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The title compound, C9H11ISe, displays the following dimensions involving selenium: Se—I 2.5360 (11) Å, Se—C1 1.923 (6) Å and C—Se—I 100.2 (2)°. Short Se...I and I...I contacts link the mol­ecules into ribbons parallel to the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802003677/bt6116sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802003677/bt6116Isup2.hkl
Contains datablock I

CCDC reference: 183772

Key indicators

  • Single-crystal X-ray study
  • T = 178 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.038
  • wR factor = 0.109
  • Data-to-parameter ratio = 17.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
ABSTM_02 Alert A The ratio of expected to reported Tmax/Tmin(RR) is > 2.00 Tmin and Tmax reported: 0.590 0.932 Tmin and Tmax expected: 0.218 0.719 RR = 2.084 Please check that your absorption correction is appropriate.
Author response: The absorption correction was based on psi-scans and appears adequate in terms of the structure refinement (no misshapen ellipsoids, no large features of residual electron density). The calculated minimum transmission may be misleading in that no X-ray beam may actually traverse the whole length of the crystal, which was a needle mounted parallel to the glass fibre.
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 0.771 Tmax scaled 0.719 Tmin scaled 0.455
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check

Computing details top

Data collection: P3 Software (Nicolet, 1987); cell refinement: P3 Software; data reduction: XDISK (Nicolet, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

mesitylselenenyl iodide top
Crystal data top
C9H11ISeF(000) = 608
Mr = 325.04Dx = 2.101 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.964 (5) ÅCell parameters from 50 reflections
b = 4.606 (2) Åθ = 10–11.5°
c = 16.214 (6) ŵ = 6.60 mm1
β = 99.87 (3)°T = 178 K
V = 1027.5 (7) Å3Needle, dark red
Z = 40.6 × 0.2 × 0.05 mm
Data collection top
Nicolet P3
diffractometer
1442 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
Graphite monochromatorθmax = 25.1°, θmin = 3.6°
ω scansh = 1616
Absorption correction: ψ scan
(XEMP; Siemens 1994)
k = 53
Tmin = 0.590, Tmax = 0.932l = 1919
5385 measured reflections3 standard reflections every 147 reflections
1811 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.19 w = 1/[σ2(Fo2) + (0.0519P)2 + 0.8646P]
where P = (Fo2 + 2Fc2)/3
1811 reflections(Δ/σ)max < 0.001
103 parametersΔρmax = 1.09 e Å3
0 restraintsΔρmin = 1.32 e Å3
Special details top

Experimental. mesitylselenenyl iodide

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*/UeqOcc. (<1)
I0.09448 (4)0.21646 (10)0.21344 (3)0.0397 (2)
Se0.20453 (6)0.52063 (16)0.13871 (4)0.0435 (2)
C10.2510 (5)0.2277 (13)0.0709 (4)0.0297 (14)
C20.1949 (5)0.1555 (15)0.0061 (4)0.0317 (14)
C30.2325 (5)0.0386 (15)0.0562 (4)0.0377 (16)
H30.19450.09230.10820.045*
C40.3240 (6)0.1589 (16)0.0335 (4)0.0400 (17)
C50.3775 (5)0.0832 (18)0.0439 (5)0.0448 (18)
H50.44050.16390.06040.054*
C60.3420 (5)0.1056 (16)0.0975 (4)0.0374 (15)
C70.0935 (5)0.2757 (16)0.0347 (5)0.0427 (18)
H7A0.06580.19120.08900.064*
H7B0.09690.48720.04000.064*
H7C0.05230.22620.00650.064*
C80.3644 (7)0.3616 (19)0.0916 (6)0.063 (3)
H8A0.43530.36850.07630.095*0.50
H8B0.34650.29200.14930.095*0.50
H8C0.33760.55650.08710.095*0.50
H8D0.31090.44280.13210.095*0.50
H8E0.39980.51940.05910.095*0.50
H8F0.40870.25480.12140.095*0.50
C90.4026 (7)0.174 (2)0.1806 (5)0.058 (2)
H9A0.46140.05370.18870.087*
H9B0.36520.13350.22520.087*
H9C0.42100.37960.18230.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I0.0506 (3)0.0378 (3)0.0361 (3)0.0022 (2)0.0227 (2)0.00297 (18)
Se0.0610 (5)0.0309 (4)0.0449 (4)0.0112 (3)0.0266 (4)0.0078 (3)
C10.038 (4)0.026 (3)0.029 (3)0.003 (3)0.016 (3)0.002 (2)
C20.031 (3)0.031 (4)0.036 (3)0.003 (3)0.014 (3)0.004 (3)
C30.048 (4)0.033 (4)0.034 (3)0.005 (3)0.014 (3)0.005 (3)
C40.054 (5)0.031 (4)0.040 (4)0.004 (3)0.024 (3)0.003 (3)
C50.034 (4)0.048 (5)0.057 (4)0.010 (3)0.020 (3)0.026 (4)
C60.040 (4)0.038 (4)0.035 (3)0.001 (3)0.010 (3)0.013 (3)
C70.035 (4)0.050 (5)0.045 (4)0.006 (3)0.010 (3)0.007 (3)
C80.081 (7)0.038 (5)0.085 (6)0.005 (5)0.051 (5)0.005 (4)
C90.050 (5)0.079 (7)0.043 (4)0.012 (5)0.000 (4)0.012 (4)
Geometric parameters (Å, º) top
I—Se2.5360 (11)C5—H50.9500
I—Sei3.8393 (15)C6—C91.496 (10)
I—Iii3.8398 (13)C7—H7A0.9800
I—Iiii3.8398 (13)C7—H7B0.9800
Se—C11.923 (6)C7—H7C0.9800
Se—Iiv3.8393 (15)C8—H8A0.9800
C1—C61.389 (10)C8—H8B0.9800
C1—C21.395 (9)C8—H8C0.9800
C2—C31.371 (9)C8—H8D0.9800
C2—C71.517 (10)C8—H8E0.9800
C3—C41.383 (11)C8—H8F0.9800
C3—H30.9500C9—H9A0.9800
C4—C51.391 (11)C9—H9B0.9800
C4—C81.502 (10)C9—H9C0.9800
C5—C61.380 (11)
Se—I—Sei90.13 (4)C1—C6—C9122.8 (7)
Se—I—Iii169.63 (3)C2—C7—H7A109.5
Sei—I—Iii86.00 (3)C2—C7—H7B109.5
Se—I—Iiii108.72 (4)H7A—C7—H7B109.5
Sei—I—Iiii158.68 (2)C2—C7—H7C109.5
Iii—I—Iiii73.71 (3)H7A—C7—H7C109.5
C1—Se—I100.21 (18)H7B—C7—H7C109.5
C1—Se—Iiv163.54 (19)C4—C8—H8A109.5
I—Se—Iiv90.13 (4)C4—C8—H8B109.5
C6—C1—C2121.7 (6)H8A—C8—H8B109.5
C6—C1—Se119.1 (5)C4—C8—H8C109.5
C2—C1—Se119.1 (5)H8A—C8—H8C109.5
C3—C2—C1118.1 (6)H8B—C8—H8C109.5
C3—C2—C7119.3 (6)C4—C8—H8D109.5
C1—C2—C7122.5 (6)C4—C8—H8E109.5
C2—C3—C4122.3 (7)H8D—C8—H8E109.5
C2—C3—H3118.8C4—C8—H8F109.5
C4—C3—H3118.8H8D—C8—H8F109.5
C3—C4—C5117.9 (7)H8E—C8—H8F109.5
C3—C4—C8120.7 (7)C6—C9—H9A109.5
C5—C4—C8121.3 (8)C6—C9—H9B109.5
C6—C5—C4122.1 (7)H9A—C9—H9B109.5
C6—C5—H5119.0C6—C9—H9C109.5
C4—C5—H5119.0H9A—C9—H9C109.5
C5—C6—C1117.9 (6)H9B—C9—H9C109.5
C5—C6—C9119.4 (7)
Sei—I—Se—C112.9 (2)Se—C1—C2—C76.7 (9)
Iii—I—Se—C155.1 (3)C1—C2—C3—C41.2 (10)
Iiii—I—Se—C1157.0 (2)C7—C2—C3—C4179.3 (6)
Sei—I—Se—Iiv180.0C2—C3—C4—C51.6 (10)
Iii—I—Se—Iiv112.05 (14)C2—C3—C4—C8177.5 (7)
Iiii—I—Se—Iiv10.15 (3)C3—C4—C5—C60.0 (10)
I—Se—C1—C699.3 (5)C8—C4—C5—C6179.2 (7)
Iiv—Se—C1—C6132.6 (6)C4—C5—C6—C12.0 (10)
I—Se—C1—C284.4 (5)C4—C5—C6—C9178.9 (7)
Iiv—Se—C1—C243.7 (10)C2—C1—C6—C52.4 (10)
C6—C1—C2—C30.8 (10)Se—C1—C6—C5173.8 (5)
Se—C1—C2—C3175.4 (5)C2—C1—C6—C9178.5 (7)
C6—C1—C2—C7177.1 (6)Se—C1—C6—C95.3 (9)
Symmetry codes: (i) x, y1, z; (ii) x, y1/2, z+1/2; (iii) x, y+1/2, z+1/2; (iv) x, y+1, z.
 

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