2-Phenyl-1,3-selenazole-4-carb­oxy­lic acid

Shen, J.-B.; Lv, X.; Chen, J.-F.; Zhou, Y.-F.; Zhao, G.-L.

doi:10.1107/S1600536811007185

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o803

doi:10.1107/S1600536811007185

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2-Phenyl-1,3-selenazole-4-carboxylic acid

Jin-Bei Shen,^a Xin Lv,^a Ji-Fei Chen,^a Yu-Feng Zhou ^a and Guo-Liang Zhao ^a,^b ^*

^aCollege of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China, and ^bZhejiang Normal University Xingzhi College, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: sky53@zjnu.cn

(Received 23 February 2011; accepted 25 February 2011; online 5 March 2011)

In the title compound, C₁₀H₇NO₂Se, the two rings are twisted, making a dihedral angle of 12.42 (9)°. In the crystal, pairs of molecules are disposed about an inversion center, generating O—H⋯O hydrogen-bonded dimers.

Related literature

For the synthesis, see: Zhao et al. (2010 ). For related structures, see: Srivastava & Robins (1983 ); Boritzki et al. (1985 ); Shen et al. (2011 ).

Experimental

Crystal data

C₁₀H₇NO₂Se
M_r = 252.13
Monoclinic, P 2₁ /c
a = 8.0817 (3) Å
b = 11.5661 (4) Å
c = 11.6295 (4) Å
β = 117.168 (2)°
V = 967.12 (6) Å³
Z = 4
Mo Kα radiation
μ = 3.85 mm⁻¹
T = 296 K
0.23 × 0.22 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.437, T_max = 0.479
7502 measured reflections
1705 independent reflections
1487 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.063
S = 1.05
1705 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H7⋯O2ⁱ	0.82	1.81	2.623 (2)	171
Symmetry code: (i) -x+1, -y-1, -z+1.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811007185/ng5124sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007185/ng5124Isup2.hkl

checkCIF report

Comment top

It has well been confirmed that the derivatives of selenazole are important in multiple fields such as chemistry and biochemistry owing to their biological activities (Srivastava et al., 1983;Boritzki et al.,1985). Interested in this field, we have been engaged in a major effort directed toward the development of syntheses of new selenazole carboxylic acid and their transition metal complexes. In a few of articles we have reported our partial research results (Zhao et al., 2010;Shen et al., 2011). Herein,we crystallize the organic ligand 2-phenyl-4-selenazole carboxylic acid.

The structure of the title, (C₁₀H₇NO₂Se),suitable for X-ray, was obtained by chance. The structure of the complex is shown in Fig.1, which reveals that all atoms in each molecule are nearly coplanar in the centrosymmetric unit. The molecule is essentially planar with the dihedral angle between two neighboring rings are 12.415 (89)°. In the molecule of 2-phenyl-4-selenazole carboxylic acid,the Se—C bond length range from 1.832 (2) Å-1.891 (2)Å and the angle C—Se—C is 84.78 (10)°.

The molecules arranged in the crystal at regular intervals with O—H···O hydrogen bonds. The end to end hydrogen-bonding interactions lead to the formation a one-dimensional structure framework along the b axis, Fig 2. Between adjacent triple-helix chains there exist weak π···π interactions.

Related literature top

For the synthesis, see: Zhao et al. (2010). For related structures, see: Srivastava & Robins (1983); Boritzki et al. (1985); Shen et al. (2011).

Experimental top

Reagents and solvents used were of commercially available quality and without purified before using. K₂Cr₂O₇ (0.588 g, 2 mmol) was added to a mixed solution of acetic acid (50 ml) with 2-phenyl-4-selenazole carbinol (0.248 g, 1 mmol) under stirred conditions at room temperature. Few minutes later lots of red deposit appeared. After the deposit was filtered out, a light red solution was kept for evaporating. Some red single crystals were obtained about 19 days later.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex, showing the atom- labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The stacking plot of the title compound, showing H-bond interactions (dashed lines) and π···π stacking interactions.

2-Phenyl-1,3-selenazole-4-carboxylic acid top

Crystal data top

C₁₀H₇NO₂Se	F(000) = 496
M_r = 252.13	D_x = 1.732 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4000 reflections
a = 8.0817 (3) Å	θ = 2.6–25.0°
b = 11.5661 (4) Å	µ = 3.85 mm⁻¹
c = 11.6295 (4) Å	T = 296 K
β = 117.168 (2)°	Block, red
V = 967.12 (6) Å³	0.23 × 0.22 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	1705 independent reflections
Radiation source: fine-focus sealed tube	1487 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: none pixels mm^-1	θ_max = 25.0°, θ_min = 2.6°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
T_min = 0.437, T_max = 0.479	l = −13→13
7502 measured reflections

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0341P)² + 0.3951P] where P = (F_o² + 2F_c²)/3
1705 reflections	(Δ/σ)_max = 0.001
127 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₀H₇NO₂Se	V = 967.12 (6) Å³
M_r = 252.13	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0817 (3) Å	µ = 3.85 mm⁻¹
b = 11.5661 (4) Å	T = 296 K
c = 11.6295 (4) Å	0.23 × 0.22 × 0.19 mm
β = 117.168 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	1705 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1487 reflections with I > 2σ(I)
T_min = 0.437, T_max = 0.479	R_int = 0.022
7502 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.05	Δρ_max = 0.43 e Å⁻³
1705 reflections	Δρ_min = −0.19 e Å⁻³
127 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Se1	0.26583 (4)	−0.04306 (2)	0.60598 (2)	0.04992 (12)
O1	0.4357 (3)	−0.41679 (16)	0.5986 (2)	0.0685 (6)
H7	0.4714	−0.4799	0.5865	0.103*
O2	0.4478 (3)	−0.37486 (15)	0.41673 (18)	0.0661 (6)
N1	0.3215 (3)	−0.15135 (15)	0.42195 (18)	0.0382 (4)
C1	0.1846 (4)	0.0295 (2)	0.2299 (3)	0.0543 (7)
H1	0.2010	−0.0436	0.2033	0.065*
C2	0.1285 (4)	0.1208 (2)	0.1426 (3)	0.0655 (8)
H2	0.1085	0.1088	0.0581	0.079*
C3	0.1028 (4)	0.2287 (2)	0.1809 (3)	0.0595 (7)
H3	0.0630	0.2894	0.1220	0.071*
C4	0.1357 (4)	0.2467 (2)	0.3054 (3)	0.0635 (8)
H4	0.1201	0.3201	0.3315	0.076*
C5	0.1921 (4)	0.1566 (2)	0.3930 (3)	0.0538 (6)
H5	0.2141	0.1696	0.4778	0.065*
C6	0.2159 (3)	0.04648 (18)	0.3548 (2)	0.0388 (5)
C7	0.2713 (3)	−0.05191 (17)	0.4454 (2)	0.0364 (5)
C8	0.3408 (3)	−0.1944 (2)	0.6245 (2)	0.0438 (5)
H8	0.3632	−0.2404	0.6957	0.053*
C9	0.3587 (3)	−0.22941 (18)	0.5206 (2)	0.0386 (5)
C10	0.4173 (4)	−0.3472 (2)	0.5075 (2)	0.0455 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.0692 (2)	0.04354 (17)	0.04006 (17)	0.01159 (11)	0.02764 (14)	0.00007 (10)
O1	0.1212 (18)	0.0434 (9)	0.0619 (13)	0.0252 (11)	0.0600 (13)	0.0203 (9)
O2	0.1187 (17)	0.0448 (10)	0.0514 (12)	0.0251 (10)	0.0533 (12)	0.0128 (8)
N1	0.0453 (11)	0.0337 (10)	0.0362 (10)	0.0043 (8)	0.0191 (8)	0.0046 (8)
C1	0.0716 (18)	0.0431 (14)	0.0488 (16)	0.0075 (12)	0.0281 (14)	0.0073 (11)
C2	0.084 (2)	0.0629 (18)	0.0483 (17)	0.0095 (15)	0.0292 (15)	0.0149 (14)
C3	0.0576 (16)	0.0517 (15)	0.068 (2)	0.0135 (12)	0.0281 (14)	0.0258 (14)
C4	0.0721 (19)	0.0394 (14)	0.084 (2)	0.0153 (13)	0.0404 (17)	0.0128 (13)
C5	0.0674 (17)	0.0421 (14)	0.0571 (17)	0.0113 (12)	0.0331 (14)	0.0054 (11)
C6	0.0363 (12)	0.0367 (12)	0.0440 (13)	0.0025 (9)	0.0187 (10)	0.0044 (9)
C7	0.0371 (11)	0.0357 (11)	0.0354 (12)	0.0012 (9)	0.0157 (9)	0.0013 (9)
C8	0.0543 (14)	0.0412 (12)	0.0357 (13)	0.0048 (11)	0.0204 (11)	0.0041 (10)
C9	0.0438 (13)	0.0357 (11)	0.0360 (12)	0.0027 (9)	0.0179 (10)	0.0031 (9)
C10	0.0620 (15)	0.0376 (12)	0.0404 (13)	0.0061 (11)	0.0264 (12)	0.0063 (10)

Geometric parameters (Å, º) top

Se1—C8	1.832 (2)	C2—H2	0.9300
Se1—C7	1.891 (2)	C3—C4	1.363 (4)
O1—C10	1.284 (3)	C3—H3	0.9300
O1—H7	0.8201	C4—C5	1.382 (4)
O2—C10	1.230 (3)	C4—H4	0.9300
N1—C7	1.289 (3)	C5—C6	1.391 (3)
N1—C9	1.381 (3)	C5—H5	0.9300
C1—C6	1.370 (4)	C6—C7	1.474 (3)
C1—C2	1.390 (4)	C8—C9	1.344 (3)
C1—H1	0.9300	C8—H8	0.9300
C2—C3	1.372 (4)	C9—C10	1.473 (3)

C8—Se1—C7	84.79 (10)	C6—C5—H5	119.9
C10—O1—H7	109.5	C1—C6—C5	119.0 (2)
C7—N1—C9	112.19 (19)	C1—C6—C7	119.7 (2)
C6—C1—C2	120.4 (2)	C5—C6—C7	121.3 (2)
C6—C1—H1	119.8	N1—C7—C6	124.0 (2)
C2—C1—H1	119.8	N1—C7—Se1	114.10 (16)
C3—C2—C1	120.1 (3)	C6—C7—Se1	121.82 (15)
C3—C2—H2	120.0	C9—C8—Se1	110.35 (17)
C1—C2—H2	120.0	C9—C8—H8	124.8
C4—C3—C2	119.9 (2)	Se1—C8—H8	124.8
C4—C3—H3	120.0	C8—C9—N1	118.6 (2)
C2—C3—H3	120.0	C8—C9—C10	123.0 (2)
C3—C4—C5	120.5 (3)	N1—C9—C10	118.48 (19)
C3—C4—H4	119.8	O2—C10—O1	123.5 (2)
C5—C4—H4	119.8	O2—C10—C9	121.9 (2)
C4—C5—C6	120.1 (3)	O1—C10—C9	114.6 (2)
C4—C5—H5	119.9

C6—C1—C2—C3	−0.5 (5)	C5—C6—C7—Se1	12.7 (3)
C1—C2—C3—C4	1.3 (5)	C8—Se1—C7—N1	−0.22 (18)
C2—C3—C4—C5	−1.0 (4)	C8—Se1—C7—C6	177.7 (2)
C3—C4—C5—C6	0.1 (4)	C7—Se1—C8—C9	−0.05 (18)
C2—C1—C6—C5	−0.5 (4)	Se1—C8—C9—N1	0.3 (3)
C2—C1—C6—C7	178.7 (3)	Se1—C8—C9—C10	179.96 (19)
C4—C5—C6—C1	0.7 (4)	C7—N1—C9—C8	−0.5 (3)
C4—C5—C6—C7	−178.4 (2)	C7—N1—C9—C10	179.8 (2)
C9—N1—C7—C6	−177.5 (2)	C8—C9—C10—O2	−173.9 (3)
C9—N1—C7—Se1	0.4 (2)	N1—C9—C10—O2	5.8 (4)
C1—C6—C7—N1	11.4 (3)	C8—C9—C10—O1	5.3 (4)
C5—C6—C7—N1	−169.5 (2)	N1—C9—C10—O1	−175.1 (2)
C1—C6—C7—Se1	−166.39 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H7···O2ⁱ	0.82	1.81	2.623 (2)	171

Symmetry code: (i) −x+1, −y−1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₇NO₂Se
M_r	252.13
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.0817 (3), 11.5661 (4), 11.6295 (4)
β (°)	117.168 (2)
V (Å³)	967.12 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.85
Crystal size (mm)	0.23 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.437, 0.479
No. of measured, independent and observed [I > 2σ(I)] reflections	7502, 1705, 1487
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.063, 1.05
No. of reflections	1705
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.19

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), 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—H7···O2ⁱ	0.82	1.81	2.623 (2)	171

Symmetry code: (i) −x+1, −y−1, −z+1.

Acknowledgements

This project was supprted by the Natural Science of Fundation of Zhejiang (Y4080256) and the Zhejiang Students' Science and Technology Innovation Plan (Young Talent Plan) Aid.

References

Boritzki, T. J., Berry, D. A., Besserer, J. A., Cook, P. D., Fry, D. W., Leopold, W. R. & Jackson, R. C. (1985). Biochem. Pharmacol. 34, 1109–1114. CrossRef CAS PubMed Web of Science Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, J.-B., Lv, X., Chen, J.-F., Zhou, Y.-F. & Zhao, G.-L. (2011). Acta Cryst. E67, m186–m187. Web of Science CSD CrossRef IUCr Journals Google Scholar
Srivastava, P. C. & Robins, R. K. (1983). J. Med. Chem. 26, 445–448. CrossRef CAS PubMed Web of Science Google Scholar
Zhao, G.-L., Shi, X., Zhang, J. P., Liu, J.-F., Xian, H.-D. & Shao, L. X. (2010). Chem. Sci. China, 40 1525–1535. Google Scholar