#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/19/2011976.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_2011976 loop_ _publ_author_name 'Cannon, Debbie' 'Low, John N.' 'Cobo, Justo' 'Molina, Sebasti\'an' 'Nogueras, Manuel' 'S\'anchez, Adolfo' 'Glidewell, Christopher' _publ_section_title ;Methyl 7-hydroxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropteridine-6-carboxylate--dimethyl sulfoxide (1/1) forms chains containing O---H···O and C---H···O hydrogen bonds and aromatic \p--\p-stacking interactions ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 608 _journal_page_last 610 _journal_paper_doi 10.1107/S0108270101003250 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C11 H12 N4 O5, C2 H6 O S' _chemical_formula_moiety 'C11 H12 N4 O5, C2 H6 O S' _chemical_formula_sum 'C13 H18 N4 O6 S' _chemical_formula_weight 358.37 _chemical_name_systematic ; Methyl 7-hydroxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropteridine-6-carboxylate-- dimethyl sulfoxide (1/1) ; _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 62.2233(10) _cell_angle_beta 82.4797(10) _cell_angle_gamma 69.1050(14) _cell_formula_units_Z 2 _cell_length_a 8.8926(2) _cell_length_b 10.2539(2) _cell_length_c 10.8500(4) _cell_measurement_reflns_used 3282 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.05 _cell_measurement_theta_min 2.91 _cell_volume 817.03(4) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full .989 _diffrn_measured_fraction_theta_max .989 _diffrn_measurement_device_type KappaCCD _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 MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .037 _diffrn_reflns_av_sigmaI/netI .060 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 7717 _diffrn_reflns_theta_full 27.0 _diffrn_reflns_theta_max 27.0 _diffrn_reflns_theta_min 3.2 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu .236 _exptl_absorpt_correction_T_max .977 _exptl_absorpt_correction_T_min .943 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description lath _exptl_crystal_F_000 376 _exptl_crystal_size_max .25 _exptl_crystal_size_mid .10 _exptl_crystal_size_min .10 _refine_diff_density_max .26 _refine_diff_density_min -.47 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 222 _refine_ls_number_reflns 3528 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.05 _refine_ls_R_factor_all .061 _refine_ls_R_factor_gt .045 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0602P)^2^+0.1126P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .121 _reflns_number_gt 2790 _reflns_number_total 3528 _reflns_threshold_expression >2\s(I) _cod_data_source_file gg1046.cif _cod_data_source_block 1 _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_values 1715 2011-07-08 13:25:40Z adriana 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_database_code 2011976 _cod_database_fobs_code 2011976 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 .20984(17) .78664(15) .49222(15) .0223(3) Uani d . 1 . . N C11 .2364(2) .62775(19) .6044(2) .0315(4) Uani d . 1 . . C C2 .19117(19) .81001(19) .35871(19) .0225(4) Uani d . 1 . . C O2 .19373(15) .70316(14) .33631(14) .0311(3) Uani d . 1 . . O N3 .16521(17) .96046(16) .25231(15) .0228(3) Uani d . 1 . . N C31 .1448(2) .9872(2) .1094(2) .0312(4) Uani d . 1 . . C C4 .1674(2) 1.08632(19) .26898(19) .0230(4) Uani d . 1 . . C C4a .18943(19) 1.05304(18) .41223(18) .0197(4) Uani d . 1 . . C O4 .14977(17) 1.21352(14) .16784(13) .0344(3) Uani d . 1 . . O N5 .18648(16) 1.17123(15) .43783(15) .0216(3) Uani d . 1 . . N C6 .20671(19) 1.13969(18) .56744(18) .0203(4) Uani d . 1 . . C C61 .1968(2) 1.26821(19) .60216(19) .0241(4) Uani d . 1 . . C O61 .47876(16) 1.17528(19) .65920(17) .0440(4) Uani d . 1 . . O C62 .3422(2) 1.23076(19) .68481(19) .0249(4) Uani d . 1 . . C O62 .30103(14) 1.27098(14) .78809(13) .0270(3) Uani d . 1 . . O C63 .4326(3) 1.2460(2) .8712(2) .0394(5) Uani d . 1 . . C C7 .2319(2) .98491(19) .67638(18) .0215(4) Uani d . 1 . . C O7 .25198(16) .95999(14) .80495(13) .0288(3) Uani d . 1 . . O N8 .23388(17) .86859(16) .65320(15) .0220(3) Uani d . 1 . . N C8a .21190(19) .90451(18) .51996(18) .0190(4) Uani d . 1 . . C S1 .25987(6) .54432(5) 1.05050(5) .02738(16) Uani d . 1 . . S C71 .0732(2) .5694(2) 1.1328(2) .0313(4) Uani d . 1 . . C C72 .3856(2) .4063(2) 1.2018(2) .0391(5) Uani d . 1 . . C O1 .29834(17) .69205(14) 1.00686(13) .0348(3) Uani d . 1 . . O H111 .1554 .5883 .5948 .047 Uiso calc R 1 . . H H112 .2274 .6293 .6947 .047 Uiso calc R 1 . . H H113 .3442 .5593 .5987 .047 Uiso calc R 1 . . H H311 .1745 .8864 .1078 .047 Uiso calc R 1 . . H H312 .2142 1.0451 .0482 .047 Uiso calc R 1 . . H H313 .0321 1.0482 .0767 .047 Uiso calc R 1 . . H H611 .1847 1.3658 .5145 .029 Uiso calc R 1 . . H H612 .0997 1.2871 .6561 .029 Uiso calc R 1 . . H H631 .4952 1.1340 .9178 .059 Uiso calc R 1 . . H H632 .3894 1.2830 .9413 .059 Uiso calc R 1 . . H H633 .5023 1.3039 .8107 .059 Uiso calc R 1 . . H H7 .2670 .8445 .8803 .035 Uiso d . 1 . . H H711 -.0141 .6436 1.0621 .047 Uiso calc R 1 . . H H712 .0746 .6102 1.1981 .047 Uiso calc R 1 . . H H713 .0558 .4684 1.1836 .047 Uiso calc R 1 . . H H721 .4984 .3812 1.1759 .059 Uiso calc R 1 . . H H722 .3572 .3108 1.2460 .059 Uiso calc R 1 . . H H723 .3709 .4505 1.2672 .059 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 N1 .0283(8) .0203(7) .0226(8) -.0112(6) .0017(6) -.0111(6) C11 .0483(12) .0204(9) .0274(11) -.0163(8) .0001(9) -.0082(8) C2 .0200(9) .0252(8) .0273(10) -.0091(7) .0015(7) -.0150(8) O2 .0406(8) .0296(7) .0345(8) -.0168(6) .0033(6) -.0204(6) N3 .0257(8) .0239(7) .0220(8) -.0077(6) -.0024(6) -.0127(6) C31 .0385(11) .0335(10) .0263(10) -.0093(9) -.0037(8) -.0180(9) C4 .0244(9) .0217(8) .0243(10) -.0075(7) -.0014(7) -.0110(8) C4a .0203(8) .0197(8) .0211(9) -.0075(7) .0000(7) -.0099(7) O4 .0549(9) .0244(7) .0222(7) -.0137(6) -.0056(6) -.0073(6) N5 .0225(7) .0207(7) .0234(8) -.0085(6) .0012(6) -.0106(6) C6 .0191(8) .0201(8) .0230(9) -.0064(7) .0005(7) -.0107(7) C61 .0281(9) .0212(8) .0258(10) -.0082(7) .0005(7) -.0128(7) O61 .0260(8) .0636(10) .0617(11) -.0150(7) .0093(7) -.0457(9) C62 .0288(10) .0219(8) .0297(10) -.0123(7) .0050(8) -.0145(8) O62 .0300(7) .0289(6) .0283(7) -.0099(5) -.0016(5) -.0172(6) C63 .0417(12) .0438(12) .0398(13) -.0138(10) -.0104(9) -.0218(10) C7 .0224(8) .0237(8) .0219(9) -.0097(7) .0037(7) -.0124(7) O7 .0462(8) .0245(6) .0192(7) -.0150(6) .0012(6) -.0103(5) N8 .0259(8) .0221(7) .0212(8) -.0107(6) .0020(6) -.0106(6) C8a .0174(8) .0212(8) .0228(9) -.0087(7) .0025(6) -.0122(7) S1 .0375(3) .0246(2) .0236(3) -.0140(2) .00578(19) -.0123(2) C71 .0286(10) .0290(9) .0352(11) -.0074(8) .0011(8) -.0153(9) C72 .0287(10) .0299(10) .0411(13) -.0105(8) .0020(9) -.0019(9) O1 .0563(9) .0267(7) .0234(7) -.0239(6) .0003(6) -.0054(6) 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 C2 N1 C8a 122.15(14) no C2 N1 C11 116.88(14) no C8a N1 C11 120.89(15) no N1 C11 H111 109.5 no N1 C11 H112 109.5 no H111 C11 H112 109.5 no N1 C11 H113 109.5 no H111 C11 H113 109.5 no H112 C11 H113 109.5 no O2 C2 N1 121.04(16) no O2 C2 N3 121.89(17) no N1 C2 N3 117.05(14) no C2 N3 C4 125.12(15) no C2 N3 C31 117.68(14) no C4 N3 C31 117.06(14) no N3 C31 H311 109.5 no N3 C31 H312 109.5 no H311 C31 H312 109.5 no N3 C31 H313 109.5 no H311 C31 H313 109.5 no H312 C31 H313 109.5 no O4 C4 N3 120.46(16) no O4 C4 C4a 124.74(16) no N3 C4 C4a 114.79(14) no N5 C4a C8a 120.82(16) no N5 C4a C4 118.42(14) no C8a C4a C4 120.76(15) no C6 N5 C4a 117.84(14) no N5 C6 C7 120.17(15) no N5 C6 C61 119.93(15) no C7 C6 C61 119.85(15) no C62 C61 C6 112.81(14) no C62 C61 H611 109.0 no C6 C61 H611 109.0 no C62 C61 H612 109.0 no C6 C61 H612 109.0 no H611 C61 H612 107.8 no O61 C62 O62 124.12(17) no O61 C62 C61 124.41(17) no O62 C62 C61 111.45(14) no C62 O62 C63 116.13(15) no O62 C63 H631 109.5 no O62 C63 H632 109.5 no H631 C63 H632 109.5 no O62 C63 H633 109.5 no H631 C63 H633 109.5 no H632 C63 H633 109.5 no O7 C7 N8 119.82(15) no O7 C7 C6 117.48(15) no N8 C7 C6 122.70(16) no C7 O7 H7 113.6 no C7 N8 C8a 115.78(15) no N8 C8a N1 117.35(14) no N8 C8a C4a 122.67(15) no N1 C8a C4a 119.97(15) no O1 S1 C72 103.63(9) no O1 S1 C71 106.23(9) no C72 S1 C71 97.93(9) no S1 C71 H711 109.5 no S1 C71 H712 109.5 no H711 C71 H712 109.5 no S1 C71 H713 109.5 no H711 C71 H713 109.5 no H712 C71 H713 109.5 no S1 C72 H721 109.5 no S1 C72 H722 109.5 no H721 C72 H722 109.5 no S1 C72 H723 109.5 no H721 C72 H723 109.5 no H722 C72 H723 109.5 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 . 1.376(2) y C2 N3 . 1.386(2) y N3 C4 . 1.391(2) y C4 C4a . 1.452(2) y N5 C4a . 1.355(2) y N5 C6 . 1.310(2) y C6 C7 . 1.426(2) y C7 N8 . 1.323(2) y N1 C8a . 1.381(2) y N8 C8a . 1.338(2) y C4a C8a . 1.382(2) y C2 O2 . 1.220(2) y C4 O4 . 1.223(2) y C62 O61 . 1.200(2) y C62 O62 . 1.332(2) y C7 O7 . 1.320(2) y N1 C11 . 1.464(2) no C11 H111 . .9800 no C11 H112 . .9800 no C11 H113 . .9800 no N3 C31 . 1.467(2) no C31 H311 . .9800 no C31 H312 . .9800 no C31 H313 . .9800 no C6 C61 . 1.502(2) no C61 C62 . 1.501(2) no C61 H611 . .9900 no C61 H612 . .9900 no O62 C63 . 1.447(2) no C63 H631 . .9800 no C63 H632 . .9800 no C63 H633 . .9800 no O7 H7 . 1.050 no S1 O1 . 1.5148(13) no S1 C72 . 1.770(2) no S1 C71 . 1.7723(19) no C71 H711 . .9800 no C71 H712 . .9800 no C71 H713 . .9800 no C72 H721 . .9800 no C72 H722 . .9800 no C72 H723 . .9800 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 O7 H7 O1 . 1.05 1.48 2.517(2) 168 y C31 H311 O1 1_554 .98 2.56 3.472(3) 156 y C61 H612 O2 2_576 .98 2.57 3.382(2) 140 y C71 H711 O4 2_576 .98 2.44 3.362(2) 157 y C71 H712 O2 1_556 .98 2.60 3.521(2) 157 y 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 C8a N1 C2 O2 178.16(15) no C11 N1 C2 O2 1.4(2) no C8a N1 C2 N3 -3.5(2) no C11 N1 C2 N3 179.70(14) no O2 C2 N3 C4 -177.14(16) no N1 C2 N3 C4 4.5(2) no O2 C2 N3 C31 -1.6(2) no N1 C2 N3 C31 -179.91(15) no C2 N3 C4 O4 176.93(15) no C31 N3 C4 O4 1.4(2) no C2 N3 C4 C4a -3.9(2) no C31 N3 C4 C4a -179.42(14) no O4 C4 C4a N5 1.8(3) no N3 C4 C4a N5 -177.41(14) no O4 C4 C4a C8a -178.62(16) no N3 C4 C4a C8a 2.2(2) no C8a C4a N5 C6 .5(2) no C4 C4a N5 C6 -179.91(14) no C4a N5 C6 C7 .4(2) no C4a N5 C6 C61 -177.14(14) no C6 C61 C62 O61 44.7(2) y C6 C61 C62 O62 -137.11(15) y C7 C6 C61 C62 55.9(2) y N5 C6 C61 C62 -126.59(17) y O61 C62 O62 C63 .7(3) no C61 C62 O62 C63 -177.54(15) no N5 C6 C7 O7 179.82(14) no C61 C6 C7 O7 -2.6(2) no N5 C6 C7 N8 -.9(3) no C61 C6 C7 N8 176.61(15) no O7 C7 N8 C8a 179.73(14) no C6 C7 N8 C8a .5(2) no C7 N8 C8a N1 -178.66(14) no C7 N8 C8a C4a .4(2) no C2 N1 C8a N8 -178.73(14) no C11 N1 C8a N8 -2.1(2) no C2 N1 C8a C4a 2.2(2) no C11 N1 C8a C4a 178.83(15) no N5 C4a C8a N8 -.9(3) no C4 C4a C8a N8 179.47(15) no N5 C4a C8a N1 178.11(14) no C4 C4a C8a N1 -1.5(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21135265 2 PubChem 139058206