(Z)-Methyl 2-[(2-eth-oxy-6-formyl-phen-oxy)meth-yl]-3-(4-ethyl-phen-yl)acrylate.

The title compound, C(22)H(24)O(5), consists of two substituted benzene rings linked by an ethyl acrylate group. The dihedral angle between the two benzene rings is 58.39 (7)°. The crystal packing is governed by two C-H⋯O inter-actions, one of which forms centrosymmetric dimers with a graph-set descriptor of R(2) (2)(18).

Related literature

For applications of acrylate derivatives, see: Xiao et al. (2008 ▶). For a related structure, see: Gong et al. (2008 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H24O5

M = 368.41

Triclinic,

a = 9.6746 (3) Å

b = 9.9435 (3) Å

c = 10.7935 (3) Å

α = 77.595 (1)°

β = 85.433 (2)°

γ = 76.752 (1)°

V = 986.59 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

25506 measured reflections

6646 independent reflections

4400 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.164

S = 1.02

6646 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046587/pv2468sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046587/pv2468Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046587/pv2468Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H24O5	Z = 2
Mr = 368.41	F(000) = 392
Triclinic, P1	Dx = 1.240 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6746 (3) Å	Cell parameters from 6646 reflections
b = 9.9435 (3) Å	θ = 1.9–31.7°
c = 10.7935 (3) Å	µ = 0.09 mm−1
α = 77.595 (1)°	T = 293 K
β = 85.433 (2)°	Block, colorless
γ = 76.752 (1)°	0.30 × 0.25 × 0.20 mm
V = 986.59 (5) Å3

Bruker SMART APEXII area-detector diffractometer	4400 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 31.7°, θmin = 1.9°
ω and φ scans	h = −13→14
25506 measured reflections	k = −14→14
6646 independent reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.083P)2 + 0.1225P] where P = (Fo2 + 2Fc2)/3
6646 reflections	(Δ/σ)max < 0.001
247 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
C1	0.31037 (15)	0.58360 (15)	1.00970 (12)	0.0513 (3)
H1	0.3275	0.4934	1.0602	0.062*
C2	0.27416 (17)	0.69925 (18)	1.06433 (12)	0.0587 (4)
H2	0.2698	0.6871	1.1523	0.070*
C3	0.24384 (16)	0.83397 (16)	0.99082 (13)	0.0544 (3)
H3	0.2180	0.9113	1.0298	0.065*
C4	0.25171 (13)	0.85470 (13)	0.85931 (12)	0.0429 (3)
C5	0.29508 (12)	0.73676 (12)	0.80276 (10)	0.0370 (2)
C6	0.32154 (13)	0.60162 (13)	0.87760 (11)	0.0407 (2)
C7	0.35960 (15)	0.47780 (13)	0.81699 (13)	0.0476 (3)
H7	0.3812	0.4937	0.7303	0.057*
C8	0.14625 (18)	1.10162 (16)	0.82610 (18)	0.0674 (4)
H8A	0.2085	1.1287	0.8779	0.081*
H8B	0.0645	1.0803	0.8781	0.081*
C9	0.1000 (2)	1.21793 (18)	0.7157 (2)	0.0875 (6)
H9A	0.1819	1.2399	0.6664	0.131*
H9B	0.0477	1.2999	0.7455	0.131*
H9C	0.0405	1.1890	0.6640	0.131*
C10	0.41026 (15)	0.83034 (13)	0.61113 (12)	0.0460 (3)
H10A	0.4742	0.8363	0.6735	0.055*
H10B	0.3643	0.9254	0.5711	0.055*
C11	0.49176 (13)	0.75448 (12)	0.51363 (11)	0.0411 (3)
C12	0.60371 (14)	0.63091 (13)	0.56688 (11)	0.0448 (3)
C13	0.79009 (18)	0.44609 (17)	0.52593 (16)	0.0675 (4)
H13A	0.8616	0.4799	0.5595	0.101*
H13B	0.8308	0.4006	0.4575	0.101*
H13C	0.7542	0.3799	0.5915	0.101*
C14	0.47471 (13)	0.79509 (12)	0.38798 (11)	0.0411 (3)
H14	0.5362	0.7412	0.3376	0.049*
C15	0.37025 (13)	0.91476 (12)	0.32064 (11)	0.0403 (3)
C16	0.41376 (13)	0.99223 (13)	0.20705 (10)	0.0415 (3)
H16	0.5049	0.9635	0.1739	0.050*
C17	0.32363 (13)	1.11147 (13)	0.14246 (11)	0.0436 (3)
H17	0.3567	1.1638	0.0687	0.052*
C18	0.18579 (14)	1.15383 (13)	0.18558 (12)	0.0438 (3)
C19	0.13937 (15)	1.07222 (15)	0.29530 (15)	0.0588 (4)
H19	0.0455	1.0962	0.3239	0.071*
C20	0.23041 (15)	0.95586 (15)	0.36287 (14)	0.0562 (4)
H20	0.1976	0.9046	0.4374	0.067*
C21	0.08788 (16)	1.28446 (14)	0.11572 (14)	0.0529 (3)
H21A	0.1371	1.3239	0.0396	0.064*
H21B	0.0058	1.2580	0.0898	0.064*
C22	0.03783 (18)	1.39611 (16)	0.19423 (17)	0.0664 (4)
H22A	−0.0149	1.3593	0.2678	0.100*
H22B	−0.0219	1.4771	0.1445	0.100*
H22C	0.1185	1.4229	0.2203	0.100*
O1	0.36468 (14)	0.35836 (11)	0.87125 (11)	0.0706 (3)
O2	0.21967 (11)	0.98154 (9)	0.77707 (9)	0.0546 (3)
O3	0.30428 (9)	0.75349 (9)	0.67258 (7)	0.0420 (2)
O4	0.62780 (13)	0.59403 (13)	0.67774 (9)	0.0718 (3)
O5	0.67596 (12)	0.56277 (10)	0.47986 (9)	0.0596 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0547 (8)	0.0589 (8)	0.0368 (6)	−0.0115 (6)	−0.0013 (5)	−0.0034 (5)
C2	0.0677 (9)	0.0775 (10)	0.0329 (6)	−0.0189 (7)	0.0017 (6)	−0.0135 (6)
C3	0.0581 (8)	0.0663 (8)	0.0470 (7)	−0.0161 (6)	0.0069 (6)	−0.0294 (6)
C4	0.0428 (6)	0.0439 (6)	0.0434 (6)	−0.0083 (5)	0.0031 (5)	−0.0150 (5)
C5	0.0374 (6)	0.0427 (6)	0.0313 (5)	−0.0076 (4)	0.0004 (4)	−0.0103 (4)
C6	0.0399 (6)	0.0442 (6)	0.0367 (5)	−0.0080 (4)	0.0002 (4)	−0.0072 (4)
C7	0.0534 (7)	0.0417 (6)	0.0442 (6)	−0.0067 (5)	0.0025 (5)	−0.0065 (5)
C8	0.0644 (10)	0.0504 (8)	0.0862 (11)	0.0030 (7)	0.0051 (8)	−0.0307 (8)
C9	0.0839 (13)	0.0477 (9)	0.1221 (17)	0.0050 (8)	−0.0087 (12)	−0.0170 (9)
C10	0.0620 (8)	0.0391 (6)	0.0384 (6)	−0.0151 (5)	0.0069 (5)	−0.0099 (4)
C11	0.0490 (7)	0.0375 (5)	0.0353 (5)	−0.0085 (5)	0.0015 (5)	−0.0061 (4)
C12	0.0506 (7)	0.0459 (6)	0.0354 (6)	−0.0084 (5)	−0.0033 (5)	−0.0043 (5)
C13	0.0659 (10)	0.0592 (9)	0.0648 (9)	0.0140 (7)	−0.0140 (7)	−0.0106 (7)
C14	0.0472 (6)	0.0359 (5)	0.0366 (5)	−0.0041 (4)	0.0007 (5)	−0.0059 (4)
C15	0.0462 (6)	0.0352 (5)	0.0372 (5)	−0.0057 (4)	−0.0009 (5)	−0.0061 (4)
C16	0.0410 (6)	0.0471 (6)	0.0335 (5)	−0.0054 (5)	−0.0007 (4)	−0.0065 (4)
C17	0.0480 (7)	0.0451 (6)	0.0351 (5)	−0.0096 (5)	−0.0041 (5)	−0.0021 (4)
C18	0.0460 (7)	0.0378 (6)	0.0463 (6)	−0.0065 (5)	−0.0064 (5)	−0.0064 (5)
C19	0.0440 (7)	0.0520 (7)	0.0676 (9)	−0.0015 (5)	0.0100 (6)	0.0019 (6)
C20	0.0522 (8)	0.0474 (7)	0.0569 (8)	−0.0064 (6)	0.0117 (6)	0.0063 (6)
C21	0.0512 (7)	0.0462 (7)	0.0557 (8)	−0.0027 (5)	−0.0115 (6)	−0.0029 (6)
C22	0.0629 (9)	0.0505 (8)	0.0788 (10)	0.0062 (7)	−0.0115 (8)	−0.0145 (7)
O1	0.0969 (9)	0.0419 (5)	0.0657 (7)	−0.0109 (5)	0.0071 (6)	−0.0030 (5)
O2	0.0641 (6)	0.0391 (5)	0.0563 (5)	−0.0010 (4)	0.0073 (5)	−0.0149 (4)
O3	0.0526 (5)	0.0433 (4)	0.0317 (4)	−0.0127 (3)	0.0005 (3)	−0.0090 (3)
O4	0.0754 (8)	0.0890 (8)	0.0372 (5)	0.0058 (6)	−0.0124 (5)	−0.0039 (5)
O5	0.0704 (7)	0.0530 (5)	0.0423 (5)	0.0145 (5)	−0.0087 (4)	−0.0085 (4)

C1—C2	1.366 (2)	C11—C12	1.4829 (17)
C1—C6	1.3969 (17)	C12—O4	1.1990 (15)
C1—H1	0.9300	C12—O5	1.3347 (16)
C2—C3	1.382 (2)	C13—O5	1.4370 (16)
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.3882 (18)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—O2	1.3632 (15)	C14—C15	1.4696 (15)
C4—C5	1.4019 (16)	C14—H14	0.9300
C5—O3	1.3771 (13)	C15—C20	1.3905 (18)
C5—C6	1.3901 (16)	C15—C16	1.3908 (16)
C6—C7	1.4763 (17)	C16—C17	1.3856 (16)
C7—O1	1.1978 (16)	C16—H16	0.9300
C7—H7	0.9300	C17—C18	1.3785 (18)
C8—O2	1.4259 (16)	C17—H17	0.9300
C8—C9	1.488 (3)	C18—C19	1.3901 (19)
C8—H8A	0.9700	C18—C21	1.5106 (17)
C8—H8B	0.9700	C19—C20	1.3853 (19)
C9—H9A	0.9600	C19—H19	0.9300
C9—H9B	0.9600	C20—H20	0.9300
C9—H9C	0.9600	C21—C22	1.509 (2)
C10—O3	1.4520 (15)	C21—H21A	0.9700
C10—C11	1.4949 (16)	C21—H21B	0.9700
C10—H10A	0.9700	C22—H22A	0.9600
C10—H10B	0.9700	C22—H22B	0.9600
C11—C14	1.3414 (16)	C22—H22C	0.9600
C2—C1—C6	119.61 (12)	O5—C12—C11	113.84 (10)
C2—C1—H1	120.2	O5—C13—H13A	109.5
C6—C1—H1	120.2	O5—C13—H13B	109.5
C1—C2—C3	121.00 (12)	H13A—C13—H13B	109.5
C1—C2—H2	119.5	O5—C13—H13C	109.5
C3—C2—H2	119.5	H13A—C13—H13C	109.5
C2—C3—C4	120.52 (12)	H13B—C13—H13C	109.5
C2—C3—H3	119.7	C11—C14—C15	127.62 (11)
C4—C3—H3	119.7	C11—C14—H14	116.2
O2—C4—C3	125.90 (11)	C15—C14—H14	116.2
O2—C4—C5	115.38 (10)	C20—C15—C16	117.66 (11)
C3—C4—C5	118.72 (12)	C20—C15—C14	124.35 (11)
O3—C5—C6	119.47 (10)	C16—C15—C14	117.99 (11)
O3—C5—C4	120.26 (10)	C17—C16—C15	121.10 (11)
C6—C5—C4	120.17 (10)	C17—C16—H16	119.4
C5—C6—C1	119.87 (11)	C15—C16—H16	119.4
C5—C6—C7	119.81 (10)	C18—C17—C16	121.16 (11)
C1—C6—C7	120.32 (11)	C18—C17—H17	119.4
O1—C7—C6	124.82 (12)	C16—C17—H17	119.4
O1—C7—H7	117.6	C17—C18—C19	117.90 (11)
C6—C7—H7	117.6	C17—C18—C21	121.17 (11)
O2—C8—C9	107.34 (15)	C19—C18—C21	120.94 (12)
O2—C8—H8A	110.2	C20—C19—C18	121.21 (13)
C9—C8—H8A	110.2	C20—C19—H19	119.4
O2—C8—H8B	110.2	C18—C19—H19	119.4
C9—C8—H8B	110.2	C19—C20—C15	120.81 (12)
H8A—C8—H8B	108.5	C19—C20—H20	119.6
C8—C9—H9A	109.5	C15—C20—H20	119.6
C8—C9—H9B	109.5	C22—C21—C18	113.21 (12)
H9A—C9—H9B	109.5	C22—C21—H21A	108.9
C8—C9—H9C	109.5	C18—C21—H21A	108.9
H9A—C9—H9C	109.5	C22—C21—H21B	108.9
H9B—C9—H9C	109.5	C18—C21—H21B	108.9
O3—C10—C11	108.76 (10)	H21A—C21—H21B	107.7
O3—C10—H10A	109.9	C21—C22—H22A	109.5
C11—C10—H10A	109.9	C21—C22—H22B	109.5
O3—C10—H10B	109.9	H22A—C22—H22B	109.5
C11—C10—H10B	109.9	C21—C22—H22C	109.5
H10A—C10—H10B	108.3	H22A—C22—H22C	109.5
C14—C11—C12	120.99 (11)	H22B—C22—H22C	109.5
C14—C11—C10	125.04 (11)	C4—O2—C8	118.22 (11)
C12—C11—C10	113.86 (10)	C5—O3—C10	114.56 (9)
O4—C12—O5	122.44 (12)	C12—O5—C13	115.99 (11)
O4—C12—C11	123.71 (12)
C6—C1—C2—C3	2.1 (2)	C10—C11—C14—C15	−3.6 (2)
C1—C2—C3—C4	−1.0 (2)	C11—C14—C15—C20	−38.7 (2)
C2—C3—C4—O2	177.56 (13)	C11—C14—C15—C16	141.38 (14)
C2—C3—C4—C5	−1.9 (2)	C20—C15—C16—C17	4.00 (19)
O2—C4—C5—O3	0.58 (17)	C14—C15—C16—C17	−176.03 (11)
C3—C4—C5—O3	−179.90 (11)	C15—C16—C17—C18	−2.89 (19)
O2—C4—C5—C6	−175.87 (11)	C16—C17—C18—C19	−0.7 (2)
C3—C4—C5—C6	3.65 (18)	C16—C17—C18—C21	179.52 (12)
O3—C5—C6—C1	−179.04 (11)	C17—C18—C19—C20	3.1 (2)
C4—C5—C6—C1	−2.56 (18)	C21—C18—C19—C20	−177.14 (14)
O3—C5—C6—C7	0.21 (18)	C18—C19—C20—C15	−1.9 (3)
C4—C5—C6—C7	176.69 (11)	C16—C15—C20—C19	−1.6 (2)
C2—C1—C6—C5	−0.3 (2)	C14—C15—C20—C19	178.41 (14)
C2—C1—C6—C7	−179.58 (13)	C17—C18—C21—C22	−118.36 (15)
C5—C6—C7—O1	−168.90 (14)	C19—C18—C21—C22	61.87 (19)
C1—C6—C7—O1	10.3 (2)	C3—C4—O2—C8	−12.8 (2)
O3—C10—C11—C14	103.91 (14)	C5—C4—O2—C8	166.63 (12)
O3—C10—C11—C12	−79.81 (13)	C9—C8—O2—C4	−169.18 (14)
C14—C11—C12—O4	176.44 (14)	C6—C5—O3—C10	−119.28 (12)
C10—C11—C12—O4	0.0 (2)	C4—C5—O3—C10	64.25 (14)
C14—C11—C12—O5	−3.89 (18)	C11—C10—O3—C5	135.17 (10)
C10—C11—C12—O5	179.67 (11)	O4—C12—O5—C13	−3.1 (2)
C12—C11—C14—C15	−179.59 (12)	C11—C12—O5—C13	177.20 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O5i	0.93	2.58	3.368 (2)	143
C17—H17···O1ii	0.93	2.56	3.454 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O5i	0.93	2.58	3.368 (2)	143
C17—H17⋯O1ii	0.93	2.56	3.454 (2)	161

Symmetry codes: (i) ; (ii) .