N-Propionyl-1,2-benzisoselenazol-3(2H)-one

The title compound, C₁₀H₉NO₂Se, crystallizes as flat mol­ecules linked by selenium–oxy­gen interactions [Se...O = 3.189 (4) Å] into a linear chain along the a axis of the triclinic cell. The bond dimensions that are derived from ab initio geometry optimization calculations are similar to those determined from the diffraction measurements.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

N-Propiolyl-1,2-benzisoselenazol-3(2H)-one

Crystal data

C10H9NO2Se	Z = 2
Mr = 254.14	F(000) = 252
Triclinic, P1	Dx = 1.747 Mg m^−3
a = 6.8865 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0840 (2) Å	Cell parameters from 2878 reflections
c = 9.8348 (1) Å	θ = 2.2–28.2°
α = 70.542 (1)°	µ = 3.86 mm^−1
β = 75.896 (1)°	T = 298 K
γ = 71.249 (1)°	Parallelepiped, colorless
V = 483.08 (2) Å^3	0.46 × 0.28 × 0.12 mm

Data collection

Siemens CCD area-detector diffractometer	2271 independent reflections
Radiation source: fine-focus sealed tube	1964 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 8.3 pixels mm^-1	θmax = 28.2°, θmin = 2.2°
ω scan	h = −8→9
Absorption correction: empirical (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.270, Tmax = 0.655	l = −7→12
3461 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0996P)^2] where P = (Fo^2 + 2Fc^2)/3
2271 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 1.49 e Å^−3
0 restraints	Δρmin = −1.59 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.71858 (6)	0.35014 (5)	0.37328 (4)	0.0372 (2)
O1	0.1466 (5)	0.2878 (5)	0.4777 (4)	0.048 (1)
O2	0.5067 (6)	0.5882 (5)	0.1428 (4)	0.051 (1)
N1	0.4425 (5)	0.3842 (5)	0.3552 (4)	0.034 (1)
C1	0.6607 (7)	0.1820 (5)	0.5546 (5)	0.035 (1)
C2	0.8010 (7)	0.0775 (7)	0.6527 (5)	0.043 (1)
C3	0.7294 (9)	−0.0372 (7)	0.7807 (6)	0.051 (1)
C4	0.5257 (9)	−0.0502 (7)	0.8140 (5)	0.050 (1)
C5	0.3881 (8)	0.0520 (6)	0.7160 (5)	0.041 (1)
C6	0.4582 (6)	0.1680 (5)	0.5852 (4)	0.033 (1)
C7	0.3260 (6)	0.2812 (5)	0.4719 (5)	0.034 (1)
C8	0.3784 (7)	0.5149 (6)	0.2277 (5)	0.038 (1)
C9	0.1588 (8)	0.5529 (7)	0.2065 (5)	0.048 (1)
C10	0.106 (1)	0.699 (1)	0.0659 (6)	0.070 (2)
H2	0.9374	0.0853	0.6322	0.064*
H3	0.8204	−0.1083	0.8469	0.076*
H4	0.4818	−0.1274	0.9021	0.074*
H5	0.2519	0.0437	0.7370	0.061*
H9a	0.0666	0.5912	0.2885	0.072*
H9b	0.1348	0.4413	0.2058	0.072*
H10a	−0.0367	0.7169	0.0584	0.105*
H10b	0.1939	0.6604	−0.0160	0.105*
H10c	0.1257	0.8103	0.0668	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.0281 (3)	0.0389 (3)	0.0386 (3)	−0.0124 (2)	−0.0013 (2)	−0.0023 (2)
O1	0.031 (2)	0.055 (2)	0.049 (2)	−0.019 (1)	−0.008 (1)	0.004 (2)
O2	0.042 (2)	0.054 (2)	0.044 (2)	−0.016 (2)	−0.001 (2)	0.005 (2)
N1	0.023 (2)	0.042 (2)	0.033 (2)	−0.009 (1)	−0.006 (1)	−0.003 (1)
C1	0.032 (2)	0.031 (2)	0.037 (2)	−0.010 (2)	−0.005 (2)	−0.004 (2)
C2	0.034 (2)	0.047 (2)	0.046 (3)	−0.015 (2)	−0.014 (2)	−0.002 (2)
C3	0.057 (3)	0.046 (2)	0.044 (3)	−0.010 (2)	−0.022 (2)	0.001 (2)
C4	0.058 (3)	0.046 (3)	0.038 (3)	−0.019 (2)	−0.009 (2)	0.004 (2)
C5	0.037 (2)	0.042 (2)	0.040 (2)	−0.018 (2)	−0.002 (2)	−0.004 (2)
C6	0.029 (2)	0.032 (2)	0.035 (2)	−0.009 (2)	−0.004 (2)	−0.006 (2)
C7	0.028 (2)	0.033 (2)	0.035 (2)	−0.010 (2)	−0.002 (2)	−0.004 (2)
C8	0.037 (2)	0.038 (2)	0.031 (2)	−0.008 (2)	−0.003 (2)	−0.004 (2)
C9	0.037 (3)	0.053 (3)	0.042 (3)	−0.005 (2)	−0.010 (2)	−0.002 (2)
C10	0.054 (4)	0.086 (5)	0.046 (3)	0.000 (3)	−0.017 (3)	0.001 (3)

Geometric parameters (Å, º)

Se1—N1	1.876 (3)	C6—C7	1.479 (6)
Se1—C1	1.890 (4)	C8—C9	1.496 (6)
O1—C7	1.207 (5)	C9—C10	1.523 (7)
O2—C8	1.215 (6)	C2—H2	0.9300
N1—C8	1.404 (5)	C3—H3	0.9300
N1—C7	1.414 (5)	C4—H4	0.9300
C1—C6	1.387 (6)	C5—H5	0.9300
C1—C2	1.402 (6)	C9—H9a	0.9700
C2—C3	1.379 (7)	C9—H9b	0.9700
C3—C4	1.391 (8)	C10—H10a	0.9600
C4—C5	1.386 (7)	C10—H10b	0.9600
C5—C6	1.397 (6)	C10—H10c	0.9600
N1—Se1—C1	85.2 (2)	C8—C9—C10	113.3 (5)
C8—N1—C7	128.9 (4)	C3—C2—H2	121.2
C8—N1—Se1	114.4 (3)	C1—C2—H2	121.2
C7—N1—Se1	116.6 (3)	C2—C3—H3	118.9
C6—C1—C2	120.8 (4)	C4—C3—H3	118.9
C6—C1—Se1	113.2 (3)	C5—C4—H4	120.0
C2—C1—Se1	126.0 (3)	C3—C4—H4	120.0
C3—C2—C1	117.6 (4)	C4—C5—H5	120.7
C2—C3—C4	122.2 (4)	C6—C5—H5	120.7
C5—C4—C3	120.0 (4)	C8—C9—H9a	108.9
C4—C5—C6	118.7 (4)	C10—C9—H9a	108.9
C1—C6—C5	120.7 (4)	C8—C9—H9b	108.9
C1—C6—C7	116.0 (4)	C10—C9—H9b	108.9
C5—C6—C7	123.3 (4)	H9a—C9—H9b	107.7
O1—C7—N1	124.9 (4)	C9—C10—H10a	109.5
O1—C7—C6	126.1 (4)	C9—C10—H10b	109.5
N1—C7—C6	109.0 (3)	H10a—C10—H10b	109.5
O2—C8—N1	117.2 (4)	C9—C10—H10c	109.5
O2—C8—C9	125.1 (4)	H10a—C10—H10c	109.5
N1—C8—C9	117.7 (4)	H10b—C10—H10c	109.5
C1—Se1—N1—C8	178.1 (3)	C8—N1—C7—O1	1.9 (7)
C1—Se1—N1—C7	0.1 (3)	Se1—N1—C7—O1	179.6 (4)
N1—Se1—C1—C6	−0.8 (3)	C8—N1—C7—C6	−177.1 (4)
N1—Se1—C1—C2	178.9 (4)	Se1—N1—C7—C6	0.5 (4)
C6—C1—C2—C3	−0.8 (7)	C1—C6—C7—O1	179.8 (4)
Se1—C1—C2—C3	179.5 (4)	C5—C6—C7—O1	0.0 (7)
C1—C2—C3—C4	−0.4 (8)	C1—C6—C7—N1	−1.2 (5)
C2—C3—C4—C5	1.1 (8)	C5—C6—C7—N1	179.0 (4)
C3—C4—C5—C6	−0.5 (7)	C7—N1—C8—O2	179.1 (4)
C2—C1—C6—C5	1.4 (7)	Se1—N1—C8—O2	1.4 (5)
Se1—C1—C6—C5	−178.9 (3)	C7—N1—C8—C9	−1.1 (7)
C2—C1—C6—C7	−178.4 (4)	Se1—N1—C8—C9	−178.8 (3)
Se1—C1—C6—C7	1.3 (5)	O2—C8—C9—C10	−1.0 (8)
C4—C5—C6—C1	−0.7 (7)	N1—C8—C9—C10	179.1 (5)
C4—C5—C6—C7	179.1 (4)