Crystal structures of two bis­(iodo­meth­yl)benzene derivatives: similarities and differences in the crystal packing

McAdam, C.J.; Hanton, L.R.; Moratti, S.C.; Simpson, J.

doi:10.1107/S2056989015021295

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Volume 71| Part 12| December 2015| Pages 1505-1509

https://doi.org/10.1107/S2056989015021295

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Crystal structures of two bis(iodomethyl)benzene derivatives: similarities and differences in the crystal packing

C. John McAdam,^a ^* Lyall R. Hanton,^a Stephen C. Moratti ^a and Jim Simpson ^a

^aDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
^*Correspondence e-mail: mcadamj@chemistry.otago.ac.nz

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 3 November 2015; accepted 9 November 2015; online 18 November 2015)

The isomeric derivatives 1,2-bis(iodomethyl)benzene, (I), and 1,3-bis(iodomethyl)benzene (II), both C₈H₈I₂, were prepared by metathesis from their dibromo analogues. The ortho-derivative, (I), lies about a crystallographic twofold axis that bisects the C—C bond between the two iodomethyl substituents. The packing in (I) relies solely on C—H⋯I hydrogen bonds supported by weak parallel slipped π–π stacking interactions [inter-centroid distance = 4.0569 (11) Å, inter-planar distance = 3.3789 (8) Å and slippage = 2.245 Å]. While C—H⋯I hydrogen bonds are also found in the packing of (II), type II, I⋯I halogen bonds [I⋯I = 3.8662 (2) Å] and C—H⋯π contacts feature prominently in stabilizing the three-dimensional structure.

Keywords: crystal structure; bis(iodomethyl)benzene derivatives; C—H⋯I hydrogen bonds; C—H⋯π(ring) contacts; π–π contacts; I⋯I halogen bonds.

CCDC references: 1436014; 1436013

1. Chemical context

The isomeric xylene derivatives reported here, 1,2-bis(iodomethyl)benzene, (I), and 1,3-bis(iodomethyl)benzene (II), are useful synthons for the preparation of a range of organic compounds. (I) is used particularly in the synthesis of polycyclic aromatic systems (see for example: Takahashi et al. 2006 ; Abreu et al., 2010 ; Wang et al., 2012 ). Similarly (II) has been used in polymer formation (Pandya & Gibson, 1991 ), in the synthesis of metacyclophanes (Ramming & Gleiter, 1997 ) and to provide aromatic spacers in organic synthesis (Kida et al., 2005 ). Our interest in such compounds is as components of ionene polymers. The compounds were readily prepared by metathesis from the bis(bromomethyl)benzene derivatives.

2. Structural commentary

The molecular structures of 1,2-bis(iodomethyl)benzene, (I), and 1,3-bis(iodomethyl)benzene, (II), are shown in Figs. 1 and 2 and are sufficiently similar to be discussed together. Each comprises a benzene ring with two iodomethyl substituents in the 1,2- and 1,3-positions for (I) and (II) respectively. The molecule of (I) lies about a twofold axis that bisects the C—C bond between the two iodomethyl substituents. For each molecule the C—I bonds of the substituents point away from opposite faces of the benzene rings with the C—C—I planes almost orthogonal to the ring planes; dihedral angles = 87.99 (14)° for (I) and 82.23 (14) and 83.61 (15)° for (II). The C1—C11 and C11—I1 bond lengths in (I) and C1—C11, C11—I1, C3—C31 and C31—I3 in (II) are reasonably self-consistent and also compare well with those found in the isomeric 1,4-bis(iodomethyl)benzene (McAdam et al. 2009 ).

Figure 1
The molecular structure of compound (I)

, with displacement ellipsoids drawn at the 50% probability level. The unlabelled atoms are related to labelled atoms by the symmetry operation (−x + 1, y, −z + $[{3\over 2}]$ ).

Figure 2
The molecular structure of compound (II)

, with displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features

3.1. Crystal packing for (I)

In the crystal of (I), weak parallel slipped π–π stacking interactions [inter-centroid distance = 4.0569 (11) Å, inter-planar distance = 3.3789 (8) Å, slippage = 2.245 Å], between the benzene rings of inversion-related molecules are supported by C3—H3⋯I1 hydrogen bonds, Table 1, to link molecules in a head-to tail-fashion, stacking them along c, Fig. 3. In addition, the iodine atoms act as bifurcated acceptors, forming weak C2—H2⋯I1 and C11—H112⋯I1 hydrogen bonds generating R₂¹(6) ring motifs (Bernstein et al., 1995 ). These contacts link the molecules into zigzag chains along [101], Fig. 4. These contacts combine to link stacked columns of molecules through weak C—H⋯I hydrogen bonds and generate a three dimensional network structure, Fig. 5.

Table 1
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯I1ⁱ	0.95	3.38	4.046 (2)	129
C11—H112⋯I1ⁱⁱ	0.99	3.33	4.179 (2)	145
C2—H2⋯I1ⁱⁱ	0.95	3.36	4.257 (2)	158
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Figure 3
π–π stacking interactions (green dotted lines) supported by C—H⋯I hydrogen bonds for (I)

. Hydrogen bonds in this and subsequent figures are drawn as blue dashed lines.

Figure 4
Chains of molecules of (I)

in [101].

Figure 5
Overall packing for (I)

viewed along the c-axis direction.

3.2. Crystal packing for (II)

In the crystal of (II), C11—H11B⋯I1 hydrogen bonds, Table 2, form a column supported by a series of C31—H31B⋯Cg1 contacts. C31—H31A⋯I3 hydrogen bonds link these in an obverse fashion, forming double chains along b, Fig. 6. C5—H5⋯I1 hydrogen bonds, Fig. 7, link the double chains into sheets in the ab plane. An extensive series of I1⋯I3 halogen bonds Fig. 8, I1⋯I3^v,vi = 3.8662 (2) Å; symmetry codes: (v) = − $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z; (vi) = $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z (Desiraju et al., 2013 ; Metrangolo et al., 2008 ), extend the structure in the third dimension, Fig. 9. The angles C11—I1—I3 = 117° and C31—I3—I1 = 165° characterize this halogen bond as type II (Pedireddi et al., 1994 ).

Table 2
Hydrogen-bond geometry (Å, °) for (II)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯I1ⁱ	0.99	3.22	4.060 (3)	144
C5—H5⋯I1ⁱⁱ	0.95	3.25	4.078 (3)	147
C31—H31A⋯I3ⁱⁱⁱ	0.99	3.27	4.224 (3)	162
C31—H31A⋯Cg^iv	0.99	2.84	3.453 (3)	121
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x, y+1, z.

Figure 6
Double chains of molecules of (II)

formed by a series of C31—H31B⋯Cg1 contacts (green dotted lines) linked by C—H⋯I hydrogen bonds.

Figure 7
Sheets of molecules of (II)

in the ab plane formed by C—H⋯I. hydrogen bonds.

Figure 8
Sheets of molecules of (II)

in the (101) plane formed by I⋯I halogen bonds, blue dashed lines, supported by C—H⋯I hydrogen bonds.

Figure 9
Overall packing for (II)

viewed along the b-axis direction.

4. Database survey

A search of the Cambridge Structural Database (Version 5.36 with three updates; Groom & Allen, 2014 ) for molecules incorporating a C₆CH₂I fragment surprisingly generated only five hits for iodomethylbenzene derivatives. One of these is the isomeric 1,4-bis(iodomethyl)benzene reported by us previously (McAdam et al., 2009), while two others are the organic compounds 2-(iodomethyl)-1,3,5-trimethylbenzene (Bats, 2014 ) and 3′-iodo-5′-(iodomethyl)biphenyl-4-carbonitrile (He et al., 2013 ). The other two entries are metal complexes (Martínez-García et al., 2010 ; Rivada-Wheelaghan et al., 2012 ). In one of these, the iodine atom of the iodomethyl unit was found to act as a ligand to a platinum(II) nucleus (Rivada-Wheelaghan et al., 2012). The structures of both the chloro- and bromo-analogues of 1,2-bis(iodomethyl)benzene (Basaran et al., 1992 ; Jones & Kus, 2007 ) and 1,3-bis(iodomethyl)benzene (Sanders et al., 2013 ; Li et al., 2006 ; Jones & Kus, 2007) have also been reported. Interestingly, 1,3-bis(bromomethyl)benzene is isostructural with (II) and the packing features for the two compounds are identical, apart from somewhat increased distances for the iodo compound. For example I1⋯I3 = 3.8662 (2) Å for (II) but the equivalent Br⋯Br distance is 3.6742 (3) Å for the meta-dibromo analogue (Jones & Kus, 2007). Similar isostructural behaviour is observed for para-bis(iodomethyl)benzene (McAdam et al., 2009) and its dibromo analogue (Jones & Kus, 2007). However, in contrast, despite (I) and the ortho-dibromo analogue both displaying twofold symmetry, compound (I) crystallizes in the monoclinic space group C2/c while that for the dibromo counterpart is found to be orthorhombic, Fdd2 (Jones & Kus, 2007).

5. Synthesis and crystallization

Preparation of the title compounds was based on literature methods (Moore & Stupp, 1986 ; Kida et al., 2005). The appropriate bis(bromomethyl)benzene (1.32 g, 5 mmol) was refluxed for 7 h with sodium iodide (2.25 g, 15 mmol) in acetone (25 ml). The solution was allowed to cool overnight, the crystals that developed were rinsed gently with water to remove sodium bromide and air dried. The product was recrystallized a second time from acetone to give X-ray quality crystals. Confirmation of the metathesised (iodo) product was by microanalysis and mass spectroscopy. ¹³C NMR spectra of the diiodo compounds are distinct from those of their dibromo precursors.

Compound (I): Analysis calculated for C₈H₈I₂: C, 26.84; H, 2.25%. Found: C, 26.86; H, 2.14%. ¹³C NMR (δ p.p.m.): 137.4, 130.8, 129.0, 1.8.

Compound (II): Analysis calculated for C₈H₈I₂: C, 26.84; H, 2.25%. Found: C, 26.63; H, 2.19%. ¹³C NMR (δ p.p.m.): 140.0, 129.4, 129.0, 128.4, 4.9.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All H atoms were refined using a riding model with d(C—H) = 0.95 Å, U_iso = 1.2U_eq(C) for aromatic and 0.99 Å, U_iso = 1.2U_eq(C) for CH₂ H atoms. For (I), a low-angle reflection with F_o << F_c, that may have been affected by the beam-stop, was omitted from the final refinement cycles.

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₈H₈I₂	C₈H₈I₂
M_r	357.94	357.94
Crystal system, space group	Monoclinic, C2/c	Monoclinic, P2₁/n
Temperature (K)	90	90
a, b, c (Å)	14.5485 (5), 8.0461 (3), 8.0582 (3)	13.5323 (3), 4.5464 (1), 15.6269 (4)
β (°)	101.637 (2)	95.203 (1)
V (Å³)	923.89 (6)	957.46 (4)
Z	4	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	6.74	6.50
Crystal size (mm)	0.31 × 0.17 × 0.15	0.45 × 0.06 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD area detector	Bruker APEXII CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )	Multi-scan (SADABS; Bruker, 2013)
T_min, T_max	0.534, 1.000	0.569, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8422, 1667, 1552	16804, 3435, 2826
R_int	0.030	0.033
(sin θ/λ)_max (Å⁻¹)	0.775	0.775

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.044, 1.15	0.024, 0.048, 1.06
No. of reflections	1667	3435
No. of parameters	46	91
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −1.23	1.24, −0.77
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), TITAN2000 (Hunter & Simpson, 1999 ), Mercury (Macrae et al., 2008 ), enCIFer (Allen et al., 2004 ), PLATON (Spek, 2009 ), WinGX (Farrugia, 2012 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 1436014; 1436013

Crystal structure: contains datablocks global, I, II. DOI: https://doi.org/10.1107/S2056989015021295/su5235sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015021295/su5235Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989015021295/su5235IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015021295/su5235Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989015021295/su5235IIsup5.cml

checkCIF report

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2013); cell refinement: APEX2 and SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), enCIFer (Allen et al., 2004), PLATON (Spek, 2009), publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).

(I) 1,2-Bis(iodomethyl)benzene top

Crystal data top

C₈H₈I₂	F(000) = 648
M_r = 357.94	D_x = 2.573 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.5485 (5) Å	Cell parameters from 5091 reflections
b = 8.0461 (3) Å	θ = 2.6–32.9°
c = 8.0582 (3) Å	µ = 6.74 mm⁻¹
β = 101.637 (2)°	T = 90 K
V = 923.89 (6) Å³	Block, colourless
Z = 4	0.31 × 0.17 × 0.15 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1552 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
ω scans	θ_max = 33.4°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −21→21
T_min = 0.534, T_max = 1.000	k = −11→12
8422 measured reflections	l = −12→10
1667 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.018	H-atom parameters constrained
wR(F²) = 0.044	w = 1/[σ²(F_o²) + (0.0175P)² + 1.2212P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max = 0.002
1667 reflections	Δρ_max = 0.52 e Å⁻³
46 parameters	Δρ_min = −1.23 e Å⁻³

Special details top

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. One low angle reflection with F_o << Fc was omitted from the final refinement cycles.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.31503 (2)	0.11885 (2)	0.75250 (2)	0.01529 (5)
C11	0.41526 (13)	0.2215 (2)	0.6102 (3)	0.0142 (3)
H111	0.4651	0.1386	0.6070	0.017*
H112	0.3826	0.2433	0.4921	0.017*
C1	0.45886 (13)	0.3782 (2)	0.6864 (2)	0.0111 (3)
C2	0.41839 (13)	0.5301 (2)	0.6268 (3)	0.0136 (3)
H2	0.3623	0.5307	0.5427	0.016*
C3	0.45882 (14)	0.6802 (2)	0.6886 (3)	0.0156 (4)
H3	0.4304	0.7823	0.6470	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01370 (7)	0.01474 (7)	0.01747 (8)	−0.00335 (4)	0.00325 (5)	0.00078 (4)
C11	0.0139 (8)	0.0163 (8)	0.0132 (9)	−0.0016 (6)	0.0044 (7)	−0.0027 (7)
C1	0.0115 (8)	0.0123 (8)	0.0102 (8)	−0.0008 (5)	0.0039 (6)	−0.0001 (6)
C2	0.0131 (8)	0.0158 (8)	0.0122 (9)	0.0026 (6)	0.0035 (7)	0.0011 (7)
C3	0.0212 (9)	0.0122 (8)	0.0153 (9)	0.0026 (7)	0.0085 (7)	0.0031 (7)

Geometric parameters (Å, º) top

I1—C11	2.1902 (19)	C1—C1ⁱ	1.410 (4)
C11—C1	1.487 (3)	C2—C3	1.391 (3)
C11—H111	0.9900	C2—H2	0.9500
C11—H112	0.9900	C3—C3ⁱ	1.392 (4)
C1—C2	1.399 (3)	C3—H3	0.9500

C1—C11—I1	112.15 (13)	C1ⁱ—C1—C11	121.93 (11)
C1—C11—H111	109.2	C3—C2—C1	121.16 (18)
I1—C11—H111	109.2	C3—C2—H2	119.4
C1—C11—H112	109.2	C1—C2—H2	119.4
I1—C11—H112	109.2	C2—C3—C3ⁱ	119.72 (12)
H111—C11—H112	107.9	C2—C3—H3	120.1
C2—C1—C1ⁱ	119.10 (11)	C3ⁱ—C3—H3	120.1
C2—C1—C11	118.94 (18)

I1—C11—C1—C2	−93.41 (19)	C11—C1—C2—C3	−177.12 (17)
I1—C11—C1—C1ⁱ	88.3 (2)	C1—C2—C3—C3ⁱ	0.2 (3)
C1ⁱ—C1—C2—C3	1.2 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···I1ⁱⁱ	0.95	3.38	4.046 (2)	129
C11—H112···I1ⁱⁱⁱ	0.99	3.33	4.179 (2)	145
C2—H2···I1ⁱⁱⁱ	0.95	3.36	4.257 (2)	158

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

(II) 1,3-Bis(iodomethyl)benzene top

Crystal data top

C₈H₈I₂	F(000) = 648
M_r = 357.94	D_x = 2.483 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.5323 (3) Å	θ = 2.6–33.0°
b = 4.5464 (1) Å	µ = 6.50 mm⁻¹
c = 15.6269 (4) Å	T = 90 K
β = 95.203 (1)°	Needle, colourless
V = 957.46 (4) Å³	0.45 × 0.06 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2826 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
ω scans	θ_max = 33.4°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −20→20
T_min = 0.569, T_max = 1.000	k = −6→5
16804 measured reflections	l = −23→24
3435 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.048	w = 1/[σ²(F_o²) + (0.0109P)² + 1.4343P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.002
3435 reflections	Δρ_max = 1.24 e Å⁻³
91 parameters	Δρ_min = −0.77 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.35561 (2)	0.36401 (4)	0.46514 (2)	0.01445 (4)
C11	0.4498 (2)	0.1469 (6)	0.37746 (17)	0.0197 (5)
H11A	0.5193	0.1461	0.4034	0.024*
H11B	0.4282	−0.0599	0.3690	0.024*
C1	0.44471 (19)	0.2984 (6)	0.29275 (16)	0.0152 (5)
C2	0.51858 (18)	0.4993 (5)	0.27547 (16)	0.0138 (5)
H2	0.5707	0.5419	0.3185	0.017*
C3	0.51650 (18)	0.6379 (5)	0.19574 (16)	0.0128 (4)
C31	0.59593 (19)	0.8514 (6)	0.17788 (17)	0.0175 (5)
H31A	0.6261	0.9352	0.2326	0.021*
H31B	0.5667	1.0148	0.1421	0.021*
I3	0.71036 (2)	0.63230 (4)	0.11079 (2)	0.01692 (5)
C4	0.43920 (19)	0.5755 (6)	0.13244 (16)	0.0171 (5)
H4	0.4369	0.6696	0.0780	0.021*
C5	0.36591 (19)	0.3753 (6)	0.14961 (17)	0.0179 (5)
H5	0.3138	0.3322	0.1066	0.022*
C6	0.36832 (19)	0.2379 (6)	0.22919 (18)	0.0178 (5)
H6	0.3177	0.1021	0.2404	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01484 (7)	0.01475 (9)	0.01451 (8)	0.00033 (6)	0.00534 (5)	0.00083 (6)
C11	0.0223 (12)	0.0167 (13)	0.0216 (12)	0.0064 (11)	0.0091 (10)	0.0020 (11)
C1	0.0174 (11)	0.0125 (12)	0.0167 (11)	0.0032 (10)	0.0065 (9)	0.0003 (9)
C2	0.0149 (11)	0.0112 (12)	0.0155 (11)	0.0011 (9)	0.0035 (9)	−0.0025 (9)
C3	0.0139 (10)	0.0097 (11)	0.0153 (10)	0.0010 (9)	0.0044 (8)	−0.0013 (9)
C31	0.0191 (12)	0.0131 (13)	0.0215 (12)	−0.0020 (10)	0.0083 (10)	−0.0037 (10)
I3	0.01582 (8)	0.01765 (9)	0.01833 (8)	−0.00134 (6)	0.00728 (6)	−0.00027 (6)
C4	0.0184 (11)	0.0182 (13)	0.0148 (11)	0.0024 (10)	0.0016 (9)	0.0005 (10)
C5	0.0152 (11)	0.0191 (13)	0.0190 (12)	0.0004 (10)	−0.0012 (9)	−0.0044 (10)
C6	0.0153 (11)	0.0147 (13)	0.0243 (13)	−0.0029 (10)	0.0057 (10)	−0.0010 (11)

Geometric parameters (Å, º) top

I1—C11	2.189 (3)	C3—C31	1.493 (3)
I1—I3ⁱ	3.8662 (2)	C31—I3	2.187 (2)
C11—C1	1.488 (4)	C31—H31A	0.9900
C11—H11A	0.9900	C31—H31B	0.9900
C11—H11B	0.9900	C4—C5	1.390 (4)
C1—C6	1.394 (4)	C4—H4	0.9500
C1—C2	1.399 (3)	C5—C6	1.390 (4)
C2—C3	1.394 (3)	C5—H5	0.9500
C2—H2	0.9500	C6—H6	0.9500
C3—C4	1.402 (3)

C11—I1—I3ⁱ	117.47 (7)	C3—C31—I3	110.27 (16)
C1—C11—I1	111.45 (17)	C3—C31—H31A	109.6
C1—C11—H11A	109.3	I3—C31—H31A	109.6
I1—C11—H11A	109.3	C3—C31—H31B	109.6
C1—C11—H11B	109.3	I3—C31—H31B	109.6
I1—C11—H11B	109.3	H31A—C31—H31B	108.1
H11A—C11—H11B	108.0	C5—C4—C3	119.7 (2)
C6—C1—C2	119.2 (2)	C5—C4—H4	120.1
C6—C1—C11	120.9 (2)	C3—C4—H4	120.1
C2—C1—C11	119.9 (2)	C6—C5—C4	120.5 (2)
C3—C2—C1	120.7 (2)	C6—C5—H5	119.7
C3—C2—H2	119.6	C4—C5—H5	119.7
C1—C2—H2	119.6	C5—C6—C1	120.3 (2)
C2—C3—C4	119.5 (2)	C5—C6—H6	119.9
C2—C3—C31	120.3 (2)	C1—C6—H6	119.9
C4—C3—C31	120.2 (2)

I1—C11—C1—C6	−83.6 (3)	C4—C3—C31—I3	−83.7 (3)
I1—C11—C1—C2	97.9 (2)	C2—C3—C4—C5	−0.3 (4)
C6—C1—C2—C3	−0.1 (4)	C31—C3—C4—C5	179.7 (2)
C11—C1—C2—C3	178.4 (2)	C3—C4—C5—C6	0.4 (4)
C1—C2—C3—C4	0.2 (4)	C4—C5—C6—C1	−0.3 (4)
C1—C2—C3—C31	−179.8 (2)	C2—C1—C6—C5	0.2 (4)
C2—C3—C31—I3	96.4 (2)	C11—C1—C6—C5	−178.4 (2)

Symmetry code: (i) x−1/2, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···I1ⁱⁱ	0.99	3.22	4.060 (3)	144
C5—H5···I1ⁱⁱⁱ	0.95	3.25	4.078 (3)	147
C31—H31A···I3^iv	0.99	3.27	4.224 (3)	162
C31—H31A···Cg^v	0.99	2.84	3.453 (3)	121

Symmetry codes: (ii) x, y−1, z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x+3/2, y+1/2, −z+1/2; (v) x, y+1, z.

Acknowledgements

We thank the NZ Ministry of Business, Innovation and Employment Science Investment Fund (grant No. UOO-X1206), for support of this work and the University of Otago for the purchase of the diffractometer. JS thanks the Department of Chemistry, University of Otago, for support of his work.

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structures of two bis­­(iodo­meth­yl)benzene derivatives: similarities and differences in the crystal packing

1. Chemical context

2. Structural commentary

3. Supra­molecular features

3.1. Crystal packing for (I)

3.2. Crystal packing for (II)

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structures of two bis(iodomethyl)benzene derivatives: similarities and differences in the crystal packing

3. Supramolecular features