2-(2-Amino-5-methylthia-zol-4-yl)phenol.

In the title compound, C(10)H(10)N(2)OS, the benzene ring is nearly co-planar with the thia-zole ring, making a dihedral angle of 2.1 (2)°. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds. An intra-molecular O-H⋯N hydrogen bond is also present.

Related literature

For background to 2-amino-4-aryl­thia­zoles and their wide-ranging anti­fungal activity, see: Hu et al. (2008 ▶); Kazzouli et al. (2002 ▶); Holla et al. (2003 ▶). For a related structure, see: He et al. (2006 ▶).

Experimental

Crystal data

C10H10N2OS

M = 206.27

Orthorhombic,

a = 12.9391 (5) Å

b = 10.3967 (4) Å

c = 14.2938 (6) Å

V = 1922.86 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 173 K

0.48 × 0.42 × 0.39 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.869, T max = 0.891

11037 measured reflections

1881 independent reflections

1706 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.150

S = 0.98

1881 reflections

129 parameters

H-atom parameters constrained

Δρmax = 1.20 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903164X/xu2563sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903164X/xu2563Isup2.hkl

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

C10H10N2OS	F(000) = 864
Mr = 206.27	Dx = 1.425 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7684 reflections
a = 12.9391 (5) Å	θ = 2.4–27.0°
b = 10.3967 (4) Å	µ = 0.30 mm−1
c = 14.2938 (6) Å	T = 173 K
V = 1922.86 (13) Å3	Block, yellow
Z = 8	0.48 × 0.42 × 0.39 mm

Bruker SMART 1000 CCD diffractometer	1881 independent reflections
Radiation source: fine-focus sealed tube	1706 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 26.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −15→14
Tmin = 0.869, Tmax = 0.891	k = −12→12
11037 measured reflections	l = −17→17

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) = 0.150	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0885P)2 + 3.3976P] where P = (Fo2 + 2Fc2)/3
1881 reflections	(Δ/σ)max < 0.001
129 parameters	Δρmax = 1.20 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Experimental. 1H NMR (CDCl3, 400 MHz): 2.48 (s, 3H, CH3), 4.97 (br, 2H, NH2), 6.86–7.42(m, 4H, phenyl-H).

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	0.29069 (5)	0.23322 (6)	0.58881 (4)	0.0269 (2)
C1	0.2598 (2)	0.3782 (2)	0.64120 (16)	0.0242 (5)
C2	0.43091 (18)	0.4000 (2)	0.61774 (16)	0.0232 (5)
C3	0.4199 (2)	0.2792 (2)	0.58181 (17)	0.0266 (6)
C4	0.52468 (18)	0.4802 (2)	0.62670 (16)	0.0241 (5)
C5	0.52103 (19)	0.6026 (2)	0.66966 (17)	0.0263 (5)
C6	0.6103 (2)	0.6770 (3)	0.67875 (18)	0.0315 (6)
H6	0.6066	0.7589	0.7081	0.038*
C7	0.7037 (2)	0.6329 (3)	0.64567 (19)	0.0344 (6)
H7	0.7642	0.6840	0.6526	0.041*
C8	0.7095 (2)	0.5136 (3)	0.6021 (2)	0.0369 (7)
H8	0.7738	0.4829	0.5790	0.044*
C9	0.6212 (2)	0.4398 (3)	0.59266 (18)	0.0314 (6)
H9	0.6261	0.3590	0.5620	0.038*
C10	0.4945 (2)	0.1822 (3)	0.5439 (2)	0.0413 (7)
H10A	0.5252	0.2149	0.4859	0.062*
H10B	0.4579	0.1016	0.5309	0.062*
H10C	0.5491	0.1665	0.5899	0.062*
N1	0.33898 (16)	0.45419 (19)	0.65168 (14)	0.0243 (5)
N2	0.16111 (17)	0.4091 (2)	0.66472 (16)	0.0316 (5)
H2A	0.1473	0.4850	0.6889	0.038*
H2B	0.1110	0.3531	0.6558	0.038*
O1	0.43180 (14)	0.65465 (18)	0.70442 (15)	0.0359 (5)
H1	0.3833	0.6015	0.6985	0.054*

	U11	U22	U33	U12	U13	U23
S1	0.0270 (4)	0.0238 (4)	0.0301 (4)	−0.0019 (2)	−0.0005 (2)	−0.0051 (2)
C1	0.0263 (12)	0.0229 (12)	0.0234 (11)	−0.0001 (9)	−0.0006 (9)	−0.0005 (9)
C2	0.0234 (12)	0.0238 (12)	0.0225 (11)	0.0026 (9)	0.0002 (9)	0.0014 (9)
C3	0.0258 (12)	0.0266 (13)	0.0274 (12)	0.0006 (10)	0.0004 (9)	−0.0009 (9)
C4	0.0236 (12)	0.0264 (12)	0.0223 (11)	0.0008 (9)	−0.0014 (9)	0.0036 (9)
C5	0.0243 (12)	0.0270 (12)	0.0277 (12)	0.0022 (10)	−0.0017 (9)	0.0022 (10)
C6	0.0313 (14)	0.0312 (13)	0.0321 (13)	−0.0040 (11)	−0.0043 (11)	0.0010 (10)
C7	0.0285 (14)	0.0421 (16)	0.0328 (13)	−0.0106 (11)	−0.0026 (10)	0.0045 (12)
C8	0.0250 (14)	0.0473 (17)	0.0385 (14)	−0.0006 (12)	0.0061 (11)	0.0019 (13)
C9	0.0274 (13)	0.0335 (14)	0.0333 (13)	0.0010 (11)	0.0047 (10)	−0.0017 (11)
C10	0.0338 (15)	0.0321 (15)	0.0581 (18)	0.0044 (12)	0.0047 (13)	−0.0131 (13)
N1	0.0221 (10)	0.0226 (10)	0.0282 (10)	0.0003 (8)	0.0016 (8)	−0.0015 (8)
N2	0.0228 (11)	0.0298 (11)	0.0422 (12)	−0.0017 (9)	0.0024 (9)	−0.0075 (10)
O1	0.0242 (9)	0.0275 (10)	0.0561 (12)	0.0006 (7)	−0.0007 (8)	−0.0113 (9)

S1—C1	1.730 (2)	C6—H6	0.9500
S1—C3	1.742 (3)	C7—C8	1.390 (4)
C1—N1	1.302 (3)	C7—H7	0.9500
C1—N2	1.359 (3)	C8—C9	1.382 (4)
C2—C3	1.364 (4)	C8—H8	0.9500
C2—N1	1.403 (3)	C9—H9	0.9500
C2—C4	1.477 (3)	C10—H10A	0.9800
C3—C10	1.498 (4)	C10—H10B	0.9800
C4—C9	1.405 (3)	C10—H10C	0.9800
C4—C5	1.414 (4)	N2—H2A	0.8800
C5—O1	1.368 (3)	N2—H2B	0.8800
C5—C6	1.397 (4)	O1—H1	0.8400
C6—C7	1.376 (4)
C1—S1—C3	90.41 (12)	C6—C7—H7	120.1
N1—C1—N2	124.6 (2)	C8—C7—H7	120.1
N1—C1—S1	113.39 (19)	C7—C8—C9	119.6 (3)
N2—C1—S1	121.98 (19)	C7—C8—H8	120.2
C3—C2—N1	114.3 (2)	C9—C8—H8	120.2
C3—C2—C4	129.6 (2)	C8—C9—C4	122.4 (3)
N1—C2—C4	116.1 (2)	C8—C9—H9	118.8
C2—C3—C10	133.6 (2)	C4—C9—H9	118.8
C2—C3—S1	109.35 (19)	C3—C10—H10A	109.5
C10—C3—S1	117.0 (2)	C3—C10—H10B	109.5
C9—C4—C5	116.7 (2)	H10A—C10—H10B	109.5
C9—C4—C2	122.1 (2)	C3—C10—H10C	109.5
C5—C4—C2	121.2 (2)	H10A—C10—H10C	109.5
O1—C5—C6	116.4 (2)	H10B—C10—H10C	109.5
O1—C5—C4	122.8 (2)	C1—N1—C2	112.6 (2)
C6—C5—C4	120.8 (2)	C1—N2—H2A	120.0
C7—C6—C5	120.6 (3)	C1—N2—H2B	120.0
C7—C6—H6	119.7	H2A—N2—H2B	120.0
C5—C6—H6	119.7	C5—O1—H1	109.5
C6—C7—C8	119.9 (2)
C3—S1—C1—N1	0.48 (19)	C9—C4—C5—C6	−1.2 (3)
C3—S1—C1—N2	177.9 (2)	C2—C4—C5—C6	179.3 (2)
N1—C2—C3—C10	−175.7 (3)	O1—C5—C6—C7	−179.8 (2)
C4—C2—C3—C10	3.6 (5)	C4—C5—C6—C7	0.3 (4)
N1—C2—C3—S1	1.0 (3)	C5—C6—C7—C8	0.5 (4)
C4—C2—C3—S1	−179.6 (2)	C6—C7—C8—C9	−0.2 (4)
C1—S1—C3—C2	−0.85 (19)	C7—C8—C9—C4	−0.8 (4)
C1—S1—C3—C10	176.5 (2)	C5—C4—C9—C8	1.5 (4)
C3—C2—C4—C9	3.0 (4)	C2—C4—C9—C8	−179.0 (2)
N1—C2—C4—C9	−177.7 (2)	N2—C1—N1—C2	−177.3 (2)
C3—C2—C4—C5	−177.6 (2)	S1—C1—N1—C2	0.0 (3)
N1—C2—C4—C5	1.8 (3)	C3—C2—N1—C1	−0.7 (3)
C9—C4—C5—O1	178.9 (2)	C4—C2—N1—C1	179.9 (2)
C2—C4—C5—O1	−0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.77	2.521 (3)	148
N2—H2B···O1i	0.88	2.25	2.961 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.77	2.521 (3)	148
N2—H2B⋯O1i	0.88	2.25	2.961 (3)	138

Symmetry code: (i) .