2-[(2-Hydr­oxy-1-naphth­yl)methyl­ene­amino]-1,3-benzothia­zole

Cui, L.; Yin, H.; Yang, M.; Quan, L.; Wang, D.

doi:10.1107/S1600536808029644

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1974

doi:10.1107/S1600536808029644

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2-[(2-Hydroxy-1-naphthyl)methyleneamino]-1,3-benzothiazole

Liansheng Cui,^a Handong Yin,^a ^* Minglei Yang,^a Li Quan ^a and Daqi Wang ^a

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

(Received 9 September 2008; accepted 16 September 2008; online 20 September 2008)

In the title compound, C₁₈H₁₂N₂OS, the dihedral angle between the mean planes of the aromatic ring systems is 7.26 (8)°. There is an intramolecular O—H⋯N hydrogen bond, forming a six-membered ring. In the crystal structure, intermolecular C—H⋯N hydrogen bonds link the molecules into a one-dimensional chain.

Related literature

For general background, see: Lindoy et al. (1976 ).

Experimental

Crystal data

C₁₈H₁₂N₂OS
M_r = 304.36
Monoclinic, P 2₁ /n
a = 9.7439 (13) Å
b = 15.1506 (16) Å
c = 9.8082 (14) Å
β = 101.788 (2)°
V = 1417.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 (2) K
0.29 × 0.24 × 0.16 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.936, T_max = 0.964
6948 measured reflections
2493 independent reflections
1492 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.122
S = 1.06
2493 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯N1ⁱ	0.93	2.63	3.389 (4)	140
O1—H1⋯N2	0.82	1.84	2.576 (2)	148
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536808029644/sg2264sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029644/sg2264Isup2.hkl

checkCIF report

Comment top

Schiff bases are known to be important due to their applications in the preparation of dyes, liquid crystals and powerful corrosion inhibitors. Further more, they are used in the mechanism of many biochemical processes (Lindoy et al., 1976). We report here the synthesis and crystal structure of the title compound, a new Schiff base compound.

The molecular structure of the title compound is shown in Fig. 1. This compound is nonplanar, with a dihedral angle of 7.39 (5)° between the two benzene rings. There exists an intramolecular O—H···N hydrogen bond, forming a six-membered ring. An E configuration with respect to the C?N bond is shown by the molecule, with a C—N?C—C torsoin angle of 178.8 (2)°.

As seen in Fig.2, the molecules are linked into a one-dimensional chain by intermolecular C—H···N hydrogen bonds (Table 1).

Related literature top

For general background, see: Lindoy et al. (1976).

Experimental top

A mixture of 2-aminobenzothiazole (1 mmol) and 2-hydroxy-1-naphthaldehyde (1 mmol) in absolute ethanol (15 ml) was heated under reflux with stirring for 5 h and then filtered. The resulting clear orange solution was diffused diethyl ether vapor at room temperature for 16 days, after which large orange block-shaped crystals of the title complex suitable for X-ray diffraction analysis were obtained.

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 structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed approximately along the c axis.

2-[(2-Hydroxy-1-naphthyl)methyleneamino]-1,3-benzothiazole top

Crystal data top

C₁₈H₁₂N₂OS	F(000) = 632
M_r = 304.36	D_x = 1.426 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1399 reflections
a = 9.7439 (13) Å	θ = 2.5–24.1°
b = 15.1506 (16) Å	µ = 0.23 mm⁻¹
c = 9.8082 (14) Å	T = 293 K
β = 101.788 (2)°	Block, orange
V = 1417.4 (3) Å³	0.29 × 0.24 × 0.16 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	2493 independent reflections
Radiation source: fine-focus sealed tube	1492 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→11
T_min = 0.936, T_max = 0.964	k = −18→16
6948 measured reflections	l = −10→11

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0495P)² + 0.1122P] where P = (F_o² + 2F_c²)/3
2493 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₈H₁₂N₂OS	V = 1417.4 (3) Å³
M_r = 304.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7439 (13) Å	µ = 0.23 mm⁻¹
b = 15.1506 (16) Å	T = 293 K
c = 9.8082 (14) Å	0.29 × 0.24 × 0.16 mm
β = 101.788 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2493 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1492 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.964	R_int = 0.048
6948 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.06	Δρ_max = 0.22 e Å⁻³
2493 reflections	Δρ_min = −0.27 e Å⁻³
199 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
N1	0.1366 (2)	0.12262 (16)	1.0288 (2)	0.0448 (6)
N2	0.2042 (2)	−0.00510 (15)	0.9113 (2)	0.0411 (6)
O1	0.2722 (2)	−0.14394 (13)	0.7886 (2)	0.0557 (6)
H1	0.2814	−0.1033	0.8450	0.084*
S1	0.39272 (8)	0.06918 (6)	1.12063 (8)	0.0516 (3)
C1	0.0880 (3)	−0.00369 (18)	0.8179 (3)	0.0392 (7)
H1A	0.0245	0.0416	0.8218	0.047*
C2	0.0532 (3)	−0.06771 (18)	0.7105 (3)	0.0345 (7)
C3	0.1482 (3)	−0.13637 (19)	0.6999 (3)	0.0412 (7)
C4	0.1156 (3)	−0.20068 (19)	0.5945 (3)	0.0474 (8)
H4	0.1790	−0.2457	0.5887	0.057*
C5	−0.0075 (3)	−0.19716 (19)	0.5022 (3)	0.0468 (8)
H5	−0.0275	−0.2408	0.4343	0.056*
C6	−0.1079 (3)	−0.12922 (18)	0.5045 (3)	0.0386 (7)
C7	−0.0773 (3)	−0.06359 (18)	0.6093 (3)	0.0340 (7)
C8	−0.1789 (3)	0.00355 (18)	0.6076 (3)	0.0435 (8)
H8	−0.1626	0.0479	0.6746	0.052*
C9	−0.3009 (3)	0.0043 (2)	0.5089 (3)	0.0520 (9)
H9	−0.3657	0.0493	0.5100	0.062*
C10	−0.3298 (3)	−0.0610 (2)	0.4072 (3)	0.0536 (9)
H10	−0.4131	−0.0598	0.3409	0.064*
C11	−0.2348 (3)	−0.1267 (2)	0.4058 (3)	0.0499 (8)
H11	−0.2542	−0.1706	0.3384	0.060*
C12	0.2275 (3)	0.06286 (19)	1.0103 (3)	0.0407 (7)
C13	0.1972 (3)	0.18005 (19)	1.1355 (3)	0.0395 (7)
C14	0.3359 (3)	0.16080 (19)	1.1995 (3)	0.0417 (7)
C15	0.4076 (3)	0.2139 (2)	1.3077 (3)	0.0507 (8)
H15	0.5000	0.2018	1.3502	0.061*
C16	0.3372 (4)	0.2847 (2)	1.3493 (3)	0.0535 (9)
H16	0.3828	0.3205	1.4214	0.064*
C17	0.1997 (3)	0.3034 (2)	1.2859 (3)	0.0526 (8)
H17	0.1551	0.3517	1.3162	0.063*
C18	0.1283 (3)	0.2523 (2)	1.1798 (3)	0.0474 (8)
H18	0.0360	0.2654	1.1380	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0401 (15)	0.0450 (16)	0.0464 (15)	−0.0018 (12)	0.0022 (12)	−0.0040 (13)
N2	0.0439 (15)	0.0404 (16)	0.0376 (14)	−0.0009 (11)	0.0051 (11)	−0.0026 (12)
O1	0.0471 (14)	0.0532 (14)	0.0624 (14)	0.0129 (10)	0.0010 (11)	−0.0064 (11)
S1	0.0419 (5)	0.0566 (6)	0.0521 (5)	0.0031 (4)	−0.0004 (4)	−0.0015 (4)
C1	0.0415 (18)	0.0363 (18)	0.0411 (17)	0.0000 (13)	0.0114 (14)	0.0002 (14)
C2	0.0372 (17)	0.0296 (16)	0.0380 (16)	−0.0015 (13)	0.0111 (13)	−0.0003 (14)
C3	0.0397 (19)	0.0419 (19)	0.0424 (17)	−0.0002 (14)	0.0094 (14)	0.0024 (15)
C4	0.051 (2)	0.0388 (19)	0.055 (2)	0.0061 (14)	0.0168 (16)	−0.0046 (16)
C5	0.057 (2)	0.040 (2)	0.0458 (18)	−0.0065 (15)	0.0164 (16)	−0.0090 (15)
C6	0.0416 (18)	0.0380 (18)	0.0370 (17)	−0.0061 (14)	0.0097 (14)	0.0037 (14)
C7	0.0389 (17)	0.0304 (16)	0.0355 (15)	−0.0019 (13)	0.0141 (13)	0.0042 (13)
C8	0.0469 (19)	0.0368 (19)	0.0482 (18)	−0.0008 (14)	0.0130 (15)	−0.0016 (14)
C9	0.040 (2)	0.051 (2)	0.063 (2)	0.0078 (15)	0.0045 (16)	0.0094 (18)
C10	0.045 (2)	0.061 (2)	0.0485 (19)	−0.0102 (17)	−0.0051 (15)	0.0084 (18)
C11	0.057 (2)	0.046 (2)	0.0450 (19)	−0.0123 (16)	0.0061 (16)	−0.0008 (16)
C12	0.0388 (18)	0.0401 (18)	0.0422 (17)	−0.0010 (14)	0.0057 (14)	0.0049 (16)
C13	0.0413 (18)	0.0428 (19)	0.0341 (16)	−0.0054 (14)	0.0072 (14)	0.0033 (14)
C14	0.0399 (18)	0.0445 (19)	0.0403 (16)	−0.0066 (14)	0.0069 (14)	0.0080 (15)
C15	0.046 (2)	0.059 (2)	0.0432 (18)	−0.0085 (16)	0.0008 (15)	0.0042 (17)
C16	0.066 (2)	0.049 (2)	0.0438 (19)	−0.0179 (17)	0.0057 (17)	−0.0044 (16)
C17	0.064 (2)	0.042 (2)	0.053 (2)	−0.0047 (16)	0.0144 (17)	0.0001 (16)
C18	0.0431 (19)	0.048 (2)	0.0494 (19)	−0.0001 (15)	0.0060 (15)	0.0004 (16)

Geometric parameters (Å, º) top

N1—C12	1.305 (3)	C7—C8	1.417 (4)
N1—C13	1.396 (3)	C8—C9	1.371 (4)
N2—C1	1.303 (3)	C8—H8	0.9300
N2—C12	1.402 (3)	C9—C10	1.393 (4)
O1—C3	1.342 (3)	C9—H9	0.9300
O1—H1	0.8200	C10—C11	1.360 (4)
S1—C14	1.734 (3)	C10—H10	0.9300
S1—C12	1.749 (3)	C11—H11	0.9300
C1—C2	1.421 (4)	C13—C14	1.399 (4)
C1—H1A	0.9300	C13—C18	1.400 (4)
C2—C3	1.410 (4)	C14—C15	1.399 (4)
C2—C7	1.446 (3)	C15—C16	1.380 (4)
C3—C4	1.409 (4)	C15—H15	0.9300
C4—C5	1.348 (4)	C16—C17	1.386 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.424 (4)	C17—C18	1.368 (4)
C5—H5	0.9300	C17—H17	0.9300
C6—C11	1.407 (4)	C18—H18	0.9300
C6—C7	1.417 (4)

C12—N1—C13	110.0 (2)	C8—C9—H9	119.4
C1—N2—C12	118.0 (2)	C10—C9—H9	119.4
C3—O1—H1	109.5	C11—C10—C9	119.2 (3)
C14—S1—C12	88.99 (14)	C11—C10—H10	120.4
N2—C1—C2	123.5 (3)	C9—C10—H10	120.4
N2—C1—H1A	118.3	C10—C11—C6	121.2 (3)
C2—C1—H1A	118.3	C10—C11—H11	119.4
C3—C2—C1	119.8 (3)	C6—C11—H11	119.4
C3—C2—C7	118.6 (2)	N1—C12—N2	126.0 (3)
C1—C2—C7	121.5 (2)	N1—C12—S1	116.2 (2)
O1—C3—C2	122.2 (3)	N2—C12—S1	117.9 (2)
O1—C3—C4	117.1 (3)	N1—C13—C14	115.3 (3)
C2—C3—C4	120.8 (3)	N1—C13—C18	124.4 (3)
C5—C4—C3	120.1 (3)	C14—C13—C18	120.3 (3)
C5—C4—H4	119.9	C15—C14—C13	120.5 (3)
C3—C4—H4	119.9	C15—C14—S1	130.0 (2)
C4—C5—C6	122.5 (3)	C13—C14—S1	109.5 (2)
C4—C5—H5	118.7	C16—C15—C14	118.0 (3)
C6—C5—H5	118.7	C16—C15—H15	121.0
C11—C6—C7	120.3 (3)	C14—C15—H15	121.0
C11—C6—C5	121.3 (3)	C15—C16—C17	121.3 (3)
C7—C6—C5	118.4 (3)	C15—C16—H16	119.3
C8—C7—C6	116.9 (2)	C17—C16—H16	119.3
C8—C7—C2	123.6 (2)	C18—C17—C16	121.4 (3)
C6—C7—C2	119.5 (2)	C18—C17—H17	119.3
C9—C8—C7	121.1 (3)	C16—C17—H17	119.3
C9—C8—H8	119.4	C17—C18—C13	118.5 (3)
C7—C8—H8	119.4	C17—C18—H18	120.8
C8—C9—C10	121.3 (3)	C13—C18—H18	120.8

C12—N2—C1—C2	178.8 (2)	C9—C10—C11—C6	−0.5 (4)
N2—C1—C2—C3	−1.2 (4)	C7—C6—C11—C10	0.9 (4)
N2—C1—C2—C7	179.9 (2)	C5—C6—C11—C10	−179.1 (3)
C1—C2—C3—O1	0.1 (4)	C13—N1—C12—N2	−179.4 (2)
C7—C2—C3—O1	179.1 (2)	C13—N1—C12—S1	0.8 (3)
C1—C2—C3—C4	179.8 (2)	C1—N2—C12—N1	8.5 (4)
C7—C2—C3—C4	−1.3 (4)	C1—N2—C12—S1	−171.67 (19)
O1—C3—C4—C5	179.8 (2)	C14—S1—C12—N1	−0.1 (2)
C2—C3—C4—C5	0.1 (4)	C14—S1—C12—N2	−180.0 (2)
C3—C4—C5—C6	1.0 (4)	C12—N1—C13—C14	−1.3 (3)
C4—C5—C6—C11	179.3 (3)	C12—N1—C13—C18	179.0 (3)
C4—C5—C6—C7	−0.8 (4)	N1—C13—C14—C15	179.9 (2)
C11—C6—C7—C8	−0.7 (3)	C18—C13—C14—C15	−0.4 (4)
C5—C6—C7—C8	179.3 (2)	N1—C13—C14—S1	1.2 (3)
C11—C6—C7—C2	179.5 (2)	C18—C13—C14—S1	−179.1 (2)
C5—C6—C7—C2	−0.5 (3)	C12—S1—C14—C15	−179.1 (3)
C3—C2—C7—C8	−178.3 (2)	C12—S1—C14—C13	−0.56 (19)
C1—C2—C7—C8	0.7 (4)	C13—C14—C15—C16	0.5 (4)
C3—C2—C7—C6	1.4 (3)	S1—C14—C15—C16	178.9 (2)
C1—C2—C7—C6	−179.6 (2)	C14—C15—C16—C17	−0.3 (4)
C6—C7—C8—C9	0.1 (4)	C15—C16—C17—C18	0.1 (4)
C2—C7—C8—C9	179.9 (2)	C16—C17—C18—C13	0.0 (4)
C7—C8—C9—C10	0.3 (4)	N1—C13—C18—C17	179.9 (2)
C8—C9—C10—C11	−0.1 (4)	C14—C13—C18—C17	0.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···N1ⁱ	0.93	2.63	3.389 (4)	140
O1—H1···N2	0.82	1.85	2.576 (2)	148

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂N₂OS
M_r	304.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.7439 (13), 15.1506 (16), 9.8082 (14)
β (°)	101.788 (2)
V (Å³)	1417.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.29 × 0.24 × 0.16

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.936, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	6948, 2493, 1492
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.122, 1.06
No. of reflections	2493
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.27

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

Selected geometric parameters (Å, º) top

N1—C12	1.305 (3)	O1—C3	1.342 (3)
N1—C13	1.396 (3)	S1—C14	1.734 (3)
N2—C1	1.303 (3)	S1—C12	1.749 (3)
N2—C12	1.402 (3)

C12—N1—C13	110.0 (2)	N1—C12—N2	126.0 (3)
C1—N2—C12	118.0 (2)	N1—C12—S1	116.2 (2)
C3—O1—H1	109.5	N2—C12—S1	117.9 (2)
C14—S1—C12	88.99 (14)

C12—N2—C1—C2	178.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···N1ⁱ	0.93	2.63	3.389 (4)	139.6
O1—H1···N2	0.82	1.845	2.576 (2)	147.9

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Acknowledgements

We acknowledge the National Natural Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (2005ZX09) for financial support. This work is also partially supported by the Shandong `Tai-Shan Scholar Research Fund'.

References

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