(E)-2-Meth­oxy-6-(thia­zol-2-ylimino­meth­yl)phenol

Li, W.; Yin, H.; Wen, L.; Fan, W.; Li, J.

doi:10.1107/S1600536809040410

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2675

https://doi.org/10.1107/S1600536809040410

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(E)-2-Methoxy-6-(thiazol-2-yliminomethyl)phenol

Wenkuan Li,^a Handong Yin,^a ^* Liyuan Wen,^a Weidong Fan ^a and Jing Li ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 19 September 2009; accepted 4 October 2009; online 10 October 2009)

The title compound, C₁₁H₁₀N₂O₂S, displays an E configuration about the C=N bond. The mean planes of the thiazole and benzene rings make a dihedral angle of 9.32 (18)°. Intramolecular 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_r = 234.27
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.110
S = 1.02
1920 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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

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 I, global. DOI: https://doi.org/10.1107/S1600536809040410/jj2011sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809040410/jj2011Isup2.hkl

checkCIF report

Comment top

Schiff bases have been extensively researched because of their important applications in coordination chemistry, catalysis and biological processes. (Lv et al. 2006, Tarafder et al. 2002, Zhou et al. 2009). Owing to the importance of these Schiff base analogue compounds, we report here the crystal structure of the title compound, C₁₁H₁₀N₂O₂S₁, (I).

The title compoud was prepared by the condensation reaction of 2-hydroxy-3-methoxybenzaldehyde with an equimolar quantity of thiazol-2 -amine (Fig. 1). The structure of (I) shows a trans or E configuration about the C=N bond. The dihedral angle between the mean planes of the thiazole and benzene rings is 9.32 (18) °. Intramolecular O1—H1···N2 hydrogen bonds are found in the crystal structure. Crystal packing is stabilized mainly by van der Waals interactions (Fig. 2).

Related literature top

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

Experimental top

2-hydroxy-3-methoxybenzaldehyde (10 mmol) was added to a ethanolic solution of thiazol-2-amine (10 mmol). Then, the reaction mixture was heated for 2 h under reflux. After filtration a yellow powder was obtained. Suitable crystals for X-ray diffraction were obtained by recrystallization from methanol. Anal. Calcd (%) for C₁₁H₁₀N₂O₂S₁ (Mr = 234.27): C,56.40; H, 4.30; N, 11.96; O, 13.66; S,13.69. Found (%): C,56.38; H, 4.35; N, 11.90; O, 13.69; S,13.68.

Structure description top

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

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (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 the title molecule, with 50% probability displacement ellipsoids. An O—H..N intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The molecular packing of the title compound, viewed along the b axis. Intramolecular hydrogen bonds are shown as dashed lines.

(E)-2-Methoxy-6-(thiazol-2-yliminomethyl)phenol top

Crystal data top

C₁₁H₁₀N₂O₂S	F(000) = 976
M_r = 234.27	D_x = 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

Data collection top

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

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) = 0.110	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0373P)² + 1.8745P] where P = (F_o² + 2F_c²)/3
1920 reflections	(Δ/σ)_max < 0.001
146 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₁H₁₀N₂O₂S	V = 2197.2 (5) Å³
M_r = 234.27	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.765 (3) Å	µ = 0.28 mm⁻¹
b = 4.9619 (8) Å	T = 298 K
c = 20.238 (2) Å	0.29 × 0.18 × 0.17 mm
β = 117.931 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	1920 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1139 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.954	R_int = 0.034
5338 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.02	Δρ_max = 0.19 e Å⁻³
1920 reflections	Δρ_min = −0.23 e Å⁻³
146 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀N₂O₂S
M_r	234.27
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	24.765 (3), 4.9619 (8), 20.238 (2)
β (°)	117.931 (2)
V (Å³)	2197.2 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.29 × 0.18 × 0.17

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.923, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	5338, 1920, 1139
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.110, 1.02
No. of reflections	1920
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.23

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···N2	0.82	1.91	2.627 (3)	145.7

Acknowledgements

We acknowledge the financial support of the Natural Science Foundation of China (No. 20771053), the Natural Science Foundation of Shandong Province (Y2008B48) and the Students Technology Cultural Innovation Fund of Liaocheng University.

References

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