Mesityl­selenenyl iodide

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.

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


 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

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

Crystal data

C9H11ISe	F(000) = 608
Mr = 325.04	Dx = 2.101 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.964 (5) Å	Cell parameters from 50 reflections
b = 4.606 (2) Å	θ = 10–11.5°
c = 16.214 (6) Å	µ = 6.60 mm^−1
β = 99.87 (3)°	T = 178 K
V = 1027.5 (7) Å^3	Needle, dark red
Z = 4	0.6 × 0.2 × 0.05 mm

Data collection

Nicolet P3 diffractometer	1442 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
Graphite monochromator	θmax = 25.1°, θmin = 3.6°
ω scans	h = −16→16
Absorption correction: ψ scan (XEMP; Siemens 1994)	k = −5→3
Tmin = 0.590, Tmax = 0.932	l = −19→19
5385 measured reflections	3 standard reflections every 147 reflections
1811 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0519P)^2 + 0.8646P] where P = (Fo^2 + 2Fc^2)/3
1811 reflections	(Δ/σ)max < 0.001
103 parameters	Δρmax = 1.09 e Å^−3
0 restraints	Δρmin = −1.32 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
I	0.09448 (4)	0.21646 (10)	0.21344 (3)	0.0397 (2)
Se	0.20453 (6)	0.52063 (16)	0.13871 (4)	0.0435 (2)
C1	0.2510 (5)	0.2277 (13)	0.0709 (4)	0.0297 (14)
C2	0.1949 (5)	0.1555 (15)	−0.0061 (4)	0.0317 (14)
C3	0.2325 (5)	−0.0386 (15)	−0.0562 (4)	0.0377 (16)
H3	0.1945	−0.0923	−0.1082	0.045*
C4	0.3240 (6)	−0.1589 (16)	−0.0335 (4)	0.0400 (17)
C5	0.3775 (5)	−0.0832 (18)	0.0439 (5)	0.0448 (18)
H5	0.4405	−0.1639	0.0604	0.054*
C6	0.3420 (5)	0.1056 (16)	0.0975 (4)	0.0374 (15)
C7	0.0935 (5)	0.2757 (16)	−0.0347 (5)	0.0427 (18)
H7A	0.0658	0.1912	−0.0890	0.064*
H7B	0.0969	0.4872	−0.0400	0.064*
H7C	0.0523	0.2262	0.0065	0.064*
C8	0.3644 (7)	−0.3616 (19)	−0.0916 (6)	0.063 (3)
H8A	0.4353	−0.3685	−0.0763	0.095*	0.50
H8B	0.3465	−0.2920	−0.1493	0.095*	0.50
H8C	0.3376	−0.5565	−0.0871	0.095*	0.50
H8D	0.3109	−0.4428	−0.1321	0.095*	0.50
H8E	0.3998	−0.5194	−0.0591	0.095*	0.50
H8F	0.4087	−0.2548	−0.1214	0.095*	0.50
C9	0.4026 (7)	0.174 (2)	0.1806 (5)	0.058 (2)
H9A	0.4614	0.0537	0.1887	0.087*
H9B	0.3652	0.1335	0.2252	0.087*
H9C	0.4210	0.3796	0.1823	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I	0.0506 (3)	0.0378 (3)	0.0361 (3)	−0.0022 (2)	0.0227 (2)	−0.00297 (18)
Se	0.0610 (5)	0.0309 (4)	0.0449 (4)	−0.0112 (3)	0.0266 (4)	−0.0078 (3)
C1	0.038 (4)	0.026 (3)	0.029 (3)	−0.003 (3)	0.016 (3)	0.002 (2)
C2	0.031 (3)	0.031 (4)	0.036 (3)	−0.003 (3)	0.014 (3)	0.004 (3)
C3	0.048 (4)	0.033 (4)	0.034 (3)	−0.005 (3)	0.014 (3)	0.005 (3)
C4	0.054 (5)	0.031 (4)	0.040 (4)	−0.004 (3)	0.024 (3)	0.003 (3)
C5	0.034 (4)	0.048 (5)	0.057 (4)	0.010 (3)	0.020 (3)	0.026 (4)
C6	0.040 (4)	0.038 (4)	0.035 (3)	−0.001 (3)	0.010 (3)	0.013 (3)
C7	0.035 (4)	0.050 (5)	0.045 (4)	0.006 (3)	0.010 (3)	0.007 (3)
C8	0.081 (7)	0.038 (5)	0.085 (6)	0.005 (5)	0.051 (5)	−0.005 (4)
C9	0.050 (5)	0.079 (7)	0.043 (4)	−0.012 (5)	0.000 (4)	0.012 (4)

Geometric parameters (Å, º)

I—Se	2.5360 (11)	C5—H5	0.9500
I—Se^i	3.8393 (15)	C6—C9	1.496 (10)
I—I^ii	3.8398 (13)	C7—H7A	0.9800
I—I^iii	3.8398 (13)	C7—H7B	0.9800
Se—C1	1.923 (6)	C7—H7C	0.9800
Se—I^iv	3.8393 (15)	C8—H8A	0.9800
C1—C6	1.389 (10)	C8—H8B	0.9800
C1—C2	1.395 (9)	C8—H8C	0.9800
C2—C3	1.371 (9)	C8—H8D	0.9800
C2—C7	1.517 (10)	C8—H8E	0.9800
C3—C4	1.383 (11)	C8—H8F	0.9800
C3—H3	0.9500	C9—H9A	0.9800
C4—C5	1.391 (11)	C9—H9B	0.9800
C4—C8	1.502 (10)	C9—H9C	0.9800
C5—C6	1.380 (11)
Se—I—Se^i	90.13 (4)	C1—C6—C9	122.8 (7)
Se—I—I^ii	169.63 (3)	C2—C7—H7A	109.5
Se^i—I—I^ii	86.00 (3)	C2—C7—H7B	109.5
Se—I—I^iii	108.72 (4)	H7A—C7—H7B	109.5
Se^i—I—I^iii	158.68 (2)	C2—C7—H7C	109.5
I^ii—I—I^iii	73.71 (3)	H7A—C7—H7C	109.5
C1—Se—I	100.21 (18)	H7B—C7—H7C	109.5
C1—Se—I^iv	163.54 (19)	C4—C8—H8A	109.5
I—Se—I^iv	90.13 (4)	C4—C8—H8B	109.5
C6—C1—C2	121.7 (6)	H8A—C8—H8B	109.5
C6—C1—Se	119.1 (5)	C4—C8—H8C	109.5
C2—C1—Se	119.1 (5)	H8A—C8—H8C	109.5
C3—C2—C1	118.1 (6)	H8B—C8—H8C	109.5
C3—C2—C7	119.3 (6)	C4—C8—H8D	109.5
C1—C2—C7	122.5 (6)	C4—C8—H8E	109.5
C2—C3—C4	122.3 (7)	H8D—C8—H8E	109.5
C2—C3—H3	118.8	C4—C8—H8F	109.5
C4—C3—H3	118.8	H8D—C8—H8F	109.5
C3—C4—C5	117.9 (7)	H8E—C8—H8F	109.5
C3—C4—C8	120.7 (7)	C6—C9—H9A	109.5
C5—C4—C8	121.3 (8)	C6—C9—H9B	109.5
C6—C5—C4	122.1 (7)	H9A—C9—H9B	109.5
C6—C5—H5	119.0	C6—C9—H9C	109.5
C4—C5—H5	119.0	H9A—C9—H9C	109.5
C5—C6—C1	117.9 (6)	H9B—C9—H9C	109.5
C5—C6—C9	119.4 (7)
Se^i—I—Se—C1	12.9 (2)	Se—C1—C2—C7	−6.7 (9)
I^ii—I—Se—C1	−55.1 (3)	C1—C2—C3—C4	−1.2 (10)
I^iii—I—Se—C1	−157.0 (2)	C7—C2—C3—C4	−179.3 (6)
Se^i—I—Se—I^iv	180.0	C2—C3—C4—C5	1.6 (10)
I^ii—I—Se—I^iv	112.05 (14)	C2—C3—C4—C8	−177.5 (7)
I^iii—I—Se—I^iv	10.15 (3)	C3—C4—C5—C6	0.0 (10)
I—Se—C1—C6	−99.3 (5)	C8—C4—C5—C6	179.2 (7)
I^iv—Se—C1—C6	132.6 (6)	C4—C5—C6—C1	−2.0 (10)
I—Se—C1—C2	84.4 (5)	C4—C5—C6—C9	178.9 (7)
I^iv—Se—C1—C2	−43.7 (10)	C2—C1—C6—C5	2.4 (10)
C6—C1—C2—C3	−0.8 (10)	Se—C1—C6—C5	−173.8 (5)
Se—C1—C2—C3	175.4 (5)	C2—C1—C6—C9	−178.5 (7)
C6—C1—C2—C7	177.1 (6)	Se—C1—C6—C9	5.3 (9)

Symmetry codes: (i) x, y−1, z; (ii) −x, y−1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) x, y+1, z.