Iodo­(triphen­yl)silane

The mol­ecular structure of the title compound, C₁₈H₁₅ISi, which crystallizes in the space group C2/c, does not exhibit any unusual features. Two weak C—H...π inter­actions may help to consolidate the packing. The present structure is not isostructural with the known Ph₃SiX (X = F, Cl or Br) compounds.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.073
• wR factor = 0.153
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.01344 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     10.774 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.087 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          7 Note

Alert level G
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      60.75 Why ?
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        64% Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015) and publCIF (Westrip, 2010).

Iodo(triphenyl)silane

Crystal data

C18H15ISi	F(000) = 1520
Mr = 386.29	Dx = 1.558 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.0488 (8) Å	Cell parameters from 12164 reflections
b = 11.2984 (6) Å	θ = 3.4–26.2°
c = 19.648 (1) Å	µ = 2.01 mm^−1
β = 112.379 (4)°	T = 173 K
V = 3294.4 (3) Å^3	Block, colourless
Z = 8	0.23 × 0.14 × 0.13 mm

Data collection

Stoe IPDS II two-circle diffractometer	2338 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.052
ω scans	θmax = 25.0°, θmin = 3.5°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −19→19
Tmin = 0.411, Tmax = 1.000	k = −13→13
12164 measured reflections	l = −23→23
2901 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.073	H-atom parameters constrained
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.0192P)^2 + 60.7486P] where P = (Fo^2 + 2Fc^2)/3
S = 1.34	(Δ/σ)max < 0.001
2901 reflections	Δρmax = 1.02 e Å^−3
181 parameters	Δρmin = −0.80 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.48451 (4)	0.29151 (7)	0.36275 (4)	0.0545 (3)
Si1	0.37819 (15)	0.2688 (2)	0.42609 (12)	0.0318 (5)
C1	0.3086 (5)	0.4064 (7)	0.4073 (4)	0.0286 (18)
C2	0.3497 (6)	0.5180 (8)	0.4247 (5)	0.040 (2)
H2	0.413607	0.523733	0.445319	0.048*
C3	0.2981 (7)	0.6198 (8)	0.4121 (5)	0.046 (2)
H3	0.326338	0.694979	0.424663	0.055*
C4	0.2059 (7)	0.6116 (8)	0.3814 (6)	0.051 (3)
H4	0.170471	0.681529	0.372985	0.062*
C5	0.1639 (6)	0.5031 (9)	0.3626 (5)	0.044 (2)
H5	0.100048	0.498101	0.340368	0.053*
C6	0.2161 (6)	0.4014 (8)	0.3766 (5)	0.0342 (19)
H6	0.187274	0.326477	0.364695	0.041*
C11	0.3062 (5)	0.1356 (7)	0.3867 (5)	0.0319 (19)
C12	0.2905 (6)	0.0529 (8)	0.4309 (5)	0.038 (2)
H12	0.319523	0.061021	0.482753	0.046*
C13	0.2340 (6)	−0.0425 (8)	0.4028 (5)	0.038 (2)
H13	0.223722	−0.098452	0.434838	0.045*
C14	0.1922 (6)	−0.0554 (8)	0.3269 (5)	0.044 (2)
H14	0.153113	−0.120504	0.306742	0.052*
C15	0.2075 (6)	0.0254 (8)	0.2818 (5)	0.044 (2)
H15	0.179228	0.016171	0.229906	0.053*
C16	0.2637 (6)	0.1206 (8)	0.3105 (5)	0.040 (2)
H16	0.273743	0.176448	0.278260	0.048*
C21	0.4477 (5)	0.2505 (7)	0.5266 (5)	0.0320 (19)
C22	0.4370 (6)	0.3288 (8)	0.5773 (5)	0.039 (2)
H22	0.395100	0.392077	0.560743	0.047*
C23	0.4872 (7)	0.3149 (9)	0.6516 (5)	0.046 (2)
H23	0.480875	0.369976	0.685812	0.055*
C24	0.5469 (6)	0.2206 (9)	0.6765 (5)	0.045 (2)
H24	0.579917	0.209497	0.727698	0.054*
C25	0.5576 (6)	0.1433 (9)	0.6260 (5)	0.047 (2)
H25	0.599434	0.079949	0.642366	0.056*
C26	0.5082 (6)	0.1578 (8)	0.5524 (5)	0.044 (2)
H26	0.515407	0.103099	0.518381	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0438 (4)	0.0704 (5)	0.0570 (4)	0.0112 (4)	0.0277 (3)	0.0091 (4)
Si1	0.0317 (12)	0.0303 (12)	0.0301 (12)	0.0037 (10)	0.0080 (10)	−0.0003 (10)
C1	0.032 (4)	0.029 (4)	0.025 (4)	0.002 (3)	0.010 (3)	0.004 (3)
C2	0.036 (5)	0.044 (5)	0.043 (5)	0.000 (4)	0.018 (4)	0.000 (4)
C3	0.056 (6)	0.027 (5)	0.058 (6)	0.003 (4)	0.025 (5)	−0.001 (4)
C4	0.063 (7)	0.030 (5)	0.069 (7)	0.018 (5)	0.034 (6)	0.013 (5)
C5	0.024 (4)	0.050 (6)	0.056 (6)	0.012 (4)	0.013 (4)	0.003 (5)
C6	0.037 (5)	0.028 (4)	0.035 (5)	−0.004 (4)	0.012 (4)	0.001 (4)
C11	0.029 (4)	0.030 (4)	0.036 (5)	0.012 (4)	0.011 (4)	0.002 (4)
C12	0.041 (5)	0.040 (5)	0.028 (5)	0.005 (4)	0.007 (4)	−0.008 (4)
C13	0.045 (5)	0.038 (5)	0.036 (5)	−0.006 (4)	0.021 (4)	−0.003 (4)
C14	0.040 (5)	0.033 (5)	0.055 (6)	−0.007 (4)	0.015 (5)	−0.012 (5)
C15	0.047 (5)	0.046 (6)	0.030 (5)	−0.002 (4)	0.003 (4)	−0.010 (4)
C16	0.048 (5)	0.042 (5)	0.026 (4)	0.011 (4)	0.010 (4)	0.008 (4)
C21	0.032 (4)	0.023 (4)	0.039 (5)	−0.006 (3)	0.011 (4)	−0.002 (3)
C22	0.036 (5)	0.045 (5)	0.034 (5)	0.011 (4)	0.010 (4)	0.006 (4)
C23	0.056 (6)	0.045 (6)	0.032 (5)	−0.004 (5)	0.011 (4)	0.000 (4)
C24	0.038 (5)	0.055 (6)	0.034 (5)	−0.001 (5)	0.005 (4)	0.013 (5)
C25	0.031 (5)	0.045 (6)	0.053 (6)	0.008 (4)	0.003 (4)	0.006 (5)
C26	0.036 (5)	0.037 (5)	0.048 (6)	0.011 (4)	0.006 (4)	−0.003 (4)

Geometric parameters (Å, º)

I1—Si1	2.478 (2)	C13—C14	1.389 (13)
Si1—C1	1.867 (8)	C13—H13	0.9500
Si1—C21	1.873 (9)	C14—C15	1.360 (13)
Si1—C11	1.876 (9)	C14—H14	0.9500
C1—C6	1.374 (11)	C15—C16	1.379 (13)
C1—C2	1.405 (12)	C15—H15	0.9500
C2—C3	1.384 (12)	C16—H16	0.9500
C2—H2	0.9500	C21—C26	1.386 (12)
C3—C4	1.373 (14)	C21—C22	1.391 (12)
C3—H3	0.9500	C22—C23	1.382 (12)
C4—C5	1.380 (14)	C22—H22	0.9500
C4—H4	0.9500	C23—C24	1.391 (13)
C5—C6	1.387 (12)	C23—H23	0.9500
C5—H5	0.9500	C24—C25	1.381 (14)
C6—H6	0.9500	C24—H24	0.9500
C11—C12	1.363 (12)	C25—C26	1.368 (13)
C11—C16	1.399 (12)	C25—H25	0.9500
C12—C13	1.382 (12)	C26—H26	0.9500
C12—H12	0.9500
C1—Si1—C21	111.8 (4)	C12—C13—C14	119.1 (8)
C1—Si1—C11	111.0 (4)	C12—C13—H13	120.5
C21—Si1—C11	111.9 (4)	C14—C13—H13	120.5
C1—Si1—I1	106.8 (3)	C15—C14—C13	119.8 (8)
C21—Si1—I1	107.0 (3)	C15—C14—H14	120.1
C11—Si1—I1	108.0 (3)	C13—C14—H14	120.1
C6—C1—C2	118.2 (8)	C14—C15—C16	120.6 (8)
C6—C1—Si1	121.2 (6)	C14—C15—H15	119.7
C2—C1—Si1	120.6 (6)	C16—C15—H15	119.7
C3—C2—C1	120.6 (8)	C15—C16—C11	120.6 (8)
C3—C2—H2	119.7	C15—C16—H16	119.7
C1—C2—H2	119.7	C11—C16—H16	119.7
C4—C3—C2	119.7 (9)	C26—C21—C22	118.6 (8)
C4—C3—H3	120.2	C26—C21—Si1	121.5 (7)
C2—C3—H3	120.2	C22—C21—Si1	119.9 (6)
C3—C4—C5	120.8 (9)	C23—C22—C21	120.2 (8)
C3—C4—H4	119.6	C23—C22—H22	119.9
C5—C4—H4	119.6	C21—C22—H22	119.9
C4—C5—C6	119.1 (8)	C22—C23—C24	120.4 (9)
C4—C5—H5	120.4	C22—C23—H23	119.8
C6—C5—H5	120.4	C24—C23—H23	119.8
C1—C6—C5	121.6 (8)	C25—C24—C23	119.2 (8)
C1—C6—H6	119.2	C25—C24—H24	120.4
C5—C6—H6	119.2	C23—C24—H24	120.4
C12—C11—C16	117.8 (8)	C26—C25—C24	120.2 (9)
C12—C11—Si1	121.4 (6)	C26—C25—H25	119.9
C16—C11—Si1	120.8 (7)	C24—C25—H25	119.9
C11—C12—C13	122.2 (8)	C25—C26—C21	121.4 (9)
C11—C12—H12	118.9	C25—C26—H26	119.3
C13—C12—H12	118.9	C21—C26—H26	119.3
C21—Si1—C1—C6	−118.2 (7)	Si1—C11—C12—C13	176.6 (7)
C11—Si1—C1—C6	7.5 (8)	C11—C12—C13—C14	0.7 (14)
I1—Si1—C1—C6	125.0 (7)	C12—C13—C14—C15	0.0 (14)
C21—Si1—C1—C2	61.3 (8)	C13—C14—C15—C16	−0.4 (14)
C11—Si1—C1—C2	−173.0 (7)	C14—C15—C16—C11	0.1 (14)
I1—Si1—C1—C2	−55.5 (7)	C12—C11—C16—C15	0.5 (13)
C6—C1—C2—C3	0.9 (13)	Si1—C11—C16—C15	−177.0 (7)
Si1—C1—C2—C3	−178.7 (7)	C1—Si1—C21—C26	−176.4 (7)
C1—C2—C3—C4	−0.9 (14)	C11—Si1—C21—C26	58.4 (8)
C2—C3—C4—C5	−0.3 (16)	I1—Si1—C21—C26	−59.8 (7)
C3—C4—C5—C6	1.4 (15)	C1—Si1—C21—C22	5.8 (8)
C2—C1—C6—C5	0.3 (13)	C11—Si1—C21—C22	−119.4 (7)
Si1—C1—C6—C5	179.8 (7)	I1—Si1—C21—C22	122.4 (7)
C4—C5—C6—C1	−1.4 (14)	C26—C21—C22—C23	1.2 (13)
C1—Si1—C11—C12	−109.8 (7)	Si1—C21—C22—C23	179.1 (7)
C21—Si1—C11—C12	15.9 (8)	C21—C22—C23—C24	−1.8 (14)
I1—Si1—C11—C12	133.5 (6)	C22—C23—C24—C25	2.1 (14)
C1—Si1—C11—C16	67.7 (8)	C23—C24—C25—C26	−1.7 (15)
C21—Si1—C11—C16	−166.6 (7)	C24—C25—C26—C21	1.2 (15)
I1—Si1—C11—C16	−49.1 (7)	C22—C21—C26—C25	−0.9 (14)
C16—C11—C12—C13	−0.9 (13)	Si1—C21—C26—C25	−178.7 (7)