[2-(4-Chloro­phen­yl)-1,3-selenazol-4-yl]methanol

Cui, J.; Li, C.; Qiao, Y.

doi:10.1107/S1600536812048088

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3458

doi:10.1107/S1600536812048088

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[2-(4-Chlorophenyl)-1,3-selenazol-4-yl]methanol

Jichun Cui,^a ^* Chuan Li ^a and Yanling Qiao ^a

^aShandong Provincial Key Laboratory of Chemical Energy Storage, and Novel Cell Technology, School of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: jchcui@163.com

(Received 2 November 2012; accepted 22 November 2012; online 28 November 2012)

In the title compound, C₁₀H₈ClNOSe, the dihedral angle between benzene and selenazole rings is 11.4 (3)° and the hydroxymethyl group is bent from the selenazole ring, making a dihedral angle of 63.8 (3)°. In the crystal, molecules are linked into inversion dimers by pairs of O—H⋯N hydrogen bonds. Roof-tile-like stacking of the molecules 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_r = 272.58
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.104
S = 1.01
1742 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.45 e Å⁻³

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) -x+1, -y, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812048088/qk2047sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812048088/qk2047Isup3.cml

checkCIF report

Comment top

It has well been confirmed that selenium-containing heterocyclic compounds are of considerable biochemical and pharmacological relevance. Thus, derivatives of selenazole have been extensively studied not only because of their interesting reactivities but also because of their pharmaceutical applications (Koketsu & Ishihara, 2003; Geisler et al., 2004). Interested in this field, the title compound, a derivative of selenazole, was prepared and its crystal structure presented (Fig. 1). In the title compound, C₁₀H₈NOClSe, the dihedral angle between the nearly planar benzene and selenazole rings is 11.4 (3)°. The dihedral angle between the selenazole ring and the hydroxymethyl group, defined by C9—C10–O1, is 63.8 (3)°. All the bond lengths and angles are normal and correspond to those observed in the related compounds (Shen et al., 2011; Shi & Zhao, 2007). In the crystal structure, pairs of molecules are disposed about an inversion center, generating dimers linked by intermolecular O—H···N hydrogen bonds (Fig. 2 and Table 1). The aromatic parts of the molecules are stacked along [010] (b = 4.5707 (4) Å) in a roof tile-like fashion enabling slipped π-π-stacking interactions. The face-to-face distance of the aromatic parts of the molecules (Se1, N1, C1 – C9) is 3.57 Å and their slippage 2.85 Å approximately parallel to the ring-to-ring bond C4—C7 (Fig. 2). This brings Cl1 in a position above/below the ring centroid of an adjacent benzene ring (Cl···centroid (C1 – C6) = 3.68 Å).

Related literature top

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 top

2-(4-Chlorophenyl)-4-chloromethyl-1,3-selenazole (0.01 mol) (Shafiee et al., 1979) was added to dilute sulfuric acid (75 ml, 3.5 mol L^-1) and heated at reflux for 8 h. The solution was made alkaline with dilute sodium hydroxide and extracted with chloroform. The organic layer was dried with Na₂SO₄, filtered, and evaporated and the obtained solid was recrystallized from ethanol. Clear block-shaped crystals were obtained.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 molecular structure of the title compound with 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound indicating H-bonds by dashed lines and π-π-stacking by red double arrows (see Table 1 and text).

[2-(4-Chlorophenyl)-1,3-selenazol-4-yl]methanol top

Crystal data top

C₁₀H₈ClNOSe	F(000) = 536
M_r = 272.58	D_x = 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

Data collection top

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

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0525P)²] where P = (F_o² + 2F_c²)/3
1742 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₀H₈ClNOSe	V = 1003.01 (16) Å³
M_r = 272.58	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.8150 (15) Å	µ = 3.97 mm⁻¹
b = 4.5707 (4) Å	T = 298 K
c = 14.9123 (14) Å	0.35 × 0.32 × 0.15 mm
β = 96.642 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	1742 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1318 reflections with I > 2σ(I)
T_min = 0.337, T_max = 0.587	R_int = 0.059
4466 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.01	Δρ_max = 0.45 e Å⁻³
1742 reflections	Δρ_min = −0.45 e Å⁻³
128 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₈ClNOSe
M_r	272.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	14.8150 (15), 4.5707 (4), 14.9123 (14)
β (°)	96.642 (1)
V (Å³)	1003.01 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.97
Crystal size (mm)	0.35 × 0.32 × 0.15

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.337, 0.587
No. of measured, independent and observed [I > 2σ(I)] reflections	4466, 1742, 1318
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.104, 1.01
No. of reflections	1742
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.45

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	2.07	2.891 (5)	173.6

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

We acknowledge the National Natural Foundation of China (21105042), the National Basic Research Program (2010CB234601) and the Natural Science Foundation of Shandong Province (ZR2011BM007, ZR2010BQ021) for financial support.

References

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