# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_arj_c58_107_1 _database_code_depnum_ccdc_archive 'CCDC 864129' #TrackingRef 'ARJ_C58_107_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19 H18 N6 S), C2 H6 O' _chemical_formula_sum 'C40 H42 N12 O S2' _chemical_formula_weight 771.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 7.6251(4) _cell_length_b 10.1757(5) _cell_length_c 12.2433(6) _cell_angle_alpha 104.3140(10) _cell_angle_beta 91.7630(10) _cell_angle_gamma 100.0410(10) _cell_volume 903.66(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6238 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 28.17 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.006 _exptl_crystal_size_mid 0.002 _exptl_crystal_size_min 0.0013 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 406.0 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Multiscan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEX-II CCD DUO' _diffrn_measurement_method '\ f and \ w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15612 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3949 _reflns_number_gt 3342 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _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^)+(0.1000P)^2^+0.4781P] 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 3949 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1426 _refine_ls_wR_factor_gt 0.1316 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 0.3524(2) 1.25446(19) 0.20486(14) 0.0162(4) Uani 1 1 d . . . C2 C 0.2024(3) 1.3222(2) 0.25332(16) 0.0209(4) Uani 1 1 d . . . H2A H 0.1351 1.3435 0.1935 0.025 Uiso 1 1 calc R . . H2B H 0.2511 1.4082 0.3087 0.025 Uiso 1 1 calc R . . C3 C 0.0781(3) 1.2283(2) 0.30943(16) 0.0197(4) Uani 1 1 d . . . H3A H 0.0042 1.2821 0.3582 0.024 Uiso 1 1 calc R . . H3B H 0.0000 1.1578 0.2519 0.024 Uiso 1 1 calc R . . C4 C 0.1850(3) 1.1602(2) 0.37859(15) 0.0188(4) Uani 1 1 d . . . H4A H 0.1041 1.1059 0.4174 0.023 Uiso 1 1 calc R . . H4B H 0.2644 1.2309 0.4353 0.023 Uiso 1 1 calc R . . C5 C 0.2949(2) 1.06680(19) 0.30375(15) 0.0161(4) Uani 1 1 d . . . H5A H 0.3759 1.0370 0.3512 0.019 Uiso 1 1 calc R . . H5B H 0.2154 0.9853 0.2583 0.019 Uiso 1 1 calc R . . C6 C 0.4012(2) 1.14029(18) 0.22679(14) 0.0142(4) Uani 1 1 d . . . C7 C 0.5530(2) 1.10351(18) 0.16458(14) 0.0134(4) Uani 1 1 d . . . C8 C 0.6063(2) 1.19565(18) 0.09604(14) 0.0153(4) Uani 1 1 d . . . C9 C 0.8168(2) 1.0817(2) 0.02120(15) 0.0175(4) Uani 1 1 d . . . H9 H 0.9021 1.0686 -0.0311 0.021 Uiso 1 1 calc R . . C10 C 0.6609(2) 1.00268(18) 0.15780(14) 0.0133(4) Uani 1 1 d . . . C11 C 0.6520(2) 0.90310(18) 0.23498(14) 0.0132(3) Uani 1 1 d . . . C12 C 0.8052(2) 0.82061(19) 0.21962(15) 0.0167(4) Uani 1 1 d . . . H12A H 0.8051 0.7728 0.1405 0.020 Uiso 1 1 calc R . . H12B H 0.9188 0.8836 0.2419 0.020 Uiso 1 1 calc R . . C13 C 0.7843(2) 0.71685(19) 0.29011(15) 0.0153(4) Uani 1 1 d . . . C14 C 0.6207(2) 0.66347(18) 0.32440(14) 0.0136(4) Uani 1 1 d . . . C15 C 0.4529(2) 0.71198(19) 0.29796(15) 0.0146(4) Uani 1 1 d . . . H15A H 0.4183 0.7690 0.3667 0.018 Uiso 1 1 calc R . . H15B H 0.3574 0.6326 0.2708 0.018 Uiso 1 1 calc R . . C16 C 0.4763(2) 0.79437(18) 0.20941(14) 0.0138(4) Uani 1 1 d . . . H16A H 0.3757 0.8407 0.2075 0.017 Uiso 1 1 calc R . . H16B H 0.4772 0.7318 0.1356 0.017 Uiso 1 1 calc R . . C17 C 0.7538(2) 0.53071(19) 0.41501(14) 0.0150(4) Uani 1 1 d . . . C18 C 0.9307(2) 0.6707(2) 0.32761(16) 0.0197(4) Uani 1 1 d . . . H18 H 1.0431 0.7065 0.3087 0.024 Uiso 1 1 calc R . . C19 C 0.6755(2) 0.98838(19) 0.35434(15) 0.0149(4) Uani 1 1 d . . . C20 C 0.1197(5) 0.6004(4) 0.0837(3) 0.0689(11) Uani 1 1 d . . . H20A H 0.2196 0.5614 0.1013 0.103 Uiso 1 1 calc R . . H20B H 0.0589 0.6280 0.1507 0.103 Uiso 1 1 calc R . . H20C H 0.1612 0.6794 0.0554 0.103 Uiso 1 1 calc R . . N1 N 0.7370(2) 1.18812(16) 0.02544(13) 0.0175(3) Uani 1 1 d . . . N2 N 0.7873(2) 0.99062(16) 0.08465(12) 0.0159(3) Uani 1 1 d . . . N3 N 0.6036(2) 0.57079(15) 0.38658(12) 0.0136(3) Uani 1 1 d . . . N4 N 0.9203(2) 0.57835(17) 0.38892(13) 0.0191(3) Uani 1 1 d . . . N5 N 0.7372(2) 0.43546(17) 0.47538(13) 0.0183(3) Uani 1 1 d . . . H5C H 0.6337 0.4031 0.4940 0.022 Uiso 1 1 calc R . . H5D H 0.8300 0.4070 0.4953 0.022 Uiso 1 1 calc R . . N6 N 0.7044(2) 1.05313(18) 0.44574(13) 0.0217(4) Uani 1 1 d . . . O1 O 0.0000 0.5000 0.0000 0.132(2) Uani 1 2 d S . . S1 S 0.48206(7) 1.32420(5) 0.11174(4) 0.01943(15) 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 0.0204(9) 0.0153(8) 0.0130(8) 0.0042(6) 0.0019(7) 0.0025(7) C2 0.0259(10) 0.0195(9) 0.0199(9) 0.0056(7) 0.0051(7) 0.0098(8) C3 0.0186(9) 0.0215(9) 0.0193(9) 0.0036(7) 0.0036(7) 0.0059(7) C4 0.0182(9) 0.0223(9) 0.0166(8) 0.0053(7) 0.0061(7) 0.0048(7) C5 0.0138(8) 0.0195(9) 0.0165(8) 0.0074(7) 0.0036(6) 0.0030(7) C6 0.0140(8) 0.0157(8) 0.0120(7) 0.0032(6) -0.0005(6) 0.0008(7) C7 0.0140(8) 0.0150(8) 0.0108(8) 0.0049(6) -0.0009(6) -0.0006(6) C8 0.0174(9) 0.0146(8) 0.0137(8) 0.0051(6) -0.0004(6) 0.0008(7) C9 0.0151(9) 0.0247(10) 0.0151(8) 0.0101(7) 0.0032(6) 0.0031(7) C10 0.0126(8) 0.0155(8) 0.0122(8) 0.0062(6) -0.0009(6) 0.0002(6) C11 0.0126(8) 0.0162(8) 0.0130(8) 0.0074(6) 0.0026(6) 0.0028(6) C12 0.0133(8) 0.0212(9) 0.0197(9) 0.0115(7) 0.0045(7) 0.0050(7) C13 0.0146(8) 0.0188(9) 0.0154(8) 0.0080(7) 0.0033(6) 0.0057(7) C14 0.0144(8) 0.0146(8) 0.0118(8) 0.0032(6) 0.0003(6) 0.0035(6) C15 0.0118(8) 0.0177(9) 0.0163(8) 0.0085(7) 0.0011(6) 0.0019(7) C16 0.0125(8) 0.0158(8) 0.0151(8) 0.0074(6) 0.0005(6) 0.0029(6) C17 0.0185(9) 0.0154(8) 0.0126(8) 0.0039(6) 0.0033(6) 0.0063(7) C18 0.0136(9) 0.0271(10) 0.0238(9) 0.0135(8) 0.0067(7) 0.0072(7) C19 0.0122(8) 0.0184(9) 0.0176(9) 0.0115(7) 0.0022(6) 0.0022(7) C20 0.068(2) 0.077(2) 0.061(2) 0.0405(18) -0.0086(17) -0.0202(19) N1 0.0190(8) 0.0202(8) 0.0153(7) 0.0099(6) 0.0030(6) 0.0012(6) N2 0.0144(7) 0.0205(8) 0.0146(7) 0.0088(6) 0.0017(6) 0.0017(6) N3 0.0145(7) 0.0138(7) 0.0140(7) 0.0059(6) 0.0007(5) 0.0035(6) N4 0.0168(8) 0.0250(8) 0.0215(8) 0.0129(7) 0.0056(6) 0.0098(6) N5 0.0177(8) 0.0211(8) 0.0225(8) 0.0139(6) 0.0040(6) 0.0081(6) N6 0.0209(8) 0.0262(9) 0.0187(8) 0.0087(7) 0.0008(6) 0.0020(7) O1 0.129(4) 0.073(3) 0.171(5) 0.044(3) -0.074(4) -0.047(3) S1 0.0285(3) 0.0151(2) 0.0182(2) 0.00869(17) 0.00646(18) 0.00622(18) _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 C6 1.363(3) . ? C1 C2 1.500(3) . ? C1 S1 1.7337(18) . ? C2 C3 1.527(3) . ? C3 C4 1.519(3) . ? C4 C5 1.529(3) . ? C5 C6 1.513(2) . ? C6 C7 1.458(2) . ? C7 C10 1.411(3) . ? C7 C8 1.423(2) . ? C8 N1 1.339(2) . ? C8 S1 1.722(2) . ? C9 N1 1.322(3) . ? C9 N2 1.345(2) . ? C10 N2 1.336(2) . ? C10 C11 1.542(2) . ? C11 C19 1.491(2) . ? C11 C12 1.543(2) . ? C11 C16 1.551(2) . ? C12 C13 1.512(2) . ? C13 C18 1.391(3) . ? C13 C14 1.392(2) . ? C14 N3 1.343(2) . ? C14 C15 1.503(2) . ? C15 C16 1.523(2) . ? C17 N3 1.344(2) . ? C17 N5 1.349(2) . ? C17 N4 1.355(2) . ? C18 N4 1.334(2) . ? C19 N6 1.142(2) . ? C20 O1 1.423(3) . ? O1 C20 1.423(3) 2_565 ? 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 C1 C2 126.48(17) . . ? C6 C1 S1 114.45(14) . . ? C2 C1 S1 119.07(14) . . ? C1 C2 C3 111.03(16) . . ? C4 C3 C2 110.63(16) . . ? C3 C4 C5 111.33(15) . . ? C6 C5 C4 111.63(15) . . ? C1 C6 C7 111.40(16) . . ? C1 C6 C5 119.65(17) . . ? C7 C6 C5 128.90(16) . . ? C10 C7 C8 113.21(16) . . ? C10 C7 C6 136.06(16) . . ? C8 C7 C6 110.71(16) . . ? N1 C8 C7 126.05(17) . . ? N1 C8 S1 121.32(14) . . ? C7 C8 S1 112.63(14) . . ? N1 C9 N2 126.75(17) . . ? N2 C10 C7 121.24(15) . . ? N2 C10 C11 114.18(15) . . ? C7 C10 C11 124.52(15) . . ? C19 C11 C10 107.54(14) . . ? C19 C11 C12 106.47(14) . . ? C10 C11 C12 112.35(14) . . ? C19 C11 C16 112.68(14) . . ? C10 C11 C16 111.70(14) . . ? C12 C11 C16 106.05(14) . . ? C13 C12 C11 110.77(14) . . ? C18 C13 C14 115.32(16) . . ? C18 C13 C12 121.51(16) . . ? C14 C13 C12 123.15(16) . . ? N3 C14 C13 122.63(16) . . ? N3 C14 C15 115.97(15) . . ? C13 C14 C15 121.34(16) . . ? C14 C15 C16 112.26(14) . . ? C15 C16 C11 111.65(14) . . ? N3 C17 N5 117.08(16) . . ? N3 C17 N4 125.65(16) . . ? N5 C17 N4 117.26(17) . . ? N4 C18 C13 124.17(17) . . ? N6 C19 C11 175.76(19) . . ? C9 N1 C8 113.84(15) . . ? C10 N2 C9 118.56(16) . . ? C14 N3 C17 116.73(15) . . ? C18 N4 C17 115.44(16) . . ? C20 O1 C20 179.998(1) . 2_565 ? C8 S1 C1 90.76(9) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.367 _refine_diff_density_min -0.656 _refine_diff_density_rms 0.072 data_c58_94_1 _database_code_depnum_ccdc_archive 'CCDC 864130' #TrackingRef 'C58_94_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 N3 O3 S' _chemical_formula_sum 'C19 H19 N3 O3 S' _chemical_formula_weight 369.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.092(5) _cell_length_b 11.448(5) _cell_length_c 15.672(7) _cell_angle_alpha 89.924(8) _cell_angle_beta 89.583(9) _cell_angle_gamma 62.283(7) _cell_volume 1761.7(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8710 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.52 _exptl_crystal_description plate _exptl_crystal_colour transparant _exptl_crystal_size_max 0.008 _exptl_crystal_size_mid 0.004 _exptl_crystal_size_min 0.002 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776.0 _exptl_absorpt_coefficient_mu 0.209 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.999 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Multiscan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEX-II CCD DUO' _diffrn_measurement_method '\ f and \ w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20533 _diffrn_reflns_av_R_equivalents 0.0810 _diffrn_reflns_av_sigmaI/netI 0.0976 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7395 _reflns_number_gt 5076 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _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^)+(0.1000P)^2^+0.5886P] 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 7395 _refine_ls_number_parameters 473 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1761 _refine_ls_R_factor_gt 0.1380 _refine_ls_wR_factor_ref 0.3472 _refine_ls_wR_factor_gt 0.3287 _refine_ls_goodness_of_fit_ref 1.920 _refine_ls_restrained_S_all 1.920 _refine_ls_shift/su_max 0.025 _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 0.4394(7) -0.1859(6) 0.4320(4) 0.0222(14) Uani 1 1 d . . . C2 C 0.4446(7) -0.3128(6) 0.4630(4) 0.0272(16) Uani 1 1 d . . . H2A H 0.4959 -0.3394 0.5156 0.033 Uiso 1 1 calc R . . H2B H 0.4915 -0.3816 0.4209 0.033 Uiso 1 1 calc R . . C3 C 0.3021(8) -0.2979(6) 0.4786(5) 0.0300(17) Uani 1 1 d . . . H3A H 0.2631 -0.3049 0.4249 0.036 Uiso 1 1 calc R . . H3B H 0.3075 -0.3680 0.5157 0.036 Uiso 1 1 calc R . . C4 C 0.2121(7) -0.1656(6) 0.5193(5) 0.0272(16) Uani 1 1 d . . . H4A H 0.2534 -0.1569 0.5717 0.033 Uiso 1 1 calc R . . H4B H 0.1243 -0.1599 0.5335 0.033 Uiso 1 1 calc R . . C5 C 0.1926(7) -0.0542(6) 0.4587(4) 0.0255(15) Uani 1 1 d . . . H5A H 0.1405 -0.0561 0.4097 0.031 Uiso 1 1 calc R . . H5B H 0.1412 0.0299 0.4875 0.031 Uiso 1 1 calc R . . C6 C 0.3282(7) -0.0664(6) 0.4287(4) 0.0204(14) Uani 1 1 d . . . C7 C 0.3617(7) 0.0351(6) 0.3985(4) 0.0197(13) Uani 1 1 d . . . C8 C 0.2886(7) 0.1736(6) 0.3811(4) 0.0214(14) Uani 1 1 d . . . C9 C 0.4885(8) 0.1726(7) 0.3417(5) 0.0324(17) Uani 1 1 d . . . H9 H 0.5305 0.2211 0.3214 0.039 Uiso 1 1 calc R . . C10 C 0.5018(7) -0.0196(6) 0.3827(4) 0.0230(14) Uani 1 1 d . . . C11 C 0.1339(7) 0.2577(5) 0.3845(4) 0.0195(13) Uani 1 1 d . . . C12 C 0.0704(6) 0.1998(5) 0.3187(4) 0.0177(13) Uani 1 1 d . . . H12A H 0.1154 0.1901 0.2640 0.021 Uiso 1 1 calc R . . H12B H 0.0875 0.1127 0.3375 0.021 Uiso 1 1 calc R . . C13 C -0.0795(7) 0.2834(5) 0.3076(4) 0.0166(12) Uani 1 1 d . . . C14 C -0.1431(7) 0.4130(6) 0.3301(4) 0.0219(14) Uani 1 1 d . . . C15 C -0.0687(7) 0.4838(6) 0.3639(4) 0.0246(15) Uani 1 1 d . . . H15A H -0.0945 0.5069 0.4231 0.030 Uiso 1 1 calc R . . H15B H -0.0969 0.5652 0.3323 0.030 Uiso 1 1 calc R . . C16 C 0.0863(7) 0.4029(5) 0.3579(4) 0.0216(14) Uani 1 1 d . . . H16A H 0.1281 0.4417 0.3947 0.026 Uiso 1 1 calc R . . H16B H 0.1158 0.4053 0.2997 0.026 Uiso 1 1 calc R . . C17 C -0.1616(7) 0.2249(6) 0.2748(4) 0.0199(13) Uani 1 1 d . . . C18 C -0.1560(8) 0.0202(7) 0.2327(5) 0.0334(18) Uani 1 1 d . . . H18A H -0.2519 0.0776 0.2275 0.050 Uiso 1 1 calc R . . H18B H -0.1407 -0.0439 0.2764 0.050 Uiso 1 1 calc R . . H18C H -0.1206 -0.0242 0.1793 0.050 Uiso 1 1 calc R . . C19 C 0.0814(7) 0.2618(5) 0.4722(4) 0.0215(14) Uani 1 1 d . . . C20 C 0.9390(7) 0.3138(6) 0.0672(4) 0.0231(14) Uani 1 1 d . . . C21 C 0.9440(7) 0.1872(6) 0.0372(4) 0.0265(15) Uani 1 1 d . . . H21A H 0.9893 0.1193 0.0798 0.032 Uiso 1 1 calc R . . H21B H 0.9970 0.1591 -0.0152 0.032 Uiso 1 1 calc R . . C22 C 0.8012(8) 0.2022(6) 0.0214(5) 0.0314(17) Uani 1 1 d . . . H22A H 0.8075 0.1322 -0.0161 0.038 Uiso 1 1 calc R . . H22B H 0.7609 0.1949 0.0750 0.038 Uiso 1 1 calc R . . C23 C 0.7125(7) 0.3343(6) -0.0187(4) 0.0273(15) Uani 1 1 d . . . H23A H 0.6248 0.3401 -0.0326 0.033 Uiso 1 1 calc R . . H23B H 0.7546 0.3422 -0.0713 0.033 Uiso 1 1 calc R . . C24 C 0.6916(7) 0.4470(6) 0.0412(4) 0.0254(15) Uani 1 1 d . . . H24A H 0.6416 0.5305 0.0120 0.030 Uiso 1 1 calc R . . H24B H 0.6381 0.4464 0.0903 0.030 Uiso 1 1 calc R . . C25 C 0.8266(7) 0.4337(6) 0.0706(4) 0.0196(13) Uani 1 1 d . . . C26 C 0.8610(7) 0.5355(6) 0.1008(4) 0.0183(13) Uani 1 1 d . . . C27 C 0.7888(7) 0.6732(6) 0.1186(4) 0.0199(13) Uani 1 1 d . . . C28 C 0.9878(8) 0.6728(6) 0.1576(5) 0.0307(16) Uani 1 1 d . . . H28 H 1.0293 0.7221 0.1767 0.037 Uiso 1 1 calc R . . C29 C 1.0038(7) 0.4793(6) 0.1167(4) 0.0244(15) Uani 1 1 d . . . C30 C 0.6337(7) 0.7577(5) 0.1148(4) 0.0185(13) Uani 1 1 d . . . C31 C 0.5732(6) 0.6985(5) 0.1808(4) 0.0170(13) Uani 1 1 d . . . H31A H 0.5915 0.6109 0.1623 0.020 Uiso 1 1 calc R . . H31B H 0.6173 0.6901 0.2353 0.020 Uiso 1 1 calc R . . C32 C 0.4205(7) 0.7837(5) 0.1917(4) 0.0182(13) Uani 1 1 d . . . C33 C 0.3580(7) 0.9127(6) 0.1699(4) 0.0198(13) Uani 1 1 d . . . C34 C 0.4323(7) 0.9827(6) 0.1355(4) 0.0266(16) Uani 1 1 d . . . H34A H 0.4032 1.0647 0.1667 0.032 Uiso 1 1 calc R . . H34B H 0.4077 1.0047 0.0762 0.032 Uiso 1 1 calc R . . C35 C 0.5862(7) 0.9030(6) 0.1414(4) 0.0243(15) Uani 1 1 d . . . H35A H 0.6145 0.9058 0.1994 0.029 Uiso 1 1 calc R . . H35B H 0.6287 0.9414 0.1043 0.029 Uiso 1 1 calc R . . C36 C 0.3383(7) 0.7243(6) 0.2244(4) 0.0231(14) Uani 1 1 d . . . C37 C 0.3431(8) 0.5208(7) 0.2662(5) 0.0353(18) Uani 1 1 d . . . H37A H 0.3772 0.4761 0.3193 0.053 Uiso 1 1 calc R . . H37B H 0.3586 0.4572 0.2221 0.053 Uiso 1 1 calc R . . H37C H 0.2472 0.5789 0.2716 0.053 Uiso 1 1 calc R . . C38 C 0.5817(7) 0.7621(5) 0.0275(4) 0.0194(14) Uani 1 1 d . . . N1 N 0.3538(6) 0.2392(5) 0.3535(4) 0.0261(13) Uani 1 1 d . . . N2 N 0.5695(6) 0.0452(5) 0.3554(4) 0.0272(13) Uani 1 1 d . . . N3 N 0.0372(6) 0.2754(5) 0.5393(4) 0.0296(14) Uani 1 1 d . . . N4 N 0.8547(6) 0.7383(5) 0.1465(4) 0.0267(13) Uani 1 1 d . . . N5 N 1.0695(6) 0.5452(5) 0.1449(4) 0.0262(13) Uani 1 1 d . . . N6 N 0.5366(7) 0.7761(6) -0.0399(4) 0.0314(14) Uani 1 1 d . . . O1 O -0.2765(5) 0.4902(4) 0.3254(3) 0.0271(11) Uani 1 1 d . . . H1 H -0.3133 0.4472 0.3079 0.041 Uiso 1 1 calc R . . O2 O -0.2871(5) 0.2837(4) 0.2668(3) 0.0274(11) Uani 1 1 d . . . O3 O -0.0873(5) 0.0974(4) 0.2550(3) 0.0270(11) Uani 1 1 d . . . O4 O 0.2220(5) 0.9906(4) 0.1746(3) 0.0262(11) Uani 1 1 d . . . H4 H 0.1857 0.9488 0.1952 0.039 Uiso 1 1 calc R . . O5 O 0.2139(5) 0.7837(4) 0.2326(3) 0.0279(11) Uani 1 1 d . . . O6 O 0.4132(5) 0.5971(4) 0.2444(3) 0.0270(11) Uani 1 1 d . . . S1 S 0.58967(18) -0.18614(15) 0.40316(11) 0.0250(4) Uani 1 1 d . . . S2 S 1.08996(18) 0.31378(15) 0.09691(11) 0.0244(4) 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 0.021(4) 0.017(3) 0.027(3) 0.000(2) 0.002(3) -0.007(3) C2 0.027(4) 0.010(3) 0.036(4) -0.001(2) 0.011(3) -0.002(3) C3 0.029(4) 0.012(3) 0.044(4) 0.003(3) 0.007(3) -0.006(3) C4 0.024(4) 0.015(3) 0.042(4) 0.004(3) 0.010(3) -0.008(3) C5 0.021(4) 0.014(3) 0.039(4) 0.006(3) 0.008(3) -0.006(3) C6 0.026(4) 0.016(3) 0.018(3) 0.000(2) 0.005(3) -0.008(3) C7 0.017(4) 0.015(3) 0.025(3) -0.006(2) 0.008(3) -0.006(3) C8 0.020(4) 0.017(3) 0.028(3) -0.002(2) 0.006(3) -0.009(3) C9 0.029(4) 0.026(3) 0.050(5) 0.001(3) 0.009(4) -0.020(3) C10 0.023(4) 0.020(3) 0.027(4) -0.004(2) 0.006(3) -0.011(3) C11 0.020(4) 0.009(2) 0.030(4) 0.000(2) 0.001(3) -0.007(3) C12 0.015(3) 0.012(2) 0.024(3) 0.000(2) 0.001(3) -0.005(2) C13 0.018(4) 0.013(3) 0.019(3) 0.001(2) -0.002(2) -0.007(2) C14 0.020(4) 0.011(3) 0.030(4) 0.003(2) 0.001(3) -0.004(3) C15 0.023(4) 0.010(3) 0.034(4) 0.000(2) 0.001(3) -0.002(3) C16 0.021(4) 0.007(2) 0.035(4) 0.002(2) -0.001(3) -0.005(2) C17 0.021(4) 0.018(3) 0.022(3) 0.003(2) 0.002(3) -0.010(3) C18 0.032(4) 0.031(4) 0.051(5) -0.015(3) 0.011(4) -0.026(3) C19 0.016(3) 0.008(2) 0.039(4) -0.006(2) -0.001(3) -0.004(2) C20 0.025(4) 0.016(3) 0.028(4) -0.001(2) 0.007(3) -0.009(3) C21 0.025(4) 0.013(3) 0.035(4) -0.002(3) -0.001(3) -0.004(3) C22 0.029(4) 0.018(3) 0.049(5) -0.007(3) -0.001(3) -0.012(3) C23 0.026(4) 0.022(3) 0.038(4) -0.008(3) 0.001(3) -0.015(3) C24 0.026(4) 0.015(3) 0.037(4) -0.005(3) -0.002(3) -0.010(3) C25 0.023(4) 0.014(3) 0.021(3) -0.002(2) 0.004(3) -0.007(3) C26 0.016(3) 0.015(3) 0.024(3) 0.000(2) 0.002(3) -0.007(3) C27 0.017(4) 0.014(3) 0.028(3) 0.001(2) 0.005(3) -0.006(3) C28 0.027(4) 0.020(3) 0.049(5) -0.005(3) 0.000(3) -0.014(3) C29 0.025(4) 0.021(3) 0.030(4) -0.007(3) 0.010(3) -0.013(3) C30 0.017(3) 0.011(3) 0.028(3) 0.000(2) 0.004(3) -0.007(2) C31 0.018(4) 0.010(2) 0.024(3) -0.001(2) 0.004(3) -0.008(2) C32 0.018(4) 0.012(2) 0.023(3) -0.003(2) 0.005(3) -0.007(2) C33 0.015(3) 0.013(3) 0.031(4) -0.004(2) 0.001(3) -0.006(3) C34 0.029(4) 0.012(3) 0.039(4) 0.000(3) 0.008(3) -0.009(3) C35 0.024(4) 0.013(3) 0.037(4) -0.004(2) 0.009(3) -0.010(3) C36 0.030(4) 0.018(3) 0.023(3) -0.005(2) 0.003(3) -0.013(3) C37 0.040(5) 0.027(3) 0.050(5) 0.011(3) 0.001(4) -0.025(4) C38 0.015(3) 0.010(2) 0.034(4) 0.004(2) 0.004(3) -0.007(2) N1 0.020(3) 0.016(2) 0.043(3) 0.003(2) 0.003(3) -0.010(2) N2 0.025(4) 0.025(3) 0.035(3) -0.001(2) 0.005(3) -0.015(3) N3 0.037(4) 0.025(3) 0.032(3) -0.010(2) 0.014(3) -0.019(3) N4 0.019(3) 0.017(2) 0.046(4) -0.004(2) 0.002(3) -0.011(2) N5 0.017(3) 0.019(3) 0.042(3) 0.000(2) 0.001(3) -0.008(2) N6 0.043(4) 0.026(3) 0.033(4) 0.004(2) 0.000(3) -0.023(3) O1 0.021(3) 0.0112(19) 0.046(3) 0.0020(19) 0.000(2) -0.0051(19) O2 0.026(3) 0.020(2) 0.039(3) 0.0029(19) -0.004(2) -0.013(2) O3 0.031(3) 0.020(2) 0.036(3) -0.0099(19) 0.010(2) -0.017(2) O4 0.019(3) 0.013(2) 0.046(3) -0.0048(19) 0.010(2) -0.0065(19) O5 0.025(3) 0.021(2) 0.042(3) -0.004(2) 0.008(2) -0.014(2) O6 0.029(3) 0.018(2) 0.040(3) 0.0078(19) 0.000(2) -0.016(2) S1 0.0207(10) 0.0166(7) 0.0325(10) -0.0028(6) 0.0065(7) -0.0044(7) S2 0.0187(9) 0.0155(7) 0.0338(10) -0.0002(6) 0.0038(7) -0.0037(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.352(9) . ? C1 C2 1.507(8) . ? C1 S1 1.723(7) . ? C2 C3 1.527(10) . ? C3 C4 1.511(8) . ? C4 C5 1.522(8) . ? C5 C6 1.516(9) . ? C6 C7 1.453(8) . ? C7 C10 1.399(9) . ? C7 C8 1.433(8) . ? C8 N1 1.333(7) . ? C8 C11 1.529(9) . ? C9 N2 1.328(9) . ? C9 N1 1.335(9) . ? C10 N2 1.345(8) . ? C10 S1 1.721(7) . ? C11 C19 1.482(9) . ? C11 C16 1.550(7) . ? C11 C12 1.563(8) . ? C12 C13 1.494(9) . ? C13 C14 1.359(8) . ? C13 C17 1.455(8) . ? C14 O1 1.328(8) . ? C14 C15 1.499(9) . ? C15 C16 1.530(9) . ? C17 O2 1.239(8) . ? C17 O3 1.336(7) . ? C18 O3 1.455(7) . ? C19 N3 1.136(8) . ? C20 C25 1.359(9) . ? C20 C21 1.500(8) . ? C20 S2 1.741(7) . ? C21 C22 1.534(10) . ? C22 C23 1.507(10) . ? C23 C24 1.524(8) . ? C24 C25 1.509(9) . ? C25 C26 1.465(8) . ? C26 C27 1.424(8) . ? C26 C29 1.429(9) . ? C27 N4 1.339(8) . ? C27 C30 1.534(9) . ? C28 N4 1.321(9) . ? C28 N5 1.327(8) . ? C29 N5 1.347(8) . ? C29 S2 1.707(6) . ? C30 C38 1.481(9) . ? C30 C31 1.546(7) . ? C30 C35 1.549(7) . ? C31 C32 1.520(8) . ? C32 C33 1.351(8) . ? C32 C36 1.458(8) . ? C33 O4 1.351(8) . ? C33 C34 1.490(8) . ? C34 C35 1.520(10) . ? C36 O5 1.229(8) . ? C36 O6 1.336(8) . ? C37 O6 1.452(7) . ? C38 N6 1.150(8) . ? 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 C1 C2 126.7(6) . . ? C6 C1 S1 114.7(5) . . ? C2 C1 S1 118.5(5) . . ? C1 C2 C3 111.5(5) . . ? C4 C3 C2 110.1(5) . . ? C3 C4 C5 110.4(5) . . ? C6 C5 C4 111.3(6) . . ? C1 C6 C7 111.8(6) . . ? C1 C6 C5 118.7(5) . . ? C7 C6 C5 129.5(5) . . ? C10 C7 C8 113.7(5) . . ? C10 C7 C6 110.0(5) . . ? C8 C7 C6 136.3(6) . . ? N1 C8 C7 120.6(6) . . ? N1 C8 C11 113.5(5) . . ? C7 C8 C11 125.7(5) . . ? N2 C9 N1 127.7(6) . . ? N2 C10 C7 126.5(6) . . ? N2 C10 S1 119.8(5) . . ? C7 C10 S1 113.7(4) . . ? C19 C11 C8 110.8(5) . . ? C19 C11 C16 106.4(5) . . ? C8 C11 C16 113.0(5) . . ? C19 C11 C12 112.3(5) . . ? C8 C11 C12 108.0(5) . . ? C16 C11 C12 106.3(5) . . ? C13 C12 C11 113.4(5) . . ? C14 C13 C17 118.5(6) . . ? C14 C13 C12 121.7(5) . . ? C17 C13 C12 119.8(5) . . ? O1 C14 C13 124.2(6) . . ? O1 C14 C15 112.7(5) . . ? C13 C14 C15 123.1(6) . . ? C14 C15 C16 113.6(5) . . ? C15 C16 C11 111.1(5) . . ? O2 C17 O3 122.3(5) . . ? O2 C17 C13 125.1(5) . . ? O3 C17 C13 112.6(6) . . ? N3 C19 C11 174.7(6) . . ? C25 C20 C21 126.2(6) . . ? C25 C20 S2 114.9(5) . . ? C21 C20 S2 118.9(5) . . ? C20 C21 C22 111.9(5) . . ? C23 C22 C21 110.0(5) . . ? C22 C23 C24 111.2(6) . . ? C25 C24 C23 110.7(5) . . ? C20 C25 C26 111.0(6) . . ? C20 C25 C24 119.5(5) . . ? C26 C25 C24 129.4(6) . . ? C27 C26 C29 113.5(5) . . ? C27 C26 C25 136.3(6) . . ? C29 C26 C25 110.2(5) . . ? N4 C27 C26 120.6(6) . . ? N4 C27 C30 114.0(5) . . ? C26 C27 C30 125.3(5) . . ? N4 C28 N5 128.0(6) . . ? N5 C29 C26 125.7(6) . . ? N5 C29 S2 120.8(5) . . ? C26 C29 S2 113.5(4) . . ? C38 C30 C27 111.7(5) . . ? C38 C30 C31 113.0(5) . . ? C27 C30 C31 106.3(5) . . ? C38 C30 C35 106.2(5) . . ? C27 C30 C35 112.7(5) . . ? C31 C30 C35 107.0(5) . . ? C32 C31 C30 111.7(5) . . ? C33 C32 C36 118.9(6) . . ? C33 C32 C31 121.8(5) . . ? C36 C32 C31 119.3(5) . . ? O4 C33 C32 123.9(5) . . ? O4 C33 C34 112.9(5) . . ? C32 C33 C34 123.2(6) . . ? C33 C34 C35 113.6(5) . . ? C34 C35 C30 110.7(5) . . ? O5 C36 O6 123.3(5) . . ? O5 C36 C32 124.1(6) . . ? O6 C36 C32 112.6(6) . . ? N6 C38 C30 174.6(6) . . ? C8 N1 C9 118.4(6) . . ? C9 N2 C10 113.0(6) . . ? C28 N4 C27 119.0(5) . . ? C28 N5 C29 113.3(6) . . ? C17 O3 C18 119.2(6) . . ? C36 O6 C37 118.3(6) . . ? C10 S1 C1 89.9(3) . . ? C29 S2 C20 90.4(3) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 2.613 _refine_diff_density_min -0.693 _refine_diff_density_rms 0.147