2-(1-Naphthyl)­cyclo­hexyl 2-methyl­furan-3-carboxyl­ate

The crystal structure of the title compound, C₂₂H₂₂O₃, contains mol­ecules that are 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 = 200 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.042
• wR factor = 0.146
• Data-to-parameter ratio = 14.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

In our continuing study to develop an asymmetric version of an intramolecular Diels–Alder reaction with a furan diene (IMDAF; Keay & Hunt, 1999), we required the synthesis of a variety of 3-furoate trans-2-arylcyclohexanol esters. AM1 calculations had indicated that the aryl group should block one face of the furan diene and we hoped an X-ray crystal structure would verify this observation. Thus, the structure of 2-(1-naphthyl)cyclohexyl 2-methylfuran-3-carboxylate, (I), was determined and is presented here.

The asymmetric unit of (I) is composed of molecules (Fig. 1) that 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 = 0.574 (3) Å, θ = 1.3 (3)° and ω = 246 (11)°. The naphthyl ring is essentially planar, with the maximum deviation of any atom from the mean plane being 0.034 (3) Å. The five-membered furan ring is also planar. The structure is devoid of any unwanted interactions.

S2. Experimental

A mixture of trans-2-(1-naphthyl)cyclohexanol (50 mg, 0.22 mmol), distilled 2-methyl-3-furoic acid (28 mg, 0.22 mmol), DCC (50 mg, 1.1 eq.), DMAP (3 mg, 10 mol%) and PPTS (3 mg, 5 mol%) in dry CH₂Cl₂ (1 ml) was stirred at room temperature under a nitrogen atmosphere for 48 h. After adding more CH₂Cl₂, the mixture was filtered through a silica pad, then washed with 5% HCl (10 ml). The organic phase was dried over MgSO₄, then filtered and the solvent removed in vacuo to give the title compound, (I), in the form of an oil that crystallized on standing in the freezer. X-ray quality crystals of (I) were grown from hexane.

S3. Refinement

The space group, C2/c, was determined from the systematic absences, packing considerations, a statistical analysis of intensity distribution, and the successful solution and refinement of the structure. 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 (non-methyl) and 1.5 (methyl) times the displacement parameters of the atoms to which they were attached and a torsional parameter was refined for the methyl group.

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 30% probability level.

2-(1-Naphthyl)cyclohexyl 2-methylfuran-3-carboxylate

Crystal data

C22H22O3	F(000) = 1424
Mr = 334.40	Dx = 1.226 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
a = 21.774 (3) Å	Cell parameters from 25 reflections
b = 10.694 (2) Å	θ = 10.0–15.0°
c = 18.430 (3) Å	µ = 0.08 mm^−1
β = 122.38 (1)°	T = 200 K
V = 3624.2 (10) Å^3	Prism, colourless
Z = 8	0.60 × 0.50 × 0.30 mm

Data collection

Rigaku AFC-6S diffractometer	Rint = 0.03
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.0°
Graphite monochromator	h = −25→0
ω/2θ scans	k = −12→0
3299 measured reflections	l = −18→21
3209 independent reflections	3 standard reflections every 200 reflections
1641 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 3.6P] where P = (Fo^2 + 2Fc^2)/3
3209 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.76460 (9)	0.11775 (17)	0.15624 (11)	0.0427 (5)
O2	0.71292 (13)	0.2932 (2)	0.08131 (16)	0.0777 (8)
O3	0.61344 (11)	0.2904 (2)	0.22661 (13)	0.0594 (6)
C1	0.79839 (13)	0.0913 (3)	0.10733 (16)	0.0401 (6)
H1	0.7835	0.1563	0.0619	0.048*
C2	0.77027 (13)	−0.0360 (2)	0.06563 (17)	0.0390 (6)
H2	0.7825	−0.0975	0.1124	0.047*
C3	0.80990 (15)	−0.0776 (3)	0.0212 (2)	0.0510 (8)
H3A	0.7943	−0.1634	−0.0015	0.061*
H3B	0.7961	−0.0214	−0.0280	0.061*
C4	0.89192 (16)	−0.0752 (3)	0.0824 (2)	0.0605 (9)
H4A	0.9155	−0.0981	0.0508	0.073*
H4B	0.9064	−0.1377	0.1285	0.073*
C5	0.91750 (15)	0.0536 (3)	0.1219 (2)	0.0598 (9)
H5A	0.9064	0.1149	0.0762	0.072*
H5B	0.9708	0.0524	0.1629	0.072*
C6	0.88031 (14)	0.0938 (3)	0.16883 (18)	0.0531 (8)
H6A	0.8945	0.0366	0.2176	0.064*
H6B	0.8961	0.1794	0.1920	0.064*
C7	0.72108 (15)	0.2171 (3)	0.13420 (18)	0.0456 (7)
C8	0.68445 (14)	0.2217 (3)	0.18200 (17)	0.0432 (7)
C9	0.68719 (16)	0.1332 (3)	0.24209 (18)	0.0503 (8)
H9	0.7142	0.0575	0.2607	0.060*
C10	0.64408 (18)	0.1790 (3)	0.2666 (2)	0.0610 (9)
H10	0.6357	0.1394	0.3067	0.073*
C11	0.63911 (15)	0.3154 (3)	0.17480 (18)	0.0482 (7)
C12	0.68788 (14)	−0.0346 (2)	0.00508 (17)	0.0399 (7)
C13	0.64089 (14)	−0.0970 (2)	0.02578 (18)	0.0419 (7)
C14	0.66574 (16)	−0.1618 (3)	0.10426 (19)	0.0506 (8)
H14	0.7164	−0.1652	0.1461	0.061*
C15	0.61867 (18)	−0.2190 (3)	0.1210 (2)	0.0637 (9)
H15	0.6370	−0.2622	0.1738	0.076*
C16	0.5437 (2)	−0.2149 (3)	0.0614 (3)	0.0744 (11)
H16	0.5112	−0.2550	0.0735	0.089*
C17	0.51761 (17)	−0.1532 (3)	−0.0140 (3)	0.0684 (10)
H17	0.4666	−0.1508	−0.0543	0.082*
C18	0.56435 (15)	−0.0922 (3)	−0.0345 (2)	0.0509 (8)
C19	0.53692 (17)	−0.0240 (3)	−0.1119 (2)	0.0645 (9)
H19	0.4860	−0.0216	−0.1526	0.077*
C20	0.58241 (17)	0.0379 (3)	−0.1288 (2)	0.0606 (9)
H20	0.5633	0.0850	−0.1802	0.073*
C21	0.65772 (15)	0.0317 (3)	−0.06973 (18)	0.0486 (7)
H21	0.6890	0.0753	−0.0823	0.058*
C22	0.61128 (19)	0.4317 (3)	0.1234 (2)	0.0683 (10)
H22A	0.5581	0.4326	0.0922	0.102*
H22B	0.6266	0.4350	0.0822	0.102*
H22C	0.6307	0.5043	0.1617	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0438 (11)	0.0513 (12)	0.0363 (10)	0.0029 (9)	0.0236 (9)	0.0029 (9)
O2	0.0985 (19)	0.0738 (16)	0.1021 (19)	0.0348 (14)	0.0812 (17)	0.0409 (15)
O3	0.0728 (14)	0.0629 (15)	0.0640 (14)	−0.0122 (12)	0.0509 (13)	−0.0122 (12)
C1	0.0368 (15)	0.0498 (17)	0.0374 (15)	−0.0009 (13)	0.0223 (13)	0.0028 (13)
C2	0.0356 (14)	0.0409 (16)	0.0417 (15)	0.0036 (12)	0.0216 (13)	0.0066 (13)
C3	0.0459 (17)	0.0499 (18)	0.064 (2)	0.0077 (14)	0.0343 (16)	0.0016 (15)
C4	0.0466 (18)	0.073 (2)	0.072 (2)	0.0170 (16)	0.0385 (18)	0.0200 (18)
C5	0.0336 (16)	0.091 (3)	0.0552 (19)	−0.0025 (16)	0.0242 (15)	0.0083 (18)
C6	0.0366 (16)	0.072 (2)	0.0460 (17)	−0.0087 (15)	0.0191 (14)	0.0024 (16)
C7	0.0417 (16)	0.0517 (18)	0.0454 (17)	−0.0030 (14)	0.0246 (14)	0.0032 (15)
C8	0.0411 (16)	0.0502 (17)	0.0409 (16)	−0.0084 (13)	0.0236 (14)	−0.0049 (14)
C9	0.0523 (18)	0.0552 (19)	0.0473 (17)	−0.0085 (15)	0.0293 (15)	−0.0017 (15)
C10	0.073 (2)	0.067 (2)	0.058 (2)	−0.0197 (18)	0.0449 (19)	−0.0061 (18)
C11	0.0530 (18)	0.0537 (19)	0.0477 (18)	−0.0102 (15)	0.0334 (15)	−0.0097 (15)
C12	0.0368 (15)	0.0391 (16)	0.0432 (16)	0.0016 (12)	0.0210 (13)	−0.0050 (13)
C13	0.0370 (15)	0.0357 (15)	0.0544 (18)	−0.0001 (12)	0.0253 (14)	−0.0086 (13)
C14	0.0470 (17)	0.0477 (18)	0.064 (2)	0.0008 (14)	0.0340 (16)	0.0024 (16)
C15	0.062 (2)	0.058 (2)	0.085 (2)	−0.0054 (17)	0.049 (2)	0.0032 (18)
C16	0.068 (2)	0.062 (2)	0.118 (3)	−0.0148 (19)	0.067 (3)	−0.010 (2)
C17	0.0399 (18)	0.064 (2)	0.099 (3)	−0.0123 (17)	0.0360 (19)	−0.023 (2)
C18	0.0369 (16)	0.0470 (18)	0.065 (2)	−0.0039 (14)	0.0250 (15)	−0.0163 (16)
C19	0.0358 (17)	0.072 (2)	0.062 (2)	0.0029 (17)	0.0106 (16)	−0.0142 (19)
C20	0.0495 (19)	0.071 (2)	0.0471 (18)	0.0051 (17)	0.0166 (16)	−0.0026 (17)
C21	0.0427 (17)	0.0549 (19)	0.0442 (17)	0.0021 (14)	0.0206 (14)	0.0011 (14)
C22	0.083 (2)	0.060 (2)	0.082 (2)	0.0086 (18)	0.057 (2)	0.0025 (19)

Geometric parameters (Å, º)

O1—C7	1.334 (3)	C9—C10	1.334 (4)
O1—C1	1.464 (3)	C9—H9	0.9500
O2—C7	1.208 (3)	C10—H10	0.9500
O3—C11	1.367 (3)	C11—C22	1.482 (4)
O3—C10	1.372 (4)	C12—C21	1.365 (4)
C1—C6	1.517 (3)	C12—C13	1.434 (4)
C1—C2	1.521 (4)	C13—C14	1.424 (4)
C1—H1	1.0000	C13—C18	1.425 (4)
C2—C12	1.523 (4)	C14—C15	1.363 (4)
C2—C3	1.539 (3)	C14—H14	0.9500
C2—H2	1.0000	C15—C16	1.398 (5)
C3—C4	1.518 (4)	C15—H15	0.9500
C3—H3A	0.9900	C16—C17	1.358 (5)
C3—H3B	0.9900	C16—H16	0.9500
C4—C5	1.519 (4)	C17—C18	1.419 (4)
C4—H4A	0.9900	C17—H17	0.9500
C4—H4B	0.9900	C18—C19	1.418 (4)
C5—C6	1.529 (4)	C19—C20	1.358 (4)
C5—H5A	0.9900	C19—H19	0.9500
C5—H5B	0.9900	C20—C21	1.402 (4)
C6—H6A	0.9900	C20—H20	0.9500
C6—H6B	0.9900	C21—H21	0.9500
C7—C8	1.472 (4)	C22—H22A	0.9800
C8—C11	1.362 (4)	C22—H22B	0.9800
C8—C9	1.433 (4)	C22—H22C	0.9800
C7—O1—C1	118.4 (2)	C10—C9—H9	127.0
C11—O3—C10	106.4 (2)	C8—C9—H9	127.0
O1—C1—C6	108.3 (2)	C9—C10—O3	111.4 (3)
O1—C1—C2	106.6 (2)	C9—C10—H10	124.3
C6—C1—C2	112.8 (2)	O3—C10—H10	124.3
O1—C1—H1	109.7	C8—C11—O3	109.5 (3)
C6—C1—H1	109.7	C8—C11—C22	134.9 (3)
C2—C1—H1	109.7	O3—C11—C22	115.5 (3)
C1—C2—C12	111.0 (2)	C21—C12—C13	119.0 (2)
C1—C2—C3	109.8 (2)	C21—C12—C2	119.1 (2)
C12—C2—C3	112.9 (2)	C13—C12—C2	121.9 (2)
C1—C2—H2	107.6	C14—C13—C18	117.3 (3)
C12—C2—H2	107.7	C14—C13—C12	124.0 (2)
C3—C2—H2	107.6	C18—C13—C12	118.6 (3)
C4—C3—C2	111.8 (3)	C15—C14—C13	121.7 (3)
C4—C3—H3A	109.2	C15—C14—H14	119.1
C2—C3—H3A	109.2	C13—C14—H14	119.1
C4—C3—H3B	109.2	C14—C15—C16	120.7 (3)
C2—C3—H3B	109.2	C14—C15—H15	119.6
H3A—C3—H3B	107.9	C16—C15—H15	119.6
C3—C4—C5	110.8 (3)	C17—C16—C15	119.5 (3)
C3—C4—H4A	109.5	C17—C16—H16	120.3
C5—C4—H4A	109.5	C15—C16—H16	120.3
C3—C4—H4B	109.5	C16—C17—C18	121.9 (3)
C5—C4—H4B	109.5	C16—C17—H17	119.0
H4A—C4—H4B	108.1	C18—C17—H17	119.0
C4—C5—C6	111.0 (3)	C19—C18—C17	121.9 (3)
C4—C5—H5A	109.4	C19—C18—C13	119.3 (3)
C6—C5—H5A	109.4	C17—C18—C13	118.8 (3)
C4—C5—H5B	109.4	C20—C19—C18	121.0 (3)
C6—C5—H5B	109.4	C20—C19—H19	119.5
H5A—C5—H5B	108.0	C18—C19—H19	119.5
C1—C6—C5	109.8 (2)	C19—C20—C21	119.5 (3)
C1—C6—H6A	109.7	C19—C20—H20	120.2
C5—C6—H6A	109.7	C21—C20—H20	120.2
C1—C6—H6B	109.7	C12—C21—C20	122.6 (3)
C5—C6—H6B	109.7	C12—C21—H21	118.7
H6A—C6—H6B	108.2	C20—C21—H21	118.7
O2—C7—O1	123.8 (3)	C11—C22—H22A	109.5
O2—C7—C8	124.6 (3)	C11—C22—H22B	109.5
O1—C7—C8	111.6 (2)	H22A—C22—H22B	109.5
C11—C8—C9	106.8 (2)	C11—C22—H22C	109.5
C11—C8—C7	124.3 (3)	H22A—C22—H22C	109.5
C9—C8—C7	128.9 (3)	H22B—C22—H22C	109.5
C10—C9—C8	105.9 (3)
C7—O1—C1—C6	120.4 (3)	C10—O3—C11—C8	0.2 (3)
C7—O1—C1—C2	−117.9 (2)	C10—O3—C11—C22	178.7 (3)
O1—C1—C2—C12	60.8 (3)	C1—C2—C12—C21	69.7 (3)
C6—C1—C2—C12	179.6 (2)	C3—C2—C12—C21	−54.0 (3)
O1—C1—C2—C3	−173.6 (2)	C1—C2—C12—C13	−108.0 (3)
C6—C1—C2—C3	−54.9 (3)	C3—C2—C12—C13	128.3 (3)
C1—C2—C3—C4	54.2 (3)	C21—C12—C13—C14	−175.7 (3)
C12—C2—C3—C4	178.6 (2)	C2—C12—C13—C14	2.0 (4)
C2—C3—C4—C5	−56.2 (3)	C21—C12—C13—C18	2.8 (4)
C3—C4—C5—C6	57.4 (3)	C2—C12—C13—C18	−179.5 (2)
O1—C1—C6—C5	174.3 (2)	C18—C13—C14—C15	1.1 (4)
C2—C1—C6—C5	56.6 (3)	C12—C13—C14—C15	179.6 (3)
C4—C5—C6—C1	−57.0 (3)	C13—C14—C15—C16	−0.6 (5)
C1—O1—C7—O2	−7.0 (4)	C14—C15—C16—C17	0.1 (5)
C1—O1—C7—C8	172.8 (2)	C15—C16—C17—C18	0.0 (5)
O2—C7—C8—C11	−2.8 (5)	C16—C17—C18—C19	−177.7 (3)
O1—C7—C8—C11	177.4 (3)	C16—C17—C18—C13	0.5 (5)
O2—C7—C8—C9	176.2 (3)	C14—C13—C18—C19	177.3 (3)
O1—C7—C8—C9	−3.6 (4)	C12—C13—C18—C19	−1.3 (4)
C11—C8—C9—C10	0.0 (3)	C14—C13—C18—C17	−1.0 (4)
C7—C8—C9—C10	−179.2 (3)	C12—C13—C18—C17	−179.6 (3)
C8—C9—C10—O3	0.2 (3)	C17—C18—C19—C20	177.4 (3)
C11—O3—C10—C9	−0.3 (3)	C13—C18—C19—C20	−0.9 (5)
C9—C8—C11—O3	−0.1 (3)	C18—C19—C20—C21	1.6 (5)
C7—C8—C11—O3	179.1 (2)	C13—C12—C21—C20	−2.2 (4)
C9—C8—C11—C22	−178.1 (3)	C2—C12—C21—C20	−179.9 (3)
C7—C8—C11—C22	1.0 (5)	C19—C20—C21—C12	−0.1 (5)