# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 188/282 data_global _audit_creation_method 'SHELXL and manual editing' # SUBMISSION DETAILS _publ_contact_author ; Prof. J. D. Wallis ; _publ_contact_author_email john.wallis@ntu.ac.uk _publ_contact_author_fax 0115-948-6636 _publ_contact_author_phone 0115-848-3149 _publ_requested_journal 'Perkin Trans 2' _publ_section_title ; Attractive and Repulsive Effects in the Interactions Between Electron Rich and Electron Deficient Groups in Peri-Substituted Naphthalenes ; loop_ _publ_author_name _publ_author_address 'Paul C. Bell' ; Department of Chemistry and Physics Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; 'Jane O'Leary' ; Department of Chemistry and Physics Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; 'John D. Wallis' ; Department of Chemistry and Physics Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; data_X27079 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-(8'-Methoxynaphthyl-1'-methylidene)-1,3-dioxan-4,6-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 O5' _chemical_formula_weight 312.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 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' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc 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' _cell_length_a 10.291(2) _cell_length_b 11.607(3) _cell_length_c 12.988(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.42 _cell_angle_gamma 90.00 _cell_volume 1495.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 14 _cell_measurement_theta_min 19.8 _cell_measurement_theta_max 25.9 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method ? _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.842 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8171 _exptl_absorpt_correction_T_max 0.8841 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method \o/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 10000s _diffrn_standards_decay_% .7 _diffrn_reflns_number 1340 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 5.87 _diffrn_reflns_theta_max 66.97 _reflns_number_total 1340 _reflns_number_gt 1317 _reflns_threshold_expression >3sigma(I) _computing_data_collection CAD4 _computing_cell_refinement CAD4 _computing_data_reduction 'MolEN (Enraf-Nonius, 1990)' _computing_structure_solution 'SIR97 (Altomare, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTO, ORTEP (Johnson, 1976)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ > 3sigma(F^2^). 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^. 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^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refU _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(15) _refine_ls_number_reflns 1317 _refine_ls_number_parameters 273 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0274 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0780 _refine_ls_goodness_of_fit_ref 0.819 _refine_ls_restrained_S_all 0.837 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.003 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 O19 O 0.50191(14) -0.25254(12) 0.15373(12) 0.0168(3) Uani 1 1 d . . . O20 O 0.47724(13) -0.12561(13) 0.00810(11) 0.0162(3) Uani 1 1 d . . . O21 O 0.61092(14) -0.19751(12) 0.31659(12) 0.0184(3) Uani 1 1 d . . . O22 O 0.56349(15) 0.04963(12) 0.03241(12) 0.0191(3) Uani 1 1 d . . . O23 O 0.75998(14) 0.13382(13) 0.35214(12) 0.0198(3) Uani 1 1 d . . . C1 C 0.49819(19) 0.15765(17) 0.22401(16) 0.0145(4) Uani 1 1 d . . . C2 C 0.37019(19) 0.17501(19) 0.15712(17) 0.0186(4) Uani 1 1 d . . . C3 C 0.3215(2) 0.28706(19) 0.12814(17) 0.0201(4) Uani 1 1 d . . . C4 C 0.3994(2) 0.38070(19) 0.16467(18) 0.0197(4) Uani 1 1 d . . . C5 C 0.6163(2) 0.46511(17) 0.26480(17) 0.0197(5) Uani 1 1 d . . . C6 C 0.7451(2) 0.45083(18) 0.32837(18) 0.0209(5) Uani 1 1 d . . . C7 C 0.7973(2) 0.33965(19) 0.35949(17) 0.0182(4) Uani 1 1 d . . . C8 C 0.7172(2) 0.24423(17) 0.32728(17) 0.0161(4) Uani 1 1 d . . . C9 C 0.5821(2) 0.25479(17) 0.26255(17) 0.0145(4) Uani 1 1 d . . . C10 C 0.5322(2) 0.36801(18) 0.23157(16) 0.0167(4) Uani 1 1 d . . . C11 C 0.53817(18) 0.03758(17) 0.25586(16) 0.0142(4) Uani 1 1 d . . . C12 C 0.53629(19) -0.04895(16) 0.18678(17) 0.0147(4) Uani 1 1 d . . . C13 C 0.55417(19) -0.16932(17) 0.22719(16) 0.0139(4) Uani 1 1 d . . . C14 C 0.41557(19) -0.21902(16) 0.05078(16) 0.0160(4) Uani 1 1 d . . . C15 C 0.52519(18) -0.03276(16) 0.07149(16) 0.0147(4) Uani 1 1 d . . . C16 C 0.4156(2) -0.31964(19) -0.02210(18) 0.0216(5) Uani 1 1 d . . . C17 C 0.2765(2) -0.18562(19) 0.06000(17) 0.0204(4) Uani 1 1 d . . . C18 C 0.9029(2) 0.1154(2) 0.38721(19) 0.0221(4) Uani 1 1 d . . . H1 H 0.315(4) 0.104(3) 0.134(3) 0.042(9) Uiso 1 1 d . . . H2 H 0.235(4) 0.297(3) 0.072(3) 0.049(10) Uiso 1 1 d . . . H3 H 0.366(3) 0.454(3) 0.148(3) 0.035(8) Uiso 1 1 d . . . H4 H 0.584(3) 0.540(2) 0.242(2) 0.017(6) Uiso 1 1 d . . . H5 H 0.800(3) 0.520(3) 0.352(2) 0.025(7) Uiso 1 1 d . . . H6 H 0.884(3) 0.334(2) 0.404(2) 0.023(7) Uiso 1 1 d . . . H7 H 0.550(2) 0.014(2) 0.331(2) 0.017(6) Uiso 1 1 d . . . H8 H 0.366(3) -0.301(3) -0.092(3) 0.029(7) Uiso 1 1 d . . . H9 H 0.507(3) -0.340(3) -0.024(3) 0.028(7) Uiso 1 1 d . . . H10 H 0.369(3) -0.385(3) 0.000(3) 0.033(8) Uiso 1 1 d . . . H11 H 0.223(4) -0.166(3) -0.003(3) 0.037(8) Uiso 1 1 d . . . H12 H 0.234(3) -0.256(2) 0.085(2) 0.020(6) Uiso 1 1 d . . . H13 H 0.274(3) -0.124(3) 0.114(2) 0.026(7) Uiso 1 1 d . . . H14 H 0.904(4) 0.032(4) 0.381(4) 0.060(11) Uiso 1 1 d . . . H15 H 0.963(3) 0.154(3) 0.346(2) 0.029(7) Uiso 1 1 d . . . H16 H 0.948(4) 0.137(3) 0.466(3) 0.046(9) 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 O19 0.0203(7) 0.0114(6) 0.0155(7) 0.0002(5) -0.0009(5) -0.0004(5) O20 0.0172(7) 0.0158(6) 0.0148(6) -0.0001(5) 0.0028(5) 0.0005(5) O21 0.0203(7) 0.0177(7) 0.0146(7) 0.0029(5) 0.0002(5) -0.0001(6) O22 0.0237(7) 0.0147(7) 0.0195(7) 0.0048(5) 0.0065(6) 0.0008(5) O23 0.0169(7) 0.0139(7) 0.0251(7) 0.0032(6) -0.0006(6) 0.0007(5) C1 0.0155(9) 0.0138(10) 0.0144(10) 0.0001(7) 0.0043(7) 0.0005(7) C2 0.0174(10) 0.0180(10) 0.0201(10) -0.0015(8) 0.0047(8) 0.0006(8) C3 0.0146(9) 0.0238(11) 0.0216(10) 0.0018(9) 0.0045(8) 0.0055(8) C4 0.0210(10) 0.0181(11) 0.0215(10) 0.0044(9) 0.0081(8) 0.0083(8) C5 0.0276(11) 0.0114(10) 0.0236(11) -0.0010(8) 0.0130(9) 0.0002(8) C6 0.0264(11) 0.0151(10) 0.0245(11) -0.0065(8) 0.0124(9) -0.0056(8) C7 0.0197(10) 0.0175(10) 0.0174(10) -0.0038(8) 0.0049(8) -0.0031(8) C8 0.0204(10) 0.0134(9) 0.0151(9) 0.0009(7) 0.0058(7) 0.0010(7) C9 0.0184(9) 0.0123(10) 0.0144(9) 0.0005(7) 0.0071(7) -0.0002(7) C10 0.0209(10) 0.0150(10) 0.0174(10) -0.0018(8) 0.0107(8) 0.0015(8) C11 0.0123(9) 0.0134(9) 0.0159(10) -0.0011(7) 0.0019(7) -0.0021(6) C12 0.0122(8) 0.0133(9) 0.0170(9) 0.0024(7) 0.0012(7) -0.0012(6) C13 0.0130(8) 0.0129(9) 0.0159(10) -0.0008(7) 0.0036(7) -0.0015(7) C14 0.0164(9) 0.0160(9) 0.0137(9) -0.0003(8) 0.0009(7) -0.0018(7) C15 0.0125(8) 0.0133(9) 0.0181(9) 0.0004(7) 0.0036(7) 0.0020(7) C16 0.0259(11) 0.0173(10) 0.0200(11) -0.0042(8) 0.0029(8) -0.0013(8) C17 0.0166(10) 0.0232(11) 0.0204(11) -0.0030(9) 0.0030(8) -0.0026(8) C18 0.0184(10) 0.0222(11) 0.0256(11) 0.0056(9) 0.0059(8) 0.0053(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 O19 C13 1.364(2) . ? O19 C14 1.448(2) . ? O20 C15 1.366(2) . ? O20 C14 1.440(3) . ? O21 C13 1.198(3) . ? O22 C15 1.197(2) . ? O23 C8 1.366(2) . ? O23 C18 1.435(3) . ? C1 C2 1.386(3) . ? C1 C9 1.428(3) . ? C1 C11 1.481(3) . ? C2 C3 1.409(3) . ? C3 C4 1.359(3) . ? C4 C10 1.418(3) . ? C5 C6 1.372(3) . ? C5 C10 1.417(3) . ? C6 C7 1.415(3) . ? C7 C8 1.378(3) . ? C8 C9 1.425(3) . ? C9 C10 1.429(3) . ? C11 C12 1.343(3) . ? C12 C15 1.483(3) . ? C12 C13 1.487(3) . ? C14 C16 1.503(3) . ? C14 C17 1.518(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 C13 O19 C14 119.12(14) . . ? C15 O20 C14 119.18(16) . . ? C8 O23 C18 116.98(16) . . ? C2 C1 C9 119.38(19) . . ? C2 C1 C11 117.33(18) . . ? C9 C1 C11 123.23(17) . . ? C1 C2 C3 120.86(19) . . ? C4 C3 C2 120.66(18) . . ? C3 C4 C10 120.91(19) . . ? C6 C5 C10 120.09(19) . . ? C5 C6 C7 120.97(19) . . ? C8 C7 C6 119.7(2) . . ? O23 C8 C7 123.59(19) . . ? O23 C8 C9 115.01(17) . . ? C7 C8 C9 121.39(18) . . ? C8 C9 C1 122.90(18) . . ? C8 C9 C10 117.79(18) . . ? C1 C9 C10 119.24(18) . . ? C5 C10 C4 121.0(2) . . ? C5 C10 C9 120.05(18) . . ? C4 C10 C9 118.92(19) . . ? C12 C11 C1 124.30(18) . . ? C11 C12 C15 124.27(17) . . ? C11 C12 C13 119.24(18) . . ? C15 C12 C13 116.39(17) . . ? O21 C13 O19 118.98(18) . . ? O21 C13 C12 125.55(19) . . ? O19 C13 C12 115.47(17) . . ? O20 C14 O19 109.44(15) . . ? O20 C14 C16 105.59(17) . . ? O19 C14 C16 105.66(16) . . ? O20 C14 C17 111.07(17) . . ? O19 C14 C17 110.83(17) . . ? C16 C14 C17 113.96(17) . . ? O22 C15 O20 118.77(18) . . ? O22 C15 C12 125.70(18) . . ? O20 C15 C12 115.28(16) . . ? 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 C9 C1 C2 C3 -0.9(3) . . . . ? C11 C1 C2 C3 176.26(18) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C3 C4 C10 0.9(3) . . . . ? C10 C5 C6 C7 1.7(3) . . . . ? C5 C6 C7 C8 -1.2(3) . . . . ? C18 O23 C8 C7 -17.6(3) . . . . ? C18 O23 C8 C9 161.15(18) . . . . ? C6 C7 C8 O23 178.90(18) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? O23 C8 C9 C1 -1.5(3) . . . . ? C7 C8 C9 C1 177.31(19) . . . . ? O23 C8 C9 C10 -178.56(17) . . . . ? C7 C8 C9 C10 0.2(3) . . . . ? C2 C1 C9 C8 -176.86(18) . . . . ? C11 C1 C9 C8 6.1(3) . . . . ? C2 C1 C9 C10 0.2(3) . . . . ? C11 C1 C9 C10 -176.84(17) . . . . ? C6 C5 C10 C4 -179.14(19) . . . . ? C6 C5 C10 C9 -1.2(3) . . . . ? C3 C4 C10 C5 176.39(19) . . . . ? C3 C4 C10 C9 -1.6(3) . . . . ? C8 C9 C10 C5 0.2(3) . . . . ? C1 C9 C10 C5 -176.96(19) . . . . ? C8 C9 C10 C4 178.24(17) . . . . ? C1 C9 C10 C4 1.0(3) . . . . ? C2 C1 C11 C12 55.9(3) . . . . ? C9 C1 C11 C12 -127.0(2) . . . . ? C1 C11 C12 C15 14.9(3) . . . . ? C1 C11 C12 C13 -168.81(18) . . . . ? C14 O19 C13 O21 170.47(18) . . . . ? C14 O19 C13 C12 -10.4(2) . . . . ? C11 C12 C13 O21 -24.9(3) . . . . ? C15 C12 C13 O21 151.65(19) . . . . ? C11 C12 C13 O19 156.01(17) . . . . ? C15 C12 C13 O19 -27.4(3) . . . . ? C15 O20 C14 O19 -48.9(2) . . . . ? C15 O20 C14 C16 -162.19(16) . . . . ? C15 O20 C14 C17 73.8(2) . . . . ? C13 O19 C14 O20 47.3(2) . . . . ? C13 O19 C14 C16 160.59(17) . . . . ? C13 O19 C14 C17 -75.5(2) . . . . ? C14 O20 C15 O22 -172.33(17) . . . . ? C14 O20 C15 C12 13.1(2) . . . . ? C11 C12 C15 O22 28.4(3) . . . . ? C13 C12 C15 O22 -148.01(19) . . . . ? C11 C12 C15 O20 -157.52(18) . . . . ? C13 C12 C15 O20 26.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 66.97 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.175 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.041 #===END data_bob _audit_creation_method SHELXL _chemical_name_systematic ; 1,1-dicyano-2-(8'-methoxynaphth-1'-yl)ethene ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H10 N2 O' _chemical_formula_weight 234.25 _chemical_melting_point ? _chemical_compound_source ? 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 P21/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 6.5046(3) _cell_length_b 17.5411(7) _cell_length_c 10.3306(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.499(2) _cell_angle_gamma 90.00 _cell_volume 1162.54(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2612 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.49 _exptl_crystal_description 'thick plate' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method ? _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995). ; _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9104 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2612 _reflns_number_observed 2046 _reflns_observed_criterion >2sigma(I) _computing_data_collection ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_cell_refinement ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_data_reduction ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 171 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[s^2^(Fo^2^)+( 0.0693P)^2^+0.1014P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2441 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_obs 0.0440 _refine_ls_wR_factor_all 0.1248 _refine_ls_wR_factor_obs 0.1135 _refine_ls_goodness_of_fit_all 1.058 _refine_ls_goodness_of_fit_obs 1.114 _refine_ls_restrained_S_all 1.073 _refine_ls_restrained_S_obs 1.114 _refine_ls_shift/esd_max 0.077 _refine_ls_shift/esd_mean 0.009 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.44390(12) 0.32353(5) 0.19459(8) 0.0320(2) Uani 1 d . . N1 N 0.4655(2) 0.43189(7) 0.65951(11) 0.0429(3) Uani 1 d . . N2 N -0.1585(2) 0.35642(10) 0.50022(12) 0.0627(4) Uani 1 d . . C1 C 0.3048(2) 0.32990(7) 0.08098(11) 0.0280(3) Uani 1 d . . C2 C 0.3289(2) 0.29609(8) -0.03532(13) 0.0359(3) Uani 1 d . . C3 C 0.1773(2) 0.30627(8) -0.14791(13) 0.0389(3) Uani 1 d . . C4 C 0.0034(2) 0.34831(8) -0.14342(12) 0.0350(3) Uani 1 d . . C5 C -0.2116(2) 0.42551(8) -0.01894(12) 0.0339(3) Uani 1 d . . C6 C -0.2444(2) 0.45907(8) 0.09501(12) 0.0361(3) Uani 1 d . . C7 C -0.0944(2) 0.45216(7) 0.20815(12) 0.0317(3) Uani 1 d . . C8 C 0.0878(2) 0.41177(7) 0.20880(11) 0.0265(3) Uani 1 d . . C9 C 0.1250(2) 0.37526(6) 0.09041(11) 0.0252(3) Uani 1 d . . C10 C -0.0281(2) 0.38293(7) -0.02412(11) 0.0287(3) Uani 1 d . . C11 C 0.2414(2) 0.41426(7) 0.32958(11) 0.0277(3) Uani 1 d . . C12 C 0.1959(2) 0.40458(7) 0.45111(11) 0.0299(3) Uani 1 d . . C13 C 0.3486(2) 0.41904(8) 0.56586(12) 0.0327(3) Uani 1 d . . C14 C -0.0033(2) 0.37827(8) 0.47666(12) 0.0399(3) Uani 1 d . . C15 C 0.6188(2) 0.27369(8) 0.1949(2) 0.0378(3) Uani 1 d . . H2 H 0.4517(25) 0.2659(9) -0.0387(16) 0.053(4) Uiso 1 d . . H3 H 0.1960(24) 0.2817(10) -0.2278(16) 0.051(4) Uiso 1 d . . H4 H -0.1032(22) 0.3563(8) -0.2204(15) 0.039(4) Uiso 1 d . . H5 H -0.3175(24) 0.4302(9) -0.0994(16) 0.045(4) Uiso 1 d . . H6 H -0.3680(26) 0.4896(9) 0.1040(16) 0.052(4) Uiso 1 d . . H7 H -0.1114(22) 0.4796(9) 0.2909(15) 0.044(4) Uiso 1 d . . H11 H 0.3825(22) 0.4272(8) 0.3249(13) 0.033(3) Uiso 1 d . . H15A H 0.5679(26) 0.2192(10) 0.1720(16) 0.055(4) Uiso 1 d . . H15B H 0.7101(25) 0.2939(9) 0.1346(15) 0.046(4) Uiso 1 d . . H15C H 0.7008(24) 0.2763(9) 0.2878(17) 0.048(4) Uiso 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 0.0262(4) 0.0379(5) 0.0314(5) -0.0020(4) 0.0032(4) 0.0046(4) N1 0.0473(7) 0.0458(7) 0.0323(6) -0.0039(5) -0.0030(5) 0.0011(5) N2 0.0503(8) 0.1026(12) 0.0376(7) 0.0001(7) 0.0143(6) -0.0156(8) C1 0.0271(6) 0.0299(7) 0.0279(6) -0.0008(5) 0.0068(5) -0.0059(5) C2 0.0363(7) 0.0387(8) 0.0354(7) -0.0061(6) 0.0138(6) -0.0025(6) C3 0.0474(8) 0.0425(8) 0.0288(7) -0.0100(6) 0.0122(6) -0.0094(6) C4 0.0410(7) 0.0403(8) 0.0229(6) -0.0022(5) 0.0031(5) -0.0116(6) C5 0.0333(6) 0.0379(8) 0.0283(6) 0.0048(5) -0.0012(5) -0.0021(5) C6 0.0337(6) 0.0383(8) 0.0347(7) 0.0039(6) 0.0015(5) 0.0078(6) C7 0.0350(6) 0.0330(7) 0.0275(6) 0.0001(5) 0.0061(5) 0.0052(5) C8 0.0290(6) 0.0272(6) 0.0231(6) 0.0017(5) 0.0040(5) -0.0021(5) C9 0.0276(6) 0.0253(6) 0.0235(6) 0.0003(5) 0.0064(5) -0.0058(5) C10 0.0309(6) 0.0307(7) 0.0241(6) 0.0017(5) 0.0036(5) -0.0073(5) C11 0.0295(6) 0.0261(6) 0.0269(6) -0.0023(5) 0.0030(5) 0.0015(5) C12 0.0329(6) 0.0322(7) 0.0235(6) -0.0033(5) 0.0013(5) 0.0018(5) C13 0.0367(6) 0.0336(7) 0.0270(6) -0.0023(5) 0.0029(5) 0.0034(5) C14 0.0411(7) 0.0565(9) 0.0221(6) -0.0023(6) 0.0051(5) -0.0015(7) C15 0.0290(6) 0.0358(8) 0.0492(8) -0.0014(6) 0.0079(6) 0.0041(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 O1 C1 1.3632(14) . ? O1 C15 1.4345(15) . ? O1 C11 2.6112(14) . ? N1 C13 1.150(2) . ? N2 C14 1.143(2) . ? C1 C2 1.372(2) . ? C1 C9 1.431(2) . ? C2 C3 1.407(2) . ? C3 C4 1.358(2) . ? C4 C10 1.419(2) . ? C5 C6 1.364(2) . ? C5 C10 1.417(2) . ? C6 C7 1.399(2) . ? C7 C8 1.379(2) . ? C8 C9 1.436(2) . ? C8 C11 1.465(2) . ? C9 C10 1.422(2) . ? C11 C12 1.347(2) . ? C12 C13 1.438(2) . ? C12 C14 1.440(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 O1 C15 117.72(10) . . ? C1 O1 C11 95.06(7) . . ? C15 O1 C11 147.16(8) . . ? O1 C1 C2 124.26(11) . . ? O1 C1 C9 114.88(9) . . ? C2 C1 C9 120.87(11) . . ? C1 C2 C3 120.21(12) . . ? C4 C3 C2 121.01(12) . . ? C3 C4 C10 120.18(12) . . ? C6 C5 C10 120.85(12) . . ? C5 C6 C7 119.79(12) . . ? C8 C7 C6 121.92(11) . . ? C7 C8 C9 119.36(11) . . ? C7 C8 C11 116.97(10) . . ? C9 C8 C11 123.46(10) . . ? C10 C9 C1 117.65(10) . . ? C10 C9 C8 118.23(10) . . ? C1 C9 C8 124.10(10) . . ? C5 C10 C4 120.11(11) . . ? C5 C10 C9 119.83(11) . . ? C4 C10 C9 120.05(11) . . ? C12 C11 C8 124.45(11) . . ? C12 C11 O1 128.95(9) . . ? C8 C11 O1 81.97(7) . . ? C11 C12 C13 121.18(11) . . ? C11 C12 C14 123.64(11) . . ? C13 C12 C14 115.17(10) . . ? N1 C13 C12 177.66(13) . . ? N2 C14 C12 178.01(15) . . ? _refine_diff_density_max 0.197 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.042