2-(1-Naphthyl)­cyclo­hexyl 3-furan­carboxyl­ate

The crystal structure of the title compound, C₂₁H₂₀O₃, contains mol­ecules separated by normal van der Waals distances. The cyclo­hexyl ring adopts a classical chair conformation, while the furan and naphthyl rings are individually planar. The molecular dimensions are as expected.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.053
• wR factor = 0.242
• Data-to-parameter ratio = 14.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSMU_01  Alert C The ratio of given/expected absorption coefficient lies
          outside the range 0.99 <> 1.01
          Calculated value of mu =     0.082
          Value of mu given      =     0.080


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

3-Furoate trans-2-arylcyclohexanol esters were prepared as model compounds as part of an investigation to create a chiral auxiliary for use in as asymmetric intramolecular Diels–Alder reaction with a furandiene (IMDAF reaction) (Keay & Hunt, 1999). Molecular modeling had suggested that such systems might be able to block one face of the furandiene. The model compound, 2-(1-naphthyl)cyclohexyl 3-furancarboxylate, (I), was prepared and the structure determined in order to verify the molecular modeling results.

The asymmetric unit of (I) is composed of molecules (Fig. 1) which are separated by normal van der Waals distances. The molecular dimensions are normal and lie within expected values for corresponding bond distances and angles (Orpen et al., 1994). The C1–C6 cyclohexyl ring adopts a classical chair conformation, with puckering parameters (Cremer & Pople, 1975) Q = 0.563 (6) Å, θ = 177.7 (6)° and ω = 123 (21)°. The naphthyl ring is essentially planar, with the maximum deviation of any atom from the mean plane being 0.027 (4) Å. The five-membered furan ring is also planar.

S2. Experimental

To a solution of 3-furoic acid (76 mg, 0.68 mmol) in dry methylene chloride (2.5 ml) and dry DMF (5 µl), oxalyl chloride (120 µl, 1.36 mmol) was added. The solution was refluxed overnight, then cooled and the solvent removed in vacuo. After redisolving the residue in dry methylene chloride (2.5 ml), a solution of trans-2-(1-naphthyl)cyclohexanol (136 mg, 0.9 equivalents) in dry methylene chloride (2 ml) was added followed by dry triethylamine (189 µl) and DMAP (9 mg). The reaction was stirred at room temperature for 36 h. After adding Et₂O (25 ml), the solution was washed with 5% HCl (10 ml) and water (20 ml), dried over MgSO₄, then filtered and evaporated in vacuo to give the crude product as an oil. Purification via a short column (silica gel, EtOAc) followed by radial chromatography (EtOAc hexanes, 20:1 to 5:1), gave recovered trans-2-(1-naphthyl)cyclohexanol (41 mg) and the title product (I) (135 mg) as a white crsytalline solid (m.p. 370 K).

S3. Refinement

The space group, P2₁/c, was uniquely determined from the systematic absences. Most of the H atoms were located from difference maps. The H atoms were included at geometrically idealized positions with C–H = 0.93–0.98 Å, in a riding mode with isotropic displacement parameters 1.2 times the displacement parameters of the atoms to which they were attached.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1994); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN; software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. ORTEPII (Johnson, 1976) drawing of (I). Displacement ellipsoids have been plotted at the 30% probability level.

2-(1-Naphthyl)cyclohexyl 3-furancarboxylate

Crystal data

C21H20O3	F(000) = 680
Mr = 320.37	Dx = 1.238 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
a = 9.1991 (11) Å	Cell parameters from 25 reflections
b = 7.3840 (5) Å	θ = 10.0–15.0°
c = 25.694 (3) Å	µ = 0.08 mm^−1
β = 100.030 (9)°	T = 296 K
V = 1718.6 (3) Å^3	Prism, colourless
Z = 4	0.40 × 0.30 × 0.24 mm

Data collection

Rigaku AFC-6S diffractometer	Rint = 0.08
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.5°
Graphite monochromator	h = 0→10
ω/2θ scans	k = 0→8
3245 measured reflections	l = −30→30
3043 independent reflections	3 standard reflections every 200 reflections
917 reflections with I > 2σ(I)	intensity decay: <0.1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.242	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.1064P)^2] where P = (Fo^2 + 2Fc^2)/3
3043 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.7451 (4)	0.0633 (5)	0.06785 (14)	0.0566 (11)
O2	0.9436 (5)	0.2165 (6)	0.05039 (17)	0.0816 (15)
O3	0.4958 (5)	0.3682 (6)	−0.04818 (16)	0.0707 (12)
C1	0.8382 (6)	−0.0498 (7)	0.1059 (2)	0.0501 (14)
H1	0.9229	0.0203	0.1238	0.060*
C2	0.7439 (6)	−0.1098 (7)	0.1459 (2)	0.0480 (14)
H2	0.6572	−0.1715	0.1262	0.058*
C3	0.8279 (7)	−0.2480 (8)	0.1842 (2)	0.0675 (18)
H3A	0.9110	−0.1886	0.2060	0.081*
H3B	0.7633	−0.2931	0.2073	0.081*
C4	0.8836 (7)	−0.4055 (9)	0.1558 (3)	0.078 (2)
H4A	0.9414	−0.4848	0.1816	0.093*
H4B	0.8000	−0.4742	0.1377	0.093*
C5	0.9774 (7)	−0.3459 (8)	0.1161 (3)	0.077 (2)
H5A	1.0051	−0.4506	0.0973	0.092*
H5B	1.0670	−0.2892	0.1344	0.092*
C6	0.8923 (6)	−0.2115 (8)	0.0767 (2)	0.0627 (17)
H6A	0.8083	−0.2720	0.0558	0.075*
H6B	0.9558	−0.1684	0.0529	0.075*
C7	0.8126 (7)	0.1888 (8)	0.0414 (2)	0.0545 (16)
C8	0.7050 (6)	0.2836 (7)	0.0023 (2)	0.0513 (14)
C9	0.7374 (7)	0.4234 (8)	−0.0320 (2)	0.0689 (18)
H9	0.8294	0.4740	−0.0332	0.083*
C10	0.6098 (9)	0.4669 (9)	−0.0619 (2)	0.0760 (19)
H10	0.5989	0.5531	−0.0887	0.091*
C11	0.5594 (7)	0.2571 (8)	−0.0082 (2)	0.0577 (15)
H11	0.5084	0.1746	0.0092	0.069*
C12	0.6878 (6)	0.0498 (7)	0.1748 (2)	0.0468 (14)
C13	0.5375 (6)	0.1068 (7)	0.1637 (2)	0.0446 (13)
C14	0.4291 (6)	0.0264 (8)	0.1265 (2)	0.0581 (15)
H14	0.4553	−0.0687	0.1062	0.070*
C15	0.2849 (7)	0.0826 (9)	0.1185 (3)	0.0761 (19)
H15	0.2152	0.0261	0.0931	0.091*
C16	0.2425 (7)	0.2252 (10)	0.1486 (3)	0.078 (2)
H16	0.1443	0.2614	0.1440	0.094*
C17	0.3437 (8)	0.3081 (8)	0.1837 (3)	0.0716 (19)
H17	0.3149	0.4055	0.2025	0.086*
C18	0.4943 (7)	0.2540 (7)	0.1937 (2)	0.0533 (15)
C19	0.5977 (9)	0.3431 (8)	0.2311 (2)	0.0701 (18)
H19	0.5690	0.4406	0.2498	0.084*
C20	0.7396 (9)	0.2873 (9)	0.2400 (2)	0.078 (2)
H20	0.8079	0.3452	0.2656	0.093*
C21	0.7853 (7)	0.1430 (8)	0.2113 (2)	0.0611 (16)
H21	0.8844	0.1101	0.2171	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.051 (2)	0.065 (3)	0.055 (2)	0.009 (2)	0.0110 (19)	0.009 (2)
O2	0.055 (3)	0.095 (4)	0.097 (4)	−0.006 (3)	0.020 (2)	0.026 (3)
O3	0.084 (3)	0.062 (3)	0.061 (3)	0.010 (3)	−0.003 (2)	0.005 (2)
C1	0.046 (3)	0.059 (4)	0.045 (3)	0.006 (3)	0.010 (3)	0.005 (3)
C2	0.046 (3)	0.052 (3)	0.046 (3)	0.003 (3)	0.008 (3)	−0.005 (3)
C3	0.077 (4)	0.059 (4)	0.074 (4)	0.017 (3)	0.032 (3)	0.013 (4)
C4	0.080 (4)	0.067 (4)	0.091 (5)	0.027 (4)	0.026 (4)	0.018 (4)
C5	0.071 (4)	0.069 (4)	0.100 (5)	0.020 (4)	0.039 (4)	0.011 (4)
C6	0.065 (4)	0.070 (4)	0.059 (4)	0.015 (3)	0.029 (3)	0.005 (3)
C7	0.064 (4)	0.055 (4)	0.050 (4)	0.000 (4)	0.024 (3)	0.000 (3)
C8	0.060 (4)	0.050 (4)	0.045 (3)	0.010 (3)	0.013 (3)	0.003 (3)
C9	0.074 (5)	0.074 (5)	0.064 (4)	0.009 (4)	0.027 (4)	0.010 (4)
C10	0.108 (6)	0.067 (4)	0.059 (5)	0.015 (5)	0.031 (4)	0.015 (4)
C11	0.075 (5)	0.049 (4)	0.047 (4)	0.006 (3)	0.005 (3)	0.006 (3)
C12	0.056 (4)	0.045 (3)	0.043 (3)	0.000 (3)	0.016 (3)	0.006 (3)
C13	0.052 (3)	0.043 (3)	0.041 (3)	−0.003 (3)	0.014 (3)	0.000 (3)
C14	0.055 (4)	0.061 (4)	0.059 (4)	0.005 (3)	0.012 (3)	0.001 (3)
C15	0.061 (4)	0.079 (5)	0.091 (5)	0.000 (4)	0.020 (4)	0.000 (4)
C16	0.059 (4)	0.080 (5)	0.101 (6)	0.017 (4)	0.031 (4)	0.010 (5)
C17	0.090 (5)	0.050 (4)	0.085 (5)	0.017 (4)	0.047 (4)	0.008 (4)
C18	0.072 (4)	0.043 (4)	0.053 (4)	0.007 (3)	0.031 (3)	0.006 (3)
C19	0.112 (6)	0.049 (4)	0.053 (4)	0.005 (4)	0.027 (4)	−0.007 (3)
C20	0.107 (6)	0.068 (5)	0.056 (4)	−0.009 (5)	0.006 (4)	−0.019 (4)
C21	0.066 (4)	0.063 (4)	0.052 (4)	−0.005 (4)	0.003 (3)	0.005 (4)

Geometric parameters (Å, º)

O1—C7	1.362 (6)	C8—C9	1.423 (7)
O1—C1	1.448 (6)	C9—C10	1.326 (8)
O2—C7	1.205 (6)	C9—H9	0.9300
O3—C11	1.364 (6)	C10—H10	0.9300
O3—C10	1.373 (7)	C11—H11	0.9300
C1—C2	1.520 (6)	C12—C21	1.365 (7)
C1—C6	1.539 (7)	C12—C13	1.426 (7)
C1—H1	0.9800	C13—C14	1.390 (7)
C2—C3	1.531 (7)	C13—C18	1.428 (7)
C2—C12	1.530 (7)	C14—C15	1.371 (7)
C2—H2	0.9800	C14—H14	0.9300
C3—C4	1.509 (8)	C15—C16	1.401 (8)
C3—H3A	0.9700	C15—H15	0.9300
C3—H3B	0.9700	C16—C17	1.328 (8)
C4—C5	1.511 (7)	C16—H16	0.9300
C4—H4A	0.9700	C17—C18	1.421 (8)
C4—H4B	0.9700	C17—H17	0.9300
C5—C6	1.532 (7)	C18—C19	1.394 (8)
C5—H5A	0.9700	C19—C20	1.350 (8)
C5—H5B	0.9700	C19—H19	0.9300
C6—H6A	0.9700	C20—C21	1.403 (8)
C6—H6B	0.9700	C20—H20	0.9300
C7—C8	1.459 (8)	C21—H21	0.9300
C8—C11	1.334 (7)
C7—O1—C1	117.6 (4)	C11—C8—C7	127.3 (6)
C11—O3—C10	105.5 (5)	C9—C8—C7	125.7 (6)
O1—C1—C2	106.5 (4)	C10—C9—C8	106.0 (6)
O1—C1—C6	108.7 (4)	C10—C9—H9	127.0
C2—C1—C6	112.0 (4)	C8—C9—H9	127.0
O1—C1—H1	109.8	C9—C10—O3	111.2 (6)
C2—C1—H1	109.8	C9—C10—H10	124.4
C6—C1—H1	109.8	O3—C10—H10	124.4
C1—C2—C3	110.2 (4)	C8—C11—O3	110.4 (5)
C1—C2—C12	112.6 (4)	C8—C11—H11	124.8
C3—C2—C12	112.1 (4)	O3—C11—H11	124.8
C1—C2—H2	107.2	C21—C12—C13	119.1 (5)
C3—C2—H2	107.2	C21—C12—C2	119.0 (5)
C12—C2—H2	107.2	C13—C12—C2	121.9 (5)
C4—C3—C2	112.3 (5)	C14—C13—C12	124.5 (5)
C4—C3—H3A	109.1	C14—C13—C18	117.6 (5)
C2—C3—H3A	109.1	C12—C13—C18	118.0 (5)
C4—C3—H3B	109.1	C15—C14—C13	122.2 (6)
C2—C3—H3B	109.1	C15—C14—H14	118.9
H3A—C3—H3B	107.9	C13—C14—H14	118.9
C5—C4—C3	112.5 (5)	C14—C15—C16	120.0 (7)
C5—C4—H4A	109.1	C14—C15—H15	120.0
C3—C4—H4A	109.1	C16—C15—H15	120.0
C5—C4—H4B	109.1	C17—C16—C15	119.5 (6)
C3—C4—H4B	109.1	C17—C16—H16	120.3
H4A—C4—H4B	107.8	C15—C16—H16	120.3
C4—C5—C6	110.4 (5)	C16—C17—C18	122.6 (6)
C4—C5—H5A	109.6	C16—C17—H17	118.7
C6—C5—H5A	109.6	C18—C17—H17	118.7
C4—C5—H5B	109.6	C19—C18—C17	121.2 (6)
C6—C5—H5B	109.6	C19—C18—C13	120.7 (6)
H5A—C5—H5B	108.1	C17—C18—C13	118.1 (6)
C5—C6—C1	110.6 (4)	C20—C19—C18	119.8 (6)
C5—C6—H6A	109.5	C20—C19—H19	120.1
C1—C6—H6A	109.5	C18—C19—H19	120.1
C5—C6—H6B	109.5	C19—C20—C21	120.8 (6)
C1—C6—H6B	109.5	C19—C20—H20	119.6
H6A—C6—H6B	108.1	C21—C20—H20	119.6
O2—C7—O1	123.2 (6)	C12—C21—C20	121.6 (6)
O2—C7—C8	125.9 (6)	C12—C21—H21	119.2
O1—C7—C8	110.9 (5)	C20—C21—H21	119.2
C11—C8—C9	107.0 (5)
C7—O1—C1—C2	154.5 (4)	C1—C2—C12—C21	−71.7 (6)
C7—O1—C1—C6	−84.6 (5)	C3—C2—C12—C21	53.2 (6)
O1—C1—C2—C3	173.5 (4)	C1—C2—C12—C13	106.6 (5)
C6—C1—C2—C3	54.7 (6)	C3—C2—C12—C13	−128.5 (5)
O1—C1—C2—C12	−60.6 (5)	C21—C12—C13—C14	178.1 (5)
C6—C1—C2—C12	−179.3 (4)	C2—C12—C13—C14	−0.2 (8)
C1—C2—C3—C4	−53.7 (7)	C21—C12—C13—C18	−3.4 (7)
C12—C2—C3—C4	−179.9 (5)	C2—C12—C13—C18	178.3 (4)
C2—C3—C4—C5	55.0 (7)	C12—C13—C14—C15	177.8 (5)
C3—C4—C5—C6	−55.5 (7)	C18—C13—C14—C15	−0.8 (8)
C4—C5—C6—C1	55.5 (7)	C13—C14—C15—C16	−0.2 (9)
O1—C1—C6—C5	−173.9 (4)	C14—C15—C16—C17	1.8 (10)
C2—C1—C6—C5	−56.4 (6)	C15—C16—C17—C18	−2.4 (10)
C1—O1—C7—O2	−4.5 (8)	C16—C17—C18—C19	−179.5 (6)
C1—O1—C7—C8	176.5 (4)	C16—C17—C18—C13	1.4 (9)
O2—C7—C8—C11	−179.3 (6)	C14—C13—C18—C19	−178.8 (6)
O1—C7—C8—C11	−0.3 (8)	C12—C13—C18—C19	2.5 (7)
O2—C7—C8—C9	0.7 (9)	C14—C13—C18—C17	0.2 (7)
O1—C7—C8—C9	179.7 (5)	C12—C13—C18—C17	−178.4 (5)
C11—C8—C9—C10	−2.0 (6)	C17—C18—C19—C20	179.4 (6)
C7—C8—C9—C10	178.0 (6)	C13—C18—C19—C20	−1.6 (9)
C8—C9—C10—O3	1.8 (7)	C18—C19—C20—C21	1.5 (10)
C11—O3—C10—C9	−0.9 (7)	C13—C12—C21—C20	3.4 (8)
C9—C8—C11—O3	1.5 (6)	C2—C12—C21—C20	−178.2 (5)
C7—C8—C11—O3	−178.5 (5)	C19—C20—C21—C12	−2.5 (9)
C10—O3—C11—C8	−0.4 (6)