[2-(4-Chloro-phen-yl)-1,3-selenazol-4-yl]methanol.

In the title compound, C10H8ClNOSe, the dihedral angle between benzene and selenazole rings is 11.4 (3)° and the hy-droxy-methyl group is bent from the selenazole ring, making a dihedral angle of 63.8 (3)°. In the crystal, mol-ecules are linked into inversion dimers by pairs of O-H⋯N hydrogen bonds. Roof-tile-like stacking of the mol-ecules along [010] [b = 4.5707 (4) Å] is observed, with the benzene and selenazole rings separated by a face-to-face distance of 3.57 Å and a mutual slippage of 2.85 Å.

Related literature

For the synthesis of 1,3-selenazoles and their biological activity, see: Shafiee et al. (1979 ▶); Koketsu & Ishihara (2003 ▶); Geisler et al. (2004 ▶). For crystal structures of 1,3-selenazole derivatives, see: Shen et al. (2011 ▶); Shi & Zhao, (2007 ▶).

Experimental

Crystal data

C10H8ClNOSe

M = 272.58

Monoclinic,

a = 14.8150 (15) Å

b = 4.5707 (4) Å

c = 14.9123 (14) Å

β = 96.642 (1)°

V = 1003.01 (16) Å3

Z = 4

Mo Kα radiation

μ = 3.97 mm−1

T = 298 K

0.35 × 0.32 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.337, T max = 0.587

4466 measured reflections

1742 independent reflections

1318 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.104

S = 1.01

1742 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.45 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048088/qk2047sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048088/qk2047Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048088/qk2047Isup3.cml

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

C10H8ClNOSe	F(000) = 536
Mr = 272.58	Dx = 1.805 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1928 reflections
a = 14.8150 (15) Å	θ = 2.8–27.1°
b = 4.5707 (4) Å	µ = 3.97 mm−1
c = 14.9123 (14) Å	T = 298 K
β = 96.642 (1)°	Block, white
V = 1003.01 (16) Å3	0.35 × 0.32 × 0.15 mm
Z = 4

Bruker SMART APEX CCD diffractometer	1742 independent reflections
Radiation source: fine-focus sealed tube	1318 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
π and ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −15→17
Tmin = 0.337, Tmax = 0.587	k = −5→5
4466 measured reflections	l = −17→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0525P)2] where P = (Fo2 + 2Fc2)/3
1742 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

	x	y	z	Uiso*/Ueq
Se1	0.74166 (3)	0.13939 (10)	0.30636 (3)	0.0423 (2)
Cl1	0.93843 (9)	1.0498 (3)	0.66855 (9)	0.0586 (4)
O1	0.4348 (2)	−0.0090 (8)	0.3910 (2)	0.0465 (8)
H1	0.4149	−0.0297	0.4396	0.070*
N1	0.6330 (2)	0.1313 (7)	0.4388 (2)	0.0313 (8)
C1	0.8698 (3)	0.8234 (9)	0.5942 (3)	0.0394 (11)
C2	0.7838 (3)	0.7563 (10)	0.6124 (3)	0.0401 (11)
H2	0.7612	0.8350	0.6628	0.048*
C3	0.7307 (3)	0.5702 (9)	0.5551 (3)	0.0352 (10)
H3	0.6722	0.5232	0.5672	0.042*
C4	0.7644 (3)	0.4523 (9)	0.4790 (2)	0.0308 (10)
C5	0.8507 (3)	0.5313 (11)	0.4624 (3)	0.0410 (11)
H5	0.8735	0.4589	0.4112	0.049*
C6	0.9042 (4)	0.7147 (11)	0.5196 (3)	0.0503 (13)
H6	0.9626	0.7637	0.5078	0.060*
C7	0.7083 (3)	0.2511 (9)	0.4200 (2)	0.0285 (9)
C8	0.6372 (3)	−0.0813 (9)	0.2973 (3)	0.0373 (11)
H8	0.6171	−0.1989	0.2481	0.045*
C9	0.5933 (3)	−0.0506 (9)	0.3712 (2)	0.0293 (9)
C10	0.5071 (3)	−0.2087 (10)	0.3850 (3)	0.0410 (11)
H10A	0.4912	−0.3417	0.3349	0.049*
H10B	0.5167	−0.3236	0.4399	0.049*

	U11	U22	U33	U12	U13	U23
Se1	0.0457 (4)	0.0490 (4)	0.0337 (3)	−0.0017 (2)	0.0118 (2)	−0.0033 (2)
Cl1	0.0543 (9)	0.0538 (9)	0.0629 (8)	−0.0135 (6)	−0.0131 (6)	−0.0081 (6)
O1	0.037 (2)	0.060 (2)	0.0427 (18)	0.0018 (18)	0.0058 (15)	0.0102 (16)
N1	0.034 (2)	0.029 (2)	0.0299 (17)	0.0012 (16)	−0.0013 (15)	−0.0014 (14)
C1	0.042 (3)	0.031 (3)	0.042 (2)	−0.002 (2)	−0.008 (2)	0.0014 (19)
C2	0.049 (3)	0.037 (3)	0.034 (2)	−0.008 (2)	0.005 (2)	−0.0008 (19)
C3	0.027 (3)	0.041 (3)	0.039 (2)	−0.004 (2)	0.0053 (19)	0.0034 (19)
C4	0.035 (3)	0.029 (2)	0.028 (2)	0.0021 (19)	0.0035 (18)	0.0047 (16)
C5	0.027 (3)	0.046 (3)	0.052 (3)	−0.002 (2)	0.013 (2)	−0.009 (2)
C6	0.036 (3)	0.047 (3)	0.069 (3)	−0.004 (2)	0.010 (3)	−0.005 (3)
C7	0.030 (3)	0.029 (2)	0.0265 (19)	0.0094 (19)	0.0022 (17)	0.0039 (17)
C8	0.040 (3)	0.039 (3)	0.032 (2)	0.004 (2)	−0.0018 (19)	−0.0006 (18)
C9	0.027 (2)	0.029 (2)	0.030 (2)	0.0053 (18)	−0.0034 (18)	0.0012 (17)
C10	0.042 (3)	0.039 (3)	0.039 (2)	−0.007 (2)	−0.004 (2)	−0.002 (2)

Se1—C8	1.839 (5)	C3—H3	0.9300
Se1—C7	1.889 (4)	C4—C5	1.378 (6)
Cl1—C1	1.753 (4)	C4—C7	1.463 (6)
O1—C10	1.419 (6)	C5—C6	1.380 (6)
O1—H1	0.8200	C5—H5	0.9300
N1—C7	1.303 (5)	C6—H6	0.9300
N1—C9	1.383 (5)	C8—C9	1.350 (6)
C1—C2	1.367 (6)	C8—H8	0.9300
C1—C6	1.370 (6)	C9—C10	1.502 (6)
C2—C3	1.385 (6)	C10—H10A	0.9700
C2—H2	0.9300	C10—H10B	0.9700
C3—C4	1.399 (5)
C8—Se1—C7	84.78 (19)	C1—C6—C5	118.8 (5)
C10—O1—H1	109.5	C1—C6—H6	120.6
C7—N1—C9	113.5 (4)	C5—C6—H6	120.6
C2—C1—C6	121.5 (4)	N1—C7—C4	125.2 (4)
C2—C1—Cl1	119.6 (4)	N1—C7—Se1	113.5 (3)
C6—C1—Cl1	118.9 (4)	C4—C7—Se1	121.3 (3)
C1—C2—C3	119.5 (4)	C9—C8—Se1	111.3 (3)
C1—C2—H2	120.3	C9—C8—H8	124.3
C3—C2—H2	120.3	Se1—C8—H8	124.3
C2—C3—C4	120.4 (4)	C8—C9—N1	116.9 (4)
C2—C3—H3	119.8	C8—C9—C10	123.9 (4)
C4—C3—H3	119.8	N1—C9—C10	119.1 (4)
C5—C4—C3	118.1 (4)	O1—C10—C9	111.1 (4)
C5—C4—C7	122.0 (4)	O1—C10—H10A	109.4
C3—C4—C7	119.9 (4)	C9—C10—H10A	109.4
C6—C5—C4	121.8 (4)	O1—C10—H10B	109.4
C6—C5—H5	119.1	C9—C10—H10B	109.4
C4—C5—H5	119.1	H10A—C10—H10B	108.0
C6—C1—C2—C3	1.1 (7)	C3—C4—C7—N1	−11.4 (6)
Cl1—C1—C2—C3	−178.0 (3)	C5—C4—C7—Se1	−11.1 (6)
C1—C2—C3—C4	−0.2 (7)	C3—C4—C7—Se1	169.0 (3)
C2—C3—C4—C5	−1.1 (6)	C8—Se1—C7—N1	0.0 (3)
C2—C3—C4—C7	178.7 (4)	C8—Se1—C7—C4	179.7 (3)
C3—C4—C5—C6	1.7 (7)	C7—Se1—C8—C9	0.3 (3)
C7—C4—C5—C6	−178.2 (5)	Se1—C8—C9—N1	−0.6 (5)
C2—C1—C6—C5	−0.6 (7)	Se1—C8—C9—C10	−178.4 (3)
Cl1—C1—C6—C5	178.5 (4)	C7—N1—C9—C8	0.6 (5)
C4—C5—C6—C1	−0.8 (7)	C7—N1—C9—C10	178.6 (4)
C9—N1—C7—C4	−180.0 (4)	C8—C9—C10—O1	−117.4 (4)
C9—N1—C7—Se1	−0.3 (4)	N1—C9—C10—O1	64.8 (5)
C5—C4—C7—N1	168.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	2.07	2.891 (5)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	2.07	2.891 (5)	174

Symmetry code: (i) .