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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2847
https://doi.org/10.1107/S1600536812037439

(Z)-1,4-Di­phenyl­but-1-en-3-ynyl acetate

Zheng-Wang Chen,a Hai-Chuan Chen,a Dong-Nai Yea and Qiao-Sheng Hua*

aKey Laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Gan Zhou 341000, People's Republic of China
*Correspondence e-mail: huqiaosheng@yahoo.com.cn

(Received 29 July 2012; accepted 30 August 2012; online 5 September 2012)

The title compound, C18H14O2, is almost planar with a dihedral angle of 1.24 (2)° between the phenyl­ethynyl and styryl groups. The acet­oxy 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[Goossen, L. J. & Paetzold, J. (2004). Angew. Chem. Int. Ed. 43, 1095-1098.]); Debergh et al. (2008[Debergh, J. R., Spivey, K. M. & Ready, J. M. (2008). J. Am. Chem. Soc. 130, 7828-7829.]); Li et al. (2010[Li, Y., Liu, X., Jiang, H. & Feng, Z. (2010). Angew. Chem. Int. Ed. 49, 3338-3341.]); Nakao et al. (2008[Nakao, Y., Hirata, Y., Tanaka, M. & Hiyama, T. (2008). Angew. Chem. Int. Ed. 47, 385-387.]); Chen et al. (2011[Chen, Z., Huang, G., Jiang, H., Huang, H. & Pan, X. (2011). J. Org. Chem. 76, 1134-1139.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C18H14O2

  • Mr = 262.29

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.987, Tmax = 0.998

  • 8119 measured reflections

  • 2611 independent reflections

  • 1678 reflections with I > 2σ(I)

  • Rint = 0.021
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 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[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812037439/hg5238sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037439/hg5238Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037439/hg5238Isup3.cml

checkCIF report


Comment top

The title compound, (I), C19H17N3O2, is a multifunctional compound, which can achieve varieties of conversion. For example, enol acetates was frequently used as intermediates in organic synthesis and pharmaceutical chemistry (Goossen et al., 2004; Debergh et al., 2008), the enyne derivatives had high synthetic potential due to wide applicability (Li et al., 2010; Nakao et al., 2008), and the enyne acetate could be converted to heterocyclic compounds through metal-catalyzed transformation or electrophilic cyclization (Chen et al., 2011). Moreover, the (Z)-enyne acetate was obtained from (Z)-2-bromoenol acetate and phenylacetylene, it proved that the Sonogashira coupling reaction was in stereospecific manner. In view of this, the crystal structure determination of the title compound was carried out and the results are presented here.

As depicted in Fig. 1, the phenylethynyl group (C1—C8) [maximum deviations of 0.007 (2) and 0.028 Å for the C7 and C8 atoms, respectively] and the styryl group (C9—C16) [maximum deviations of 0.058 (2) and 0.041 (3) Å for the C9 and C10 atoms, respectively] are almost planar with maximum deviation of 1.24 (2) °. The acetoxy group (C17/C18/O1/O2) is slight tilted with respect to the benzene mean planes by 82.46 (2) (C11—C16) and 82.26 (3) ° (C1—C6). The bond lengths are within normal range (Allen et al., 1987). The molecules are linked into an infinite chain through intermolecular C18—H18A···O2 hydrogen bonding interactions. In addition, intramolecular C16—H16···O1 are also observed.

Related literature top

For general background to title compound, see: Goossen et al. (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 top

To the mixture of (Z)-2-bromoenol acetate (1 mmol, 0.241 g), Pd(OAc)2 (0.05 mmol, 0.011 g) and PPh3 (0.1 mmol, 0.026 g) in THF (2 ml) solvent, TEA (1 mmol, 0.101 g) and CuI (0.05 mmol, 0.0098 g) were added successively, stirred for five minutes at room temperature, phenylacetylene (2.0 mmol, 0.204 g) was added, the flask was then sealed and stirred at 323 K for 6 h. The solution was washed with water (10 ml) and extracted with ethyl acetate (24 ml), and the combined extract was dried with anhydrous MgSO4. Solvent was removed, and the residue was purified by silica gel (200–300 mesh) column by elution with petroleum ether: ethyl acetate (10:1) to give 20 fractions (200 ml per fraction). The title compound (252.8 mg) was isolated from the fractions 5–16 (yield 96.5%). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Refinement top

All H atoms were located on the difference maps, and were treated as riding atoms with C—H distances of 0.96Å for methyl, with Uiso(H) = 1.5Ueq (methyl C-atoms) and 1.2Ueq(non-methyl C-atoms). The hightest peak is located 1.07Å from O2 and the deepest hole is located 0.97 Å from C6.

Structure description top

The title compound, (I), C19H17N3O2, is a multifunctional compound, which can achieve varieties of conversion. For example, enol acetates was frequently used as intermediates in organic synthesis and pharmaceutical chemistry (Goossen et al., 2004; Debergh et al., 2008), the enyne derivatives had high synthetic potential due to wide applicability (Li et al., 2010; Nakao et al., 2008), and the enyne acetate could be converted to heterocyclic compounds through metal-catalyzed transformation or electrophilic cyclization (Chen et al., 2011). Moreover, the (Z)-enyne acetate was obtained from (Z)-2-bromoenol acetate and phenylacetylene, it proved that the Sonogashira coupling reaction was in stereospecific manner. In view of this, the crystal structure determination of the title compound was carried out and the results are presented here.

As depicted in Fig. 1, the phenylethynyl group (C1—C8) [maximum deviations of 0.007 (2) and 0.028 Å for the C7 and C8 atoms, respectively] and the styryl group (C9—C16) [maximum deviations of 0.058 (2) and 0.041 (3) Å for the C9 and C10 atoms, respectively] are almost planar with maximum deviation of 1.24 (2) °. The acetoxy group (C17/C18/O1/O2) is slight tilted with respect to the benzene mean planes by 82.46 (2) (C11—C16) and 82.26 (3) ° (C1—C6). The bond lengths are within normal range (Allen et al., 1987). The molecules are linked into an infinite chain through intermolecular C18—H18A···O2 hydrogen bonding interactions. In addition, intramolecular C16—H16···O1 are also observed.

For general background to title compound, see: Goossen et al. (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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the tile compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. An infinite chain of the title compound; C—H···O interactions are shown as dashed lines. The H-atoms not involved in H-bonds have been excluded for clarity.
(Z)-1,4-Diphenylbut-1-en-3-ynyl acetate top
Crystal data top
C18H14O2F(000) = 552
Mr = 262.29Dx = 1.200 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5837 reflections
a = 13.1480 (5) Åθ = 2.8–27.9°
b = 5.5912 (2) ŵ = 0.08 mm−1
c = 19.7579 (7) ÅT = 296 K
β = 91.558 (2)°Block, colorless
V = 1451.93 (9) Å30.33 × 0.28 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII area-detector
diffractometer		2611 independent reflections
Radiation source: fine-focus sealed tube1678 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scanθmax = 25.2°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→15
Tmin = 0.987, Tmax = 0.998k = −6→6
8119 measured reflectionsl = −23→23
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-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 parametersΔρmax = 0.09 e Å−3
0 restraintsΔρmin = −0.14 e Å−3
Crystal data top
C18H14O2V = 1451.93 (9) Å3
Mr = 262.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.1480 (5) ŵ = 0.08 mm−1
b = 5.5912 (2) ÅT = 296 K
c = 19.7579 (7) Å0.33 × 0.28 × 0.20 mm
β = 91.558 (2)°
Data collection top
Bruker APEXII area-detector
diffractometer		2611 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1678 reflections with I > 2σ(I)
Tmin = 0.987, Tmax = 0.998Rint = 0.021
8119 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.02Δρmax = 0.09 e Å−3
2611 reflectionsΔρmin = −0.14 e Å−3
182 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.30322 (13)−0.0799 (4)0.49684 (9)0.0692 (5)
C20.28690 (17)−0.2708 (5)0.53970 (12)0.0953 (7)
H20.2419−0.39160.52660.114*
C30.3369 (3)−0.2826 (7)0.60151 (15)0.1280 (11)
H30.3254−0.41110.63020.154*
C40.4031 (3)−0.1080 (9)0.62109 (15)0.1426 (16)
H40.4372−0.11810.66280.171*
C50.4196 (2)0.0823 (8)0.57961 (17)0.1327 (12)
H50.46470.20210.59330.159*
C60.36951 (17)0.0975 (5)0.51739 (11)0.0974 (7)
H60.38070.22800.48940.117*
C70.25155 (13)−0.0651 (4)0.43211 (10)0.0701 (5)
C80.20928 (13)−0.0556 (4)0.37789 (10)0.0685 (5)
C90.15912 (12)−0.0526 (4)0.31331 (9)0.0652 (5)
H90.1158−0.17900.30230.078*
C100.17019 (11)0.1197 (3)0.26765 (8)0.0550 (4)
C110.11939 (11)0.1374 (3)0.20075 (8)0.0536 (4)
C120.04989 (12)−0.0339 (3)0.17850 (8)0.0650 (5)
H120.0366−0.16500.20580.078*
C130.00025 (14)−0.0127 (4)0.11645 (10)0.0748 (5)
H13−0.0463−0.12900.10240.090*
C140.01901 (15)0.1784 (4)0.07548 (9)0.0752 (6)
H14−0.01480.19290.03370.090*
C150.08782 (15)0.3482 (4)0.09637 (10)0.0799 (6)
H150.10120.47760.06840.096*
C160.13779 (13)0.3297 (3)0.15865 (10)0.0708 (5)
H160.18400.44720.17230.085*
C170.33312 (11)0.2969 (3)0.28114 (8)0.0565 (4)
C180.38508 (13)0.5103 (4)0.30975 (10)0.0770 (6)
H18A0.45590.50520.29920.116*
H18B0.37830.51210.35800.116*
H18C0.35480.65210.29060.116*
O10.23034 (7)0.3175 (2)0.28623 (6)0.0629 (3)
O20.37147 (8)0.1261 (2)0.25663 (7)0.0784 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0638 (10)0.0764 (14)0.0674 (11)0.0162 (10)0.0031 (9)−0.0050 (11)
C20.0945 (15)0.0937 (18)0.0979 (16)0.0216 (13)0.0047 (12)0.0187 (14)
C30.146 (3)0.151 (3)0.0871 (19)0.074 (2)0.0098 (17)0.0319 (19)
C40.136 (3)0.212 (5)0.0786 (19)0.094 (3)−0.0156 (18)−0.027 (2)
C50.122 (2)0.164 (3)0.111 (2)0.018 (2)−0.0324 (18)−0.054 (2)
C60.0986 (16)0.1039 (19)0.0890 (15)−0.0034 (15)−0.0102 (12)−0.0148 (14)
C70.0626 (10)0.0702 (14)0.0776 (13)0.0052 (9)0.0032 (9)0.0003 (10)
C80.0592 (10)0.0669 (13)0.0792 (12)−0.0019 (9)0.0016 (9)0.0049 (10)
C90.0571 (9)0.0617 (13)0.0767 (12)−0.0069 (9)−0.0037 (8)0.0016 (10)
C100.0426 (8)0.0485 (11)0.0743 (11)−0.0014 (7)0.0055 (7)−0.0032 (9)
C110.0447 (8)0.0499 (11)0.0667 (10)0.0022 (8)0.0108 (7)−0.0005 (8)
C120.0709 (11)0.0572 (12)0.0670 (11)−0.0081 (9)0.0066 (8)0.0003 (9)
C130.0796 (12)0.0722 (14)0.0725 (12)−0.0078 (11)−0.0020 (9)−0.0111 (11)
C140.0783 (12)0.0820 (15)0.0654 (11)0.0095 (12)0.0042 (9)−0.0022 (11)
C150.0782 (12)0.0777 (15)0.0842 (13)0.0033 (11)0.0102 (10)0.0242 (12)
C160.0594 (10)0.0629 (13)0.0900 (13)−0.0070 (9)0.0010 (9)0.0126 (11)
C170.0472 (9)0.0560 (11)0.0664 (10)0.0011 (8)0.0024 (7)0.0011 (9)
C180.0659 (11)0.0718 (14)0.0930 (13)−0.0169 (10)−0.0036 (9)−0.0095 (11)
O10.0477 (6)0.0512 (8)0.0900 (8)−0.0005 (5)0.0040 (5)−0.0097 (6)
O20.0554 (7)0.0700 (9)0.1103 (10)0.0034 (6)0.0143 (6)−0.0190 (8)
Geometric parameters (Å, º) top
C1—C61.374 (3)C11—C161.385 (2)
C1—C21.383 (3)C11—C121.387 (2)
C1—C71.434 (2)C12—C131.378 (2)
C2—C31.373 (4)C12—H120.9300
C2—H20.9300C13—C141.367 (3)
C3—C41.357 (5)C13—H130.9300
C3—H30.9300C14—C151.367 (3)
C4—C51.364 (5)C14—H140.9300
C4—H40.9300C15—C161.383 (2)
C5—C61.381 (3)C15—H150.9300
C5—H50.9300C16—H160.9300
C6—H60.9300C17—O21.1894 (19)
C7—C81.194 (2)C17—O11.3626 (18)
C8—C91.420 (2)C17—C181.479 (2)
C9—C101.330 (2)C18—H18A0.9600
C9—H90.9300C18—H18B0.9600
C10—O11.4025 (18)C18—H18C0.9600
C10—C111.468 (2)
C6—C1—C2118.9 (2)C16—C11—C10120.70 (15)
C6—C1—C7120.2 (2)C12—C11—C10121.23 (15)
C2—C1—C7120.9 (2)C13—C12—C11120.95 (18)
C3—C2—C1120.2 (3)C13—C12—H12119.5
C3—C2—H2119.9C11—C12—H12119.5
C1—C2—H2119.9C14—C13—C12120.35 (19)
C4—C3—C2120.5 (3)C14—C13—H13119.8
C4—C3—H3119.8C12—C13—H13119.8
C2—C3—H3119.8C13—C14—C15119.51 (18)
C3—C4—C5120.1 (3)C13—C14—H14120.2
C3—C4—H4120.0C15—C14—H14120.2
C5—C4—H4120.0C14—C15—C16120.74 (18)
C4—C5—C6120.2 (3)C14—C15—H15119.6
C4—C5—H5119.9C16—C15—H15119.6
C6—C5—H5119.9C15—C16—C11120.39 (17)
C1—C6—C5120.1 (3)C15—C16—H16119.8
C1—C6—H6120.0C11—C16—H16119.8
C5—C6—H6120.0O2—C17—O1122.01 (16)
C8—C7—C1179.1 (2)O2—C17—C18127.35 (15)
C7—C8—C9178.1 (2)O1—C17—C18110.64 (15)
C10—C9—C8124.12 (17)C17—C18—H18A109.5
C10—C9—H9117.9C17—C18—H18B109.5
C8—C9—H9117.9H18A—C18—H18B109.5
C9—C10—O1117.69 (15)C17—C18—H18C109.5
C9—C10—C11127.15 (15)H18A—C18—H18C109.5
O1—C10—C11114.96 (14)H18B—C18—H18C109.5
C16—C11—C12118.06 (16)C17—O1—C10117.88 (12)

Experimental details

Crystal data
Chemical formulaC18H14O2
Mr262.29
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)13.1480 (5), 5.5912 (2), 19.7579 (7)
β (°) 91.558 (2)
V (Å3)1451.93 (9)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.33 × 0.28 × 0.20
Data collection
DiffractometerBruker APEXII area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.987, 0.998
No. of measured, independent and
observed [I > 2σ(I)] reflections		8119, 2611, 1678
Rint0.021
(sin θ/λ)max (Å−1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.123, 1.02
No. of reflections2611
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.09, −0.14

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

 

Acknowledgements

We thank the Natural Science Foundation of Jiangxi Province (20114BAB213006) and the Educational Commission of Jiangxi Province (GJJ12579) for financial support.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
 First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChen, Z., Huang, G., Jiang, H., Huang, H. & Pan, X. (2011). J. Org. Chem. 76, 1134–1139.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationDebergh, J. R., Spivey, K. M. & Ready, J. M. (2008). J. Am. Chem. Soc. 130, 7828–7829.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationGoossen, L. J. & Paetzold, J. (2004). Angew. Chem. Int. Ed. 43, 1095–1098.  CAS Google Scholar
 First citationLi, Y., Liu, X., Jiang, H. & Feng, Z. (2010). Angew. Chem. Int. Ed. 49, 3338–3341.  Web of Science CrossRef CAS Google Scholar
 First citationNakao, Y., Hirata, Y., Tanaka, M. & Hiyama, T. (2008). Angew. Chem. Int. Ed. 47, 385–387.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2847
https://doi.org/10.1107/S1600536812037439
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