Monoclinic polymorph of 2-(pyrimidin-2-ylsulfan-yl)acetic acid.

The title compound, C(6)H(6)N(2)O(2)S, is a new polymorphic form of 2-(pyrimidin-2-ylsulfan-yl)acetic acid. Unlike the previous orthorhombic polymorph [Pan & Chen (2009 ▶) Acta Cryst. E65, o652], the mol-ecules are not planar: the aromatic ring makes an angle of 80.67 (17)° with the carboxyl plane. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds into chains along [02].

Related literature

For the previously reported orthorhombic polymorph, see: Pan & Chen (2009 ▶).

Experimental

Crystal data

C6H6N2O2S

M = 170.19

Monoclinic,

a = 8.2617 (3) Å

b = 10.3028 (4) Å

c = 9.9289 (3) Å

β = 119.845 (2)°

V = 733.05 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 293 K

0.40 × 0.23 × 0.20 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.891, T max = 0.999

14257 measured reflections

1688 independent reflections

1532 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.133

S = 1.17

1688 reflections

100 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000651/bt5454sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000651/bt5454Isup2.hkl

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

C6H6N2O2S	F(000) = 352
Mr = 170.19	Dx = 1.542 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.2617 (3) Å	Cell parameters from 6019 reflections
b = 10.3028 (4) Å	θ = 2.8–27.2°
c = 9.9289 (3) Å	µ = 0.39 mm−1
β = 119.845 (2)°	T = 293 K
V = 733.05 (4) Å3	Prism, yellow
Z = 4	0.40 × 0.23 × 0.20 mm

Bruker APEX CCD area-detector diffractometer	1688 independent reflections
Radiation source: fine-focus sealed tube	1532 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 27.6°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −10→10
Tmin = 0.891, Tmax = 0.999	k = −13→13
14257 measured reflections	l = −12→12

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.3572P] where P = (Fo2 + 2Fc2)/3
1688 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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	0.79236 (8)	0.78200 (6)	0.43768 (7)	0.0451 (2)
O2	0.2618 (3)	0.7405 (2)	0.1323 (3)	0.0642 (6)
H2	0.2106	0.7051	0.0572	0.096*
O1	0.5054 (3)	0.63141 (18)	0.1564 (2)	0.0544 (5)
C1	0.4398 (3)	0.7107 (2)	0.2002 (3)	0.0383 (5)
C2	0.5444 (3)	0.7939 (2)	0.3434 (3)	0.0411 (5)
H2A	0.5048	0.7701	0.4171	0.049*
H2B	0.5094	0.8838	0.3146	0.049*
C3	0.8442 (3)	0.8782 (2)	0.3184 (2)	0.0358 (5)
N1	0.7074 (2)	0.92846 (19)	0.1883 (2)	0.0407 (4)
C6	0.7635 (4)	1.0039 (2)	0.1100 (3)	0.0495 (6)
H6	0.6732	1.0425	0.0185	0.059*
C5	0.9468 (4)	1.0271 (3)	0.1575 (3)	0.0544 (7)
H5	0.9820	1.0810	0.1013	0.065*
C4	1.0766 (4)	0.9677 (3)	0.2916 (3)	0.0536 (7)
H4	1.2028	0.9803	0.3261	0.064*
N2	1.0268 (3)	0.8926 (2)	0.3736 (2)	0.0459 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0382 (3)	0.0520 (4)	0.0360 (3)	−0.0017 (2)	0.0116 (2)	0.0089 (2)
O2	0.0394 (10)	0.0662 (13)	0.0664 (13)	0.0044 (8)	0.0108 (9)	−0.0106 (10)
O1	0.0514 (10)	0.0554 (11)	0.0595 (11)	−0.0035 (8)	0.0299 (9)	−0.0133 (9)
C1	0.0362 (11)	0.0383 (12)	0.0411 (12)	−0.0037 (8)	0.0197 (9)	0.0045 (9)
C2	0.0398 (12)	0.0454 (13)	0.0418 (12)	−0.0021 (9)	0.0233 (10)	−0.0007 (10)
C3	0.0341 (10)	0.0336 (11)	0.0360 (11)	0.0000 (8)	0.0147 (9)	−0.0030 (8)
N1	0.0371 (9)	0.0426 (11)	0.0396 (10)	0.0039 (8)	0.0169 (8)	0.0058 (8)
C6	0.0604 (15)	0.0433 (14)	0.0478 (13)	0.0062 (11)	0.0291 (12)	0.0072 (11)
C5	0.0705 (17)	0.0440 (14)	0.0667 (17)	−0.0068 (12)	0.0477 (15)	−0.0022 (12)
C4	0.0437 (13)	0.0522 (15)	0.0729 (18)	−0.0101 (11)	0.0350 (13)	−0.0138 (13)
N2	0.0325 (9)	0.0479 (12)	0.0511 (12)	−0.0016 (8)	0.0161 (9)	−0.0032 (9)

S1—C3	1.753 (2)	C3—N2	1.333 (3)
S1—C2	1.783 (2)	N1—C6	1.335 (3)
O2—C1	1.313 (3)	C6—C5	1.365 (4)
O2—H2	0.7449	C6—H6	0.9300
O1—C1	1.177 (3)	C5—C4	1.370 (4)
C1—C2	1.510 (3)	C5—H5	0.9300
C2—H2A	0.9700	C4—N2	1.328 (3)
C2—H2B	0.9700	C4—H4	0.9300
C3—N1	1.327 (3)
C3—S1—C2	102.08 (10)	N2—C3—S1	113.08 (16)
C1—O2—H2	109.4	C3—N1—C6	114.8 (2)
O1—C1—O2	125.2 (2)	N1—C6—C5	123.2 (2)
O1—C1—C2	126.1 (2)	N1—C6—H6	118.4
O2—C1—C2	108.7 (2)	C5—C6—H6	118.4
C1—C2—S1	115.15 (16)	C6—C5—C4	117.1 (2)
C1—C2—H2A	108.5	C6—C5—H5	121.5
S1—C2—H2A	108.5	C4—C5—H5	121.5
C1—C2—H2B	108.5	N2—C4—C5	121.6 (2)
S1—C2—H2B	108.5	N2—C4—H4	119.2
H2A—C2—H2B	107.5	C5—C4—H4	119.2
N1—C3—N2	126.8 (2)	C4—N2—C3	116.5 (2)
N1—C3—S1	120.15 (16)
O1—C1—C2—S1	8.2 (3)	C3—N1—C6—C5	0.8 (4)
O2—C1—C2—S1	−172.38 (16)	N1—C6—C5—C4	0.8 (4)
C3—S1—C2—C1	77.84 (18)	C6—C5—C4—N2	−1.2 (4)
C2—S1—C3—N1	−4.9 (2)	C5—C4—N2—C3	0.0 (4)
C2—S1—C3—N2	174.94 (16)	N1—C3—N2—C4	1.8 (4)
N2—C3—N1—C6	−2.2 (3)	S1—C3—N2—C4	−177.99 (18)
S1—C3—N1—C6	177.60 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2i	0.74	1.97	2.700 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2i	0.74	1.97	2.700 (3)	166

Symmetry code: (i) .