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In the structure of the title compound, C7H10N2O4S2·H2O, the 4-hydroxy group hydrogen bonds to the water O atom, which in turn associates via one water H atom with one sulfonate O atom to create an intramolecular R22(12) hydrogen-bonded ring. The other water H atom and the pyrimidinium H atom associate with adjacent and separate sulfonate O atoms.
Supporting information
CCDC reference: 236080
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.032
- wR factor = 0.082
- Data-to-parameter ratio = 11.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
PLAT417_ALERT_2_B Short Inter D-H..H-D H1W .. H41 = 2.01 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D H2W .. H41 = 2.01 Ang.
Alert level C
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.45 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H232 .. N3 = 2.70 Ang.
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO, SCALEPACK (Otwinowski & Minor, 1997) and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
4-Hydroxy-6-methyl-2-(sulfonatoethylsulfanyl)pyrimidin-1-ium monohydrate
top
Crystal data top
C7H10N2O4S2·H2O | F(000) = 560 |
Mr = 268.31 | Dx = 1.628 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7654 reflections |
a = 6.1137 (2) Å | θ = 2.9–27.5° |
b = 11.2202 (3) Å | µ = 0.50 mm−1 |
c = 15.9632 (6) Å | T = 120 K |
β = 91.0483 (18)° | Prism, colourless |
V = 1094.84 (6) Å3 | 0.35 × 0.20 × 0.08 mm |
Z = 4 | |
Data collection top
Bruker–Nonius KappaCCD area-detector diffractometer | 1920 independent reflections |
Radiation source: Bruker–Nonius FR591 rotating anode | 1619 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
Detector resolution: 9.091 pixels mm-1 | θmax = 25.0°, θmin = 3.1° |
φ and ω scans | h = −7→7 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −13→13 |
Tmin = 0.932, Tmax = 0.961 | l = −18→18 |
11989 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0425P)2 + 0.5029P] where P = (Fo2 + 2Fc2)/3 |
1920 reflections | (Δ/σ)max < 0.001 |
162 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.5271 (3) | 0.37582 (15) | 0.10006 (11) | 0.0146 (4) | |
H1 | 0.559 (4) | 0.451 (2) | 0.1012 (16) | 0.027 (7)* | |
C2 | 0.3494 (3) | 0.33538 (17) | 0.14014 (12) | 0.0139 (4) | |
S21 | 0.20999 (8) | 0.44136 (4) | 0.19888 (3) | 0.01700 (17) | |
C22 | −0.0187 (3) | 0.35287 (18) | 0.23366 (13) | 0.0163 (5) | |
H221 | −0.1402 | 0.4071 | 0.2478 | 0.020* | |
H222 | −0.0697 | 0.3018 | 0.1867 | 0.020* | |
C23 | 0.0318 (3) | 0.27423 (18) | 0.30892 (13) | 0.0161 (4) | |
H231 | 0.0684 | 0.3244 | 0.3582 | 0.020* | |
H232 | 0.1595 | 0.2230 | 0.2972 | 0.020* | |
S24 | −0.19989 (8) | 0.18388 (4) | 0.33057 (3) | 0.01565 (16) | |
O25 | −0.3790 (2) | 0.26434 (13) | 0.34850 (11) | 0.0264 (4) | |
O26 | −0.1371 (2) | 0.11032 (12) | 0.40262 (9) | 0.0213 (4) | |
O27 | −0.2422 (3) | 0.11280 (13) | 0.25562 (10) | 0.0247 (4) | |
N3 | 0.2810 (3) | 0.22453 (14) | 0.13575 (11) | 0.0160 (4) | |
C4 | 0.4018 (3) | 0.14818 (18) | 0.09037 (13) | 0.0170 (5) | |
O41 | 0.3365 (3) | 0.03806 (12) | 0.08472 (10) | 0.0231 (4) | |
H41 | 0.183 (6) | 0.026 (3) | 0.104 (2) | 0.069 (11)* | |
C5 | 0.5926 (3) | 0.18368 (18) | 0.04977 (13) | 0.0167 (5) | |
H5 | 0.6789 | 0.1275 | 0.0205 | 0.021* | |
C6 | 0.6509 (3) | 0.30021 (18) | 0.05327 (13) | 0.0155 (4) | |
C61 | 0.8393 (3) | 0.35392 (19) | 0.00879 (13) | 0.0197 (5) | |
H611 | 0.9377 | 0.2905 | −0.0096 | 0.025* | |
H612 | 0.9189 | 0.4078 | 0.0468 | 0.025* | |
H613 | 0.7852 | 0.3987 | −0.0401 | 0.025* | |
O1W | −0.0506 (3) | 0.00014 (15) | 0.12299 (11) | 0.0227 (4) | |
H1W | −0.105 (5) | 0.035 (3) | 0.163 (2) | 0.048 (9)* | |
H2W | −0.076 (5) | −0.076 (3) | 0.1329 (19) | 0.046 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) |
Geometric parameters (Å, º) top
N1—C2 | 1.349 (3) | S24—O26 | 1.4612 (15) |
N1—C6 | 1.368 (3) | N3—C4 | 1.350 (3) |
N1—H1 | 0.87 (3) | C4—O41 | 1.301 (3) |
C2—N3 | 1.314 (3) | C4—C5 | 1.403 (3) |
C2—S21 | 1.746 (2) | O41—H41 | 1.00 (4) |
S21—C22 | 1.810 (2) | C5—C6 | 1.356 (3) |
C22—C23 | 1.518 (3) | C5—H5 | 0.95 |
C22—H221 | 0.99 | C6—C61 | 1.491 (3) |
C22—H222 | 0.99 | C61—H611 | 0.98 |
C23—S24 | 1.7810 (19) | C61—H612 | 0.98 |
C23—H231 | 0.99 | C61—H613 | 0.98 |
C23—H232 | 0.99 | O1W—H1W | 0.83 (3) |
S24—O25 | 1.4518 (15) | O1W—H2W | 0.88 (3) |
S24—O27 | 1.4572 (16) | | |
| | | |
C2—N1—C6 | 120.58 (17) | O25—S24—C23 | 106.85 (9) |
C2—N1—H1 | 120.1 (17) | O27—S24—C23 | 106.38 (9) |
C6—N1—H1 | 119.2 (17) | O26—S24—C23 | 106.01 (9) |
N3—C2—N1 | 123.47 (18) | C2—N3—C4 | 116.90 (17) |
N3—C2—S21 | 121.01 (15) | O41—C4—N3 | 118.01 (18) |
N1—C2—S21 | 115.52 (14) | O41—C4—C5 | 119.62 (18) |
C2—S21—C22 | 100.28 (9) | N3—C4—C5 | 122.37 (18) |
C23—C22—S21 | 114.49 (15) | C4—O41—H41 | 114 (2) |
C23—C22—H221 | 108.6 | C6—C5—C4 | 118.35 (18) |
S21—C22—H221 | 108.6 | C6—C5—H5 | 120.8 |
C23—C22—H222 | 108.6 | C4—C5—H5 | 120.8 |
S21—C22—H222 | 108.6 | C5—C6—N1 | 118.22 (18) |
H221—C22—H222 | 107.6 | C5—C6—C61 | 125.08 (19) |
C22—C23—S24 | 109.48 (14) | N1—C6—C61 | 116.70 (18) |
C22—C23—H231 | 109.8 | C6—C61—H611 | 109.5 |
S24—C23—H231 | 109.8 | C6—C61—H612 | 109.5 |
C22—C23—H232 | 109.8 | H611—C61—H612 | 109.5 |
S24—C23—H232 | 109.8 | C6—C61—H613 | 109.5 |
H231—C23—H232 | 108.2 | H611—C61—H613 | 109.5 |
O25—S24—O27 | 112.27 (10) | H612—C61—H613 | 109.5 |
O25—S24—O26 | 112.60 (9) | H1W—O1W—H2W | 104 (3) |
O27—S24—O26 | 112.16 (9) | | |
| | | |
C6—N1—C2—N3 | −1.7 (3) | S21—C2—N3—C4 | −178.58 (15) |
C6—N1—C2—S21 | 178.96 (15) | C2—N3—C4—O41 | −179.61 (19) |
N3—C2—S21—C22 | −3.3 (2) | C2—N3—C4—C5 | 0.4 (3) |
N1—C2—S21—C22 | 176.12 (16) | O41—C4—C5—C6 | 176.8 (2) |
C2—S21—C22—C23 | 81.06 (16) | N3—C4—C5—C6 | −3.2 (3) |
S21—C22—C23—S24 | −175.24 (10) | C4—C5—C6—N1 | 3.5 (3) |
C22—C23—S24—O25 | −60.42 (16) | C4—C5—C6—C61 | −175.5 (2) |
C22—C23—S24—O27 | 59.71 (16) | C2—N1—C6—C5 | −1.3 (3) |
C22—C23—S24—O26 | 179.27 (13) | C2—N1—C6—C61 | 177.84 (18) |
N1—C2—N3—C4 | 2.1 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O26i | 0.87 (3) | 1.85 (3) | 2.716 (2) | 176 (2) |
O41—H41···O1W | 1.00 (4) | 1.50 (4) | 2.491 (2) | 174 (3) |
O1W—H1W···O27 | 0.83 (3) | 1.92 (4) | 2.747 (2) | 177 (3) |
O1W—H2W···O25ii | 0.88 (3) | 1.84 (4) | 2.720 (2) | 178 (3) |
C22—H222···N3 | 0.99 | 2.46 | 2.824 (3) | 101 |
C23—H232···N3 | 0.99 | 2.70 | 3.229 (3) | 114 |
C22—H221···O27iii | 0.99 | 2.42 | 3.268 (2) | 144 |
C5—H5···O41iv | 0.95 | 2.51 | 3.320 (2) | 144 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x−1/2, y−1/2, −z+1/2; (iii) −x−1/2, y+1/2, −z+1/2; (iv) −x+1, −y, −z. |
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