#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:53:41 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102155.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_2102155 loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John N' 'Wardell, James L' _publ_section_title ; Conformational preferences and supramolecular aggregation in 2-nitrophenylthiolates: disulfides and thiosulfonates ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 893 _journal_page_last 905 _journal_paper_doi 10.1107/S0108768100007114 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C9 H8 N2 O6 S2' _chemical_formula_weight 304.30 _chemical_name_systematic ; 2,4-Dinitrophenyl-2'-methoxycarbonylmethyl disulfide ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 72.1417(15) _cell_angle_beta 83.3965(14) _cell_angle_gamma 80.332(3) _cell_formula_units_Z 2 _cell_length_a 8.1655(3) _cell_length_b 8.2415(3) _cell_length_c 9.3887(4) _cell_measurement_reflns_used 2629 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 29.31 _cell_measurement_theta_min 2.92 _cell_volume 591.48(4) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa-CCD server software (Nonius, 1997)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1976), PLATON (Spek, 1999)' _computing_publication_material 'SHELXL-97 and WordPerfect macro PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full .962 _diffrn_measured_fraction_theta_max .962 _diffrn_measurement_device_type Kappa-CCD _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .050 _diffrn_reflns_av_sigmaI/netI .0678 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6105 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.92 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu .476 _exptl_absorpt_correction_T_max .9882 _exptl_absorpt_correction_T_min .8512 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sortav (Blessing, 1995 & 1997)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 312 _exptl_crystal_size_max .35 _exptl_crystal_size_mid .05 _exptl_crystal_size_min .03 _refine_diff_density_max .356 _refine_diff_density_min -.376 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2629 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all .0684 _refine_ls_R_factor_gt .0435 _refine_ls_shift/su_max .008 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0536P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1105 _reflns_number_gt 1969 _reflns_number_total 2629 _reflns_threshold_expression >2\s(I) _cod_data_source_file na0107.cif _cod_data_source_block 4 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w=1/[\s^2^(Fo^2^)+(0.0536P)^2^] 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^)+(0.0536P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M P-1 _cod_database_code 2102155 _cod_database_fobs_code 2102155 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 .31637(7) .86272(8) .91373(7) .02245(18) Uani d . 1 S S2 .09158(7) .89766(8) .82419(7) .02167(18) Uani d . 1 S C1 .4109(3) 1.0481(3) .7967(3) .0205(5) Uani d . 1 C C2 .3239(3) 1.2169(3) .8142(3) .0201(5) Uani d . 1 C O3 .2542(2) 1.3296(2) .7165(2) .0309(4) Uani d . 1 O O4 .3370(2) 1.2272(2) .95141(18) .0254(4) Uani d . 1 O C5 .2645(3) 1.3890(3) .9787(3) .0344(6) Uani d . 1 C C21 .1368(3) .8092(3) .6714(3) .0180(5) Uani d . 1 C C22 .0110(2) .7859(3) .5912(3) .0179(5) Uani d . 1 C N22 -.1648(2) .8353(3) .6329(2) .0212(5) Uani d . 1 N O221 -.19512(18) .9202(2) .7223(2) .0281(4) Uani d . 1 O O222 -.27220(19) .7932(2) .5763(2) .0330(5) Uani d . 1 O C23 .0430(3) .7170(3) .4719(3) .0191(5) Uani d . 1 C C24 .2073(3) .6735(3) .4288(3) .0177(5) Uani d . 1 C N24 .2445(2) .6046(3) .3001(2) .0232(5) Uani d . 1 N O241 .1278(2) .5881(3) .2372(2) .0362(5) Uani d . 1 O O242 .39156(19) .5679(2) .2617(2) .0305(4) Uani d . 1 O C25 .3360(3) .6936(3) .5019(3) .0194(5) Uani d . 1 C C26 .3011(3) .7597(3) .6213(3) .0190(5) Uani d . 1 C H1A .5280 1.0337 .8215 .025 Uiso calc R 1 H H1B .4116 1.0512 .6904 .025 Uiso calc R 1 H H5A .2800 1.3831 1.0822 .052 Uiso calc PR .50 H H5B .1453 1.4105 .9628 .052 Uiso calc PR .50 H H5C .3193 1.4827 .9094 .052 Uiso calc PR .50 H H5D .2165 1.4678 .8874 .052 Uiso calc PR .50 H H5E .3511 1.4403 1.0068 .052 Uiso calc PR .50 H H5F .1771 1.3682 1.0602 .052 Uiso calc PR .50 H H23 -.0449 .7005 .4219 .023 Uiso calc R 1 H H25 .4482 .6619 .4698 .023 Uiso calc R 1 H H26 .3906 .7724 .6715 .023 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 .0278(3) .0206(3) .0201(3) -.0042(2) -.0066(2) -.0055(3) S2 .0221(3) .0239(4) .0210(4) -.0034(2) -.0008(2) -.0095(3) C1 .0206(11) .0229(13) .0208(13) -.0038(9) -.0001(9) -.0105(11) C2 .0166(11) .0223(13) .0227(14) -.0054(9) -.0016(9) -.0070(11) O3 .0348(10) .0244(10) .0335(11) -.0015(7) -.0181(8) -.0041(9) O4 .0380(9) .0184(9) .0200(10) .0002(7) -.0022(7) -.0081(8) C5 .0484(16) .0199(14) .0367(17) -.0043(11) .0080(12) -.0149(13) C21 .0211(11) .0148(12) .0177(12) -.0032(8) -.0020(9) -.0034(10) C22 .0160(11) .0156(12) .0200(13) -.0009(8) -.0011(8) -.0029(10) N22 .0175(10) .0220(11) .0215(11) -.0033(7) -.0009(8) -.0025(9) O221 .0236(9) .0316(11) .0308(11) .0002(7) .0013(7) -.0150(9) O222 .0189(9) .0468(12) .0395(12) -.0058(7) -.0048(7) -.0203(10) C23 .0204(11) .0164(12) .0204(13) -.0037(8) -.0045(9) -.0036(10) C24 .0205(11) .0151(12) .0173(13) -.0028(8) .0000(9) -.0050(10) N24 .0219(11) .0254(12) .0234(12) -.0043(8) -.0007(8) -.0085(9) O241 .0252(9) .0556(14) .0401(12) -.0047(8) -.0068(8) -.0309(10) O242 .0221(9) .0413(12) .0313(11) -.0007(7) .0029(7) -.0192(9) C25 .0193(11) .0155(12) .0209(13) -.0007(8) -.0018(9) -.0026(10) C26 .0198(11) .0184(13) .0189(13) -.0024(8) -.0045(8) -.0046(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 '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 .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .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 C1 S1 S2 102.72(8) no C21 S2 S1 104.16(7) no C2 C1 S1 113.96(15) no O221 N22 O222 123.66(18) no O221 N22 C22 117.16(18) no O222 N22 C22 119.17(19) no O241 N24 O242 124.0(2) no O241 N24 C24 118.23(18) no O242 N24 C24 117.72(18) no C2 C1 H1A 108.8 no S1 C1 H1A 108.8 no C2 C1 H1B 108.8 no S1 C1 H1B 108.8 no H1A C1 H1B 107.7 no O3 C2 O4 124.4(2) no O3 C2 C1 124.5(2) no O4 C2 C1 111.07(19) no C2 O4 C5 115.87(19) no O4 C5 H5A 109.5 no O4 C5 H5B 109.5 no H5A C5 H5B 109.5 no O4 C5 H5C 109.5 no H5A C5 H5C 109.5 no H5B C5 H5C 109.5 no O4 C5 H5D 109.5 no H5A C5 H5D 141.1 no H5B C5 H5D 56.3 no H5C C5 H5D 56.3 no O4 C5 H5E 109.5 no H5A C5 H5E 56.3 no H5B C5 H5E 141.1 no H5C C5 H5E 56.3 no H5D C5 H5E 109.5 no O4 C5 H5F 109.5 no H5A C5 H5F 56.3 no H5B C5 H5F 56.3 no H5C C5 H5F 141.1 no H5D C5 H5F 109.5 no H5E C5 H5F 109.5 no C26 C21 C22 115.6(2) no C26 C21 S2 121.94(17) no C22 C21 S2 122.43(16) no C23 C22 C21 123.56(19) no C23 C22 N22 116.32(19) no C21 C22 N22 120.1(2) no C24 C23 C22 117.2(2) no C24 C23 H23 121.4 no C22 C23 H23 121.4 no C23 C24 C25 122.1(2) no C23 C24 N24 118.29(19) no C25 C24 N24 119.56(18) no C26 C25 C24 119.5(2) no C26 C25 H25 120.2 no C24 C25 H25 120.2 no C25 C26 C21 121.9(2) no C25 C26 H26 119.0 no C21 C26 H26 119.0 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 S2 2.0464(8) no S1 C1 1.819(2) no S2 C21 1.777(2) no N22 O221 1.229(3) no N22 O222 1.222(2) no N24 O241 1.224(3) no N24 O242 1.228(2) no C1 C2 1.499(3) no C1 H1A .9900 no C1 H1B .9900 no C2 O3 1.202(3) no C2 O4 1.335(3) no O4 C5 1.450(3) no C5 H5A .9800 no C5 H5B .9800 no C5 H5C .9800 no C5 H5D .9800 no C5 H5E .9800 no C5 H5F .9800 no C21 C26 1.405(3) no C21 C22 1.411(3) no C22 C23 1.384(3) no C22 N22 1.467(3) no C23 C24 1.377(3) no C23 H23 .9500 no C24 C25 1.377(3) no C24 N24 1.468(3) no C25 C26 1.373(3) no C25 H25 .9500 no C26 H26 .9500 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 _geom_hbond_publ_flag C23 H23 O3 2_576 .95 2.35 3.299(3) 176 yes 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 C1 S1 S2 C21 83.97(11) no S1 S2 C21 C22 171.14(18) no S1 S2 C21 C26 -9.7(2) no C21 C22 N22 O221 11.0(3) no C21 C22 N22 O222 -170.2(2) no C23 C22 N22 O221 -169.1(2) no C23 C22 N22 O222 9.7(3) no C23 C24 N24 O241 -.4(3) no C23 C24 N24 O242 179.3(2) no C25 C24 N24 O241 -180.0(2) no C25 C24 N24 O242 -.3(3) no S2 S1 C1 C2 67.02(17) no S1 C1 C2 O3 -115.4(2) no S1 C1 C2 O4 66.0(2) no O3 C2 O4 C5 -1.7(3) no C1 C2 O4 C5 176.97(19) no C26 C21 C22 C23 .9(3) no S2 C21 C22 C23 -179.88(18) no C26 C21 C22 N22 -179.26(19) no S2 C21 C22 N22 .0(3) no C21 C22 C23 C24 -1.6(3) no N22 C22 C23 C24 178.57(19) no C22 C23 C24 C25 1.3(3) no C22 C23 C24 N24 -178.3(2) no C23 C24 C25 C26 -.3(3) no N24 C24 C25 C26 179.3(2) no C24 C25 C26 C21 -.4(3) no C22 C21 C26 C25 .2(3) no S2 C21 C26 C25 -179.07(18) no