organic compounds
The title compound, C10H9NO2Se, crystallizes as flat molecules linked by selenium–oxygen interactions [SeO = 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.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100011276/de1150sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011276/de1150Isup2.hkl |
CCDC reference: 153916
Computing details top
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 top
Crystal data top
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) Å3 | 0.46 × 0.28 × 0.12 mm |
Data collection top
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 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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0996P)2] where P = (Fo2 + 2Fc2)/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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) |
Relative Mulliken partial charges of the atoms of
N-propiolyl-1,2-benzisoselenazol-3(2H)-one and
N-methyl-1,2-benzisoselenazol-3(2H)-onea top
Atomb | N-Propiolyl | N-Methyl |
Se1 | 0.913 | 0.851 |
O1 | -0.634 | -0.658 |
O2 | -0.611 | |
N1 | -1.189 | -1.061 |
C1 | -0.501 | -0.485 |
C2 | 0.023 | 0.019 |
C3 | 0.049 | 0.039 |
C4 | 0.007 | 0.005 |
C5 | 0.116 | 0.110 |
C6 | -0.144 | -0.141 |
C7 | 0.979 | 0.972 |
C8 | 0.931 | 0.351 |
C9 | -0.007 | |
C10 | 0.069 |
Notes: (a) The charges of the hydrogen atoms were summed into the charges of the carbon atoms; (b) Atom-numbering scheme for the calculated structures uses the labels of the C7H4NOSe entity in Fig. 1; C8 in the N-methyl derivative refers to the methyl carbon atom. |