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Di­iodo­durene (1,4-diodo-2,3,5,6-tetra­methyl­benzene), C10H12I2, packs with four mol­ecules in the asymmetric unit. All four of these moleules violate Kitaigorodsky's suggestion that mol­ecules with centers of symmetry will lie on crystallographic centers of symmetry. There is 5.6% disorder at one of the sites. Most of the I atoms are in contact with other I atoms, but only six of the I...I contacts are shorter than 4.2 Å. Of these six contacts, one set of three contacts forms a triangular set in which all of the I...I distances are less than 3.9 Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103012769/de1213sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103012769/de1213Isup2.hkl
Contains datablock I

CCDC reference: 219572

Comment top

Following the determination of the structure of the complex p-C6(CH3)4I2/p-C6F4(CN)2 (Britton & Gleason, 2002), we have determined the crystal structure of diiododurene, (I). There are four molecules in the asymmetric unit. In the notation of Zorky and co-workers (Zorky et al., 1967; Belsky et al., 1995; Zorky, 1996), the description of the unit cell would be P1, Z = 8(14). This is remarkable in that none of the four independent molecules lies on a center of symmetry. Kitaigorodsky (1961, 1973) went so far as to state that a molecular center of symmetry always coincides with a crystallographic center of symmetry, even though he described pyrene as an exception to this rule. Recently, the program CSDSymmetry (Yao et al., 2002) has been used to re-examine this question and finds that out of 18 008 molecules with approximate molecular symmetry 1, only 15 156 lie on the crystallographic inversion center.

Three of the four independent molecules of (I) are free of measurable disorder, but the fourth shows a disorder with the minor component having an occupancy of 5.61 (6)%. Fig. 1 shows the labelling and the anisotropic displacement ellipsoids for the disordered pair; the numbering and ellispsoids for the remaining molecules are similar. To check the disorder, a second set of data was collected on a new crystal. The disorder from this refinement was 5.52 (7)%.

The bond lengths and angles are normal and agree within experimental error among the four molecules. The Crystal Data section of the Experimental reports the refinement with all four molecules independent of each other. To obtain the best possible estimates for the bond lengths and angles in an isolated molecule, the data were refined with all chemically equivalent bond lengths and angles constrained to be the same. The constraints only increased R from 0.027 to 0.028. The results are: C1—I = 2.124 (2) Å, C1—C2 = 1.398 (1) Å, C2—C3 = 1.406 (2) Å, C2—CH3 = 1.516 (2) Å, C2—C1—C2' = 123.72 (13)° and C1—C2—C2' = 118.14 (8)°. The angles can be compared with those found in two separate determinations of triiodomesitylene (Boudjada et al., 2001), viz. 123.8 (3) and 116.2 (3)° (Bosch & Barnes, 2002), and 123.5 (6) and 116.5 (6)°. The results in both molecules agree with the trends described by Domenicano (1992).

Fig. 2 shows a view approximately along the a axis. The molecules pack in two kinds of stacks, with molecules 1 and 2 alternating in one, and molecules 3 and 4 alternating in the other. The stacks are aligned in an hexagonal array of parallel stacks with each stack surrounded by two of the same kind and four of the other kind. In stack-12, molecule 1 is tilted 23.1 (2)° away from the normal to the stack direction (a axis), while molecule 2 is tilted 24.1 (2)°. The perpendicular distances between the planes are both 3.75 (2) Å. In stack-34, the tilts are molecule 3 = 25.2 (2)° and molecule 4 = 24.9 (2)°. The distances between the planes are alternately 3.69 (2) and 3.66 (2) Å.

In addition to the stacks involving π interactions, there are approximately planar ribbons of molecules at angles to the stacks. Fig. 3 shows two views of these ribbons. There are two types of ribbons, one involving molecules 1 and 2, the other molecules 3 and 4. In ribbon-12, the molecular order is −1–1-2–2-1–1-, while in ribbon-34, the order is −3–4-3–4-.

Before discussing the intermolecular σ contacts, we will look at some earlier I···I and CMe···CMe contacts. It is well known (Bent, 1968) that the shortest X—I1···I2—Y intermolecular interactions involving small molecules usually occur with a nearly linear X—I1···I2 angle and a nearly tetrahedral I1···I2—Y angle. This is interpreted that I1 is a Lewis acid (electron acceptor) and I2 is a Lewis base (electron donor). Incentrosymetric diiodides, this leads to linear chains of molecules. In triiodides with approximate threefold symmetry, such interactions can lead to cyclic I···I···I groups. Table 1 gives the distances and angles for some of these interactions. The linear interactions have distances slightly larger than 4.0 Å, while the I···I···I cylic arrangements have distances slightly less than 4.0 Å. This suggests that the I···I interactions in the cylic arrangement are stronger than those in the linear arrangement. Both the occurrence of this cyclic arrangement and the shortening of the distances were described by Anthony et al. (1998) for Cl and Br atoms in 2,4,6-tris(4-halophenoxy)-1,3,5-triazine.

It is also well known that similar cyclic C···C···C contacts occur in hexamethylbenzene (Lonsdale-Yardley, 1929). In the most recent determination of the structure (Le Maguères et al., 2001), the three C···C distances are 3.85, 3.94, and 3.95 Å.

Based on the distances quoted above, we report in Table 2 all of the I···I, I···CMe, and CMe···CMe distances that are shorter than 4.20 Å and that lie approximately in the plane of one or both of the molecules. The distances shorter than 4.20 Å that arise from the π contacts are not included. The arrangement is such that every entry has the C—Y···Z angle larger than the Y···Z—C angle, i.e. that Y is the Lewis acid and Z the Lewis base.

There are five I···I contacts where the angles are consistent with a Lewis acid–base interaction and one where they are not. The first three I···I contacts in the list form a cyclic I···I···I group, with distances comparable to those in the I···I···I groups in hexaiodobenzene and triiodomesitylene. An arrangement of this sort would not be possible if there were only one-half or one molecule in the asymmetric unit; this may be the reason for the complexity of the structure.

There are three I···CMe and three CMe···I contacts where the angles are consistant with a Lewis acid–base interaction, and three I···CMe and two CMe···I contacts where they are not. If the angles do tell us something meaningful about the interactions, then the methyl and iodo groups appear to be roughly interchangeable with respect to these Lewis acid–base interactions.

There are six CMe···CMe contacts where the angles are similar to those in the short I···I interactions. All have distances slightly larger than those in hexamethylbenzene, but none is involved in a cyclic arrangement. It is, however, difficult to regard these as Lewis acid–base interactions.

Although there are four crystallographically different molecules in the unit cell and the details of the packing as shown above are complex, there is also a certain simplicity about the packing. The coordinates of the molecular centers are, approximately: molecule 1 (5/8, 3/4, 7/8), molecule 2 (7/8, 1/4, 1/8), molecule 3 (3/8, 3/4, 3/8), and molecule 4 (1/8, 1/4, 5/8). If the molecules were spherical, which would require the a axis to be about twice as large, then the packing of the spheres would be roughly hexagonal close-packed with b the hexagonal axis.

Refinement top

The structure was refined initially without considering disorder and converged with R = 0.033. The difference map suggested that molecule 1 might be disordered; there were peaks of 1.77 and 1.63 e Å−3 at the positions where I atoms bonded to C103 and C106 might be expected. The minor component of the disorder was constrained to have the same geometry as the major component with identical anisotropic displacement parameters for atoms in near coincidence. The refinement with disorder converged with R = 0.027 for 5.61 (6)% disorder. The minor component has been ignored in the discussion of the packing. The disorder leads to one unreasonably short I···I distance of 3.44 Å between I31 and I51(1 − x, 2 − y, 1 − z). This is presumably a consequence of inaccuracy in the position of the minor component plus the failure to find the small amount of disorder in molecule 3 that must be also be present.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Molecule 1 of (I). Displacement ellipsoids are drawn at the 50% probability level. Molecule 5, the minor component of the disorder at molecule 1 is shown with open bonds. Only the I atoms in the minor component are labelled. Molecules 2, 3, and 4, all ordered, have very similar displacement ellipsoids to molecule 1.
[Figure 2] Fig. 2. The unit cell, viewed normal to (100), showing stacks of molecules. There are two types of stacks, namely molecule 1 alternating with molecule 2, and moleclule 3 alternating with molecule 4. These stacks are parallel to a. Atoms labelled with the suffix A are related by an inversion center to the unlabelled atoms.
[Figure 3] Fig. 3. The molecular ribbons. Top: view along a. Bottom: view along c. Heavy dashed lines show I···I or I···CMe contact distances less than 4.00 Å, dashed lines show distances detween 4.00 and 4.20 Å, and dotted lines show longer distances and are only present to define the ribbons.
1,4-Diiodo-2,3,5,6-tetramethylbenzene top
Crystal data top
C10H12I2Z = 8
Mr = 386.00F(000) = 1424
Triclinic, P1Dx = 2.305 Mg m3
Hall symbol: -P 1Melting point = 410–411 K
a = 8.152 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.622 (4) ÅCell parameters from 3385 reflections
c = 18.080 (5) Åθ = 2.6–27.2°
α = 86.60 (1)°µ = 5.61 mm1
β = 86.93 (1)°T = 174 K
γ = 75.57 (1)°Needle, colorless
V = 2224.1 (10) Å30.50 × 0.10 × 0.05 mm
Data collection top
Siemens SMART area-detector
diffractometer
10118 independent reflections
Radiation source: fine-focus sealed tube7650 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
h = 1010
Tmin = 0.55, Tmax = 0.76k = 2020
26644 measured reflectionsl = 2323
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.061 w = 1/[σ2(Fo2) + (0.024P)2 + 1.06P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.004
10118 reflectionsΔρmax = 0.93 e Å3
471 parametersΔρmin = 0.99 e Å3
39 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00038 (4)
Crystal data top
C10H12I2γ = 75.57 (1)°
Mr = 386.00V = 2224.1 (10) Å3
Triclinic, P1Z = 8
a = 8.152 (2) ÅMo Kα radiation
b = 15.622 (4) ŵ = 5.61 mm1
c = 18.080 (5) ÅT = 174 K
α = 86.60 (1)°0.50 × 0.10 × 0.05 mm
β = 86.93 (1)°
Data collection top
Siemens SMART area-detector
diffractometer
10118 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
7650 reflections with I > 2σ(I)
Tmin = 0.55, Tmax = 0.76Rint = 0.029
26644 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.02739 restraints
wR(F2) = 0.061H-atom parameters constrained
S = 1.00Δρmax = 0.93 e Å3
10118 reflectionsΔρmin = 0.99 e Å3
471 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1010.6550 (5)0.8321 (2)0.8833 (2)0.0293 (8)0.9439 (6)
C1020.6339 (5)0.7786 (3)0.9466 (2)0.0304 (8)0.9439 (6)
C1030.6077 (5)0.6947 (3)0.9365 (2)0.0310 (9)0.9439 (6)
C1040.6042 (5)0.6689 (3)0.8644 (2)0.0303 (9)0.9439 (6)
C1050.6238 (5)0.7225 (3)0.8007 (2)0.0328 (9)0.9439 (6)
C1060.6492 (5)0.8061 (3)0.8108 (2)0.0313 (9)0.9439 (6)
I110.69383 (4)0.95888 (2)0.89954 (2)0.04205 (9)0.9439 (6)
C120.6417 (7)0.8094 (3)1.0240 (2)0.0422 (10)0.9439 (6)
H12A0.65660.86991.02080.063*0.9439 (6)
H12B0.73740.77001.04910.063*0.9439 (6)
H12C0.53600.80831.05210.063*0.9439 (6)
C130.5845 (10)0.6347 (4)1.0037 (4)0.0432 (11)0.9439 (6)
H13A0.56810.57890.98710.065*0.9439 (6)
H13B0.48490.66401.03380.065*0.9439 (6)
H13C0.68530.62261.03350.065*0.9439 (6)
I140.57274 (4)0.54028 (2)0.84903 (2)0.04691 (9)0.9439 (6)
C150.6166 (8)0.6911 (3)0.7237 (2)0.0473 (11)0.9439 (6)
H15A0.60990.74080.68730.071*0.9439 (6)
H15B0.51630.66770.72100.071*0.9439 (6)
H15C0.71880.64450.71290.071*0.9439 (6)
C160.6731 (10)0.8681 (5)0.7456 (3)0.0474 (12)0.9439 (6)
H16A0.68120.83720.69940.071*0.9439 (6)
H16B0.77750.88720.75090.071*0.9439 (6)
H16C0.57620.91990.74440.071*0.9439 (6)
C2010.8663 (5)0.2220 (2)0.05396 (19)0.0289 (8)
C2020.8938 (5)0.3044 (2)0.0651 (2)0.0294 (8)
C2030.8991 (5)0.3296 (2)0.1381 (2)0.0297 (8)
C2040.8740 (5)0.2698 (2)0.1962 (2)0.0301 (8)
C2050.8448 (5)0.1877 (2)0.1853 (2)0.0294 (8)
C2060.8405 (5)0.1624 (2)0.1119 (2)0.0294 (8)
I210.86485 (4)0.18231 (2)0.05622 (2)0.04449 (8)
C220.9210 (6)0.3685 (3)0.0005 (2)0.0446 (11)
H22A0.91550.34170.04660.067*
H22B1.03240.38100.00360.067*
H22C0.83250.42380.00340.067*
C230.9301 (6)0.4183 (3)0.1520 (2)0.0422 (10)
H23A0.95880.44650.10480.063*
H23B1.02410.41020.18540.063*
H23C0.82760.45600.17470.063*
I240.88390 (4)0.30704 (2)0.30673 (2)0.04166 (8)
C250.8204 (6)0.1234 (3)0.2489 (2)0.0441 (11)
H25A0.82210.15070.29620.066*
H25B0.91210.06930.24660.066*
H25C0.71120.10870.24510.066*
C260.8080 (6)0.0746 (3)0.0968 (2)0.0424 (10)
H26A0.82280.06530.04350.064*
H26B0.69190.07400.11340.064*
H26C0.88820.02720.12360.064*
C3010.3043 (5)0.8407 (2)0.3928 (2)0.0294 (8)
C3020.3932 (5)0.7911 (2)0.45133 (19)0.0309 (8)
C3030.4831 (5)0.7036 (2)0.43933 (19)0.0294 (8)
C3040.4787 (5)0.6709 (2)0.3691 (2)0.0275 (8)
C3050.3901 (5)0.7214 (2)0.31015 (19)0.0275 (8)
C3060.2978 (5)0.8081 (2)0.3230 (2)0.0285 (8)
I310.17426 (4)0.97406 (2)0.41006 (2)0.04619 (8)
C320.3922 (6)0.8295 (3)0.5286 (2)0.0455 (11)
H32A0.30630.88580.53090.068*
H32B0.50400.83920.53660.068*
H32C0.36560.78760.56720.068*
C330.5801 (5)0.6462 (3)0.5007 (2)0.0418 (10)
H33A0.57150.68070.54490.063*
H33B0.69940.62560.48460.063*
H33C0.53210.59520.51240.063*
I340.60906 (3)0.53802 (2)0.35037 (2)0.03506 (7)
C350.3913 (5)0.6861 (2)0.2332 (2)0.0352 (9)
H35A0.47670.62970.23000.053*
H35B0.41860.72880.19570.053*
H35C0.27930.67700.22450.053*
C360.1955 (5)0.8624 (3)0.2618 (2)0.0386 (10)
H36A0.11790.91480.28230.058*
H36B0.13010.82670.23920.058*
H36C0.27210.88100.22400.058*
C4010.0143 (4)0.3152 (2)0.58656 (19)0.0259 (8)
C4020.0124 (4)0.3505 (2)0.65602 (19)0.0265 (8)
C4030.1030 (5)0.2962 (2)0.71270 (19)0.0287 (8)
C4040.1910 (5)0.2101 (2)0.69641 (19)0.0276 (8)
C4050.1938 (5)0.1746 (2)0.62679 (19)0.0277 (8)
C4060.1034 (5)0.2291 (2)0.5703 (2)0.0278 (8)
I410.12381 (3)0.39625 (2)0.50143 (2)0.03326 (7)
C420.0838 (5)0.4445 (2)0.6709 (2)0.0367 (9)
H42A0.14950.47050.62770.055*
H42B0.00340.47960.68020.055*
H42C0.16080.44420.71440.055*
C430.1041 (6)0.3327 (3)0.7888 (2)0.0400 (10)
H43A0.14700.28390.82480.060*
H43B0.01140.36390.80410.060*
H43C0.17750.37390.78650.060*
I440.32471 (3)0.12637 (2)0.78180 (2)0.03778 (7)
C450.2896 (5)0.0811 (2)0.6125 (2)0.0402 (10)
H45A0.28030.06920.56050.060*
H45B0.24190.03990.64470.060*
H45C0.40920.07330.62310.060*
C460.1029 (6)0.1955 (3)0.4936 (2)0.0429 (10)
H46A0.07420.24590.45760.064*
H46B0.01880.16040.49290.064*
H46C0.21550.15860.48060.064*
C5010.6449 (14)0.7999 (5)0.8079 (4)0.0313 (9)0.0561 (6)
C5020.650 (4)0.8290 (9)0.8795 (4)0.0293 (8)0.0561 (6)
C5030.629 (4)0.7719 (9)0.9403 (4)0.0304 (8)0.0561 (6)
C5040.605 (2)0.6896 (6)0.9264 (4)0.0310 (9)0.0561 (6)
C5050.599 (4)0.6599 (10)0.8546 (4)0.0303 (9)0.0561 (6)
C5060.620 (4)0.7168 (10)0.7942 (4)0.0328 (9)0.0561 (6)
I510.6768 (12)0.8869 (5)0.7167 (3)0.0474 (12)0.0561 (6)
C520.678 (8)0.9195 (16)0.8916 (5)0.04205 (9)0.0561 (6)
H52A0.68950.95030.84350.063*0.0561 (6)
H52B0.78130.91280.91900.063*0.0561 (6)
H52C0.58080.95400.92020.063*0.0561 (6)
C530.634 (8)0.8011 (17)1.0189 (4)0.0422 (10)0.0561 (6)
H53A0.61770.75401.05450.063*0.0561 (6)
H53B0.54430.85481.02670.063*0.0561 (6)
H53C0.74470.81321.02600.063*0.0561 (6)
I540.5729 (12)0.6032 (4)1.0183 (4)0.0432 (11)0.0561 (6)
C550.571 (8)0.5696 (17)0.8431 (5)0.04691 (9)0.0561 (6)
H55A0.56970.56120.78990.070*0.0561 (6)
H55B0.46260.56510.86690.070*0.0561 (6)
H55C0.66310.52390.86500.070*0.0561 (6)
C560.616 (8)0.6906 (17)0.7151 (5)0.0473 (11)0.0561 (6)
H56A0.59560.63130.71520.071*0.0561 (6)
H56B0.72450.69060.68920.071*0.0561 (6)
H56C0.52440.73310.68960.071*0.0561 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1010.0232 (19)0.0239 (19)0.041 (2)0.0047 (15)0.0040 (16)0.0027 (16)
C1020.028 (2)0.029 (2)0.032 (2)0.0033 (16)0.0030 (16)0.0019 (16)
C1030.026 (2)0.027 (2)0.037 (2)0.0033 (16)0.0006 (17)0.0021 (17)
C1040.023 (2)0.0249 (19)0.042 (2)0.0029 (16)0.0008 (17)0.0055 (17)
C1050.027 (2)0.038 (2)0.032 (2)0.0037 (17)0.0030 (17)0.0063 (17)
C1060.025 (2)0.031 (2)0.036 (2)0.0030 (16)0.0019 (16)0.0032 (17)
I110.03916 (17)0.02601 (15)0.0618 (2)0.00878 (13)0.00703 (14)0.00114 (13)
C120.050 (3)0.042 (2)0.037 (2)0.014 (2)0.010 (2)0.0064 (19)
C130.055 (2)0.033 (4)0.043 (3)0.016 (3)0.006 (2)0.006 (2)
I140.04444 (18)0.03200 (17)0.0674 (2)0.01301 (15)0.00082 (15)0.01358 (14)
C150.050 (3)0.053 (3)0.039 (2)0.011 (2)0.008 (2)0.008 (2)
C160.054 (2)0.049 (3)0.035 (4)0.007 (2)0.002 (3)0.005 (3)
C2010.029 (2)0.032 (2)0.0249 (18)0.0036 (16)0.0005 (15)0.0059 (15)
C2020.0253 (19)0.029 (2)0.032 (2),-0.0041 (16)0.0016 (16)0.0004 (16)
C2030.025 (2)0.0255 (19)0.036 (2)0.0012 (16)0.0043 (16)0.0028 (16)
C2040.028 (2)0.032 (2)0.0284 (19)0.0025 (16)0.0035 (16)0.0047 (16)
C2050.027 (2)0.0256 (19)0.033 (2)0.0020 (16)0.0011 (16)0.0036 (16)
C2060.027 (2)0.0235 (19)0.037 (2)0.0041 (16)0.0018 (16)0.0017 (16)
I210.05500 (19)0.04967 (17)0.03035 (14)0.01407 (14)0.00356 (12)0.00773 (12)
C220.055 (3)0.037 (2)0.042 (2)0.014 (2)0.003 (2)0.0006 (19)
C230.046 (3)0.034 (2)0.047 (3)0.008 (2)0.003 (2)0.0083 (19)
I240.04568 (17)0.04407 (16)0.03250 (14)0.00307 (13)0.00678 (12)0.00965 (12)
C250.059 (3)0.038 (2)0.034 (2)0.013 (2)0.002 (2)0.0068 (18)
C260.058 (3)0.030 (2)0.044 (2)0.020 (2)0.007 (2)0.0012 (18)
C3010.032 (2)0.0224 (18)0.032 (2)0.0051 (16)0.0038 (16)0.0019 (15)
C3020.035 (2)0.033 (2)0.028 (2)0.0142 (17)0.0026 (16)0.0033 (16)
C3030.030 (2)0.034 (2)0.0261 (19)0.0139 (17)0.0031 (15)0.0061 (16)
C3040.0263 (19)0.0224 (18)0.034 (2)0.0077 (15)0.0009 (16)0.0033 (15)
C3050.027 (2)0.0291 (19)0.0282 (19)0.0111 (16)0.0023 (15)0.0003 (15)
C3060.027 (2)0.0285 (19)0.031 (2)0.0095 (16)0.0003 (16)0.0014 (15)
I310.05187 (18)0.03191 (15)0.04865 (17)0.00185 (13)0.00270 (14)0.00891 (12)
C320.052 (3)0.046 (3)0.037 (2)0.010 (2)0.007 (2)0.0056 (19)
C330.046 (3)0.039 (2)0.039 (2)0.008 (2)0.011 (2)0.0006 (19)
I340.03664 (15)0.02573 (13)0.04096 (15)0.00419 (11)0.00423 (11)0.00065 (11)
C350.042 (2)0.026 (2)0.038 (2)0.0076 (18)0.0113 (18)0.0010 (17)
C360.039 (2)0.036 (2)0.037 (2)0.0021 (19)0.0051 (18)0.0009 (18)
C4010.0278 (19)0.0259 (18)0.0253 (18)0.0100 (15)0.0051 (15)0.0068 (15)
C4020.0254 (19)0.0240 (18)0.0313 (19)0.0086 (15)0.0009 (15)0.0019 (15)
C4030.032 (2)0.034 (2)0.0244 (18)0.0160 (17)0.0006 (15)0.0021 (15)
C4040.027 (2)0.0289 (19)0.0282 (19)0.0100 (16)0.0057 (15)0.0051 (15)
C4050.033 (2)0.0228 (18)0.0287 (19)0.0114 (16)0.0006 (16)0.0011 (15)
C4060.030 (2)0.0249 (19)0.0299 (19)0.0103 (16)0.0011 (16)0.0014 (15)
I410.03578 (15)0.03000 (13)0.03390 (14)0.00815 (11)0.00821 (11)0.00552 (10)
C420.040 (2)0.032 (2)0.036 (2)0.0039 (18)0.0032 (18)0.0060 (17)
C430.050 (3)0.036 (2)0.034 (2)0.011 (2)0.0051 (19)0.0009 (18)
I440.04448 (16)0.03661 (14)0.03343 (14)0.01281 (12)0.01109 (12)0.00945 (11)
C450.046 (3)0.031 (2)0.041 (2)0.0036 (19)0.0071 (19)0.0020 (18)
C460.054 (3)0.036 (2)0.035 (2)0.001 (2)0.012 (2)0.0047 (18)
C5010.025 (2)0.031 (2)0.036 (2)0.0030 (16)0.0019 (16)0.0032 (17)
C5020.0232 (19)0.0239 (19)0.041 (2)0.0047 (15)0.0040 (16)0.0027 (16)
C5030.028 (2)0.029 (2)0.032 (2)0.0033 (16)0.0030 (16)0.0019 (16)
C5040.026 (2)0.027 (2)0.037 (2)0.0033 (16)0.0006 (17)0.0021 (17)
C5050.023 (2)0.0249 (19)0.042 (2)0.0029 (16)0.0008 (17)0.0055 (17)
C5060.027 (2)0.038 (2)0.032 (2)0.0037 (17)0.0030 (17)0.0063 (17)
I510.054 (2)0.049 (3)0.035 (4)0.007 (2)0.002 (3)0.005 (3)
C520.03916 (17)0.02601 (15)0.0618 (2)0.00878 (13)0.00703 (14)0.00114 (13)
C530.050 (3)0.042 (2)0.037 (2)0.014 (2)0.010 (2)0.0064 (19)
I540.055 (2)0.033 (4)0.043 (3)0.016 (3)0.006 (2)0.006 (2)
C550.04444 (18)0.03200 (17)0.0674 (2)0.01301 (15)0.00082 (15)0.01358 (14)
C560.050 (3)0.053 (3)0.039 (2)0.011 (2)0.008 (2)0.008 (2)
Geometric parameters (Å, º) top
C101—C1061.402 (5)C32—H32A0.9800
C101—C1021.405 (5)C32—H32B0.9800
C101—I112.121 (4)C32—H32C0.9800
C102—C1031.403 (5)C33—H33A0.9800
C102—C121.515 (5)C33—H33B0.9800
C103—C1041.390 (5)C33—H33C0.9800
C103—C131.524 (6)C35—H35A0.9800
C104—C1051.410 (5)C35—H35B0.9800
C104—I142.124 (4)C35—H35C0.9800
C105—C1061.396 (6)C36—H36A0.9800
C105—C151.512 (6)C36—H36B0.9800
C106—C161.516 (6)C36—H36C0.9800
C12—H12A0.9800C401—C4021.399 (5)
C12—H12B0.9800C401—C4061.401 (5)
C12—H12C0.9800C401—I412.118 (3)
C13—H13A0.9800C402—C4031.408 (5)
C13—H13B0.9800C402—C421.514 (5)
C13—H13C0.9800C403—C4041.397 (5)
C15—H15A0.9800C403—C431.522 (5)
C15—H15B0.9800C404—C4051.403 (5)
C15—H15C0.9800C404—I442.124 (3)
C16—H16A0.9800C405—C4061.406 (5)
C16—H16B0.9800C405—C451.504 (5)
C16—H16C0.9800C406—C461.511 (5)
C201—C2021.388 (5)C42—H42A0.9800
C201—C2061.404 (5)C42—H42B0.9800
C201—I212.123 (3)C42—H42C0.9800
C202—C2031.404 (5)C43—H43A0.9800
C202—C221.536 (5)C43—H43B0.9800
C203—C2041.406 (5)C43—H43C0.9800
C203—C231.506 (5)C45—H45A0.9800
C204—C2051.389 (5)C45—H45B0.9800
C204—I242.124 (4)C45—H45C0.9800
C205—C2061.411 (5)C46—H46A0.9800
C205—C251.520 (5)C46—H46B0.9800
C206—C261.503 (5)C46—H46C0.9800
C22—H22A0.9800C501—C5061.402 (6)
C22—H22B0.9800C501—C5021.405 (5)
C22—H22C0.9800C501—I512.121 (4)
C23—H23A0.9800C502—C5031.403 (6)
C23—H23B0.9800C502—C521.515 (5)
C23—H23C0.9800C503—C5041.390 (5)
C25—H25A0.9800C503—C531.524 (6)
C25—H25B0.9800C504—C5051.410 (6)
C25—H25C0.9800C504—I542.124 (4)
C26—H26A0.9800C505—C5061.396 (6)
C26—H26B0.9800C505—C551.512 (6)
C26—H26C0.9800C506—C561.516 (6)
C301—C3021.396 (5)C52—H52A0.9800
C301—C3061.397 (5)C52—H52B0.9800
C301—I312.122 (3)C52—H52C0.9800
C302—C3031.404 (5)C53—H53A0.9800
C302—C321.551 (5)C53—H53B0.9800
C303—C3041.402 (5)C53—H53C0.9800
C303—C331.511 (5)C55—H55A0.9800
C304—C3051.407 (5)C55—H55B0.9800
C304—I342.121 (3)C55—H55C0.9800
C305—C3061.402 (5)C56—H56A0.9800
C305—C351.526 (5)C56—H56B0.9800
C306—C361.509 (5)C56—H56C0.9800
C106—C101—C102123.2 (4)C302—C32—H32C109.5
C106—C101—I11119.1 (3)H32A—C32—H32C109.5
C102—C101—I11117.8 (3)H32B—C32—H32C109.5
C103—C102—C101118.2 (4)C303—C33—H33A109.5
C103—C102—C12120.5 (4)C303—C33—H33B109.5
C101—C102—C12121.4 (4)H33A—C33—H33B109.5
C104—C103—C102118.3 (4)C303—C33—H33C109.5
C104—C103—C13121.9 (4)H33A—C33—H33C109.5
C102—C103—C13119.8 (4)H33B—C33—H33C109.5
C103—C104—C105123.8 (4)C305—C35—H35A109.5
C103—C104—I14118.3 (3)C305—C35—H35B109.5
C105—C104—I14117.9 (3)H35A—C35—H35B109.5
C106—C105—C104117.9 (4)C305—C35—H35C109.5
C106—C105—C15120.8 (4)H35A—C35—H35C109.5
C104—C105—C15121.3 (4)H35B—C35—H35C109.5
C105—C106—C101118.6 (4)C306—C36—H36A109.5
C105—C106—C16121.7 (4)C306—C36—H36B109.5
C101—C106—C16119.7 (4)H36A—C36—H36B109.5
C102—C12—H12A109.5C306—C36—H36C109.5
C102—C12—H12B109.5H36A—C36—H36C109.5
H12A—C12—H12B109.5H36B—C36—H36C109.5
C102—C12—H12C109.5C402—C401—C406123.4 (3)
H12A—C12—H12C109.5C402—C401—I41118.3 (2)
H12B—C12—H12C109.5C406—C401—I41118.2 (3)
C103—C13—H13A109.5C401—C402—C403118.2 (3)
C103—C13—H13B109.5C401—C402—C42121.7 (3)
H13A—C13—H13B109.5C403—C402—C42120.1 (3)
C103—C13—H13C109.5C404—C403—C402118.3 (3)
H13A—C13—H13C109.5C404—C403—C43122.2 (3)
H13B—C13—H13C109.5C402—C403—C43119.5 (3)
C105—C15—H15A109.5C403—C404—C405123.7 (3)
C105—C15—H15B109.5C403—C404—I44118.8 (3)
H15A—C15—H15B109.5C405—C404—I44117.5 (3)
C105—C15—H15C109.5C404—C405—C406117.9 (3)
H15A—C15—H15C109.5C404—C405—C45121.5 (3)
H15B—C15—H15C109.5C406—C405—C45120.7 (3)
C106—C16—H16A109.5C401—C406—C405118.5 (3)
C106—C16—H16B109.5C401—C406—C46120.8 (3)
H16A—C16—H16B109.5C405—C406—C46120.7 (3)
C106—C16—H16C109.5C402—C42—H42A109.5
H16A—C16—H16C109.5C402—C42—H42B109.5
H16B—C16—H16C109.5H42A—C42—H42B109.5
C202—C201—C206123.5 (3)C402—C42—H42C109.5
C202—C201—I21119.0 (3)H42A—C42—H42C109.5
C206—C201—I21117.5 (3)H42B—C42—H42C109.5
C201—C202—C203118.9 (3)C403—C43—H43A109.5
C201—C202—C22122.3 (3)C403—C43—H43B109.5
C203—C202—C22118.8 (3)H43A—C43—H43B109.5
C202—C203—C204117.7 (3)C403—C43—H43C109.5
C202—C203—C23120.1 (3)H43A—C43—H43C109.5
C204—C203—C23122.2 (3)H43B—C43—H43C109.5
C205—C204—C203123.6 (3)C405—C45—H45A109.5
C205—C204—I24118.5 (3)C405—C45—H45B109.5
C203—C204—I24117.9 (3)H45A—C45—H45B109.5
C204—C205—C206118.5 (3)C405—C45—H45C109.5
C204—C205—C25122.8 (3)H45A—C45—H45C109.5
C206—C205—C25118.7 (3)H45B—C45—H45C109.5
C201—C206—C205117.8 (3)C406—C46—H46A109.5
C201—C206—C26121.4 (3)C406—C46—H46B109.5
C205—C206—C26120.8 (3)H46A—C46—H46B109.5
C202—C22—H22A109.5C406—C46—H46C109.5
C202—C22—H22B109.5H46A—C46—H46C109.5
H22A—C22—H22B109.5H46B—C46—H46C109.5
C202—C22—H22C109.5C506—C501—C502123.2 (4)
H22A—C22—H22C109.5C506—C501—I51119.1 (3)
H22B—C22—H22C109.5C502—C501—I51117.8 (3)
C203—C23—H23A109.5C503—C502—C501118.2 (4)
C203—C23—H23B109.5C503—C502—C52120.5 (4)
H23A—C23—H23B109.5C501—C502—C52121.4 (4)
C203—C23—H23C109.5C504—C503—C502118.3 (4)
H23A—C23—H23C109.5C504—C503—C53121.9 (4)
H23B—C23—H23C109.5C502—C503—C53119.8 (4)
C205—C25—H25A109.5C503—C504—C505123.8 (4)
C205—C25—H25B109.5C503—C504—I54118.3 (3)
H25A—C25—H25B109.5C505—C504—I54117.9 (3)
C205—C25—H25C109.5C506—C505—C504117.9 (4)
H25A—C25—H25C109.5C506—C505—C55120.8 (4)
H25B—C25—H25C109.5C504—C505—C55121.3 (4)
C206—C26—H26A109.5C505—C506—C501118.6 (4)
C206—C26—H26B109.5C505—C506—C56121.7 (4)
H26A—C26—H26B109.5C501—C506—C56119.7 (4)
C206—C26—H26C109.5C502—C52—H52A109.5
H26A—C26—H26C109.5C502—C52—H52B109.5
H26B—C26—H26C109.5H52A—C52—H52B109.5
C302—C301—C306123.9 (3)C502—C52—H52C109.5
C302—C301—I31118.3 (3)H52A—C52—H52C109.5
C306—C301—I31117.8 (3)H52B—C52—H52C109.5
C301—C302—C303118.3 (3)C503—C53—H53A109.5
C301—C302—C32121.9 (3)C503—C53—H53B109.5
C303—C302—C32119.8 (3)H53A—C53—H53B109.5
C304—C303—C302118.1 (3)C503—C53—H53C109.5
C304—C303—C33121.1 (3)H53A—C53—H53C109.5
C302—C303—C33120.8 (3)H53B—C53—H53C109.5
C303—C304—C305123.4 (3)C505—C55—H55A109.5
C303—C304—I34118.7 (3)C505—C55—H55B109.5
C305—C304—I34117.9 (3)H55A—C55—H55B109.5
C306—C305—C304118.2 (3)C505—C55—H55C109.5
C306—C305—C35119.0 (3)H55A—C55—H55C109.5
C304—C305—C35122.8 (3)H55B—C55—H55C109.5
C301—C306—C305118.2 (3)C506—C56—H56A109.5
C301—C306—C36122.6 (3)C506—C56—H56B109.5
C305—C306—C36119.2 (3)H56A—C56—H56B109.5
C302—C32—H32A109.5C506—C56—H56C109.5
C302—C32—H32B109.5H56A—C56—H56C109.5
H32A—C32—H32B109.5H56B—C56—H56C109.5

Experimental details

Crystal data
Chemical formulaC10H12I2
Mr386.00
Crystal system, space groupTriclinic, P1
Temperature (K)174
a, b, c (Å)8.152 (2), 15.622 (4), 18.080 (5)
α, β, γ (°)86.60 (1), 86.93 (1), 75.57 (1)
V3)2224.1 (10)
Z8
Radiation typeMo Kα
µ (mm1)5.61
Crystal size (mm)0.50 × 0.10 × 0.05
Data collection
DiffractometerSiemens SMART area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
Tmin, Tmax0.55, 0.76
No. of measured, independent and
observed [I > 2σ(I)] reflections
26644, 10118, 7650
Rint0.029
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.061, 1.00
No. of reflections10118
No. of parameters471
No. of restraints39
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.93, 0.99

Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL.

Distances and angles (Å, °)a in X—I···I—X contacts top
MoleculeX—I···II···II···I—XReference
I21713.63104d
p-I2C6H4b1604.1397e
p-I2C6H4c1644.1198e
p-I2C6F41614.0699f
C6I61753.77115g
C6I61773.78124g
C6I61754.03122g
C6(CH3)3I31733.89120h
C6(CH3)3I31733.93120h
C6(CH3)3I31653.97119h
C6(CH3)3I31733.85120i
C6(CH3)3I31743.90119i
C6(CH3)3I31663.93120i
Notes: (a) for purposes of comparison, the angles have been rounded to the nearest degree and the distances to the nearest 0.01 Å; the s.u. values have been omitted; (b) polymorph 1; (c) polymorph ?; (d) Wycoff (1963); (e) Boese & Miebach (1996); (f) Chaplot et al. (1981); (g) Steer et al. (1970); (h) Boudjada et al. (2001); (i) Bosch & Barnes (2002).
Distances and angles (Å, °)a in (I) for the C—Y···Z—C contacts, where X and Y are I or CMe top
YZC—Y···ZY···ZY···Z—C
I41iI341773.82120
I34I241743.85115
I24I41i1753.85120
I44I11ii1634.07104
C12iiiI441773.75126
I11ivI211694.20121
I21C36v1723.90133
I14C35vi1623.85137
C13iiiI141654.09130
I31C46vii1553.76137
C16viiiI311693.99109
C15C331714.17132
C42iC151744.15119
C43C22ix1524.05133
C23viC431664.03131
C45C32ii1584.17136
C25xC451674.19118
I31I31xi1184.18118
C26xI441374.06129
C36viiiI111324.14127
I21C35v1304.08126
I24C46i1374.01133
I41C33xii1314.05131
Notes: (a) for purposes of comparison, the angles have been rounded to the nearest degree and the distances to the nearest 0.01 Å; the s.u. values have been omitted. Each entry has been ordered so that the larger angle is given first. Symmetry codes: (i) 1 + x, y, z; (ii) x, y − 1, z; (iii) 1 − x, 1 − y, 2 − z; (iv) x, y − 1, z − 1; (v) 1 − x, 1 − y, −z; (vi) 1 − x, 1 − y, 1 − z; (vii) x, 1 + y, z; (viii) 1 − x, 2 − y, 1 − z; (ix) x − 1, y, 1 + z; (x) 1 − x, −y, 1 − z; (xi) −x, 2 − y, 1 − z; (xii) x − 1, y, z.
 

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