(E)-2-[(6-Ethoxy-benzothia-zol-2-yl)imino-meth-yl]-6-methoxy-phenol.

In the title mol-ecule, C(17)H(16)N(2)O(3)S, the benzothia-zole fragment and the benzene ring form a dihedral angle of 13.8 (4)°, and an intramolecular O-H⋯N hydrogen bond occurs. In the crystal structure, pairs of weak inter-molecular O-H⋯S and C-H⋯(O,O) hydrogen bonds link mol-ecules into centrosymmetric dimers. These dimers are related by translation along the a axis and form stacks via π-π inter-actions, with a short inter-molecular distance of 3.766 (5) Å between the centroids of the benzene and thia-zole rings.

Related literature

For a related crystal structure, see: Zhao et al. (2008 ▶). For details of the crystallography and coordination chemistry of Schiff base compounds, see: Garnovski et al. (1993 ▶).

Experimental

Crystal data

C17H16N2O3S

M = 328.38

Triclinic,

a = 6.0178 (14) Å

b = 10.941 (3) Å

c = 12.164 (3) Å

α = 85.479 (4)°

β = 83.693 (5)°

γ = 76.486 (3)°

V = 772.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 298 K

0.12 × 0.08 × 0.06 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.973, T max = 0.987

4102 measured reflections

2720 independent reflections

1911 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.114

S = 1.03

2720 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.21 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 global, I. DOI: 10.1107/S1600536809009337/cv2526sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009337/cv2526Isup2.hkl

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

C17H16N2O3S	Z = 2
Mr = 328.38	F(000) = 344
Triclinic, P1	Dx = 1.411 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0178 (14) Å	Cell parameters from 982 reflections
b = 10.941 (3) Å	θ = 2.6–22.3°
c = 12.164 (3) Å	µ = 0.23 mm−1
α = 85.479 (4)°	T = 298 K
β = 83.693 (5)°	Block, yellow
γ = 76.486 (3)°	0.12 × 0.08 × 0.06 mm
V = 772.9 (3) Å3

Bruker SMART APEX diffractometer	2720 independent reflections
Radiation source: fine-focus sealed tube	1911 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.973, Tmax = 0.987	k = −12→12
4102 measured reflections	l = −14→9

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) = 0.114	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0548P)2 + 0.0301P] where P = (Fo2 + 2Fc2)/3
2720 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.21 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	0.46082 (11)	0.40652 (6)	0.37670 (5)	0.0489 (2)
O1	0.8898 (3)	0.68081 (19)	0.43648 (14)	0.0622 (5)
H1	0.8120	0.6363	0.4157	0.093*
O2	1.1451 (3)	0.83142 (17)	0.47463 (15)	0.0609 (5)
O3	−0.0448 (3)	0.15300 (16)	0.22235 (13)	0.0528 (5)
N1	0.7555 (3)	0.54862 (17)	0.29849 (16)	0.0439 (5)
N2	0.5822 (3)	0.45416 (18)	0.16878 (16)	0.0447 (5)
C1	1.0271 (4)	0.7137 (2)	0.3503 (2)	0.0437 (6)
C2	1.0358 (4)	0.6701 (2)	0.2444 (2)	0.0413 (6)
C3	1.1832 (4)	0.7085 (2)	0.1588 (2)	0.0498 (7)
H3	1.1915	0.6787	0.0886	0.060*
C4	1.3155 (4)	0.7898 (2)	0.1772 (2)	0.0539 (7)
H4	1.4111	0.8161	0.1194	0.065*
C5	1.3068 (4)	0.8329 (2)	0.2824 (2)	0.0518 (7)
H5	1.3978	0.8877	0.2945	0.062*
C6	1.1657 (4)	0.7957 (2)	0.3686 (2)	0.0458 (6)
C7	1.2911 (5)	0.9082 (3)	0.5008 (2)	0.0687 (9)
H7A	1.4484	0.8668	0.4822	0.103*
H7B	1.2668	0.9221	0.5786	0.103*
H7C	1.2566	0.9876	0.4593	0.103*
C8	0.8943 (4)	0.5867 (2)	0.2223 (2)	0.0436 (6)
H8	0.9036	0.5596	0.1511	0.052*
C9	0.6154 (4)	0.4739 (2)	0.2685 (2)	0.0413 (6)
C10	0.4252 (4)	0.3792 (2)	0.17276 (19)	0.0406 (6)
C11	0.3392 (4)	0.3421 (2)	0.27927 (19)	0.0397 (6)
C12	0.1811 (4)	0.2670 (2)	0.2947 (2)	0.0418 (6)
H12	0.1246	0.2435	0.3655	0.050*
C13	0.1098 (4)	0.2280 (2)	0.2018 (2)	0.0423 (6)
C14	0.1905 (4)	0.2659 (2)	0.0958 (2)	0.0473 (6)
H14	0.1394	0.2394	0.0343	0.057*
C15	0.3456 (4)	0.3422 (2)	0.0812 (2)	0.0477 (6)
H15	0.3963	0.3686	0.0103	0.057*
C16	−0.1092 (4)	0.1015 (2)	0.1306 (2)	0.0520 (7)
H16A	0.0253	0.0516	0.0905	0.062*
H16B	−0.1827	0.1684	0.0805	0.062*
C17	−0.2723 (4)	0.0206 (2)	0.1744 (2)	0.0595 (8)
H17A	−0.1959	−0.0472	0.2216	0.089*
H17B	−0.3230	−0.0133	0.1137	0.089*
H17C	−0.4023	0.0703	0.2160	0.089*

	U11	U22	U33	U12	U13	U23
S1	0.0572 (4)	0.0570 (4)	0.0411 (4)	−0.0323 (3)	−0.0019 (3)	0.0001 (3)
O1	0.0725 (13)	0.0819 (14)	0.0470 (11)	−0.0529 (11)	0.0118 (9)	−0.0104 (10)
O2	0.0722 (13)	0.0712 (12)	0.0521 (11)	−0.0419 (10)	−0.0002 (9)	−0.0115 (10)
O3	0.0598 (11)	0.0620 (11)	0.0476 (10)	−0.0381 (9)	0.0015 (8)	−0.0062 (9)
N1	0.0431 (11)	0.0474 (12)	0.0461 (12)	−0.0220 (10)	−0.0008 (10)	−0.0009 (10)
N2	0.0443 (12)	0.0506 (12)	0.0429 (12)	−0.0211 (10)	0.0007 (9)	−0.0006 (10)
C1	0.0410 (13)	0.0452 (14)	0.0464 (15)	−0.0183 (12)	0.0033 (11)	0.0027 (12)
C2	0.0393 (13)	0.0419 (14)	0.0443 (14)	−0.0154 (11)	−0.0021 (11)	0.0033 (11)
C3	0.0490 (15)	0.0566 (16)	0.0474 (15)	−0.0225 (13)	0.0015 (12)	−0.0016 (13)
C4	0.0519 (16)	0.0616 (17)	0.0519 (16)	−0.0289 (14)	0.0097 (13)	0.0014 (14)
C5	0.0498 (15)	0.0530 (16)	0.0602 (17)	−0.0306 (13)	0.0020 (13)	−0.0012 (14)
C6	0.0473 (14)	0.0462 (14)	0.0473 (15)	−0.0183 (12)	−0.0024 (12)	−0.0025 (12)
C7	0.081 (2)	0.0717 (19)	0.0689 (19)	−0.0453 (17)	−0.0054 (16)	−0.0165 (16)
C8	0.0402 (13)	0.0486 (15)	0.0432 (14)	−0.0146 (12)	0.0006 (11)	−0.0032 (12)
C9	0.0391 (13)	0.0418 (14)	0.0453 (15)	−0.0158 (11)	−0.0010 (11)	−0.0010 (12)
C10	0.0390 (13)	0.0435 (14)	0.0418 (14)	−0.0177 (11)	0.0031 (11)	−0.0028 (11)
C11	0.0414 (13)	0.0401 (13)	0.0394 (13)	−0.0140 (11)	−0.0008 (11)	−0.0035 (11)
C12	0.0450 (14)	0.0446 (14)	0.0390 (13)	−0.0208 (12)	0.0046 (11)	−0.0012 (11)
C13	0.0403 (13)	0.0423 (14)	0.0475 (15)	−0.0181 (11)	0.0011 (11)	−0.0024 (12)
C14	0.0487 (15)	0.0580 (16)	0.0409 (14)	−0.0245 (13)	0.0004 (11)	−0.0070 (12)
C15	0.0490 (15)	0.0600 (16)	0.0381 (14)	−0.0248 (13)	0.0042 (11)	−0.0014 (12)
C16	0.0538 (16)	0.0576 (16)	0.0527 (16)	−0.0279 (13)	−0.0038 (13)	−0.0075 (13)
C17	0.0587 (17)	0.0564 (17)	0.0731 (19)	−0.0333 (14)	−0.0030 (15)	−0.0058 (15)

S1—C11	1.732 (2)	C5—H5	0.9300
S1—C9	1.743 (2)	C7—H7A	0.9600
O1—C1	1.342 (3)	C7—H7B	0.9600
O1—H1	0.8200	C7—H7C	0.9600
O2—C6	1.361 (3)	C8—H8	0.9300
O2—C7	1.425 (3)	C10—C15	1.383 (3)
O3—C13	1.370 (3)	C10—C11	1.407 (3)
O3—C16	1.417 (3)	C11—C12	1.385 (3)
N1—C8	1.289 (3)	C12—C13	1.382 (3)
N1—C9	1.396 (3)	C12—H12	0.9300
N2—C9	1.293 (3)	C13—C14	1.394 (3)
N2—C10	1.383 (3)	C14—C15	1.380 (3)
C1—C2	1.399 (3)	C14—H14	0.9300
C1—C6	1.405 (3)	C15—H15	0.9300
C2—C3	1.397 (3)	C16—C17	1.500 (3)
C2—C8	1.443 (3)	C16—H16A	0.9700
C3—C4	1.370 (3)	C16—H16B	0.9700
C3—H3	0.9300	C17—H17A	0.9600
C4—C5	1.390 (4)	C17—H17B	0.9600
C4—H4	0.9300	C17—H17C	0.9600
C5—C6	1.373 (3)
C11—S1—C9	88.69 (11)	N2—C9—N1	126.4 (2)
C1—O1—H1	109.5	N2—C9—S1	117.12 (17)
C6—O2—C7	117.7 (2)	N1—C9—S1	116.38 (18)
C13—O3—C16	117.82 (18)	C15—C10—N2	124.9 (2)
C8—N1—C9	118.2 (2)	C15—C10—C11	119.1 (2)
C9—N2—C10	109.4 (2)	N2—C10—C11	115.9 (2)
O1—C1—C2	122.7 (2)	C12—C11—C10	121.7 (2)
O1—C1—C6	117.7 (2)	C12—C11—S1	129.48 (19)
C2—C1—C6	119.6 (2)	C10—C11—S1	108.82 (16)
C3—C2—C1	119.4 (2)	C13—C12—C11	118.0 (2)
C3—C2—C8	119.6 (2)	C13—C12—H12	121.0
C1—C2—C8	121.1 (2)	C11—C12—H12	121.0
C4—C3—C2	120.6 (2)	O3—C13—C12	115.4 (2)
C4—C3—H3	119.7	O3—C13—C14	123.7 (2)
C2—C3—H3	119.7	C12—C13—C14	120.9 (2)
C3—C4—C5	120.0 (2)	C15—C14—C13	120.6 (2)
C3—C4—H4	120.0	C15—C14—H14	119.7
C5—C4—H4	120.0	C13—C14—H14	119.7
C6—C5—C4	120.8 (2)	C14—C15—C10	119.6 (2)
C6—C5—H5	119.6	C14—C15—H15	120.2
C4—C5—H5	119.6	C10—C15—H15	120.2
O2—C6—C5	125.7 (2)	O3—C16—C17	107.7 (2)
O2—C6—C1	114.7 (2)	O3—C16—H16A	110.2
C5—C6—C1	119.7 (2)	C17—C16—H16A	110.2
O2—C7—H7A	109.5	O3—C16—H16B	110.2
O2—C7—H7B	109.5	C17—C16—H16B	110.2
H7A—C7—H7B	109.5	H16A—C16—H16B	108.5
O2—C7—H7C	109.5	C16—C17—H17A	109.5
H7A—C7—H7C	109.5	C16—C17—H17B	109.5
H7B—C7—H7C	109.5	H17A—C17—H17B	109.5
N1—C8—C2	121.9 (2)	C16—C17—H17C	109.5
N1—C8—H8	119.0	H17A—C17—H17C	109.5
C2—C8—H8	119.0	H17B—C17—H17C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.606 (3)	147
O1—H1···S1i	0.82	2.92	3.1746 (18)	100
C12—H12···O1i	0.93	2.59	3.328 (3)	136
C12—H12···O2i	0.93	2.60	3.491 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.606 (3)	147
O1—H1⋯S1i	0.82	2.92	3.1746 (18)	100
C12—H12⋯O1i	0.93	2.59	3.328 (3)	136
C12—H12⋯O2i	0.93	2.60	3.491 (3)	160

Symmetry code: (i) .