Bis[5-(4-methoxy-benz-yl)furan-3-yl]methanone.

The title compound, C(25)H(22)O(5), was obtained by a dehydrogenative carbonyl-ation reaction. It crystallizes with one half-mol-ecule in the asymmetric unit. The mol-ecules have crystallographic C(2) symmetry and the two atoms of the carbonyl group are located on the rotation axis. The meth-oxy groups are coplanar with the benzene ring to which they are attached [C-C-O-C = 1.0 (6)°]. The two furan rings are inclined at 17.3 (3)° with respect to each other and the dihedral angle between the furan ring and the benzene ring is 75.83 (12)°. The crystal structure is stabilized by C-H⋯O hydrogen bonds.

Related literature

The palladium-catalysed cyclo­isomerization of allenyl ketones delivers furan derivatives, see: Hashmi (1995 ▶); Hashmi & Schwarz (1997 ▶); Hashmi et al. (1999 ▶, 2000 ▶, 2004 ▶); Hashmi, Ruppert, Knöfel & Bats (1997 ▶).

Experimental

Crystal data

C25H22O5

M = 402.43

Monoclinic,

a = 42.050 (2) Å

b = 5.9183 (2) Å

c = 8.3269 (3) Å

β = 99.594 (2)°

V = 2043.29 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 183 K

0.60 × 0.30 × 0.05 mm

Data collection

Siemens CCD three-circle diffractometer

Absorption correction: none

8458 measured reflections

1854 independent reflections

1506 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.195

S = 1.25

1854 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.23 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809034333/at2869sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034333/at2869Isup2.hkl

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

C25H22O5	F(000) = 848
Mr = 402.43	Dx = 1.308 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5761 reflections
a = 42.050 (2) Å	θ = 5.2–24.8°
b = 5.9183 (2) Å	µ = 0.09 mm−1
c = 8.3269 (3) Å	T = 183 K
β = 99.594 (2)°	Plate, colourless
V = 2043.29 (14) Å3	0.60 × 0.30 × 0.05 mm
Z = 4

Siemens CCD three-circle diffractometer	1506 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
graphite	θmax = 26.2°, θmin = 2.0°
ω scans	h = −50→51
8458 measured reflections	k = −7→7
1854 independent reflections	l = −10→9

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)] = 0.081	H-atom parameters constrained
wR(F2) = 0.195	w = 1/[σ2(Fo2) + (0.0374P)2 + 9.4535P] where P = (Fo2 + 2Fc2)/3
S = 1.25	(Δ/σ)max < 0.001
1854 reflections	Δρmax = 0.31 e Å−3
138 parameters	Δρmin = −0.23 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: 0.0039 (8)

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	0.37264 (9)	0.2789 (7)	0.4374 (5)	0.0332 (9)
C2	0.35544 (9)	0.0841 (7)	0.4534 (5)	0.0385 (10)
H2	0.3643	−0.0267	0.5307	0.046*
C3	0.32526 (9)	0.0460 (7)	0.3586 (5)	0.0389 (10)
H3	0.3137	−0.0887	0.3716	0.047*
C4	0.31251 (9)	0.2064 (7)	0.2458 (5)	0.0328 (9)
O41	0.28319 (6)	0.1887 (5)	0.1431 (4)	0.0422 (8)
C42	0.26472 (10)	−0.0101 (9)	0.1577 (6)	0.0534 (13)
H42A	0.2618	−0.0290	0.2712	0.080*
H42B	0.2761	−0.1418	0.1237	0.080*
H42C	0.2436	0.0038	0.0881	0.080*
C5	0.32947 (9)	0.4037 (7)	0.2275 (5)	0.0363 (10)
H5	0.3207	0.5142	0.1499	0.044*
C6	0.35934 (9)	0.4378 (7)	0.3238 (5)	0.0364 (10)
H6	0.3709	0.5729	0.3114	0.044*
C7	0.40530 (9)	0.3207 (8)	0.5416 (5)	0.0415 (11)
H7A	0.4047	0.4680	0.5974	0.050*
H7B	0.4092	0.2022	0.6265	0.050*
C11	0.43293 (9)	0.3219 (7)	0.4488 (5)	0.0339 (9)
C12	0.45192 (8)	0.4804 (7)	0.4054 (4)	0.0308 (9)
H12	0.4509	0.6373	0.4279	0.037*
C13	0.47441 (8)	0.3727 (6)	0.3184 (5)	0.0297 (9)
C31	0.5000	0.4907 (9)	0.2500	0.0297 (12)
O32	0.5000	0.6987 (7)	0.2500	0.0418 (10)
C14	0.46659 (10)	0.1524 (7)	0.3128 (6)	0.0418 (11)
H14	0.4774	0.0387	0.2618	0.050*
O15	0.44090 (7)	0.1147 (5)	0.3907 (4)	0.0466 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0262 (19)	0.044 (2)	0.032 (2)	0.0024 (17)	0.0115 (16)	−0.0021 (18)
C2	0.034 (2)	0.045 (3)	0.037 (2)	0.0054 (18)	0.0087 (18)	0.0062 (19)
C3	0.035 (2)	0.039 (2)	0.045 (2)	−0.0023 (18)	0.0119 (19)	0.005 (2)
C4	0.0239 (18)	0.041 (2)	0.035 (2)	0.0018 (16)	0.0100 (16)	−0.0027 (18)
O41	0.0297 (14)	0.0454 (18)	0.0502 (18)	−0.0019 (13)	0.0032 (13)	0.0012 (14)
C42	0.040 (2)	0.054 (3)	0.063 (3)	−0.014 (2)	−0.002 (2)	−0.003 (3)
C5	0.032 (2)	0.036 (2)	0.041 (2)	0.0020 (17)	0.0063 (18)	0.0038 (18)
C6	0.031 (2)	0.037 (2)	0.044 (2)	−0.0043 (17)	0.0144 (18)	−0.0009 (19)
C7	0.030 (2)	0.060 (3)	0.036 (2)	0.000 (2)	0.0095 (17)	−0.001 (2)
C11	0.0252 (19)	0.045 (2)	0.031 (2)	0.0035 (17)	0.0023 (16)	−0.0062 (18)
C12	0.0280 (19)	0.035 (2)	0.028 (2)	0.0045 (16)	0.0011 (16)	−0.0044 (17)
C13	0.0245 (18)	0.030 (2)	0.035 (2)	0.0011 (16)	0.0040 (15)	0.0000 (17)
C31	0.028 (3)	0.026 (3)	0.035 (3)	0.000	0.004 (2)	0.000
O32	0.040 (2)	0.031 (2)	0.055 (3)	0.000	0.012 (2)	0.000
C14	0.036 (2)	0.032 (2)	0.063 (3)	0.0020 (18)	0.023 (2)	−0.002 (2)
O15	0.0380 (16)	0.0336 (17)	0.074 (2)	−0.0051 (13)	0.0252 (15)	−0.0007 (15)

C1—C2	1.380 (6)	C6—H6	0.9500
C1—C6	1.384 (6)	C7—C11	1.498 (5)
C1—C7	1.518 (5)	C7—H7A	0.9900
C2—C3	1.397 (6)	C7—H7B	0.9900
C2—H2	0.9500	C11—C12	1.321 (6)
C3—C4	1.380 (6)	C11—O15	1.380 (5)
C3—H3	0.9500	C12—C13	1.433 (5)
C4—O41	1.383 (5)	C12—H12	0.9500
C4—C5	1.390 (6)	C13—C14	1.344 (6)
O41—C42	1.426 (5)	C13—C31	1.474 (4)
C42—H42A	0.9800	C31—O32	1.231 (7)
C42—H42B	0.9800	C31—C13i	1.474 (4)
C42—H42C	0.9800	C14—O15	1.368 (5)
C5—C6	1.388 (5)	C14—H14	0.9500
C5—H5	0.9500
C2—C1—C6	118.4 (4)	C5—C6—H6	119.3
C2—C1—C7	121.3 (4)	C11—C7—C1	114.3 (3)
C6—C1—C7	120.3 (4)	C11—C7—H7A	108.7
C1—C2—C3	121.5 (4)	C1—C7—H7A	108.7
C1—C2—H2	119.3	C11—C7—H7B	108.7
C3—C2—H2	119.3	C1—C7—H7B	108.7
C4—C3—C2	119.1 (4)	H7A—C7—H7B	107.6
C4—C3—H3	120.4	C12—C11—O15	110.0 (3)
C2—C3—H3	120.4	C12—C11—C7	134.5 (4)
C3—C4—O41	125.1 (4)	O15—C11—C7	115.5 (4)
C3—C4—C5	120.3 (4)	C11—C12—C13	107.6 (4)
O41—C4—C5	114.6 (4)	C11—C12—H12	126.2
C4—O41—C42	116.9 (3)	C13—C12—H12	126.2
O41—C42—H42A	109.5	C14—C13—C12	105.7 (3)
O41—C42—H42B	109.5	C14—C13—C31	129.5 (4)
H42A—C42—H42B	109.5	C12—C13—C31	124.8 (4)
O41—C42—H42C	109.5	O32—C31—C13i	118.3 (2)
H42A—C42—H42C	109.5	O32—C31—C13	118.3 (2)
H42B—C42—H42C	109.5	C13i—C31—C13	123.4 (5)
C6—C5—C4	119.4 (4)	C13—C14—O15	110.5 (3)
C6—C5—H5	120.3	C13—C14—H14	124.8
C4—C5—H5	120.3	O15—C14—H14	124.8
C1—C6—C5	121.3 (4)	C14—O15—C11	106.2 (3)
C1—C6—H6	119.3
C6—C1—C2—C3	−0.2 (6)	C1—C7—C11—O15	−70.6 (5)
C7—C1—C2—C3	179.5 (4)	O15—C11—C12—C13	−1.9 (4)
C1—C2—C3—C4	0.4 (6)	C7—C11—C12—C13	179.3 (4)
C2—C3—C4—O41	179.1 (4)	C11—C12—C13—C14	1.3 (5)
C2—C3—C4—C5	−0.3 (6)	C11—C12—C13—C31	−179.5 (3)
C3—C4—O41—C42	1.0 (6)	C14—C13—C31—O32	170.0 (4)
C5—C4—O41—C42	−179.6 (4)	C12—C13—C31—O32	−9.0 (4)
C3—C4—C5—C6	0.0 (6)	C14—C13—C31—C13i	−10.0 (4)
O41—C4—C5—C6	−179.4 (3)	C12—C13—C31—C13i	171.0 (4)
C2—C1—C6—C5	−0.1 (6)	C12—C13—C14—O15	−0.2 (5)
C7—C1—C6—C5	−179.8 (4)	C31—C13—C14—O15	−179.3 (3)
C4—C5—C6—C1	0.2 (6)	C13—C14—O15—C11	−0.9 (5)
C2—C1—C7—C11	113.0 (4)	C12—C11—O15—C14	1.8 (5)
C6—C1—C7—C11	−67.3 (5)	C7—C11—O15—C14	−179.2 (3)
C1—C7—C11—C12	108.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O32ii	0.95	2.23	3.114 (5)	154
C12—H12···O15iii	0.95	2.87	3.782 (5)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O32i	0.95	2.23	3.114 (5)	154
C12—H12⋯O15ii	0.95	2.87	3.782 (5)	163

Symmetry codes: (i) ; (ii) .