(E)-2-[(6-Ethoxy­benzothia­zol-2-yl)imino­meth­yl]-6-methoxy­phenol

Kong, L.-Q.

doi:10.1107/S1600536809009337

organic compounds

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Volume 65| Part 4| April 2009| Page o832

doi:10.1107/S1600536809009337

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(E)-2-[(6-Ethoxybenzothiazol-2-yl)iminomethyl]-6-methoxyphenol

Ling-Qian Kong ^a ^*

^aDongchang College, Liaocheng University, 250059 Liaocheng, Shandong, People's Republic of China
^*Correspondence e-mail: imlijikun@163.com

(Received 25 February 2009; accepted 13 March 2009; online 25 March 2009)

In the title molecule, C₁₇H₁₆N₂O₃S, the benzothiazole 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 intermolecular O—H⋯S and C—H⋯(O,O) hydrogen bonds link molecules into centrosymmetric dimers. These dimers are related by translation along the a axis and form stacks via π–π interactions, with a short intermolecular distance of 3.766 (5) Å between the centroids of the benzene and thiazole 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_r = 328.38
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.114
S = 1.03
2720 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) -x+1, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009337/cv2526sup1.cif

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

checkCIF report

Comment top

Recently, a number of Schiff base compounds have been investigated in terms of their crystallography and coordination chemistry (Garnovski et al., 1993). In order to continue our studies on Schiff bases, we now report the synthesis and crystal structure of the title compound, (I).

In (I) (Fig. 1), all the geometric parameters are in a good agreement with those found in (E)-2-methoxy-6-[(5-methylisoxazol-3-yl)-iminomethyl] phenol (Zhao et al., 2008). The benzene and the benzothiazole rings make a dihedral angle of 13.8 (4)° showing that the Schiff base ligand adopts a non-planar conformation in the case. Moreover, weak intermolecular O—H···S and C—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers. These dimers related by translation along axis a form stacks via π–π interactions proved by short intermolecular distance of 3.766 (5) Å between the centroids of benzene and thiazole rings.

Related literature top

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 top

The title compound was synthesized by the reaction of 2-hydroxy-3-methoxybenzaldehyde (0.152 g, 1 mmol) and 6-ethoxybenzothiazol-2-amine (0.194 g, 1 mmol) in ethanol solution and stirred under reflux conditions (353 K) for 5 h. When cooled to room temperature the solution was filtered and after a week yellow crystals suitable for X-ray diffraction study were obtained. Yield, 0.283 g, 86%. m.p. 342–344 K.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme.

(E)-2-[(6-Ethoxybenzothiazol-2-yl)iminomethyl]-6-methoxyphenol top

Crystal data top

C₁₇H₁₆N₂O₃S	Z = 2
M_r = 328.38	F(000) = 344
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0548P)² + 0.0301P] where P = (F_o² + 2F_c²)/3
2720 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₇H₁₆N₂O₃S	γ = 76.486 (3)°
M_r = 328.38	V = 772.9 (3) Å³
Triclinic, P1	Z = 2
a = 6.0178 (14) Å	Mo Kα radiation
b = 10.941 (3) Å	µ = 0.23 mm⁻¹
c = 12.164 (3) Å	T = 298 K
α = 85.479 (4)°	0.12 × 0.08 × 0.06 mm
β = 83.693 (5)°

Data collection top

Bruker SMART APEX diffractometer	2720 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1911 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.987	R_int = 0.020
4102 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
2720 reflections	Δρ_min = −0.21 e Å⁻³
209 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂O₃S
M_r	328.38
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.0178 (14), 10.941 (3), 12.164 (3)
α, β, γ (°)	85.479 (4), 83.693 (5), 76.486 (3)
V (Å³)	772.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.12 × 0.08 × 0.06

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.973, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	4102, 2720, 1911
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.114, 1.03
No. of reflections	2720
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	100.2
C12—H12···O1ⁱ	0.93	2.59	3.328 (3)	136.1
C12—H12···O2ⁱ	0.93	2.60	3.491 (3)	160.4

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The author is grateful for financial support from the Natural Science Foundation of Dongchang College of Liaocheng University (grant No. LG0801).

References

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