Methyl 3,5-bis(cyclo-hexyl-meth-oxy)benzoate.

In the title compound, C22H32O4, the atoms of the methyl ester group and the alk-oxy O atoms are all coplanar with the central aromatic ring, with an r.m.s. deviation of 0.008 Å. Bonds to the methyl-ene and cyclo-hexyl groups are also very close to this plane, so that the mol-ecule is essentially flat, apart from the cyclo-hexyl groups. The mean planes through the cyclo-hexyl groups are tilted by 30.08 (9) and 36.14 (7)° with respect to the central aromatic ring. In the crystal, pairs of mol-ecules linked by C-H⋯O hydrogen bonds form planar units which are stacked along the a axis, with an average inter-planar distance of 3.549 (2) Å. Stacking appears to be stabilized by further weak C-H⋯O hydrogen bonds.

Related literature

The title compound was synthesized as a monomer for novel dendrimers, as part of a continuing study of how dendrimers effectively complex with organic pollutants in aqueous environments. For a project review, see: Monaco et al. (2013 ▶); Corfield & Balija (2013 ▶). For a review of the role of C—H⋯O hydrogen bonds in organic reactions, see: Johnston & Cheong (2013 ▶). For an example of an organic crystal structure involving the cyclo­hexyl­meth­oxy­benzene fragment, see: Yang et al. (2008 ▶).

Experimental

Crystal data

C22H32O4

M = 360.48

Triclinic,

a = 6.649 (1) Å

b = 12.668 (1) Å

c = 12.873 (1) Å

α = 87.64 (1)°

β = 79.46 (1)°

γ = 75.06 (1)°

V = 1029.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.75 × 0.75 × 0.53 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

5155 measured reflections

4051 independent reflections

3013 reflections with I > 2σ(I)

R int = 0.008

3 standard reflections every 120 min intensity decay: 1.3 (5)%

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.128

S = 1.03

4051 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CAD-4 (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4; data reduction: followed procedures in Corfield et al. (1973 ▶) and data were averaged with a local version of SORTAV (Blessing, 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814004607/pk2519sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004607/pk2519Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004607/pk2519Isup3.cml

CCDC reference: 989172

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H32O4	Z = 2
Mr = 360.48	F(000) = 392
Triclinic, P1	Dx = 1.162 Mg m−3
Hall symbol: -P 1	Melting point: 344.8 K
a = 6.649 (1) Å	Mo Kα radiation, λ = 0.71070 Å
b = 12.668 (1) Å	Cell parameters from 25 reflections
c = 12.873 (1) Å	θ = 3.2–9.7°
α = 87.64 (1)°	µ = 0.08 mm−1
β = 79.46 (1)°	T = 298 K
γ = 75.06 (1)°	Block, colourless
V = 1029.9 (2) Å3	0.75 × 0.75 × 0.53 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.008
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.3°
Graphite monochromator	h = −1→8
θ/2θ scans	k = −15→15
5155 measured reflections	l = −15→15
4051 independent reflections	3 standard reflections every 120 min
3013 reflections with I > 2σ(I)	intensity decay: 1.3(5)

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.033P)2 + 0.270P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.002
4051 reflections	Δρmax = 0.17 e Å−3
237 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (2)

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.

	x	y	z	Uiso*/Ueq
O1	−0.2343 (2)	0.20265 (10)	0.34241 (8)	0.0613 (3)
O2	−0.0616 (2)	0.25640 (11)	0.67501 (8)	0.0628 (4)
O3	0.2878 (2)	0.42136 (12)	0.25302 (9)	0.0756 (4)
O4	0.37753 (19)	0.44700 (10)	0.40594 (8)	0.0602 (3)
C1	0.1250 (2)	0.34685 (12)	0.40804 (11)	0.0450 (4)
C2	0.0091 (3)	0.30219 (13)	0.35244 (11)	0.0486 (4)
H2	0.0217	0.3118	0.2797	0.058*
C3	−0.1264 (3)	0.24282 (13)	0.40479 (11)	0.0490 (4)
C4	−0.1455 (3)	0.22817 (14)	0.51302 (12)	0.0512 (4)
H4	−0.2355	0.1878	0.5482	0.061*
C5	−0.0280 (3)	0.27471 (13)	0.56870 (11)	0.0495 (4)
C6	0.1076 (3)	0.33363 (13)	0.51749 (11)	0.0485 (4)
H6	0.1862	0.3641	0.5549	0.058*
C7	0.2697 (3)	0.40810 (13)	0.34645 (12)	0.0483 (4)
C8	0.5185 (3)	0.50921 (17)	0.35207 (14)	0.0655 (5)
H8A	0.6079	0.4683	0.2922	0.079*
H8B	0.6042	0.5236	0.3995	0.079*
H8C	0.4372	0.5771	0.3286	0.079*
C9	−0.3584 (3)	0.13030 (15)	0.38765 (12)	0.0554 (4)
H9A	−0.4655	0.1661	0.4459	0.067*
H9B	−0.2692	0.0658	0.4145	0.067*
C10	−0.4621 (3)	0.09842 (14)	0.30275 (12)	0.0516 (4)
H10	−0.5436	0.1657	0.2746	0.062*
C11	−0.3030 (3)	0.03691 (16)	0.21158 (14)	0.0621 (5)
H11A	−0.2114	0.0823	0.1795	0.075*
H11B	−0.2157	−0.0286	0.2379	0.075*
C12	−0.4151 (4)	0.00567 (19)	0.12867 (16)	0.0777 (6)
H12A	−0.3110	−0.0377	0.0735	0.093*
H12B	−0.4894	0.0714	0.0967	0.093*
C13	−0.5711 (4)	−0.05892 (19)	0.17717 (19)	0.0862 (7)
H13A	−0.6463	−0.0733	0.1237	0.103*
H13B	−0.4946	−0.1286	0.2016	0.103*
C14	−0.7281 (4)	0.00134 (19)	0.26845 (18)	0.0795 (6)
H14A	−0.8190	−0.0444	0.3005	0.095*
H14B	−0.8163	0.0670	0.2428	0.095*
C15	−0.6158 (3)	0.03203 (17)	0.35076 (15)	0.0665 (5)
H15A	−0.7197	0.0742	0.4067	0.080*
H15B	−0.5395	−0.0339	0.3816	0.080*
C16	0.0433 (3)	0.30659 (15)	0.73897 (11)	0.0525 (4)
H16A	0.0098	0.3849	0.7276	0.063*
H16B	0.1953	0.2778	0.7200	0.063*
C17	−0.0299 (3)	0.28262 (14)	0.85363 (11)	0.0500 (4)
H17	0.0038	0.2032	0.8626	0.060*
C18	−0.2652 (3)	0.32768 (16)	0.88989 (12)	0.0571 (4)
H18A	−0.3025	0.4059	0.8784	0.069*
H18B	−0.3411	0.2949	0.8482	0.069*
C19	−0.3324 (3)	0.3047 (2)	1.00661 (13)	0.0713 (6)
H19A	−0.4822	0.3385	1.0281	0.086*
H19B	−0.3101	0.2265	1.0167	0.086*
C20	−0.2097 (3)	0.3479 (2)	1.07503 (13)	0.0755 (6)
H20A	−0.2480	0.4271	1.0729	0.091*
H20B	−0.2473	0.3259	1.1476	0.091*
C21	0.0244 (3)	0.3063 (2)	1.03912 (14)	0.0855 (7)
H21A	0.0658	0.2281	1.0511	0.103*
H21B	0.0976	0.3409	1.0807	0.103*
C22	0.0908 (3)	0.3291 (2)	0.92233 (13)	0.0706 (6)
H22A	0.0649	0.4073	0.9117	0.085*
H22B	0.2413	0.2969	0.9010	0.085*

	U11	U22	U33	U12	U13	U23
O1	0.0823 (8)	0.0788 (8)	0.0403 (6)	−0.0437 (7)	−0.0227 (6)	0.0013 (5)
O2	0.0878 (9)	0.0868 (9)	0.0294 (5)	−0.0490 (7)	−0.0117 (5)	−0.0017 (5)
O3	0.1073 (11)	0.0992 (10)	0.0400 (7)	−0.0588 (9)	−0.0200 (6)	0.0126 (6)
O4	0.0700 (8)	0.0812 (8)	0.0408 (6)	−0.0389 (7)	−0.0108 (5)	−0.0017 (5)
C1	0.0534 (9)	0.0468 (8)	0.0358 (7)	−0.0132 (7)	−0.0093 (6)	−0.0030 (6)
C2	0.0623 (10)	0.0546 (9)	0.0326 (7)	−0.0175 (8)	−0.0140 (7)	−0.0004 (6)
C3	0.0596 (10)	0.0563 (9)	0.0364 (7)	−0.0190 (8)	−0.0150 (7)	−0.0059 (7)
C4	0.0612 (10)	0.0616 (10)	0.0379 (8)	−0.0272 (8)	−0.0092 (7)	−0.0034 (7)
C5	0.0618 (10)	0.0586 (10)	0.0311 (7)	−0.0193 (8)	−0.0094 (6)	−0.0058 (6)
C6	0.0580 (9)	0.0581 (10)	0.0349 (7)	−0.0208 (8)	−0.0122 (7)	−0.0056 (6)
C7	0.0581 (9)	0.0508 (9)	0.0376 (8)	−0.0144 (7)	−0.0108 (7)	−0.0023 (6)
C8	0.0700 (12)	0.0821 (13)	0.0543 (10)	−0.0387 (10)	−0.0084 (9)	−0.0001 (9)
C9	0.0628 (10)	0.0688 (11)	0.0424 (8)	−0.0274 (9)	−0.0130 (7)	−0.0026 (8)
C10	0.0554 (9)	0.0567 (10)	0.0491 (9)	−0.0192 (8)	−0.0186 (7)	−0.0024 (7)
C11	0.0644 (11)	0.0728 (12)	0.0551 (10)	−0.0219 (9)	−0.0170 (8)	−0.0115 (8)
C12	0.0951 (15)	0.0896 (15)	0.0598 (11)	−0.0326 (12)	−0.0261 (11)	−0.0183 (10)
C13	0.1146 (18)	0.0749 (14)	0.0933 (16)	−0.0410 (13)	−0.0549 (14)	−0.0056 (12)
C14	0.0806 (14)	0.0876 (15)	0.0923 (16)	−0.0464 (12)	−0.0389 (12)	0.0143 (12)
C15	0.0657 (12)	0.0796 (13)	0.0647 (11)	−0.0324 (10)	−0.0199 (9)	0.0060 (10)
C16	0.0600 (10)	0.0700 (11)	0.0344 (8)	−0.0261 (8)	−0.0110 (7)	−0.0060 (7)
C17	0.0632 (10)	0.0591 (10)	0.0320 (7)	−0.0201 (8)	−0.0122 (7)	−0.0030 (6)
C18	0.0603 (10)	0.0788 (12)	0.0414 (8)	−0.0310 (9)	−0.0132 (7)	0.0013 (8)
C19	0.0726 (12)	0.1068 (16)	0.0428 (9)	−0.0418 (12)	−0.0042 (8)	0.0003 (9)
C20	0.0836 (14)	0.1131 (17)	0.0355 (9)	−0.0389 (13)	−0.0022 (8)	−0.0136 (9)
C21	0.0782 (14)	0.148 (2)	0.0381 (9)	−0.0345 (14)	−0.0178 (9)	−0.0129 (11)
C22	0.0581 (11)	0.1212 (17)	0.0398 (9)	−0.0323 (11)	−0.0101 (8)	−0.0153 (10)

O1—C3	1.3608 (17)	C12—H12A	0.9700
O1—C9	1.4245 (19)	C12—H12B	0.9700
O2—C5	1.3658 (18)	C13—C14	1.506 (3)
O2—C16	1.4322 (17)	C13—H13A	0.9700
O3—C7	1.1959 (18)	C13—H13B	0.9700
O4—C7	1.3256 (18)	C14—C15	1.518 (2)
O4—C8	1.4415 (19)	C14—H14A	0.9700
C1—C2	1.373 (2)	C14—H14B	0.9700
C1—C6	1.399 (2)	C15—H15A	0.9700
C1—C7	1.487 (2)	C15—H15B	0.9700
C2—C3	1.385 (2)	C16—C17	1.511 (2)
C2—H2	0.9300	C16—H16A	0.9700
C3—C4	1.385 (2)	C16—H16B	0.9700
C4—C5	1.396 (2)	C17—C22	1.523 (2)
C4—H4	0.9300	C17—C18	1.512 (2)
C5—C6	1.376 (2)	C17—H17	0.9800
C6—H6	0.9300	C18—C19	1.526 (2)
C8—H8A	0.9600	C18—H18A	0.9700
C8—H8B	0.9600	C18—H18B	0.9700
C8—H8C	0.9600	C19—C20	1.508 (2)
C9—C10	1.513 (2)	C19—H19A	0.9700
C9—H9A	0.9700	C19—H19B	0.9700
C9—H9B	0.9700	C20—C21	1.499 (3)
C10—C15	1.518 (2)	C20—H20A	0.9700
C10—C11	1.516 (2)	C20—H20B	0.9700
C10—H10	0.9800	C21—C22	1.525 (2)
C11—C12	1.526 (2)	C21—H21A	0.9700
C11—H11A	0.9700	C21—H21B	0.9700
C11—H11B	0.9700	C22—H22A	0.9700
C12—C13	1.514 (3)	C22—H22B	0.9700
C3—O1—C9	118.71 (12)	C14—C13—H13B	109.3
C5—O2—C16	117.86 (12)	C12—C13—H13B	109.3
C7—O4—C8	116.24 (12)	H13A—C13—H13B	107.9
C2—C1—C6	120.88 (14)	C13—C14—C15	110.87 (17)
C2—C1—C7	116.97 (13)	C13—C14—H14A	109.5
C6—C1—C7	122.15 (13)	C15—C14—H14A	109.5
C1—C2—C3	119.89 (14)	C13—C14—H14B	109.5
C1—C2—H2	120.1	C15—C14—H14B	109.5
C3—C2—H2	120.1	H14A—C14—H14B	108.1
O1—C3—C4	124.58 (14)	C10—C15—C14	111.39 (16)
O1—C3—C2	115.13 (13)	C10—C15—H15A	109.3
C4—C3—C2	120.28 (14)	C14—C15—H15A	109.3
C3—C4—C5	119.23 (15)	C10—C15—H15B	109.3
C3—C4—H4	120.4	C14—C15—H15B	109.3
C5—C4—H4	120.4	H15A—C15—H15B	108.0
O2—C5—C6	124.79 (13)	O2—C16—C17	108.62 (13)
O2—C5—C4	114.21 (14)	O2—C16—H16A	110.0
C6—C5—C4	121.00 (13)	C17—C16—H16A	110.0
C5—C6—C1	118.70 (14)	O2—C16—H16B	110.0
C5—C6—H6	120.6	C17—C16—H16B	110.0
C1—C6—H6	120.6	H16A—C16—H16B	108.3
O3—C7—O4	123.11 (15)	C16—C17—C22	109.33 (14)
O3—C7—C1	123.90 (14)	C16—C17—C18	113.02 (14)
O4—C7—C1	112.99 (12)	C22—C17—C18	109.76 (13)
O4—C8—H8A	109.5	C16—C17—H17	108.2
O4—C8—H8B	109.5	C22—C17—H17	108.2
H8A—C8—H8B	109.5	C18—C17—H17	108.2
O4—C8—H8C	109.5	C19—C18—C17	111.55 (15)
H8A—C8—H8C	109.5	C19—C18—H18A	109.3
H8B—C8—H8C	109.5	C17—C18—H18A	109.3
O1—C9—C10	108.22 (13)	C19—C18—H18B	109.3
O1—C9—H9A	110.1	C17—C18—H18B	109.3
C10—C9—H9A	110.1	H18A—C18—H18B	108.0
O1—C9—H9B	110.1	C20—C19—C18	111.71 (15)
C10—C9—H9B	110.1	C20—C19—H19A	109.3
H9A—C9—H9B	108.4	C18—C19—H19A	109.3
C9—C10—C15	109.83 (14)	C20—C19—H19B	109.3
C9—C10—C11	112.77 (14)	C18—C19—H19B	109.3
C15—C10—C11	110.74 (15)	H19A—C19—H19B	107.9
C9—C10—H10	107.8	C21—C20—C19	111.69 (16)
C15—C10—H10	107.8	C21—C20—H20A	109.3
C11—C10—H10	107.8	C19—C20—H20A	109.3
C12—C11—C10	110.79 (15)	C21—C20—H20B	109.3
C12—C11—H11A	109.5	C19—C20—H20B	109.3
C10—C11—H11A	109.5	H20A—C20—H20B	107.9
C12—C11—H11B	109.5	C20—C21—C22	111.75 (17)
C10—C11—H11B	109.5	C20—C21—H21A	109.3
H11A—C11—H11B	108.1	C22—C21—H21A	109.3
C11—C12—C13	111.22 (17)	C20—C21—H21B	109.3
C11—C12—H12A	109.4	C22—C21—H21B	109.3
C13—C12—H12A	109.4	H21A—C21—H21B	107.9
C11—C12—H12B	109.4	C17—C22—C21	111.58 (16)
C13—C12—H12B	109.4	C17—C22—H22A	109.3
H12A—C12—H12B	108.0	C21—C22—H22A	109.3
C14—C13—C12	111.78 (17)	C17—C22—H22B	109.3
C14—C13—H13A	109.3	C21—C22—H22B	109.3
C12—C13—H13A	109.3	H22A—C22—H22B	108.0
C2—C3—O1—C9	172.88 (15)	C4—C5—O2—C16	−176.46 (15)
C4—C3—O1—C9	−7.4 (3)	C6—C5—O2—C16	3.3 (3)
C3—O1—C9—C10	179.66 (14)	C5—O2—C16—C17	175.59 (14)
O1—C9—C10—C11	62.55 (19)	O2—C16—C17—C18	−61.10 (19)
O1—C9—C10—C15	−173.41 (15)	O2—C16—C17—C22	176.33 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O4i	0.96	2.58	3.409 (2)	145
C16—H16A···O3ii	0.97	2.71	3.573 (2)	148
C18—H18A···O3ii	0.97	2.72	3.590 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O4i	0.96	2.58	3.409 (2)	145
C16—H16A⋯O3ii	0.97	2.71	3.573 (2)	148
C18—H18A⋯O3ii	0.97	2.72	3.590 (2)	149

Symmetry codes: (i) ; (ii) .