# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name 'Olivier Siri' _publ_contact_author_address ; CINaM, UPR 3118 CNRS, campus de Luminy, Marseille, France ; _publ_requested_category FO _publ_contact_author_email olivier.siri@univmed.fr loop_ _publ_author_name J.-M.Raimundo O.Siri 'Zhongrui Chen' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-02-17 at 15:05:23 # Using CIFtbx version 2.6.2 16 Jun 1998 data_jmr46 _database_code_depnum_ccdc_archive 'CCDC 818496' #TrackingRef '13.cif' _audit_creation_date 2011-02-17T15:05:23-00:00 _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 'C28 H27 N7 O10 S3' _chemical_formula_sum 'C28 H27 N7 O10 S3' _chemical_formula_weight 717.75 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.235(1) _cell_length_b 19.2584(9) _cell_length_c 14.094(1) _cell_angle_alpha 90 _cell_angle_beta 101.675(3) _cell_angle_gamma 90 _cell_volume 3518.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 228(2) _cell_measurement_reflns_used 31875 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 28.35 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.273 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 228(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'Omega + Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_reflns_av_R_equivalents 0.158 _diffrn_reflns_av_unetI/netI 0.0794 _diffrn_reflns_number 31875 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.35 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.956 _diffrn_measured_fraction_theta_max 0.956 _reflns_number_total 8411 _reflns_number_gt 4517 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^)+(0.1706P)^2^+14.1890P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8411 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2512 _refine_ls_R_factor_gt 0.167 _refine_ls_wR_factor_ref 0.4496 _refine_ls_wR_factor_gt 0.3922 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.606 _refine_diff_density_min -0.837 _refine_diff_density_rms 0.1 #----------------------------------------------------------------------------# # 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0566(5) 0.0952(3) 0.3652(5) 0.0497(15) Uani 1 1 d . . . H1 H -0.0552 0.1432 0.3586 0.06 Uiso 1 1 calc R . . C2 C -0.1530(5) 0.0637(3) 0.3614(4) 0.0477(14) Uani 1 1 d . . . C3 C -0.1518(5) -0.0095(3) 0.3696(5) 0.0501(15) Uani 1 1 d . . . C4 C -0.0623(6) -0.0462(3) 0.3814(5) 0.0546(17) Uani 1 1 d . . . H4 H -0.0641 -0.0943 0.3867 0.066 Uiso 1 1 calc R . . C5 C 0.0315(6) -0.0131(3) 0.3858(5) 0.0526(16) Uani 1 1 d . . . C6 C 0.0370(6) 0.0600(3) 0.3780(4) 0.0516(16) Uani 1 1 d . . . C7 C 0.1204(5) 0.1832(4) 0.3632(5) 0.0542(16) Uani 1 1 d . . . C8 C 0.0869(6) 0.2054(4) 0.2687(5) 0.0635(19) Uani 1 1 d . . . H8 H 0.078 0.1731 0.2186 0.076 Uiso 1 1 calc R . . C9 C 0.0662(7) 0.2755(4) 0.2469(6) 0.071(2) Uani 1 1 d . . . H9 H 0.0428 0.2901 0.1834 0.085 Uiso 1 1 calc R . . C10 C 0.0815(7) 0.3223(4) 0.3224(5) 0.069(2) Uani 1 1 d . . . H10 H 0.0687 0.3691 0.3094 0.083 Uiso 1 1 calc R . . C11 C 0.1154(6) 0.3010(3) 0.4169(5) 0.0550(16) Uani 1 1 d . . . C12 C 0.1350(5) 0.2315(4) 0.4382(5) 0.0524(16) Uani 1 1 d . . . H12 H 0.1577 0.2173 0.502 0.063 Uiso 1 1 calc R . . C13 C 0.0437(6) 0.3811(3) 0.5230(4) 0.0537(17) Uani 1 1 d . . . C14 C -0.0529(6) 0.3547(3) 0.4843(5) 0.0570(17) Uani 1 1 d . . . H14 H -0.0563 0.3185 0.4399 0.068 Uiso 1 1 calc R . . C15 C -0.1459(6) 0.3775(3) 0.5058(5) 0.0550(17) Uani 1 1 d . . . C16 C -0.1383(6) 0.4333(3) 0.5724(5) 0.0583(18) Uani 1 1 d . . . C17 C -0.0457(7) 0.4606(3) 0.6129(5) 0.061(2) Uani 1 1 d . . . H17 H -0.0429 0.4965 0.6575 0.073 Uiso 1 1 calc R . . C18 C 0.0447(7) 0.4370(3) 0.5904(5) 0.063(2) Uani 1 1 d . . . C19 C -0.2371(5) 0.2955(3) 0.3864(5) 0.0481(14) Uani 1 1 d . . . C20 C -0.2343(6) 0.3178(4) 0.2939(5) 0.0589(17) Uani 1 1 d . . . H20 H -0.2341 0.3651 0.2807 0.071 Uiso 1 1 calc R . . C21 C -0.2319(7) 0.2709(4) 0.2215(5) 0.064(2) Uani 1 1 d . . . H21 H -0.2287 0.2866 0.1597 0.077 Uiso 1 1 calc R . . C22 C -0.2342(6) 0.2001(4) 0.2396(5) 0.0602(18) Uani 1 1 d . . . H22 H -0.2337 0.1682 0.1901 0.072 Uiso 1 1 calc R . . C23 C -0.2372(5) 0.1779(3) 0.3317(5) 0.0506(15) Uani 1 1 d . . . C24 C -0.2390(5) 0.2246(3) 0.4056(5) 0.0496(15) Uani 1 1 d . . . H24 H -0.2415 0.2089 0.4675 0.059 Uiso 1 1 calc R . . N1 N 0.1399(7) 0.3539(3) 0.4976(4) 0.073(2) Uani 1 1 d . . . H1A H 0.2012 0.3666 0.5251 0.088 Uiso 1 1 calc R . . N2 N -0.2390(5) 0.3461(3) 0.4635(4) 0.0607(15) Uani 1 1 d . . . H2 H -0.2953 0.356 0.482 0.073 Uiso 1 1 calc R . . N3 N -0.2434(5) 0.1031(3) 0.3503(4) 0.0587(15) Uani 1 1 d . . . H3 H -0.3012 0.084 0.3543 0.07 Uiso 1 1 calc R . . N4 N 0.1213(6) -0.0574(4) 0.4009(4) 0.0655(17) Uani 1 1 d . . . N5 N 0.1383(7) 0.4721(3) 0.6355(5) 0.0717(19) Uani 1 1 d . . . N6 N -0.2292(7) 0.4642(3) 0.5985(4) 0.0682(18) Uani 1 1 d . . . N7 N -0.2459(6) -0.0500(3) 0.3621(5) 0.0640(16) Uani 1 1 d . . . O1 O 0.2056(5) -0.0283(4) 0.4182(4) 0.0848(18) Uani 1 1 d . . . O2 O 0.1109(5) -0.1204(3) 0.3995(5) 0.0904(19) Uani 1 1 d . . . O3 O 0.2192(6) 0.4541(4) 0.6141(6) 0.103(2) Uani 1 1 d . . . O4 O 0.1347(6) 0.5196(3) 0.6920(4) 0.092(2) Uani 1 1 d . . . O5 O -0.2140(6) 0.5158(3) 0.6523(4) 0.0889(19) Uani 1 1 d . . . O6 O -0.3131(6) 0.4397(3) 0.5662(5) 0.0911(19) Uani 1 1 d . . . O7 O -0.3269(5) -0.0193(3) 0.3597(5) 0.0883(19) Uani 1 1 d . . . O8 O -0.2397(5) -0.1133(3) 0.3588(5) 0.0899(19) Uani 1 1 d . . . S1 S 0.1554(2) 0.09807(13) 0.38617(19) 0.0863(8) Uani 1 1 d . . . S2 S 0.3840(4) 0.3293(4) 0.6891(5) 0.227(3) Uani 1 1 d . . . O9 O 0.3197(8) 0.3162(7) 0.5923(9) 0.193(5) Uani 1 1 d . . . C25 C 0.4580(19) 0.4039(16) 0.693(3) 0.34(2) Uani 1 1 d . . . H25A H 0.5237 0.3925 0.6785 0.507 Uiso 1 1 calc R . . H25B H 0.468 0.4238 0.7569 0.507 Uiso 1 1 calc R . . H25C H 0.4231 0.4368 0.6466 0.507 Uiso 1 1 calc R . . C26 C 0.477(2) 0.2711(19) 0.709(3) 0.38(3) Uani 1 1 d . . . H26A H 0.4557 0.2304 0.6711 0.568 Uiso 1 1 calc R . . H26B H 0.4918 0.2588 0.7768 0.568 Uiso 1 1 calc R . . H26C H 0.5379 0.29 0.6919 0.568 Uiso 1 1 calc R . . S3A S -0.4403(6) 0.1370(4) 0.5194(7) 0.085(2) Uani 0.3 1 d P A 1 O10A O -0.4317(9) 0.1125(8) 0.4118(12) 0.110(5) Uani 0.3 1 d P A 1 C27A C -0.586(2) 0.1565(17) 0.484(2) 0.147(11) Uani 0.3 1 d P A 1 H27A H -0.5974 0.1954 0.4403 0.221 Uiso 0.3 1 calc PR A 1 H27B H -0.6123 0.1673 0.541 0.221 Uiso 0.3 1 calc PR A 1 H27C H -0.6217 0.1166 0.4526 0.221 Uiso 0.3 1 calc PR A 1 C28A C -0.4382(17) 0.076(2) 0.6032(19) 0.152(13) Uani 0.3 1 d P A 1 H28A H -0.4916 0.0425 0.5807 0.228 Uiso 0.3 1 calc PR A 1 H28B H -0.4492 0.0967 0.6621 0.228 Uiso 0.3 1 calc PR A 1 H28C H -0.3723 0.0529 0.615 0.228 Uiso 0.3 1 calc PR A 1 S3B S -0.4982(11) 0.0974(8) 0.4592(10) 0.098(4) Uani 0.2 1 d P B 2 O10B O -0.4317(9) 0.1125(8) 0.4118(12) 0.110(5) Uani 0.2 1 d P B 2 C27B C -0.586(2) 0.1565(17) 0.484(2) 0.147(11) Uani 0.2 1 d P B 2 H27D H -0.5598 0.1783 0.5451 0.221 Uiso 0.2 1 calc PR B 2 H27E H -0.6498 0.1332 0.4865 0.221 Uiso 0.2 1 calc PR B 2 H27F H -0.5986 0.1911 0.4338 0.221 Uiso 0.2 1 calc PR B 2 C28B C -0.4382(17) 0.076(2) 0.6032(19) 0.152(13) Uani 0.2 1 d P B 2 H28D H -0.3777 0.0474 0.608 0.228 Uiso 0.2 1 calc PR B 2 H28E H -0.4887 0.0515 0.6307 0.228 Uiso 0.2 1 calc PR B 2 H28F H -0.4202 0.1184 0.6378 0.228 Uiso 0.2 1 calc PR B 2 S4A S -0.5276(5) 0.3817(4) 0.4396(6) 0.0573(17) Uani 0.25 1 d P C 3 O11A O -0.4472(7) 0.3216(5) 0.4609(8) 0.066(3) Uani 0.25 1 d P C 3 C29A C -0.504(2) 0.4270(17) 0.358(3) 0.20(2) Uani 0.25 1 d P C 3 H29A H -0.4535 0.4613 0.3844 0.296 Uiso 0.25 1 calc PR C 3 H29B H -0.5661 0.4496 0.3254 0.296 Uiso 0.25 1 calc PR C 3 H29C H -0.4776 0.3985 0.3126 0.296 Uiso 0.25 1 calc PR C 3 C30A C -0.6407(18) 0.3324(19) 0.363(2) 0.156(13) Uani 0.25 1 d P C 3 H30A H -0.6149 0.2939 0.3313 0.234 Uiso 0.25 1 calc PR C 3 H30B H -0.6786 0.363 0.3144 0.234 Uiso 0.25 1 calc PR C 3 H30C H -0.6853 0.3156 0.4033 0.234 Uiso 0.25 1 calc PR C 3 S4B S -0.5090(7) 0.3423(6) 0.3644(8) 0.094(3) Uani 0.25 1 d P D 4 O11B O -0.4472(7) 0.3216(5) 0.4609(8) 0.066(3) Uani 0.25 1 d P D 4 C29B C -0.504(2) 0.4270(17) 0.358(3) 0.20(2) Uani 0.25 1 d P D 4 H29D H -0.5636 0.4467 0.3767 0.296 Uiso 0.25 1 calc PR D 4 H29E H -0.5026 0.4405 0.2926 0.296 Uiso 0.25 1 calc PR D 4 H29F H -0.4428 0.4435 0.4006 0.296 Uiso 0.25 1 calc PR D 4 C30B C -0.6407(18) 0.3324(19) 0.363(2) 0.156(13) Uani 0.25 1 d P D 4 H30D H -0.6497 0.3091 0.4205 0.234 Uiso 0.25 1 calc PR D 4 H30E H -0.6718 0.3055 0.307 0.234 Uiso 0.25 1 calc PR D 4 H30F H -0.6728 0.3773 0.3592 0.234 Uiso 0.25 1 calc PR D 4 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 0.059(4) 0.044(3) 0.046(3) -0.003(3) 0.008(3) 0.000(3) C2 0.059(4) 0.044(3) 0.039(3) -0.005(3) 0.008(3) -0.004(3) C3 0.066(4) 0.042(3) 0.040(3) -0.002(3) 0.006(3) -0.005(3) C4 0.084(5) 0.039(3) 0.041(3) -0.007(3) 0.013(3) -0.005(3) C5 0.078(5) 0.043(3) 0.037(3) -0.005(3) 0.011(3) 0.011(3) C6 0.068(4) 0.053(4) 0.034(3) -0.004(3) 0.010(3) -0.003(3) C7 0.053(4) 0.056(4) 0.054(4) 0.000(3) 0.011(3) -0.001(3) C8 0.088(5) 0.050(4) 0.054(4) -0.006(3) 0.018(4) -0.001(4) C9 0.107(7) 0.056(4) 0.050(4) 0.003(3) 0.017(4) -0.013(4) C10 0.099(6) 0.044(4) 0.059(4) -0.007(3) 0.003(4) -0.015(4) C11 0.063(4) 0.051(4) 0.048(4) -0.005(3) 0.003(3) -0.012(3) C12 0.050(4) 0.064(4) 0.043(3) 0.002(3) 0.008(3) -0.007(3) C13 0.087(5) 0.034(3) 0.037(3) -0.005(2) 0.005(3) -0.008(3) C14 0.082(5) 0.046(4) 0.039(3) -0.006(3) 0.004(3) -0.003(3) C15 0.080(5) 0.043(3) 0.040(3) -0.001(3) 0.007(3) 0.002(3) C16 0.092(5) 0.041(3) 0.040(4) -0.003(3) 0.009(3) -0.006(3) C17 0.109(6) 0.035(3) 0.039(3) -0.002(3) 0.018(4) 0.005(4) C18 0.099(6) 0.038(3) 0.042(4) 0.005(3) -0.008(4) -0.015(4) C19 0.049(4) 0.047(3) 0.047(3) -0.003(3) 0.007(3) -0.002(3) C20 0.070(5) 0.048(4) 0.057(4) 0.000(3) 0.009(3) 0.000(3) C21 0.097(6) 0.055(4) 0.041(4) -0.002(3) 0.012(4) -0.007(4) C22 0.081(5) 0.050(4) 0.050(4) -0.010(3) 0.014(3) -0.009(3) C23 0.054(4) 0.049(4) 0.048(4) -0.002(3) 0.009(3) -0.001(3) C24 0.052(4) 0.049(3) 0.046(3) -0.001(3) 0.005(3) -0.001(3) N1 0.151(7) 0.032(3) 0.041(3) -0.010(2) 0.028(4) -0.005(3) N2 0.089(4) 0.045(3) 0.048(3) -0.012(2) 0.011(3) -0.009(3) N3 0.084(4) 0.035(3) 0.058(3) 0.004(2) 0.018(3) 0.015(3) N4 0.079(5) 0.074(5) 0.043(3) -0.001(3) 0.011(3) 0.026(4) N5 0.113(6) 0.051(4) 0.046(4) -0.003(3) 0.004(4) -0.016(4) N6 0.114(6) 0.047(3) 0.048(3) -0.003(3) 0.027(4) 0.022(4) N7 0.079(5) 0.048(3) 0.061(4) -0.004(3) 0.006(3) -0.016(3) O1 0.074(4) 0.102(5) 0.078(4) 0.014(3) 0.017(3) 0.028(4) O2 0.112(5) 0.061(4) 0.095(5) -0.004(3) 0.014(4) 0.038(3) O3 0.095(5) 0.089(5) 0.115(6) -0.034(4) -0.002(4) -0.024(4) O4 0.149(6) 0.064(3) 0.057(3) -0.019(3) 0.011(3) -0.037(4) O5 0.144(6) 0.065(3) 0.061(3) -0.012(3) 0.027(4) 0.023(3) O6 0.089(5) 0.082(4) 0.104(5) -0.027(4) 0.026(4) 0.000(3) O7 0.067(4) 0.073(4) 0.120(5) 0.002(4) 0.007(3) -0.013(3) O8 0.117(5) 0.049(3) 0.104(5) -0.011(3) 0.022(4) -0.025(3) S1 0.0978(18) 0.0736(14) 0.0881(17) 0.0004(12) 0.0199(13) -0.0054(12) S2 0.108(3) 0.316(8) 0.226(6) -0.045(6) -0.038(4) 0.025(4) O9 0.124(8) 0.221(12) 0.197(11) -0.024(9) -0.057(8) 0.000(8) C25 0.18(2) 0.36(4) 0.41(4) 0.01(3) -0.09(2) -0.15(2) C26 0.25(3) 0.41(5) 0.40(5) -0.18(4) -0.12(3) 0.18(3) S3A 0.061(4) 0.093(5) 0.111(6) -0.026(5) 0.041(4) -0.020(4) O10A 0.051(7) 0.123(11) 0.172(14) -0.038(10) 0.063(8) -0.021(7) C27A 0.13(2) 0.18(3) 0.16(3) 0.00(2) 0.09(2) 0.007(19) C28A 0.067(13) 0.29(4) 0.108(19) -0.03(2) 0.033(13) -0.018(18) S3B 0.099(9) 0.105(9) 0.097(9) -0.013(7) 0.032(8) -0.047(8) O10B 0.051(7) 0.123(11) 0.172(14) -0.038(10) 0.063(8) -0.021(7) C27B 0.13(2) 0.18(3) 0.16(3) 0.00(2) 0.09(2) 0.007(19) C28B 0.067(13) 0.29(4) 0.108(19) -0.03(2) 0.033(13) -0.018(18) S4A 0.037(3) 0.073(5) 0.061(4) -0.004(4) 0.007(3) 0.015(3) O11A 0.044(5) 0.063(6) 0.091(8) 0.001(5) 0.017(5) 0.006(4) C29A 0.081(17) 0.15(3) 0.31(5) -0.04(3) -0.10(2) 0.017(17) C30A 0.078(16) 0.24(3) 0.15(2) 0.08(2) 0.008(15) -0.016(18) S4B 0.061(5) 0.118(8) 0.106(8) -0.010(6) 0.024(5) 0.005(5) O11B 0.044(5) 0.063(6) 0.091(8) 0.001(5) 0.017(5) 0.006(4) C29B 0.081(17) 0.15(3) 0.31(5) -0.04(3) -0.10(2) 0.017(17) C30B 0.078(16) 0.24(3) 0.15(2) 0.08(2) 0.008(15) -0.016(18) #----------------------------------------------------------------------------# # 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 C6 1.392(9) . ? C1 C2 1.404(9) . ? C1 H1 0.93 . ? C2 N3 1.399(9) . ? C2 C3 1.415(9) . ? C3 C4 1.360(10) . ? C3 N7 1.454(9) . ? C4 C5 1.386(10) . ? C4 H4 0.93 . ? C5 C6 1.415(9) . ? C5 N4 1.444(9) . ? C6 S1 1.713(7) . ? C7 C8 1.385(10) . ? C7 C12 1.392(9) . ? C7 S1 1.717(7) . ? C8 C9 1.399(10) . ? C8 H8 0.93 . ? C9 C10 1.377(10) . ? C9 H9 0.93 . ? C10 C11 1.379(10) . ? C10 H10 0.93 . ? C11 C12 1.383(10) . ? C11 N1 1.513(8) . ? C12 H12 0.93 . ? C13 C14 1.382(10) . ? C13 C18 1.433(9) . ? C13 N1 1.486(10) . ? C14 C15 1.397(10) . ? C14 H14 0.93 . ? C15 N2 1.393(9) . ? C15 C16 1.417(9) . ? C16 C17 1.350(11) . ? C16 N6 1.455(10) . ? C17 C18 1.376(11) . ? C17 H17 0.93 . ? C18 N5 1.441(10) . ? C19 C20 1.379(9) . ? C19 C24 1.395(9) . ? C19 N2 1.463(8) . ? C20 C21 1.368(10) . ? C20 H20 0.93 . ? C21 C22 1.389(10) . ? C21 H21 0.93 . ? C22 C23 1.375(9) . ? C22 H22 0.93 . ? C23 C24 1.380(9) . ? C23 N3 1.469(8) . ? C24 H24 0.93 . ? N1 H1A 0.86 . ? N2 H2 0.86 . ? N3 H3 0.86 . ? N4 O2 1.221(9) . ? N4 O1 1.228(9) . ? N5 O3 1.219(10) . ? N5 O4 1.220(8) . ? N6 O6 1.207(9) . ? N6 O5 1.242(8) . ? N7 O7 1.220(8) . ? N7 O8 1.224(8) . ? S2 O9 1.475(12) . ? S2 C26 1.65(2) . ? S2 C25 1.73(2) . ? C25 H25A 0.96 . ? C25 H25B 0.96 . ? C25 H25C 0.96 . ? C26 H26A 0.96 . ? C26 H26B 0.96 . ? C26 H26C 0.96 . ? S3A O10A 1.614(17) . ? S3A C28A 1.66(3) . ? S3A C27A 1.93(3) . ? C27A H27A 0.96 . ? C27A H27B 0.96 . ? C27A H27C 0.96 . ? C28A H28A 0.96 . ? C28A H28B 0.96 . ? C28A H28C 0.96 . ? S4A C29A 1.53(5) . ? S4A O11A 1.559(12) . ? S4A C30A 1.91(3) . ? C29A H29A 0.96 . ? C29A H29B 0.96 . ? C29A H29C 0.96 . ? C30A H30A 0.96 . ? C30A H30B 0.96 . ? C30A H30C 0.96 . ? 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 124.9(6) . . ? C6 C1 H1 117.5 . . ? C2 C1 H1 117.5 . . ? N3 C2 C1 121.4(6) . . ? N3 C2 C3 123.0(6) . . ? C1 C2 C3 115.6(6) . . ? C4 C3 C2 121.5(6) . . ? C4 C3 N7 116.2(6) . . ? C2 C3 N7 122.2(6) . . ? C3 C4 C5 121.1(6) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 121.0(6) . . ? C4 C5 N4 115.9(6) . . ? C6 C5 N4 123.0(7) . . ? C1 C6 C5 115.8(6) . . ? C1 C6 S1 125.3(5) . . ? C5 C6 S1 118.8(6) . . ? C8 C7 C12 119.5(6) . . ? C8 C7 S1 119.9(5) . . ? C12 C7 S1 120.3(5) . . ? C7 C8 C9 121.3(7) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C10 C9 C8 118.0(7) . . ? C10 C9 H9 121 . . ? C8 C9 H9 121 . . ? C9 C10 C11 121.3(7) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C10 C11 C12 120.5(6) . . ? C10 C11 N1 120.2(6) . . ? C12 C11 N1 119.1(6) . . ? C11 C12 C7 119.4(6) . . ? C11 C12 H12 120.3 . . ? C7 C12 H12 120.3 . . ? C14 C13 C18 115.0(7) . . ? C14 C13 N1 123.0(6) . . ? C18 C13 N1 122.0(6) . . ? C13 C14 C15 125.7(6) . . ? C13 C14 H14 117.2 . . ? C15 C14 H14 117.2 . . ? N2 C15 C14 120.8(6) . . ? N2 C15 C16 123.4(7) . . ? C14 C15 C16 115.8(7) . . ? C17 C16 C15 120.8(7) . . ? C17 C16 N6 117.4(6) . . ? C15 C16 N6 121.7(7) . . ? C16 C17 C18 122.1(6) . . ? C16 C17 H17 119 . . ? C18 C17 H17 119 . . ? C17 C18 C13 120.6(7) . . ? C17 C18 N5 117.0(7) . . ? C13 C18 N5 122.4(8) . . ? C20 C19 C24 119.6(6) . . ? C20 C19 N2 120.2(6) . . ? C24 C19 N2 120.2(6) . . ? C21 C20 C19 120.6(7) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 120.4(7) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C23 C22 C21 119.0(6) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C22 C23 C24 121.2(6) . . ? C22 C23 N3 119.2(6) . . ? C24 C23 N3 119.5(6) . . ? C23 C24 C19 119.2(6) . . ? C23 C24 H24 120.4 . . ? C19 C24 H24 120.4 . . ? C13 N1 C11 110.8(6) . . ? C13 N1 H1A 124.6 . . ? C11 N1 H1A 124.6 . . ? C15 N2 C19 117.4(6) . . ? C15 N2 H2 121.3 . . ? C19 N2 H2 121.3 . . ? C2 N3 C23 118.3(6) . . ? C2 N3 H3 120.9 . . ? C23 N3 H3 120.9 . . ? O2 N4 O1 123.5(7) . . ? O2 N4 C5 119.9(8) . . ? O1 N4 C5 116.5(7) . . ? O3 N5 O4 121.8(8) . . ? O3 N5 C18 118.5(7) . . ? O4 N5 C18 119.7(9) . . ? O6 N6 O5 124.4(7) . . ? O6 N6 C16 119.3(6) . . ? O5 N6 C16 116.2(8) . . ? O7 N7 O8 123.2(7) . . ? O7 N7 C3 118.5(6) . . ? O8 N7 C3 118.3(7) . . ? C6 S1 C7 100.8(4) . . ? O9 S2 C26 108.4(13) . . ? O9 S2 C25 112.9(13) . . ? C26 S2 C25 99.3(18) . . ? S2 C25 H25A 109.5 . . ? S2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? S2 C26 H26A 109.5 . . ? S2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? S2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O10A S3A C28A 117.7(13) . . ? O10A S3A C27A 94.0(11) . . ? C28A S3A C27A 101.2(12) . . ? S3A C27A H27A 109.5 . . ? S3A C27A H27B 109.5 . . ? H27A C27A H27B 109.5 . . ? S3A C27A H27C 109.5 . . ? H27A C27A H27C 109.5 . . ? H27B C27A H27C 109.5 . . ? S3A C28A H28A 109.5 . . ? S3A C28A H28B 109.5 . . ? H28A C28A H28B 109.5 . . ? S3A C28A H28C 109.5 . . ? H28A C28A H28C 109.5 . . ? H28B C28A H28C 109.5 . . ? C29A S4A O11A 109.5(13) . . ? C29A S4A C30A 96.4(13) . . ? O11A S4A C30A 99.6(12) . . ? S4A C29A H29A 109.5 . . ? S4A C29A H29B 109.5 . . ? H29A C29A H29B 109.5 . . ? S4A C29A H29C 109.5 . . ? H29A C29A H29C 109.5 . . ? H29B C29A H29C 109.5 . . ? S4A C30A H30A 109.5 . . ? S4A C30A H30B 109.5 . . ? H30A C30A H30B 109.5 . . ? S4A C30A H30C 109.5 . . ? H30A C30A H30C 109.5 . . ? H30B C30A H30C 109.5 . . ? #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-02-08 at 11:08:39 # Using CIFtbx version 2.6.2 16 Jun 1998 data_sc55 _database_code_depnum_ccdc_archive 'CCDC 818497' #TrackingRef '14.cif' _audit_creation_date 2011-02-08T11:08:39-00:00 _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 'C28 H26 N6 O10 S4' _chemical_formula_sum 'C28 H26 N6 O10 S4' _chemical_formula_weight 734.79 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.4209(6) _cell_length_b 9.2343(3) _cell_length_c 14.7501(4) _cell_angle_alpha 90 _cell_angle_beta 99.044(2) _cell_angle_gamma 90 _cell_volume 3284.94(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22018 _cell_measurement_theta_min 1.69 _cell_measurement_theta_max 28.64 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.354 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'Omega + Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_reflns_av_R_equivalents 0.068 _diffrn_reflns_av_unetI/netI 0.0364 _diffrn_reflns_number 22018 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 28.64 _diffrn_reflns_theta_full 28.64 _diffrn_measured_fraction_theta_full 0.96 _diffrn_measured_fraction_theta_max 0.96 _reflns_number_total 4060 _reflns_number_gt 2822 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^)+(0.1575P)^2^+4.6592P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4060 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.114 _refine_ls_R_factor_gt 0.0736 _refine_ls_wR_factor_ref 0.279 _refine_ls_wR_factor_gt 0.2275 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.572 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.128 #----------------------------------------------------------------------------# # 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.14085(4) 0.22531(12) 0.92386(6) 0.0551(3) Uani 1 1 d . . . S2 S 1.22047(6) -0.1532(3) 1.14011(11) 0.1126(8) Uani 1 1 d . . . O2 O 0.95388(14) 0.4521(4) 1.17431(19) 0.0808(10) Uani 1 1 d . . . O3 O 1.14309(14) 0.4523(4) 1.1812(2) 0.0788(10) Uani 1 1 d . . . O1 O 0.89666(13) 0.3533(4) 1.0689(2) 0.0747(9) Uani 1 1 d . . . N1 N 1.07121(13) 0.2267(3) 0.57350(17) 0.0452(7) Uani 1 1 d . . . H1N H 1.1002 0.2493 0.5501 0.054 Uiso 1 1 calc R . . N2 N 0.94349(14) 0.3843(3) 1.10318(18) 0.0482(7) Uani 1 1 d . . . C2 C 0.98069(14) 0.2668(3) 0.9711(2) 0.0399(7) Uani 1 1 d . . . C6 C 1.08228(15) 0.2701(3) 0.9738(2) 0.0407(7) Uani 1 1 d . . . N3 N 1.14124(14) 0.3859(4) 1.10924(19) 0.0530(8) Uani 1 1 d . . . C3 C 0.98917(14) 0.3414(3) 1.0564(2) 0.0399(7) Uani 1 1 d . . . C12 C 1.09774(14) 0.2171(4) 0.7410(2) 0.0434(7) Uani 1 1 d . . . H12 H 1.1038 0.3165 0.7414 0.052 Uiso 1 1 calc R . . C5 C 1.08751(14) 0.3453(3) 1.0591(2) 0.0417(7) Uani 1 1 d . . . O4 O 1.18310(14) 0.3508(5) 1.0787(2) 0.0859(11) Uani 1 1 d . . . C11 C 1.07732(14) 0.1467(4) 0.6597(2) 0.0415(7) Uani 1 1 d . . . O5 O 1.18086(15) -0.1983(7) 1.0571(3) 0.125(2) Uani 1 1 d . . . C1 C 1.02883(14) 0.2345(4) 0.9335(2) 0.0418(7) Uani 1 1 d . . . H1 H 1.0244 0.1858 0.8777 0.05 Uiso 1 1 calc R . . C7 C 1.10913(14) 0.1381(4) 0.8219(2) 0.0443(7) Uani 1 1 d . . . C4 C 1.04160(15) 0.3802(3) 1.0980(2) 0.0428(7) Uani 1 1 d . . . H4 H 1.046 0.4307 1.1532 0.051 Uiso 1 1 calc R . . C8 C 1.0997(2) -0.0088(4) 0.8224(2) 0.0580(10) Uani 1 1 d . . . H8 H 1.1083 -0.0614 0.8765 0.07 Uiso 1 1 calc R . . C9 C 1.0772(2) -0.0780(4) 0.7415(3) 0.0700(13) Uani 1 1 d . . . H9 H 1.069 -0.1763 0.7419 0.084 Uiso 1 1 calc R . . C10 C 1.0670(2) -0.0006(4) 0.6601(2) 0.0589(10) Uani 1 1 d . . . H10 H 1.0531 -0.0478 0.6056 0.071 Uiso 1 1 calc R . . C13 C 1.2654(3) -0.0229(8) 1.0998(6) 0.118(2) Uani 1 1 d . . . H13A H 1.2455 0.0659 1.0853 0.177 Uiso 1 1 calc R . . H13B H 1.2781 -0.0595 1.0458 0.177 Uiso 1 1 calc R . . H13C H 1.2967 -0.0054 1.1467 0.177 Uiso 1 1 calc R . . C14 C 1.2715(4) -0.2943(10) 1.1600(6) 0.143(3) Uani 1 1 d . . . H14A H 1.2552 -0.3791 1.1823 0.214 Uiso 1 1 calc R . . H14B H 1.302 -0.2624 1.2047 0.214 Uiso 1 1 calc R . . H14C H 1.2846 -0.3167 1.1036 0.214 Uiso 1 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 0.0521(5) 0.0752(7) 0.0372(5) -0.0079(4) 0.0049(4) -0.0007(4) S2 0.0684(8) 0.191(2) 0.0835(10) -0.0457(11) 0.0267(7) -0.0396(10) O2 0.083(2) 0.122(3) 0.0389(15) -0.0247(16) 0.0115(13) 0.019(2) O3 0.072(2) 0.100(2) 0.0593(17) -0.0378(17) -0.0085(14) -0.0005(18) O1 0.0571(17) 0.098(2) 0.073(2) -0.0314(18) 0.0228(14) -0.0083(16) N1 0.0596(17) 0.0481(15) 0.0272(12) 0.0064(11) 0.0041(11) 0.0063(13) N2 0.0644(19) 0.0515(16) 0.0305(13) 0.0019(11) 0.0126(12) 0.0057(14) C2 0.0540(18) 0.0384(15) 0.0271(13) 0.0027(11) 0.0055(12) -0.0016(13) C6 0.0542(18) 0.0395(16) 0.0284(14) 0.0004(11) 0.0063(12) 0.0003(13) N3 0.0610(19) 0.0595(18) 0.0356(15) -0.0050(13) -0.0013(13) -0.0013(15) C3 0.0554(18) 0.0382(15) 0.0276(14) 0.0023(11) 0.0112(12) 0.0028(13) C12 0.0477(17) 0.0465(17) 0.0364(16) -0.0001(13) 0.0076(13) 0.0028(14) C5 0.0521(18) 0.0429(16) 0.0284(14) 0.0014(12) 0.0011(12) -0.0042(14) O4 0.0579(18) 0.135(3) 0.0626(19) -0.033(2) 0.0020(14) -0.0087(19) C11 0.0458(16) 0.0471(17) 0.0321(15) 0.0012(12) 0.0081(12) 0.0080(14) O5 0.056(2) 0.219(6) 0.102(3) -0.061(3) 0.019(2) -0.035(3) C1 0.0547(18) 0.0444(16) 0.0265(14) -0.0042(12) 0.0073(12) -0.0038(14) C7 0.0488(18) 0.0522(19) 0.0321(15) -0.0006(13) 0.0072(13) 0.0069(14) C4 0.065(2) 0.0378(15) 0.0250(13) 0.0022(11) 0.0053(13) 0.0034(14) C8 0.086(3) 0.049(2) 0.0385(18) 0.0028(14) 0.0074(17) 0.0075(19) C9 0.123(4) 0.0402(19) 0.045(2) -0.0014(15) 0.008(2) 0.004(2) C10 0.095(3) 0.0454(19) 0.0351(17) -0.0075(14) 0.0068(17) 0.0073(19) C13 0.097(5) 0.114(5) 0.135(6) 0.009(4) -0.007(4) -0.013(4) C14 0.136(7) 0.145(7) 0.130(7) 0.031(5) -0.035(5) -0.029(6) #----------------------------------------------------------------------------# # 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 C6 1.759(3) . ? S1 C7 1.773(3) . ? S2 O5 1.496(4) . ? S2 C13 1.792(8) . ? S2 C14 1.795(9) . ? O2 N2 1.214(4) . ? O3 N3 1.221(4) . ? O1 N2 1.210(4) . ? N1 C2 1.384(4) 2_756 ? N1 C11 1.458(4) . ? N1 H1N 0.86 . ? N2 C3 1.456(4) . ? C2 N1 1.383(4) 2_756 ? C2 C1 1.408(5) . ? C2 C3 1.421(4) . ? C6 C1 1.386(5) . ? C6 C5 1.425(4) . ? N3 O4 1.224(5) . ? N3 C5 1.450(4) . ? C3 C4 1.377(5) . ? C12 C11 1.387(4) . ? C12 C7 1.389(4) . ? C12 H12 0.93 . ? C5 C4 1.375(5) . ? C11 C10 1.384(5) . ? C1 H1 0.93 . ? C7 C8 1.377(5) . ? C4 H4 0.93 . ? C8 C9 1.388(5) . ? C8 H8 0.93 . ? C9 C10 1.386(5) . ? C9 H9 0.93 . ? C10 H10 0.93 . ? C13 H13A 0.96 . ? C13 H13B 0.96 . ? C13 H13C 0.96 . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? 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 S1 C7 100.75(16) . . ? O5 S2 C13 105.5(3) . . ? O5 S2 C14 106.0(4) . . ? C13 S2 C14 95.5(4) . . ? C2 N1 C11 120.7(3) 2_756 . ? C2 N1 H1N 119.6 2_756 . ? C11 N1 H1N 119.6 . . ? O1 N2 O2 122.6(3) . . ? O1 N2 C3 118.8(3) . . ? O2 N2 C3 118.6(3) . . ? N1 C2 C1 121.0(3) 2_756 . ? N1 C2 C3 123.1(3) 2_756 . ? C1 C2 C3 115.9(3) . . ? C1 C6 C5 116.2(3) . . ? C1 C6 S1 122.5(2) . . ? C5 C6 S1 121.2(3) . . ? O3 N3 O4 122.3(3) . . ? O3 N3 C5 118.7(3) . . ? O4 N3 C5 119.0(3) . . ? C4 C3 C2 121.1(3) . . ? C4 C3 N2 116.5(3) . . ? C2 C3 N2 122.4(3) . . ? C11 C12 C7 119.6(3) . . ? C11 C12 H12 120.2 . . ? C7 C12 H12 120.2 . . ? C4 C5 C6 121.1(3) . . ? C4 C5 N3 117.3(3) . . ? C6 C5 N3 121.6(3) . . ? C10 C11 C12 119.9(3) . . ? C10 C11 N1 120.6(3) . . ? C12 C11 N1 119.4(3) . . ? C6 C1 C2 124.7(3) . . ? C6 C1 H1 117.7 . . ? C2 C1 H1 117.7 . . ? C8 C7 C12 120.7(3) . . ? C8 C7 S1 119.7(3) . . ? C12 C7 S1 119.5(3) . . ? C5 C4 C3 121.0(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C7 C8 C9 119.6(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 120.1(4) . . ? C10 C9 H9 120 . . ? C8 C9 H9 120 . . ? C11 C10 C9 120.1(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? S2 C13 H13A 109.5 . . ? S2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? S2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? S2 C14 H14A 109.5 . . ? S2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? S2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ?