# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_mmce1b _database_code_depnum_ccdc_archive 'CCDC 910336' #TrackingRef 'mmce1b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H19 N3 O5' _chemical_formula_weight 417.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.2862(8) _cell_length_b 20.0798(16) _cell_length_c 9.6427(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.1550(10) _cell_angle_gamma 90.00 _cell_volume 1991.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5615 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 28.22 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9583 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details 'SADABS v2004/1, Sheldrick, G.M., (2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20407 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 28.33 _reflns_number_total 4961 _reflns_number_gt 3830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0565P)^2^+0.4618P] 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 4961 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 N1 N 0.77038(12) 0.39015(6) 1.06052(12) 0.0322(3) Uani 1 1 d . . . C1 C 0.82691(15) 0.43936(7) 0.99158(16) 0.0358(3) Uani 1 1 d . . . H1 H 0.8005 0.4837 1.0110 0.043 Uiso 1 1 calc R . . C2 C 0.92344(14) 0.42947(7) 0.89169(15) 0.0323(3) Uani 1 1 d . . . H2 H 0.9615 0.4664 0.8454 0.039 Uiso 1 1 calc R . . C3 C 0.96241(13) 0.36571(6) 0.86149(14) 0.0263(3) Uani 1 1 d . . . H3 H 1.0281 0.3579 0.7943 0.032 Uiso 1 1 calc R . . C4 C 0.90382(12) 0.31204(6) 0.93134(13) 0.0226(3) Uani 1 1 d . . . C5 C 0.93562(12) 0.24365(6) 0.90176(12) 0.0219(2) Uani 1 1 d . . . C6 C 0.87240(12) 0.19361(6) 0.96958(13) 0.0230(3) Uani 1 1 d . . . C7 C 0.77415(12) 0.20662(6) 1.07093(13) 0.0240(3) Uani 1 1 d . . . C8 C 0.70786(13) 0.15533(7) 1.14098(14) 0.0293(3) Uani 1 1 d . . . H8 H 0.7262 0.1100 1.1211 0.035 Uiso 1 1 calc R . . C9 C 0.61680(14) 0.17183(8) 1.23803(16) 0.0355(3) Uani 1 1 d . . . H9 H 0.5712 0.1383 1.2874 0.043 Uiso 1 1 calc R . . C10 C 0.59240(14) 0.23913(8) 1.26285(15) 0.0368(3) Uani 1 1 d . . . H10 H 0.5290 0.2500 1.3307 0.044 Uiso 1 1 calc R . . N2 N 0.65128(11) 0.28901(6) 1.19854(12) 0.0323(3) Uani 1 1 d . . . C11 C 0.74229(12) 0.27318(6) 1.10262(13) 0.0252(3) Uani 1 1 d . . . C12 C 0.80790(12) 0.32715(6) 1.03060(13) 0.0245(3) Uani 1 1 d . . . O1 O 0.89387(9) 0.12835(4) 0.94060(10) 0.0271(2) Uani 1 1 d . . . C13 C 1.01707(12) 0.11237(6) 0.87467(13) 0.0243(3) Uani 1 1 d . . . H13 H 1.0035 0.0721 0.8153 0.029 Uiso 1 1 calc R . . C14 C 1.12076(12) 0.09615(6) 0.97983(13) 0.0228(3) Uani 1 1 d . . . C15 C 1.15474(12) 0.03057(6) 1.00807(14) 0.0271(3) Uani 1 1 d . . . H15 H 1.1146 -0.0044 0.9572 0.033 Uiso 1 1 calc R . . C16 C 1.24601(13) 0.01501(6) 1.10894(15) 0.0301(3) Uani 1 1 d . . . H16 H 1.2663 -0.0302 1.1283 0.036 Uiso 1 1 calc R . . C17 C 1.30793(13) 0.06592(7) 1.18193(14) 0.0279(3) Uani 1 1 d . . . O2 O 1.39717(10) 0.05439(5) 1.28249(11) 0.0378(3) Uani 1 1 d . . . C18 C 1.27745(13) 0.13189(6) 1.15097(14) 0.0277(3) Uani 1 1 d . . . H18 H 1.3209 0.1670 1.1982 0.033 Uiso 1 1 calc R . . C19 C 1.18469(13) 0.14661(6) 1.05228(13) 0.0256(3) Uani 1 1 d . . . H19 H 1.1640 0.1918 1.0333 0.031 Uiso 1 1 calc R . . C20 C 1.05975(12) 0.16882(6) 0.78206(13) 0.0237(3) Uani 1 1 d . . . C21 C 1.15285(13) 0.14768(6) 0.67115(13) 0.0271(3) Uani 1 1 d . . . O3 O 1.16138(11) 0.09071(5) 0.63444(11) 0.0415(3) Uani 1 1 d . . . O4 O 1.22465(11) 0.19749(5) 0.62286(11) 0.0373(3) Uani 1 1 d . . . C22 C 1.31587(18) 0.17887(9) 0.51510(18) 0.0494(4) Uani 1 1 d . . . H22A H 1.3648 0.2183 0.4856 0.074 Uiso 1 1 calc R . . H22B H 1.2682 0.1605 0.4357 0.074 Uiso 1 1 calc R . . H22C H 1.3762 0.1453 0.5512 0.074 Uiso 1 1 calc R . . N3 N 1.02597(10) 0.22989(5) 0.79583(10) 0.0234(2) Uani 1 1 d . . . O31 O 1.46316(10) -0.07209(5) 1.28928(12) 0.0405(3) Uani 1 1 d . . . C32 C 1.52879(18) -0.09499(10) 1.1693(2) 0.0544(5) Uani 1 1 d . . . H32A H 1.5877 -0.0602 1.1359 0.082 Uiso 1 1 calc R . . H32B H 1.4651 -0.1056 1.0968 0.082 Uiso 1 1 calc R . . H32C H 1.5789 -0.1350 1.1922 0.082 Uiso 1 1 calc R . . H2O H 1.4135(16) 0.0087(9) 1.2894(17) 0.040 Uiso 1 1 d . . . H31 H 1.4065(18) -0.1005(9) 1.3122(18) 0.040 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0359(6) 0.0247(6) 0.0360(6) -0.0010(5) 0.0083(5) 0.0045(5) C1 0.0453(8) 0.0197(6) 0.0425(8) -0.0016(6) 0.0084(7) 0.0043(6) C2 0.0383(8) 0.0213(6) 0.0373(8) 0.0029(5) 0.0062(6) -0.0019(5) C3 0.0285(7) 0.0220(6) 0.0285(6) 0.0016(5) 0.0041(5) -0.0004(5) C4 0.0231(6) 0.0210(6) 0.0238(6) 0.0003(5) -0.0009(5) -0.0001(5) C5 0.0221(6) 0.0204(6) 0.0233(6) 0.0010(4) 0.0005(5) -0.0001(4) C6 0.0226(6) 0.0187(6) 0.0276(6) 0.0009(5) -0.0025(5) -0.0005(4) C7 0.0205(6) 0.0256(6) 0.0259(6) 0.0034(5) -0.0022(5) -0.0024(5) C8 0.0248(6) 0.0295(7) 0.0337(7) 0.0064(5) -0.0021(5) -0.0051(5) C9 0.0264(7) 0.0424(8) 0.0377(8) 0.0110(6) 0.0026(6) -0.0083(6) C10 0.0269(7) 0.0457(9) 0.0378(8) 0.0044(6) 0.0100(6) -0.0021(6) N2 0.0274(6) 0.0368(6) 0.0326(6) 0.0014(5) 0.0069(5) 0.0004(5) C11 0.0214(6) 0.0290(7) 0.0253(6) 0.0024(5) 0.0003(5) 0.0007(5) C12 0.0248(6) 0.0228(6) 0.0259(6) 0.0000(5) 0.0014(5) 0.0016(5) O1 0.0260(5) 0.0176(4) 0.0378(5) 0.0013(4) 0.0031(4) -0.0019(3) C13 0.0276(6) 0.0170(5) 0.0283(6) -0.0013(5) 0.0026(5) -0.0003(5) C14 0.0247(6) 0.0191(6) 0.0246(6) 0.0005(5) 0.0039(5) -0.0010(5) C15 0.0268(6) 0.0176(6) 0.0368(7) -0.0002(5) -0.0009(5) -0.0030(5) C16 0.0287(7) 0.0194(6) 0.0422(8) 0.0051(5) -0.0015(6) -0.0017(5) C17 0.0259(6) 0.0282(7) 0.0296(7) 0.0045(5) 0.0006(5) -0.0020(5) O2 0.0389(6) 0.0316(5) 0.0427(6) 0.0075(4) -0.0126(5) -0.0032(4) C18 0.0316(7) 0.0230(6) 0.0285(6) -0.0031(5) 0.0004(5) -0.0046(5) C19 0.0316(7) 0.0182(6) 0.0271(6) -0.0003(5) 0.0036(5) -0.0013(5) C20 0.0269(6) 0.0208(6) 0.0233(6) 0.0003(5) -0.0014(5) 0.0001(5) C21 0.0332(7) 0.0235(6) 0.0247(6) 0.0007(5) -0.0001(5) 0.0045(5) O3 0.0545(7) 0.0266(5) 0.0435(6) -0.0106(4) 0.0116(5) 0.0019(5) O4 0.0468(6) 0.0263(5) 0.0389(6) 0.0044(4) 0.0201(5) 0.0060(4) C22 0.0570(11) 0.0489(10) 0.0426(9) 0.0050(7) 0.0275(8) 0.0125(8) N3 0.0262(5) 0.0206(5) 0.0235(5) 0.0007(4) 0.0012(4) 0.0012(4) O31 0.0329(6) 0.0373(6) 0.0515(7) 0.0159(5) 0.0078(5) -0.0020(4) C32 0.0430(10) 0.0640(12) 0.0561(11) 0.0090(9) 0.0094(8) 0.0019(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3262(18) . ? N1 C12 1.3539(16) . ? C1 C2 1.399(2) . ? C2 C3 1.3730(18) . ? C3 C4 1.4072(17) . ? C4 C12 1.4096(17) . ? C4 C5 1.4405(17) . ? C5 C6 1.3647(17) . ? C5 N3 1.4101(16) . ? C6 O1 1.3580(15) . ? C6 C7 1.4318(18) . ? C7 C8 1.4087(17) . ? C7 C11 1.4098(18) . ? C8 C9 1.367(2) . ? C9 C10 1.395(2) . ? C10 N2 1.3254(18) . ? N2 C11 1.3556(17) . ? C11 C12 1.4542(18) . ? O1 C13 1.4552(15) . ? C13 C14 1.5053(18) . ? C13 C20 1.5089(17) . ? C14 C15 1.3893(17) . ? C14 C19 1.3945(17) . ? C15 C16 1.3856(19) . ? C16 C17 1.3942(19) . ? C17 O2 1.3534(16) . ? C17 C18 1.3933(18) . ? C18 C19 1.3778(19) . ? C20 N3 1.2817(16) . ? C20 C21 1.4989(18) . ? C21 O3 1.2006(16) . ? C21 O4 1.3284(16) . ? O4 C22 1.4509(17) . ? O31 C32 1.418(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 C1 N1 C12 117.63(12) . . ? N1 C1 C2 123.52(12) . . ? C3 C2 C1 119.10(12) . . ? C2 C3 C4 119.14(12) . . ? C3 C4 C12 117.49(11) . . ? C3 C4 C5 122.52(11) . . ? C12 C4 C5 119.96(11) . . ? C6 C5 N3 121.25(11) . . ? C6 C5 C4 119.89(11) . . ? N3 C5 C4 118.72(10) . . ? O1 C6 C5 122.26(11) . . ? O1 C6 C7 115.60(11) . . ? C5 C6 C7 122.06(11) . . ? C8 C7 C11 118.42(12) . . ? C8 C7 C6 122.50(12) . . ? C11 C7 C6 119.08(11) . . ? C9 C8 C7 119.00(13) . . ? C8 C9 C10 118.43(13) . . ? N2 C10 C9 124.68(13) . . ? C10 N2 C11 117.34(12) . . ? N2 C11 C7 122.12(12) . . ? N2 C11 C12 118.25(12) . . ? C7 C11 C12 119.64(11) . . ? N1 C12 C4 123.11(12) . . ? N1 C12 C11 117.49(11) . . ? C4 C12 C11 119.37(11) . . ? C6 O1 C13 116.42(9) . . ? O1 C13 C14 111.69(10) . . ? O1 C13 C20 110.37(10) . . ? C14 C13 C20 110.76(10) . . ? C15 C14 C19 118.19(12) . . ? C15 C14 C13 120.97(11) . . ? C19 C14 C13 120.84(11) . . ? C16 C15 C14 121.39(12) . . ? C15 C16 C17 119.79(12) . . ? O2 C17 C18 117.90(12) . . ? O2 C17 C16 122.97(12) . . ? C18 C17 C16 119.12(12) . . ? C19 C18 C17 120.46(12) . . ? C18 C19 C14 120.99(12) . . ? N3 C20 C21 121.25(11) . . ? N3 C20 C13 125.31(11) . . ? C21 C20 C13 113.39(10) . . ? O3 C21 O4 124.95(13) . . ? O3 C21 C20 121.84(12) . . ? O4 C21 C20 113.19(11) . . ? C21 O4 C22 114.72(12) . . ? C20 N3 C5 116.22(11) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O31 0.935(18) 1.700(18) 2.6295(15) 171.8(16) . O31 H31 N1 0.846(18) 2.205(18) 2.9090(16) 140.7(15) 2_747 O31 H31 N2 0.846(18) 2.299(18) 3.0297(17) 144.8(15) 2_747 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.290 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.042 _iucr_refine_instructions_details ; TITL MMCe1b in P2(1)/c CELL 0.71073 10.2862 20.0798 9.6427 90.000 90.155 90.000 ZERR 4.00 0.0008 0.0016 0.0008 0.000 0.001 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 92 76 12 20 TEMP -123 SIZE 0.14 0.35 0.43 L.S. 8 acta 52 htab eqiv $1 -x+2, y-1/2, -z+5/2 htab O2 O31 htab O31 N1_$1 htab O31 N2_$1 eqiv $2 x, 0.5-y, 0.5+z mpla 14 n1 > C12 C1_$2 C3_$2 C3_$2 C4_$2 c5_$2 n1_$2 n2_$2 C6_$2 c7_$2 C12_$2 WGHT 0.056500 0.461800 FVAR 0.34108 N1 3 0.770376 0.390149 1.060523 11.00000 0.03594 0.02469 = 0.03602 -0.00105 0.00826 0.00447 C1 1 0.826906 0.439363 0.991578 11.00000 0.04525 0.01973 = 0.04255 -0.00157 0.00838 0.00430 AFIX 43 H1 2 0.800451 0.483710 1.011043 11.00000 -1.20000 AFIX 0 C2 1 0.923443 0.429471 0.891685 11.00000 0.03833 0.02133 = 0.03727 0.00286 0.00623 -0.00190 AFIX 43 H2 2 0.961500 0.466373 0.845393 11.00000 -1.20000 AFIX 0 C3 1 0.962407 0.365712 0.861490 11.00000 0.02851 0.02201 = 0.02851 0.00158 0.00407 -0.00037 AFIX 43 H3 2 1.028066 0.357929 0.794316 11.00000 -1.20000 AFIX 0 C4 1 0.903824 0.312043 0.931336 11.00000 0.02306 0.02100 = 0.02382 0.00029 -0.00089 -0.00009 C5 1 0.935623 0.243646 0.901764 11.00000 0.02206 0.02040 = 0.02326 0.00097 0.00045 -0.00010 C6 1 0.872402 0.193606 0.969585 11.00000 0.02256 0.01868 = 0.02762 0.00088 -0.00246 -0.00048 C7 1 0.774154 0.206623 1.070927 11.00000 0.02054 0.02558 = 0.02588 0.00344 -0.00224 -0.00238 C8 1 0.707861 0.155333 1.140983 11.00000 0.02475 0.02951 = 0.03369 0.00639 -0.00205 -0.00505 AFIX 43 H8 2 0.726182 0.109965 1.121062 11.00000 -1.20000 AFIX 0 C9 1 0.616799 0.171826 1.238031 11.00000 0.02642 0.04242 = 0.03769 0.01101 0.00261 -0.00826 AFIX 43 H9 2 0.571185 0.138261 1.287431 11.00000 -1.20000 AFIX 0 C10 1 0.592398 0.239134 1.262851 11.00000 0.02689 0.04570 = 0.03785 0.00439 0.01002 -0.00214 AFIX 43 H10 2 0.529044 0.249980 1.330704 11.00000 -1.20000 AFIX 0 N2 3 0.651282 0.289015 1.198537 11.00000 0.02735 0.03679 = 0.03265 0.00136 0.00691 0.00042 C11 1 0.742295 0.273180 1.102624 11.00000 0.02138 0.02905 = 0.02529 0.00240 0.00033 0.00066 C12 1 0.807901 0.327152 1.030600 11.00000 0.02484 0.02276 = 0.02589 0.00003 0.00141 0.00156 O1 4 0.893872 0.128352 0.940602 11.00000 0.02601 0.01758 = 0.03783 0.00127 0.00315 -0.00189 C13 1 1.017072 0.112372 0.874666 11.00000 0.02762 0.01698 = 0.02832 -0.00134 0.00264 -0.00031 AFIX 13 H13 2 1.003533 0.072128 0.815269 11.00000 -1.20000 AFIX 0 C14 1 1.120756 0.096154 0.979828 11.00000 0.02469 0.01907 = 0.02463 0.00047 0.00385 -0.00099 C15 1 1.154743 0.030568 1.008075 11.00000 0.02682 0.01765 = 0.03678 -0.00018 -0.00088 -0.00304 AFIX 43 H15 2 1.114559 -0.004353 0.957157 11.00000 -1.20000 AFIX 0 C16 1 1.246007 0.015015 1.108937 11.00000 0.02870 0.01935 = 0.04217 0.00509 -0.00147 -0.00172 AFIX 43 H16 2 1.266322 -0.030197 1.128294 11.00000 -1.20000 AFIX 0 C17 1 1.307932 0.065925 1.181928 11.00000 0.02594 0.02821 = 0.02963 0.00449 0.00063 -0.00199 O2 4 1.397168 0.054388 1.282495 11.00000 0.03893 0.03158 = 0.04273 0.00754 -0.01256 -0.00320 C18 1 1.277454 0.131890 1.150970 11.00000 0.03161 0.02299 = 0.02845 -0.00307 0.00039 -0.00456 AFIX 43 H18 2 1.320932 0.166960 1.198233 11.00000 -1.20000 AFIX 0 C19 1 1.184694 0.146611 1.052285 11.00000 0.03160 0.01816 = 0.02710 -0.00031 0.00364 -0.00131 AFIX 43 H19 2 1.163981 0.191814 1.033316 11.00000 -1.20000 AFIX 0 C20 1 1.059749 0.168817 0.782060 11.00000 0.02687 0.02083 = 0.02334 0.00026 -0.00137 0.00009 C21 1 1.152848 0.147675 0.671146 11.00000 0.03320 0.02349 = 0.02468 0.00069 -0.00009 0.00451 O3 4 1.161377 0.090712 0.634440 11.00000 0.05452 0.02661 = 0.04355 -0.01061 0.01160 0.00187 O4 4 1.224649 0.197491 0.622858 11.00000 0.04678 0.02630 = 0.03888 0.00441 0.02014 0.00596 C22 1 1.315867 0.178874 0.515104 11.00000 0.05697 0.04888 = 0.04265 0.00505 0.02749 0.01250 AFIX 33 H22A 2 1.364787 0.218265 0.485627 11.00000 -1.50000 H22B 2 1.268210 0.160506 0.435711 11.00000 -1.50000 H22C 2 1.376217 0.145277 0.551191 11.00000 -1.50000 AFIX 0 N3 3 1.025968 0.229894 0.795828 11.00000 0.02623 0.02058 = 0.02345 0.00065 0.00116 0.00119 O31 4 1.463160 -0.072087 1.289279 11.00000 0.03292 0.03725 = 0.05148 0.01595 0.00777 -0.00197 C32 1 1.528795 -0.094994 1.169274 11.00000 0.04298 0.06402 = 0.05610 0.00897 0.00935 0.00190 AFIX 137 H32A 2 1.587722 -0.060200 1.135859 11.00000 -1.50000 H32B 2 1.465088 -0.105590 1.096814 11.00000 -1.50000 H32C 2 1.578936 -0.135024 1.192211 11.00000 -1.50000 AFIX 0 H2O 2 1.413547 0.008688 1.289446 11.00000 10.04000 H31 2 1.406456 -0.100518 1.312249 11.00000 10.04000 HKLF 4 ;