1,2,4,5-Tetra­chloro-3,6-di­iodo­benzene benzene monosolvate

The title compound, C₆Cl₄I₂·C₆H₆, crystallizes from benzene solution as cube-shaped crystals in the triclinic space group P with Z = 1. The asymmetric unit of the crystal structure contains one half of each mol­ecule. In the crystal, the benzene ring is almost orthogonal to the perhalo­benzene ring and the mol­ecules are linked by C—I...π inter­actions, with a close contact between the iodine atom and the benzene ring of 3.412 (1) Å.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.013
• wR factor = 0.032
• Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT432_ALERT_2_G Short Inter X...Y Contact  I1       ..C4               3.43 Ang.
                                                      x,y,z  =      1_555 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 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

   1 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
   0 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


checkCIF publication errors

Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 503
                  I:\XRAYDATA\EB829G~1\eb829_a.res
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: SMART (Bruker, 2014); cell refinement: SMART (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED (Barbour, 2001).

1,2,4,5-Tetrachloro-3,6-diiodobenzene benzene monosolvate

Crystal data

C6Cl4I2·C6H6	Z = 1
Mr = 545.77	F(000) = 252
Triclinic, P1	Dx = 2.425 Mg m^−3
a = 5.4399 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.3599 (4) Å	Cell parameters from 4302 reflections
c = 11.0232 (8) Å	θ = 3.3–27.3°
α = 96.702 (1)°	µ = 4.90 mm^−1
β = 92.728 (1)°	T = 100 K
γ = 98.599 (1)°	Cut cube, colourless
V = 373.69 (5) Å^3	0.39 × 0.12 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer	1668 independent reflections
Radiation source: fine-focus sealed tube	1634 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 8.3660 pixels mm^-1	θmax = 27.3°, θmin = 1.9°
phi and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −8→8
Tmin = 0.611, Tmax = 1.000	l = −14→14
4913 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.013	H-atom parameters constrained
wR(F^2) = 0.032	w = 1/[σ^2(Fo^2) + (0.0129P)^2 + 0.2107P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
1668 reflections	Δρmax = 0.46 e Å^−3
82 parameters	Δρmin = −0.39 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	0.63204 (2)	0.24241 (2)	0.70975 (2)	0.01586 (5)
Cl1	0.70962 (8)	0.35540 (7)	0.42245 (4)	0.01743 (9)
C1	0.8497 (3)	0.0970 (3)	0.58350 (15)	0.0125 (3)
Cl2	1.04287 (8)	0.14760 (7)	0.24148 (4)	0.01843 (9)
C2	0.8716 (3)	0.1608 (3)	0.46708 (16)	0.0130 (3)
C3	1.0207 (3)	0.0648 (3)	0.38431 (16)	0.0127 (3)
C4	0.2926 (4)	0.4936 (3)	0.92088 (17)	0.0220 (4)
H4	0.150280	0.488464	0.866558	0.026*
C5	0.4738 (4)	0.6732 (3)	0.93667 (18)	0.0216 (4)
H5	0.455940	0.791629	0.893655	0.026*
C6	0.6826 (4)	0.6801 (3)	1.01573 (18)	0.0217 (4)
H6	0.808105	0.803023	1.026540	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01473 (7)	0.01688 (7)	0.01605 (7)	0.00549 (4)	0.00276 (4)	−0.00209 (4)
Cl1	0.0194 (2)	0.01586 (19)	0.0194 (2)	0.00981 (16)	0.00007 (16)	0.00377 (15)
C1	0.0112 (7)	0.0113 (7)	0.0143 (8)	0.0021 (6)	0.0016 (6)	−0.0017 (6)
Cl2	0.0233 (2)	0.0205 (2)	0.0141 (2)	0.00780 (16)	0.00371 (16)	0.00617 (16)
C2	0.0122 (7)	0.0100 (7)	0.0170 (8)	0.0031 (6)	−0.0016 (6)	0.0017 (6)
C3	0.0129 (8)	0.0132 (8)	0.0117 (7)	0.0014 (6)	−0.0004 (6)	0.0013 (6)
C4	0.0160 (8)	0.0363 (11)	0.0149 (8)	0.0092 (8)	0.0013 (7)	0.0019 (7)
C5	0.0240 (9)	0.0251 (9)	0.0182 (9)	0.0086 (8)	0.0063 (7)	0.0052 (7)
C6	0.0192 (9)	0.0257 (10)	0.0191 (9)	0.0015 (7)	0.0050 (7)	−0.0008 (7)

Geometric parameters (Å, º)

I1—C1	2.0922 (17)	C4—C5	1.381 (3)
Cl1—C2	1.7254 (17)	C4—C6^ii	1.394 (3)
C1—C2	1.396 (2)	C4—H4	0.9500
C1—C3^i	1.400 (2)	C5—C6	1.390 (3)
Cl2—C3	1.7215 (17)	C5—H5	0.9500
C2—C3	1.397 (2)	C6—H6	0.9500
C2—C1—C3^i	118.86 (15)	C5—C4—C6^ii	120.31 (18)
C2—C1—I1	121.01 (12)	C5—C4—H4	119.8
C3^i—C1—I1	120.13 (12)	C6^ii—C4—H4	119.8
C1—C2—C3	120.44 (15)	C4—C5—C6	119.78 (18)
C1—C2—Cl1	120.37 (13)	C4—C5—H5	120.1
C3—C2—Cl1	119.17 (13)	C6—C5—H5	120.1
C2—C3—C1^i	120.70 (16)	C5—C6—C4^ii	119.90 (19)
C2—C3—Cl2	119.10 (13)	C5—C6—H6	120.0
C1^i—C3—Cl2	120.21 (13)	C4^ii—C6—H6	120.0

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