1,4-Bis[(3,5-dimethoxy-phen-yl)ethyn-yl]benzene.

The title compound, C(26)H(22)O(4), is a derivative of 1,4-bis-(phenyl-ethyn-yl)benzene substituted by four meth-oxy groups on the terminal benzene rings. The mol-ecule is almost planar with an r.m.s. deviation of 0.266 Å. The dihedral angles between the two terminal benzene rings and the central benzene ring are 7.96 (6) and 13.32 (7)°. In the crystal structure, mol-ecules aggregate via C-H⋯O inter-actions, forming mol-ecular tapes along the a axis, which aggregate to form a herring-bone structure.

Related literature

For the crystal structure of 1,4-bis­[(2,6-dimethoxy­phen­yl)ethyn­yl]benzene, see: Ono et al. (2008 ▶). For related sructures, including a 1,4-bis­(phenyl­ethyn­yl)benzene system, see: Watt et al. (2004 ▶); Li et al. (1998 ▶); Filatov & Petrukhina (2005 ▶).

Experimental

Crystal data

C26H22O4

M = 398.44

Monoclinic,

a = 8.8980 (5) Å

b = 19.4610 (8) Å

c = 12.2820 (5) Å

β = 100.607 (1)°

V = 2090.46 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 (1) K

0.30 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: none

15238 measured reflections

4638 independent reflections

3914 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.140

S = 1.11

4638 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900155X/ci2753sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900155X/ci2753Isup2.hkl

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

C26H22O4	F(000) = 840
Mr = 398.44	Dx = 1.266 Mg m−3
Monoclinic, P21/a	Melting point: 431 K
Hall symbol: -P 2yab	Mo Kα radiation, λ = 0.71073 Å
a = 8.8980 (5) Å	Cell parameters from 5437 reflections
b = 19.4610 (8) Å	θ = 3.1–27.5°
c = 12.2820 (5) Å	µ = 0.09 mm−1
β = 100.607 (1)°	T = 173 K
V = 2090.46 (17) Å3	Block, yellow
Z = 4	0.30 × 0.25 × 0.15 mm

Rigaku Mercury CCD diffractometer	3914 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.024
Graphite Monochromator	θmax = 27.5°, θmin = 3.1°
Detector resolution: 14.7059 pixels mm-1	h = −11→10
φ and ω scans	k = −22→25
15238 measured reflections	l = −15→12
4638 independent reflections

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0818P)2 + 0.1522P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
4638 reflections	Δρmax = 0.26 e Å−3
271 parameters	Δρmin = −0.17 e Å−3
0 restraints

Experimental. IR (KBr, cm-1): 1605, 1580, 1345, 1254, 1202, 1161, 1065, 841; 1H NMR (CDCl3, δ p.p.m.): 3.81 (s, 12H), 6.48 (t, J = 2.3 Hz, 2H), 6.70 (d, J = 2.3 Hz, 4H), 7.51 (s, 4H); 13C NMR (CDCl3, δ p.p.m.): 55.3, 88.6, 91.3, 102.0, 109.4, 123.0, 124.3, 131.6, 160.6; MS (EI): m/z 398 (M+), 199.

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	0.04347 (14)	0.17522 (6)	0.71287 (10)	0.0266 (3)
C2	−0.11459 (14)	0.17481 (6)	0.67760 (11)	0.0266 (3)
H2	−0.1799	0.1980	0.7185	0.032*
C3	−0.17430 (13)	0.13932 (6)	0.58033 (11)	0.0265 (3)
C4	−0.07979 (14)	0.10623 (6)	0.51948 (11)	0.0277 (3)
H4	−0.1225	0.0824	0.4535	0.033*
C5	0.07839 (14)	0.10787 (6)	0.55512 (10)	0.0261 (3)
C6	0.14059 (14)	0.14194 (6)	0.65309 (11)	0.0283 (3)
H6	0.2480	0.1424	0.6787	0.034*
C7	0.17340 (14)	0.07642 (6)	0.48619 (11)	0.0288 (3)
C8	0.24292 (14)	0.05168 (7)	0.42138 (11)	0.0288 (3)
C9	0.32492 (14)	0.02180 (6)	0.34289 (10)	0.0262 (3)
C10	0.24597 (14)	−0.01164 (7)	0.24864 (11)	0.0286 (3)
H10	0.1377	−0.0150	0.2371	0.034*
C11	0.32439 (14)	−0.03986 (7)	0.17214 (11)	0.0303 (3)
H11	0.2695	−0.0621	0.1081	0.036*
C12	0.48372 (14)	−0.03594 (6)	0.18839 (10)	0.0273 (3)
C13	0.56275 (14)	−0.00329 (6)	0.28348 (11)	0.0297 (3)
H13	0.6712	−0.0009	0.2959	0.036*
C14	0.48439 (14)	0.02550 (7)	0.35943 (11)	0.0295 (3)
H14	0.5392	0.0479	0.4233	0.035*
C15	0.56748 (14)	−0.06453 (7)	0.10994 (11)	0.0305 (3)
C16	0.64138 (15)	−0.08764 (7)	0.04662 (11)	0.0313 (3)
C17	0.73414 (14)	−0.11338 (6)	−0.02860 (11)	0.0289 (3)
C18	0.67256 (14)	−0.15780 (7)	−0.11433 (11)	0.0309 (3)
H18	0.5689	−0.1720	−0.1231	0.037*
C19	0.76419 (14)	−0.18118 (7)	−0.18695 (11)	0.0289 (3)
C20	0.91672 (14)	−0.16179 (7)	−0.17484 (11)	0.0289 (3)
H20	0.9792	−0.1787	−0.2238	0.035*
C21	0.97568 (14)	−0.11696 (7)	−0.08931 (11)	0.0310 (3)
C22	0.88622 (14)	−0.09254 (7)	−0.01627 (11)	0.0316 (3)
H22	0.9283	−0.0619	0.0416	0.038*
C23	0.02302 (18)	0.24526 (8)	0.87014 (12)	0.0434 (4)
H23A	0.0889	0.2677	0.9328	0.065*
H23B	−0.0440	0.2122	0.8980	0.065*
H23C	−0.0392	0.2800	0.8247	0.065*
C24	−0.43253 (15)	0.17035 (8)	0.58918 (13)	0.0409 (4)
H24A	−0.5365	0.1618	0.5488	0.061*
H24B	−0.4108	0.2197	0.5890	0.061*
H24C	−0.4236	0.1543	0.6657	0.061*
C25	0.77935 (17)	−0.24753 (8)	−0.34851 (12)	0.0398 (3)
H25A	0.7151	−0.2772	−0.4025	0.060*
H25B	0.8679	−0.2737	−0.3107	0.060*
H25C	0.8146	−0.2082	−0.3868	0.060*
C26	1.22202 (17)	−0.11600 (9)	−0.14105 (15)	0.0506 (4)
H26A	1.3229	−0.0950	−0.1178	0.076*
H26B	1.1803	−0.1025	−0.2175	0.076*
H26C	1.2316	−0.1661	−0.1366	0.076*
O1	0.11541 (10)	0.21008 (5)	0.80454 (8)	0.0360 (2)
O2	−0.32622 (10)	0.13442 (5)	0.53688 (8)	0.0352 (2)
O3	0.69301 (10)	−0.22363 (5)	−0.26936 (9)	0.0396 (3)
O4	1.12292 (11)	−0.09341 (6)	−0.07075 (9)	0.0477 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0340 (6)	0.0247 (6)	0.0213 (6)	0.0006 (5)	0.0059 (5)	−0.0006 (5)
C2	0.0318 (6)	0.0241 (6)	0.0263 (7)	0.0011 (5)	0.0113 (5)	−0.0004 (5)
C3	0.0273 (6)	0.0244 (6)	0.0287 (7)	−0.0013 (4)	0.0073 (5)	0.0015 (5)
C4	0.0345 (6)	0.0257 (6)	0.0235 (6)	−0.0007 (5)	0.0068 (5)	−0.0036 (5)
C5	0.0322 (6)	0.0232 (6)	0.0249 (6)	0.0034 (5)	0.0106 (5)	0.0016 (5)
C6	0.0280 (6)	0.0281 (6)	0.0291 (7)	0.0025 (5)	0.0058 (5)	−0.0005 (5)
C7	0.0314 (6)	0.0279 (6)	0.0277 (7)	0.0016 (5)	0.0071 (5)	−0.0007 (5)
C8	0.0324 (6)	0.0280 (6)	0.0266 (7)	0.0020 (5)	0.0069 (5)	−0.0004 (5)
C9	0.0309 (6)	0.0248 (6)	0.0243 (6)	0.0033 (5)	0.0089 (5)	0.0012 (5)
C10	0.0266 (6)	0.0331 (7)	0.0265 (7)	0.0027 (5)	0.0061 (5)	−0.0005 (5)
C11	0.0340 (6)	0.0338 (7)	0.0226 (6)	0.0014 (5)	0.0042 (5)	−0.0045 (5)
C12	0.0330 (6)	0.0269 (6)	0.0238 (6)	0.0043 (5)	0.0103 (5)	0.0000 (5)
C13	0.0277 (6)	0.0333 (7)	0.0293 (7)	0.0007 (5)	0.0083 (5)	−0.0012 (5)
C14	0.0325 (6)	0.0316 (6)	0.0248 (7)	−0.0015 (5)	0.0064 (5)	−0.0051 (5)
C15	0.0346 (6)	0.0303 (7)	0.0278 (7)	0.0033 (5)	0.0086 (5)	−0.0006 (5)
C16	0.0358 (6)	0.0316 (7)	0.0278 (7)	0.0036 (5)	0.0092 (5)	−0.0007 (5)
C17	0.0344 (6)	0.0299 (6)	0.0238 (6)	0.0062 (5)	0.0089 (5)	0.0002 (5)
C18	0.0286 (6)	0.0338 (7)	0.0322 (7)	−0.0007 (5)	0.0109 (5)	−0.0034 (6)
C19	0.0317 (6)	0.0294 (6)	0.0259 (7)	−0.0011 (5)	0.0065 (5)	−0.0044 (5)
C20	0.0296 (6)	0.0330 (7)	0.0255 (7)	0.0018 (5)	0.0091 (5)	−0.0038 (5)
C21	0.0286 (6)	0.0363 (7)	0.0285 (7)	−0.0008 (5)	0.0057 (5)	−0.0029 (5)
C22	0.0356 (7)	0.0348 (7)	0.0244 (7)	0.0003 (5)	0.0057 (5)	−0.0071 (5)
C23	0.0512 (8)	0.0486 (9)	0.0291 (8)	0.0112 (7)	0.0037 (6)	−0.0135 (7)
C24	0.0286 (6)	0.0471 (9)	0.0487 (9)	0.0001 (6)	0.0112 (6)	−0.0110 (7)
C25	0.0459 (8)	0.0429 (8)	0.0324 (8)	−0.0052 (6)	0.0121 (6)	−0.0150 (6)
C26	0.0339 (7)	0.0718 (12)	0.0499 (10)	−0.0131 (7)	0.0179 (7)	−0.0190 (8)
O1	0.0364 (5)	0.0429 (6)	0.0274 (5)	0.0056 (4)	0.0023 (4)	−0.0123 (4)
O2	0.0271 (4)	0.0380 (5)	0.0403 (6)	−0.0022 (4)	0.0062 (4)	−0.0102 (4)
O3	0.0361 (5)	0.0459 (6)	0.0390 (6)	−0.0091 (4)	0.0123 (4)	−0.0198 (5)
O4	0.0302 (5)	0.0698 (7)	0.0446 (7)	−0.0122 (5)	0.0112 (4)	−0.0260 (6)

C1—O1	1.3684 (15)	C17—C22	1.3940 (18)
C1—C6	1.3924 (16)	C17—C18	1.3942 (18)
C1—C2	1.3933 (17)	C18—C19	1.3911 (16)
C2—C3	1.3975 (18)	C18—H18	0.95
C2—H2	0.95	C19—O3	1.3683 (15)
C3—O2	1.3622 (15)	C19—C20	1.3900 (17)
C3—C4	1.3826 (16)	C20—C21	1.3917 (18)
C4—C5	1.3953 (17)	C20—H20	0.95
C4—H4	0.95	C21—O4	1.3670 (15)
C5—C6	1.3960 (18)	C21—C22	1.3882 (17)
C5—C7	1.4386 (16)	C22—H22	0.95
C6—H6	0.95	C23—O1	1.4274 (16)
C7—C8	1.1956 (17)	C23—H23A	0.98
C8—C9	1.4348 (16)	C23—H23B	0.98
C9—C14	1.3977 (17)	C23—H23C	0.98
C9—C10	1.3991 (18)	C24—O2	1.4213 (15)
C10—C11	1.3831 (17)	C24—H24A	0.98
C10—H10	0.95	C24—H24B	0.98
C11—C12	1.3969 (17)	C24—H24C	0.98
C11—H11	0.95	C25—O3	1.4236 (16)
C12—C13	1.3999 (18)	C25—H25A	0.98
C12—C15	1.4345 (16)	C25—H25B	0.98
C13—C14	1.3820 (17)	C25—H25C	0.98
C13—H13	0.95	C26—O4	1.4130 (17)
C14—H14	0.95	C26—H26A	0.98
C15—C16	1.1949 (18)	C26—H26B	0.98
C16—C17	1.4375 (17)	C26—H26C	0.98
O1—C1—C6	115.01 (10)	C19—C18—C17	119.46 (11)
O1—C1—C2	123.44 (11)	C19—C18—H18	120.3
C6—C1—C2	121.49 (11)	C17—C18—H18	120.3
C1—C2—C3	118.14 (11)	O3—C19—C20	123.57 (11)
C1—C2—H2	120.9	O3—C19—C18	115.19 (11)
C3—C2—H2	120.9	C20—C19—C18	121.24 (12)
O2—C3—C4	114.46 (11)	C19—C20—C21	118.42 (11)
O2—C3—C2	124.28 (11)	C19—C20—H20	120.8
C4—C3—C2	121.26 (11)	C21—C20—H20	120.8
C3—C4—C5	119.91 (11)	O4—C21—C22	115.05 (12)
C3—C4—H4	120.0	O4—C21—C20	123.55 (11)
C5—C4—H4	120.0	C22—C21—C20	121.40 (11)
C4—C5—C6	119.88 (11)	C21—C22—C17	119.40 (12)
C4—C5—C7	118.29 (11)	C21—C22—H22	120.3
C6—C5—C7	121.78 (11)	C17—C22—H22	120.3
C1—C6—C5	119.30 (11)	O1—C23—H23A	109.5
C1—C6—H6	120.4	O1—C23—H23B	109.5
C5—C6—H6	120.4	H23A—C23—H23B	109.5
C8—C7—C5	174.44 (14)	O1—C23—H23C	109.5
C7—C8—C9	179.42 (15)	H23A—C23—H23C	109.5
C14—C9—C10	119.07 (11)	H23B—C23—H23C	109.5
C14—C9—C8	120.64 (11)	O2—C24—H24A	109.5
C10—C9—C8	120.29 (11)	O2—C24—H24B	109.5
C11—C10—C9	120.50 (11)	H24A—C24—H24B	109.5
C11—C10—H10	119.8	O2—C24—H24C	109.5
C9—C10—H10	119.8	H24A—C24—H24C	109.5
C10—C11—C12	120.45 (11)	H24B—C24—H24C	109.5
C10—C11—H11	119.8	O3—C25—H25A	109.5
C12—C11—H11	119.8	O3—C25—H25B	109.5
C11—C12—C13	119.00 (11)	H25A—C25—H25B	109.5
C11—C12—C15	121.46 (11)	O3—C25—H25C	109.5
C13—C12—C15	119.54 (11)	H25A—C25—H25C	109.5
C14—C13—C12	120.58 (11)	H25B—C25—H25C	109.5
C14—C13—H13	119.7	O4—C26—H26A	109.5
C12—C13—H13	119.7	O4—C26—H26B	109.5
C13—C14—C9	120.39 (12)	H26A—C26—H26B	109.5
C13—C14—H14	119.8	O4—C26—H26C	109.5
C9—C14—H14	119.8	H26A—C26—H26C	109.5
C16—C15—C12	177.95 (14)	H26B—C26—H26C	109.5
C15—C16—C17	177.90 (14)	C1—O1—C23	118.13 (10)
C22—C17—C18	120.08 (11)	C3—O2—C24	118.91 (10)
C22—C17—C16	119.31 (12)	C19—O3—C25	117.90 (10)
C18—C17—C16	120.60 (11)	C21—O4—C26	118.72 (11)
O1—C1—C2—C3	177.69 (11)	C8—C9—C14—C13	−179.92 (12)
C6—C1—C2—C3	0.59 (18)	C22—C17—C18—C19	0.2 (2)
C1—C2—C3—O2	179.60 (11)	C16—C17—C18—C19	179.07 (12)
C1—C2—C3—C4	−0.90 (18)	C17—C18—C19—O3	−178.99 (12)
O2—C3—C4—C5	179.63 (11)	C17—C18—C19—C20	0.8 (2)
C2—C3—C4—C5	0.08 (18)	O3—C19—C20—C21	178.44 (12)
C3—C4—C5—C6	1.06 (18)	C18—C19—C20—C21	−1.4 (2)
C3—C4—C5—C7	−176.30 (11)	C19—C20—C21—O4	−178.72 (13)
O1—C1—C6—C5	−176.80 (11)	C19—C20—C21—C22	0.9 (2)
C2—C1—C6—C5	0.53 (19)	O4—C21—C22—C17	179.75 (12)
C4—C5—C6—C1	−1.36 (18)	C20—C21—C22—C17	0.1 (2)
C7—C5—C6—C1	175.90 (11)	C18—C17—C22—C21	−0.6 (2)
C14—C9—C10—C11	−0.84 (19)	C16—C17—C22—C21	−179.55 (12)
C8—C9—C10—C11	179.30 (12)	C6—C1—O1—C23	−179.78 (12)
C9—C10—C11—C12	0.59 (19)	C2—C1—O1—C23	2.94 (18)
C10—C11—C12—C13	0.28 (19)	C4—C3—O2—C24	−175.99 (12)
C10—C11—C12—C15	−179.69 (12)	C2—C3—O2—C24	3.55 (18)
C11—C12—C13—C14	−0.90 (19)	C20—C19—O3—C25	−1.8 (2)
C15—C12—C13—C14	179.07 (12)	C18—C19—O3—C25	178.03 (12)
C12—C13—C14—C9	0.65 (19)	C22—C21—O4—C26	179.71 (14)
C10—C9—C14—C13	0.22 (19)	C20—C21—O4—C26	−0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4i	0.95	2.42	3.3511 (17)	167
C14—H14···O2ii	0.95	2.37	3.2758 (16)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O4i	0.95	2.42	3.3511 (17)	167
C14—H14⋯O2ii	0.95	2.37	3.2758 (16)	160

Symmetry codes: (i) ; (ii) .