N-(2-Methyl-phen-yl)-1,2-benzoselen-azol-3(2H)-one.

IN THE TITLE EBSELEN [SYSTEMATIC NAME: (2-phenyl-1,2-benzoisoselenazol-3-(2H)-one)] analogue, C14H11NOSe, the benzisoselenazolyl moiety (r.m.s. deviation = 0.0209 Å) is nearly perpendicular to the N-arenyl ring, making a dihedral angle of 78.15 (11)°. In the crystal, mol-ecules are linked by C-H⋯O and Se⋯O inter-actions into chains along the c-axis direction. The Se⋯O distance [2.733 (3) Å] is longer than that in Ebselen (2.571 (3) Å].

Related literature

For general background to the properties of Ebselen, see: Bhabak & Mugesh (2010 ▶); Mugesh et al. (2001a ▶,b ▶); Mugesh & Singh (2000 ▶); Engman (1989 ▶); Parnham & Graf (1991 ▶). For related structures, see: Balkrishna et al. (2010 ▶); Bhabak & Mugesh (2007 ▶); Chang et al. (2003 ▶); Dupont et al. (1990 ▶).

Experimental

Crystal data

C14H11NOSe

M = 288.20

Monoclinic,

a = 7.7319 (14) Å

b = 13.491 (2) Å

c = 11.913 (2) Å

β = 102.625 (3)°

V = 1212.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.08 mm−1

T = 273 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.459, T max = 0.578

4948 measured reflections

2133 independent reflections

1840 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.095

S = 1.10

2133 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.27 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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813024744/bg2515sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024744/bg2515Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024744/bg2515Isup3.cml

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

C14H11NOSe	Z = 4
Mr = 288.20	F(000) = 576
Monoclinic, P21/n	Dx = 1.579 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.7319 (14) Å	µ = 3.08 mm−1
b = 13.491 (2) Å	T = 273 K
c = 11.913 (2) Å	Plate, yellow
β = 102.625 (3)°	0.30 × 0.20 × 0.20 mm
V = 1212.6 (4) Å3

Bruker SMART CCD area-detector diffractometer	2133 independent reflections
Radiation source: fine-focus sealed tube	1840 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
phi and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
Tmin = 0.459, Tmax = 0.578	k = −15→16
4948 measured reflections	l = −13→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) = 0.095	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0461P)2 + 0.4966P] where P = (Fo2 + 2Fc2)/3
2133 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.27 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
Se	1.09550 (5)	0.78392 (3)	0.72071 (3)	0.04308 (16)
N	0.9365 (4)	0.8320 (2)	0.5900 (2)	0.0409 (7)
O	0.8278 (4)	0.8041 (2)	0.3987 (2)	0.0515 (7)
C1	1.1450 (5)	0.6833 (3)	0.6215 (3)	0.0397 (9)
C2	1.2625 (5)	0.6048 (3)	0.6512 (3)	0.0510 (10)
H2	1.3234	0.5952	0.7269	0.061*
C3	1.2857 (6)	0.5417 (3)	0.5648 (4)	0.0621 (12)
H3	1.3649	0.4892	0.5825	0.074*
C4	1.1934 (6)	0.5548 (4)	0.4520 (4)	0.0656 (12)
H4	1.2105	0.5111	0.3951	0.079*
C5	1.0771 (6)	0.6323 (3)	0.4247 (3)	0.0550 (11)
H5	1.0157	0.6415	0.3491	0.066*
C6	1.0513 (5)	0.6967 (3)	0.5096 (3)	0.0407 (9)
C7	0.9274 (5)	0.7807 (3)	0.4903 (3)	0.0412 (9)
C8	0.8145 (5)	0.9075 (3)	0.6062 (3)	0.0403 (9)
C9	0.6444 (5)	0.8811 (3)	0.6142 (3)	0.0489 (10)
C10	0.5347 (6)	0.9574 (4)	0.6363 (3)	0.0626 (12)
H10	0.4197	0.9423	0.6423	0.075*
C11	0.5907 (8)	1.0532 (4)	0.6493 (4)	0.0677 (14)
H11	0.5142	1.1022	0.6643	0.081*
C12	0.7594 (8)	1.0778 (3)	0.6403 (4)	0.0682 (13)
H12	0.7974	1.1433	0.6494	0.082*
C13	0.8721 (6)	1.0048 (3)	0.6179 (3)	0.0525 (10)
H13	0.9861	1.0209	0.6107	0.063*
C14	0.5808 (7)	0.7763 (3)	0.6001 (5)	0.0706 (14)
H14A	0.5574	0.7586	0.5202	0.106*
H14B	0.4741	0.7699	0.6282	0.106*
H14C	0.6701	0.7332	0.6429	0.106*

	U11	U22	U33	U12	U13	U23
Se	0.0454 (3)	0.0501 (3)	0.0297 (2)	0.00016 (19)	−0.00047 (16)	−0.00060 (16)
N	0.0423 (17)	0.0472 (17)	0.0286 (16)	0.0005 (15)	−0.0025 (13)	0.0000 (13)
O	0.0548 (17)	0.0605 (17)	0.0323 (14)	0.0018 (14)	−0.0057 (13)	0.0014 (12)
C1	0.039 (2)	0.047 (2)	0.0308 (19)	−0.0045 (17)	0.0041 (16)	−0.0007 (16)
C2	0.052 (2)	0.054 (2)	0.042 (2)	0.005 (2)	−0.0005 (19)	0.0055 (19)
C3	0.063 (3)	0.062 (3)	0.058 (3)	0.014 (2)	0.007 (2)	−0.002 (2)
C4	0.073 (3)	0.070 (3)	0.053 (3)	0.010 (3)	0.011 (2)	−0.015 (2)
C5	0.061 (3)	0.065 (3)	0.037 (2)	0.002 (2)	0.0058 (19)	−0.003 (2)
C6	0.043 (2)	0.046 (2)	0.0316 (19)	−0.0042 (17)	0.0047 (17)	0.0005 (16)
C7	0.040 (2)	0.047 (2)	0.034 (2)	−0.0079 (18)	0.0030 (17)	0.0010 (16)
C8	0.043 (2)	0.047 (2)	0.0281 (18)	0.0034 (18)	0.0023 (16)	0.0016 (16)
C9	0.048 (2)	0.062 (3)	0.036 (2)	0.003 (2)	0.0066 (18)	0.0096 (18)
C10	0.053 (3)	0.094 (4)	0.041 (2)	0.016 (3)	0.012 (2)	0.013 (2)
C11	0.091 (4)	0.070 (3)	0.042 (2)	0.032 (3)	0.015 (2)	−0.001 (2)
C12	0.104 (4)	0.050 (3)	0.047 (3)	0.005 (3)	0.009 (3)	−0.005 (2)
C13	0.059 (3)	0.056 (3)	0.040 (2)	−0.008 (2)	0.004 (2)	−0.0039 (19)
C14	0.061 (3)	0.070 (3)	0.081 (4)	−0.017 (3)	0.016 (3)	0.014 (3)

Se—N	1.876 (3)	C6—C7	1.470 (5)
Se—C1	1.894 (4)	C8—C13	1.384 (5)
N—C7	1.364 (5)	C8—C9	1.386 (5)
N—C8	1.429 (5)	C9—C10	1.394 (6)
O—C7	1.231 (4)	C9—C14	1.494 (6)
C1—C6	1.383 (5)	C10—C11	1.361 (7)
C1—C2	1.389 (5)	C10—H10	0.9300
C2—C3	1.377 (6)	C11—C12	1.373 (7)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.388 (6)	C12—C13	1.380 (6)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.371 (6)	C13—H13	0.9300
C4—H4	0.9300	C14—H14A	0.9600
C5—C6	1.380 (5)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
N—Se—C1	85.13 (14)	C13—C8—C9	121.7 (4)
C7—N—C8	124.7 (3)	C13—C8—N	118.9 (4)
C7—N—Se	116.6 (2)	C9—C8—N	119.4 (3)
C8—N—Se	117.8 (2)	C8—C9—C10	116.7 (4)
C6—C1—C2	121.4 (4)	C8—C9—C14	121.9 (4)
C6—C1—Se	111.9 (3)	C10—C9—C14	121.3 (4)
C2—C1—Se	126.7 (3)	C11—C10—C9	122.0 (5)
C3—C2—C1	117.7 (4)	C11—C10—H10	119.0
C3—C2—H2	121.1	C9—C10—H10	119.0
C1—C2—H2	121.1	C10—C11—C12	120.4 (5)
C2—C3—C4	121.5 (4)	C10—C11—H11	119.8
C2—C3—H3	119.3	C12—C11—H11	119.8
C4—C3—H3	119.3	C11—C12—C13	119.5 (4)
C5—C4—C3	119.9 (4)	C11—C12—H12	120.2
C5—C4—H4	120.1	C13—C12—H12	120.2
C3—C4—H4	120.1	C12—C13—C8	119.6 (4)
C4—C5—C6	119.9 (4)	C12—C13—H13	120.2
C4—C5—H5	120.1	C8—C13—H13	120.2
C6—C5—H5	120.1	C9—C14—H14A	109.5
C5—C6—C1	119.7 (4)	C9—C14—H14B	109.5
C5—C6—C7	124.3 (3)	H14A—C14—H14B	109.5
C1—C6—C7	116.0 (3)	C9—C14—H14C	109.5
O—C7—N	123.0 (4)	H14A—C14—H14C	109.5
O—C7—C6	126.7 (3)	H14B—C14—H14C	109.5
N—C7—C6	110.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Oi	0.93	2.45	3.132 (4)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Oi	0.93	2.45	3.132 (4)	130

Symmetry code: (i) .