# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2002 data_c29h24n2 _database_code_CSD 194360 # 0. AUDIT DETAILS _audit_creation_date '2001-04-04 15:18:49' _audit_creation_method 'PLATON <TABLE ACC> option' _audit_update_record ; ? ; _journal_coden_Cambridge ? loop_ _publ_author_name 'B.L.Feringa' _publ_contact_author_name 'Prof Ben L. Feringa' _publ_contact_author_address ; Organic and Molecular Inorganic Chemistry University of Groningen Nijenborgh 4 Groningen 9747 AG NETHERLANDS ; _publ_contact_author_email 'B.L.FERINGA@CHEM.RUG.NL' _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; A donor-acceptor substituted molecular motor: unidirectional rotation driven by visible light. ; _publ_section_references ; Beurskens, P.T., Beurskens, G., Gelder, R. de Garcia-Granda, S. Gould, R.O. Israel, & Smits, J.M.M. (1999). The DIRDIF99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Bruker, (2000). SMART, SAINT, SADABS, XPREP and SHELXTL/NT. Software Reference Manual Bruker AXS Inc. Madison, Wisconsin, USA. Flack, H.D. (1983). Acta Cryst. A39, 876-881. International Tables for Crystallography (1983). Vol. A. Space-group symmetry, edited by T. Hahn. Dordrecht: Reidel. (Present distributor Kluwer Academic Publishers, Dordrecht). International Tables for Crystallography (1992). Vol. C. Edited by A.J.C Wilson, Kluwer Academic Publishers, Dordrecht, The Netherlands. Le Page, Y. (1987). J. Appl. Cryst. 20, 264-269. Le Page, Y. (1988). J. Appl. Cryst. 21, 983-984. Meetsma, A. (2000). Extended version of the program PLUTO. Groningen University, The Netherlands. (unpublished). Sheldrick, G.M. SHELXL97. Program for Crystal Structure refinement. University of Gottingen, Germany, 1997. Sheldrick, G.M. SADABS. Version 2. Empirical Absorption Correction Program. University of Gottingen, Germany, 2001 Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579. Spek, A.L. (1990). Acta Cryst. A46, C-34. Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht University, The Netherlands. Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66. ; _publ_section_figure_captions ; Fig. 1. Chemical structural diagram (scheme 1) of the title compound Fig. 2. Perspective PLUTO drawing of the molecule illustrating the configuration and the adopted numbering scheme. Fig. 3. Molecular packing viewed down unit cell axes. Fig. 4. Perspective ORTEP drawing of the title compound. All non-hydrogen atoms are represented by thermal vibrational ellipsoids drawn to encompass 50% of the electron density. The hydrogen atoms are drawn with an arbitrary radius. ; #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H24 N2 O2 S2' _chemical_formula_structural ? # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_sum 'C29 H24 N2 O2 S2' _chemical_formula_weight 496.64 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 7.7426(3) _cell_length_b 12.4048(5) _cell_length_c 24.867(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2388.36(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 8722 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 29.58 _cell_special_details ; The final unit cell was obtained from the xyz centroids of 8722 reflections after integration using the SAINT software package (Bruker, 2000). The intensity data were corrected for decay and absorption using SADABS (Sheldrick, 2000). ; _exptl_crystal_description 'platelet' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.520 _exptl_crystal_size_mid 0.440 _exptl_crystal_size_min 0.330 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.254 _exptl_absorpt_correction_type 'Semi-empirical' _exptl_absorpt_process_detais '(SADABS (Sheldrick, Bruker, 2000))' _exptl_absorpt_correction_T_min 0.8792 _exptl_absorpt_correction_T_max 0.9209 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed Siemens Mo tube ' _diffrn_radiation_monochromator 'parallel mounted graphite' _diffrn_radiation_detector ; CCD area-detector ; _diffrn_measurement_device_type ; Bruker Smart Apex Enraf Nonius CAD-4F diffractometer ; _diffrn_measurement_method 'phi and omega scans' _diffrn_special_details ; Crystal into the cold nitrogen stream of the low-temparature unit (KRYOFLEX, (Bruker, 2000)). ; _diffrn_detector_area_resol_mean ' 512x512 / 62x62' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 22638 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 29.69 _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 29.69 _diffrn_measured_fraction_theta_full 0.956 _diffrn_reflns_reduction_process ; Intensity data were corrected for Lorentz and polarization effects, decay and absorption and reduced to F~o~^2^ using SAINT (Bruker, 2000) and SABABS (Sheldrick, 2000) Intensity data were corrected for Lorentz and polarization effects, scale variation, for absorption and reduced to F~o~^2^ ; # number of unique reflections _reflns_number_total 6379 _reflns_number_gt 6253 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker Version 5.168, 2000' _computing_cell_refinement 'SAINT, Bruker Version 6.02A, 2000' _computing_data_reduction 'XPREP, Bruker Version 5.1/NT, 2000' _computing_structure_solution ; DIRDIF-99 (Beurskens et al., 1999) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTO (Meetsma, 2000) PLATON (Spek, 1994) ; _computing_publication_material ; PLATON (Spek, 1990) SHELXL (Sheldrick, 1997) ; #=============================================================================== # 8. REFINEMENT DATA _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_sheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.3510P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary Patterson _atom_sites_solution_secondary direct _atom_sites_solution_hydrogens difmap/geom _refine_ls_hydrogen_treatment refall/mixed/constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.59(4) _refine_ls_number_reflns 6379 _refine_ls_number_parameters 412 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0291 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0769 _refine_ls_wR_factor_gt 0.0763 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.389 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.051 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags S1 S Uani 1.20021(4) 0.22629(2) 0.02101(1) 1.000 0.0189(1) . . S2 S Uani 0.72965(4) 0.68509(2) 0.11201(1) 1.000 0.0173(1) . . O1 O Uani 0.67744(16) 0.15916(8) 0.15771(4) 1.000 0.0291(3) . . O2 O Uani 0.55610(14) 0.21798(9) 0.23076(4) 1.000 0.0270(3) . . N1 N Uani 0.62478(14) 0.23235(9) 0.18667(4) 1.000 0.0198(3) . . N2 N Uani 0.79484(15) 0.60899(9) -0.12482(4) 1.000 0.0183(3) . . C1 C Uani 0.78452(14) 0.46717(8) 0.10709(4) 1.000 0.0124(3) . . C2 C Uani 0.75090(15) 0.36149(9) 0.12354(4) 1.000 0.0138(3) . . C3 C Uani 0.64729(16) 0.34386(9) 0.16819(5) 1.000 0.0159(3) . . C4 C Uani 0.56811(17) 0.42731(11) 0.19643(5) 1.000 0.0189(3) . . C5 C Uani 0.59256(16) 0.53184(10) 0.17852(5) 1.000 0.0177(3) . . C6 C Uani 0.69906(15) 0.55164(9) 0.13392(4) 1.000 0.0140(3) . . C7 C Uani 0.75415(15) 0.66148(9) 0.04230(4) 1.000 0.0141(3) . . C8 C Uani 0.68217(16) 0.73445(9) 0.00631(5) 1.000 0.0174(3) . . C9 C Uani 0.69951(16) 0.72034(9) -0.04904(5) 1.000 0.0180(3) . . C10 C Uani 0.78422(16) 0.62881(9) -0.06958(5) 1.000 0.0150(3) . . C11 C Uani 0.85118(15) 0.55352(9) -0.03244(4) 1.000 0.0135(3) . . C12 C Uani 0.84148(14) 0.56995(8) 0.02310(5) 1.000 0.0124(3) . . C13 C Uani 0.90897(15) 0.49077(8) 0.06295(4) 1.000 0.0117(3) . . C14 C Uani 1.06758(15) 0.44459(9) 0.06188(4) 1.000 0.0120(3) . . C15 C Uani 1.12326(15) 0.36760(9) 0.10429(5) 1.000 0.0133(3) . . C16 C Uani 1.12763(15) 0.39475(10) 0.16050(5) 1.000 0.0153(3) . . C17 C Uani 1.10576(16) 0.50244(10) 0.17915(5) 1.000 0.0181(3) . . C18 C Uani 1.11231(18) 0.52586(12) 0.23331(5) 1.000 0.0229(4) . . C19 C Uani 1.13729(18) 0.44321(13) 0.27155(5) 1.000 0.0267(4) . . C20 C Uani 1.15890(18) 0.33900(12) 0.25471(5) 1.000 0.0240(3) . . C21 C Uani 1.15740(16) 0.31193(11) 0.19915(5) 1.000 0.0186(3) . . C22 C Uani 1.18814(17) 0.20479(11) 0.18111(5) 1.000 0.0220(3) . . C23 C Uani 1.20062(17) 0.18234(10) 0.12746(5) 1.000 0.0205(3) . . C24 C Uani 1.17368(15) 0.26505(9) 0.08851(5) 1.000 0.0154(3) . . C25 C Uani 1.19774(16) 0.35254(9) -0.01698(5) 1.000 0.0163(3) . . C26 C Uani 1.19911(15) 0.45647(9) 0.01700(4) 1.000 0.0136(3) . . C27 C Uani 1.37951(17) 0.48299(10) 0.03874(5) 1.000 0.0188(3) . . C28 C Uani 0.95129(18) 0.55915(11) -0.14616(5) 1.000 0.0209(3) . . C29 C Uani 0.7247(2) 0.69030(12) -0.16081(5) 1.000 0.0273(4) . . H2 H Uiso 0.808(2) 0.3015(14) 0.1054(7) 1.000 0.021(4) . . H4 H Uiso 0.501(2) 0.4099(14) 0.2264(7) 1.000 0.021(4) . . H5 H Uiso 0.538(3) 0.5907(16) 0.1972(7) 1.000 0.027(5) . . H8 H Uiso 0.617(2) 0.7897(14) 0.0201(7) 1.000 0.023(4) . . H9 H Uiso 0.649(2) 0.7729(13) -0.0724(6) 1.000 0.017(4) . . H11 H Uiso 0.902(2) 0.4877(12) -0.0437(6) 1.000 0.014(4) . . H17 H Uiso 1.087(2) 0.5586(15) 0.1534(7) 1.000 0.021(4) . . H18 H Uiso 1.101(3) 0.5984(16) 0.2441(8) 1.000 0.031(5) . . H19 H Uiso 1.139(3) 0.4601(16) 0.3070(8) 1.000 0.028(5) . . H20 H Uiso 1.178(3) 0.2815(19) 0.2780(9) 1.000 0.046(6) . . H22 H Uiso 1.204(2) 0.1470(13) 0.2068(6) 1.000 0.015(4) . . H23 H Uiso 1.224(3) 0.1097(16) 0.1170(8) 1.000 0.033(5) . . H25 H Uiso 1.104(2) 0.3475(14) -0.0389(7) 1.000 0.017(4) . . H25' H Uiso 1.295(2) 0.3512(14) -0.0384(7) 1.000 0.020(4) . . H26 H Uiso 1.166(2) 0.5136(13) -0.0068(6) 1.000 0.015(4) . . H27 H Uiso 1.426(2) 0.4243(14) 0.0602(7) 1.000 0.018(4) . . H27' H Uiso 1.456(3) 0.4954(18) 0.0093(9) 1.000 0.040(6) . . H27" H Uiso 1.376(2) 0.5457(15) 0.0609(7) 1.000 0.025(4) . . H28 H Uiso 0.921(3) 0.5213(16) -0.1798(8) 1.000 0.028(5) . . H28' H Uiso 0.989(3) 0.5090(16) -0.1235(8) 1.000 0.026(5) . . H28" H Uiso 1.034(3) 0.6115(19) -0.1514(9) 1.000 0.044(6) . . H29 H Uiso 0.729(3) 0.6688(16) -0.1943(8) 1.000 0.031(5) . . H29' H Uiso 0.599(3) 0.7049(16) -0.1508(8) 1.000 0.031(5) . . H29" H Uiso 0.788(3) 0.7574(19) -0.1602(8) 1.000 0.043(6) . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0242(2) 0.0138(1) 0.0189(1) -0.0022(1) 0.0008(1) 0.0028(1) S2 0.0234(2) 0.0131(1) 0.0154(1) -0.0027(1) 0.0012(1) 0.0029(1) O1 0.0405(6) 0.0191(4) 0.0277(5) 0.0034(4) 0.0042(4) -0.0054(4) O2 0.0265(5) 0.0343(5) 0.0203(4) 0.0118(4) 0.0037(4) -0.0040(4) N1 0.0186(5) 0.0224(5) 0.0184(5) 0.0058(4) -0.0015(4) -0.0049(4) N2 0.0199(5) 0.0213(5) 0.0138(4) 0.0030(4) -0.0009(4) 0.0023(4) C1 0.0104(4) 0.0145(4) 0.0122(5) 0.0000(4) -0.0007(4) 0.0004(4) C2 0.0127(5) 0.0156(5) 0.0132(5) 0.0006(4) -0.0006(4) -0.0007(4) C3 0.0143(5) 0.0185(5) 0.0148(5) 0.0039(4) -0.0009(4) -0.0030(4) C4 0.0161(5) 0.0272(6) 0.0134(5) 0.0005(4) 0.0018(4) -0.0009(5) C5 0.0160(5) 0.0231(5) 0.0139(5) -0.0028(4) 0.0019(4) 0.0027(4) C6 0.0133(5) 0.0154(4) 0.0134(5) -0.0012(4) -0.0009(4) 0.0009(4) C7 0.0144(5) 0.0136(4) 0.0143(5) -0.0010(4) 0.0008(4) 0.0005(4) C8 0.0183(5) 0.0139(5) 0.0201(5) 0.0004(4) 0.0005(4) 0.0045(4) C9 0.0187(5) 0.0162(5) 0.0191(5) 0.0036(4) -0.0019(4) 0.0032(5) C10 0.0143(5) 0.0153(5) 0.0153(5) 0.0019(4) -0.0007(4) -0.0016(4) C11 0.0130(5) 0.0118(4) 0.0157(5) 0.0002(4) -0.0005(4) -0.0002(4) C12 0.0105(4) 0.0117(4) 0.0149(5) 0.0010(4) -0.0008(4) -0.0001(4) C13 0.0137(5) 0.0109(4) 0.0106(5) -0.0006(4) 0.0004(4) -0.0003(4) C14 0.0129(5) 0.0112(4) 0.0118(5) -0.0009(4) -0.0009(4) -0.0001(4) C15 0.0110(5) 0.0152(5) 0.0137(5) 0.0017(4) -0.0003(4) 0.0006(4) C16 0.0108(5) 0.0201(5) 0.0151(5) 0.0017(4) -0.0008(4) 0.0008(4) C17 0.0151(5) 0.0225(5) 0.0167(5) -0.0012(4) -0.0018(4) -0.0002(4) C18 0.0189(6) 0.0302(7) 0.0195(6) -0.0062(5) -0.0003(5) -0.0002(5) C19 0.0224(6) 0.0436(8) 0.0140(5) -0.0013(5) 0.0000(5) 0.0008(6) C20 0.0194(6) 0.0360(7) 0.0165(5) 0.0070(5) -0.0006(5) 0.0023(5) C21 0.0139(5) 0.0243(5) 0.0175(5) 0.0052(4) -0.0003(4) 0.0017(5) C22 0.0188(6) 0.0239(6) 0.0232(6) 0.0091(5) 0.0007(5) 0.0030(5) C23 0.0195(6) 0.0164(5) 0.0257(6) 0.0043(4) 0.0004(5) 0.0035(5) C24 0.0126(5) 0.0162(5) 0.0175(5) 0.0006(4) -0.0002(4) 0.0018(4) C25 0.0180(5) 0.0159(4) 0.0149(5) -0.0014(4) 0.0016(4) 0.0016(4) C26 0.0119(5) 0.0149(5) 0.0139(5) -0.0006(4) 0.0010(4) 0.0006(4) C27 0.0131(5) 0.0216(6) 0.0216(6) 0.0001(5) -0.0003(4) -0.0012(4) C28 0.0246(6) 0.0211(6) 0.0171(6) 0.0001(4) 0.0036(5) 0.0003(5) C29 0.0337(8) 0.0319(7) 0.0163(6) 0.0071(5) -0.0028(5) 0.0071(6) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C24 1.7581(13) . . yes S1 C25 1.8291(12) . . yes S2 C6 1.7588(11) . . yes S2 C7 1.7683(10) . . yes O1 N1 1.2285(15) . . yes O2 N1 1.2315(14) . . yes N1 C3 1.4680(16) . . yes N2 C10 1.3979(16) . . yes N2 C28 1.4599(18) . . yes N2 C29 1.4537(18) . . yes C1 C2 1.3977(15) . . no C1 C6 1.4074(15) . . no C1 C13 1.4896(15) . . no C2 C3 1.3871(16) . . no C3 C4 1.3930(18) . . no C4 C5 1.3840(18) . . no C5 C6 1.4037(16) . . no C7 C8 1.3896(16) . . no C7 C12 1.4051(15) . . no C8 C9 1.3940(18) . . no C9 C10 1.4072(16) . . no C10 C11 1.4121(16) . . no C11 C12 1.3981(16) . . no C12 C13 1.4899(15) . . no C13 C14 1.3554(16) . . no C14 C15 1.4867(16) . . no C14 C26 1.5180(15) . . no C15 C16 1.4382(18) . . no C15 C24 1.3873(16) . . no C16 C17 1.4242(18) . . no C16 C21 1.4256(18) . . no C17 C18 1.3787(18) . . no C18 C19 1.412(2) . . no C19 C20 1.369(2) . . no C20 C21 1.4219(18) . . no C21 C22 1.4228(19) . . no C22 C23 1.3663(18) . . no C23 C24 1.4263(17) . . no C25 C26 1.5415(16) . . no C26 C27 1.5334(17) . . no C2 H2 0.976(17) . . no C4 H4 0.934(17) . . no C5 H5 0.96(2) . . no C8 H8 0.918(17) . . no C9 H9 0.957(16) . . no C11 H11 0.949(15) . . no C17 H17 0.957(18) . . no C18 H18 0.94(2) . . no C19 H19 0.91(2) . . no C20 H20 0.93(2) . . no C22 H22 0.968(16) . . no C23 H23 0.96(2) . . no C25 H25 0.910(16) . . no C25 H25' 0.923(16) . . no C26 H26 0.958(16) . . no C27 H27 0.972(17) . . no C27 H27' 0.95(2) . . no C27 H27" 0.954(18) . . no C28 H28 0.99(2) . . no C28 H28' 0.89(2) . . no C28 H28" 0.92(2) . . no C29 H29 0.88(2) . . no C29 H29' 1.02(2) . . no C29 H29" 0.97(2) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C24 S1 C25 104.94(5) . . . yes C6 S2 C7 99.34(5) . . . yes O1 N1 O2 123.93(11) . . . yes O1 N1 C3 118.26(10) . . . yes O2 N1 C3 117.80(11) . . . yes C10 N2 C28 118.72(10) . . . yes C10 N2 C29 117.45(10) . . . yes C28 N2 C29 112.34(10) . . . yes C2 C1 C6 118.16(10) . . . no C2 C1 C13 121.36(9) . . . no C6 C1 C13 120.47(9) . . . no C1 C2 C3 119.33(10) . . . no N1 C3 C2 117.89(10) . . . yes N1 C3 C4 119.35(11) . . . yes C2 C3 C4 122.74(11) . . . no C3 C4 C5 118.28(11) . . . no C4 C5 C6 119.90(11) . . . no S2 C6 C1 119.38(8) . . . yes S2 C6 C5 119.25(9) . . . yes C1 C6 C5 121.36(10) . . . no S2 C7 C8 118.72(9) . . . yes S2 C7 C12 121.24(8) . . . yes C8 C7 C12 120.04(10) . . . no C7 C8 C9 121.03(11) . . . no C8 C9 C10 120.30(11) . . . no N2 C10 C9 121.74(11) . . . yes N2 C10 C11 120.32(10) . . . yes C9 C10 C11 117.86(11) . . . no C10 C11 C12 122.00(10) . . . no C7 C12 C11 118.64(10) . . . no C7 C12 C13 118.39(10) . . . no C11 C12 C13 122.83(9) . . . no C1 C13 C12 113.13(9) . . . no C1 C13 C14 121.16(9) . . . no C12 C13 C14 125.69(10) . . . no C13 C14 C15 121.36(10) . . . no C13 C14 C26 125.54(10) . . . no C15 C14 C26 112.91(10) . . . no C14 C15 C16 123.08(10) . . . no C14 C15 C24 118.04(11) . . . no C16 C15 C24 118.88(11) . . . no C15 C16 C17 122.23(11) . . . no C15 C16 C21 119.36(11) . . . no C17 C16 C21 118.40(11) . . . no C16 C17 C18 120.76(12) . . . no C17 C18 C19 120.67(13) . . . no C18 C19 C20 119.77(12) . . . no C19 C20 C21 121.28(12) . . . no C16 C21 C20 119.09(12) . . . no C16 C21 C22 119.19(11) . . . no C20 C21 C22 121.71(12) . . . no C21 C22 C23 120.67(12) . . . no C22 C23 C24 120.41(12) . . . no S1 C24 C15 123.62(9) . . . yes S1 C24 C23 115.76(9) . . . yes C15 C24 C23 120.58(11) . . . no S1 C25 C26 115.65(8) . . . yes C14 C26 C25 108.49(9) . . . no C14 C26 C27 111.88(9) . . . no C25 C26 C27 112.27(10) . . . no C1 C2 H2 119.7(10) . . . no C3 C2 H2 120.8(10) . . . no C3 C4 H4 118.4(11) . . . no C5 C4 H4 123.3(11) . . . no C4 C5 H5 119.7(12) . . . no C6 C5 H5 120.4(12) . . . no C7 C8 H8 117.8(11) . . . no C9 C8 H8 121.0(11) . . . no C8 C9 H9 118.3(9) . . . no C10 C9 H9 121.3(9) . . . no C10 C11 H11 121.9(9) . . . no C12 C11 H11 116.1(9) . . . no C16 C17 H17 118.9(11) . . . no C18 C17 H17 120.4(11) . . . no C17 C18 H18 118.4(12) . . . no C19 C18 H18 120.9(12) . . . no C18 C19 H19 119.3(13) . . . no C20 C19 H19 120.9(13) . . . no C19 C20 H20 123.6(14) . . . no C21 C20 H20 115.2(14) . . . no C21 C22 H22 120.3(9) . . . no C23 C22 H22 119.0(9) . . . no C22 C23 H23 118.1(12) . . . no C24 C23 H23 121.4(12) . . . no S1 C25 H25 105.0(11) . . . no S1 C25 H25' 105.9(11) . . . no C26 C25 H25 113.0(11) . . . no C26 C25 H25' 109.0(11) . . . no H25 C25 H25' 107.7(15) . . . no C14 C26 H26 110.3(9) . . . no C25 C26 H26 106.1(9) . . . no C27 C26 H26 107.6(9) . . . no C26 C27 H27 111.7(10) . . . no C26 C27 H27' 109.2(14) . . . no C26 C27 H27" 110.7(9) . . . no H27 C27 H27' 108.2(17) . . . no H27 C27 H27" 107.7(15) . . . no H27' C27 H27" 109.2(17) . . . no N2 C28 H28 108.2(13) . . . no N2 C28 H28' 109.8(14) . . . no N2 C28 H28" 109.2(14) . . . no H28 C28 H28' 106.4(18) . . . no H28 C28 H28" 112.4(19) . . . no H28' C28 H28" 111(2) . . . no N2 C29 H29 111.1(14) . . . no N2 C29 H29' 109.2(11) . . . no N2 C29 H29" 113.5(13) . . . no H29 C29 H29' 108.8(19) . . . no H29 C29 H29" 105.0(18) . . . no H29' C29 H29" 109.1(18) . . . no 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 C25 S1 C24 C15 12.77(12) . . . . no C25 S1 C24 C23 -169.70(9) . . . . no C24 S1 C25 C26 7.83(10) . . . . no C7 S2 C6 C1 33.38(10) . . . . no C7 S2 C6 C5 -147.90(10) . . . . no C6 S2 C7 C8 141.86(10) . . . . no C6 S2 C7 C12 -36.91(11) . . . . no O1 N1 C3 C4 171.19(12) . . . . no O1 N1 C3 C2 -10.22(17) . . . . no O2 N1 C3 C4 -9.77(17) . . . . no O2 N1 C3 C2 168.81(11) . . . . no C28 N2 C10 C11 -38.86(17) . . . . no C29 N2 C10 C9 3.94(18) . . . . no C28 N2 C10 C9 144.56(12) . . . . no C29 N2 C10 C11 -179.47(12) . . . . no C6 C1 C13 C12 -47.10(13) . . . . no C6 C1 C2 C3 -5.45(16) . . . . no C13 C1 C2 C3 173.70(10) . . . . no C2 C1 C6 S2 -176.72(8) . . . . no C2 C1 C6 C5 4.58(16) . . . . no C13 C1 C6 S2 4.12(14) . . . . no C13 C1 C6 C5 -174.58(10) . . . . no C2 C1 C13 C12 133.77(10) . . . . no C2 C1 C13 C14 -47.75(15) . . . . no C6 C1 C13 C14 131.38(11) . . . . no C1 C2 C3 N1 -175.69(10) . . . . no C1 C2 C3 C4 2.85(18) . . . . no C2 C3 C4 C5 0.89(19) . . . . no N1 C3 C4 C5 179.41(11) . . . . no C3 C4 C5 C6 -1.84(18) . . . . no C4 C5 C6 S2 -179.60(10) . . . . no C4 C5 C6 C1 -0.91(18) . . . . no C8 C7 C12 C11 -1.11(17) . . . . no C12 C7 C8 C9 -2.00(18) . . . . no C8 C7 C12 C13 -176.91(10) . . . . no S2 C7 C8 C9 179.21(9) . . . . no S2 C7 C12 C11 177.65(9) . . . . no S2 C7 C12 C13 1.85(15) . . . . no C7 C8 C9 C10 2.84(18) . . . . no C8 C9 C10 C11 -0.53(18) . . . . no C8 C9 C10 N2 176.14(11) . . . . no N2 C10 C11 C12 -179.35(11) . . . . no C9 C10 C11 C12 -2.64(17) . . . . no C10 C11 C12 C7 3.46(17) . . . . no C10 C11 C12 C13 179.06(11) . . . . no C11 C12 C13 C1 -132.40(11) . . . . no C7 C12 C13 C1 43.21(13) . . . . no C7 C12 C13 C14 -135.18(12) . . . . no C11 C12 C13 C14 49.21(16) . . . . no C1 C13 C14 C26 175.32(10) . . . . no C1 C13 C14 C15 0.71(16) . . . . no C12 C13 C14 C15 178.99(10) . . . . no C12 C13 C14 C26 -6.40(18) . . . . no C26 C14 C15 C16 126.91(11) . . . . no C13 C14 C15 C16 -57.85(16) . . . . no C13 C14 C15 C24 122.37(12) . . . . no C13 C14 C26 C25 -103.00(13) . . . . no C13 C14 C26 C27 132.60(12) . . . . no C26 C14 C15 C24 -52.87(14) . . . . no C15 C14 C26 C27 -52.40(13) . . . . no C15 C14 C26 C25 72.00(12) . . . . no C14 C15 C16 C21 170.60(11) . . . . no C14 C15 C16 C17 -10.38(18) . . . . no C16 C15 C24 C23 10.72(17) . . . . no C14 C15 C24 S1 7.94(16) . . . . no C24 C15 C16 C17 169.40(11) . . . . no C24 C15 C16 C21 -9.62(17) . . . . no C14 C15 C24 C23 -169.48(11) . . . . no C16 C15 C24 S1 -171.86(9) . . . . no C15 C16 C21 C20 -179.03(11) . . . . no C21 C16 C17 C18 -0.35(18) . . . . no C15 C16 C17 C18 -179.37(12) . . . . no C17 C16 C21 C22 -176.88(11) . . . . no C15 C16 C21 C22 2.18(17) . . . . no C17 C16 C21 C20 1.91(18) . . . . no C16 C17 C18 C19 -1.3(2) . . . . no C17 C18 C19 C20 1.4(2) . . . . no C18 C19 C20 C21 0.2(2) . . . . no C19 C20 C21 C16 -1.9(2) . . . . no C19 C20 C21 C22 176.87(13) . . . . no C20 C21 C22 C23 -174.41(13) . . . . no C16 C21 C22 C23 4.35(19) . . . . no C21 C22 C23 C24 -3.4(2) . . . . no C22 C23 C24 C15 -4.30(19) . . . . no C22 C23 C24 S1 178.09(10) . . . . no S1 C25 C26 C27 78.10(11) . . . . no S1 C25 C26 C14 -46.07(12) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 C11 3.6735(12) . 3_555 no S1 H27 3.168(17) . . no S1 H11 3.131(15) . 3_555 no S2 H28" 3.10(2) . 3_465 no S2 H20 3.07(2) . 4_755 no O1 C28 3.2376(17) . 3_455 no O2 C21 3.3920(17) . 1_455 no O2 C29 3.3831(17) . 2_665 no O2 C22 3.1093(17) . 1_455 no O1 H28' 2.68(2) . 3_455 no O1 H2 2.415(17) . . no O2 H4 2.421(17) . . no O2 H29 2.87(2) . 2_665 no O2 H5 2.497(19) . 4_645 no N1 C22 3.4008(17) . 1_455 no N2 H23 2.77(2) . 3_455 no C1 C16 3.1030(16) . . no C1 C17 3.0966(16) . . no C1 C27 3.5722(17) . 1_455 no C2 C16 3.0859(16) . . no C2 C17 3.5381(17) . . no C2 C15 2.9235(16) . . no C2 C24 3.5924(16) . . no C4 C16 3.5486(18) . 1_455 no C4 C21 3.4879(18) . 1_455 no C6 C17 3.3990(17) . . no C6 C27 3.5283(17) . 1_455 no C11 C26 3.1965(16) . . no C11 S1 3.6735(12) . 3_455 no C13 C17 3.2699(16) . . no C15 C2 2.9235(16) . . no C16 C4 3.5486(18) . 1_655 no C16 C1 3.1030(16) . . no C16 C2 3.0859(16) . . no C17 C13 3.2699(16) . . no C17 C2 3.5381(17) . . no C17 C1 3.0966(16) . . no C17 C6 3.3990(17) . . no C21 C4 3.4879(18) . 1_655 no C21 O2 3.3920(17) . 1_655 no C22 O2 3.1093(17) . 1_655 no C22 N1 3.4008(17) . 1_655 no C23 C28 3.5996(19) . 3_555 no C24 C27 3.3735(17) . . no C24 C2 3.5924(16) . . no C26 C11 3.1965(16) . . no C27 C6 3.5283(17) . 1_655 no C27 C24 3.3735(17) . . no C27 C1 3.5722(17) . 1_655 no C28 C23 3.5996(19) . 3_455 no C28 O1 3.2376(17) . 3_555 no C29 O2 3.3831(17) . 2_664 no C1 H17 2.846(16) . . no C1 H27 3.057(16) . 1_455 no C2 H27 3.069(16) . 1_455 no C6 H27" 3.092(16) . 1_455 no C6 H17 3.044(16) . . no C9 H29" 2.88(2) . . no C9 H29' 2.65(2) . . no C10 H8 3.029(16) . 3_565 no C11 H8 2.848(16) . 3_565 no C11 H26 2.568(16) . . no C11 H28' 2.56(2) . . no C11 H23 3.08(2) . 3_455 no C12 H8 2.956(16) . 3_565 no C12 H26 2.712(16) . . no C13 H17 2.769(17) . . no C14 H11 2.970(15) . . no C14 H17 2.684(18) . . no C14 H2 2.892(17) . . no C15 H27 2.682(16) . . no C15 H2 2.575(16) . . no C16 H2 3.056(16) . . no C19 H4 3.060(16) . 1_655 no C20 H4 2.878(16) . 1_655 no C21 H4 3.002(16) . 1_655 no C24 H27 2.866(17) . . no C24 H2 2.898(16) . . no C25 H2 3.036(17) . 3_555 no C25 H11 2.915(15) . . no C26 H11 2.779(15) . . no C28 H11 2.724(15) . . no C28 H23 2.83(2) . 3_455 no C29 H9 2.495(15) . . no H2 O1 2.415(17) . . no H2 C14 2.892(17) . . no H2 C15 2.575(16) . . no H2 C16 3.056(16) . . no H2 C24 2.898(16) . . no H2 C25 3.036(17) . 3_455 no H2 H25' 2.52(2) . 3_455 no H4 O2 2.421(17) . . no H4 C19 3.060(16) . 1_455 no H4 C20 2.878(16) . 1_455 no H4 C21 3.002(16) . 1_455 no H4 H28 2.56(3) . 2_665 no H5 O2 2.497(19) . 4_655 no H8 C10 3.029(16) . 3_465 no H8 C11 2.848(16) . 3_465 no H8 C12 2.956(16) . 3_465 no H8 H26 2.49(2) . 3_465 no H9 C29 2.495(15) . . no H9 H29' 2.16(3) . . no H9 H29" 2.44(3) . . no H11 C14 2.970(15) . . no H11 C25 2.915(15) . . no H11 C26 2.779(15) . . no H11 C28 2.724(15) . . no H11 H25 2.34(2) . . no H11 H26 2.26(2) . . no H11 H28' 2.11(3) . . no H11 S1 3.131(15) . 3_455 no H11 H23 2.58(3) . 3_455 no H17 C1 2.846(16) . . no H17 C6 3.044(16) . . no H17 C13 2.769(17) . . no H17 C14 2.684(18) . . no H20 H22 2.44(3) . . no H20 S2 3.07(2) . 4_745 no H22 H20 2.44(3) . . no H23 N2 2.77(2) . 3_555 no H23 C11 3.08(2) . 3_555 no H23 C28 2.83(2) . 3_555 no H23 H11 2.58(3) . 3_555 no H23 H28' 2.53(3) . 3_555 no H25 H11 2.34(2) . . no H25' H27' 2.48(3) . . no H25' H2 2.52(2) . 3_555 no H26 C11 2.568(16) . . no H26 C12 2.712(16) . . no H26 H11 2.26(2) . . no H26 H8 2.49(2) . 3_565 no H27 S1 3.168(17) . . no H27 C1 3.057(16) . 1_655 no H27 C2 3.069(16) . 1_655 no H27 C15 2.682(16) . . no H27 C24 2.866(17) . . no H27' H25' 2.48(3) . . no H27" C6 3.092(16) . 1_655 no H28 H29 2.38(3) . . no H28 H4 2.56(3) . 2_664 no H28' C11 2.56(2) . . no H28' H11 2.11(3) . . no H28' O1 2.68(2) . 3_555 no H28' H23 2.53(3) . 3_455 no H28" S2 3.10(2) . 3_565 no H29 H28 2.38(3) . . no H29 O2 2.87(2) . 2_664 no H29' C9 2.65(2) . . no H29' H9 2.16(3) . . no H29" C9 2.88(2) . . no H29" H9 2.44(3) . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C5 H5 O2 0.96(2) 2.497(19) 3.4272(16) 162.5(15) 4_655 yes # End of Crystallographic Information File