Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_global _publ_contact_author 'Masakatsu Sugahara' _publ_contact_author_address ; Masakatsu Sugahara DISCOVERY RESEARCH LABORATORY TANABE SEIYAKU CO., LTD. 16-89,KASHIMA 3-CHOME, YODOGAWA-KU, OSAKA, 532-8505 JAPAN ; _publ_contact_author_phone '81-6-6300-2578' _publ_contact_author_fax '81-6-6300-2564' _publ_contact_author_email 'm-suga @tanabe.co.jp' _publ_requested_journal 'Perkin Transactions 1' _journal_coden_Cambridge 207 _publ_requested_coeditor_name ? _publ_contact_letter ; Author Masakatsu Sugahara, Yasunori Moritani, Tooru Kuroda, Kazuhiko Kondo and Tatsuzo Ukita ; loop_ _publ_author_name 'Masakatsu Sugahara' 'Yasunori Moritani' 'Tooru Kuroda' 'Kazuhiko Kondo' 'Tatsuzo Ukita' data_compound1 _database_code_CSD 156919 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-Epoxynaphthalene-2,3-dicarboxylic acid, 1-(4-pyridyl)- 1,2,3,4-tetrahydro-6,7-dimethoxy-, dimethyl ester, (1beta, 2beta , 3beta , 4beta)-rel- (9CI) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 N O7' _chemical_formula_weight 399.39 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' '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 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 9.159(2) _cell_length_b 16.895(1) _cell_length_c 13.252(1) _cell_angle_alpha 90.00 _cell_angle_beta 109.87(1) _cell_angle_gamma 90.00 _cell_volume 1928.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 35 _cell_measurement_theta_max 45 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.872 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'nomal-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5R diffractometer' _diffrn_measurement_method ot _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3515 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0138 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.41 _diffrn_reflns_theta_max 65.08 _reflns_number_total 3296 _reflns_number_gt 2914 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku/MSC AFC5R software 1992' _computing_cell_refinement 'Rigaku/MSC AFC5R software 1992' _computing_data_reduction 'Rigaku/MSC AFC5R software 1992' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3296 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1786 _refine_ls_wR_factor_gt 0.1726 _refine_ls_goodness_of_fit_ref 1.450 _refine_ls_restrained_S_all 1.450 _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 O11 O 0.37267(15) 0.23412(7) 0.66595(11) 0.0437(4) Uani 1 1 d . . . O13 O 0.6412(2) 0.35990(9) 0.69864(16) 0.0687(5) Uani 1 1 d . . . O14 O 0.84551(17) 0.28195(10) 0.77219(16) 0.0667(5) Uani 1 1 d . . . O17 O 0.6358(2) 0.23225(11) 0.90295(14) 0.0710(5) Uani 1 1 d . . . O18 O 0.78849(18) 0.12902(10) 0.90462(12) 0.0598(4) Uani 1 1 d . . . O26 O 0.23634(18) -0.06810(8) 0.43814(13) 0.0556(4) Uani 1 1 d . . . O28 O 0.28008(19) 0.02898(8) 0.29153(12) 0.0558(4) Uani 1 1 d . . . N23 N 0.1981(3) 0.07959(15) 0.92872(17) 0.0703(6) Uani 1 1 d . . . C1 C 0.4501(2) 0.23486(11) 0.58763(16) 0.0438(5) Uani 1 1 d . . . C2 C 0.6198(2) 0.21980(11) 0.66023(16) 0.0433(5) Uani 1 1 d . . . C3 C 0.5976(2) 0.15713(11) 0.74076(16) 0.0410(4) Uani 1 1 d . . . C4 C 0.4144(2) 0.15441(11) 0.70403(15) 0.0399(5) Uani 1 1 d . . . C5 C 0.3647(2) 0.10863(11) 0.59895(15) 0.0408(4) Uani 1 1 d . . . C6 C 0.3147(2) 0.03172(11) 0.57210(16) 0.0415(4) Uani 1 1 d . . . C7 C 0.2856(2) 0.00813(11) 0.46726(16) 0.0422(5) Uani 1 1 d . . . C8 C 0.3125(2) 0.05948(12) 0.39158(15) 0.0428(5) Uani 1 1 d . . . C9 C 0.3680(2) 0.13604(11) 0.42106(16) 0.0438(5) Uani 1 1 d . . . C10 C 0.3894(2) 0.15987(11) 0.52486(15) 0.0414(4) Uani 1 1 d . . . C12 C 0.6988(2) 0.29558(12) 0.71183(18) 0.0496(5) Uani 1 1 d . . . C15 C 0.9289(4) 0.34977(19) 0.8315(3) 0.0986(12) Uani 1 1 d . . . C16 C 0.6727(2) 0.17885(12) 0.85769(17) 0.0468(5) Uani 1 1 d . . . C19 C 0.8765(3) 0.1436(2) 1.0152(2) 0.0821(9) Uani 1 1 d . . . C20 C 0.3421(2) 0.13004(11) 0.78474(15) 0.0420(5) Uani 1 1 d . . . C21 C 0.3864(3) 0.06048(15) 0.8422(2) 0.0597(6) Uani 1 1 d . . . C22 C 0.3118(3) 0.03887(16) 0.9130(2) 0.0692(7) Uani 1 1 d . . . C24 C 0.1579(3) 0.14533(17) 0.8734(2) 0.0677(7) Uani 1 1 d . . . C25 C 0.2244(2) 0.17302(13) 0.80136(18) 0.0523(5) Uani 1 1 d . . . C27 C 0.0825(4) -0.07712(18) 0.3775(3) 0.0868(9) Uani 1 1 d . . . C29 C 0.2881(3) 0.07937(15) 0.2089(2) 0.0662(7) Uani 1 1 d . . . H30 H 0.4361 0.2816 0.5458 0.052 Uiso 1 1 d . . . H31 H 0.6758 0.1968 0.6191 0.051 Uiso 1 1 d . . . H32 H 0.6354 0.1074 0.7280 0.049 Uiso 1 1 d . . . H33 H 0.3011 -0.0037 0.6240 0.050 Uiso 1 1 d . . . H34 H 0.3901 0.1707 0.3719 0.052 Uiso 1 1 d . . . H35 H 0.9267 0.3915 0.7830 0.117 Uiso 1 1 d . . . H36 H 1.0337 0.3352 0.8692 0.117 Uiso 1 1 d . . . H37 H 0.8814 0.3667 0.8812 0.117 Uiso 1 1 d . . . H38 H 0.9257 0.1937 1.0219 0.098 Uiso 1 1 d . . . H39 H 0.9530 0.1035 1.0407 0.098 Uiso 1 1 d . . . H40 H 0.8092 0.1431 1.0561 0.098 Uiso 1 1 d . . . H41 H 0.4674 0.0290 0.8335 0.071 Uiso 1 1 d . . . H42 H 0.3448 -0.0091 0.9518 0.082 Uiso 1 1 d . . . H43 H 0.0768 0.1761 0.8829 0.084 Uiso 1 1 d . . . H44 H 0.1895 0.2206 0.7628 0.064 Uiso 1 1 d . . . H45 H 0.0631 -0.0541 0.3090 0.103 Uiso 1 1 d . . . H46 H 0.0574 -0.1319 0.3696 0.103 Uiso 1 1 d . . . H47 H 0.0201 -0.0517 0.4125 0.103 Uiso 1 1 d . . . H48 H 0.2254 0.1247 0.2055 0.079 Uiso 1 1 d . . . H49 H 0.2515 0.0520 0.1423 0.079 Uiso 1 1 d . . . H50 H 0.3926 0.0953 0.2229 0.079 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 O11 0.0430(7) 0.0345(7) 0.0545(8) -0.0012(5) 0.0176(6) 0.0016(5) O13 0.0613(10) 0.0383(9) 0.1011(14) -0.0098(8) 0.0204(9) -0.0063(7) O14 0.0425(8) 0.0543(9) 0.0933(13) -0.0121(8) 0.0101(8) -0.0095(7) O17 0.0669(10) 0.0759(12) 0.0655(10) -0.0303(9) 0.0162(8) 0.0070(8) O18 0.0554(9) 0.0728(11) 0.0472(8) -0.0005(7) 0.0124(7) 0.0121(7) O26 0.0561(9) 0.0395(8) 0.0680(10) -0.0132(7) 0.0171(7) -0.0093(6) O28 0.0747(10) 0.0469(8) 0.0437(8) -0.0060(6) 0.0175(7) -0.0043(7) N23 0.0688(13) 0.0911(16) 0.0575(12) 0.0054(11) 0.0299(10) -0.0063(12) C1 0.0469(11) 0.0351(10) 0.0501(11) 0.0010(8) 0.0173(9) -0.0032(8) C2 0.0431(10) 0.0369(10) 0.0526(11) -0.0053(8) 0.0198(9) -0.0023(8) C3 0.0398(9) 0.0355(9) 0.0480(10) -0.0051(7) 0.0152(8) -0.0004(7) C4 0.0395(10) 0.0342(9) 0.0461(10) -0.0021(7) 0.0145(8) 0.0000(7) C5 0.0376(9) 0.0382(10) 0.0454(10) -0.0023(7) 0.0128(8) -0.0030(7) C6 0.0407(9) 0.0365(9) 0.0476(10) -0.0002(7) 0.0157(8) -0.0034(7) C7 0.0384(9) 0.0340(9) 0.0516(11) -0.0037(8) 0.0118(8) -0.0016(7) C8 0.0397(9) 0.0441(10) 0.0417(10) -0.0034(8) 0.0102(8) 0.0014(8) C9 0.0443(10) 0.0414(10) 0.0442(10) 0.0038(8) 0.0130(8) -0.0014(8) C10 0.0400(9) 0.0363(9) 0.0466(10) -0.0007(7) 0.0130(8) -0.0026(7) C12 0.0449(11) 0.0428(11) 0.0639(13) -0.0065(9) 0.0222(10) -0.0070(8) C15 0.0641(16) 0.0722(19) 0.133(3) -0.0259(19) -0.0016(18) -0.0221(14) C16 0.0409(10) 0.0498(11) 0.0517(11) -0.0077(9) 0.0184(9) -0.0041(8) C19 0.0663(16) 0.126(3) 0.0474(13) 0.0016(14) 0.0102(12) 0.0056(16) C20 0.0399(10) 0.0423(10) 0.0421(10) -0.0064(7) 0.0118(8) -0.0056(8) C21 0.0614(13) 0.0592(13) 0.0642(14) 0.0086(11) 0.0287(11) 0.0061(11) C22 0.0747(16) 0.0742(17) 0.0622(14) 0.0177(12) 0.0279(12) 0.0012(13) C24 0.0587(14) 0.0873(18) 0.0654(15) -0.0020(13) 0.0318(12) 0.0033(12) C25 0.0491(11) 0.0554(12) 0.0554(12) -0.0054(9) 0.0215(9) -0.0007(9) C27 0.0707(17) 0.0729(18) 0.102(2) -0.0132(16) 0.0100(16) -0.0187(14) C29 0.0867(18) 0.0646(15) 0.0511(13) -0.0005(11) 0.0284(12) 0.0006(13) _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 O11 C1 1.442(2) . ? O11 C4 1.443(2) . ? O13 C12 1.194(3) . ? O14 C12 1.330(3) . ? O14 C15 1.452(3) . ? O17 C16 1.194(3) . ? O18 C16 1.331(3) . ? O18 C19 1.434(3) . ? O26 C27 1.373(3) . ? O26 C7 1.376(2) . ? O28 C8 1.358(2) . ? O28 C29 1.409(3) . ? N23 C24 1.313(3) . ? N23 C22 1.322(4) . ? C1 C10 1.514(3) . ? C1 C2 1.546(3) . ? C2 C12 1.515(3) . ? C2 C3 1.565(3) . ? C3 C16 1.511(3) . ? C3 C4 1.581(2) . ? C4 C20 1.494(3) . ? C4 C5 1.521(3) . ? C5 C6 1.383(3) . ? C5 C10 1.384(3) . ? C6 C7 1.382(3) . ? C7 C8 1.409(3) . ? C8 C9 1.396(3) . ? C9 C10 1.382(3) . ? C20 C25 1.378(3) . ? C20 C21 1.384(3) . ? C21 C22 1.384(3) . ? C24 C25 1.377(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 O11 C4 97.08(13) . . ? C12 O14 C15 115.3(2) . . ? C16 O18 C19 116.8(2) . . ? C27 O26 C7 116.21(19) . . ? C8 O28 C29 118.55(17) . . ? C24 N23 C22 116.0(2) . . ? O11 C1 C10 102.09(14) . . ? O11 C1 C2 100.77(15) . . ? C10 C1 C2 107.94(15) . . ? C12 C2 C1 111.51(16) . . ? C12 C2 C3 114.64(17) . . ? C1 C2 C3 101.50(15) . . ? C16 C3 C2 114.54(16) . . ? C16 C3 C4 112.87(15) . . ? C2 C3 C4 100.37(15) . . ? O11 C4 C20 112.23(15) . . ? O11 C4 C5 101.14(14) . . ? C20 C4 C5 116.59(15) . . ? O11 C4 C3 101.99(14) . . ? C20 C4 C3 118.01(15) . . ? C5 C4 C3 104.63(14) . . ? C6 C5 C10 121.64(18) . . ? C6 C5 C4 133.08(17) . . ? C10 C5 C4 105.13(16) . . ? C7 C6 C5 117.62(18) . . ? O26 C7 C6 119.00(18) . . ? O26 C7 C8 119.78(17) . . ? C6 C7 C8 121.15(17) . . ? O28 C8 C9 124.24(18) . . ? O28 C8 C7 115.34(17) . . ? C9 C8 C7 120.42(17) . . ? C10 C9 C8 117.60(17) . . ? C9 C10 C5 121.46(17) . . ? C9 C10 C1 133.79(17) . . ? C5 C10 C1 104.59(16) . . ? O13 C12 O14 123.45(19) . . ? O13 C12 C2 125.71(19) . . ? O14 C12 C2 110.79(17) . . ? O17 C16 O18 124.0(2) . . ? O17 C16 C3 126.19(19) . . ? O18 C16 C3 109.78(16) . . ? C25 C20 C21 117.29(19) . . ? C25 C20 C4 122.02(18) . . ? C21 C20 C4 120.62(18) . . ? C20 C21 C22 118.5(2) . . ? N23 C22 C21 124.5(2) . . ? N23 C24 C25 124.7(2) . . ? C24 C25 C20 119.1(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 65.08 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.671 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.039 data_compound2 _database_code_CSD 156920 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-Epoxynaphthalene-2,3-dicarboxylic acid, 1-(4-pyridyl)- 1,2,3,4-tetrahydro-6,7-dimethoxy-, dimethyl ester, (1beta, 2alpha , 3alpha , 4beta)-rel- (9CI) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 N O7' _chemical_formula_weight 399.39 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' '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 C2/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 34.619(2) _cell_length_b 6.874(2) _cell_length_c 16.426(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.73(1) _cell_angle_gamma 90.00 _cell_volume 3863.7(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 35 _cell_measurement_theta_max 45 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.870 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'nomal-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5R diffractometer' _diffrn_measurement_method ot _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3345 _diffrn_reflns_av_R_equivalents 0.0103 _diffrn_reflns_av_sigmaI/netI 0.0112 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 65.07 _reflns_number_total 3288 _reflns_number_gt 2972 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku/MSC AFC5R software 1992' _computing_cell_refinement 'Rigaku/MSC AFC5R software 1992' _computing_data_reduction 'Rigaku/MSC AFC5R software 1992' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0021(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3288 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1788 _refine_ls_wR_factor_gt 0.1740 _refine_ls_goodness_of_fit_ref 1.539 _refine_ls_restrained_S_all 1.539 _refine_ls_shift/su_max 0.017 _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 O11 O -0.40266(4) -0.16650(18) 0.00722(8) 0.0442(4) Uani 1 1 d . . . O13 O -0.35376(6) 0.1465(3) -0.19351(15) 0.0950(8) Uani 1 1 d . . . O14 O -0.32795(4) -0.1462(2) -0.17310(10) 0.0560(4) Uani 1 1 d . . . O17 O -0.40334(6) 0.4035(2) -0.09869(10) 0.0749(6) Uani 1 1 d . . . O18 O -0.43643(5) 0.2598(2) -0.20801(10) 0.0638(5) Uani 1 1 d . . . O26 O -0.29580(4) 0.4534(2) 0.13939(9) 0.0543(4) Uani 1 1 d . . . O28 O -0.24934(4) 0.1910(2) 0.10039(9) 0.0527(4) Uani 1 1 d . . . N23 N -0.49956(5) 0.2140(3) 0.13676(11) 0.0523(5) Uani 1 1 d . . . C1 C -0.36916(5) -0.1771(3) -0.03483(11) 0.0414(4) Uani 1 1 d . . . C2 C -0.38613(5) -0.0921(3) -0.12104(11) 0.0415(5) Uani 1 1 d . . . C3 C -0.41632(5) 0.0574(3) -0.09657(11) 0.0395(4) Uani 1 1 d . . . C4 C -0.40854(5) 0.0430(3) -0.00101(11) 0.0396(4) Uani 1 1 d . . . C5 C -0.36773(5) 0.1156(3) 0.03159(10) 0.0375(4) Uani 1 1 d . . . C6 C -0.35377(5) 0.2823(3) 0.07378(11) 0.0393(4) Uani 1 1 d . . . C7 C -0.31372(5) 0.3004(3) 0.09591(11) 0.0406(4) Uani 1 1 d . . . C8 C -0.28803(5) 0.1556(3) 0.07423(11) 0.0412(4) Uani 1 1 d . . . C9 C -0.30256(5) -0.0067(3) 0.03061(11) 0.0409(4) Uani 1 1 d . . . C10 C -0.34276(5) -0.0259(3) 0.01076(11) 0.0385(4) Uani 1 1 d . . . C12 C -0.35516(6) -0.0142(3) -0.16705(11) 0.0445(5) Uani 1 1 d . . . C15 C -0.29561(7) -0.0849(3) -0.21278(15) 0.0601(6) Uani 1 1 d . . . C16 C -0.41616(5) 0.2594(3) -0.13266(12) 0.0433(5) Uani 1 1 d . . . C19 C -0.43879(10) 0.4427(4) -0.25160(18) 0.0832(9) Uani 1 1 d . . . C20 C -0.44077(5) 0.1067(3) 0.04540(11) 0.0407(4) Uani 1 1 d . . . C21 C -0.47230(6) 0.2180(3) 0.01092(12) 0.0480(5) Uani 1 1 d . . . C22 C -0.50067(6) 0.2669(3) 0.05866(14) 0.0511(5) Uani 1 1 d . . . C24 C -0.46878(6) 0.1072(4) 0.16908(13) 0.0551(5) Uani 1 1 d . . . C25 C -0.43926(6) 0.0514(3) 0.12697(13) 0.0507(5) Uani 1 1 d . . . C27 C -0.31950(7) 0.5804(3) 0.17889(15) 0.0570(6) Uani 1 1 d . . . C29 C -0.22230(6) 0.0469(3) 0.08400(15) 0.0580(6) Uani 1 1 d . . . H30 H -0.3579 -0.3033 -0.0363 0.050 Uiso 1 1 d . . . H31 H -0.3999 -0.1917 -0.1529 0.049 Uiso 1 1 d . . . H32 H -0.4415 0.0045 -0.1140 0.047 Uiso 1 1 d . . . H33 H -0.3710 0.3803 0.0866 0.047 Uiso 1 1 d . . . H34 H -0.2857 -0.1032 0.0141 0.049 Uiso 1 1 d . . . H35 H -0.3052 -0.0211 -0.2632 0.073 Uiso 1 1 d . . . H36 H -0.2806 -0.1950 -0.2237 0.073 Uiso 1 1 d . . . H37 H -0.2795 0.0026 -0.1778 0.073 Uiso 1 1 d . . . H38 H -0.4495 0.5398 -0.2202 0.102 Uiso 1 1 d . . . H39 H -0.4545 0.4297 -0.3036 0.102 Uiso 1 1 d . . . H40 H -0.4130 0.4826 -0.2594 0.102 Uiso 1 1 d . . . H41 H -0.4745 0.2599 -0.0446 0.056 Uiso 1 1 d . . . H42 H -0.5221 0.3427 0.0340 0.062 Uiso 1 1 d . . . H43 H -0.4674 0.0672 0.2246 0.067 Uiso 1 1 d . . . H44 H -0.4181 -0.0241 0.1530 0.060 Uiso 1 1 d . . . H45 H -0.3346 0.5063 0.2115 0.070 Uiso 1 1 d . . . H46 H -0.3034 0.6687 0.2132 0.070 Uiso 1 1 d . . . H47 H -0.3365 0.6512 0.1385 0.070 Uiso 1 1 d . . . H48 H -0.2273 -0.0712 0.1108 0.070 Uiso 1 1 d . . . H49 H -0.1964 0.0890 0.1034 0.070 Uiso 1 1 d . . . H50 H -0.2250 0.0244 0.0261 0.070 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 O11 0.0486(7) 0.0347(7) 0.0508(7) 0.0022(5) 0.0121(6) -0.0070(5) O13 0.0886(13) 0.0701(12) 0.1412(19) 0.0510(12) 0.0655(13) 0.0244(10) O14 0.0627(9) 0.0418(8) 0.0692(9) 0.0018(7) 0.0282(7) 0.0013(6) O17 0.1158(14) 0.0432(9) 0.0583(10) 0.0023(7) -0.0104(9) -0.0260(9) O18 0.0785(11) 0.0489(9) 0.0553(9) 0.0072(7) -0.0176(8) -0.0048(7) O26 0.0450(7) 0.0523(9) 0.0652(9) -0.0253(7) 0.0074(6) -0.0074(6) O28 0.0350(7) 0.0587(9) 0.0626(9) -0.0130(7) 0.0011(6) 0.0003(6) N23 0.0426(9) 0.0575(10) 0.0586(10) -0.0040(8) 0.0127(7) -0.0061(8) C1 0.0459(10) 0.0320(9) 0.0469(10) -0.0011(7) 0.0092(8) -0.0034(7) C2 0.0456(10) 0.0354(9) 0.0427(10) -0.0068(7) 0.0045(8) -0.0095(7) C3 0.0392(9) 0.0374(10) 0.0411(10) -0.0030(7) 0.0034(7) -0.0094(7) C4 0.0409(9) 0.0349(9) 0.0429(10) 0.0006(7) 0.0058(7) -0.0069(7) C5 0.0389(9) 0.0382(9) 0.0350(8) 0.0017(7) 0.0036(7) -0.0023(7) C6 0.0398(9) 0.0376(9) 0.0411(9) -0.0041(7) 0.0074(7) 0.0009(7) C7 0.0407(9) 0.0408(10) 0.0402(9) -0.0067(7) 0.0056(7) -0.0041(7) C8 0.0382(9) 0.0461(10) 0.0387(9) -0.0007(7) 0.0041(7) -0.0005(7) C9 0.0437(10) 0.0385(9) 0.0406(9) -0.0003(7) 0.0074(7) 0.0041(8) C10 0.0438(9) 0.0341(9) 0.0379(9) 0.0013(7) 0.0076(7) 0.0000(7) C12 0.0501(10) 0.0418(10) 0.0412(9) -0.0006(8) 0.0054(8) -0.0039(8) C15 0.0626(13) 0.0556(13) 0.0668(14) -0.0014(10) 0.0258(11) -0.0022(10) C16 0.0452(10) 0.0411(10) 0.0431(9) -0.0001(8) 0.0044(7) -0.0042(8) C19 0.112(2) 0.0602(15) 0.0695(16) 0.0218(13) -0.0130(15) 0.0065(15) C20 0.0365(9) 0.0402(9) 0.0454(10) -0.0019(7) 0.0059(7) -0.0088(7) C21 0.0462(10) 0.0456(11) 0.0524(11) 0.0068(8) 0.0081(8) -0.0025(8) C22 0.0425(10) 0.0458(11) 0.0648(12) 0.0039(9) 0.0081(9) 0.0012(8) C24 0.0474(11) 0.0724(14) 0.0463(11) 0.0045(10) 0.0094(8) -0.0013(10) C25 0.0410(9) 0.0635(13) 0.0475(11) 0.0051(9) 0.0066(8) 0.0015(9) C27 0.0590(12) 0.0500(12) 0.0614(13) -0.0199(10) 0.0068(10) -0.0008(9) C29 0.0415(10) 0.0589(13) 0.0720(14) 0.0042(11) 0.0038(9) 0.0078(9) _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 O11 C1 1.439(2) . ? O11 C4 1.457(2) . ? O13 C12 1.191(3) . ? O14 C12 1.323(2) . ? O14 C15 1.441(3) . ? O17 C16 1.189(2) . ? O18 C16 1.327(2) . ? O18 C19 1.443(3) . ? O26 C7 1.366(2) . ? O26 C27 1.420(2) . ? O28 C8 1.365(2) . ? O28 C29 1.417(3) . ? N23 C22 1.329(3) . ? N23 C24 1.336(3) . ? C1 C10 1.506(3) . ? C1 C2 1.562(3) . ? C2 C12 1.501(3) . ? C2 C3 1.561(3) . ? C3 C16 1.510(3) . ? C3 C4 1.555(2) . ? C4 C20 1.509(2) . ? C4 C5 1.518(2) . ? C5 C10 1.379(3) . ? C5 C6 1.388(3) . ? C6 C7 1.384(3) . ? C7 C8 1.416(3) . ? C8 C9 1.379(3) . ? C9 C10 1.387(3) . ? C20 C21 1.382(3) . ? C20 C25 1.386(3) . ? C21 C22 1.388(3) . ? C24 C25 1.373(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 O11 C4 96.72(13) . . ? C12 O14 C15 116.37(16) . . ? C16 O18 C19 116.54(18) . . ? C7 O26 C27 117.63(15) . . ? C8 O28 C29 117.43(16) . . ? C22 N23 C24 116.04(17) . . ? O11 C1 C10 101.46(14) . . ? O11 C1 C2 101.33(14) . . ? C10 C1 C2 108.00(14) . . ? C12 C2 C3 116.89(15) . . ? C12 C2 C1 113.01(15) . . ? C3 C2 C1 100.80(14) . . ? C16 C3 C4 116.41(14) . . ? C16 C3 C2 117.49(15) . . ? C4 C3 C2 101.41(14) . . ? O11 C4 C20 110.11(14) . . ? O11 C4 C5 100.54(14) . . ? C20 C4 C5 116.51(14) . . ? O11 C4 C3 99.04(13) . . ? C20 C4 C3 117.61(15) . . ? C5 C4 C3 110.15(13) . . ? C10 C5 C6 121.52(16) . . ? C10 C5 C4 105.40(15) . . ? C6 C5 C4 133.08(16) . . ? C7 C6 C5 117.68(16) . . ? O26 C7 C6 124.31(16) . . ? O26 C7 C8 114.83(16) . . ? C6 C7 C8 120.85(16) . . ? O28 C8 C9 124.79(17) . . ? O28 C8 C7 114.80(16) . . ? C9 C8 C7 120.41(16) . . ? C8 C9 C10 118.24(16) . . ? C5 C10 C9 121.27(17) . . ? C5 C10 C1 104.73(15) . . ? C9 C10 C1 133.98(17) . . ? O13 C12 O14 122.69(19) . . ? O13 C12 C2 125.90(19) . . ? O14 C12 C2 111.38(16) . . ? O17 C16 O18 122.87(19) . . ? O17 C16 C3 127.22(17) . . ? O18 C16 C3 109.59(15) . . ? C21 C20 C25 117.36(18) . . ? C21 C20 C4 123.54(16) . . ? C25 C20 C4 119.10(17) . . ? C20 C21 C22 119.03(18) . . ? N23 C22 C21 124.05(19) . . ? N23 C24 C25 124.27(19) . . ? C24 C25 C20 119.25(19) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 65.07 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.339 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.046 data_compound3 _database_code_CSD 156921 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-Epoxynaphthalene-2,3-dicarboxylic acid, 1-(4-pyridyl)- 1,2,3,4-tetrahydro-6,7-dimethoxy-, dimethyl ester, (1beta, 2beta , 3alpha , 4beta)-rel- (9CI) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 N O7' _chemical_formula_weight 399.39 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' '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 P21/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 8.529(2) _cell_length_b 13.759(1) _cell_length_c 16.822(1) _cell_angle_alpha 90.00 _cell_angle_beta 98.84(1) _cell_angle_gamma 90.00 _cell_volume 1950.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 35 _cell_measurement_theta_max 45 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.862 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'nomal-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5R diffractometer' _diffrn_measurement_method ot _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3562 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 65.06 _reflns_number_total 3322 _reflns_number_gt 2785 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku/MSC AFC5R software 1992' _computing_cell_refinement 'Rigaku/MSC AFC5R software 1992' _computing_data_reduction 'Rigaku/MSC AFC5R software 1992' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0021(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3322 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1715 _refine_ls_wR_factor_gt 0.1634 _refine_ls_goodness_of_fit_ref 1.317 _refine_ls_restrained_S_all 1.317 _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 O11 O -0.77204(17) 0.32912(11) -0.27042(8) 0.0540(4) Uani 1 1 d . . . O13 O -1.2199(2) 0.27692(13) -0.44070(10) 0.0745(5) Uani 1 1 d . . . O14 O -1.22050(18) 0.19228(13) -0.32820(9) 0.0655(5) Uani 1 1 d . . . O17 O -0.9738(2) 0.51414(13) -0.26490(11) 0.0798(5) Uani 1 1 d . . . O18 O -0.9999(2) 0.56434(12) -0.39248(11) 0.0696(5) Uani 1 1 d . . . O26 O -0.6817(2) 0.10661(12) -0.55722(10) 0.0749(5) Uani 1 1 d . . . O28 O -0.8009(2) -0.01842(10) -0.47154(9) 0.0613(4) Uani 1 1 d . . . N23 N -0.4272(3) 0.57788(18) -0.37844(18) 0.0862(7) Uani 1 1 d . . . C1 C -0.8942(2) 0.25639(15) -0.28474(11) 0.0503(5) Uani 1 1 d . . . C2 C -1.0392(2) 0.31932(15) -0.32160(12) 0.0496(5) Uani 1 1 d . . . C3 C -0.9610(2) 0.39684(15) -0.36909(11) 0.0478(5) Uani 1 1 d . . . C4 C -0.7824(2) 0.36257(15) -0.35250(11) 0.0476(5) Uani 1 1 d . . . C5 C -0.7739(2) 0.26653(14) -0.39689(12) 0.0465(5) Uani 1 1 d . . . C6 C -0.7203(2) 0.24080(15) -0.46758(12) 0.0484(5) Uani 1 1 d . . . C7 C -0.7322(2) 0.14375(15) -0.49042(12) 0.0497(5) Uani 1 1 d . . . C8 C -0.7987(2) 0.07431(14) -0.44352(12) 0.0487(5) Uani 1 1 d . . . C9 C -0.8566(2) 0.10233(15) -0.37428(12) 0.0495(5) Uani 1 1 d . . . C10 C -0.8414(2) 0.19850(15) -0.35196(11) 0.0485(5) Uani 1 1 d . . . C12 C -1.1692(2) 0.26207(16) -0.37177(12) 0.0515(5) Uani 1 1 d . . . C15 C -1.3446(3) 0.1306(2) -0.36870(16) 0.0778(8) Uani 1 1 d . . . C16 C -0.9790(2) 0.49658(16) -0.33492(13) 0.0552(5) Uani 1 1 d . . . C19 C -1.0073(4) 0.6632(2) -0.3639(2) 0.0943(10) Uani 1 1 d . . . C20 C -0.6576(2) 0.43682(15) -0.36145(13) 0.0524(5) Uani 1 1 d . . . C21 C -0.6745(3) 0.50018(18) -0.42592(15) 0.0662(6) Uani 1 1 d . . . C22 C -0.5569(3) 0.5688(2) -0.4308(2) 0.0804(8) Uani 1 1 d . . . C24 C -0.4103(3) 0.5156(2) -0.3178(2) 0.0838(8) Uani 1 1 d . . . C25 C -0.5206(3) 0.44436(19) -0.30586(16) 0.0680(6) Uani 1 1 d . . . C27 C -0.5775(4) 0.1623(2) -0.59549(17) 0.0811(8) Uani 1 1 d . . . C29 C -0.8535(3) -0.09215(16) -0.42247(15) 0.0664(6) Uani 1 1 d . . . H30 H -0.9091 0.2187 -0.2391 0.061 Uiso 1 1 d . . . H31 H -1.0810 0.3501 -0.2792 0.057 Uiso 1 1 d . . . H32 H -1.0023 0.3943 -0.4247 0.055 Uiso 1 1 d . . . H33 H -0.6761 0.2875 -0.4987 0.056 Uiso 1 1 d . . . H34 H -0.9060 0.0570 -0.3441 0.056 Uiso 1 1 d . . . H35 H -1.4304 0.1702 -0.3946 0.078 Uiso 1 1 d . . . H36 H -1.3828 0.0888 -0.3301 0.078 Uiso 1 1 d . . . H37 H -1.3037 0.0920 -0.4083 0.078 Uiso 1 1 d . . . H38 H -1.1035 0.6724 -0.3419 0.094 Uiso 1 1 d . . . H39 H -1.0053 0.7075 -0.4080 0.094 Uiso 1 1 d . . . H40 H -0.9178 0.6756 -0.3231 0.094 Uiso 1 1 d . . . H41 H -0.7663 0.4981 -0.4660 0.079 Uiso 1 1 d . . . H42 H -0.5720 0.6134 -0.4735 0.096 Uiso 1 1 d . . . H43 H -0.3145 0.5178 -0.2788 0.100 Uiso 1 1 d . . . H44 H -0.5029 0.4027 -0.2601 0.079 Uiso 1 1 d . . . H45 H -0.4941 0.1846 -0.5557 0.105 Uiso 1 1 d . . . H46 H -0.5340 0.1209 -0.6322 0.105 Uiso 1 1 d . . . H47 H -0.6320 0.2140 -0.6226 0.105 Uiso 1 1 d . . . H48 H -0.7918 -0.0892 -0.3702 0.083 Uiso 1 1 d . . . H49 H -0.8413 -0.1537 -0.4455 0.083 Uiso 1 1 d . . . H50 H -0.9619 -0.0813 -0.4181 0.083 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 O11 0.0524(8) 0.0659(9) 0.0435(7) -0.0044(6) 0.0066(6) -0.0062(7) O13 0.0796(12) 0.0805(12) 0.0594(10) 0.0118(8) -0.0027(8) -0.0265(9) O14 0.0566(9) 0.0807(11) 0.0595(9) 0.0136(8) 0.0099(7) -0.0197(8) O17 0.1005(14) 0.0716(11) 0.0706(11) -0.0182(9) 0.0236(10) 0.0080(10) O18 0.0732(11) 0.0541(9) 0.0803(11) 0.0018(8) 0.0079(9) -0.0021(8) O26 0.0985(13) 0.0650(10) 0.0730(11) -0.0180(8) 0.0503(10) -0.0212(9) O28 0.0754(11) 0.0483(8) 0.0642(9) -0.0018(7) 0.0242(8) -0.0053(7) N23 0.0674(14) 0.0766(15) 0.118(2) -0.0091(14) 0.0262(14) -0.0232(11) C1 0.0533(11) 0.0583(12) 0.0407(10) 0.0025(8) 0.0119(8) -0.0058(9) C2 0.0487(11) 0.0583(12) 0.0451(10) -0.0065(9) 0.0172(8) -0.0033(9) C3 0.0460(10) 0.0538(11) 0.0449(10) -0.0042(8) 0.0110(8) -0.0049(8) C4 0.0441(10) 0.0557(11) 0.0444(10) -0.0049(8) 0.0115(8) -0.0046(8) C5 0.0400(9) 0.0522(11) 0.0483(10) -0.0009(8) 0.0097(8) -0.0034(8) C6 0.0453(10) 0.0527(11) 0.0498(10) 0.0018(8) 0.0158(8) -0.0062(8) C7 0.0477(11) 0.0545(12) 0.0501(11) -0.0042(9) 0.0179(9) -0.0036(8) C8 0.0468(10) 0.0473(11) 0.0530(11) 0.0003(8) 0.0104(8) 0.0002(8) C9 0.0484(11) 0.0524(11) 0.0492(11) 0.0066(8) 0.0125(8) -0.0027(8) C10 0.0442(10) 0.0569(11) 0.0452(10) 0.0028(8) 0.0096(8) -0.0001(8) C12 0.0466(11) 0.0603(12) 0.0502(11) 0.0012(9) 0.0156(9) -0.0033(9) C15 0.0662(15) 0.0890(18) 0.0763(16) 0.0157(14) 0.0047(12) -0.0297(13) C16 0.0462(11) 0.0589(12) 0.0621(13) -0.0059(10) 0.0135(9) -0.0011(9) C19 0.101(2) 0.0497(14) 0.128(3) -0.0021(15) 0.0011(19) -0.0032(14) C20 0.0441(11) 0.0545(12) 0.0607(12) -0.0137(9) 0.0147(9) -0.0051(8) C21 0.0547(13) 0.0720(15) 0.0741(14) 0.0074(12) 0.0171(11) -0.0127(11) C22 0.0655(16) 0.0724(16) 0.108(2) 0.0099(15) 0.0284(15) -0.0116(13) C24 0.0554(14) 0.092(2) 0.102(2) -0.0278(18) 0.0077(14) -0.0209(14) C25 0.0542(13) 0.0758(15) 0.0732(15) -0.0127(12) 0.0075(11) -0.0078(11) C27 0.095(2) 0.0910(19) 0.0671(15) -0.0056(13) 0.0447(14) -0.0091(15) C29 0.0831(17) 0.0502(12) 0.0684(14) 0.0058(10) 0.0199(12) -0.0041(11) _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 O11 C1 1.438(2) . ? O11 C4 1.445(2) . ? O13 C12 1.191(3) . ? O14 C12 1.323(2) . ? O14 C15 1.444(3) . ? O17 C16 1.196(3) . ? O18 C16 1.336(3) . ? O18 C19 1.448(3) . ? O26 C7 1.363(2) . ? O26 C27 1.402(3) . ? O28 C8 1.359(2) . ? O28 C29 1.423(3) . ? N23 C22 1.310(4) . ? N23 C24 1.324(4) . ? C1 C10 1.508(3) . ? C1 C2 1.558(3) . ? C2 C12 1.508(3) . ? C2 C3 1.544(3) . ? C3 C16 1.505(3) . ? C3 C4 1.578(3) . ? C4 C20 1.500(3) . ? C4 C5 1.525(3) . ? C5 C10 1.383(3) . ? C5 C6 1.384(3) . ? C6 C7 1.389(3) . ? C7 C8 1.412(3) . ? C8 C9 1.388(3) . ? C9 C10 1.376(3) . ? C20 C21 1.382(3) . ? C20 C25 1.384(3) . ? C21 C22 1.389(3) . ? C24 C25 1.394(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 C1 O11 C4 97.19(13) . . ? C12 O14 C15 116.53(17) . . ? C16 O18 C19 115.0(2) . . ? C7 O26 C27 118.46(18) . . ? C8 O28 C29 117.18(16) . . ? C22 N23 C24 116.0(2) . . ? O11 C1 C10 101.59(15) . . ? O11 C1 C2 100.96(16) . . ? C10 C1 C2 107.79(16) . . ? C12 C2 C3 114.21(17) . . ? C12 C2 C1 113.75(17) . . ? C3 C2 C1 102.15(15) . . ? C16 C3 C2 110.79(16) . . ? C16 C3 C4 110.92(16) . . ? C2 C3 C4 100.60(15) . . ? O11 C4 C20 111.88(16) . . ? O11 C4 C5 101.03(15) . . ? C20 C4 C5 116.96(16) . . ? O11 C4 C3 100.36(14) . . ? C20 C4 C3 117.36(17) . . ? C5 C4 C3 106.83(15) . . ? C10 C5 C6 121.11(18) . . ? C10 C5 C4 105.30(16) . . ? C6 C5 C4 133.56(18) . . ? C5 C6 C7 117.63(17) . . ? O26 C7 C6 124.71(18) . . ? O26 C7 C8 114.32(18) . . ? C6 C7 C8 120.96(18) . . ? O28 C8 C9 124.33(18) . . ? O28 C8 C7 115.25(17) . . ? C9 C8 C7 120.42(18) . . ? C10 C9 C8 117.71(18) . . ? C9 C10 C5 122.12(18) . . ? C9 C10 C1 133.31(18) . . ? C5 C10 C1 104.46(17) . . ? O13 C12 O14 124.2(2) . . ? O13 C12 C2 125.51(19) . . ? O14 C12 C2 110.28(17) . . ? O17 C16 O18 123.6(2) . . ? O17 C16 C3 124.7(2) . . ? O18 C16 C3 111.69(18) . . ? C21 C20 C25 117.3(2) . . ? C21 C20 C4 121.25(19) . . ? C25 C20 C4 121.5(2) . . ? C20 C21 C22 119.1(2) . . ? N23 C22 C21 124.6(3) . . ? N23 C24 C25 124.8(3) . . ? C20 C25 C24 118.3(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 65.06 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.241 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.038 data_compound4 _database_code_CSD 156922 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-Epoxynaphthalene-2,3-dicarboxylic acid, 1-(4-pyridyl)- 1,2,3,4-tetrahydro-6,7-dimethoxy-, dimethyl ester, (1beta, 2alpha , 3beta , 4beta)-rel- (9CI) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 N O7' _chemical_formula_weight 399.39 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 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 10.839(1) _cell_length_b 11.534(1) _cell_length_c 15.677(1) _cell_angle_alpha 90.00 _cell_angle_beta 105.51(1) _cell_angle_gamma 90.00 _cell_volume 1888.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 35 _cell_measurement_theta_max 45 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.890 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'nomal-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5R diffractometer' _diffrn_measurement_method ot _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3407 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0126 _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 -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.23 _diffrn_reflns_theta_max 65.07 _reflns_number_total 3224 _reflns_number_gt 2911 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku/MSC AFC5R software 1992' _computing_cell_refinement 'Rigaku/MSC AFC5R software 1992' _computing_data_reduction 'Rigaku/MSC AFC5R software 1992' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0024(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3224 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1363 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _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 O11 O 0.13253(10) -0.35219(9) 0.05609(7) 0.0434(3) Uani 1 1 d . . . O13 O 0.37001(18) -0.55756(11) 0.05347(9) 0.0772(5) Uani 1 1 d . . . O14 O 0.37889(13) -0.52837(9) 0.19469(7) 0.0545(3) Uani 1 1 d . . . O17 O 0.49453(12) -0.18784(11) 0.04999(8) 0.0593(4) Uani 1 1 d . . . O18 O 0.37936(11) -0.19779(11) -0.09083(7) 0.0508(3) Uani 1 1 d . . . O26 O 0.19977(12) 0.15457(9) 0.07432(8) 0.0521(3) Uani 1 1 d . . . O28 O 0.27150(13) 0.09484(9) 0.23697(7) 0.0542(3) Uani 1 1 d . . . N23 N -0.07629(14) -0.32247(16) -0.26699(10) 0.0624(4) Uani 1 1 d . . . C1 C 0.23092(15) -0.32333(12) 0.13466(10) 0.0411(4) Uani 1 1 d . . . C2 C 0.35033(14) -0.36319(12) 0.10578(10) 0.0387(3) Uani 1 1 d . . . C3 C 0.31718(14) -0.32064(12) 0.00931(9) 0.0376(3) Uani 1 1 d . . . C4 C 0.17345(13) -0.27536(12) -0.00411(10) 0.0385(3) Uani 1 1 d . . . C5 C 0.18567(13) -0.16104(12) 0.04628(10) 0.0375(3) Uani 1 1 d . . . C6 C 0.17681(14) -0.04469(13) 0.02172(10) 0.0395(4) Uani 1 1 d . . . C7 C 0.20593(14) 0.03798(13) 0.08846(10) 0.0397(3) Uani 1 1 d . . . C8 C 0.24488(14) 0.00519(13) 0.17846(10) 0.0409(4) Uani 1 1 d . . . C9 C 0.25448(15) -0.11142(13) 0.20181(10) 0.0412(4) Uani 1 1 d . . . C10 C 0.22441(14) -0.19283(12) 0.13429(10) 0.0399(4) Uani 1 1 d . . . C12 C 0.36624(15) -0.49394(13) 0.11217(10) 0.0425(4) Uani 1 1 d . . . C15 C 0.3938(2) -0.65173(14) 0.21214(14) 0.0621(5) Uani 1 1 d . . . C16 C 0.40791(14) -0.22899(13) -0.00596(10) 0.0402(4) Uani 1 1 d . . . C19 C 0.4569(2) -0.10530(19) -0.11167(14) 0.0686(6) Uani 1 1 d . . . C20 C 0.08648(14) -0.28886(13) -0.09572(10) 0.0415(4) Uani 1 1 d . . . C21 C 0.00992(17) -0.38676(15) -0.11754(12) 0.0535(4) Uani 1 1 d . . . C22 C -0.06760(19) -0.39866(17) -0.20241(14) 0.0634(5) Uani 1 1 d . . . C24 C -0.00316(17) -0.22907(18) -0.24530(12) 0.0563(4) Uani 1 1 d . . . C25 C 0.07852(16) -0.20842(15) -0.16251(11) 0.0496(4) Uani 1 1 d . . . C27 C 0.17044(18) 0.19340(14) -0.01494(12) 0.0549(4) Uani 1 1 d . . . C29 C 0.29235(18) 0.06960(15) 0.32828(11) 0.0523(4) Uani 1 1 d . . . H30 H 0.2225 -0.3589 0.1878 0.051 Uiso 1 1 d . . . H31 H 0.4254 -0.3257 0.1401 0.049 Uiso 1 1 d . . . H32 H 0.3170 -0.3843 -0.0289 0.049 Uiso 1 1 d . . . H33 H 0.1513 -0.0222 -0.0388 0.049 Uiso 1 1 d . . . H34 H 0.2799 -0.1340 0.2615 0.049 Uiso 1 1 d . . . H35 H 0.3191 -0.6914 0.1777 0.071 Uiso 1 1 d . . . H36 H 0.4038 -0.6657 0.2724 0.071 Uiso 1 1 d . . . H37 H 0.4662 -0.6789 0.1947 0.071 Uiso 1 1 d . . . H38 H 0.4377 -0.0352 -0.0871 0.081 Uiso 1 1 d . . . H39 H 0.4350 -0.0967 -0.1755 0.081 Uiso 1 1 d . . . H40 H 0.5437 -0.1238 -0.0910 0.081 Uiso 1 1 d . . . H41 H 0.0125 -0.4450 -0.0748 0.064 Uiso 1 1 d . . . H42 H -0.1186 -0.4663 -0.2145 0.077 Uiso 1 1 d . . . H43 H -0.0064 -0.1727 -0.2900 0.064 Uiso 1 1 d . . . H44 H 0.1278 -0.1396 -0.1514 0.064 Uiso 1 1 d . . . H45 H 0.0867 0.1694 -0.0448 0.068 Uiso 1 1 d . . . H46 H 0.1748 0.2761 -0.0147 0.068 Uiso 1 1 d . . . H47 H 0.2305 0.1626 -0.0425 0.068 Uiso 1 1 d . . . H48 H 0.3667 0.0228 0.3476 0.066 Uiso 1 1 d . . . H49 H 0.3042 0.1401 0.3609 0.066 Uiso 1 1 d . . . H50 H 0.2204 0.0296 0.3371 0.066 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 O11 0.0493(6) 0.0363(6) 0.0467(6) 0.0023(4) 0.0164(5) -0.0072(4) O13 0.1405(14) 0.0374(7) 0.0598(8) -0.0055(6) 0.0372(9) 0.0071(7) O14 0.0831(8) 0.0305(6) 0.0457(6) 0.0024(5) 0.0100(6) 0.0042(5) O17 0.0607(7) 0.0648(8) 0.0469(7) 0.0035(6) 0.0049(6) -0.0240(6) O18 0.0525(7) 0.0579(7) 0.0412(6) 0.0076(5) 0.0111(5) -0.0116(5) O26 0.0793(8) 0.0301(6) 0.0463(6) 0.0049(5) 0.0155(6) 0.0009(5) O28 0.0877(9) 0.0355(6) 0.0414(6) -0.0031(4) 0.0206(6) -0.0022(5) N23 0.0499(8) 0.0779(11) 0.0531(9) -0.0109(8) 0.0029(7) -0.0076(7) C1 0.0540(9) 0.0328(7) 0.0389(8) 0.0024(6) 0.0166(6) -0.0020(6) C2 0.0472(8) 0.0304(7) 0.0382(7) -0.0011(6) 0.0106(6) -0.0019(6) C3 0.0446(8) 0.0321(7) 0.0359(7) -0.0030(6) 0.0106(6) -0.0013(6) C4 0.0420(7) 0.0333(7) 0.0411(8) 0.0004(6) 0.0129(6) -0.0039(6) C5 0.0401(7) 0.0338(7) 0.0400(8) 0.0000(6) 0.0131(6) -0.0008(6) C6 0.0438(8) 0.0363(8) 0.0390(8) 0.0043(6) 0.0121(6) 0.0010(6) C7 0.0462(8) 0.0314(7) 0.0438(8) 0.0027(6) 0.0158(6) 0.0016(6) C8 0.0510(8) 0.0344(8) 0.0404(8) -0.0017(6) 0.0175(6) 0.0000(6) C9 0.0538(8) 0.0359(8) 0.0364(7) 0.0025(6) 0.0166(6) 0.0027(6) C10 0.0482(8) 0.0331(7) 0.0419(8) 0.0032(6) 0.0182(6) 0.0020(6) C12 0.0510(8) 0.0326(8) 0.0427(8) -0.0008(6) 0.0102(6) -0.0006(6) C15 0.0843(13) 0.0329(9) 0.0635(11) 0.0100(8) 0.0102(9) 0.0067(8) C16 0.0447(8) 0.0387(8) 0.0384(8) -0.0004(6) 0.0129(6) -0.0008(6) C19 0.0770(13) 0.0738(13) 0.0560(11) 0.0173(10) 0.0194(9) -0.0206(10) C20 0.0390(7) 0.0410(8) 0.0448(8) -0.0044(6) 0.0118(6) -0.0022(6) C21 0.0587(10) 0.0453(9) 0.0547(10) -0.0042(7) 0.0119(8) -0.0119(7) C22 0.0639(11) 0.0600(11) 0.0614(11) -0.0131(9) 0.0079(9) -0.0212(9) C24 0.0536(9) 0.0665(11) 0.0453(9) 0.0024(8) 0.0072(7) -0.0018(8) C25 0.0508(9) 0.0493(9) 0.0467(9) 0.0004(7) 0.0094(7) -0.0063(7) C27 0.0702(11) 0.0397(9) 0.0530(10) 0.0124(7) 0.0132(8) 0.0024(7) C29 0.0668(10) 0.0496(9) 0.0407(8) -0.0053(7) 0.0150(7) -0.0029(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 O11 C1 1.4362(18) . ? O11 C4 1.4479(17) . ? O13 C12 1.186(2) . ? O14 C12 1.3248(18) . ? O14 C15 1.4497(19) . ? O17 C16 1.1982(18) . ? O18 C16 1.3325(18) . ? O18 C19 1.448(2) . ? O26 C7 1.3616(18) . ? O26 C27 1.422(2) . ? O28 C8 1.3610(18) . ? O28 C29 1.4184(19) . ? N23 C22 1.325(3) . ? N23 C24 1.327(3) . ? C1 C10 1.507(2) . ? C1 C2 1.551(2) . ? C2 C12 1.518(2) . ? C2 C3 1.538(2) . ? C3 C16 1.506(2) . ? C3 C4 1.6027(19) . ? C4 C20 1.500(2) . ? C4 C5 1.525(2) . ? C5 C10 1.380(2) . ? C5 C6 1.392(2) . ? C6 C7 1.388(2) . ? C7 C8 1.412(2) . ? C8 C9 1.390(2) . ? C9 C10 1.387(2) . ? C20 C25 1.384(2) . ? C20 C21 1.389(2) . ? C21 C22 1.377(3) . ? C24 C25 1.382(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 O11 C4 97.50(10) . . ? C12 O14 C15 117.10(13) . . ? C16 O18 C19 115.50(13) . . ? C7 O26 C27 117.36(13) . . ? C8 O28 C29 118.17(12) . . ? C22 N23 C24 115.29(15) . . ? O11 C1 C10 101.83(12) . . ? O11 C1 C2 99.62(11) . . ? C10 C1 C2 109.69(12) . . ? C12 C2 C3 111.98(12) . . ? C12 C2 C1 111.36(12) . . ? C3 C2 C1 101.45(11) . . ? C16 C3 C2 112.91(12) . . ? C16 C3 C4 113.80(11) . . ? C2 C3 C4 101.32(11) . . ? O11 C4 C20 109.69(11) . . ? O11 C4 C5 101.00(11) . . ? C20 C4 C5 122.07(12) . . ? O11 C4 C3 99.87(11) . . ? C20 C4 C3 115.58(12) . . ? C5 C4 C3 105.49(11) . . ? C10 C5 C6 120.84(14) . . ? C10 C5 C4 104.44(12) . . ? C6 C5 C4 134.45(14) . . ? C7 C6 C5 117.94(14) . . ? O26 C7 C6 124.35(14) . . ? O26 C7 C8 114.57(13) . . ? C6 C7 C8 121.08(14) . . ? O28 C8 C9 124.75(14) . . ? O28 C8 C7 115.01(13) . . ? C9 C8 C7 120.23(13) . . ? C10 C9 C8 117.91(14) . . ? C5 C10 C9 121.98(14) . . ? C5 C10 C1 105.70(13) . . ? C9 C10 C1 132.23(14) . . ? O13 C12 O14 123.79(14) . . ? O13 C12 C2 126.16(15) . . ? O14 C12 C2 110.03(12) . . ? O17 C16 O18 123.45(14) . . ? O17 C16 C3 125.38(14) . . ? O18 C16 C3 111.17(12) . . ? C25 C20 C21 116.50(15) . . ? C25 C20 C4 123.41(14) . . ? C21 C20 C4 120.08(15) . . ? C22 C21 C20 119.27(17) . . ? N23 C22 C21 124.92(16) . . ? N23 C24 C25 124.70(18) . . ? C24 C25 C20 119.31(16) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 65.07 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.248 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.036