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In the course of a study of 1,2-benzoselenazin-4-one heterocyclic homologues of ebselen, a well known anti-oxidizing agent, the crystal structure determination of the title compound, C13H8N2O3Se, was carried out and revealed a monoclinic polymorph of the previously reported triclinic form. In both polymorphs, the centroids of the heterocyclic rings are nearly superimposed in projection along their normal. In the title compound, the molecular planes pack along two directions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803006433/dn6061sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803006433/dn6061Isup2.hkl
Contains datablock I

CCDC reference: 209982

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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








Comment top

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).

Experimental top

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.

Refinement top

All H atoms were included in the refinement in the riding-model approximation, with Uiso values fixed at 1.2Ueq of the parent atom.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-labelling scheme. Displacement ellipsoids are shown at the 50% probability level.
[Figure 2] Fig. 2. Mercury (Bruno et al., 2002) view of the packing of (I). H atoms have been omitted for clarity.
[Figure 3] Fig. 3. Mercury (Bruno et al., 2002) view of the packing of (II). H atoms have been omitted for clarity.
7-nitro-2-phenyl-1,2-benzisoselenazol-3(2H)-one top
Crystal data top
C13H8N2O3SeF(000) = 632
Mr = 319.17Dx = 1.771 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ynCell parameters from 36 reflections
a = 8.069 (1) Åθ = 33.0–37.3°
b = 6.322 (2) ŵ = 4.32 mm1
c = 23.512 (3) ÅT = 293 K
β = 93.38 (2)°Tablet, red
V = 1197.3 (4) Å30.58 × 0.57 × 0.08 mm
Z = 4
Data collection top
Stoe–Siemens AED four-circle
diffractometer
1675 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 68.1°, θmin = 3.8°
ω scansh = 09
Absorption correction: ψ scan
(EMPIR; Stoe & Cie, 1987)
k = 07
Tmin = 0.157, Tmax = 0.724l = 2828
2310 measured reflections2 standard reflections every 60 min
2146 independent reflections intensity decay: 5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-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 reflectionsΔρmax = 1.05 e Å3
173 parametersΔρmin = 0.70 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0082 (9)
Crystal data top
C13H8N2O3SeV = 1197.3 (4) Å3
Mr = 319.17Z = 4
Monoclinic, P21/nCu Kα radiation
a = 8.069 (1) ŵ = 4.32 mm1
b = 6.322 (2) ÅT = 293 K
c = 23.512 (3) Å0.58 × 0.57 × 0.08 mm
β = 93.38 (2)°
Data collection top
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 = 0.7242 standard reflections every 60 min
2310 measured reflections intensity decay: 5%
2146 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.145H-atom parameters constrained
S = 0.99Δρmax = 1.05 e Å3
2146 reflectionsΔρmin = 0.70 e Å3
173 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Se10.85582 (5)0.21384 (7)0.02096 (2)0.0576 (3)
O10.8795 (5)0.4112 (6)0.07337 (16)0.0811 (10)
O20.7788 (6)0.3661 (9)0.16024 (18)0.1021 (13)
O30.6425 (5)0.3188 (6)0.06868 (16)0.0759 (10)
N10.7979 (6)0.3090 (7)0.1110 (2)0.0728 (11)
N20.7961 (4)0.0077 (6)0.07019 (15)0.0583 (9)
C10.7424 (4)0.0602 (7)0.03597 (18)0.0563 (10)
C20.7242 (5)0.1141 (8)0.0929 (2)0.0633 (11)
C30.6344 (6)0.0130 (9)0.1316 (2)0.0726 (13)
H30.62150.02500.16980.087*
C40.5637 (7)0.1991 (10)0.1122 (2)0.0780 (15)
H40.50310.28550.13780.094*
C50.5826 (6)0.2571 (8)0.0551 (2)0.0702 (13)
H50.53550.38160.04260.084*
C60.6735 (5)0.1260 (8)0.01661 (19)0.0601 (11)
C70.6987 (5)0.1680 (8)0.0444 (2)0.0595 (11)
C80.8511 (5)0.0019 (8)0.12865 (19)0.0605 (10)
C90.9371 (8)0.1758 (11)0.1478 (2)0.0881 (18)
H90.95390.28680.12280.106*
C101.0003 (9)0.1906 (12)0.2041 (3)0.102 (2)
H101.05920.31010.21650.123*
C110.9753 (9)0.0292 (13)0.2410 (3)0.101 (2)
H111.01590.03770.27880.122*
C120.8898 (9)0.1454 (14)0.2216 (3)0.109 (2)
H120.87410.25700.24650.131*
C130.8265 (8)0.1600 (11)0.1664 (3)0.0893 (16)
H130.76680.27940.15440.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.0545 (3)0.0479 (4)0.0701 (4)0.00223 (18)0.0004 (2)0.0048 (2)
O10.083 (2)0.067 (2)0.091 (2)0.0099 (19)0.0086 (19)0.0075 (19)
O20.112 (3)0.106 (3)0.086 (2)0.002 (3)0.008 (2)0.026 (3)
O30.087 (2)0.056 (2)0.086 (2)0.0245 (17)0.0082 (19)0.0001 (17)
N10.068 (3)0.071 (3)0.079 (3)0.010 (2)0.003 (2)0.008 (2)
N20.0562 (19)0.052 (2)0.066 (2)0.0045 (15)0.0023 (16)0.0066 (16)
C10.0406 (19)0.057 (3)0.071 (2)0.0049 (16)0.0002 (17)0.007 (2)
C20.054 (2)0.061 (3)0.075 (3)0.007 (2)0.0001 (19)0.006 (2)
C30.064 (3)0.084 (4)0.068 (3)0.012 (2)0.008 (2)0.008 (2)
C40.064 (3)0.089 (4)0.080 (3)0.004 (3)0.008 (2)0.026 (3)
C50.061 (3)0.062 (3)0.088 (3)0.003 (2)0.006 (2)0.026 (2)
C60.049 (2)0.059 (3)0.073 (3)0.0053 (19)0.0056 (19)0.016 (2)
C70.054 (2)0.055 (2)0.070 (3)0.0004 (19)0.0046 (19)0.014 (2)
C80.053 (2)0.062 (3)0.066 (2)0.0004 (19)0.0033 (18)0.006 (2)
C90.114 (5)0.084 (4)0.068 (3)0.036 (3)0.013 (3)0.011 (3)
C100.121 (5)0.108 (5)0.077 (3)0.043 (4)0.005 (3)0.016 (3)
C110.116 (5)0.110 (5)0.075 (3)0.025 (4)0.014 (3)0.003 (3)
C120.132 (6)0.106 (5)0.085 (4)0.023 (4)0.025 (4)0.029 (4)
C130.104 (4)0.078 (4)0.083 (3)0.020 (3)0.016 (3)0.010 (3)
Geometric parameters (Å, º) top
Se1—C11.852 (4)C5—C61.402 (7)
Se1—N21.897 (4)C5—H50.9300
O1—N11.251 (6)C6—C71.461 (6)
O2—N11.215 (6)C8—C91.362 (7)
O3—C71.213 (6)C8—C131.377 (8)
N1—C21.442 (7)C9—C101.395 (8)
N2—C71.399 (6)C9—H90.9300
N2—C81.421 (6)C10—C111.362 (10)
C1—C21.381 (6)C10—H100.9300
C1—C61.389 (7)C11—C121.366 (10)
C2—C31.386 (7)C11—H110.9300
C3—C41.396 (8)C12—C131.370 (8)
C3—H30.9300C12—H120.9300
C4—C51.391 (8)C13—H130.9300
C4—H40.9300
C1—Se1—N285.48 (17)C1—C6—C7116.1 (4)
O2—N1—O1123.5 (5)C5—C6—C7124.3 (5)
O2—N1—C2120.2 (5)O3—C7—N2125.5 (4)
O1—N1—C2116.3 (4)O3—C7—C6124.8 (4)
C7—N2—C8125.9 (4)N2—C7—C6109.7 (4)
C7—N2—Se1115.2 (3)C9—C8—C13118.5 (5)
C8—N2—Se1118.8 (3)C9—C8—N2118.6 (5)
C2—C1—C6120.4 (4)C13—C8—N2122.9 (4)
C2—C1—Se1126.2 (4)C8—C9—C10121.2 (6)
C6—C1—Se1113.4 (3)C8—C9—H9119.4
C1—C2—C3121.0 (5)C10—C9—H9119.4
C1—C2—N1118.3 (4)C11—C10—C9119.7 (6)
C3—C2—N1120.7 (5)C11—C10—H10120.2
C2—C3—C4118.8 (5)C9—C10—H10120.2
C2—C3—H3120.6C10—C11—C12118.9 (6)
C4—C3—H3120.6C10—C11—H11120.5
C5—C4—C3120.9 (5)C12—C11—H11120.5
C5—C4—H4119.6C11—C12—C13121.6 (7)
C3—C4—H4119.6C11—C12—H12119.2
C4—C5—C6119.4 (5)C13—C12—H12119.2
C4—C5—H5120.3C12—C13—C8120.0 (6)
C6—C5—H5120.3C12—C13—H13120.0
C1—C6—C5119.5 (5)C8—C13—H13120.0
C1—Se1—N2—C71.8 (3)C4—C5—C6—C7178.6 (5)
C1—Se1—N2—C8178.6 (3)C8—N2—C7—O32.5 (7)
N2—Se1—C1—C2179.0 (4)Se1—N2—C7—O3177.1 (4)
N2—Se1—C1—C60.4 (3)C8—N2—C7—C6177.8 (4)
C6—C1—C2—C31.4 (7)Se1—N2—C7—C62.6 (5)
Se1—C1—C2—C3179.2 (4)C1—C6—C7—O3177.4 (4)
C6—C1—C2—N1180.0 (4)C5—C6—C7—O30.9 (8)
Se1—C1—C2—N10.7 (6)C1—C6—C7—N22.3 (5)
O2—N1—C2—C1177.0 (4)C5—C6—C7—N2179.4 (4)
O1—N1—C2—C12.8 (6)C7—N2—C8—C9176.0 (5)
O2—N1—C2—C31.6 (7)Se1—N2—C8—C93.5 (6)
O1—N1—C2—C3178.6 (5)C7—N2—C8—C136.3 (7)
C1—C2—C3—C40.8 (7)Se1—N2—C8—C13174.1 (4)
N1—C2—C3—C4179.3 (4)C13—C8—C9—C100.5 (10)
C2—C3—C4—C50.1 (8)N2—C8—C9—C10177.3 (6)
C3—C4—C5—C60.3 (8)C8—C9—C10—C110.4 (12)
C2—C1—C6—C51.2 (6)C9—C10—C11—C120.6 (13)
Se1—C1—C6—C5179.4 (3)C10—C11—C12—C131.1 (13)
C2—C1—C6—C7179.6 (4)C11—C12—C13—C81.2 (12)
Se1—C1—C6—C71.0 (5)C9—C8—C13—C120.9 (10)
C4—C5—C6—C10.4 (7)N2—C8—C13—C12176.7 (6)

Experimental details

Crystal data
Chemical formulaC13H8N2O3Se
Mr319.17
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)8.069 (1), 6.322 (2), 23.512 (3)
β (°) 93.38 (2)
V3)1197.3 (4)
Z4
Radiation typeCu Kα
µ (mm1)4.32
Crystal size (mm)0.58 × 0.57 × 0.08
Data collection
DiffractometerStoe–Siemens AED four-circle
diffractometer
Absorption correctionψ scan
(EMPIR; Stoe & Cie, 1987)
Tmin, Tmax0.157, 0.724
No. of measured, independent and
observed [I > 2σ(I)] reflections
2310, 2146, 1675
Rint0.035
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.145, 0.99
No. of reflections2146
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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.

Selected geometric parameters (Å, º) top
Se1—C11.852 (4)O3—C71.213 (6)
Se1—N21.897 (4)N1—C21.442 (7)
O1—N11.251 (6)N2—C71.399 (6)
O2—N11.215 (6)N2—C81.421 (6)
C1—Se1—N285.48 (17)C8—N2—Se1118.8 (3)
O2—N1—O1123.5 (5)C2—C1—Se1126.2 (4)
O2—N1—C2120.2 (5)C6—C1—Se1113.4 (3)
O1—N1—C2116.3 (4)O3—C7—N2125.5 (4)
C7—N2—C8125.9 (4)O3—C7—C6124.8 (4)
C7—N2—Se1115.2 (3)N2—C7—C6109.7 (4)
C7—N2—C8—C136.3 (7)Se1—N2—C8—C13174.1 (4)
 

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