#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/69/2006999.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_2006999 loop_ _publ_author_name 'Gould, Robert O.' 'Harris, Steven G.' 'McNab, Hamish' 'Parsons, Simon' 'Withell, Kirsti' _publ_section_title ; Two Methylsulfanylmethylene Derivatives of Meldrum's Acid ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 234 _journal_page_last 236 _journal_paper_doi 10.1107/S0108270197014170 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety ' C18 H22 O4 S1' _chemical_formula_sum 'C18 H22 O4 S' _chemical_formula_weight 334.43 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method CRYSTALS _cell_angle_alpha 93.469(8) _cell_angle_beta 113.697(5) _cell_angle_gamma 97.890(8) _cell_formula_units_Z 2 _cell_length_a 9.4818(9) _cell_length_b 9.7365(4) _cell_length_c 10.6089(10) _cell_measurement_reflns_used 60 _cell_measurement_temperature 220.0(2) _cell_measurement_theta_max 22 _cell_measurement_theta_min 20 _cell_volume 881.08(13) _computing_cell_refinement DIF4 _computing_data_collection 'DIF4 (Stoe & Cie, 1990a)' _computing_data_reduction 'REDU4 (Stoe & Cie, 1990b)' _computing_molecular_graphics SHELXTL _computing_structure_refinement 'CRYSTALS (Watkin, Prout, Carruthers & Betteridge, 1996)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 220.0(2) _diffrn_measurement_device ; Stoe Stadi-4 diffractometer equipped with an Oxford Cryosystems low temperature device (Cosier & Glazer, 1986) ; _diffrn_measurement_method '\w-\q scans with on-line profile fitting (Clegg, 1981)' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.014 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 7548 _diffrn_reflns_theta_max 70.17 _diffrn_reflns_theta_min 4.59 _diffrn_standards_decay_% 1.0 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.73 _exptl_absorpt_correction_T_max 0.673 _exptl_absorpt_correction_T_min 0.405 _exptl_absorpt_correction_type '\y scans (North, Phillips & Mathews, 1968)' _exptl_crystal_colour ' orange ' _exptl_crystal_density_diffrn 1.26 _exptl_crystal_density_meas ? _exptl_crystal_description ' block ' _exptl_crystal_F_000 357.59 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.23 _refine_diff_density_max 0.23 _refine_diff_density_min -0.22 _refine_ls_extinction_coef 50.0(31) _refine_ls_extinction_method 'Larson (1970)' _refine_ls_goodness_of_fit_obs 1.1073 _refine_ls_hydrogen_treatment 'H atoms placed geometrically after each cycle' _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 2785 _refine_ls_R_factor_obs .0338 _refine_ls_shift/esd_max 0.004708 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme ; Weighting: Chebychev polynomial (Carruthers & Watkin, 1979) ; _refine_ls_wR_factor_obs .0402 _reflns_number_observed 2785 _reflns_number_total 3123 _reflns_observed_criterion >2\s(I) _cod_data_source_file cf1192.cif _cod_data_source_block 2 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 881.08(16) _cod_original_formula_sum ' C18 H22 O4 S1' _cod_database_code 2006999 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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 .0426(2) .0292(2) .0412(2) .01410(10) .0128(2) .00170(10) O1 .0422(6) .0307(5) .0586(7) .0082(4) .0088(5) -.0117(5) C2 .0420(8) .0333(7) .0454(8) .0099(6) .0115(7) -.0080(6) O3 .0398(6) .0366(5) .0447(6) .0093(4) .0170(5) -.0053(4) O4 .0545(6) .0430(6) .0370(5) .0151(5) .0190(5) -.0042(4) C4 .0422(8) .0296(6) .0376(7) .0088(5) .0181(6) .0031(5) C5 .0429(8) .0271(6) .0330(7) .0100(5) .0145(6) .0000(5) O6 .0540(7) .0313(5) .0675(8) .0141(5) .0156(6) -.0099(5) C6 .0425(8) .0292(7) .0447(8) .0075(6) .0151(7) -.0027(6) C7 .0431(8) .0283(6) .0285(6) .0128(5) .0141(6) .0048(5) C8 .0377(7) .0292(6) .0302(6) .0093(5) .0131(6) .0017(5) C9 .0409(8) .0332(6) .0278(6) .0114(5) .0127(6) .0043(5) C10 .0411(8) .0301(6) .0350(7) .0091(5) .0179(6) .0067(5) C11 .0358(7) .0304(6) .0346(7) .0040(5) .0170(6) .0011(5) C12 .0447(8) .0360(7) .0283(6) .0055(6) .0108(6) .0034(5) C13 .0448(8) .0307(6) .0325(7) .0081(6) .0117(6) .0056(5) C14 .0436(9) .0426(8) .0610(10) .0146(7) .0169(8) .0004(7) C21 .0530(10) .0543(9) .0438(8) .0189(7) .0162(7) .0020(7) C22 .0414(9) .0456(9) .0690(10) .0089(7) .0092(8) -.0123(8) C111 .0468(9) .0316(7) .0384(7) -.0017(6) .0182(7) -.0016(6) C112 .0810(10) .0331(7) .0560(10) -.0068(8) .0315(9) .0017(7) C113 .0470(10) .0560(10) .0660(10) -.0073(8) .0145(9) -.0135(9) C114 .0700(10) .0359(8) .0540(9) .0017(7) .0357(9) -.0049(7) 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_occupancy S1 .96104(4) .32678(3) .89270(4) .0385 Uani 1.0000 O1 1.46650(10) .36920(10) 1.12180(10) .0484 Uani 1.0000 C2 1.5249(2) .23900(10) 1.1328(2) .0427 Uani 1.0000 O3 1.48440(10) .17190(10) .99550(10) .0408 Uani 1.0000 O4 1.29710(10) .08210(10) .79310(10) .0446 Uani 1.0000 C4 1.3344(2) .15570(10) .90040(10) .0358 Uani 1.0000 C5 1.2339(2) .24090(10) .93570(10) .0346 Uani 1.0000 O6 1.25750(10) .46760(10) 1.04570(10) .0541 Uani 1.0000 C6 1.3148(2) .36670(10) 1.0362(2) .0400 Uani 1.0000 C7 1.0742(2) .20970(10) .86980(10) .0328 Uani 1.0000 C8 .9929(2) .07340(10) .78200(10) .0325 Uani 1.0000 C9 1.0087(2) -.05010(10) .84100(10) .0340 Uani 1.0000 C10 .9350(2) -.17860(10) .76110(10) .0343 Uani 1.0000 C11 .8477(2) -.18790(10) .61870(10) .0331 Uani 1.0000 C12 .8326(2) -.06300(10) .56030(10) .0380 Uani 1.0000 C13 .9014(2) .06550(10) .64050(10) .0372 Uani 1.0000 C14 .7643(2) .2295(2) .8207(2) .0503 Uani 1.0000 C21 1.4592(2) .1461(2) 1.2119(2) .0507 Uani 1.0000 C22 1.7002(2) .2768(2) 1.1984(2) .0574 Uani 1.0000 C111 .7734(2) -.32810(10) .5257(2) .0399 Uani 1.0000 C112 .7904(2) -.4523(2) .6093(2) .0575 Uani 1.0000 C113 .6005(2) -.3296(2) .4370(2) .0617 Uani 1.0000 C114 .8563(2) -.3448(2) .4294(2) .0513 Uani 1.0000 H91 1.0741 -.0466 .9427 .0401 Uiso 1.0000 H101 .9450 -.2658 .8065 .0422 Uiso 1.0000 H121 .7703 -.0665 .4579 .0428 Uiso 1.0000 H131 .8853 .1533 .5965 .0425 Uiso 1.0000 H211 1.5013 .0568 1.2183 .0599 Uiso 1.0000 H212 1.4907 .1946 1.3076 .0599 Uiso 1.0000 H213 1.3427 .1254 1.1627 .0599 Uiso 1.0000 H221 1.7462 .1893 1.2083 .0610 Uiso 1.0000 H222 1.7353 .3310 1.2920 .0610 Uiso 1.0000 H223 1.7357 .3346 1.1385 .0610 Uiso 1.0000 H1121 .7406 -.5411 .5446 .0633 Uiso 1.0000 H1122 .9041 -.4536 .6643 .0633 Uiso 1.0000 H1123 .7381 -.4429 .6737 .0633 Uiso 1.0000 H1131 .5530 -.4210 .3764 .0666 Uiso 1.0000 H1132 .5455 -.3157 .4985 .0666 Uiso 1.0000 H1133 .5899 -.2520 .3775 .0666 Uiso 1.0000 H1141 .8093 -.4358 .3677 .0616 Uiso 1.0000 H1142 .9701 -.3431 .4864 .0616 Uiso 1.0000 H1143 .8436 -.2663 .3714 .0616 Uiso 1.0000 H141 .6917 .2908 .8302 .0577 Uiso 1.0000 H142 .7597 .1469 .8715 .0577 Uiso 1.0000 H143 .7316 .1966 .7202 .0577 Uiso 1.0000 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C ' 0.0170 0.0090 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0470 0.0320 International_Tables_Vol_IV_Table_2.2B 'S ' 0.3190 0.5570 International_Tables_Vol_IV_Table_2.2B 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 C7 S1 C14 104.94(7) yes C2 O1 C6 118.00(10) no O1 C2 O3 108.70(10) no O1 C2 C21 110.80(10) no O3 C2 C21 111.10(10) no O1 C2 C22 106.50(10) no O3 C2 C22 105.70(10) no C21 C2 C22 113.80(10) no C2 O3 C4 119.00(10) no O3 C4 O4 118.30(10) no O3 C4 C5 115.60(10) no O4 C4 C5 125.90(10) no C4 C5 C6 116.40(10) yes C4 C5 C7 121.60(10) yes C6 C5 C7 121.80(10) yes O1 C6 C5 116.70(10) no O1 C6 O6 118.30(10) no C5 C6 O6 125.00(10) no S1 C7 C5 120.30(10) yes S1 C7 C8 118.40(10) yes C5 C7 C8 121.30(10) yes C7 C8 C9 119.90(10) no C7 C8 C13 121.70(10) no C9 C8 C13 118.30(10) no C8 C9 C10 121.00(10) no C8 C9 H91 119.50(10) no C10 C9 H91 119.40(10) no C9 C10 C11 121.10(10) no C9 C10 H101 119.50(10) no C11 C10 H101 119.40(10) no C10 C11 C12 117.50(10) no C10 C11 C111 122.60(10) no C12 C11 C111 119.90(10) no C11 C12 C13 121.50(10) no C11 C12 H121 119.20(10) no C13 C12 H121 119.20(10) no C8 C13 C12 120.50(10) no C8 C13 H131 119.70(10) no C12 C13 H131 119.80(10) no S1 C14 H141 109.50(10) no S1 C14 H142 109.60(10) no H141 C14 H142 109.4(2) no S1 C14 H143 109.60(10) no H141 C14 H143 109.3(2) no H142 C14 H143 109.50(10) no C2 C21 H211 109.40(10) no C2 C21 H212 109.4(2) no H211 C21 H212 109.3(2) no C2 C21 H213 109.50(10) no H211 C21 H213 109.6(2) no H212 C21 H213 109.6(2) no C2 C22 H221 109.40(10) no C2 C22 H222 109.4(2) no H221 C22 H222 109.4(2) no C2 C22 H223 109.5(2) no H221 C22 H223 109.5(2) no H222 C22 H223 109.6(2) no C11 C111 C112 112.30(10) no C11 C111 C113 110.00(10) no C112 C111 C113 109.40(10) no C11 C111 C114 108.30(10) no C112 C111 C114 108.10(10) no C113 C111 C114 108.60(10) no C111 C112 H1121 109.5(2) no C111 C112 H1122 109.30(10) no H1121 C112 H1122 109.4(2) no C111 C112 H1123 109.5(2) no H1121 C112 H1123 109.6(2) no H1122 C112 H1123 109.5(2) no C111 C113 H1131 109.6(2) no C111 C113 H1132 109.5(2) no H1131 C113 H1132 109.7(2) no C111 C113 H1133 109.3(2) no H1131 C113 H1133 109.4(2) no H1132 C113 H1133 109.3(2) no C111 C114 H1141 109.40(10) no C111 C114 H1142 109.40(10) no H1141 C114 H1142 109.6(2) no C111 C114 H1143 109.40(10) no H1141 C114 H1143 109.5(2) no H1142 C114 H1143 109.5(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C7 . . 1.7380(10) yes S1 C14 . . 1.801(2) yes O1 C2 . . 1.444(2) yes O1 C6 . . 1.353(2) yes C2 O3 . . 1.436(2) yes C2 C21 . . 1.505(2) no C2 C22 . . 1.502(2) no O3 C4 . . 1.353(2) yes O4 C4 . . 1.200(2) yes C4 C5 . . 1.485(2) yes C5 C6 . . 1.467(2) yes C5 C7 . . 1.368(2) yes O6 C6 . . 1.204(2) yes C7 C8 . . 1.488(2) yes C8 C9 . . 1.388(2) no C8 C13 . . 1.390(2) no C9 C10 . . 1.388(2) no C9 H91 . . 1.0010(10) no C10 C11 . . 1.390(2) no C10 H101 . . .9990(10) no C11 C12 . . 1.397(2) no C11 C111 . . 1.532(2) no C12 C13 . . 1.384(2) no C12 H121 . . 1.0020(10) no C13 H131 . . .9990(10) no C14 H141 . . 1.002(2) no C14 H142 . . 1.000(2) no C14 H143 . . 1.000(2) no C21 H211 . . 1.001(2) no C21 H212 . . 1.001(2) no C21 H213 . . .998(2) no C22 H221 . . 1.001(2) no C22 H222 . . 1.000(2) no C22 H223 . . .999(2) no C111 C112 . . 1.531(2) no C111 C113 . . 1.525(3) no C111 C114 . . 1.533(2) no C112 H1121 . . 1.000(2) no C112 H1122 . . 1.001(2) no C112 H1123 . . .998(2) no C113 H1131 . . .998(2) no C113 H1132 . . .999(2) no C113 H1133 . . 1.003(2) no C114 H1141 . . .999(2) no C114 H1142 . . 1.000(2) no C114 H1143 . . 1.000(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 10596858 2 PubChem 14591613