(Z)-1,4-Diphenyl-but-1-en-3-ynyl acetate.

The title compound, C(18)H(14)O(2), is almost planar with a dihedral angle of 1.24 (2)° between the phenyl-ethynyl and styryl groups. The acet-oxy group is tilted by 82.46 (2) and 82.26 (3)° with respect to the benzene ring planes.

Related literature

For general background to title compound, see: Goossen & Paetzold (2004 ▶); Debergh et al. (2008 ▶); Li et al. (2010 ▶); Nakao et al. (2008 ▶); Chen et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H14O2

M = 262.29

Monoclinic,

a = 13.1480 (5) Å

b = 5.5912 (2) Å

c = 19.7579 (7) Å

β = 91.558 (2)°

V = 1451.93 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.33 × 0.28 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.987, T max = 0.998

8119 measured reflections

2611 independent reflections

1678 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.123

S = 1.02

2611 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.09 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037439/hg5238sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037439/hg5238Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037439/hg5238Isup3.cml

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

C18H14O2	F(000) = 552
Mr = 262.29	Dx = 1.200 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5837 reflections
a = 13.1480 (5) Å	θ = 2.8–27.9°
b = 5.5912 (2) Å	µ = 0.08 mm−1
c = 19.7579 (7) Å	T = 296 K
β = 91.558 (2)°	Block, colorless
V = 1451.93 (9) Å3	0.33 × 0.28 × 0.20 mm
Z = 4

Bruker APEXII area-detector diffractometer	2611 independent reflections
Radiation source: fine-focus sealed tube	1678 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scan	θmax = 25.2°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.987, Tmax = 0.998	k = −6→6
8119 measured reflections	l = −23→23

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.1384P] where P = (Fo2 + 2Fc2)/3
2611 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.09 e Å−3
0 restraints	Δρmin = −0.14 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	0.30322 (13)	−0.0799 (4)	0.49684 (9)	0.0692 (5)
C2	0.28690 (17)	−0.2708 (5)	0.53970 (12)	0.0953 (7)
H2	0.2419	−0.3916	0.5266	0.114*
C3	0.3369 (3)	−0.2826 (7)	0.60151 (15)	0.1280 (11)
H3	0.3254	−0.4111	0.6302	0.154*
C4	0.4031 (3)	−0.1080 (9)	0.62109 (15)	0.1426 (16)
H4	0.4372	−0.1181	0.6628	0.171*
C5	0.4196 (2)	0.0823 (8)	0.57961 (17)	0.1327 (12)
H5	0.4647	0.2021	0.5933	0.159*
C6	0.36951 (17)	0.0975 (5)	0.51739 (11)	0.0974 (7)
H6	0.3807	0.2280	0.4894	0.117*
C7	0.25155 (13)	−0.0651 (4)	0.43211 (10)	0.0701 (5)
C8	0.20928 (13)	−0.0556 (4)	0.37789 (10)	0.0685 (5)
C9	0.15912 (12)	−0.0526 (4)	0.31331 (9)	0.0652 (5)
H9	0.1158	−0.1790	0.3023	0.078*
C10	0.17019 (11)	0.1197 (3)	0.26765 (8)	0.0550 (4)
C11	0.11939 (11)	0.1374 (3)	0.20075 (8)	0.0536 (4)
C12	0.04989 (12)	−0.0339 (3)	0.17850 (8)	0.0650 (5)
H12	0.0366	−0.1650	0.2058	0.078*
C13	0.00025 (14)	−0.0127 (4)	0.11645 (10)	0.0748 (5)
H13	−0.0463	−0.1290	0.1024	0.090*
C14	0.01901 (15)	0.1784 (4)	0.07548 (9)	0.0752 (6)
H14	−0.0148	0.1929	0.0337	0.090*
C15	0.08782 (15)	0.3482 (4)	0.09637 (10)	0.0799 (6)
H15	0.1012	0.4776	0.0684	0.096*
C16	0.13779 (13)	0.3297 (3)	0.15865 (10)	0.0708 (5)
H16	0.1840	0.4472	0.1723	0.085*
C17	0.33312 (11)	0.2969 (3)	0.28114 (8)	0.0565 (4)
C18	0.38508 (13)	0.5103 (4)	0.30975 (10)	0.0770 (6)
H18A	0.4559	0.5052	0.2992	0.116*
H18B	0.3783	0.5121	0.3580	0.116*
H18C	0.3548	0.6521	0.2906	0.116*
O1	0.23034 (7)	0.3175 (2)	0.28623 (6)	0.0629 (3)
O2	0.37147 (8)	0.1261 (2)	0.25663 (7)	0.0784 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0638 (10)	0.0764 (14)	0.0674 (11)	0.0162 (10)	0.0031 (9)	−0.0050 (11)
C2	0.0945 (15)	0.0937 (18)	0.0979 (16)	0.0216 (13)	0.0047 (12)	0.0187 (14)
C3	0.146 (3)	0.151 (3)	0.0871 (19)	0.074 (2)	0.0098 (17)	0.0319 (19)
C4	0.136 (3)	0.212 (5)	0.0786 (19)	0.094 (3)	−0.0156 (18)	−0.027 (2)
C5	0.122 (2)	0.164 (3)	0.111 (2)	0.018 (2)	−0.0324 (18)	−0.054 (2)
C6	0.0986 (16)	0.1039 (19)	0.0890 (15)	−0.0034 (15)	−0.0102 (12)	−0.0148 (14)
C7	0.0626 (10)	0.0702 (14)	0.0776 (13)	0.0052 (9)	0.0032 (9)	0.0003 (10)
C8	0.0592 (10)	0.0669 (13)	0.0792 (12)	−0.0019 (9)	0.0016 (9)	0.0049 (10)
C9	0.0571 (9)	0.0617 (13)	0.0767 (12)	−0.0069 (9)	−0.0037 (8)	0.0016 (10)
C10	0.0426 (8)	0.0485 (11)	0.0743 (11)	−0.0014 (7)	0.0055 (7)	−0.0032 (9)
C11	0.0447 (8)	0.0499 (11)	0.0667 (10)	0.0022 (8)	0.0108 (7)	−0.0005 (8)
C12	0.0709 (11)	0.0572 (12)	0.0670 (11)	−0.0081 (9)	0.0066 (8)	0.0003 (9)
C13	0.0796 (12)	0.0722 (14)	0.0725 (12)	−0.0078 (11)	−0.0020 (9)	−0.0111 (11)
C14	0.0783 (12)	0.0820 (15)	0.0654 (11)	0.0095 (12)	0.0042 (9)	−0.0022 (11)
C15	0.0782 (12)	0.0777 (15)	0.0842 (13)	0.0033 (11)	0.0102 (10)	0.0242 (12)
C16	0.0594 (10)	0.0629 (13)	0.0900 (13)	−0.0070 (9)	0.0010 (9)	0.0126 (11)
C17	0.0472 (9)	0.0560 (11)	0.0664 (10)	0.0011 (8)	0.0024 (7)	0.0011 (9)
C18	0.0659 (11)	0.0718 (14)	0.0930 (13)	−0.0169 (10)	−0.0036 (9)	−0.0095 (11)
O1	0.0477 (6)	0.0512 (8)	0.0900 (8)	−0.0005 (5)	0.0040 (5)	−0.0097 (6)
O2	0.0554 (7)	0.0700 (9)	0.1103 (10)	0.0034 (6)	0.0143 (6)	−0.0190 (8)

C1—C6	1.374 (3)	C11—C16	1.385 (2)
C1—C2	1.383 (3)	C11—C12	1.387 (2)
C1—C7	1.434 (2)	C12—C13	1.378 (2)
C2—C3	1.373 (4)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.367 (3)
C3—C4	1.357 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.367 (3)
C4—C5	1.364 (5)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.383 (2)
C5—C6	1.381 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—O2	1.1894 (19)
C7—C8	1.194 (2)	C17—O1	1.3626 (18)
C8—C9	1.420 (2)	C17—C18	1.479 (2)
C9—C10	1.330 (2)	C18—H18A	0.9600
C9—H9	0.9300	C18—H18B	0.9600
C10—O1	1.4025 (18)	C18—H18C	0.9600
C10—C11	1.468 (2)
C6—C1—C2	118.9 (2)	C16—C11—C10	120.70 (15)
C6—C1—C7	120.2 (2)	C12—C11—C10	121.23 (15)
C2—C1—C7	120.9 (2)	C13—C12—C11	120.95 (18)
C3—C2—C1	120.2 (3)	C13—C12—H12	119.5
C3—C2—H2	119.9	C11—C12—H12	119.5
C1—C2—H2	119.9	C14—C13—C12	120.35 (19)
C4—C3—C2	120.5 (3)	C14—C13—H13	119.8
C4—C3—H3	119.8	C12—C13—H13	119.8
C2—C3—H3	119.8	C13—C14—C15	119.51 (18)
C3—C4—C5	120.1 (3)	C13—C14—H14	120.2
C3—C4—H4	120.0	C15—C14—H14	120.2
C5—C4—H4	120.0	C14—C15—C16	120.74 (18)
C4—C5—C6	120.2 (3)	C14—C15—H15	119.6
C4—C5—H5	119.9	C16—C15—H15	119.6
C6—C5—H5	119.9	C15—C16—C11	120.39 (17)
C1—C6—C5	120.1 (3)	C15—C16—H16	119.8
C1—C6—H6	120.0	C11—C16—H16	119.8
C5—C6—H6	120.0	O2—C17—O1	122.01 (16)
C8—C7—C1	179.1 (2)	O2—C17—C18	127.35 (15)
C7—C8—C9	178.1 (2)	O1—C17—C18	110.64 (15)
C10—C9—C8	124.12 (17)	C17—C18—H18A	109.5
C10—C9—H9	117.9	C17—C18—H18B	109.5
C8—C9—H9	117.9	H18A—C18—H18B	109.5
C9—C10—O1	117.69 (15)	C17—C18—H18C	109.5
C9—C10—C11	127.15 (15)	H18A—C18—H18C	109.5
O1—C10—C11	114.96 (14)	H18B—C18—H18C	109.5
C16—C11—C12	118.06 (16)	C17—O1—C10	117.88 (12)