1-Cyclo­hexyl-6,7-dimeth­oxy-1,4-di­hydro­naphthalene

Chen, S.-Y.; Zhang, Y.-P.; Huang, B.; Yu, J.-J.; Shi, W.-Y.

doi:10.1107/S1600536814010204

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o671

doi:10.1107/S1600536814010204

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1-Cyclohexyl-6,7-dimethoxy-1,4-dihydronaphthalene

Shao-Yuan Chen,^a Ya-Ping Zhang,^a Bing Huang,^b Jia-Jun Yu ^c and Wei-Yong Shi ^d ^*

^aInstitute of Biotechnology, Zhejiang University, People's Republic of China, ^bCollege of Pharmaceutical Science, Zhejiang University, People's Republic of China, ^cCollege of Agriculture and Biotechnology, Zhejiang University, People's Republic of China, and ^dCollege of Environmental & Resource Sciences, Zhejiang University, People's Republic of China
^*Correspondence e-mail: wyshi@zju.edu.cn

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 24 April 2014; accepted 6 May 2014; online 17 May 2014)

The title compound, C₁₈H₂₄O₂, was isolated from the leaves extract of Ficus carica L. The cyclohexane ring displays a chair conformation whereas the cyclohexa-1,4-diene ring adopts a flattened boat conformation with methyl C atoms at the prow and stern. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds into supramolecular chains propagated along the b-axis direction.

CCDC reference: 990756

Related literature

For the bioactivity of the title compound, see: Fang et al. (2008 ); Xie & Zhuang (2010 ). For biological activity of compounds isolated from Ficus carica L, see: Joseph & Raj (2011 ).

Experimental

Crystal data

C₁₈H₂₄O₂
M_r = 272.37
Monoclinic, P 2₁
a = 9.0635 (4) Å
b = 6.3973 (3) Å
c = 13.9872 (7) Å
β = 104.241 (5)°
V = 786.08 (6) Å³
Z = 2
Cu Kα radiation
μ = 0.57 mm⁻¹
T = 294 K
0.28 × 0.15 × 0.12 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.76, T_max = 0.85
5062 measured reflections
2737 independent reflections
2318 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.114
S = 1.04
2737 reflections
184 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯O2ⁱ	0.96	2.59	3.272 (3)	129
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 990756

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814010204/xu5788sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814010204/xu5788Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814010204/xu5788Isup3.cml

checkCIF report

Comment top

Ficus carica L. is a deciduous tree belonging to the Moraceae family. Different biologically activity compounds have been isolated from this plant (Joseph & Raj, 2011). The leaf extracts of Ficus carica L. show the potential activity of inhibit the growth of the cancer cell, antioxidative and antibiosis (Xie & Zhuang, 2010; Fang et al., 2008). The title compound is one of leaves extracts from Ficus carica L.

In the title compound, the cyclohexane ring displays the chair conformation whereas the cyclohexadiene ring adopts the flattened boat conformation with the methyl-C atoms (C7 and C10) on the prow and stern, respectively. In the crystal, the molecules are linked by weak C—H···O hydrogen bonds into the supramolecular chains running along the b-axis direction.

Related literature top

For the bioactivity of the title compound, see: Fang et al. (2008); Xie & Zhuang (2010). For biologically activity compounds isolated from Ficus carica L., see: Joseph & Raj (2011).

Experimental top

The leaves of Ficus carica was be extracted by petroleum ether. The upper phase was filtered and evaporated in vacuo to obtain the crystals. The single crystals were recrystallized from a hexane solution.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

1-Cyclohexyl-6,7-dimethoxy-1,4-dihydronaphthalene top

Crystal data top

C₁₈H₂₄O₂	F(000) = 296
M_r = 272.37	D_x = 1.151 Mg m⁻³
Monoclinic, P2₁	Melting point: 423 K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54180 Å
a = 9.0635 (4) Å	Cell parameters from 5062 reflections
b = 6.3973 (3) Å	θ = 3.2–67.6°
c = 13.9872 (7) Å	µ = 0.57 mm⁻¹
β = 104.241 (5)°	T = 294 K
V = 786.08 (6) Å³	Needle, colourless
Z = 2	0.28 × 0.15 × 0.12 mm

Data collection top

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	2737 independent reflections
Radiation source: fine-focus sealed tube	2318 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 67.6°, θ_min = 3.3°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −10→10
T_min = 0.76, T_max = 0.85	k = −7→7
5062 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0621P)² + 0.0278P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2737 reflections	Δρ_max = 0.10 e Å⁻³
184 parameters	Δρ_min = −0.10 e Å⁻³
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0191 (17)

Crystal data top

C₁₈H₂₄O₂	V = 786.08 (6) Å³
M_r = 272.37	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 9.0635 (4) Å	µ = 0.57 mm⁻¹
b = 6.3973 (3) Å	T = 294 K
c = 13.9872 (7) Å	0.28 × 0.15 × 0.12 mm
β = 104.241 (5)°

Data collection top

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	2737 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2318 reflections with I > 2σ(I)
T_min = 0.76, T_max = 0.85	R_int = 0.027
5062 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.114	H-atom parameters constrained
S = 1.04	Δρ_max = 0.10 e Å⁻³
2737 reflections	Δρ_min = −0.10 e Å⁻³
184 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
O1	0.67571 (16)	0.5524 (2)	0.46174 (9)	0.0672 (4)
O2	0.83494 (17)	0.8807 (2)	0.52180 (12)	0.0718 (4)
C1	0.2221 (5)	0.3458 (6)	0.8467 (4)	0.1353 (15)
H1A	0.2527	0.3728	0.9170	0.162*
H1B	0.1118	0.3393	0.8273	0.162*
C2	0.2869 (5)	0.1400 (6)	0.8249 (3)	0.1189 (12)
H2A	0.2463	0.1053	0.7559	0.143*
H2B	0.2559	0.0314	0.8642	0.143*
C3	0.4597 (4)	0.1463 (4)	0.8472 (2)	0.0911 (8)
H3A	0.4972	0.0133	0.8296	0.109*
H3B	0.5010	0.1678	0.9173	0.109*
C4	0.5140 (3)	0.3217 (3)	0.78985 (15)	0.0649 (5)
H4	0.4671	0.2958	0.7199	0.078*
C5	0.4514 (3)	0.5281 (4)	0.8149 (2)	0.0806 (6)
H5A	0.4832	0.6389	0.7771	0.097*
H5B	0.4921	0.5582	0.8843	0.097*
C6	0.2766 (4)	0.5223 (6)	0.7919 (3)	0.1258 (13)
H6A	0.2393	0.6543	0.8107	0.151*
H6B	0.2357	0.5039	0.7215	0.151*
C7	0.6876 (3)	0.3242 (3)	0.80090 (15)	0.0650 (5)
H7	0.7156	0.1848	0.7823	0.078*
C8	0.7775 (3)	0.3614 (5)	0.90618 (18)	0.0876 (8)
H8	0.7745	0.2588	0.9528	0.105*
C9	0.8597 (3)	0.5300 (6)	0.93588 (19)	0.0947 (9)
H9	0.9077	0.5409	1.0026	0.114*
C10	0.8806 (3)	0.7015 (5)	0.87079 (18)	0.0859 (8)
H10A	0.9882	0.7343	0.8837	0.103*
H10B	0.8287	0.8247	0.8865	0.103*
C11	0.8579 (2)	0.7884 (3)	0.69386 (17)	0.0616 (5)
H11	0.9169	0.9059	0.7159	0.074*
C12	0.8086 (2)	0.7530 (3)	0.59475 (15)	0.0552 (5)
C13	0.72044 (19)	0.5754 (3)	0.56185 (13)	0.0501 (4)
C14	0.6851 (2)	0.4408 (3)	0.62918 (14)	0.0514 (4)
H14	0.6274	0.3224	0.6068	0.062*
C15	0.7338 (2)	0.4775 (3)	0.73125 (14)	0.0539 (5)
C16	0.8218 (2)	0.6528 (3)	0.76285 (14)	0.0610 (5)
C17	0.5812 (3)	0.3808 (4)	0.42523 (17)	0.0823 (7)
H17A	0.5560	0.3826	0.3544	0.123*
H17B	0.4896	0.3895	0.4478	0.123*
H17C	0.6336	0.2532	0.4485	0.123*
C18	0.9424 (3)	1.0441 (4)	0.5498 (2)	0.0919 (8)
H18A	0.9578	1.1121	0.4919	0.138*
H18B	1.0373	0.9872	0.5870	0.138*
H18C	0.9051	1.1436	0.5896	0.138*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0746 (9)	0.0747 (10)	0.0547 (7)	−0.0196 (8)	0.0205 (6)	−0.0016 (7)
O2	0.0705 (8)	0.0596 (9)	0.0941 (11)	−0.0131 (7)	0.0367 (7)	0.0036 (8)
C1	0.136 (3)	0.106 (3)	0.203 (4)	−0.003 (2)	0.117 (3)	0.007 (3)
C2	0.154 (3)	0.091 (2)	0.141 (3)	−0.035 (2)	0.092 (2)	−0.010 (2)
C3	0.140 (2)	0.0570 (13)	0.0913 (17)	−0.0017 (15)	0.0577 (16)	0.0064 (12)
C4	0.0840 (13)	0.0572 (11)	0.0592 (11)	0.0032 (10)	0.0287 (10)	0.0082 (9)
C5	0.0939 (16)	0.0562 (12)	0.1033 (17)	0.0071 (12)	0.0465 (13)	0.0113 (12)
C6	0.097 (2)	0.102 (2)	0.202 (4)	0.015 (2)	0.081 (2)	0.028 (3)
C7	0.0811 (13)	0.0583 (11)	0.0562 (11)	0.0179 (11)	0.0183 (9)	0.0064 (9)
C8	0.0953 (17)	0.103 (2)	0.0590 (13)	0.0274 (17)	0.0093 (12)	0.0216 (14)
C9	0.0919 (18)	0.123 (3)	0.0570 (12)	0.0246 (19)	−0.0047 (12)	−0.0068 (17)
C10	0.0874 (16)	0.094 (2)	0.0661 (14)	0.0091 (15)	0.0004 (11)	−0.0205 (14)
C11	0.0474 (9)	0.0562 (12)	0.0812 (13)	−0.0035 (8)	0.0157 (9)	−0.0141 (10)
C12	0.0431 (8)	0.0527 (10)	0.0743 (12)	0.0006 (8)	0.0229 (8)	−0.0012 (9)
C13	0.0449 (9)	0.0532 (10)	0.0545 (10)	−0.0011 (7)	0.0169 (7)	−0.0041 (8)
C14	0.0488 (9)	0.0498 (10)	0.0570 (10)	−0.0028 (8)	0.0157 (8)	−0.0043 (8)
C15	0.0546 (10)	0.0544 (11)	0.0532 (10)	0.0115 (8)	0.0140 (8)	−0.0018 (8)
C16	0.0533 (10)	0.0637 (12)	0.0623 (11)	0.0095 (9)	0.0070 (9)	−0.0139 (10)
C17	0.0982 (16)	0.0818 (16)	0.0584 (12)	−0.0295 (14)	0.0032 (11)	−0.0050 (11)
C18	0.0838 (16)	0.0603 (14)	0.146 (2)	−0.0186 (13)	0.0553 (16)	−0.0067 (15)

Geometric parameters (Å, º) top

O1—C13	1.367 (2)	C7—C8	1.516 (3)
O1—C17	1.409 (3)	C7—H7	0.9800
O2—C12	1.373 (2)	C8—C9	1.318 (4)
O2—C18	1.417 (3)	C8—H8	0.9300
C1—C2	1.503 (5)	C9—C10	1.468 (5)
C1—C6	1.514 (5)	C9—H9	0.9300
C1—H1A	0.9700	C10—C16	1.505 (3)
C1—H1B	0.9700	C10—H10A	0.9700
C2—C3	1.520 (5)	C10—H10B	0.9700
C2—H2A	0.9700	C11—C12	1.367 (3)
C2—H2B	0.9700	C11—C16	1.395 (3)
C3—C4	1.529 (3)	C11—H11	0.9300
C3—H3A	0.9700	C12—C13	1.400 (3)
C3—H3B	0.9700	C13—C14	1.371 (3)
C4—C5	1.512 (3)	C14—C15	1.406 (3)
C4—C7	1.543 (3)	C14—H14	0.9300
C4—H4	0.9800	C15—C16	1.384 (3)
C5—C6	1.537 (4)	C17—H17A	0.9600
C5—H5A	0.9700	C17—H17B	0.9600
C5—H5B	0.9700	C17—H17C	0.9600
C6—H6A	0.9700	C18—H18A	0.9600
C6—H6B	0.9700	C18—H18B	0.9600
C7—C15	1.512 (3)	C18—H18C	0.9600

C13—O1—C17	117.13 (16)	C4—C7—H7	106.8
C12—O2—C18	117.82 (19)	C9—C8—C7	124.2 (2)
C2—C1—C6	111.0 (3)	C9—C8—H8	117.9
C2—C1—H1A	109.4	C7—C8—H8	117.9
C6—C1—H1A	109.4	C8—C9—C10	124.4 (2)
C2—C1—H1B	109.4	C8—C9—H9	117.8
C6—C1—H1B	109.4	C10—C9—H9	117.8
H1A—C1—H1B	108.0	C9—C10—C16	113.5 (2)
C1—C2—C3	111.7 (3)	C9—C10—H10A	108.9
C1—C2—H2A	109.3	C16—C10—H10A	108.9
C3—C2—H2A	109.3	C9—C10—H10B	108.9
C1—C2—H2B	109.3	C16—C10—H10B	108.9
C3—C2—H2B	109.3	H10A—C10—H10B	107.7
H2A—C2—H2B	107.9	C12—C11—C16	121.65 (18)
C2—C3—C4	111.1 (2)	C12—C11—H11	119.2
C2—C3—H3A	109.4	C16—C11—H11	119.2
C4—C3—H3A	109.4	C11—C12—O2	125.58 (18)
C2—C3—H3B	109.4	C11—C12—C13	119.05 (17)
C4—C3—H3B	109.4	O2—C12—C13	115.35 (16)
H3A—C3—H3B	108.0	O1—C13—C14	125.16 (16)
C5—C4—C3	109.39 (18)	O1—C13—C12	115.19 (15)
C5—C4—C7	113.54 (19)	C14—C13—C12	119.65 (16)
C3—C4—C7	114.01 (19)	C13—C14—C15	121.65 (17)
C5—C4—H4	106.4	C13—C14—H14	119.2
C3—C4—H4	106.4	C15—C14—H14	119.2
C7—C4—H4	106.4	C16—C15—C14	118.14 (17)
C4—C5—C6	110.9 (3)	C16—C15—C7	123.28 (18)
C4—C5—H5A	109.5	C14—C15—C7	118.58 (17)
C6—C5—H5A	109.5	C15—C16—C11	119.85 (17)
C4—C5—H5B	109.5	C15—C16—C10	121.5 (2)
C6—C5—H5B	109.5	C11—C16—C10	118.7 (2)
H5A—C5—H5B	108.0	O1—C17—H17A	109.5
C1—C6—C5	111.1 (3)	O1—C17—H17B	109.5
C1—C6—H6A	109.4	H17A—C17—H17B	109.5
C5—C6—H6A	109.4	O1—C17—H17C	109.5
C1—C6—H6B	109.4	H17A—C17—H17C	109.5
C5—C6—H6B	109.4	H17B—C17—H17C	109.5
H6A—C6—H6B	108.0	O2—C18—H18A	109.5
C15—C7—C8	110.8 (2)	O2—C18—H18B	109.5
C15—C7—C4	112.31 (16)	H18A—C18—H18B	109.5
C8—C7—C4	112.98 (18)	O2—C18—H18C	109.5
C15—C7—H7	106.8	H18A—C18—H18C	109.5
C8—C7—H7	106.8	H18B—C18—H18C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O2ⁱ	0.96	2.59	3.272 (3)	129

Symmetry code: (i) −x+2, y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O2ⁱ	0.96	2.59	3.272 (3)	129

Symmetry code: (i) −x+2, y+1/2, −z+1.

Acknowledgements

Diffraction data was collected at the Analytical Center of the Chemistry Department of Zhejiang University, China.

References

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