data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Janet Scott' 'Masaya Asami' 'Koichi Tanaka' _publ_contact_author_name 'Dr Janet Scott' _publ_contact_author_address ; Centre for Green Chemistry Monash University P.O. Box 23 Monash University Victoria 3800 AUSTRALIA ; _publ_contact_author_email JANET.SCOTT@SCI.MONASH.EDU.AU _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Novel Chromogenic, Guest-sensitive Host Compounds. ; data_c: _database_code_CSD 195725 _publ_section_title ; Novel Chromogenic, Guest-sensitive Host Compounds. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-{4-[4-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-phenylazo]-phenyl}-1, 1-diphenyl-prop-2-yn-1-ol dimethylformamide solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H44 N4 O4' _chemical_formula_weight 740.87 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7114(2) _cell_length_b 10.4231(2) _cell_length_c 11.8636(3) _cell_angle_alpha 70.9510(10) _cell_angle_beta 70.7580(10) _cell_angle_gamma 70.1610(10) _cell_volume 1034.91(4) _cell_formula_units_Z 1 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour 'red/pale orange dichroic' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9629 _exptl_absorpt_correction_T_max 0.9775 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 4924 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0717 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 28.35 _reflns_number_total 4924 _reflns_number_gt 2365 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XSeed _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^)+(0.0812P)^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 4924 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1320 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1559 _refine_ls_wR_factor_gt 0.1290 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _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 0.83310(13) 0.40049(11) 0.14485(10) 0.0512(3) Uani 1 1 d . . . N2 N 0.51954(15) 0.05626(13) 0.47946(12) 0.0505(4) Uani 1 1 d . . . C1 C 0.45119(18) 0.14888(16) 0.55936(14) 0.0463(4) Uani 1 1 d . . . C2 C 0.52370(19) 0.25283(16) 0.53863(14) 0.0486(4) Uani 1 1 d . . . C6 C 0.3195(2) 0.14240(18) 0.65103(16) 0.0579(5) Uani 1 1 d . . . H6 H 0.2713 0.0738 0.6635 0.069 Uiso 1 1 calc R . . C10 C 0.97622(18) 0.15916(17) 0.21212(15) 0.0471(4) Uani 1 1 d . . . C8 C 0.7608(2) 0.28231(17) 0.35427(16) 0.0527(5) Uani 1 1 d . . . C20 C 0.99771(19) 0.36165(17) 0.26950(15) 0.0484(4) Uani 1 1 d . . . C7 C 0.6555(2) 0.26598(16) 0.43899(16) 0.0523(5) Uani 1 1 d . . . C9 C 0.88908(18) 0.30122(16) 0.24505(14) 0.0449(4) Uani 1 1 d . . . C3 C 0.4635(2) 0.34449(18) 0.61684(16) 0.0603(5) Uani 1 1 d . . . H3 H 0.5122 0.4116 0.6074 0.072 Uiso 1 1 calc R . . C21 C 1.0800(2) 0.44388(17) 0.17451(16) 0.0556(5) Uani 1 1 d . . . H21 H 1.0662 0.4668 0.0957 0.067 Uiso 1 1 calc R . . N1G N 0.47372(17) 0.20179(17) 0.10908(16) 0.0674(5) Uani 1 1 d . . . C4 C 0.3324(2) 0.33608(19) 0.70780(16) 0.0661(6) Uani 1 1 d . . . H4 H 0.2930 0.3980 0.7588 0.079 Uiso 1 1 calc R . . C11 C 1.0407(2) 0.1529(2) 0.09140(17) 0.0619(5) Uani 1 1 d . . . H11 H 1.0288 0.2350 0.0293 0.074 Uiso 1 1 calc R . . C5 C 0.2598(2) 0.23711(19) 0.72357(17) 0.0659(5) Uani 1 1 d . . . H5 H 0.1698 0.2340 0.7835 0.079 Uiso 1 1 calc R . . O1G O 0.64162(18) 0.32136(18) 0.08005(14) 0.0947(5) Uani 1 1 d . . . C15 C 0.9957(2) 0.0366(2) 0.30059(19) 0.0785(6) Uani 1 1 d . . . H15 H 0.9539 0.0377 0.3831 0.094 Uiso 1 1 calc R . . C1G C 0.5667(2) 0.2386(2) 0.1449(2) 0.0682(5) Uani 1 1 d . . . H1G H 0.5758 0.1987 0.2254 0.082 Uiso 1 1 calc R . . C22 C 1.1825(2) 0.4928(2) 0.1945(2) 0.0752(6) Uani 1 1 d . . . H22 H 1.2374 0.5483 0.1291 0.090 Uiso 1 1 calc R . . C13 C 1.1403(2) -0.0944(2) 0.1493(2) 0.0765(6) Uani 1 1 d . . . H13 H 1.1944 -0.1794 0.1283 0.092 Uiso 1 1 calc R . . C12 C 1.1230(3) 0.0266(2) 0.0609(2) 0.0753(6) Uani 1 1 d . . . H12 H 1.1669 0.0248 -0.0212 0.090 Uiso 1 1 calc R . . C25 C 1.0196(3) 0.3307(3) 0.38545(19) 0.0808(6) Uani 1 1 d . . . H25 H 0.9641 0.2761 0.4513 0.097 Uiso 1 1 calc R . . C23 C 1.2044(3) 0.4605(3) 0.3091(3) 0.0908(8) Uani 1 1 d . . . H23 H 1.2744 0.4933 0.3222 0.109 Uiso 1 1 calc R . . C14 C 1.0779(3) -0.0904(2) 0.2686(2) 0.0965(8) Uani 1 1 d . . . H14 H 1.0899 -0.1732 0.3299 0.116 Uiso 1 1 calc R . . C3G C 0.4483(3) 0.2650(3) -0.0130(2) 0.0971(8) Uani 1 1 d . . . H3G1 H 0.4806 0.3502 -0.0470 0.146 Uiso 1 1 calc R . . H3G2 H 0.3426 0.2860 -0.0083 0.146 Uiso 1 1 calc R . . H3G3 H 0.5047 0.2008 -0.0647 0.146 Uiso 1 1 calc R . . C2G C 0.3894(3) 0.1024(3) 0.1927(3) 0.1031(8) Uani 1 1 d . . . H2G1 H 0.4077 0.0783 0.2727 0.155 Uiso 1 1 calc R . . H2G2 H 0.4211 0.0192 0.1628 0.155 Uiso 1 1 calc R . . H2G3 H 0.2835 0.1439 0.1980 0.155 Uiso 1 1 calc R . . C24 C 1.1227(3) 0.3798(3) 0.4047(2) 0.1019(8) Uani 1 1 d . . . H24 H 1.1369 0.3577 0.4833 0.122 Uiso 1 1 calc R . . H1O H 0.761(3) 0.368(2) 0.1255(19) 0.097(7) 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 0.0531(7) 0.0505(7) 0.0492(7) -0.0071(6) -0.0130(6) -0.0170(6) N2 0.0548(9) 0.0449(8) 0.0455(8) -0.0120(7) 0.0039(7) -0.0197(7) C1 0.0499(10) 0.0410(9) 0.0383(9) -0.0092(7) 0.0034(7) -0.0142(8) C2 0.0552(10) 0.0413(9) 0.0401(9) -0.0068(8) -0.0001(8) -0.0152(8) C6 0.0583(11) 0.0522(10) 0.0510(11) -0.0120(9) 0.0065(9) -0.0192(9) C10 0.0455(10) 0.0467(9) 0.0489(10) -0.0074(8) -0.0069(8) -0.0203(8) C8 0.0578(11) 0.0479(10) 0.0514(11) -0.0134(9) -0.0035(9) -0.0210(8) C20 0.0517(10) 0.0504(10) 0.0433(10) -0.0112(8) -0.0071(8) -0.0182(8) C7 0.0603(11) 0.0438(9) 0.0499(11) -0.0116(8) -0.0013(9) -0.0215(8) C9 0.0471(9) 0.0465(9) 0.0371(9) -0.0049(8) -0.0034(8) -0.0190(8) C3 0.0784(13) 0.0480(10) 0.0495(11) -0.0145(9) -0.0015(10) -0.0213(9) C21 0.0619(12) 0.0566(11) 0.0521(11) -0.0101(9) -0.0083(9) -0.0284(9) N1G 0.0524(9) 0.0784(11) 0.0799(12) -0.0209(10) -0.0237(9) -0.0183(8) C4 0.0869(15) 0.0518(11) 0.0439(11) -0.0182(9) 0.0011(10) -0.0091(10) C11 0.0749(13) 0.0574(11) 0.0531(12) -0.0181(10) -0.0162(10) -0.0118(10) C5 0.0669(13) 0.0569(11) 0.0490(11) -0.0132(9) 0.0127(9) -0.0110(10) O1G 0.0924(12) 0.1219(13) 0.0880(11) 0.0033(10) -0.0356(9) -0.0645(11) C15 0.0859(15) 0.0570(12) 0.0582(13) -0.0022(10) 0.0076(11) -0.0121(11) C1G 0.0612(12) 0.0796(14) 0.0706(13) -0.0136(11) -0.0255(11) -0.0220(11) C22 0.0750(14) 0.0749(14) 0.0881(16) -0.0216(12) -0.0121(12) -0.0406(11) C13 0.0674(13) 0.0581(13) 0.0976(18) -0.0282(13) -0.0025(13) -0.0166(11) C12 0.0840(15) 0.0717(14) 0.0728(14) -0.0337(13) -0.0151(12) -0.0120(12) C25 0.0923(16) 0.1102(17) 0.0519(12) -0.0066(12) -0.0201(11) -0.0510(14) C23 0.0845(17) 0.1082(19) 0.112(2) -0.0445(17) -0.0305(16) -0.0406(15) C14 0.0978(18) 0.0490(12) 0.0934(19) 0.0050(12) 0.0071(15) -0.0092(12) C3G 0.0745(15) 0.149(2) 0.0819(17) -0.0366(16) -0.0269(13) -0.0298(15) C2G 0.0904(18) 0.0903(17) 0.141(2) -0.0016(16) -0.0509(17) -0.0419(15) C24 0.114(2) 0.145(2) 0.0751(17) -0.0274(17) -0.0396(15) -0.0512(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 C9 1.421(2) . ? N2 N2 1.251(2) 2_656 ? N2 C1 1.4209(19) . ? C1 C6 1.385(2) . ? C1 C2 1.400(2) . ? C2 C3 1.399(2) . ? C2 C7 1.439(2) . ? C6 C5 1.374(2) . ? C10 C15 1.364(3) . ? C10 C11 1.375(2) . ? C10 C9 1.540(2) . ? C8 C7 1.189(2) . ? C8 C9 1.485(2) . ? C20 C21 1.373(2) . ? C20 C25 1.378(2) . ? C20 C9 1.538(2) . ? C3 C4 1.379(2) . ? C21 C22 1.373(2) . ? N1G C1G 1.318(2) . ? N1G C3G 1.448(3) . ? N1G C2G 1.448(3) . ? C4 C5 1.370(2) . ? C11 C12 1.381(2) . ? O1G C1G 1.220(2) . ? C15 C14 1.395(3) . ? C22 C23 1.361(3) . ? C13 C12 1.352(3) . ? C13 C14 1.352(3) . ? C25 C24 1.376(3) . ? C23 C24 1.364(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N2 C1 113.65(15) 2_656 . ? C6 C1 C2 120.43(14) . . ? C6 C1 N2 123.82(14) . . ? C2 C1 N2 115.73(13) . . ? C3 C2 C1 118.09(14) . . ? C3 C2 C7 120.92(14) . . ? C1 C2 C7 120.99(13) . . ? C5 C6 C1 120.18(16) . . ? C15 C10 C11 117.81(17) . . ? C15 C10 C9 121.71(15) . . ? C11 C10 C9 120.46(15) . . ? C7 C8 C9 177.45(17) . . ? C21 C20 C25 118.29(16) . . ? C21 C20 C9 120.39(15) . . ? C25 C20 C9 121.28(15) . . ? C8 C7 C2 177.1(2) . . ? O1 C9 C8 109.31(14) . . ? O1 C9 C20 106.58(12) . . ? C8 C9 C20 111.05(12) . . ? O1 C9 C10 110.78(12) . . ? C8 C9 C10 109.90(12) . . ? C20 C9 C10 109.18(13) . . ? C4 C3 C2 120.52(16) . . ? C22 C21 C20 120.80(18) . . ? C1G N1G C3G 120.59(19) . . ? C1G N1G C2G 120.85(19) . . ? C3G N1G C2G 118.49(18) . . ? C5 C4 C3 120.49(15) . . ? C10 C11 C12 120.99(19) . . ? C4 C5 C6 120.18(17) . . ? C10 C15 C14 120.65(19) . . ? O1G C1G N1G 124.8(2) . . ? C23 C22 C21 120.5(2) . . ? C12 C13 C14 119.23(19) . . ? C13 C12 C11 120.7(2) . . ? C24 C25 C20 120.6(2) . . ? C22 C23 C24 119.43(19) . . ? C13 C14 C15 120.6(2) . . ? C23 C24 C25 120.4(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 N2 N2 C1 C6 -20.9(3) 2_656 . . . ? N2 N2 C1 C2 160.55(19) 2_656 . . . ? C6 C1 C2 C3 3.1(3) . . . . ? N2 C1 C2 C3 -178.29(16) . . . . ? C6 C1 C2 C7 -176.25(17) . . . . ? N2 C1 C2 C7 2.3(2) . . . . ? C2 C1 C6 C5 -0.8(3) . . . . ? N2 C1 C6 C5 -179.27(17) . . . . ? C9 C8 C7 C2 -73(6) . . . . ? C3 C2 C7 C8 -67(3) . . . . ? C1 C2 C7 C8 112(3) . . . . ? C7 C8 C9 O1 54(4) . . . . ? C7 C8 C9 C20 172(4) . . . . ? C7 C8 C9 C10 -67(4) . . . . ? C21 C20 C9 O1 -31.7(2) . . . . ? C25 C20 C9 O1 150.82(17) . . . . ? C21 C20 C9 C8 -150.71(16) . . . . ? C25 C20 C9 C8 31.9(2) . . . . ? C21 C20 C9 C10 87.95(18) . . . . ? C25 C20 C9 C10 -89.5(2) . . . . ? C15 C10 C9 O1 -157.11(16) . . . . ? C11 C10 C9 O1 24.7(2) . . . . ? C15 C10 C9 C8 -36.2(2) . . . . ? C11 C10 C9 C8 145.59(16) . . . . ? C15 C10 C9 C20 85.8(2) . . . . ? C11 C10 C9 C20 -92.38(18) . . . . ? C1 C2 C3 C4 -3.0(3) . . . . ? C7 C2 C3 C4 176.41(18) . . . . ? C25 C20 C21 C22 0.6(3) . . . . ? C9 C20 C21 C22 -176.89(16) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C15 C10 C11 C12 -0.2(3) . . . . ? C9 C10 C11 C12 178.06(16) . . . . ? C3 C4 C5 C6 1.9(3) . . . . ? C1 C6 C5 C4 -1.8(3) . . . . ? C11 C10 C15 C14 -0.4(3) . . . . ? C9 C10 C15 C14 -178.62(19) . . . . ? C3G N1G C1G O1G -3.1(3) . . . . ? C2G N1G C1G O1G 179.9(2) . . . . ? C20 C21 C22 C23 0.0(3) . . . . ? C14 C13 C12 C11 -1.0(3) . . . . ? C10 C11 C12 C13 0.9(3) . . . . ? C21 C20 C25 C24 -0.8(3) . . . . ? C9 C20 C25 C24 176.7(2) . . . . ? C21 C22 C23 C24 -0.4(4) . . . . ? C12 C13 C14 C15 0.4(4) . . . . ? C10 C15 C14 C13 0.3(4) . . . . ? C22 C23 C24 C25 0.3(4) . . . . ? C20 C25 C24 C23 0.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.155 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.041 data_1 _database_code_CSD 196890 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-{4-[4-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-phenylazo]-phenyl}-1, 1-diphenyl-prop-2-yn-1-ol ; _chemical_name_common ? _chemical_melting_point 224-227 _chemical_formula_moiety 'C42 H30 N2 O2' _chemical_formula_sum 'C42 H30 N2 O2' _chemical_formula_weight 594.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8554(2) _cell_length_b 9.3045(5) _cell_length_c 14.6994(5) _cell_angle_alpha 71.827(3) _cell_angle_beta 89.422(3) _cell_angle_gamma 78.702(2) _cell_volume 745.04(5) _cell_formula_units_Z 1 _cell_measurement_temperature 123(2) _exptl_crystal_description needles _exptl_crystal_colour 'red/orange dichromic' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9839 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2518 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.97 _reflns_number_total 2518 _reflns_number_gt 2079 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XSeed _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^)+(0.0500P)^2^+0.2020P] 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 2518 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.07193(17) 0.90951(12) 0.29633(7) 0.0245(3) Uani 1 1 d . . . N1 N 0.9517(2) 0.96549(14) 0.47734(8) 0.0216(3) Uani 1 1 d . . . C24 C 0.2927(3) 0.83740(18) 0.04408(11) 0.0273(4) Uani 1 1 d . . . H24 H 0.1820 0.8437 -0.0046 0.033 Uiso 1 1 calc R . . C20 C 0.3796(3) 0.88083(17) 0.19222(10) 0.0212(3) Uani 1 1 d . . . C11 C 0.4457(3) 1.20001(19) 0.23681(11) 0.0263(4) Uani 1 1 d . . . H11 H 0.5842 1.1423 0.2743 0.032 Uiso 1 1 calc R . . C2 C 0.7610(3) 0.74817(18) 0.50467(10) 0.0225(3) Uani 1 1 d . . . C1 C 0.9393(3) 0.81059(17) 0.53143(10) 0.0217(3) Uani 1 1 d . . . C8 C 0.4588(3) 0.88710(18) 0.35689(11) 0.0238(4) Uani 1 1 d . . . C21 C 0.6138(3) 0.82154(18) 0.18571(11) 0.0262(4) Uani 1 1 d . . . H21 H 0.7251 0.8160 0.2339 0.031 Uiso 1 1 calc R . . C3 C 0.7475(3) 0.59588(19) 0.55579(11) 0.0268(4) Uani 1 1 d . . . H3 H 0.6232 0.5537 0.5407 0.032 Uiso 1 1 calc R . . C25 C 0.2189(3) 0.88718(17) 0.12110(10) 0.0246(4) Uani 1 1 d . . . H25 H 0.0579 0.9259 0.1254 0.030 Uiso 1 1 calc R . . C9 C 0.2933(2) 0.95043(17) 0.27145(10) 0.0212(3) Uani 1 1 d . . . C10 C 0.2660(3) 1.12656(18) 0.22865(10) 0.0218(3) Uani 1 1 d . . . C13 C 0.2247(3) 1.44196(19) 0.13560(12) 0.0308(4) Uani 1 1 d . . . H13 H 0.2115 1.5493 0.1034 0.037 Uiso 1 1 calc R . . C6 C 1.1070(3) 0.71863(18) 0.60363(11) 0.0259(4) Uani 1 1 d . . . H6 H 1.2299 0.7604 0.6204 0.031 Uiso 1 1 calc R . . C12 C 0.4247(3) 1.35707(19) 0.19069(12) 0.0299(4) Uani 1 1 d . . . H12 H 0.5484 1.4065 0.1970 0.036 Uiso 1 1 calc R . . C7 C 0.5953(3) 0.83294(17) 0.42488(10) 0.0234(4) Uani 1 1 d . . . C14 C 0.0434(3) 1.37006(19) 0.12744(11) 0.0291(4) Uani 1 1 d . . . H14 H -0.0946 1.4283 0.0899 0.035 Uiso 1 1 calc R . . C23 C 0.5261(3) 0.77852(18) 0.03748(11) 0.0293(4) Uani 1 1 d . . . H23 H 0.5762 0.7443 -0.0153 0.035 Uiso 1 1 calc R . . C4 C 0.9132(3) 0.50573(19) 0.62820(11) 0.0296(4) Uani 1 1 d . . . H4 H 0.9025 0.4023 0.6622 0.036 Uiso 1 1 calc R . . C15 C 0.0631(3) 1.21338(18) 0.17397(11) 0.0252(4) Uani 1 1 d . . . H15 H -0.0623 1.1648 0.1686 0.030 Uiso 1 1 calc R . . C22 C 0.6857(3) 0.77015(19) 0.10863(12) 0.0307(4) Uani 1 1 d . . . H22 H 0.8460 0.7289 0.1049 0.037 Uiso 1 1 calc R . . C5 C 1.0943(3) 0.56682(19) 0.65078(11) 0.0295(4) Uani 1 1 d . . . H5 H 1.2106 0.5040 0.6990 0.035 Uiso 1 1 calc R . . H1O H 0.0217 0.9445 0.3622 0.100(9) Uiso 1 1 d 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 0.0209(6) 0.0316(6) 0.0228(6) -0.0081(5) 0.0016(4) -0.0105(5) N1 0.0194(7) 0.0248(7) 0.0217(7) -0.0085(5) 0.0002(5) -0.0052(5) C24 0.0329(9) 0.0264(8) 0.0226(8) -0.0076(7) -0.0029(6) -0.0062(7) C20 0.0222(8) 0.0188(7) 0.0214(8) -0.0040(6) 0.0000(6) -0.0049(6) C11 0.0235(8) 0.0300(9) 0.0257(9) -0.0089(7) -0.0014(6) -0.0055(7) C2 0.0228(8) 0.0262(8) 0.0192(8) -0.0082(6) 0.0001(6) -0.0049(6) C1 0.0238(8) 0.0241(8) 0.0178(8) -0.0072(6) 0.0015(6) -0.0053(6) C8 0.0233(8) 0.0259(8) 0.0244(9) -0.0091(7) 0.0015(6) -0.0082(6) C21 0.0233(8) 0.0267(8) 0.0291(9) -0.0094(7) -0.0013(6) -0.0053(7) C3 0.0287(9) 0.0296(9) 0.0245(9) -0.0083(7) -0.0006(6) -0.0119(7) C25 0.0236(8) 0.0241(8) 0.0249(8) -0.0073(7) -0.0020(6) -0.0022(6) C9 0.0182(8) 0.0257(8) 0.0197(8) -0.0059(6) -0.0008(6) -0.0067(6) C10 0.0219(8) 0.0271(8) 0.0185(8) -0.0102(6) 0.0019(6) -0.0049(6) C13 0.0354(10) 0.0227(8) 0.0322(9) -0.0069(7) 0.0061(7) -0.0044(7) C6 0.0254(9) 0.0290(9) 0.0239(8) -0.0090(7) -0.0048(6) -0.0057(7) C12 0.0311(9) 0.0299(9) 0.0331(9) -0.0129(7) 0.0044(7) -0.0117(7) C7 0.0222(8) 0.0261(8) 0.0235(8) -0.0081(7) 0.0004(6) -0.0084(6) C14 0.0268(9) 0.0287(9) 0.0278(9) -0.0077(7) 0.0005(7) 0.0015(7) C23 0.0373(10) 0.0265(9) 0.0284(9) -0.0130(7) 0.0078(7) -0.0097(7) C4 0.0369(10) 0.0247(8) 0.0252(9) -0.0047(7) -0.0021(7) -0.0067(7) C15 0.0225(8) 0.0297(9) 0.0243(8) -0.0100(7) 0.0009(6) -0.0051(7) C22 0.0242(9) 0.0313(9) 0.0398(10) -0.0160(8) 0.0071(7) -0.0057(7) C5 0.0325(9) 0.0283(9) 0.0248(9) -0.0059(7) -0.0076(6) -0.0031(7) _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 C9 1.4341(17) . ? N1 N1 1.262(2) 2_776 ? N1 C1 1.4281(19) . ? C24 C23 1.384(2) . ? C24 C25 1.386(2) . ? C20 C21 1.389(2) . ? C20 C25 1.393(2) . ? C20 C9 1.537(2) . ? C11 C10 1.388(2) . ? C11 C12 1.387(2) . ? C2 C3 1.399(2) . ? C2 C1 1.404(2) . ? C2 C7 1.444(2) . ? C1 C6 1.396(2) . ? C8 C7 1.198(2) . ? C8 C9 1.484(2) . ? C21 C22 1.392(2) . ? C3 C4 1.386(2) . ? C9 C10 1.537(2) . ? C10 C15 1.396(2) . ? C13 C12 1.382(2) . ? C13 C14 1.385(2) . ? C6 C5 1.382(2) . ? C14 C15 1.386(2) . ? C23 C22 1.383(2) . ? C4 C5 1.385(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 N1 N1 C1 114.30(14) 2_776 . ? C23 C24 C25 120.54(14) . . ? C21 C20 C25 119.09(14) . . ? C21 C20 C9 122.15(13) . . ? C25 C20 C9 118.61(13) . . ? C10 C11 C12 120.46(14) . . ? C3 C2 C1 118.56(13) . . ? C3 C2 C7 118.64(13) . . ? C1 C2 C7 122.78(13) . . ? C6 C1 C2 120.17(14) . . ? C6 C1 N1 122.09(13) . . ? C2 C1 N1 117.56(12) . . ? C7 C8 C9 178.23(16) . . ? C20 C21 C22 120.07(15) . . ? C4 C3 C2 120.86(14) . . ? C24 C25 C20 120.38(15) . . ? O1 C9 C8 109.89(11) . . ? O1 C9 C20 106.49(11) . . ? C8 C9 C20 111.02(12) . . ? O1 C9 C10 110.75(12) . . ? C8 C9 C10 111.40(12) . . ? C20 C9 C10 107.15(11) . . ? C11 C10 C15 118.99(14) . . ? C11 C10 C9 121.44(13) . . ? C15 C10 C9 119.39(13) . . ? C12 C13 C14 119.77(15) . . ? C5 C6 C1 120.04(14) . . ? C13 C12 C11 120.28(15) . . ? C8 C7 C2 172.36(16) . . ? C13 C14 C15 120.13(14) . . ? C22 C23 C24 119.23(15) . . ? C5 C4 C3 119.83(15) . . ? C14 C15 C10 120.37(15) . . ? C23 C22 C21 120.68(15) . . ? C6 C5 C4 120.42(14) . . ? _diffrn_measured_fraction_theta_max 0.860 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.860 _refine_diff_density_max 0.197 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.046 data_1.2DMSO _database_code_CSD 196891 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-{2-[2-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-phenylazo]-phenyl} -1,1-diphenyl-prop-2-yn-1-ol DMSO solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H30 N2 O2.2(C2 H6 S O)' _chemical_formula_sum 'C46 H42 N2 O4 S2' _chemical_formula_weight 750.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.7388(3) _cell_length_b 12.0389(2) _cell_length_c 16.7993(3) _cell_angle_alpha 76.2520(10) _cell_angle_beta 72.5340(10) _cell_angle_gamma 61.2400(10) _cell_volume 1972.92(7) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour 'orange/red (dichromic)' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.181 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9476 _exptl_absorpt_correction_T_max 0.9646 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method '\phi + w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9553 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1320 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 28.32 _reflns_number_total 9553 _reflns_number_gt 4543 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XSeed _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^)+(0.0568P)^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 9553 _refine_ls_number_parameters 530 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1481 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1287 _refine_ls_wR_factor_gt 0.1046 _refine_ls_goodness_of_fit_ref 0.893 _refine_ls_restrained_S_all 0.893 _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 S1G S 0.59206(6) 0.42155(6) 0.21912(4) 0.04190(19) Uani 1 1 d . . . S2G S 0.93983(7) 0.58260(7) 0.24032(5) 0.0408(2) Uani 0.85 1 d P . . O1 O 0.90658(16) 0.11401(15) 0.12475(8) 0.0288(4) Uani 1 1 d . . . O1' O 1.60805(15) -0.14309(15) 0.36481(9) 0.0288(4) Uani 1 1 d . . . O1G O 0.67906(15) 0.33377(14) 0.15245(8) 0.0373(4) Uani 1 1 d . . . N1 N 1.02116(17) 0.44918(15) 0.02354(9) 0.0259(4) Uani 1 1 d . . . N1' N 1.48145(17) -0.45781(16) 0.47078(9) 0.0276(4) Uani 1 1 d . . . C6 C 1.2236(2) 0.4797(2) 0.00030(12) 0.0252(5) Uani 1 1 d . . . H6 H 1.1891 0.5555 -0.0363 0.030 Uiso 1 1 calc R . . C20 C 1.1116(2) -0.06075(19) 0.14751(11) 0.0206(5) Uani 1 1 d . . . C10 C 0.94441(19) 0.06207(19) 0.26654(11) 0.0209(5) Uani 1 1 d . . . C4' C 1.0875(2) -0.3219(2) 0.45000(12) 0.0291(5) Uani 1 1 d . . . H4' H 0.9994 -0.2913 0.4432 0.035 Uiso 1 1 calc R . . C7' C 1.3687(2) -0.23057(19) 0.37383(11) 0.0229(5) Uani 1 1 d . . . C10' C 1.4032(2) 0.0418(2) 0.35441(11) 0.0228(5) Uani 1 1 d . . . C8 C 1.0713(2) 0.15778(19) 0.14846(11) 0.0238(5) Uani 1 1 d . . . C25' C 1.5356(2) -0.1229(2) 0.17082(11) 0.0262(5) Uani 1 1 d . . . H25' H 1.4891 -0.1739 0.1906 0.031 Uiso 1 1 calc R . . C8' C 1.4293(2) -0.1689(2) 0.34609(11) 0.0239(5) Uani 1 1 d . . . C3' C 1.1622(2) -0.2575(2) 0.40584(11) 0.0266(5) Uani 1 1 d . . . H3' H 1.1246 -0.1823 0.3694 0.032 Uiso 1 1 calc R . . C9 C 1.0053(2) 0.07158(19) 0.17190(11) 0.0215(5) Uani 1 1 d . . . C1' C 1.3462(2) -0.41407(19) 0.46792(11) 0.0220(5) Uani 1 1 d . . . C21' C 1.62152(19) 0.0058(2) 0.19725(12) 0.0255(5) Uani 1 1 d . . . H21' H 1.6328 0.0447 0.2355 0.031 Uiso 1 1 calc R . . C9' C 1.5012(2) -0.08813(19) 0.32232(11) 0.0223(5) Uani 1 1 d . . . C22' C 1.6727(2) 0.0243(2) 0.11196(12) 0.0292(5) Uani 1 1 d . . . H22' H 1.7207 0.0739 0.0921 0.035 Uiso 1 1 calc R . . C3 C 1.3247(2) 0.2588(2) 0.10759(12) 0.0267(5) Uani 1 1 d . . . H3 H 1.3596 0.1835 0.1445 0.032 Uiso 1 1 calc R . . O2G O 0.83304(17) 0.64248(17) 0.31418(10) 0.0600(6) Uani 1 1 d . . . C4 C 1.3977(2) 0.3272(2) 0.07137(12) 0.0289(5) Uani 1 1 d . . . H4 H 1.4819 0.2992 0.0836 0.035 Uiso 1 1 calc R . . C7 C 1.1277(2) 0.2232(2) 0.12419(11) 0.0234(5) Uani 1 1 d . . . C5 C 1.3470(2) 0.4371(2) 0.01695(12) 0.0271(5) Uani 1 1 d . . . H5 H 1.3979 0.4832 -0.0089 0.032 Uiso 1 1 calc R . . C1 C 1.1498(2) 0.41182(19) 0.03701(11) 0.0223(5) Uani 1 1 d . . . C2 C 1.2002(2) 0.29873(19) 0.09072(11) 0.0216(5) Uani 1 1 d . . . C11' C 1.4311(2) 0.0902(2) 0.40940(11) 0.0261(5) Uani 1 1 d . . . H11' H 1.5120 0.0421 0.4283 0.031 Uiso 1 1 calc R . . C2' C 1.2921(2) -0.30181(19) 0.41420(11) 0.0227(5) Uani 1 1 d . . . C25 C 1.2155(2) -0.1296(2) 0.19003(12) 0.0260(5) Uani 1 1 d . . . H25 H 1.2204 -0.0934 0.2327 0.031 Uiso 1 1 calc R . . C15 C 0.9583(2) 0.1203(2) 0.32240(12) 0.0286(5) Uani 1 1 d . . . H15 H 1.0063 0.1699 0.3023 0.034 Uiso 1 1 calc R . . C13' C 1.2244(2) 0.2804(2) 0.40894(12) 0.0312(6) Uani 1 1 d . . . H13' H 1.1641 0.3621 0.4270 0.037 Uiso 1 1 calc R . . C14' C 1.1954(2) 0.2323(2) 0.35409(13) 0.0327(6) Uani 1 1 d . . . H14' H 1.1147 0.2809 0.3349 0.039 Uiso 1 1 calc R . . C12' C 1.3413(2) 0.2090(2) 0.43706(12) 0.0308(6) Uani 1 1 d . . . H12' H 1.3606 0.2409 0.4754 0.037 Uiso 1 1 calc R . . C20' C 1.55360(19) -0.06923(19) 0.22732(11) 0.0212(5) Uani 1 1 d . . . C23 C 1.3073(2) -0.3019(2) 0.10691(13) 0.0305(6) Uani 1 1 d . . . H23 H 1.3736 -0.3845 0.0934 0.037 Uiso 1 1 calc R . . C21 C 1.1078(2) -0.1137(2) 0.08424(11) 0.0269(5) Uani 1 1 d . . . H21 H 1.0373 -0.0680 0.0551 0.032 Uiso 1 1 calc R . . C11 C 0.8736(2) -0.01037(19) 0.29735(12) 0.0250(5) Uani 1 1 d . . . H11 H 0.8640 -0.0516 0.2598 0.030 Uiso 1 1 calc R . . C6' C 1.2693(2) -0.4777(2) 0.51317(12) 0.0263(5) Uani 1 1 d . . . H6' H 1.3056 -0.5528 0.5499 0.032 Uiso 1 1 calc R . . C12 C 0.8171(2) -0.0230(2) 0.38220(12) 0.0311(6) Uani 1 1 d . . . H12 H 0.7682 -0.0718 0.4024 0.037 Uiso 1 1 calc R . . C24 C 1.3112(2) -0.2500(2) 0.17043(13) 0.0306(5) Uani 1 1 d . . . H24 H 1.3799 -0.2973 0.2008 0.037 Uiso 1 1 calc R . . C22 C 1.2067(2) -0.2336(2) 0.06295(12) 0.0331(6) Uani 1 1 d . . . H22 H 1.2051 -0.2684 0.0183 0.040 Uiso 1 1 calc R . . C23' C 1.6539(2) -0.0297(2) 0.05572(12) 0.0329(6) Uani 1 1 d . . . H23' H 1.6881 -0.0165 -0.0028 0.039 Uiso 1 1 calc R . . C5' C 1.1404(2) -0.4310(2) 0.50427(12) 0.0290(5) Uani 1 1 d . . . H5' H 1.0878 -0.4737 0.5354 0.035 Uiso 1 1 calc R . . C24' C 1.5852(2) -0.1028(2) 0.08501(12) 0.0321(6) Uani 1 1 d . . . H24' H 1.5717 -0.1396 0.0465 0.038 Uiso 1 1 calc R . . C15' C 1.2839(2) 0.1136(2) 0.32738(12) 0.0284(5) Uani 1 1 d . . . H15' H 1.2631 0.0809 0.2903 0.034 Uiso 1 1 calc R . . C14 C 0.9026(2) 0.1071(2) 0.40752(13) 0.0384(6) Uani 1 1 d . . . H14 H 0.9131 0.1473 0.4453 0.046 Uiso 1 1 calc R . . C13 C 0.8317(2) 0.0355(2) 0.43750(13) 0.0354(6) Uani 1 1 d . . . H13 H 0.7934 0.0266 0.4957 0.042 Uiso 1 1 calc R . . C4G C 0.9074(3) 0.6953(3) 0.15217(16) 0.0459(7) Uani 1 1 d D . . C3G C 1.0863(3) 0.5804(4) 0.24848(18) 0.0592(9) Uani 1 1 d D . . C1G C 0.5700(3) 0.3222(3) 0.31314(16) 0.0747(11) Uani 1 1 d . . . H1G1 H 0.5205 0.2793 0.3074 0.112 Uiso 1 1 calc R . . H1G2 H 0.5201 0.3741 0.3601 0.112 Uiso 1 1 calc R . . H1G3 H 0.6572 0.2582 0.3239 0.112 Uiso 1 1 calc R . . C2G C 0.6931(3) 0.4709(3) 0.24731(17) 0.0681(9) Uani 1 1 d . . . H2G1 H 0.7714 0.3957 0.2627 0.102 Uiso 1 1 calc R . . H2G2 H 0.6420 0.5206 0.2952 0.102 Uiso 1 1 calc R . . H2G3 H 0.7219 0.5235 0.1996 0.102 Uiso 1 1 calc R . . S3G S 0.9258(4) 0.6871(4) 0.2487(2) 0.0344(10) Uani 0.15 1 d P . . H1O H 0.841(3) 0.183(3) 0.1431(16) 0.066(9) Uiso 1 1 d . . . H4G3 H 0.9792(19) 0.671(2) 0.1025(11) 0.047(7) Uiso 1 1 d D . . H1'O H 1.676(3) -0.204(3) 0.3404(15) 0.066(9) Uiso 1 1 d . . . H4G2 H 0.8234(19) 0.721(2) 0.1371(15) 0.068(9) Uiso 1 1 d D . . H3G2 H 1.122(2) 0.520(2) 0.2974(13) 0.074(9) Uiso 1 1 d D . . H4G1 H 0.897(3) 0.778(2) 0.1618(17) 0.084(11) Uiso 1 1 d D . . H3G1 H 1.054(4) 0.668(2) 0.261(2) 0.142(17) Uiso 1 1 d D . . H3G3 H 1.162(2) 0.540(3) 0.2036(16) 0.106(12) Uiso 1 1 d 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 S1G 0.0348(4) 0.0293(4) 0.0512(4) -0.0054(3) -0.0061(3) -0.0076(3) S2G 0.0299(4) 0.0304(5) 0.0536(5) -0.0016(3) -0.0027(3) -0.0118(4) O1 0.0257(9) 0.0309(10) 0.0280(8) -0.0024(7) -0.0130(7) -0.0074(8) O1' 0.0252(9) 0.0317(10) 0.0276(8) -0.0005(7) -0.0121(7) -0.0086(8) O1G 0.0334(10) 0.0324(10) 0.0342(8) -0.0036(7) -0.0026(7) -0.0082(8) N1 0.0244(10) 0.0213(11) 0.0295(10) 0.0037(7) -0.0085(8) -0.0096(9) N1' 0.0241(11) 0.0263(11) 0.0286(10) 0.0037(7) -0.0065(8) -0.0108(9) C6 0.0244(13) 0.0218(12) 0.0273(11) -0.0012(9) -0.0047(9) -0.0098(11) C20 0.0229(12) 0.0211(12) 0.0177(10) 0.0000(8) -0.0011(8) -0.0125(10) C10 0.0170(11) 0.0199(12) 0.0221(10) 0.0000(8) -0.0045(8) -0.0061(10) C4' 0.0216(12) 0.0316(14) 0.0318(12) -0.0032(10) -0.0071(9) -0.0095(11) C7' 0.0240(12) 0.0207(12) 0.0188(10) 0.0002(8) -0.0065(9) -0.0058(11) C10' 0.0240(12) 0.0288(13) 0.0174(10) 0.0013(9) -0.0019(8) -0.0162(11) C8 0.0252(13) 0.0213(12) 0.0188(10) 0.0000(8) -0.0051(9) -0.0063(11) C25' 0.0243(13) 0.0296(13) 0.0274(11) -0.0018(9) -0.0060(9) -0.0143(11) C8' 0.0235(12) 0.0234(12) 0.0200(10) 0.0003(8) -0.0049(8) -0.0078(11) C3' 0.0284(13) 0.0252(13) 0.0250(11) 0.0002(9) -0.0067(9) -0.0116(11) C9 0.0223(12) 0.0221(12) 0.0198(10) 0.0014(8) -0.0086(8) -0.0089(10) C1' 0.0219(12) 0.0223(12) 0.0200(10) -0.0020(8) -0.0020(8) -0.0101(10) C21' 0.0195(12) 0.0282(13) 0.0279(11) -0.0032(9) -0.0065(9) -0.0090(11) C9' 0.0209(12) 0.0261(12) 0.0202(10) 0.0022(8) -0.0074(8) -0.0112(10) C22' 0.0265(13) 0.0302(14) 0.0287(12) 0.0030(9) -0.0038(9) -0.0150(11) C3 0.0301(13) 0.0253(13) 0.0243(11) -0.0001(9) -0.0073(9) -0.0124(11) O2G 0.0403(11) 0.0505(12) 0.0442(10) 0.0076(8) 0.0118(8) -0.0030(9) C4 0.0213(12) 0.0317(14) 0.0324(12) -0.0048(10) -0.0075(9) -0.0092(11) C7 0.0239(12) 0.0217(12) 0.0205(11) -0.0002(8) -0.0069(9) -0.0068(11) C5 0.0249(13) 0.0256(13) 0.0315(12) -0.0054(9) -0.0007(9) -0.0139(11) C1 0.0226(12) 0.0220(12) 0.0211(10) -0.0028(8) -0.0026(8) -0.0101(10) C2 0.0235(12) 0.0197(12) 0.0215(10) -0.0031(8) -0.0020(8) -0.0107(10) C11' 0.0290(13) 0.0323(14) 0.0196(10) 0.0009(9) -0.0062(9) -0.0167(11) C2' 0.0237(13) 0.0221(12) 0.0182(10) -0.0010(8) -0.0019(8) -0.0090(10) C25 0.0248(13) 0.0255(13) 0.0310(11) -0.0061(9) -0.0082(9) -0.0110(11) C15 0.0282(13) 0.0326(14) 0.0269(11) -0.0053(9) -0.0025(9) -0.0159(11) C13' 0.0324(14) 0.0271(13) 0.0308(12) -0.0067(10) 0.0010(10) -0.0136(12) C14' 0.0275(13) 0.0293(14) 0.0402(13) -0.0055(10) -0.0092(10) -0.0098(12) C12' 0.0389(15) 0.0363(14) 0.0220(11) -0.0048(9) -0.0024(10) -0.0220(13) C20' 0.0162(11) 0.0230(12) 0.0233(10) 0.0003(8) -0.0050(8) -0.0086(10) C23 0.0253(13) 0.0239(13) 0.0357(12) -0.0080(10) 0.0023(10) -0.0088(11) C21 0.0361(14) 0.0253(13) 0.0198(10) 0.0023(9) -0.0081(9) -0.0150(11) C11 0.0212(12) 0.0256(13) 0.0271(11) -0.0015(9) -0.0069(9) -0.0093(10) C6' 0.0291(13) 0.0225(12) 0.0259(11) 0.0009(9) -0.0068(9) -0.0115(11) C12 0.0225(13) 0.0302(14) 0.0334(12) 0.0040(10) -0.0018(9) -0.0119(11) C24 0.0240(13) 0.0265(13) 0.0430(13) -0.0045(10) -0.0112(10) -0.0099(11) C22 0.0486(16) 0.0291(14) 0.0216(11) -0.0063(9) 0.0006(10) -0.0203(13) C23' 0.0259(13) 0.0411(15) 0.0215(11) 0.0007(10) -0.0007(9) -0.0114(12) C5' 0.0287(14) 0.0308(14) 0.0292(12) -0.0037(9) -0.0009(9) -0.0175(11) C24' 0.0308(14) 0.0431(15) 0.0236(11) -0.0068(10) -0.0061(9) -0.0160(12) C15' 0.0285(13) 0.0319(14) 0.0291(11) -0.0052(10) -0.0071(9) -0.0155(12) C14 0.0433(16) 0.0490(16) 0.0263(12) -0.0135(11) -0.0006(10) -0.0230(14) C13 0.0305(14) 0.0430(15) 0.0237(12) -0.0026(10) 0.0021(10) -0.0144(12) C4G 0.0337(17) 0.056(2) 0.0374(15) -0.0077(13) -0.0046(12) -0.0126(15) C3G 0.0421(19) 0.082(3) 0.0475(18) 0.0099(17) -0.0176(14) -0.0254(19) C1G 0.097(3) 0.055(2) 0.0557(18) -0.0162(15) 0.0262(16) -0.040(2) C2G 0.090(2) 0.071(2) 0.0642(18) -0.0127(16) -0.0167(16) -0.049(2) S3G 0.052(3) 0.018(2) 0.032(2) -0.0029(15) -0.0003(17) -0.019(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 S1G O1G 1.5005(15) . ? S1G C2G 1.770(3) . ? S1G C1G 1.774(3) . ? S2G O2G 1.5008(16) . ? S2G C4G 1.751(3) . ? S2G C3G 1.753(3) . ? O1 C9 1.421(2) . ? O1' C9' 1.427(2) . ? N1 N1 1.249(3) 2_765 ? N1 C1 1.427(3) . ? N1' N1' 1.242(3) 2_846 ? N1' C1' 1.425(3) . ? C6 C5 1.379(3) . ? C6 C1 1.385(3) . ? C20 C21 1.384(3) . ? C20 C25 1.398(3) . ? C20 C9 1.534(3) . ? C10 C15 1.383(3) . ? C10 C11 1.394(3) . ? C10 C9 1.537(2) . ? C4' C3' 1.382(3) . ? C4' C5' 1.389(3) . ? C7' C8' 1.191(3) . ? C7' C2' 1.450(3) . ? C10' C11' 1.386(3) . ? C10' C15' 1.395(3) . ? C10' C9' 1.535(3) . ? C8 C7 1.189(3) . ? C8 C9 1.493(3) . ? C25' C20' 1.381(3) . ? C25' C24' 1.393(3) . ? C8' C9' 1.489(3) . ? C3' C2' 1.393(3) . ? C1' C6' 1.398(3) . ? C1' C2' 1.408(3) . ? C21' C22' 1.387(3) . ? C21' C20' 1.393(3) . ? C9' C20' 1.533(2) . ? C22' C23' 1.385(3) . ? C3 C4 1.382(3) . ? C3 C2 1.398(3) . ? O2G S3G 1.498(4) . ? C4 C5 1.391(3) . ? C7 C2 1.442(3) . ? C1 C2 1.407(3) . ? C11' C12' 1.394(3) . ? C25 C24 1.382(3) . ? C15 C14 1.389(3) . ? C13' C12' 1.381(3) . ? C13' C14' 1.391(3) . ? C14' C15' 1.385(3) . ? C23 C24 1.380(3) . ? C23 C22 1.385(3) . ? C21 C22 1.394(3) . ? C11 C12 1.386(3) . ? C6' C5' 1.379(3) . ? C12 C13 1.382(3) . ? C23' C24' 1.381(3) . ? C14 C13 1.387(3) . ? C4G S3G 1.674(5) . ? C3G S3G 1.694(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1G S1G C2G 107.26(12) . . ? O1G S1G C1G 105.97(11) . . ? C2G S1G C1G 97.55(15) . . ? O2G S2G C4G 107.04(12) . . ? O2G S2G C3G 107.43(15) . . ? C4G S2G C3G 99.24(15) . . ? N1 N1 C1 114.0(2) 2_765 . ? N1' N1' C1' 114.3(2) 2_846 . ? C5 C6 C1 119.94(19) . . ? C21 C20 C25 119.03(19) . . ? C21 C20 C9 121.79(18) . . ? C25 C20 C9 119.17(18) . . ? C15 C10 C11 118.72(18) . . ? C15 C10 C9 123.10(18) . . ? C11 C10 C9 118.17(18) . . ? C3' C4' C5' 120.4(2) . . ? C8' C7' C2' 175.3(2) . . ? C11' C10' C15' 119.0(2) . . ? C11' C10' C9' 121.39(19) . . ? C15' C10' C9' 119.63(19) . . ? C7 C8 C9 175.2(2) . . ? C20' C25' C24' 120.5(2) . . ? C7' C8' C9' 172.8(2) . . ? C4' C3' C2' 120.62(19) . . ? O1 C9 C8 110.25(16) . . ? O1 C9 C20 107.19(16) . . ? C8 C9 C20 107.56(16) . . ? O1 C9 C10 110.63(16) . . ? C8 C9 C10 111.51(16) . . ? C20 C9 C10 109.55(15) . . ? C6' C1' C2' 120.30(19) . . ? C6' C1' N1' 123.67(18) . . ? C2' C1' N1' 116.02(17) . . ? C22' C21' C20' 120.5(2) . . ? O1' C9' C8' 109.41(16) . . ? O1' C9' C20' 110.20(15) . . ? C8' C9' C20' 112.94(17) . . ? O1' C9' C10' 107.15(17) . . ? C8' C9' C10' 107.37(16) . . ? C20' C9' C10' 109.58(15) . . ? C23' C22' C21' 120.0(2) . . ? C4 C3 C2 121.02(19) . . ? S3G O2G S2G 48.20(15) . . ? C3 C4 C5 119.6(2) . . ? C8 C7 C2 176.8(2) . . ? C6 C5 C4 120.52(19) . . ? C6 C1 C2 120.6(2) . . ? C6 C1 N1 123.66(18) . . ? C2 C1 N1 115.74(17) . . ? C3 C2 C1 118.28(18) . . ? C3 C2 C7 121.06(18) . . ? C1 C2 C7 120.60(19) . . ? C10' C11' C12' 120.4(2) . . ? C3' C2' C1' 118.68(18) . . ? C3' C2' C7' 121.61(18) . . ? C1' C2' C7' 119.56(19) . . ? C24 C25 C20 120.4(2) . . ? C10 C15 C14 120.7(2) . . ? C12' C13' C14' 119.7(2) . . ? C15' C14' C13' 120.1(2) . . ? C13' C12' C11' 120.2(2) . . ? C25' C20' C21' 119.06(18) . . ? C25' C20' C9' 122.66(18) . . ? C21' C20' C9' 118.28(18) . . ? C24 C23 C22 120.0(2) . . ? C20 C21 C22 120.4(2) . . ? C12 C11 C10 120.8(2) . . ? C5' C6' C1' 119.80(19) . . ? C13 C12 C11 120.1(2) . . ? C23 C24 C25 120.3(2) . . ? C23 C22 C21 119.9(2) . . ? C24' C23' C22' 119.74(19) . . ? C6' C5' C4' 120.21(19) . . ? C23' C24' C25' 120.2(2) . . ? C14' C15' C10' 120.6(2) . . ? C13 C14 C15 120.2(2) . . ? C12 C13 C14 119.6(2) . . ? S3G C4G S2G 41.83(14) . . ? S3G C3G S2G 41.58(16) . . ? O2G S3G C4G 111.2(3) . . ? O2G S3G C3G 110.6(3) . . ? C4G S3G C3G 104.8(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 C2' C7' C8' C9' 5(4) . . . . ? C5' C4' C3' C2' 0.8(3) . . . . ? C7 C8 C9 O1 -67(3) . . . . ? C7 C8 C9 C20 49(3) . . . . ? C7 C8 C9 C10 169(3) . . . . ? C21 C20 C9 O1 5.6(2) . . . . ? C25 C20 C9 O1 -174.71(16) . . . . ? C21 C20 C9 C8 -113.0(2) . . . . ? C25 C20 C9 C8 66.7(2) . . . . ? C21 C20 C9 C10 125.67(19) . . . . ? C25 C20 C9 C10 -54.6(2) . . . . ? C15 C10 C9 O1 -127.1(2) . . . . ? C11 C10 C9 O1 53.9(2) . . . . ? C15 C10 C9 C8 -4.0(3) . . . . ? C11 C10 C9 C8 176.98(18) . . . . ? C15 C10 C9 C20 115.0(2) . . . . ? C11 C10 C9 C20 -64.1(2) . . . . ? N1' N1' C1' C6' -14.0(3) 2_846 . . . ? N1' N1' C1' C2' 167.5(2) 2_846 . . . ? C7' C8' C9' O1' 62.0(18) . . . . ? C7' C8' C9' C20' -174.9(17) . . . . ? C7' C8' C9' C10' -54.0(19) . . . . ? C11' C10' C9' O1' 4.7(2) . . . . ? C15' C10' C9' O1' -175.83(16) . . . . ? C11' C10' C9' C8' 122.2(2) . . . . ? C15' C10' C9' C8' -58.4(2) . . . . ? C11' C10' C9' C20' -114.8(2) . . . . ? C15' C10' C9' C20' 64.6(2) . . . . ? C20' C21' C22' C23' 1.5(3) . . . . ? C4G S2G O2G S3G -52.4(3) . . . . ? C3G S2G O2G S3G 53.4(3) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C9 C8 C7 C2 -11(6) . . . . ? C1 C6 C5 C4 -0.9(3) . . . . ? C3 C4 C5 C6 1.3(3) . . . . ? C5 C6 C1 C2 -0.6(3) . . . . ? C5 C6 C1 N1 179.75(18) . . . . ? N1 N1 C1 C6 -1.2(3) 2_765 . . . ? N1 N1 C1 C2 179.1(2) 2_765 . . . ? C4 C3 C2 C1 -1.1(3) . . . . ? C4 C3 C2 C7 176.02(19) . . . . ? C6 C1 C2 C3 1.6(3) . . . . ? N1 C1 C2 C3 -178.73(17) . . . . ? C6 C1 C2 C7 -175.57(18) . . . . ? N1 C1 C2 C7 4.1(3) . . . . ? C8 C7 C2 C3 -87(4) . . . . ? C8 C7 C2 C1 90(4) . . . . ? C15' C10' C11' C12' -0.1(3) . . . . ? C9' C10' C11' C12' 179.33(16) . . . . ? C4' C3' C2' C1' 0.6(3) . . . . ? C4' C3' C2' C7' -174.99(19) . . . . ? C6' C1' C2' C3' -1.4(3) . . . . ? N1' C1' C2' C3' 177.16(17) . . . . ? C6' C1' C2' C7' 174.25(18) . . . . ? N1' C1' C2' C7' -7.2(3) . . . . ? C8' C7' C2' C3' 99(3) . . . . ? C8' C7' C2' C1' -76(3) . . . . ? C21 C20 C25 C24 -1.5(3) . . . . ? C9 C20 C25 C24 178.79(17) . . . . ? C11 C10 C15 C14 -0.1(3) . . . . ? C9 C10 C15 C14 -179.13(19) . . . . ? C12' C13' C14' C15' -0.5(3) . . . . ? C14' C13' C12' C11' 1.2(3) . . . . ? C10' C11' C12' C13' -0.9(3) . . . . ? C24' C25' C20' C21' 0.3(3) . . . . ? C24' C25' C20' C9' 179.98(18) . . . . ? C22' C21' C20' C25' -1.3(3) . . . . ? C22' C21' C20' C9' 179.00(18) . . . . ? O1' C9' C20' C25' 122.4(2) . . . . ? C8' C9' C20' C25' -0.3(3) . . . . ? C10' C9' C20' C25' -120.0(2) . . . . ? O1' C9' C20' C21' -57.9(2) . . . . ? C8' C9' C20' C21' 179.36(18) . . . . ? C10' C9' C20' C21' 59.7(2) . . . . ? C25 C20 C21 C22 -0.4(3) . . . . ? C9 C20 C21 C22 179.28(17) . . . . ? C15 C10 C11 C12 0.6(3) . . . . ? C9 C10 C11 C12 179.65(18) . . . . ? C2' C1' C6' C5' 0.8(3) . . . . ? N1' C1' C6' C5' -177.60(19) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C22 C23 C24 C25 -0.4(3) . . . . ? C20 C25 C24 C23 1.9(3) . . . . ? C24 C23 C22 C21 -1.5(3) . . . . ? C20 C21 C22 C23 1.9(3) . . . . ? C21' C22' C23' C24' -0.6(3) . . . . ? C1' C6' C5' C4' 0.6(3) . . . . ? C3' C4' C5' C6' -1.4(3) . . . . ? C22' C23' C24' C25' -0.4(3) . . . . ? C20' C25' C24' C23' 0.5(3) . . . . ? C13' C14' C15' C10' -0.6(3) . . . . ? C11' C10' C15' C14' 0.9(3) . . . . ? C9' C10' C15' C14' -178.58(17) . . . . ? C10 C15 C14 C13 -0.3(3) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C15 C14 C13 C12 0.2(4) . . . . ? O2G S2G C4G S3G 52.5(2) . . . . ? C3G S2G C4G S3G -59.1(3) . . . . ? O2G S2G C3G S3G -52.9(2) . . . . ? C4G S2G C3G S3G 58.4(2) . . . . ? S2G O2G S3G C4G 58.3(2) . . . . ? S2G O2G S3G C3G -57.8(2) . . . . ? S2G C4G S3G O2G -54.6(2) . . . . ? S2G C4G S3G C3G 65.0(2) . . . . ? S2G C3G S3G O2G 54.5(2) . . . . ? S2G C3G S3G C4G -65.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.229 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.058 data_2.DMSO _database_code_CSD 196892 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-{3-[3-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-phenylazo]-phenyl} -1,1-diphenyl-prop-2-yn-1-ol DMSO solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H30 N2 O2.C2 H6 S O' _chemical_formula_sum 'C44 H36 N2 O3 S' _chemical_formula_weight 672.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 29.7426(2) _cell_length_b 12.4739(2) _cell_length_c 9.5222(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.8750(10) _cell_angle_gamma 90.00 _cell_volume 3528.35(16) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour 'orange (dichromic)' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9477 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method '\phi + w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8137 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 28.34 _reflns_number_total 4379 _reflns_number_gt 2974 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XSeed _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^)+(0.0948P)^2^+0.5276P] 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 4379 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1628 _refine_ls_wR_factor_gt 0.1456 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.43991(4) 0.78675(11) 0.16333(12) 0.0411(3) Uani 1 1 d . . . N1 N 0.25793(5) 1.20346(11) 0.00299(13) 0.0331(3) Uani 1 1 d . . . C4 C 0.33165(6) 1.11740(14) 0.37291(16) 0.0349(4) Uani 1 1 d . . . H4 H 0.3497 1.0980 0.4541 0.042 Uiso 1 1 calc R . . C7 C 0.35391(6) 0.94926(14) 0.25596(15) 0.0320(4) Uani 1 1 d . . . C8 C 0.37485(6) 0.86744(14) 0.25325(16) 0.0334(4) Uani 1 1 d . . . C3 C 0.32937(5) 1.04905(13) 0.25576(16) 0.0313(4) Uani 1 1 d . . . C5 C 0.30794(6) 1.21264(14) 0.37133(17) 0.0376(4) Uani 1 1 d . . . H5 H 0.3087 1.2563 0.4531 0.045 Uiso 1 1 calc R . . C1 C 0.28129(5) 1.17861(13) 0.13436(15) 0.0308(4) Uani 1 1 d . . . C10 C 0.37399(5) 0.68001(13) 0.16857(15) 0.0310(4) Uani 1 1 d . . . C2 C 0.30325(5) 1.08093(13) 0.13688(16) 0.0316(4) Uani 1 1 d . . . H2 H 0.3006 1.0351 0.0572 0.038 Uiso 1 1 calc R . . C6 C 0.28297(6) 1.24543(14) 0.25169(17) 0.0356(4) Uani 1 1 d . . . H6 H 0.2674 1.3119 0.2500 0.043 Uiso 1 1 calc R . . C20 C 0.41657(5) 0.72754(13) 0.39352(16) 0.0318(4) Uani 1 1 d . . . C9 C 0.40210(5) 0.76786(14) 0.24517(16) 0.0312(4) Uani 1 1 d . . . C25 C 0.39106(6) 0.74796(15) 0.50801(16) 0.0379(4) Uani 1 1 d . . . H25 H 0.3653 0.7928 0.4972 0.045 Uiso 1 1 calc R . . C11 C 0.33167(5) 0.65326(14) 0.21415(16) 0.0343(4) Uani 1 1 d . . . H11 H 0.3198 0.6907 0.2910 0.041 Uiso 1 1 calc R . . C15 C 0.39041(6) 0.62516(15) 0.05535(18) 0.0410(4) Uani 1 1 d . . . H15 H 0.4192 0.6428 0.0232 0.049 Uiso 1 1 calc R . . C12 C 0.30667(6) 0.57208(14) 0.14783(18) 0.0380(4) Uani 1 1 d . . . H12 H 0.2779 0.5538 0.1799 0.046 Uiso 1 1 calc R . . C13 C 0.32351(6) 0.51783(14) 0.03548(19) 0.0415(4) Uani 1 1 d . . . H13 H 0.3065 0.4620 -0.0096 0.050 Uiso 1 1 calc R . . C23 C 0.44040(7) 0.64083(18) 0.65650(19) 0.0512(5) Uani 1 1 d . . . H23 H 0.4485 0.6107 0.7458 0.061 Uiso 1 1 calc R . . C14 C 0.36537(7) 0.54528(16) -0.0111(2) 0.0474(5) Uani 1 1 d . . . H14 H 0.3769 0.5089 -0.0893 0.057 Uiso 1 1 calc R . . C24 C 0.40268(7) 0.70354(17) 0.63907(18) 0.0464(5) Uani 1 1 d . . . H24 H 0.3845 0.7167 0.7164 0.056 Uiso 1 1 calc R . . C22 C 0.46639(7) 0.62193(19) 0.5440(2) 0.0552(5) Uani 1 1 d . . . H22 H 0.4932 0.5809 0.5574 0.066 Uiso 1 1 calc R . . C21 C 0.45444(3) 0.66137(6) 0.41173(9) 0.0460(5) Uani 1 1 d . . . H21 H 0.4718 0.6437 0.3338 0.055 Uiso 1 1 calc R . . S1 S 0.48375(3) 1.05270(6) 0.21095(9) 0.0465(3) Uani 0.50 1 d PR . . O2 O 0.50000(3) 0.93892(6) 0.25000(9) 0.0487(5) Uani 1 2 d SR . . H1O H 0.4557(8) 0.8381(19) 0.207(2) 0.060(7) Uiso 1 1 d . . . C1G C 0.5335(4) 1.1059(7) 0.1401(12) 0.077(3) Uani 0.50 1 d P . 1 C2G C 0.5154(4) 1.1256(9) 0.1282(10) 0.074(3) Uani 0.50 1 d P . 2 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 0.0366(7) 0.0524(9) 0.0349(7) -0.0047(6) 0.0082(5) -0.0097(6) N1 0.0375(8) 0.0314(7) 0.0300(7) 0.0006(6) -0.0013(5) 0.0016(6) C4 0.0429(9) 0.0325(9) 0.0287(8) 0.0038(7) -0.0050(6) -0.0035(7) C7 0.0370(9) 0.0339(9) 0.0249(8) 0.0014(6) -0.0027(6) -0.0020(7) C8 0.0374(9) 0.0356(10) 0.0269(8) 0.0029(7) -0.0033(6) -0.0046(8) C3 0.0354(9) 0.0290(9) 0.0294(8) 0.0036(6) -0.0002(6) -0.0037(7) C5 0.0484(10) 0.0353(10) 0.0287(8) -0.0038(7) -0.0033(7) -0.0018(8) C1 0.0337(8) 0.0313(9) 0.0274(8) 0.0038(6) 0.0003(6) -0.0028(7) C10 0.0343(8) 0.0309(9) 0.0277(8) 0.0024(6) -0.0016(6) 0.0028(7) C2 0.0368(9) 0.0301(9) 0.0277(8) -0.0004(6) -0.0003(6) -0.0030(7) C6 0.0397(9) 0.0309(9) 0.0357(9) 0.0001(7) -0.0018(7) -0.0003(7) C20 0.0292(8) 0.0356(9) 0.0303(8) -0.0024(7) -0.0026(6) 0.0024(7) C9 0.0294(8) 0.0360(9) 0.0282(8) -0.0004(6) 0.0025(6) -0.0004(7) C25 0.0389(9) 0.0449(11) 0.0297(8) -0.0017(7) 0.0005(7) 0.0095(8) C11 0.0376(9) 0.0378(10) 0.0276(8) 0.0011(7) 0.0024(6) 0.0011(7) C15 0.0365(9) 0.0437(11) 0.0433(10) -0.0084(8) 0.0059(7) 0.0029(8) C12 0.0393(9) 0.0350(10) 0.0396(9) 0.0047(7) 0.0012(7) -0.0052(8) C13 0.0493(11) 0.0291(9) 0.0456(10) -0.0056(7) -0.0027(8) -0.0023(8) C23 0.0583(12) 0.0593(13) 0.0344(10) 0.0023(8) -0.0124(8) 0.0115(10) C14 0.0492(11) 0.0424(11) 0.0510(11) -0.0150(8) 0.0064(8) 0.0049(9) C24 0.0522(11) 0.0564(13) 0.0304(9) -0.0010(8) 0.0009(7) 0.0107(10) C22 0.0488(11) 0.0659(15) 0.0495(11) 0.0021(10) -0.0103(9) 0.0208(10) C21 0.0344(9) 0.0627(13) 0.0407(10) -0.0029(8) 0.0009(7) 0.0135(9) S1 0.0683(7) 0.0321(5) 0.0381(5) -0.0003(4) -0.0058(4) 0.0058(4) O2 0.0553(11) 0.0276(10) 0.0632(12) 0.000 0.0025(9) 0.000 C1G 0.129(8) 0.028(4) 0.078(5) 0.002(3) 0.037(5) -0.025(5) C2G 0.135(8) 0.054(4) 0.036(3) 0.007(2) 0.027(4) 0.017(4) _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 C9 1.4197(19) . ? N1 N1 1.253(3) 7_575 ? N1 C1 1.4340(19) . ? C4 C5 1.381(2) . ? C4 C3 1.403(2) . ? C7 C8 1.197(2) . ? C7 C3 1.443(2) . ? C8 C9 1.487(2) . ? C3 C2 1.398(2) . ? C5 C6 1.390(2) . ? C1 C2 1.382(2) . ? C1 C6 1.393(2) . ? C10 C15 1.386(2) . ? C10 C11 1.392(2) . ? C10 C9 1.540(2) . ? C20 C25 1.383(2) . ? C20 C21 1.4003(18) . ? C20 C9 1.540(2) . ? C25 C24 1.393(2) . ? C11 C12 1.389(2) . ? C15 C14 1.379(3) . ? C12 C13 1.381(3) . ? C13 C14 1.386(3) . ? C23 C24 1.371(3) . ? C23 C22 1.373(3) . ? C22 C21 1.382(2) . ? S1 S1 1.1896(17) 2_655 ? S1 O2 1.5389 . ? S1 C2G 1.552(12) . ? S1 C1G 1.670(10) 2_655 ? S1 C2G 1.781(10) 2_655 ? S1 C1G 1.784(10) . ? O2 S1 1.5388 2_655 ? C1G S1 1.670(10) 2_655 ? C2G S1 1.781(10) 2_655 ? 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 N1 N1 C1 113.87(16) 7_575 . ? C5 C4 C3 120.64(14) . . ? C8 C7 C3 178.31(18) . . ? C7 C8 C9 177.51(17) . . ? C2 C3 C4 118.27(15) . . ? C2 C3 C7 120.46(14) . . ? C4 C3 C7 121.26(14) . . ? C4 C5 C6 120.90(15) . . ? C2 C1 C6 121.05(14) . . ? C2 C1 N1 114.43(14) . . ? C6 C1 N1 124.52(15) . . ? C15 C10 C11 118.91(16) . . ? C15 C10 C9 121.02(15) . . ? C11 C10 C9 120.06(14) . . ? C1 C2 C3 120.51(15) . . ? C5 C6 C1 118.53(16) . . ? C25 C20 C21 118.73(13) . . ? C25 C20 C9 121.59(14) . . ? C21 C20 C9 119.47(13) . . ? O1 C9 C8 109.78(13) . . ? O1 C9 C10 106.52(12) . . ? C8 C9 C10 109.54(13) . . ? O1 C9 C20 111.41(12) . . ? C8 C9 C20 110.68(13) . . ? C10 C9 C20 108.80(13) . . ? C20 C25 C24 120.78(16) . . ? C12 C11 C10 120.30(15) . . ? C14 C15 C10 120.69(17) . . ? C13 C12 C11 120.19(17) . . ? C12 C13 C14 119.58(17) . . ? C24 C23 C22 119.54(17) . . ? C15 C14 C13 120.32(17) . . ? C23 C24 C25 120.01(17) . . ? C23 C22 C21 121.40(17) . . ? C22 C21 C20 119.42(13) . . ? S1 S1 O2 67.3 2_655 . ? S1 S1 C2G 79.8(4) 2_655 . ? O2 S1 C2G 118.2(3) . . ? S1 S1 C1G 75.1(4) 2_655 2_655 ? O2 S1 C1G 105.5(4) . 2_655 ? C2G S1 C1G 114.7(4) . 2_655 ? S1 S1 C2G 59.1(4) 2_655 2_655 ? O2 S1 C2G 105.8(4) . 2_655 ? C2G S1 C2G 98.9(6) . 2_655 ? C1G S1 C2G 19.6(6) 2_655 2_655 ? S1 S1 C1G 64.7(4) 2_655 . ? O2 S1 C1G 100.3(3) . . ? C2G S1 C1G 19.0(5) . . ? C1G S1 C1G 118.0(6) 2_655 . ? C2G S1 C1G 99.1(4) 2_655 . ? S1 O2 S1 45.47(6) . 2_655 ? S1 C1G S1 40.1(2) 2_655 . ? S1 C2G S1 41.1(2) . 2_655 ? 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 C3 C7 C8 C9 7(9) . . . . ? C5 C4 C3 C2 1.2(2) . . . . ? C5 C4 C3 C7 -179.93(16) . . . . ? C8 C7 C3 C2 59(6) . . . . ? C8 C7 C3 C4 -119(6) . . . . ? C3 C4 C5 C6 -3.0(3) . . . . ? N1 N1 C1 C2 -173.06(17) 7_575 . . . ? N1 N1 C1 C6 6.3(3) 7_575 . . . ? C6 C1 C2 C3 -2.8(2) . . . . ? N1 C1 C2 C3 176.56(14) . . . . ? C4 C3 C2 C1 1.6(2) . . . . ? C7 C3 C2 C1 -177.19(15) . . . . ? C4 C5 C6 C1 1.8(3) . . . . ? C2 C1 C6 C5 1.1(2) . . . . ? N1 C1 C6 C5 -178.23(15) . . . . ? C7 C8 C9 O1 9(4) . . . . ? C7 C8 C9 C10 -107(4) . . . . ? C7 C8 C9 C20 133(4) . . . . ? C15 C10 C9 O1 9.0(2) . . . . ? C11 C10 C9 O1 -172.03(14) . . . . ? C15 C10 C9 C8 127.73(16) . . . . ? C11 C10 C9 C8 -53.35(19) . . . . ? C15 C10 C9 C20 -111.17(17) . . . . ? C11 C10 C9 C20 67.76(18) . . . . ? C25 C20 C9 O1 150.78(16) . . . . ? C21 C20 C9 O1 -34.5(2) . . . . ? C25 C20 C9 C8 28.3(2) . . . . ? C21 C20 C9 C8 -156.92(13) . . . . ? C25 C20 C9 C10 -92.08(19) . . . . ? C21 C20 C9 C10 82.68(17) . . . . ? C21 C20 C25 C24 -0.1(3) . . . . ? C9 C20 C25 C24 174.70(17) . . . . ? C15 C10 C11 C12 0.7(2) . . . . ? C9 C10 C11 C12 -178.26(14) . . . . ? C11 C10 C15 C14 -0.1(3) . . . . ? C9 C10 C15 C14 178.84(16) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? C11 C12 C13 C14 -0.4(3) . . . . ? C10 C15 C14 C13 -0.7(3) . . . . ? C12 C13 C14 C15 1.0(3) . . . . ? C22 C23 C24 C25 -0.3(3) . . . . ? C20 C25 C24 C23 1.6(3) . . . . ? C24 C23 C22 C21 -2.6(3) . . . . ? C23 C22 C21 C20 4.0(3) . . . . ? C25 C20 C21 C22 -2.6(2) . . . . ? C9 C20 C21 C22 -177.56(15) . . . . ? C2G S1 O2 S1 63.8(5) . . . 2_655 ? C1G S1 O2 S1 -66.1(4) 2_655 . . 2_655 ? C2G S1 O2 S1 -45.7(4) 2_655 . . 2_655 ? C1G S1 O2 S1 56.9(4) . . . 2_655 ? O2 S1 C1G S1 -58.7(2) . . . 2_655 ? C2G S1 C1G S1 140(2) . . . 2_655 ? C1G S1 C1G S1 55.2(5) 2_655 . . 2_655 ? C2G S1 C1G S1 49.3(4) 2_655 . . 2_655 ? O2 S1 C2G S1 -57.2(3) . . . 2_655 ? C1G S1 C2G S1 68.3(5) 2_655 . . 2_655 ? C2G S1 C2G S1 56.2(4) 2_655 . . 2_655 ? C1G S1 C2G S1 -36(2) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.431 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.051 data_2.2DMF _database_code_CSD 196893 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-{3-[3-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-phenylazo]-phenyl} -1,1-diphenyl-prop-2-yn-1-ol DMF solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H30 N2 O2.2(C2 H7 N O)' _chemical_formula_sum 'C48 H44 N4 O4' _chemical_formula_weight 740.87 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 8.64420(10) _cell_length_b 11.6634(2) _cell_length_c 20.1599(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.2480(10) _cell_angle_gamma 90.00 _cell_volume 1993.50(6) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour 'orange (dichromic)' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9767 _exptl_absorpt_correction_T_max 0.9844 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method '\phi + w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4909 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0751 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4909 _reflns_number_gt 2887 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XSeed _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^)+(0.0596P)^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 4909 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1013 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1120 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _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 0.02067(11) 0.05639(8) 0.16225(5) 0.0274(3) Uani 1 1 d . . . N1 N 0.45400(11) 0.54251(10) -0.00576(5) 0.0220(3) Uani 1 1 d . . . C3 C 0.14587(15) 0.43846(12) 0.08769(7) 0.0231(3) Uani 1 1 d . . . C9 C -0.00049(15) 0.16614(12) 0.18975(7) 0.0220(3) Uani 1 1 d . . . C2 C 0.27800(14) 0.43661(12) 0.05761(7) 0.0225(3) Uani 1 1 d . . . H2 H 0.3386 0.3685 0.0584 0.027 Uiso 1 1 calc R . . C7 C 0.09587(15) 0.33825(13) 0.11968(7) 0.0253(3) Uani 1 1 d . . . C25 C -0.26200(15) 0.27693(12) 0.17575(7) 0.0255(3) Uani 1 1 d . . . H25 H -0.2230 0.3319 0.1484 0.031 Uiso 1 1 calc R . . C8 C 0.04888(15) 0.25916(13) 0.14759(7) 0.0254(3) Uani 1 1 d . . . C20 C -0.17100(14) 0.18235(12) 0.19972(7) 0.0218(3) Uani 1 1 d . . . C1 C 0.32085(14) 0.53484(12) 0.02652(7) 0.0211(3) Uani 1 1 d . . . C11 C 0.20409(14) 0.08210(12) 0.28615(7) 0.0219(3) Uani 1 1 d . . . H11 H 0.2008 0.0123 0.2616 0.026 Uiso 1 1 calc R . . C10 C 0.10978(14) 0.17346(12) 0.25963(7) 0.0210(3) Uani 1 1 d . . . C4 C 0.05886(15) 0.54037(13) 0.08634(7) 0.0271(3) Uani 1 1 d . . . H4 H -0.0301 0.5428 0.1075 0.032 Uiso 1 1 calc R . . C6 C 0.23171(15) 0.63427(13) 0.02381(7) 0.0256(3) Uani 1 1 d . . . H6 H 0.2597 0.7002 0.0011 0.031 Uiso 1 1 calc R . . C23 C -0.46896(16) 0.21207(13) 0.23109(7) 0.0300(4) Uani 1 1 d . . . H23 H -0.5696 0.2228 0.2425 0.036 Uiso 1 1 calc R . . C24 C -0.41072(15) 0.29158(13) 0.19175(7) 0.0288(4) Uani 1 1 d . . . H24 H -0.4722 0.3569 0.1754 0.035 Uiso 1 1 calc R . . C14 C 0.21351(16) 0.28487(13) 0.35916(8) 0.0292(4) Uani 1 1 d . . . H14 H 0.2159 0.3541 0.3841 0.035 Uiso 1 1 calc R . . C15 C 0.11419(15) 0.27446(13) 0.29683(7) 0.0268(3) Uani 1 1 d . . . H15 H 0.0482 0.3369 0.2792 0.032 Uiso 1 1 calc R . . C21 C -0.23190(15) 0.10118(13) 0.23822(7) 0.0290(4) Uani 1 1 d . . . H21 H -0.1717 0.0349 0.2538 0.035 Uiso 1 1 calc R . . C5 C 0.10098(16) 0.63678(13) 0.05469(7) 0.0287(4) Uani 1 1 d . . . H5 H 0.0408 0.7051 0.0539 0.034 Uiso 1 1 calc R . . C13 C 0.30957(15) 0.19381(12) 0.38507(7) 0.0262(3) Uani 1 1 d . . . H13 H 0.3791 0.2009 0.4276 0.031 Uiso 1 1 calc R . . C12 C 0.30403(15) 0.09308(13) 0.34909(7) 0.0252(3) Uani 1 1 d . . . H12 H 0.3689 0.0305 0.3673 0.030 Uiso 1 1 calc R . . C22 C -0.37930(16) 0.11612(14) 0.25396(8) 0.0330(4) Uani 1 1 d . . . H22 H -0.4194 0.0604 0.2806 0.040 Uiso 1 1 calc R . . O1G O 0.16857(15) 0.50483(10) 0.45925(6) 0.0500(3) Uani 1 1 d . . . N1G N 0.31224(15) 0.52099(12) 0.56604(6) 0.0374(3) Uani 1 1 d . . . C1G C 0.19692(18) 0.55006(14) 0.51518(8) 0.0347(4) Uani 1 1 d . . . H1G H 0.1303 0.6115 0.5228 0.042 Uiso 1 1 calc R . . C2G C 0.3369(2) 0.57934(16) 0.63062(8) 0.0477(5) Uani 1 1 d . . . H2G1 H 0.2583 0.6403 0.6291 0.072 Uiso 1 1 calc R . . H2G2 H 0.4429 0.6128 0.6403 0.072 Uiso 1 1 calc R . . H2G3 H 0.3262 0.5244 0.6662 0.072 Uiso 1 1 calc R . . C3G C 0.4124(3) 0.4222(2) 0.56103(11) 0.0874(9) Uani 1 1 d . . . H3G1 H 0.3829 0.3591 0.5881 0.131 Uiso 1 1 calc R . . H3G2 H 0.5229 0.4429 0.5779 0.131 Uiso 1 1 calc R . . H3G3 H 0.3987 0.3982 0.5137 0.131 Uiso 1 1 calc R . . H1O H -0.042(2) 0.0509(18) 0.1175(11) 0.081(7) 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 0.0285(5) 0.0292(6) 0.0239(6) -0.0028(5) 0.0034(4) 0.0032(4) N1 0.0184(6) 0.0274(7) 0.0204(6) -0.0006(5) 0.0044(5) -0.0021(4) C3 0.0193(7) 0.0319(9) 0.0181(7) 0.0024(6) 0.0034(5) -0.0036(6) C9 0.0218(7) 0.0233(8) 0.0215(7) 0.0017(6) 0.0057(5) 0.0001(6) C2 0.0197(7) 0.0271(8) 0.0205(7) 0.0024(6) 0.0031(5) 0.0010(6) C7 0.0183(7) 0.0359(9) 0.0226(8) 0.0015(7) 0.0064(6) 0.0008(6) C25 0.0232(7) 0.0270(8) 0.0262(8) 0.0034(6) 0.0047(6) -0.0034(6) C8 0.0191(7) 0.0335(9) 0.0234(8) 0.0020(7) 0.0038(6) 0.0036(6) C20 0.0200(6) 0.0255(8) 0.0197(7) -0.0001(6) 0.0031(5) -0.0031(6) C1 0.0177(6) 0.0280(8) 0.0178(7) -0.0005(6) 0.0038(5) -0.0036(6) C11 0.0218(7) 0.0232(8) 0.0224(8) 0.0008(6) 0.0082(5) 0.0001(6) C10 0.0175(6) 0.0257(8) 0.0211(7) 0.0029(6) 0.0072(5) -0.0020(5) C4 0.0200(7) 0.0376(9) 0.0249(8) 0.0004(7) 0.0079(6) 0.0003(6) C6 0.0245(7) 0.0257(8) 0.0272(8) 0.0020(6) 0.0067(6) -0.0023(6) C23 0.0193(7) 0.0392(10) 0.0323(9) -0.0018(7) 0.0071(6) -0.0030(6) C24 0.0225(7) 0.0286(9) 0.0345(9) 0.0025(7) 0.0034(6) 0.0027(6) C14 0.0297(8) 0.0265(9) 0.0312(8) -0.0052(7) 0.0052(6) -0.0015(6) C15 0.0239(7) 0.0259(9) 0.0301(8) 0.0037(7) 0.0037(6) 0.0018(6) C21 0.0237(7) 0.0300(9) 0.0329(9) 0.0083(7) 0.0049(6) 0.0010(6) C5 0.0249(7) 0.0286(9) 0.0335(9) 0.0000(7) 0.0082(6) 0.0031(6) C13 0.0247(7) 0.0310(9) 0.0221(8) -0.0004(7) 0.0021(6) -0.0012(6) C12 0.0218(7) 0.0299(9) 0.0243(8) 0.0044(7) 0.0057(6) 0.0019(6) C22 0.0272(8) 0.0379(10) 0.0356(9) 0.0103(8) 0.0100(6) -0.0064(7) O1G 0.0674(8) 0.0463(8) 0.0291(7) -0.0075(6) -0.0085(6) 0.0148(6) N1G 0.0431(8) 0.0422(9) 0.0254(7) 0.0001(6) 0.0028(6) 0.0023(6) C1G 0.0388(9) 0.0306(9) 0.0334(9) -0.0005(8) 0.0038(7) 0.0003(7) C2G 0.0502(10) 0.0604(13) 0.0316(10) -0.0091(9) 0.0055(8) -0.0171(9) C3G 0.113(2) 0.0905(19) 0.0463(13) -0.0056(13) -0.0147(13) 0.0584(16) _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 C9 1.4210(16) . ? N1 N1 1.264(2) 3_665 ? N1 C1 1.4312(17) . ? C3 C2 1.3938(19) . ? C3 C4 1.404(2) . ? C3 C7 1.441(2) . ? C9 C8 1.491(2) . ? C9 C20 1.5376(18) . ? C9 C10 1.5417(18) . ? C2 C1 1.3905(19) . ? C7 C8 1.192(2) . ? C25 C20 1.3860(19) . ? C25 C24 1.3957(19) . ? C20 C21 1.3910(19) . ? C1 C6 1.3875(19) . ? C11 C10 1.3841(19) . ? C11 C12 1.3947(18) . ? C10 C15 1.393(2) . ? C4 C5 1.377(2) . ? C6 C5 1.3928(19) . ? C23 C24 1.378(2) . ? C23 C22 1.388(2) . ? C14 C15 1.3820(19) . ? C14 C13 1.3860(19) . ? C21 C22 1.383(2) . ? C13 C12 1.377(2) . ? O1G C1G 1.2255(18) . ? N1G C1G 1.3272(19) . ? N1G C2G 1.447(2) . ? N1G C3G 1.456(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 N1 N1 C1 113.60(14) 3_665 . ? C2 C3 C4 119.08(13) . . ? C2 C3 C7 121.65(13) . . ? C4 C3 C7 119.27(12) . . ? O1 C9 C8 111.11(11) . . ? O1 C9 C20 111.19(10) . . ? C8 C9 C20 111.92(11) . . ? O1 C9 C10 107.62(10) . . ? C8 C9 C10 106.61(10) . . ? C20 C9 C10 108.14(11) . . ? C1 C2 C3 119.76(13) . . ? C8 C7 C3 176.35(15) . . ? C20 C25 C24 120.17(13) . . ? C7 C8 C9 173.57(15) . . ? C25 C20 C21 119.04(12) . . ? C25 C20 C9 123.07(12) . . ? C21 C20 C9 117.77(12) . . ? C6 C1 C2 120.77(12) . . ? C6 C1 N1 114.81(12) . . ? C2 C1 N1 124.41(12) . . ? C10 C11 C12 119.62(13) . . ? C11 C10 C15 119.40(12) . . ? C11 C10 C9 121.52(12) . . ? C15 C10 C9 119.07(11) . . ? C5 C4 C3 120.76(13) . . ? C1 C6 C5 119.53(14) . . ? C24 C23 C22 119.40(13) . . ? C23 C24 C25 120.47(13) . . ? C15 C14 C13 119.71(14) . . ? C14 C15 C10 120.71(13) . . ? C22 C21 C20 120.54(13) . . ? C4 C5 C6 120.07(14) . . ? C12 C13 C14 119.91(13) . . ? C13 C12 C11 120.63(13) . . ? C21 C22 C23 120.35(14) . . ? C1G N1G C2G 122.11(15) . . ? C1G N1G C3G 121.03(14) . . ? C2G N1G C3G 116.68(14) . . ? O1G C1G N1G 125.89(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 C3 C2 C1 -0.43(19) . . . . ? C7 C3 C2 C1 179.15(12) . . . . ? C2 C3 C7 C8 169(2) . . . . ? C4 C3 C7 C8 -12(2) . . . . ? C3 C7 C8 C9 -70(3) . . . . ? O1 C9 C8 C7 -134.4(12) . . . . ? C20 C9 C8 C7 100.6(13) . . . . ? C10 C9 C8 C7 -17.5(13) . . . . ? C24 C25 C20 C21 1.7(2) . . . . ? C24 C25 C20 C9 -174.18(12) . . . . ? O1 C9 C20 C25 -128.96(14) . . . . ? C8 C9 C20 C25 -4.04(18) . . . . ? C10 C9 C20 C25 113.09(14) . . . . ? O1 C9 C20 C21 55.08(16) . . . . ? C8 C9 C20 C21 179.99(12) . . . . ? C10 C9 C20 C21 -62.87(16) . . . . ? C3 C2 C1 C6 -1.33(19) . . . . ? C3 C2 C1 N1 179.94(11) . . . . ? N1 N1 C1 C6 170.18(13) 3_665 . . . ? N1 N1 C1 C2 -11.0(2) 3_665 . . . ? C12 C11 C10 C15 -1.10(19) . . . . ? C12 C11 C10 C9 178.95(12) . . . . ? O1 C9 C10 C11 -1.52(16) . . . . ? C8 C9 C10 C11 -120.81(13) . . . . ? C20 C9 C10 C11 118.68(13) . . . . ? O1 C9 C10 C15 178.53(11) . . . . ? C8 C9 C10 C15 59.25(15) . . . . ? C20 C9 C10 C15 -61.26(15) . . . . ? C2 C3 C4 C5 1.3(2) . . . . ? C7 C3 C4 C5 -178.32(13) . . . . ? C2 C1 C6 C5 2.3(2) . . . . ? N1 C1 C6 C5 -178.90(12) . . . . ? C22 C23 C24 C25 -0.9(2) . . . . ? C20 C25 C24 C23 -0.4(2) . . . . ? C13 C14 C15 C10 -0.2(2) . . . . ? C11 C10 C15 C14 1.2(2) . . . . ? C9 C10 C15 C14 -178.91(12) . . . . ? C25 C20 C21 C22 -1.8(2) . . . . ? C9 C20 C21 C22 174.36(13) . . . . ? C3 C4 C5 C6 -0.3(2) . . . . ? C1 C6 C5 C4 -1.4(2) . . . . ? C15 C14 C13 C12 -0.9(2) . . . . ? C14 C13 C12 C11 0.9(2) . . . . ? C10 C11 C12 C13 0.1(2) . . . . ? C20 C21 C22 C23 0.5(2) . . . . ? C24 C23 C22 C21 0.9(2) . . . . ? C2G N1G C1G O1G -179.93(16) . . . . ? C3G N1G C1G O1G -4.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.188 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.053 data_3.2DMSO _database_code_CSD 196894 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-{4-[4-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-phenylazo]-phenyl} -1,1-diphenyl-prop-2-yn-1-ol 3 DMSO solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H30 N2 O2.2(C2 H6 S O)' _chemical_formula_sum 'C46 H42 N2 O4 S2' _chemical_formula_weight 750.94 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' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 '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 11.8006(2) _cell_length_b 22.0051(4) _cell_length_c 15.1395(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.6580(10) _cell_angle_gamma 90.00 _cell_volume 3929.68(12) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9145 _exptl_absorpt_correction_T_max 0.9645 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method '\phi + w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15961 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0987 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 28.29 _reflns_number_total 9616 _reflns_number_gt 5466 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XSeed _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^)+(0.0471P)^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 9616 _refine_ls_number_parameters 504 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1264 _refine_ls_wR_factor_gt 0.1128 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.017 _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 0.26341(11) 0.32466(6) 0.55316(10) 0.0220(3) Uani 1 1 d . . . H1O H 0.2456(19) 0.3093(11) 0.5008(17) 0.050(8) Uiso 1 1 d . . . O1' O 1.23329(11) -0.32430(6) 0.45725(10) 0.0223(3) Uani 1 1 d . . . H1'O H 1.2563(19) -0.2980(11) 0.4170(17) 0.056(8) Uiso 1 1 d . . . O2G O 0.22741(11) 0.21344(6) 0.88127(9) 0.0288(4) Uani 1 1 d . . . N1' N 0.79381(14) 0.00167(7) 0.47508(12) 0.0258(4) Uani 1 1 d . . . N1 N 0.70757(14) 0.00537(7) 0.52222(12) 0.0246(4) Uani 1 1 d . . . C10' C 1.08106(16) -0.38099(9) 0.51494(13) 0.0198(5) Uani 1 1 d . . . C8 C 0.44679(16) 0.28270(9) 0.54473(13) 0.0212(5) Uani 1 1 d . . . C3' C 0.85276(16) -0.16382(9) 0.51028(13) 0.0229(5) Uani 1 1 d . . . H3' H 0.8230 -0.1983 0.5395 0.028 Uiso 1 1 calc R . . C3 C 0.66009(17) 0.17286(9) 0.50084(14) 0.0241(5) Uani 1 1 d . . . H3 H 0.6970 0.2085 0.4810 0.029 Uiso 1 1 calc R . . C7 C 0.49378(17) 0.23517(9) 0.53959(13) 0.0217(5) Uani 1 1 d . . . C9 C 0.38154(15) 0.33949(8) 0.55849(13) 0.0177(4) Uani 1 1 d . . . C2' C 0.79826(17) -0.10878(9) 0.51539(14) 0.0226(5) Uani 1 1 d . . . H2' H 0.7311 -0.1052 0.5481 0.027 Uiso 1 1 calc R . . C22' C 1.14579(18) -0.41239(9) 0.22048(14) 0.0244(5) Uani 1 1 d . . . H22' H 1.2031 -0.4324 0.1886 0.029 Uiso 1 1 calc R . . C4' C 0.95237(16) -0.16949(8) 0.46207(13) 0.0205(5) Uani 1 1 d . . . C7' C 1.00924(16) -0.22780(9) 0.45767(13) 0.0206(5) Uani 1 1 d . . . C14 C 0.34994(18) 0.46521(9) 0.38544(14) 0.0277(5) Uani 1 1 d . . . H14 H 0.2904 0.4870 0.3561 0.033 Uiso 1 1 calc R . . C9' C 1.11377(16) -0.33486(8) 0.44474(13) 0.0178(4) Uani 1 1 d . . . C15 C 0.32449(17) 0.42124(9) 0.44740(14) 0.0228(5) Uani 1 1 d . . . H15 H 0.2477 0.4138 0.4611 0.027 Uiso 1 1 calc R . . C6 C 0.55437(17) 0.06933(9) 0.56310(14) 0.0252(5) Uani 1 1 d . . . H6 H 0.5196 0.0340 0.5860 0.030 Uiso 1 1 calc R . . C11' C 1.14013(18) -0.43598(9) 0.52042(14) 0.0272(5) Uani 1 1 d . . . H11' H 1.2005 -0.4435 0.4817 0.033 Uiso 1 1 calc R . . C2 C 0.71376(17) 0.11751(9) 0.49534(14) 0.0239(5) Uani 1 1 d . . . H2 H 0.7869 0.1149 0.4710 0.029 Uiso 1 1 calc R . . C21' C 1.17058(17) -0.38980(8) 0.30464(14) 0.0218(5) Uani 1 1 d . . . H21' H 1.2450 -0.3940 0.3296 0.026 Uiso 1 1 calc R . . C25' C 0.97780(17) -0.35680(9) 0.31526(14) 0.0230(5) Uani 1 1 d . . . H25' H 0.9192 -0.3388 0.3481 0.028 Uiso 1 1 calc R . . C1 C 0.66045(17) 0.06512(9) 0.52568(13) 0.0213(5) Uani 1 1 d . . . C8' C 1.05344(16) -0.27612(9) 0.45395(13) 0.0200(5) Uani 1 1 d . . . C21 C 0.50630(16) 0.35000(9) 0.69790(14) 0.0232(5) Uani 1 1 d . . . H21 H 0.5607 0.3242 0.6721 0.028 Uiso 1 1 calc R . . C1' C 0.84192(17) -0.05806(9) 0.47228(14) 0.0218(5) Uani 1 1 d . . . C24 C 0.35004(18) 0.42617(9) 0.77363(14) 0.0264(5) Uani 1 1 d . . . H24 H 0.2966 0.4527 0.7992 0.032 Uiso 1 1 calc R . . C20' C 1.08700(16) -0.36112(8) 0.35239(13) 0.0183(4) Uani 1 1 d . . . C10 C 0.41032(16) 0.38796(8) 0.48969(13) 0.0177(4) Uani 1 1 d . . . C14' C 0.96695(18) -0.41507(10) 0.63518(15) 0.0307(5) Uani 1 1 d . . . H14' H 0.9077 -0.4076 0.6750 0.037 Uiso 1 1 calc R . . C5 C 0.49938(17) 0.12472(9) 0.56706(14) 0.0244(5) Uani 1 1 d . . . H5 H 0.4261 0.1271 0.5913 0.029 Uiso 1 1 calc R . . C15' C 0.99376(17) -0.37125(9) 0.57240(14) 0.0248(5) Uani 1 1 d . . . H15' H 0.9517 -0.3345 0.5691 0.030 Uiso 1 1 calc R . . C4G C 0.42032(18) 0.20718(10) 0.79676(15) 0.0347(6) Uani 1 1 d . . . H4G1 H 0.4696 0.2178 0.8477 0.052 Uiso 1 1 calc R . . H4G2 H 0.4558 0.2203 0.7422 0.052 Uiso 1 1 calc R . . H4G3 H 0.4089 0.1631 0.7952 0.052 Uiso 1 1 calc R . . C5G C 0.21999(19) 0.21449(11) 0.70892(15) 0.0386(6) Uani 1 1 d . . . H5G1 H 0.2251 0.1700 0.7096 0.058 Uiso 1 1 calc R . . H5G2 H 0.2579 0.2303 0.6570 0.058 Uiso 1 1 calc R . . H5G3 H 0.1401 0.2267 0.7065 0.058 Uiso 1 1 calc R . . C20 C 0.40646(16) 0.36406(8) 0.65138(13) 0.0183(4) Uani 1 1 d . . . C11 C 0.52224(17) 0.40060(9) 0.46998(14) 0.0232(5) Uani 1 1 d . . . H11 H 0.5820 0.3785 0.4985 0.028 Uiso 1 1 calc R . . C13' C 1.02594(18) -0.46900(10) 0.63966(15) 0.0328(6) Uani 1 1 d . . . H13' H 1.0079 -0.4988 0.6824 0.039 Uiso 1 1 calc R . . C22 C 0.52676(18) 0.37351(9) 0.78175(14) 0.0269(5) Uani 1 1 d . . . H22 H 0.5951 0.3635 0.8131 0.032 Uiso 1 1 calc R . . C23' C 1.03804(17) -0.40592(9) 0.18281(14) 0.0252(5) Uani 1 1 d . . . H23' H 1.0219 -0.4201 0.1245 0.030 Uiso 1 1 calc R . . C6' C 0.93936(17) -0.06375(9) 0.42374(14) 0.0278(5) Uani 1 1 d . . . H6' H 0.9685 -0.0294 0.3940 0.033 Uiso 1 1 calc R . . C12 C 0.54734(18) 0.44540(9) 0.40893(14) 0.0276(5) Uani 1 1 d . . . H12 H 0.6241 0.4540 0.3964 0.033 Uiso 1 1 calc R . . C4 C 0.55124(17) 0.17708(9) 0.53556(14) 0.0223(5) Uani 1 1 d . . . C5' C 0.99426(17) -0.11894(9) 0.41830(14) 0.0265(5) Uani 1 1 d . . . H5' H 1.0607 -0.1225 0.3847 0.032 Uiso 1 1 calc R . . C13 C 0.46099(18) 0.47755(9) 0.36622(14) 0.0278(5) Uani 1 1 d . . . H13 H 0.4782 0.5079 0.3240 0.033 Uiso 1 1 calc R . . C25 C 0.32893(17) 0.40258(9) 0.69003(14) 0.0231(5) Uani 1 1 d . . . H25 H 0.2607 0.4129 0.6587 0.028 Uiso 1 1 calc R . . C23 C 0.44923(18) 0.41116(9) 0.82011(14) 0.0279(5) Uani 1 1 d . . . H23 H 0.4634 0.4268 0.8779 0.033 Uiso 1 1 calc R . . C12' C 1.11143(19) -0.47920(10) 0.58143(15) 0.0321(6) Uani 1 1 d . . . H12' H 1.1512 -0.5167 0.5835 0.038 Uiso 1 1 calc R . . C24' C 0.95425(18) -0.37854(9) 0.23103(14) 0.0267(5) Uani 1 1 d . . . H24' H 0.8798 -0.3746 0.2060 0.032 Uiso 1 1 calc R . . S2G S 0.28683(5) 0.24417(2) 0.80628(4) 0.02814(15) Uani 1 1 d . . . S1G S 1.20171(5) -0.20867(3) 0.27489(4) 0.02754(16) Uani 0.90 1 d P A 1 O1G O 1.28777(12) -0.24729(6) 0.32139(10) 0.0335(4) Uani 1 1 d . A 1 C1G C 1.2738(2) -0.14758(12) 0.2269(2) 0.0622(9) Uani 1 1 d . A 1 H1G1 H 1.3091 -0.1225 0.2735 0.093 Uiso 1 1 calc R A 1 H1G2 H 1.2199 -0.1229 0.1919 0.093 Uiso 1 1 calc R A 1 H1G3 H 1.3324 -0.1633 0.1885 0.093 Uiso 1 1 calc R A 1 C2G C 1.1571(3) -0.24619(15) 0.1796(2) 0.0860(11) Uiso 1 1 d . A 1 H2G1 H 1.2231 -0.2566 0.1447 0.129 Uiso 1 1 calc R A 1 H2G2 H 1.1061 -0.2198 0.1447 0.129 Uiso 1 1 calc R A 1 H2G3 H 1.1169 -0.2834 0.1954 0.129 Uiso 1 1 calc R A 1 S1G2 S 1.2715(5) -0.2334(3) 0.2234(4) 0.0375(16) Uani 0.10 1 d P B 2 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 0.0199(8) 0.0244(8) 0.0215(9) -0.0012(7) 0.0002(6) -0.0017(6) O1' 0.0196(8) 0.0229(8) 0.0244(9) 0.0032(7) -0.0011(6) 0.0003(7) O2G 0.0313(8) 0.0342(9) 0.0210(9) 0.0056(7) 0.0038(7) 0.0010(7) N1' 0.0300(10) 0.0215(10) 0.0261(11) 0.0002(8) 0.0055(8) 0.0070(8) N1 0.0266(10) 0.0204(10) 0.0269(11) -0.0003(8) 0.0024(8) 0.0058(8) C10' 0.0216(11) 0.0189(11) 0.0188(11) -0.0011(9) -0.0039(9) 0.0013(9) C8 0.0225(11) 0.0233(12) 0.0177(12) 0.0003(9) 0.0004(9) -0.0001(10) C3' 0.0264(11) 0.0206(11) 0.0220(12) 0.0011(9) 0.0024(9) 0.0006(10) C3 0.0276(12) 0.0192(11) 0.0258(13) -0.0009(9) 0.0036(10) 0.0012(10) C7 0.0249(11) 0.0211(11) 0.0192(12) -0.0002(9) 0.0008(9) -0.0006(10) C9 0.0158(10) 0.0181(10) 0.0190(11) -0.0016(9) -0.0001(8) 0.0029(9) C2' 0.0223(11) 0.0238(12) 0.0218(12) -0.0013(9) 0.0038(9) 0.0045(10) C22' 0.0311(12) 0.0195(11) 0.0231(12) -0.0015(9) 0.0074(10) 0.0015(10) C4' 0.0229(11) 0.0182(10) 0.0203(12) -0.0020(9) -0.0017(9) 0.0025(9) C7' 0.0208(11) 0.0204(11) 0.0206(12) 0.0006(9) 0.0011(9) -0.0005(10) C14 0.0328(13) 0.0217(11) 0.0284(13) 0.0038(10) -0.0025(10) 0.0055(10) C9' 0.0177(10) 0.0169(10) 0.0189(11) -0.0014(9) -0.0001(8) 0.0047(9) C15 0.0226(11) 0.0208(11) 0.0250(12) -0.0020(9) 0.0020(9) 0.0012(9) C6 0.0276(12) 0.0181(11) 0.0301(13) 0.0000(9) 0.0028(10) 0.0021(10) C11' 0.0309(12) 0.0260(12) 0.0247(13) -0.0001(10) 0.0012(10) 0.0056(10) C2 0.0238(11) 0.0250(12) 0.0230(12) -0.0032(9) 0.0035(9) 0.0043(10) C21' 0.0236(11) 0.0188(11) 0.0232(12) 0.0013(9) 0.0025(9) 0.0034(9) C25' 0.0219(11) 0.0235(11) 0.0238(12) -0.0024(9) 0.0012(9) 0.0022(9) C1 0.0258(11) 0.0170(11) 0.0211(12) -0.0011(9) 0.0000(9) 0.0067(9) C8' 0.0206(11) 0.0228(11) 0.0165(11) 0.0001(9) 0.0002(9) -0.0011(10) C21 0.0227(11) 0.0233(11) 0.0235(13) 0.0009(9) 0.0015(9) 0.0033(9) C1' 0.0261(12) 0.0171(11) 0.0219(12) 0.0004(9) -0.0007(9) 0.0059(9) C24 0.0306(12) 0.0227(12) 0.0265(13) -0.0022(10) 0.0086(10) -0.0004(10) C20' 0.0242(11) 0.0146(10) 0.0163(11) 0.0015(8) 0.0013(9) 0.0014(9) C10 0.0216(11) 0.0146(10) 0.0171(11) -0.0037(8) 0.0013(9) 0.0010(9) C14' 0.0289(12) 0.0360(13) 0.0275(13) 0.0053(11) 0.0038(10) -0.0023(11) C5 0.0211(11) 0.0254(12) 0.0270(13) -0.0017(10) 0.0020(9) 0.0040(10) C15' 0.0233(11) 0.0243(12) 0.0267(13) 0.0010(10) -0.0011(10) 0.0028(10) C4G 0.0352(13) 0.0408(14) 0.0285(14) 0.0053(11) 0.0090(11) 0.0028(11) C5G 0.0427(14) 0.0492(15) 0.0235(14) 0.0037(11) -0.0036(11) -0.0053(12) C20 0.0220(11) 0.0151(10) 0.0178(11) 0.0027(8) 0.0026(9) -0.0017(9) C11 0.0233(11) 0.0238(11) 0.0225(12) -0.0026(9) 0.0001(9) 0.0028(10) C13' 0.0361(13) 0.0316(13) 0.0304(14) 0.0112(11) -0.0031(11) -0.0051(12) C22 0.0270(12) 0.0297(12) 0.0238(13) 0.0019(10) -0.0039(10) -0.0033(10) C23' 0.0331(12) 0.0238(11) 0.0189(12) -0.0031(9) 0.0014(10) -0.0023(10) C6' 0.0328(12) 0.0200(11) 0.0311(14) 0.0044(10) 0.0104(10) 0.0023(10) C12 0.0273(12) 0.0261(12) 0.0299(14) -0.0019(10) 0.0066(10) -0.0033(10) C4 0.0261(12) 0.0206(11) 0.0200(12) -0.0032(9) -0.0027(9) 0.0050(10) C5' 0.0245(11) 0.0233(12) 0.0321(14) 0.0006(10) 0.0082(10) 0.0052(10) C13 0.0375(13) 0.0222(11) 0.0240(13) 0.0039(10) 0.0064(10) -0.0021(11) C25 0.0257(11) 0.0208(11) 0.0228(12) -0.0018(9) 0.0005(9) 0.0020(9) C23 0.0388(13) 0.0265(12) 0.0185(12) -0.0015(10) 0.0021(10) -0.0079(11) C12' 0.0409(14) 0.0225(12) 0.0326(14) 0.0047(10) -0.0025(11) 0.0063(11) C24' 0.0276(12) 0.0283(12) 0.0237(13) -0.0010(10) -0.0055(10) -0.0010(10) S2G 0.0349(3) 0.0248(3) 0.0248(3) 0.0017(2) 0.0032(2) -0.0002(3) S1G 0.0298(3) 0.0281(3) 0.0248(4) 0.0039(3) 0.0015(3) 0.0049(3) O1G 0.0299(8) 0.0348(9) 0.0353(10) 0.0124(7) -0.0063(7) 0.0010(7) C1G 0.0573(18) 0.0469(16) 0.081(2) 0.0365(16) -0.0218(16) -0.0205(15) S1G2 0.030(3) 0.035(3) 0.048(4) 0.005(3) 0.021(3) 0.014(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 C9 1.432(2) . ? O1' C9' 1.437(2) . ? O2G S2G 1.5113(14) . ? N1' N1 1.262(2) . ? N1' C1' 1.433(2) . ? N1 C1 1.429(2) . ? C10' C15' 1.384(3) . ? C10' C11' 1.398(3) . ? C10' C9' 1.527(3) . ? C8 C7 1.187(3) . ? C8 C9 1.486(3) . ? C3' C2' 1.374(3) . ? C3' C4' 1.407(3) . ? C3 C2 1.376(3) . ? C3 C4 1.405(3) . ? C7 C4 1.449(3) . ? C9 C20 1.527(3) . ? C9 C10 1.536(3) . ? C2' C1' 1.399(3) . ? C22' C23' 1.386(3) . ? C22' C21' 1.391(3) . ? C4' C5' 1.393(3) . ? C4' C7' 1.450(3) . ? C7' C8' 1.187(3) . ? C14 C13 1.378(3) . ? C14 C15 1.387(3) . ? C9' C8' 1.484(3) . ? C9' C20' 1.537(3) . ? C15 C10 1.391(3) . ? C6 C5 1.383(3) . ? C6 C1 1.392(3) . ? C11' C12' 1.375(3) . ? C2 C1 1.397(3) . ? C21' C20' 1.391(3) . ? C25' C24' 1.383(3) . ? C25' C20' 1.394(3) . ? C21 C22 1.386(3) . ? C21 C20 1.390(3) . ? C1' C6' 1.388(3) . ? C24 C25 1.384(3) . ? C24 C23 1.388(3) . ? C10 C11 1.390(3) . ? C14' C13' 1.376(3) . ? C14' C15' 1.397(3) . ? C5 C4 1.395(3) . ? C4G S2G 1.783(2) . ? C5G S2G 1.776(2) . ? C20 C25 1.389(3) . ? C11 C12 1.389(3) . ? C13' C12' 1.377(3) . ? C22 C23 1.375(3) . ? C23' C24' 1.384(3) . ? C6' C5' 1.380(3) . ? C12 C13 1.385(3) . ? S1G O1G 1.4860(15) . ? S1G C2G 1.731(3) . ? S1G C1G 1.759(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 N1 N1' C1' 113.73(17) . . ? N1' N1 C1 113.64(17) . . ? C15' C10' C11' 118.41(19) . . ? C15' C10' C9' 122.83(17) . . ? C11' C10' C9' 118.75(18) . . ? C7 C8 C9 174.3(2) . . ? C2' C3' C4' 120.44(19) . . ? C2 C3 C4 120.56(19) . . ? C8 C7 C4 178.7(2) . . ? O1 C9 C8 107.95(15) . . ? O1 C9 C20 107.09(15) . . ? C8 C9 C20 109.88(16) . . ? O1 C9 C10 110.74(15) . . ? C8 C9 C10 111.30(16) . . ? C20 C9 C10 109.77(15) . . ? C3' C2' C1' 119.84(19) . . ? C23' C22' C21' 120.43(19) . . ? C5' C4' C3' 119.29(18) . . ? C5' C4' C7' 120.91(18) . . ? C3' C4' C7' 119.80(18) . . ? C8' C7' C4' 178.5(2) . . ? C13 C14 C15 120.4(2) . . ? O1' C9' C8' 108.58(15) . . ? O1' C9' C10' 106.42(15) . . ? C8' C9' C10' 112.45(16) . . ? O1' C9' C20' 110.85(15) . . ? C8' C9' C20' 109.05(16) . . ? C10' C9' C20' 109.49(15) . . ? C14 C15 C10 120.65(19) . . ? C5 C6 C1 120.32(19) . . ? C12' C11' C10' 120.4(2) . . ? C3 C2 C1 119.85(19) . . ? C20' C21' C22' 120.31(19) . . ? C24' C25' C20' 120.47(19) . . ? C6 C1 C2 119.84(18) . . ? C6 C1 N1 115.57(18) . . ? C2 C1 N1 124.58(18) . . ? C7' C8' C9' 176.1(2) . . ? C22 C21 C20 120.25(19) . . ? C6' C1' C2' 119.80(18) . . ? C6' C1' N1' 115.68(18) . . ? C2' C1' N1' 124.51(18) . . ? C25 C24 C23 120.08(19) . . ? C21' C20' C25' 118.84(19) . . ? C21' C20' C9' 120.87(17) . . ? C25' C20' C9' 120.28(17) . . ? C15 C10 C11 118.64(18) . . ? C15 C10 C9 120.36(17) . . ? C11 C10 C9 120.97(17) . . ? C13' C14' C15' 120.3(2) . . ? C6 C5 C4 120.14(19) . . ? C10' C15' C14' 120.55(19) . . ? C25 C20 C21 118.78(19) . . ? C25 C20 C9 119.49(17) . . ? C21 C20 C9 121.71(17) . . ? C12 C11 C10 120.46(19) . . ? C14' C13' C12' 119.2(2) . . ? C23 C22 C21 120.8(2) . . ? C24' C23' C22' 119.3(2) . . ? C5' C6' C1' 120.56(19) . . ? C13 C12 C11 120.32(19) . . ? C5 C4 C3 119.22(18) . . ? C5 C4 C7 120.24(18) . . ? C3 C4 C7 120.53(19) . . ? C6' C5' C4' 120.05(19) . . ? C14 C13 C12 119.5(2) . . ? C24 C25 C20 120.7(2) . . ? C22 C23 C24 119.4(2) . . ? C11' C12' C13' 121.1(2) . . ? C23' C24' C25' 120.63(19) . . ? O2G S2G C5G 104.73(10) . . ? O2G S2G C4G 106.66(9) . . ? C5G S2G C4G 97.89(11) . . ? O1G S1G C2G 108.01(13) . . ? O1G S1G C1G 107.51(11) . . ? C2G S1G C1G 99.16(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1' N1' N1 C1 179.37(16) . . . . ? C9 C8 C7 C4 -40(10) . . . . ? C7 C8 C9 O1 -54(2) . . . . ? C7 C8 C9 C20 62(2) . . . . ? C7 C8 C9 C10 -176(2) . . . . ? C4' C3' C2' C1' 0.1(3) . . . . ? C2' C3' C4' C5' -1.0(3) . . . . ? C2' C3' C4' C7' 179.68(19) . . . . ? C5' C4' C7' C8' -141(8) . . . . ? C3' C4' C7' C8' 38(9) . . . . ? C15' C10' C9' O1' 126.96(19) . . . . ? C11' C10' C9' O1' -54.4(2) . . . . ? C15' C10' C9' C8' 8.2(3) . . . . ? C11' C10' C9' C8' -173.13(18) . . . . ? C15' C10' C9' C20' -113.2(2) . . . . ? C11' C10' C9' C20' 65.5(2) . . . . ? C13 C14 C15 C10 -1.4(3) . . . . ? C15' C10' C11' C12' 0.2(3) . . . . ? C9' C10' C11' C12' -178.53(19) . . . . ? C4 C3 C2 C1 -1.0(3) . . . . ? C23' C22' C21' C20' 0.8(3) . . . . ? C5 C6 C1 C2 2.7(3) . . . . ? C5 C6 C1 N1 -177.85(19) . . . . ? C3 C2 C1 C6 -1.4(3) . . . . ? C3 C2 C1 N1 179.20(19) . . . . ? N1' N1 C1 C6 168.75(18) . . . . ? N1' N1 C1 C2 -11.8(3) . . . . ? C4' C7' C8' C9' 133(7) . . . . ? O1' C9' C8' C7' 54(3) . . . . ? C10' C9' C8' C7' 171(3) . . . . ? C20' C9' C8' C7' -67(3) . . . . ? C3' C2' C1' C6' 0.7(3) . . . . ? C3' C2' C1' N1' -178.30(19) . . . . ? N1 N1' C1' C6' -177.78(19) . . . . ? N1 N1' C1' C2' 1.3(3) . . . . ? C22' C21' C20' C25' 1.5(3) . . . . ? C22' C21' C20' C9' -178.82(17) . . . . ? C24' C25' C20' C21' -2.5(3) . . . . ? C24' C25' C20' C9' 177.83(18) . . . . ? O1' C9' C20' C21' 21.0(2) . . . . ? C8' C9' C20' C21' 140.47(18) . . . . ? C10' C9' C20' C21' -96.1(2) . . . . ? O1' C9' C20' C25' -159.36(17) . . . . ? C8' C9' C20' C25' -39.9(2) . . . . ? C10' C9' C20' C25' 83.5(2) . . . . ? C14 C15 C10 C11 1.4(3) . . . . ? C14 C15 C10 C9 179.78(18) . . . . ? O1 C9 C10 C15 14.9(2) . . . . ? C8 C9 C10 C15 134.98(18) . . . . ? C20 C9 C10 C15 -103.1(2) . . . . ? O1 C9 C10 C11 -166.77(17) . . . . ? C8 C9 C10 C11 -46.7(2) . . . . ? C20 C9 C10 C11 75.2(2) . . . . ? C1 C6 C5 C4 -1.6(3) . . . . ? C11' C10' C15' C14' 1.0(3) . . . . ? C9' C10' C15' C14' 179.71(19) . . . . ? C13' C14' C15' C10' -1.1(3) . . . . ? C22 C21 C20 C25 0.9(3) . . . . ? C22 C21 C20 C9 179.39(18) . . . . ? O1 C9 C20 C25 -40.4(2) . . . . ? C8 C9 C20 C25 -157.36(17) . . . . ? C10 C9 C20 C25 79.9(2) . . . . ? O1 C9 C20 C21 141.12(18) . . . . ? C8 C9 C20 C21 24.1(2) . . . . ? C10 C9 C20 C21 -98.6(2) . . . . ? C15 C10 C11 C12 -0.3(3) . . . . ? C9 C10 C11 C12 -178.69(18) . . . . ? C15' C14' C13' C12' -0.1(3) . . . . ? C20 C21 C22 C23 -0.2(3) . . . . ? C21' C22' C23' C24' -2.2(3) . . . . ? C2' C1' C6' C5' -0.6(3) . . . . ? N1' C1' C6' C5' 178.49(19) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C6 C5 C4 C3 -0.7(3) . . . . ? C6 C5 C4 C7 179.97(19) . . . . ? C2 C3 C4 C5 2.0(3) . . . . ? C2 C3 C4 C7 -178.66(19) . . . . ? C8 C7 C4 C5 64(9) . . . . ? C8 C7 C4 C3 -115(9) . . . . ? C1' C6' C5' C4' -0.3(3) . . . . ? C3' C4' C5' C6' 1.1(3) . . . . ? C7' C4' C5' C6' -179.6(2) . . . . ? C15 C14 C13 C12 0.4(3) . . . . ? C11 C12 C13 C14 0.7(3) . . . . ? C23 C24 C25 C20 -0.4(3) . . . . ? C21 C20 C25 C24 -0.6(3) . . . . ? C9 C20 C25 C24 -179.13(18) . . . . ? C21 C22 C23 C24 -0.7(3) . . . . ? C25 C24 C23 C22 1.0(3) . . . . ? C10' C11' C12' C13' -1.4(3) . . . . ? C14' C13' C12' C11' 1.4(3) . . . . ? C22' C23' C24' C25' 1.2(3) . . . . ? C20' C25' C24' C23' 1.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.320 _refine_diff_density_min -0.651 _refine_diff_density_rms 0.063