6 53.39(7) . . . . ? C4 Zr C5 C6 142.22(10) . . . . ? C3 Zr C5 C6 119.35(8) . . . . ? C8 Zr C5 C6 -67.81(10) . . . . ? N2 Zr C5 C6 -78.39(7) . . . . ? N1 Zr C5 C6 -143.64(9) . . . . ? C10 Zr C5 C6 -111.95(7) . . . . ? C9 Zr C5 C6 -142.92(6) . . . . ? C7 Zr C5 C4 -119.37(8) . . . . ? C2 Zr C5 C4 -53.29(7) . . . . ? C1 Zr C5 C4 -88.84(7) . . . . ? C6 Zr C5 C4 -142.22(10) . . . . ? C3 Zr C5 C4 -22.88(7) . . . . ? C8 Zr C5 C4 149.97(8) . . . . ? N2 Zr C5 C4 139.38(6) . . . . ? N1 Zr C5 C4 74.13(12) . . . . ? C10 Zr C5 C4 105.82(7) . . . . ? C9 Zr C5 C4 74.86(8) . . . . ? C4 C5 C6 C7 -0.1(2) . . . . ? Zr C5 C6 C7 -48.14(12) . . . . ? C4 C5 C6 Zr 48.05(12) . . . . ? C7 Zr C6 C5 -142.26(11) . . . . ? C2 Zr C6 C5 -88.79(7) . . . . ? C1 Zr C6 C5 -119.31(8) . . . . ? C4 Zr C6 C5 -22.78(7) . . . . ? C3 Zr C6 C5 -53.23(7) . . . . ? C8 Zr C6 C5 144.42(6) . . . . ? N2 Zr C6 C5 115.88(7) . . . . ? N1 Zr C6 C5 143.64(9) . . . . ? C10 Zr C6 C5 82.80(7) . . . . ? C9 Zr C6 C5 69.22(10) . . . . ? C2 Zr C6 C7 53.46(7) . . . . ? C1 Zr C6 C7 22.95(7) . . . . ? C4 Zr C6 C7 119.48(8) . . . . ? C3 Zr C6 C7 89.03(7) . . . . ? C5 Zr C6 C7 142.26(11) . . . . ? C8 Zr C6 C7 -73.32(8) . . . . ? N2 Zr C6 C7 -101.86(7) . . . . ? N1 Zr C6 C7 -74.10(12) . . . . ? C10 Zr C6 C7 -134.94(7) . . . . ? C9 Zr C6 C7 -148.52(8) . . . . ? C2 C1 C7 C6 0.7(2) . . . . ? Zr C1 C7 C6 48.84(12) . . . . ? C2 C1 C7 Zr -48.16(12) . . . . ? C5 C6 C7 C1 -0.5(2) . . . . ? Zr C6 C7 C1 -48.85(12) . . . . ? C5 C6 C7 Zr 48.36(12) . . . . ? C2 Zr C7 C1 22.80(7) . . . . ? C6 Zr C7 C1 141.94(11) . . . . ? C4 Zr C7 C1 88.85(7) . . . . ? C3 Zr C7 C1 53.33(7) . . . . ? C5 Zr C7 C1 119.24(8) . . . . ? C8 Zr C7 C1 -93.42(7) . . . . ? N2 Zr C7 C1 -127.77(7) . . . . ? N1 Zr C7 C1 -67.65(8) . . . . ? C10 Zr C7 C1 -149.26(7) . . . . ? C9 Zr C7 C1 -101.54(14) . . . . ? C2 Zr C7 C6 -119.14(8) . . . . ? C1 Zr C7 C6 -141.94(11) . . . . ? C4 Zr C7 C6 -53.09(7) . . . . ? C3 Zr C7 C6 -88.61(7) . . . . ? C5 Zr C7 C6 -22.70(7) . . . . ? C8 Zr C7 C6 124.64(7) . . . . ? N2 Zr C7 C6 90.30(7) . . . . ? N1 Zr C7 C6 150.41(6) . . . . ? C10 Zr C7 C6 68.80(9) . . . . ? C9 Zr C7 C6 116.52(13) . . . . ? C9 N1 C8 N2 4.29(12) . . . . ? Zr N1 C8 N2 -65.47(8) . . . . ? C9 N1 C8 C11 -166.05(10) . . . . ? Zr N1 C8 C11 124.19(10) . . . . ? C9 N1 C8 Zr 69.76(7) . . . . ? C10 N2 C8 N1 -4.24(12) . . . . ? Zr N2 C8 N1 65.77(8) . . . . ? C10 N2 C8 C11 166.06(10) . . . . ? Zr N2 C8 C11 -123.93(10) . . . . ? C10 N2 C8 Zr -70.01(7) . . . . ? C7 Zr C8 N1 144.03(6) . . . . ? C2 Zr C8 N1 69.69(7) . . . . ? C1 Zr C8 N1 106.35(6) . . . . ? C6 Zr C8 N1 -179.46(6) . . . . ? C4 Zr C8 N1 -43.79(16) . . . . ? C3 Zr C8 N1 31.17(10) . . . . ? C5 Zr C8 N1 -137.74(8) . . . . ? N2 Zr C8 N1 -120.05(9) . . . . ? C10 Zr C8 N1 -80.89(6) . . . . ? C9 Zr C8 N1 -39.09(6) . . . . ? C7 Zr C8 N2 -95.93(6) . . . . ? C2 Zr C8 N2 -170.27(6) . . . . ? C1 Zr C8 N2 -133.60(6) . . . . ? C6 Zr C8 N2 -59.41(7) . . . . ? C4 Zr C8 N2 76.26(15) . . . . ? C3 Zr C8 N2 151.22(7) . . . . ? C5 Zr C8 N2 -17.70(11) . . . . ? N1 Zr C8 N2 120.05(9) . . . . ? C10 Zr C8 N2 39.16(6) . . . . ? C9 Zr C8 N2 80.96(6) . . . . ? C7 Zr C8 C11 24.10(10) . . . . ? C2 Zr C8 C11 -50.24(10) . . . . ? C1 Zr C8 C11 -13.57(10) . . . . ? C6 Zr C8 C11 60.62(10) . . . . ? C4 Zr C8 C11 -163.71(12) . . . . ? C3 Zr C8 C11 -88.76(10) . . . . ? C5 Zr C8 C11 102.33(11) . . . . ? N2 Zr C8 C11 120.03(11) . . . . ? N1 Zr C8 C11 -119.92(11) . . . . ? C10 Zr C8 C11 159.19(10) . . . . ? C9 Zr C8 C11 -159.02(10) . . . . ? C8 N1 C9 C10 -2.52(11) . . . . ? Zr N1 C9 C10 64.92(7) . . . . ? C8 N1 C9 C15 170.66(9) . . . . ? Zr N1 C9 C15 -121.90(9) . . . . ? C8 N1 C9 Zr -67.44(7) . . . . ? C7 Zr C9 N1 48.40(15) . . . . ? C2 Zr C9 N1 -67.79(7) . . . . ? C1 Zr C9 N1 -28.08(9) . . . . ? C6 Zr C9 N1 138.46(8) . . . . ? C4 Zr C9 N1 -142.71(6) . . . . ? C3 Zr C9 N1 -104.87(6) . . . . ? C5 Zr C9 N1 -179.50(6) . . . . ? C8 Zr C9 N1 38.75(6) . . . . ? N2 Zr C9 N1 79.16(6) . . . . ? C10 Zr C9 N1 115.77(9) . . . . ? C7 Zr C9 C10 -67.37(14) . . . . ? C2 Zr C9 C10 176.44(6) . . . . ? C1 Zr C9 C10 -143.85(7) . . . . ? C6 Zr C9 C10 22.69(10) . . . . ? C4 Zr C9 C10 101.52(7) . . . . ? C3 Zr C9 C10 139.36(6) . . . . ? C5 Zr C9 C10 64.73(7) . . . . ? C8 Zr C9 C10 -77.02(7) . . . . ? N2 Zr C9 C10 -36.61(6) . . . . ? N1 Zr C9 C10 -115.77(9) . . . . ? C7 Zr C9 C15 158.36(12) . . . . ? C2 Zr C9 C15 42.17(10) . . . . ? C1 Zr C9 C15 81.87(11) . . . . ? C6 Zr C9 C15 -111.58(10) . . . . ? C4 Zr C9 C15 -32.75(9) . . . . ? C3 Zr C9 C15 5.09(9) . . . . ? C5 Zr C9 C15 -69.54(10) . . . . ? C8 Zr C9 C15 148.71(10) . . . . ? N2 Zr C9 C15 -170.89(10) . . . . ? N1 Zr C9 C15 109.96(11) . . . . ? C10 Zr C9 C15 -134.27(12) . . . . ? C8 N2 C10 C9 2.39(11) . . . . ? Zr N2 C10 C9 -65.51(7) . . . . ? C8 N2 C10 C19 -169.28(9) . . . . ? Zr N2 C10 C19 122.82(8) . . . . ? C8 N2 C10 Zr 67.90(7) . . . . ? N1 C9 C10 N2 0.08(11) . . . . ? C15 C9 C10 N2 -171.26(11) . . . . ? Zr C9 C10 N2 63.83(7) . . . . ? N1 C9 C10 C19 169.20(11) . . . . ? C15 C9 C10 C19 -2.1(2) . . . . ? Zr C9 C10 C19 -127.04(13) . . . . ? N1 C9 C10 Zr -63.76(7) . . . . ? C15 C9 C10 Zr 124.91(12) . . . . ? C7 Zr C10 N2 39.91(8) . . . . ? C2 Zr C10 N2 -122.63(9) . . . . ? C1 Zr C10 N2 -18.73(14) . . . . ? C6 Zr C10 N2 77.56(7) . . . . ? C4 Zr C10 N2 152.19(6) . . . . ? C3 Zr C10 N2 -171.11(6) . . . . ? C5 Zr C10 N2 114.70(6) . . . . ? C8 Zr C10 N2 -38.84(6) . . . . ? N1 Zr C10 N2 -79.09(6) . . . . ? C9 Zr C10 N2 -115.51(9) . . . . ? C7 Zr C10 C9 155.42(7) . . . . ? C2 Zr C10 C9 -7.12(12) . . . . ? C1 Zr C10 C9 96.78(12) . . . . ? C6 Zr C10 C9 -166.93(6) . . . . ? C4 Zr C10 C9 -92.30(7) . . . . ? C3 Zr C10 C9 -55.60(8) . . . . ? C5 Zr C10 C9 -129.79(6) . . . . ? C8 Zr C10 C9 76.67(6) . . . . ? N2 Zr C10 C9 115.51(9) . . . . ? N1 Zr C10 C9 36.42(6) . . . . ? C7 Zr C10 C19 -68.38(11) . . . . ? C2 Zr C10 C19 129.08(10) . . . . ? C1 Zr C10 C19 -127.02(12) . . . . ? C6 Zr C10 C19 -30.74(10) . . . . ? C4 Zr C10 C19 43.90(10) . . . . ? C3 Zr C10 C19 80.59(10) . . . . ? C5 Zr C10 C19 6.40(10) . . . . ? C8 Zr C10 C19 -147.14(10) . . . . ? N2 Zr C10 C19 -108.30(11) . . . . ? N1 Zr C10 C19 172.61(10) . . . . ? C9 Zr C10 C19 136.20(12) . . . . ? N1 C8 C11 C13 -150.38(11) . . . . ? N2 C8 C11 C13 40.21(15) . . . . ? Zr C8 C11 C13 -54.87(13) . . . . ? N1 C8 C11 C12 -26.60(14) . . . . ? N2 C8 C11 C12 163.98(10) . . . . ? Zr C8 C11 C12 68.91(11) . . . . ? N1 C8 C11 C14 91.56(12) . . . . ? N2 C8 C11 C14 -77.86(12) . . . . ? Zr C8 C11 C14 -172.94(8) . . . . ? N1 C9 C15 C18 125.95(11) . . . . ? C10 C9 C15 C18 -63.28(16) . . . . ? Zr C9 C15 C18 40.08(13) . . . . ? N1 C9 C15 C16 6.24(13) . . . . ? C10 C9 C15 C16 177.00(12) . . . . ? Zr C9 C15 C16 -79.63(11) . . . . ? N1 C9 C15 C17 -110.11(10) . . . . ? C10 C9 C15 C17 60.66(15) . . . . ? Zr C9 C15 C17 164.02(7) . . . . ? N2 C10 C19 C20 -160.72(9) . . . . ? C9 C10 C19 C20 30.76(17) . . . . ? Zr C10 C19 C20 -75.59(12) . . . . ? N2 C10 C19 C22 78.35(11) . . . . ? C9 C10 C19 C22 -90.17(15) . . . . ? Zr C10 C19 C22 163.48(7) . . . . ? N2 C10 C19 C21 -39.25(12) . . . . ? C9 C10 C19 C21 152.23(12) . . . . ? Zr C10 C19 C21 45.89(12) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.381 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.055 _iucr_refine_instructions_details ; TITL MK60 in P2(1)/c CELL 0.71073 9.360634 25.441026 9.994873 90.0000 116.9294 90.0000 ZERR 4.00 0.000200 0.000400 0.000300 0.0000 0.0030 0.0000 LATT 1 SYMM -x, y+1/2,-z+1/2 SFAC C H N Zr UNIT 88.00 136.00 8.00 4.00 TEMP -173 SIZE 0.4 0.2 0.2 L.S. 4 ACTA 61 CONF OMIT 0 8 3 OMIT 1 4 3 OMIT -1 27 2 FMAP 2 PLAN 10 WGHT 0.017000 1.099900 FVAR 3.84747 ZR 4 0.416828 0.361904 0.465547 11.00000 0.01022 0.01403 = 0.01338 0.00005 0.00603 0.00106 N1 3 0.254305 0.427023 0.520691 11.00000 0.01184 0.01264 = 0.01120 0.00067 0.00506 0.00163 N2 3 0.240736 0.341725 0.581843 11.00000 0.01331 0.01324 = 0.01273 0.00056 0.00728 0.00065 C1 1 0.692396 0.378893 0.585406 11.00000 0.01245 0.02103 = 0.01969 -0.00457 0.00618 -0.00122 H1 2 0.753403 0.397573 0.673386 11.00000 0.02526 C2 1 0.623721 0.409047 0.450570 11.00000 0.01670 0.01843 = 0.02307 -0.00329 0.01084 -0.00416 H2 2 0.643210 0.445500 0.461695 11.00000 0.02505 C3 1 0.516187 0.392253 0.302446 11.00000 0.01962 0.02086 = 0.01794 0.00068 0.01089 -0.00225 H3 2 0.476925 0.419256 0.230708 11.00000 0.02463 C4 1 0.449861 0.341267 0.252883 11.00000 0.01768 0.02197 = 0.01636 -0.00330 0.00934 -0.00235 H4 2 0.371406 0.338930 0.149494 11.00000 0.01849 C5 1 0.475580 0.294267 0.338480 11.00000 0.01697 0.01728 = 0.02210 -0.00471 0.01100 -0.00165 H5 2 0.413535 0.265051 0.288478 11.00000 0.02227 C6 1 0.573103 0.286858 0.495261 11.00000 0.01695 0.01560 = 0.02380 0.00048 0.01051 0.00287 H6 2 0.563001 0.253950 0.534828 11.00000 0.02237 C7 1 0.669314 0.324592 0.605374 11.00000 0.01305 0.02182 = 0.01860 0.00104 0.00598 0.00464 H7 2 0.715219 0.313440 0.703223 11.00000 0.02666 C8 1 0.303354 0.390259 0.631255 11.00000 0.01287 0.01262 = 0.01170 0.00043 0.00628 0.00228 C9 1 0.143223 0.401528 0.391959 11.00000 0.01031 0.01275 = 0.01146 0.00013 0.00512 0.00083 C10 1 0.134867 0.348018 0.430358 11.00000 0.01098 0.01285 = 0.01253 0.00003 0.00689 0.00071 C11 1 0.395761 0.404117 0.796212 11.00000 0.01737 0.01572 = 0.01039 -0.00062 0.00458 0.00271 C12 1 0.489739 0.455122 0.816194 11.00000 0.02732 0.02447 = 0.01641 -0.00555 0.00512 -0.00726 AFIX 137 H12A 2 0.570347 0.450053 0.780261 11.00000 -1.50000 H12B 2 0.543003 0.464739 0.922671 11.00000 -1.50000 H12C 2 0.416095 0.483261 0.758455 11.00000 -1.50000 AFIX 0 C13 1 0.507055 0.359479 0.886114 11.00000 0.02976 0.02500 = 0.01312 0.00157 0.00348 0.01183 AFIX 137 H13A 2 0.592460 0.355307 0.855889 11.00000 -1.50000 H13B 2 0.445742 0.326729 0.866713 11.00000 -1.50000 H13C 2 0.554346 0.367769 0.993404 11.00000 -1.50000 AFIX 0 C14 1 0.267882 0.412293 0.851096 11.00000 0.02691 0.02963 = 0.01671 -0.00132 0.01201 0.00498 AFIX 137 H14A 2 0.319696 0.423974 0.955887 11.00000 -1.50000 H14B 2 0.211525 0.379105 0.843408 11.00000 -1.50000 H14C 2 0.191051 0.439004 0.788917 11.00000 -1.50000 AFIX 0 C15 1 0.047894 0.436180 0.254197 11.00000 0.01428 0.01472 = 0.01245 0.00229 0.00381 0.00146 C16 1 0.113686 0.492664 0.287772 11.00000 0.02254 0.01496 = 0.02014 0.00566 0.00444 -0.00016 AFIX 137 H16A 2 0.103500 0.506281 0.374776 11.00000 -1.50000 H16B 2 0.052625 0.515025 0.200433 11.00000 -1.50000 H16C 2 0.226819 0.492646 0.309483 11.00000 -1.50000 AFIX 0 C17 1 -0.127131 0.438145 0.228432 11.00000 0.01387 0.02132 = 0.02163 0.00239 0.00313 0.00422 AFIX 137 H17A 2 -0.130384 0.451127 0.319327 11.00000 -1.50000 H17B 2 -0.173526 0.402787 0.205113 11.00000 -1.50000 H17C 2 -0.188880 0.461771 0.144458 11.00000 -1.50000 AFIX 0 C18 1 0.056609 0.418532 0.111052 11.00000 0.02900 0.02616 = 0.01359 0.00436 0.00928 0.00320 AFIX 137 H18A 2 -0.011988 0.441229 0.027227 11.00000 -1.50000 H18B 2 0.019863 0.382060 0.088129 11.00000 -1.50000 H18C 2 0.167509 0.421051 0.126501 11.00000 -1.50000 AFIX 0 C19 1 0.025889 0.300970 0.355553 11.00000 0.01342 0.01307 = 0.01750 -0.00237 0.00846 -0.00175 C20 1 -0.048659 0.299796 0.184451 11.00000 0.02193 0.01961 = 0.01919 -0.00680 0.00797 -0.00413 AFIX 137 H20A 2 -0.113193 0.267855 0.147071 11.00000 -1.50000 H20B 2 0.036472 0.300038 0.153027 11.00000 -1.50000 H20C 2 -0.117102 0.330741 0.143440 11.00000 -1.50000 AFIX 0 C21 1 0.120673 0.249490 0.413810 11.00000 0.01887 0.01199 = 0.02991 -0.00101 0.01307 -0.00106 AFIX 137 H21A 2 0.169516 0.248888 0.523680 11.00000 -1.50000 H21B 2 0.204817 0.247366 0.381322 11.00000 -1.50000 H21C 2 0.047978 0.219469 0.373486 11.00000 -1.50000 AFIX 0 C22 1 -0.108520 0.303203 0.403828 11.00000 0.01693 0.01777 = 0.02988 -0.00259 0.01491 -0.00284 AFIX 137 H22A 2 -0.177871 0.272352 0.364728 11.00000 -1.50000 H22B 2 -0.171952 0.335211 0.363869 11.00000 -1.50000 H22C 2 -0.061319 0.303467 0.513627 11.00000 -1.50000 HKLF 4 ; data_mk64 _database_code_depnum_ccdc_archive 'CCDC 902363' #TrackingRef 'combined_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H25 N O2' _chemical_formula_weight 239.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 8.7383(8) _cell_length_b 9.5314(8) _cell_length_c 9.7570(8) _cell_angle_alpha 81.310(7) _cell_angle_beta 63.418(8) _cell_angle_gamma 82.113(7) _cell_volume 716.17(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 17074 _cell_measurement_theta_min 4.7040 _cell_measurement_theta_max 75.9515 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.110 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.574 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.64940 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30721 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0103 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.71 _diffrn_reflns_theta_max 76.14 _reflns_number_total 2965 _reflns_number_gt 2774 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _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. The hydrogen at O2 was refined freely. The methyl groups were refined as idealised groups allowed to rotate but not tip. ; _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^)+(0.0522P)^2^+0.2349P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2965 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.001 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 N N 0.12432(11) 0.29970(9) 0.50796(10) 0.0232(2) Uani 1 1 d . . . O1 O 0.06046(10) 0.48343(8) 0.67063(9) 0.02656(19) Uani 1 1 d . . . O2 O 0.15618(10) 0.57599(8) 0.53214(9) 0.0296(2) Uani 1 1 d . . . H02 H 0.052(3) 0.625(2) 0.517(2) 0.069(6) Uiso 1 1 d . . . C1 C 0.13385(13) 0.34250(11) 0.64259(12) 0.0230(2) Uani 1 1 d . . . C2 C 0.32393(14) 0.32580(11) 0.60319(12) 0.0243(2) Uani 1 1 d . . . C3 C 0.40809(14) 0.26819(11) 0.46904(12) 0.0247(2) Uani 1 1 d . . . C4 C 0.27608(14) 0.25457(11) 0.41464(12) 0.0234(2) Uani 1 1 d . . . C5 C 0.01675(14) 0.24842(12) 0.79035(12) 0.0276(2) Uani 1 1 d . . . C6 C 0.10234(16) 0.09668(13) 0.78689(14) 0.0343(3) Uani 1 1 d . . . H6A H 0.0234 0.0344 0.8710 0.051 Uiso 1 1 calc R . . H6B H 0.2075 0.0967 0.7994 0.051 Uiso 1 1 calc R . . H6C H 0.1308 0.0619 0.6881 0.051 Uiso 1 1 calc R . . C7 C -0.15885(15) 0.24369(14) 0.79175(14) 0.0341(3) Uani 1 1 d . . . H7A H -0.1449 0.1923 0.7066 0.051 Uiso 1 1 calc R . . H7B H -0.2079 0.3410 0.7798 0.051 Uiso 1 1 calc R . . H7C H -0.2359 0.1947 0.8897 0.051 Uiso 1 1 calc R . . C8 C -0.01094(18) 0.30909(14) 0.93775(13) 0.0372(3) Uani 1 1 d . . . H8A H -0.0804 0.2466 1.0280 0.056 Uiso 1 1 calc R . . H8B H -0.0706 0.4044 0.9421 0.056 Uiso 1 1 calc R . . H8C H 0.1005 0.3149 0.9371 0.056 Uiso 1 1 calc R . . C9 C 0.39732(15) 0.37115(13) 0.69990(13) 0.0310(3) Uani 1 1 d . . . H9A H 0.3944 0.2938 0.7794 0.046 Uiso 1 1 calc R . . H9B H 0.3294 0.4556 0.7489 0.046 Uiso 1 1 calc R . . H9C H 0.5163 0.3938 0.6348 0.046 Uiso 1 1 calc R . . C10 C 0.59738(15) 0.22816(14) 0.39043(14) 0.0333(3) Uani 1 1 d . . . H10A H 0.6562 0.2753 0.4337 0.050 Uiso 1 1 calc R . . H10B H 0.6407 0.2583 0.2799 0.050 Uiso 1 1 calc R . . H10C H 0.6189 0.1247 0.4064 0.050 Uiso 1 1 calc R . . C11 C 0.31008(15) 0.20129(12) 0.26347(13) 0.0289(3) Uani 1 1 d . . . C12 C 0.39747(19) 0.31753(15) 0.13315(14) 0.0417(3) Uani 1 1 d . . . H12A H 0.3196 0.4042 0.1472 0.063 Uiso 1 1 calc R . . H12B H 0.4254 0.2844 0.0337 0.063 Uiso 1 1 calc R . . H12C H 0.5031 0.3381 0.1355 0.063 Uiso 1 1 calc R . . C13 C 0.42478(19) 0.06110(15) 0.23799(16) 0.0407(3) Uani 1 1 d . . . H13A H 0.5390 0.0784 0.2244 0.061 Uiso 1 1 calc R . . H13B H 0.4349 0.0239 0.1457 0.061 Uiso 1 1 calc R . . H13C H 0.3737 -0.0085 0.3276 0.061 Uiso 1 1 calc R . . C14 C 0.14174(17) 0.17494(15) 0.26211(15) 0.0376(3) Uani 1 1 d . . . H14A H 0.0804 0.1066 0.3498 0.056 Uiso 1 1 calc R . . H14B H 0.1669 0.1365 0.1659 0.056 Uiso 1 1 calc R . . H14C H 0.0703 0.2649 0.2698 0.056 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 N 0.0239(4) 0.0254(4) 0.0220(4) -0.0038(3) -0.0118(4) 0.0006(3) O1 0.0287(4) 0.0252(4) 0.0247(4) -0.0032(3) -0.0118(3) 0.0029(3) O2 0.0264(4) 0.0298(4) 0.0322(4) 0.0026(3) -0.0140(3) -0.0032(3) C1 0.0235(5) 0.0251(5) 0.0215(5) -0.0049(4) -0.0112(4) 0.0024(4) C2 0.0245(5) 0.0253(5) 0.0247(5) -0.0022(4) -0.0130(4) 0.0011(4) C3 0.0234(5) 0.0266(5) 0.0247(5) -0.0028(4) -0.0117(4) 0.0009(4) C4 0.0250(5) 0.0235(5) 0.0223(5) -0.0022(4) -0.0116(4) 0.0008(4) C5 0.0266(5) 0.0294(6) 0.0226(5) -0.0026(4) -0.0079(4) 0.0009(4) C6 0.0358(6) 0.0302(6) 0.0311(6) 0.0019(5) -0.0119(5) 0.0003(5) C7 0.0255(6) 0.0360(6) 0.0330(6) -0.0012(5) -0.0067(5) -0.0022(5) C8 0.0408(7) 0.0429(7) 0.0218(5) -0.0041(5) -0.0091(5) 0.0000(5) C9 0.0306(6) 0.0375(6) 0.0306(6) -0.0076(5) -0.0184(5) 0.0016(5) C10 0.0235(6) 0.0423(7) 0.0335(6) -0.0107(5) -0.0118(5) 0.0041(5) C11 0.0316(6) 0.0324(6) 0.0246(5) -0.0095(4) -0.0146(5) 0.0065(5) C12 0.0482(8) 0.0502(8) 0.0238(6) -0.0034(5) -0.0145(5) 0.0009(6) C13 0.0475(8) 0.0411(7) 0.0415(7) -0.0203(6) -0.0268(6) 0.0159(6) C14 0.0408(7) 0.0443(7) 0.0379(6) -0.0179(5) -0.0248(6) 0.0064(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 N C4 1.2860(14) . ? N C1 1.4724(13) . ? O1 C1 1.4171(13) . ? O1 O2 1.4610(11) . ? C1 C2 1.5187(15) . ? C1 C5 1.5718(15) . ? C2 C3 1.3418(15) . ? C2 C9 1.4932(15) . ? C3 C4 1.4964(14) . ? C3 C10 1.4999(15) . ? C4 C11 1.5214(14) . ? C5 C6 1.5321(16) . ? C5 C7 1.5352(16) . ? C5 C8 1.5371(16) . ? C11 C14 1.5319(17) . ? C11 C13 1.5368(16) . ? C11 C12 1.5379(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N C1 108.08(9) . . ? C1 O1 O2 107.08(7) . . ? O1 C1 N 111.07(8) . . ? O1 C1 C2 112.82(9) . . ? N C1 C2 104.67(8) . . ? O1 C1 C5 104.22(8) . . ? N C1 C5 108.61(8) . . ? C2 C1 C5 115.51(9) . . ? C3 C2 C9 128.03(10) . . ? C3 C2 C1 108.15(9) . . ? C9 C2 C1 123.80(9) . . ? C2 C3 C4 106.26(9) . . ? C2 C3 C10 126.06(10) . . ? C4 C3 C10 127.68(10) . . ? N C4 C3 112.58(9) . . ? N C4 C11 121.25(10) . . ? C3 C4 C11 126.11(9) . . ? C6 C5 C7 108.80(10) . . ? C6 C5 C8 109.62(10) . . ? C7 C5 C8 108.61(10) . . ? C6 C5 C1 108.94(9) . . ? C7 C5 C1 109.80(9) . . ? C8 C5 C1 111.04(9) . . ? C4 C11 C14 110.82(9) . . ? C4 C11 C13 111.08(9) . . ? C14 C11 C13 108.08(10) . . ? C4 C11 C12 107.64(9) . . ? C14 C11 C12 108.73(10) . . ? C13 C11 C12 110.47(10) . . ? 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 O1 C1 N -59.20(10) . . . . ? O2 O1 C1 C2 57.96(10) . . . . ? O2 O1 C1 C5 -175.97(7) . . . . ? C4 N C1 O1 126.90(9) . . . . ? C4 N C1 C2 4.86(11) . . . . ? C4 N C1 C5 -119.05(9) . . . . ? O1 C1 C2 C3 -125.89(9) . . . . ? N C1 C2 C3 -5.01(11) . . . . ? C5 C1 C2 C3 114.36(10) . . . . ? O1 C1 C2 C9 52.73(13) . . . . ? N C1 C2 C9 173.62(10) . . . . ? C5 C1 C2 C9 -67.02(13) . . . . ? C9 C2 C3 C4 -175.28(10) . . . . ? C1 C2 C3 C4 3.26(12) . . . . ? C9 C2 C3 C10 3.96(19) . . . . ? C1 C2 C3 C10 -177.49(10) . . . . ? C1 N C4 C3 -3.12(12) . . . . ? C1 N C4 C11 179.68(9) . . . . ? C2 C3 C4 N -0.16(13) . . . . ? C10 C3 C4 N -179.39(11) . . . . ? C2 C3 C4 C11 176.88(10) . . . . ? C10 C3 C4 C11 -2.34(17) . . . . ? O1 C1 C5 C6 -169.71(9) . . . . ? N C1 C5 C6 71.82(11) . . . . ? C2 C1 C5 C6 -45.36(12) . . . . ? O1 C1 C5 C7 71.23(10) . . . . ? N C1 C5 C7 -47.24(11) . . . . ? C2 C1 C5 C7 -164.41(9) . . . . ? O1 C1 C5 C8 -48.90(11) . . . . ? N C1 C5 C8 -167.36(9) . . . . ? C2 C1 C5 C8 75.46(12) . . . . ? N C4 C11 C14 -14.26(15) . . . . ? C3 C4 C11 C14 168.94(10) . . . . ? N C4 C11 C13 -134.42(12) . . . . ? C3 C4 C11 C13 48.78(15) . . . . ? N C4 C11 C12 104.52(12) . . . . ? C3 C4 C11 C12 -72.29(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H02 N 1.02(2) 1.72(2) 2.7360(12) 177.2(17) 2_566 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 75.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.282 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.035 _iucr_refine_instructions_details ; TITL mk64 in P-1 CELL 1.54184 8.738326 9.531408 9.756979 81.3103 63.4183 82.1125 ZERR 2.00 0.000800 0.000800 0.000800 0.0070 0.0080 0.0070 LATT 1 SFAC C H N O UNIT 28.00 50.00 2.00 4.00 TEMP -173 SIZE 0.25 0.15 0.1 MERG 2 FMAP 2 ACTA 150 CONF PLAN 10 L.S. 4 EQIV_$1 -x, -y+1, -z+1 HTAB O2 N_$1 WGHT 0.052200 0.234900 FVAR 14.30033 N 3 0.124322 0.299704 0.507957 11.00000 0.02393 0.02540 = 0.02199 -0.00384 -0.01176 0.00059 O1 4 0.060462 0.483430 0.670632 11.00000 0.02870 0.02520 = 0.02468 -0.00318 -0.01184 0.00292 O2 4 0.156180 0.575994 0.532144 11.00000 0.02644 0.02980 = 0.03225 0.00257 -0.01404 -0.00319 H02 2 0.052475 0.625426 0.517332 11.00000 0.06893 C1 1 0.133845 0.342498 0.642594 11.00000 0.02348 0.02508 = 0.02154 -0.00486 -0.01115 0.00239 C2 1 0.323928 0.325800 0.603191 11.00000 0.02454 0.02527 = 0.02469 -0.00218 -0.01300 0.00108 C3 1 0.408092 0.268189 0.469038 11.00000 0.02339 0.02660 = 0.02468 -0.00280 -0.01169 0.00091 C4 1 0.276079 0.254569 0.414639 11.00000 0.02495 0.02350 = 0.02225 -0.00216 -0.01158 0.00081 C5 1 0.016751 0.248417 0.790350 11.00000 0.02660 0.02940 = 0.02260 -0.00264 -0.00789 0.00094 C6 1 0.102340 0.096684 0.786895 11.00000 0.03583 0.03024 = 0.03111 0.00193 -0.01192 0.00033 AFIX 137 H6A 2 0.023442 0.034355 0.870995 11.00000 -1.50000 H6B 2 0.207549 0.096748 0.799376 11.00000 -1.50000 H6C 2 0.130776 0.061896 0.688104 11.00000 -1.50000 AFIX 0 C7 1 -0.158849 0.243691 0.791750 11.00000 0.02546 0.03604 = 0.03300 -0.00118 -0.00665 -0.00225 AFIX 137 H7A 2 -0.144881 0.192315 0.706618 11.00000 -1.50000 H7B 2 -0.207869 0.341003 0.779787 11.00000 -1.50000 H7C 2 -0.235893 0.194738 0.889738 11.00000 -1.50000 AFIX 0 C8 1 -0.010940 0.309087 0.937746 11.00000 0.04081 0.04294 = 0.02182 -0.00407 -0.00910 -0.00001 AFIX 137 H8A 2 -0.080360 0.246619 1.027981 11.00000 -1.50000 H8B 2 -0.070583 0.404386 0.942106 11.00000 -1.50000 H8C 2 0.100467 0.314939 0.937126 11.00000 -1.50000 AFIX 0 C9 1 0.397322 0.371152 0.699903 11.00000 0.03062 0.03746 = 0.03056 -0.00762 -0.01836 0.00163 AFIX 137 H9A 2 0.394363 0.293815 0.779418 11.00000 -1.50000 H9B 2 0.329443 0.455625 0.748948 11.00000 -1.50000 H9C 2 0.516330 0.393781 0.634819 11.00000 -1.50000 AFIX 0 C10 1 0.597384 0.228159 0.390429 11.00000 0.02350 0.04230 = 0.03354 -0.01072 -0.01176 0.00407 AFIX 137 H10A 2 0.656239 0.275341 0.433717 11.00000 -1.50000 H10B 2 0.640704 0.258257 0.279851 11.00000 -1.50000 H10C 2 0.618888 0.124725 0.406356 11.00000 -1.50000 AFIX 0 C11 1 0.310076 0.201287 0.263466 11.00000 0.03161 0.03242 = 0.02464 -0.00947 -0.01461 0.00647 C12 1 0.397474 0.317530 0.133151 11.00000 0.04817 0.05016 = 0.02384 -0.00337 -0.01452 0.00088 AFIX 137 H12A 2 0.319610 0.404186 0.147225 11.00000 -1.50000 H12B 2 0.425417 0.284415 0.033686 11.00000 -1.50000 H12C 2 0.503087 0.338066 0.135498 11.00000 -1.50000 AFIX 0 C13 1 0.424778 0.061098 0.237986 11.00000 0.04753 0.04109 = 0.04147 -0.02031 -0.02680 0.01585 AFIX 137 H13A 2 0.538950 0.078436 0.224384 11.00000 -1.50000 H13B 2 0.434862 0.023938 0.145721 11.00000 -1.50000 H13C 2 0.373667 -0.008479 0.327603 11.00000 -1.50000 AFIX 0 C14 1 0.141744 0.174942 0.262115 11.00000 0.04083 0.04433 = 0.03789 -0.01795 -0.02479 0.00637 AFIX 137 H14A 2 0.080354 0.106609 0.349769 11.00000 -1.50000 H14B 2 0.166876 0.136509 0.165936 11.00000 -1.50000 H14C 2 0.070315 0.264854 0.269775 11.00000 -1.50000 HKLF 4 ; data_mwal15 _database_code_depnum_ccdc_archive 'CCDC 902364' #TrackingRef 'mwal15.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H52 Li N3' _chemical_formula_weight 677.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Li Li 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/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 20.6834(4) _cell_length_b 17.2623(2) _cell_length_c 11.8317(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.377(2) _cell_angle_gamma 90.00 _cell_volume 3960.07(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16466 _cell_measurement_theta_min 3.4251 _cell_measurement_theta_max 75.8881 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.137 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.492 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.65569 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26512 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0138 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 76.08 _reflns_number_total 4114 _reflns_number_gt 3761 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _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. Restraints were applied to the displacement parameters and bond lengths of the toluene molecules in order to improve refinement stability. ; _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^)+(0.0628P)^2^+3.0547P] 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 4114 _refine_ls_number_parameters 277 _refine_ls_number_restraints 98 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1341 _refine_ls_wR_factor_gt 0.1309 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.065 _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 Li Li 0.5000 0.45664(18) 0.2500 0.0389(8) Uani 1 2 d S . . N1 N 0.5000 0.56832(8) 0.2500 0.0259(3) Uani 1 2 d S . . N2 N 0.47910(8) 0.37290(8) 0.35627(12) 0.0460(3) Uani 1 1 d . . . C1 C 0.55637(6) 0.61584(7) 0.28122(11) 0.0248(3) Uani 1 1 d . . . C2 C 0.53680(6) 0.69389(7) 0.27041(11) 0.0232(3) Uani 1 1 d . . . C3 C 0.62491(6) 0.57893(7) 0.31324(11) 0.0267(3) Uani 1 1 d . . . C4 C 0.64097(7) 0.51521(8) 0.39090(12) 0.0321(3) Uani 1 1 d . . . H4 H 0.6088 0.4986 0.4269 0.038 Uiso 1 1 calc R . . C5 C 0.70296(8) 0.47549(8) 0.41673(14) 0.0387(3) Uani 1 1 d . . . H5 H 0.7127 0.4323 0.4697 0.046 Uiso 1 1 calc R . . C6 C 0.75030(8) 0.49890(9) 0.36524(15) 0.0414(4) Uani 1 1 d . . . H6 H 0.7925 0.4717 0.3820 0.050 Uiso 1 1 calc R . . C7 C 0.73557(7) 0.56240(9) 0.28887(14) 0.0391(3) Uani 1 1 d . . . H7 H 0.7681 0.5788 0.2537 0.047 Uiso 1 1 calc R . . C8 C 0.67381(7) 0.60231(8) 0.26314(13) 0.0324(3) Uani 1 1 d . . . H8 H 0.6647 0.6459 0.2110 0.039 Uiso 1 1 calc R . . C9 C 0.58368(6) 0.76119(7) 0.29425(11) 0.0231(3) Uani 1 1 d . . . C10 C 0.64381(6) 0.76351(7) 0.39603(12) 0.0297(3) Uani 1 1 d . . . H10 H 0.6539 0.7217 0.4517 0.036 Uiso 1 1 calc R . . C11 C 0.68919(7) 0.82576(8) 0.41739(13) 0.0336(3) Uani 1 1 d . . . H11 H 0.7300 0.8258 0.4867 0.040 Uiso 1 1 calc R . . C12 C 0.67522(7) 0.88770(7) 0.33793(13) 0.0312(3) Uani 1 1 d . . . H12 H 0.7064 0.9301 0.3520 0.037 Uiso 1 1 calc R . . C13 C 0.61539(7) 0.88713(8) 0.23787(13) 0.0304(3) Uani 1 1 d . . . H13 H 0.6050 0.9298 0.1838 0.037 Uiso 1 1 calc R . . C14 C 0.57029(6) 0.82460(7) 0.21572(11) 0.0262(3) Uani 1 1 d . . . H14 H 0.5297 0.8249 0.1461 0.031 Uiso 1 1 calc R . . C15 C 0.47496(16) 0.30515(11) 0.2801(2) 0.0809(8) Uani 1 1 d . . . H15A H 0.4816 0.2579 0.3304 0.097 Uiso 1 1 calc R . . H15B H 0.4281 0.3027 0.2184 0.097 Uiso 1 1 calc R . . C16 C 0.41153(15) 0.3811(2) 0.3700(3) 0.0965(9) Uani 1 1 d . . . H16A H 0.3757 0.3865 0.2904 0.145 Uiso 1 1 calc R . . H16B H 0.4117 0.4272 0.4185 0.145 Uiso 1 1 calc R . . H16C H 0.4021 0.3351 0.4104 0.145 Uiso 1 1 calc R . . C17 C 0.53176(14) 0.36497(16) 0.4739(2) 0.0868(9) Uani 1 1 d . . . H17A H 0.5330 0.4119 0.5212 0.130 Uiso 1 1 calc R . . H17B H 0.5767 0.3575 0.4649 0.130 Uiso 1 1 calc R . . H17C H 0.5213 0.3201 0.5154 0.130 Uiso 1 1 calc R . . C91 C 0.47431(11) -0.02444(11) -0.0175(2) 0.0344(6) Uani 0.50 1 d PGDU A -1 C92 C 0.45953(11) 0.01157(13) 0.0757(2) 0.0433(11) Uani 0.50 1 d PGDU A -1 H92 H 0.4233 -0.0075 0.1000 0.052 Uiso 0.50 1 calc PR A -1 C93 C 0.49779(13) 0.07544(13) 0.1335(2) 0.0442(7) Uani 0.50 1 d PGDU A -1 H93 H 0.4877 0.1001 0.1972 0.053 Uiso 0.50 1 calc PR A -1 C94 C 0.55083(12) 0.10330(12) 0.0980(2) 0.0438(15) Uani 0.50 1 d PGDU A -1 H94 H 0.5770 0.1469 0.1375 0.053 Uiso 0.50 1 calc PR A -1 C95 C 0.56562(10) 0.06728(13) 0.0047(2) 0.0364(6) Uani 0.50 1 d PGDU A -1 H95 H 0.6019 0.0863 -0.0195 0.044 Uiso 0.50 1 calc PR A -1 C96 C 0.52736(10) 0.00342(12) -0.05302(19) 0.0341(8) Uani 0.50 1 d PGDU A -1 H96 H 0.5375 -0.0212 -0.1168 0.041 Uiso 0.50 1 calc PR A -1 C97 C 0.4329(3) -0.0925(3) -0.0826(5) 0.0471(11) Uani 0.50 1 d PDU A -1 H97A H 0.4011 -0.1087 -0.0420 0.071 Uiso 0.50 1 calc PR A -1 H97B H 0.4640 -0.1354 -0.0822 0.071 Uiso 0.50 1 calc PR A -1 H97C H 0.4065 -0.0779 -0.1660 0.071 Uiso 0.50 1 calc PR A -1 C81 C 0.8029(3) 0.7094(3) 0.0211(4) 0.0460(11) Uani 0.50 1 d PGDU B -1 C82 C 0.7737(3) 0.7282(3) -0.1004(4) 0.0440(9) Uani 0.50 1 d PGDU B -1 H82 H 0.7944 0.7104 -0.1558 0.053 Uiso 0.50 1 calc PR B -1 C83 C 0.7142(3) 0.7730(4) -0.1409(3) 0.0560(14) Uani 0.50 1 d PGDU B -1 H83 H 0.6942 0.7858 -0.2239 0.067 Uiso 0.50 1 calc PR B -1 C84 C 0.6839(3) 0.7991(4) -0.0599(4) 0.077(2) Uani 0.50 1 d PGDU B -1 H84 H 0.6433 0.8297 -0.0875 0.092 Uiso 0.50 1 calc PR B -1 C85 C 0.7131(3) 0.7803(4) 0.0617(4) 0.090(3) Uani 0.50 1 d PGDU B -1 H85 H 0.6924 0.7981 0.1170 0.108 Uiso 0.50 1 calc PR B -1 C86 C 0.7726(3) 0.7355(4) 0.1022(3) 0.065(2) Uani 0.50 1 d PGDU B -1 H86 H 0.7926 0.7227 0.1852 0.078 Uiso 0.50 1 calc PR B -1 C87 C 0.8634(2) 0.6589(2) 0.0610(4) 0.0569(9) Uani 0.50 1 d PDU B -1 H87A H 0.8489 0.6058 0.0690 0.085 Uiso 0.50 1 calc PR B -1 H87B H 0.8952 0.6769 0.1391 0.085 Uiso 0.50 1 calc PR B -1 H87C H 0.8866 0.6602 0.0016 0.085 Uiso 0.50 1 calc PR B -1 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 Li 0.068(2) 0.0199(15) 0.0317(16) 0.000 0.0211(16) 0.000 N1 0.0245(7) 0.0218(7) 0.0313(8) 0.000 0.0094(6) 0.000 N2 0.0723(10) 0.0378(7) 0.0343(7) 0.0042(5) 0.0268(7) -0.0042(6) C1 0.0233(6) 0.0231(6) 0.0281(6) 0.0004(4) 0.0090(5) 0.0007(4) C2 0.0215(6) 0.0228(6) 0.0252(6) 0.0003(4) 0.0079(5) 0.0005(5) C3 0.0252(6) 0.0239(6) 0.0299(6) -0.0039(5) 0.0080(5) 0.0026(5) C4 0.0325(7) 0.0280(6) 0.0355(7) 0.0009(5) 0.0115(6) 0.0056(5) C5 0.0402(8) 0.0313(7) 0.0406(8) 0.0027(6) 0.0090(6) 0.0134(6) C6 0.0321(7) 0.0420(8) 0.0478(8) -0.0048(6) 0.0109(6) 0.0154(6) C7 0.0295(7) 0.0456(8) 0.0450(8) -0.0037(6) 0.0165(6) 0.0058(6) C8 0.0283(6) 0.0327(7) 0.0366(7) 0.0008(5) 0.0117(5) 0.0035(5) C9 0.0199(6) 0.0218(6) 0.0287(6) -0.0019(4) 0.0100(5) 0.0012(4) C10 0.0229(6) 0.0253(6) 0.0367(7) 0.0029(5) 0.0051(5) 0.0020(5) C11 0.0206(6) 0.0306(7) 0.0431(8) -0.0028(5) 0.0030(5) -0.0007(5) C12 0.0247(6) 0.0248(6) 0.0450(8) -0.0049(5) 0.0135(6) -0.0044(5) C13 0.0321(7) 0.0252(6) 0.0360(7) 0.0020(5) 0.0144(6) -0.0025(5) C14 0.0248(6) 0.0274(6) 0.0259(6) 0.0000(5) 0.0084(5) -0.0012(5) C15 0.147(2) 0.0357(9) 0.0757(15) -0.0057(9) 0.0578(16) -0.0285(12) C16 0.0952(19) 0.133(3) 0.0812(17) 0.0361(17) 0.0560(16) 0.0035(18) C17 0.1026(19) 0.0972(18) 0.0453(11) 0.0327(12) 0.0064(11) -0.0329(15) C91 0.0271(13) 0.0360(15) 0.0372(16) 0.0107(12) 0.0075(12) 0.0041(11) C92 0.0335(17) 0.056(2) 0.046(2) 0.0184(18) 0.0205(16) 0.0060(16) C93 0.0550(19) 0.0431(17) 0.0377(15) 0.0032(13) 0.0202(14) 0.0137(14) C94 0.046(3) 0.035(2) 0.043(2) 0.0032(15) 0.0055(18) 0.0054(17) C95 0.0338(14) 0.0388(15) 0.0362(16) 0.0084(13) 0.0116(12) 0.0020(12) C96 0.0299(16) 0.0444(18) 0.0288(16) 0.0080(15) 0.0113(14) 0.0038(14) C97 0.0355(19) 0.040(2) 0.060(3) 0.0107(19) 0.010(2) -0.0071(18) C81 0.050(3) 0.036(2) 0.049(2) -0.004(2) 0.013(2) -0.0197(19) C82 0.043(2) 0.037(2) 0.057(2) -0.0054(18) 0.0241(19) -0.0111(16) C83 0.051(2) 0.051(2) 0.056(4) -0.006(2) 0.007(3) -0.0117(18) C84 0.052(3) 0.052(3) 0.132(7) -0.010(4) 0.040(4) -0.014(3) C85 0.130(7) 0.071(5) 0.101(6) -0.043(5) 0.082(6) -0.054(5) C86 0.100(6) 0.065(4) 0.034(3) -0.013(2) 0.028(3) -0.051(4) C87 0.057(2) 0.052(2) 0.056(2) -0.0116(17) 0.0113(17) -0.0002(17) _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 Li N1 1.928(4) . ? Li N2 2.058(3) . ? Li N2 2.058(3) 2_655 ? Li C15 2.713(4) 2_655 ? Li C15 2.713(4) . ? N1 C1 1.3670(15) . ? N1 C1 1.3670(15) 2_655 ? N2 C17 1.444(3) . ? N2 C15 1.461(2) . ? N2 C16 1.469(3) . ? C1 C2 1.3997(17) . ? C1 C3 1.4783(16) . ? C2 C2 1.428(2) 2_655 ? C2 C9 1.4761(16) . ? C3 C4 1.3971(18) . ? C3 C8 1.3981(19) . ? C4 C5 1.3910(19) . ? C5 C6 1.381(2) . ? C6 C7 1.385(2) . ? C7 C8 1.3886(19) . ? C9 C10 1.3984(17) . ? C9 C14 1.3996(17) . ? C10 C11 1.3910(18) . ? C11 C12 1.386(2) . ? C12 C13 1.383(2) . ? C13 C14 1.3905(17) . ? C15 C15 1.447(5) 2_655 ? C91 C92 1.3900 . ? C91 C96 1.3900 . ? C91 C97 1.499(4) . ? C92 C93 1.3900 . ? C93 C94 1.3900 . ? C94 C95 1.3900 . ? C95 C96 1.3900 . ? C81 C82 1.3900 . ? C81 C86 1.3900 . ? C81 C87 1.462(6) . ? C82 C83 1.3900 . ? C83 C84 1.3900 . ? C84 C85 1.3900 . ? C85 C86 1.3900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Li N2 134.62(7) . . ? N1 Li N2 134.61(7) . 2_655 ? N2 Li N2 90.77(15) . 2_655 ? N1 Li C15 164.54(6) . 2_655 ? N2 Li C15 59.57(10) . 2_655 ? N2 Li C15 32.08(7) 2_655 2_655 ? N1 Li C15 164.54(6) . . ? N2 Li C15 32.08(7) . . ? N2 Li C15 59.57(10) 2_655 . ? C15 Li C15 30.92(11) 2_655 . ? C1 N1 C1 106.24(14) . 2_655 ? C1 N1 Li 126.88(7) . . ? C1 N1 Li 126.88(7) 2_655 . ? C17 N2 C15 112.4(2) . . ? C17 N2 C16 109.25(18) . . ? C15 N2 C16 107.0(2) . . ? C17 N2 Li 114.00(12) . . ? C15 N2 Li 99.49(12) . . ? C16 N2 Li 114.22(14) . . ? N1 C1 C2 111.14(11) . . ? N1 C1 C3 117.52(11) . . ? C2 C1 C3 131.25(11) . . ? C1 C2 C2 105.74(7) . 2_655 ? C1 C2 C9 126.18(11) . . ? C2 C2 C9 128.07(6) 2_655 . ? C4 C3 C8 117.69(12) . . ? C4 C3 C1 119.67(12) . . ? C8 C3 C1 122.53(12) . . ? C5 C4 C3 121.49(13) . . ? C6 C5 C4 119.97(14) . . ? C5 C6 C7 119.38(13) . . ? C6 C7 C8 120.80(14) . . ? C7 C8 C3 120.66(13) . . ? C10 C9 C14 117.41(11) . . ? C10 C9 C2 121.01(11) . . ? C14 C9 C2 121.58(11) . . ? C11 C10 C9 121.34(12) . . ? C12 C11 C10 120.30(12) . . ? C13 C12 C11 119.22(12) . . ? C12 C13 C14 120.56(12) . . ? C13 C14 C9 121.15(12) . . ? C15 C15 N2 113.91(19) 2_655 . ? C15 C15 Li 74.54(6) 2_655 . ? N2 C15 Li 48.43(7) . . ? C92 C91 C96 120.0 . . ? C92 C91 C97 120.9(3) . . ? C96 C91 C97 119.1(3) . . ? C91 C92 C93 120.0 . . ? C94 C93 C92 120.0 . . ? C95 C94 C93 120.0 . . ? C96 C95 C94 120.0 . . ? C95 C96 C91 120.0 . . ? C82 C81 C86 120.0 . . ? C82 C81 C87 119.2(3) . . ? C86 C81 C87 120.7(3) . . ? C83 C82 C81 120.0 . . ? C84 C83 C82 120.0 . . ? C85 C84 C83 120.0 . . ? C86 C85 C84 120.0 . . ? C85 C86 C81 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Li N1 C1 107.98(9) . . . . ? N2 Li N1 C1 -72.02(9) 2_655 . . . ? C15 Li N1 C1 -45.9(2) 2_655 . . . ? C15 Li N1 C1 134.1(2) . . . . ? N2 Li N1 C1 -72.03(9) . . . 2_655 ? N2 Li N1 C1 107.98(9) 2_655 . . 2_655 ? C15 Li N1 C1 134.1(2) 2_655 . . 2_655 ? C15 Li N1 C1 -45.9(2) . . . 2_655 ? N1 Li N2 C17 -72.92(18) . . . . ? N2 Li N2 C17 107.08(18) 2_655 . . . ? C15 Li N2 C17 99.25(19) 2_655 . . . ? C15 Li N2 C17 119.8(2) . . . . ? N1 Li N2 C15 167.24(13) . . . . ? N2 Li N2 C15 -12.77(13) 2_655 . . . ? C15 Li N2 C15 -20.6(2) 2_655 . . . ? N1 Li N2 C16 53.67(19) . . . . ? N2 Li N2 C16 -126.34(19) 2_655 . . . ? C15 Li N2 C16 -134.2(2) 2_655 . . . ? C15 Li N2 C16 -113.6(2) . . . . ? C1 N1 C1 C2 0.01(6) 2_655 . . . ? Li N1 C1 C2 -179.99(6) . . . . ? C1 N1 C1 C3 -176.93(13) 2_655 . . . ? Li N1 C1 C3 3.07(13) . . . . ? N1 C1 C2 C2 -0.04(16) . . . 2_655 ? C3 C1 C2 C2 176.35(13) . . . 2_655 ? N1 C1 C2 C9 -178.79(10) . . . . ? C3 C1 C2 C9 -2.4(2) . . . . ? N1 C1 C3 C4 -45.67(16) . . . . ? C2 C1 C3 C4 138.13(14) . . . . ? N1 C1 C3 C8 130.44(12) . . . . ? C2 C1 C3 C8 -45.8(2) . . . . ? C8 C3 C4 C5 -0.8(2) . . . . ? C1 C3 C4 C5 175.49(13) . . . . ? C3 C4 C5 C6 0.1(2) . . . . ? C4 C5 C6 C7 0.5(2) . . . . ? C5 C6 C7 C8 -0.4(2) . . . . ? C6 C7 C8 C3 -0.4(2) . . . . ? C4 C3 C8 C7 1.0(2) . . . . ? C1 C3 C8 C7 -175.21(13) . . . . ? C1 C2 C9 C10 -44.04(18) . . . . ? C2 C2 C9 C10 137.49(16) 2_655 . . . ? C1 C2 C9 C14 135.25(13) . . . . ? C2 C2 C9 C14 -43.2(2) 2_655 . . . ? C14 C9 C10 C11 -1.10(19) . . . . ? C2 C9 C10 C11 178.22(12) . . . . ? C9 C10 C11 C12 0.6(2) . . . . ? C10 C11 C12 C13 0.5(2) . . . . ? C11 C12 C13 C14 -1.2(2) . . . . ? C12 C13 C14 C9 0.69(19) . . . . ? C10 C9 C14 C13 0.45(18) . . . . ? C2 C9 C14 C13 -178.87(11) . . . . ? C17 N2 C15 C15 -82.5(3) . . . 2_655 ? C16 N2 C15 C15 157.5(3) . . . 2_655 ? Li N2 C15 C15 38.5(3) . . . 2_655 ? C17 N2 C15 Li -121.00(17) . . . . ? C16 N2 C15 Li 119.08(16) . . . . ? N1 Li C15 C15 180.0 . . . 2_655 ? N2 Li C15 C15 -143.8(3) . . . 2_655 ? N2 Li C15 C15 21.31(19) 2_655 . . 2_655 ? N1 Li C15 N2 -36.2(3) . . . . ? N2 Li C15 N2 165.15(15) 2_655 . . . ? C15 Li C15 N2 143.8(3) 2_655 . . . ? C96 C91 C92 C93 0.0 . . . . ? C97 C91 C92 C93 -178.9(3) . . . . ? C91 C92 C93 C94 0.0 . . . . ? C92 C93 C94 C95 0.0 . . . . ? C93 C94 C95 C96 0.0 . . . . ? C94 C95 C96 C91 0.0 . . . . ? C92 C91 C96 C95 0.0 . . . . ? C97 C91 C96 C95 178.9(3) . . . . ? C86 C81 C82 C83 0.0 . . . . ? C87 C81 C82 C83 176.8(3) . . . . ? C81 C82 C83 C84 0.0 . . . . ? C82 C83 C84 C85 0.0 . . . . ? C83 C84 C85 C86 0.0 . . . . ? C84 C85 C86 C81 0.0 . . . . ? C82 C81 C86 C85 0.0 . . . . ? C87 C81 C86 C85 -176.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 75.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.448 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.039 _iucr_refine_instructions_details ; TITL mwal15 in C2/c CELL 1.54184 20.6834 17.2623 11.8317 90.000 110.377 90.000 ZERR 4.00 0.0004 0.0002 0.0002 0.000 0.002 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H LI N UNIT 192 208 4 12 SIZE 0.07 0.07 0.06 TEMP -173 ACTA 150 CONF FMAP 2 PLAN 10 L.S. 4 OMIT 4 2 5 WGHT 0.062800 3.054700 FVAR 3.15641 LI 3 0.500000 0.456635 0.250000 10.50000 0.06825 0.01986 = 0.03168 0.00000 0.02110 0.00000 N1 4 0.500000 0.568324 0.250000 10.50000 0.02447 0.02176 = 0.03133 0.00000 0.00939 0.00000 N2 4 0.479097 0.372896 0.356268 11.00000 0.07227 0.03782 = 0.03433 0.00418 0.02675 -0.00416 C1 1 0.556366 0.615843 0.281220 11.00000 0.02326 0.02305 = 0.02805 0.00040 0.00896 0.00073 C2 1 0.536799 0.693886 0.270408 11.00000 0.02152 0.02280 = 0.02525 0.00034 0.00792 0.00053 C3 1 0.624909 0.578928 0.313240 11.00000 0.02517 0.02385 = 0.02987 -0.00388 0.00801 0.00261 C4 1 0.640966 0.515207 0.390900 11.00000 0.03247 0.02798 = 0.03550 0.00093 0.01149 0.00565 AFIX 43 H4 2 0.608815 0.498631 0.426883 11.00000 -1.20000 AFIX 0 C5 1 0.702960 0.475486 0.416726 11.00000 0.04022 0.03128 = 0.04057 0.00270 0.00900 0.01342 AFIX 43 H5 2 0.712744 0.432274 0.469748 11.00000 -1.20000 AFIX 0 C6 1 0.750296 0.498902 0.365238 11.00000 0.03207 0.04199 = 0.04778 -0.00478 0.01092 0.01539 AFIX 43 H6 2 0.792548 0.471716 0.382046 11.00000 -1.20000 AFIX 0 C7 1 0.735571 0.562397 0.288870 11.00000 0.02954 0.04558 = 0.04497 -0.00371 0.01646 0.00584 AFIX 43 H7 2 0.768121 0.578839 0.253670 11.00000 -1.20000 AFIX 0 C8 1 0.673810 0.602305 0.263143 11.00000 0.02829 0.03273 = 0.03659 0.00081 0.01173 0.00349 AFIX 43 H8 2 0.664694 0.645929 0.210980 11.00000 -1.20000 AFIX 0 C9 1 0.583678 0.761186 0.294247 11.00000 0.01995 0.02181 = 0.02868 -0.00192 0.00998 0.00121 C10 1 0.643805 0.763509 0.396034 11.00000 0.02295 0.02531 = 0.03673 0.00293 0.00509 0.00199 AFIX 43 H10 2 0.653858 0.721718 0.451730 11.00000 -1.20000 AFIX 0 C11 1 0.689195 0.825764 0.417390 11.00000 0.02056 0.03062 = 0.04312 -0.00276 0.00297 -0.00073 AFIX 43 H11 2 0.729960 0.825831 0.486748 11.00000 -1.20000 AFIX 0 C12 1 0.675216 0.887702 0.337934 11.00000 0.02470 0.02484 = 0.04504 -0.00485 0.01348 -0.00441 AFIX 43 H12 2 0.706366 0.930052 0.352042 11.00000 -1.20000 AFIX 0 C13 1 0.615386 0.887126 0.237870 11.00000 0.03214 0.02520 = 0.03597 0.00199 0.01443 -0.00253 AFIX 43 H13 2 0.605010 0.929812 0.183813 11.00000 -1.20000 AFIX 0 C14 1 0.570292 0.824595 0.215723 11.00000 0.02484 0.02742 = 0.02588 0.00000 0.00840 -0.00121 AFIX 43 H14 2 0.529688 0.824920 0.146073 11.00000 -1.20000 AFIX 0 C15 1 0.474955 0.305146 0.280057 11.00000 0.14657 0.03571 = 0.07569 -0.00573 0.05779 -0.02847 AFIX 23 H15A 2 0.481633 0.257944 0.330370 11.00000 -1.20000 H15B 2 0.428134 0.302655 0.218377 11.00000 -1.20000 AFIX 0 C16 1 0.411533 0.381107 0.370034 11.00000 0.09521 0.13306 = 0.08117 0.03607 0.05599 0.00352 AFIX 33 H16A 2 0.375664 0.386495 0.290376 11.00000 -1.50000 H16B 2 0.411715 0.427185 0.418527 11.00000 -1.50000 H16C 2 0.402145 0.335118 0.410383 11.00000 -1.50000 AFIX 0 C17 1 0.531762 0.364967 0.473898 11.00000 0.10258 0.09716 = 0.04534 0.03268 0.00636 -0.03290 AFIX 33 H17A 2 0.533031 0.411903 0.521220 11.00000 -1.50000 H17B 2 0.576689 0.357477 0.464905 11.00000 -1.50000 H17C 2 0.521296 0.320143 0.515374 11.00000 -1.50000 AFIX 66 FLAT C91 > C97 FLAT C81 > C87 SADI C92 C97 C96 C97 C82 C87 C86 C87 SIMU 0.02 0.04 0.9 C81 > C87 PART -1 ISOR 0.015 C91 > C87 C91 1 0.474313 -0.024440 -0.017527 10.50000 0.02708 0.03605 = 0.03716 0.01074 0.00749 0.00410 C92 1 0.459530 0.011572 0.075720 10.50000 0.03351 0.05600 = 0.04558 0.01836 0.02049 0.00597 AFIX 43 H92 2 0.423277 -0.007467 0.099979 10.50000 -1.20000 AFIX 65 C93 1 0.497789 0.075439 0.133474 10.50000 0.05497 0.04308 = 0.03767 0.00322 0.02018 0.01366 AFIX 43 H93 2 0.487685 0.100051 0.197205 10.50000 -1.20000 AFIX 65 C94 1 0.550832 0.103295 0.097981 10.50000 0.04557 0.03524 = 0.04266 0.00320 0.00550 0.00541 AFIX 43 H94 2 0.576981 0.146946 0.137454 10.50000 -1.20000 AFIX 65 C95 1 0.565617 0.067284 0.004734 10.50000 0.03377 0.03879 = 0.03619 0.00835 0.01158 0.00202 AFIX 43 H95 2 0.601869 0.086323 -0.019523 10.50000 -1.20000 AFIX 65 C96 1 0.527358 0.003417 -0.053021 10.50000 0.02990 0.04437 = 0.02879 0.00802 0.01133 0.00382 AFIX 43 H96 2 0.537462 -0.021195 -0.116751 10.50000 -1.20000 AFIX 0 C97 1 0.432877 -0.092495 -0.082551 10.50000 0.03552 0.04004 = 0.06015 0.01067 0.00971 -0.00708 AFIX 137 H97A 2 0.401101 -0.108697 -0.041974 10.50000 -1.50000 H97B 2 0.463959 -0.135409 -0.082231 10.50000 -1.50000 H97C 2 0.406482 -0.077868 -0.165953 10.50000 -1.50000 AFIX 66 PART -1 10.5 C81 1 0.802923 0.709444 0.021130 10.50000 0.05010 0.03558 = 0.04872 -0.00376 0.01251 -0.01967 C82 1 0.773711 0.728206 -0.100386 10.50000 0.04316 0.03739 = 0.05665 -0.00541 0.02410 -0.01105 AFIX 43 H82 2 0.794414 0.710398 -0.155762 10.50000 -1.20000 AFIX 65 C83 1 0.714210 0.773024 -0.140877 10.50000 0.05120 0.05129 = 0.05645 -0.00571 0.00744 -0.01173 AFIX 43 H83 2 0.694245 0.785847 -0.223927 10.50000 -1.20000 AFIX 65 C84 1 0.683919 0.799079 -0.059853 10.50000 0.05212 0.05198 = 0.13225 -0.01003 0.03950 -0.01350 AFIX 43 H84 2 0.643252 0.829710 -0.087527 10.50000 -1.20000 AFIX 65 C85 1 0.713130 0.780317 0.061663 10.50000 0.12952 0.07075 = 0.10144 -0.04257 0.08150 -0.05414 AFIX 43 H85 2 0.692428 0.798126 0.117038 10.50000 -1.20000 AFIX 65 C86 1 0.772632 0.735500 0.102155 10.50000 0.09975 0.06512 = 0.03415 -0.01325 0.02782 -0.05134 AFIX 43 H86 2 0.792596 0.722677 0.185206 10.50000 -1.20000 AFIX 0 C87 1 0.863410 0.658917 0.061012 10.50000 0.05664 0.05200 = 0.05564 -0.01165 0.01131 -0.00017 AFIX 137 H87A 2 0.848907 0.605772 0.069021 10.50000 -1.50000 H87B 2 0.895226 0.676923 0.139132 10.50000 -1.50000 H87C 2 0.886642 0.660189 0.001616 10.50000 -1.50000 HKLF 4 ;