#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012859.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_2012859 loop_ _publ_author_name 'Crozet, M. D.' 'Vanelle, P.' 'Giorgi, M.' 'Gellis, A.' _publ_section_title ; 2-[2-Methyl-5-nitro-4-(phenylsulfonylmethyl)imidazol-1-yl]ethanol and 2-methyl-5-nitro-4-phenylsulfonylmethyl-1,3-thiazole ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o496 _journal_page_last o498 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C13 H15 N3 O5 S1' _chemical_formula_moiety 'C13 H15 N3 O5 S1' _chemical_formula_structural 'C13 H15 N3 O5 S' _chemical_formula_sum 'C13 H15 N3 O5 S' _chemical_formula_weight 325.343 _chemical_name_systematic ; 2-(4-benzenesulfonylmethyl-2-methyl-5-nitro-imidazol-1-yl)-ethanol ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method maXus _cell_angle_alpha 90. _cell_angle_beta 94.427(2) _cell_angle_gamma 90. _cell_formula_units_Z 4 _cell_length_a 12.5976(3) _cell_length_b 7.7874(3) _cell_length_c 14.8929(5) _cell_measurement_reflns_used 2911 _cell_measurement_temperature 293 _cell_measurement_theta_max 26.4 _cell_measurement_theta_min 2.4 _cell_volume 1456.67(8) _computing_cell_refinement 'KappaCCD Reference' _computing_data_collection 'KappaCCD Reference Manual (Nonius, 1998)' _computing_data_reduction 'DENZO and SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.917 _diffrn_measured_fraction_theta_max 0.917 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method \f _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 2911 _diffrn_reflns_theta_full 26.38 _diffrn_reflns_theta_max 26.38 _diffrn_reflns_theta_min 2.4 _diffrn_standards_decay_% <0.1 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.250 _exptl_absorpt_correction_type none _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.4 _refine_diff_density_max 0.217 _refine_diff_density_min -0.276 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 2726 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0462 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.6408P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1087 _refine_ls_wR_factor_ref 0.1129 _reflns_number_gt 2509 _reflns_number_total 2726 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file dn1013.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _[local]_cod_chemical_formula_sum_orig 'C13 H15 N3 O5 S1' _cod_database_code 2012859 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol S1 0.21423(4) 0.02005(6) 0.10308(3) 0.05482(19) Uani d . 1 S O1 0.14467(15) -0.10385(19) 0.05876(12) 0.0865(6) Uani d . 1 O O2 0.32604(12) -0.0151(2) 0.11349(11) 0.0763(5) Uani d . 1 O O3 0.15023(17) 0.6036(2) 0.28117(17) 0.1074(7) Uani d . 1 O O4 0.06922(12) 0.3935(2) 0.21328(12) 0.0743(5) Uani d . 1 O O5 0.45589(12) 0.80584(17) 0.33634(13) 0.0762(5) Uani d . 1 O H5B 0.4093 0.8795 0.3350 0.114 Uiso calc R 1 H N1 0.32903(10) 0.10909(16) 0.31418(9) 0.0388(3) Uani d . 1 N N2 0.31723(11) 0.38808(16) 0.34262(8) 0.0392(3) Uani d . 1 N N3 0.14515(13) 0.4535(2) 0.25888(11) 0.0540(4) Uani d . 1 N C1 0.19509(13) 0.2181(2) 0.04813(11) 0.0461(4) Uani d . 1 C C2 0.10579(15) 0.2396(3) -0.01101(12) 0.0520(4) Uani d . 1 C H2 0.0578 0.1499 -0.0221 0.062 Uiso calc R 1 H C3 0.08906(17) 0.3957(3) -0.05324(13) 0.0602(5) Uani d . 1 C H3 0.0304 0.4108 -0.0943 0.072 Uiso calc R 1 H C4 0.15864(19) 0.5290(3) -0.03497(15) 0.0656(6) Uani d . 1 C H4 0.1457 0.6349 -0.0626 0.079 Uiso calc R 1 H C5 0.24722(18) 0.5075(3) 0.02373(15) 0.0634(5) Uani d . 1 C H5 0.2936 0.5990 0.0357 0.076 Uiso calc R 1 H C6 0.26790(14) 0.3511(3) 0.06516(12) 0.0527(4) Uani d . 1 C H6 0.3289 0.3349 0.1035 0.063 Uiso calc R 1 H C7 0.16892(14) 0.0505(2) 0.21300(13) 0.0491(4) Uani d . 1 C H7A 0.0972 0.0966 0.2071 0.059 Uiso calc R 1 H H7B 0.1663 -0.0600 0.2429 0.059 Uiso calc R 1 H C8 0.23837(12) 0.1683(2) 0.26970(10) 0.0374(3) Uani d . 1 C C9 0.37456(12) 0.2425(2) 0.35730(10) 0.0377(3) Uani d . 1 C C10 0.22990(12) 0.3413(2) 0.28604(10) 0.0386(3) Uani d . 1 C C11 0.47418(15) 0.2306(2) 0.41651(12) 0.0519(4) Uani d . 1 C H11A 0.5009 0.1152 0.4158 0.078 Uiso calc R 1 H H11B 0.4601 0.2613 0.4769 0.078 Uiso calc R 1 H H11C 0.5262 0.3077 0.3952 0.078 Uiso calc R 1 H C12 0.35328(16) 0.5592(2) 0.37392(12) 0.0510(4) Uani d . 1 C H12A 0.3999 0.5475 0.4285 0.061 Uiso calc R 1 H H12B 0.2922 0.6273 0.3879 0.061 Uiso calc R 1 H C13 0.41195(17) 0.6501(2) 0.30297(14) 0.0555(5) Uani d . 1 C H13A 0.4684 0.5766 0.2843 0.067 Uiso calc R 1 H H13B 0.3632 0.6729 0.2507 0.067 Uiso calc R 1 H 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 S1 0.0532(3) 0.0423(3) 0.0657(3) 0.01013(18) -0.0171(2) -0.01797(19) O1 0.1042(13) 0.0465(8) 0.1007(12) -0.0015(8) -0.0432(10) -0.0254(8) O2 0.0625(9) 0.0831(11) 0.0809(10) 0.0370(8) -0.0100(7) -0.0232(8) O3 0.1008(14) 0.0509(10) 0.164(2) 0.0333(9) -0.0323(13) -0.0187(11) O4 0.0509(8) 0.0752(10) 0.0934(11) 0.0187(7) -0.0154(7) 0.0023(8) O5 0.0624(9) 0.0306(6) 0.1301(14) -0.0031(6) -0.0278(9) 0.0022(7) N1 0.0364(7) 0.0323(6) 0.0470(7) -0.0025(5) -0.0023(5) 0.0057(5) N2 0.0457(7) 0.0336(7) 0.0384(6) -0.0020(5) 0.0035(5) -0.0010(5) N3 0.0510(9) 0.0498(9) 0.0612(9) 0.0154(7) 0.0040(7) 0.0040(7) C1 0.0408(9) 0.0523(10) 0.0450(8) 0.0059(7) 0.0017(7) -0.0127(7) C2 0.0446(9) 0.0609(11) 0.0495(9) 0.0043(8) -0.0036(7) -0.0098(8) C3 0.0574(11) 0.0756(14) 0.0474(10) 0.0159(10) 0.0036(8) 0.0003(9) C4 0.0770(15) 0.0629(13) 0.0592(11) 0.0081(11) 0.0192(10) 0.0068(9) C5 0.0643(13) 0.0629(12) 0.0648(12) -0.0115(10) 0.0172(10) -0.0032(10) C6 0.0430(9) 0.0652(12) 0.0504(9) -0.0016(8) 0.0061(7) -0.0118(8) C7 0.0393(9) 0.0403(9) 0.0656(11) -0.0074(7) -0.0087(7) 0.0054(8) C8 0.0340(7) 0.0356(8) 0.0424(8) -0.0026(6) 0.0016(6) 0.0061(6) C9 0.0383(8) 0.0350(7) 0.0395(7) -0.0043(6) 0.0015(6) 0.0049(6) C10 0.0386(8) 0.0376(8) 0.0398(7) 0.0042(6) 0.0042(6) 0.0033(6) C11 0.0452(9) 0.0515(10) 0.0567(10) -0.0084(8) -0.0106(8) 0.0038(8) C12 0.0676(12) 0.0363(8) 0.0486(9) -0.0016(8) 0.0010(8) -0.0105(7) C13 0.0646(12) 0.0317(8) 0.0695(12) -0.0049(8) 0.0005(9) 0.0020(8) 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' 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 O1 S1 O2 118.94(10) y O1 S1 C1 108.70(9) ? O2 S1 C1 108.49(10) ? O1 S1 C7 106.50(11) ? O2 S1 C7 107.86(9) ? C1 S1 C7 105.56(8) y C13 O5 H5B 109.5 ? C9 N1 C8 106.62(13) y C9 N2 C10 105.50(12) y C9 N2 C12 124.03(14) ? C10 N2 C12 130.06(14) ? O3 N3 O4 122.80(17) ? O3 N3 C10 119.58(17) ? O4 N3 C10 117.62(16) ? C2 C1 C6 121.13(18) ? C2 C1 S1 118.62(15) ? C6 C1 S1 120.25(14) ? C3 C2 C1 119.04(19) ? C3 C2 H2 120.5 ? C1 C2 H2 120.5 ? C4 C3 C2 120.29(19) ? C4 C3 H3 119.9 ? C2 C3 H3 119.9 ? C3 C4 C5 120.6(2) ? C3 C4 H4 119.7 ? C5 C4 H4 119.7 ? C4 C5 C6 120.5(2) ? C4 C5 H5 119.7 ? C6 C5 H5 119.7 ? C5 C6 C1 118.38(18) ? C5 C6 H6 120.8 ? C1 C6 H6 120.8 ? C8 C7 S1 112.71(12) y C8 C7 H7A 109.0 ? S1 C7 H7A 109.0 ? C8 C7 H7B 109.0 ? S1 C7 H7B 109.0 ? H7A C7 H7B 107.8 ? N1 C8 C10 108.71(13) y N1 C8 C7 120.29(14) ? C10 C8 C7 130.98(15) ? N1 C9 N2 111.85(13) y N1 C9 C11 123.64(15) ? N2 C9 C11 124.48(15) ? C8 C10 N2 107.30(13) y C8 C10 N3 128.49(15) ? N2 C10 N3 123.98(15) ? C9 C11 H11A 109.5 ? C9 C11 H11B 109.5 ? H11A C11 H11B 109.5 ? C9 C11 H11C 109.5 ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? N2 C12 C13 110.99(14) y N2 C12 H12A 109.4 ? C13 C12 H12A 109.4 ? N2 C12 H12B 109.4 ? C13 C12 H12B 109.4 ? H12A C12 H12B 108.0 ? O5 C13 C12 110.91(17) y O5 C13 H13A 109.5 ? C12 C13 H13A 109.5 ? O5 C13 H13B 109.5 ? C12 C13 H13B 109.5 ? H13A C13 H13B 108.0 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 O1 1.4300(15) y S1 O2 1.4314(15) y S1 C1 1.7537(19) y S1 C7 1.791(2) y O3 N3 1.215(2) ? O4 N3 1.222(2) ? O5 C13 1.408(2) y O5 H5B 0.8200 ? N1 C9 1.328(2) y N1 C8 1.3562(19) y N2 C9 1.353(2) y N2 C10 1.382(2) y N2 C12 1.472(2) y N3 C10 1.415(2) ? C1 C2 1.384(2) ? C1 C6 1.394(3) ? C2 C3 1.377(3) ? C2 H2 0.9300 ? C3 C4 1.373(3) ? C3 H3 0.9300 ? C4 C5 1.374(3) ? C4 H4 0.9300 ? C5 C6 1.381(3) ? C5 H5 0.9300 ? C6 H6 0.9300 ? C7 C8 1.486(2) ? C7 H7A 0.9700 ? C7 H7B 0.9700 ? C8 C10 1.374(2) y C9 C11 1.480(2) ? C11 H11A 0.9600 ? C11 H11B 0.9600 ? C11 H11C 0.9600 ? C12 C13 1.511(3) y C12 H12A 0.9700 ? C12 H12B 0.9700 ? C13 H13A 0.9700 ? C13 H13B 0.9700 ? 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 O5 H5B N1 1_565 0.82 2.07 2.8562(19) 162