2-(1,3-Benzothia­zol-2-ylimino­meth­yl)-2-naphthol

Badahdaha, K.O.; Asiri, A.M.; Ng, S.W.

doi:10.1107/S1600536809008514

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o759

doi:10.1107/S1600536809008514

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2-(1,3-Benzothiazol-2-yliminomethyl)-2-naphthol

Khadija O. Badahdaha,^a Abdullah Mohamed Asiri ^a and Seik Weng Ng ^b ^*

^aChemistry Department, Faculty of Science, King Abdul Aziz University, Jeddah, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 5 March 2009; accepted 9 March 2009; online 14 March 2009)

In the title molecule, C₁₈H₁₂N₂OS, the dihedral angle between the two fused-ring systems is 7.2 (1)°. The hydroxy group forms an intramolecular hydrogen bond with the imino group.

Related literature

For the crystal structures of other Schiff bases derived by condensing benzthiazolyl-2-amine with aldehydes/ketones, see: Büyükgüngör et al. (2004 ); Cannon et al. (2001 ); Guo et al. (2002 ); Saraçoğlu et al. (2004 ).

Experimental

Crystal data

C₁₈H₁₂N₂OS
M_r = 304.36
Monoclinic, P 2₁ /n
a = 9.6398 (2) Å
b = 14.9687 (4) Å
c = 9.6646 (2) Å
β = 101.323 (2)°
V = 1367.41 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 123 K
0.25 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.943, T_max = 0.988
12442 measured reflections
3139 independent reflections
2396 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.122
S = 1.02
3139 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 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⋯N1	0.84 (1)	1.82 (2)	2.573 (2)	148 (3)

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008514/lh2783sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008514/lh2783Isup2.hkl

checkCIF report

Comment top

The molecular structure of the title compound is shown in Fig. 1.

Related literature top

For the crystal structures of other Schiff bases derived by condensing benzthiazolyl-2-amine with aldehydes/ketones, see: Büyükgüngör et al. (2004); Cannon et al. (2001); Guo et al. (2002); Saraçoğlu et al. (2004).

Experimental top

2-Aminobenzothiazole (4.0 g, 26.6 mmol) dissolved in ethanol (25 ml) was added to 2-hydroxybenzaldehyde (4.58 g, 26.6 mmol) dissolved in ethanol (25 ml). The mixture was heated for another hour. The solid that separated from the reaction mixture was isolated and recrystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellisoid plot (Barbour, 2001) of C₁₈H₁₂N₂OS; probability levels are set at 70% and H-atoms are drawn as spheres of arbitrary radius. The dashed line denotes the hydrogen bond.

2-(1,3-Benzothiazol-2-yliminomethyl)-2-naphthol top

Crystal data top

C₁₈H₁₂N₂OS	F(000) = 632
M_r = 304.36	D_x = 1.481 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2677 reflections
a = 9.6398 (2) Å	θ = 2.5–28.1°
b = 14.9687 (4) Å	µ = 0.24 mm⁻¹
c = 9.6646 (2) Å	T = 123 K
β = 101.323 (2)°	Irregular block, orange
V = 1367.41 (5) Å³	0.25 × 0.20 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3139 independent reflections
Radiation source: fine-focus sealed tube	2396 reflections with I > 2˘I)
Graphite monochromator	R_int = 0.051
ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.943, T_max = 0.988	k = −19→19
12442 measured reflections	l = −12→12

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0612P)² + 0.543P] where P = (F_o² + 2F_c²)/3
3139 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.53 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₁₂N₂OS	V = 1367.41 (5) Å³
M_r = 304.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.6398 (2) Å	µ = 0.24 mm⁻¹
b = 14.9687 (4) Å	T = 123 K
c = 9.6646 (2) Å	0.25 × 0.20 × 0.05 mm
β = 101.323 (2)°

Data collection top

Bruker SMART APEX diffractometer	3139 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2396 reflections with I > 2˘I)
T_min = 0.943, T_max = 0.988	R_int = 0.051
12442 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.53 e Å⁻³
3139 reflections	Δρ_min = −0.23 e Å⁻³
203 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.

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

	x	y	z	U_iso*/U_eq
S1	0.62414 (5)	0.57067 (3)	0.89471 (5)	0.02326 (15)
O1	0.28598 (15)	0.35583 (9)	0.77536 (15)	0.0261 (3)
H1	0.348 (2)	0.3964 (14)	0.782 (3)	0.057 (9)*
N1	0.41330 (16)	0.49518 (10)	0.70645 (17)	0.0214 (4)
N2	0.53279 (16)	0.62326 (11)	0.63631 (17)	0.0218 (3)
C1	0.19789 (19)	0.36352 (12)	0.6498 (2)	0.0207 (4)
C2	0.0903 (2)	0.29840 (13)	0.6173 (2)	0.0236 (4)
H2	0.0831	0.2524	0.6833	0.028*
C3	−0.0028 (2)	0.30118 (13)	0.4924 (2)	0.0227 (4)
H3	−0.0733	0.2562	0.4715	0.027*
C4	0.00270 (19)	0.37013 (12)	0.3918 (2)	0.0205 (4)
C5	−0.0966 (2)	0.37268 (13)	0.2635 (2)	0.0242 (4)
H5	−0.1667	0.3274	0.2434	0.029*
C6	−0.0935 (2)	0.43936 (14)	0.1678 (2)	0.0257 (4)
H6	−0.1613	0.4407	0.0819	0.031*
C7	0.0109 (2)	0.50600 (13)	0.1975 (2)	0.0246 (4)
H7	0.0131	0.5526	0.1312	0.030*
C8	0.1093 (2)	0.50481 (13)	0.3206 (2)	0.0219 (4)
H8	0.1790	0.5504	0.3380	0.026*
C9	0.10912 (19)	0.43680 (12)	0.42252 (19)	0.0189 (4)
C10	0.20982 (19)	0.43225 (12)	0.5546 (2)	0.0190 (4)
C11	0.3197 (2)	0.49736 (13)	0.5896 (2)	0.0210 (4)
H11	0.3245	0.5443	0.5245	0.025*
C12	0.51359 (19)	0.56351 (12)	0.7280 (2)	0.0205 (4)
C13	0.64047 (19)	0.68133 (12)	0.6951 (2)	0.0199 (4)
C14	0.6849 (2)	0.75430 (13)	0.6250 (2)	0.0230 (4)
H14	0.6414	0.7675	0.5303	0.028*
C15	0.7934 (2)	0.80674 (13)	0.6964 (2)	0.0251 (4)
H15	0.8252	0.8562	0.6495	0.030*
C16	0.8576 (2)	0.78866 (13)	0.8360 (2)	0.0256 (4)
H16	0.9320	0.8260	0.8826	0.031*
C17	0.8139 (2)	0.71684 (13)	0.9077 (2)	0.0245 (4)
H17	0.8570	0.7046	1.0029	0.029*
C18	0.7052 (2)	0.66319 (13)	0.8359 (2)	0.0214 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0230 (3)	0.0244 (3)	0.0214 (3)	−0.00141 (19)	0.00199 (18)	0.00103 (19)
O1	0.0272 (7)	0.0245 (8)	0.0252 (7)	−0.0027 (6)	0.0017 (6)	0.0047 (6)
N1	0.0198 (8)	0.0208 (8)	0.0237 (8)	−0.0009 (6)	0.0049 (6)	−0.0016 (7)
N2	0.0210 (8)	0.0221 (8)	0.0220 (8)	−0.0008 (6)	0.0034 (6)	−0.0001 (7)
C1	0.0204 (9)	0.0202 (9)	0.0224 (10)	0.0019 (7)	0.0065 (7)	−0.0006 (7)
C2	0.0261 (10)	0.0194 (9)	0.0276 (10)	−0.0001 (8)	0.0112 (8)	0.0027 (8)
C3	0.0211 (9)	0.0188 (9)	0.0301 (11)	−0.0030 (7)	0.0098 (8)	−0.0036 (8)
C4	0.0197 (9)	0.0193 (9)	0.0241 (10)	0.0010 (7)	0.0081 (7)	−0.0031 (8)
C5	0.0198 (9)	0.0231 (10)	0.0295 (11)	−0.0015 (8)	0.0045 (8)	−0.0066 (8)
C6	0.0240 (10)	0.0278 (11)	0.0235 (10)	0.0055 (8)	0.0006 (8)	−0.0047 (8)
C7	0.0280 (10)	0.0238 (10)	0.0230 (10)	0.0048 (8)	0.0074 (8)	0.0007 (8)
C8	0.0227 (9)	0.0194 (9)	0.0249 (10)	−0.0009 (7)	0.0078 (8)	−0.0013 (8)
C9	0.0185 (9)	0.0178 (9)	0.0216 (9)	0.0025 (7)	0.0067 (7)	−0.0019 (7)
C10	0.0183 (9)	0.0176 (9)	0.0223 (9)	0.0018 (7)	0.0072 (7)	−0.0015 (7)
C11	0.0218 (9)	0.0192 (9)	0.0236 (10)	0.0007 (7)	0.0082 (7)	0.0005 (8)
C12	0.0191 (9)	0.0213 (9)	0.0210 (9)	0.0024 (7)	0.0035 (7)	−0.0024 (7)
C13	0.0181 (9)	0.0186 (9)	0.0236 (10)	0.0031 (7)	0.0053 (7)	−0.0030 (7)
C14	0.0229 (9)	0.0213 (10)	0.0247 (10)	0.0020 (8)	0.0050 (8)	−0.0003 (8)
C15	0.0256 (10)	0.0201 (10)	0.0311 (11)	0.0003 (8)	0.0093 (8)	−0.0006 (8)
C16	0.0214 (9)	0.0235 (10)	0.0319 (11)	−0.0011 (8)	0.0057 (8)	−0.0065 (8)
C17	0.0223 (10)	0.0280 (11)	0.0229 (10)	0.0028 (8)	0.0037 (8)	−0.0041 (8)
C18	0.0204 (9)	0.0220 (9)	0.0227 (10)	0.0028 (8)	0.0067 (7)	−0.0026 (8)

Geometric parameters (Å, º) top

S1—C18	1.740 (2)	C6—H6	0.9500
S1—C12	1.7519 (19)	C7—C8	1.368 (3)
O1—C1	1.343 (2)	C7—H7	0.9500
O1—H1	0.843 (10)	C8—C9	1.417 (3)
N1—C11	1.300 (2)	C8—H8	0.9500
N1—C12	1.395 (2)	C9—C10	1.445 (3)
N2—C12	1.298 (2)	C10—C11	1.430 (3)
N2—C13	1.387 (2)	C11—H11	0.9500
C1—C10	1.400 (3)	C13—C14	1.396 (3)
C1—C2	1.413 (3)	C13—C18	1.408 (3)
C2—C3	1.356 (3)	C14—C15	1.380 (3)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.426 (3)	C15—C16	1.397 (3)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.410 (3)	C16—C17	1.388 (3)
C4—C9	1.420 (3)	C16—H16	0.9500
C5—C6	1.365 (3)	C17—C18	1.392 (3)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.406 (3)

C18—S1—C12	88.83 (9)	C8—C9—C10	123.76 (17)
C1—O1—H1	109 (2)	C4—C9—C10	118.92 (17)
C11—N1—C12	116.99 (16)	C1—C10—C11	119.86 (17)
C12—N2—C13	110.36 (16)	C1—C10—C9	119.17 (17)
O1—C1—C10	122.56 (17)	C11—C10—C9	120.96 (17)
O1—C1—C2	116.63 (17)	N1—C11—C10	122.94 (18)
C10—C1—C2	120.82 (18)	N1—C11—H11	118.5
C3—C2—C1	120.34 (18)	C10—C11—H11	118.5
C3—C2—H2	119.8	N2—C12—N1	126.25 (17)
C1—C2—H2	119.8	N2—C12—S1	116.32 (14)
C2—C3—C4	121.51 (18)	N1—C12—S1	117.44 (14)
C2—C3—H3	119.2	N2—C13—C14	124.58 (17)
C4—C3—H3	119.2	N2—C13—C18	115.42 (17)
C5—C4—C9	120.17 (18)	C14—C13—C18	120.00 (17)
C5—C4—C3	120.62 (17)	C15—C14—C13	118.50 (18)
C9—C4—C3	119.21 (18)	C15—C14—H14	120.8
C6—C5—C4	120.93 (18)	C13—C14—H14	120.7
C6—C5—H5	119.5	C14—C15—C16	121.43 (19)
C4—C5—H5	119.5	C14—C15—H15	119.3
C5—C6—C7	119.37 (19)	C16—C15—H15	119.3
C5—C6—H6	120.3	C17—C16—C15	120.81 (19)
C7—C6—H6	120.3	C17—C16—H16	119.6
C8—C7—C6	120.97 (19)	C15—C16—H16	119.6
C8—C7—H7	119.5	C16—C17—C18	118.07 (19)
C6—C7—H7	119.5	C16—C17—H17	121.0
C7—C8—C9	121.24 (18)	C18—C17—H17	121.0
C7—C8—H8	119.4	C17—C18—C13	121.18 (18)
C9—C8—H8	119.4	C17—C18—S1	129.72 (16)
C8—C9—C4	117.32 (17)	C13—C18—S1	109.07 (14)

O1—C1—C2—C3	−179.77 (17)	C12—N1—C11—C10	−179.24 (16)
C10—C1—C2—C3	0.5 (3)	C1—C10—C11—N1	1.6 (3)
C1—C2—C3—C4	−1.3 (3)	C9—C10—C11—N1	−179.23 (17)
C2—C3—C4—C5	−178.90 (18)	C13—N2—C12—N1	179.17 (17)
C2—C3—C4—C9	0.7 (3)	C13—N2—C12—S1	−0.3 (2)
C9—C4—C5—C6	−0.8 (3)	C11—N1—C12—N2	−8.4 (3)
C3—C4—C5—C6	178.85 (18)	C11—N1—C12—S1	171.09 (14)
C4—C5—C6—C7	0.4 (3)	C18—S1—C12—N2	−0.17 (15)
C5—C6—C7—C8	0.2 (3)	C18—S1—C12—N1	−179.72 (15)
C6—C7—C8—C9	−0.3 (3)	C12—N2—C13—C14	−178.50 (17)
C7—C8—C9—C4	−0.1 (3)	C12—N2—C13—C18	0.8 (2)
C7—C8—C9—C10	−179.70 (17)	N2—C13—C14—C15	179.92 (17)
C5—C4—C9—C8	0.6 (3)	C18—C13—C14—C15	0.6 (3)
C3—C4—C9—C8	−179.03 (16)	C13—C14—C15—C16	−0.6 (3)
C5—C4—C9—C10	−179.76 (16)	C14—C15—C16—C17	0.1 (3)
C3—C4—C9—C10	0.6 (3)	C15—C16—C17—C18	0.4 (3)
O1—C1—C10—C11	0.4 (3)	C16—C17—C18—C13	−0.4 (3)
C2—C1—C10—C11	−179.91 (17)	C16—C17—C18—S1	−178.59 (15)
O1—C1—C10—C9	−178.88 (16)	N2—C13—C18—C17	−179.46 (17)
C2—C1—C10—C9	0.9 (3)	C14—C13—C18—C17	−0.1 (3)
C8—C9—C10—C1	178.24 (17)	N2—C13—C18—S1	−0.9 (2)
C4—C9—C10—C1	−1.4 (3)	C14—C13—C18—S1	178.42 (14)
C8—C9—C10—C11	−1.0 (3)	C12—S1—C18—C17	178.94 (19)
C4—C9—C10—C11	179.39 (17)	C12—S1—C18—C13	0.60 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84 (1)	1.82 (2)	2.573 (2)	148 (3)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂N₂OS
M_r	304.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	9.6398 (2), 14.9687 (4), 9.6646 (2)
β (°)	101.323 (2)
V (Å³)	1367.41 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.25 × 0.20 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.943, 0.988
No. of measured, independent and observed [I > 2˘I)] reflections	12442, 3139, 2396
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.122, 1.02
No. of reflections	3139
No. of parameters	203
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.23

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84 (1)	1.82 (2)	2.573 (2)	148 (3)

Acknowledgements

We thank King Abdul Aziz University (grant No. 171/428) and the University of Malaya for supporting this study.

References

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