4,6-Dimeth-oxy-2-(methyl-sulfan-yl)pyrimidine-4-hy-droxy-benzoic acid (1/1).

The base mol-ecule of the title co-crystal, C7H10N2O2S·C7H6O3, is essentially planar, with a maximum deviation of 0.0806 (14) Å for all non-H atoms. The acid mol-ecule is also nearly planar, with a dihedral angle of 8.12 (14)° between the benzene ring and the carb-oxy group. In the crystal, the acid mol-ecules form an inversion dimer through a pair of O-H⋯O hydrogen bonds with an R2(2)(8) ring motif. The pyrimidine mol-ecules are linked on both sides of the dimer into a heterotetra-mer via O-H⋯N and C-H⋯O hydrogen bonds with R2(2)(8) ring motifs. The heterotetra-mers are further linked by weak C-H⋯O hydrogen bonds, forming a tape structure along [1-10].

Related literature

For general background to substituted pyrimidines, see: Hunt et al. (1980 ▶); Baker & Santi (1965 ▶); Holy et al. (1974 ▶). For 4-hy­droxy­benzoic acid, see: Vishweshwar et al. (2003 ▶). For related structures, see: Balasubramani & Fun (2009 ▶); Hemamalini & Fun (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C7H10N2O2S·C7H6O3

M = 324.35

Triclinic,

a = 6.9923 (5) Å

b = 10.2887 (8) Å

c = 10.7578 (8) Å

α = 77.419 (2)°

β = 83.381 (2)°

γ = 89.209 (2)°

V = 750.27 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 100 K

0.44 × 0.37 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.901, T max = 0.947

13682 measured reflections

3393 independent reflections

3105 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.093

S = 1.10

3393 reflections

210 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812046338/is5216sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046338/is5216Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046338/is5216Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H10N2O2S·C7H6O3	Z = 2
Mr = 324.35	F(000) = 340
Triclinic, P1	Dx = 1.436 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9923 (5) Å	Cell parameters from 9952 reflections
b = 10.2887 (8) Å	θ = 2.5–32.6°
c = 10.7578 (8) Å	µ = 0.24 mm−1
α = 77.419 (2)°	T = 100 K
β = 83.381 (2)°	Block, colourless
γ = 89.209 (2)°	0.44 × 0.37 × 0.23 mm
V = 750.27 (10) Å3

Bruker SMART APEXII CCD area-detector diffractometer	3393 independent reflections
Radiation source: fine-focus sealed tube	3105 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.901, Tmax = 0.947	k = −13→13
13682 measured reflections	l = −13→13

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) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0508P)2 + 0.2589P] where P = (Fo2 + 2Fc2)/3
3393 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.46 e Å−3
1 restraint	Δρmin = −0.27 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.22119 (4)	0.45956 (3)	0.93029 (3)	0.02129 (10)
O1	0.78663 (12)	0.67424 (9)	0.67045 (9)	0.0237 (2)
O2	0.81296 (13)	0.20863 (9)	0.83750 (9)	0.0261 (2)
O3	0.31596 (13)	0.39971 (9)	0.58570 (9)	0.0251 (2)
O4	0.61173 (13)	0.34673 (10)	0.50895 (9)	0.0272 (2)
O5	0.28845 (14)	−0.22653 (9)	0.78692 (9)	0.0260 (2)
N1	0.53552 (14)	0.56189 (10)	0.79118 (10)	0.0195 (2)
N2	0.54001 (14)	0.32727 (10)	0.87876 (10)	0.0199 (2)
C1	0.71747 (17)	0.55457 (12)	0.73576 (11)	0.0197 (2)
C2	0.81861 (17)	0.43673 (13)	0.74714 (12)	0.0214 (2)
H2A	0.9460	0.4324	0.7067	0.026*
C3	0.71973 (17)	0.32502 (13)	0.82225 (11)	0.0207 (2)
C4	0.45790 (16)	0.44686 (12)	0.85972 (11)	0.0185 (2)
C5	0.7153 (2)	0.09621 (13)	0.92394 (13)	0.0300 (3)
H5A	0.8014	0.0196	0.9344	0.045*
H5B	0.5998	0.0741	0.8888	0.045*
H5C	0.6784	0.1185	1.0074	0.045*
C6	0.16623 (18)	0.28891 (13)	1.00996 (13)	0.0261 (3)
H6A	0.0352	0.2828	1.0546	0.039*
H6B	0.2579	0.2581	1.0721	0.039*
H6C	0.1756	0.2331	0.9464	0.039*
C7	0.98129 (18)	0.67934 (14)	0.60767 (13)	0.0271 (3)
H7A	1.0168	0.7718	0.5665	0.041*
H7B	0.9897	0.6253	0.5427	0.041*
H7C	1.0694	0.6444	0.6712	0.041*
C8	0.55397 (17)	0.07913 (13)	0.62423 (12)	0.0219 (2)
H8A	0.6798	0.1082	0.5862	0.026*
C9	0.51922 (17)	−0.05487 (13)	0.67699 (12)	0.0220 (2)
H9A	0.6210	−0.1170	0.6762	0.026*
C10	0.33342 (18)	−0.09825 (12)	0.73148 (11)	0.0213 (2)
C11	0.18445 (18)	−0.00551 (13)	0.73189 (13)	0.0266 (3)
H11A	0.0576	−0.0348	0.7674	0.032*
C12	0.22154 (18)	0.12821 (13)	0.68095 (12)	0.0248 (3)
H12A	0.1205	0.1906	0.6833	0.030*
C13	0.40666 (17)	0.17230 (12)	0.62604 (11)	0.0199 (2)
C14	0.44409 (17)	0.31494 (12)	0.57134 (11)	0.0201 (2)
H1O4	0.625 (4)	0.4317 (11)	0.482 (3)	0.095 (10)*
H1O5	0.377 (3)	−0.275 (3)	0.781 (2)	0.063 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.01540 (15)	0.01880 (17)	0.02680 (17)	0.00153 (11)	0.00292 (11)	−0.00160 (12)
O1	0.0193 (4)	0.0201 (4)	0.0286 (4)	−0.0013 (3)	0.0057 (3)	−0.0024 (4)
O2	0.0238 (4)	0.0198 (5)	0.0323 (5)	0.0059 (4)	0.0029 (4)	−0.0040 (4)
O3	0.0258 (4)	0.0179 (4)	0.0298 (5)	0.0025 (3)	0.0014 (4)	−0.0040 (4)
O4	0.0218 (4)	0.0204 (5)	0.0345 (5)	−0.0021 (4)	0.0034 (4)	0.0010 (4)
O5	0.0235 (5)	0.0152 (4)	0.0350 (5)	0.0010 (4)	0.0047 (4)	−0.0008 (4)
N1	0.0164 (4)	0.0196 (5)	0.0216 (5)	0.0012 (4)	0.0002 (4)	−0.0037 (4)
N2	0.0174 (5)	0.0196 (5)	0.0223 (5)	0.0013 (4)	−0.0004 (4)	−0.0049 (4)
C1	0.0178 (5)	0.0205 (6)	0.0203 (5)	−0.0006 (4)	−0.0001 (4)	−0.0045 (4)
C2	0.0169 (5)	0.0228 (6)	0.0240 (6)	0.0019 (4)	0.0014 (4)	−0.0061 (5)
C3	0.0188 (5)	0.0209 (6)	0.0228 (5)	0.0039 (4)	−0.0019 (4)	−0.0065 (5)
C4	0.0166 (5)	0.0198 (6)	0.0193 (5)	0.0004 (4)	−0.0015 (4)	−0.0050 (4)
C5	0.0351 (7)	0.0196 (6)	0.0313 (7)	0.0053 (5)	0.0039 (5)	−0.0011 (5)
C6	0.0207 (6)	0.0216 (6)	0.0325 (6)	−0.0009 (5)	0.0041 (5)	−0.0019 (5)
C7	0.0185 (6)	0.0287 (7)	0.0308 (7)	−0.0037 (5)	0.0054 (5)	−0.0032 (5)
C8	0.0193 (5)	0.0202 (6)	0.0247 (6)	0.0005 (5)	0.0009 (4)	−0.0037 (5)
C9	0.0199 (6)	0.0195 (6)	0.0254 (6)	0.0031 (4)	−0.0002 (4)	−0.0037 (5)
C10	0.0237 (6)	0.0173 (6)	0.0212 (5)	0.0002 (5)	0.0009 (4)	−0.0023 (4)
C11	0.0211 (6)	0.0210 (6)	0.0331 (7)	0.0007 (5)	0.0070 (5)	−0.0012 (5)
C12	0.0228 (6)	0.0198 (6)	0.0288 (6)	0.0037 (5)	0.0043 (5)	−0.0027 (5)
C13	0.0221 (6)	0.0169 (6)	0.0197 (5)	0.0006 (4)	0.0007 (4)	−0.0034 (4)
C14	0.0217 (6)	0.0185 (6)	0.0195 (5)	0.0004 (4)	−0.0012 (4)	−0.0037 (4)

S1—C4	1.7552 (12)	C5—H5B	0.9800
S1—C6	1.8034 (14)	C5—H5C	0.9800
O1—C1	1.3434 (15)	C6—H6A	0.9800
O1—C7	1.4444 (14)	C6—H6B	0.9800
O2—C3	1.3429 (15)	C6—H6C	0.9800
O2—C5	1.4406 (16)	C7—H7A	0.9800
O3—C14	1.2619 (15)	C7—H7B	0.9800
O4—C14	1.2904 (15)	C7—H7C	0.9800
O4—H1O4	0.862 (10)	C8—C9	1.3851 (17)
O5—C10	1.3497 (15)	C8—C13	1.3987 (17)
O5—H1O5	0.79 (3)	C8—H8A	0.9500
N1—C4	1.3358 (16)	C9—C10	1.3990 (17)
N1—C1	1.3497 (15)	C9—H9A	0.9500
N2—C3	1.3336 (15)	C10—C11	1.4032 (17)
N2—C4	1.3354 (16)	C11—C12	1.3816 (18)
C1—C2	1.3845 (17)	C11—H11A	0.9500
C2—C3	1.3930 (17)	C12—C13	1.3977 (17)
C2—H2A	0.9500	C12—H12A	0.9500
C5—H5A	0.9800	C13—C14	1.4722 (17)
C4—S1—C6	101.55 (6)	H6A—C6—H6C	109.5
C1—O1—C7	117.10 (10)	H6B—C6—H6C	109.5
C3—O2—C5	116.61 (10)	O1—C7—H7A	109.5
C14—O4—H1O4	112 (2)	O1—C7—H7B	109.5
C10—O5—H1O5	112.7 (18)	H7A—C7—H7B	109.5
C4—N1—C1	115.43 (10)	O1—C7—H7C	109.5
C3—N2—C4	115.10 (11)	H7A—C7—H7C	109.5
O1—C1—N1	111.95 (10)	H7B—C7—H7C	109.5
O1—C1—C2	124.93 (11)	C9—C8—C13	121.05 (11)
N1—C1—C2	123.11 (11)	C9—C8—H8A	119.5
C1—C2—C3	115.03 (11)	C13—C8—H8A	119.5
C1—C2—H2A	122.5	C8—C9—C10	119.61 (11)
C3—C2—H2A	122.5	C8—C9—H9A	120.2
N2—C3—O2	118.77 (11)	C10—C9—H9A	120.2
N2—C3—C2	124.02 (11)	O5—C10—C9	123.27 (11)
O2—C3—C2	117.20 (11)	O5—C10—C11	117.12 (11)
N2—C4—N1	127.30 (11)	C9—C10—C11	119.60 (11)
N2—C4—S1	118.35 (9)	C12—C11—C10	120.27 (12)
N1—C4—S1	114.35 (9)	C12—C11—H11A	119.9
O2—C5—H5A	109.5	C10—C11—H11A	119.9
O2—C5—H5B	109.5	C11—C12—C13	120.47 (12)
H5A—C5—H5B	109.5	C11—C12—H12A	119.8
O2—C5—H5C	109.5	C13—C12—H12A	119.8
H5A—C5—H5C	109.5	C12—C13—C8	118.99 (11)
H5B—C5—H5C	109.5	C12—C13—C14	119.95 (11)
S1—C6—H6A	109.5	C8—C13—C14	121.05 (11)
S1—C6—H6B	109.5	O3—C14—O4	122.92 (12)
H6A—C6—H6B	109.5	O3—C14—C13	120.49 (11)
S1—C6—H6C	109.5	O4—C14—C13	116.60 (11)
C7—O1—C1—N1	179.48 (10)	C6—S1—C4—N2	−0.74 (11)
C7—O1—C1—C2	0.01 (18)	C6—S1—C4—N1	179.09 (9)
C4—N1—C1—O1	−178.96 (10)	C13—C8—C9—C10	0.86 (19)
C4—N1—C1—C2	0.52 (17)	C8—C9—C10—O5	−178.72 (11)
O1—C1—C2—C3	178.46 (11)	C8—C9—C10—C11	0.08 (19)
N1—C1—C2—C3	−0.95 (18)	O5—C10—C11—C12	177.68 (12)
C4—N2—C3—O2	179.53 (10)	C9—C10—C11—C12	−1.2 (2)
C4—N2—C3—C2	−0.63 (17)	C10—C11—C12—C13	1.4 (2)
C5—O2—C3—N2	−5.20 (16)	C11—C12—C13—C8	−0.42 (19)
C5—O2—C3—C2	174.95 (11)	C11—C12—C13—C14	179.62 (12)
C1—C2—C3—N2	1.02 (18)	C9—C8—C13—C12	−0.70 (19)
C1—C2—C3—O2	−179.14 (11)	C9—C8—C13—C14	179.26 (11)
C3—N2—C4—N1	0.13 (18)	C12—C13—C14—O3	7.67 (17)
C3—N2—C4—S1	179.94 (8)	C8—C13—C14—O3	−172.29 (11)
C1—N1—C4—N2	−0.08 (18)	C12—C13—C14—O4	−172.05 (11)
C1—N1—C4—S1	−179.89 (8)	C8—C13—C14—O4	7.99 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O3i	0.86 (2)	1.76 (2)	2.6189 (14)	172 (3)
O5—H1O5···N1ii	0.80 (3)	1.99 (3)	2.7562 (14)	162 (3)
C9—H9A···O1ii	0.95	2.44	3.3437 (16)	160
C12—H12A···O2iii	0.95	2.59	3.3340 (16)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O3i	0.86 (2)	1.76 (2)	2.6189 (14)	172 (3)
O5—H1O5⋯N1ii	0.80 (3)	1.99 (3)	2.7562 (14)	162 (3)
C9—H9A⋯O1ii	0.95	2.44	3.3437 (16)	160
C12—H12A⋯O2iii	0.95	2.59	3.3340 (16)	135

Symmetry codes: (i) ; (ii) ; (iii) .