1-[4-(Iodo-meth-yl)cyclo-hex-yl]-4-methyl-benzene.

In the title compound, C(14)H(19)I, the cyclo-hexane ring adopts a chair conformation and the substituents are in equatorial sites. The dihedral angle between the mean planes of the cyclo-hexane 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 = 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) 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[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.074

S = 1.13

2264 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −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 ▶).

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

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

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

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

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

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 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

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.

	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*

	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)

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)