# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Mireille Blanchard-Desce' _publ_contact_author_email MIREILLE.BLANCHARD-DESCE@UNIV-RENNES1.FR _publ_section_title ; Novel chromophores from alternated pyridine-ethylenedioxythiophene units oligomers: dramatic enhancement of photoluminescence properties in elongated derivatives ; _publ_requested_category FO loop_ _publ_author_name 'Mireille Blanchard-Desce' 'Marina Charlot' 'Floris Chevallier' 'Claudine Katan' 'Florence Mongin' # Attachment 'CIF ESI CC B815656E.cif' # # CCDC ELECTRONIC DATA DEPOSITION FORM (CIF) # # This electronic data deposition form can be used: # # (a) WHEN SUBMITTING A PAPER TO A JOURNAL FOR PUBLICATION or # (b) WHEN SUBMITTING A PRIVATE COMMUNICATION TO THE CCDC # # A comprehensive archive of CIF resources is maintained by the IUCr # at its Chester office. This can be accessed # by anonymous ftp to ftp.iucr.org # or via the WWW at http://www.iucr.org/cif/home.html # If data items in this form are not available or not applicable # then ignore these items # A few items specific to CCDC input are indicated by _ccdc_ # # Submission and help information is provided at the end of this form #------------------------------------------------------------------------- #1 Global data block identification for start of deposition data_cpd3 _database_code_depnum_ccdc_archive 'CCDC 699627' _audit_creation_date 2007-04-03T09:45:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H12 N2 O2 S1' _chemical_formula_sum 'C16 H12 N2 O2 S' _chemical_formula_weight 296.34 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4925(3) _cell_length_b 9.8365(3) _cell_length_c 13.1153(4) _cell_angle_alpha 90 _cell_angle_beta 97.7390(10) _cell_angle_gamma 90 _cell_volume 1341.29(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5586 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.49 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.875 _exptl_absorpt_correction_T_max 0.929 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_av_unetI/netI 0.0179 _diffrn_reflns_number 15609 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 3044 _reflns_number_gt 2856 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0346P)^2^+0.7929P] 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_number_reflns 3044 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0313 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.076 _refine_ls_wR_factor_gt 0.0745 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.33 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.049 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.47977(3) 0.09055(3) 0.87389(2) 0.01253(9) Uani 1 d . . . C1 C 0.64346(11) 0.10028(11) 0.91441(8) 0.0126(2) Uani 1 d . . . C11 C 0.73314(11) 0.02540(11) 0.85919(8) 0.0134(2) Uani 1 d . . . C12 C 0.86601(12) 0.03044(12) 0.88842(9) 0.0171(2) Uani 1 d . . . H12 H 0.9013 0.0798 0.9479 0.021 Uiso 1 calc R . . C13 C 0.94579(12) -0.03770(13) 0.82934(9) 0.0191(2) Uani 1 d . . . H13 H 1.0365 -0.0346 0.8472 0.023 Uiso 1 calc R . . C14 C 0.89114(12) -0.11057(13) 0.74375(9) 0.0194(3) Uani 1 d . . . H14 H 0.9433 -0.1575 0.7014 0.023 Uiso 1 calc R . . C15 C 0.75839(12) -0.11267(13) 0.72201(9) 0.0195(3) Uani 1 d . . . H15 H 0.7212 -0.1645 0.6645 0.023 Uiso 1 calc R . . N16 N 0.67888(10) -0.04652(10) 0.77664(8) 0.0166(2) Uani 1 d . . . C2 C 0.66800(11) 0.18841(11) 0.99614(8) 0.0128(2) Uani 1 d . . . O3 O 0.78880(8) 0.22028(9) 1.04262(6) 0.01681(18) Uani 1 d . . . C4 C 0.78679(12) 0.28707(14) 1.14069(9) 0.0205(3) Uani 1 d . . . H4A H 0.872 0.328 1.1636 0.025 Uiso 1 calc R . . H4B H 0.7691 0.2192 1.1928 0.025 Uiso 1 calc R . . C21 C 0.44487(11) 0.20569(11) 0.96639(8) 0.0132(2) Uani 1 d . . . C31 C 0.31217(11) 0.24908(11) 0.96900(8) 0.0138(2) Uani 1 d . . . C32 C 0.27291(11) 0.31038(12) 1.05617(9) 0.0160(2) Uani 1 d . . . H32 H 0.3318 0.3225 1.1171 0.019 Uiso 1 calc R . . C33 C 0.14672(12) 0.35281(13) 1.05156(9) 0.0186(2) Uani 1 d . . . H33 H 0.1172 0.3931 1.1099 0.022 Uiso 1 calc R . . C34 C 0.06354(12) 0.33590(13) 0.96068(10) 0.0209(3) Uani 1 d . . . H34 H -0.023 0.3666 0.955 0.025 Uiso 1 calc R . . C35 C 0.11010(12) 0.27301(13) 0.87836(10) 0.0206(3) Uani 1 d . . . H35 H 0.0529 0.2609 0.8165 0.025 Uiso 1 calc R . . N36 N 0.23086(10) 0.22861(11) 0.88142(8) 0.0173(2) Uani 1 d . . . C22 C 0.55515(11) 0.24789(11) 1.02603(8) 0.0132(2) Uani 1 d . . . O23 O 0.55862(8) 0.33817(9) 1.10559(6) 0.01652(18) Uani 1 d . . . C24 C 0.68512(12) 0.39630(13) 1.13231(10) 0.0189(2) Uani 1 d . . . H24A H 0.6892 0.4449 1.1988 0.023 Uiso 1 calc R . . H24B H 0.7017 0.463 1.0791 0.023 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01249(15) 0.01245(14) 0.01261(14) -0.00028(9) 0.00154(10) -0.00025(9) C1 0.0127(5) 0.0125(5) 0.0125(5) 0.0024(4) 0.0015(4) 0.0002(4) C11 0.0167(6) 0.0113(5) 0.0123(5) 0.0018(4) 0.0020(4) 0.0016(4) C12 0.0172(6) 0.0172(6) 0.0167(5) -0.0033(4) 0.0009(4) 0.0010(4) C13 0.0153(6) 0.0191(6) 0.0229(6) -0.0020(5) 0.0025(4) 0.0030(4) C14 0.0218(6) 0.0185(6) 0.0186(6) -0.0027(4) 0.0047(5) 0.0062(5) C15 0.0232(6) 0.0186(6) 0.0158(5) -0.0043(4) 0.0000(5) 0.0046(5) N16 0.0181(5) 0.0162(5) 0.0149(5) -0.0017(4) 0.0000(4) 0.0025(4) C2 0.0129(5) 0.0135(5) 0.0120(5) 0.0022(4) 0.0014(4) -0.0004(4) O3 0.0130(4) 0.0228(4) 0.0144(4) -0.0057(3) 0.0006(3) 0.0000(3) C4 0.0185(6) 0.0277(7) 0.0146(5) -0.0073(5) -0.0007(4) 0.0022(5) C21 0.0158(6) 0.0117(5) 0.0125(5) 0.0016(4) 0.0040(4) 0.0003(4) C31 0.0140(5) 0.0120(5) 0.0160(5) 0.0019(4) 0.0035(4) -0.0017(4) C32 0.0169(6) 0.0165(5) 0.0150(5) 0.0004(4) 0.0032(4) -0.0012(4) C33 0.0173(6) 0.0186(6) 0.0213(6) -0.0036(5) 0.0072(4) -0.0012(5) C34 0.0126(6) 0.0226(6) 0.0277(6) -0.0038(5) 0.0033(5) 0.0006(5) C35 0.0143(6) 0.0253(6) 0.0219(6) -0.0039(5) 0.0004(4) -0.0017(5) N36 0.0148(5) 0.0194(5) 0.0179(5) -0.0023(4) 0.0025(4) -0.0011(4) C22 0.0167(6) 0.0119(5) 0.0115(5) 0.0010(4) 0.0035(4) -0.0001(4) O23 0.0157(4) 0.0181(4) 0.0161(4) -0.0054(3) 0.0034(3) -0.0008(3) C24 0.0171(6) 0.0195(6) 0.0199(6) -0.0066(5) 0.0020(4) -0.0026(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 1.7308(12) . ? S1 C21 1.7345(12) . ? C1 C2 1.3756(15) . ? C1 C11 1.4615(16) . ? C11 N16 1.3530(15) . ? C11 C12 1.3962(16) . ? C12 C13 1.3875(17) . ? C12 H12 0.95 . ? C13 C14 1.3890(17) . ? C13 H13 0.95 . ? C14 C15 1.3838(18) . ? C14 H14 0.95 . ? C15 N16 1.3393(16) . ? C15 H15 0.95 . ? C2 O3 1.3669(13) . ? C2 C22 1.4223(16) . ? O3 C4 1.4469(14) . ? C4 C24 1.5077(17) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C21 C22 1.3708(15) . ? C21 C31 1.4611(16) . ? C31 N36 1.3504(15) . ? C31 C32 1.4026(16) . ? C32 C33 1.3817(17) . ? C32 H32 0.95 . ? C33 C34 1.3892(17) . ? C33 H33 0.95 . ? C34 C35 1.3889(17) . ? C34 H34 0.95 . ? C35 N36 1.3357(16) . ? C35 H35 0.95 . ? C22 O23 1.3670(13) . ? O23 C24 1.4443(14) . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C21 92.49(5) . . ? C2 C1 C11 129.66(10) . . ? C2 C1 S1 110.36(8) . . ? C11 C1 S1 119.90(8) . . ? N16 C11 C12 122.37(11) . . ? N16 C11 C1 115.50(10) . . ? C12 C11 C1 122.12(10) . . ? C13 C12 C11 118.99(11) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 119.09(12) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C15 C14 C13 117.95(11) . . ? C15 C14 H14 121 . . ? C13 C14 H14 121 . . ? N16 C15 C14 124.39(11) . . ? N16 C15 H15 117.8 . . ? C14 C15 H15 117.8 . . ? C15 N16 C11 117.18(11) . . ? O3 C2 C1 123.85(10) . . ? O3 C2 C22 122.63(10) . . ? C1 C2 C22 113.49(10) . . ? C2 O3 C4 112.14(9) . . ? O3 C4 C24 110.71(10) . . ? O3 C4 H4A 109.5 . . ? C24 C4 H4A 109.5 . . ? O3 C4 H4B 109.5 . . ? C24 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C22 C21 C31 129.20(11) . . ? C22 C21 S1 110.81(8) . . ? C31 C21 S1 119.92(8) . . ? N36 C31 C32 122.42(11) . . ? N36 C31 C21 115.56(10) . . ? C32 C31 C21 122.01(10) . . ? C33 C32 C31 118.62(11) . . ? C33 C32 H32 120.7 . . ? C31 C32 H32 120.7 . . ? C32 C33 C34 119.27(11) . . ? C32 C33 H33 120.4 . . ? C34 C33 H33 120.4 . . ? C35 C34 C33 118.30(11) . . ? C35 C34 H34 120.9 . . ? C33 C34 H34 120.9 . . ? N36 C35 C34 123.63(11) . . ? N36 C35 H35 118.2 . . ? C34 C35 H35 118.2 . . ? C35 N36 C31 117.70(11) . . ? O23 C22 C21 124.47(10) . . ? O23 C22 C2 122.68(10) . . ? C21 C22 C2 112.85(10) . . ? C22 O23 C24 111.81(9) . . ? O23 C24 C4 110.71(10) . . ? O23 C24 H24A 109.5 . . ? C4 C24 H24A 109.5 . . ? O23 C24 H24B 109.5 . . ? C4 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? 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 C21 S1 C1 C2 0.33(9) . . . . ? C21 S1 C1 C11 -176.81(9) . . . . ? C2 C1 C11 N16 -175.46(11) . . . . ? S1 C1 C11 N16 1.05(14) . . . . ? C2 C1 C11 C12 3.13(19) . . . . ? S1 C1 C11 C12 179.65(9) . . . . ? N16 C11 C12 C13 1.74(18) . . . . ? C1 C11 C12 C13 -176.76(11) . . . . ? C11 C12 C13 C14 -0.95(18) . . . . ? C12 C13 C14 C15 -0.61(18) . . . . ? C13 C14 C15 N16 1.6(2) . . . . ? C14 C15 N16 C11 -0.88(18) . . . . ? C12 C11 N16 C15 -0.83(17) . . . . ? C1 C11 N16 C15 177.76(10) . . . . ? C11 C1 C2 O3 -1.07(19) . . . . ? S1 C1 C2 O3 -177.85(9) . . . . ? C11 C1 C2 C22 176.80(11) . . . . ? S1 C1 C2 C22 0.02(12) . . . . ? C1 C2 O3 C4 -165.64(11) . . . . ? C22 C2 O3 C4 16.68(15) . . . . ? C2 O3 C4 C24 -45.54(14) . . . . ? C1 S1 C21 C22 -0.60(9) . . . . ? C1 S1 C21 C31 176.59(9) . . . . ? C22 C21 C31 N36 157.48(12) . . . . ? S1 C21 C31 N36 -19.14(14) . . . . ? C22 C21 C31 C32 -21.29(18) . . . . ? S1 C21 C31 C32 162.10(9) . . . . ? N36 C31 C32 C33 -0.83(18) . . . . ? C21 C31 C32 C33 177.85(11) . . . . ? C31 C32 C33 C34 -1.17(18) . . . . ? C32 C33 C34 C35 1.80(19) . . . . ? C33 C34 C35 N36 -0.5(2) . . . . ? C34 C35 N36 C31 -1.46(19) . . . . ? C32 C31 N36 C35 2.12(17) . . . . ? C21 C31 N36 C35 -176.64(11) . . . . ? C31 C21 C22 O23 3.39(19) . . . . ? S1 C21 C22 O23 -179.75(9) . . . . ? C31 C21 C22 C2 -176.14(11) . . . . ? S1 C21 C22 C2 0.72(12) . . . . ? O3 C2 C22 O23 -2.13(17) . . . . ? C1 C2 C22 O23 179.97(10) . . . . ? O3 C2 C22 C21 177.41(10) . . . . ? C1 C2 C22 C21 -0.49(14) . . . . ? C21 C22 O23 C24 -161.41(11) . . . . ? C2 C22 O23 C24 18.08(15) . . . . ? C22 O23 C24 C4 -46.95(13) . . . . ? O3 C4 C24 O23 62.98(13) . . . . ? data_cpd5 _database_code_depnum_ccdc_archive 'CCDC 699628' _audit_creation_date 2008-06-10T17:20:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H13 N1 O4 S2' _chemical_formula_sum 'C17 H13 N O4 S2' _chemical_formula_weight 359.4 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.2617(9) _cell_length_b 6.9926(9) _cell_length_c 28.988(4) _cell_angle_alpha 90 _cell_angle_beta 90.338(4) _cell_angle_gamma 90 _cell_volume 1471.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4139 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 27.55 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 1.622 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.385 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.837 _exptl_absorpt_correction_T_max 0.951 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_unetI/netI 0.0399 _diffrn_reflns_number 10756 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.5 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.961 _diffrn_measured_fraction_theta_max 0.935 _reflns_number_total 3148 _reflns_number_gt 2790 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0478P)^2^+0.8959P] 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_number_reflns 3148 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.037 _refine_ls_wR_factor_ref 0.0971 _refine_ls_wR_factor_gt 0.093 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.5 _refine_diff_density_min -0.3 _refine_diff_density_rms 0.071 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1362(2) 0.2960(3) 0.62026(6) 0.0167(4) Uani 1 d . . . H1A H 0.1558 0.2668 0.6533 0.02 Uiso 1 calc R . . H1B H 0.1395 0.4367 0.6164 0.02 Uiso 1 calc R . . C2 C 0.2881(2) 0.2065(3) 0.59228(6) 0.0159(4) Uani 1 d . . . H2A H 0.409 0.2472 0.6048 0.019 Uiso 1 calc R . . H2B H 0.2805 0.0655 0.5947 0.019 Uiso 1 calc R . . O3 O -0.04140(17) 0.2245(2) 0.60574(4) 0.0172(3) Uani 1 d . . . O4 O 0.27316(16) 0.2624(2) 0.54443(4) 0.0150(3) Uani 1 d . . . C5 C -0.0587(2) 0.2300(3) 0.55864(6) 0.0142(4) Uani 1 d . . . C6 C 0.0955(2) 0.2497(3) 0.52851(6) 0.0123(4) Uani 1 d . . . C7 C -0.2216(2) 0.2168(3) 0.53554(6) 0.0153(4) Uani 1 d . . . H7 H -0.3379 0.2017 0.5499 0.018 Uiso 1 calc R . . S8 S -0.19043(6) 0.23112(7) 0.477052(14) 0.01448(13) Uani 1 d . . . C9 C 0.0456(2) 0.2548(3) 0.48270(6) 0.0122(4) Uani 1 d . . . C10 C 0.1577(2) 0.2777(3) 0.44149(6) 0.0117(4) Uani 1 d . . . C11 C 0.3471(2) 0.3160(3) 0.44363(6) 0.0153(4) Uani 1 d . . . H11 H 0.4096 0.322 0.4725 0.018 Uiso 1 calc R . . C12 C 0.4407(2) 0.3450(3) 0.40285(6) 0.0152(4) Uani 1 d . . . H12 H 0.5688 0.3728 0.4035 0.018 Uiso 1 calc R . . N13 N 0.0665(2) 0.2625(2) 0.40093(5) 0.0126(3) Uani 1 d . . . C21 C 0.1380(2) 0.3519(3) 0.18324(6) 0.0176(4) Uani 1 d . . . H21A H 0.111 0.4881 0.1896 0.021 Uiso 1 calc R . . H21B H 0.163 0.3386 0.1499 0.021 Uiso 1 calc R . . C22 C 0.3054(2) 0.2909(3) 0.21056(6) 0.0155(4) Uani 1 d . . . H22A H 0.3302 0.1537 0.2048 0.019 Uiso 1 calc R . . H22B H 0.4138 0.3648 0.2002 0.019 Uiso 1 calc R . . O23 O -0.01974(17) 0.2365(2) 0.19529(4) 0.0174(3) Uani 1 d . . . O24 O 0.27842(16) 0.3213(2) 0.25939(4) 0.0151(3) Uani 1 d . . . C25 C -0.0414(2) 0.2293(3) 0.24207(6) 0.0135(4) Uani 1 d . . . C26 C 0.1046(2) 0.2726(3) 0.27354(6) 0.0122(4) Uani 1 d . . . C27 C -0.2007(2) 0.1818(3) 0.26389(6) 0.0158(4) Uani 1 d . . . H27 H -0.3116 0.1474 0.2485 0.019 Uiso 1 calc R . . S28 S -0.17578(6) 0.19167(7) 0.322805(14) 0.01509(14) Uani 1 d . . . C29 C 0.0529(2) 0.2610(3) 0.31906(6) 0.0125(4) Uani 1 d . . . C30 C 0.1611(2) 0.2876(3) 0.36144(6) 0.0122(4) Uani 1 d . . . C31 C 0.3483(2) 0.3335(3) 0.36088(6) 0.0147(4) Uani 1 d . . . H31 H 0.4104 0.3562 0.3327 0.018 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0178(8) 0.0211(12) 0.0111(8) -0.0012(7) -0.0013(6) -0.0011(7) C2 0.0176(8) 0.0211(12) 0.0090(8) 0.0017(7) -0.0010(6) 0.0023(7) O3 0.0163(6) 0.0253(9) 0.0100(6) -0.0012(5) 0.0019(5) -0.0024(5) O4 0.0125(6) 0.0218(8) 0.0106(6) 0.0019(5) -0.0008(4) -0.0004(5) C5 0.0168(8) 0.0146(11) 0.0113(8) -0.0007(7) 0.0017(6) 0.0003(7) C6 0.0131(8) 0.0103(10) 0.0136(8) -0.0004(7) -0.0007(6) 0.0009(6) C7 0.0162(8) 0.0168(11) 0.0130(8) -0.0013(7) 0.0043(6) 0.0016(7) S8 0.0119(2) 0.0188(3) 0.0128(2) -0.00071(17) -0.00048(15) 0.00077(16) C9 0.0111(7) 0.0135(11) 0.0120(8) 0.0000(7) -0.0002(6) 0.0015(6) C10 0.0153(8) 0.0092(10) 0.0105(8) -0.0003(6) 0.0001(6) 0.0019(6) C11 0.0152(8) 0.0184(12) 0.0124(8) 0.0017(7) -0.0010(6) 0.0005(7) C12 0.0142(8) 0.0157(11) 0.0156(8) 0.0002(7) 0.0004(6) -0.0013(7) N13 0.0139(7) 0.0124(9) 0.0116(7) -0.0004(6) 0.0002(5) 0.0014(6) C21 0.0186(8) 0.0226(12) 0.0116(8) 0.0029(7) 0.0012(6) -0.0036(8) C22 0.0182(8) 0.0167(11) 0.0117(8) -0.0010(7) 0.0044(6) -0.0008(7) O23 0.0180(6) 0.0251(9) 0.0092(6) 0.0003(5) 0.0002(5) -0.0041(5) O24 0.0136(6) 0.0215(8) 0.0101(6) -0.0007(5) 0.0016(4) -0.0027(5) C25 0.0180(8) 0.0133(11) 0.0093(8) 0.0006(7) -0.0011(6) 0.0009(7) C26 0.0138(8) 0.0100(10) 0.0129(8) 0.0003(7) 0.0014(6) 0.0016(6) C27 0.0160(8) 0.0188(12) 0.0125(8) 0.0008(7) -0.0024(6) -0.0007(7) S28 0.0128(2) 0.0206(3) 0.0119(2) 0.00058(17) 0.00157(14) -0.00170(17) C29 0.0131(8) 0.0118(11) 0.0126(8) 0.0006(7) 0.0005(6) -0.0003(6) C30 0.0160(8) 0.0101(10) 0.0104(8) 0.0001(6) -0.0006(6) 0.0014(6) C31 0.0171(8) 0.0137(11) 0.0134(8) 0.0010(7) 0.0022(6) -0.0006(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O3 1.444(2) . ? C1 C2 1.509(2) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 O4 1.4445(19) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? O3 C5 1.371(2) . ? O4 C6 1.371(2) . ? C5 C7 1.359(2) . ? C5 C6 1.431(2) . ? C6 C9 1.375(2) . ? C7 S8 1.7146(18) . ? C7 H7 0.95 . ? S8 C9 1.7284(17) . ? C9 C10 1.459(2) . ? C10 N13 1.350(2) . ? C10 C11 1.402(2) . ? C11 C12 1.382(2) . ? C11 H11 0.95 . ? C12 C31 1.388(2) . ? C12 H12 0.95 . ? N13 C30 1.350(2) . ? C21 O23 1.446(2) . ? C21 C22 1.509(2) . ? C21 H21A 0.99 . ? C21 H21B 0.99 . ? C22 O24 1.4457(19) . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? O23 C25 1.3671(19) . ? O24 C26 1.372(2) . ? C25 C27 1.363(2) . ? C25 C26 1.427(2) . ? C26 C29 1.376(2) . ? C27 S28 1.7176(17) . ? C27 H27 0.95 . ? S28 C29 1.7338(18) . ? C29 C30 1.466(2) . ? C30 C31 1.397(2) . ? C31 H31 0.95 . ? 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 O3 C1 C2 110.71(15) . . ? O3 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? O3 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? O4 C2 C1 110.68(14) . . ? O4 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? O4 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C5 O3 C1 110.92(13) . . ? C6 O4 C2 111.76(13) . . ? C7 C5 O3 124.27(15) . . ? C7 C5 C6 112.82(15) . . ? O3 C5 C6 122.90(15) . . ? O4 C6 C9 124.47(15) . . ? O4 C6 C5 122.63(15) . . ? C9 C6 C5 112.90(15) . . ? C5 C7 S8 111.32(13) . . ? C5 C7 H7 124.3 . . ? S8 C7 H7 124.3 . . ? C7 S8 C9 92.79(8) . . ? C6 C9 C10 130.42(16) . . ? C6 C9 S8 110.16(12) . . ? C10 C9 S8 119.42(13) . . ? N13 C10 C11 121.98(15) . . ? N13 C10 C9 115.53(15) . . ? C11 C10 C9 122.49(16) . . ? C12 C11 C10 118.53(16) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C31 120.22(16) . . ? C11 C12 H12 119.9 . . ? C31 C12 H12 119.9 . . ? C30 N13 C10 118.61(15) . . ? O23 C21 C22 110.63(15) . . ? O23 C21 H21A 109.5 . . ? C22 C21 H21A 109.5 . . ? O23 C21 H21B 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 108.1 . . ? O24 C22 C21 111.03(14) . . ? O24 C22 H22A 109.4 . . ? C21 C22 H22A 109.4 . . ? O24 C22 H22B 109.4 . . ? C21 C22 H22B 109.4 . . ? H22A C22 H22B 108 . . ? C25 O23 C21 110.85(13) . . ? C26 O24 C22 112.72(13) . . ? C27 C25 O23 124.90(15) . . ? C27 C25 C26 112.61(15) . . ? O23 C25 C26 122.49(15) . . ? O24 C26 C29 123.91(15) . . ? O24 C26 C25 122.87(15) . . ? C29 C26 C25 113.22(15) . . ? C25 C27 S28 111.53(13) . . ? C25 C27 H27 124.2 . . ? S28 C27 H27 124.2 . . ? C27 S28 C29 92.53(8) . . ? C26 C29 C30 130.38(16) . . ? C26 C29 S28 110.09(13) . . ? C30 C29 S28 119.44(13) . . ? N13 C30 C31 122.66(16) . . ? N13 C30 C29 114.93(15) . . ? C31 C30 C29 122.41(15) . . ? C12 C31 C30 117.93(15) . . ? C12 C31 H31 121 . . ? C30 C31 H31 121 . . ? 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 O3 C1 C2 O4 64.8(2) . . . . ? C2 C1 O3 C5 -47.8(2) . . . . ? C1 C2 O4 C6 -45.2(2) . . . . ? C1 O3 C5 C7 -163.35(19) . . . . ? C1 O3 C5 C6 16.9(2) . . . . ? C2 O4 C6 C9 -165.81(18) . . . . ? C2 O4 C6 C5 14.4(2) . . . . ? C7 C5 C6 O4 -178.98(17) . . . . ? O3 C5 C6 O4 0.8(3) . . . . ? C7 C5 C6 C9 1.2(2) . . . . ? O3 C5 C6 C9 -179.08(17) . . . . ? O3 C5 C7 S8 179.51(15) . . . . ? C6 C5 C7 S8 -0.7(2) . . . . ? C5 C7 S8 C9 0.14(16) . . . . ? O4 C6 C9 C10 -1.5(3) . . . . ? C5 C6 C9 C10 178.35(18) . . . . ? O4 C6 C9 S8 179.12(15) . . . . ? C5 C6 C9 S8 -1.0(2) . . . . ? C7 S8 C9 C6 0.52(15) . . . . ? C7 S8 C9 C10 -178.94(15) . . . . ? C6 C9 C10 N13 175.35(19) . . . . ? S8 C9 C10 N13 -5.3(2) . . . . ? C6 C9 C10 C11 -5.6(3) . . . . ? S8 C9 C10 C11 173.70(15) . . . . ? N13 C10 C11 C12 2.1(3) . . . . ? C9 C10 C11 C12 -176.83(18) . . . . ? C10 C11 C12 C31 -0.8(3) . . . . ? C11 C10 N13 C30 -0.9(3) . . . . ? C9 C10 N13 C30 178.14(16) . . . . ? O23 C21 C22 O24 -63.3(2) . . . . ? C22 C21 O23 C25 50.2(2) . . . . ? C21 C22 O24 C26 40.9(2) . . . . ? C21 O23 C25 C27 160.06(19) . . . . ? C21 O23 C25 C26 -19.8(2) . . . . ? C22 O24 C26 C29 169.92(17) . . . . ? C22 O24 C26 C25 -10.3(2) . . . . ? C27 C25 C26 O24 178.97(17) . . . . ? O23 C25 C26 O24 -1.2(3) . . . . ? C27 C25 C26 C29 -1.3(2) . . . . ? O23 C25 C26 C29 178.60(16) . . . . ? O23 C25 C27 S28 -179.16(15) . . . . ? C26 C25 C27 S28 0.7(2) . . . . ? C25 C27 S28 C29 0.00(16) . . . . ? O24 C26 C29 C30 -2.6(3) . . . . ? C25 C26 C29 C30 177.67(19) . . . . ? O24 C26 C29 S28 -179.01(14) . . . . ? C25 C26 C29 S28 1.2(2) . . . . ? C27 S28 C29 C26 -0.70(15) . . . . ? C27 S28 C29 C30 -177.60(16) . . . . ? C10 N13 C30 C31 -1.7(3) . . . . ? C10 N13 C30 C29 177.67(16) . . . . ? C26 C29 C30 N13 -178.97(19) . . . . ? S28 C29 C30 N13 -2.8(2) . . . . ? C26 C29 C30 C31 0.4(3) . . . . ? S28 C29 C30 C31 176.57(15) . . . . ? C11 C12 C31 C30 -1.6(3) . . . . ? N13 C30 C31 C12 2.9(3) . . . . ? C29 C30 C31 C12 -176.41(18) . . . . ? data_cpd6 _database_code_depnum_ccdc_archive 'CCDC 707007' _audit_creation_date 2008-09-10T17:07:51-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H16 N2 O4 S2' _chemical_formula_sum 'C22 H16 N2 O4 S2' _chemical_formula_weight 436.49 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 c 1' _symmetry_space_group_name_Hall 'C -2yc' _symmetry_Int_Tables_number 9 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' _cell_length_a 49.259(5) _cell_length_b 4.9656(4) _cell_length_c 15.3119(13) _cell_angle_alpha 90 _cell_angle_beta 90.604(6) _cell_angle_gamma 90 _cell_volume 3745.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2234 _cell_measurement_theta_min 4.27 _cell_measurement_theta_max 24.7 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.22 _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1808 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.320 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.836 _exptl_absorpt_correction_T_max 0.932 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0645 _diffrn_reflns_av_unetI/netI 0.098 _diffrn_reflns_number 11164 _diffrn_reflns_limit_h_min -48 _diffrn_reflns_limit_h_max 63 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.964 _diffrn_measured_fraction_theta_max 0.951 _reflns_number_total 6033 _reflns_number_gt 5081 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0992P)^2^+8.6775P] 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_number_reflns 6033 _refine_ls_number_parameters 541 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0724 _refine_ls_wR_factor_ref 0.1901 _refine_ls_wR_factor_gt 0.1789 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(11) _refine_diff_density_max 1.006 _refine_diff_density_min -0.713 _refine_diff_density_rms 0.118 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.93149(10) 0.9336(9) 0.7836(3) 0.0217(10) Uani 1 d . . . C2 C 0.95539(15) 1.0160(12) 0.7394(4) 0.0231(14) Uani 1 d . . . H2A H 0.9585 0.896 0.6889 0.028 Uiso 1 calc R . . H2B H 0.9712 1.0016 0.7794 0.028 Uiso 1 calc R . . C3 C 0.95252(14) 1.3046(12) 0.7079(4) 0.0240(14) Uani 1 d . . . H3A H 0.9485 1.4235 0.7581 0.029 Uiso 1 calc R . . H3B H 0.9698 1.3647 0.6818 0.029 Uiso 1 calc R . . O4 O 0.93074(9) 1.3251(8) 0.6433(3) 0.0220(10) Uani 1 d . . . C5 C 0.90839(13) 1.1766(11) 0.6649(4) 0.0190(13) Uani 1 d . . . C6 C 0.90870(14) 0.9793(11) 0.7331(4) 0.0199(14) Uani 1 d . . . C7 C 0.88439(15) 0.8481(13) 0.7413(4) 0.0227(14) Uani 1 d . . . H7 H 0.8809 0.7114 0.783 0.027 Uiso 1 calc R . . S8 S 0.86114(3) 0.9645(3) 0.66563(10) 0.0194(3) Uani 1 d . . . C9 C 0.88384(13) 1.1886(11) 0.6209(4) 0.0173(12) Uani 1 d . . . C10 C 0.87554(14) 1.3506(12) 0.5449(4) 0.0203(13) Uani 1 d . . . C11 C 0.89147(13) 1.5627(12) 0.5138(4) 0.0185(13) Uani 1 d . . . H11 H 0.908 1.6115 0.5422 0.022 Uiso 1 calc R . . C12 C 0.88250(14) 1.6979(12) 0.4409(4) 0.0205(13) Uani 1 d . . . H12 H 0.893 1.8432 0.4191 0.025 Uiso 1 calc R . . C13 C 0.85860(13) 1.6284(11) 0.3983(4) 0.0178(13) Uani 1 d . . . H13 H 0.8524 1.7236 0.3481 0.021 Uiso 1 calc R . . C14 C 0.84383(13) 1.4099(11) 0.4327(4) 0.0179(13) Uani 1 d . . . N15 N 0.85207(11) 1.2773(9) 0.5063(3) 0.0186(11) Uani 1 d . . . C16 C 0.81922(13) 1.3054(11) 0.3916(4) 0.0196(13) Uani 1 d . . . C17 C 0.80858(14) 1.3582(12) 0.3103(4) 0.0201(13) Uani 1 d . . . O18 O 0.81948(10) 1.5275(8) 0.2511(3) 0.0200(9) Uani 1 d . . . C19 C 0.80249(18) 1.5678(17) 0.1760(5) 0.0366(19) Uani 1 d . . . H19A H 0.8137 1.6366 0.1276 0.044 Uiso 1 calc R . . H19B H 0.7888 1.7069 0.1896 0.044 Uiso 1 calc R . . C20 C 0.78844(18) 1.3222(16) 0.1467(5) 0.0373(19) Uani 1 d . . . H20A H 0.7775 1.3631 0.0937 0.045 Uiso 1 calc R . . H20B H 0.8021 1.1841 0.1311 0.045 Uiso 1 calc R . . O21 O 0.77104(10) 1.2170(9) 0.2126(3) 0.0254(11) Uani 1 d . . . C22 C 0.78445(14) 1.2010(12) 0.2920(4) 0.0216(14) Uani 1 d . . . C23 C 0.77751(13) 1.0352(11) 0.3608(4) 0.0172(13) Uani 1 d . . . S24 S 0.80034(3) 1.0642(3) 0.44640(10) 0.0200(3) Uani 1 d . . . C25 C 0.75551(13) 0.8424(12) 0.3659(4) 0.0210(13) Uani 1 d . . . C26 C 0.73602(16) 0.8099(13) 0.2994(5) 0.0288(16) Uani 1 d . . . H26 H 0.7364 0.9192 0.2485 0.035 Uiso 1 calc R . . C27 C 0.71608(14) 0.6148(14) 0.3093(5) 0.0260(15) Uani 1 d . . . H27 H 0.7026 0.5894 0.2653 0.031 Uiso 1 calc R . . C28 C 0.71610(15) 0.4582(14) 0.3837(5) 0.0275(15) Uani 1 d . . . H28 H 0.7029 0.3214 0.3916 0.033 Uiso 1 calc R . . C29 C 0.73618(15) 0.5066(12) 0.4473(5) 0.0237(14) Uani 1 d . . . H29 H 0.7364 0.3975 0.4983 0.028 Uiso 1 calc R . . N30 N 0.75490(12) 0.6981(11) 0.4397(4) 0.0242(12) Uani 1 d . . . O51 O 0.48084(10) 0.4860(8) 1.0343(3) 0.0205(10) Uani 1 d . . . C52 C 0.45700(15) 0.5822(12) 0.9907(5) 0.0238(14) Uani 1 d . . . H52A H 0.4414 0.5749 1.0308 0.029 Uiso 1 calc R . . H52B H 0.4528 0.4662 0.9397 0.029 Uiso 1 calc R . . C53 C 0.46137(15) 0.8698(13) 0.9605(4) 0.0249(14) Uani 1 d . . . H53A H 0.4442 0.9422 0.9359 0.03 Uiso 1 calc R . . H53B H 0.4667 0.983 1.0111 0.03 Uiso 1 calc R . . O54 O 0.48226(10) 0.8814(8) 0.8951(3) 0.0219(10) Uani 1 d . . . C55 C 0.50402(14) 0.7158(12) 0.9140(4) 0.0188(13) Uani 1 d . . . C56 C 0.50328(13) 0.5176(11) 0.9821(4) 0.0158(12) Uani 1 d . . . C57 C 0.52636(15) 0.3765(12) 0.9896(4) 0.0218(14) Uani 1 d . . . H57 H 0.5296 0.2404 1.0321 0.026 Uiso 1 calc R . . S58 S 0.54957(3) 0.4747(3) 0.91186(10) 0.0182(3) Uani 1 d . . . C59 C 0.52781(13) 0.7113(11) 0.8690(4) 0.0179(13) Uani 1 d . . . C60 C 0.53587(13) 0.8643(11) 0.7902(4) 0.0179(13) Uani 1 d . . . C61 C 0.52038(13) 1.0769(12) 0.7567(4) 0.0178(13) Uani 1 d . . . H61 H 0.5042 1.1317 0.7851 0.021 Uiso 1 calc R . . C62 C 0.52879(14) 1.2066(11) 0.6819(4) 0.0204(13) Uani 1 d . . . H62 H 0.5187 1.353 0.6582 0.024 Uiso 1 calc R . . C63 C 0.55271(14) 1.1160(12) 0.6417(4) 0.0209(14) Uani 1 d . . . H63 H 0.5591 1.2015 0.5904 0.025 Uiso 1 calc R . . C64 C 0.56694(14) 0.8983(11) 0.6783(4) 0.0179(13) Uani 1 d . . . N65 N 0.55906(11) 0.7796(9) 0.7527(3) 0.0182(11) Uani 1 d . . . C66 C 0.59094(14) 0.7827(11) 0.6392(4) 0.0199(13) Uani 1 d . . . C67 C 0.60217(15) 0.8229(12) 0.5579(4) 0.0234(14) Uani 1 d . . . O68 O 0.59115(10) 0.9981(8) 0.4970(3) 0.0188(9) Uani 1 d . . . C69 C 0.60813(18) 1.0251(18) 0.4222(5) 0.039(2) Uani 1 d . . . H69A H 0.5968 1.0895 0.3726 0.047 Uiso 1 calc R . . H69B H 0.6219 1.1654 0.4347 0.047 Uiso 1 calc R . . C70 C 0.62170(19) 0.7876(18) 0.3961(5) 0.043(2) Uani 1 d . . . H70A H 0.6331 0.8293 0.3449 0.051 Uiso 1 calc R . . H70B H 0.608 0.6528 0.3775 0.051 Uiso 1 calc R . . O71 O 0.63893(10) 0.6691(9) 0.4646(3) 0.0232(10) Uani 1 d . . . C72 C 0.62517(14) 0.6621(12) 0.5418(4) 0.0228(14) Uani 1 d . . . C73 C 0.63170(14) 0.4944(11) 0.6103(4) 0.0172(13) Uani 1 d . . . S74 S 0.60914(3) 0.5349(3) 0.69535(10) 0.0197(3) Uani 1 d . . . C75 C 0.65307(13) 0.2924(11) 0.6199(4) 0.0194(13) Uani 1 d . . . C76 C 0.67255(15) 0.2504(13) 0.5530(5) 0.0286(16) Uani 1 d . . . H76 H 0.6727 0.3594 0.5021 0.034 Uiso 1 calc R . . C77 C 0.69128(15) 0.0434(13) 0.5654(5) 0.0286(16) Uani 1 d . . . H77 H 0.7044 0.0069 0.5218 0.034 Uiso 1 calc R . . C78 C 0.69088(15) -0.1064(13) 0.6396(5) 0.0266(15) Uani 1 d . . . H78 H 0.7034 -0.2499 0.648 0.032 Uiso 1 calc R . . C79 C 0.67195(14) -0.0466(13) 0.7027(4) 0.0211(14) Uani 1 d . . . H79 H 0.6724 -0.1473 0.7555 0.025 Uiso 1 calc R . . N80 N 0.65305(12) 0.1442(11) 0.6940(4) 0.0253(13) Uani 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 0.015(2) 0.031(2) 0.019(2) -0.0022(18) 0.0011(19) 0.0026(18) C2 0.021(3) 0.028(3) 0.021(3) 0.003(3) -0.001(3) 0.004(3) C3 0.021(3) 0.025(3) 0.025(3) 0.000(3) -0.005(3) 0.001(3) O4 0.019(2) 0.023(2) 0.024(2) 0.0056(17) 0.002(2) -0.0035(18) C5 0.017(3) 0.015(3) 0.025(3) -0.006(2) 0.002(3) 0.001(2) C6 0.022(4) 0.018(3) 0.020(3) -0.003(2) 0.000(3) 0.000(2) C7 0.028(4) 0.022(3) 0.018(3) 0.002(2) 0.003(3) 0.006(3) S8 0.0148(8) 0.0189(7) 0.0245(8) 0.0020(6) 0.0048(7) -0.0016(6) C9 0.019(3) 0.015(2) 0.017(3) -0.001(2) 0.006(3) 0.000(2) C10 0.019(3) 0.022(3) 0.020(3) 0.001(2) 0.004(3) 0.005(2) C11 0.015(3) 0.020(3) 0.020(3) 0.000(2) 0.000(3) -0.001(2) C12 0.017(3) 0.018(3) 0.027(3) -0.001(2) 0.000(3) 0.002(2) C13 0.017(3) 0.016(3) 0.020(3) 0.001(2) 0.003(3) 0.004(2) C14 0.016(3) 0.016(3) 0.022(3) -0.002(2) 0.003(3) 0.002(2) N15 0.018(3) 0.013(2) 0.025(3) -0.0059(19) 0.003(2) -0.0026(19) C16 0.013(3) 0.019(3) 0.026(3) -0.005(2) 0.003(3) 0.003(2) C17 0.020(3) 0.020(3) 0.021(3) -0.006(2) 0.005(3) -0.004(2) O18 0.020(2) 0.024(2) 0.016(2) 0.0045(16) 0.0018(19) -0.0060(18) C19 0.036(5) 0.048(4) 0.026(4) 0.015(3) -0.004(4) -0.012(4) C20 0.038(5) 0.042(4) 0.032(4) 0.005(3) -0.009(4) -0.002(4) O21 0.025(3) 0.031(2) 0.020(2) 0.0017(18) -0.003(2) -0.006(2) C22 0.021(3) 0.024(3) 0.019(3) 0.000(2) 0.000(3) -0.001(2) C23 0.013(3) 0.018(3) 0.021(3) -0.001(2) -0.001(3) 0.003(2) S24 0.0144(8) 0.0271(7) 0.0184(8) -0.0010(6) 0.0001(6) -0.0048(6) C25 0.016(3) 0.024(3) 0.023(3) -0.006(2) 0.003(3) 0.002(2) C26 0.035(4) 0.027(3) 0.024(4) -0.001(3) 0.001(3) 0.008(3) C27 0.012(3) 0.033(3) 0.033(4) -0.008(3) 0.003(3) -0.003(3) C28 0.016(4) 0.032(3) 0.034(4) -0.004(3) 0.005(3) -0.004(3) C29 0.019(4) 0.027(3) 0.026(4) -0.001(3) 0.009(3) 0.000(3) N30 0.022(3) 0.027(3) 0.024(3) -0.007(2) 0.002(3) -0.003(2) O51 0.017(2) 0.024(2) 0.020(2) 0.0037(17) 0.001(2) 0.0046(17) C52 0.020(4) 0.026(3) 0.026(4) 0.003(3) 0.007(3) 0.003(3) C53 0.021(4) 0.029(3) 0.024(3) 0.003(3) 0.007(3) 0.003(3) O54 0.020(2) 0.019(2) 0.027(2) 0.0035(17) 0.005(2) 0.0055(17) C55 0.020(3) 0.021(3) 0.016(3) -0.002(2) 0.002(3) 0.004(2) C56 0.015(3) 0.016(2) 0.016(3) -0.001(2) 0.001(3) 0.001(2) C57 0.027(4) 0.017(3) 0.021(3) 0.001(2) -0.003(3) -0.001(2) S58 0.0136(8) 0.0179(6) 0.0232(8) 0.0015(6) -0.0020(6) 0.0026(6) C59 0.018(3) 0.014(2) 0.022(3) -0.001(2) -0.006(3) 0.002(2) C60 0.017(3) 0.015(3) 0.022(3) -0.005(2) -0.002(3) -0.002(2) C61 0.009(3) 0.022(3) 0.022(3) -0.008(2) 0.001(3) 0.003(2) C62 0.025(4) 0.016(2) 0.020(3) -0.001(2) -0.005(3) 0.003(2) C63 0.025(4) 0.019(3) 0.019(3) -0.002(2) -0.001(3) 0.001(3) C64 0.018(3) 0.018(3) 0.018(3) -0.001(2) -0.003(3) -0.005(2) N65 0.015(3) 0.017(2) 0.023(3) -0.0041(19) -0.001(2) -0.0022(19) C66 0.023(3) 0.015(2) 0.022(3) -0.001(2) -0.001(3) -0.001(2) C67 0.024(4) 0.022(3) 0.023(3) -0.002(2) -0.005(3) -0.003(3) O68 0.019(2) 0.0217(19) 0.016(2) 0.0033(16) 0.0022(19) 0.0023(17) C69 0.021(4) 0.062(5) 0.033(4) 0.018(4) 0.009(4) 0.011(4) C70 0.039(5) 0.061(5) 0.028(4) 0.010(4) -0.001(4) -0.004(4) O71 0.024(3) 0.027(2) 0.019(2) 0.0010(17) 0.006(2) -0.0011(19) C72 0.025(4) 0.023(3) 0.021(3) -0.003(2) 0.001(3) -0.007(3) C73 0.017(3) 0.015(3) 0.020(3) -0.001(2) 0.001(3) -0.004(2) S74 0.0148(8) 0.0234(7) 0.0210(8) 0.0026(6) 0.0007(7) 0.0013(6) C75 0.014(3) 0.019(3) 0.025(3) 0.000(2) 0.005(3) -0.001(2) C76 0.028(4) 0.027(3) 0.031(4) 0.001(3) 0.010(3) 0.004(3) C77 0.016(4) 0.031(3) 0.039(4) 0.002(3) 0.007(3) 0.004(3) C78 0.019(4) 0.025(3) 0.036(4) -0.008(3) -0.003(3) 0.004(3) C79 0.016(3) 0.027(3) 0.020(3) -0.003(2) -0.003(3) 0.001(2) N80 0.020(3) 0.030(3) 0.026(3) -0.004(2) -0.002(3) 0.002(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C6 1.375(8) . ? O1 C2 1.424(9) . ? C2 C3 1.518(8) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 O4 1.455(7) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? O4 C5 1.368(8) . ? C5 C9 1.379(9) . ? C5 C6 1.431(9) . ? C6 C7 1.370(10) . ? C7 S8 1.720(7) . ? C7 H7 0.95 . ? S8 C9 1.724(6) . ? C9 C10 1.469(8) . ? C10 N15 1.343(8) . ? C10 C11 1.401(9) . ? C11 C12 1.371(9) . ? C11 H11 0.95 . ? C12 C13 1.384(9) . ? C12 H12 0.95 . ? C13 C14 1.411(9) . ? C13 H13 0.95 . ? C14 N15 1.364(8) . ? C14 C16 1.456(8) . ? C16 C17 1.370(9) . ? C16 S24 1.738(7) . ? C17 O18 1.352(8) . ? C17 C22 1.447(9) . ? O18 C19 1.429(9) . ? C19 C20 1.470(11) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 O21 1.430(9) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? O21 C22 1.380(7) . ? C22 C23 1.383(9) . ? C23 C25 1.449(9) . ? C23 S24 1.724(6) . ? C25 N30 1.339(9) . ? C25 C26 1.401(9) . ? C26 C27 1.389(10) . ? C26 H26 0.95 . ? C27 C28 1.380(10) . ? C27 H27 0.95 . ? C28 C29 1.402(10) . ? C28 H28 0.95 . ? C29 N30 1.331(9) . ? C29 H29 0.95 . ? O51 C56 1.380(8) . ? O51 C52 1.427(8) . ? C52 C53 1.517(9) . ? C52 H52A 0.99 . ? C52 H52B 0.99 . ? C53 O54 1.445(8) . ? C53 H53A 0.99 . ? C53 H53B 0.99 . ? O54 C55 1.380(7) . ? C55 C59 1.366(10) . ? C55 C56 1.434(9) . ? C56 C57 1.339(9) . ? C57 S58 1.729(7) . ? C57 H57 0.95 . ? S58 C59 1.716(6) . ? C59 C60 1.484(9) . ? C60 N65 1.351(8) . ? C60 C61 1.397(8) . ? C61 C62 1.382(9) . ? C61 H61 0.95 . ? C62 C63 1.409(10) . ? C62 H62 0.95 . ? C63 C64 1.402(8) . ? C63 H63 0.95 . ? C64 N65 1.343(8) . ? C64 C66 1.449(9) . ? C66 C67 1.382(10) . ? C66 S74 1.744(6) . ? C67 O68 1.382(8) . ? C67 C72 1.410(10) . ? O68 C69 1.432(10) . ? C69 C70 1.415(12) . ? C69 H69A 0.99 . ? C69 H69B 0.99 . ? C70 O71 1.466(9) . ? C70 H70A 0.99 . ? C70 H70B 0.99 . ? O71 C72 1.369(8) . ? C72 C73 1.375(9) . ? C73 C75 1.460(8) . ? C73 S74 1.733(7) . ? C75 N80 1.352(8) . ? C75 C76 1.426(10) . ? C76 C77 1.393(9) . ? C76 H76 0.95 . ? C77 C78 1.359(11) . ? C77 H77 0.95 . ? C78 C79 1.382(11) . ? C78 H78 0.95 . ? C79 N80 1.334(9) . ? C79 H79 0.95 . ? 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 C6 O1 C2 111.1(5) . . ? O1 C2 C3 110.3(6) . . ? O1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? O1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? O4 C3 C2 110.3(5) . . ? O4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? O4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C5 O4 C3 112.8(5) . . ? O4 C5 C9 124.2(6) . . ? O4 C5 C6 122.9(6) . . ? C9 C5 C6 112.8(6) . . ? C7 C6 O1 125.4(6) . . ? C7 C6 C5 112.9(6) . . ? O1 C6 C5 121.7(6) . . ? C6 C7 S8 110.8(5) . . ? C6 C7 H7 124.6 . . ? S8 C7 H7 124.6 . . ? C7 S8 C9 93.1(3) . . ? C5 C9 C10 130.2(6) . . ? C5 C9 S8 110.3(5) . . ? C10 C9 S8 119.5(5) . . ? N15 C10 C11 122.5(5) . . ? N15 C10 C9 115.5(6) . . ? C11 C10 C9 122.0(6) . . ? C12 C11 C10 117.9(6) . . ? C12 C11 H11 121 . . ? C10 C11 H11 121 . . ? C11 C12 C13 121.8(6) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C12 C13 C14 117.1(5) . . ? C12 C13 H13 121.5 . . ? C14 C13 H13 121.5 . . ? N15 C14 C13 122.0(6) . . ? N15 C14 C16 115.1(5) . . ? C13 C14 C16 122.9(6) . . ? C10 N15 C14 118.7(5) . . ? C17 C16 C14 129.3(6) . . ? C17 C16 S24 111.7(5) . . ? C14 C16 S24 119.0(5) . . ? O18 C17 C16 125.3(6) . . ? O18 C17 C22 122.4(6) . . ? C16 C17 C22 112.2(6) . . ? C17 O18 C19 113.2(5) . . ? O18 C19 C20 113.5(6) . . ? O18 C19 H19A 108.9 . . ? C20 C19 H19A 108.9 . . ? O18 C19 H19B 108.9 . . ? C20 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? O21 C20 C19 111.8(7) . . ? O21 C20 H20A 109.3 . . ? C19 C20 H20A 109.3 . . ? O21 C20 H20B 109.3 . . ? C19 C20 H20B 109.3 . . ? H20A C20 H20B 107.9 . . ? C22 O21 C20 111.0(5) . . ? O21 C22 C23 125.8(6) . . ? O21 C22 C17 121.6(5) . . ? C23 C22 C17 112.5(6) . . ? C22 C23 C25 128.7(6) . . ? C22 C23 S24 111.4(5) . . ? C25 C23 S24 119.8(5) . . ? C23 S24 C16 92.2(3) . . ? N30 C25 C26 122.1(6) . . ? N30 C25 C23 115.0(6) . . ? C26 C25 C23 123.0(6) . . ? C27 C26 C25 118.7(6) . . ? C27 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? C28 C27 C26 119.3(7) . . ? C28 C27 H27 120.4 . . ? C26 C27 H27 120.4 . . ? C27 C28 C29 118.1(6) . . ? C27 C28 H28 120.9 . . ? C29 C28 H28 120.9 . . ? N30 C29 C28 123.1(7) . . ? N30 C29 H29 118.5 . . ? C28 C29 H29 118.5 . . ? C29 N30 C25 118.6(6) . . ? C56 O51 C52 110.5(5) . . ? O51 C52 C53 109.8(6) . . ? O51 C52 H52A 109.7 . . ? C53 C52 H52A 109.7 . . ? O51 C52 H52B 109.7 . . ? C53 C52 H52B 109.7 . . ? H52A C52 H52B 108.2 . . ? O54 C53 C52 110.7(5) . . ? O54 C53 H53A 109.5 . . ? C52 C53 H53A 109.5 . . ? O54 C53 H53B 109.5 . . ? C52 C53 H53B 109.5 . . ? H53A C53 H53B 108.1 . . ? C55 O54 C53 112.8(5) . . ? C59 C55 O54 124.9(6) . . ? C59 C55 C56 112.6(6) . . ? O54 C55 C56 122.4(6) . . ? C57 C56 O51 125.1(6) . . ? C57 C56 C55 113.2(6) . . ? O51 C56 C55 121.7(5) . . ? C56 C57 S58 111.1(5) . . ? C56 C57 H57 124.4 . . ? S58 C57 H57 124.4 . . ? C59 S58 C57 92.4(3) . . ? C55 C59 C60 129.8(5) . . ? C55 C59 S58 110.7(5) . . ? C60 C59 S58 119.3(5) . . ? N65 C60 C61 122.7(6) . . ? N65 C60 C59 114.9(5) . . ? C61 C60 C59 122.4(6) . . ? C62 C61 C60 119.3(6) . . ? C62 C61 H61 120.4 . . ? C60 C61 H61 120.4 . . ? C61 C62 C63 118.2(6) . . ? C61 C62 H62 120.9 . . ? C63 C62 H62 120.9 . . ? C64 C63 C62 119.2(6) . . ? C64 C63 H63 120.4 . . ? C62 C63 H63 120.4 . . ? N65 C64 C63 122.0(6) . . ? N65 C64 C66 114.9(5) . . ? C63 C64 C66 123.1(6) . . ? C64 N65 C60 118.5(5) . . ? C67 C66 C64 130.6(6) . . ? C67 C66 S74 109.7(5) . . ? C64 C66 S74 119.6(5) . . ? O68 C67 C66 122.7(6) . . ? O68 C67 C72 123.3(6) . . ? C66 C67 C72 113.9(6) . . ? C67 O68 C69 111.7(5) . . ? C70 C69 O68 115.4(7) . . ? C70 C69 H69A 108.4 . . ? O68 C69 H69A 108.4 . . ? C70 C69 H69B 108.4 . . ? O68 C69 H69B 108.4 . . ? H69A C69 H69B 107.5 . . ? C69 C70 O71 113.8(7) . . ? C69 C70 H70A 108.8 . . ? O71 C70 H70A 108.8 . . ? C69 C70 H70B 108.8 . . ? O71 C70 H70B 108.8 . . ? H70A C70 H70B 107.7 . . ? C72 O71 C70 109.9(6) . . ? O71 C72 C73 124.0(6) . . ? O71 C72 C67 122.9(6) . . ? C73 C72 C67 113.1(6) . . ? C72 C73 C75 131.0(7) . . ? C72 C73 S74 110.9(5) . . ? C75 C73 S74 118.1(5) . . ? C73 S74 C66 92.4(3) . . ? N80 C75 C76 121.9(6) . . ? N80 C75 C73 116.8(6) . . ? C76 C75 C73 121.2(6) . . ? C77 C76 C75 117.4(6) . . ? C77 C76 H76 121.3 . . ? C75 C76 H76 121.3 . . ? C78 C77 C76 120.1(7) . . ? C78 C77 H77 119.9 . . ? C76 C77 H77 119.9 . . ? C77 C78 C79 118.9(6) . . ? C77 C78 H78 120.6 . . ? C79 C78 H78 120.6 . . ? N80 C79 C78 123.9(7) . . ? N80 C79 H79 118.1 . . ? C78 C79 H79 118.1 . . ? C79 N80 C75 117.7(6) . . ? 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 C6 O1 C2 C3 52.6(7) . . . . ? O1 C2 C3 O4 -64.0(7) . . . . ? C2 C3 O4 C5 41.5(7) . . . . ? C3 O4 C5 C9 171.2(6) . . . . ? C3 O4 C5 C6 -12.6(8) . . . . ? C2 O1 C6 C7 156.9(6) . . . . ? C2 O1 C6 C5 -23.3(8) . . . . ? O4 C5 C6 C7 -177.8(6) . . . . ? C9 C5 C6 C7 -1.2(8) . . . . ? O4 C5 C6 O1 2.4(9) . . . . ? C9 C5 C6 O1 178.9(6) . . . . ? O1 C6 C7 S8 -180.0(5) . . . . ? C5 C6 C7 S8 0.2(7) . . . . ? C6 C7 S8 C9 0.7(5) . . . . ? O4 C5 C9 C10 0.0(11) . . . . ? C6 C5 C9 C10 -176.5(6) . . . . ? O4 C5 C9 S8 178.2(5) . . . . ? C6 C5 C9 S8 1.7(7) . . . . ? C7 S8 C9 C5 -1.4(5) . . . . ? C7 S8 C9 C10 177.0(5) . . . . ? C5 C9 C10 N15 166.8(6) . . . . ? S8 C9 C10 N15 -11.2(8) . . . . ? C5 C9 C10 C11 -11.5(11) . . . . ? S8 C9 C10 C11 170.5(5) . . . . ? N15 C10 C11 C12 -0.2(10) . . . . ? C9 C10 C11 C12 178.1(6) . . . . ? C10 C11 C12 C13 -0.5(10) . . . . ? C11 C12 C13 C14 -0.5(9) . . . . ? C12 C13 C14 N15 2.1(9) . . . . ? C12 C13 C14 C16 -176.3(6) . . . . ? C11 C10 N15 C14 1.7(9) . . . . ? C9 C10 N15 C14 -176.7(5) . . . . ? C13 C14 N15 C10 -2.7(9) . . . . ? C16 C14 N15 C10 175.8(5) . . . . ? N15 C14 C16 C17 -166.6(6) . . . . ? C13 C14 C16 C17 11.9(10) . . . . ? N15 C14 C16 S24 9.4(7) . . . . ? C13 C14 C16 S24 -172.1(5) . . . . ? C14 C16 C17 O18 -0.7(10) . . . . ? S24 C16 C17 O18 -176.9(5) . . . . ? C14 C16 C17 C22 176.6(6) . . . . ? S24 C16 C17 C22 0.4(7) . . . . ? C16 C17 O18 C19 -173.2(7) . . . . ? C22 C17 O18 C19 9.8(9) . . . . ? C17 O18 C19 C20 -38.7(9) . . . . ? O18 C19 C20 O21 60.6(9) . . . . ? C19 C20 O21 C22 -48.6(8) . . . . ? C20 O21 C22 C23 -157.7(7) . . . . ? C20 O21 C22 C17 20.4(8) . . . . ? O18 C17 C22 O21 -0.5(10) . . . . ? C16 C17 C22 O21 -177.9(6) . . . . ? O18 C17 C22 C23 177.9(6) . . . . ? C16 C17 C22 C23 0.5(8) . . . . ? O21 C22 C23 C25 0.8(11) . . . . ? C17 C22 C23 C25 -177.4(6) . . . . ? O21 C22 C23 S24 177.2(5) . . . . ? C17 C22 C23 S24 -1.1(7) . . . . ? C22 C23 S24 C16 1.1(5) . . . . ? C25 C23 S24 C16 177.8(5) . . . . ? C17 C16 S24 C23 -0.8(5) . . . . ? C14 C16 S24 C23 -177.6(5) . . . . ? C22 C23 C25 N30 176.0(6) . . . . ? S24 C23 C25 N30 -0.1(8) . . . . ? C22 C23 C25 C26 -4.7(11) . . . . ? S24 C23 C25 C26 179.2(5) . . . . ? N30 C25 C26 C27 -2.4(10) . . . . ? C23 C25 C26 C27 178.4(6) . . . . ? C25 C26 C27 C28 -0.3(10) . . . . ? C26 C27 C28 C29 1.0(10) . . . . ? C27 C28 C29 N30 0.9(11) . . . . ? C28 C29 N30 C25 -3.6(10) . . . . ? C26 C25 N30 C29 4.3(10) . . . . ? C23 C25 N30 C29 -176.4(6) . . . . ? C56 O51 C52 C53 -53.9(7) . . . . ? O51 C52 C53 O54 65.1(7) . . . . ? C52 C53 O54 C55 -41.1(7) . . . . ? C53 O54 C55 C59 -171.9(6) . . . . ? C53 O54 C55 C56 11.2(8) . . . . ? C52 O51 C56 C57 -157.4(6) . . . . ? C52 O51 C56 C55 24.1(7) . . . . ? C59 C55 C56 C57 2.4(8) . . . . ? O54 C55 C56 C57 179.6(5) . . . . ? C59 C55 C56 O51 -178.9(5) . . . . ? O54 C55 C56 O51 -1.7(9) . . . . ? O51 C56 C57 S58 179.8(4) . . . . ? C55 C56 C57 S58 -1.6(7) . . . . ? C56 C57 S58 C59 0.3(5) . . . . ? O54 C55 C59 C60 -2.9(10) . . . . ? C56 C55 C59 C60 174.3(6) . . . . ? O54 C55 C59 S58 -179.2(5) . . . . ? C56 C55 C59 S58 -2.0(7) . . . . ? C57 S58 C59 C55 1.0(5) . . . . ? C57 S58 C59 C60 -175.7(5) . . . . ? C55 C59 C60 N65 -168.9(6) . . . . ? S58 C59 C60 N65 7.2(7) . . . . ? C55 C59 C60 C61 10.1(9) . . . . ? S58 C59 C60 C61 -173.8(5) . . . . ? N65 C60 C61 C62 0.4(9) . . . . ? C59 C60 C61 C62 -178.5(5) . . . . ? C60 C61 C62 C63 0.7(9) . . . . ? C61 C62 C63 C64 0.4(9) . . . . ? C62 C63 C64 N65 -2.7(9) . . . . ? C62 C63 C64 C66 176.8(6) . . . . ? C63 C64 N65 C60 3.7(8) . . . . ? C66 C64 N65 C60 -175.8(5) . . . . ? C61 C60 N65 C64 -2.6(8) . . . . ? C59 C60 N65 C64 176.4(5) . . . . ? N65 C64 C66 C67 168.6(6) . . . . ? C63 C64 C66 C67 -10.9(10) . . . . ? N65 C64 C66 S74 -6.9(7) . . . . ? C63 C64 C66 S74 173.6(5) . . . . ? C64 C66 C67 O68 0.8(10) . . . . ? S74 C66 C67 O68 176.6(5) . . . . ? C64 C66 C67 C72 -177.0(6) . . . . ? S74 C66 C67 C72 -1.2(7) . . . . ? C66 C67 O68 C69 173.7(6) . . . . ? C72 C67 O68 C69 -8.7(8) . . . . ? C67 O68 C69 C70 36.3(9) . . . . ? O68 C69 C70 O71 -57.4(10) . . . . ? C69 C70 O71 C72 45.8(9) . . . . ? C70 O71 C72 C73 159.1(6) . . . . ? C70 O71 C72 C67 -19.0(8) . . . . ? O68 C67 C72 O71 1.2(9) . . . . ? C66 C67 C72 O71 178.9(6) . . . . ? O68 C67 C72 C73 -177.1(5) . . . . ? C66 C67 C72 C73 0.7(8) . . . . ? O71 C72 C73 C75 -0.4(10) . . . . ? C67 C72 C73 C75 177.9(6) . . . . ? O71 C72 C73 S74 -178.1(5) . . . . ? C67 C72 C73 S74 0.2(7) . . . . ? C72 C73 S74 C66 -0.7(5) . . . . ? C75 C73 S74 C66 -178.7(5) . . . . ? C67 C66 S74 C73 1.1(5) . . . . ? C64 C66 S74 C73 177.5(5) . . . . ? C72 C73 C75 N80 -175.3(6) . . . . ? S74 C73 C75 N80 2.2(7) . . . . ? C72 C73 C75 C76 3.2(10) . . . . ? S74 C73 C75 C76 -179.2(5) . . . . ? N80 C75 C76 C77 2.0(10) . . . . ? C73 C75 C76 C77 -176.4(6) . . . . ? C75 C76 C77 C78 -1.2(10) . . . . ? C76 C77 C78 C79 -1.1(10) . . . . ? C77 C78 C79 N80 2.9(10) . . . . ? C78 C79 N80 C75 -2.1(10) . . . . ? C76 C75 N80 C79 -0.4(9) . . . . ? C73 C75 N80 C79 178.1(5) . . . . ?