Phenyl 3-meth-oxy-4-phen-oxy-benzoate.

In the title mol-ecule, C(20)H(16)O(4), the two outermost phenyl rings form dihedral angles of 79.80 (7) and 69.35 (7)° with the central benzene ring. In the crystal structure, weak inter-molecular C-H⋯O inter-actions link the mol-ecules into ribbons propagating along [1[Formula: see text]0].

Related literature

For the general synthesis of derivatives of diphenyl­ethers, see: Paul & Gupta (2004 ▶). For related structures, see: Chen et al. (2006 ▶); Petek et al. (2005 ▶); Chantrapromma et al.(2001 ▶); Nakamura et al. (1983 ▶); Gopal et al. (1980 ▶). For applications of diphenyl­ether derivatives, see: Dey & Desiraju (2005 ▶); Wang et al. (2005 ▶).

Experimental

Crystal data

C20H16O4

M = 320.33

Monoclinic,

a = 11.0261 (10) Å

b = 11.9624 (11) Å

c = 24.961 (2) Å

β = 97.842 (1)°

V = 3261.5 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.49 × 0.42 × 0.40 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.957, T max = 0.965

7972 measured reflections

2878 independent reflections

1785 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.118

S = 1.05

2878 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033678/cv5133sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033678/cv5133Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033678/cv5133Isup3.cml

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

C20H16O4	Dx = 1.305 Mg m−3
Mr = 320.33	Melting point: 383 K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.0261 (10) Å	Cell parameters from 2372 reflections
b = 11.9624 (11) Å	θ = 2.5–27.3°
c = 24.961 (2) Å	µ = 0.09 mm−1
β = 97.842 (1)°	T = 298 K
V = 3261.5 (5) Å3	Block, white
Z = 8	0.49 × 0.42 × 0.40 mm
F(000) = 1344

Bruker SMART APEXII CCD area-detector diffractometer	2878 independent reflections
Radiation source: fine-focus sealed tube	1785 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→13
Tmin = 0.957, Tmax = 0.965	k = −14→8
7972 measured reflections	l = −29→29

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0413P)2 + 1.7982P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2878 reflections	Δρmax = 0.16 e Å−3
219 parameters	Δρmin = −0.17 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: 0.0053 (4)

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	0.20235 (14)	0.40188 (12)	0.47155 (6)	0.0542 (5)
O2	0.22859 (15)	0.58572 (13)	0.46169 (6)	0.0617 (5)
O3	0.55526 (13)	0.68666 (12)	0.61835 (6)	0.0510 (4)
O4	0.59538 (14)	0.50787 (12)	0.67467 (5)	0.0562 (5)
C1	0.25750 (19)	0.50110 (18)	0.48580 (8)	0.0416 (5)
C2	0.35069 (17)	0.49359 (16)	0.53388 (7)	0.0365 (5)
C3	0.40974 (17)	0.59252 (17)	0.55134 (7)	0.0383 (5)
H3	0.3923	0.6579	0.5316	0.046*
C4	0.49363 (17)	0.59433 (16)	0.59748 (8)	0.0362 (5)
C5	0.51873 (18)	0.49544 (17)	0.62679 (7)	0.0393 (5)
C6	0.4624 (2)	0.39727 (18)	0.60920 (8)	0.0484 (6)
H6	0.4809	0.3316	0.6285	0.058*
C7	0.37782 (19)	0.39605 (18)	0.56250 (8)	0.0454 (6)
H7	0.3396	0.3296	0.5506	0.054*
C8	0.5401 (3)	0.7870 (2)	0.58760 (11)	0.0768 (9)
H8A	0.5629	0.7742	0.5524	0.115*
H8B	0.5911	0.8444	0.6056	0.115*
H8C	0.4560	0.8101	0.5841	0.115*
C9	0.6653 (2)	0.41886 (18)	0.69837 (8)	0.0459 (6)
C10	0.6668 (2)	0.4066 (2)	0.75311 (9)	0.0601 (7)
H10	0.6174	0.4510	0.7718	0.072*
C11	0.7429 (3)	0.3271 (3)	0.77982 (10)	0.0760 (9)
H11	0.7440	0.3173	0.8169	0.091*
C12	0.8166 (2)	0.2624 (2)	0.75287 (12)	0.0739 (9)
H12	0.8679	0.2094	0.7714	0.089*
C13	0.8145 (2)	0.2764 (2)	0.69818 (11)	0.0663 (7)
H13	0.8648	0.2329	0.6796	0.080*
C14	0.7378 (2)	0.3548 (2)	0.67055 (9)	0.0566 (7)
H14	0.7357	0.3638	0.6334	0.068*
C15	0.1108 (2)	0.40450 (17)	0.42591 (8)	0.0436 (6)
C16	−0.0096 (2)	0.40588 (19)	0.43430 (9)	0.0548 (6)
H16	−0.0307	0.4064	0.4691	0.066*
C17	−0.0987 (2)	0.4065 (2)	0.38964 (10)	0.0623 (7)
H17	−0.1809	0.4077	0.3944	0.075*
C18	−0.0671 (2)	0.4055 (2)	0.33860 (10)	0.0606 (7)
H18	−0.1276	0.4068	0.3088	0.073*
C19	0.0534 (2)	0.4024 (2)	0.33141 (9)	0.0620 (7)
H19	0.0747	0.4013	0.2966	0.074*
C20	0.1434 (2)	0.40105 (19)	0.37542 (9)	0.0539 (6)
H20	0.2255	0.3978	0.3706	0.065*

	U11	U22	U33	U12	U13	U23
O1	0.0618 (10)	0.0448 (9)	0.0481 (9)	−0.0063 (8)	−0.0211 (8)	0.0062 (7)
O2	0.0733 (11)	0.0466 (10)	0.0555 (10)	−0.0032 (8)	−0.0256 (8)	0.0097 (8)
O3	0.0550 (9)	0.0386 (9)	0.0528 (9)	−0.0041 (7)	−0.0163 (7)	0.0042 (7)
O4	0.0706 (11)	0.0496 (10)	0.0405 (8)	0.0025 (8)	−0.0208 (8)	0.0034 (7)
C1	0.0434 (12)	0.0420 (13)	0.0374 (12)	−0.0009 (11)	−0.0016 (10)	0.0005 (10)
C2	0.0368 (11)	0.0383 (12)	0.0328 (10)	0.0004 (9)	−0.0008 (9)	0.0020 (9)
C3	0.0383 (11)	0.0392 (12)	0.0361 (11)	0.0030 (10)	0.0000 (9)	0.0093 (9)
C4	0.0348 (11)	0.0366 (12)	0.0359 (11)	0.0007 (9)	−0.0001 (9)	−0.0001 (9)
C5	0.0412 (12)	0.0430 (13)	0.0309 (10)	0.0019 (10)	−0.0053 (9)	0.0030 (9)
C6	0.0592 (14)	0.0394 (13)	0.0423 (12)	0.0007 (11)	−0.0086 (11)	0.0114 (10)
C7	0.0496 (13)	0.0397 (13)	0.0434 (12)	−0.0039 (10)	−0.0061 (10)	0.0018 (10)
C8	0.0853 (19)	0.0437 (15)	0.089 (2)	−0.0156 (14)	−0.0321 (16)	0.0169 (14)
C9	0.0454 (13)	0.0466 (13)	0.0403 (12)	−0.0045 (11)	−0.0131 (10)	0.0126 (11)
C10	0.0530 (14)	0.0817 (18)	0.0419 (13)	−0.0012 (13)	−0.0065 (11)	0.0126 (13)
C11	0.0707 (19)	0.104 (2)	0.0473 (15)	−0.0006 (18)	−0.0142 (14)	0.0313 (16)
C12	0.0597 (17)	0.078 (2)	0.0744 (19)	0.0020 (15)	−0.0244 (15)	0.0286 (16)
C13	0.0544 (15)	0.0668 (17)	0.0740 (18)	0.0055 (13)	−0.0047 (13)	0.0088 (14)
C14	0.0622 (16)	0.0592 (15)	0.0452 (13)	−0.0011 (13)	−0.0039 (12)	0.0090 (12)
C15	0.0481 (14)	0.0376 (12)	0.0405 (12)	−0.0027 (10)	−0.0108 (10)	0.0020 (10)
C16	0.0587 (16)	0.0583 (15)	0.0466 (13)	−0.0017 (12)	0.0044 (11)	−0.0078 (11)
C17	0.0422 (13)	0.0724 (18)	0.0694 (17)	0.0012 (12)	−0.0025 (12)	−0.0132 (14)
C18	0.0569 (16)	0.0643 (17)	0.0534 (15)	−0.0035 (13)	−0.0183 (12)	−0.0025 (12)
C19	0.0620 (17)	0.0809 (19)	0.0408 (13)	−0.0123 (14)	−0.0015 (11)	0.0036 (12)
C20	0.0456 (13)	0.0633 (16)	0.0514 (14)	−0.0077 (12)	0.0010 (11)	0.0023 (12)

O1—C1	1.359 (2)	C9—C10	1.372 (3)
O1—C15	1.415 (2)	C10—C11	1.379 (3)
O2—C1	1.198 (2)	C10—H10	0.9300
O3—C4	1.362 (2)	C11—C12	1.364 (4)
O3—C8	1.422 (3)	C11—H11	0.9300
O4—C5	1.375 (2)	C12—C13	1.372 (4)
O4—C9	1.398 (2)	C12—H12	0.9300
C1—C2	1.472 (3)	C13—C14	1.383 (3)
C2—C7	1.379 (3)	C13—H13	0.9300
C2—C3	1.392 (3)	C14—H14	0.9300
C3—C4	1.375 (3)	C15—C20	1.358 (3)
C3—H3	0.9300	C15—C16	1.372 (3)
C4—C5	1.399 (3)	C16—C17	1.382 (3)
C5—C6	1.372 (3)	C16—H16	0.9300
C6—C7	1.390 (3)	C17—C18	1.366 (3)
C6—H6	0.9300	C17—H17	0.9300
C7—H7	0.9300	C18—C19	1.365 (3)
C8—H8A	0.9600	C18—H18	0.9300
C8—H8B	0.9600	C19—C20	1.377 (3)
C8—H8C	0.9600	C19—H19	0.9300
C9—C14	1.363 (3)	C20—H20	0.9300
C1—O1—C15	115.84 (15)	C9—C10—C11	118.6 (3)
C4—O3—C8	117.53 (15)	C9—C10—H10	120.7
C5—O4—C9	121.60 (16)	C11—C10—H10	120.7
O2—C1—O1	121.84 (18)	C12—C11—C10	121.1 (2)
O2—C1—C2	124.68 (19)	C12—C11—H11	119.4
O1—C1—C2	113.44 (18)	C10—C11—H11	119.4
C7—C2—C3	119.86 (17)	C11—C12—C13	119.4 (2)
C7—C2—C1	123.48 (19)	C11—C12—H12	120.3
C3—C2—C1	116.62 (17)	C13—C12—H12	120.3
C4—C3—C2	120.53 (18)	C12—C13—C14	120.4 (3)
C4—C3—H3	119.7	C12—C13—H13	119.8
C2—C3—H3	119.7	C14—C13—H13	119.8
O3—C4—C3	125.18 (17)	C9—C14—C13	119.2 (2)
O3—C4—C5	115.66 (16)	C9—C14—H14	120.4
C3—C4—C5	119.15 (18)	C13—C14—H14	120.4
C6—C5—O4	124.64 (18)	C20—C15—C16	121.75 (19)
C6—C5—C4	120.53 (17)	C20—C15—O1	119.8 (2)
O4—C5—C4	114.69 (17)	C16—C15—O1	118.42 (19)
C5—C6—C7	119.99 (19)	C15—C16—C17	118.3 (2)
C5—C6—H6	120.0	C15—C16—H16	120.9
C7—C6—H6	120.0	C17—C16—H16	120.9
C2—C7—C6	119.91 (19)	C18—C17—C16	120.6 (2)
C2—C7—H7	120.0	C18—C17—H17	119.7
C6—C7—H7	120.0	C16—C17—H17	119.7
O3—C8—H8A	109.5	C19—C18—C17	120.0 (2)
O3—C8—H8B	109.5	C19—C18—H18	120.0
H8A—C8—H8B	109.5	C17—C18—H18	120.0
O3—C8—H8C	109.5	C18—C19—C20	120.3 (2)
H8A—C8—H8C	109.5	C18—C19—H19	119.9
H8B—C8—H8C	109.5	C20—C19—H19	119.9
C14—C9—C10	121.3 (2)	C15—C20—C19	119.1 (2)
C14—C9—O4	122.70 (19)	C15—C20—H20	120.4
C10—C9—O4	115.7 (2)	C19—C20—H20	120.4
C15—O1—C1—O2	1.3 (3)	C5—C6—C7—C2	0.1 (3)
C15—O1—C1—C2	179.29 (18)	C5—O4—C9—C14	50.8 (3)
O2—C1—C2—C7	176.6 (2)	C5—O4—C9—C10	−135.7 (2)
O1—C1—C2—C7	−1.3 (3)	C14—C9—C10—C11	−0.4 (3)
O2—C1—C2—C3	−1.1 (3)	O4—C9—C10—C11	−174.1 (2)
O1—C1—C2—C3	−179.05 (17)	C9—C10—C11—C12	0.7 (4)
C7—C2—C3—C4	−1.1 (3)	C10—C11—C12—C13	−0.4 (4)
C1—C2—C3—C4	176.72 (19)	C11—C12—C13—C14	−0.3 (4)
C8—O3—C4—C3	−5.9 (3)	C10—C9—C14—C13	−0.3 (3)
C8—O3—C4—C5	175.0 (2)	O4—C9—C14—C13	172.91 (19)
C2—C3—C4—O3	−179.20 (19)	C12—C13—C14—C9	0.6 (4)
C2—C3—C4—C5	−0.2 (3)	C1—O1—C15—C20	81.7 (2)
C9—O4—C5—C6	28.7 (3)	C1—O1—C15—C16	−100.9 (2)
C9—O4—C5—C4	−155.67 (19)	C20—C15—C16—C17	−1.6 (3)
O3—C4—C5—C6	−179.50 (19)	O1—C15—C16—C17	−178.9 (2)
C3—C4—C5—C6	1.4 (3)	C15—C16—C17—C18	0.2 (4)
O3—C4—C5—O4	4.6 (3)	C16—C17—C18—C19	0.8 (4)
C3—C4—C5—O4	−174.49 (18)	C17—C18—C19—C20	−0.4 (4)
O4—C5—C6—C7	174.1 (2)	C16—C15—C20—C19	2.0 (3)
C4—C5—C6—C7	−1.3 (3)	O1—C15—C20—C19	179.3 (2)
C3—C2—C7—C6	1.1 (3)	C18—C19—C20—C15	−1.0 (4)
C1—C2—C7—C6	−176.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8C···O2i	0.96	2.52	3.408 (4)	153
C14—H14···O2ii	0.93	2.53	3.446 (3)	167
C20—H20···O3ii	0.93	2.60	3.468 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8C⋯O2i	0.96	2.52	3.408 (4)	153
C14—H14⋯O2ii	0.93	2.53	3.446 (3)	167
C20—H20⋯O3ii	0.93	2.60	3.468 (3)	155

Symmetry codes: (i) ; (ii) .