2-Phenyl-1,3-selenazole-4-carb-oxy-lic acid.

In the title compound, C(10)H(7)NO(2)Se, the two rings are twisted, making a dihedral angle of 12.42 (9)°. In the crystal, pairs of mol-ecules 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 = 252.13

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.063

S = 1.05

1705 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.19 e Å−3

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.

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

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

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

C10H7NO2Se	F(000) = 496
Mr = 252.13	Dx = 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

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

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(Fo2) + (0.0341P)2 + 0.3951P] where P = (Fo2 + 2Fc2)/3
1705 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.18 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.

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .