Triclinic form of 1,2,4,5-tetra­cyclo­hexyl­benzene

Mague, J.T.; Linhardt, L.; Medina, I.; Sattler, D.J.; Fink, M.J.

doi:10.1107/S1600536807067578

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o376

doi:10.1107/S1600536807067578

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Triclinic form of 1,2,4,5-tetracyclohexylbenzene

Joel T. Mague,^a ^* Lisa Linhardt,^a Iliana Medina,^a Daniel J. Sattler ^a and Mark J. Fink ^a

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: joelt@tulane.edu

(Received 13 December 2007; accepted 18 December 2007; online 4 January 2008)

The molecule of the title compound, C₃₀H₄₆, has a crystallographically imposed inversion center and the cyclohexyl groups are oriented with their methine H atoms pointing towards one another (H⋯H = 2.04 Å).

Related literature

For related structures, see: Mague et al. (2008a ,b ).

Experimental

Crystal data

C₃₀H₄₆
M_r = 406.67
Triclinic, $[P \overline 1]$
a = 6.014 (1) Å
b = 10.001 (1) Å
c = 10.513 (2) Å
α = 91.164 (2)°
β = 94.815 (2)°
γ = 106.336 (3)°
V = 604.01 (16) Å³
Z = 1
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 100 (2) K
0.20 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.940, T_max = 0.993
4730 measured reflections
2363 independent reflections
1862 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.147
S = 1.03
2363 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus (Bruker, 2004 ); data reduction: SAINT-Plus program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067578/gk2128sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807067578/gk2128Isup2.hkl

checkCIF report

Comment top

Crystallization of 1,2,4,5-tetracylohexylbenzene (C₃₀H₄₆) from hot methylcyclohexane forms colorless needle-shaped crystals together with a smaller quantity having a distinctly different block-shaped morphology. Many of the needles appear twinned but a fragment cut from a larger needle proved to be single and to be a triclinic modification. The molecule has crystallographically imposed centrosymmetry with the cyclohexyl rings adopting the chair conformation and oriented with their methine hydrogen atoms pointed towards one another (H4···H10 distance 2.04 Å) as is the case in the monoclinic modification (Mague et al., 2008a). Again, there are very few close contacts between the ortho-disposed cyclohexyl rings, the shortest being H4···H15b (2.30 Å). Additional short contacts are H3···H9b (2.28 Å) and H3···H11a' (2.14 Å). The plane defined by the atoms C5, C6, C8, C9 ("seat" of the chair) is inclined to the plane of the aromatic ring by 87.3 (2)° while that for the other cyclohexyl ring (C11, C12, C14, C15) is inclined at an angle of only 49.4 (2)°, a much greater disparity in orientation than observed in the monoclinic modification. Another difference is the absence of any significant C—H···π interactions in the triclinic form.

Related literature top

For related structures, see: Mague et al. 2008a, 2008b).

Experimental top

The title compound was prepared by the literature method (Mague et al., 2008a)

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level and H-atoms are represented by spheres of arbitrary radius. Primed atoms are related to unprimed atoms by the symmetry operation -x, 1 - y, -z.

1,2,4,5-tetracyclohexylbenzene top

Crystal data top

C₃₀H₄₆	Z = 1
M_r = 406.67	F(000) = 226
Triclinic, P1	D_x = 1.118 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.014 (1) Å	Cell parameters from 2522 reflections
b = 10.001 (1) Å	θ = 2.8–28.3°
c = 10.513 (2) Å	µ = 0.06 mm⁻¹
α = 91.164 (2)°	T = 100 K
β = 94.815 (2)°	Plate, colorless
γ = 106.336 (3)°	0.20 × 0.13 × 0.10 mm
V = 604.01 (16) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2363 independent reflections
Radiation source: fine-focus sealed tube	1862 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 0 pixels mm^-1	θ_max = 26.0°, θ_min = 2.0°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −12→12
T_min = 0.940, T_max = 0.993	l = −12→12
4730 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0804P)² + 0.1811P] where P = (F_o² + 2F_c²)/3
2363 reflections	(Δ/σ)_max < 0.001
136 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₃₀H₄₆	γ = 106.336 (3)°
M_r = 406.67	V = 604.01 (16) Å³
Triclinic, P1	Z = 1
a = 6.014 (1) Å	Mo Kα radiation
b = 10.001 (1) Å	µ = 0.06 mm⁻¹
c = 10.513 (2) Å	T = 100 K
α = 91.164 (2)°	0.20 × 0.13 × 0.10 mm
β = 94.815 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2363 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	1862 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.993	R_int = 0.023
4730 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.03	Δρ_max = 0.44 e Å⁻³
2363 reflections	Δρ_min = −0.26 e Å⁻³
136 parameters

Special details top

Experimental. The diffraction data were collected in three sets of 606 frames (ω scans, 0.3°/scan) at ϕ settings of 0, 120 and 240°.

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. H-atoms were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms.

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

	x	y	z	U_iso*/U_eq
C1	0.1622 (3)	0.08720 (17)	0.92456 (15)	0.0140 (4)
C2	0.0316 (3)	−0.04621 (17)	0.87681 (15)	0.0141 (4)
C3	−0.1264 (3)	−0.12910 (17)	0.95305 (15)	0.0147 (4)
H3	−0.2148	−0.2192	0.9199	0.018*
C4	0.0526 (3)	−0.10585 (17)	0.74528 (15)	0.0147 (4)
H4	0.1660	−0.0318	0.7022	0.018*
C5	0.1482 (3)	−0.23296 (18)	0.75408 (16)	0.0179 (4)
H5A	0.3031	−0.2056	0.8033	0.021*
H5B	0.0431	−0.3065	0.8002	0.021*
C6	0.1695 (3)	−0.29087 (19)	0.62131 (16)	0.0207 (4)
H6A	0.2875	−0.2207	0.5789	0.025*
H6B	0.2235	−0.3754	0.6301	0.025*
C7	−0.0612 (3)	−0.32752 (18)	0.53844 (16)	0.0211 (4)
H7A	−0.1747	−0.4051	0.5756	0.025*
H7B	−0.0386	−0.3589	0.4518	0.025*
C8	−0.1570 (3)	−0.20179 (19)	0.52917 (16)	0.0201 (4)
H8A	−0.3118	−0.2296	0.4798	0.024*
H8B	−0.0522	−0.1283	0.4829	0.024*
C9	−0.1790 (3)	−0.14328 (18)	0.66175 (15)	0.0178 (4)
H9A	−0.2333	−0.0590	0.6525	0.021*
H9B	−0.2969	−0.2133	0.7043	0.021*
C10	0.3406 (3)	0.18370 (17)	0.84830 (15)	0.0146 (4)
H10	0.2704	0.1748	0.7578	0.018*
C11	0.4030 (3)	0.33832 (18)	0.88976 (16)	0.0178 (4)
H11A	0.4788	0.3524	0.9782	0.021*
H11B	0.2591	0.3680	0.8887	0.021*
C12	0.5673 (3)	0.42760 (18)	0.80049 (16)	0.0190 (4)
H12A	0.4885	0.4178	0.7128	0.023*
H12B	0.6075	0.5270	0.8296	0.023*
C13	0.7888 (3)	0.38188 (18)	0.79954 (17)	0.0197 (4)
H13A	0.8902	0.4373	0.7386	0.024*
H13B	0.8746	0.4000	0.8856	0.024*
C14	0.7330 (3)	0.22785 (18)	0.76158 (16)	0.0184 (4)
H14A	0.8788	0.1998	0.7672	0.022*
H14B	0.6637	0.2117	0.6718	0.022*
C15	0.5639 (3)	0.13813 (18)	0.84782 (16)	0.0166 (4)
H15A	0.6398	0.1461	0.9360	0.020*
H15B	0.5238	0.0392	0.8174	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0186 (9)	0.0177 (9)	0.0079 (8)	0.0082 (7)	0.0026 (6)	0.0007 (6)
C2	0.0180 (9)	0.0197 (9)	0.0065 (8)	0.0083 (7)	0.0020 (6)	0.0006 (6)
C3	0.0197 (9)	0.0159 (9)	0.0085 (8)	0.0046 (7)	0.0031 (6)	−0.0002 (6)
C4	0.0219 (9)	0.0135 (8)	0.0084 (8)	0.0031 (7)	0.0066 (7)	−0.0004 (6)
C5	0.0230 (9)	0.0215 (9)	0.0100 (8)	0.0071 (7)	0.0044 (7)	−0.0016 (7)
C6	0.0276 (10)	0.0217 (10)	0.0151 (9)	0.0092 (8)	0.0076 (7)	−0.0024 (7)
C7	0.0317 (11)	0.0208 (9)	0.0101 (8)	0.0051 (8)	0.0067 (7)	−0.0047 (7)
C8	0.0274 (10)	0.0239 (10)	0.0077 (8)	0.0047 (8)	0.0023 (7)	−0.0005 (7)
C9	0.0254 (10)	0.0220 (9)	0.0078 (8)	0.0091 (7)	0.0043 (7)	−0.0002 (7)
C10	0.0194 (9)	0.0187 (9)	0.0061 (8)	0.0051 (7)	0.0046 (6)	0.0002 (6)
C11	0.0220 (9)	0.0197 (9)	0.0138 (8)	0.0071 (7)	0.0093 (7)	0.0008 (7)
C12	0.0264 (10)	0.0176 (9)	0.0143 (9)	0.0066 (7)	0.0083 (7)	0.0008 (7)
C13	0.0215 (9)	0.0221 (10)	0.0155 (9)	0.0045 (7)	0.0081 (7)	0.0027 (7)
C14	0.0205 (9)	0.0250 (10)	0.0122 (8)	0.0087 (7)	0.0070 (7)	0.0025 (7)
C15	0.0215 (9)	0.0179 (9)	0.0112 (8)	0.0059 (7)	0.0045 (7)	0.0017 (7)

Geometric parameters (Å, º) top

C1—C3ⁱ	1.397 (2)	C8—H8B	0.9900
C1—C2	1.402 (2)	C9—H9A	0.9900
C1—C10	1.523 (2)	C9—H9B	0.9900
C2—C3	1.395 (2)	C10—C11	1.530 (2)
C2—C4	1.524 (2)	C10—C15	1.535 (2)
C3—C1ⁱ	1.397 (2)	C10—H10	1.0000
C3—H3	0.9500	C11—C12	1.532 (2)
C4—C9	1.529 (2)	C11—H11A	0.9900
C4—C5	1.537 (2)	C11—H11B	0.9900
C4—H4	1.0000	C12—C13	1.526 (2)
C5—C6	1.529 (2)	C12—H12A	0.9900
C5—H5A	0.9900	C12—H12B	0.9900
C5—H5B	0.9900	C13—C14	1.519 (2)
C6—C7	1.522 (3)	C13—H13A	0.9900
C6—H6A	0.9900	C13—H13B	0.9900
C6—H6B	0.9900	C14—C15	1.529 (2)
C7—C8	1.525 (2)	C14—H14A	0.9900
C7—H7A	0.9900	C14—H14B	0.9900
C7—H7B	0.9900	C15—H15A	0.9900
C8—C9	1.531 (2)	C15—H15B	0.9900
C8—H8A	0.9900

C3ⁱ—C1—C2	117.64 (15)	C8—C9—H9A	109.3
C3ⁱ—C1—C10	120.34 (15)	C4—C9—H9B	109.3
C2—C1—C10	122.00 (14)	C8—C9—H9B	109.3
C3—C2—C1	118.62 (14)	H9A—C9—H9B	107.9
C3—C2—C4	117.96 (14)	C1—C10—C11	114.86 (13)
C1—C2—C4	123.43 (14)	C1—C10—C15	111.62 (13)
C2—C3—C1ⁱ	123.74 (16)	C11—C10—C15	109.51 (14)
C2—C3—H3	118.1	C1—C10—H10	106.8
C1ⁱ—C3—H3	118.1	C11—C10—H10	106.8
C2—C4—C9	111.87 (13)	C15—C10—H10	106.8
C2—C4—C5	111.95 (13)	C10—C11—C12	110.82 (13)
C9—C4—C5	110.22 (14)	C10—C11—H11A	109.5
C2—C4—H4	107.5	C12—C11—H11A	109.5
C9—C4—H4	107.5	C10—C11—H11B	109.5
C5—C4—H4	107.5	C12—C11—H11B	109.5
C6—C5—C4	111.24 (14)	H11A—C11—H11B	108.1
C6—C5—H5A	109.4	C13—C12—C11	110.19 (14)
C4—C5—H5A	109.4	C13—C12—H12A	109.6
C6—C5—H5B	109.4	C11—C12—H12A	109.6
C4—C5—H5B	109.4	C13—C12—H12B	109.6
H5A—C5—H5B	108.0	C11—C12—H12B	109.6
C7—C6—C5	111.78 (14)	H12A—C12—H12B	108.1
C7—C6—H6A	109.3	C14—C13—C12	111.15 (15)
C5—C6—H6A	109.3	C14—C13—H13A	109.4
C7—C6—H6B	109.3	C12—C13—H13A	109.4
C5—C6—H6B	109.3	C14—C13—H13B	109.4
H6A—C6—H6B	107.9	C12—C13—H13B	109.4
C6—C7—C8	110.76 (14)	H13A—C13—H13B	108.0
C6—C7—H7A	109.5	C13—C14—C15	111.44 (14)
C8—C7—H7A	109.5	C13—C14—H14A	109.3
C6—C7—H7B	109.5	C15—C14—H14A	109.3
C8—C7—H7B	109.5	C13—C14—H14B	109.3
H7A—C7—H7B	108.1	C15—C14—H14B	109.3
C7—C8—C9	111.34 (14)	H14A—C14—H14B	108.0
C7—C8—H8A	109.4	C14—C15—C10	111.17 (14)
C9—C8—H8A	109.4	C14—C15—H15A	109.4
C7—C8—H8B	109.4	C10—C15—H15A	109.4
C9—C8—H8B	109.4	C14—C15—H15B	109.4
H8A—C8—H8B	108.0	C10—C15—H15B	109.4
C4—C9—C8	111.79 (14)	H15A—C15—H15B	108.0
C4—C9—H9A	109.3

C3ⁱ—C1—C2—C3	0.3 (3)	C2—C4—C9—C8	179.42 (14)
C10—C1—C2—C3	179.24 (15)	C5—C4—C9—C8	−55.33 (18)
C3ⁱ—C1—C2—C4	−179.88 (15)	C7—C8—C9—C4	55.87 (19)
C10—C1—C2—C4	−0.9 (2)	C3ⁱ—C1—C10—C11	−21.8 (2)
C1—C2—C3—C1ⁱ	−0.3 (3)	C2—C1—C10—C11	159.29 (15)
C4—C2—C3—C1ⁱ	179.86 (15)	C3ⁱ—C1—C10—C15	103.66 (18)
C3—C2—C4—C9	59.29 (19)	C2—C1—C10—C15	−75.29 (19)
C1—C2—C4—C9	−120.57 (17)	C1—C10—C11—C12	−175.25 (14)
C3—C2—C4—C5	−65.00 (19)	C15—C10—C11—C12	58.25 (18)
C1—C2—C4—C5	115.15 (17)	C10—C11—C12—C13	−58.39 (19)
C2—C4—C5—C6	−179.65 (14)	C11—C12—C13—C14	56.47 (18)
C9—C4—C5—C6	55.15 (18)	C12—C13—C14—C15	−55.38 (19)
C4—C5—C6—C7	−55.97 (19)	C13—C14—C15—C10	55.66 (19)
C5—C6—C7—C8	55.61 (19)	C1—C10—C15—C14	175.04 (13)
C6—C7—C8—C9	−55.23 (19)	C11—C10—C15—C14	−56.63 (17)

Symmetry code: (i) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₃₀H₄₆
M_r	406.67
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.014 (1), 10.001 (1), 10.513 (2)
α, β, γ (°)	91.164 (2), 94.815 (2), 106.336 (3)
V (Å³)	604.01 (16)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.20 × 0.13 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.940, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	4730, 2363, 1862
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.147, 1.03
No. of reflections	2363
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.26

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).

Acknowledgements

We thank the Chemistry Department of Tulane University for support of the X-ray laboratory, and the Louisiana Board of Regents through the Louisiana Educational Quality Support Fund (Grant LEQSF (2003–2003)-ENH –TR-67) for the purchase of the APEX diffractometer.

References

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Bruker (2004). SAINT-Plus. Version 7.03. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Mague, J. T., Linhardt, L., Medina, I. & Fink, M. J. (2008b). Acta Cryst. E64, o335. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2002). SADABS. Version 2.05. University of Göttingen, Germany. Google Scholar