#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:08:28 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201955 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/82/2008242.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2008242 loop_ _publ_author_name 'D. Prahadeeswaran' 'T. Parthasarathy Seshadri' _publ_section_title ; 5'-O-(Toluenesulfonyl)adenosine ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 389 _journal_page_last 391 _journal_paper_doi 10.1107/S0108270198013262 _journal_volume 55 _journal_year 1999 _chemical_formula_structural 'C17 H19 N5 O6 S' _chemical_formula_sum 'C17 H19 N5 O6 S' _chemical_formula_weight 421.43 _chemical_name_systematic ; 5'-(toluenesulfonyl)adenosine ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90.000(10) _cell_angle_beta 90.000(10) _cell_angle_gamma 90.00(2) _cell_formula_units_Z 4 _cell_length_a 8.045(2) _cell_length_b 8.937(2) _cell_length_c 26.773(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12 _cell_measurement_theta_min 6 _cell_volume 1924.9(7) _computing_cell_refinement 'CAD-4 Diffractometer Control Software' _computing_data_collection 'CAD-4 Diffractometer Control Software (Enraf-Nonius, 1985a)' _computing_data_reduction 'Structure Determination Package (Enraf--Nonius, 1985b)' _computing_molecular_graphics 'INSIGHT II (Biosym Technologies, 1995) and Xtal_GX (Hall & du Boulay, 1995)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Enraf--Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed X-ray tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_av_sigmaI/netI 0.033 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1960 _diffrn_reflns_theta_max 69.96 _diffrn_reflns_theta_min 3.3 _diffrn_standards_decay_% none _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.912 _exptl_absorpt_correction_T_max 0.682 _exptl_absorpt_correction_T_min 0.627 _exptl_absorpt_correction_type \y-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Parallelepiped _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.267 _refine_diff_density_min -0.230 _refine_ls_abs_structure_Flack -0.08(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.032 _refine_ls_goodness_of_fit_obs 1.049 _refine_ls_hydrogen_treatment 'H atoms: see below' _refine_ls_matrix_type full _refine_ls_number_parameters 285 _refine_ls_number_reflns 1960 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_restrained_S_obs 1.049 _refine_ls_R_factor_all 0.055 _refine_ls_R_factor_obs 0.039 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.1143P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.129 _refine_ls_wR_factor_obs 0.115 _reflns_number_observed 1573 _reflns_number_total 1960 _reflns_observed_criterion I>2\s(I) _cod_data_source_file de1093.cif _cod_data_source_block 5TA _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_geom_bond_publ_flag' value 'No' changed to 'no' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (30 times). '_geom_bond_publ_flag' value 'NO' changed to 'no' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.1143P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.1143P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2008242 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, -y, z+1/2' 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 N1 0.040(2) 0.049(2) 0.033(2) 0.005(2) -0.001(2) 0.003(2) C2 0.038(2) 0.049(3) 0.035(2) 0.009(2) -0.002(2) -0.001(2) N3 0.039(2) 0.040(2) 0.026(2) 0.001(2) 0.004(2) 0.001(2) C4 0.032(2) 0.032(2) 0.027(2) -0.001(2) -0.002(2) 0.002(2) C5 0.037(2) 0.041(2) 0.028(2) 0.000(2) 0.000(2) 0.006(2) C6 0.040(2) 0.042(2) 0.032(2) -0.002(2) -0.004(2) 0.007(2) N6 0.038(2) 0.088(3) 0.031(2) 0.004(2) -0.003(2) 0.021(2) N7 0.034(2) 0.074(3) 0.032(2) 0.004(2) 0.006(2) 0.018(2) C8 0.036(3) 0.064(3) 0.035(2) 0.003(3) 0.001(2) 0.015(2) N9 0.031(2) 0.041(2) 0.027(2) 0.003(2) 0.0006(15) 0.0060(14) C1' 0.033(2) 0.037(2) 0.022(2) 0.002(2) -0.002(2) -0.001(2) C2' 0.034(2) 0.042(2) 0.025(2) -0.005(2) 0.000(2) 0.003(2) O2' 0.058(2) 0.047(2) 0.041(2) 0.013(2) 0.018(2) 0.0129(15) C3' 0.038(2) 0.031(2) 0.023(2) -0.003(2) 0.003(2) 0.004(2) O3' 0.051(2) 0.0303(15) 0.0320(15) -0.0031(14) 0.0089(13) 0.0019(12) C4' 0.039(2) 0.027(2) 0.027(2) 0.000(2) -0.003(2) 0.003(2) O4' 0.036(2) 0.0276(14) 0.0351(14) -0.0013(13) -0.0072(13) 0.0047(11) C5' 0.034(2) 0.043(2) 0.041(2) 0.002(2) -0.006(2) 0.006(2) O5' 0.052(2) 0.050(2) 0.040(2) 0.016(2) 0.0095(15) 0.0063(14) S 0.0481(7) 0.0438(6) 0.0518(7) 0.0072(6) 0.0003(6) -0.0027(5) OS1 0.110(3) 0.047(2) 0.073(2) -0.016(2) -0.011(3) 0.013(2) OS2 0.042(2) 0.109(3) 0.071(2) 0.020(2) -0.006(2) -0.015(2) C10 0.045(3) 0.043(2) 0.050(3) -0.002(2) 0.001(2) -0.008(2) C11 0.102(5) 0.047(3) 0.055(3) -0.015(3) 0.004(3) -0.007(2) C12 0.122(6) 0.066(4) 0.061(4) -0.011(4) 0.008(4) 0.001(3) C13 0.064(3) 0.088(4) 0.052(3) -0.002(4) 0.001(3) -0.004(3) C14 0.131(7) 0.089(5) 0.067(4) -0.035(5) 0.005(4) -0.030(4) C15 0.124(6) 0.060(4) 0.059(3) -0.022(4) 0.007(4) -0.019(3) C13' 0.112(6) 0.158(8) 0.049(3) -0.002(7) 0.005(4) 0.002(4) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N1 -0.2131(5) 1.2679(4) 0.06652(13) 0.0406(9) Uani d . 1 . N C2 -0.2397(6) 1.2468(5) 0.11530(15) 0.0403(11) Uani d . 1 . C H2 -0.3447(6) 1.2739(5) 0.12661(15) 0.029(10) Uiso calc R 1 . H N3 -0.1380(4) 1.1926(4) 0.15002(11) 0.0351(8) Uani d . 1 . N C4 0.0128(5) 1.1630(4) 0.13049(13) 0.0303(9) Uani d . 1 . C C5 0.0590(5) 1.1818(5) 0.08111(14) 0.0355(10) Uani d . 1 . C C6 -0.0622(6) 1.2342(5) 0.04791(15) 0.0379(10) Uani d . 1 . C N6 -0.0347(5) 1.2499(6) -0.00104(14) 0.0525(11) Uani d . 1 . N H61 -0.1129(5) 1.2813(6) -0.02026(14) 0.044(13) Uiso calc R 1 . H H62 0.0612(5) 1.2286(6) -0.01331(14) 0.071(19) Uiso calc R 1 . H N7 0.2230(5) 1.1399(5) 0.07440(13) 0.0465(10) Uani d . 1 . N C8 0.2706(6) 1.0968(6) 0.1186(2) 0.0452(12) Uani d . 1 . C H8 0.3772(6) 1.0620(6) 0.1253(2) 0.037(12) Uiso calc R 1 . H N9 0.1499(4) 1.1073(4) 0.15426(11) 0.0329(7) Uani d . 1 . N C1' 0.1651(5) 1.0710(5) 0.20783(13) 0.0308(9) Uani d . 1 . C H1' 0.1216(5) 1.1536(5) 0.22805(13) 0.015(9) Uiso calc R 1 . H C2' 0.0756(5) 0.9256(5) 0.22129(14) 0.0336(9) Uani d . 1 . C H2' -0.0133(5) 0.9019(5) 0.19756(14) 0.023(10) Uiso calc R 1 . H O2' 0.0178(4) 0.9285(4) 0.27093(11) 0.0486(8) Uani d . 1 . O HO2' -0.045(6) 1.000(4) 0.2746(6) 0.08(2) Uiso calc R 1 . H C3' 0.2180(5) 0.8117(5) 0.21893(14) 0.0305(9) Uani d . 1 . C H3' 0.2361(5) 0.7852(5) 0.18383(14) 0.022(9) Uiso calc R 1 . H O3' 0.1937(4) 0.6787(3) 0.24594(11) 0.0377(7) Uani d . 1 . O HO3' 0.188(6) 0.6996(13) 0.2785(17) 0.043(13) Uiso calc R 1 . H C4' 0.3657(5) 0.9027(4) 0.23647(14) 0.0309(9) Uani d . 1 . C H4' 0.3637(5) 0.9067(4) 0.27305(14) 0.019(9) Uiso calc R 1 . H O4' 0.3364(3) 1.0511(3) 0.21747(9) 0.0327(6) Uani d . 1 . O C5' 0.5353(5) 0.8509(5) 0.2201(2) 0.0393(10) Uani d . 1 . C H5'1 0.6187(5) 0.9232(5) 0.2302(2) 0.030(11) Uiso calc R 1 . H H5'2 0.5614(5) 0.7557(5) 0.2356(2) 0.051(15) Uiso calc R 1 . H O5' 0.5349(4) 0.8352(4) 0.16564(11) 0.0474(8) Uani d . 1 . O S 0.6376(2) 0.69992(14) 0.14459(4) 0.0479(3) Uani d . 1 . S OS1 0.5466(6) 0.5661(4) 0.15316(15) 0.0766(13) Uani d . 1 . O OS2 0.8023(4) 0.7096(5) 0.16405(14) 0.0738(12) Uani d . 1 . O C10 0.6321(7) 0.7459(5) 0.0812(2) 0.0460(11) Uani d . 1 . C C11 0.6751(8) 0.8843(6) 0.0647(2) 0.068(2) Uani d . 1 . C H11 0.7044(8) 0.9583(6) 0.0874(2) 0.070(18) Uiso calc R 1 . H C12 0.6754(10) 0.9150(8) 0.0147(2) 0.083(2) Uani d . 1 . C H12 0.7057(10) 1.0103(8) 0.0041(2) 0.10(2) Uiso calc R 1 . H C13 0.6327(8) 0.8105(8) -0.0202(2) 0.068(2) Uani d . 1 . C C14 0.5940(11) 0.6705(8) -0.0027(3) 0.096(3) Uani d . 1 . C H14 0.5685(11) 0.5956(8) -0.0256(3) 0.10(2) Uiso calc R 1 . H C15 0.5913(10) 0.6365(7) 0.0477(2) 0.081(2) Uani d . 1 . C H15 0.5623(10) 0.5412(7) 0.0585(2) 0.12(3) Uiso calc R 1 . H C13' 0.6319(11) 0.8445(11) -0.0758(2) 0.107(3) Uani d . 1 . C H1M 0.6621(11) 0.9472(11) -0.0810(2) 0.128 Uiso calc R 1 . H H2M 0.5227(11) 0.8270(11) -0.0890(2) 0.128 Uiso calc R 1 . H H3M 0.7102(11) 0.7807(11) -0.0924(2) 0.128 Uiso calc R 1 . H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .3331 .5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -2 -2 0 -1 5 0 0 2 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 C2 N1 C6 118.3(4) no N3 C2 N1 129.5(4) no C2 N3 C4 110.8(3) no N3 C4 N9 128.1(3) no N3 C4 C5 126.1(4) no N9 C4 C5 105.8(3) no N7 C5 C4 110.3(4) no N7 C5 C6 132.3(4) no C4 C5 C6 117.4(4) no N6 C6 N1 119.2(4) no N6 C6 C5 122.8(4) no N1 C6 C5 117.9(4) no C8 N7 C5 104.0(4) no N7 C8 N9 114.0(4) no C8 N9 C4 105.9(3) no C8 N9 C1' 127.3(3) no C4 N9 C1' 126.8(3) no O4' C1' N9 106.6(3) no O4' C1' C2' 108.0(3) no N9 C1' C2' 112.1(3) no O2' C2' C1' 111.2(3) no O2' C2' C3' 107.3(3) no C1' C2' C3' 101.7(3) no O3' C3' C4' 113.8(3) no O3' C3' C2' 115.9(3) no C4' C3' C2' 102.5(3) no O4' C4' C5' 109.2(3) no O4' C4' C3' 104.9(3) no C5' C4' C3' 117.1(3) no C1' O4' C4' 109.9(3) no O5' C5' C4' 108.5(3) no C5' O5' S 115.5(3) no OS1 S OS2 118.1(3) no OS1 S O5' 108.6(2) no OS2 S O5' 108.1(2) no OS1 S C10 110.0(2) no OS2 S C10 111.4(3) no O5' S C10 98.9(2) no C11 C10 C15 119.8(5) no C11 C10 S 121.6(4) no C15 C10 S 118.5(4) no C10 C11 C12 120.2(5) no C11 C12 C13 122.3(6) no C14 C13 C12 116.5(6) no C14 C13 C13' 121.1(7) no C12 C13 C13' 122.4(7) no C13 C14 C15 122.5(6) no C10 C15 C14 118.7(6) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 . 1.337(5) no N1 C6 . 1.346(6) no C2 N3 . 1.329(5) no N3 C4 . 1.348(5) no C4 N9 . 1.367(5) no C4 C5 . 1.384(5) no C5 N7 . 1.383(6) no C5 C6 . 1.400(6) no C6 N6 . 1.336(5) no N7 C8 . 1.302(5) no C8 N9 . 1.365(5) no N9 C1' . 1.475(4) no C1' O4' . 1.413(5) no C1' C2' . 1.529(6) no C2' O2' . 1.408(5) no C2' C3' . 1.534(6) no C3' O3' . 1.405(5) no C3' C4' . 1.514(6) no C4' O4' . 1.440(4) no C4' C5' . 1.505(6) no C5' O5' . 1.466(5) no O5' S . 1.569(3) no S OS1 . 1.421(4) no S OS2 . 1.426(4) no S C10 . 1.746(5) no C10 C11 . 1.359(7) no C10 C15 . 1.368(7) no C11 C12 . 1.365(8) no C12 C13 . 1.366(8) no C13 C14 . 1.372(9) no C13 C13' . 1.518(8) no C14 C15 . 1.382(8) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N6 H61 N7 3_475 0.860(6) 2.082(6) 2.937(6) 172.2(5) N6 H62 N1 3_575 0.860(6) 2.310(6) 3.131(6) 159.8(5) O3' HO3' N3 2_545 0.859(4) 1.990(5) 2.826(4) 170.1(2) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C6 N1 C2 N3 -1.5(7) no N1 C2 N3 C4 2.7(7) no C2 N3 C4 N9 179.6(4) no C2 N3 C4 C5 -1.3(6) no N3 C4 C5 N7 -179.9(4) no N9 C4 C5 N7 -0.6(5) no N3 C4 C5 C6 -1.1(7) no N9 C4 C5 C6 178.1(4) no C2 N1 C6 N6 177.9(4) no C2 N1 C6 C5 -1.3(6) no N7 C5 C6 N6 1.7(8) no C4 C5 C6 N6 -176.7(4) no N7 C5 C6 N1 -179.1(5) no C4 C5 C6 N1 2.5(6) no C4 C5 N7 C8 0.4(5) no C6 C5 N7 C8 -178.1(5) no C5 N7 C8 N9 -0.1(6) no N7 C8 N9 C4 -0.3(6) no N7 C8 N9 C1' -178.4(4) no N3 C4 N9 C8 179.8(4) no C5 C4 N9 C8 0.6(5) no N3 C4 N9 C1' -2.1(7) no C5 C4 N9 C1' 178.7(4) no C8 N9 C1' O4' 11.2(6) no C4 N9 C1' O4' -166.5(4) no C8 N9 C1' C2' -106.8(5) no C4 N9 C1' C2' 75.5(5) no O4' C1' C2' O2' 92.6(4) no N9 C1' C2' O2' -150.2(3) no O4' C1' C2' C3' -21.4(4) yes N9 C1' C2' C3' 95.8(4) no O2' C2' C3' O3' 41.2(4) no C1' C2' C3' O3' 158.1(3) no O2' C2' C3' C4' -83.3(4) no C1' C2' C3' C4' 33.5(3) yes O3' C3' C4' O4' -160.7(3) no C2' C3' C4' O4' -34.8(4) yes O3' C3' C4' C5' 78.1(4) no C2' C3' C4' C5' -156.0(3) no N9 C1' O4' C4' -120.8(3) no C2' C1' O4' C4' -0.1(4) yes C5' C4' O4' C1' 148.5(3) no C3' C4' O4' C1' 22.2(4) yes O4' C4' C5' O5' -65.7(4) yes C3' C4' C5' O5' 53.2(5) yes C4' C5' O5' S -142.8(3) yes C5' O5' S OS1 75.4(3) no C5' O5' S OS2 -53.9(4) no C5' O5' S C10 -170.0(3) yes OS1 S C10 C11 164.5(5) no OS2 S C10 C11 -62.7(6) no O5' S C10 C11 50.8(6) yes OS1 S C10 C15 -18.9(6) no OS2 S C10 C15 114.0(6) no O5' S C10 C15 -132.5(5) yes C15 C10 C11 C12 0.9(10) no S C10 C11 C12 177.5(5) no C10 C11 C12 C13 0.3(11) no C11 C12 C13 C14 -1.9(11) no C11 C12 C13 C13' 179.6(7) no C12 C13 C14 C15 2.5(12) no C13' C13 C14 C15 -179.0(8) no C11 C10 C15 C14 -0.4(11) no S C10 C15 C14 -177.1(6) no C13 C14 C15 C10 -1.4(12) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 2006500