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

Wang, J.; Duan, E.; Zhou, E.; Yao, Q.; Zhang, W.

doi:10.1107/S160053681101765X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1414

doi:10.1107/S160053681101765X

Open

access

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

Juan Wang,^a ^* Erhong Duan,^b Erpeng Zhou,^a Qingguo Yao ^a and Wenna Zhang ^a

^aSchool of Chemical Engineering, Shijiazhuang University, Shijiazhuang 050035, People's Republic of China, and ^bSchool of Environmental Science and Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, People's Republic of China
^*Correspondence e-mail: wangjuantju@yahoo.com.cn

(Received 8 May 2011; accepted 10 May 2011; online 14 May 2011)

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, P 2₁ /c
a = 17.593 (4) Å
b = 5.7722 (12) Å
c = 13.319 (3) Å
β = 105.71 (3)°
V = 1302.0 (5) Å³
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[F² > 2σ(F²)] = 0.028
wR(F²) = 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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101765X/hb5876sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101765X/hb5876Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681101765X/hb5876Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

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).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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).

Figures top

Fig. 1. The molecular structure of (I) with 50% probability displacement ellipsoids.

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

Crystal data top

C₁₄H₁₉I	F(000) = 624
M_r = 314.19	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0482P)²] where P = (F_o² + 2F_c²)/3
2264 reflections	(Δ/σ)_max = 0.002
137 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −1.49 e Å⁻³

Crystal data top

C₁₄H₁₉I	V = 1302.0 (5) Å³
M_r = 314.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.593 (4) Å	µ = 2.43 mm⁻¹
b = 5.7722 (12) Å	T = 113 K
c = 13.319 (3) Å	0.20 × 0.18 × 0.12 mm
β = 105.71 (3)°

Data collection top

Rigaku Saturn CCD diffractometer	2264 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2077 reflections with I > 2σ(I)
T_min = 0.642, T_max = 0.759	R_int = 0.030
8233 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.13	Δρ_max = 0.52 e Å⁻³
2264 reflections	Δρ_min = −1.49 e Å⁻³
137 parameters

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. 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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₉I
M_r	314.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	17.593 (4), 5.7722 (12), 13.319 (3)
β (°)	105.71 (3)
V (Å³)	1302.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.43
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.642, 0.759
No. of measured, independent and observed [I > 2σ(I)] reflections	8233, 2264, 2077
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.074, 1.13
No. of reflections	2264
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −1.49

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

References

Demus, D. & Hauser, A. (1990). Selected Topics in Liquid Crystal Research, edited by H.-D. Koswig, p. 19. Berlin: Akademie-Verlag. Google Scholar
Kozhushkov, S. I., Langer, R. & Yufit, D. S. (2004). Eur. J. Org. Chem. pp. 289–303. CrossRef Google Scholar
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar