4-Hydro­xy-6-methyl-2-(sulfonatoethyl­sulfanyl)­pyrimidin-1-ium monohydrate

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.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.35 × 0.20 × 0.08 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0425P)^2 + 0.5029P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	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)

Geometric parameters (Å, º)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O26^i	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···O25^ii	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···O27^iii	0.99	2.42	3.268 (2)	144
C5—H5···O41^iv	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.