A monoclinic modification of 2-[(1,3-benzothia-zol-2-yl)imino-meth-yl]phenol.

In the title Schiff base, C(14)H(10)N(2)OS, the azomethine double bond is in an E configuration; the benzothiazolyl ring (r.m.s. deviation = 0.007 Å) is coplanar with the phenyl-ene ring (r.m.s. deviation = 0.007 Å), the two rings being slightly bent at 2.6 (1)°. The hy-droxy H atom forms an intra-molecular hydrogen bond to the imino group. The bond dimensions of the monoclinic modification are similar to those of the ortho-rhom-bic modification [Liu et al. (2009 ▶). Acta Cryst. E65, o738].

Related literature

For an ortho­rhom­bic modification of this structure, see: Liu et al. (2009 ▶).

Experimental

Crystal data

C14H10N2OS

M = 254.30

Monoclinic,

a = 8.6391 (4) Å

b = 6.2313 (4) Å

c = 11.4459 (8) Å

β = 108.893 (1)°

V = 582.97 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.14 × 0.13 × 0.08 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.964, T max = 0.979

5307 measured reflections

2599 independent reflections

2512 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.05

2599 reflections

164 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1242 Friedel pairs

Flack parameter: 0.27 (8)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023755/nk2043sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023755/nk2043Isup2.hkl

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

C14H10N2OS	F(000) = 264
Mr = 254.30	Dx = 1.449 Mg m−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 3896 reflections
a = 8.6391 (4) Å	θ = 2.6–28.3°
b = 6.2313 (4) Å	µ = 0.26 mm−1
c = 11.4459 (8) Å	T = 100 K
β = 108.893 (1)°	Prism, orange
V = 582.97 (6) Å3	0.14 × 0.13 × 0.08 mm
Z = 2

Bruker SMART APEX diffractometer	2599 independent reflections
Radiation source: fine-focus sealed tube	2512 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
Tmin = 0.964, Tmax = 0.979	k = −8→8
5307 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0831P)2 + 0.0645P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2599 reflections	Δρmax = 0.40 e Å−3
164 parameters	Δρmin = −0.25 e Å−3
2 restraints	Absolute structure: Flack (1983), 1242 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.27 (8)

	x	y	z	Uiso*/Ueq
S1	0.50007 (6)	0.06429 (7)	0.49993 (5)	0.01864 (15)
O1	0.7048 (2)	0.5684 (3)	0.89741 (16)	0.0277 (4)
H1	0.6924	0.4623	0.8462	0.042*
N1	0.6095 (2)	0.3254 (3)	0.70823 (16)	0.0186 (4)
N2	0.7613 (2)	0.0261 (3)	0.69409 (17)	0.0193 (4)
C1	0.5700 (3)	0.6867 (4)	0.84466 (19)	0.0195 (4)
C2	0.5445 (3)	0.8696 (4)	0.9059 (2)	0.0222 (4)
H2	0.6227	0.9096	0.9825	0.027*
C3	0.4058 (3)	0.9936 (4)	0.8561 (2)	0.0226 (5)
H3	0.3895	1.1183	0.8985	0.027*
C4	0.2898 (3)	0.9363 (3)	0.7441 (2)	0.0228 (5)
H4	0.1937	1.0201	0.7108	0.027*
C5	0.3153 (3)	0.7571 (4)	0.68168 (19)	0.0214 (4)
H5	0.2366	0.7193	0.6049	0.026*
C6	0.4554 (3)	0.6303 (3)	0.72981 (19)	0.0175 (4)
C7	0.4806 (3)	0.4437 (3)	0.6638 (2)	0.0188 (4)
H7	0.4019	0.4071	0.5868	0.023*
C8	0.6349 (3)	0.1448 (3)	0.64566 (19)	0.0184 (4)
C9	0.7588 (3)	−0.1475 (3)	0.61665 (18)	0.0178 (4)
C10	0.8777 (3)	−0.3090 (4)	0.6428 (2)	0.0228 (4)
H10	0.9681	−0.3056	0.7170	0.027*
C11	0.8612 (3)	−0.4729 (4)	0.5589 (2)	0.0249 (5)
H11	0.9414	−0.5832	0.5757	0.030*
C12	0.7290 (3)	−0.4798 (4)	0.4498 (2)	0.0229 (5)
H12	0.7212	−0.5939	0.3931	0.027*
C13	0.6081 (3)	−0.3219 (4)	0.4225 (2)	0.0213 (4)
H13	0.5170	−0.3277	0.3488	0.026*
C14	0.6257 (3)	−0.1556 (3)	0.5070 (2)	0.0190 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0181 (2)	0.0172 (2)	0.0187 (2)	−0.0003 (2)	0.00322 (17)	−0.00262 (19)
O1	0.0216 (9)	0.0314 (10)	0.0232 (9)	0.0063 (7)	−0.0024 (7)	−0.0064 (6)
N1	0.0193 (8)	0.0166 (8)	0.0183 (8)	−0.0016 (7)	0.0040 (7)	−0.0015 (7)
N2	0.0222 (10)	0.0148 (8)	0.0191 (9)	−0.0020 (7)	0.0042 (7)	−0.0008 (7)
C1	0.0181 (10)	0.0220 (10)	0.0181 (9)	−0.0008 (8)	0.0051 (8)	−0.0004 (8)
C2	0.0235 (11)	0.0215 (10)	0.0211 (10)	−0.0032 (9)	0.0066 (9)	−0.0052 (8)
C3	0.0265 (12)	0.0193 (10)	0.0263 (11)	−0.0017 (9)	0.0144 (9)	−0.0023 (8)
C4	0.0228 (12)	0.0211 (11)	0.0255 (11)	0.0054 (8)	0.0095 (9)	0.0051 (8)
C5	0.0197 (10)	0.0245 (10)	0.0190 (9)	0.0002 (9)	0.0048 (8)	0.0025 (8)
C6	0.0179 (10)	0.0178 (9)	0.0164 (9)	−0.0011 (8)	0.0050 (8)	−0.0012 (8)
C7	0.0173 (10)	0.0200 (11)	0.0177 (10)	−0.0029 (8)	0.0035 (8)	−0.0002 (7)
C8	0.0196 (10)	0.0168 (10)	0.0182 (9)	−0.0025 (8)	0.0051 (8)	0.0001 (7)
C9	0.0221 (10)	0.0148 (9)	0.0175 (9)	−0.0025 (8)	0.0077 (8)	−0.0021 (8)
C10	0.0228 (11)	0.0209 (10)	0.0249 (10)	0.0016 (9)	0.0081 (8)	0.0032 (8)
C11	0.0245 (12)	0.0224 (11)	0.0311 (12)	0.0032 (9)	0.0136 (10)	0.0047 (9)
C12	0.0282 (13)	0.0182 (10)	0.0276 (12)	−0.0036 (9)	0.0166 (10)	−0.0058 (9)
C13	0.0205 (10)	0.0224 (11)	0.0208 (10)	−0.0043 (9)	0.0063 (8)	−0.0018 (8)
C14	0.0178 (10)	0.0156 (9)	0.0249 (10)	0.0012 (8)	0.0088 (8)	0.0022 (8)

S1—C14	1.733 (2)	C4—H4	0.9500
S1—C8	1.770 (2)	C5—C6	1.400 (3)
O1—C1	1.345 (3)	C5—H5	0.9500
O1—H1	0.8672	C6—C7	1.442 (3)
N1—C7	1.294 (3)	C7—H7	0.9500
N1—C8	1.389 (3)	C9—C10	1.399 (3)
N2—C8	1.286 (3)	C9—C14	1.402 (3)
N2—C9	1.394 (3)	C10—C11	1.378 (3)
C1—C2	1.393 (3)	C10—H10	0.9500
C1—C6	1.410 (3)	C11—C12	1.393 (4)
C2—C3	1.383 (4)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.395 (3)
C3—C4	1.394 (4)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.392 (3)
C4—C5	1.381 (3)	C13—H13	0.9500
C14—S1—C8	88.21 (11)	N1—C7—H7	119.7
C1—O1—H1	102.4	C6—C7—H7	119.7
C7—N1—C8	121.20 (18)	N2—C8—N1	119.83 (19)
C8—N2—C9	109.65 (18)	N2—C8—S1	116.81 (16)
O1—C1—C2	118.56 (19)	N1—C8—S1	123.36 (17)
O1—C1—C6	121.8 (2)	N2—C9—C10	124.3 (2)
C2—C1—C6	119.7 (2)	N2—C9—C14	115.84 (19)
C3—C2—C1	120.4 (2)	C10—C9—C14	119.9 (2)
C3—C2—H2	119.8	C11—C10—C9	118.8 (2)
C1—C2—H2	119.8	C11—C10—H10	120.6
C2—C3—C4	120.3 (2)	C9—C10—H10	120.6
C2—C3—H3	119.8	C10—C11—C12	121.1 (2)
C4—C3—H3	119.8	C10—C11—H11	119.4
C5—C4—C3	119.7 (2)	C12—C11—H11	119.4
C5—C4—H4	120.2	C13—C12—C11	121.1 (2)
C3—C4—H4	120.2	C13—C12—H12	119.5
C4—C5—C6	121.0 (2)	C11—C12—H12	119.5
C4—C5—H5	119.5	C14—C13—C12	117.7 (2)
C6—C5—H5	119.5	C14—C13—H13	121.2
C5—C6—C1	118.87 (19)	C12—C13—H13	121.2
C5—C6—C7	120.47 (19)	C13—C14—C9	121.5 (2)
C1—C6—C7	120.7 (2)	C13—C14—S1	129.07 (18)
N1—C7—C6	120.7 (2)	C9—C14—S1	109.47 (16)
O1—C1—C2—C3	−178.7 (2)	C14—S1—C8—N2	1.30 (18)
C6—C1—C2—C3	1.4 (3)	C14—S1—C8—N1	−178.28 (18)
C1—C2—C3—C4	0.2 (4)	C8—N2—C9—C10	−179.1 (2)
C2—C3—C4—C5	−1.2 (4)	C8—N2—C9—C14	0.2 (3)
C3—C4—C5—C6	0.6 (3)	N2—C9—C10—C11	179.7 (2)
C4—C5—C6—C1	0.9 (3)	C14—C9—C10—C11	0.4 (3)
C4—C5—C6—C7	−180.0 (2)	C9—C10—C11—C12	−0.1 (3)
O1—C1—C6—C5	178.2 (2)	C10—C11—C12—C13	−0.6 (4)
C2—C1—C6—C5	−1.9 (3)	C11—C12—C13—C14	1.1 (3)
O1—C1—C6—C7	−0.9 (3)	C12—C13—C14—C9	−0.8 (3)
C2—C1—C6—C7	179.0 (2)	C12—C13—C14—S1	179.15 (17)
C8—N1—C7—C6	179.8 (2)	N2—C9—C14—C13	−179.33 (19)
C5—C6—C7—N1	−179.6 (2)	C10—C9—C14—C13	0.0 (3)
C1—C6—C7—N1	−0.5 (3)	N2—C9—C14—S1	0.7 (2)
C9—N2—C8—N1	178.51 (18)	C10—C9—C14—S1	−179.89 (17)
C9—N2—C8—S1	−1.1 (2)	C8—S1—C14—C13	179.0 (2)
C7—N1—C8—N2	−177.6 (2)	C8—S1—C14—C9	−1.04 (16)
C7—N1—C8—S1	2.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.87	1.73	2.550 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.87	1.73	2.550 (2)	156