# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/418 data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C13H22N2O4 _chemical_formula_sum 'C13 H22 N2 O4' _chemical_formula_weight 270.33 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 ? _symmetry_space_group_name_H-M P4(2) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z+1/2' 'y, -x, z+1/2' _cell_length_a 12.6541(2) _cell_length_b 12.6541(2) _cell_length_c 9.2145(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1475.48(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16161 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 30.57 _reflns_number_total 4323 _reflns_number_gt 3861 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; 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^)+(0.0550P)^2^+0.3400P] 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 0.4(10) _refine_ls_number_reflns 4323 _refine_ls_number_parameters 266 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1212 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.369 _refine_ls_shift/su_mean 0.056 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 O1A O 0.0784(7) 0.3986(6) 0.0300(13) 0.0372(14) Uani 0.50 1 d P A 1 O1B O 0.0969(8) 0.3673(7) 0.0307(13) 0.0437(17) Uani 0.50 1 d P A 2 O2 O 0.08688(9) 0.38131(11) 0.61134(14) 0.0306(3) Uani 1 1 d . . . O3 O 0.38779(9) 0.55632(10) 0.59959(15) 0.0299(3) Uani 1 1 d . A . HO3 H 0.393(2) 0.565(2) 0.692(4) 0.047(7) Uiso 1 1 d . . . O4 O 0.44288(9) 0.39544(10) 0.40820(15) 0.0269(2) Uani 1 1 d . . . HO4 H 0.497(2) 0.416(2) 0.448(3) 0.038(6) Uiso 1 1 d . . . N1 N 0.18129(12) 0.40819(13) 0.23777(18) 0.0322(3) Uani 1 1 d . A . N2 N -0.00229(10) 0.34931(12) 0.40251(17) 0.0270(3) Uani 1 1 d . . . C1 C 0.09656(16) 0.38029(18) 0.1763(2) 0.0360(4) Uani 1 1 d . . . C2 C -0.00378(13) 0.34082(16) 0.2448(2) 0.0330(4) Uani 1 1 d . A . H2B H -0.067(2) 0.383(2) 0.202(3) 0.041(6) Uiso 1 1 d . . . C3 C 0.08269(12) 0.37592(13) 0.46448(18) 0.0240(3) Uani 1 1 d . A . C4 C 0.18873(12) 0.40138(13) 0.39594(19) 0.0243(3) Uani 1 1 d . . . C5 C 0.23670(12) 0.50620(13) 0.4532(2) 0.0243(3) Uani 1 1 d . A . H5A H 0.1866(17) 0.5547(17) 0.480(2) 0.022(5) Uiso 1 1 d . . . H5B H 0.2805(17) 0.5340(17) 0.375(2) 0.026(5) Uiso 1 1 d . . . C6 C 0.31311(12) 0.47412(13) 0.57317(17) 0.0238(3) Uani 1 1 d . . . H6A H 0.2761(18) 0.4586(19) 0.657(3) 0.031(6) Uiso 1 1 d . . . C7 C 0.36399(12) 0.37204(13) 0.51482(19) 0.0249(3) Uani 1 1 d . A . H7A H 0.3952(15) 0.3331(15) 0.593(3) 0.023(5) Uiso 1 1 d . . . C8 C 0.27236(13) 0.31515(14) 0.4399(2) 0.0304(4) Uani 1 1 d . A . H8A H 0.2989(19) 0.275(2) 0.356(3) 0.037(7) Uiso 1 1 d . . . H8B H 0.247(2) 0.267(2) 0.502(3) 0.040(6) Uiso 1 1 d . . . C9 C -0.02761(19) 0.2258(2) 0.1982(3) 0.0526(6) Uani 1 1 d . . . H9A H -0.038(2) 0.225(2) 0.097(3) 0.051(7) Uiso 1 1 d . . . C10 C -0.1297(2) 0.1872(3) 0.2692(4) 0.0649(8) Uani 1 1 d . A . H10A H -0.189(3) 0.236(3) 0.257(4) 0.074(10) Uiso 1 1 d . . . H10B H -0.146(3) 0.122(3) 0.234(4) 0.068(9) Uiso 1 1 d . . . H10C H -0.114(3) 0.181(3) 0.372(5) 0.076(11) Uiso 1 1 d . . . C11 C 0.0646(3) 0.1538(2) 0.2300(6) 0.0799(12) Uani 1 1 d . A . H11A H 0.135(4) 0.172(3) 0.192(4) 0.091(12) Uiso 1 1 d . . . H11B H 0.0707(18) 0.1416(18) 0.323(3) 0.026(6) Uiso 1 1 d . . . H11C H 0.069(5) 0.071(6) 0.210(7) 0.16(2) Uiso 1 1 d . . . C12A C 0.1669(7) 0.4462(7) -0.0436(10) 0.0485(18) Uani 0.50 1 d P A 1 H12A H 0.1484 0.4588 -0.1454 0.073 Uiso 0.50 1 calc PR A 1 H12B H 0.2279 0.3986 -0.0386 0.073 Uiso 0.50 1 calc PR A 1 H12C H 0.1845 0.5135 0.0032 0.073 Uiso 0.50 1 calc PR A 1 C12B C 0.1909(7) 0.4021(8) -0.0443(11) 0.057(2) Uani 0.50 1 d P A 2 H12D H 0.1836 0.3874 -0.1482 0.085 Uiso 0.50 1 calc PR A 2 H12E H 0.2524 0.3643 -0.0060 0.085 Uiso 0.50 1 calc PR A 2 H12F H 0.2003 0.4782 -0.0295 0.085 Uiso 0.50 1 calc PR A 2 C13 C -0.00925(15) 0.3513(2) 0.6864(2) 0.0358(4) Uani 1 1 d . . . H13A H 0.002(3) 0.351(2) 0.787(4) 0.066(9) Uiso 1 1 d . . . H13B H -0.064(2) 0.403(2) 0.668(3) 0.038(6) Uiso 1 1 d . . . H13C H -0.034(2) 0.284(2) 0.655(3) 0.046(7) 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 O1A 0.031(3) 0.058(4) 0.0228(17) 0.000(3) -0.001(2) -0.018(2) O1B 0.035(3) 0.074(5) 0.0222(18) -0.006(4) -0.001(2) -0.014(3) O2 0.0225(5) 0.0486(7) 0.0207(6) 0.0024(5) 0.0016(4) -0.0055(5) O3 0.0247(5) 0.0406(7) 0.0244(6) -0.0109(5) 0.0025(5) -0.0085(5) O4 0.0195(5) 0.0351(6) 0.0262(6) -0.0061(5) 0.0028(5) -0.0027(4) N1 0.0287(7) 0.0454(8) 0.0225(7) -0.0055(6) 0.0021(6) -0.0131(6) N2 0.0214(6) 0.0343(7) 0.0253(6) 0.0008(6) 0.0000(6) -0.0013(5) C1 0.0342(9) 0.0508(12) 0.0231(9) -0.0038(7) 0.0010(7) -0.0138(8) C2 0.0230(7) 0.0477(10) 0.0281(8) -0.0032(8) -0.0017(7) -0.0103(7) C3 0.0208(6) 0.0294(7) 0.0219(8) 0.0015(6) 0.0024(6) 0.0003(6) C4 0.0206(6) 0.0314(7) 0.0210(7) -0.0036(6) 0.0010(6) -0.0049(6) C5 0.0209(6) 0.0268(7) 0.0252(7) -0.0032(6) -0.0008(6) -0.0003(6) C6 0.0197(6) 0.0317(7) 0.0200(7) -0.0049(6) 0.0021(5) -0.0026(6) C7 0.0208(7) 0.0298(8) 0.0240(8) 0.0008(6) 0.0012(6) 0.0006(6) C8 0.0238(7) 0.0264(7) 0.0411(10) -0.0041(7) 0.0023(7) -0.0019(6) C9 0.0439(12) 0.0599(14) 0.0541(14) -0.0224(11) 0.0063(10) -0.0249(10) C10 0.0518(14) 0.0796(19) 0.0632(18) -0.0116(15) 0.0036(13) -0.0400(14) C11 0.070(2) 0.0432(14) 0.127(4) -0.028(2) 0.012(2) -0.0098(13) C12A 0.038(4) 0.085(5) 0.023(2) 0.001(4) 0.000(2) -0.024(3) C12B 0.041(4) 0.107(7) 0.023(2) -0.007(4) 0.005(2) -0.026(4) C13 0.0252(8) 0.0567(13) 0.0254(9) 0.0078(8) 0.0030(6) -0.0049(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 O1A C1 1.388(12) . ? O1A C12A 1.441(14) . ? O1B C1 1.352(12) . ? O1B C12B 1.444(15) . ? O2 C3 1.356(2) . ? O2 C13 1.450(2) . ? O3 C6 1.4263(19) . ? O3 HO3 0.86(3) . ? O4 C7 1.432(2) . ? O4 HO4 0.82(3) . ? N1 C1 1.263(2) . ? N1 C4 1.463(2) . ? N2 C3 1.263(2) . ? N2 C2 1.457(2) . ? C1 C2 1.503(3) . ? C2 C9 1.548(3) . ? C2 H2B 1.04(3) . ? C3 C4 1.518(2) . ? C4 C5 1.551(2) . ? C4 C8 1.573(2) . ? C5 C6 1.524(2) . ? C5 H5A 0.92(2) . ? C5 H5B 0.98(2) . ? C6 C7 1.540(2) . ? C6 H6A 0.92(2) . ? C7 C8 1.529(2) . ? C7 H7A 0.95(2) . ? C8 H8A 0.98(2) . ? C8 H8B 0.89(3) . ? C9 C11 1.509(5) . ? C9 C10 1.528(3) . ? C9 H9A 0.95(3) . ? C10 H10A 0.97(4) . ? C10 H10B 0.91(4) . ? C10 H10C 0.97(4) . ? C11 H11A 0.98(4) . ? C11 H11B 0.88(3) . ? C11 H11C 1.07(7) . ? C12A H12A 0.9800 . ? C12A H12B 0.9800 . ? C12A H12C 0.9800 . ? C12B H12D 0.9800 . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? C13 H13A 0.93(4) . ? C13 H13B 0.96(3) . ? C13 H13C 0.95(3) . ? 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 O1A C12A 113.5(8) . . ? C1 O1B C12B 116.2(9) . . ? C3 O2 C13 115.49(14) . . ? C6 O3 HO3 108.2(18) . . ? C7 O4 HO4 109.9(19) . . ? C1 N1 C4 118.99(15) . . ? C3 N2 C2 118.78(15) . . ? N1 C1 O1B 118.4(5) . . ? N1 C1 O1A 122.0(5) . . ? O1B C1 O1A 19.3(5) . . ? N1 C1 C2 128.45(18) . . ? O1B C1 C2 112.3(5) . . ? O1A C1 C2 108.9(4) . . ? N2 C2 C1 112.53(14) . . ? N2 C2 C9 110.41(18) . . ? C1 C2 C9 111.13(17) . . ? N2 C2 H2B 110.4(14) . . ? C1 C2 H2B 109.1(14) . . ? C9 C2 H2B 102.8(14) . . ? N2 C3 O2 119.85(15) . . ? N2 C3 C4 128.40(16) . . ? O2 C3 C4 111.72(14) . . ? N1 C4 C3 111.73(13) . . ? N1 C4 C5 108.29(14) . . ? C3 C4 C5 112.70(14) . . ? N1 C4 C8 109.92(15) . . ? C3 C4 C8 109.89(14) . . ? C5 C4 C8 104.02(12) . . ? C6 C5 C4 105.50(13) . . ? C6 C5 H5A 114.8(12) . . ? C4 C5 H5A 113.2(13) . . ? C6 C5 H5B 105.9(12) . . ? C4 C5 H5B 106.1(13) . . ? H5A C5 H5B 110.7(17) . . ? O3 C6 C5 110.49(14) . . ? O3 C6 C7 113.22(12) . . ? C5 C6 C7 103.63(12) . . ? O3 C6 H6A 110.3(14) . . ? C5 C6 H6A 110.0(14) . . ? C7 C6 H6A 109.0(15) . . ? O4 C7 C8 108.44(14) . . ? O4 C7 C6 110.95(13) . . ? C8 C7 C6 103.61(12) . . ? O4 C7 H7A 109.5(12) . . ? C8 C7 H7A 114.1(12) . . ? C6 C7 H7A 110.1(13) . . ? C7 C8 C4 107.44(13) . . ? C7 C8 H8A 109.7(14) . . ? C4 C8 H8A 112.7(14) . . ? C7 C8 H8B 107.8(17) . . ? C4 C8 H8B 112.8(16) . . ? H8A C8 H8B 106(2) . . ? C11 C9 C10 112.2(3) . . ? C11 C9 C2 111.3(2) . . ? C10 C9 C2 110.3(2) . . ? C11 C9 H9A 107.0(16) . . ? C10 C9 H9A 107.4(17) . . ? C2 C9 H9A 108.5(16) . . ? C9 C10 H10A 114(2) . . ? C9 C10 H10B 109(2) . . ? H10A C10 H10B 111(3) . . ? C9 C10 H10C 106(2) . . ? H10A C10 H10C 108(3) . . ? H10B C10 H10C 109(3) . . ? C9 C11 H11A 119(2) . . ? C9 C11 H11B 111.4(16) . . ? H11A C11 H11B 108(3) . . ? C9 C11 H11C 127(3) . . ? H11A C11 H11C 97(4) . . ? H11B C11 H11C 90(4) . . ? O1A C12A H12A 109.5 . . ? O1A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? O1A C12A H12C 109.4 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? O1B C12B H12D 109.3 . . ? O1B C12B H12E 109.6 . . ? H12D C12B H12E 109.5 . . ? O1B C12B H12F 109.4 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? O2 C13 H13A 110(2) . . ? O2 C13 H13B 109.8(15) . . ? H13A C13 H13B 107(2) . . ? O2 C13 H13C 111.2(17) . . ? H13A C13 H13C 111(3) . . ? H13B C13 H13C 108(2) . . ? 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 N1 C1 O1B -167.4(4) . . . . ? C4 N1 C1 O1A 170.6(4) . . . . ? C4 N1 C1 C2 1.2(3) . . . . ? C12B O1B C1 N1 -9.0(8) . . . . ? C12B O1B C1 O1A 97(3) . . . . ? C12B O1B C1 C2 -179.4(6) . . . . ? C12A O1A C1 N1 3.2(8) . . . . ? C12A O1A C1 O1B -82(3) . . . . ? C12A O1A C1 C2 174.5(5) . . . . ? C3 N2 C2 C1 -7.7(3) . . . . ? C3 N2 C2 C9 117.10(18) . . . . ? N1 C1 C2 N2 7.7(3) . . . . ? O1B C1 C2 N2 176.9(4) . . . . ? O1A C1 C2 N2 -162.8(4) . . . . ? N1 C1 C2 C9 -116.7(3) . . . . ? O1B C1 C2 C9 52.5(4) . . . . ? O1A C1 C2 C9 72.7(4) . . . . ? C2 N2 C3 O2 -178.05(16) . . . . ? C2 N2 C3 C4 -0.2(3) . . . . ? C13 O2 C3 N2 2.2(3) . . . . ? C13 O2 C3 C4 -176.06(16) . . . . ? C1 N1 C4 C3 -8.8(3) . . . . ? C1 N1 C4 C5 -133.50(18) . . . . ? C1 N1 C4 C8 113.5(2) . . . . ? N2 C3 C4 N1 8.9(3) . . . . ? O2 C3 C4 N1 -173.08(14) . . . . ? N2 C3 C4 C5 131.08(19) . . . . ? O2 C3 C4 C5 -50.88(19) . . . . ? N2 C3 C4 C8 -113.4(2) . . . . ? O2 C3 C4 C8 64.62(18) . . . . ? N1 C4 C5 C6 -139.46(14) . . . . ? C3 C4 C5 C6 96.43(15) . . . . ? C8 C4 C5 C6 -22.56(17) . . . . ? C4 C5 C6 O3 159.84(12) . . . . ? C4 C5 C6 C7 38.26(16) . . . . ? O3 C6 C7 O4 -42.11(18) . . . . ? C5 C6 C7 O4 77.62(15) . . . . ? O3 C6 C7 C8 -158.29(14) . . . . ? C5 C6 C7 C8 -38.57(16) . . . . ? O4 C7 C8 C4 -93.42(16) . . . . ? C6 C7 C8 C4 24.53(17) . . . . ? N1 C4 C8 C7 114.25(16) . . . . ? C3 C4 C8 C7 -122.38(15) . . . . ? C5 C4 C8 C7 -1.50(18) . . . . ? N2 C2 C9 C11 -70.9(3) . . . . ? C1 C2 C9 C11 54.7(3) . . . . ? N2 C2 C9 C10 54.3(3) . . . . ? C1 C2 C9 C10 179.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.57 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.308 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.039 #=END data_13 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C16H28N2O4 _chemical_formula_sum 'C16 H28 N2 O4' _chemical_formula_weight 312.40 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 ? _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.7253(2) _cell_length_b 8.7384(2) _cell_length_c 10.9031(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.0130(10) _cell_angle_gamma 90.00 _cell_volume 876.03(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7818 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0565 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 24.71 _reflns_number_total 2953 _reflns_number_gt 2632 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; 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^)+(0.1200P)^2^+0.1400P] 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 -1.8(17) _refine_ls_number_reflns 2953 _refine_ls_number_parameters 311 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1777 _refine_ls_wR_factor_gt 0.1684 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.038 _refine_ls_shift/su_mean 0.007 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0645(3) -0.2587(3) 0.2113(2) 0.0340(6) Uani 1 1 d . . . O2 O -0.0124(3) 0.3506(3) 0.1938(2) 0.0303(6) Uani 1 1 d . . . O3 O 0.3787(3) 0.2338(3) 0.0008(2) 0.0323(6) Uani 1 1 d . . . O4 O 0.4374(2) 0.4039(3) 0.2353(2) 0.0302(6) Uani 1 1 d . . . N1 N 0.1649(3) -0.0233(3) 0.2122(3) 0.0272(7) Uani 1 1 d . . . N2 N -0.1081(3) 0.1145(3) 0.2051(3) 0.0270(6) Uani 1 1 d . . . C1 C 0.1525(4) 0.1447(4) 0.2142(3) 0.0245(7) Uani 1 1 d . . . C2 C 0.0574(4) -0.1030(4) 0.2129(3) 0.0260(7) Uani 1 1 d . . . C3 C -0.0895(3) -0.0519(3) 0.2153(3) 0.0253(7) Uani 1 1 d . . . H3A H -0.165(4) -0.099(5) 0.142(4) 0.026(9) Uiso 1 1 d . . . C4 C -0.0007(3) 0.1952(3) 0.2037(3) 0.0231(7) Uani 1 1 d . . . C5 C 0.1980(5) -0.3229(5) 0.2064(6) 0.0478(11) Uani 1 1 d . . . H5A H 0.190(5) -0.426(7) 0.204(5) 0.047(13) Uiso 1 1 d . . . H5B H 0.281(7) -0.289(7) 0.275(5) 0.070(17) Uiso 1 1 d . . . H5C H 0.220(9) -0.301(9) 0.131(8) 0.11(3) Uiso 1 1 d . . . C6 C -0.1203(4) -0.1131(4) 0.3384(3) 0.0307(8) Uani 1 1 d . . . H6A H -0.120(4) -0.221(6) 0.333(3) 0.031(10) Uiso 1 1 d . . . C7 C -0.0056(5) -0.0618(6) 0.4630(4) 0.0460(10) Uani 1 1 d . . . H7A H -0.034(5) -0.102(6) 0.541(5) 0.052(13) Uiso 1 1 d . . . H7B H -0.004(5) 0.054(6) 0.466(4) 0.044(12) Uiso 1 1 d . . . H7C H 0.098(5) -0.103(6) 0.467(4) 0.048(12) Uiso 1 1 d . . . C8 C -0.2721(5) -0.0689(5) 0.3362(5) 0.0423(10) Uani 1 1 d . . . H8A H -0.300(4) -0.113(5) 0.415(4) 0.038(11) Uiso 1 1 d . . . H8B H -0.344(5) -0.077(6) 0.256(5) 0.048(13) Uiso 1 1 d . . . H8C H -0.273(5) 0.043(7) 0.362(5) 0.055(14) Uiso 1 1 d . . . C9 C -0.1537(4) 0.4139(4) 0.1763(4) 0.0330(8) Uani 1 1 d . . . H9A H -0.138(4) 0.530(5) 0.180(3) 0.025(9) Uiso 1 1 d . . . H9B H -0.189(4) 0.378(5) 0.240(4) 0.027(9) Uiso 1 1 d . . . H9C H -0.226(4) 0.384(5) 0.092(4) 0.026(9) Uiso 1 1 d . . . C10 C 0.1945(3) 0.2097(4) 0.0993(3) 0.0243(7) Uani 1 1 d . . . H10A H 0.132(4) 0.178(5) 0.022(4) 0.029(9) Uiso 1 1 d . . . H10B H 0.182(4) 0.327(5) 0.095(4) 0.030(10) Uiso 1 1 d . . . C11 C 0.3526(4) 0.1745(4) 0.1133(3) 0.0261(7) Uani 1 1 d . . . H11A H 0.365(3) 0.057(4) 0.115(3) 0.013(8) Uiso 1 1 d . . . C12 C 0.4553(3) 0.2411(4) 0.2392(3) 0.0259(7) Uani 1 1 d . . . H12A H 0.564(4) 0.216(4) 0.251(3) 0.015(7) Uiso 1 1 d . . . C13 C 0.4194(4) 0.1696(4) 0.3535(3) 0.0287(7) Uani 1 1 d . . . H13A H 0.489(4) 0.216(4) 0.439(3) 0.025(9) Uiso 1 1 d . . . H13B H 0.432(4) 0.053(5) 0.347(4) 0.033(10) Uiso 1 1 d . . . C14 C 0.2614(4) 0.2043(4) 0.3439(3) 0.0274(7) Uani 1 1 d . . . H14A H 0.247(4) 0.316(5) 0.346(3) 0.025(9) Uiso 1 1 d . . . H14B H 0.234(5) 0.161(5) 0.415(4) 0.043(11) Uiso 1 1 d . . . C15 C 0.5002(5) 0.1634(6) -0.0222(4) 0.0399(9) Uani 1 1 d . . . H15A H 0.510(5) 0.216(5) -0.098(4) 0.044(11) Uiso 1 1 d . . . H15B H 0.476(5) 0.059(6) -0.043(4) 0.038(11) Uiso 1 1 d . . . H15C H 0.592(5) 0.163(5) 0.051(4) 0.037(10) Uiso 1 1 d . . . C16 C 0.5404(4) 0.4811(5) 0.3386(4) 0.0390(9) Uani 1 1 d . . . H16A H 0.538(5) 0.582(6) 0.320(4) 0.037(11) Uiso 1 1 d . . . H16B H 0.644(6) 0.446(6) 0.352(5) 0.050(13) Uiso 1 1 d . . . H16C H 0.525(5) 0.464(6) 0.415(5) 0.045(12) 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 O1 0.0301(12) 0.0216(12) 0.0497(14) -0.0003(11) 0.0122(11) 0.0009(10) O2 0.0306(12) 0.0188(12) 0.0443(14) 0.0030(10) 0.0161(11) 0.0047(9) O3 0.0327(13) 0.0374(14) 0.0298(11) 0.0016(10) 0.0142(10) 0.0035(10) O4 0.0274(12) 0.0270(13) 0.0320(12) 0.0014(10) 0.0041(9) -0.0037(10) N1 0.0275(15) 0.0217(14) 0.0321(15) -0.0020(11) 0.0093(11) 0.0025(12) N2 0.0278(15) 0.0233(14) 0.0289(13) 0.0029(11) 0.0080(11) 0.0012(12) C1 0.0284(17) 0.0177(16) 0.0271(15) 0.0011(12) 0.0088(13) -0.0008(12) C2 0.0286(17) 0.0168(16) 0.0295(17) -0.0024(12) 0.0052(13) 0.0031(13) C3 0.0246(16) 0.0193(16) 0.0285(17) 0.0008(12) 0.0039(14) -0.0017(13) C4 0.0284(17) 0.0174(16) 0.0233(15) 0.0014(11) 0.0081(13) 0.0016(13) C5 0.038(2) 0.019(2) 0.088(4) -0.003(2) 0.023(2) 0.0079(17) C6 0.0302(17) 0.0237(19) 0.0390(19) 0.0058(14) 0.0125(14) 0.0037(14) C7 0.044(2) 0.060(3) 0.033(2) 0.0047(18) 0.0120(18) -0.006(2) C8 0.037(2) 0.045(2) 0.049(2) 0.0123(19) 0.0202(19) 0.0041(18) C9 0.0337(19) 0.0215(19) 0.045(2) 0.0058(16) 0.0147(17) 0.0050(15) C10 0.0246(16) 0.0249(18) 0.0210(15) -0.0013(12) 0.0040(12) 0.0015(13) C11 0.0274(16) 0.0239(16) 0.0277(16) 0.0013(12) 0.0100(13) 0.0006(13) C12 0.0224(16) 0.0251(17) 0.0294(15) -0.0006(14) 0.0075(13) 0.0013(13) C13 0.0286(17) 0.0277(17) 0.0272(16) 0.0032(13) 0.0057(13) 0.0015(14) C14 0.0317(17) 0.0266(18) 0.0244(15) 0.0011(13) 0.0097(13) -0.0025(14) C15 0.0331(19) 0.049(2) 0.040(2) 0.0007(18) 0.0148(17) 0.0016(18) C16 0.038(2) 0.040(2) 0.037(2) -0.0088(17) 0.0096(16) -0.0033(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 O1 C2 1.362(4) . ? O1 C5 1.432(5) . ? O2 C4 1.364(4) . ? O2 C9 1.436(4) . ? O3 C11 1.428(4) . ? O3 C15 1.425(5) . ? O4 C16 1.411(5) . ? O4 C12 1.432(4) . ? N1 C2 1.259(4) . ? N1 C1 1.474(4) . ? N2 C4 1.264(4) . ? N2 C3 1.465(4) . ? C1 C4 1.522(4) . ? C1 C10 1.547(5) . ? C1 C14 1.555(4) . ? C2 C3 1.505(5) . ? C3 C6 1.561(5) . ? C3 H3A 0.98(4) . ? C5 H5A 0.91(6) . ? C5 H5B 0.95(6) . ? C5 H5C 0.93(8) . ? C6 C7 1.518(6) . ? C6 C8 1.519(5) . ? C6 H6A 0.95(5) . ? C7 H7A 1.04(5) . ? C7 H7B 1.01(5) . ? C7 H7C 1.06(5) . ? C8 H8A 1.05(4) . ? C8 H8B 0.93(5) . ? C8 H8C 1.02(6) . ? C9 H9A 1.03(4) . ? C9 H9B 0.92(4) . ? C9 H9C 0.99(4) . ? C10 C11 1.527(5) . ? C10 H10A 0.91(4) . ? C10 H10B 1.03(5) . ? C11 C12 1.526(4) . ? C11 H11A 1.03(4) . ? C12 C13 1.533(5) . ? C12 H12A 1.04(3) . ? C13 C14 1.537(5) . ? C13 H13A 1.04(4) . ? C13 H13B 1.04(5) . ? C14 H14A 0.98(4) . ? C14 H14B 0.97(5) . ? C15 H15A 0.98(5) . ? C15 H15B 0.95(5) . ? C15 H15C 0.98(4) . ? C16 H16A 0.90(5) . ? C16 H16B 1.01(5) . ? C16 H16C 0.91(5) . ? 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 C2 O1 C5 116.2(3) . . ? C4 O2 C9 116.4(3) . . ? C11 O3 C15 112.6(3) . . ? C16 O4 C12 113.7(3) . . ? C2 N1 C1 118.6(3) . . ? C4 N2 C3 118.2(3) . . ? N1 C1 C4 111.8(3) . . ? N1 C1 C10 108.0(3) . . ? C4 C1 C10 110.1(2) . . ? N1 C1 C14 108.2(3) . . ? C4 C1 C14 109.3(3) . . ? C10 C1 C14 109.4(3) . . ? N1 C2 O1 120.5(3) . . ? N1 C2 C3 129.1(3) . . ? O1 C2 C3 110.4(3) . . ? N2 C3 C2 112.8(3) . . ? N2 C3 C6 110.6(3) . . ? C2 C3 C6 111.3(3) . . ? N2 C3 H3A 108(2) . . ? C2 C3 H3A 109(2) . . ? C6 C3 H3A 104(2) . . ? N2 C4 O2 120.6(3) . . ? N2 C4 C1 129.0(3) . . ? O2 C4 C1 110.4(3) . . ? O1 C5 H5A 109(3) . . ? O1 C5 H5B 113(3) . . ? H5A C5 H5B 112(5) . . ? O1 C5 H5C 115(5) . . ? H5A C5 H5C 103(6) . . ? H5B C5 H5C 104(6) . . ? C7 C6 C8 111.5(3) . . ? C7 C6 C3 112.2(3) . . ? C8 C6 C3 110.9(3) . . ? C7 C6 H6A 110(2) . . ? C8 C6 H6A 106(2) . . ? C3 C6 H6A 106(2) . . ? C6 C7 H7A 109(3) . . ? C6 C7 H7B 109(3) . . ? H7A C7 H7B 108(4) . . ? C6 C7 H7C 110(2) . . ? H7A C7 H7C 111(4) . . ? H7B C7 H7C 110(4) . . ? C6 C8 H8A 114(2) . . ? C6 C8 H8B 115(3) . . ? H8A C8 H8B 115(4) . . ? C6 C8 H8C 110(3) . . ? H8A C8 H8C 95(4) . . ? H8B C8 H8C 105(4) . . ? O2 C9 H9A 105(2) . . ? O2 C9 H9B 110(2) . . ? H9A C9 H9B 113(3) . . ? O2 C9 H9C 112(2) . . ? H9A C9 H9C 111(3) . . ? H9B C9 H9C 106(3) . . ? C11 C10 C1 111.6(3) . . ? C11 C10 H10A 112(2) . . ? C1 C10 H10A 112(2) . . ? C11 C10 H10B 108(2) . . ? C1 C10 H10B 110(2) . . ? H10A C10 H10B 104(3) . . ? O3 C11 C12 112.8(3) . . ? O3 C11 C10 107.2(3) . . ? C12 C11 C10 110.9(3) . . ? O3 C11 H11A 109.1(18) . . ? C12 C11 H11A 108.7(18) . . ? C10 C11 H11A 108.0(18) . . ? O4 C12 C11 108.3(3) . . ? O4 C12 C13 111.8(3) . . ? C11 C12 C13 108.7(3) . . ? O4 C12 H12A 108.8(19) . . ? C11 C12 H12A 111.8(18) . . ? C13 C12 H12A 107.5(17) . . ? C12 C13 C14 110.6(3) . . ? C12 C13 H13A 108(2) . . ? C14 C13 H13A 109(2) . . ? C12 C13 H13B 106(2) . . ? C14 C13 H13B 109(2) . . ? H13A C13 H13B 113(3) . . ? C13 C14 C1 111.4(3) . . ? C13 C14 H14A 110(2) . . ? C1 C14 H14A 107(2) . . ? C13 C14 H14B 113(2) . . ? C1 C14 H14B 108(3) . . ? H14A C14 H14B 107(3) . . ? O3 C15 H15A 105(3) . . ? O3 C15 H15B 107(3) . . ? H15A C15 H15B 110(4) . . ? O3 C15 H15C 117(2) . . ? H15A C15 H15C 112(4) . . ? H15B C15 H15C 106(4) . . ? O4 C16 H16A 109(3) . . ? O4 C16 H16B 113(3) . . ? H16A C16 H16B 106(4) . . ? O4 C16 H16C 112(3) . . ? H16A C16 H16C 112(4) . . ? H16B C16 H16C 106(4) . . ? 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 C2 N1 C1 C4 -5.4(4) . . . . ? C2 N1 C1 C10 -126.7(3) . . . . ? C2 N1 C1 C14 114.9(3) . . . . ? C1 N1 C2 O1 -179.9(3) . . . . ? C1 N1 C2 C3 0.1(5) . . . . ? C5 O1 C2 N1 -1.2(5) . . . . ? C5 O1 C2 C3 178.8(3) . . . . ? C4 N2 C3 C2 -4.2(4) . . . . ? C4 N2 C3 C6 121.1(3) . . . . ? N1 C2 C3 N2 5.3(5) . . . . ? O1 C2 C3 N2 -174.8(3) . . . . ? N1 C2 C3 C6 -119.7(4) . . . . ? O1 C2 C3 C6 60.3(3) . . . . ? C3 N2 C4 O2 179.7(3) . . . . ? C3 N2 C4 C1 -1.5(5) . . . . ? C9 O2 C4 N2 -4.1(4) . . . . ? C9 O2 C4 C1 176.8(3) . . . . ? N1 C1 C4 N2 6.6(4) . . . . ? C10 C1 C4 N2 126.7(3) . . . . ? C14 C1 C4 N2 -113.1(3) . . . . ? N1 C1 C4 O2 -174.4(3) . . . . ? C10 C1 C4 O2 -54.4(3) . . . . ? C14 C1 C4 O2 65.9(3) . . . . ? N2 C3 C6 C7 -68.2(4) . . . . ? C2 C3 C6 C7 57.9(4) . . . . ? N2 C3 C6 C8 57.2(4) . . . . ? C2 C3 C6 C8 -176.7(3) . . . . ? N1 C1 C10 C11 -63.2(3) . . . . ? C4 C1 C10 C11 174.5(3) . . . . ? C14 C1 C10 C11 54.3(4) . . . . ? C15 O3 C11 C12 79.0(4) . . . . ? C15 O3 C11 C10 -158.7(3) . . . . ? C1 C10 C11 O3 177.8(2) . . . . ? C1 C10 C11 C12 -58.7(4) . . . . ? C16 O4 C12 C11 -171.8(3) . . . . ? C16 O4 C12 C13 68.4(4) . . . . ? O3 C11 C12 O4 58.8(3) . . . . ? C10 C11 C12 O4 -61.4(3) . . . . ? O3 C11 C12 C13 -179.5(3) . . . . ? C10 C11 C12 C13 60.2(3) . . . . ? O4 C12 C13 C14 59.7(4) . . . . ? C11 C12 C13 C14 -59.8(4) . . . . ? C12 C13 C14 C1 57.8(4) . . . . ? N1 C1 C14 C13 63.5(3) . . . . ? C4 C1 C14 C13 -174.6(3) . . . . ? C10 C1 C14 C13 -54.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.244 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.045