#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/29/2012961.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_2012961 loop_ _publ_author_name 'Fujihara, Takashi' 'Ohba, Takeshi' 'Nagasawa, Akira' 'Nakayama, Juzo' 'Yoza, Kenji' _publ_section_title ; The stable inner salt 2,2-dimorpholino-2-ethylium-1-dithioate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o558 _journal_page_last o559 _journal_paper_doi 10.1107/S0108270102013756 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C10 H16 N2 O2 S2' _chemical_formula_moiety 'C10 H16 N2 O2 S2' _chemical_formula_sum 'C10 H16 N2 O2 S2' _chemical_formula_weight 260.37 _chemical_name_systematic ; 2,2-Dimorphorino-2-ethylium-1-dithioate ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 14.9910(10) _cell_length_b 10.6330(10) _cell_length_c 15.0640(10) _cell_measurement_reflns_used 4110 _cell_measurement_temperature 100 _cell_measurement_theta_max 30.956 _cell_measurement_theta_min 2.704 _cell_volume 2401.2(3) _computing_cell_refinement 'SMART (Bruker, 1995)' _computing_data_collection 'SMART (Bruker, 1995)' _computing_data_reduction 'SHELXTL (Sheldrick, 2001)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 83.66 _diffrn_measured_fraction_theta_full 0.954 _diffrn_measured_fraction_theta_max 0.954 _diffrn_measurement_device_type 'Bruker CCD area-detector' _diffrn_measurement_method '\h and \w' _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 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 18623 _diffrn_reflns_theta_full 30.96 _diffrn_reflns_theta_max 30.96 _diffrn_reflns_theta_min 2.70 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 740 _diffrn_standards_number 119 _exptl_absorpt_coefficient_mu 0.431 _exptl_absorpt_correction_T_max 0.9421 _exptl_absorpt_correction_T_min 0.8816 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.367 _refine_diff_density_min -0.276 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3638 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.092 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0453 _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^)+(0.0372P)^2^+1.4616P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0972 _refine_ls_wR_factor_ref 0.1032 _reflns_number_gt 3021 _reflns_number_total 3638 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ta1383.cif _cod_data_source_block I _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. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 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. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012961 _cod_database_fobs_code 2012961 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.28498(11) 0.25376(18) 0.60986(12) 0.0159(3) Uani d . 1 . . C C2 0.34088(12) 0.37232(18) 0.61439(12) 0.0184(3) Uani d . 1 . . C C3 0.27008(12) 0.43506(18) 0.74512(12) 0.0182(3) Uani d . 1 . . C C4 0.21124(11) 0.31897(18) 0.74779(11) 0.0155(3) Uani d . 1 . . C C5 0.03496(11) 0.18953(17) 0.74419(11) 0.0150(3) Uani d . 1 . . C C6 -0.02966(11) 0.07980(17) 0.73417(12) 0.0173(3) Uani d . 1 . . C C7 -0.10195(12) 0.17133(18) 0.61357(12) 0.0180(3) Uani d . 1 . . C C8 -0.04234(11) 0.28616(17) 0.61723(11) 0.0152(3) Uani d . 1 . . C C9 0.12116(10) 0.26882(15) 0.61460(11) 0.0123(3) Uani d . 1 . . C C10 0.11938(11) 0.28218(17) 0.51480(11) 0.0143(3) Uani d . 1 . . C H1 0.2742(14) 0.227(2) 0.5522(14) 0.021(5) Uiso d . 1 . . H H2 0.3135(14) 0.185(2) 0.6370(14) 0.020(5) Uiso d . 1 . . H H3 0.3134(13) 0.436(2) 0.5805(14) 0.014(5) Uiso d . 1 . . H H4 0.4001(15) 0.355(2) 0.5881(15) 0.026(6) Uiso d . 1 . . H H5 0.2389(14) 0.502(2) 0.7132(13) 0.019(5) Uiso d . 1 . . H H6 0.2835(15) 0.462(2) 0.8058(15) 0.025(6) Uiso d . 1 . . H H7 0.1528(14) 0.344(2) 0.7705(13) 0.016(5) Uiso d . 1 . . H H8 0.2365(14) 0.259(2) 0.7810(14) 0.020(5) Uiso d . 1 . . H H9 0.0137(13) 0.2501(19) 0.7867(13) 0.013(5) Uiso d . 1 . . H H10 0.0908(14) 0.1548(19) 0.7617(13) 0.012(5) Uiso d . 1 . . H H11 -0.0422(14) 0.041(2) 0.7942(15) 0.024(6) Uiso d . 1 . . H H12 -0.0059(14) 0.020(2) 0.6965(13) 0.017(5) Uiso d . 1 . . H H13 -0.1599(16) 0.196(2) 0.5918(15) 0.030(6) Uiso d . 1 . . H H14 -0.0772(13) 0.112(2) 0.5741(14) 0.016(5) Uiso d . 1 . . H H15 -0.0677(13) 0.3493(19) 0.6544(13) 0.010(5) Uiso d . 1 . . H H16 -0.0333(14) 0.322(2) 0.5580(14) 0.019(5) Uiso d . 1 . . H N1 0.19925(9) 0.27269(14) 0.65624(9) 0.0133(3) Uani d . 1 . . N N2 0.04439(9) 0.25281(14) 0.65719(9) 0.0127(3) Uani d . 1 . . N O1 0.35417(8) 0.41056(13) 0.70414(8) 0.0192(3) Uani d . 1 . . O O2 -0.11381(8) 0.11813(12) 0.69987(8) 0.0173(3) Uani d . 1 . . O S1 0.10528(3) 0.14676(4) 0.46107(3) 0.02035(12) Uani d . 1 . . S S2 0.13231(3) 0.42912(5) 0.47783(3) 0.02289(12) Uani d . 1 . . S 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 C1 0.0123(7) 0.0191(9) 0.0164(8) 0.0007(6) 0.0033(6) 0.0008(6) C2 0.0152(8) 0.0235(9) 0.0166(8) -0.0028(7) 0.0024(6) 0.0047(7) C3 0.0155(8) 0.0188(9) 0.0202(8) -0.0013(7) -0.0003(6) -0.0027(7) C4 0.0147(8) 0.0216(9) 0.0102(7) -0.0008(7) -0.0015(6) -0.0016(6) C5 0.0150(8) 0.0186(8) 0.0113(7) 0.0001(6) 0.0000(6) 0.0036(6) C6 0.0139(8) 0.0163(8) 0.0218(8) 0.0003(6) 0.0004(6) 0.0033(7) C7 0.0145(8) 0.0241(9) 0.0154(8) -0.0008(7) -0.0018(6) -0.0002(7) C8 0.0123(7) 0.0180(8) 0.0154(8) 0.0034(6) -0.0013(6) 0.0012(6) C9 0.0137(7) 0.0103(7) 0.0128(7) 0.0011(6) 0.0007(6) 0.0005(6) C10 0.0141(7) 0.0175(8) 0.0112(7) 0.0010(6) 0.0009(6) 0.0028(6) N1 0.0122(6) 0.0161(7) 0.0115(6) -0.0010(5) 0.0018(5) -0.0008(5) N2 0.0126(6) 0.0154(7) 0.0103(6) 0.0001(5) 0.0001(5) 0.0016(5) O1 0.0129(6) 0.0242(7) 0.0204(6) -0.0032(5) 0.0000(5) -0.0005(5) O2 0.0120(5) 0.0211(6) 0.0188(6) -0.0012(5) 0.0014(5) 0.0019(5) S1 0.0297(2) 0.0196(2) 0.01174(19) 0.00058(18) -0.00091(16) -0.00211(15) S2 0.0296(2) 0.0186(2) 0.0205(2) -0.00104(18) 0.00022(18) 0.00820(17) 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 N1 C1 C2 110.28(15) no N1 C1 H1 109.5(13) no C2 C1 H1 113.2(14) no N1 C1 H2 107.2(13) no C2 C1 H2 112.1(13) no H1 C1 H2 104.2(19) no O1 C2 C1 110.93(14) no O1 C2 H3 111.8(13) no C1 C2 H3 109.3(13) no O1 C2 H4 107.9(14) no C1 C2 H4 108.6(14) no H3 C2 H4 108.2(18) no O1 C3 C4 112.10(15) no O1 C3 H5 110.0(12) no C4 C3 H5 109.0(13) no O1 C3 H6 106.0(13) no C4 C3 H6 109.5(14) no H5 C3 H6 110.2(18) no N1 C4 C3 108.50(14) no N1 C4 H7 107.9(12) no C3 C4 H7 108.2(12) no N1 C4 H8 109.8(14) no C3 C4 H8 110.3(14) no H7 C4 H8 112.1(18) no N2 C5 C6 108.73(14) no N2 C5 H9 108.4(12) no C6 C5 H9 111.6(12) no N2 C5 H10 109.7(12) no C6 C5 H10 106.8(12) no H9 C5 H10 111.5(17) no O2 C6 C5 112.35(14) no O2 C6 H11 106.0(12) no C5 C6 H11 109.8(13) no O2 C6 H12 108.4(13) no C5 C6 H12 110.0(13) no H11 C6 H12 110.2(18) no O2 C7 C8 111.07(14) no O2 C7 H13 107.7(14) no C8 C7 H13 109.1(15) no O2 C7 H14 110.9(13) no C8 C7 H14 109.3(13) no H13 C7 H14 108.6(19) no N2 C8 C7 109.93(14) no N2 C8 H15 106.3(12) no C7 C8 H15 110.8(12) no N2 C8 H16 110.1(12) no C7 C8 H16 111.2(13) no H15 C8 H16 108.4(17) no N2 C9 N1 122.62(14) yes N2 C9 C10 118.53(14) yes N1 C9 C10 118.85(14) yes C9 C10 S1 113.87(12) yes C9 C10 S2 114.71(12) yes S1 C10 S2 131.42(10) yes C9 N1 C4 123.99(14) no C9 N1 C1 122.63(13) no C4 N1 C1 112.44(13) yes C9 N2 C8 122.36(14) yes C9 N2 C5 124.66(14) no C8 N2 C5 112.72(13) no C2 O1 C3 109.80(13) no C6 O2 C7 109.49(13) 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 C1 N1 . 1.476(2) yes C1 C2 . 1.515(3) no C1 H1 . 0.93(2) no C1 H2 . 0.94(2) no C2 O1 . 1.426(2) no C2 H3 . 0.94(2) no C2 H4 . 0.99(2) no C3 O1 . 1.428(2) no C3 C4 . 1.518(3) no C3 H5 . 0.98(2) no C3 H6 . 0.98(2) no C4 N1 . 1.475(2) yes C4 H7 . 0.98(2) no C4 H8 . 0.89(2) no C5 N2 . 1.480(2) yes C5 C6 . 1.524(2) no C5 H9 . 0.96(2) no C5 H10 . 0.95(2) no C6 O2 . 1.423(2) no C6 H11 . 1.01(2) no C6 H12 . 0.92(2) no C7 O2 . 1.429(2) no C7 C8 . 1.514(3) no C7 H13 . 0.96(2) no C7 H14 . 0.94(2) no C8 N2 . 1.476(2) yes C8 H15 . 0.95(2) no C8 H16 . 0.98(2) no C9 N2 . 1.328(2) yes C9 N1 . 1.329(2) yes C9 C10 . 1.510(2) yes C10 S1 . 1.6653(18) yes C10 S2 . 1.6699(18) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30652350 2 PubChem 15877444