(E)-2-Meth-oxy-6-(thia-zol-2-ylimino-meth-yl)phenol.

The title compound, C(11)H(10)N(2)O(2)S, displays an E configuration about the C=N bond. The mean planes of the thia-zole and benzene rings make a dihedral angle of 9.32 (18)°. Intra-molecular O-H⋯N hydrogen bonds are found in the crystal structure.

Related literature

For general background to Schiff bases, see: Lv et al. (2006 ▶); Tarafder et al. (2002 ▶); Zhou et al. (2009 ▶).

Experimental

Crystal data

C11H10N2O2S

M = 234.27

Monoclinic,

a = 24.765 (3) Å

b = 4.9619 (8) Å

c = 20.238 (2) Å

β = 117.931 (2)°

V = 2197.2 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.28 mm−1

T = 298 K

0.29 × 0.18 × 0.17 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.923, T max = 0.954

5338 measured reflections

1920 independent reflections

1139 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.110

S = 1.02

1920 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040410/jj2011sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040410/jj2011Isup2.hkl

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

C11H10N2O2S	F(000) = 976
Mr = 234.27	Dx = 1.416 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1208 reflections
a = 24.765 (3) Å	θ = 3.3–21.9°
b = 4.9619 (8) Å	µ = 0.28 mm−1
c = 20.238 (2) Å	T = 298 K
β = 117.931 (2)°	Block, colorless
V = 2197.2 (5) Å3	0.29 × 0.18 × 0.17 mm
Z = 8

Siemens SMART CCD area-detector diffractometer	1920 independent reflections
Radiation source: fine-focus sealed tube	1139 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→26
Tmin = 0.923, Tmax = 0.954	k = −5→5
5338 measured reflections	l = −24→22

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0373P)2 + 1.8745P] where P = (Fo2 + 2Fc2)/3
1920 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.10966 (12)	1.1575 (6)	0.46446 (14)	0.0681 (8)
N2	0.09882 (10)	0.9199 (5)	0.35514 (12)	0.0495 (6)
O1	0.09126 (9)	0.6986 (4)	0.23318 (10)	0.0582 (6)
H1	0.0833	0.8091	0.2575	0.087*
O2	0.13089 (10)	0.3468 (4)	0.17130 (12)	0.0687 (6)
S1	0.01303 (4)	1.2680 (2)	0.34433 (5)	0.0702 (3)
C1	0.14555 (13)	0.7692 (6)	0.39241 (16)	0.0512 (7)
H1A	0.1658	0.7842	0.4442	0.061*
C2	0.16805 (12)	0.5776 (6)	0.35747 (15)	0.0458 (7)
C3	0.13974 (12)	0.5484 (6)	0.27981 (16)	0.0457 (7)
C4	0.16169 (13)	0.3571 (6)	0.24731 (17)	0.0514 (8)
C5	0.21123 (14)	0.2002 (6)	0.29263 (19)	0.0608 (9)
H5	0.2259	0.0724	0.2714	0.073*
C6	0.23948 (14)	0.2313 (7)	0.3698 (2)	0.0642 (9)
H6	0.2730	0.1246	0.3999	0.077*
C7	0.21848 (13)	0.4170 (6)	0.40180 (18)	0.0576 (8)
H7	0.2378	0.4370	0.4535	0.069*
C8	0.14472 (19)	0.1291 (7)	0.1360 (2)	0.0966 (13)
H8A	0.1856	0.1494	0.1428	0.145*
H8B	0.1164	0.1291	0.0835	0.145*
H8C	0.1415	−0.0380	0.1578	0.145*
C9	0.08023 (13)	1.1000 (6)	0.39362 (16)	0.0500 (7)
C10	0.07640 (17)	1.3433 (7)	0.48042 (19)	0.0747 (10)
H10	0.0900	1.4100	0.5286	0.090*
C11	0.02367 (16)	1.4240 (7)	0.42374 (18)	0.0678 (9)
H11	−0.0031	1.5471	0.4274	0.081*

	U11	U22	U33	U12	U13	U23
N1	0.0747 (18)	0.082 (2)	0.0432 (15)	0.0066 (16)	0.0239 (14)	−0.0087 (14)
N2	0.0487 (15)	0.0539 (15)	0.0471 (14)	−0.0046 (13)	0.0234 (12)	−0.0034 (13)
O1	0.0626 (13)	0.0576 (13)	0.0500 (12)	0.0124 (11)	0.0227 (10)	−0.0032 (10)
O2	0.0912 (17)	0.0617 (15)	0.0625 (14)	0.0129 (12)	0.0438 (13)	−0.0047 (12)
S1	0.0629 (5)	0.0897 (7)	0.0526 (5)	0.0103 (5)	0.0227 (4)	−0.0114 (5)
C1	0.0543 (18)	0.0540 (19)	0.0412 (16)	−0.0111 (16)	0.0188 (15)	−0.0017 (15)
C2	0.0451 (17)	0.0415 (17)	0.0498 (18)	−0.0068 (14)	0.0214 (14)	0.0009 (14)
C3	0.0438 (17)	0.0396 (17)	0.0557 (19)	−0.0002 (14)	0.0250 (15)	0.0022 (15)
C4	0.0572 (19)	0.0481 (19)	0.058 (2)	−0.0037 (16)	0.0343 (17)	0.0010 (16)
C5	0.061 (2)	0.049 (2)	0.088 (3)	0.0018 (16)	0.048 (2)	0.0035 (18)
C6	0.0493 (19)	0.059 (2)	0.079 (3)	0.0027 (17)	0.0254 (18)	0.0138 (19)
C7	0.0516 (19)	0.056 (2)	0.0569 (19)	−0.0035 (16)	0.0189 (16)	0.0046 (17)
C8	0.162 (4)	0.068 (3)	0.084 (3)	0.021 (3)	0.077 (3)	−0.002 (2)
C9	0.0572 (18)	0.0507 (18)	0.0481 (18)	−0.0063 (15)	0.0298 (15)	−0.0029 (15)
C10	0.093 (3)	0.083 (3)	0.051 (2)	0.000 (2)	0.036 (2)	−0.018 (2)
C11	0.075 (2)	0.078 (2)	0.060 (2)	0.004 (2)	0.0391 (19)	−0.0082 (19)

N1—C9	1.300 (3)	C3—C4	1.401 (4)
N1—C10	1.372 (4)	C4—C5	1.378 (4)
N2—C1	1.284 (3)	C5—C6	1.389 (4)
N2—C9	1.398 (3)	C5—H5	0.9300
O1—C3	1.351 (3)	C6—C7	1.361 (4)
O1—H1	0.8200	C6—H6	0.9300
O2—C4	1.361 (3)	C7—H7	0.9300
O2—C8	1.423 (4)	C8—H8A	0.9600
S1—C11	1.689 (3)	C8—H8B	0.9600
S1—C9	1.704 (3)	C8—H8C	0.9600
C1—C2	1.443 (4)	C10—C11	1.333 (4)
C1—H1A	0.9300	C10—H10	0.9300
C2—C3	1.397 (4)	C11—H11	0.9300
C2—C7	1.397 (4)
C9—N1—C10	108.6 (3)	C7—C6—H6	119.8
C1—N2—C9	119.1 (2)	C5—C6—H6	119.8
C3—O1—H1	109.5	C6—C7—C2	120.5 (3)
C4—O2—C8	117.2 (3)	C6—C7—H7	119.8
C11—S1—C9	89.58 (16)	C2—C7—H7	119.8
N2—C1—C2	123.0 (3)	O2—C8—H8A	109.5
N2—C1—H1A	118.5	O2—C8—H8B	109.5
C2—C1—H1A	118.5	H8A—C8—H8B	109.5
C3—C2—C7	119.3 (3)	O2—C8—H8C	109.5
C3—C2—C1	121.0 (3)	H8A—C8—H8C	109.5
C7—C2—C1	119.7 (3)	H8B—C8—H8C	109.5
O1—C3—C2	122.8 (3)	N1—C9—N2	126.4 (3)
O1—C3—C4	117.3 (3)	N1—C9—S1	115.3 (2)
C2—C3—C4	119.9 (3)	N2—C9—S1	118.2 (2)
O2—C4—C5	125.7 (3)	C11—C10—N1	116.9 (3)
O2—C4—C3	114.9 (3)	C11—C10—H10	121.5
C5—C4—C3	119.4 (3)	N1—C10—H10	121.5
C4—C5—C6	120.5 (3)	C10—C11—S1	109.5 (3)
C4—C5—H5	119.7	C10—C11—H11	125.2
C6—C5—H5	119.7	S1—C11—H11	125.2
C7—C6—C5	120.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.91	2.627 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.82	1.91	2.627 (3)	146