# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Kumar Biradha' _publ_contact_author_email KBIRADHA@CHEM.IITKGP.ERNET.IN _publ_section_title ; Stepwise Dimerization of Double [2+2] reaction in the Co-crystals of 1,5-bis(4-pyridyl)-1,4-pentadiene-3-one and Phloroglucinol: A Single Crystal to Single Crystal Transformation ; loop_ _publ_author_name 'Kumar Biradha' 'Ramkinkar Santra' data_1 _database_code_depnum_ccdc_archive 'CCDC 688730' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 N2 O' _chemical_formula_weight 236.27 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.1243(4) _cell_length_b 15.3477(7) _cell_length_c 10.0546(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.0370(10) _cell_angle_gamma 90.00 _cell_volume 1216.26(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2932 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 28 _exptl_crystal_description Needle _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _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 'Bruker-APEX-2 CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16461 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2932 _reflns_number_gt 2089 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0672P)^2^+0.1537P] 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 2932 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _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 N11 N -0.19182(17) 0.07310(10) 0.55406(13) 0.0739(4) Uani 1 1 d . . . C11 C -0.1683(2) 0.14889(11) 0.61959(17) 0.0684(4) Uani 1 1 d . . . H11 H -0.2268 0.1971 0.5757 0.082 Uiso 1 1 calc R . . C12 C -0.06386(17) 0.16098(9) 0.74751(15) 0.0575(4) Uani 1 1 d . . . H12 H -0.0526 0.2160 0.7876 0.069 Uiso 1 1 calc R . . C13 C 0.02499(15) 0.09074(8) 0.81685(13) 0.0486(3) Uani 1 1 d . . . C14 C 0.00234(18) 0.01176(9) 0.74938(15) 0.0568(3) Uani 1 1 d . . . H14 H 0.0589 -0.0376 0.7908 0.068 Uiso 1 1 calc R . . C15 C -0.1038(2) 0.00634(11) 0.62108(16) 0.0677(4) Uani 1 1 d . . . H15 H -0.1153 -0.0476 0.5776 0.081 Uiso 1 1 calc R . . C16 C 0.13525(17) 0.10233(8) 0.95491(14) 0.0527(3) Uani 1 1 d . . . H16 H 0.1261 0.1549 0.9984 0.063 Uiso 1 1 calc R . . N21 N 0.75924(16) -0.29953(8) 1.40153(12) 0.0643(3) Uani 1 1 d . . . C21 C 0.71400(19) -0.23288(11) 1.46978(14) 0.0635(4) Uani 1 1 d . . . H21 H 0.7470 -0.2343 1.5650 0.076 Uiso 1 1 calc R . . C22 C 0.62177(17) -0.16195(9) 1.40903(13) 0.0551(3) Uani 1 1 d . . . H22 H 0.5940 -0.1173 1.4622 0.066 Uiso 1 1 calc R . . C23 C 0.57072(14) -0.15840(8) 1.26623(12) 0.0451(3) Uani 1 1 d . . . C24 C 0.61543(16) -0.22785(8) 1.19529(12) 0.0484(3) Uani 1 1 d . . . H24 H 0.5820 -0.2291 1.1001 0.058 Uiso 1 1 calc R . . C25 C 0.70963(17) -0.29519(9) 1.26573(14) 0.0562(3) Uani 1 1 d . . . H25 H 0.7404 -0.3404 1.2152 0.067 Uiso 1 1 calc R . . C26 C 0.47053(15) -0.08662(8) 1.19091(12) 0.0474(3) Uani 1 1 d . . . H26 H 0.4095 -0.0983 1.1018 0.057 Uiso 1 1 calc R . . O32 O 0.34614(16) 0.13314(6) 1.21846(12) 0.0771(3) Uani 1 1 d . . . C31 C 0.24521(17) 0.04594(8) 1.02290(13) 0.0520(3) Uani 1 1 d . . . H31 H 0.2577 -0.0071 0.9816 0.062 Uiso 1 1 calc R . . C32 C 0.35019(17) 0.06299(8) 1.16242(13) 0.0515(3) Uani 1 1 d . . . C33 C 0.45863(17) -0.00688(8) 1.23757(13) 0.0528(3) Uani 1 1 d . . . H33 H 0.5239 0.0062 1.3248 0.063 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 N11 0.0701(8) 0.0936(11) 0.0568(7) 0.0124(7) 0.0134(6) 0.0068(7) C11 0.0635(9) 0.0728(10) 0.0710(9) 0.0300(8) 0.0204(7) 0.0170(8) C12 0.0575(8) 0.0455(7) 0.0731(9) 0.0146(6) 0.0230(7) 0.0064(6) C13 0.0464(6) 0.0428(6) 0.0595(7) 0.0099(5) 0.0182(6) 0.0024(5) C14 0.0589(8) 0.0472(7) 0.0647(8) 0.0072(6) 0.0155(6) 0.0074(6) C15 0.0724(10) 0.0684(9) 0.0637(9) -0.0054(7) 0.0196(7) 0.0004(8) C16 0.0562(7) 0.0364(6) 0.0669(8) 0.0011(6) 0.0173(6) -0.0015(5) N21 0.0676(8) 0.0622(8) 0.0597(7) 0.0164(6) 0.0086(6) 0.0089(6) C21 0.0618(8) 0.0793(10) 0.0444(7) 0.0100(7) 0.0029(6) 0.0061(7) C22 0.0537(7) 0.0616(8) 0.0464(7) -0.0027(6) 0.0051(5) 0.0030(6) C23 0.0402(6) 0.0460(6) 0.0455(6) 0.0031(5) 0.0037(5) -0.0051(5) C24 0.0497(6) 0.0480(7) 0.0439(6) 0.0011(5) 0.0046(5) -0.0056(5) C25 0.0601(8) 0.0466(7) 0.0599(8) 0.0029(6) 0.0110(6) 0.0000(6) C26 0.0473(6) 0.0475(7) 0.0438(6) -0.0001(5) 0.0044(5) -0.0024(5) O32 0.0944(8) 0.0431(6) 0.0849(7) -0.0151(5) 0.0048(6) -0.0014(5) C31 0.0589(8) 0.0418(7) 0.0557(7) 0.0028(5) 0.0145(6) 0.0010(6) C32 0.0567(7) 0.0383(6) 0.0597(7) -0.0017(5) 0.0144(6) -0.0059(5) C33 0.0559(7) 0.0497(7) 0.0493(7) -0.0045(5) 0.0057(6) -0.0050(6) _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 N11 C11 1.328(2) . ? N11 C15 1.335(2) . ? C11 C12 1.371(2) . ? C12 C13 1.3875(17) . ? C13 C14 1.3795(18) . ? C13 C16 1.4689(19) . ? C14 C15 1.369(2) . ? C16 C31 1.3108(18) . ? N21 C25 1.3283(18) . ? N21 C21 1.332(2) . ? C21 C22 1.3776(19) . ? C22 C23 1.3956(17) . ? C23 C24 1.3793(17) . ? C23 C26 1.4664(16) . ? C24 C25 1.3757(17) . ? C26 C33 1.3226(17) . ? O32 C32 1.2193(15) . ? C31 C32 1.4777(19) . ? C32 C33 1.4745(18) . ? 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 C11 N11 C15 115.29(14) . . ? N11 C11 C12 124.46(14) . . ? C11 C12 C13 119.63(14) . . ? C14 C13 C12 116.39(13) . . ? C14 C13 C16 123.31(12) . . ? C12 C13 C16 120.29(12) . . ? C15 C14 C13 119.67(13) . . ? N11 C15 C14 124.53(15) . . ? C31 C16 C13 126.53(13) . . ? C25 N21 C21 115.99(12) . . ? N21 C21 C22 124.52(13) . . ? C21 C22 C23 118.76(13) . . ? C24 C23 C22 116.87(11) . . ? C24 C23 C26 119.76(11) . . ? C22 C23 C26 123.36(12) . . ? C25 C24 C23 119.85(12) . . ? N21 C25 C24 123.99(13) . . ? C33 C26 C23 126.24(11) . . ? C16 C31 C32 122.80(12) . . ? O32 C32 C33 119.02(12) . . ? O32 C32 C31 121.40(12) . . ? C33 C32 C31 119.55(11) . . ? C26 C33 C32 125.25(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.146 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.041 data_2 _database_code_depnum_ccdc_archive 'CCDC 688731' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 N2 O3' _chemical_formula_weight 346.37 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 9.543(4) _cell_length_b 21.387(9) _cell_length_c 8.802(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.868(13) _cell_angle_gamma 90.00 _cell_volume 1790.0(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3912 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 27.16 _exptl_crystal_description blocks _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 'Bruker-APEX-2 CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23691 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.16 _reflns_number_total 3912 _reflns_number_gt 2520 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+0.2049P] 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 3912 _refine_ls_number_parameters 243 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _refine_ls_shift/su_max 0.002 _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 -0.76694(13) 0.02859(6) 0.05457(15) 0.0769(4) Uani 1 1 d . . . C1 C -0.74622(16) 0.06507(8) 0.16073(19) 0.0521(4) Uani 1 1 d . . . C2 C -0.85144(15) 0.07507(7) 0.27238(18) 0.0525(4) Uani 1 1 d . . . H2 H -0.8296 0.1027 0.3525 0.063 Uiso 1 1 calc R . . C3 C -0.97463(15) 0.04680(7) 0.26399(18) 0.0487(4) Uani 1 1 d . . . H3 H -0.9938 0.0191 0.1834 0.058 Uiso 1 1 calc R . . C4 C -0.61742(16) 0.10271(8) 0.18400(19) 0.0562(4) Uani 1 1 d . . . H4 H -0.6113 0.1315 0.2635 0.067 Uiso 1 1 calc R . . C5 C -0.51004(15) 0.09846(7) 0.09991(17) 0.0520(4) Uani 1 1 d . . . H5 H -0.5160 0.0686 0.0228 0.062 Uiso 1 1 calc R . . N11 N -1.29881(13) 0.06846(7) 0.56525(16) 0.0580(4) Uani 1 1 d . . . C11 C -1.17733(18) 0.09844(9) 0.5890(2) 0.0646(5) Uani 1 1 d . . . H11 H -1.1646 0.1246 0.6735 0.077 Uiso 1 1 calc R . . C12 C -1.06918(16) 0.09327(8) 0.49619(19) 0.0595(4) Uani 1 1 d . . . H12 H -0.9862 0.1155 0.5184 0.071 Uiso 1 1 calc R . . C13 C -1.08453(14) 0.05473(7) 0.36938(17) 0.0453(4) Uani 1 1 d . . . C14 C -1.21057(15) 0.02322(7) 0.34478(18) 0.0527(4) Uani 1 1 d . . . H14 H -1.2263 -0.0035 0.2617 0.063 Uiso 1 1 calc R . . C15 C -1.31307(16) 0.03159(8) 0.4442(2) 0.0585(4) Uani 1 1 d . . . H15 H -1.3973 0.0100 0.4250 0.070 Uiso 1 1 calc R . . N21 N -0.13353(14) 0.20755(7) 0.15006(18) 0.0669(4) Uani 1 1 d . . . C21 C -0.2416(2) 0.21903(9) 0.2321(2) 0.0729(5) Uani 1 1 d . . . H21 H -0.2327 0.2514 0.3028 0.087 Uiso 1 1 calc R . . C22 C -0.36546(17) 0.18592(8) 0.2185(2) 0.0630(5) Uani 1 1 d . . . H22 H -0.4381 0.1967 0.2775 0.076 Uiso 1 1 calc R . . C23 C -0.38182(15) 0.13662(7) 0.11699(17) 0.0487(4) Uani 1 1 d . . . C24 C -0.26948(16) 0.12454(8) 0.03134(18) 0.0557(4) Uani 1 1 d . . . H24 H -0.2748 0.0921 -0.0393 0.067 Uiso 1 1 calc R . . C25 C -0.14972(17) 0.16078(9) 0.0513(2) 0.0612(4) Uani 1 1 d . . . H25 H -0.0761 0.1519 -0.0080 0.073 Uiso 1 1 calc R . . O1A O 0.05679(12) 0.29812(6) 0.25435(15) 0.0654(3) Uani 1 1 d . . . O2A O 0.47616(12) 0.41236(5) 0.23583(13) 0.0590(3) Uani 1 1 d . . . C1A C 0.18271(15) 0.30395(7) 0.19387(18) 0.0490(4) Uani 1 1 d . . . C2A C 0.26774(15) 0.35360(7) 0.24346(17) 0.0484(4) Uani 1 1 d . . . H2A H 0.2382 0.3812 0.3159 0.058 Uiso 1 1 calc R . . C3A C 0.39704(15) 0.36228(7) 0.18532(16) 0.0447(3) Uani 1 1 d . . . C4A C 0.44157(16) 0.32063(8) 0.07961(18) 0.0577(4) Uani 1 1 d . . . H4A H 0.5290 0.3255 0.0418 0.069 Uiso 1 1 calc R . . C5A C 0.35522(19) 0.27177(9) 0.0307(2) 0.0697(5) Uani 1 1 d . . . H5A H 0.3850 0.2440 -0.0412 0.084 Uiso 1 1 calc R . . C6A C 0.22566(18) 0.26307(8) 0.0858(2) 0.0613(4) Uani 1 1 d . . . H6A H 0.1681 0.2301 0.0507 0.074 Uiso 1 1 calc R . . H2AO H 0.555(2) 0.4168(9) 0.182(2) 0.094(7) Uiso 1 1 d . . . H1AO H 0.010(3) 0.2639(12) 0.211(3) 0.122(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0637(8) 0.0920(9) 0.0792(9) -0.0288(7) 0.0295(7) -0.0273(7) C1 0.0424(8) 0.0591(9) 0.0563(10) -0.0010(8) 0.0121(7) -0.0049(7) C2 0.0416(9) 0.0609(9) 0.0562(10) -0.0047(8) 0.0119(7) -0.0042(7) C3 0.0410(8) 0.0545(9) 0.0517(9) -0.0019(7) 0.0101(7) -0.0028(7) C4 0.0458(9) 0.0661(10) 0.0580(10) -0.0069(8) 0.0124(7) -0.0092(7) C5 0.0450(9) 0.0606(9) 0.0514(9) -0.0012(7) 0.0105(7) -0.0063(7) N11 0.0432(8) 0.0683(9) 0.0649(9) 0.0029(7) 0.0178(6) 0.0093(6) C11 0.0547(10) 0.0760(11) 0.0650(11) -0.0147(9) 0.0171(8) 0.0011(9) C12 0.0411(9) 0.0722(11) 0.0663(11) -0.0146(9) 0.0111(8) -0.0073(8) C13 0.0355(8) 0.0505(8) 0.0507(9) 0.0026(7) 0.0079(6) 0.0030(6) C14 0.0417(9) 0.0581(9) 0.0590(10) -0.0043(8) 0.0089(7) -0.0046(7) C15 0.0383(9) 0.0693(10) 0.0693(11) 0.0038(9) 0.0134(8) -0.0045(7) N21 0.0478(9) 0.0812(10) 0.0726(10) 0.0073(8) 0.0098(7) -0.0168(7) C21 0.0637(12) 0.0792(12) 0.0772(13) -0.0130(10) 0.0148(10) -0.0223(10) C22 0.0489(10) 0.0760(11) 0.0665(11) -0.0065(9) 0.0193(8) -0.0122(8) C23 0.0399(8) 0.0588(9) 0.0482(9) 0.0070(7) 0.0076(6) -0.0036(7) C24 0.0464(9) 0.0669(10) 0.0555(10) 0.0024(8) 0.0139(7) -0.0053(8) C25 0.0420(9) 0.0776(12) 0.0658(11) 0.0132(10) 0.0149(8) -0.0018(8) O1A 0.0429(7) 0.0773(8) 0.0779(9) 0.0029(7) 0.0153(6) -0.0117(6) O2A 0.0486(7) 0.0685(7) 0.0620(7) -0.0096(6) 0.0163(5) -0.0158(5) C1A 0.0371(8) 0.0575(9) 0.0524(9) 0.0105(7) 0.0041(7) -0.0028(7) C2A 0.0425(8) 0.0540(9) 0.0497(9) 0.0009(7) 0.0098(7) -0.0001(7) C3A 0.0391(8) 0.0521(8) 0.0429(8) 0.0044(7) 0.0039(6) -0.0034(6) C4A 0.0447(9) 0.0696(10) 0.0610(10) -0.0073(8) 0.0182(8) -0.0057(8) C5A 0.0636(11) 0.0729(11) 0.0752(12) -0.0215(10) 0.0208(9) -0.0082(9) C6A 0.0542(10) 0.0622(10) 0.0675(11) -0.0065(9) 0.0051(8) -0.0135(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 O1 C1 1.2204(19) . ? C1 C4 1.469(2) . ? C1 C2 1.479(2) . ? C2 C3 1.318(2) . ? C3 C13 1.468(2) . ? C4 C5 1.317(2) . ? C5 C23 1.468(2) . ? N11 C15 1.324(2) . ? N11 C11 1.326(2) . ? C11 C12 1.374(2) . ? C12 C13 1.385(2) . ? C13 C14 1.380(2) . ? C14 C15 1.378(2) . ? N21 C25 1.326(2) . ? N21 C21 1.331(2) . ? C21 C22 1.375(2) . ? C22 C23 1.382(2) . ? C23 C24 1.386(2) . ? C24 C25 1.380(2) . ? O1A C1A 1.3607(18) . ? O2A C3A 1.3631(18) . ? C1A C6A 1.379(2) . ? C1A C2A 1.384(2) . ? C2A C3A 1.388(2) . ? C3A C4A 1.381(2) . ? C4A C5A 1.377(2) . ? C5A C6A 1.379(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 O1 C1 C4 122.44(14) . . ? O1 C1 C2 121.74(14) . . ? C4 C1 C2 115.81(14) . . ? C3 C2 C1 123.30(15) . . ? C2 C3 C13 126.39(15) . . ? C5 C4 C1 124.43(16) . . ? C4 C5 C23 125.85(15) . . ? C15 N11 C11 116.34(14) . . ? N11 C11 C12 123.96(16) . . ? C11 C12 C13 119.56(15) . . ? C14 C13 C12 116.64(13) . . ? C14 C13 C3 120.30(14) . . ? C12 C13 C3 123.06(13) . . ? C15 C14 C13 119.55(15) . . ? N11 C15 C14 123.96(15) . . ? C25 N21 C21 116.25(14) . . ? N21 C21 C22 123.93(18) . . ? C21 C22 C23 119.89(16) . . ? C22 C23 C24 116.32(14) . . ? C22 C23 C5 122.53(14) . . ? C24 C23 C5 121.15(15) . . ? C25 C24 C23 119.77(16) . . ? N21 C25 C24 123.83(15) . . ? O1A C1A C6A 122.38(14) . . ? O1A C1A C2A 117.42(14) . . ? C6A C1A C2A 120.20(14) . . ? C1A C2A C3A 120.14(14) . . ? O2A C3A C4A 122.21(13) . . ? O2A C3A C2A 118.04(13) . . ? C4A C3A C2A 119.75(14) . . ? C5A C4A C3A 119.33(15) . . ? C4A C5A C6A 121.56(16) . . ? C5A C6A C1A 119.00(15) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.16 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.128 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.032 data_3 _database_code_depnum_ccdc_archive 'CCDC 688732' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H21 N3 O4' _chemical_formula_weight 403.43 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.7801(13) _cell_length_b 13.6092(11) _cell_length_c 19.7644(16) _cell_angle_alpha 90.00 _cell_angle_beta 91.767(3) _cell_angle_gamma 90.00 _cell_volume 4242.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4169 _cell_measurement_theta_min 1.98 _cell_measurement_theta_max 26.00 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.989 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 'BRUKER-APEX-2 CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26692 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4169 _reflns_number_gt 2160 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. To correct the Hirshfeld test differences of C-C bonds of C33-C36, N21-C25 and C10-C11 three following restraints were applied. DELU 0.002 0.002 C33 C36 DELU 0.003 0.003 N21 C25 DELU 0.003 0.003 C10 C11 ; _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^)+(0.0748P)^2^+0.4044P] 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 4169 _refine_ls_number_parameters 283 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1225 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1556 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.023 _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 -0.17441(11) 0.35003(18) 0.13601(9) 0.0946(7) Uani 1 1 d . . . O3 O 0.02158(13) 0.33991(16) -0.04353(9) 0.0878(6) Uani 1 1 d . . . O5 O 0.09355(12) 0.20917(14) 0.17371(9) 0.0726(5) Uani 1 1 d . . . C1 C -0.09797(13) 0.32636(19) 0.11088(11) 0.0630(7) Uani 1 1 d . . . C2 C -0.07805(14) 0.34810(18) 0.04508(11) 0.0638(7) Uani 1 1 d . . . H2 H -0.1171 0.3802 0.0167 0.077 Uiso 1 1 calc R . . C3 C 0.00020(14) 0.32186(18) 0.02159(11) 0.0602(6) Uani 1 1 d . . . C4 C 0.05885(14) 0.27528(17) 0.06370(11) 0.0598(6) Uani 1 1 d . . . H4 H 0.1118 0.2579 0.0481 0.072 Uiso 1 1 calc R . . C5 C 0.03747(13) 0.25513(17) 0.12910(11) 0.0556(6) Uani 1 1 d . . . C6 C -0.04031(13) 0.27855(18) 0.15336(11) 0.0618(7) Uani 1 1 d . . . H6 H -0.0540 0.2626 0.1975 0.074 Uiso 1 1 calc R . . O10 O 0.57712(12) 0.32790(18) 0.17905(10) 0.0979(7) Uani 1 1 d . . . C10 C 0.57254(15) 0.4171(3) 0.18051(13) 0.0710(7) Uani 1 1 d U . . C11 C 0.63188(16) 0.4779(2) 0.22405(12) 0.0715(7) Uani 1 1 d U . . H11 H 0.6188 0.5436 0.2311 0.086 Uiso 1 1 calc R . . C12 C 0.51156(15) 0.4700(2) 0.13818(12) 0.0682(7) Uani 1 1 d . . . H12 H 0.5141 0.5382 0.1380 0.082 Uiso 1 1 calc R . . N21 N 0.27588(14) 0.5611(2) -0.03751(11) 0.0818(7) Uani 1 1 d U . . C21 C 0.34259(17) 0.6089(2) -0.01324(14) 0.0798(8) Uani 1 1 d . . . H21 H 0.3507 0.6731 -0.0278 0.096 Uiso 1 1 calc R . . C22 C 0.40079(15) 0.5702(2) 0.03215(12) 0.0706(7) Uani 1 1 d . . . H22 H 0.4464 0.6080 0.0478 0.085 Uiso 1 1 calc R . . C23 C 0.39156(14) 0.4750(2) 0.05448(12) 0.0603(6) Uani 1 1 d . . . C24 C 0.32049(16) 0.4251(2) 0.03073(14) 0.0808(8) Uani 1 1 d . . . H24 H 0.3104 0.3611 0.0449 0.097 Uiso 1 1 calc R . . C25 C 0.26497(18) 0.4706(3) -0.01392(16) 0.0922(9) Uani 1 1 d U . . H25 H 0.2169 0.4362 -0.0285 0.111 Uiso 1 1 calc R . . C26 C 0.45297(14) 0.4273(2) 0.10012(12) 0.0662(7) Uani 1 1 d . . . H26 H 0.4503 0.3592 0.1025 0.079 Uiso 1 1 calc R . . N31 N 0.88488(15) 0.58717(19) 0.37768(10) 0.0730(6) Uani 1 1 d . . . C31 C 0.89568(17) 0.4986(2) 0.35297(14) 0.0808(8) Uani 1 1 d . . . H31 H 0.9460 0.4662 0.3642 0.097 Uiso 1 1 calc R . . C32 C 0.83769(17) 0.4509(2) 0.31182(14) 0.0770(7) Uani 1 1 d . . . H32 H 0.8496 0.3886 0.2952 0.092 Uiso 1 1 calc R . . C33 C 0.76213(15) 0.49548(19) 0.29524(11) 0.0622(6) Uani 1 1 d U . . C34 C 0.74880(16) 0.5892(2) 0.32131(12) 0.0700(7) Uani 1 1 d . . . H34 H 0.6985 0.6227 0.3116 0.084 Uiso 1 1 calc R . . C35 C 0.81175(18) 0.6312(2) 0.36187(12) 0.0751(8) Uani 1 1 d . . . H35 H 0.8025 0.6938 0.3791 0.090 Uiso 1 1 calc R . . C36 C 0.69974(15) 0.4431(2) 0.25191(12) 0.0709(7) Uani 1 1 d U . . H36 H 0.7109 0.3771 0.2438 0.085 Uiso 1 1 calc R . . N100 N 0.26677(16) 0.2036(2) 0.14123(14) 0.1088(9) Uani 1 1 d . . . C100 C 0.32963(17) 0.1825(2) 0.16410(14) 0.0785(8) Uani 1 1 d . . . C101 C 0.40955(16) 0.1550(3) 0.19418(14) 0.1078(12) Uani 1 1 d . . . H10A H 0.4540 0.1905 0.1728 0.162 Uiso 1 1 calc R . . H10B H 0.4181 0.0857 0.1883 0.162 Uiso 1 1 calc R . . H10C H 0.4102 0.1703 0.2416 0.162 Uiso 1 1 calc R . . H5O H 0.140(2) 0.210(2) 0.1554(15) 0.107(12) Uiso 1 1 d . . . H3O H -0.0245(18) 0.361(2) -0.0644(15) 0.098(10) Uiso 1 1 d . . . H1O H -0.206(2) 0.379(3) 0.1028(18) 0.135(13) 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 0.0550(11) 0.165(2) 0.0632(11) 0.0081(12) 0.0011(9) 0.0296(12) O3 0.0756(13) 0.1359(18) 0.0521(11) 0.0145(10) 0.0036(9) 0.0332(12) O5 0.0645(11) 0.0804(13) 0.0716(11) 0.0132(9) -0.0188(10) 0.0133(10) C1 0.0461(13) 0.0897(19) 0.0529(14) -0.0007(13) -0.0060(11) 0.0050(12) C2 0.0542(14) 0.0849(19) 0.0514(14) 0.0042(12) -0.0098(11) 0.0183(12) C3 0.0587(14) 0.0738(17) 0.0479(13) -0.0011(12) -0.0032(11) 0.0098(12) C4 0.0493(12) 0.0701(17) 0.0597(14) -0.0023(12) -0.0053(11) 0.0133(11) C5 0.0530(13) 0.0572(15) 0.0555(13) 0.0016(11) -0.0159(11) 0.0032(11) C6 0.0539(14) 0.0834(19) 0.0476(13) 0.0064(12) -0.0078(11) 0.0003(12) O10 0.0849(14) 0.0923(17) 0.1138(16) 0.0061(13) -0.0402(12) 0.0066(12) C10 0.0571(15) 0.087(2) 0.0680(16) 0.0067(15) -0.0114(12) -0.0009(14) C11 0.0697(16) 0.0821(19) 0.0621(15) 0.0089(13) -0.0083(13) 0.0033(13) C12 0.0614(15) 0.0798(19) 0.0628(14) -0.0003(13) -0.0099(13) -0.0006(14) N21 0.0626(14) 0.1066(18) 0.0749(14) -0.0108(14) -0.0173(11) 0.0216(14) C21 0.0670(17) 0.097(2) 0.0742(17) 0.0086(16) -0.0119(15) 0.0106(16) C22 0.0573(15) 0.088(2) 0.0656(15) 0.0026(15) -0.0117(12) -0.0058(14) C23 0.0478(13) 0.0775(19) 0.0551(13) -0.0107(13) -0.0049(11) 0.0101(13) C24 0.0685(16) 0.0740(19) 0.098(2) -0.0169(16) -0.0288(16) 0.0086(15) C25 0.0712(18) 0.098(2) 0.106(2) -0.0266(18) -0.0313(17) 0.0112(18) C26 0.0567(14) 0.0735(18) 0.0678(15) -0.0038(14) -0.0060(13) 0.0002(13) N31 0.0817(15) 0.0786(17) 0.0576(12) -0.0001(12) -0.0144(11) -0.0154(13) C31 0.0799(18) 0.075(2) 0.0859(19) 0.0105(17) -0.0276(16) -0.0097(16) C32 0.0739(17) 0.0684(18) 0.0874(18) -0.0007(15) -0.0186(15) -0.0038(15) C33 0.0674(16) 0.0699(18) 0.0489(13) 0.0012(12) -0.0016(11) -0.0152(12) C34 0.0635(15) 0.088(2) 0.0586(14) -0.0032(15) 0.0008(12) -0.0020(14) C35 0.0823(19) 0.080(2) 0.0629(16) -0.0146(14) 0.0013(15) -0.0065(16) C36 0.0624(15) 0.0823(19) 0.0674(15) 0.0022(13) -0.0063(12) -0.0066(13) N100 0.0708(16) 0.133(2) 0.121(2) -0.0055(18) -0.0193(15) 0.0173(16) C100 0.0575(16) 0.108(2) 0.0702(17) -0.0046(16) -0.0017(14) -0.0005(16) C101 0.0601(16) 0.191(4) 0.0721(18) 0.030(2) -0.0007(14) 0.0019(19) _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 1.357(3) . ? O3 C3 1.363(3) . ? O5 C5 1.380(3) . ? C1 C2 1.379(3) . ? C1 C6 1.381(3) . ? C2 C3 1.380(3) . ? C3 C4 1.380(3) . ? C4 C5 1.374(3) . ? C5 C6 1.369(3) . ? O10 C10 1.217(3) . ? C10 C12 1.447(4) . ? C10 C11 1.500(4) . ? C11 C36 1.279(3) . ? C12 C26 1.309(3) . ? N21 C21 1.315(3) . ? N21 C25 1.330(4) . ? C21 C22 1.369(3) . ? C22 C23 1.377(3) . ? C23 C24 1.381(3) . ? C23 C26 1.456(3) . ? C24 C25 1.372(4) . ? N31 C31 1.313(3) . ? N31 C35 1.329(3) . ? C31 C32 1.369(3) . ? C32 C33 1.368(3) . ? C33 C34 1.394(3) . ? C33 C36 1.469(3) . ? C34 C35 1.381(3) . ? N100 C100 1.115(3) . ? C100 C101 1.428(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 O1 C1 C2 121.7(2) . . ? O1 C1 C6 117.7(2) . . ? C2 C1 C6 120.6(2) . . ? C1 C2 C3 119.6(2) . . ? O3 C3 C4 118.1(2) . . ? O3 C3 C2 121.4(2) . . ? C4 C3 C2 120.4(2) . . ? C5 C4 C3 118.7(2) . . ? C6 C5 C4 122.1(2) . . ? C6 C5 O5 116.5(2) . . ? C4 C5 O5 121.4(2) . . ? C5 C6 C1 118.5(2) . . ? O10 C10 C12 121.4(3) . . ? O10 C10 C11 121.8(2) . . ? C12 C10 C11 116.8(3) . . ? C36 C11 C10 122.9(3) . . ? C26 C12 C10 123.9(3) . . ? C21 N21 C25 116.2(2) . . ? N21 C21 C22 124.2(3) . . ? C21 C22 C23 119.8(3) . . ? C22 C23 C24 116.5(2) . . ? C22 C23 C26 122.9(2) . . ? C24 C23 C26 120.6(3) . . ? C25 C24 C23 119.5(3) . . ? N21 C25 C24 123.8(3) . . ? C12 C26 C23 127.1(3) . . ? C31 N31 C35 116.6(2) . . ? N31 C31 C32 124.3(3) . . ? C33 C32 C31 119.6(3) . . ? C32 C33 C34 117.2(2) . . ? C32 C33 C36 119.2(3) . . ? C34 C33 C36 123.6(2) . . ? C35 C34 C33 118.7(2) . . ? N31 C35 C34 123.6(3) . . ? C11 C36 C33 127.5(3) . . ? N100 C100 C101 179.2(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.301 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.032 data_4 _database_code_depnum_ccdc_archive 'CCDC 688733' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H42 N6 O8' _chemical_formula_weight 806.86 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.333(7) _cell_length_b 13.061(6) _cell_length_c 20.359(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.412(16) _cell_angle_gamma 90.00 _cell_volume 4077(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3205 _cell_measurement_theta_min 2 _cell_measurement_theta_max 24 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.989 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 'Bruker-APpex-2 CCD area Detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21363 _diffrn_reflns_av_R_equivalents 0.1465 _diffrn_reflns_av_sigmaI/netI 0.0958 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 24.00 _reflns_number_total 3205 _reflns_number_gt 1439 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. To correct the Hirshfeld test differences of C-O bonds of C1-O1 SIMU 0.005 0.005 C1 O1 has been applied. Which created the following six restrains SIMU U11 O1 C1 SIMU U22 O1 C1 SIMU U33 O1 C1 SIMU U23 O1 C1 SIMU U12 O1 C1 ; _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^)+(0.1014P)^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 SHELXL _refine_ls_extinction_coef 0.0049(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3205 _refine_ls_number_parameters 284 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1779 _refine_ls_R_factor_gt 0.0678 _refine_ls_wR_factor_ref 0.1914 _refine_ls_wR_factor_gt 0.1573 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 1.013 _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 0.9166(3) 0.3735(4) 0.6783(2) 0.1152(15) Uani 1 1 d U . . C1 C 0.9440(3) 0.4516(5) 0.6998(3) 0.0695(14) Uani 1 1 d U . . C2 C 0.9053(3) 0.5050(4) 0.7577(3) 0.0673(16) Uani 1 1 d . . . H2 H 0.8900 0.5762 0.7477 0.081 Uiso 1 1 calc R . . C3 C 0.8339(3) 0.4507(4) 0.7967(2) 0.0551(13) Uani 1 1 d . . . H3 H 0.8164 0.3865 0.7754 0.066 Uiso 1 1 calc R . . C4 C 0.9711(3) 0.4964(3) 0.8192(2) 0.0600(14) Uani 1 1 d . . . H4 H 0.9789 0.5628 0.8409 0.072 Uiso 1 1 calc R . . C5 C 0.9036(3) 0.4301(3) 0.8553(2) 0.0521(13) Uani 1 1 d . . . H5 H 0.9221 0.3583 0.8544 0.063 Uiso 1 1 calc R . . N11 N 0.6166(3) 0.6144(3) 0.87567(18) 0.0583(11) Uani 1 1 d . . . C11 C 0.6120(3) 0.5163(4) 0.8594(2) 0.0609(14) Uani 1 1 d . . . H11 H 0.5607 0.4813 0.8685 0.073 Uiso 1 1 calc R . . C12 C 0.6787(3) 0.4631(4) 0.8300(2) 0.0569(13) Uani 1 1 d . . . H12 H 0.6711 0.3948 0.8185 0.068 Uiso 1 1 calc R . . C13 C 0.7562(3) 0.5111(3) 0.8175(2) 0.0444(11) Uani 1 1 d . . . C14 C 0.7598(3) 0.6144(4) 0.8323(2) 0.0578(13) Uani 1 1 d . . . H14 H 0.8101 0.6515 0.8232 0.069 Uiso 1 1 calc R . . C15 C 0.6900(3) 0.6624(4) 0.8602(2) 0.0581(13) Uani 1 1 d . . . H15 H 0.6941 0.7322 0.8687 0.070 Uiso 1 1 calc R . . N21 N 0.7956(3) 0.5189(4) 1.0410(2) 0.0688(13) Uani 1 1 d . . . C21 C 0.7706(4) 0.4358(5) 1.0093(3) 0.0739(16) Uani 1 1 d . . . H21 H 0.7242 0.3984 1.0261 0.089 Uiso 1 1 calc R . . C22 C 0.8091(3) 0.4015(4) 0.9528(2) 0.0643(14) Uani 1 1 d . . . H22 H 0.7912 0.3398 0.9342 0.077 Uiso 1 1 calc R . . C23 C 0.8738(3) 0.4575(4) 0.9234(2) 0.0489(12) Uani 1 1 d . . . C24 C 0.9018(3) 0.5420(4) 0.9573(2) 0.0701(15) Uani 1 1 d . . . H24 H 0.9477 0.5810 0.9414 0.084 Uiso 1 1 calc R . . C25 C 0.8612(4) 0.5693(4) 1.0155(2) 0.0727(16) Uani 1 1 d . . . H25 H 0.8818 0.6267 1.0378 0.087 Uiso 1 1 calc R . . O1A O 0.4257(3) 0.2274(3) 0.67993(17) 0.0659(10) Uani 1 1 d . . . O2A O 0.6887(2) 0.3945(3) 0.63516(16) 0.0714(11) Uani 1 1 d . . . O3A O 0.4918(2) 0.3097(3) 0.45869(18) 0.0842(13) Uani 1 1 d . . . C1A C 0.4804(3) 0.2693(3) 0.6337(2) 0.0494(12) Uani 1 1 d . . . C2A C 0.5566(3) 0.3102(3) 0.6552(2) 0.0523(12) Uani 1 1 d . . . H2A H 0.5707 0.3088 0.6997 0.063 Uiso 1 1 calc R . . C3A C 0.6130(3) 0.3541(4) 0.6111(2) 0.0526(12) Uani 1 1 d . . . C4A C 0.5923(3) 0.3555(4) 0.5441(2) 0.0578(13) Uani 1 1 d . . . H4A H 0.6304 0.3848 0.5141 0.069 Uiso 1 1 calc R . . C5A C 0.5158(3) 0.3134(4) 0.5233(2) 0.0587(13) Uani 1 1 d . . . C6A C 0.4570(3) 0.2694(3) 0.5678(3) 0.0588(13) Uani 1 1 d . . . H6A H 0.4044 0.2413 0.5535 0.071 Uiso 1 1 calc R . . N100 N 0.7514(3) -0.1843(4) 0.3436(2) 0.0835(15) Uani 1 1 d . . . C101 C 0.9031(4) -0.1218(5) 0.3105(3) 0.098(2) Uani 1 1 d . . . H10A H 0.9453 -0.1471 0.3415 0.147 Uiso 1 1 calc R . . H10B H 0.9043 -0.0483 0.3103 0.147 Uiso 1 1 calc R . . H10C H 0.9167 -0.1469 0.2674 0.147 Uiso 1 1 calc R . . C100 C 0.8167(4) -0.1567(4) 0.3289(2) 0.0612(14) Uani 1 1 d . . . H1AO H 0.373(4) 0.200(4) 0.661(2) 0.09(2) Uiso 1 1 d . . . H3AO H 0.534(4) 0.343(4) 0.429(3) 0.096(18) Uiso 1 1 d . . . H2AO H 0.725(5) 0.436(6) 0.601(4) 0.18(3) 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 0.066(3) 0.185(4) 0.095(3) -0.051(3) 0.028(2) -0.042(3) C1 0.048(3) 0.091(4) 0.070(3) -0.007(3) 0.025(3) -0.011(3) C2 0.060(4) 0.064(3) 0.078(4) 0.019(3) 0.038(3) 0.019(3) C3 0.051(3) 0.057(3) 0.057(3) -0.001(2) 0.019(2) 0.001(3) C4 0.060(4) 0.056(3) 0.065(3) -0.018(2) 0.024(3) -0.019(3) C5 0.053(3) 0.047(3) 0.056(3) -0.001(2) 0.013(2) 0.000(2) N11 0.044(3) 0.072(3) 0.059(3) -0.001(2) 0.011(2) 0.010(2) C11 0.038(3) 0.067(4) 0.078(4) 0.010(3) 0.011(3) -0.003(3) C12 0.042(3) 0.050(3) 0.079(3) 0.005(3) 0.015(3) -0.001(3) C13 0.035(3) 0.048(3) 0.050(3) -0.001(2) 0.010(2) 0.005(2) C14 0.036(3) 0.060(3) 0.078(4) -0.005(3) 0.007(3) -0.001(2) C15 0.042(3) 0.054(3) 0.078(4) -0.009(3) 0.006(3) 0.005(3) N21 0.064(3) 0.090(3) 0.053(3) -0.001(2) 0.016(2) 0.008(3) C21 0.073(4) 0.086(4) 0.062(4) 0.010(3) 0.028(3) -0.007(3) C22 0.073(4) 0.061(3) 0.060(3) 0.008(3) 0.027(3) -0.002(3) C23 0.041(3) 0.058(3) 0.048(3) 0.004(2) 0.013(2) 0.004(2) C24 0.062(4) 0.089(4) 0.059(3) 0.001(3) 0.022(3) -0.014(3) C25 0.068(4) 0.090(4) 0.060(3) -0.011(3) 0.014(3) -0.005(3) O1A 0.056(3) 0.074(2) 0.069(2) 0.0175(18) 0.018(2) -0.006(2) O2A 0.049(2) 0.106(3) 0.059(2) 0.009(2) 0.0021(19) -0.015(2) O3A 0.062(3) 0.136(3) 0.055(2) 0.012(2) 0.0015(19) -0.040(2) C1A 0.039(3) 0.051(3) 0.059(3) 0.009(2) 0.017(3) 0.005(2) C2A 0.039(3) 0.068(3) 0.050(3) 0.012(2) 0.006(2) 0.007(3) C3A 0.039(3) 0.064(3) 0.054(3) 0.006(2) 0.008(2) -0.002(3) C4A 0.048(3) 0.070(3) 0.056(3) 0.009(2) 0.014(3) -0.009(3) C5A 0.046(3) 0.077(4) 0.053(3) 0.007(3) 0.010(3) -0.011(3) C6A 0.043(3) 0.059(3) 0.075(4) 0.005(3) 0.007(3) -0.003(2) N100 0.067(4) 0.098(4) 0.086(3) -0.004(3) 0.023(3) -0.017(3) C101 0.053(4) 0.130(5) 0.110(5) 0.037(4) -0.006(3) -0.011(4) C100 0.053(4) 0.072(3) 0.059(3) 0.004(3) 0.008(3) -0.006(3) _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 1.186(6) . ? C1 C4 1.482(7) 2_756 ? C1 C2 1.495(7) . ? C2 C3 1.532(6) . ? C2 C4 1.607(7) . ? C3 C13 1.493(6) . ? C3 C5 1.619(7) . ? C4 C1 1.482(7) 2_756 ? C4 C5 1.540(6) . ? C5 C23 1.506(6) . ? N11 C11 1.325(6) . ? N11 C15 1.329(5) . ? C11 C12 1.377(6) . ? C12 C13 1.368(6) . ? C13 C14 1.383(6) . ? C14 C15 1.368(6) . ? N21 C25 1.313(6) . ? N21 C21 1.319(6) . ? C21 C22 1.372(6) . ? C22 C23 1.374(6) . ? C23 C24 1.369(7) . ? C24 C25 1.389(6) . ? O1A C1A 1.379(5) . ? O2A C3A 1.362(5) . ? O3A C5A 1.364(6) . ? C1A C2A 1.355(6) . ? C1A C6A 1.386(6) . ? C2A C3A 1.377(6) . ? C3A C4A 1.398(6) . ? C4A C5A 1.359(6) . ? C5A C6A 1.406(6) . ? N100 C100 1.108(6) . ? C101 C100 1.452(7) . ? 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 O1 C1 C4 123.6(5) . 2_756 ? O1 C1 C2 123.4(5) . . ? C4 C1 C2 112.1(5) 2_756 . ? C1 C2 C3 118.8(4) . . ? C1 C2 C4 109.4(4) . . ? C3 C2 C4 90.6(4) . . ? C13 C3 C2 118.5(4) . . ? C13 C3 C5 113.7(4) . . ? C2 C3 C5 89.3(4) . . ? C1 C4 C5 119.8(4) 2_756 . ? C1 C4 C2 111.8(4) 2_756 . ? C5 C4 C2 89.5(4) . . ? C23 C5 C4 121.0(4) . . ? C23 C5 C3 115.8(4) . . ? C4 C5 C3 89.9(3) . . ? C11 N11 C15 116.1(4) . . ? N11 C11 C12 124.0(5) . . ? C13 C12 C11 119.9(5) . . ? C12 C13 C14 116.1(4) . . ? C12 C13 C3 120.4(4) . . ? C14 C13 C3 123.1(4) . . ? C15 C14 C13 120.5(5) . . ? N11 C15 C14 123.3(5) . . ? C25 N21 C21 116.1(4) . . ? N21 C21 C22 123.7(5) . . ? C21 C22 C23 120.5(5) . . ? C24 C23 C22 115.8(4) . . ? C24 C23 C5 124.1(4) . . ? C22 C23 C5 119.9(4) . . ? C23 C24 C25 119.8(5) . . ? N21 C25 C24 123.9(5) . . ? C2A C1A O1A 117.6(4) . . ? C2A C1A C6A 122.0(4) . . ? O1A C1A C6A 120.5(5) . . ? C1A C2A C3A 119.9(4) . . ? O2A C3A C2A 117.7(4) . . ? O2A C3A C4A 122.2(4) . . ? C2A C3A C4A 120.1(5) . . ? C5A C4A C3A 119.2(4) . . ? C4A C5A O3A 122.8(4) . . ? C4A C5A C6A 121.4(5) . . ? O3A C5A C6A 115.8(5) . . ? C1A C6A C5A 117.4(5) . . ? N100 C100 C101 179.0(7) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.394 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.061 data_5 _database_code_depnum_ccdc_archive 'CCDC 688736' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H42 N6 O8' _chemical_formula_weight 806.86 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.415(3) _cell_length_b 13.170(3) _cell_length_c 20.423(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.224(6) _cell_angle_gamma 90.00 _cell_volume 4145.1(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3636 _cell_measurement_theta_min 1.99 _cell_measurement_theta_max 25.00 _exptl_crystal_description needle _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _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 'Bruker-APEX-2 CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23872 _diffrn_reflns_av_R_equivalents 0.1032 _diffrn_reflns_av_sigmaI/netI 0.0708 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3636 _reflns_number_gt 1757 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0983P)^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 3636 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1617 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.1878 _refine_ls_wR_factor_gt 0.1604 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _refine_ls_shift/su_max 0.073 _refine_ls_shift/su_mean 0.004 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 C1 C 1.0585(2) 0.5672(4) 0.6972(2) 0.0719(11) Uani 1 1 d . . . O1 O 1.0727(2) 0.6548(3) 0.6869(2) 0.1516(17) Uani 1 1 d . A . C2 C 1.1069(18) 0.5016(19) 0.7442(15) 0.122(12) Uani 0.411(8) 1 d P A 1 H2 H 1.0834 0.4443 0.7638 0.146 Uiso 0.411(8) 1 calc PR A 1 C3 C 1.1918(6) 0.5354(7) 0.7557(6) 0.059(3) Uani 0.411(8) 1 d P A 1 H3 H 1.2140 0.5864 0.7294 0.071 Uiso 0.411(8) 1 calc PR A 1 C4 C 1.0128(7) 0.5346(7) 0.6437(5) 0.059(3) Uani 0.411(8) 1 d P A 1 H4 H 1.0226 0.4676 0.6315 0.071 Uiso 0.411(8) 1 calc PR A 1 C5 C 0.9570(6) 0.5841(7) 0.6071(5) 0.058(3) Uani 0.411(8) 1 d P A 1 H5 H 0.9649 0.6540 0.6042 0.070 Uiso 0.411(8) 1 calc PR A 1 C2' C 1.1025(10) 0.5082(7) 0.7495(7) 0.064(5) Uani 0.589(8) 1 d P . 2 H2' H 1.1190 0.4394 0.7363 0.077 Uiso 0.589(8) 1 calc PR A 2 C3' C 1.1672(4) 0.5585(5) 0.7968(4) 0.0542(19) Uani 0.589(8) 1 d P . 2 H3' H 1.1849 0.6246 0.7796 0.065 Uiso 0.589(8) 1 calc PR A 2 C4' C 0.9674(4) 0.5119(5) 0.6842(4) 0.061(2) Uani 0.589(8) 1 d P . 2 H4' H 0.9750 0.4444 0.6649 0.073 Uiso 0.589(8) 1 calc PR A 2 C5' C 0.9007(4) 0.5740(4) 0.6457(3) 0.050(2) Uani 0.589(8) 1 d P . 2 H5' H 0.9195 0.6450 0.6462 0.060 Uiso 0.589(8) 1 calc PR A 2 C24 C 0.8136(3) 0.5938(3) 0.5426(2) 0.0817(12) Uani 1 1 d . A . H24 H 0.7982 0.6561 0.5604 0.098 Uiso 1 1 calc R . . C23 C 0.8817(3) 0.5408(3) 0.5696(2) 0.0928(15) Uani 1 1 d . . . N11 N 1.3812(2) 0.3912(2) 0.87875(14) 0.0650(8) Uani 1 1 d . A . C11 C 1.3880(2) 0.4868(3) 0.86152(18) 0.0655(10) Uani 1 1 d . . . H11 H 1.4384 0.5215 0.8736 0.079 Uiso 1 1 calc R . . C12 C 1.3253(2) 0.5379(3) 0.82693(18) 0.0687(11) Uani 1 1 d . A . H12 H 1.3345 0.6050 0.8147 0.082 Uiso 1 1 calc R . . C13 C 1.2487(2) 0.4908(3) 0.81016(18) 0.0644(10) Uani 1 1 d . . . C14 C 1.2417(2) 0.3901(3) 0.82681(17) 0.0634(10) Uani 1 1 d . A . H14 H 1.1919 0.3537 0.8155 0.076 Uiso 1 1 calc R . . C15 C 1.3087(3) 0.3438(3) 0.86013(18) 0.0693(10) Uani 1 1 d . . . H15 H 1.3033 0.2753 0.8703 0.083 Uiso 1 1 calc R A . N21 N 0.7884(2) 0.4711(3) 0.46088(15) 0.0766(9) Uani 1 1 d . A . C21 C 0.8553(3) 0.4212(3) 0.4860(2) 0.0887(13) Uani 1 1 d . . . H21 H 0.8715 0.3607 0.4662 0.106 Uiso 1 1 calc R A . C22 C 0.9025(3) 0.4536(3) 0.5399(2) 0.0974(15) Uani 1 1 d . A . H22 H 0.9490 0.4151 0.5557 0.117 Uiso 1 1 calc R . . C25 C 0.7680(3) 0.5568(4) 0.49030(19) 0.0812(12) Uani 1 1 d . . . H25 H 0.7204 0.5934 0.4745 0.097 Uiso 1 1 calc R A . O1A O 0.68338(17) 0.3855(2) 0.36501(13) 0.0786(8) Uani 1 1 d . . . O2A O 0.41933(19) 0.22063(19) 0.32078(13) 0.0725(8) Uani 1 1 d . . . O3A O 0.48869(18) 0.3157(2) 0.53967(13) 0.0847(9) Uani 1 1 d . . . C1A C 0.6079(2) 0.3470(3) 0.38907(17) 0.0571(9) Uani 1 1 d . . . C2A C 0.5511(2) 0.3023(2) 0.34450(17) 0.0579(9) Uani 1 1 d . . . H2A H 0.5646 0.2981 0.3004 0.069 Uiso 1 1 calc R . . C3A C 0.4738(2) 0.2638(2) 0.36696(17) 0.0543(9) Uani 1 1 d . . . C4A C 0.4524(2) 0.2693(2) 0.43175(18) 0.0593(9) Uani 1 1 d . . . H4A H 0.4000 0.2434 0.4461 0.071 Uiso 1 1 calc R . . C5A C 0.5111(2) 0.3144(3) 0.47538(17) 0.0586(9) Uani 1 1 d . . . C6A C 0.5879(2) 0.3535(3) 0.45488(17) 0.0603(9) Uani 1 1 d . . . H6A H 0.6263 0.3840 0.4846 0.072 Uiso 1 1 calc R . . C100 C 0.1781(3) 0.1596(3) 0.33090(19) 0.0743(11) Uani 1 1 d . . . C101 C 0.0936(3) 0.1237(4) 0.3103(2) 0.1014(15) Uani 1 1 d . . . H10A H 0.0617 0.1034 0.3480 0.152 Uiso 1 1 calc R . . H10B H 0.0999 0.0667 0.2815 0.152 Uiso 1 1 calc R . . H10C H 0.0629 0.1771 0.2878 0.152 Uiso 1 1 calc R . . N100 N 0.2435(3) 0.1876(3) 0.34737(18) 0.0993(12) Uani 1 1 d . . . H1AO H 0.717(3) 0.423(3) 0.397(2) 0.107(15) Uiso 1 1 d . . . H3AO H 0.538(3) 0.341(3) 0.568(2) 0.109(14) Uiso 1 1 d . . . H2AO H 0.367(3) 0.206(3) 0.337(2) 0.107(17) 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 C1 0.060(3) 0.089(3) 0.066(3) -0.003(2) -0.016(2) 0.008(2) O1 0.081(2) 0.158(3) 0.215(4) 0.106(3) -0.041(2) -0.029(2) C2 0.065(16) 0.19(2) 0.11(2) -0.024(14) -0.047(13) 0.052(13) C3 0.042(6) 0.069(6) 0.067(8) 0.004(5) 0.004(5) 0.002(5) C4 0.061(6) 0.067(6) 0.049(6) -0.005(5) -0.004(6) 0.000(5) C5 0.051(6) 0.068(6) 0.055(6) 0.014(4) -0.001(5) -0.006(5) C2' 0.083(11) 0.033(4) 0.076(9) 0.004(5) -0.042(7) -0.024(5) C3' 0.049(4) 0.062(4) 0.051(5) -0.001(3) -0.013(4) 0.000(3) C4' 0.052(4) 0.056(4) 0.073(6) -0.011(4) -0.028(4) 0.010(3) C5' 0.052(4) 0.041(3) 0.057(4) 0.007(3) -0.024(4) -0.004(3) C24 0.107(3) 0.065(2) 0.072(3) 0.007(2) -0.037(2) 0.001(2) C23 0.109(3) 0.053(2) 0.113(4) 0.015(2) -0.072(3) -0.018(2) N11 0.058(2) 0.069(2) 0.068(2) 0.0043(16) -0.0107(16) 0.0100(16) C11 0.053(2) 0.065(2) 0.077(3) -0.010(2) -0.0164(19) 0.0028(18) C12 0.057(2) 0.054(2) 0.094(3) -0.0010(19) -0.018(2) -0.0035(18) C13 0.054(2) 0.058(2) 0.080(3) 0.0101(19) -0.018(2) -0.0014(18) C14 0.048(2) 0.070(2) 0.072(3) 0.0061(19) -0.0114(19) -0.0043(18) C15 0.064(3) 0.062(2) 0.082(3) 0.013(2) -0.004(2) 0.001(2) N21 0.067(2) 0.109(3) 0.053(2) -0.0018(19) -0.0111(17) -0.005(2) C21 0.087(3) 0.100(3) 0.078(3) -0.005(2) -0.016(3) 0.002(3) C22 0.090(3) 0.083(3) 0.116(4) -0.001(3) -0.056(3) 0.007(2) C25 0.075(3) 0.106(3) 0.061(3) 0.005(2) -0.023(2) 0.005(2) O1A 0.0573(17) 0.120(2) 0.0581(17) -0.0101(16) -0.0024(14) -0.0165(15) O2A 0.0682(19) 0.0775(17) 0.0710(18) -0.0179(14) -0.0166(16) -0.0067(14) O3A 0.0734(19) 0.130(2) 0.0508(17) -0.0095(15) 0.0025(14) -0.0392(16) C1A 0.052(2) 0.066(2) 0.053(2) -0.0040(18) -0.0045(18) 0.0027(18) C2A 0.055(2) 0.067(2) 0.051(2) -0.0106(17) -0.0086(18) 0.0061(18) C3A 0.053(2) 0.0472(19) 0.062(3) -0.0108(17) -0.0182(19) 0.0061(16) C4A 0.055(2) 0.064(2) 0.059(2) -0.0036(18) -0.0052(19) -0.0062(17) C5A 0.055(2) 0.068(2) 0.052(2) -0.0043(17) -0.0063(18) -0.0105(18) C6A 0.055(2) 0.075(2) 0.051(2) -0.0083(18) -0.0081(17) -0.0103(18) C100 0.065(3) 0.094(3) 0.063(3) -0.003(2) -0.003(2) -0.012(2) C101 0.064(3) 0.135(4) 0.106(4) -0.033(3) 0.004(2) -0.014(3) N100 0.082(3) 0.124(3) 0.091(3) -0.001(2) -0.014(2) -0.025(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 C1 O1 1.194(5) . ? C1 C4 1.357(9) . ? C1 C2' 1.475(14) . ? C1 C2 1.48(3) . ? C1 C4' 1.599(8) . ? C2 C3 1.40(3) . ? C3 C13 1.519(11) . ? C4 C5 1.303(11) . ? C5 C23 1.490(9) . ? C2' C3' 1.525(14) . ? C2' C4' 1.749(19) 2_756 ? C3' C13 1.560(7) . ? C3' C5' 1.602(14) 2_756 ? C4' C5' 1.519(7) . ? C4' C2' 1.749(19) 2_756 ? C5' C23 1.635(7) . ? C5' C3' 1.602(14) 2_756 ? C24 C23 1.367(5) . ? C24 C25 1.357(5) . ? C23 C22 1.341(6) . ? N11 C11 1.312(4) . ? N11 C15 1.328(4) . ? C11 C12 1.364(5) . ? C12 C13 1.371(5) . ? C13 C14 1.374(4) . ? C14 C15 1.369(5) . ? N21 C21 1.317(5) . ? N21 C25 1.320(5) . ? C21 C22 1.374(5) . ? O1A C1A 1.370(4) . ? O2A C3A 1.373(4) . ? O3A C5A 1.365(4) . ? C1A C6A 1.388(4) . ? C1A C2A 1.381(4) . ? C2A C3A 1.383(5) . ? C3A C4A 1.372(4) . ? C4A C5A 1.389(4) . ? C5A C6A 1.364(5) . ? C100 N100 1.118(5) . ? C100 C101 1.439(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 O1 C1 C4 104.9(6) . . ? O1 C1 C2' 123.6(5) . . ? C4 C1 C2' 129.7(7) . . ? O1 C1 C2 125.9(11) . . ? C4 C1 C2 125.6(11) . . ? C2' C1 C2 6.0(16) . . ? O1 C1 C4' 125.0(4) . . ? C4 C1 C4' 44.2(4) . . ? C2' C1 C4' 105.6(6) . . ? C2 C1 C4' 105.7(11) . . ? C3 C2 C1 112(2) . . ? C2 C3 C13 121.6(14) . . ? C5 C4 C1 129.0(8) . . ? C4 C5 C23 126.9(8) . . ? C1 C2' C3' 120.9(6) . . ? C1 C2' C4' 105.3(9) . 2_756 ? C3' C2' C4' 84.4(8) . 2_756 ? C2' C3' C13 112.1(7) . . ? C2' C3' C5' 95.2(7) . 2_756 ? C13 C3' C5' 118.7(5) . 2_756 ? C5' C4' C1 115.1(5) . . ? C5' C4' C2' 89.7(6) . 2_756 ? C1 C4' C2' 115.9(6) . 2_756 ? C23 C5' C4' 117.0(5) . . ? C23 C5' C3' 123.8(4) . 2_756 ? C4' C5' C3' 89.9(5) . 2_756 ? C23 C24 C25 121.0(4) . . ? C24 C23 C22 116.4(4) . . ? C24 C23 C5' 111.5(4) . . ? C22 C23 C5' 128.3(4) . . ? C24 C23 C5 126.5(5) . . ? C22 C23 C5 111.7(5) . . ? C5' C23 C5 44.5(4) . . ? C11 N11 C15 116.5(3) . . ? N11 C11 C12 123.6(3) . . ? C11 C12 C13 120.2(3) . . ? C14 C13 C12 116.6(3) . . ? C14 C13 C3 120.5(5) . . ? C12 C13 C3 119.2(5) . . ? C14 C13 C3' 121.9(4) . . ? C12 C13 C3' 118.1(4) . . ? C3 C13 C3' 37.0(4) . . ? C13 C14 C15 119.4(3) . . ? N11 C15 C14 123.7(3) . . ? C21 N21 C25 116.2(3) . . ? N21 C21 C22 123.6(4) . . ? C21 C22 C23 120.0(4) . . ? N21 C25 C24 122.7(4) . . ? O1A C1A C6A 122.2(3) . . ? O1A C1A C2A 116.9(3) . . ? C6A C1A C2A 120.9(3) . . ? C3A C2A C1A 118.4(3) . . ? C2A C3A C4A 121.8(3) . . ? C2A C3A O2A 116.3(3) . . ? C4A C3A O2A 121.9(3) . . ? C3A C4A C5A 118.3(3) . . ? O3A C5A C6A 122.0(3) . . ? O3A C5A C4A 116.6(3) . . ? C6A C5A C4A 121.4(3) . . ? C5A C6A C1A 119.1(3) . . ? N100 C100 C101 179.4(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.204 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.038 data_6 _database_code_depnum_ccdc_archive 'CCDC 688737' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H32 N4 O4' _chemical_formula_weight 536.62 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)/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 9.1425(8) _cell_length_b 18.5623(16) _cell_length_c 16.1103(15) _cell_angle_alpha 90.00 _cell_angle_beta 102.989(3) _cell_angle_gamma 90.00 _cell_volume 2664.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4589 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 25.00 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.989 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 'Bruker-Apex-2 CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30448 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4589 _reflns_number_gt 2928 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The two methanol molecules are haveing high thermal parameters and unusually short C...O distances. Therefore, the final structure was refined without MeOH molecules by using PLATON squeeze option. ; _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^)+(0.2000P)^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 Constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4589 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.2014 _refine_ls_wR_factor_gt 0.1625 _refine_ls_goodness_of_fit_ref 0.710 _refine_ls_restrained_S_all 0.710 _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 O1A O -0.0094(2) -0.00121(9) 0.61605(12) 0.0645(5) Uani 1 1 d . . . C11A C -0.0776(3) -0.05259(12) 0.63403(13) 0.0455(5) Uani 1 1 d . . . C12A C -0.2001(2) -0.04494(11) 0.68231(13) 0.0429(5) Uani 1 1 d . . . H12A H -0.1606 -0.0513 0.7436 0.052 Uiso 1 1 calc R . . C13A C -0.0570(3) -0.12857(11) 0.60489(13) 0.0444(5) Uani 1 1 d . . . H13A H -0.0124 -0.1608 0.6519 0.053 Uiso 1 1 calc R . . N21A N -0.2462(4) 0.20587(16) 0.8300(2) 0.1007(10) Uani 1 1 d . . . N31A N 0.2914(4) -0.31998(19) 0.5115(2) 0.1013(10) Uani 1 1 d . . . C21A C -0.1587(4) 0.1489(2) 0.8475(2) 0.0942(11) Uani 1 1 d . . . H21A H -0.0843 0.1495 0.8975 0.113 Uiso 1 1 calc R . . C22A C -0.1701(3) 0.08905(16) 0.79682(18) 0.0710(8) Uani 1 1 d . . . H22A H -0.1035 0.0509 0.8123 0.085 Uiso 1 1 calc R . . C23A C -0.2790(3) 0.08528(13) 0.72361(14) 0.0497(6) Uani 1 1 d . . . C24A C -0.3715(4) 0.14447(16) 0.70523(19) 0.0849(10) Uani 1 1 d . . . H24A H -0.4472 0.1455 0.6558 0.102 Uiso 1 1 calc R . . C25A C -0.3516(5) 0.2013(2) 0.7596(2) 0.1078(14) Uani 1 1 d . . . H25A H -0.4174 0.2399 0.7460 0.129 Uiso 1 1 calc R . . C26A C -0.3015(3) 0.02210(12) 0.66397(13) 0.0453(5) Uani 1 1 d . . . H26A H -0.3005 0.0396 0.6067 0.054 Uiso 1 1 calc R . . C31A C 0.3194(5) -0.2559(3) 0.4859(4) 0.1299(17) Uani 1 1 d . . . H31A H 0.4019 -0.2505 0.4616 0.156 Uiso 1 1 calc R . . C32A C 0.2354(4) -0.19620(19) 0.4924(3) 0.0970(12) Uani 1 1 d . . . H32A H 0.2623 -0.1520 0.4730 0.116 Uiso 1 1 calc R . . C33A C 0.1124(3) -0.20069(13) 0.52707(15) 0.0522(6) Uani 1 1 d . . . C34A C 0.0834(3) -0.26709(14) 0.55609(18) 0.0642(7) Uani 1 1 d . . . H34A H 0.0026 -0.2736 0.5815 0.077 Uiso 1 1 calc R . . C35A C 0.1756(4) -0.32497(17) 0.5474(2) 0.0804(9) Uani 1 1 d . . . H35A H 0.1544 -0.3696 0.5681 0.096 Uiso 1 1 calc R . . C36A C 0.0141(3) -0.13654(12) 0.52754(14) 0.0478(6) Uani 1 1 d . . . H36A H 0.0623 -0.0919 0.5152 0.057 Uiso 1 1 calc R . . O1B O -0.44756(19) -0.10198(11) 0.50037(10) 0.0654(5) Uani 1 1 d . . . C11B C -0.3463(3) -0.11692(12) 0.56040(14) 0.0454(5) Uani 1 1 d . . . C12B C -0.3424(3) -0.09208(12) 0.65005(13) 0.0457(5) Uani 1 1 d . . . H12B H -0.3516 -0.1317 0.6888 0.055 Uiso 1 1 calc R . . C13B C -0.2094(2) -0.15681(11) 0.55110(12) 0.0425(5) Uani 1 1 d . . . H13B H -0.2204 -0.2084 0.5611 0.051 Uiso 1 1 calc R . . N21B N -0.6525(3) -0.01338(16) 0.87090(17) 0.0795(7) Uani 1 1 d . . . N31B N -0.2366(4) -0.29840(19) 0.26362(17) 0.0976(10) Uani 1 1 d . . . C21B C -0.5188(4) -0.0420(2) 0.87798(19) 0.0853(10) Uani 1 1 d . . . H21B H -0.4689 -0.0583 0.9315 0.102 Uiso 1 1 calc R . . C22B C -0.4476(4) -0.04958(19) 0.81224(17) 0.0755(9) Uani 1 1 d . . . H22B H -0.3535 -0.0712 0.8217 0.091 Uiso 1 1 calc R . . C23B C -0.5151(3) -0.02535(12) 0.73269(14) 0.0497(6) Uani 1 1 d . . . C24B C -0.6551(3) 0.0031(2) 0.72517(19) 0.0785(9) Uani 1 1 d . . . H24B H -0.7083 0.0194 0.6724 0.094 Uiso 1 1 calc R . . C25B C -0.7177(4) 0.0078(2) 0.7941(2) 0.0893(10) Uani 1 1 d . . . H25B H -0.8134 0.0275 0.7860 0.107 Uiso 1 1 calc R . . C26B C -0.4434(3) -0.02756(12) 0.65770(13) 0.0477(6) Uani 1 1 d . . . H26B H -0.5175 -0.0193 0.6043 0.057 Uiso 1 1 calc R . . C31B C -0.1501(5) -0.2406(3) 0.26412(19) 0.0979(12) Uani 1 1 d . . . H31B H -0.1076 -0.2335 0.2175 0.118 Uiso 1 1 calc R . . C32B C -0.1191(4) -0.19061(18) 0.32902(16) 0.0765(9) Uani 1 1 d . . . H32B H -0.0574 -0.1514 0.3254 0.092 Uiso 1 1 calc R . . C33B C -0.1799(3) -0.19903(13) 0.39909(14) 0.0518(6) Uani 1 1 d . . . C34B C -0.2679(3) -0.25923(15) 0.39984(17) 0.0637(7) Uani 1 1 d . . . H34B H -0.3102 -0.2683 0.4462 0.076 Uiso 1 1 calc R . . C35B C -0.2929(4) -0.30607(18) 0.3312(2) 0.0861(10) Uani 1 1 d . . . H35B H -0.3540 -0.3458 0.3331 0.103 Uiso 1 1 calc R . . C36B C -0.1495(3) -0.14493(12) 0.47025(13) 0.0459(6) Uani 1 1 d . . . H36B H -0.1835 -0.0976 0.4466 0.055 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 O1A 0.0650(11) 0.0470(10) 0.0863(13) -0.0103(9) 0.0270(10) -0.0100(9) C11A 0.0478(13) 0.0426(13) 0.0423(11) 0.0003(9) 0.0021(10) 0.0026(10) C12A 0.0505(13) 0.0424(12) 0.0341(10) -0.0009(8) 0.0055(9) 0.0042(10) C13A 0.0527(13) 0.0389(11) 0.0403(11) 0.0033(9) 0.0076(10) 0.0064(10) N21A 0.120(2) 0.0791(19) 0.097(2) -0.0453(16) 0.0115(19) 0.0196(18) N31A 0.076(2) 0.088(2) 0.137(3) -0.0243(19) 0.0197(19) 0.0276(17) C21A 0.101(3) 0.087(2) 0.080(2) -0.0368(18) -0.0103(18) 0.007(2) C22A 0.0754(19) 0.0618(17) 0.0675(16) -0.0187(13) -0.0012(14) 0.0054(14) C23A 0.0585(14) 0.0473(13) 0.0458(12) -0.0034(10) 0.0170(11) 0.0040(11) C24A 0.106(3) 0.073(2) 0.0659(17) -0.0193(15) -0.0008(17) 0.0378(18) C25A 0.131(3) 0.085(2) 0.096(2) -0.038(2) -0.001(2) 0.046(2) C26A 0.0569(14) 0.0424(12) 0.0371(10) 0.0006(9) 0.0113(10) 0.0086(10) C31A 0.089(3) 0.111(4) 0.212(5) -0.006(3) 0.078(3) 0.024(3) C32A 0.076(2) 0.074(2) 0.158(3) 0.004(2) 0.064(2) 0.0106(17) C33A 0.0516(14) 0.0513(15) 0.0522(13) -0.0067(10) 0.0088(11) 0.0046(11) C34A 0.0734(18) 0.0497(15) 0.0706(16) 0.0017(12) 0.0188(14) 0.0130(13) C35A 0.090(2) 0.0555(17) 0.086(2) -0.0094(14) -0.0007(18) 0.0190(16) C36A 0.0526(13) 0.0408(12) 0.0521(12) -0.0013(10) 0.0162(11) -0.0010(10) O1B 0.0532(10) 0.0842(13) 0.0526(10) -0.0161(8) -0.0014(8) 0.0059(9) C11B 0.0502(13) 0.0407(12) 0.0453(12) -0.0028(9) 0.0108(11) -0.0074(10) C12B 0.0544(14) 0.0415(12) 0.0427(11) 0.0017(9) 0.0142(10) 0.0003(10) C13B 0.0548(13) 0.0335(11) 0.0398(11) 0.0029(8) 0.0118(9) 0.0003(9) N21B 0.0811(18) 0.0928(19) 0.0734(16) -0.0038(13) 0.0360(14) 0.0085(15) N31B 0.131(3) 0.096(2) 0.0582(16) -0.0203(14) 0.0045(16) 0.020(2) C21B 0.090(2) 0.116(3) 0.0530(16) 0.0183(16) 0.0227(15) 0.019(2) C22B 0.0699(18) 0.105(2) 0.0533(15) 0.0144(14) 0.0170(13) 0.0249(17) C23B 0.0494(13) 0.0507(13) 0.0482(12) -0.0027(10) 0.0094(10) 0.0004(11) C24B 0.0623(18) 0.113(3) 0.0622(16) 0.0137(16) 0.0180(14) 0.0266(18) C25B 0.075(2) 0.121(3) 0.082(2) 0.0139(19) 0.0370(17) 0.032(2) C26B 0.0497(13) 0.0535(14) 0.0377(11) -0.0007(9) 0.0051(9) 0.0070(10) C31B 0.129(3) 0.116(3) 0.0518(17) -0.0125(18) 0.0271(18) 0.021(3) C32B 0.102(2) 0.085(2) 0.0460(14) 0.0003(13) 0.0237(14) 0.0086(18) C33B 0.0608(15) 0.0502(14) 0.0411(11) 0.0019(10) 0.0043(10) 0.0149(12) C34B 0.0721(18) 0.0611(16) 0.0563(14) -0.0077(12) 0.0115(13) 0.0005(14) C35B 0.107(3) 0.0668(19) 0.075(2) -0.0166(15) -0.0001(18) 0.0001(18) C36B 0.0590(14) 0.0397(12) 0.0398(11) 0.0060(9) 0.0132(10) 0.0068(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 O1A C11A 1.210(3) . ? C11A C12A 1.507(3) . ? C11A C13A 1.512(3) . ? C12A C26A 1.540(3) . ? C12A C12B 1.556(3) . ? C13A C36A 1.537(3) . ? C13A C13B 1.557(3) . ? N21A C25A 1.316(5) . ? N21A C21A 1.317(4) . ? N31A C31A 1.302(6) . ? N31A C35A 1.320(5) . ? C21A C22A 1.370(4) . ? C22A C23A 1.364(4) . ? C23A C24A 1.378(4) . ? C23A C26A 1.501(3) . ? C24A C25A 1.356(4) . ? C26A C26B 1.576(3) . ? C31A C32A 1.366(5) . ? C32A C33A 1.367(4) . ? C33A C34A 1.365(4) . ? C33A C36A 1.493(3) . ? C34A C35A 1.392(4) . ? C36A C36B 1.579(3) . ? O1B C11B 1.211(3) . ? C11B C13B 1.491(3) . ? C11B C12B 1.509(3) . ? C12B C26B 1.534(3) . ? C13B C36B 1.538(3) . ? N21B C21B 1.314(4) . ? N21B C25B 1.307(4) . ? N31B C35B 1.313(5) . ? N31B C31B 1.332(5) . ? C21B C22B 1.369(4) . ? C22B C23B 1.367(4) . ? C23B C24B 1.364(4) . ? C23B C26B 1.499(3) . ? C24B C25B 1.362(4) . ? C31B C32B 1.379(5) . ? C32B C33B 1.375(4) . ? C33B C34B 1.379(4) . ? C33B C36B 1.502(3) . ? C34B C35B 1.385(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 O1A C11A C12A 122.2(2) . . ? O1A C11A C13A 123.7(2) . . ? C12A C11A C13A 114.01(19) . . ? C11A C12A C26A 117.52(18) . . ? C11A C12A C12B 115.89(17) . . ? C26A C12A C12B 88.21(16) . . ? C11A C13A C36A 116.52(18) . . ? C11A C13A C13B 109.20(18) . . ? C36A C13A C13B 90.29(16) . . ? C25A N21A C21A 115.1(3) . . ? C31A N31A C35A 115.9(3) . . ? N21A C21A C22A 124.2(3) . . ? C23A C22A C21A 120.0(3) . . ? C22A C23A C24A 116.0(2) . . ? C22A C23A C26A 124.2(2) . . ? C24A C23A C26A 119.8(2) . . ? C23A C24A C25A 119.6(3) . . ? N21A C25A C24A 125.0(3) . . ? C23A C26A C12A 121.24(18) . . ? C23A C26A C26B 119.38(19) . . ? C12A C26A C26B 89.47(16) . . ? N31A C31A C32A 124.3(4) . . ? C31A C32A C33A 120.7(4) . . ? C34A C33A C32A 115.9(3) . . ? C34A C33A C36A 123.7(2) . . ? C32A C33A C36A 120.3(2) . . ? C33A C34A C35A 119.6(3) . . ? N31A C35A C34A 123.6(3) . . ? C33A C36A C13A 116.47(19) . . ? C33A C36A C36B 114.24(18) . . ? C13A C36A C36B 88.02(16) . . ? O1B C11B C13B 122.8(2) . . ? O1B C11B C12B 123.0(2) . . ? C13B C11B C12B 114.08(18) . . ? C11B C12B C26B 115.48(18) . . ? C11B C12B C12A 109.27(18) . . ? C26B C12B C12A 90.42(16) . . ? C11B C13B C36B 118.73(18) . . ? C11B C13B C13A 116.32(17) . . ? C36B C13B C13A 88.78(16) . . ? C21B N21B C25B 114.9(3) . . ? C35B N31B C31B 115.2(3) . . ? N21B C21B C22B 124.7(3) . . ? C23B C22B C21B 119.9(3) . . ? C22B C23B C24B 115.3(2) . . ? C22B C23B C26B 124.0(2) . . ? C24B C23B C26B 120.7(2) . . ? C25B C24B C23B 120.7(3) . . ? N21B C25B C24B 124.5(3) . . ? C23B C26B C12B 117.80(18) . . ? C23B C26B C26A 115.80(18) . . ? C12B C26B C26A 87.70(16) . . ? N31B C31B C32B 124.5(3) . . ? C31B C32B C33B 119.6(3) . . ? C34B C33B C32B 116.4(2) . . ? C34B C33B C36B 122.9(2) . . ? C32B C33B C36B 120.7(2) . . ? C33B C34B C35B 119.6(3) . . ? N31B C35B C34B 124.7(3) . . ? C33B C36B C13B 120.69(19) . . ? C33B C36B C36A 120.03(19) . . ? C13B C36B C36A 89.42(16) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.160 _refine_diff_density_min -0.126 _refine_diff_density_rms 0.028 ######END