1-[4-(Iodo­meth­yl)cyclo­hex­yl]-4-methyl­benzene

Abstract

In the title compound, C₁₄H₁₉I, the cyclo­hexane ring adopts a chair conformation and the substituents are in equatorial sites. The dihedral angle between the mean planes of the cyclo­hexane and benzene rings is 67.23 (13)°.

Related literature

The title compound is an inter­mediate in the praparation of liquid crystals. For background to liquid crystals, see: Demus & Hauser (1990 ▶). For the synthesis, see: Kozhushkov et al. (2004 ▶).

Experimental

Crystal data

• C₁₄H₁₉I

• M _r = 314.19

• Monoclinic,

• a = 17.593 (4) Å

• b = 5.7722 (12) Å

• c = 13.319 (3) Å

• β = 105.71 (3)°

• V = 1302.0 (5) ų

• Z = 4

• Mo Kα radiation

• μ = 2.43 mm⁻¹

• T = 113 K

• 0.20 × 0.18 × 0.12 mm

Data collection

• Rigaku Saturn CCD diffractometer

• Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.642, T _max = 0.759

• 8233 measured reflections

• 2264 independent reflections

• 2077 reflections with I > 2σ(I)

• R _int = 0.030

Refinement

• R[F ² > 2σ(F ²)] = 0.028

• wR(F ²) = 0.074

• S = 1.13

• 2264 reflections

• 137 parameters

• H-atom parameters constrained

• Δρ_max = 0.52 e Å⁻³

• Δρ_min = −1.49 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 ▶).

Supplementary Material

Supplementary material file. DOI: 10.1107/S160053681101765X/hb5876Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

The title compound, (I), is an intermediate of liquid crystal compounds (Demus et al.,1990), which is synthesized from 1-bromo- 4-methylbenzene and 1-bromo-4-(iodomethyl)cyclohexane using diethyl ether as solvent (Kozhushkov et al.,2004). Herein, we report the title compound crystal structure.

In the molecule, Fig 1, a cyclohexane ring was attached at the para position of a benzene ring. The cyclohexyl ring has a typical chair conformation, with the tosion angles C3/C4/C5/C6 and C4/C5/C6/C7 being 56.7 (3) ° and -56.4 (3)°. No significant H-bonding or stacking interactions occur in the molecule packing.

Experimental

1-(4-(Iodomethyl)cyclohexyl)-4-methylbenzene was synthesized according to the method described by Kozhushkov et al. (2004). Colourless prisms of (I) were obtained by evaporation from its ethanoic solution at room temperature (m.p. 318–319 K).

Refinement

All H atoms were positioned geometrically and constrained to ride on their parent atoms [C—H distances are 0.95, 0.99 and 1.0Å with U_iso(H) = 1.2 U_eq(C) for aromatic and other aliphatic atoms, 0.98Å with U_iso = 1.5U_eq (C) for CH₃ atoms].

Figures

Fig. 1.

The molecular structure of (I) with 50% probability displacement ellipsoids.

Crystal data

C14H19I	F(000) = 624
Mr = 314.19	Dx = 1.603 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4209 reflections
a = 17.593 (4) Å	θ = 2.4–27.9°
b = 5.7722 (12) Å	µ = 2.43 mm−1
c = 13.319 (3) Å	T = 113 K
β = 105.71 (3)°	Prism, colourless
V = 1302.0 (5) Å3	0.20 × 0.18 × 0.12 mm
Z = 4

Data collection

Rigaku Saturn CCD diffractometer	2264 independent reflections
Radiation source: rotating anode	2077 reflections with I > 2σ(I)
confocal	Rint = 0.030
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 2.4°
ω and φ scans	h = −20→19
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −5→6
Tmin = 0.642, Tmax = 0.759	l = −15→15
8233 measured reflections

Refinement

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0482P)2] where P = (Fo2 + 2Fc2)/3
2264 reflections	(Δ/σ)max = 0.002
137 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −1.49 e Å−3

Special details

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
I1	0.069728 (10)	1.27167 (3)	0.586560 (14)	0.02224 (11)
C1	0.08795 (15)	0.9476 (4)	0.6716 (2)	0.0203 (6)
H1A	0.0358	0.8786	0.6681	0.024*
H1B	0.1162	0.8396	0.6364	0.024*
C2	0.13409 (14)	0.9681 (4)	0.78479 (19)	0.0141 (5)
H2	0.1054	1.0764	0.8205	0.017*
C3	0.13670 (19)	0.7272 (4)	0.8348 (2)	0.0189 (6)
H3A	0.0821	0.6747	0.8291	0.023*
H3B	0.1610	0.6158	0.7961	0.023*
C4	0.18367 (18)	0.7284 (4)	0.9493 (2)	0.0182 (6)
H4A	0.1856	0.5694	0.9777	0.022*
H4B	0.1567	0.8288	0.9892	0.022*
C5	0.26817 (15)	0.8169 (4)	0.9629 (2)	0.0153 (5)
H5	0.2931	0.7121	0.9211	0.018*
C6	0.26524 (15)	1.0592 (4)	0.9148 (2)	0.0192 (6)
H6A	0.3197	1.1131	0.9206	0.023*
H6B	0.2407	1.1686	0.9540	0.023*
C7	0.21762 (14)	1.0587 (4)	0.79919 (19)	0.0183 (6)
H7A	0.2152	1.2184	0.7713	0.022*
H7B	0.2450	0.9606	0.7589	0.022*
C8	0.31731 (17)	0.8004 (4)	1.0745 (2)	0.0176 (6)
C9	0.36274 (15)	0.6031 (4)	1.1085 (2)	0.0196 (6)
H9	0.3623	0.4812	1.0605	0.024*
C10	0.40846 (15)	0.5803 (5)	1.2105 (2)	0.0219 (6)
H10	0.4389	0.4438	1.2307	0.026*
C11	0.41059 (18)	0.7517 (4)	1.2830 (3)	0.0202 (7)
C12	0.36493 (16)	0.9486 (4)	1.2509 (2)	0.0236 (6)
H12	0.3654	1.0694	1.2995	0.028*
C13	0.31856 (15)	0.9713 (4)	1.1484 (2)	0.0213 (6)
H13	0.2872	1.1063	1.1287	0.026*
C14	0.4619 (2)	0.7254 (5)	1.3942 (3)	0.0281 (7)
H14A	0.4348	0.6273	1.4337	0.042*
H14B	0.4719	0.8782	1.4272	0.042*
H14C	0.5123	0.6535	1.3935	0.042*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
I1	0.02506 (16)	0.01680 (15)	0.02078 (17)	−0.00064 (6)	−0.00077 (11)	0.00342 (6)
C1	0.0228 (15)	0.0154 (13)	0.0209 (15)	−0.0007 (11)	0.0028 (12)	0.0017 (11)
C2	0.0136 (13)	0.0133 (13)	0.0153 (14)	0.0027 (9)	0.0037 (11)	−0.0018 (10)
C3	0.0193 (16)	0.0200 (14)	0.0175 (17)	−0.0035 (10)	0.0053 (13)	0.0004 (10)
C4	0.0207 (16)	0.0166 (14)	0.0201 (17)	−0.0014 (10)	0.0100 (13)	0.0026 (10)
C5	0.0156 (14)	0.0148 (12)	0.0155 (14)	0.0024 (10)	0.0044 (11)	−0.0013 (10)
C6	0.0158 (14)	0.0206 (14)	0.0191 (15)	−0.0035 (11)	0.0012 (11)	0.0038 (11)
C7	0.0175 (14)	0.0179 (13)	0.0193 (15)	−0.0023 (10)	0.0044 (11)	0.0045 (10)
C8	0.0168 (15)	0.0171 (13)	0.0198 (16)	−0.0007 (10)	0.0067 (12)	0.0019 (11)
C9	0.0193 (15)	0.0191 (14)	0.0197 (15)	0.0047 (11)	0.0038 (12)	−0.0021 (11)
C10	0.0192 (15)	0.0253 (14)	0.0212 (16)	0.0062 (11)	0.0051 (12)	0.0035 (11)
C11	0.0167 (16)	0.0292 (16)	0.0153 (17)	−0.0044 (10)	0.0050 (13)	0.0038 (10)
C12	0.0293 (16)	0.0245 (14)	0.0187 (16)	−0.0012 (12)	0.0092 (13)	−0.0032 (11)
C13	0.0267 (16)	0.0186 (13)	0.0194 (15)	0.0071 (11)	0.0079 (12)	0.0020 (11)
C14	0.0184 (17)	0.046 (2)	0.0187 (18)	−0.0042 (12)	0.0027 (14)	0.0033 (12)

Geometric parameters (Å, °)

I1—C1	2.165 (3)	C6—H6B	0.9900
C1—C2	1.511 (3)	C7—H7A	0.9900
C1—H1A	0.9900	C7—H7B	0.9900
C1—H1B	0.9900	C8—C13	1.389 (4)
C2—C7	1.522 (3)	C8—C9	1.394 (3)
C2—C3	1.537 (3)	C9—C10	1.385 (4)
C2—H2	1.0000	C9—H9	0.9500
C3—C4	1.525 (4)	C10—C11	1.376 (4)
C3—H3A	0.9900	C10—H10	0.9500
C3—H3B	0.9900	C11—C12	1.391 (4)
C4—C5	1.536 (4)	C11—C14	1.519 (5)
C4—H4A	0.9900	C12—C13	1.393 (4)
C4—H4B	0.9900	C12—H12	0.9500
C5—C8	1.507 (4)	C13—H13	0.9500
C5—C6	1.533 (3)	C14—H14A	0.9800
C5—H5	1.0000	C14—H14B	0.9800
C6—C7	1.541 (3)	C14—H14C	0.9800
C6—H6A	0.9900
C2—C1—I1	114.67 (17)	C5—C6—H6B	109.4
C2—C1—H1A	108.6	C7—C6—H6B	109.4
I1—C1—H1A	108.6	H6A—C6—H6B	108.0
C2—C1—H1B	108.6	C2—C7—C6	111.81 (19)
I1—C1—H1B	108.6	C2—C7—H7A	109.3
H1A—C1—H1B	107.6	C6—C7—H7A	109.3
C1—C2—C7	113.1 (2)	C2—C7—H7B	109.3
C1—C2—C3	107.8 (2)	C6—C7—H7B	109.3
C7—C2—C3	110.0 (2)	H7A—C7—H7B	107.9
C1—C2—H2	108.6	C13—C8—C9	116.9 (3)
C7—C2—H2	108.6	C13—C8—C5	123.3 (2)
C3—C2—H2	108.6	C9—C8—C5	119.8 (2)
C4—C3—C2	111.9 (2)	C10—C9—C8	121.7 (2)
C4—C3—H3A	109.2	C10—C9—H9	119.1
C2—C3—H3A	109.2	C8—C9—H9	119.1
C4—C3—H3B	109.2	C11—C10—C9	121.2 (2)
C2—C3—H3B	109.2	C11—C10—H10	119.4
H3A—C3—H3B	107.9	C9—C10—H10	119.4
C3—C4—C5	111.4 (2)	C10—C11—C12	117.9 (3)
C3—C4—H4A	109.3	C10—C11—C14	120.6 (2)
C5—C4—H4A	109.3	C12—C11—C14	121.6 (2)
C3—C4—H4B	109.3	C11—C12—C13	121.0 (3)
C5—C4—H4B	109.3	C11—C12—H12	119.5
H4A—C4—H4B	108.0	C13—C12—H12	119.5
C8—C5—C6	114.5 (2)	C8—C13—C12	121.3 (2)
C8—C5—C4	112.0 (2)	C8—C13—H13	119.4
C6—C5—C4	109.4 (2)	C12—C13—H13	119.4
C8—C5—H5	106.8	C11—C14—H14A	109.5
C6—C5—H5	106.8	C11—C14—H14B	109.5
C4—C5—H5	106.8	H14A—C14—H14B	109.5
C5—C6—C7	111.3 (2)	C11—C14—H14C	109.5
C5—C6—H6A	109.4	H14A—C14—H14C	109.5
C7—C6—H6A	109.4	H14B—C14—H14C	109.5
I1—C1—C2—C7	−61.9 (2)	C4—C5—C8—C13	−85.8 (3)
I1—C1—C2—C3	176.26 (17)	C6—C5—C8—C9	−142.4 (2)
C1—C2—C3—C4	178.9 (2)	C4—C5—C8—C9	92.3 (3)
C7—C2—C3—C4	55.1 (3)	C13—C8—C9—C10	−1.5 (4)
C2—C3—C4—C5	−56.9 (3)	C5—C8—C9—C10	−179.7 (2)
C3—C4—C5—C8	−175.25 (19)	C8—C9—C10—C11	0.4 (4)
C3—C4—C5—C6	56.7 (3)	C9—C10—C11—C12	0.3 (4)
C8—C5—C6—C7	177.0 (2)	C9—C10—C11—C14	−179.2 (2)
C4—C5—C6—C7	−56.4 (3)	C10—C11—C12—C13	0.0 (4)
C1—C2—C7—C6	−175.4 (2)	C14—C11—C12—C13	179.5 (2)
C3—C2—C7—C6	−54.8 (3)	C9—C8—C13—C12	1.8 (4)
C5—C6—C7—C2	56.8 (3)	C5—C8—C13—C12	180.0 (2)
C6—C5—C8—C13	39.4 (3)	C11—C12—C13—C8	−1.1 (4)