Electronic Supplementary Material for CrystEngComm This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Qingdao Zeng' _publ_contact_author_address ; Institute of Chemistry Chinese Academy of Sciences Beijing 100080 CHINA ; _publ_contact_author_email STMZQD@ICCAS.AC.CN _publ_section_title ; Polymeric Hydrogen-Bonded Supramolecules by Self-Assembling of Adamantane Derivatives with Bipyridines ; loop_ _publ_author_name 'Qingdao Zeng' 'Chuying Shu' 'Chen Wang' 'Dongxia Wu' # Attachment '1.CIF.txt' data_a _database_code_depnum_ccdc_archive 'CCDC 221571' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H34 N2 O2' _chemical_formula_weight 502.66 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 Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 6.3316(13) _cell_length_b 12.517(3) _cell_length_c 33.042(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2618.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 16481 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.563 _exptl_absorpt_correction_T_max 0.992 _exptl_special_details ; ABSCOR by T.Higashi 8 March, 1995 ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean '100x100 microns' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16481 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2928 _reflns_number_gt 1553 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Molecular Structure Corporation (1994) MSC/AFC Diffractometer Control Software MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. ; _computing_cell_refinement ; Molecular Structure Corporation (1994) MSC/AFC Diffractometer Control Software MSC, 3200 Research Forest Drive, The Woodlands, TX 77381 USA. ; _computing_data_reduction ; Sheldrick, G. M. (1998) SHELXS98, Program for the Solution of Crystal Structure, University of Gottingen, Germany. ; _computing_structure_solution ; Sheldrick, G. M. (1998) SHELXS98, Program for the Solution of Crystal Structure, University of Gottingen, Germany. ; _computing_structure_refinement ; Sheldrick, G. M. (1998) SHELXL98, Program for the Refinement of Crystal Structure, University of Gottingen, Germany. ; _computing_molecular_graphics ; Interactive Molecular Graphics XP, Virsion 4.2 for MSDOS (1990), Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. ; _computing_publication_material ; Sheldrick, G. M. (1998) SHELXL98, Program for the refinement of Crystal Structure, University of Gottingen, Germany. ; _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^)+(0.0237P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ; hydrogen atoms are generated by HFIX instructions or difmap ; _refine_ls_hydrogen_treatment ; hydrogen coordinates ride on the coordinates of the previous atom, the isotropic U values are 1.2 OR 1.5 time over the U values of the previous atom. ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2928 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0796 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.0852 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_restrained_S_all 0.901 _refine_ls_shift/su_max 0.006 _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 O O 0.2631(2) -0.11807(9) 0.09164(3) 0.0584(3) Uani 1 1 d . . . N N -0.0655(2) -0.24917(10) 0.06603(4) 0.0558(4) Uani 1 1 d . . . C1 C 0.2056(3) -0.04202(11) 0.11940(4) 0.0419(4) Uani 1 1 d . . . C2 C 0.0086(3) -0.03866(11) 0.13734(4) 0.0458(4) Uani 1 1 d . . . H2 H -0.0934 -0.0886 0.1301 0.055 Uiso 1 1 calc R . . C3 C -0.0378(2) 0.03819(10) 0.16589(4) 0.0412(4) Uani 1 1 d . . . H3 H -0.1712 0.0383 0.1777 0.049 Uiso 1 1 calc R . . C4 C 0.1074(2) 0.11571(10) 0.17771(4) 0.0333(3) Uani 1 1 d . . . C5 C 0.3015(2) 0.11268(11) 0.15823(4) 0.0423(4) Uani 1 1 d . . . H5 H 0.4020 0.1641 0.1646 0.051 Uiso 1 1 calc R . . C6 C 0.3512(3) 0.03568(11) 0.12952(4) 0.0457(4) Uani 1 1 d . . . H6 H 0.4829 0.0364 0.1171 0.055 Uiso 1 1 calc R . . C7 C 0.0551(2) 0.19196(10) 0.21231(4) 0.0318(3) Uani 1 1 d . . . C8 C -0.1346(2) 0.26491(10) 0.20287(4) 0.0382(4) Uani 1 1 d . . . H8A H -0.1011 0.3102 0.1799 0.046 Uiso 1 1 calc R . . H8B H -0.2559 0.2215 0.1957 0.046 Uiso 1 1 calc R . . C9 C -0.1888(2) 0.33468(10) 0.23960(4) 0.0403(4) Uani 1 1 d . . . H9 H -0.3106 0.3798 0.2331 0.048 Uiso 1 1 calc R . . C10 C 0.0000 0.40570(15) 0.2500 0.0478(6) Uani 1 2 d S . . H10A H -0.0343 0.4511 0.2729 0.057 Uiso 0.50 1 calc PR . . H10B H 0.0343 0.4511 0.2271 0.057 Uiso 0.50 1 calc PR . . C11 C 0.0000 0.12466(13) 0.2500 0.0314(5) Uani 1 2 d S . . H11A H -0.1191 0.0789 0.2436 0.038 Uiso 0.50 1 calc PR . . H11B H 0.1191 0.0789 0.2564 0.038 Uiso 0.50 1 calc PR . . C12 C 0.2425(2) 0.26444(11) 0.22379(4) 0.0378(4) Uani 1 1 d . . . H12A H 0.3644 0.2206 0.2301 0.045 Uiso 1 1 calc R . . H12B H 0.2785 0.3096 0.2009 0.045 Uiso 1 1 calc R . . C13 C -0.5080(3) -0.47334(11) 0.01681(5) 0.0568(5) Uani 1 1 d . . . H13 H -0.6292 -0.4842 0.0322 0.068 Uiso 1 1 calc R . . C14 C -0.3506(3) -0.39693(11) 0.03278(5) 0.0486(4) Uani 1 1 d . . . C15 C -0.1533(3) -0.37972(12) 0.01587(5) 0.0534(5) Uani 1 1 d . . . H15 H -0.1127 -0.4170 -0.0072 0.064 Uiso 1 1 calc R . . C16 C -0.0170(3) -0.30676(11) 0.03342(5) 0.0548(5) Uani 1 1 d . . . H16 H 0.1156 -0.2974 0.0218 0.066 Uiso 1 1 calc R . . C17 C -0.2563(3) -0.26509(14) 0.08141(5) 0.0655(5) Uani 1 1 d . . . H17 H -0.2950 -0.2247 0.1038 0.079 Uiso 1 1 calc R . . C18 C -0.4004(3) -0.33665(12) 0.06667(5) 0.0594(5) Uani 1 1 d . . . H18 H -0.5307 -0.3448 0.0793 0.071 Uiso 1 1 calc R . . HO H 0.139(3) -0.1588(13) 0.0845(5) 0.088(6) 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 O 0.0588(8) 0.0578(7) 0.0585(7) -0.0222(6) 0.0050(7) 0.0003(7) N 0.0642(11) 0.0508(8) 0.0525(9) -0.0080(7) 0.0004(8) -0.0127(8) C1 0.0476(11) 0.0423(8) 0.0359(8) -0.0041(7) -0.0017(8) 0.0016(8) C2 0.0459(10) 0.0444(9) 0.0470(9) -0.0086(8) -0.0002(8) -0.0128(8) C3 0.0378(10) 0.0460(8) 0.0398(9) -0.0054(7) 0.0036(8) -0.0093(8) C4 0.0324(9) 0.0359(7) 0.0316(7) 0.0017(6) -0.0039(7) -0.0028(7) C5 0.0373(10) 0.0466(8) 0.0431(9) -0.0057(7) -0.0012(8) -0.0087(8) C6 0.0373(10) 0.0561(9) 0.0438(9) -0.0038(8) 0.0044(8) -0.0017(8) C7 0.0275(8) 0.0330(7) 0.0349(7) -0.0001(6) -0.0041(7) -0.0029(6) C8 0.0379(9) 0.0390(8) 0.0375(8) 0.0071(7) -0.0055(7) -0.0004(7) C9 0.0411(10) 0.0343(7) 0.0455(9) 0.0039(7) -0.0040(8) 0.0086(7) C10 0.0612(16) 0.0315(11) 0.0506(14) 0.000 -0.0024(13) 0.000 C11 0.0285(11) 0.0312(10) 0.0347(11) 0.000 -0.0031(9) 0.000 C12 0.0354(8) 0.0384(7) 0.0394(8) 0.0007(7) -0.0026(7) -0.0066(7) C13 0.0648(12) 0.0504(10) 0.0554(11) -0.0036(8) 0.0027(10) -0.0049(10) C14 0.0574(12) 0.0400(8) 0.0486(10) 0.0014(8) -0.0062(9) -0.0074(9) C15 0.0636(12) 0.0456(9) 0.0508(10) -0.0108(8) -0.0014(10) 0.0009(9) C16 0.0557(12) 0.0509(9) 0.0578(10) 0.0011(9) 0.0030(9) -0.0036(10) C17 0.0776(14) 0.0659(11) 0.0530(11) -0.0165(9) 0.0081(11) -0.0195(11) C18 0.0646(12) 0.0607(10) 0.0529(10) -0.0078(9) 0.0071(10) -0.0173(10) _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 O C1 1.3714(16) . ? N C17 1.326(2) . ? N C16 1.3324(19) . ? C1 C6 1.3810(19) . ? C1 C2 1.381(2) . ? C2 C3 1.3790(19) . ? C3 C4 1.3929(18) . ? C4 C5 1.388(2) . ? C4 C7 1.5256(18) . ? C5 C6 1.3885(19) . ? C7 C12 1.5411(18) . ? C7 C8 1.5404(18) . ? C7 C11 1.5435(15) . ? C8 C9 1.5342(18) . ? C9 C10 1.5289(17) . ? C9 C12 1.5335(17) 3 ? C10 C9 1.5289(17) 3 ? C11 C7 1.5435(15) 3 ? C12 C9 1.5335(17) 3 ? C13 C13 1.300(3) 5_445 ? C13 C14 1.479(2) . ? C14 C18 1.387(2) . ? C14 C15 1.385(2) . ? C15 C16 1.384(2) . ? C17 C18 1.368(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 C17 N C16 116.01(15) . . ? O C1 C6 118.26(14) . . ? O C1 C2 123.23(14) . . ? C6 C1 C2 118.51(14) . . ? C3 C2 C1 120.48(14) . . ? C2 C3 C4 122.48(14) . . ? C5 C4 C3 115.81(13) . . ? C5 C4 C7 123.85(12) . . ? C3 C4 C7 120.17(13) . . ? C4 C5 C6 122.45(14) . . ? C1 C6 C5 120.20(14) . . ? C4 C7 C12 112.68(11) . . ? C4 C7 C8 112.86(11) . . ? C12 C7 C8 107.52(10) . . ? C4 C7 C11 108.19(10) . . ? C12 C7 C11 107.25(10) . . ? C8 C7 C11 108.11(10) . . ? C9 C8 C7 110.59(11) . . ? C10 C9 C12 109.23(10) . 3 ? C10 C9 C8 109.50(11) . . ? C12 C9 C8 110.32(10) 3 . ? C9 C10 C9 108.89(14) . 3 ? C7 C11 C7 113.85(14) 3 . ? C9 C12 C7 111.17(12) 3 . ? C13 C13 C14 125.7(2) 5_445 . ? C18 C14 C15 116.49(15) . . ? C18 C14 C13 119.14(16) . . ? C15 C14 C13 124.36(15) . . ? C16 C15 C14 119.74(16) . . ? N C16 C15 123.51(17) . . ? N C17 C18 124.74(16) . . ? C17 C18 C14 119.48(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 O C1 C2 C3 178.23(13) . . . . ? C6 C1 C2 C3 -2.6(2) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? C2 C3 C4 C5 1.5(2) . . . . ? C2 C3 C4 C7 -174.07(12) . . . . ? C3 C4 C5 C6 -1.7(2) . . . . ? C7 C4 C5 C6 173.67(13) . . . . ? O C1 C6 C5 -178.40(12) . . . . ? C2 C1 C6 C5 2.3(2) . . . . ? C4 C5 C6 C1 -0.2(2) . . . . ? C5 C4 C7 C12 -0.86(18) . . . . ? C3 C4 C7 C12 174.34(12) . . . . ? C5 C4 C7 C8 121.16(15) . . . . ? C3 C4 C7 C8 -63.64(16) . . . . ? C5 C4 C7 C11 -119.26(13) . . . . ? C3 C4 C7 C11 55.94(15) . . . . ? C4 C7 C8 C9 176.40(11) . . . . ? C12 C7 C8 C9 -58.72(14) . . . . ? C11 C7 C8 C9 56.77(13) . . . . ? C7 C8 C9 C10 61.01(13) . . . . ? C7 C8 C9 C12 -59.23(15) . . . 3 ? C12 C9 C10 C9 60.19(8) 3 . . 3 ? C8 C9 C10 C9 -60.72(8) . . . 3 ? C4 C7 C11 C7 179.56(12) . . . 3 ? C12 C7 C11 C7 57.76(8) . . . 3 ? C8 C7 C11 C7 -57.90(8) . . . 3 ? C4 C7 C12 C9 -176.28(10) . . . 3 ? C8 C7 C12 C9 58.73(14) . . . 3 ? C11 C7 C12 C9 -57.33(13) . . . 3 ? C13 C13 C14 C18 172.5(2) 5_445 . . . ? C13 C13 C14 C15 -6.8(3) 5_445 . . . ? C18 C14 C15 C16 1.1(2) . . . . ? C13 C14 C15 C16 -179.52(14) . . . . ? C17 N C16 C15 -0.1(2) . . . . ? C14 C15 C16 N -1.1(2) . . . . ? C16 N C17 C18 1.4(3) . . . . ? N C17 C18 C14 -1.3(3) . . . . ? C15 C14 C18 C17 0.0(2) . . . . ? C13 C14 C18 C17 -179.40(15) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.188 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.036 # Attachment '2.CIF.txt' data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 221572' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H32 N2 O2 S' _chemical_formula_weight 508.66 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 12.632(3) _cell_length_b 32.034(6) _cell_length_c 6.2215(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2517.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12032 _cell_measurement_theta_min 1.27 _cell_measurement_theta_max 17.48 _exptl_crystal_description ? _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.163 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.705 _exptl_absorpt_correction_T_max 0.989 _exptl_special_details ; ABSCOR by T.Higashi 8 March, 1995 ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean '100x100 microns' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12032 _diffrn_reflns_av_R_equivalents 0.0816 _diffrn_reflns_av_sigmaI/netI 0.1305 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2839 _reflns_number_gt 1025 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Molecular Structure Corporation (1994) MSC/AFC Diffractometer Control Software MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. ; _computing_cell_refinement ; Molecular Structure Corporation (1994) MSC/AFC Diffractometer Control Software MSC, 3200 Research Forest Drive, The Woodlands, TX 77381 USA. ; _computing_data_reduction ; Sheldrick, G. M. (1998) SHELXS98, Program for the Solution of Crystal Structure, University of Gottingen, Germany. ; _computing_structure_solution ; Sheldrick, G. M. (1998) SHELXS98, Program for the Solution of Crystal Structure, University of Gottingen, Germany. ; _computing_structure_refinement ; Sheldrick, G. M. (1998) SHELXL98, Program for the Refinement of Crystal Structure, University of Gottingen, Germany. ; _computing_molecular_graphics ; Interactive Molecular Graphics XP, Virsion 4.2 for MSDOS (1990), Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. ; _computing_publication_material ; Sheldrick, G. M. (1998) SHELXL98, Program for the refinement of Crystal Structure, University of Gottingen, Germany. ; _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^)+(0.0154P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ; hydrogen atoms are generated by HFIX instructions' or difmap ; _refine_ls_hydrogen_treatment ; hydrogen coordinates ride on the coordinates of the previous atom, the isotropic U values are 1.2 OR 1.5 time over the U values of the previous atom. ; _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0078(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2839 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1351 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.0769 _refine_ls_wR_factor_gt 0.0634 _refine_ls_goodness_of_fit_ref 0.826 _refine_ls_restrained_S_all 0.826 _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 S1 S 0.2500 0.5000 1.23820(18) 0.0872(4) Uani 1 2 d S . . O1 O 0.62019(12) 0.41034(4) 0.4848(3) 0.0714(5) Uani 1 1 d . . . HO1 H 0.5580 0.4178 0.5826 0.080 Uiso 1 1 d . . . N1 N 0.48898(16) 0.43445(6) 0.8175(3) 0.0654(6) Uani 1 1 d . . . C1 C 0.92890(15) 0.28856(6) 0.6953(3) 0.0362(5) Uani 1 1 d . . . C2 C 1.00036(16) 0.27723(5) 0.5065(4) 0.0424(5) Uani 1 1 d . . . H2A H 1.0450 0.3009 0.4711 0.051 Uiso 1 1 calc R . . H2B H 0.9571 0.2709 0.3818 0.051 Uiso 1 1 calc R . . C3 C 0.8623(2) 0.2500 0.7500 0.0365(7) Uani 1 2 d S . . H3A H 0.8170 0.2565 0.8714 0.044 Uiso 0.50 1 calc PR . . H3B H 0.8170 0.2435 0.6286 0.044 Uiso 0.50 1 calc PR . . C4 C 1.00026(17) 0.29780(5) 0.8855(3) 0.0449(6) Uani 1 1 d . . . H4A H 0.9572 0.3049 1.0093 0.054 Uiso 1 1 calc R . . H4B H 1.0447 0.3217 0.8523 0.054 Uiso 1 1 calc R . . C5 C 1.06995(15) 0.23955(6) 0.5602(3) 0.0453(6) Uani 1 1 d . . . H5 H 1.1140 0.2327 0.4354 0.054 Uiso 1 1 calc R . . C6 C 1.1410(2) 0.2500 0.7500 0.0478(8) Uani 1 2 d S . . H6A H 1.1859 0.2736 0.7155 0.057 Uiso 0.50 1 calc PR . . H6B H 1.1859 0.2264 0.7845 0.057 Uiso 0.50 1 calc PR . . C7 C 0.85326(16) 0.32382(6) 0.6433(3) 0.0374(5) Uani 1 1 d . . . C8 C 0.77616(16) 0.33526(6) 0.7895(4) 0.0461(6) Uani 1 1 d . . . H8 H 0.7763 0.3230 0.9249 0.055 Uiso 1 1 calc R . . C9 C 0.69886(16) 0.36430(6) 0.7416(4) 0.0505(6) Uani 1 1 d . . . H9 H 0.6486 0.3715 0.8444 0.061 Uiso 1 1 calc R . . C10 C 0.69638(18) 0.38247(7) 0.5419(4) 0.0492(6) Uani 1 1 d . . . C11 C 0.77389(18) 0.37306(7) 0.3983(4) 0.0551(6) Uani 1 1 d . . . H11 H 0.7753 0.3863 0.2652 0.066 Uiso 1 1 calc R . . C12 C 0.85091(18) 0.34384(6) 0.4495(4) 0.0487(6) Uani 1 1 d . . . H12 H 0.9028 0.3377 0.3483 0.058 Uiso 1 1 calc R . . C13 C 0.46178(19) 0.42132(7) 1.0111(5) 0.0672(8) Uani 1 1 d . . . H13 H 0.4957 0.3977 1.0645 0.081 Uiso 1 1 calc R . . C14 C 0.38763(18) 0.43986(7) 1.1381(4) 0.0629(7) Uani 1 1 d . . . H14 H 0.3702 0.4286 1.2712 0.075 Uiso 1 1 calc R . . C15 C 0.33913(16) 0.47548(7) 1.0660(4) 0.0541(7) Uani 1 1 d . . . C16 C 0.36898(16) 0.49052(8) 0.8700(4) 0.0604(7) Uani 1 1 d . . . H16 H 0.3403 0.5152 0.8173 0.072 Uiso 1 1 calc R . . C17 C 0.44203(17) 0.46862(7) 0.7517(4) 0.0630(7) Uani 1 1 d . . . H17 H 0.4593 0.4787 0.6160 0.076 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0691(6) 0.1352(9) 0.0574(6) 0.000 0.000 0.0325(7) O1 0.0646(10) 0.0774(10) 0.0721(11) 0.0060(12) -0.0031(10) 0.0294(10) N1 0.0626(14) 0.0564(12) 0.0771(17) 0.0042(13) 0.0028(13) 0.0071(12) C1 0.0392(12) 0.0381(11) 0.0314(12) -0.0053(11) 0.0036(10) 0.0007(11) C2 0.0499(13) 0.0420(11) 0.0355(11) -0.0044(12) 0.0090(11) -0.0076(12) C3 0.0377(16) 0.0391(16) 0.0328(17) -0.0038(16) 0.000 0.000 C4 0.0513(14) 0.0444(12) 0.0391(12) -0.0063(11) 0.0017(13) -0.0083(12) C5 0.0438(13) 0.0519(13) 0.0402(14) -0.0051(12) 0.0104(11) 0.0053(11) C6 0.0385(17) 0.0494(18) 0.056(2) -0.0041(19) 0.000 0.000 C7 0.0400(12) 0.0356(12) 0.0365(12) -0.0047(11) 0.0040(12) -0.0047(10) C8 0.0501(15) 0.0454(12) 0.0428(14) 0.0042(12) 0.0051(12) 0.0003(12) C9 0.0430(13) 0.0555(13) 0.0531(15) -0.0034(14) 0.0072(13) 0.0062(13) C10 0.0504(14) 0.0480(13) 0.0491(15) -0.0027(14) -0.0041(13) 0.0057(12) C11 0.0673(16) 0.0561(15) 0.0419(13) 0.0069(13) 0.0014(14) 0.0079(14) C12 0.0601(15) 0.0450(12) 0.0410(14) -0.0003(12) 0.0074(13) 0.0017(13) C13 0.0667(19) 0.0501(14) 0.085(2) 0.0169(18) -0.0017(18) 0.0041(15) C14 0.0610(18) 0.0652(16) 0.0625(17) 0.0157(16) 0.0076(16) -0.0096(15) C15 0.0443(14) 0.0600(15) 0.0578(17) 0.0035(14) -0.0021(13) 0.0010(12) C16 0.0499(15) 0.0607(17) 0.0706(18) 0.0169(15) 0.0022(15) 0.0065(14) C17 0.0574(16) 0.0687(16) 0.0629(17) 0.0185(17) 0.0058(16) 0.0002(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C15 1.741(2) . ? S1 C15 1.741(2) 2_565 ? O1 C10 1.360(2) . ? N1 C17 1.310(3) . ? N1 C13 1.321(3) . ? C1 C7 1.514(3) . ? C1 C4 1.517(3) . ? C1 C2 1.525(3) . ? C1 C3 1.533(2) . ? C2 C5 1.530(2) . ? C3 C1 1.533(2) 4_556 ? C4 C5 1.523(2) 4_556 ? C5 C6 1.521(2) . ? C5 C4 1.523(2) 4_556 ? C6 C5 1.521(2) 4_556 ? C7 C12 1.366(3) . ? C7 C8 1.382(3) . ? C8 C9 1.381(2) . ? C9 C10 1.372(3) . ? C10 C11 1.359(3) . ? C11 C12 1.387(3) . ? C13 C14 1.362(3) . ? C14 C15 1.371(3) . ? C15 C16 1.364(3) . ? C16 C17 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 C15 S1 C15 104.06(17) . 2_565 ? C17 N1 C13 115.6(2) . . ? C7 C1 C4 113.34(17) . . ? C7 C1 C2 112.72(16) . . ? C4 C1 C2 107.19(16) . . ? C7 C1 C3 107.60(15) . . ? C4 C1 C3 108.08(15) . . ? C2 C1 C3 107.69(14) . . ? C1 C2 C5 111.07(17) . . ? C1 C3 C1 113.4(2) 4_556 . ? C1 C4 C5 111.31(16) . 4_556 ? C6 C5 C4 109.97(16) . 4_556 ? C6 C5 C2 109.58(15) . . ? C4 C5 C2 109.63(15) 4_556 . ? C5 C6 C5 107.6(2) . 4_556 ? C12 C7 C8 116.17(19) . . ? C12 C7 C1 123.53(19) . . ? C8 C7 C1 120.12(18) . . ? C9 C8 C7 122.3(2) . . ? C10 C9 C8 119.8(2) . . ? C11 C10 O1 118.9(2) . . ? C11 C10 C9 119.0(2) . . ? O1 C10 C9 122.1(2) . . ? C10 C11 C12 120.3(2) . . ? C7 C12 C11 122.3(2) . . ? N1 C13 C14 124.7(2) . . ? C13 C14 C15 118.7(2) . . ? C16 C15 C14 117.6(2) . . ? C16 C15 S1 124.7(2) . . ? C14 C15 S1 117.6(2) . . ? C15 C16 C17 119.0(2) . . ? N1 C17 C16 124.3(2) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.211 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.050 # Attachment '3.CIF.txt' data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 221573' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H32 N2 O4' _chemical_formula_weight 508.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.823(4) _cell_length_b 10.157(2) _cell_length_c 13.869(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.44(3) _cell_angle_gamma 90.00 _cell_volume 2607.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 19282 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.678 _exptl_absorpt_correction_T_max 0.987 _exptl_special_details ; ABSCOR by T.Higashi 8 March, 1995 ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean '100x100 microns' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19282 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0760 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5918 _reflns_number_gt 2849 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Molecular Structure Corporation (1994) MSC/AFC Diffractometer Control Software MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. ; _computing_cell_refinement ; Molecular Structure Corporation (1994) MSC/AFC Diffractometer Control Software MSC, 3200 Research Forest Drive, The Woodlands, TX 77381 USA. ; _computing_data_reduction ; Sheldrick, G. M. (1998) SHELXS98, Program for the Solution of Crystal Structure, University of Gottingen, Germany. ; _computing_structure_solution ; Sheldrick, G. M. (1998) SHELXS98, Program for the Solution of Crystal Structure, University of Gottingen, Germany. ; _computing_structure_refinement ; Sheldrick, G. M. (1998) SHELXL98, Program for the Refinement of Crystal Structure, University of Gottingen, Germany. ; _computing_molecular_graphics ; Interactive Molecular Graphics XP, Virsion 4.2 for MSDOS (1990), Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. ; _computing_publication_material ; Sheldrick, G. M. (1998) SHELXL98, Program for the refinement of Crystal Structure, University of Gottingen, Germany. ; _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^)+(0.0218P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ; hydrogen atoms are generated by HFIX instructions or difmap ; _refine_ls_hydrogen_treatment ; hydrogen coordinates ride on the coordinates of the previous atom, the isotropic U values are 1.2 OR 1.5 time over the U values of the previous atom. ; _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0064(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5918 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0980 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.0772 _refine_ls_wR_factor_gt 0.0710 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.15763(6) 0.27095(14) -0.13115(8) 0.0561(4) Uani 1 1 d . . . O2 O 0.77346(6) 0.34172(13) 0.20639(10) 0.0632(4) Uani 1 1 d . . . O3 O -0.12279(6) -0.82921(11) -0.13324(9) 0.0632(4) Uani 1 1 d . . . O4 O 0.07675(6) 0.04992(12) -0.12240(10) 0.0720(4) Uani 1 1 d . . . N1 N -0.09530(7) -0.70921(14) -0.13201(10) 0.0477(4) Uani 1 1 d . . . N2 N 0.05082(7) -0.06945(14) -0.12541(10) 0.0492(4) Uani 1 1 d . . . C1 C 0.40121(8) 0.45599(15) 0.38336(11) 0.0406(4) Uani 1 1 d . . . H1 H 0.3941 0.5373 0.4185 0.049 Uiso 1 1 calc R . . C2 C 0.39658(8) 0.33747(16) 0.45039(11) 0.0457(4) Uani 1 1 d . . . H2A H 0.4333 0.3446 0.5090 0.055 Uiso 1 1 calc R . . H2B H 0.3496 0.3356 0.4699 0.055 Uiso 1 1 calc R . . C3 C 0.47580(8) 0.45849(15) 0.35400(10) 0.0387(4) Uani 1 1 d . . . H3A H 0.5127 0.4670 0.4123 0.046 Uiso 1 1 calc R . . H3B H 0.4792 0.5344 0.3126 0.046 Uiso 1 1 calc R . . C4 C 0.34271(8) 0.44523(15) 0.29139(10) 0.0395(4) Uani 1 1 d . . . H4A H 0.3452 0.5211 0.2497 0.047 Uiso 1 1 calc R . . H4B H 0.2955 0.4446 0.3100 0.047 Uiso 1 1 calc R . . C5 C 0.40788(8) 0.21158(16) 0.39542(10) 0.0403(4) Uani 1 1 d . . . H5 H 0.4046 0.1355 0.4379 0.048 Uiso 1 1 calc R . . C6 C 0.48252(8) 0.21372(15) 0.36619(10) 0.0394(4) Uani 1 1 d . . . H6A H 0.4899 0.1326 0.3324 0.047 Uiso 1 1 calc R . . H6B H 0.5195 0.2194 0.4246 0.047 Uiso 1 1 calc R . . C7 C 0.48937(7) 0.33232(14) 0.29866(10) 0.0333(4) Uani 1 1 d . . . C8 C 0.42912(7) 0.32149(15) 0.20757(10) 0.0333(4) Uani 1 1 d . . . H8A H 0.4363 0.2419 0.1719 0.040 Uiso 1 1 calc R . . H8B H 0.4324 0.3959 0.1647 0.040 Uiso 1 1 calc R . . C9 C 0.35285(7) 0.31842(15) 0.23453(10) 0.0332(4) Uani 1 1 d . . . C10 C 0.35025(8) 0.19984(15) 0.30277(10) 0.0390(4) Uani 1 1 d . . . H10A H 0.3029 0.1949 0.3208 0.047 Uiso 1 1 calc R . . H10B H 0.3580 0.1194 0.2684 0.047 Uiso 1 1 calc R . . C11 C 0.56444(8) 0.33492(14) 0.27216(11) 0.0360(4) Uani 1 1 d . . . C12 C 0.57743(8) 0.32885(15) 0.17642(11) 0.0418(4) Uani 1 1 d . . . H12 H 0.5384 0.3232 0.1248 0.050 Uiso 1 1 calc R . . C13 C 0.64677(8) 0.33100(16) 0.15570(12) 0.0473(4) Uani 1 1 d . . . H13 H 0.6534 0.3274 0.0909 0.057 Uiso 1 1 calc R . . C14 C 0.70584(8) 0.33843(16) 0.23021(13) 0.0449(4) Uani 1 1 d . . . C15 C 0.69476(8) 0.34462(16) 0.32585(12) 0.0492(5) Uani 1 1 d . . . H15 H 0.7341 0.3499 0.3771 0.059 Uiso 1 1 calc R . . C16 C 0.62556(8) 0.34293(16) 0.34553(11) 0.0468(4) Uani 1 1 d . . . H16 H 0.6194 0.3473 0.4105 0.056 Uiso 1 1 calc R . . C17 C 0.29675(7) 0.30786(15) 0.14044(10) 0.0343(4) Uani 1 1 d . . . C18 C 0.25445(8) 0.19569(15) 0.11748(11) 0.0396(4) Uani 1 1 d . . . H18 H 0.2578 0.1279 0.1632 0.048 Uiso 1 1 calc R . . C19 C 0.20737(7) 0.18197(16) 0.02837(11) 0.0428(4) Uani 1 1 d . . . H19 H 0.1799 0.1058 0.0149 0.051 Uiso 1 1 calc R . . C20 C 0.20159(7) 0.28187(17) -0.03993(11) 0.0417(4) Uani 1 1 d . . . C21 C 0.24092(8) 0.39602(16) -0.01894(11) 0.0412(4) Uani 1 1 d . . . H21 H 0.2360 0.4647 -0.0640 0.049 Uiso 1 1 calc R . . C22 C 0.28805(7) 0.40770(16) 0.07014(11) 0.0393(4) Uani 1 1 d . . . H22 H 0.3147 0.4847 0.0834 0.047 Uiso 1 1 calc R . . C23 C -0.13853(9) -0.60279(18) -0.13880(13) 0.0597(5) Uani 1 1 d . . . H23 H -0.1880 -0.6141 -0.1432 0.072 Uiso 1 1 calc R . . C24 C -0.11091(9) -0.47859(17) -0.13938(12) 0.0547(5) Uani 1 1 d . . . H24 H -0.1420 -0.4068 -0.1441 0.066 Uiso 1 1 calc R . . C25 C -0.03694(8) -0.45721(16) -0.13301(11) 0.0402(4) Uani 1 1 d . . . C26 C 0.00515(8) -0.56976(16) -0.12542(11) 0.0451(4) Uani 1 1 d . . . H26 H 0.0549 -0.5610 -0.1201 0.054 Uiso 1 1 calc R . . C27 C -0.02361(8) -0.69359(17) -0.12541(11) 0.0472(4) Uani 1 1 d . . . H27 H 0.0064 -0.7669 -0.1208 0.057 Uiso 1 1 calc R . . C28 C -0.02066(9) -0.08844(17) -0.13097(12) 0.0546(5) Uani 1 1 d . . . H28 H -0.0511 -0.0161 -0.1322 0.066 Uiso 1 1 calc R . . C29 C -0.04881(8) -0.21233(17) -0.13482(12) 0.0524(5) Uani 1 1 d . . . H29 H -0.0984 -0.2224 -0.1398 0.063 Uiso 1 1 calc R . . C30 C -0.00626(8) -0.32316(15) -0.13163(10) 0.0387(4) Uani 1 1 d . . . C31 C 0.06713(8) -0.30031(17) -0.12610(11) 0.0482(4) Uani 1 1 d . . . H31 H 0.0983 -0.3716 -0.1246 0.058 Uiso 1 1 calc R . . C32 C 0.09452(9) -0.17516(18) -0.12278(12) 0.0525(5) Uani 1 1 d . . . H32 H 0.1439 -0.1629 -0.1186 0.063 Uiso 1 1 calc R . . HO1 H 0.1377(12) 0.186(2) -0.1328(17) 0.134(10) Uiso 1 1 d . . . HO2 H 0.8073(10) 0.3357(19) 0.2648(13) 0.093(8) 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 0.0443(7) 0.0745(10) 0.0441(7) 0.0005(7) -0.0061(6) -0.0049(7) O2 0.0385(7) 0.0775(10) 0.0769(10) 0.0114(8) 0.0189(7) 0.0050(7) O3 0.0500(7) 0.0427(8) 0.0948(10) -0.0015(7) 0.0077(7) -0.0053(6) O4 0.0633(8) 0.0439(8) 0.1045(11) -0.0103(7) 0.0038(7) -0.0156(6) N1 0.0421(9) 0.0388(9) 0.0617(10) -0.0013(7) 0.0076(7) -0.0014(7) N2 0.0478(9) 0.0428(9) 0.0540(9) -0.0075(7) 0.0014(7) -0.0034(8) C1 0.0475(10) 0.0410(10) 0.0357(9) -0.0106(8) 0.0135(8) -0.0027(8) C2 0.0484(10) 0.0599(12) 0.0307(8) -0.0060(9) 0.0120(7) -0.0083(9) C3 0.0422(9) 0.0408(10) 0.0323(9) -0.0046(8) 0.0049(7) -0.0082(7) C4 0.0390(9) 0.0436(10) 0.0372(9) -0.0049(8) 0.0106(7) -0.0003(8) C5 0.0473(10) 0.0429(10) 0.0315(9) 0.0055(8) 0.0089(7) -0.0087(8) C6 0.0442(10) 0.0414(10) 0.0314(8) 0.0010(8) 0.0034(7) -0.0033(8) C7 0.0335(8) 0.0394(9) 0.0263(8) -0.0027(7) 0.0037(7) -0.0036(7) C8 0.0351(8) 0.0351(9) 0.0309(8) -0.0025(7) 0.0092(7) -0.0024(7) C9 0.0327(8) 0.0375(9) 0.0300(8) -0.0044(8) 0.0067(7) -0.0035(7) C10 0.0410(9) 0.0419(10) 0.0349(9) 0.0005(8) 0.0093(7) -0.0086(8) C11 0.0356(9) 0.0359(9) 0.0368(9) -0.0020(8) 0.0073(7) -0.0021(7) C12 0.0361(9) 0.0484(10) 0.0415(10) -0.0029(9) 0.0082(7) -0.0050(8) C13 0.0469(10) 0.0537(12) 0.0438(10) -0.0013(9) 0.0151(9) -0.0016(9) C14 0.0343(9) 0.0409(10) 0.0618(12) 0.0050(9) 0.0153(9) 0.0019(8) C15 0.0341(10) 0.0570(12) 0.0539(11) 0.0024(9) 0.0012(8) 0.0010(8) C16 0.0405(10) 0.0605(12) 0.0393(10) -0.0027(9) 0.0075(8) -0.0011(8) C17 0.0306(8) 0.0401(10) 0.0335(8) -0.0037(8) 0.0096(7) -0.0007(7) C18 0.0379(9) 0.0424(10) 0.0382(9) 0.0024(8) 0.0060(7) -0.0042(8) C19 0.0358(9) 0.0458(11) 0.0461(10) -0.0037(9) 0.0053(8) -0.0076(8) C20 0.0274(9) 0.0596(12) 0.0373(10) -0.0041(9) 0.0033(7) 0.0014(8) C21 0.0342(9) 0.0478(11) 0.0417(10) 0.0038(8) 0.0072(8) 0.0039(8) C22 0.0359(9) 0.0412(10) 0.0415(10) -0.0003(8) 0.0091(8) -0.0012(8) C23 0.0357(10) 0.0483(12) 0.0966(15) -0.0080(11) 0.0156(9) 0.0028(9) C24 0.0399(10) 0.0430(11) 0.0832(14) -0.0047(10) 0.0166(9) 0.0039(9) C25 0.0371(10) 0.0430(10) 0.0408(10) -0.0039(8) 0.0081(7) 0.0052(8) C26 0.0333(9) 0.0453(11) 0.0553(11) -0.0040(9) 0.0039(8) -0.0001(8) C27 0.0336(10) 0.0479(12) 0.0577(11) -0.0029(9) 0.0018(8) 0.0059(8) C28 0.0414(10) 0.0464(12) 0.0763(13) -0.0053(10) 0.0113(9) 0.0050(9) C29 0.0396(10) 0.0437(11) 0.0753(13) -0.0035(10) 0.0147(9) -0.0004(9) C30 0.0371(9) 0.0403(10) 0.0392(9) -0.0038(8) 0.0083(7) 0.0016(8) C31 0.0389(10) 0.0454(11) 0.0593(11) -0.0016(9) 0.0058(8) 0.0032(8) C32 0.0359(9) 0.0545(12) 0.0643(12) -0.0046(10) 0.0013(8) -0.0004(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 O1 C20 1.3851(18) . ? O2 C14 1.3719(17) . ? O3 N1 1.3231(16) . ? O4 N2 1.3049(16) . ? N1 C27 1.3454(18) . ? N1 C23 1.346(2) . ? N2 C28 1.3475(19) . ? N2 C32 1.349(2) . ? C1 C4 1.5306(19) . ? C1 C3 1.531(2) . ? C1 C2 1.533(2) . ? C2 C5 1.523(2) . ? C3 C7 1.5387(19) . ? C4 C9 1.5400(19) . ? C5 C10 1.5288(19) . ? C5 C6 1.5314(19) . ? C6 C7 1.5456(19) . ? C7 C11 1.5233(19) . ? C7 C8 1.5411(18) . ? C8 C9 1.5480(18) . ? C9 C17 1.5263(19) . ? C9 C10 1.5380(19) . ? C11 C16 1.3934(19) . ? C11 C12 1.3945(19) . ? C12 C13 1.3864(19) . ? C13 C14 1.376(2) . ? C14 C15 1.381(2) . ? C15 C16 1.3786(19) . ? C17 C18 1.3934(18) . ? C17 C22 1.3957(19) . ? C18 C19 1.3913(19) . ? C19 C20 1.379(2) . ? C20 C21 1.378(2) . ? C21 C22 1.3894(19) . ? C23 C24 1.365(2) . ? C24 C25 1.396(2) . ? C25 C26 1.384(2) . ? C25 C30 1.478(2) . ? C26 C27 1.369(2) . ? C28 C29 1.363(2) . ? C29 C30 1.378(2) . ? C30 C31 1.389(2) . ? C31 C32 1.369(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 O3 N1 C27 119.65(13) . . ? O3 N1 C23 120.59(13) . . ? C27 N1 C23 119.76(15) . . ? O4 N2 C28 119.91(14) . . ? O4 N2 C32 121.06(14) . . ? C28 N2 C32 119.03(14) . . ? C4 C1 C3 109.60(12) . . ? C4 C1 C2 109.76(12) . . ? C3 C1 C2 109.26(13) . . ? C5 C2 C1 109.10(12) . . ? C1 C3 C7 111.22(12) . . ? C1 C4 C9 110.45(12) . . ? C2 C5 C10 110.12(13) . . ? C2 C5 C6 109.79(12) . . ? C10 C5 C6 108.90(12) . . ? C5 C6 C7 110.65(12) . . ? C11 C7 C3 110.55(12) . . ? C11 C7 C8 112.37(11) . . ? C3 C7 C8 107.72(12) . . ? C11 C7 C6 110.03(12) . . ? C3 C7 C6 107.89(11) . . ? C8 C7 C6 108.14(11) . . ? C7 C8 C9 112.36(11) . . ? C17 C9 C10 112.14(12) . . ? C17 C9 C4 111.46(12) . . ? C10 C9 C4 108.61(12) . . ? C17 C9 C8 108.86(11) . . ? C10 C9 C8 107.37(12) . . ? C4 C9 C8 108.25(11) . . ? C5 C10 C9 111.06(12) . . ? C16 C11 C12 115.71(14) . . ? C16 C11 C7 120.28(13) . . ? C12 C11 C7 124.01(13) . . ? C13 C12 C11 122.05(15) . . ? C14 C13 C12 120.55(15) . . ? O2 C14 C13 118.64(15) . . ? O2 C14 C15 122.56(15) . . ? C13 C14 C15 118.79(15) . . ? C16 C15 C14 120.14(15) . . ? C15 C16 C11 122.75(15) . . ? C18 C17 C22 116.39(13) . . ? C18 C17 C9 122.07(13) . . ? C22 C17 C9 121.44(13) . . ? C19 C18 C17 122.05(14) . . ? C20 C19 C18 119.66(14) . . ? C21 C20 C19 120.11(14) . . ? C21 C20 O1 118.00(15) . . ? C19 C20 O1 121.89(15) . . ? C20 C21 C22 119.45(15) . . ? C21 C22 C17 122.31(15) . . ? N1 C23 C24 121.10(15) . . ? C23 C24 C25 121.33(16) . . ? C26 C25 C24 115.27(15) . . ? C26 C25 C30 122.89(14) . . ? C24 C25 C30 121.81(14) . . ? C27 C26 C25 122.54(15) . . ? N1 C27 C26 120.00(15) . . ? N2 C28 C29 120.77(15) . . ? C28 C29 C30 122.25(15) . . ? C29 C30 C31 115.58(15) . . ? C29 C30 C25 121.93(14) . . ? C31 C30 C25 122.48(14) . . ? C32 C31 C30 121.43(16) . . ? N2 C32 C31 120.93(15) . . ? 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 C1 C2 C5 60.12(16) . . . . ? C3 C1 C2 C5 -60.08(16) . . . . ? C4 C1 C3 C7 -60.15(16) . . . . ? C2 C1 C3 C7 60.15(16) . . . . ? C3 C1 C4 C9 59.80(16) . . . . ? C2 C1 C4 C9 -60.19(16) . . . . ? C1 C2 C5 C10 -59.42(16) . . . . ? C1 C2 C5 C6 60.49(16) . . . . ? C2 C5 C6 C7 -60.33(15) . . . . ? C10 C5 C6 C7 60.31(15) . . . . ? C1 C3 C7 C11 -178.64(12) . . . . ? C1 C3 C7 C8 58.24(15) . . . . ? C1 C3 C7 C6 -58.28(15) . . . . ? C5 C6 C7 C11 178.69(12) . . . . ? C5 C6 C7 C3 58.01(14) . . . . ? C5 C6 C7 C8 -58.24(15) . . . . ? C11 C7 C8 C9 179.83(12) . . . . ? C3 C7 C8 C9 -58.18(15) . . . . ? C6 C7 C8 C9 58.18(15) . . . . ? C1 C4 C9 C17 -177.94(12) . . . . ? C1 C4 C9 C10 58.03(15) . . . . ? C1 C4 C9 C8 -58.25(15) . . . . ? C7 C8 C9 C17 179.91(12) . . . . ? C7 C8 C9 C10 -58.48(15) . . . . ? C7 C8 C9 C4 58.60(15) . . . . ? C2 C5 C10 C9 59.09(16) . . . . ? C6 C5 C10 C9 -61.35(16) . . . . ? C17 C9 C10 C5 178.90(12) . . . . ? C4 C9 C10 C5 -57.48(15) . . . . ? C8 C9 C10 C5 59.37(15) . . . . ? C3 C7 C11 C16 60.35(18) . . . . ? C8 C7 C11 C16 -179.28(13) . . . . ? C6 C7 C11 C16 -58.72(18) . . . . ? C3 C7 C11 C12 -120.08(15) . . . . ? C8 C7 C11 C12 0.3(2) . . . . ? C6 C7 C11 C12 120.85(15) . . . . ? C16 C11 C12 C13 -0.2(2) . . . . ? C7 C11 C12 C13 -179.74(14) . . . . ? C11 C12 C13 C14 0.4(2) . . . . ? C12 C13 C14 O2 -179.32(14) . . . . ? C12 C13 C14 C15 -0.4(2) . . . . ? O2 C14 C15 C16 179.01(15) . . . . ? C13 C14 C15 C16 0.2(2) . . . . ? C14 C15 C16 C11 0.1(3) . . . . ? C12 C11 C16 C15 -0.1(2) . . . . ? C7 C11 C16 C15 179.50(14) . . . . ? C10 C9 C17 C18 -6.20(19) . . . . ? C4 C9 C17 C18 -128.22(14) . . . . ? C8 C9 C17 C18 112.45(15) . . . . ? C10 C9 C17 C22 177.45(13) . . . . ? C4 C9 C17 C22 55.43(17) . . . . ? C8 C9 C17 C22 -63.89(17) . . . . ? C22 C17 C18 C19 1.6(2) . . . . ? C9 C17 C18 C19 -174.90(13) . . . . ? C17 C18 C19 C20 -0.3(2) . . . . ? C18 C19 C20 C21 -1.6(2) . . . . ? C18 C19 C20 O1 177.47(13) . . . . ? C19 C20 C21 C22 2.1(2) . . . . ? O1 C20 C21 C22 -177.06(13) . . . . ? C20 C21 C22 C17 -0.6(2) . . . . ? C18 C17 C22 C21 -1.2(2) . . . . ? C9 C17 C22 C21 175.38(13) . . . . ? O3 N1 C23 C24 -178.81(16) . . . . ? C27 N1 C23 C24 0.2(3) . . . . ? N1 C23 C24 C25 0.0(3) . . . . ? C23 C24 C25 C26 -0.5(3) . . . . ? C23 C24 C25 C30 -178.80(16) . . . . ? C24 C25 C26 C27 0.8(2) . . . . ? C30 C25 C26 C27 179.08(15) . . . . ? O3 N1 C27 C26 179.12(14) . . . . ? C23 N1 C27 C26 0.1(2) . . . . ? C25 C26 C27 N1 -0.7(3) . . . . ? O4 N2 C28 C29 179.58(16) . . . . ? C32 N2 C28 C29 -0.6(3) . . . . ? N2 C28 C29 C30 1.1(3) . . . . ? C28 C29 C30 C31 -1.2(2) . . . . ? C28 C29 C30 C25 178.23(16) . . . . ? C26 C25 C30 C29 -177.01(16) . . . . ? C24 C25 C30 C29 1.2(2) . . . . ? C26 C25 C30 C31 2.4(2) . . . . ? C24 C25 C30 C31 -179.47(16) . . . . ? C29 C30 C31 C32 0.9(2) . . . . ? C25 C30 C31 C32 -178.56(15) . . . . ? O4 N2 C32 C31 -179.90(15) . . . . ? C28 N2 C32 C31 0.3(2) . . . . ? C30 C31 C32 N2 -0.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 HO2 O3 0.938(18) 1.749(18) 2.6839(19) 174.2(17) 4_656 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.205 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.048 # Attachment '4.CIF.txt' data_compound_4 _database_code_depnum_ccdc_archive 'CCDC 289578' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H26 N2 O4' _chemical_formula_weight 406.47 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.525(3) _cell_length_b 12.772(3) _cell_length_c 26.458(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4232.5(15) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 31224 _cell_measurement_theta_min 1.54 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.77 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9356 _exptl_absorpt_correction_T_max 0.9907 _exptl_absorpt_process_details Abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis Rapid IP' _diffrn_measurement_method '\w Oscillation' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31224 _diffrn_reflns_av_R_equivalents 0.1150 _diffrn_reflns_av_sigmaI/netI 0.1425 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4851 _reflns_number_gt 1666 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _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^)+(0.0404P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4851 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1860 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.1846 _refine_ls_wR_factor_gt 0.1630 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.2457(3) 0.3511(4) 0.59289(14) 0.1442(17) Uani 1 1 d . . . O2 O -0.3491(2) 0.3246(3) 0.65678(11) 0.1035(11) Uani 1 1 d . . . H2A H -0.3939 0.3439 0.6362 0.155 Uiso 1 1 calc R . . O3 O 0.1133(2) 0.1885(2) 0.58694(11) 0.0810(9) Uani 1 1 d . . . O4 O 0.1971(2) 0.1443(2) 0.65723(10) 0.0775(9) Uani 1 1 d . . . H4B H 0.2478 0.1380 0.6378 0.116 Uiso 1 1 calc R . . N1 N 0.3666(3) 0.1062(2) 0.59856(13) 0.0585(9) Uani 1 1 d . . . N2 N 0.9927(3) 0.1201(2) 0.40409(15) 0.0687(10) Uani 1 1 d . . . C1 C -0.2579(3) 0.3208(3) 0.63564(16) 0.0695(11) Uani 1 1 d . . . C2 C -0.1676(3) 0.2790(3) 0.66743(13) 0.0508(9) Uani 1 1 d . . . C3 C -0.1332(3) 0.3630(3) 0.70573(14) 0.0612(10) Uani 1 1 d . . . H3A H -0.1117 0.4260 0.6879 0.073 Uiso 1 1 calc R . . H3B H -0.1928 0.3804 0.7276 0.073 Uiso 1 1 calc R . . C4 C -0.0410(3) 0.3229(3) 0.73730(14) 0.0622(10) Uani 1 1 d . . . H4A H -0.0193 0.3773 0.7613 0.075 Uiso 1 1 calc R . . C5 C 0.0540(3) 0.2949(3) 0.70354(14) 0.0569(9) Uani 1 1 d . . . H5A H 0.1128 0.2702 0.7242 0.068 Uiso 1 1 calc R . . H5B H 0.0776 0.3566 0.6853 0.068 Uiso 1 1 calc R . . C6 C 0.0211(2) 0.2094(3) 0.66596(12) 0.0455(8) Uani 1 1 d . . . C7 C -0.0722(3) 0.2514(3) 0.63415(12) 0.0480(8) Uani 1 1 d . . . H7A H -0.0492 0.3132 0.6158 0.058 Uiso 1 1 calc R . . H7B H -0.0933 0.1989 0.6096 0.058 Uiso 1 1 calc R . . C8 C -0.0758(3) 0.2272(3) 0.76594(14) 0.0749(12) Uani 1 1 d . . . H8A H -0.1352 0.2449 0.7879 0.090 Uiso 1 1 calc R . . H8B H -0.0175 0.2024 0.7869 0.090 Uiso 1 1 calc R . . C9 C -0.1096(3) 0.1413(3) 0.72953(16) 0.0667(11) Uani 1 1 d . . . H9A H -0.1325 0.0795 0.7486 0.080 Uiso 1 1 calc R . . C10 C -0.2022(3) 0.1811(3) 0.69702(16) 0.0618(10) Uani 1 1 d . . . H10A H -0.2626 0.1980 0.7185 0.074 Uiso 1 1 calc R . . H10B H -0.2241 0.1268 0.6736 0.074 Uiso 1 1 calc R . . C11 C -0.0153(3) 0.1128(3) 0.69569(14) 0.0584(10) Uani 1 1 d . . . H11A H -0.0361 0.0578 0.6724 0.070 Uiso 1 1 calc R . . H11B H 0.0432 0.0869 0.7162 0.070 Uiso 1 1 calc R . . C12 C 0.1142(3) 0.1804(3) 0.63238(15) 0.0548(9) Uani 1 1 d . . . C13 C 0.4630(3) 0.0786(3) 0.61523(15) 0.0612(11) Uani 1 1 d . . . H13A H 0.4700 0.0585 0.6489 0.073 Uiso 1 1 calc R . . C14 C 0.5523(3) 0.0783(3) 0.58547(15) 0.0591(10) Uani 1 1 d . . . H14A H 0.6178 0.0580 0.5989 0.071 Uiso 1 1 calc R . . C15 C 0.5447(3) 0.1087(2) 0.53449(15) 0.0510(10) Uani 1 1 d . . . C16 C 0.4440(3) 0.1356(2) 0.51757(15) 0.0557(10) Uani 1 1 d . . . H16A H 0.4338 0.1553 0.4841 0.067 Uiso 1 1 calc R . . C17 C 0.3580(3) 0.1332(2) 0.55053(17) 0.0601(10) Uani 1 1 d . . . H17A H 0.2910 0.1514 0.5382 0.072 Uiso 1 1 calc R . . C18 C 0.6362(3) 0.1148(3) 0.49948(15) 0.0599(10) Uani 1 1 d . . . H18A H 0.6210 0.1357 0.4666 0.072 Uiso 1 1 calc R . . C19 C 0.7360(3) 0.0942(2) 0.50942(16) 0.0605(10) Uani 1 1 d . . . H19A H 0.7528 0.0741 0.5422 0.073 Uiso 1 1 calc R . . C20 C 0.8238(3) 0.1003(2) 0.47269(16) 0.0535(10) Uani 1 1 d . . . C21 C 0.9285(3) 0.1081(3) 0.48911(17) 0.0636(11) Uani 1 1 d . . . H21A H 0.9442 0.1062 0.5234 0.076 Uiso 1 1 calc R . . C22 C 1.0102(3) 0.1191(3) 0.4536(2) 0.0680(12) Uani 1 1 d . . . H22A H 1.0800 0.1259 0.4651 0.082 Uiso 1 1 calc R . . C23 C 0.8931(4) 0.1110(3) 0.38845(17) 0.0708(12) Uani 1 1 d . . . H23A H 0.8802 0.1107 0.3538 0.085 Uiso 1 1 calc R . . C24 C 0.8078(3) 0.1019(3) 0.42033(15) 0.0609(10) Uani 1 1 d . . . H24A H 0.7391 0.0968 0.4072 0.073 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0542(19) 0.271(5) 0.107(3) 0.086(3) -0.003(2) 0.032(3) O2 0.0384(16) 0.195(3) 0.077(2) 0.019(2) -0.0047(17) 0.037(2) O3 0.0565(18) 0.135(2) 0.0518(16) 0.0131(18) 0.0174(15) 0.0246(15) O4 0.0371(14) 0.132(2) 0.0635(18) -0.0002(17) 0.0072(14) 0.0249(15) N1 0.050(2) 0.0577(17) 0.068(2) -0.0048(17) 0.0188(18) 0.0020(15) N2 0.057(2) 0.069(2) 0.081(3) 0.003(2) 0.025(2) -0.0020(17) C1 0.039(2) 0.114(3) 0.056(2) 0.019(3) -0.006(2) 0.006(2) C2 0.0338(19) 0.067(2) 0.052(2) 0.004(2) -0.0005(18) 0.0085(16) C3 0.050(2) 0.072(2) 0.062(2) -0.010(2) 0.002(2) 0.0095(19) C4 0.052(2) 0.086(3) 0.048(2) -0.014(2) -0.004(2) 0.008(2) C5 0.039(2) 0.079(2) 0.053(2) 0.000(2) -0.0079(19) 0.0034(18) C6 0.0332(18) 0.064(2) 0.039(2) 0.0032(19) 0.0038(17) 0.0029(15) C7 0.0349(18) 0.067(2) 0.0418(18) -0.0031(19) 0.0017(19) -0.0008(16) C8 0.066(3) 0.116(3) 0.043(2) 0.008(3) 0.006(2) 0.022(2) C9 0.052(2) 0.077(2) 0.071(3) 0.024(2) 0.017(2) 0.0056(19) C10 0.039(2) 0.078(2) 0.068(2) -0.001(2) 0.015(2) 0.0022(18) C11 0.044(2) 0.072(2) 0.060(2) 0.010(2) 0.011(2) 0.0097(18) C12 0.038(2) 0.072(2) 0.055(2) 0.007(2) 0.009(2) 0.0024(17) C13 0.052(2) 0.068(2) 0.064(3) 0.003(2) 0.017(2) 0.0080(19) C14 0.050(2) 0.062(2) 0.065(3) 0.003(2) 0.009(2) 0.0102(18) C15 0.044(2) 0.0419(18) 0.067(3) -0.0065(19) 0.018(2) -0.0048(15) C16 0.059(3) 0.049(2) 0.059(2) -0.0026(18) 0.010(2) -0.0009(18) C17 0.039(2) 0.051(2) 0.090(3) -0.009(2) 0.008(3) 0.0030(17) C18 0.058(3) 0.054(2) 0.067(3) -0.0031(19) 0.020(2) -0.0053(19) C19 0.057(3) 0.055(2) 0.070(3) -0.006(2) 0.015(2) -0.0036(19) C20 0.047(2) 0.0393(18) 0.074(3) -0.005(2) 0.023(2) -0.0033(16) C21 0.056(3) 0.055(2) 0.079(3) -0.005(2) 0.011(3) -0.0021(19) C22 0.042(2) 0.051(2) 0.111(4) 0.000(3) 0.007(3) -0.0002(17) C23 0.062(3) 0.075(3) 0.075(3) 0.002(2) 0.023(3) -0.007(2) C24 0.055(2) 0.064(2) 0.064(3) -0.004(2) 0.013(2) -0.0087(18) _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 1.205(4) . ? O2 C1 1.273(5) . ? O3 C12 1.207(4) . ? O4 C12 1.313(4) . ? N1 C17 1.321(5) . ? N1 C13 1.334(5) . ? N2 C23 1.320(5) . ? N2 C22 1.328(5) . ? C1 C2 1.507(5) . ? C2 C7 1.526(4) . ? C2 C3 1.537(5) . ? C2 C10 1.538(5) . ? C3 C4 1.515(5) . ? C4 C8 1.503(5) . ? C4 C5 1.530(5) . ? C5 C6 1.533(4) . ? C6 C12 1.512(5) . ? C6 C11 1.533(4) . ? C6 C7 1.537(4) . ? C8 C9 1.521(5) . ? C9 C11 1.527(5) . ? C9 C10 1.531(5) . ? C13 C14 1.368(5) . ? C14 C15 1.407(5) . ? C15 C16 1.382(5) . ? C15 C18 1.476(5) . ? C16 C17 1.385(5) . ? C18 C19 1.303(5) . ? C19 C20 1.470(5) . ? C20 C21 1.385(5) . ? C20 C24 1.400(5) . ? C21 C22 1.397(5) . ? C23 C24 1.366(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 C17 N1 C13 117.4(3) . . ? C23 N2 C22 117.7(4) . . ? O1 C1 O2 120.9(4) . . ? O1 C1 C2 122.9(4) . . ? O2 C1 C2 116.2(3) . . ? C1 C2 C7 110.3(3) . . ? C1 C2 C3 109.3(3) . . ? C7 C2 C3 108.8(3) . . ? C1 C2 C10 111.2(3) . . ? C7 C2 C10 109.0(3) . . ? C3 C2 C10 108.1(3) . . ? C4 C3 C2 110.0(3) . . ? C8 C4 C3 109.3(3) . . ? C8 C4 C5 109.3(3) . . ? C3 C4 C5 110.5(3) . . ? C4 C5 C6 109.7(3) . . ? C12 C6 C5 110.4(3) . . ? C12 C6 C11 109.5(3) . . ? C5 C6 C11 108.7(3) . . ? C12 C6 C7 110.5(3) . . ? C5 C6 C7 108.1(3) . . ? C11 C6 C7 109.6(3) . . ? C2 C7 C6 111.1(3) . . ? C4 C8 C9 110.4(3) . . ? C8 C9 C11 109.2(3) . . ? C8 C9 C10 109.1(3) . . ? C11 C9 C10 109.6(3) . . ? C9 C10 C2 110.1(3) . . ? C9 C11 C6 109.8(3) . . ? O3 C12 O4 122.4(4) . . ? O3 C12 C6 123.9(4) . . ? O4 C12 C6 113.7(3) . . ? N1 C13 C14 123.4(4) . . ? C13 C14 C15 119.7(4) . . ? C16 C15 C14 116.2(3) . . ? C16 C15 C18 119.5(4) . . ? C14 C15 C18 124.3(4) . . ? C15 C16 C17 120.0(4) . . ? N1 C17 C16 123.3(4) . . ? C19 C18 C15 127.4(4) . . ? C18 C19 C20 125.0(4) . . ? C21 C20 C24 116.4(4) . . ? C21 C20 C19 120.3(4) . . ? C24 C20 C19 123.2(4) . . ? C20 C21 C22 119.4(4) . . ? N2 C22 C21 122.9(4) . . ? N2 C23 C24 123.6(4) . . ? C23 C24 C20 120.0(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A N2 0.82 1.83 2.649(4) 172.4 4_356 O4 H4B N1 0.82 1.86 2.675(4) 172.0 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.270 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.052 # Attachment '5.CIF.txt' data_compound_5 _database_code_depnum_ccdc_archive 'CCDC 289579' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H44 N2 O8' _chemical_formula_weight 632.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3034(19) _cell_length_b 10.198(2) _cell_length_c 10.295(2) _cell_angle_alpha 60.47(3) _cell_angle_beta 76.13(3) _cell_angle_gamma 72.88(3) _cell_volume 807.0(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5583 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.48 _exptl_crystal_description 'Thin platelet' _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.56 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 338 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9372 _exptl_absorpt_correction_T_max 0.9928 _exptl_absorpt_process_details Abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku raxis Rapid IP' _diffrn_measurement_method '\w Oscillation' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5583 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3304 _reflns_number_gt 2160 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _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^)+(0.0866P)^2^+0.7223P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3304 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1198 _refine_ls_R_factor_gt 0.0795 _refine_ls_wR_factor_ref 0.2142 _refine_ls_wR_factor_gt 0.1884 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.020 _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 O1 O 0.4895(3) 0.1769(3) 0.5003(4) 0.0929(12) Uani 1 1 d . . . H1A H 0.4429 0.1133 0.5142 0.111 Uiso 1 1 calc R . . O2 O 0.6767(3) 0.0206(3) 0.4388(4) 0.0793(9) Uani 1 1 d . . . O3 O 1.1680(3) 0.1581(3) 0.1955(4) 0.0819(10) Uani 1 1 d . . . O4 O 1.2303(2) 0.3571(3) 0.1822(3) 0.0657(7) Uani 1 1 d . . . H4B H 1.3103 0.3259 0.1416 0.079 Uiso 1 1 calc R . . N1 N 1.5056(3) 0.2463(3) 0.0616(4) 0.0600(8) Uani 1 1 d . . . C1 C 0.6277(3) 0.1396(3) 0.4516(4) 0.0458(7) Uani 1 1 d . . . C2 C 0.7259(3) 0.2519(3) 0.4107(3) 0.0364(6) Uani 1 1 d . . . C3 C 0.6498(3) 0.4146(3) 0.3020(4) 0.0433(7) Uani 1 1 d . . . H3A H 0.6354 0.4148 0.2116 0.052 Uiso 1 1 calc R . . H3B H 0.5513 0.4458 0.3488 0.052 Uiso 1 1 calc R . . C4 C 0.7495(3) 0.5274(3) 0.2617(4) 0.0464(7) Uani 1 1 d . . . H4A H 0.7008 0.6309 0.1923 0.056 Uiso 1 1 calc R . . C5 C 0.7705(4) 0.5294(4) 0.4028(4) 0.0563(9) Uani 1 1 d . . . H5A H 0.6729 0.5618 0.4501 0.068 Uiso 1 1 calc R . . H5B H 0.8328 0.6022 0.3764 0.068 Uiso 1 1 calc R . . C6 C 0.8465(4) 0.3678(4) 0.5125(4) 0.0488(8) Uani 1 1 d . . . H6A H 0.8595 0.3696 0.6033 0.059 Uiso 1 1 calc R . . C7 C 0.7466(3) 0.2541(4) 0.5548(3) 0.0463(7) Uani 1 1 d . . . H7A H 0.6487 0.2848 0.6029 0.056 Uiso 1 1 calc R . . H7B H 0.7934 0.1518 0.6250 0.056 Uiso 1 1 calc R . . C8 C 1.0015(3) 0.3187(4) 0.4382(4) 0.0460(7) Uani 1 1 d . . . H8A H 1.0503 0.2168 0.5073 0.055 Uiso 1 1 calc R . . H8B H 1.0652 0.3900 0.4130 0.055 Uiso 1 1 calc R . . C9 C 0.9817(3) 0.3172(3) 0.2948(3) 0.0375(6) Uani 1 1 d . . . C10 C 0.9036(3) 0.4793(3) 0.1854(3) 0.0436(7) Uani 1 1 d . . . H10A H 0.9662 0.5525 0.1568 0.052 Uiso 1 1 calc R . . H10B H 0.8903 0.4784 0.0952 0.052 Uiso 1 1 calc R . . C11 C 0.8814(3) 0.2042(3) 0.3351(3) 0.0374(6) Uani 1 1 d . . . H11A H 0.9295 0.1011 0.4026 0.045 Uiso 1 1 calc R . . H11B H 0.8689 0.2032 0.2447 0.045 Uiso 1 1 calc R . . C12 C 1.1355(3) 0.2678(4) 0.2195(4) 0.0490(8) Uani 1 1 d . . . C13 C 1.5340(5) 0.0972(5) 0.1082(6) 0.0843(14) Uani 1 1 d . . . H13A H 1.4585 0.0423 0.1662 0.101 Uiso 1 1 calc R . . C14 C 1.6806(5) 0.0170(5) 0.0711(7) 0.0999(18) Uani 1 1 d . . . H14A H 1.6999 -0.0887 0.1038 0.120 Uiso 1 1 calc R . . C15 C 1.7906(3) 0.0993(4) -0.0129(5) 0.0604(10) Uani 1 1 d . . . C16 C 1.7528(4) 0.2534(4) -0.0557(5) 0.0628(10) Uani 1 1 d . . . H16A H 1.8254 0.3128 -0.1113 0.075 Uiso 1 1 calc R . . C17 C 1.6133(4) 0.3214(4) -0.0193(5) 0.0615(10) Uani 1 1 d . . . H17A H 1.5921 0.4275 -0.0534 0.074 Uiso 1 1 calc R . . C18 C 1.9497(4) 0.0289(6) -0.0586(6) 0.0821(13) Uani 1 1 d . . . H18A H 1.9462 -0.0555 -0.0756 0.098 Uiso 1 1 calc R . . H18B H 1.9905 0.1058 -0.1520 0.098 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0429(13) 0.0793(19) 0.180(3) -0.086(2) 0.0357(16) -0.0339(13) O2 0.0459(13) 0.0637(16) 0.149(3) -0.0688(18) 0.0174(15) -0.0254(11) O3 0.0526(14) 0.0795(19) 0.135(3) -0.077(2) 0.0293(15) -0.0228(13) O4 0.0338(11) 0.0662(16) 0.102(2) -0.0474(15) 0.0166(12) -0.0197(10) N1 0.0384(14) 0.0607(19) 0.076(2) -0.0324(16) -0.0031(13) -0.0040(13) C1 0.0342(14) 0.0420(16) 0.064(2) -0.0264(15) 0.0001(13) -0.0132(12) C2 0.0318(13) 0.0362(14) 0.0443(16) -0.0200(12) -0.0003(11) -0.0113(11) C3 0.0312(14) 0.0437(16) 0.0534(19) -0.0234(14) -0.0033(12) -0.0043(11) C4 0.0381(15) 0.0326(14) 0.058(2) -0.0159(13) 0.0014(13) -0.0069(11) C5 0.0472(17) 0.0526(19) 0.083(3) -0.0452(19) 0.0111(16) -0.0174(14) C6 0.0547(18) 0.065(2) 0.0450(18) -0.0350(16) 0.0013(14) -0.0247(15) C7 0.0485(17) 0.0518(18) 0.0383(16) -0.0192(14) 0.0047(13) -0.0200(14) C8 0.0413(16) 0.0506(17) 0.0513(19) -0.0218(15) -0.0072(13) -0.0179(13) C9 0.0305(13) 0.0374(14) 0.0451(16) -0.0201(12) 0.0005(11) -0.0094(11) C10 0.0395(15) 0.0386(15) 0.0420(17) -0.0119(12) 0.0028(12) -0.0116(12) C11 0.0312(13) 0.0363(14) 0.0465(16) -0.0204(12) -0.0045(11) -0.0068(11) C12 0.0341(15) 0.0529(18) 0.055(2) -0.0229(15) 0.0009(13) -0.0103(13) C13 0.061(2) 0.072(3) 0.107(4) -0.030(3) 0.003(2) -0.026(2) C14 0.055(2) 0.059(3) 0.178(6) -0.050(3) -0.019(3) -0.0045(19) C15 0.0320(16) 0.071(2) 0.093(3) -0.053(2) -0.0116(16) 0.0022(15) C16 0.0462(18) 0.071(2) 0.076(3) -0.042(2) -0.0043(17) -0.0063(17) C17 0.0453(18) 0.057(2) 0.080(3) -0.0332(19) -0.0046(17) -0.0046(15) C18 0.050(2) 0.110(4) 0.108(4) -0.077(3) -0.019(2) 0.012(2) _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 1.280(4) . ? O2 C1 1.225(4) . ? O3 C12 1.200(4) . ? O4 C12 1.312(4) . ? N1 C17 1.306(4) . ? N1 C13 1.310(5) . ? C1 C2 1.511(4) . ? C2 C11 1.535(4) . ? C2 C3 1.538(4) . ? C2 C7 1.552(4) . ? C3 C4 1.526(4) . ? C4 C5 1.522(5) . ? C4 C10 1.529(4) . ? C5 C6 1.534(5) . ? C6 C8 1.529(4) . ? C6 C7 1.531(4) . ? C8 C9 1.539(4) . ? C9 C12 1.527(4) . ? C9 C11 1.532(4) . ? C9 C10 1.542(4) . ? C13 C14 1.440(6) . ? C14 C15 1.366(6) . ? C15 C16 1.362(5) . ? C15 C18 1.516(5) . ? C16 C17 1.342(5) . ? C18 C18 1.482(8) 2_955 ? 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 C17 N1 C13 118.6(3) . . ? O2 C1 O1 122.1(3) . . ? O2 C1 C2 122.3(3) . . ? O1 C1 C2 115.7(3) . . ? C1 C2 C11 110.0(2) . . ? C1 C2 C3 109.7(2) . . ? C11 C2 C3 109.2(2) . . ? C1 C2 C7 109.6(2) . . ? C11 C2 C7 109.4(2) . . ? C3 C2 C7 108.9(2) . . ? C4 C3 C2 109.3(2) . . ? C5 C4 C10 109.8(3) . . ? C5 C4 C3 110.0(3) . . ? C10 C4 C3 109.6(2) . . ? C4 C5 C6 109.7(2) . . ? C8 C6 C7 109.9(2) . . ? C8 C6 C5 109.4(3) . . ? C7 C6 C5 109.3(3) . . ? C6 C7 C2 109.3(2) . . ? C6 C8 C9 109.5(2) . . ? C12 C9 C11 109.2(2) . . ? C12 C9 C8 110.2(2) . . ? C11 C9 C8 109.6(2) . . ? C12 C9 C10 109.8(2) . . ? C11 C9 C10 108.3(2) . . ? C8 C9 C10 109.6(2) . . ? C4 C10 C9 109.4(2) . . ? C9 C11 C2 110.1(2) . . ? O3 C12 O4 122.5(3) . . ? O3 C12 C9 123.8(3) . . ? O4 C12 C9 113.7(3) . . ? N1 C13 C14 121.0(4) . . ? C15 C14 C13 118.7(4) . . ? C16 C15 C14 116.8(3) . . ? C16 C15 C18 119.2(4) . . ? C14 C15 C18 124.0(4) . . ? C17 C16 C15 121.5(4) . . ? N1 C17 C16 123.3(4) . . ? C18 C18 C15 111.4(4) 2_955 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O2 0.82 1.82 2.639(3) 173.0 2_656 O4 H4B N1 0.82 1.93 2.745(4) 175.1 . _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.892 _refine_diff_density_max 0.461 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.048 # Attachment '6.CIF.txt' data_compound_6 _database_code_depnum_ccdc_archive 'CCDC 289580' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 N2 O4 S2' _chemical_formula_weight 444.55 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monclinic _symmetry_space_group_name_H-M P2(1)/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 11.764(2) _cell_length_b 15.841(3) _cell_length_c 12.322(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.90(3) _cell_angle_gamma 90.00 _cell_volume 2099.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 18372 _cell_measurement_theta_min 2.02 _cell_measurement_theta_max 27.33 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.58 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.286 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8352 _exptl_absorpt_correction_T_max 0.9557 _exptl_absorpt_process_details Abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis Rapid IP' _diffrn_measurement_method '\w oscillation' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18372 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.33 _reflns_number_total 4711 _reflns_number_gt 3754 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _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^)+(0.0709P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4711 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1115 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 S1 S 0.51693(4) 0.19360(3) 0.11210(4) 0.04439(13) Uani 1 1 d . . . S2 S 0.63501(4) 0.29100(3) 0.12801(3) 0.04622(13) Uani 1 1 d . . . O1 O -0.07231(12) 0.05319(8) -0.13855(12) 0.0593(4) Uani 1 1 d . . . O2 O 0.12256(11) 0.06890(8) -0.11892(11) 0.0526(3) Uani 1 1 d . . . H2A H 0.1002 0.0355 -0.1745 0.063 Uiso 1 1 calc R . . O3 O -0.03957(11) 0.41829(8) -0.15084(11) 0.0565(3) Uani 1 1 d . . . H3C H -0.0349 0.4550 -0.1958 0.068 Uiso 1 1 calc R . . O4 O 0.16472(12) 0.43344(9) -0.07044(13) 0.0681(4) Uani 1 1 d . . . N1 N 0.53864(13) 0.02764(8) -0.18137(11) 0.0427(3) Uani 1 1 d . . . N2 N 0.44955(15) 0.46226(9) -0.19336(13) 0.0501(3) Uani 1 1 d . . . C1 C 0.02670(14) 0.08876(9) -0.09378(13) 0.0359(3) Uani 1 1 d . . . C2 C 0.05218(12) 0.16247(9) -0.00830(11) 0.0299(3) Uani 1 1 d . . . C3 C -0.05302(14) 0.17014(10) 0.03453(13) 0.0356(3) Uani 1 1 d . . . H3A H -0.1321 0.1754 -0.0333 0.043 Uiso 1 1 calc R . . H3B H -0.0557 0.1196 0.0779 0.043 Uiso 1 1 calc R . . C4 C -0.03203(15) 0.24749(10) 0.11491(14) 0.0401(4) Uani 1 1 d . . . H4A H -0.0993 0.2512 0.1424 0.048 Uiso 1 1 calc R . . C5 C -0.03260(15) 0.32697(10) 0.04419(14) 0.0382(3) Uani 1 1 d . . . H5A H -0.0220 0.3765 0.0936 0.046 Uiso 1 1 calc R . . H5B H -0.1117 0.3318 -0.0237 0.046 Uiso 1 1 calc R . . C6 C 0.07374(13) 0.32204(9) 0.00180(12) 0.0316(3) Uani 1 1 d . . . C7 C 0.19845(14) 0.31303(10) 0.11006(13) 0.0394(3) Uani 1 1 d . . . H7A H 0.2658 0.3098 0.0840 0.047 Uiso 1 1 calc R . . H7B H 0.2122 0.3620 0.1611 0.047 Uiso 1 1 calc R . . C8 C 0.19673(15) 0.23294(10) 0.17926(13) 0.0415(4) Uani 1 1 d . . . H8A H 0.2763 0.2278 0.2482 0.050 Uiso 1 1 calc R . . C9 C 0.17690(13) 0.15446(10) 0.10042(13) 0.0380(3) Uani 1 1 d . . . H9A H 0.1764 0.1042 0.1452 0.046 Uiso 1 1 calc R . . H9B H 0.2443 0.1494 0.0746 0.046 Uiso 1 1 calc R . . C10 C 0.05539(12) 0.24312(8) -0.07730(12) 0.0297(3) Uani 1 1 d . . . H10A H -0.0219 0.2482 -0.1472 0.036 Uiso 1 1 calc R . . H10B H 0.1229 0.2392 -0.1032 0.036 Uiso 1 1 calc R . . C11 C 0.09204(17) 0.23859(12) 0.22199(14) 0.0489(4) Uani 1 1 d . . . H11A H 0.1052 0.2869 0.2740 0.059 Uiso 1 1 calc R . . H11B H 0.0913 0.1882 0.2663 0.059 Uiso 1 1 calc R . . C12 C 0.07291(14) 0.39785(9) -0.07457(13) 0.0381(3) Uani 1 1 d . . . C13 C 0.43071(16) 0.04800(11) -0.17646(15) 0.0483(4) Uani 1 1 d . . . H13A H 0.3580 0.0268 -0.2350 0.058 Uiso 1 1 calc R . . C14 C 0.42075(15) 0.09864(11) -0.08962(15) 0.0435(4) Uani 1 1 d . . . H14A H 0.3436 0.1108 -0.0893 0.052 Uiso 1 1 calc R . . C15 C 0.52878(14) 0.13078(9) -0.00302(12) 0.0341(3) Uani 1 1 d . . . C16 C 0.64174(14) 0.10974(10) -0.00611(13) 0.0385(3) Uani 1 1 d . . . H16A H 0.7159 0.1299 0.0515 0.046 Uiso 1 1 calc R . . C17 C 0.64224(15) 0.05839(10) -0.09625(14) 0.0412(3) Uani 1 1 d . . . H17A H 0.7183 0.0445 -0.0979 0.049 Uiso 1 1 calc R . . C18 C 0.38461(16) 0.40124(11) -0.17059(15) 0.0468(4) Uani 1 1 d . . . H18A H 0.3014 0.3950 -0.2218 0.056 Uiso 1 1 calc R . . C19 C 0.43346(15) 0.34649(11) -0.07528(14) 0.0420(4) Uani 1 1 d . . . H19A H 0.3844 0.3045 -0.0635 0.050 Uiso 1 1 calc R . . C20 C 0.55660(14) 0.35556(9) 0.00210(12) 0.0364(3) Uani 1 1 d . . . C21 C 0.62529(17) 0.41962(11) -0.01867(15) 0.0466(4) Uani 1 1 d . . . H21A H 0.7080 0.4282 0.0323 0.056 Uiso 1 1 calc R . . C22 C 0.56798(19) 0.47068(11) -0.11706(16) 0.0536(5) Uani 1 1 d . . . H22A H 0.6148 0.5134 -0.1308 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0590(3) 0.0428(2) 0.0426(2) 0.00106(16) 0.0322(2) -0.00034(17) S2 0.0507(3) 0.0436(2) 0.0371(2) -0.00381(16) 0.01034(18) -0.00371(17) O1 0.0498(7) 0.0592(8) 0.0724(8) -0.0306(7) 0.0284(6) -0.0211(6) O2 0.0499(7) 0.0516(7) 0.0651(8) -0.0235(6) 0.0323(6) -0.0064(5) O3 0.0497(7) 0.0541(8) 0.0607(7) 0.0270(6) 0.0172(6) 0.0025(6) O4 0.0546(8) 0.0644(9) 0.0799(9) 0.0269(7) 0.0218(7) -0.0166(6) N1 0.0536(8) 0.0329(7) 0.0431(7) -0.0037(6) 0.0212(6) -0.0044(6) N2 0.0667(10) 0.0410(8) 0.0495(8) 0.0042(6) 0.0306(7) 0.0021(7) C1 0.0396(8) 0.0314(7) 0.0377(7) 0.0002(6) 0.0169(6) -0.0011(6) C2 0.0277(7) 0.0297(7) 0.0322(7) -0.0004(5) 0.0122(5) -0.0019(5) C3 0.0342(7) 0.0358(8) 0.0414(8) 0.0006(6) 0.0199(6) -0.0056(6) C4 0.0468(9) 0.0407(9) 0.0443(8) -0.0026(7) 0.0304(7) -0.0024(7) C5 0.0408(8) 0.0345(8) 0.0455(8) -0.0033(6) 0.0238(7) 0.0020(6) C6 0.0321(7) 0.0291(7) 0.0346(7) 0.0003(5) 0.0144(6) -0.0033(5) C7 0.0365(8) 0.0385(8) 0.0381(8) -0.0042(6) 0.0100(6) -0.0103(6) C8 0.0392(8) 0.0442(8) 0.0304(7) 0.0010(6) 0.0030(6) -0.0055(7) C9 0.0327(7) 0.0366(8) 0.0394(8) 0.0053(6) 0.0092(6) 0.0013(6) C10 0.0270(7) 0.0328(7) 0.0294(6) 0.0000(5) 0.0116(5) -0.0028(5) C11 0.0711(12) 0.0462(9) 0.0331(8) -0.0021(7) 0.0251(8) -0.0084(8) C12 0.0432(8) 0.0305(7) 0.0420(8) -0.0006(6) 0.0186(7) -0.0044(6) C13 0.0463(9) 0.0426(9) 0.0493(9) -0.0057(7) 0.0126(8) -0.0099(7) C14 0.0361(8) 0.0462(9) 0.0495(9) 0.0007(7) 0.0186(7) -0.0017(7) C15 0.0414(8) 0.0299(7) 0.0351(7) 0.0048(6) 0.0197(6) -0.0010(6) C16 0.0370(8) 0.0410(8) 0.0389(8) -0.0026(6) 0.0167(6) -0.0038(6) C17 0.0442(9) 0.0374(8) 0.0464(8) -0.0023(7) 0.0229(7) -0.0010(6) C18 0.0468(9) 0.0482(9) 0.0458(9) 0.0024(7) 0.0192(7) 0.0026(7) C19 0.0413(8) 0.0425(9) 0.0454(8) 0.0016(7) 0.0210(7) -0.0033(6) C20 0.0457(8) 0.0339(7) 0.0350(7) -0.0065(6) 0.0218(7) -0.0010(6) C21 0.0509(9) 0.0440(9) 0.0463(9) -0.0095(7) 0.0211(8) -0.0133(7) C22 0.0726(13) 0.0399(9) 0.0583(11) -0.0031(8) 0.0367(10) -0.0140(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 S1 C15 1.7839(15) . ? S1 S2 2.0318(7) . ? S2 C20 1.7733(16) . ? O1 C1 1.2074(19) . ? O2 C1 1.3228(19) . ? O3 C12 1.316(2) . ? O4 C12 1.2011(19) . ? N1 C13 1.335(2) . ? N1 C17 1.337(2) . ? N2 C18 1.331(2) . ? N2 C22 1.335(3) . ? C1 C2 1.519(2) . ? C2 C3 1.534(2) . ? C2 C9 1.540(2) . ? C2 C10 1.5436(19) . ? C3 C4 1.531(2) . ? C4 C11 1.527(2) . ? C4 C5 1.530(2) . ? C5 C6 1.541(2) . ? C6 C12 1.523(2) . ? C6 C7 1.538(2) . ? C6 C10 1.5457(19) . ? C7 C8 1.533(2) . ? C8 C11 1.526(3) . ? C8 C9 1.536(2) . ? C13 C14 1.380(2) . ? C14 C15 1.384(2) . ? C15 C16 1.386(2) . ? C16 C17 1.379(2) . ? C18 C19 1.384(2) . ? C19 C20 1.382(2) . ? C20 C21 1.384(2) . ? C21 C22 1.384(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 C15 S1 S2 103.28(5) . . ? C20 S2 S1 105.10(6) . . ? C13 N1 C17 117.25(14) . . ? C18 N2 C22 116.66(15) . . ? O1 C1 O2 122.56(14) . . ? O1 C1 C2 123.95(14) . . ? O2 C1 C2 113.44(12) . . ? C1 C2 C3 109.84(11) . . ? C1 C2 C9 113.01(12) . . ? C3 C2 C9 108.92(11) . . ? C1 C2 C10 107.24(11) . . ? C3 C2 C10 109.09(11) . . ? C9 C2 C10 108.67(11) . . ? C4 C3 C2 110.16(12) . . ? C11 C4 C5 110.51(13) . . ? C11 C4 C3 109.40(13) . . ? C5 C4 C3 109.13(12) . . ? C4 C5 C6 109.55(12) . . ? C12 C6 C5 111.51(12) . . ? C12 C6 C7 111.96(12) . . ? C5 C6 C7 109.32(12) . . ? C12 C6 C10 106.49(11) . . ? C5 C6 C10 109.25(12) . . ? C7 C6 C10 108.20(12) . . ? C8 C7 C6 109.64(12) . . ? C11 C8 C7 109.74(14) . . ? C11 C8 C9 109.19(13) . . ? C7 C8 C9 110.53(13) . . ? C8 C9 C2 109.30(12) . . ? C2 C10 C6 110.52(11) . . ? C8 C11 C4 109.27(12) . . ? O4 C12 O3 122.79(15) . . ? O4 C12 C6 124.29(15) . . ? O3 C12 C6 112.84(13) . . ? N1 C13 C14 123.83(15) . . ? C13 C14 C15 118.17(15) . . ? C14 C15 C16 118.81(14) . . ? C14 C15 S1 118.38(12) . . ? C16 C15 S1 122.74(12) . . ? C17 C16 C15 118.77(14) . . ? N1 C17 C16 123.17(15) . . ? N2 C18 C19 123.90(16) . . ? C20 C19 C18 118.65(15) . . ? C19 C20 C21 118.43(15) . . ? C19 C20 S2 124.90(12) . . ? C21 C20 S2 116.67(12) . . ? C22 C21 C20 118.46(16) . . ? N2 C22 C21 123.89(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A N2 0.82 1.89 2.7082(19) 177.4 2_544 O3 H3C N1 0.82 1.89 2.7006(18) 170.9 2_554 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.33 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.229 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.071 # Attachment '7.CIF.txt' data_compound_7 _database_code_depnum_ccdc_archive 'CCDC 289581' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H30 N2 O4' _chemical_formula_weight 434.52 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5551(17) _cell_length_b 11.840(2) _cell_length_c 12.496(3) _cell_angle_alpha 106.27(3) _cell_angle_beta 104.97(3) _cell_angle_gamma 98.65(3) _cell_volume 1139.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9789 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.79 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9353 _exptl_absorpt_correction_T_max 0.9740 _exptl_absorpt_process_details Abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis Rapid IP Area Detector' _diffrn_measurement_method '\w Oscillation' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9789 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5055 _reflns_number_gt 3616 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _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^)+(0.1623P)^2^+0.5936P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5055 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1132 _refine_ls_R_factor_gt 0.0873 _refine_ls_wR_factor_ref 0.2816 _refine_ls_wR_factor_gt 0.2538 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0861(4) -0.19928(19) 0.2871(2) 0.0772(8) Uani 1 1 d . . . H1A H 0.1246 -0.2521 0.2523 0.116 Uiso 1 1 calc R . . O2 O 0.1885(5) -0.1012(2) 0.1878(3) 0.1010(11) Uani 1 1 d . . . O3 O 0.3208(6) 0.5551(3) 0.7862(3) 0.1288(16) Uani 1 1 d . . . O4 O 0.2067(4) 0.6132(2) 0.6416(2) 0.0830(8) Uani 1 1 d . . . H4C H 0.2662 0.6788 0.6876 0.124 Uiso 1 1 calc R . . N1 N 0.3252(4) 0.8493(2) 0.7930(3) 0.0690(8) Uani 1 1 d . . . N2 N 0.1767(4) 1.6074(2) 1.1710(3) 0.0663(7) Uani 1 1 d . . . C1 C 0.1168(4) -0.1045(2) 0.2577(3) 0.0504(6) Uani 1 1 d . . . C2 C 0.0511(3) -0.0011(2) 0.3185(2) 0.0464(6) Uani 1 1 d . . . H2B H -0.0132 -0.0296 0.3634 0.056 Uiso 1 1 calc R . . H2C H -0.0244 0.0201 0.2588 0.056 Uiso 1 1 calc R . . C3 C 0.1846(3) 0.1145(2) 0.4016(2) 0.0366(5) Uani 1 1 d . . . C4 C 0.3174(4) 0.0870(2) 0.4935(2) 0.0499(6) Uani 1 1 d . . . H4A H 0.2644 0.0480 0.5381 0.060 Uiso 1 1 calc R . . H4B H 0.3746 0.0322 0.4544 0.060 Uiso 1 1 calc R . . C5 C 0.4433(4) 0.2049(3) 0.5768(3) 0.0615(8) Uani 1 1 d . . . H5A H 0.5283 0.1867 0.6346 0.074 Uiso 1 1 calc R . . C6 C 0.3540(4) 0.2909(3) 0.6405(2) 0.0555(7) Uani 1 1 d . . . H6A H 0.3007 0.2528 0.6855 0.067 Uiso 1 1 calc R . . H6B H 0.4344 0.3646 0.6947 0.067 Uiso 1 1 calc R . . C7 C 0.2230(3) 0.3218(2) 0.5513(2) 0.0424(6) Uani 1 1 d . . . C8 C 0.0982(3) 0.2030(2) 0.4667(2) 0.0384(5) Uani 1 1 d . . . H8A H 0.0138 0.2211 0.4098 0.046 Uiso 1 1 calc R . . H8B H 0.0430 0.1648 0.5108 0.046 Uiso 1 1 calc R . . C9 C 0.5265(4) 0.2657(3) 0.5060(3) 0.0714(10) Uani 1 1 d . . . H9A H 0.5842 0.2120 0.4660 0.086 Uiso 1 1 calc R . . H9B H 0.6079 0.3397 0.5585 0.086 Uiso 1 1 calc R . . C10 C 0.3069(4) 0.3807(2) 0.4795(3) 0.0536(7) Uani 1 1 d . . . H10A H 0.2237 0.4000 0.4227 0.064 Uiso 1 1 calc R . . H10B H 0.3870 0.4556 0.5312 0.064 Uiso 1 1 calc R . . C11 C 0.3949(4) 0.2951(3) 0.4159(3) 0.0576(8) Uani 1 1 d . . . H11A H 0.4490 0.3339 0.3707 0.069 Uiso 1 1 calc R . . C12 C 0.2686(4) 0.1775(2) 0.3326(2) 0.0477(6) Uani 1 1 d . . . H12A H 0.1849 0.1955 0.2751 0.057 Uiso 1 1 calc R . . H12B H 0.3249 0.1240 0.2909 0.057 Uiso 1 1 calc R . . C13 C 0.1252(4) 0.4038(2) 0.6115(3) 0.0531(7) Uani 1 1 d . . . H13A H 0.0335 0.4110 0.5512 0.064 Uiso 1 1 calc R . . H13B H 0.0776 0.3644 0.6582 0.064 Uiso 1 1 calc R . . C14 C 0.2255(4) 0.5297(2) 0.6900(3) 0.0546(7) Uani 1 1 d . . . C15 C 0.2665(5) 0.8567(3) 0.8802(3) 0.0732(10) Uani 1 1 d . . . H15A H 0.2283 0.7853 0.8928 0.088 Uiso 1 1 calc R . . C16 C 0.2572(5) 0.9668(3) 0.9568(3) 0.0666(8) Uani 1 1 d . . . H16A H 0.2155 0.9677 1.0187 0.080 Uiso 1 1 calc R . . C17 C 0.3121(4) 1.0743(2) 0.9375(2) 0.0502(7) Uani 1 1 d . . . C18 C 0.3793(4) 1.0633(3) 0.8469(3) 0.0567(7) Uani 1 1 d . . . H18A H 0.4237 1.1321 0.8325 0.068 Uiso 1 1 calc R . . C19 C 0.3805(4) 0.9505(3) 0.7780(3) 0.0655(8) Uani 1 1 d . . . H19A H 0.4238 0.9462 0.7163 0.079 Uiso 1 1 calc R . . C20 C 0.2898(5) 1.1887(3) 1.0086(3) 0.0628(8) Uani 1 1 d . . . H20A H 0.2712 1.1894 1.0788 0.075 Uiso 1 1 calc R . . C21 C 0.2930(5) 1.2877(3) 0.9859(3) 0.0642(8) Uani 1 1 d . . . H21A H 0.3220 1.2898 0.9195 0.077 Uiso 1 1 calc R . . C22 C 0.2561(4) 1.3986(3) 1.0523(2) 0.0545(7) Uani 1 1 d . . . C23 C 0.2772(5) 1.5002(3) 1.0193(3) 0.0722(10) Uani 1 1 d . . . H23A H 0.3174 1.5000 0.9569 0.087 Uiso 1 1 calc R . . C24 C 0.2363(5) 1.6047(3) 1.0823(4) 0.0781(10) Uani 1 1 d . . . H24A H 0.2517 1.6737 1.0610 0.094 Uiso 1 1 calc R . . C25 C 0.1612(5) 1.5104(3) 1.2017(3) 0.0714(9) Uani 1 1 d . . . H25A H 0.1230 1.5128 1.2653 0.086 Uiso 1 1 calc R . . C26 C 0.1976(5) 1.4064(3) 1.1459(3) 0.0676(9) Uani 1 1 d . . . H26A H 0.1827 1.3401 1.1714 0.081 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.116(2) 0.0419(11) 0.1048(19) 0.0306(12) 0.0694(17) 0.0355(12) O2 0.169(3) 0.0547(14) 0.112(2) 0.0221(14) 0.104(2) 0.0288(17) O3 0.213(4) 0.0610(17) 0.0675(18) 0.0126(14) -0.010(2) 0.016(2) O4 0.106(2) 0.0382(11) 0.0801(16) 0.0088(10) 0.0023(14) 0.0156(12) N1 0.0788(19) 0.0509(15) 0.0655(17) 0.0060(12) 0.0126(14) 0.0248(13) N2 0.0766(18) 0.0506(14) 0.0691(17) 0.0114(12) 0.0228(14) 0.0253(13) C1 0.0551(15) 0.0331(12) 0.0568(16) 0.0073(11) 0.0185(13) 0.0060(11) C2 0.0447(13) 0.0323(11) 0.0583(15) 0.0110(10) 0.0160(12) 0.0065(10) C3 0.0400(11) 0.0307(10) 0.0413(12) 0.0133(9) 0.0143(10) 0.0103(9) C4 0.0539(15) 0.0467(14) 0.0509(15) 0.0153(11) 0.0136(12) 0.0243(12) C5 0.0512(16) 0.0682(19) 0.0497(15) 0.0040(13) 0.0015(13) 0.0253(14) C6 0.0596(16) 0.0557(16) 0.0432(14) 0.0054(12) 0.0139(13) 0.0158(13) C7 0.0501(13) 0.0330(11) 0.0473(13) 0.0106(10) 0.0239(11) 0.0099(10) C8 0.0398(12) 0.0312(11) 0.0490(13) 0.0151(10) 0.0191(10) 0.0103(9) C9 0.0428(15) 0.069(2) 0.077(2) -0.0126(16) 0.0231(15) 0.0002(14) C10 0.0679(17) 0.0316(12) 0.0598(16) 0.0080(11) 0.0334(14) -0.0013(11) C11 0.0606(17) 0.0449(14) 0.0624(17) 0.0056(12) 0.0357(15) -0.0067(12) C12 0.0596(16) 0.0387(12) 0.0461(14) 0.0118(10) 0.0247(12) 0.0059(11) C13 0.0622(16) 0.0362(12) 0.0666(17) 0.0114(12) 0.0349(14) 0.0133(12) C14 0.0754(19) 0.0386(13) 0.0519(16) 0.0106(11) 0.0276(15) 0.0149(13) C15 0.084(2) 0.0473(16) 0.081(2) 0.0278(16) 0.008(2) 0.0139(16) C16 0.081(2) 0.069(2) 0.0529(17) 0.0237(15) 0.0200(16) 0.0224(17) C17 0.0542(15) 0.0453(14) 0.0403(13) 0.0037(11) 0.0051(11) 0.0179(12) C18 0.0562(16) 0.0460(15) 0.0605(17) 0.0087(12) 0.0172(14) 0.0104(12) C19 0.0659(19) 0.0567(18) 0.0658(19) 0.0021(14) 0.0216(16) 0.0247(15) C20 0.080(2) 0.0530(16) 0.0501(16) 0.0065(13) 0.0182(15) 0.0264(15) C21 0.083(2) 0.0507(16) 0.0589(17) 0.0103(13) 0.0259(16) 0.0244(15) C22 0.0654(17) 0.0458(14) 0.0464(14) 0.0069(11) 0.0128(13) 0.0207(13) C23 0.108(3) 0.0566(18) 0.0585(18) 0.0213(15) 0.0317(19) 0.0240(18) C24 0.096(3) 0.0541(19) 0.084(2) 0.0307(18) 0.018(2) 0.0224(18) C25 0.089(2) 0.0590(19) 0.073(2) 0.0167(16) 0.0366(19) 0.0285(18) C26 0.094(2) 0.0532(17) 0.0661(19) 0.0199(15) 0.0364(18) 0.0281(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 C1 1.287(3) . ? O2 C1 1.195(4) . ? O3 C14 1.191(4) . ? O4 C14 1.305(4) . ? N1 C15 1.300(5) . ? N1 C19 1.303(5) . ? N2 C25 1.307(4) . ? N2 C24 1.330(5) . ? C1 C2 1.517(4) . ? C2 C3 1.542(3) . ? C3 C12 1.528(3) . ? C3 C4 1.537(3) . ? C3 C8 1.541(3) . ? C4 C5 1.532(4) . ? C5 C9 1.527(5) . ? C5 C6 1.533(4) . ? C6 C7 1.530(4) . ? C7 C10 1.529(4) . ? C7 C8 1.539(3) . ? C7 C13 1.539(3) . ? C9 C11 1.529(5) . ? C10 C11 1.522(4) . ? C11 C12 1.531(4) . ? C13 C14 1.510(4) . ? C15 C16 1.412(5) . ? C16 C17 1.396(4) . ? C17 C18 1.381(4) . ? C17 C20 1.467(4) . ? C18 C19 1.374(4) . ? C20 C21 1.279(5) . ? C21 C22 1.470(4) . ? C22 C26 1.373(4) . ? C22 C23 1.378(4) . ? C23 C24 1.413(5) . ? C25 C26 1.359(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 C15 N1 C19 117.1(3) . . ? C25 N2 C24 117.7(3) . . ? O2 C1 O1 122.2(3) . . ? O2 C1 C2 124.5(3) . . ? O1 C1 C2 113.4(2) . . ? C1 C2 C3 115.5(2) . . ? C12 C3 C4 109.6(2) . . ? C12 C3 C8 107.68(19) . . ? C4 C3 C8 108.27(19) . . ? C12 C3 C2 111.1(2) . . ? C4 C3 C2 111.7(2) . . ? C8 C3 C2 108.37(19) . . ? C5 C4 C3 109.9(2) . . ? C9 C5 C4 109.4(2) . . ? C9 C5 C6 109.3(3) . . ? C4 C5 C6 109.9(2) . . ? C7 C6 C5 110.0(2) . . ? C10 C7 C6 109.6(2) . . ? C10 C7 C8 108.2(2) . . ? C6 C7 C8 108.3(2) . . ? C10 C7 C13 111.2(2) . . ? C6 C7 C13 111.6(2) . . ? C8 C7 C13 107.9(2) . . ? C7 C8 C3 111.79(19) . . ? C5 C9 C11 109.8(2) . . ? C11 C10 C7 110.1(2) . . ? C10 C11 C9 109.3(2) . . ? C10 C11 C12 109.9(2) . . ? C9 C11 C12 109.2(3) . . ? C3 C12 C11 110.3(2) . . ? C14 C13 C7 115.3(2) . . ? O3 C14 O4 120.1(3) . . ? O3 C14 C13 125.6(3) . . ? O4 C14 C13 114.2(3) . . ? N1 C15 C16 123.8(3) . . ? C17 C16 C15 118.5(3) . . ? C18 C17 C16 116.0(3) . . ? C18 C17 C20 124.2(3) . . ? C16 C17 C20 119.8(3) . . ? C19 C18 C17 119.9(3) . . ? N1 C19 C18 124.6(3) . . ? C21 C20 C17 128.0(3) . . ? C20 C21 C22 127.6(3) . . ? C26 C22 C23 117.2(3) . . ? C26 C22 C21 123.2(3) . . ? C23 C22 C21 119.6(3) . . ? C22 C23 C24 118.7(3) . . ? N2 C24 C23 122.1(3) . . ? N2 C25 C26 123.8(3) . . ? C25 C26 C22 120.4(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A N2 0.82 1.87 2.683(3) 169.3 1_534 O4 H4C N1 0.82 1.98 2.759(4) 158.2 . _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.543 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.076 # Attachment '8.CIF.txt' data_compound_8 _database_code_depnum_ccdc_archive 'CCDC 289582' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H32 N2 O4' _chemical_formula_weight 436.54 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6721(17) _cell_length_b 11.845(2) _cell_length_c 12.364(3) _cell_angle_alpha 106.23(3) _cell_angle_beta 104.28(3) _cell_angle_gamma 98.19(3) _cell_volume 1150.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10439 _cell_measurement_theta_min 1.80 _cell_measurement_theta_max 27.47 _exptl_crystal_description prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.77 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type Empircial _exptl_absorpt_correction_T_min 0.9379 _exptl_absorpt_correction_T_max 0.9752 _exptl_absorpt_process_details Abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis Rapid IP' _diffrn_measurement_method '\w Oscillation' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10439 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5155 _reflns_number_gt 3607 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _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^)+(0.0964P)^2^+0.8193P] 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 SHELXL _refine_ls_extinction_coef 0.021(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5155 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1067 _refine_ls_R_factor_gt 0.0761 _refine_ls_wR_factor_ref 0.2220 _refine_ls_wR_factor_gt 0.1981 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1692(5) -0.0578(2) 0.2207(3) 0.1211(13) Uani 1 1 d . . . O2 O 0.3196(4) -0.11551(19) 0.3489(3) 0.1214(14) Uani 1 1 d . . . H2A H 0.2660 -0.1816 0.3024 0.182 Uiso 1 1 calc R . . O3 O 0.3068(4) 0.60135(19) 0.8110(2) 0.0889(9) Uani 1 1 d . . . O4 O 0.3876(3) 0.69152(16) 0.6956(2) 0.0656(6) Uani 1 1 d . . . H4C H 0.3615 0.7482 0.7369 0.098 Uiso 1 1 calc R . . N1 N 0.3104(3) -1.1135(2) -0.1810(2) 0.0609(6) Uani 1 1 d . . . N2 N 0.2044(4) -0.3503(2) 0.2029(3) 0.0840(10) Uani 1 1 d . . . C1 C 0.2772(4) -0.0329(2) 0.3090(2) 0.0511(6) Uani 1 1 d . . . C2 C 0.3717(3) 0.0929(2) 0.3855(3) 0.0507(6) Uani 1 1 d . . . H2B H 0.4176 0.1314 0.3372 0.061 Uiso 1 1 calc R . . H2C H 0.4623 0.0868 0.4462 0.061 Uiso 1 1 calc R . . C3 C 0.2743(3) 0.17552(19) 0.4463(2) 0.0388(5) Uani 1 1 d . . . C4 C 0.1461(3) 0.2073(2) 0.3568(2) 0.0513(6) Uani 1 1 d . . . H4A H 0.1988 0.2445 0.3106 0.062 Uiso 1 1 calc R . . H4B H 0.0676 0.1342 0.3032 0.062 Uiso 1 1 calc R . . C5 C 0.0581(3) 0.2939(3) 0.4209(2) 0.0579(7) Uani 1 1 d . . . H5A H -0.0249 0.3126 0.3629 0.069 Uiso 1 1 calc R . . C6 C 0.1803(3) 0.4105(2) 0.5035(2) 0.0480(6) Uani 1 1 d . . . H6A H 0.1235 0.4656 0.5432 0.058 Uiso 1 1 calc R . . H6B H 0.2325 0.4491 0.4580 0.058 Uiso 1 1 calc R . . C7 C 0.3098(3) 0.38283(18) 0.59510(19) 0.0348(5) Uani 1 1 d . . . C8 C 0.3953(3) 0.29379(18) 0.5296(2) 0.0377(5) Uani 1 1 d . . . H8A H 0.4782 0.2757 0.5869 0.045 Uiso 1 1 calc R . . H8B H 0.4494 0.3311 0.4842 0.045 Uiso 1 1 calc R . . C9 C -0.0243(3) 0.2341(3) 0.4933(3) 0.0697(9) Uani 1 1 d . . . H9A H -0.0821 0.2880 0.5334 0.084 Uiso 1 1 calc R . . H9B H -0.1031 0.1605 0.4413 0.084 Uiso 1 1 calc R . . C10 C 0.2268(3) 0.3219(2) 0.6664(2) 0.0459(6) Uani 1 1 d . . . H10A H 0.1710 0.3762 0.7082 0.055 Uiso 1 1 calc R . . H10B H 0.3086 0.3037 0.7243 0.055 Uiso 1 1 calc R . . C11 C 0.1035(4) 0.2049(2) 0.5839(2) 0.0580(8) Uani 1 1 d . . . H11A H 0.0500 0.1671 0.6302 0.070 Uiso 1 1 calc R . . C12 C 0.1911(4) 0.1181(2) 0.5198(2) 0.0522(7) Uani 1 1 d . . . H12A H 0.1130 0.0438 0.4687 0.063 Uiso 1 1 calc R . . H12B H 0.2722 0.0985 0.5771 0.063 Uiso 1 1 calc R . . C13 C 0.4387(3) 0.49818(19) 0.6765(2) 0.0453(6) Uani 1 1 d . . . H13A H 0.5121 0.4781 0.7377 0.054 Uiso 1 1 calc R . . H13B H 0.5027 0.5254 0.6306 0.054 Uiso 1 1 calc R . . C14 C 0.3709(3) 0.6010(2) 0.7347(2) 0.0476(6) Uani 1 1 d . . . C15 C 0.3400(4) -1.0150(3) -0.2086(3) 0.0673(8) Uani 1 1 d . . . H15A H 0.3737 -1.0197 -0.2752 0.081 Uiso 1 1 calc R . . C16 C 0.3236(5) -0.9058(3) -0.1434(3) 0.0706(9) Uani 1 1 d . . . H16A H 0.3461 -0.8382 -0.1660 0.085 Uiso 1 1 calc R . . C17 C 0.2737(4) -0.8955(3) -0.0442(2) 0.0633(8) Uani 1 1 d . . . C18 C 0.2378(5) -0.9984(3) -0.0169(3) 0.0754(10) Uani 1 1 d . . . H18A H 0.1996 -0.9970 0.0474 0.090 Uiso 1 1 calc R . . C19 C 0.2601(5) -1.1060(3) -0.0881(3) 0.0740(9) Uani 1 1 d . . . H19A H 0.2381 -1.1756 -0.0685 0.089 Uiso 1 1 calc R . . C20 C 0.2647(7) -0.7739(3) 0.0322(3) 0.1049(16) Uani 1 1 d . . . H20A H 0.2367 -0.7844 0.1006 0.126 Uiso 1 1 calc R . . H20B H 0.3729 -0.7213 0.0606 0.126 Uiso 1 1 calc R . . C21 C 0.1517(5) -0.7129(3) -0.0211(3) 0.0847(12) Uani 1 1 d . . . H21A H 0.0413 -0.7584 -0.0382 0.102 Uiso 1 1 calc R . . H21B H 0.1684 -0.7119 -0.0956 0.102 Uiso 1 1 calc R . . C22 C 0.1681(4) -0.5846(2) 0.0551(2) 0.0527(7) Uani 1 1 d . . . C23 C 0.1138(4) -0.5605(3) 0.1523(3) 0.0592(7) Uani 1 1 d . . . H23A H 0.0620 -0.6236 0.1708 0.071 Uiso 1 1 calc R . . C24 C 0.1354(4) -0.4442(3) 0.2221(3) 0.0727(10) Uani 1 1 d . . . H24A H 0.0982 -0.4315 0.2879 0.087 Uiso 1 1 calc R . . C25 C 0.2559(5) -0.3700(3) 0.1095(4) 0.0896(13) Uani 1 1 d . . . H25A H 0.3044 -0.3038 0.0935 0.107 Uiso 1 1 calc R . . C26 C 0.2415(4) -0.4865(3) 0.0320(3) 0.0716(9) Uani 1 1 d . . . H26A H 0.2804 -0.4969 -0.0330 0.086 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.171(3) 0.0507(14) 0.0851(19) 0.0062(13) -0.033(2) 0.0101(16) O2 0.137(2) 0.0321(11) 0.126(2) -0.0015(13) -0.0520(19) 0.0227(13) O3 0.145(2) 0.0504(12) 0.0951(18) 0.0194(12) 0.0798(18) 0.0275(14) O4 0.0933(16) 0.0365(9) 0.0824(14) 0.0200(9) 0.0455(12) 0.0280(10) N1 0.0674(15) 0.0431(12) 0.0664(15) 0.0058(11) 0.0186(12) 0.0223(11) N2 0.096(2) 0.0445(15) 0.081(2) 0.0017(14) -0.0115(17) 0.0290(15) C1 0.0641(17) 0.0348(12) 0.0484(15) 0.0041(11) 0.0172(13) 0.0118(11) C2 0.0555(15) 0.0317(11) 0.0631(16) 0.0069(11) 0.0243(13) 0.0108(10) C3 0.0440(12) 0.0296(10) 0.0420(12) 0.0079(9) 0.0170(10) 0.0068(9) C4 0.0548(15) 0.0520(14) 0.0396(13) 0.0053(11) 0.0104(11) 0.0154(12) C5 0.0489(15) 0.0638(17) 0.0481(15) 0.0047(13) 0.0016(12) 0.0236(13) C6 0.0528(14) 0.0458(13) 0.0466(14) 0.0128(11) 0.0125(11) 0.0243(11) C7 0.0374(11) 0.0270(10) 0.0400(12) 0.0107(9) 0.0117(9) 0.0078(8) C8 0.0394(12) 0.0278(10) 0.0482(13) 0.0120(9) 0.0165(10) 0.0099(8) C9 0.0403(14) 0.0701(19) 0.0707(19) -0.0148(15) 0.0188(13) -0.0012(13) C10 0.0570(15) 0.0375(12) 0.0403(13) 0.0070(10) 0.0198(11) 0.0036(10) C11 0.0634(17) 0.0471(14) 0.0558(16) 0.0029(12) 0.0339(14) -0.0112(12) C12 0.0658(17) 0.0329(12) 0.0520(15) 0.0078(11) 0.0229(13) -0.0040(11) C13 0.0443(13) 0.0284(11) 0.0590(15) 0.0088(10) 0.0151(11) 0.0073(9) C14 0.0536(14) 0.0298(11) 0.0526(15) 0.0042(10) 0.0173(12) 0.0055(10) C15 0.080(2) 0.0551(17) 0.070(2) 0.0144(15) 0.0309(17) 0.0265(15) C16 0.097(2) 0.0453(15) 0.074(2) 0.0179(15) 0.0297(18) 0.0268(16) C17 0.090(2) 0.0464(15) 0.0466(15) 0.0044(12) 0.0106(14) 0.0332(15) C18 0.112(3) 0.067(2) 0.0599(19) 0.0257(16) 0.0340(19) 0.038(2) C19 0.090(2) 0.0491(17) 0.086(2) 0.0272(16) 0.023(2) 0.0202(16) C20 0.179(5) 0.068(2) 0.060(2) 0.0032(17) 0.017(2) 0.074(3) C21 0.109(3) 0.0584(19) 0.0618(19) -0.0098(15) 0.0010(18) 0.0445(19) C22 0.0640(16) 0.0424(13) 0.0441(14) 0.0045(11) 0.0064(12) 0.0261(12) C23 0.0627(17) 0.0478(15) 0.0622(17) 0.0093(13) 0.0201(14) 0.0126(13) C24 0.074(2) 0.065(2) 0.067(2) -0.0038(16) 0.0186(16) 0.0353(17) C25 0.084(3) 0.056(2) 0.115(3) 0.050(2) -0.008(2) -0.0021(17) C26 0.078(2) 0.083(2) 0.066(2) 0.0373(18) 0.0222(16) 0.0254(18) _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 1.180(4) . ? O2 C1 1.272(3) . ? O3 C14 1.207(3) . ? O4 C14 1.297(3) . ? N1 C19 1.311(4) . ? N1 C15 1.312(4) . ? N2 C24 1.296(5) . ? N2 C25 1.312(6) . ? C1 C2 1.507(3) . ? C2 C3 1.540(3) . ? C3 C12 1.530(3) . ? C3 C4 1.532(4) . ? C3 C8 1.538(3) . ? C4 C5 1.527(4) . ? C5 C6 1.528(4) . ? C5 C9 1.530(5) . ? C6 C7 1.528(3) . ? C7 C10 1.528(3) . ? C7 C8 1.536(3) . ? C7 C13 1.540(3) . ? C9 C11 1.522(5) . ? C10 C11 1.534(3) . ? C11 C12 1.525(4) . ? C13 C14 1.506(3) . ? C15 C16 1.368(4) . ? C16 C17 1.378(5) . ? C17 C18 1.367(4) . ? C17 C20 1.510(4) . ? C18 C19 1.401(5) . ? C20 C21 1.437(5) . ? C21 C22 1.513(4) . ? C22 C23 1.369(4) . ? C22 C26 1.379(4) . ? C23 C24 1.363(4) . ? C25 C26 1.411(6) . ? 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 C19 N1 C15 117.9(3) . . ? C24 N2 C25 116.9(3) . . ? O1 C1 O2 120.2(3) . . ? O1 C1 C2 125.6(3) . . ? O2 C1 C2 114.2(3) . . ? C1 C2 C3 115.9(2) . . ? C12 C3 C4 109.5(2) . . ? C12 C3 C8 108.28(19) . . ? C4 C3 C8 107.80(19) . . ? C12 C3 C2 111.5(2) . . ? C4 C3 C2 111.8(2) . . ? C8 C3 C2 107.85(19) . . ? C5 C4 C3 110.1(2) . . ? C6 C5 C4 110.0(2) . . ? C6 C5 C9 109.3(2) . . ? C4 C5 C9 109.1(2) . . ? C5 C6 C7 110.0(2) . . ? C10 C7 C6 109.4(2) . . ? C10 C7 C8 108.00(18) . . ? C6 C7 C8 108.42(19) . . ? C10 C7 C13 111.06(19) . . ? C6 C7 C13 111.16(19) . . ? C8 C7 C13 108.72(18) . . ? C7 C8 C3 111.96(18) . . ? C11 C9 C5 109.9(2) . . ? C7 C10 C11 110.07(19) . . ? C12 C11 C9 109.2(2) . . ? C12 C11 C10 109.9(2) . . ? C9 C11 C10 109.4(2) . . ? C11 C12 C3 110.1(2) . . ? C14 C13 C7 115.1(2) . . ? O3 C14 O4 121.9(2) . . ? O3 C14 C13 124.2(2) . . ? O4 C14 C13 113.9(2) . . ? N1 C15 C16 122.8(3) . . ? C15 C16 C17 120.2(3) . . ? C18 C17 C16 117.4(3) . . ? C18 C17 C20 122.1(3) . . ? C16 C17 C20 120.5(3) . . ? C17 C18 C19 118.3(3) . . ? N1 C19 C18 123.4(3) . . ? C21 C20 C17 117.3(3) . . ? C20 C21 C22 113.7(3) . . ? C23 C22 C26 116.7(3) . . ? C23 C22 C21 121.4(3) . . ? C26 C22 C21 121.9(3) . . ? C24 C23 C22 120.3(3) . . ? N2 C24 C23 124.4(3) . . ? N2 C25 C26 123.4(3) . . ? C22 C26 C25 118.3(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A N2 0.82 1.95 2.739(4) 162.4 . O4 H4C N1 0.82 1.85 2.661(3) 173.0 1_576 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.445 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.049