# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Peter Langer' 'Katrin Marie Driller' 'Manuela Harms' 'Martin Hein' 'Michael Lalk' 'Stefanie Libnow' 'Dirk Michalik' 'Helmut Reinke' 'Kristian Wende' _publ_contact_author_name 'ProfD Peter Langer' _publ_contact_author_email PETER.LANGER@UNI-ROSTOCK.DE _publ_section_title ; Synthesis of 6H-Indolo-[2,3-b]quinoxaline-N-glycosides and their Cytotoxic Activity against Human Ceratinocytes (HaCaT) ; # Attachment 'kd39_and_kd42.cif' #====================================================================== data_kd42_(beta3c) _database_code_depnum_ccdc_archive 'CCDC 695574' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 13-(2',3',4'-Tri-O-acetyl-\b-L-rhamnopyranosyl)-5,12,13- triazaindeno[1,2-b]anthracene ; _chemical_name_common ? _chemical_melting_point 569 _chemical_formula_moiety 'C30 H27 N3 O7' _chemical_formula_sum 'C30 H27 N3 O7' _chemical_formula_weight 541.55 _chemical_absolute_configuration syn 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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) ' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.1230(9) _cell_length_b 7.1019(5) _cell_length_c 14.4491(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.077(4) _cell_angle_gamma 90.00 _cell_volume 1346.63(16) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3480 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 25.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9313 _exptl_absorpt_correction_T_max 0.9971 _exptl_absorpt_process_details 'SADABS; (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26733 _diffrn_reflns_av_R_equivalents 0.0891 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 28.74 _reflns_number_total 3742 _reflns_number_gt 2327 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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 absolute structure could not be determined from the diffraction experiment. So in the final step of the refinement the MERG 4 instruction was used. ; _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^)+(0.0450P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 3742 _refine_ls_number_parameters 365 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1021 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.0966 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.007 _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 0.79990(14) -0.0315(3) 0.13704(12) 0.0276(5) Uani 1 1 d . . . O2 O 0.63899(13) 0.2015(3) 0.06231(12) 0.0274(5) Uani 1 1 d . . . O3 O 0.57709(18) 0.4641(4) 0.12876(17) 0.0586(7) Uani 1 1 d . . . O4 O 0.74868(14) 0.3183(3) -0.08880(13) 0.0292(5) Uani 1 1 d . . . O5 O 0.89412(16) 0.4291(4) -0.15250(14) 0.0465(6) Uani 1 1 d . . . O6 O 0.88527(14) -0.0065(3) -0.10287(13) 0.0287(5) Uani 1 1 d . . . O7 O 0.75628(18) -0.0848(4) -0.19758(15) 0.0589(8) Uani 1 1 d . . . N1 N 0.73224(17) 0.1816(3) 0.24035(15) 0.0258(5) Uani 1 1 d . . . N2 N 0.80763(17) 0.4748(4) 0.28085(15) 0.0278(5) Uani 1 1 d . . . N3 N 0.66216(17) 0.4612(4) 0.43296(15) 0.0297(6) Uani 1 1 d . . . C1 C 0.7903(2) 0.1629(4) 0.15582(18) 0.0267(7) Uani 1 1 d . . . H1 H 0.8599 0.2158 0.1667 0.032 Uiso 1 1 calc R . . C2 C 0.7415(2) 0.2699(4) 0.07581(19) 0.0250(6) Uani 1 1 d . . . H2 H 0.7400 0.4076 0.0901 0.030 Uiso 1 1 calc R . . C3 C 0.8023(2) 0.2357(4) -0.01156(18) 0.0248(6) Uani 1 1 d . . . H3 H 0.8707 0.2964 -0.0054 0.030 Uiso 1 1 calc R . . C4 C 0.8160(2) 0.0250(4) -0.02681(18) 0.0237(6) Uani 1 1 d . . . H4 H 0.7486 -0.0348 -0.0404 0.028 Uiso 1 1 calc R . . C5 C 0.8640(2) -0.0665(4) 0.05808(18) 0.0277(7) Uani 1 1 d . . . H5 H 0.9331 -0.0117 0.0691 0.033 Uiso 1 1 calc R . . C6 C 0.8720(3) -0.2775(5) 0.0488(2) 0.0412(8) Uani 1 1 d . . . H6A H 0.8044 -0.3302 0.0361 0.062 Uiso 1 1 calc R . . H6B H 0.8985 -0.3308 0.1066 0.062 Uiso 1 1 calc R . . H6C H 0.9182 -0.3085 -0.0022 0.062 Uiso 1 1 calc R . . C7 C 0.5625(2) 0.3148(5) 0.0923(2) 0.0392(8) Uani 1 1 d . . . C8 C 0.4608(2) 0.2254(6) 0.0743(3) 0.0583(11) Uani 1 1 d . . . H8A H 0.4072 0.3009 0.1034 0.087 Uiso 1 1 calc R . . H8B H 0.4601 0.0980 0.1003 0.087 Uiso 1 1 calc R . . H8C H 0.4488 0.2189 0.0074 0.087 Uiso 1 1 calc R . . C9 C 0.8038(2) 0.4021(5) -0.15719(19) 0.0319(7) Uani 1 1 d . . . C10 C 0.7378(3) 0.4496(5) -0.2378(2) 0.0441(9) Uani 1 1 d . . . H10A H 0.7103 0.3335 -0.2648 0.066 Uiso 1 1 calc R . . H10B H 0.7781 0.5165 -0.2844 0.066 Uiso 1 1 calc R . . H10C H 0.6815 0.5300 -0.2173 0.066 Uiso 1 1 calc R . . C11 C 0.8457(2) -0.0661(4) -0.1843(2) 0.0318(7) Uani 1 1 d . . . C12 C 0.9275(3) -0.1038(6) -0.2527(2) 0.0486(9) Uani 1 1 d . . . H12A H 0.8971 -0.1499 -0.3104 0.073 Uiso 1 1 calc R . . H12B H 0.9741 -0.1991 -0.2279 0.073 Uiso 1 1 calc R . . H12C H 0.9652 0.0126 -0.2649 0.073 Uiso 1 1 calc R . . C13 C 0.7429(2) 0.3397(4) 0.29501(19) 0.0265(7) Uani 1 1 d . . . C14 C 0.6683(2) 0.3304(4) 0.36898(19) 0.0256(6) Uani 1 1 d . . . C15 C 0.6505(2) 0.0707(4) 0.27503(18) 0.0251(6) Uani 1 1 d . . . C16 C 0.6116(2) -0.0990(4) 0.24320(19) 0.0299(7) Uani 1 1 d . . . H16 H 0.6384 -0.1579 0.1894 0.036 Uiso 1 1 calc R . . C17 C 0.5317(2) -0.1803(5) 0.2929(2) 0.0330(7) Uani 1 1 d . . . H17 H 0.5040 -0.2967 0.2725 0.040 Uiso 1 1 calc R . . C18 C 0.4918(2) -0.0943(5) 0.3718(2) 0.0330(7) Uani 1 1 d . . . H18 H 0.4374 -0.1527 0.4043 0.040 Uiso 1 1 calc R . . C19 C 0.5307(2) 0.0748(4) 0.40320(19) 0.0309(7) Uani 1 1 d . . . H19 H 0.5035 0.1330 0.4570 0.037 Uiso 1 1 calc R . . C20 C 0.6105(2) 0.1588(4) 0.35476(18) 0.0264(7) Uani 1 1 d . . . C21 C 0.7318(2) 0.6071(4) 0.42397(18) 0.0280(7) Uani 1 1 d . . . C22 C 0.7311(2) 0.7522(4) 0.4884(2) 0.0314(7) Uani 1 1 d . . . H22 H 0.6848 0.7464 0.5388 0.038 Uiso 1 1 calc R . . C23 C 0.7965(2) 0.9062(5) 0.48111(19) 0.0302(7) Uani 1 1 d . . . C24 C 0.7953(3) 1.0601(5) 0.5456(2) 0.0403(8) Uani 1 1 d . . . H24 H 0.7488 1.0591 0.5960 0.048 Uiso 1 1 calc R . . C25 C 0.8608(3) 1.2079(5) 0.5348(2) 0.0456(9) Uani 1 1 d . . . H25 H 0.8594 1.3086 0.5781 0.055 Uiso 1 1 calc R . . C26 C 0.9302(3) 1.2138(5) 0.4610(2) 0.0419(8) Uani 1 1 d . . . H26 H 0.9749 1.3182 0.4549 0.050 Uiso 1 1 calc R . . C27 C 0.9339(2) 1.0722(5) 0.3985(2) 0.0357(8) Uani 1 1 d . . . H27 H 0.9815 1.0780 0.3491 0.043 Uiso 1 1 calc R . . C28 C 0.8673(2) 0.9145(4) 0.40592(19) 0.0297(7) Uani 1 1 d . . . C29 C 0.8690(2) 0.7671(4) 0.3410(2) 0.0287(7) Uani 1 1 d . . . H29 H 0.9162 0.7719 0.2913 0.034 Uiso 1 1 calc R . . C30 C 0.8036(2) 0.6156(4) 0.34801(18) 0.0258(7) Uani 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 0.0330(11) 0.0249(12) 0.0250(10) 0.0018(8) 0.0084(9) 0.0028(9) O2 0.0221(11) 0.0306(12) 0.0293(11) -0.0013(9) 0.0054(9) 0.0023(9) O3 0.0516(15) 0.0505(18) 0.0736(17) -0.0202(15) 0.0008(13) 0.0199(13) O4 0.0292(11) 0.0338(12) 0.0248(10) 0.0040(9) 0.0036(9) 0.0008(9) O5 0.0341(13) 0.0656(18) 0.0397(13) 0.0139(12) 0.0034(10) -0.0117(12) O6 0.0227(10) 0.0371(12) 0.0265(11) -0.0063(9) 0.0076(8) -0.0034(9) O7 0.0343(14) 0.102(2) 0.0406(14) -0.0267(15) 0.0015(11) -0.0009(15) N1 0.0265(13) 0.0269(14) 0.0240(13) -0.0007(10) 0.0059(10) -0.0020(10) N2 0.0278(13) 0.0302(14) 0.0254(13) -0.0005(11) 0.0032(10) -0.0017(11) N3 0.0308(14) 0.0333(15) 0.0249(12) -0.0022(11) 0.0039(10) -0.0003(11) C1 0.0270(16) 0.0282(17) 0.0250(16) -0.0025(12) 0.0077(13) -0.0015(12) C2 0.0223(15) 0.0225(16) 0.0302(16) -0.0020(11) 0.0067(13) -0.0028(11) C3 0.0241(15) 0.0287(17) 0.0216(15) 0.0035(12) 0.0034(12) -0.0009(13) C4 0.0202(15) 0.0243(17) 0.0265(15) -0.0030(11) 0.0071(12) -0.0026(11) C5 0.0266(16) 0.0292(19) 0.0273(15) -0.0015(12) 0.0071(13) 0.0014(12) C6 0.047(2) 0.031(2) 0.045(2) 0.0025(15) 0.0121(17) 0.0130(16) C7 0.0355(19) 0.046(2) 0.0356(18) 0.0003(16) 0.0062(15) 0.0132(16) C8 0.0267(19) 0.078(3) 0.070(3) -0.006(2) 0.0108(18) 0.0121(19) C9 0.0372(19) 0.0301(17) 0.0283(16) -0.0007(13) 0.0064(14) 0.0013(14) C10 0.050(2) 0.052(2) 0.0304(17) 0.0044(16) -0.0048(15) 0.0029(18) C11 0.0333(18) 0.0324(19) 0.0299(17) -0.0022(13) 0.0082(14) -0.0021(14) C12 0.043(2) 0.067(3) 0.0355(18) -0.0105(18) 0.0140(16) 0.0042(19) C13 0.0284(16) 0.0308(18) 0.0202(15) 0.0017(12) 0.0026(13) 0.0047(13) C14 0.0244(16) 0.0306(17) 0.0218(15) 0.0035(13) 0.0009(12) 0.0010(12) C15 0.0233(15) 0.0298(17) 0.0224(15) 0.0052(13) 0.0025(12) 0.0019(13) C16 0.0322(17) 0.0297(17) 0.0279(16) -0.0017(13) 0.0030(13) -0.0001(14) C17 0.0288(17) 0.0303(18) 0.0400(18) 0.0017(14) -0.0006(14) -0.0010(14) C18 0.0311(16) 0.0385(18) 0.0295(16) 0.0044(14) 0.0039(13) -0.0029(15) C19 0.0301(17) 0.0399(19) 0.0226(15) 0.0015(13) 0.0039(13) -0.0008(14) C20 0.0232(15) 0.0313(17) 0.0248(16) 0.0022(12) 0.0004(13) -0.0002(12) C21 0.0257(16) 0.0331(19) 0.0251(16) 0.0009(13) 0.0011(13) 0.0039(13) C22 0.0289(16) 0.0380(19) 0.0273(16) -0.0047(14) 0.0006(14) 0.0012(14) C23 0.0280(16) 0.0337(18) 0.0288(16) -0.0010(13) -0.0076(13) 0.0069(14) C24 0.044(2) 0.040(2) 0.0366(18) -0.0071(15) -0.0046(16) 0.0072(16) C25 0.061(2) 0.036(2) 0.039(2) -0.0101(16) -0.0075(18) -0.0008(18) C26 0.056(2) 0.030(2) 0.0390(19) 0.0008(15) -0.0116(18) -0.0036(16) C27 0.0431(19) 0.0318(19) 0.0321(17) 0.0068(14) -0.0025(15) -0.0040(15) C28 0.0315(16) 0.0301(17) 0.0275(15) 0.0043(13) -0.0068(13) 0.0017(14) C29 0.0286(17) 0.0304(18) 0.0271(16) 0.0013(12) 0.0003(13) 0.0016(12) C30 0.0267(17) 0.0297(18) 0.0211(14) 0.0014(12) -0.0009(13) 0.0027(12) _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 1.413(3) . ? O1 C5 1.440(3) . ? O2 C7 1.357(4) . ? O2 C2 1.443(3) . ? O3 C7 1.199(4) . ? O4 C9 1.362(3) . ? O4 C3 1.443(3) . ? O5 C9 1.202(3) . ? O6 C11 1.354(3) . ? O6 C4 1.445(3) . ? O7 C11 1.196(3) . ? N1 C13 1.380(4) . ? N1 C15 1.423(4) . ? N1 C1 1.446(3) . ? N2 C13 1.298(4) . ? N2 C30 1.394(3) . ? N3 C14 1.313(4) . ? N3 C21 1.388(4) . ? C1 C2 1.524(4) . ? C1 H1 1.0000 . ? C2 C3 1.514(4) . ? C2 H2 1.0000 . ? C3 C4 1.523(4) . ? C3 H3 1.0000 . ? C4 C5 1.524(4) . ? C4 H4 1.0000 . ? C5 C6 1.508(4) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.500(5) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.490(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.484(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.452(4) . ? C14 C20 1.450(4) . ? C15 C16 1.387(4) . ? C15 C20 1.412(4) . ? C16 C17 1.396(4) . ? C16 H16 0.9500 . ? C17 C18 1.397(4) . ? C17 H17 0.9500 . ? C18 C19 1.381(4) . ? C18 H18 0.9500 . ? C19 C20 1.394(4) . ? C19 H19 0.9500 . ? C21 C22 1.389(4) . ? C21 C30 1.449(4) . ? C22 C23 1.394(4) . ? C22 H22 0.9500 . ? C23 C28 1.432(4) . ? C23 C24 1.437(4) . ? C24 C25 1.365(5) . ? C24 H24 0.9500 . ? C25 C26 1.405(4) . ? C25 H25 0.9500 . ? C26 C27 1.352(4) . ? C26 H26 0.9500 . ? C27 C28 1.425(4) . ? C27 H27 0.9500 . ? C28 C29 1.406(4) . ? C29 C30 1.380(4) . ? C29 H29 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C5 111.9(2) . . ? C7 O2 C2 116.5(2) . . ? C9 O4 C3 118.6(2) . . ? C11 O6 C4 117.9(2) . . ? C13 N1 C15 109.0(2) . . ? C13 N1 C1 120.3(2) . . ? C15 N1 C1 130.2(2) . . ? C13 N2 C30 113.3(2) . . ? C14 N3 C21 114.9(2) . . ? O1 C1 N1 107.4(2) . . ? O1 C1 C2 112.3(2) . . ? N1 C1 C2 111.9(2) . . ? O1 C1 H1 108.4 . . ? N1 C1 H1 108.4 . . ? C2 C1 H1 108.4 . . ? O2 C2 C3 109.0(2) . . ? O2 C2 C1 109.0(2) . . ? C3 C2 C1 109.3(2) . . ? O2 C2 H2 109.8 . . ? C3 C2 H2 109.8 . . ? C1 C2 H2 109.8 . . ? O4 C3 C2 108.8(2) . . ? O4 C3 C4 110.2(2) . . ? C2 C3 C4 109.9(2) . . ? O4 C3 H3 109.3 . . ? C2 C3 H3 109.3 . . ? C4 C3 H3 109.3 . . ? O6 C4 C3 109.7(2) . . ? O6 C4 C5 106.6(2) . . ? C3 C4 C5 110.5(2) . . ? O6 C4 H4 110.0 . . ? C3 C4 H4 110.0 . . ? C5 C4 H4 110.0 . . ? O1 C5 C6 106.4(2) . . ? O1 C5 C4 108.9(2) . . ? C6 C5 C4 112.4(3) . . ? O1 C5 H5 109.7 . . ? C6 C5 H5 109.7 . . ? C4 C5 H5 109.7 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O3 C7 O2 123.1(3) . . ? O3 C7 C8 126.3(3) . . ? O2 C7 C8 110.6(3) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O5 C9 O4 123.6(3) . . ? O5 C9 C10 125.5(3) . . ? O4 C9 C10 110.9(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O7 C11 O6 123.3(3) . . ? O7 C11 C12 125.7(3) . . ? O6 C11 C12 111.0(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 N1 125.3(2) . . ? N2 C13 C14 126.3(3) . . ? N1 C13 C14 108.4(2) . . ? N3 C14 C20 131.5(2) . . ? N3 C14 C13 121.8(3) . . ? C20 C14 C13 106.7(2) . . ? C16 C15 C20 121.2(3) . . ? C16 C15 N1 129.9(3) . . ? C20 C15 N1 108.9(2) . . ? C15 C16 C17 117.7(3) . . ? C15 C16 H16 121.1 . . ? C17 C16 H16 121.1 . . ? C16 C17 C18 121.5(3) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C19 C18 C17 120.6(3) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 119.0(3) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? C19 C20 C15 120.0(3) . . ? C19 C20 C14 132.9(3) . . ? C15 C20 C14 107.0(2) . . ? N3 C21 C22 119.1(2) . . ? N3 C21 C30 122.1(2) . . ? C22 C21 C30 118.8(3) . . ? C21 C22 C23 121.8(3) . . ? C21 C22 H22 119.1 . . ? C23 C22 H22 119.1 . . ? C22 C23 C28 119.3(3) . . ? C22 C23 C24 122.7(3) . . ? C28 C23 C24 117.9(3) . . ? C25 C24 C23 120.2(3) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 121.2(3) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C27 C26 C25 120.6(3) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C26 C27 C28 120.8(3) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C29 C28 C27 121.6(3) . . ? C29 C28 C23 119.1(3) . . ? C27 C28 C23 119.3(3) . . ? C30 C29 C28 121.4(3) . . ? C30 C29 H29 119.3 . . ? C28 C29 H29 119.3 . . ? C29 C30 N2 119.0(2) . . ? C29 C30 C21 119.5(2) . . ? N2 C30 C21 121.5(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O1 C1 N1 -175.2(2) . . . . ? C5 O1 C1 C2 61.4(3) . . . . ? C13 N1 C1 O1 154.8(2) . . . . ? C15 N1 C1 O1 -34.8(4) . . . . ? C13 N1 C1 C2 -81.6(3) . . . . ? C15 N1 C1 C2 88.8(3) . . . . ? C7 O2 C2 C3 -135.8(3) . . . . ? C7 O2 C2 C1 104.9(3) . . . . ? O1 C1 C2 O2 63.2(3) . . . . ? N1 C1 C2 O2 -57.7(3) . . . . ? O1 C1 C2 C3 -55.9(3) . . . . ? N1 C1 C2 C3 -176.8(2) . . . . ? C9 O4 C3 C2 142.8(2) . . . . ? C9 O4 C3 C4 -96.7(3) . . . . ? O2 C2 C3 O4 54.0(3) . . . . ? C1 C2 C3 O4 173.1(2) . . . . ? O2 C2 C3 C4 -66.7(3) . . . . ? C1 C2 C3 C4 52.4(3) . . . . ? C11 O6 C4 C3 -106.1(3) . . . . ? C11 O6 C4 C5 134.2(3) . . . . ? O4 C3 C4 O6 67.8(3) . . . . ? C2 C3 C4 O6 -172.3(2) . . . . ? O4 C3 C4 C5 -174.9(2) . . . . ? C2 C3 C4 C5 -55.1(3) . . . . ? C1 O1 C5 C6 177.2(2) . . . . ? C1 O1 C5 C4 -61.4(3) . . . . ? O6 C4 C5 O1 177.4(2) . . . . ? C3 C4 C5 O1 58.3(3) . . . . ? O6 C4 C5 C6 -65.0(3) . . . . ? C3 C4 C5 C6 175.9(2) . . . . ? C2 O2 C7 O3 -0.3(4) . . . . ? C2 O2 C7 C8 -179.7(3) . . . . ? C3 O4 C9 O5 -8.2(4) . . . . ? C3 O4 C9 C10 170.4(3) . . . . ? C4 O6 C11 O7 3.8(4) . . . . ? C4 O6 C11 C12 -176.1(3) . . . . ? C30 N2 C13 N1 -178.7(2) . . . . ? C30 N2 C13 C14 2.9(4) . . . . ? C15 N1 C13 N2 -177.1(3) . . . . ? C1 N1 C13 N2 -4.9(4) . . . . ? C15 N1 C13 C14 1.6(3) . . . . ? C1 N1 C13 C14 173.8(2) . . . . ? C21 N3 C14 C20 179.8(3) . . . . ? C21 N3 C14 C13 0.2(4) . . . . ? N2 C13 C14 N3 -2.7(4) . . . . ? N1 C13 C14 N3 178.7(3) . . . . ? N2 C13 C14 C20 177.6(3) . . . . ? N1 C13 C14 C20 -1.0(3) . . . . ? C13 N1 C15 C16 180.0(3) . . . . ? C1 N1 C15 C16 8.7(5) . . . . ? C13 N1 C15 C20 -1.5(3) . . . . ? C1 N1 C15 C20 -172.8(3) . . . . ? C20 C15 C16 C17 -0.2(4) . . . . ? N1 C15 C16 C17 178.2(3) . . . . ? C15 C16 C17 C18 0.2(4) . . . . ? C16 C17 C18 C19 -0.1(5) . . . . ? C17 C18 C19 C20 0.1(4) . . . . ? C18 C19 C20 C15 -0.1(4) . . . . ? C18 C19 C20 C14 -179.2(3) . . . . ? C16 C15 C20 C19 0.2(4) . . . . ? N1 C15 C20 C19 -178.5(2) . . . . ? C16 C15 C20 C14 179.5(2) . . . . ? N1 C15 C20 C14 0.8(3) . . . . ? N3 C14 C20 C19 -0.4(5) . . . . ? C13 C14 C20 C19 179.3(3) . . . . ? N3 C14 C20 C15 -179.5(3) . . . . ? C13 C14 C20 C15 0.1(3) . . . . ? C14 N3 C21 C22 179.9(3) . . . . ? C14 N3 C21 C30 1.6(4) . . . . ? N3 C21 C22 C23 -177.5(3) . . . . ? C30 C21 C22 C23 0.9(4) . . . . ? C21 C22 C23 C28 -0.8(4) . . . . ? C21 C22 C23 C24 178.4(3) . . . . ? C22 C23 C24 C25 -179.7(3) . . . . ? C28 C23 C24 C25 -0.5(4) . . . . ? C23 C24 C25 C26 0.2(5) . . . . ? C24 C25 C26 C27 -0.1(5) . . . . ? C25 C26 C27 C28 0.3(5) . . . . ? C26 C27 C28 C29 179.2(3) . . . . ? C26 C27 C28 C23 -0.6(4) . . . . ? C22 C23 C28 C29 0.1(4) . . . . ? C24 C23 C28 C29 -179.1(3) . . . . ? C22 C23 C28 C27 179.9(3) . . . . ? C24 C23 C28 C27 0.7(4) . . . . ? C27 C28 C29 C30 -179.4(3) . . . . ? C23 C28 C29 C30 0.4(4) . . . . ? C28 C29 C30 N2 179.0(3) . . . . ? C28 C29 C30 C21 -0.3(4) . . . . ? C13 N2 C30 C29 179.8(2) . . . . ? C13 N2 C30 C21 -1.0(4) . . . . ? N3 C21 C30 C29 178.0(3) . . . . ? C22 C21 C30 C29 -0.4(4) . . . . ? N3 C21 C30 N2 -1.3(4) . . . . ? C22 C21 C30 N2 -179.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.74 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.198 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.046 #====================================================================== #_eof-next_file_follows #====================================================================== data_kd39_(beta3g) _database_code_depnum_ccdc_archive 'CCDC 695575' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3-Dimethyl-6-(2',3',4',6'-tetra-O-acetyl-\b-D-manno- pyranosyl)indolo[2,3-b]quinoxaline ; _chemical_name_common ? _chemical_melting_point 543 _chemical_formula_moiety 'C30 H31 N3 O9' _chemical_formula_sum 'C30 H31 N3 O9' _chemical_formula_weight 577.58 _chemical_absolute_configuration syn 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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' _cell_length_a 6.48000(10) _cell_length_b 10.5889(2) _cell_length_c 41.9162(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2876.12(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6984 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 29.78 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.79 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method ? _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9255 _exptl_absorpt_correction_T_max 0.9784 _exptl_absorpt_process_details 'SADABS; (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41892 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -58 _diffrn_reflns_limit_l_max 58 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4779 _reflns_number_gt 4318 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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 absolute structure could not be determined from the diffraction experiment. So in the final step of the refinement the MERG 4 instruction was used. ; _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^)+(0.0644P)^2^+0.8614P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 4779 _refine_ls_number_parameters 385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1196 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.008 _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 0.1433(2) 0.46436(14) 0.14144(3) 0.0235(3) Uani 1 1 d . . . O2 O 0.3111(3) 0.70212(14) 0.16482(4) 0.0282(3) Uani 1 1 d . . . O3 O 0.5963(4) 0.8067(2) 0.14897(7) 0.0672(7) Uani 1 1 d . . . O4 O 0.4363(3) 0.59865(15) 0.22211(3) 0.0284(3) Uani 1 1 d . . . O5 O 0.5996(5) 0.4409(2) 0.24766(6) 0.0660(8) Uani 1 1 d . . . O6 O 0.1435(3) 0.38464(16) 0.22572(3) 0.0303(4) Uani 1 1 d . . . O7 O 0.0528(4) 0.5400(2) 0.25951(5) 0.0527(6) Uani 1 1 d . . . O8 O -0.0969(3) 0.23689(15) 0.14494(4) 0.0291(3) Uani 1 1 d . . . O9 O -0.4390(3) 0.21658(17) 0.15063(5) 0.0380(4) Uani 1 1 d . . . N1 N 0.3708(3) 0.56091(17) 0.10649(4) 0.0234(4) Uani 1 1 d . . . N2 N 0.6842(3) 0.45539(17) 0.09223(4) 0.0238(4) Uani 1 1 d . . . N3 N 0.6229(3) 0.58275(17) 0.03168(4) 0.0252(4) Uani 1 1 d . . . C1 C 0.3522(3) 0.50120(19) 0.13739(4) 0.0222(4) Uani 1 1 d . . . H1 H 0.4392 0.4232 0.1373 0.027 Uiso 1 1 calc R . . C2 C 0.4236(4) 0.5852(2) 0.16491(5) 0.0240(4) Uani 1 1 d . . . H2 H 0.5745 0.6030 0.1626 0.029 Uiso 1 1 calc R . . C3 C 0.3852(4) 0.5153(2) 0.19614(5) 0.0241(4) Uani 1 1 d . . . H3 H 0.4789 0.4403 0.1970 0.029 Uiso 1 1 calc R . . C4 C 0.1626(4) 0.4694(2) 0.19888(5) 0.0240(4) Uani 1 1 d . . . H4 H 0.0638 0.5416 0.2005 0.029 Uiso 1 1 calc R . . C5 C 0.1186(3) 0.3883(2) 0.16951(5) 0.0228(4) Uani 1 1 d . . . H5 H 0.2188 0.3166 0.1688 0.027 Uiso 1 1 calc R . . C6 C -0.0986(4) 0.3368(2) 0.16869(5) 0.0285(5) Uani 1 1 d . . . H6A H -0.1381 0.3029 0.1898 0.034 Uiso 1 1 calc R . . H6B H -0.1978 0.4038 0.1627 0.034 Uiso 1 1 calc R . . C7 C 0.4165(5) 0.8076(3) 0.15613(6) 0.0402(6) Uani 1 1 d . . . C8 C 0.2780(7) 0.9201(3) 0.15614(9) 0.0595(9) Uani 1 1 d . . . H8A H 0.2445 0.9433 0.1782 0.089 Uiso 1 1 calc R . . H8B H 0.1506 0.9000 0.1446 0.089 Uiso 1 1 calc R . . H8C H 0.3478 0.9909 0.1456 0.089 Uiso 1 1 calc R . . C9 C 0.5375(4) 0.5473(2) 0.24742(6) 0.0356(6) Uani 1 1 d . . . C10 C 0.5521(5) 0.6384(3) 0.27436(6) 0.0431(6) Uani 1 1 d . . . H10A H 0.4691 0.6078 0.2923 0.065 Uiso 1 1 calc R . . H10B H 0.5004 0.7210 0.2675 0.065 Uiso 1 1 calc R . . H10C H 0.6965 0.6464 0.2810 0.065 Uiso 1 1 calc R . . C11 C 0.0866(4) 0.4301(3) 0.25458(6) 0.0376(6) Uani 1 1 d . . . C12 C 0.0751(7) 0.3249(3) 0.27838(7) 0.0602(9) Uani 1 1 d . . . H12A H 0.0306 0.3585 0.2991 0.090 Uiso 1 1 calc R . . H12B H 0.2114 0.2858 0.2806 0.090 Uiso 1 1 calc R . . H12C H -0.0243 0.2615 0.2710 0.090 Uiso 1 1 calc R . . C13 C -0.2813(4) 0.1866(2) 0.13755(6) 0.0295(5) Uani 1 1 d . . . C14 C -0.2612(5) 0.0903(3) 0.11140(7) 0.0453(7) Uani 1 1 d . . . H14A H -0.3045 0.0075 0.1194 0.068 Uiso 1 1 calc R . . H14B H -0.1170 0.0859 0.1044 0.068 Uiso 1 1 calc R . . H14C H -0.3487 0.1147 0.0934 0.068 Uiso 1 1 calc R . . C15 C 0.5303(3) 0.53073(19) 0.08582(5) 0.0218(4) Uani 1 1 d . . . C16 C 0.4980(4) 0.59642(19) 0.05602(5) 0.0229(4) Uani 1 1 d . . . C17 C 0.2344(4) 0.64430(19) 0.09090(5) 0.0235(4) Uani 1 1 d . . . C18 C 0.0499(4) 0.6965(2) 0.10140(5) 0.0279(4) Uani 1 1 d . . . H18 H -0.0024 0.6788 0.1221 0.033 Uiso 1 1 calc R . . C19 C -0.0556(4) 0.7758(2) 0.08048(6) 0.0325(5) Uani 1 1 d . . . H19 H -0.1813 0.8136 0.0872 0.039 Uiso 1 1 calc R . . C20 C 0.0185(4) 0.8014(2) 0.04983(6) 0.0347(5) Uani 1 1 d . . . H20 H -0.0569 0.8560 0.0362 0.042 Uiso 1 1 calc R . . C21 C 0.2008(4) 0.7477(2) 0.03923(6) 0.0313(5) Uani 1 1 d . . . H21 H 0.2506 0.7646 0.0183 0.038 Uiso 1 1 calc R . . C22 C 0.3099(4) 0.6684(2) 0.05977(5) 0.0252(4) Uani 1 1 d . . . C23 C 0.7872(4) 0.50353(19) 0.03714(5) 0.0235(4) Uani 1 1 d . . . C24 C 0.9322(4) 0.4829(2) 0.01236(5) 0.0274(4) Uani 1 1 d . . . H24A H 0.9120 0.5236 -0.0076 0.033 Uiso 1 1 calc R . . C25 C 1.1017(4) 0.4057(2) 0.01625(5) 0.0265(4) Uani 1 1 d . . . C26 C 1.1318(4) 0.3438(2) 0.04622(5) 0.0264(4) Uani 1 1 d . . . C27 C 0.9928(4) 0.3632(2) 0.07058(5) 0.0250(4) Uani 1 1 d . . . H27A H 1.0152 0.3226 0.0905 0.030 Uiso 1 1 calc R . . C28 C 0.8190(3) 0.44115(19) 0.06695(5) 0.0227(4) Uani 1 1 d . . . C29 C 1.2530(4) 0.3861(3) -0.01066(5) 0.0347(5) Uani 1 1 d . . . H29B H 1.2089 0.4350 -0.0293 0.052 Uiso 1 1 calc R . . H29C H 1.2580 0.2962 -0.0162 0.052 Uiso 1 1 calc R . . H29D H 1.3904 0.4142 -0.0039 0.052 Uiso 1 1 calc R . . C30 C 1.3132(4) 0.2576(3) 0.05119(6) 0.0371(6) Uani 1 1 d . . . H30A H 1.3097 0.2237 0.0730 0.056 Uiso 1 1 calc R . . H30B H 1.4415 0.3049 0.0480 0.056 Uiso 1 1 calc R . . H30C H 1.3066 0.1878 0.0359 0.056 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 0.0231(7) 0.0276(7) 0.0199(6) 0.0019(5) 0.0012(6) -0.0017(6) O2 0.0329(9) 0.0239(7) 0.0278(7) 0.0001(6) 0.0023(7) -0.0027(7) O3 0.0526(14) 0.0458(12) 0.103(2) 0.0173(13) 0.0205(15) -0.0153(11) O4 0.0371(9) 0.0270(7) 0.0212(6) -0.0028(6) -0.0011(7) -0.0017(7) O5 0.092(2) 0.0377(10) 0.0688(14) -0.0068(10) -0.0503(15) 0.0114(12) O6 0.0347(9) 0.0344(8) 0.0219(6) 0.0045(6) 0.0069(7) 0.0001(8) O7 0.0614(15) 0.0583(12) 0.0384(10) -0.0095(9) 0.0202(10) 0.0037(12) O8 0.0284(8) 0.0276(7) 0.0314(8) -0.0041(6) 0.0046(7) -0.0029(7) O9 0.0305(9) 0.0344(9) 0.0490(10) 0.0013(8) 0.0052(8) -0.0050(8) N1 0.0232(9) 0.0268(8) 0.0202(7) 0.0016(6) 0.0033(7) 0.0028(8) N2 0.0244(9) 0.0279(8) 0.0191(7) 0.0006(6) 0.0010(7) 0.0002(7) N3 0.0293(9) 0.0249(8) 0.0214(7) 0.0016(6) 0.0007(7) -0.0014(8) C1 0.0235(10) 0.0243(9) 0.0189(8) 0.0023(7) 0.0025(8) 0.0009(8) C2 0.0248(10) 0.0269(9) 0.0203(8) -0.0010(7) 0.0012(8) -0.0026(9) C3 0.0282(11) 0.0252(9) 0.0188(8) -0.0006(7) 0.0010(8) -0.0011(9) C4 0.0260(11) 0.0255(9) 0.0203(8) 0.0012(7) 0.0037(8) -0.0004(8) C5 0.0232(10) 0.0247(9) 0.0206(8) 0.0009(7) 0.0032(8) -0.0002(8) C6 0.0270(11) 0.0296(10) 0.0289(10) -0.0052(8) 0.0067(9) -0.0028(9) C7 0.0499(17) 0.0315(11) 0.0392(12) 0.0044(10) 0.0041(12) -0.0092(12) C8 0.075(2) 0.0267(12) 0.077(2) 0.0033(13) 0.010(2) -0.0058(15) C9 0.0414(15) 0.0343(11) 0.0311(11) -0.0003(9) -0.0110(11) -0.0066(11) C10 0.0531(17) 0.0482(14) 0.0280(11) -0.0063(10) -0.0075(12) -0.0045(14) C11 0.0360(13) 0.0512(15) 0.0257(10) 0.0011(10) 0.0082(10) 0.0009(12) C12 0.080(2) 0.068(2) 0.0330(13) 0.0136(13) 0.0165(16) 0.001(2) C13 0.0332(12) 0.0236(9) 0.0317(10) 0.0037(8) -0.0005(10) -0.0042(9) C14 0.0504(17) 0.0366(13) 0.0488(15) -0.0126(11) 0.0033(13) -0.0095(13) C15 0.0240(10) 0.0228(8) 0.0185(8) -0.0010(7) 0.0026(8) -0.0018(8) C16 0.0269(10) 0.0222(8) 0.0196(8) 0.0009(7) -0.0016(8) -0.0020(8) C17 0.0273(10) 0.0191(8) 0.0243(9) -0.0004(7) -0.0020(8) -0.0011(8) C18 0.0295(11) 0.0246(9) 0.0295(10) -0.0016(8) 0.0027(9) 0.0013(10) C19 0.0318(12) 0.0245(10) 0.0413(12) -0.0040(9) -0.0035(11) 0.0074(10) C20 0.0391(14) 0.0276(10) 0.0372(12) 0.0023(9) -0.0073(11) 0.0060(11) C21 0.0404(13) 0.0248(10) 0.0286(10) 0.0051(8) -0.0035(10) 0.0012(10) C22 0.0288(11) 0.0232(9) 0.0236(9) 0.0015(7) -0.0002(9) -0.0019(9) C23 0.0275(10) 0.0226(9) 0.0204(8) -0.0030(7) 0.0025(8) -0.0034(8) C24 0.0331(11) 0.0290(10) 0.0203(8) -0.0021(8) 0.0051(9) -0.0058(9) C25 0.0260(10) 0.0291(10) 0.0245(9) -0.0072(8) 0.0052(8) -0.0047(9) C26 0.0240(10) 0.0275(10) 0.0278(9) -0.0065(8) 0.0004(8) -0.0007(9) C27 0.0263(11) 0.0266(9) 0.0221(8) -0.0019(8) 0.0002(8) -0.0022(9) C28 0.0241(10) 0.0242(9) 0.0197(8) -0.0024(7) 0.0019(8) -0.0030(8) C29 0.0337(12) 0.0431(13) 0.0274(10) -0.0072(9) 0.0090(10) -0.0031(11) C30 0.0321(13) 0.0413(13) 0.0378(12) -0.0072(10) 0.0034(11) 0.0085(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.419(3) . ? O1 C5 1.435(2) . ? O2 C7 1.359(3) . ? O2 C2 1.437(3) . ? O3 C7 1.204(4) . ? O4 C9 1.360(3) . ? O4 C3 1.440(2) . ? O5 C9 1.196(3) . ? O6 C11 1.353(3) . ? O6 C4 1.444(2) . ? O7 C11 1.202(4) . ? O8 C13 1.345(3) . ? O8 C6 1.453(3) . ? O9 C13 1.202(3) . ? N1 C15 1.386(3) . ? N1 C17 1.410(3) . ? N1 C1 1.446(2) . ? N2 C15 1.305(3) . ? N2 C28 1.382(3) . ? N3 C16 1.311(3) . ? N3 C23 1.375(3) . ? C1 C2 1.529(3) . ? C1 H1 1.0000 . ? C2 C3 1.524(3) . ? C2 H2 1.0000 . ? C3 C4 1.526(3) . ? C3 H3 1.0000 . ? C4 C5 1.528(3) . ? C4 H4 1.0000 . ? C5 C6 1.510(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.492(5) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.489(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.498(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.503(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.445(3) . ? C16 C22 1.446(3) . ? C17 C18 1.388(3) . ? C17 C22 1.417(3) . ? C18 C19 1.394(3) . ? C18 H18 0.9500 . ? C19 C20 1.398(4) . ? C19 H19 0.9500 . ? C20 C21 1.384(4) . ? C20 H20 0.9500 . ? C21 C22 1.395(3) . ? C21 H21 0.9500 . ? C23 C24 1.418(3) . ? C23 C28 1.428(3) . ? C24 C25 1.379(3) . ? C24 H24A 0.9500 . ? C25 C26 1.430(3) . ? C25 C29 1.509(3) . ? C26 C27 1.377(3) . ? C26 C30 1.503(3) . ? C27 C28 1.404(3) . ? C27 H27A 0.9500 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C29 H29D 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C5 111.04(15) . . ? C7 O2 C2 117.0(2) . . ? C9 O4 C3 117.08(17) . . ? C11 O6 C4 119.90(19) . . ? C13 O8 C6 116.06(18) . . ? C15 N1 C17 108.79(17) . . ? C15 N1 C1 121.42(18) . . ? C17 N1 C1 129.52(18) . . ? C15 N2 C28 113.07(17) . . ? C16 N3 C23 114.59(17) . . ? O1 C1 N1 107.89(17) . . ? O1 C1 C2 111.02(17) . . ? N1 C1 C2 113.33(17) . . ? O1 C1 H1 108.2 . . ? N1 C1 H1 108.2 . . ? C2 C1 H1 108.2 . . ? O2 C2 C3 109.75(17) . . ? O2 C2 C1 110.22(17) . . ? C3 C2 C1 108.40(16) . . ? O2 C2 H2 109.5 . . ? C3 C2 H2 109.5 . . ? C1 C2 H2 109.5 . . ? O4 C3 C2 108.28(16) . . ? O4 C3 C4 110.84(17) . . ? C2 C3 C4 111.97(18) . . ? O4 C3 H3 108.6 . . ? C2 C3 H3 108.6 . . ? C4 C3 H3 108.6 . . ? O6 C4 C3 109.73(17) . . ? O6 C4 C5 105.24(16) . . ? C3 C4 C5 107.13(17) . . ? O6 C4 H4 111.5 . . ? C3 C4 H4 111.5 . . ? C5 C4 H4 111.5 . . ? O1 C5 C6 106.77(17) . . ? O1 C5 C4 108.97(16) . . ? C6 C5 C4 113.29(17) . . ? O1 C5 H5 109.2 . . ? C6 C5 H5 109.2 . . ? C4 C5 H5 109.2 . . ? O8 C6 C5 105.76(17) . . ? O8 C6 H6A 110.6 . . ? C5 C6 H6A 110.6 . . ? O8 C6 H6B 110.6 . . ? C5 C6 H6B 110.6 . . ? H6A C6 H6B 108.7 . . ? O3 C7 O2 123.2(3) . . ? O3 C7 C8 126.1(3) . . ? O2 C7 C8 110.7(3) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O5 C9 O4 123.0(2) . . ? O5 C9 C10 125.6(3) . . ? O4 C9 C10 111.3(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O7 C11 O6 123.2(2) . . ? O7 C11 C12 126.6(3) . . ? O6 C11 C12 110.1(2) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O9 C13 O8 123.1(2) . . ? O9 C13 C14 125.9(2) . . ? O8 C13 C14 111.1(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 N1 125.58(18) . . ? N2 C15 C16 125.68(19) . . ? N1 C15 C16 108.74(18) . . ? N3 C16 C15 122.0(2) . . ? N3 C16 C22 131.56(19) . . ? C15 C16 C22 106.39(18) . . ? C18 C17 N1 130.0(2) . . ? C18 C17 C22 121.1(2) . . ? N1 C17 C22 108.86(19) . . ? C17 C18 C19 117.6(2) . . ? C17 C18 H18 121.2 . . ? C19 C18 H18 121.2 . . ? C18 C19 C20 121.7(2) . . ? C18 C19 H19 119.1 . . ? C20 C19 H19 119.1 . . ? C21 C20 C19 120.6(2) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 118.8(2) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? C21 C22 C17 120.1(2) . . ? C21 C22 C16 132.6(2) . . ? C17 C22 C16 107.22(18) . . ? N3 C23 C24 119.05(18) . . ? N3 C23 C28 122.65(19) . . ? C24 C23 C28 118.3(2) . . ? C25 C24 C23 122.2(2) . . ? C25 C24 H24A 118.9 . . ? C23 C24 H24A 118.9 . . ? C24 C25 C26 118.96(19) . . ? C24 C25 C29 120.7(2) . . ? C26 C25 C29 120.3(2) . . ? C27 C26 C25 119.6(2) . . ? C27 C26 C30 120.0(2) . . ? C25 C26 C30 120.5(2) . . ? C26 C27 C28 122.1(2) . . ? C26 C27 H27A 118.9 . . ? C28 C27 H27A 118.9 . . ? N2 C28 C27 119.22(18) . . ? N2 C28 C23 122.0(2) . . ? C27 C28 C23 118.82(19) . . ? C25 C29 H29B 109.5 . . ? C25 C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C25 C29 H29D 109.5 . . ? H29B C29 H29D 109.5 . . ? H29C C29 H29D 109.5 . . ? C26 C30 H30A 109.5 . . ? C26 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C26 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? 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 C5 O1 C1 N1 171.66(15) . . . . ? C5 O1 C1 C2 -63.6(2) . . . . ? C15 N1 C1 O1 -133.84(19) . . . . ? C17 N1 C1 O1 39.6(3) . . . . ? C15 N1 C1 C2 102.8(2) . . . . ? C17 N1 C1 C2 -83.8(3) . . . . ? C7 O2 C2 C3 131.7(2) . . . . ? C7 O2 C2 C1 -108.9(2) . . . . ? O1 C1 C2 O2 -64.9(2) . . . . ? N1 C1 C2 O2 56.7(2) . . . . ? O1 C1 C2 C3 55.2(2) . . . . ? N1 C1 C2 C3 176.80(18) . . . . ? C9 O4 C3 C2 -139.4(2) . . . . ? C9 O4 C3 C4 97.4(2) . . . . ? O2 C2 C3 O4 -54.8(2) . . . . ? C1 C2 C3 O4 -175.24(18) . . . . ? O2 C2 C3 C4 67.7(2) . . . . ? C1 C2 C3 C4 -52.7(2) . . . . ? C11 O6 C4 C3 93.0(2) . . . . ? C11 O6 C4 C5 -152.0(2) . . . . ? O4 C3 C4 O6 -69.5(2) . . . . ? C2 C3 C4 O6 169.50(16) . . . . ? O4 C3 C4 C5 176.78(16) . . . . ? C2 C3 C4 C5 55.8(2) . . . . ? C1 O1 C5 C6 -170.86(16) . . . . ? C1 O1 C5 C4 66.4(2) . . . . ? O6 C4 C5 O1 -177.48(17) . . . . ? C3 C4 C5 O1 -60.7(2) . . . . ? O6 C4 C5 C6 63.8(2) . . . . ? C3 C4 C5 C6 -179.41(17) . . . . ? C13 O8 C6 C5 -172.70(18) . . . . ? O1 C5 C6 O8 75.4(2) . . . . ? C4 C5 C6 O8 -164.68(17) . . . . ? C2 O2 C7 O3 -0.7(4) . . . . ? C2 O2 C7 C8 178.1(2) . . . . ? C3 O4 C9 O5 6.6(4) . . . . ? C3 O4 C9 C10 -171.4(2) . . . . ? C4 O6 C11 O7 -1.1(4) . . . . ? C4 O6 C11 C12 179.3(3) . . . . ? C6 O8 C13 O9 -3.6(3) . . . . ? C6 O8 C13 C14 176.5(2) . . . . ? C28 N2 C15 N1 179.1(2) . . . . ? C28 N2 C15 C16 -0.9(3) . . . . ? C17 N1 C15 N2 -179.7(2) . . . . ? C1 N1 C15 N2 -5.1(3) . . . . ? C17 N1 C15 C16 0.3(2) . . . . ? C1 N1 C15 C16 174.91(18) . . . . ? C23 N3 C16 C15 -1.2(3) . . . . ? C23 N3 C16 C22 -179.0(2) . . . . ? N2 C15 C16 N3 1.8(3) . . . . ? N1 C15 C16 N3 -178.17(19) . . . . ? N2 C15 C16 C22 -179.9(2) . . . . ? N1 C15 C16 C22 0.1(2) . . . . ? C15 N1 C17 C18 177.4(2) . . . . ? C1 N1 C17 C18 3.3(4) . . . . ? C15 N1 C17 C22 -0.5(2) . . . . ? C1 N1 C17 C22 -174.6(2) . . . . ? N1 C17 C18 C19 -179.2(2) . . . . ? C22 C17 C18 C19 -1.5(3) . . . . ? C17 C18 C19 C20 0.8(3) . . . . ? C18 C19 C20 C21 0.2(4) . . . . ? C19 C20 C21 C22 -0.5(4) . . . . ? C20 C21 C22 C17 -0.2(3) . . . . ? C20 C21 C22 C16 178.2(2) . . . . ? C18 C17 C22 C21 1.2(3) . . . . ? N1 C17 C22 C21 179.3(2) . . . . ? C18 C17 C22 C16 -177.55(19) . . . . ? N1 C17 C22 C16 0.6(2) . . . . ? N3 C16 C22 C21 -0.9(4) . . . . ? C15 C16 C22 C21 -178.9(2) . . . . ? N3 C16 C22 C17 177.6(2) . . . . ? C15 C16 C22 C17 -0.4(2) . . . . ? C16 N3 C23 C24 -179.7(2) . . . . ? C16 N3 C23 C28 0.0(3) . . . . ? N3 C23 C24 C25 179.4(2) . . . . ? C28 C23 C24 C25 -0.3(3) . . . . ? C23 C24 C25 C26 0.3(3) . . . . ? C23 C24 C25 C29 -179.9(2) . . . . ? C24 C25 C26 C27 -0.5(3) . . . . ? C29 C25 C26 C27 179.7(2) . . . . ? C24 C25 C26 C30 179.2(2) . . . . ? C29 C25 C26 C30 -0.6(3) . . . . ? C25 C26 C27 C28 0.8(3) . . . . ? C30 C26 C27 C28 -178.9(2) . . . . ? C15 N2 C28 C27 179.56(19) . . . . ? C15 N2 C28 C23 -0.4(3) . . . . ? C26 C27 C28 N2 179.2(2) . . . . ? C26 C27 C28 C23 -0.9(3) . . . . ? N3 C23 C28 N2 0.8(3) . . . . ? C24 C23 C28 N2 -179.5(2) . . . . ? N3 C23 C28 C27 -179.09(19) . . . . ? C24 C23 C28 C27 0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.362 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.049 #====================================================================== #_eof # End of Crystallographic Information File # Attachment 'slp175a.cif' #====================================================================== data_slp175a _database_code_depnum_ccdc_archive 'CCDC 695576' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-(2',3',4'-Tri-O-acetyl-\b-L-rhamnopyranosyl)indolo[2,3-b]quinoxaline ; _chemical_name_common ? _chemical_melting_point 514 _chemical_formula_moiety 'C26 H25 N3 O7' _chemical_formula_sum 'C26 H25 N3 O7' _chemical_formula_weight 491.49 _chemical_absolute_configuration syn 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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' _cell_length_a 6.3601(2) _cell_length_b 11.2214(5) _cell_length_c 35.0578(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2502.05(17) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3805 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 21.66 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9428 _exptl_absorpt_correction_T_max 0.9924 _exptl_absorpt_process_details 'SADABS; (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14471 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 24.66 _reflns_number_total 2482 _reflns_number_gt 2028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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 absolute structure could not be determined from the diffraction experiment. So in the final step of the refinement the MERG 4 instruction was used. ; _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^)+(0.0486P)^2^+0.2577P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 2482 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0904 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.031 _refine_ls_shift/su_mean 0.001 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 -0.5668(3) -0.33249(15) -0.09664(5) 0.0427(5) Uani 1 1 d . . . O2 O -0.4530(3) -0.22283(16) -0.16729(5) 0.0446(5) Uani 1 1 d . . . O3 O -0.2189(6) -0.1012(3) -0.19318(9) 0.1221(13) Uani 1 1 d . . . O4 O -0.2245(3) -0.41438(19) -0.19340(6) 0.0550(6) Uani 1 1 d . . . O5 O 0.1056(4) -0.3532(3) -0.18209(8) 0.0854(8) Uani 1 1 d . . . O6 O -0.4016(4) -0.59988(17) -0.14835(7) 0.0661(7) Uani 1 1 d . . . O7 O -0.6598(8) -0.6407(3) -0.18895(10) 0.1301(15) Uani 1 1 d . . . N1 N -0.4089(4) -0.14855(19) -0.08712(6) 0.0408(5) Uani 1 1 d . . . N2 N -0.1019(4) -0.14752(19) -0.04782(6) 0.0402(5) Uani 1 1 d . . . N3 N -0.2192(4) 0.09843(19) -0.03476(6) 0.0424(6) Uani 1 1 d . . . C1 C -0.3778(4) -0.2684(2) -0.10119(7) 0.0396(7) Uani 1 1 d . . . H1 H -0.2716 -0.3063 -0.0850 0.048 Uiso 1 1 calc R . . C2 C -0.2986(4) -0.2738(2) -0.14212(7) 0.0406(7) Uani 1 1 d . . . H2 H -0.1652 -0.2307 -0.1444 0.049 Uiso 1 1 calc R . . C3 C -0.2689(5) -0.4036(2) -0.15311(7) 0.0415(7) Uani 1 1 d . . . H3 H -0.1507 -0.4366 -0.1386 0.050 Uiso 1 1 calc R . . C4 C -0.4639(5) -0.4763(2) -0.14485(8) 0.0434(7) Uani 1 1 d . . . H4 H -0.5767 -0.4570 -0.1629 0.052 Uiso 1 1 calc R . . C5 C -0.5358(5) -0.4575(2) -0.10372(8) 0.0432(7) Uani 1 1 d . . . H5 H -0.4263 -0.4871 -0.0865 0.052 Uiso 1 1 calc R . . C6 C -0.7395(5) -0.5190(3) -0.09429(9) 0.0579(8) Uani 1 1 d . . . H6A H -0.8532 -0.4792 -0.1070 0.087 Uiso 1 1 calc R . . H6B H -0.7621 -0.5166 -0.0672 0.087 Uiso 1 1 calc R . . H6C H -0.7331 -0.6004 -0.1026 0.087 Uiso 1 1 calc R . . C7 C -0.3928(6) -0.1399(3) -0.19238(9) 0.0594(9) Uani 1 1 d . . . C8 C -0.5664(7) -0.1052(3) -0.21790(10) 0.0815(12) Uani 1 1 d . . . H8A H -0.5122 -0.0579 -0.2385 0.122 Uiso 1 1 calc R . . H8B H -0.6681 -0.0597 -0.2038 0.122 Uiso 1 1 calc R . . H8C H -0.6321 -0.1755 -0.2280 0.122 Uiso 1 1 calc R . . C9 C -0.0260(6) -0.3861(3) -0.20410(11) 0.0665(10) Uani 1 1 d . . . C10 C 0.0002(9) -0.3972(5) -0.24622(13) 0.125(2) Uani 1 1 d . . . H10A H 0.1276 -0.3581 -0.2539 0.188 Uiso 1 1 calc R . . H10B H -0.1173 -0.3607 -0.2588 0.188 Uiso 1 1 calc R . . H10C H 0.0072 -0.4800 -0.2531 0.188 Uiso 1 1 calc R . . C11 C -0.5055(9) -0.6704(3) -0.17222(12) 0.0830(14) Uani 1 1 d . . . C12 C -0.4023(10) -0.7907(3) -0.17396(12) 0.126(2) Uani 1 1 d . . . H12A H -0.2674 -0.7835 -0.1860 0.189 Uiso 1 1 calc R . . H12B H -0.4890 -0.8442 -0.1884 0.189 Uiso 1 1 calc R . . H12C H -0.3846 -0.8211 -0.1486 0.189 Uiso 1 1 calc R . . C13 C -0.5648(5) -0.0647(2) -0.09661(7) 0.0381(6) Uani 1 1 d . . . C14 C -0.7452(5) -0.0773(2) -0.11886(7) 0.0455(7) Uani 1 1 d . . . H14 H -0.7776 -0.1494 -0.1306 0.055 Uiso 1 1 calc R . . C15 C -0.8735(5) 0.0205(3) -0.12293(9) 0.0517(8) Uani 1 1 d . . . H15 H -0.9933 0.0142 -0.1380 0.062 Uiso 1 1 calc R . . C16 C -0.8290(5) 0.1292(3) -0.10509(9) 0.0546(8) Uani 1 1 d . . . H16 H -0.9190 0.1936 -0.1085 0.066 Uiso 1 1 calc R . . C17 C -0.6525(5) 0.1413(3) -0.08245(8) 0.0486(8) Uani 1 1 d . . . H17 H -0.6235 0.2132 -0.0703 0.058 Uiso 1 1 calc R . . C18 C -0.5195(4) 0.0444(2) -0.07817(7) 0.0386(7) Uani 1 1 d . . . C19 C -0.3283(4) 0.0262(2) -0.05660(7) 0.0376(7) Uani 1 1 d . . . C20 C -0.2663(5) -0.0956(2) -0.06265(7) 0.0364(6) Uani 1 1 d . . . C21 C 0.0144(5) -0.0729(2) -0.02485(7) 0.0392(7) Uani 1 1 d . . . C22 C 0.1976(5) -0.1183(3) -0.00764(7) 0.0477(8) Uani 1 1 d . . . H22 H 0.2355 -0.1974 -0.0115 0.057 Uiso 1 1 calc R . . C23 C 0.3202(5) -0.0466(3) 0.01469(8) 0.0534(8) Uani 1 1 d . . . H23 H 0.4396 -0.0778 0.0263 0.064 Uiso 1 1 calc R . . C24 C 0.2674(6) 0.0736(3) 0.02025(8) 0.0559(8) Uani 1 1 d . . . H24 H 0.3541 0.1219 0.0350 0.067 Uiso 1 1 calc R . . C25 C 0.0901(5) 0.1202(3) 0.00421(7) 0.0493(8) Uani 1 1 d . . . H25 H 0.0559 0.1997 0.0083 0.059 Uiso 1 1 calc R . . C26 C -0.0419(5) 0.0483(2) -0.01860(7) 0.0395(7) Uani 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 0.0448(11) 0.0340(10) 0.0494(11) -0.0021(8) 0.0022(10) -0.0016(9) O2 0.0447(12) 0.0430(11) 0.0462(10) 0.0052(9) -0.0047(9) -0.0028(9) O3 0.107(3) 0.138(3) 0.121(2) 0.072(2) -0.027(2) -0.062(2) O4 0.0431(13) 0.0671(14) 0.0548(12) -0.0201(10) 0.0077(11) -0.0110(11) O5 0.0432(14) 0.106(2) 0.107(2) -0.0207(17) 0.0038(15) -0.0076(15) O6 0.0795(17) 0.0336(11) 0.0851(16) -0.0128(11) 0.0074(14) 0.0043(11) O7 0.182(4) 0.089(2) 0.119(3) -0.031(2) -0.048(3) -0.033(3) N1 0.0446(14) 0.0335(12) 0.0445(12) -0.0048(9) -0.0068(11) -0.0010(12) N2 0.0478(15) 0.0336(12) 0.0391(12) -0.0003(10) -0.0020(11) -0.0033(11) N3 0.0499(16) 0.0359(12) 0.0413(12) -0.0048(10) 0.0033(12) -0.0027(12) C1 0.0441(17) 0.0316(15) 0.0432(15) -0.0021(11) -0.0061(13) -0.0004(13) C2 0.0320(16) 0.0435(16) 0.0462(15) -0.0027(12) -0.0045(13) -0.0077(13) C3 0.0350(16) 0.0441(15) 0.0456(15) -0.0076(12) -0.0053(13) 0.0037(13) C4 0.0456(18) 0.0306(14) 0.0541(16) -0.0036(12) -0.0043(14) 0.0005(13) C5 0.0464(18) 0.0326(14) 0.0507(16) 0.0037(12) -0.0062(14) -0.0005(13) C6 0.061(2) 0.0453(17) 0.0675(19) 0.0047(14) 0.0055(18) -0.0102(17) C7 0.073(3) 0.0514(19) 0.0537(19) 0.0068(15) -0.0067(19) -0.0132(19) C8 0.109(3) 0.071(2) 0.064(2) 0.0162(18) -0.019(2) 0.005(3) C9 0.047(2) 0.073(2) 0.080(2) -0.0258(19) 0.017(2) -0.0101(19) C10 0.101(3) 0.179(5) 0.096(3) -0.055(3) 0.050(3) -0.054(4) C11 0.127(4) 0.049(2) 0.073(3) -0.018(2) 0.034(3) -0.020(3) C12 0.211(6) 0.049(2) 0.118(4) -0.026(2) 0.078(4) -0.009(3) C13 0.0375(16) 0.0389(15) 0.0378(14) 0.0007(11) 0.0011(13) -0.0009(13) C14 0.0451(19) 0.0454(16) 0.0460(15) -0.0036(12) -0.0006(15) -0.0024(15) C15 0.0407(18) 0.060(2) 0.0548(17) 0.0046(15) -0.0035(14) 0.0015(16) C16 0.050(2) 0.0497(19) 0.064(2) 0.0042(15) 0.0012(17) 0.0125(15) C17 0.052(2) 0.0406(16) 0.0530(17) -0.0010(13) 0.0031(16) 0.0048(15) C18 0.0414(18) 0.0377(15) 0.0368(14) 0.0007(11) 0.0064(13) 0.0015(13) C19 0.0449(17) 0.0342(14) 0.0336(13) -0.0009(11) 0.0049(13) -0.0043(12) C20 0.0423(17) 0.0334(13) 0.0335(13) -0.0007(10) -0.0003(13) -0.0041(13) C21 0.0462(18) 0.0407(15) 0.0307(12) 0.0017(11) 0.0000(12) -0.0087(13) C22 0.053(2) 0.0455(17) 0.0446(16) 0.0063(13) -0.0078(15) -0.0064(15) C23 0.053(2) 0.064(2) 0.0423(16) 0.0070(14) -0.0077(14) -0.0106(16) C24 0.063(2) 0.065(2) 0.0397(15) -0.0010(14) -0.0053(16) -0.0225(19) C25 0.063(2) 0.0444(17) 0.0401(15) -0.0088(12) -0.0005(16) -0.0125(16) C26 0.0466(18) 0.0387(15) 0.0332(13) -0.0016(11) 0.0022(13) -0.0074(14) _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 1.410(3) . ? O1 C5 1.438(3) . ? O2 C7 1.337(4) . ? O2 C2 1.439(3) . ? O3 C7 1.188(4) . ? O4 C9 1.355(4) . ? O4 C3 1.445(3) . ? O5 C9 1.197(4) . ? O6 C11 1.328(5) . ? O6 C4 1.448(3) . ? O7 C11 1.191(6) . ? N1 C20 1.382(3) . ? N1 C13 1.407(3) . ? N1 C1 1.446(3) . ? N2 C20 1.305(3) . ? N2 C21 1.378(3) . ? N3 C19 1.313(3) . ? N3 C26 1.382(4) . ? C1 C2 1.522(4) . ? C1 H1 0.9800 . ? C2 C3 1.519(4) . ? C2 H2 0.9800 . ? C3 C4 1.512(4) . ? C3 H3 0.9800 . ? C4 C5 1.527(4) . ? C4 H4 0.9800 . ? C5 C6 1.504(4) . ? C5 H5 0.9800 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.474(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.491(5) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.501(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.395(4) . ? C13 C18 1.415(4) . ? C14 C15 1.374(4) . ? C14 H14 0.9300 . ? C15 C16 1.400(4) . ? C15 H15 0.9300 . ? C16 C17 1.382(4) . ? C16 H16 0.9300 . ? C17 C18 1.386(4) . ? C17 H17 0.9300 . ? C18 C19 1.447(4) . ? C19 C20 1.439(4) . ? C21 C22 1.407(4) . ? C21 C26 1.423(4) . ? C22 C23 1.366(4) . ? C22 H22 0.9300 . ? C23 C24 1.404(4) . ? C23 H23 0.9300 . ? C24 C25 1.365(4) . ? C24 H24 0.9300 . ? C25 C26 1.412(4) . ? C25 H25 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C5 111.2(2) . . ? C7 O2 C2 119.0(2) . . ? C9 O4 C3 115.7(2) . . ? C11 O6 C4 119.2(3) . . ? C20 N1 C13 108.8(2) . . ? C20 N1 C1 121.4(2) . . ? C13 N1 C1 129.6(2) . . ? C20 N2 C21 113.1(2) . . ? C19 N3 C26 114.8(2) . . ? O1 C1 N1 108.6(2) . . ? O1 C1 C2 111.6(2) . . ? N1 C1 C2 113.8(2) . . ? O1 C1 H1 107.5 . . ? N1 C1 H1 107.5 . . ? C2 C1 H1 107.5 . . ? O2 C2 C3 108.1(2) . . ? O2 C2 C1 109.7(2) . . ? C3 C2 C1 108.6(2) . . ? O2 C2 H2 110.2 . . ? C3 C2 H2 110.2 . . ? C1 C2 H2 110.2 . . ? O4 C3 C4 107.6(2) . . ? O4 C3 C2 110.6(2) . . ? C4 C3 C2 111.5(2) . . ? O4 C3 H3 109.0 . . ? C4 C3 H3 109.0 . . ? C2 C3 H3 109.0 . . ? O6 C4 C3 106.0(2) . . ? O6 C4 C5 107.1(2) . . ? C3 C4 C5 110.6(2) . . ? O6 C4 H4 111.0 . . ? C3 C4 H4 111.0 . . ? C5 C4 H4 111.0 . . ? O1 C5 C6 107.0(2) . . ? O1 C5 C4 109.8(2) . . ? C6 C5 C4 113.7(2) . . ? O1 C5 H5 108.8 . . ? C6 C5 H5 108.8 . . ? C4 C5 H5 108.8 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O3 C7 O2 122.5(3) . . ? O3 C7 C8 125.9(3) . . ? O2 C7 C8 111.6(3) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O5 C9 O4 123.0(3) . . ? O5 C9 C10 125.9(4) . . ? O4 C9 C10 111.0(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O7 C11 O6 123.6(4) . . ? O7 C11 C12 126.3(5) . . ? O6 C11 C12 110.1(5) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 N1 130.1(2) . . ? C14 C13 C18 120.7(2) . . ? N1 C13 C18 109.1(2) . . ? C15 C14 C13 117.8(3) . . ? C15 C14 H14 121.1 . . ? C13 C14 H14 121.1 . . ? C14 C15 C16 122.0(3) . . ? C14 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C17 C16 C15 120.4(3) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 118.7(3) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 120.6 . . ? C17 C18 C13 120.4(3) . . ? C17 C18 C19 132.9(3) . . ? C13 C18 C19 106.7(2) . . ? N3 C19 C20 121.8(2) . . ? N3 C19 C18 131.4(3) . . ? C20 C19 C18 106.7(2) . . ? N2 C20 N1 125.5(2) . . ? N2 C20 C19 125.8(2) . . ? N1 C20 C19 108.7(2) . . ? N2 C21 C22 118.4(3) . . ? N2 C21 C26 122.4(3) . . ? C22 C21 C26 119.2(3) . . ? C23 C22 C21 120.3(3) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 120.6(3) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C25 C24 C23 120.6(3) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 120.4(3) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? N3 C26 C25 119.0(3) . . ? N3 C26 C21 122.1(2) . . ? C25 C26 C21 118.9(3) . . ? 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 C5 O1 C1 N1 -169.7(2) . . . . ? C5 O1 C1 C2 64.0(3) . . . . ? C20 N1 C1 O1 132.1(2) . . . . ? C13 N1 C1 O1 -53.3(3) . . . . ? C20 N1 C1 C2 -102.9(3) . . . . ? C13 N1 C1 C2 71.8(4) . . . . ? C7 O2 C2 C3 -112.2(3) . . . . ? C7 O2 C2 C1 129.5(2) . . . . ? O1 C1 C2 O2 60.3(3) . . . . ? N1 C1 C2 O2 -63.1(3) . . . . ? O1 C1 C2 C3 -57.6(3) . . . . ? N1 C1 C2 C3 179.0(2) . . . . ? C9 O4 C3 C4 -161.0(3) . . . . ? C9 O4 C3 C2 76.9(3) . . . . ? O2 C2 C3 O4 52.5(3) . . . . ? C1 C2 C3 O4 171.3(2) . . . . ? O2 C2 C3 C4 -67.3(3) . . . . ? C1 C2 C3 C4 51.6(3) . . . . ? C11 O6 C4 C3 -124.4(3) . . . . ? C11 O6 C4 C5 117.4(3) . . . . ? O4 C3 C4 O6 70.9(3) . . . . ? C2 C3 C4 O6 -167.6(2) . . . . ? O4 C3 C4 C5 -173.3(2) . . . . ? C2 C3 C4 C5 -51.8(3) . . . . ? C1 O1 C5 C6 174.4(2) . . . . ? C1 O1 C5 C4 -61.8(3) . . . . ? O6 C4 C5 O1 170.5(2) . . . . ? C3 C4 C5 O1 55.4(3) . . . . ? O6 C4 C5 C6 -69.7(3) . . . . ? C3 C4 C5 C6 175.2(2) . . . . ? C2 O2 C7 O3 -4.7(5) . . . . ? C2 O2 C7 C8 175.2(3) . . . . ? C3 O4 C9 O5 -0.6(5) . . . . ? C3 O4 C9 C10 -178.5(3) . . . . ? C4 O6 C11 O7 -6.4(6) . . . . ? C4 O6 C11 C12 174.8(3) . . . . ? C20 N1 C13 C14 -176.9(3) . . . . ? C1 N1 C13 C14 7.9(5) . . . . ? C20 N1 C13 C18 0.7(3) . . . . ? C1 N1 C13 C18 -174.5(2) . . . . ? N1 C13 C14 C15 179.0(3) . . . . ? C18 C13 C14 C15 1.6(4) . . . . ? C13 C14 C15 C16 -1.0(4) . . . . ? C14 C15 C16 C17 -0.2(4) . . . . ? C15 C16 C17 C18 0.8(4) . . . . ? C16 C17 C18 C13 -0.2(4) . . . . ? C16 C17 C18 C19 -178.8(3) . . . . ? C14 C13 C18 C17 -1.0(4) . . . . ? N1 C13 C18 C17 -178.9(2) . . . . ? C14 C13 C18 C19 177.9(2) . . . . ? N1 C13 C18 C19 0.0(3) . . . . ? C26 N3 C19 C20 0.5(3) . . . . ? C26 N3 C19 C18 -180.0(2) . . . . ? C17 C18 C19 N3 -1.6(5) . . . . ? C13 C18 C19 N3 179.7(3) . . . . ? C17 C18 C19 C20 178.0(3) . . . . ? C13 C18 C19 C20 -0.7(3) . . . . ? C21 N2 C20 N1 179.1(2) . . . . ? C21 N2 C20 C19 -0.3(4) . . . . ? C13 N1 C20 N2 179.4(2) . . . . ? C1 N1 C20 N2 -4.9(4) . . . . ? C13 N1 C20 C19 -1.1(3) . . . . ? C1 N1 C20 C19 174.5(2) . . . . ? N3 C19 C20 N2 0.2(4) . . . . ? C18 C19 C20 N2 -179.4(2) . . . . ? N3 C19 C20 N1 -179.3(2) . . . . ? C18 C19 C20 N1 1.1(3) . . . . ? C20 N2 C21 C22 -179.1(2) . . . . ? C20 N2 C21 C26 -0.3(3) . . . . ? N2 C21 C22 C23 178.6(2) . . . . ? C26 C21 C22 C23 -0.2(4) . . . . ? C21 C22 C23 C24 -1.1(4) . . . . ? C22 C23 C24 C25 1.6(4) . . . . ? C23 C24 C25 C26 -0.7(4) . . . . ? C19 N3 C26 C25 177.6(2) . . . . ? C19 N3 C26 C21 -1.0(3) . . . . ? C24 C25 C26 N3 -179.4(2) . . . . ? C24 C25 C26 C21 -0.6(4) . . . . ? N2 C21 C26 N3 1.0(4) . . . . ? C22 C21 C26 N3 179.8(2) . . . . ? N2 C21 C26 C25 -177.7(2) . . . . ? C22 C21 C26 C25 1.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.66 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.149 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.031 #====================================================================== #_eof # End of Crystallographic Information File