Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803006433/dn6061sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803006433/dn6061Isup2.hkl |
CCDC reference: 209982
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.054
- wR factor = 0.145
- Data-to-parameter ratio = 12.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound was prepared by treatment of 2-methylseleno-3-nitrobenzanilide first with Br2 and then with Na2CO3 (Messali, 2001). Red single crystals were obtained by slow evaporation of a chloroform solution.
All H atoms were included in the refinement in the riding-model approximation, with Uiso values fixed at 1.2Ueq of the parent atom.
Data collection: DIF4 (Stoe & Cie, 1987); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.
C13H8N2O3Se | F(000) = 632 |
Mr = 319.17 | Dx = 1.771 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2yn | Cell parameters from 36 reflections |
a = 8.069 (1) Å | θ = 33.0–37.3° |
b = 6.322 (2) Å | µ = 4.32 mm−1 |
c = 23.512 (3) Å | T = 293 K |
β = 93.38 (2)° | Tablet, red |
V = 1197.3 (4) Å3 | 0.58 × 0.57 × 0.08 mm |
Z = 4 |
Stoe–Siemens AED four-circle diffractometer | 1675 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 68.1°, θmin = 3.8° |
ω scans | h = 0→9 |
Absorption correction: ψ scan (EMPIR; Stoe & Cie, 1987) | k = 0→7 |
Tmin = 0.157, Tmax = 0.724 | l = −28→28 |
2310 measured reflections | 2 standard reflections every 60 min |
2146 independent reflections | intensity decay: 5% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.1196P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
2146 reflections | Δρmax = 1.05 e Å−3 |
173 parameters | Δρmin = −0.70 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0082 (9) |
C13H8N2O3Se | V = 1197.3 (4) Å3 |
Mr = 319.17 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 8.069 (1) Å | µ = 4.32 mm−1 |
b = 6.322 (2) Å | T = 293 K |
c = 23.512 (3) Å | 0.58 × 0.57 × 0.08 mm |
β = 93.38 (2)° |
Stoe–Siemens AED four-circle diffractometer | 1675 reflections with I > 2σ(I) |
Absorption correction: ψ scan (EMPIR; Stoe & Cie, 1987) | Rint = 0.035 |
Tmin = 0.157, Tmax = 0.724 | 2 standard reflections every 60 min |
2310 measured reflections | intensity decay: 5% |
2146 independent reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 0.99 | Δρmax = 1.05 e Å−3 |
2146 reflections | Δρmin = −0.70 e Å−3 |
173 parameters |
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 | 0.85582 (5) | 0.21384 (7) | 0.02096 (2) | 0.0576 (3) | |
O1 | 0.8795 (5) | 0.4112 (6) | −0.07337 (16) | 0.0811 (10) | |
O2 | 0.7788 (6) | 0.3661 (9) | −0.16024 (18) | 0.1021 (13) | |
O3 | 0.6425 (5) | −0.3188 (6) | 0.06868 (16) | 0.0759 (10) | |
N1 | 0.7979 (6) | 0.3090 (7) | −0.1110 (2) | 0.0728 (11) | |
N2 | 0.7961 (4) | −0.0077 (6) | 0.07019 (15) | 0.0583 (9) | |
C1 | 0.7424 (4) | 0.0602 (7) | −0.03597 (18) | 0.0563 (10) | |
C2 | 0.7242 (5) | 0.1141 (8) | −0.0929 (2) | 0.0633 (11) | |
C3 | 0.6344 (6) | −0.0130 (9) | −0.1316 (2) | 0.0726 (13) | |
H3 | 0.6215 | 0.0250 | −0.1698 | 0.087* | |
C4 | 0.5637 (7) | −0.1991 (10) | −0.1122 (2) | 0.0780 (15) | |
H4 | 0.5031 | −0.2855 | −0.1378 | 0.094* | |
C5 | 0.5826 (6) | −0.2571 (8) | −0.0551 (2) | 0.0702 (13) | |
H5 | 0.5355 | −0.3816 | −0.0426 | 0.084* | |
C6 | 0.6735 (5) | −0.1260 (8) | −0.01661 (19) | 0.0601 (11) | |
C7 | 0.6987 (5) | −0.1680 (8) | 0.0444 (2) | 0.0595 (11) | |
C8 | 0.8511 (5) | 0.0019 (8) | 0.12865 (19) | 0.0605 (10) | |
C9 | 0.9371 (8) | 0.1758 (11) | 0.1478 (2) | 0.0881 (18) | |
H9 | 0.9539 | 0.2868 | 0.1228 | 0.106* | |
C10 | 1.0003 (9) | 0.1906 (12) | 0.2041 (3) | 0.102 (2) | |
H10 | 1.0592 | 0.3101 | 0.2165 | 0.123* | |
C11 | 0.9753 (9) | 0.0292 (13) | 0.2410 (3) | 0.101 (2) | |
H11 | 1.0159 | 0.0377 | 0.2788 | 0.122* | |
C12 | 0.8898 (9) | −0.1454 (14) | 0.2216 (3) | 0.109 (2) | |
H12 | 0.8741 | −0.2570 | 0.2465 | 0.131* | |
C13 | 0.8265 (8) | −0.1600 (11) | 0.1664 (3) | 0.0893 (16) | |
H13 | 0.7668 | −0.2794 | 0.1544 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.0545 (3) | 0.0479 (4) | 0.0701 (4) | −0.00223 (18) | −0.0004 (2) | −0.0048 (2) |
O1 | 0.083 (2) | 0.067 (2) | 0.091 (2) | −0.0099 (19) | −0.0086 (19) | 0.0075 (19) |
O2 | 0.112 (3) | 0.106 (3) | 0.086 (2) | −0.002 (3) | −0.008 (2) | 0.026 (3) |
O3 | 0.087 (2) | 0.056 (2) | 0.086 (2) | −0.0245 (17) | 0.0082 (19) | −0.0001 (17) |
N1 | 0.068 (3) | 0.071 (3) | 0.079 (3) | 0.010 (2) | 0.003 (2) | 0.008 (2) |
N2 | 0.0562 (19) | 0.052 (2) | 0.066 (2) | −0.0045 (15) | 0.0023 (16) | −0.0066 (16) |
C1 | 0.0406 (19) | 0.057 (3) | 0.071 (2) | 0.0049 (16) | −0.0002 (17) | −0.007 (2) |
C2 | 0.054 (2) | 0.061 (3) | 0.075 (3) | 0.007 (2) | −0.0001 (19) | −0.006 (2) |
C3 | 0.064 (3) | 0.084 (4) | 0.068 (3) | 0.012 (2) | −0.008 (2) | −0.008 (2) |
C4 | 0.064 (3) | 0.089 (4) | 0.080 (3) | −0.004 (3) | −0.008 (2) | −0.026 (3) |
C5 | 0.061 (3) | 0.062 (3) | 0.088 (3) | −0.003 (2) | 0.006 (2) | −0.026 (2) |
C6 | 0.049 (2) | 0.059 (3) | 0.073 (3) | 0.0053 (19) | 0.0056 (19) | −0.016 (2) |
C7 | 0.054 (2) | 0.055 (2) | 0.070 (3) | 0.0004 (19) | 0.0046 (19) | −0.014 (2) |
C8 | 0.053 (2) | 0.062 (3) | 0.066 (2) | 0.0004 (19) | 0.0033 (18) | −0.006 (2) |
C9 | 0.114 (5) | 0.084 (4) | 0.068 (3) | −0.036 (3) | 0.013 (3) | −0.011 (3) |
C10 | 0.121 (5) | 0.108 (5) | 0.077 (3) | −0.043 (4) | −0.005 (3) | −0.016 (3) |
C11 | 0.116 (5) | 0.110 (5) | 0.075 (3) | −0.025 (4) | −0.014 (3) | 0.003 (3) |
C12 | 0.132 (6) | 0.106 (5) | 0.085 (4) | −0.023 (4) | −0.025 (4) | 0.029 (4) |
C13 | 0.104 (4) | 0.078 (4) | 0.083 (3) | −0.020 (3) | −0.016 (3) | 0.010 (3) |
Se1—C1 | 1.852 (4) | C5—C6 | 1.402 (7) |
Se1—N2 | 1.897 (4) | C5—H5 | 0.9300 |
O1—N1 | 1.251 (6) | C6—C7 | 1.461 (6) |
O2—N1 | 1.215 (6) | C8—C9 | 1.362 (7) |
O3—C7 | 1.213 (6) | C8—C13 | 1.377 (8) |
N1—C2 | 1.442 (7) | C9—C10 | 1.395 (8) |
N2—C7 | 1.399 (6) | C9—H9 | 0.9300 |
N2—C8 | 1.421 (6) | C10—C11 | 1.362 (10) |
C1—C2 | 1.381 (6) | C10—H10 | 0.9300 |
C1—C6 | 1.389 (7) | C11—C12 | 1.366 (10) |
C2—C3 | 1.386 (7) | C11—H11 | 0.9300 |
C3—C4 | 1.396 (8) | C12—C13 | 1.370 (8) |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C5 | 1.391 (8) | C13—H13 | 0.9300 |
C4—H4 | 0.9300 | ||
C1—Se1—N2 | 85.48 (17) | C1—C6—C7 | 116.1 (4) |
O2—N1—O1 | 123.5 (5) | C5—C6—C7 | 124.3 (5) |
O2—N1—C2 | 120.2 (5) | O3—C7—N2 | 125.5 (4) |
O1—N1—C2 | 116.3 (4) | O3—C7—C6 | 124.8 (4) |
C7—N2—C8 | 125.9 (4) | N2—C7—C6 | 109.7 (4) |
C7—N2—Se1 | 115.2 (3) | C9—C8—C13 | 118.5 (5) |
C8—N2—Se1 | 118.8 (3) | C9—C8—N2 | 118.6 (5) |
C2—C1—C6 | 120.4 (4) | C13—C8—N2 | 122.9 (4) |
C2—C1—Se1 | 126.2 (4) | C8—C9—C10 | 121.2 (6) |
C6—C1—Se1 | 113.4 (3) | C8—C9—H9 | 119.4 |
C1—C2—C3 | 121.0 (5) | C10—C9—H9 | 119.4 |
C1—C2—N1 | 118.3 (4) | C11—C10—C9 | 119.7 (6) |
C3—C2—N1 | 120.7 (5) | C11—C10—H10 | 120.2 |
C2—C3—C4 | 118.8 (5) | C9—C10—H10 | 120.2 |
C2—C3—H3 | 120.6 | C10—C11—C12 | 118.9 (6) |
C4—C3—H3 | 120.6 | C10—C11—H11 | 120.5 |
C5—C4—C3 | 120.9 (5) | C12—C11—H11 | 120.5 |
C5—C4—H4 | 119.6 | C11—C12—C13 | 121.6 (7) |
C3—C4—H4 | 119.6 | C11—C12—H12 | 119.2 |
C4—C5—C6 | 119.4 (5) | C13—C12—H12 | 119.2 |
C4—C5—H5 | 120.3 | C12—C13—C8 | 120.0 (6) |
C6—C5—H5 | 120.3 | C12—C13—H13 | 120.0 |
C1—C6—C5 | 119.5 (5) | C8—C13—H13 | 120.0 |
C1—Se1—N2—C7 | −1.8 (3) | C4—C5—C6—C7 | 178.6 (5) |
C1—Se1—N2—C8 | 178.6 (3) | C8—N2—C7—O3 | 2.5 (7) |
N2—Se1—C1—C2 | −179.0 (4) | Se1—N2—C7—O3 | −177.1 (4) |
N2—Se1—C1—C6 | 0.4 (3) | C8—N2—C7—C6 | −177.8 (4) |
C6—C1—C2—C3 | 1.4 (7) | Se1—N2—C7—C6 | 2.6 (5) |
Se1—C1—C2—C3 | −179.2 (4) | C1—C6—C7—O3 | 177.4 (4) |
C6—C1—C2—N1 | 180.0 (4) | C5—C6—C7—O3 | −0.9 (8) |
Se1—C1—C2—N1 | −0.7 (6) | C1—C6—C7—N2 | −2.3 (5) |
O2—N1—C2—C1 | −177.0 (4) | C5—C6—C7—N2 | 179.4 (4) |
O1—N1—C2—C1 | 2.8 (6) | C7—N2—C8—C9 | −176.0 (5) |
O2—N1—C2—C3 | 1.6 (7) | Se1—N2—C8—C9 | 3.5 (6) |
O1—N1—C2—C3 | −178.6 (5) | C7—N2—C8—C13 | 6.3 (7) |
C1—C2—C3—C4 | −0.8 (7) | Se1—N2—C8—C13 | −174.1 (4) |
N1—C2—C3—C4 | −179.3 (4) | C13—C8—C9—C10 | 0.5 (10) |
C2—C3—C4—C5 | −0.1 (8) | N2—C8—C9—C10 | −177.3 (6) |
C3—C4—C5—C6 | 0.3 (8) | C8—C9—C10—C11 | −0.4 (12) |
C2—C1—C6—C5 | −1.2 (6) | C9—C10—C11—C12 | 0.6 (13) |
Se1—C1—C6—C5 | 179.4 (3) | C10—C11—C12—C13 | −1.1 (13) |
C2—C1—C6—C7 | −179.6 (4) | C11—C12—C13—C8 | 1.2 (12) |
Se1—C1—C6—C7 | 1.0 (5) | C9—C8—C13—C12 | −0.9 (10) |
C4—C5—C6—C1 | 0.4 (7) | N2—C8—C13—C12 | 176.7 (6) |
Experimental details
Crystal data | |
Chemical formula | C13H8N2O3Se |
Mr | 319.17 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 8.069 (1), 6.322 (2), 23.512 (3) |
β (°) | 93.38 (2) |
V (Å3) | 1197.3 (4) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 4.32 |
Crystal size (mm) | 0.58 × 0.57 × 0.08 |
Data collection | |
Diffractometer | Stoe–Siemens AED four-circle diffractometer |
Absorption correction | ψ scan (EMPIR; Stoe & Cie, 1987) |
Tmin, Tmax | 0.157, 0.724 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2310, 2146, 1675 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.145, 0.99 |
No. of reflections | 2146 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.05, −0.70 |
Computer programs: DIF4 (Stoe & Cie, 1987), DIF4, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Bruno et al., 2002), SHELXL97.
Se1—C1 | 1.852 (4) | O3—C7 | 1.213 (6) |
Se1—N2 | 1.897 (4) | N1—C2 | 1.442 (7) |
O1—N1 | 1.251 (6) | N2—C7 | 1.399 (6) |
O2—N1 | 1.215 (6) | N2—C8 | 1.421 (6) |
C1—Se1—N2 | 85.48 (17) | C8—N2—Se1 | 118.8 (3) |
O2—N1—O1 | 123.5 (5) | C2—C1—Se1 | 126.2 (4) |
O2—N1—C2 | 120.2 (5) | C6—C1—Se1 | 113.4 (3) |
O1—N1—C2 | 116.3 (4) | O3—C7—N2 | 125.5 (4) |
C7—N2—C8 | 125.9 (4) | O3—C7—C6 | 124.8 (4) |
C7—N2—Se1 | 115.2 (3) | N2—C7—C6 | 109.7 (4) |
C7—N2—C8—C13 | 6.3 (7) | Se1—N2—C8—C13 | −174.1 (4) |
Ebselen (Natterman/RP, 1981; Dupont et al., 1990), a well known anti-inflammatory drug, exhibits some physicochemical failings, mainly a low solubility. In the course of studying new molecules of the benzo[e][1,2]selenazin-4-one family which could be better anti-oxidizing agents, crystals of the title compound, (I), were obtained from a chloroform solution. The structure of (I) was determined by X-ray diffraction and shown to be 7-nitro-2-phenyl-1,2-benzisoselenazol-3-one crystallized in a monoclinic form. The triclinic structure, (II), determined from a sample crystallized from a water–methanol solution, has been described previously [Dupont et al. (1988); Cambridge Structural Database (Allen, 2002) refcode JABZAN].
In (I), the maximum and minimum residuals in the final difference map are located at 1.11 and 0.86 Å, respectively, from the Se1 position. The distances and angles are quite similar to those found in (II). The most significant deviation with regard to the bond lengths is for C7—O3, viz. 1.213 (6) Å in (I) and 1.234 (5) Å in (II). In (I), the dihedral angle between the phenyl and heterocycle mean planes is 6.0 (3)°, whereas the corresponding value in (II) is 13.2 (1)°. The C1—C2—N1—O1 torsion angles are also significantly different, viz. 2.8 (6)° in (I) and 4.9 (5)° in (II). The molecular conformation is consequently more planar in the monoclinic polymorph. The Se1—O1 distances are nevertheless quite similar, viz. 2.562 (4) Å in (I) and 2.573 (3) Å in (II). In both polymorphs, the molecules are approximately elongated in the direction of the c axis. Each molecule is superposed on its equivalent by a 1 symmetry operation. The result is a stacking of almost equidistant molecular planes [alternating distances of 3.333 (5)/3.528 (5) Å in (I) and 3.373 (4)/3.510 (4) Å in (II); distances are those between the five-membered-ring mean planes (P1)], the centroids of the heterocyclic rings being nearly superimposed. In (II), the normal to P1 is almost parallel to the b axis, whereas in (I), the molecular planes are packed along two directions. The angle between the corresponding P1 planes is 59.4 (4)°. There is no hydrogen bonding in the crystal structure of (I).