2-(1,3-Benzothia-zol-2-ylimino-meth-yl)-2-naphthol.

In the title mol-ecule, C(18)H(12)N(2)OS, the dihedral angle between the two fused-ring systems is 7.2 (1)°. The hydr-oxy group forms an intra-molecular 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 = 304.36

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.122

S = 1.02

3139 reflections

203 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.23 e Å−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 ▶).

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

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

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

C18H12N2OS	F(000) = 632
Mr = 304.36	Dx = 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

Bruker SMART APEX diffractometer	3139 independent reflections
Radiation source: fine-focus sealed tube	2396 reflections with I > 2˘I)
graphite	Rint = 0.051
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.943, Tmax = 0.988	k = −19→19
12442 measured reflections	l = −12→12

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(Fo2) + (0.0612P)2 + 0.543P] where P = (Fo2 + 2Fc2)/3
3139 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.53 e Å−3
1 restraint	Δρmin = −0.23 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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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)

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)