2,2'-[Ethane-1,2-diylbis(-oxy)]dibenz-alde-hyde.

In the title compound, C16H14O4, the benzene rings are inclined at a dihedral angle of 75.14 (9)°. The torsion angle of the bridging O-C-C-O group is -76.50 (11)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming C(6) chains along [100]. Furthermore, C-H⋯π inter-actions and π-π stacking inter-actions [centroid-centroid distances = 3.6957 (7) and 3.6735 (8) Å] contribute to the stability of the crystal packing.

Related literature

For the synthesis and utlization of bis-funtionalized compounds, see: Holland et al. (2007 ▶); Pedras et al. (2010 ▶); Mabkhot et al. (2012 ▶); Gavrilova & Bosnich (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H14O4

M = 270.27

Triclinic,

a = 7.7571 (1) Å

b = 8.3277 (1) Å

c = 11.2965 (1) Å

α = 82.283 (7)°

β = 75.839 (7)°

γ = 66.823 (6)°

V = 649.87 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 120 K

0.62 × 0.44 × 0.22 mm

Data collection

Rigaku R-AXIS conversion diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012 ▶) T min = 0.878, T max = 1.000

9715 measured reflections

2969 independent reflections

2862 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.101

S = 1.07

2969 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2012 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019156/bt6920sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019156/bt6920Isup2.hkl

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

C16H14O4	Z = 2
Mr = 270.27	F(000) = 284
Triclinic, P1	Dx = 1.381 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 7.7571 (1) Å	Cell parameters from 4015 reflections
b = 8.3277 (1) Å	θ = 1.9–27.5°
c = 11.2965 (1) Å	µ = 0.10 mm−1
α = 82.283 (7)°	T = 120 K
β = 75.839 (7)°	Block, colourless
γ = 66.823 (6)°	0.62 × 0.44 × 0.22 mm
V = 649.87 (4) Å3

Rigaku R-AXIS conversion diffractometer	2969 independent reflections
Radiation source: Sealed Tube	2862 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.031
Detector resolution: 10.0000 pixels mm-1	θmax = 27.5°, θmin = 2.9°
profile data from ω–scans	h = −10→8
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	k = −10→10
Tmin = 0.878, Tmax = 1.000	l = −14→14
9715 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039	W = 1/[Σ2(FO2) + (0.0397P)2 + 0.2051P] WHERE P = (FO2 + 2FC2)/3
wR(F2) = 0.101	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.34 e Å−3
2969 reflections	Δρmin = −0.19 e Å−3
182 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
0 restraints	Extinction coefficient: 0.039 (4)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.02681 (11)	0.67683 (11)	0.39979 (7)	0.0234 (2)
O2	0.09562 (12)	0.63138 (10)	0.13897 (7)	0.0229 (2)
O3	0.42624 (12)	0.70766 (12)	0.54585 (8)	0.0310 (3)
O4	0.29048 (14)	0.91784 (11)	−0.12808 (8)	0.0335 (3)
C1	−0.10587 (16)	0.66169 (14)	0.33728 (10)	0.0222 (3)
C2	0.00997 (16)	0.53887 (14)	0.23588 (10)	0.0221 (3)
C3	−0.04430 (16)	0.76808 (13)	0.50371 (9)	0.0198 (3)
C4	0.09320 (16)	0.78082 (14)	0.55953 (10)	0.0203 (3)
C5	0.03276 (17)	0.87486 (14)	0.66511 (10)	0.0238 (3)
C6	−0.16055 (18)	0.95186 (15)	0.71668 (10)	0.0264 (3)
C7	−0.29501 (17)	0.93499 (15)	0.66234 (10)	0.0254 (3)
C8	−0.23910 (16)	0.84489 (14)	0.55568 (10)	0.0225 (3)
C9	0.29937 (16)	0.69362 (15)	0.50767 (10)	0.0235 (3)
C10	0.20867 (15)	0.54157 (14)	0.03822 (10)	0.0201 (3)
C11	0.28537 (16)	0.63720 (14)	−0.05755 (10)	0.0205 (3)
C12	0.40808 (16)	0.55234 (15)	−0.16216 (10)	0.0237 (3)
C13	0.45243 (17)	0.37632 (16)	−0.17322 (11)	0.0267 (3)
C14	0.37194 (17)	0.28415 (15)	−0.07953 (11)	0.0255 (3)
C15	0.25049 (17)	0.36520 (15)	0.02579 (10)	0.0228 (3)
C16	0.23854 (17)	0.82470 (15)	−0.04713 (11)	0.0252 (3)
H1A	−0.18070	0.77750	0.30370	0.0270*
H1B	−0.19620	0.61520	0.39420	0.0270*
H2A	0.11090	0.43660	0.26590	0.0270*
H2B	−0.07370	0.49650	0.20600	0.0270*
H5	0.12500	0.88620	0.70190	0.0290*
H6	−0.20120	1.01580	0.78860	0.0320*
H7	−0.42750	0.98600	0.69880	0.0300*
H8	−0.33240	0.83580	0.51880	0.0270*
H9	0.33550	0.62190	0.44020	0.0280*
H12	0.46170	0.61600	−0.22640	0.0280*
H13	0.53720	0.31880	−0.24420	0.0320*
H14	0.40060	0.16380	−0.08780	0.0310*
H15	0.19620	0.30080	0.08900	0.0270*
H16	0.16270	0.87630	0.02780	0.0300*

	U11	U22	U33	U12	U13	U23
O1	0.0200 (4)	0.0302 (4)	0.0205 (4)	−0.0089 (3)	−0.0034 (3)	−0.0061 (3)
O2	0.0284 (4)	0.0212 (4)	0.0187 (4)	−0.0107 (3)	−0.0016 (3)	−0.0015 (3)
O3	0.0251 (5)	0.0358 (5)	0.0361 (5)	−0.0147 (4)	−0.0104 (4)	0.0025 (4)
O4	0.0444 (6)	0.0263 (4)	0.0336 (5)	−0.0190 (4)	−0.0086 (4)	0.0051 (4)
C1	0.0208 (5)	0.0257 (5)	0.0218 (5)	−0.0099 (4)	−0.0053 (4)	−0.0010 (4)
C2	0.0255 (6)	0.0231 (5)	0.0197 (5)	−0.0118 (4)	−0.0047 (4)	0.0009 (4)
C3	0.0227 (5)	0.0180 (5)	0.0180 (5)	−0.0084 (4)	−0.0031 (4)	0.0013 (4)
C4	0.0231 (5)	0.0192 (5)	0.0193 (5)	−0.0100 (4)	−0.0044 (4)	0.0035 (4)
C5	0.0310 (6)	0.0215 (5)	0.0222 (5)	−0.0123 (5)	−0.0090 (4)	0.0026 (4)
C6	0.0341 (6)	0.0218 (5)	0.0203 (5)	−0.0087 (5)	−0.0028 (5)	−0.0026 (4)
C7	0.0240 (6)	0.0220 (5)	0.0244 (5)	−0.0059 (4)	0.0002 (4)	−0.0003 (4)
C8	0.0215 (5)	0.0230 (5)	0.0228 (5)	−0.0090 (4)	−0.0043 (4)	0.0006 (4)
C9	0.0240 (6)	0.0250 (5)	0.0219 (5)	−0.0107 (4)	−0.0056 (4)	0.0035 (4)
C10	0.0199 (5)	0.0228 (5)	0.0190 (5)	−0.0077 (4)	−0.0068 (4)	−0.0013 (4)
C11	0.0210 (5)	0.0220 (5)	0.0210 (5)	−0.0093 (4)	−0.0077 (4)	0.0009 (4)
C12	0.0245 (6)	0.0262 (6)	0.0212 (5)	−0.0103 (4)	−0.0055 (4)	0.0005 (4)
C13	0.0284 (6)	0.0272 (6)	0.0217 (5)	−0.0079 (5)	−0.0029 (4)	−0.0045 (4)
C14	0.0299 (6)	0.0206 (5)	0.0264 (6)	−0.0082 (4)	−0.0079 (5)	−0.0030 (4)
C15	0.0264 (6)	0.0224 (5)	0.0219 (5)	−0.0111 (4)	−0.0071 (4)	0.0015 (4)
C16	0.0296 (6)	0.0234 (5)	0.0246 (5)	−0.0106 (5)	−0.0087 (5)	−0.0001 (4)

O1—C1	1.4337 (16)	C12—C13	1.3834 (17)
O1—C3	1.3611 (13)	C13—C14	1.3910 (18)
O2—C2	1.4332 (14)	C14—C15	1.3876 (17)
O2—C10	1.3593 (13)	C1—H1A	0.9900
O3—C9	1.2166 (17)	C1—H1B	0.9900
O4—C16	1.2147 (15)	C2—H2A	0.9900
C1—C2	1.5011 (15)	C2—H2B	0.9900
C3—C4	1.4081 (18)	C5—H5	0.9500
C3—C8	1.3940 (18)	C6—H6	0.9500
C4—C5	1.3942 (15)	C7—H7	0.9500
C4—C9	1.4731 (18)	C8—H8	0.9500
C5—C6	1.3839 (19)	C9—H9	0.9500
C6—C7	1.392 (2)	C12—H12	0.9500
C7—C8	1.3906 (16)	C13—H13	0.9500
C10—C11	1.4090 (16)	C14—H14	0.9500
C10—C15	1.3929 (16)	C15—H15	0.9500
C11—C12	1.3951 (16)	C16—H16	0.9500
C11—C16	1.4717 (16)
C1—O1—C3	118.45 (10)	C2—C1—H1A	110.00
C2—O2—C10	117.35 (8)	C2—C1—H1B	110.00
O1—C1—C2	107.09 (10)	H1A—C1—H1B	109.00
O2—C2—C1	108.23 (9)	O2—C2—H2A	110.00
O1—C3—C4	115.69 (11)	O2—C2—H2B	110.00
O1—C3—C8	124.17 (11)	C1—C2—H2A	110.00
C4—C3—C8	120.14 (10)	C1—C2—H2B	110.00
C3—C4—C5	119.49 (11)	H2A—C2—H2B	108.00
C3—C4—C9	120.26 (10)	C4—C5—H5	120.00
C5—C4—C9	120.24 (12)	C6—C5—H5	120.00
C4—C5—C6	120.50 (12)	C5—C6—H6	120.00
C5—C6—C7	119.52 (11)	C7—C6—H6	120.00
C6—C7—C8	121.24 (12)	C6—C7—H7	119.00
C3—C8—C7	119.08 (12)	C8—C7—H7	119.00
O3—C9—C4	124.12 (11)	C3—C8—H8	120.00
O2—C10—C11	116.23 (9)	C7—C8—H8	120.00
O2—C10—C15	123.99 (10)	O3—C9—H9	118.00
C11—C10—C15	119.79 (10)	C4—C9—H9	118.00
C10—C11—C12	119.48 (10)	C11—C12—H12	120.00
C10—C11—C16	120.45 (10)	C13—C12—H12	120.00
C12—C11—C16	120.07 (11)	C12—C13—H13	120.00
C11—C12—C13	120.59 (11)	C14—C13—H13	120.00
C12—C13—C14	119.48 (11)	C13—C14—H14	119.00
C13—C14—C15	121.06 (11)	C15—C14—H14	119.00
C10—C15—C14	119.57 (11)	C10—C15—H15	120.00
O4—C16—C11	124.30 (11)	C14—C15—H15	120.00
O1—C1—H1A	110.00	O4—C16—H16	118.00
O1—C1—H1B	110.00	C11—C16—H16	118.00
C3—O1—C1—C2	−173.57 (9)	C4—C5—C6—C7	−0.04 (16)
C1—O1—C3—C8	1.68 (15)	C5—C6—C7—C8	−1.24 (17)
C1—O1—C3—C4	−178.90 (9)	C6—C7—C8—C3	0.98 (17)
C10—O2—C2—C1	179.42 (10)	O2—C10—C11—C12	177.80 (11)
C2—O2—C10—C15	−2.20 (18)	O2—C10—C11—C16	−1.51 (18)
C2—O2—C10—C11	177.73 (11)	C15—C10—C11—C12	−2.27 (19)
O1—C1—C2—O2	−76.50 (11)	C15—C10—C11—C16	178.42 (12)
O1—C3—C4—C9	−1.99 (15)	O2—C10—C15—C14	−178.22 (12)
C8—C3—C4—C5	−1.78 (16)	C11—C10—C15—C14	1.9 (2)
O1—C3—C8—C7	179.93 (9)	C10—C11—C12—C13	1.0 (2)
C4—C3—C8—C7	0.54 (16)	C16—C11—C12—C13	−179.70 (13)
C8—C3—C4—C9	177.46 (10)	C10—C11—C16—O4	−175.87 (13)
O1—C3—C4—C5	178.78 (10)	C12—C11—C16—O4	4.8 (2)
C3—C4—C9—O3	175.10 (11)	C11—C12—C13—C14	0.7 (2)
C5—C4—C9—O3	−5.67 (18)	C12—C13—C14—C15	−1.1 (2)
C3—C4—C5—C6	1.53 (16)	C13—C14—C15—C10	−0.2 (2)
C9—C4—C5—C6	−177.71 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3i	0.95	2.44	3.2508 (17)	144
C9—H9···O1	0.95	2.40	2.7412 (16)	101
C16—H16···O2	0.95	2.42	2.7561 (15)	101
C2—H2A···Cg1ii	0.99	2.68	3.4220 (12)	132
C2—H2B···Cg2iii	0.99	2.70	3.5964 (14)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C3–C8 and C10–C15 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O3i	0.95	2.44	3.2508 (17)	144
C2—H2A⋯Cg1ii	0.99	2.68	3.4220 (12)	132
C2—H2B⋯Cg2iii	0.99	2.70	3.5964 (14)	151

Symmetry codes: (i) ; (ii) ; (iii) .