2-Phenyl­cyclo­hexyl 3-furan­carboxyl­ate

The crystal structure of the title compound, C₁₇H₁₈O₃, contains mol­ecules that are separated by normal van der Waals distances. The cyclo­hexyl ring adopts a classical chair conformation, while the furan and phenyl rings are individually planar. The molecular dimensions are as expected.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.050
• wR factor = 0.221
• Data-to-parameter ratio = 13.9

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 =     0.086
          Value of mu given      =     0.090


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

The intramolecular Diels–Alder reaction with a furandiene (IMDAF reaction) is a useful reaction for the creation of three rings with up to five stereogenic centers in one reaction (Keay & Hunt, 1999). To date, no-one has reported an asymmetric version of this reaction. trans-2-Arylcyclohexanol esters of 3-furoic acid were prepared as potential chiral auxiliaries for studying the asymmetric IMDAF reaction. AM1 calculations indicated that the large aryl ring would preferentially block one face of the furandiene thereby leading to high diastereoselectivity in the IMDAF reaction. The structure of 2-phenylcyclohexyl 3-furancarboxylate, (I), was obtained to determine if in the solid state, the large aryl ring would block one face of the furan ring.

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 = 0.568 (5) Å, θ = 177.3 (5)° and ω = 55 (9)°. The phenyl ring is essentially planar with the maximum deviation of any atom from the mean plane being 0.007 (3) Å. The five-membered furan ring is also planar. The structure is devoid of any unwanted interactions.

S2. Experimental

To a mixture of 3-furoic acid (111 mg, 0.99 mmol) in dry methylene chloride (2 ml) and dry DMF (5 µl) at 273 K under a nitrogen atmosphere, oxalyl chloride (86 µl, 1.1 equivalents) was added. The solution was stirred at 273 K for 15 min, then at room temperature for 3 h. after which the solvent was removed in vacuo. After redissolving the residue in dry methylene chloride (2 ml), a solution of trans-2-phenylcyclohexanol (164 mg, 0.93 mmol) in dry methylene chloride (2 ml) was added followed by dry pyridine (80 µl). The reaction mixture was stirred at room temperature overnight. After adding CH₂Cl₂ (20 ml), the solution was washed with 5% HCl (25 ml). Et₂O (20 ml) was added, then the organic phase was washed with water (25 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, 7:1) gave the desired ester, (I).

S3. Refinement

The space group, P21/n, 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 = 0.95–1.00 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 50% probability level.

2-Phenyl-cyclohexyl-3-furan carboxylate

Crystal data

C17H18O3	F(000) = 576
Mr = 270.31	Dx = 1.266 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
a = 5.5332 (11) Å	Cell parameters from 25 reflections
b = 12.841 (2) Å	θ = 10.0–15.0°
c = 20.088 (3) Å	µ = 0.09 mm^−1
β = 96.52 (2)°	T = 200 K
V = 1418.1 (4) Å^3	Block, colourless
Z = 4	0.50 × 0.40 × 0.22 mm

Data collection

Rigaku AFC-6S diffractometer	Rint = 0.06
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.0°
Graphite monochromator	h = 0→6
ω/2θ scans	k = 0→15
2796 measured reflections	l = −23→23
2520 independent reflections	3 standard reflections every 200 reflections
1156 reflections with I > 2σ(I)	intensity decay: <1.0%

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.221	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.12P)^2 + 0.066P] where P = (Fo^2 + 2Fc^2)/3
2520 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.0682 (5)	0.06778 (19)	0.83568 (13)	0.0382 (7)
O2	−0.3129 (5)	0.0041 (3)	0.83018 (16)	0.0593 (9)
O3	0.2568 (6)	−0.1239 (2)	0.99418 (14)	0.0481 (8)
C1	0.0150 (7)	0.1301 (3)	0.77534 (18)	0.0332 (9)
H1	−0.1455	0.1658	0.7755	0.040*
C2	0.2193 (7)	0.2100 (3)	0.77882 (19)	0.0333 (9)
H2	0.3764	0.1708	0.7841	0.040*
C3	0.2088 (9)	0.2716 (3)	0.7130 (2)	0.0442 (11)
H3A	0.0614	0.3159	0.7082	0.053*
H3B	0.3525	0.3179	0.7146	0.053*
C4	0.2040 (9)	0.1998 (3)	0.6523 (2)	0.0494 (12)
H4A	0.1882	0.2420	0.6108	0.059*
H4B	0.3591	0.1608	0.6546	0.059*
C5	−0.0062 (9)	0.1235 (4)	0.6498 (2)	0.0489 (12)
H5A	−0.0023	0.0762	0.6111	0.059*
H5B	−0.1622	0.1620	0.6441	0.059*
C6	0.0118 (9)	0.0602 (3)	0.7144 (2)	0.0449 (11)
H6A	−0.1286	0.0121	0.7129	0.054*
H6B	0.1621	0.0177	0.7181	0.054*
C7	−0.1048 (7)	0.0057 (3)	0.8557 (2)	0.0354 (9)
C8	−0.0029 (7)	−0.0590 (3)	0.91227 (19)	0.0326 (9)
C9	−0.1248 (8)	−0.1363 (3)	0.9471 (2)	0.0397 (10)
H9	−0.2898	−0.1572	0.9377	0.048*
C10	0.0374 (9)	−0.1733 (3)	0.9952 (2)	0.0458 (11)
H10	0.0058	−0.2265	1.0260	0.055*
C11	0.2246 (8)	−0.0548 (3)	0.9426 (2)	0.0402 (10)
H11	0.3473	−0.0097	0.9299	0.048*
C12	0.2197 (7)	0.2814 (3)	0.83913 (18)	0.0317 (9)
C13	0.0344 (8)	0.3531 (3)	0.8442 (2)	0.0419 (10)
H13	−0.0974	0.3569	0.8096	0.050*
C14	0.0389 (9)	0.4192 (3)	0.8990 (2)	0.0498 (12)
H14	−0.0884	0.4683	0.9011	0.060*
C15	0.2262 (8)	0.4144 (3)	0.9505 (2)	0.0480 (11)
H15	0.2285	0.4594	0.9881	0.058*
C16	0.4103 (9)	0.3429 (3)	0.9462 (2)	0.0491 (12)
H16	0.5412	0.3390	0.9810	0.059*
C17	0.4059 (8)	0.2769 (3)	0.8917 (2)	0.0408 (10)
H17	0.5328	0.2275	0.8901	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0383 (16)	0.0351 (15)	0.0405 (17)	−0.0050 (13)	0.0013 (12)	0.0112 (13)
O2	0.0345 (17)	0.070 (2)	0.071 (2)	−0.0095 (16)	−0.0020 (15)	0.0271 (19)
O3	0.0524 (19)	0.0453 (17)	0.0461 (18)	0.0052 (15)	0.0037 (14)	0.0131 (14)
C1	0.034 (2)	0.033 (2)	0.033 (2)	0.0014 (17)	0.0058 (17)	0.0055 (18)
C2	0.035 (2)	0.031 (2)	0.034 (2)	0.0028 (17)	0.0066 (17)	0.0039 (18)
C3	0.059 (3)	0.037 (2)	0.039 (2)	−0.007 (2)	0.011 (2)	0.003 (2)
C4	0.064 (3)	0.047 (3)	0.040 (3)	−0.004 (2)	0.014 (2)	0.003 (2)
C5	0.064 (3)	0.051 (3)	0.033 (2)	−0.004 (2)	0.010 (2)	−0.004 (2)
C6	0.060 (3)	0.032 (2)	0.043 (3)	−0.006 (2)	0.008 (2)	0.0003 (19)
C7	0.031 (2)	0.033 (2)	0.044 (2)	−0.0026 (18)	0.0084 (18)	0.0005 (19)
C8	0.037 (2)	0.029 (2)	0.033 (2)	0.0020 (18)	0.0085 (17)	−0.0001 (17)
C9	0.042 (2)	0.033 (2)	0.046 (2)	0.002 (2)	0.013 (2)	0.0053 (19)
C10	0.057 (3)	0.039 (2)	0.044 (3)	0.003 (2)	0.019 (2)	0.009 (2)
C11	0.047 (3)	0.034 (2)	0.040 (2)	0.0020 (19)	0.0061 (19)	0.0080 (19)
C12	0.038 (2)	0.0247 (19)	0.034 (2)	−0.0023 (17)	0.0092 (18)	0.0052 (17)
C13	0.045 (2)	0.040 (2)	0.039 (2)	0.005 (2)	0.0000 (19)	0.001 (2)
C14	0.058 (3)	0.041 (3)	0.053 (3)	0.011 (2)	0.015 (2)	0.003 (2)
C15	0.060 (3)	0.044 (2)	0.041 (3)	−0.004 (2)	0.011 (2)	−0.004 (2)
C16	0.052 (3)	0.054 (3)	0.039 (3)	−0.005 (2)	−0.003 (2)	−0.005 (2)
C17	0.037 (2)	0.041 (2)	0.044 (2)	0.000 (2)	0.0040 (19)	0.005 (2)

Geometric parameters (Å, º)

O1—C7	1.342 (5)	C6—H6A	0.9900
O1—C1	1.454 (4)	C6—H6B	0.9900
O2—C7	1.207 (5)	C7—C8	1.467 (5)
O3—C11	1.360 (5)	C8—C11	1.336 (6)
O3—C10	1.372 (5)	C8—C9	1.428 (5)
C1—C6	1.517 (6)	C9—C10	1.330 (6)
C1—C2	1.523 (6)	C9—H9	0.9500
C1—H1	1.0000	C10—H10	0.9500
C2—C12	1.519 (5)	C11—H11	0.9500
C2—C3	1.537 (5)	C12—C17	1.390 (5)
C2—H2	1.0000	C12—C13	1.390 (5)
C3—C4	1.527 (6)	C13—C14	1.389 (6)
C3—H3A	0.9900	C13—H13	0.9500
C3—H3B	0.9900	C14—C15	1.380 (6)
C4—C5	1.517 (6)	C14—H14	0.9500
C4—H4A	0.9900	C15—C16	1.382 (6)
C4—H4B	0.9900	C15—H15	0.9500
C5—C6	1.524 (6)	C16—C17	1.382 (6)
C5—H5A	0.9900	C16—H16	0.9500
C5—H5B	0.9900	C17—H17	0.9500
C7—O1—C1	119.5 (3)	C5—C6—H6B	109.4
C11—O3—C10	105.9 (3)	H6A—C6—H6B	108.0
O1—C1—C6	109.3 (3)	O2—C7—O1	124.2 (4)
O1—C1—C2	104.7 (3)	O2—C7—C8	125.7 (4)
C6—C1—C2	112.1 (3)	O1—C7—C8	110.1 (3)
O1—C1—H1	110.2	C11—C8—C9	106.1 (4)
C6—C1—H1	110.2	C11—C8—C7	126.1 (4)
C2—C1—H1	110.2	C9—C8—C7	127.7 (4)
C12—C2—C1	112.2 (3)	C10—C9—C8	106.7 (4)
C12—C2—C3	111.8 (3)	C10—C9—H9	126.6
C1—C2—C3	110.6 (3)	C8—C9—H9	126.6
C12—C2—H2	107.3	C9—C10—O3	110.4 (4)
C1—C2—H2	107.3	C9—C10—H10	124.8
C3—C2—H2	107.3	O3—C10—H10	124.8
C4—C3—C2	111.8 (3)	C8—C11—O3	110.9 (4)
C4—C3—H3A	109.3	C8—C11—H11	124.5
C2—C3—H3A	109.3	O3—C11—H11	124.5
C4—C3—H3B	109.3	C17—C12—C13	117.5 (4)
C2—C3—H3B	109.3	C17—C12—C2	121.0 (4)
H3A—C3—H3B	107.9	C13—C12—C2	121.6 (4)
C5—C4—C3	111.1 (4)	C12—C13—C14	121.1 (4)
C5—C4—H4A	109.4	C12—C13—H13	119.5
C3—C4—H4A	109.4	C14—C13—H13	119.5
C5—C4—H4B	109.4	C15—C14—C13	120.8 (4)
C3—C4—H4B	109.4	C15—C14—H14	119.6
H4A—C4—H4B	108.0	C13—C14—H14	119.6
C4—C5—C6	110.0 (4)	C14—C15—C16	118.6 (4)
C4—C5—H5A	109.7	C14—C15—H15	120.7
C6—C5—H5A	109.7	C16—C15—H15	120.7
C4—C5—H5B	109.7	C15—C16—C17	120.7 (4)
C6—C5—H5B	109.7	C15—C16—H16	119.7
H5A—C5—H5B	108.2	C17—C16—H16	119.7
C1—C6—C5	111.4 (3)	C16—C17—C12	121.4 (4)
C1—C6—H6A	109.4	C16—C17—H17	119.3
C5—C6—H6A	109.4	C12—C17—H17	119.3
C1—C6—H6B	109.4
C7—O1—C1—C6	−74.8 (4)	C11—C8—C9—C10	−0.4 (5)
C7—O1—C1—C2	164.9 (3)	C7—C8—C9—C10	−178.9 (4)
O1—C1—C2—C12	−62.7 (4)	C8—C9—C10—O3	0.6 (5)
C6—C1—C2—C12	178.9 (3)	C11—O3—C10—C9	−0.6 (5)
O1—C1—C2—C3	171.6 (3)	C9—C8—C11—O3	0.1 (5)
C6—C1—C2—C3	53.3 (4)	C7—C8—C11—O3	178.6 (4)
C12—C2—C3—C4	−179.0 (4)	C10—O3—C11—C8	0.3 (5)
C1—C2—C3—C4	−53.2 (5)	C1—C2—C12—C17	111.8 (4)
C2—C3—C4—C5	56.0 (5)	C3—C2—C12—C17	−123.2 (4)
C3—C4—C5—C6	−57.4 (5)	C1—C2—C12—C13	−67.8 (4)
O1—C1—C6—C5	−171.7 (3)	C3—C2—C12—C13	57.2 (5)
C2—C1—C6—C5	−56.1 (5)	C17—C12—C13—C14	1.5 (6)
C4—C5—C6—C1	57.4 (5)	C2—C12—C13—C14	−178.9 (4)
C1—O1—C7—O2	−6.8 (6)	C12—C13—C14—C15	−1.0 (6)
C1—O1—C7—C8	172.9 (3)	C13—C14—C15—C16	0.5 (7)
O2—C7—C8—C11	−177.2 (4)	C14—C15—C16—C17	−0.5 (7)
O1—C7—C8—C11	3.1 (6)	C15—C16—C17—C12	1.1 (7)
O2—C7—C8—C9	1.0 (7)	C13—C12—C17—C16	−1.6 (6)
O1—C7—C8—C9	−178.6 (3)	C2—C12—C17—C16	178.8 (4)