# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2013 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address # Address of author for correspondence ; ? ; _publ_contact_author_email glen.miller@unh.edu _publ_contact_author_fax ? _publ_contact_author_phone ? #TrackingRef 'Pentacene Diacid_3.cif' # Added by publCIF - use a unique identifier for each data block #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Glen P. Miller' # Name of author for correspondence _publ_contact_letter ; ? ; _publ_requested_category ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Pentacene Diacid ; loop_ _publ_author_name C.Pramanik Y.Li A.Singh W.Lin J.L.Hodgson J.L.Briggs ; J.B.Ellis ; P.Muller N.McGruer G.P.Miller #============================================================================== # Formatted by publCIF data_Pentacene_Diacid _database_code_depnum_ccdc_archive 'CCDC 902874' #TrackingRef 'Pentacene Diacid_3.cif' _audit_update_record ; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H22 O4 S2, 2(C2 H4 O2)' _chemical_formula_sum 'C32 H30 O8 S2' _chemical_formula_weight 606.68 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' 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 5.0554(4) _cell_length_b 10.5514(8) _cell_length_c 13.4788(10) _cell_angle_alpha 100.067(2) _cell_angle_beta 94.337(2) _cell_angle_gamma 92.778(2) _cell_volume 704.49(9) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9965 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 30.41 _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9418 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2009)' _exptl_special_details ; Bruker X8 Kappa DUO four-circle diffractometer, Bruker APEX2 CCD. The instrument was purchased with the help of funding from the National Science Foundation (NSF) under Grant Number CHE-0946721. Please acknowledge this grant in all publications of this structure. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'ImuS micro-focus sealed tube' _diffrn_radiation_monochromator 'Incoatech ImuS multilayer optics' _diffrn_measurement_device_type 'Bruker Smart APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 25794 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 30.51 _reflns_number_total 4176 _reflns_number_gt 3313 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2011.4.0 (Bruker-AXS, 2011)' _computing_cell_refinement 'SAINT 7.46A (Bruker-AXS, 2011)' _computing_data_reduction 'SAINT 7.46A (Bruker-AXS, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1264P)^2^+1.4688P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4176 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1669 _refine_ls_wR_factor_gt 0.1410 _refine_ls_goodness_of_fit_ref 0.748 _refine_ls_restrained_S_all 0.748 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0118(4) 0.5044(2) 0.31925(16) 0.0273(4) Uani 1 1 d . . . H1 H 1.0474 0.4157 0.3098 0.033 Uiso 1 1 calc R . . C2 C 0.8374(4) 0.5508(2) 0.38687(16) 0.0260(4) Uani 1 1 d . . . H2 H 0.7525 0.4943 0.4240 0.031 Uiso 1 1 calc R . . C3 C 0.7814(4) 0.68378(18) 0.40225(14) 0.0213(4) Uani 1 1 d . . . C4 C 0.6047(4) 0.73437(18) 0.47043(14) 0.0210(4) Uani 1 1 d . . . H4 H 0.5164 0.6783 0.5071 0.025 Uiso 1 1 calc R . . C5 C 0.5516(4) 0.86658(18) 0.48731(13) 0.0190(3) Uani 1 1 d . . . C6 C 0.3777(4) 0.91820(18) 0.55918(13) 0.0190(3) Uani 1 1 d . . . C7 C 0.3222(4) 1.04983(17) 0.57276(13) 0.0185(3) Uani 1 1 d . . . C8 C 0.1482(4) 1.10463(19) 0.64307(14) 0.0217(4) Uani 1 1 d . . . H8 H 0.0679 1.0513 0.6838 0.026 Uiso 1 1 calc R . . C9 C 0.0896(4) 1.23257(19) 0.65515(14) 0.0207(3) Uani 1 1 d . . . C10 C -0.0950(4) 1.2860(2) 0.72509(15) 0.0252(4) Uani 1 1 d . . . H10 H -0.1848 1.2318 0.7628 0.030 Uiso 1 1 calc R . . C11 C -0.1414(4) 1.4132(2) 0.73747(16) 0.0270(4) Uani 1 1 d . . . H11 H -0.2617 1.4476 0.7845 0.032 Uiso 1 1 calc R . . C12 C 0.4892(4) 0.78049(19) 0.71527(14) 0.0221(4) Uani 1 1 d . . . H12A H 0.4187 0.7242 0.7600 0.027 Uiso 1 1 calc R . . H12B H 0.6172 0.7315 0.6741 0.027 Uiso 1 1 calc R . . C13 C 0.6364(4) 0.89825(18) 0.78048(14) 0.0208(3) Uani 1 1 d . . . H13A H 0.7087 0.9553 0.7367 0.025 Uiso 1 1 calc R . . H13B H 0.5116 0.9470 0.8234 0.025 Uiso 1 1 calc R . . C14 C 0.8597(4) 0.85897(19) 0.84636(14) 0.0215(4) Uani 1 1 d . . . C15 C 0.4336(4) 0.7471(2) 0.00909(15) 0.0273(4) Uani 1 1 d . . . C16 C 0.6546(5) 0.7054(3) 0.07368(18) 0.0347(5) Uani 1 1 d . . . H16A H 0.8041 0.7703 0.0840 0.052 Uiso 1 1 calc R . . H16B H 0.7124 0.6226 0.0401 0.052 Uiso 1 1 calc R . . H16C H 0.5921 0.6960 0.1392 0.052 Uiso 1 1 calc R . . O1 O 0.8831(3) 0.74730(14) 0.85701(11) 0.0260(3) Uani 1 1 d . . . O2 O 1.0265(3) 0.95564(14) 0.89125(11) 0.0254(3) Uani 1 1 d . . . H2A H 1.1417 0.9283 0.9291 0.038 Uiso 1 1 calc R . . O3 O 0.4061(3) 0.85949(16) 0.00284(13) 0.0323(4) Uani 1 1 d . . . O4 O 0.2707(3) 0.65131(17) -0.03928(14) 0.0356(4) Uani 1 1 d . . . H4A H 0.1443 0.6809 -0.0703 0.053 Uiso 1 1 calc R . . S1 S 0.21600(9) 0.81635(5) 0.63114(3) 0.02082(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0250(11) 0.0232(9) 0.0321(10) -0.0007(7) 0.0024(8) 0.0062(7) C2 0.0266(11) 0.0239(9) 0.0273(9) 0.0030(7) 0.0032(7) 0.0043(7) C3 0.0183(9) 0.0236(9) 0.0204(8) -0.0002(6) -0.0006(6) 0.0035(6) C4 0.0184(9) 0.0237(8) 0.0206(8) 0.0025(6) 0.0020(6) 0.0032(6) C5 0.0139(8) 0.0240(9) 0.0180(7) 0.0002(6) -0.0004(6) 0.0035(6) C6 0.0133(8) 0.0243(8) 0.0187(7) 0.0023(6) 0.0007(6) 0.0013(6) C7 0.0136(8) 0.0231(8) 0.0174(7) 0.0003(6) -0.0006(6) 0.0021(6) C8 0.0173(9) 0.0257(9) 0.0220(8) 0.0028(7) 0.0037(6) 0.0041(6) C9 0.0142(8) 0.0260(9) 0.0205(8) 0.0001(6) 0.0000(6) 0.0038(6) C10 0.0176(9) 0.0317(10) 0.0248(9) -0.0003(7) 0.0039(7) 0.0042(7) C11 0.0205(10) 0.0307(10) 0.0279(9) -0.0023(7) 0.0041(7) 0.0061(7) C12 0.0183(9) 0.0255(9) 0.0222(8) 0.0034(7) 0.0000(6) 0.0030(7) C13 0.0151(9) 0.0243(8) 0.0225(8) 0.0020(6) 0.0015(6) 0.0026(6) C14 0.0144(9) 0.0305(9) 0.0191(8) 0.0012(7) 0.0038(6) 0.0033(7) C15 0.0188(10) 0.0398(11) 0.0239(9) 0.0056(8) 0.0034(7) 0.0059(8) C16 0.0244(11) 0.0491(14) 0.0325(11) 0.0124(10) -0.0016(8) 0.0101(9) O1 0.0207(7) 0.0285(7) 0.0283(7) 0.0040(5) -0.0017(5) 0.0051(5) O2 0.0173(7) 0.0308(7) 0.0259(7) 0.0005(5) -0.0023(5) 0.0030(5) O3 0.0238(8) 0.0358(8) 0.0339(8) -0.0011(6) -0.0048(6) 0.0061(6) O4 0.0247(9) 0.0362(9) 0.0456(10) 0.0109(7) -0.0068(7) 0.0032(6) S1 0.0144(2) 0.0256(2) 0.0223(2) 0.00361(16) 0.00180(15) 0.00200(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.362(3) . ? C1 C11 1.422(3) 2_676 ? C1 H1 0.9500 . ? C2 C3 1.427(3) . ? C2 H2 0.9500 . ? C3 C4 1.388(3) . ? C3 C9 1.436(3) 2_676 ? C4 C5 1.416(3) . ? C4 H4 0.9500 . ? C5 C6 1.414(2) . ? C5 C7 1.454(3) 2_676 ? C6 C7 1.413(3) . ? C6 S1 1.7785(19) . ? C7 C8 1.411(2) . ? C7 C5 1.454(3) 2_676 ? C8 C9 1.380(3) . ? C8 H8 0.9500 . ? C9 C3 1.436(3) 2_676 ? C9 C10 1.440(3) . ? C10 C11 1.358(3) . ? C10 H10 0.9500 . ? C11 C1 1.422(3) 2_676 ? C11 H11 0.9500 . ? C12 C13 1.517(3) . ? C12 S1 1.817(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.502(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O1 1.222(2) . ? C14 O2 1.320(2) . ? C15 O3 1.217(3) . ? C15 O4 1.317(3) . ? C15 C16 1.495(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? O2 H2A 0.8400 . ? O4 H4A 0.8400 . ? 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 C2 C1 C11 120.95(19) . 2_676 ? C2 C1 H1 119.5 . . ? C11 C1 H1 119.5 2_676 . ? C1 C2 C3 120.4(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 121.99(19) . . ? C4 C3 C9 119.07(18) . 2_676 ? C2 C3 C9 118.94(18) . 2_676 ? C3 C4 C5 122.30(18) . . ? C3 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C6 C5 C4 121.98(17) . . ? C6 C5 C7 119.66(16) . 2_676 ? C4 C5 C7 118.36(16) . 2_676 ? C7 C6 C5 120.93(17) . . ? C7 C6 S1 118.89(13) . . ? C5 C6 S1 120.14(14) . . ? C8 C7 C6 122.60(17) . . ? C8 C7 C5 118.00(17) . 2_676 ? C6 C7 C5 119.40(16) . 2_676 ? C9 C8 C7 122.73(18) . . ? C9 C8 H8 118.6 . . ? C7 C8 H8 118.6 . . ? C8 C9 C3 119.44(17) . 2_676 ? C8 C9 C10 121.99(18) . . ? C3 C9 C10 118.56(18) 2_676 . ? C11 C10 C9 120.44(19) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C1 120.67(19) . 2_676 ? C10 C11 H11 119.7 . . ? C1 C11 H11 119.7 2_676 . ? C13 C12 S1 114.47(13) . . ? C13 C12 H12A 108.6 . . ? S1 C12 H12A 108.6 . . ? C13 C12 H12B 108.6 . . ? S1 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C14 C13 C12 110.51(16) . . ? C14 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? O1 C14 O2 123.42(18) . . ? O1 C14 C13 122.62(18) . . ? O2 C14 C13 113.96(17) . . ? O3 C15 O4 123.4(2) . . ? O3 C15 C16 122.9(2) . . ? O4 C15 C16 113.7(2) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 O2 H2A 109.5 . . ? C15 O4 H4A 109.5 . . ? C6 S1 C12 102.16(9) . . ? 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 C11 C1 C2 C3 -0.1(3) 2_676 . . . ? C1 C2 C3 C4 180.0(2) . . . . ? C1 C2 C3 C9 0.4(3) . . . 2_676 ? C2 C3 C4 C5 178.92(18) . . . . ? C9 C3 C4 C5 -1.5(3) 2_676 . . . ? C3 C4 C5 C6 -177.99(18) . . . . ? C3 C4 C5 C7 3.0(3) . . . 2_676 ? C4 C5 C6 C7 -178.29(17) . . . . ? C7 C5 C6 C7 0.7(3) 2_676 . . . ? C4 C5 C6 S1 -0.4(3) . . . . ? C7 C5 C6 S1 178.57(13) 2_676 . . . ? C5 C6 C7 C8 179.46(17) . . . . ? S1 C6 C7 C8 1.6(3) . . . . ? C5 C6 C7 C5 -0.7(3) . . . 2_676 ? S1 C6 C7 C5 -178.59(13) . . . 2_676 ? C6 C7 C8 C9 -178.72(18) . . . . ? C5 C7 C8 C9 1.5(3) 2_676 . . . ? C7 C8 C9 C3 -3.0(3) . . . 2_676 ? C7 C8 C9 C10 178.04(18) . . . . ? C8 C9 C10 C11 177.84(19) . . . . ? C3 C9 C10 C11 -1.2(3) 2_676 . . . ? C9 C10 C11 C1 0.9(3) . . . 2_676 ? S1 C12 C13 C14 -179.39(13) . . . . ? C12 C13 C14 O1 -11.9(2) . . . . ? C12 C13 C14 O2 168.12(15) . . . . ? C7 C6 S1 C12 -111.35(15) . . . . ? C5 C6 S1 C12 70.76(16) . . . . ? C13 C12 S1 C6 57.64(15) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.670 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.082 data_jb1222 _database_code_depnum_ccdc_archive 'CCDC 902875' #TrackingRef 'Compound2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 O4 S2' _chemical_formula_sum 'C28 H24 O4 S2' _chemical_formula_weight 488.59 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' 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 9.2953(19) _cell_length_b 26.199(5) _cell_length_c 9.9218(17) _cell_angle_alpha 90.00 _cell_angle_beta 98.104(7) _cell_angle_gamma 90.00 _cell_volume 2392.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 3842 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 21.89 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9045 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'XOS X-beam microfocus source' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'Bruker SMART X2S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25095 _diffrn_reflns_av_R_equivalents 0.0616 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.45 _reflns_number_total 4372 _reflns_number_gt 2829 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker GIS' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0388P)^2^+0.6956P] 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 4372 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.20564(8) 0.38635(3) 0.57168(7) 0.0527(2) Uani 1 1 d . . . S2 S -0.02808(7) 0.31875(3) 0.78778(8) 0.0550(2) Uani 1 1 d . . . O1 O 0.1949(3) 0.55571(8) 0.6273(3) 0.0938(8) Uani 1 1 d . . . O2 O 0.3529(2) 0.57235(8) 0.4873(2) 0.0685(6) Uani 1 1 d . . . H2 H 0.313(4) 0.6094(16) 0.502(4) 0.146(15) Uiso 1 1 d . . . O3 O -0.2655(2) 0.16798(7) 0.9872(2) 0.0619(5) Uani 1 1 d . . . O4 O -0.1133(2) 0.14917(9) 0.8406(2) 0.0695(6) Uani 1 1 d . . . H4 H -0.139(5) 0.1151(16) 0.851(4) 0.153(18) Uiso 1 1 d . . . C1 C 0.4010(3) 0.15948(11) 0.7670(3) 0.0585(8) Uani 1 1 d . . . H1 H 0.349(3) 0.1422(9) 0.821(2) 0.044(7) Uiso 1 1 d . . . C2 C 0.4913(3) 0.13533(12) 0.6911(3) 0.0633(8) Uani 1 1 d . . . H2A H 0.503(3) 0.0990(11) 0.700(3) 0.063(8) Uiso 1 1 d . . . C3 C 0.5678(3) 0.16338(12) 0.6047(3) 0.0647(9) Uani 1 1 d . . . H3 H 0.629(3) 0.1465(10) 0.556(3) 0.066(9) Uiso 1 1 d . . . C4 C 0.5542(3) 0.21476(12) 0.5973(3) 0.0579(8) Uani 1 1 d . . . H4A H 0.598(3) 0.2314(10) 0.542(3) 0.056(9) Uiso 1 1 d . . . C5 C 0.4619(3) 0.24115(10) 0.6753(3) 0.0474(6) Uani 1 1 d . . . C6 C 0.4460(3) 0.29464(10) 0.6706(3) 0.0486(7) Uani 1 1 d . . . H6 H 0.496(3) 0.3118(8) 0.619(2) 0.043(7) Uiso 1 1 d . . . C7 C 0.3505(2) 0.31951(9) 0.7405(2) 0.0425(6) Uani 1 1 d . . . C8 C 0.3336(3) 0.37638(10) 0.7302(3) 0.0453(6) Uani 1 1 d . . . H8 H 0.423(2) 0.3905(8) 0.719(2) 0.041(6) Uiso 1 1 d . . . C9 C 0.2806(2) 0.40064(9) 0.8514(2) 0.0417(6) Uani 1 1 d . . . C10 C 0.3174(3) 0.44972(10) 0.8881(3) 0.0479(7) Uani 1 1 d . . . H10 H 0.381(3) 0.4667(9) 0.842(2) 0.055(8) Uiso 1 1 d . . . C11 C 0.2601(3) 0.47492(10) 0.9948(3) 0.0469(6) Uani 1 1 d . . . C12 C 0.2910(3) 0.52643(11) 1.0292(3) 0.0599(8) Uani 1 1 d . . . H12 H 0.357(3) 0.5414(10) 0.981(3) 0.063(8) Uiso 1 1 d . . . C13 C 0.2285(3) 0.55004(13) 1.1272(3) 0.0663(9) Uani 1 1 d . . . H13 H 0.248(3) 0.5839(11) 1.147(3) 0.073(10) Uiso 1 1 d . . . C14 C 0.1305(4) 0.52354(13) 1.1964(3) 0.0663(9) Uani 1 1 d . . . H14 H 0.089(3) 0.5419(10) 1.260(3) 0.061(8) Uiso 1 1 d . . . C15 C 0.0989(3) 0.47419(13) 1.1679(3) 0.0592(8) Uani 1 1 d . . . H15 H 0.039(3) 0.4561(10) 1.212(3) 0.058(8) Uiso 1 1 d . . . C16 C 0.1620(3) 0.44783(10) 1.0663(2) 0.0472(6) Uani 1 1 d . . . C17 C 0.1320(3) 0.39648(11) 1.0310(3) 0.0479(7) Uani 1 1 d . . . H17 H 0.073(2) 0.3779(8) 1.077(2) 0.032(6) Uiso 1 1 d . . . C18 C 0.1881(2) 0.37287(9) 0.9269(2) 0.0421(6) Uani 1 1 d . . . C19 C 0.1529(3) 0.31796(10) 0.8924(3) 0.0441(6) Uani 1 1 d . . . H19 H 0.138(2) 0.3003(8) 0.972(2) 0.036(6) Uiso 1 1 d . . . C20 C 0.2647(2) 0.29104(9) 0.8215(2) 0.0410(6) Uani 1 1 d . . . C21 C 0.2844(3) 0.23955(10) 0.8323(3) 0.0471(7) Uani 1 1 d . . . H21 H 0.235(3) 0.2214(9) 0.890(2) 0.053(8) Uiso 1 1 d . . . C22 C 0.3817(3) 0.21290(9) 0.7601(3) 0.0452(6) Uani 1 1 d . . . C23 C 0.1788(3) 0.45402(9) 0.5668(3) 0.0506(7) Uani 1 1 d . . . H23A H 0.0946 0.4615 0.5003 0.061 Uiso 1 1 calc R . . H23B H 0.1564 0.4649 0.6550 0.061 Uiso 1 1 calc R . . C24 C 0.3058(3) 0.48587(9) 0.5323(3) 0.0528(7) Uani 1 1 d . . . H24A H 0.3940 0.4755 0.5899 0.063 Uiso 1 1 calc R . . H24B H 0.3189 0.4798 0.4384 0.063 Uiso 1 1 calc R . . C25 C 0.2806(3) 0.54121(10) 0.5522(3) 0.0516(7) Uani 1 1 d . . . C26 C -0.0810(3) 0.25272(10) 0.7853(3) 0.0528(7) Uani 1 1 d . . . H26A H -0.1670 0.2483 0.7186 0.063 Uiso 1 1 calc R . . H26B H -0.0039 0.2323 0.7563 0.063 Uiso 1 1 calc R . . C27 C -0.1127(3) 0.23317(11) 0.9207(3) 0.0665(9) Uani 1 1 d . . . H27A H -0.0237 0.2343 0.9848 0.080 Uiso 1 1 calc R . . H27B H -0.1819 0.2559 0.9541 0.080 Uiso 1 1 calc R . . C28 C -0.1716(3) 0.18035(10) 0.9179(3) 0.0499(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0683(5) 0.0445(4) 0.0459(4) 0.0038(3) 0.0108(3) -0.0024(3) S2 0.0416(4) 0.0505(4) 0.0722(5) 0.0047(4) 0.0060(3) -0.0074(3) O1 0.1225(19) 0.0496(13) 0.129(2) -0.0012(13) 0.0850(17) 0.0016(12) O2 0.0760(14) 0.0461(12) 0.0923(16) 0.0042(11) 0.0432(12) 0.0005(10) O3 0.0611(12) 0.0578(12) 0.0726(13) -0.0044(10) 0.0296(11) -0.0151(9) O4 0.0812(15) 0.0553(14) 0.0796(15) 0.0000(12) 0.0374(12) -0.0012(11) C1 0.0622(19) 0.0479(19) 0.064(2) 0.0064(15) 0.0042(16) -0.0009(15) C2 0.071(2) 0.0446(19) 0.070(2) -0.0029(17) -0.0028(18) 0.0096(16) C3 0.0573(19) 0.062(2) 0.074(2) -0.0121(18) 0.0076(17) 0.0157(16) C4 0.0490(17) 0.062(2) 0.064(2) -0.0006(16) 0.0111(16) 0.0026(15) C5 0.0389(14) 0.0511(17) 0.0511(16) -0.0001(13) 0.0023(12) 0.0026(12) C6 0.0443(15) 0.0506(18) 0.0527(17) 0.0067(14) 0.0126(14) -0.0044(13) C7 0.0407(13) 0.0431(15) 0.0438(15) 0.0027(12) 0.0063(12) -0.0027(12) C8 0.0434(15) 0.0450(16) 0.0496(17) 0.0055(12) 0.0137(13) -0.0060(12) C9 0.0397(14) 0.0453(16) 0.0399(15) 0.0016(12) 0.0053(12) -0.0047(11) C10 0.0462(16) 0.0501(17) 0.0489(17) 0.0014(13) 0.0118(13) -0.0091(13) C11 0.0440(15) 0.0514(17) 0.0438(16) -0.0031(13) 0.0007(12) -0.0046(12) C12 0.0600(19) 0.0529(19) 0.068(2) -0.0078(16) 0.0141(17) -0.0101(15) C13 0.069(2) 0.055(2) 0.074(2) -0.0185(18) 0.0079(18) -0.0048(17) C14 0.069(2) 0.072(2) 0.059(2) -0.0201(17) 0.0123(17) 0.0033(18) C15 0.0557(18) 0.073(2) 0.0506(19) -0.0069(16) 0.0142(15) -0.0065(16) C16 0.0450(15) 0.0551(17) 0.0404(16) -0.0023(13) 0.0023(13) -0.0019(13) C17 0.0441(15) 0.0591(19) 0.0422(16) 0.0057(14) 0.0118(13) -0.0061(13) C18 0.0386(14) 0.0458(15) 0.0416(15) 0.0025(12) 0.0049(12) -0.0048(11) C19 0.0426(14) 0.0475(16) 0.0439(16) 0.0077(13) 0.0116(12) -0.0070(12) C20 0.0378(14) 0.0423(16) 0.0422(15) 0.0030(12) 0.0038(12) -0.0050(11) C21 0.0484(16) 0.0447(17) 0.0489(17) 0.0055(13) 0.0093(13) -0.0056(13) C22 0.0417(15) 0.0449(16) 0.0460(16) 0.0025(12) -0.0040(12) -0.0013(12) C23 0.0535(16) 0.0484(16) 0.0519(17) 0.0070(13) 0.0148(13) 0.0082(13) C24 0.0583(17) 0.0457(16) 0.0575(17) 0.0105(13) 0.0196(14) 0.0087(13) C25 0.0525(16) 0.0473(17) 0.0576(18) 0.0020(14) 0.0170(14) 0.0010(13) C26 0.0499(16) 0.0586(18) 0.0515(17) -0.0037(13) 0.0127(13) -0.0166(13) C27 0.078(2) 0.065(2) 0.063(2) -0.0096(15) 0.0329(17) -0.0243(16) C28 0.0511(16) 0.0521(17) 0.0485(16) -0.0016(14) 0.0137(14) -0.0081(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C23 1.790(3) . ? S1 C8 1.852(3) . ? S2 C26 1.798(3) . ? S2 C19 1.848(3) . ? O1 C25 1.225(3) . ? O2 C25 1.286(3) . ? O2 H2 1.06(4) . ? O3 C28 1.229(3) . ? O4 C28 1.291(3) . ? O4 H4 0.93(4) . ? C1 C2 1.360(4) . ? C1 C22 1.412(4) . ? C1 H1 0.89(2) . ? C2 C3 1.397(4) . ? C2 H2A 0.96(3) . ? C3 C4 1.353(4) . ? C3 H3 0.91(3) . ? C4 C5 1.414(4) . ? C4 H4A 0.85(3) . ? C5 C6 1.409(3) . ? C5 C22 1.410(3) . ? C6 C7 1.366(3) . ? C6 H6 0.86(2) . ? C7 C20 1.421(3) . ? C7 C8 1.500(3) . ? C8 C9 1.503(3) . ? C8 H8 0.93(2) . ? C9 C10 1.367(3) . ? C9 C18 1.419(3) . ? C10 C11 1.413(3) . ? C10 H10 0.92(2) . ? C11 C12 1.412(4) . ? C11 C16 1.422(3) . ? C12 C13 1.351(4) . ? C12 H12 0.92(3) . ? C13 C14 1.400(4) . ? C13 H13 0.92(3) . ? C14 C15 1.347(4) . ? C14 H14 0.92(3) . ? C15 C16 1.416(4) . ? C15 H15 0.89(3) . ? C16 C17 1.408(4) . ? C17 C18 1.369(3) . ? C17 H17 0.90(2) . ? C18 C19 1.504(3) . ? C19 C20 1.508(3) . ? C19 H19 0.94(2) . ? C20 C21 1.364(3) . ? C21 C22 1.415(3) . ? C21 H21 0.91(2) . ? C23 C24 1.523(3) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.486(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C26 C27 1.505(3) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.487(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? 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 C23 S1 C8 103.47(12) . . ? C26 S2 C19 102.87(12) . . ? C25 O2 H2 107(2) . . ? C28 O4 H4 114(3) . . ? C2 C1 C22 121.2(3) . . ? C2 C1 H1 121.6(15) . . ? C22 C1 H1 117.1(15) . . ? C1 C2 C3 120.1(3) . . ? C1 C2 H2A 118.8(16) . . ? C3 C2 H2A 121.0(16) . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 120.8(17) . . ? C2 C3 H3 118.8(17) . . ? C3 C4 C5 121.0(3) . . ? C3 C4 H4A 119.7(18) . . ? C5 C4 H4A 119.2(18) . . ? C6 C5 C22 118.7(2) . . ? C6 C5 C4 122.5(2) . . ? C22 C5 C4 118.9(3) . . ? C7 C6 C5 122.0(2) . . ? C7 C6 H6 119.6(15) . . ? C5 C6 H6 118.3(15) . . ? C6 C7 C20 119.6(2) . . ? C6 C7 C8 120.6(2) . . ? C20 C7 C8 119.9(2) . . ? C7 C8 C9 114.1(2) . . ? C7 C8 S1 104.26(17) . . ? C9 C8 S1 112.10(17) . . ? C7 C8 H8 108.4(13) . . ? C9 C8 H8 109.1(13) . . ? S1 C8 H8 108.6(14) . . ? C10 C9 C18 119.3(2) . . ? C10 C9 C8 120.9(2) . . ? C18 C9 C8 119.8(2) . . ? C9 C10 C11 122.2(2) . . ? C9 C10 H10 118.6(15) . . ? C11 C10 H10 119.2(15) . . ? C12 C11 C10 122.9(2) . . ? C12 C11 C16 118.6(2) . . ? C10 C11 C16 118.4(2) . . ? C13 C12 C11 121.2(3) . . ? C13 C12 H12 124.5(17) . . ? C11 C12 H12 114.2(17) . . ? C12 C13 C14 120.1(3) . . ? C12 C13 H13 120.5(18) . . ? C14 C13 H13 119.3(18) . . ? C15 C14 C13 120.7(3) . . ? C15 C14 H14 123.2(17) . . ? C13 C14 H14 116.1(17) . . ? C14 C15 C16 121.2(3) . . ? C14 C15 H15 122.4(17) . . ? C16 C15 H15 116.3(17) . . ? C17 C16 C15 123.7(2) . . ? C17 C16 C11 118.1(2) . . ? C15 C16 C11 118.1(3) . . ? C18 C17 C16 122.4(2) . . ? C18 C17 H17 117.5(13) . . ? C16 C17 H17 120.1(13) . . ? C17 C18 C9 119.4(2) . . ? C17 C18 C19 120.7(2) . . ? C9 C18 C19 119.9(2) . . ? C18 C19 C20 114.30(19) . . ? C18 C19 S2 105.59(17) . . ? C20 C19 S2 112.07(17) . . ? C18 C19 H19 109.4(13) . . ? C20 C19 H19 110.6(13) . . ? S2 C19 H19 104.3(13) . . ? C21 C20 C7 118.9(2) . . ? C21 C20 C19 121.3(2) . . ? C7 C20 C19 119.8(2) . . ? C20 C21 C22 122.5(2) . . ? C20 C21 H21 119.4(15) . . ? C22 C21 H21 118.1(15) . . ? C5 C22 C1 118.4(2) . . ? C5 C22 C21 118.2(2) . . ? C1 C22 C21 123.4(2) . . ? C24 C23 S1 116.07(17) . . ? C24 C23 H23A 108.3 . . ? S1 C23 H23A 108.3 . . ? C24 C23 H23B 108.3 . . ? S1 C23 H23B 108.3 . . ? H23A C23 H23B 107.4 . . ? C25 C24 C23 111.3(2) . . ? C25 C24 H24A 109.4 . . ? C23 C24 H24A 109.4 . . ? C25 C24 H24B 109.4 . . ? C23 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? O1 C25 O2 122.6(2) . . ? O1 C25 C24 120.8(2) . . ? O2 C25 C24 116.7(2) . . ? C27 C26 S2 113.76(18) . . ? C27 C26 H26A 108.8 . . ? S2 C26 H26A 108.8 . . ? C27 C26 H26B 108.8 . . ? S2 C26 H26B 108.8 . . ? H26A C26 H26B 107.7 . . ? C28 C27 C26 114.7(2) . . ? C28 C27 H27A 108.6 . . ? C26 C27 H27A 108.6 . . ? C28 C27 H27B 108.6 . . ? C26 C27 H27B 108.6 . . ? H27A C27 H27B 107.6 . . ? O3 C28 O4 123.8(2) . . ? O3 C28 C27 121.6(2) . . ? O4 C28 C27 114.6(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 C22 C1 C2 C3 0.4(5) . . . . ? C1 C2 C3 C4 0.9(5) . . . . ? C2 C3 C4 C5 -0.6(5) . . . . ? C3 C4 C5 C6 179.6(3) . . . . ? C3 C4 C5 C22 -1.0(4) . . . . ? C22 C5 C6 C7 -3.2(4) . . . . ? C4 C5 C6 C7 176.3(3) . . . . ? C5 C6 C7 C20 0.5(4) . . . . ? C5 C6 C7 C8 -178.4(2) . . . . ? C6 C7 C8 C9 -154.5(2) . . . . ? C20 C7 C8 C9 26.6(3) . . . . ? C6 C7 C8 S1 82.9(3) . . . . ? C20 C7 C8 S1 -96.0(2) . . . . ? C23 S1 C8 C7 176.73(15) . . . . ? C23 S1 C8 C9 52.8(2) . . . . ? C7 C8 C9 C10 151.2(2) . . . . ? S1 C8 C9 C10 -90.5(3) . . . . ? C7 C8 C9 C18 -30.4(3) . . . . ? S1 C8 C9 C18 87.9(2) . . . . ? C18 C9 C10 C11 -3.5(4) . . . . ? C8 C9 C10 C11 174.9(2) . . . . ? C9 C10 C11 C12 -176.6(3) . . . . ? C9 C10 C11 C16 0.5(4) . . . . ? C10 C11 C12 C13 176.6(3) . . . . ? C16 C11 C12 C13 -0.5(4) . . . . ? C11 C12 C13 C14 -0.3(5) . . . . ? C12 C13 C14 C15 1.0(5) . . . . ? C13 C14 C15 C16 -0.9(5) . . . . ? C14 C15 C16 C17 -179.3(3) . . . . ? C14 C15 C16 C11 0.1(4) . . . . ? C12 C11 C16 C17 180.0(2) . . . . ? C10 C11 C16 C17 2.8(4) . . . . ? C12 C11 C16 C15 0.6(4) . . . . ? C10 C11 C16 C15 -176.6(2) . . . . ? C15 C16 C17 C18 176.1(3) . . . . ? C11 C16 C17 C18 -3.2(4) . . . . ? C16 C17 C18 C9 0.3(4) . . . . ? C16 C17 C18 C19 -179.8(2) . . . . ? C10 C9 C18 C17 3.1(4) . . . . ? C8 C9 C18 C17 -175.3(2) . . . . ? C10 C9 C18 C19 -176.8(2) . . . . ? C8 C9 C18 C19 4.8(3) . . . . ? C17 C18 C19 C20 -155.5(2) . . . . ? C9 C18 C19 C20 24.3(3) . . . . ? C17 C18 C19 S2 80.8(3) . . . . ? C9 C18 C19 S2 -99.3(2) . . . . ? C26 S2 C19 C18 -166.72(16) . . . . ? C26 S2 C19 C20 68.24(19) . . . . ? C6 C7 C20 C21 2.8(4) . . . . ? C8 C7 C20 C21 -178.3(2) . . . . ? C6 C7 C20 C19 -176.5(2) . . . . ? C8 C7 C20 C19 2.4(3) . . . . ? C18 C19 C20 C21 152.7(2) . . . . ? S2 C19 C20 C21 -87.2(3) . . . . ? C18 C19 C20 C7 -28.0(3) . . . . ? S2 C19 C20 C7 92.1(2) . . . . ? C7 C20 C21 C22 -3.5(4) . . . . ? C19 C20 C21 C22 175.8(2) . . . . ? C6 C5 C22 C1 -178.4(2) . . . . ? C4 C5 C22 C1 2.2(4) . . . . ? C6 C5 C22 C21 2.5(4) . . . . ? C4 C5 C22 C21 -176.9(2) . . . . ? C2 C1 C22 C5 -1.9(4) . . . . ? C2 C1 C22 C21 177.2(3) . . . . ? C20 C21 C22 C5 0.8(4) . . . . ? C20 C21 C22 C1 -178.3(3) . . . . ? C8 S1 C23 C24 72.7(2) . . . . ? S1 C23 C24 C25 -171.15(19) . . . . ? C23 C24 C25 O1 21.9(4) . . . . ? C23 C24 C25 O2 -158.2(2) . . . . ? C19 S2 C26 C27 69.1(2) . . . . ? S2 C26 C27 C28 173.9(2) . . . . ? C26 C27 C28 O3 -142.5(3) . . . . ? C26 C27 C28 O4 39.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O3 1.06(4) 1.61(4) 2.657(3) 173(4) 2_556 O4 H4 O1 0.93(4) 1.67(4) 2.596(3) 176(4) 2_546 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.246 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.039