data_2203323
loop_
_publ_author_name
'Daniel E. Lynch'
'Ian McClenaghan'
_publ_section_title
;
4-Hydroxy-6-methyl-2-(sulfonatoethylsulfanyl)pyrimidin-1-ium monohydrate
;
_journal_issue                 3
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o376
_journal_page_last             o377
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C7 H10 N2 O4 S2, H2 O'
_chemical_formula_moiety       'C7 H10 N2 O4 S2, H2 O'
_chemical_formula_sum          'C7 H12 N2 O5 S2'
_chemical_formula_weight       268.31
_chemical_name_common          ?
_chemical_name_systematic
;
4-Hydroxy-6-methyl-2-(sulfonatoethylsulfanyl)pyrimidin-1-ium monohydrate
;
_symmetry_cell_setting         Monoclinic
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_space_group_name_H-M 'P 21/n'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         SHELXL-97
_cell_angle_alpha              90.00
_cell_angle_beta               91.0483(18)
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 6.1137(2)
_cell_length_b                 11.2202(3)
_cell_length_c                 15.9632(6)
_cell_measurement_reflns_used  7654
_cell_measurement_temperature  120(2)
_cell_measurement_theta_max    27.48
_cell_measurement_theta_min    2.91
_cell_volume                   1094.84(6)
_computing_cell_refinement     'DENZO and COLLECT'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO, SCALEPACK (Otwinowski & Minor, 1997) and COLLECT'
_computing_molecular_graphics  'PLATON97 (Spek, 1997)'
_computing_publication_material SHELXL97
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature    120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type 'Bruker--Nonius KappaCCD area-detector'
_diffrn_measurement_method     '\f and \w'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source       'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.0519
_diffrn_reflns_av_sigmaI/netI  0.0334
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_l_max     18
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_number          11989
_diffrn_reflns_theta_full      25.00
_diffrn_reflns_theta_max       24.99
_diffrn_reflns_theta_min       3.13
_diffrn_standards_decay_%      0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.495
_exptl_absorpt_correction_T_max 0.961
_exptl_absorpt_correction_T_min 0.932
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_process_details '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour          colourless
_exptl_crystal_density_diffrn  1.628
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           560
_exptl_crystal_size_max        0.35
_exptl_crystal_size_mid        0.20
_exptl_crystal_size_min        0.08
_refine_diff_density_max       0.215
_refine_diff_density_min       -0.485
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.073
_refine_ls_hydrogen_treatment  mixed
_refine_ls_matrix_type         full
_refine_ls_number_parameters   162
_refine_ls_number_reflns       1920
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.073
_refine_ls_R_factor_all        0.0423
_refine_ls_R_factor_gt         0.0321
_refine_ls_shift/su_max        0.000
_refine_ls_shift/su_mean       0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0425P)^2^+0.5029P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.0771
_refine_ls_wR_factor_ref       0.0819
_reflns_number_gt              1619
_reflns_number_total           1920
_reflns_threshold_expression   I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.5271(3) 0.37582(15) 0.10006(11) 0.0146(4) Uani d . 1 . . N
H1 0.559(4) 0.451(2) 0.1012(16) 0.027(7) Uiso d . 1 . . H
C2 0.3494(3) 0.33538(17) 0.14014(12) 0.0139(4) Uani d . 1 . . C
S21 0.20999(8) 0.44136(4) 0.19888(3) 0.01700(17) Uani d . 1 . . S
C22 -0.0187(3) 0.35287(18) 0.23366(13) 0.0163(5) Uani d . 1 . . C
H221 -0.1402 0.4071 0.2478 0.020 Uiso calc R 1 . . H
H222 -0.0697 0.3018 0.1867 0.020 Uiso calc R 1 . . H
C23 0.0318(3) 0.27423(18) 0.30892(13) 0.0161(4) Uani d . 1 . . C
H231 0.0684 0.3244 0.3582 0.020 Uiso calc R 1 . . H
H232 0.1595 0.2230 0.2972 0.020 Uiso calc R 1 . . H
S24 -0.19989(8) 0.18388(4) 0.33057(3) 0.01565(16) Uani d . 1 . . S
O25 -0.3790(2) 0.26434(13) 0.34850(11) 0.0264(4) Uani d . 1 . . O
O26 -0.1371(2) 0.11032(12) 0.40262(9) 0.0213(4) Uani d . 1 . . O
O27 -0.2422(3) 0.11280(13) 0.25562(10) 0.0247(4) Uani d . 1 . . O
N3 0.2810(3) 0.22453(14) 0.13575(11) 0.0160(4) Uani d . 1 . . N
C4 0.4018(3) 0.14818(18) 0.09037(13) 0.0170(5) Uani d . 1 . . C
O41 0.3365(3) 0.03806(12) 0.08472(10) 0.0231(4) Uani d . 1 . . O
H41 0.183(6) 0.026(3) 0.104(2) 0.069(11) Uiso d . 1 . . H
C5 0.5926(3) 0.18368(18) 0.04977(13) 0.0167(5) Uani d . 1 . . C
H5 0.6789 0.1275 0.0205 0.021 Uiso calc R 1 . . H
C6 0.6509(3) 0.30021(18) 0.05327(13) 0.0155(4) Uani d . 1 . . C
C61 0.8393(3) 0.35392(19) 0.00879(13) 0.0197(5) Uani d . 1 . . C
H611 0.9377 0.2905 -0.0096 0.025 Uiso calc R 1 . . H
H612 0.9189 0.4078 0.0468 0.025 Uiso calc R 1 . . H
H613 0.7852 0.3987 -0.0401 0.025 Uiso calc R 1 . . H
O1W -0.0506(3) 0.00014(15) 0.12299(11) 0.0227(4) Uani d . 1 . . O
H1W -0.105(5) 0.035(3) 0.163(2) 0.048(9) Uiso d . 1 . . H
H2W -0.076(5) -0.076(3) 0.1329(19) 0.046(8) Uiso d . 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 0.0156(9) 0.0125(9) 0.0157(9) -0.0010(7) 0.0015(7) -0.0008(7)
C2 0.0139(10) 0.0142(10) 0.0137(10) 0.0014(8) 0.0000(8) 0.0009(8)
S21 0.0192(3) 0.0107(3) 0.0214(3) -0.00097(19) 0.0074(2) -0.00142(19)
C22 0.0145(11) 0.0140(10) 0.0204(11) 0.0007(8) 0.0047(9) 0.0007(8)
C23 0.0158(11) 0.0137(10) 0.0189(11) -0.0020(8) 0.0022(9) 0.0003(8)
S24 0.0167(3) 0.0108(3) 0.0197(3) 0.00051(18) 0.0053(2) 0.00069(19)
O25 0.0211(8) 0.0151(8) 0.0435(10) 0.0052(6) 0.0145(7) 0.0044(7)
O26 0.0264(9) 0.0152(7) 0.0223(8) 0.0006(6) 0.0050(7) 0.0049(6)
O27 0.0266(9) 0.0226(8) 0.0249(8) -0.0095(6) 0.0043(7) -0.0050(7)
N3 0.0175(9) 0.0123(9) 0.0182(9) -0.0004(7) 0.0032(7) -0.0013(7)
C4 0.0213(11) 0.0135(10) 0.0161(11) 0.0029(8) 0.0003(9) -0.0006(8)
O41 0.0269(9) 0.0124(8) 0.0304(9) -0.0030(6) 0.0083(7) -0.0048(6)
C5 0.0174(11) 0.0160(10) 0.0166(11) 0.0040(8) 0.0033(9) -0.0009(8)
C6 0.0145(10) 0.0194(11) 0.0124(10) 0.0024(8) 0.0000(8) 0.0010(8)
C61 0.0186(11) 0.0217(11) 0.0190(11) -0.0009(8) 0.0036(9) 0.0003(9)
O1W 0.0255(9) 0.0168(9) 0.0258(9) -0.0021(6) 0.0033(7) -0.0015(7)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C6 . . 120.58(17) ?
C2 N1 H1 . . 120.1(17) ?
C6 N1 H1 . . 119.2(17) ?
N3 C2 N1 . . 123.47(18) ?
N3 C2 S21 . . 121.01(15) ?
N1 C2 S21 . . 115.52(14) ?
C2 S21 C22 . . 100.28(9) ?
C23 C22 S21 . . 114.49(15) ?
C23 C22 H221 . . 108.6 ?
S21 C22 H221 . . 108.6 ?
C23 C22 H222 . . 108.6 ?
S21 C22 H222 . . 108.6 ?
H221 C22 H222 . . 107.6 ?
C22 C23 S24 . . 109.48(14) ?
C22 C23 H231 . . 109.8 ?
S24 C23 H231 . . 109.8 ?
C22 C23 H232 . . 109.8 ?
S24 C23 H232 . . 109.8 ?
H231 C23 H232 . . 108.2 ?
O25 S24 O27 . . 112.27(10) ?
O25 S24 O26 . . 112.60(9) ?
O27 S24 O26 . . 112.16(9) ?
O25 S24 C23 . . 106.85(9) ?
O27 S24 C23 . . 106.38(9) ?
O26 S24 C23 . . 106.01(9) ?
C2 N3 C4 . . 116.90(17) ?
O41 C4 N3 . . 118.01(18) ?
O41 C4 C5 . . 119.62(18) ?
N3 C4 C5 . . 122.37(18) ?
C4 O41 H41 . . 114(2) ?
C6 C5 C4 . . 118.35(18) ?
C6 C5 H5 . . 120.8 ?
C4 C5 H5 . . 120.8 ?
C5 C6 N1 . . 118.22(18) ?
C5 C6 C61 . . 125.08(19) ?
N1 C6 C61 . . 116.70(18) ?
C6 C61 H611 . . 109.5 ?
C6 C61 H612 . . 109.5 ?
H611 C61 H612 . . 109.5 ?
C6 C61 H613 . . 109.5 ?
H611 C61 H613 . . 109.5 ?
H612 C61 H613 . . 109.5 ?
H1W O1W H2W . . 104(3) ?
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 . 1.349(3) ?
N1 C6 . 1.368(3) ?
N1 H1 . 0.87(3) ?
C2 N3 . 1.314(3) ?
C2 S21 . 1.746(2) ?
S21 C22 . 1.810(2) ?
C22 C23 . 1.518(3) ?
C22 H221 . 0.99 ?
C22 H222 . 0.99 ?
C23 S24 . 1.7810(19) ?
C23 H231 . 0.99 ?
C23 H232 . 0.99 ?
S24 O25 . 1.4518(15) ?
S24 O27 . 1.4572(16) ?
S24 O26 . 1.4612(15) ?
N3 C4 . 1.350(3) ?
C4 O41 . 1.301(3) ?
C4 C5 . 1.403(3) ?
O41 H41 . 1.00(4) ?
C5 C6 . 1.356(3) ?
C5 H5 . 0.95 ?
C6 C61 . 1.491(3) ?
C61 H611 . 0.98 ?
C61 H612 . 0.98 ?
C61 H613 . 0.98 ?
O1W H1W . 0.83(3) ?
O1W H2W . 0.88(3) ?
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
N1 H1 O26 2 0.87(3) 1.85(3) 2.716(2) 176(2) yes
O41 H41 O1W . 1.00(4) 1.50(4) 2.491(2) 174(3) yes
O1W H1W O27 . 0.83(3) 1.92(4) 2.747(2) 177(3) yes
O1W H2W O25 2_445 0.88(3) 1.84(4) 2.720(2) 178(3) yes
C22 H222 N3 . 0.99 2.46 2.824(3) 101 yes
C23 H232 N3 . 0.99 2.70 3.229(3) 114 yes
C22 H221 O27 2_455 0.99 2.42 3.268(2) 144 yes
C5 H5 O41 3_655 0.95 2.51 3.320(2) 144 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 N3 . . . . -1.7(3) ?
C6 N1 C2 S21 . . . . 178.96(15) ?
N3 C2 S21 C22 . . . . -3.3(2) ?
N1 C2 S21 C22 . . . . 176.12(16) ?
C2 S21 C22 C23 . . . . 81.06(16) ?
S21 C22 C23 S24 . . . . -175.24(10) ?
C22 C23 S24 O25 . . . . -60.42(16) ?
C22 C23 S24 O27 . . . . 59.71(16) ?
C22 C23 S24 O26 . . . . 179.27(13) ?
N1 C2 N3 C4 . . . . 2.1(3) ?
S21 C2 N3 C4 . . . . -178.58(15) ?
C2 N3 C4 O41 . . . . -179.61(19) ?
C2 N3 C4 C5 . . . . 0.4(3) ?
O41 C4 C5 C6 . . . . 176.8(2) ?
N3 C4 C5 C6 . . . . -3.2(3) ?
C4 C5 C6 N1 . . . . 3.5(3) ?
C4 C5 C6 C61 . . . . -175.5(2) ?
C2 N1 C6 C5 . . . . -1.3(3) ?
C2 N1 C6 C61 . . . . 177.84(18) ?