# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_YI04059 _database_code_depnum_ccdc_archive 'CCDC 911911' _chemical_formula_moiety 'C16 H16 N2 O5 S' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C16 H16 N2 O5 S' _chemical_formula_weight 348.37 _chemical_melting_point ? #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 _chemical_absolute_configuration . _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 4.92063(10) _cell_length_b 15.6607(4) _cell_length_c 10.4554(3) _cell_angle_alpha 90.0000 _cell_angle_beta 99.6328(14) _cell_angle_gamma 90.0000 _cell_volume 794.34(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6947 _cell_measurement_theta_min 4.29 _cell_measurement_theta_max 68.21 _cell_measurement_temperature 173 _exptl_crystal_size_max 0.370 _exptl_crystal_size_mid 0.190 _exptl_crystal_size_min 0.150 _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364.00 _exptl_absorpt_coefficient_mu 2.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.543 _exptl_absorpt_correction_T_max 0.731 _diffrn_radiation_probe ? _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 8867 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_theta_max 68.24 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2825 _reflns_number_gt 2585 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0951 _refine_ls_number_restraints ? _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2825 _refine_ls_number_parameters 235 _refine_ls_goodness_of_fit_ref 0.487 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0010Fo^2^ + 3.0000\s(Fo^2^) + 0.5000]/(4Fo^2^)' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.605 _refine_diff_density_min -0.524 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 13(4) _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1328 Friedel Pairs' _refine_ls_abs_structure_Flack 0.998(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.3331 0.5567 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S(1) S -0.08037(12) 0.33270(5) 0.66419(6) 0.02402(15) Uani 1.0 2 d . . . O(1) O 0.8176(4) 0.82675(14) 0.70174(17) 0.0369(6) Uani 1.0 2 d . . . O(2) O 1.0785(4) 0.77497(11) 0.88081(18) 0.0306(6) Uani 1.0 2 d . . . O(3) O 0.2525(4) 0.42480(11) 0.87912(16) 0.0246(5) Uani 1.0 2 d . . . O(4) O -0.2138(4) 0.32445(13) 0.53252(17) 0.0321(5) Uani 1.0 2 d . . . O(6) O -0.2417(4) 0.34744(11) 0.76348(19) 0.0314(6) Uani 1.0 2 d . . . N(1) N 0.1316(5) 0.41870(13) 0.65940(19) 0.0220(6) Uani 1.0 2 d . . . N(3) N 0.2345(5) 0.43353(14) 0.5430(2) 0.0292(6) Uani 1.0 2 d . . . C(1) C 0.7244(5) 0.68724(15) 0.7743(3) 0.0204(6) Uani 1.0 2 d . . . C(2) C 0.2703(5) 0.45443(15) 0.7737(3) 0.0209(7) Uani 1.0 2 d . . . C(9) C 0.6788(6) 0.54369(15) 0.8502(3) 0.0215(6) Uani 1.0 2 d . . . C(10) C 0.8754(6) 0.77026(16) 0.7798(3) 0.0249(7) Uani 1.0 2 d . . . C(12) C 0.3367(6) 0.60137(16) 0.6798(3) 0.0241(7) Uani 1.0 2 d . . . C(14) C 0.2417(7) 0.22686(17) 0.8336(3) 0.0283(8) Uani 1.0 2 d . . . C(15) C 0.8239(6) 0.61903(15) 0.8562(3) 0.0232(7) Uani 1.0 2 d . . . C(16) C 0.4790(6) 0.67766(16) 0.6870(3) 0.0246(7) Uani 1.0 2 d . . . C(17) C 0.4345(6) 0.53427(15) 0.7625(3) 0.0211(7) Uani 1.0 2 d . . . C(18) C 0.4055(6) 0.13058(18) 0.6359(3) 0.0337(8) Uani 1.0 2 d . . . C(19) C 0.7126(7) 0.03861(19) 0.7971(4) 0.0413(9) Uani 1.0 2 d . . . C(20) C 0.5102(6) 0.11177(16) 0.7637(3) 0.0293(8) Uani 1.0 2 d . . . C(21) C 0.1407(6) 0.24533(16) 0.7034(3) 0.0246(7) Uani 1.0 2 d . . . C(22) C 0.4283(6) 0.16076(17) 0.8619(3) 0.0300(8) Uani 1.0 2 d . . . C(23) C 0.2227(6) 0.19798(17) 0.6042(3) 0.0303(8) Uani 1.0 2 d . . . C(24) C 1.2366(7) 0.85317(17) 0.8926(4) 0.0411(9) Uani 1.0 2 d . . . H(1) H 0.0838 0.4344 0.4864 0.0354 Uiso 1.0 2 calc R . . H(2) H 0.3388 0.3984 0.5303 0.0352 Uiso 1.0 2 calc R . . H(3) H 0.1679 0.5966 0.6211 0.0285 Uiso 1.0 2 calc R . . H(4) H 1.0027 0.6283 0.9134 0.0281 Uiso 1.0 2 calc R . . H(5) H 0.4241 0.7261 0.6152 0.0296 Uiso 1.0 2 calc R . . H(6) H 0.4297 0.0922 0.5622 0.0419 Uiso 1.0 2 calc R . . H(7) H 0.7266 0.0256 0.8855 0.0500 Uiso 1.0 2 calc R . . H(8) H 0.6526 -0.0084 0.7055 0.0505 Uiso 1.0 2 calc R . . H(9) H 0.8566 0.0546 0.7935 0.0502 Uiso 1.0 2 calc R . . H(10) H 0.4702 0.1436 0.9491 0.0361 Uiso 1.0 2 calc R . . H(11) H 0.1575 0.2092 0.5233 0.0361 Uiso 1.0 2 calc R . . H(12) H 1.2785 0.8688 0.8103 0.0484 Uiso 1.0 2 calc R . . H(13) H 1.1322 0.8973 0.9237 0.0482 Uiso 1.0 2 calc R . . H(14) H 0.7445 0.4980 0.9067 0.0255 Uiso 1.0 2 calc R . . H(15) H 1.4030 0.8448 0.9520 0.0480 Uiso 1.0 2 calc R . . H(16) H 0.1832 0.2592 0.9009 0.0348 Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(1) 0.0185(3) 0.0198(3) 0.0330(4) -0.0015(3) 0.0022(2) -0.0034(3) O(1) 0.0491(12) 0.0252(10) 0.0330(10) -0.0121(11) -0.0028(9) 0.0065(10) O(2) 0.0321(12) 0.0222(10) 0.0336(11) -0.0077(8) -0.0054(8) -0.0007(8) O(3) 0.0241(10) 0.0245(10) 0.0247(9) -0.0017(8) 0.0023(7) 0.0021(8) O(4) 0.0267(10) 0.0283(10) 0.0369(11) -0.0042(9) -0.0073(8) -0.0070(9) O(6) 0.0211(10) 0.0269(11) 0.0485(12) -0.0025(7) 0.0126(8) -0.0057(8) N(1) 0.0234(12) 0.0171(10) 0.0251(11) -0.0026(9) 0.0028(9) -0.0025(9) N(3) 0.0309(13) 0.0302(12) 0.0265(12) -0.0021(10) 0.0050(9) -0.0025(9) C(1) 0.0240(14) 0.0177(12) 0.0197(12) -0.0008(10) 0.0037(10) -0.0001(9) C(2) 0.0146(13) 0.0204(12) 0.0269(13) 0.0042(10) 0.0012(10) -0.0016(10) C(9) 0.0237(14) 0.0198(12) 0.0197(12) 0.0024(10) -0.0005(10) 0.0019(10) C(10) 0.0278(14) 0.0220(13) 0.0264(13) -0.0011(10) 0.0086(11) -0.0034(10) C(12) 0.0200(14) 0.0267(14) 0.0240(13) 0.0024(10) -0.0005(10) 0.0004(11) C(14) 0.0316(17) 0.0237(14) 0.0321(15) -0.0029(11) 0.0131(12) -0.0004(12) C(15) 0.0229(13) 0.0232(13) 0.0239(13) -0.0001(11) 0.0052(11) -0.0007(10) C(16) 0.0285(15) 0.0215(13) 0.0232(13) 0.0031(10) 0.0030(11) 0.0039(10) C(17) 0.0243(15) 0.0176(12) 0.0221(12) 0.0018(10) 0.0061(10) -0.0026(10) C(18) 0.0394(17) 0.0268(14) 0.0383(16) 0.0029(12) 0.0164(13) -0.0026(12) C(19) 0.0378(19) 0.0356(17) 0.052(2) 0.0103(14) 0.0110(15) 0.0054(14) C(20) 0.0281(16) 0.0199(13) 0.0413(16) 0.0003(12) 0.0097(13) 0.0042(11) C(21) 0.0219(15) 0.0182(12) 0.0352(14) -0.0019(10) 0.0095(12) -0.0010(11) C(22) 0.0333(17) 0.0275(14) 0.0299(15) 0.0023(11) 0.0071(12) 0.0083(11) C(23) 0.0343(16) 0.0288(15) 0.0275(15) 0.0020(12) 0.0047(12) -0.0005(11) C(24) 0.0405(18) 0.0268(17) 0.052(2) -0.0116(12) -0.0025(14) -0.0076(13) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution SIR97 _computing_structure_refinement 'CRYSTALS (Carruthers, et al., 1999)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S(1) O(4) 1.4285(18) yes . . S(1) O(6) 1.427(3) yes . . S(1) N(1) 1.709(3) yes . . S(1) C(21) 1.753(3) yes . . O(1) C(10) 1.205(4) yes . . O(2) C(10) 1.329(3) yes . . O(2) C(24) 1.445(4) yes . . O(3) C(2) 1.212(3) yes . . N(1) N(3) 1.414(4) yes . . N(1) C(2) 1.391(3) yes . . C(1) C(10) 1.494(4) yes . . C(1) C(15) 1.405(4) yes . . C(1) C(16) 1.395(4) yes . . C(2) C(17) 1.504(4) yes . . C(9) C(15) 1.375(4) yes . . C(9) C(17) 1.393(4) yes . . C(12) C(16) 1.380(4) yes . . C(12) C(17) 1.394(4) yes . . C(14) C(21) 1.399(4) yes . . C(14) C(22) 1.382(4) yes . . C(18) C(20) 1.382(4) yes . . C(18) C(23) 1.390(4) yes . . C(19) C(20) 1.520(4) yes . . C(20) C(22) 1.394(5) yes . . C(21) C(23) 1.389(4) yes . . N(3) H(1) 0.868 no . . N(3) H(2) 0.779 no . . C(9) H(14) 0.950 no . . C(12) H(3) 0.949 no . . C(14) H(16) 0.950 no . . C(15) H(4) 0.988 no . . C(16) H(5) 1.069 no . . C(18) H(6) 0.999 no . . C(19) H(7) 0.937 no . . C(19) H(8) 1.205 no . . C(19) H(9) 0.759 no . . C(22) H(10) 0.940 no . . C(23) H(11) 0.871 no . . C(24) H(12) 0.950 no . . C(24) H(13) 0.950 no . . C(24) H(15) 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O(4) S(1) O(6) 119.57(11) yes . . . O(4) S(1) N(1) 103.14(11) yes . . . O(4) S(1) C(21) 108.79(13) yes . . . O(6) S(1) N(1) 108.08(11) yes . . . O(6) S(1) C(21) 110.79(13) yes . . . N(1) S(1) C(21) 105.31(12) yes . . . C(10) O(2) C(24) 115.9(2) yes . . . S(1) N(1) N(3) 117.57(16) yes . . . S(1) N(1) C(2) 120.39(18) yes . . . N(3) N(1) C(2) 118.6(2) yes . . . C(10) C(1) C(15) 121.2(2) yes . . . C(10) C(1) C(16) 119.3(3) yes . . . C(15) C(1) C(16) 119.5(3) yes . . . O(3) C(2) N(1) 121.8(3) yes . . . O(3) C(2) C(17) 120.7(3) yes . . . N(1) C(2) C(17) 117.4(3) yes . . . C(15) C(9) C(17) 120.3(3) yes . . . O(1) C(10) O(2) 123.9(3) yes . . . O(1) C(10) C(1) 123.6(3) yes . . . O(2) C(10) C(1) 112.4(2) yes . . . C(16) C(12) C(17) 119.9(3) yes . . . C(21) C(14) C(22) 118.6(3) yes . . . C(1) C(15) C(9) 120.0(3) yes . . . C(1) C(16) C(12) 120.3(3) yes . . . C(2) C(17) C(9) 116.9(2) yes . . . C(2) C(17) C(12) 122.8(3) yes . . . C(9) C(17) C(12) 119.9(3) yes . . . C(20) C(18) C(23) 120.9(3) yes . . . C(18) C(20) C(19) 120.5(3) yes . . . C(18) C(20) C(22) 119.2(3) yes . . . C(19) C(20) C(22) 120.3(3) yes . . . S(1) C(21) C(14) 119.6(3) yes . . . S(1) C(21) C(23) 119.2(2) yes . . . C(14) C(21) C(23) 121.1(3) yes . . . C(14) C(22) C(20) 121.2(3) yes . . . C(18) C(23) C(21) 119.0(3) yes . . . N(1) N(3) H(1) 101.635 no . . . N(1) N(3) H(2) 111.765 no . . . H(1) N(3) H(2) 114.054 no . . . C(15) C(9) H(14) 119.909 no . . . C(17) C(9) H(14) 119.752 no . . . C(16) C(12) H(3) 118.991 no . . . C(17) C(12) H(3) 120.987 no . . . C(21) C(14) H(16) 120.521 no . . . C(22) C(14) H(16) 120.904 no . . . C(1) C(15) H(4) 116.182 no . . . C(9) C(15) H(4) 123.798 no . . . C(1) C(16) H(5) 118.209 no . . . C(12) C(16) H(5) 120.578 no . . . C(20) C(18) H(6) 123.001 no . . . C(23) C(18) H(6) 115.345 no . . . C(20) C(19) H(7) 109.130 no . . . C(20) C(19) H(8) 102.368 no . . . C(20) C(19) H(9) 108.746 no . . . H(7) C(19) H(8) 128.224 no . . . H(7) C(19) H(9) 101.871 no . . . H(8) C(19) H(9) 105.554 no . . . C(14) C(22) H(10) 116.895 no . . . C(20) C(22) H(10) 120.871 no . . . C(18) C(23) H(11) 120.199 no . . . C(21) C(23) H(11) 120.794 no . . . O(2) C(24) H(12) 109.650 no . . . O(2) C(24) H(13) 109.369 no . . . O(2) C(24) H(15) 109.395 no . . . H(12) C(24) H(13) 109.474 no . . . H(12) C(24) H(15) 109.469 no . . . H(13) C(24) H(15) 109.470 no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O(4) S(1) N(1) N(3) -30.06(18) no . . . . O(4) S(1) N(1) C(2) 171.10(16) no . . . . O(4) S(1) C(21) C(14) -163.99(18) no . . . . O(4) S(1) C(21) C(23) 19.0(3) no . . . . O(6) S(1) N(1) N(3) -157.60(14) no . . . . O(6) S(1) N(1) C(2) 43.55(19) no . . . . O(6) S(1) C(21) C(14) -30.6(3) no . . . . O(6) S(1) C(21) C(23) 152.37(17) no . . . . N(1) S(1) C(21) C(14) 86.0(2) no . . . . N(1) S(1) C(21) C(23) -91.0(2) no . . . . C(21) S(1) N(1) N(3) 83.95(17) no . . . . C(21) S(1) N(1) C(2) -74.90(19) no . . . . C(24) O(2) C(10) O(1) -1.1(4) no . . . . C(24) O(2) C(10) C(1) 179.5(3) no . . . . S(1) N(1) C(2) O(3) 2.2(4) no . . . . S(1) N(1) C(2) C(17) -175.07(14) no . . . . N(3) N(1) C(2) O(3) -156.5(2) no . . . . N(3) N(1) C(2) C(17) 26.3(3) no . . . . C(10) C(1) C(15) C(9) 179.2(3) no . . . . C(15) C(1) C(10) O(1) 170.7(3) no . . . . C(15) C(1) C(10) O(2) -9.9(4) no . . . . C(10) C(1) C(16) C(12) 179.7(3) no . . . . C(16) C(1) C(10) O(1) -9.8(4) no . . . . C(16) C(1) C(10) O(2) 169.6(3) no . . . . C(15) C(1) C(16) C(12) -0.9(4) no . . . . C(16) C(1) C(15) C(9) -0.3(4) no . . . . O(3) C(2) C(17) C(9) 38.1(4) no . . . . O(3) C(2) C(17) C(12) -134.4(3) no . . . . N(1) C(2) C(17) C(9) -144.7(2) no . . . . N(1) C(2) C(17) C(12) 42.8(4) no . . . . C(15) C(9) C(17) C(2) -172.4(3) no . . . . C(15) C(9) C(17) C(12) 0.3(4) no . . . . C(17) C(9) C(15) C(1) 0.6(4) no . . . . C(16) C(12) C(17) C(2) 170.8(3) no . . . . C(16) C(12) C(17) C(9) -1.4(4) no . . . . C(17) C(12) C(16) C(1) 1.8(4) no . . . . C(21) C(14) C(22) C(20) -1.6(4) no . . . . C(22) C(14) C(21) S(1) -176.3(3) no . . . . C(22) C(14) C(21) C(23) 0.7(4) no . . . . C(20) C(18) C(23) C(21) -1.5(5) no . . . . C(23) C(18) C(20) C(19) -179.3(3) no . . . . C(23) C(18) C(20) C(22) 0.7(5) no . . . . C(18) C(20) C(22) C(14) 0.9(4) no . . . . C(19) C(20) C(22) C(14) -179.2(3) no . . . . S(1) C(21) C(23) C(18) 177.81(18) no . . . . C(14) C(21) C(23) C(18) 0.8(4) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 S(1) O(3) 2.9293(18) no . . O(1) C(16) 2.857(4) no . . O(1) C(24) 2.651(4) no . . O(2) C(15) 2.737(3) no . . O(3) O(6) 2.804(3) no . . O(3) N(3) 3.504(3) no . . O(3) C(9) 2.858(4) no . . O(3) C(12) 3.529(4) no . . O(3) C(14) 3.135(4) no . . O(3) C(21) 3.352(3) no . . O(4) N(3) 2.778(3) no . . O(4) C(23) 2.926(4) no . . O(6) C(2) 3.013(3) no . . O(6) C(14) 3.030(4) no . . N(1) C(12) 3.029(4) no . . N(1) C(14) 3.508(4) no . . N(1) C(23) 3.545(4) no . . N(3) C(12) 2.995(4) no . . N(3) C(17) 2.823(4) no . . N(3) C(21) 3.460(4) no . . C(1) C(17) 2.781(4) no . . C(2) C(21) 3.393(4) no . . C(9) C(16) 2.778(4) no . . C(12) C(15) 2.783(4) no . . C(14) C(18) 2.785(5) no . . C(20) C(21) 2.774(4) no . . C(22) C(23) 2.777(4) no . . O(1) O(4) 3.520(3) no . 2_556 O(1) O(4) 3.376(3) no . 2_656 O(1) N(3) 3.031(3) no . 2_656 O(1) C(19) 3.527(4) no . 1_565 O(2) C(16) 3.413(4) no . 1_655 O(3) O(6) 3.183(3) no . 1_655 O(3) C(9) 3.353(3) no . 1_455 O(3) C(24) 3.356(4) no . 2_747 O(4) O(1) 3.520(3) no . 2_546 O(4) O(1) 3.376(3) no . 2_646 O(4) N(3) 3.225(3) no . 1_455 O(4) C(16) 3.355(3) no . 2_546 O(4) C(23) 3.587(4) no . 1_455 O(6) O(3) 3.183(3) no . 1_455 O(6) N(1) 3.289(3) no . 1_455 O(6) N(3) 3.433(3) no . 1_455 O(6) C(2) 2.944(3) no . 1_455 O(6) C(9) 3.247(3) no . 1_455 O(6) C(14) 3.345(4) no . 1_455 O(6) C(17) 3.331(3) no . 1_455 O(6) C(21) 3.398(4) no . 1_455 O(6) C(22) 3.578(4) no . 1_455 O(6) C(24) 3.592(4) no . 2_647 N(1) O(6) 3.289(3) no . 1_655 N(3) O(1) 3.031(3) no . 2_646 N(3) O(4) 3.225(3) no . 1_655 N(3) O(6) 3.433(3) no . 1_655 C(1) C(12) 3.586(4) no . 1_655 C(2) O(6) 2.944(3) no . 1_655 C(2) C(9) 3.442(4) no . 1_455 C(2) C(15) 3.584(4) no . 1_455 C(9) O(3) 3.353(3) no . 1_655 C(9) O(6) 3.247(3) no . 1_655 C(9) C(2) 3.442(4) no . 1_655 C(10) C(16) 3.582(4) no . 1_655 C(12) C(1) 3.586(4) no . 1_455 C(12) C(15) 3.377(4) no . 1_455 C(14) O(6) 3.345(4) no . 1_655 C(15) C(2) 3.584(4) no . 1_655 C(15) C(12) 3.377(4) no . 1_655 C(15) C(17) 3.568(4) no . 1_655 C(15) C(22) 3.447(4) no . 2_657 C(16) O(2) 3.413(4) no . 1_455 C(16) O(4) 3.355(3) no . 2_556 C(16) C(10) 3.582(4) no . 1_455 C(16) C(18) 3.592(4) no . 2_656 C(17) O(6) 3.331(3) no . 1_655 C(17) C(15) 3.568(4) no . 1_455 C(18) C(16) 3.592(4) no . 2_646 C(19) O(1) 3.527(4) no . 1_545 C(21) O(6) 3.398(4) no . 1_655 C(22) O(6) 3.578(4) no . 1_655 C(22) C(15) 3.447(4) no . 2_647 C(23) O(4) 3.587(4) no . 1_655 C(24) O(3) 3.356(4) no . 2_757 C(24) O(6) 3.592(4) no . 2_657 S(1) H(1) 2.6737 no . . S(1) H(2) 2.8701 no . . S(1) H(11) 2.8032 no . . S(1) H(16) 2.8385 no . . O(1) H(5) 2.5432 no . . O(1) H(12) 2.4504 no . . O(1) H(13) 2.7926 no . . O(1) H(15) 3.5639 no . . O(2) H(4) 2.3608 no . . O(3) H(14) 2.6503 no . . O(3) H(16) 2.6302 no . . O(4) H(1) 2.3620 no . . O(4) H(2) 2.9593 no . . O(4) H(11) 2.5817 no . . O(6) H(16) 2.7093 no . . N(1) H(3) 2.8244 no . . N(1) H(11) 3.5872 no . . N(1) H(16) 3.5303 no . . N(3) H(3) 2.7177 no . . N(3) H(11) 3.5361 no . . C(1) H(3) 3.2577 no . . C(1) H(14) 3.2661 no . . C(2) H(1) 3.0074 no . . C(2) H(2) 2.7651 no . . C(2) H(3) 2.7362 no . . C(2) H(14) 2.5996 no . . C(2) H(16) 3.3895 no . . C(9) H(3) 3.2755 no . . C(10) H(4) 2.6447 no . . C(10) H(5) 2.6632 no . . C(10) H(12) 2.4911 no . . C(10) H(13) 2.6800 no . . C(10) H(15) 3.1275 no . . C(12) H(1) 3.4110 no . . C(12) H(2) 3.5428 no . . C(12) H(14) 3.2690 no . . C(14) H(11) 3.2130 no . . C(15) H(5) 3.3718 no . . C(16) H(4) 3.2862 no . . C(17) H(1) 3.4772 no . . C(17) H(2) 3.2027 no . . C(17) H(4) 3.3168 no . . C(17) H(5) 3.3718 no . . C(18) H(7) 3.2603 no . . C(18) H(8) 2.5395 no . . C(18) H(9) 2.7989 no . . C(18) H(10) 3.2434 no . . C(19) H(6) 2.7445 no . . C(19) H(10) 2.6988 no . . C(20) H(11) 3.1934 no . . C(20) H(16) 3.2788 no . . C(21) H(2) 3.2497 no . . C(21) H(6) 3.2640 no . . C(21) H(10) 3.2207 no . . C(22) H(6) 3.3136 no . . C(22) H(7) 2.5642 no . . C(22) H(8) 3.3936 no . . C(22) H(9) 2.8676 no . . C(23) H(2) 3.3045 no . . C(23) H(16) 3.2838 no . . H(1) H(3) 2.9008 no . . H(1) H(11) 3.5598 no . . H(2) H(3) 3.3927 no . . H(2) H(11) 3.0918 no . . H(3) H(5) 2.3939 no . . H(4) H(14) 2.3992 no . . H(6) H(8) 2.3199 no . . H(6) H(9) 2.9847 no . . H(6) H(11) 2.2651 no . . H(7) H(10) 2.3934 no . . H(9) H(10) 3.0397 no . . H(10) H(16) 2.3001 no . . S(1) H(2) 3.1377 no . 1_455 S(1) H(5) 3.5395 no . 2_546 O(1) H(1) 2.6950 no . 2_656 O(1) H(2) 2.6672 no . 2_656 O(1) H(8) 2.7085 no . 1_565 O(1) H(11) 3.0065 no . 2_656 O(1) H(12) 3.1254 no . 1_455 O(1) H(15) 3.5880 no . 1_455 O(2) H(5) 3.5741 no . 1_655 O(2) H(10) 3.3176 no . 2_757 O(2) H(16) 2.8128 no . 2_657 O(3) H(4) 3.4558 no . 1_455 O(3) H(7) 2.9113 no . 2_657 O(3) H(13) 3.0540 no . 2_647 O(3) H(13) 3.3934 no . 2_747 O(3) H(14) 2.8080 no . 1_455 O(3) H(15) 2.5611 no . 2_747 O(4) H(2) 2.4838 no . 1_455 O(4) H(5) 2.3010 no . 2_546 O(4) H(11) 3.5691 no . 1_455 O(6) H(2) 3.0254 no . 1_455 O(6) H(13) 3.3181 no . 2_647 O(6) H(14) 2.7996 no . 1_455 O(6) H(15) 3.2048 no . 2_647 N(3) H(6) 3.2749 no . 2_656 N(3) H(8) 2.8922 no . 2_656 C(1) H(3) 3.2422 no . 1_655 C(1) H(10) 3.2673 no . 2_657 C(1) H(11) 3.2777 no . 2_656 C(1) H(16) 3.5345 no . 2_657 C(2) H(4) 3.4530 no . 1_455 C(2) H(14) 3.2088 no . 1_455 C(2) H(15) 3.4947 no . 2_747 C(9) H(10) 2.8109 no . 2_657 C(9) H(13) 3.3127 no . 2_747 C(10) H(5) 3.5050 no . 1_655 C(10) H(11) 3.2879 no . 2_656 C(10) H(12) 3.3803 no . 1_455 C(10) H(15) 3.3780 no . 1_455 C(10) H(16) 3.4035 no . 2_657 C(12) H(4) 3.1919 no . 1_455 C(12) H(6) 2.9518 no . 2_656 C(12) H(11) 3.3977 no . 2_556 C(14) H(4) 3.4485 no . 2_647 C(14) H(9) 3.2831 no . 1_455 C(14) H(15) 3.1909 no . 2_747 C(15) H(3) 3.2280 no . 1_655 C(15) H(7) 3.5114 no . 2_757 C(15) H(10) 2.7155 no . 2_657 C(15) H(16) 3.3620 no . 2_657 C(16) H(6) 3.0283 no . 2_656 C(16) H(11) 3.5474 no . 2_556 C(16) H(11) 3.0975 no . 2_656 C(16) H(12) 3.4675 no . 1_455 C(17) H(4) 3.2082 no . 1_455 C(17) H(10) 3.4308 no . 2_657 C(18) H(3) 3.5954 no . 2_546 C(18) H(5) 3.2502 no . 2_646 C(18) H(9) 3.5939 no . 1_455 C(19) H(4) 3.4174 no . 2_747 C(19) H(12) 3.4280 no . 1_445 C(19) H(13) 3.1619 no . 1_545 C(20) H(9) 3.4024 no . 1_455 C(21) H(9) 3.4932 no . 1_455 C(22) H(4) 3.4560 no . 2_647 C(22) H(4) 3.3785 no . 2_747 C(22) H(9) 3.2428 no . 1_455 C(22) H(15) 3.4990 no . 2_747 C(23) H(3) 3.2014 no . 2_546 C(23) H(5) 3.1316 no . 2_646 C(24) H(14) 3.0799 no . 2_757 C(24) H(16) 3.5474 no . 2_657 C(24) H(16) 3.5934 no . 2_757 H(1) O(1) 2.6950 no . 2_646 H(1) H(6) 3.5107 no . 2_556 H(1) H(6) 3.5364 no . 2_656 H(1) H(8) 2.7161 no . 2_656 H(1) H(9) 3.5322 no . 2_656 H(1) H(12) 3.4647 no . 2_646 H(2) S(1) 3.1377 no . 1_655 H(2) O(1) 2.6672 no . 2_646 H(2) O(4) 2.4838 no . 1_655 H(2) O(6) 3.0254 no . 1_655 H(2) H(5) 3.3988 no . 2_646 H(2) H(6) 3.4379 no . 2_656 H(2) H(8) 2.8717 no . 2_656 H(3) C(1) 3.2422 no . 1_455 H(3) C(15) 3.2280 no . 1_455 H(3) C(18) 3.5954 no . 2_556 H(3) C(23) 3.2014 no . 2_556 H(3) H(4) 3.3281 no . 1_455 H(3) H(6) 3.2307 no . 2_556 H(3) H(6) 2.9780 no . 2_656 H(3) H(11) 2.6727 no . 2_556 H(4) O(3) 3.4558 no . 1_655 H(4) C(2) 3.4530 no . 1_655 H(4) C(12) 3.1919 no . 1_655 H(4) C(14) 3.4485 no . 2_657 H(4) C(17) 3.2082 no . 1_655 H(4) C(19) 3.4174 no . 2_757 H(4) C(22) 3.4560 no . 2_657 H(4) C(22) 3.3785 no . 2_757 H(4) H(3) 3.3281 no . 1_655 H(4) H(7) 2.8011 no . 2_757 H(4) H(9) 3.2397 no . 2_757 H(4) H(10) 2.9429 no . 2_657 H(4) H(10) 2.7571 no . 2_757 H(4) H(16) 3.0669 no . 2_657 H(5) S(1) 3.5395 no . 2_556 H(5) O(2) 3.5741 no . 1_455 H(5) O(4) 2.3010 no . 2_556 H(5) C(10) 3.5050 no . 1_455 H(5) C(18) 3.2502 no . 2_656 H(5) C(23) 3.1316 no . 2_656 H(5) H(2) 3.3988 no . 2_656 H(5) H(6) 2.9655 no . 2_656 H(5) H(11) 2.9950 no . 2_556 H(5) H(11) 2.7208 no . 2_656 H(5) H(12) 3.1882 no . 1_455 H(6) N(3) 3.2749 no . 2_646 H(6) C(12) 2.9518 no . 2_646 H(6) C(16) 3.0283 no . 2_646 H(6) H(1) 3.5107 no . 2_546 H(6) H(1) 3.5364 no . 2_646 H(6) H(2) 3.4379 no . 2_646 H(6) H(3) 3.2307 no . 2_546 H(6) H(3) 2.9780 no . 2_646 H(6) H(5) 2.9655 no . 2_646 H(7) O(3) 2.9113 no . 2_647 H(7) C(15) 3.5114 no . 2_747 H(7) H(4) 2.8011 no . 2_747 H(7) H(12) 3.3059 no . 1_445 H(7) H(13) 2.8130 no . 1_545 H(7) H(14) 3.4595 no . 2_647 H(7) H(14) 3.1286 no . 2_747 H(7) H(15) 3.3772 no . 1_445 H(8) O(1) 2.7085 no . 1_545 H(8) N(3) 2.8922 no . 2_646 H(8) H(1) 2.7161 no . 2_646 H(8) H(2) 2.8717 no . 2_646 H(8) H(12) 2.9941 no . 1_445 H(8) H(13) 3.3395 no . 1_545 H(9) C(14) 3.2831 no . 1_655 H(9) C(18) 3.5939 no . 1_655 H(9) C(20) 3.4024 no . 1_655 H(9) C(21) 3.4932 no . 1_655 H(9) C(22) 3.2428 no . 1_655 H(9) H(1) 3.5322 no . 2_646 H(9) H(4) 3.2397 no . 2_747 H(9) H(10) 3.4730 no . 1_655 H(9) H(12) 3.5614 no . 1_545 H(9) H(13) 3.0237 no . 1_545 H(9) H(14) 3.5222 no . 2_747 H(10) O(2) 3.3176 no . 2_747 H(10) C(1) 3.2673 no . 2_647 H(10) C(9) 2.8109 no . 2_647 H(10) C(15) 2.7155 no . 2_647 H(10) C(17) 3.4308 no . 2_647 H(10) H(4) 2.9429 no . 2_647 H(10) H(4) 2.7571 no . 2_747 H(10) H(9) 3.4730 no . 1_455 H(10) H(14) 3.0202 no . 2_647 H(10) H(15) 3.3430 no . 2_747 H(11) O(1) 3.0065 no . 2_646 H(11) O(4) 3.5691 no . 1_655 H(11) C(1) 3.2777 no . 2_646 H(11) C(10) 3.2879 no . 2_646 H(11) C(12) 3.3977 no . 2_546 H(11) C(16) 3.5474 no . 2_546 H(11) C(16) 3.0975 no . 2_646 H(11) H(3) 2.6727 no . 2_546 H(11) H(5) 2.9950 no . 2_546 H(11) H(5) 2.7208 no . 2_646 H(12) O(1) 3.1254 no . 1_655 H(12) C(10) 3.3803 no . 1_655 H(12) C(16) 3.4675 no . 1_655 H(12) C(19) 3.4280 no . 1_665 H(12) H(1) 3.4647 no . 2_656 H(12) H(5) 3.1882 no . 1_655 H(12) H(7) 3.3059 no . 1_665 H(12) H(8) 2.9941 no . 1_665 H(12) H(9) 3.5614 no . 1_565 H(13) O(3) 3.0540 no . 2_657 H(13) O(3) 3.3934 no . 2_757 H(13) O(6) 3.3181 no . 2_657 H(13) C(9) 3.3127 no . 2_757 H(13) C(19) 3.1619 no . 1_565 H(13) H(7) 2.8130 no . 1_565 H(13) H(8) 3.3395 no . 1_565 H(13) H(9) 3.0237 no . 1_565 H(13) H(14) 2.3745 no . 2_757 H(13) H(16) 3.3768 no . 2_657 H(14) O(3) 2.8080 no . 1_655 H(14) O(6) 2.7996 no . 1_655 H(14) C(2) 3.2088 no . 1_655 H(14) C(24) 3.0799 no . 2_747 H(14) H(7) 3.4595 no . 2_657 H(14) H(7) 3.1286 no . 2_757 H(14) H(9) 3.5222 no . 2_757 H(14) H(10) 3.0202 no . 2_657 H(14) H(13) 2.3745 no . 2_747 H(14) H(15) 2.9698 no . 2_747 H(15) O(1) 3.5880 no . 1_655 H(15) O(3) 2.5611 no . 2_757 H(15) O(6) 3.2048 no . 2_657 H(15) C(2) 3.4947 no . 2_757 H(15) C(10) 3.3780 no . 1_655 H(15) C(14) 3.1909 no . 2_757 H(15) C(22) 3.4990 no . 2_757 H(15) H(7) 3.3772 no . 1_665 H(15) H(10) 3.3430 no . 2_757 H(15) H(14) 2.9698 no . 2_757 H(15) H(16) 2.6945 no . 2_757 H(16) O(2) 2.8128 no . 2_647 H(16) C(1) 3.5345 no . 2_647 H(16) C(10) 3.4035 no . 2_647 H(16) C(15) 3.3620 no . 2_647 H(16) C(24) 3.5474 no . 2_647 H(16) C(24) 3.5934 no . 2_747 H(16) H(4) 3.0669 no . 2_647 H(16) H(13) 3.3768 no . 2_647 H(16) H(15) 2.6945 no . 2_747 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N(3) H(1) O(4) . . . 2.778(3) 0.868 2.362 109.7 no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================