Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802003422/dn6021sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802003422/dn6021Isup2.hkl |
CCDC reference: 182643
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.041
- wR factor = 0.111
- Data-to-parameter ratio = 11.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(8) - C(9) = 1.49 Ang. General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.787 Tmax scaled 0.295 Tmin scaled 0.110
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
The synthesis of the title compound was carried out in two steps. o-Methylselenobenzoic acid was treated with α,α-dichloromethyl ether and then with KCN (Messali, 2001). A yellow single-crystal was obtained by slow evaporation of a toluene solution.
All H atoms were included in the refinement in the-riding model approximation, with isotropic displacement parameters fixed at 1.2Ueq of the parent atom (1.5 Ueq for methyl H atoms).
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); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (I) with the atom-labelling scheme. Displacement ellipsoids are shown at the 50% probability level. |
C9H7NOSe | F(000) = 880 |
Mr = 224.12 | Dx = 1.677 Mg m−3 |
Orthorhombic, Cmca | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -C 2bc 2 | Cell parameters from 32 reflections |
a = 6.8433 (19) Å | θ = 31.5–36.3° |
b = 15.585 (9) Å | µ = 5.31 mm−1 |
c = 16.6460 (12) Å | T = 293 K |
V = 1775.4 (12) Å3 | Prism, yellow |
Z = 8 | 0.61 × 0.38 × 0.23 mm |
Stoe–Siemens AED four-circle diffractometer | 624 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 67.9°, θmin = 5.3° |
ω scans | h = 0→8 |
Absorption correction: ψ scan (EMPIR; Stoe & Cie, 1987) | k = 0→18 |
Tmin = 0.140, Tmax = 0.375 | l = 0→20 |
848 measured reflections | 2 standard reflections every 60 min |
848 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)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0712P)2 + 0.7549P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
848 reflections | Δρmax = 0.41 e Å−3 |
74 parameters | Δρmin = −0.34 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: 0.0078 (6) |
C9H7NOSe | V = 1775.4 (12) Å3 |
Mr = 224.12 | Z = 8 |
Orthorhombic, Cmca | Cu Kα radiation |
a = 6.8433 (19) Å | µ = 5.31 mm−1 |
b = 15.585 (9) Å | T = 293 K |
c = 16.6460 (12) Å | 0.61 × 0.38 × 0.23 mm |
Stoe–Siemens AED four-circle diffractometer | 624 reflections with I > 2σ(I) |
Absorption correction: ψ scan (EMPIR; Stoe & Cie, 1987) | Rint = 0.000 |
Tmin = 0.140, Tmax = 0.375 | 2 standard reflections every 60 min |
848 measured reflections | intensity decay: 5% |
848 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.41 e Å−3 |
848 reflections | Δρmin = −0.34 e Å−3 |
74 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 | Occ. (<1) | |
Se1 | 0.0000 | 0.09438 (4) | 0.45132 (3) | 0.0814 (4) | |
O1 | 0.0000 | 0.1952 (2) | 0.5863 (2) | 0.0840 (11) | |
N1 | 0.0000 | 0.3958 (3) | 0.6510 (3) | 0.0974 (16) | |
C1 | 0.0000 | 0.2081 (3) | 0.4125 (3) | 0.0691 (12) | |
C2 | 0.0000 | 0.2265 (4) | 0.3304 (3) | 0.0767 (14) | |
H2 | 0.0000 | 0.1816 | 0.2936 | 0.092* | |
C3 | 0.0000 | 0.3098 (4) | 0.3028 (3) | 0.0869 (17) | |
H3 | 0.0000 | 0.3205 | 0.2479 | 0.104* | |
C4 | 0.0000 | 0.3766 (4) | 0.3554 (4) | 0.0887 (16) | |
H4 | 0.0000 | 0.4327 | 0.3361 | 0.106* | |
C5 | 0.0000 | 0.3620 (4) | 0.4361 (3) | 0.0808 (15) | |
H5 | 0.0000 | 0.4082 | 0.4714 | 0.097* | |
C6 | 0.0000 | 0.2779 (3) | 0.4665 (3) | 0.0700 (13) | |
C7 | 0.0000 | 0.0321 (4) | 0.3510 (3) | 0.0968 (19) | |
H7A | 0.0000 | −0.0284 | 0.3617 | 0.145* | |
H7B | 0.1145 | 0.0469 | 0.3207 | 0.145* | 0.50 |
H7C | −0.1145 | 0.0469 | 0.3207 | 0.145* | 0.50 |
C8 | 0.0000 | 0.2641 (4) | 0.5529 (3) | 0.0748 (14) | |
C9 | 0.0000 | 0.3414 (4) | 0.6056 (3) | 0.0804 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.1192 (6) | 0.0709 (5) | 0.0542 (4) | 0.000 | 0.000 | 0.0010 (2) |
O1 | 0.111 (3) | 0.084 (2) | 0.0572 (19) | 0.000 | 0.000 | 0.0011 (17) |
N1 | 0.134 (5) | 0.093 (3) | 0.066 (3) | 0.000 | 0.000 | −0.014 (2) |
C1 | 0.081 (3) | 0.072 (3) | 0.055 (2) | 0.000 | 0.000 | 0.003 (2) |
C2 | 0.100 (4) | 0.078 (3) | 0.052 (2) | 0.000 | 0.000 | 0.000 (2) |
C3 | 0.119 (5) | 0.087 (3) | 0.054 (3) | 0.000 | 0.000 | 0.007 (2) |
C4 | 0.113 (5) | 0.082 (3) | 0.071 (3) | 0.000 | 0.000 | 0.009 (3) |
C5 | 0.109 (4) | 0.067 (3) | 0.066 (3) | 0.000 | 0.000 | 0.002 (2) |
C6 | 0.081 (3) | 0.074 (3) | 0.055 (3) | 0.000 | 0.000 | 0.000 (2) |
C7 | 0.150 (6) | 0.079 (3) | 0.062 (3) | 0.000 | 0.000 | −0.007 (3) |
C8 | 0.092 (4) | 0.080 (4) | 0.052 (2) | 0.000 | 0.000 | −0.005 (2) |
C9 | 0.097 (4) | 0.089 (3) | 0.056 (2) | 0.000 | 0.000 | −0.001 (3) |
Se1—C1 | 1.887 (5) | C4—C5 | 1.362 (7) |
Se1—C7 | 1.932 (5) | C4—H4 | 0.9300 |
O1—C8 | 1.210 (7) | C5—C6 | 1.405 (8) |
N1—C9 | 1.135 (7) | C5—H5 | 0.9300 |
C1—C2 | 1.398 (6) | C6—C8 | 1.454 (5) |
C1—C6 | 1.410 (7) | C7—H7A | 0.9600 |
C2—C3 | 1.377 (8) | C7—H7B | 0.9600 |
C2—H2 | 0.9300 | C7—H7C | 0.9600 |
C3—C4 | 1.360 (8) | C8—C9 | 1.491 (8) |
C3—H3 | 0.9300 | ||
C1—Se1—C7 | 100.2 (2) | C6—C5—H5 | 119.6 |
C2—C1—C6 | 117.8 (5) | C5—C6—C1 | 119.3 (4) |
C2—C1—Se1 | 121.8 (4) | C5—C6—C8 | 119.6 (5) |
C6—C1—Se1 | 120.5 (4) | C1—C6—C8 | 121.1 (5) |
C3—C2—C1 | 121.2 (5) | Se1—C7—H7A | 109.5 |
C3—C2—H2 | 119.4 | Se1—C7—H7B | 109.5 |
C1—C2—H2 | 119.4 | H7A—C7—H7B | 109.5 |
C4—C3—C2 | 120.6 (5) | Se1—C7—H7C | 109.5 |
C4—C3—H3 | 119.7 | H7A—C7—H7C | 109.5 |
C2—C3—H3 | 119.7 | H7B—C7—H7C | 109.5 |
C3—C4—C5 | 120.4 (5) | O1—C8—C6 | 125.9 (5) |
C3—C4—H4 | 119.8 | O1—C8—C9 | 116.5 (4) |
C5—C4—H4 | 119.8 | C6—C8—C9 | 117.6 (5) |
C4—C5—C6 | 120.8 (5) | N1—C9—C8 | 174.4 (6) |
C4—C5—H5 | 119.6 |
Experimental details
Crystal data | |
Chemical formula | C9H7NOSe |
Mr | 224.12 |
Crystal system, space group | Orthorhombic, Cmca |
Temperature (K) | 293 |
a, b, c (Å) | 6.8433 (19), 15.585 (9), 16.6460 (12) |
V (Å3) | 1775.4 (12) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 5.31 |
Crystal size (mm) | 0.61 × 0.38 × 0.23 |
Data collection | |
Diffractometer | Stoe–Siemens AED four-circle diffractometer |
Absorption correction | ψ scan (EMPIR; Stoe & Cie, 1987) |
Tmin, Tmax | 0.140, 0.375 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 848, 848, 624 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.111, 1.01 |
No. of reflections | 848 |
No. of parameters | 74 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.41, −0.34 |
Computer programs: DIF4 (Stoe & Cie, 1987), DIF4, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97.
Se1—C1 | 1.887 (5) | N1—C9 | 1.135 (7) |
Se1—C7 | 1.932 (5) | C6—C8 | 1.454 (5) |
O1—C8 | 1.210 (7) | ||
C1—Se1—C7 | 100.2 (2) | C6—C8—C9 | 117.6 (5) |
O1—C8—C6 | 125.9 (5) | N1—C9—C8 | 174.4 (6) |
O1—C8—C9 | 116.5 (4) |
Some modifications of the molecular structure of Ebselen (Natterman/RP, 1981; Dupont et al., 1990), an anti-inflammatory compound, have been attempted in order to obtain a more soluble derivative which retains the pharmacological properties. The crystal structure of the title compound, (I), was determined in order to identify without ambiguity a potential antioxidant derivative. All the atomic positions, except for two H atoms of the methyl group, were refined in the plane (0,y,z) of the unit cell. All the atoms have an occupation factor of 0.5. The crystal packing is governed by van der Waals interactions. There is an Se···Sei close contact [symmetry code: (i) x, -y, 1 - z) of 3.359 (2) Å, rather less than the sum of Se atom radii (3.8 Å; Bondi, 1964). The distance is nevertheless larger than that of a covalent Se—Se bond [2.3229 (6) Å; Kumar & Nangia, 2000].