Methyl phenyl terephthalate

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organic papers

o680

Fuet al. _C

15H12O4 doi:10.1107/S1600536806001760 Acta Cryst.(2006). E62, o680–o681

Acta Crystallographica Section E Structure Reports Online

ISSN 1600-5368

Methyl phenyl terephthalate

Xian-Shu Fu,aFa Chengb* and Yong-Mei Xiec

a

College of Life Sciences, China Jiliang University, Hangzhou 310018, People’s Republic of China,b_{Department of Chemistry,} Tianjin University, Tianjin 300072, People’s Republic of China, andc_{Department of} Chemical Engineering, Hangzhou Vocational Technology Institute, Hangzhou 310018, People’s Republic of China

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 294 K

Mean(C–C) = 0.003 A˚

Rfactor = 0.043

wRfactor = 0.117

Data-to-parameter ratio = 14.5

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 21 December 2005 Accepted 16 January 2006

#2006 International Union of Crystallography

The title compound, C15H12O4, was synthesized in an

anhydrous medium. The aromatic rings make a dihedral angle of 37.43 (5)_{. Weak intermolecular C—H}_{O hydrogen bonds} involving one of the carbonyl O atoms stabilize the crystal packing.

Comment

Organic electroluminescence – the emission of light by organic molecules exposed to an electric field – has been extensively investigated in academic and industrial laboratories (Cui & Kim, 2004). The title compound, (I) (Fig. 1), prepared by our group, belongs to the family of organic electroluminescent materials. We report here its X-ray crystal structure.

The bond lengths and angles in (I) (Table 1) show normal values. The two aromatic rings make a dihedral angle of 37.43 (5)_{. Weak intermolecular C—H}_{O hydrogen bonds} (Table 2) stabilize the crystal packing (Fig. 2).

Experimental

The title compound was prepared according to a known procedure (Li et al., 2000), which resulted in a colourless powder (m.p. 405– 406 K). Single crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloromethane solution.

Crystal data C15H12O4

Mr= 256.25

Monoclinic,P21=c

a= 6.1654 (13) A˚

b= 29.374 (6) A˚

c= 7.2827 (16) A˚

= 111.188 (4)

V= 1229.8 (5) A˚3

Z= 4

Dx= 1.384 Mg m

3 MoKradiation Cell parameters from 2124

reflections

= 2.8–25.8 = 0.10 mm1

T= 294 (2) K Block, colourless 0.300.280.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

’and!scans

Absorption correction: multi-scan (SADABS; Sheldrick, 2002)

Tmin= 0.967,Tmax= 0.980 6896 measured reflections

2526 independent reflections 1623 reflections withI> 2(I)

Rint= 0.047

max= 26.5

h=3!7

k=36!36

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Refinement Refinement onF2 R[F2_{> 2}₍_F2_{)] = 0.043}

wR(F2) = 0.117

S= 1.01 2526 reflections 174 parameters

H-atom parameters constrained

w= 1/[2

(Fo2) + (0.0459P)2 + 0.2662P]

whereP= (Fo2+ 2Fc2)/3 (/)max= 0.001

max= 0.16 e A˚

3

min=0.19 e A˚

3

Extinction correction:SHELXL97

[image:2.610.316.565.74.210.2]

Extinction coefficient: 0.018 (2)

Table 1

Selected geometric parameters (A˚ ,_).

O1—C7 1.194 (2) O2—C7 1.352 (2)

O2—C8 1.401 (2) C6—C7 1.478 (2)

C5—C6—C7 118.13 (16) O1—C7—C6 125.13 (16)

C9—C8—O2 123.42 (16)

C8—O2—C7—C6 177.84 (15) C5—C6—C7—O1 6.9 (3)

C5—C6—C7—O2 174.25 (15) O2—C8—C9—C10 173.84 (16)

Table 2

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

C13—H13 O1i

0.93 2.46 3.362 (2) 164 C15—H15A O1ii

0.96 2.57 3.443 (2) 152

Symmetry codes: (i)x1;y;z; (ii)xþ1;yþ1;zþ2.

All H atoms were positioned geometrically and refined as riding (C—H = 0.93 or 0.96 A˚ ). For CH groups, Uiso(H) values were set

equal to 1.2Ueq(C) and for the methyl groups they were set equal to

1.5Ueq(C).

Data collection:SMART(Bruker, 1997); cell refinement:SAINT

(Bruker, 1997); data reduction:SAINT; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:

SHELXTL (Bruker, 1997); software used to prepare material for publication:SHELXTL.

This work was supported by the Scientific Research Foundation for Returned Overseas Chinese Scholars and the Ministry of Education.

References

Bruker (1997).SMART,SAINTandSHELXTL(Version 5.10). Bruker AXS Inc, Madison, Wiscosin, USA.

Cui, J. Z. & Kim, S. H. (2004).Chin. Sci. Bull.49, 797–802. Li, W. R., Yo, Y. C. & Lin, Y. S. (2000).Tetrahedron,56, 8867–8875. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of

Go¨ttingen, Germany.

[image:2.610.46.299.74.158.2]

Sheldrick, G. M. (2002).SADABS. Version 2.03. University of Go¨ttingen, Germany.

Figure 1

View of (I), showing the atom-numbering scheme and displacement ellipsoids drawn at the 35% probability level.

Figure 2

[image:2.610.44.297.362.436.2]

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supporting information

sup-1 Acta Cryst. (2006). E62, o680–o681

supporting information

Acta Cryst. (2006). E62, o680–o681 [https://doi.org/10.1107/S1600536806001760]

Methyl phenyl terephthalate

Xian-Shu Fu, Fa Cheng and Yong-Mei Xie

Methyl phenyl terephthalate

Crystal data

C15H12O4 Mr = 256.25 Monoclinic, P21/c a = 6.1654 (13) Å

b = 29.374 (6) Å

c = 7.2827 (16) Å

β = 111.188 (4)°

V = 1229.8 (5) Å3 Z = 4

F(000) = 536

Dx = 1.384 Mg m−3

Melting point: 405 K

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 2124 reflections

θ = 2.8–25.8°

µ = 0.10 mm−1 T = 294 K Block, colourless 0.30 × 0.28 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

φ and ω scans

Absorption correction: multi-scan (SADABS; Sheldrick, 2002)

Tmin = 0.967, Tmax = 0.980

6896 measured reflections 2526 independent reflections 1623 reflections with I > 2σ(I)

Rint = 0.047

θmax = 26.5°, θmin = 1.4° h = −3→7

k = −36→36

l = −9→9

Refinement

Refinement on F2

Least-squares matrix: full

R[F2_{> 2}_σ₍_F2_{)] = 0.043} wR(F2_{) = 0.117} S = 1.01 2526 reflections 174 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2₍_F

o2) + (0.0459P)2 + 0.2662P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001

Δρmax = 0.16 e Å−3

Δρmin = −0.19 e Å−3

Extinction correction: SHELXL97, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2_θ_)]-1/4

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Special details

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₎

x y z Uiso*/Ueq

O1 0.8236 (2) 0.33457 (4) 0.9330 (2) 0.0562 (4)

O2 0.4342 (2) 0.33467 (4) 0.79063 (19) 0.0470 (4)

O3 0.3580 (3) 0.55076 (4) 0.6906 (2) 0.0640 (4)

O4 0.0482 (2) 0.53167 (4) 0.76334 (19) 0.0507 (4)

C1 0.4101 (3) 0.24240 (6) 0.7940 (3) 0.0501 (5)

H1 0.2740 0.2594 0.7591 0.060*

C2 0.3988 (4) 0.19530 (7) 0.7851 (3) 0.0624 (6)

H2 0.2552 0.1807 0.7423 0.075*

C3 0.5987 (4) 0.17031 (7) 0.8392 (3) 0.0617 (6)

H3 0.5910 0.1387 0.8334 0.074*

C4 0.8102 (4) 0.19157 (7) 0.9018 (3) 0.0644 (6)

H4 0.9460 0.1744 0.9404 0.077*

C5 0.8226 (3) 0.23852 (7) 0.9080 (3) 0.0525 (5)

H5 0.9666 0.2529 0.9487 0.063*

C6 0.6222 (3) 0.26409 (6) 0.8543 (2) 0.0368 (4)

C7 0.6446 (3) 0.31421 (6) 0.8650 (3) 0.0383 (4)

C8 0.4107 (3) 0.38211 (6) 0.7909 (3) 0.0395 (4)

C9 0.5444 (3) 0.41156 (6) 0.7299 (3) 0.0445 (5)

H9 0.6676 0.4009 0.6971 0.053*

C10 0.4916 (3) 0.45736 (6) 0.7184 (3) 0.0447 (5)

H10 0.5821 0.4778 0.6796 0.054*

C11 0.3060 (3) 0.47338 (6) 0.7637 (2) 0.0376 (4)

C12 0.1765 (3) 0.44305 (6) 0.8270 (3) 0.0454 (5)

H12 0.0534 0.4536 0.8605 0.054*

C13 0.2293 (3) 0.39713 (6) 0.8407 (3) 0.0454 (5)

H13 0.1424 0.3767 0.8834 0.055*

C14 0.2462 (3) 0.52242 (6) 0.7359 (3) 0.0421 (4)

C15 −0.0304 (4) 0.57823 (6) 0.7333 (3) 0.0553 (5)

H15A 0.0782 0.5972 0.8309 0.083*

H15B −0.1805 0.5805 0.7443 0.083*

H15C −0.0412 0.5880 0.6045 0.083*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

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supporting information

sup-3 Acta Cryst. (2006). E62, o680–o681

O2 0.0392 (7) 0.0302 (7) 0.0666 (9) 0.0000 (5) 0.0131 (6) −0.0001 (6) O3 0.0714 (10) 0.0365 (8) 0.0958 (12) −0.0030 (7) 0.0443 (9) 0.0113 (7) O4 0.0544 (8) 0.0328 (7) 0.0687 (9) 0.0050 (6) 0.0268 (7) 0.0051 (6) C1 0.0433 (11) 0.0388 (10) 0.0640 (13) −0.0016 (9) 0.0145 (10) −0.0020 (9) C2 0.0635 (14) 0.0409 (11) 0.0814 (16) −0.0127 (11) 0.0244 (12) −0.0062 (11) C3 0.0898 (18) 0.0318 (11) 0.0681 (14) 0.0013 (11) 0.0339 (13) −0.0018 (10) C4 0.0671 (15) 0.0441 (12) 0.0778 (16) 0.0166 (11) 0.0212 (13) 0.0028 (11) C5 0.0462 (11) 0.0465 (12) 0.0612 (13) 0.0027 (9) 0.0150 (10) −0.0009 (10) C6 0.0428 (10) 0.0329 (9) 0.0347 (9) 0.0010 (8) 0.0139 (8) −0.0005 (7) C7 0.0375 (10) 0.0369 (10) 0.0394 (10) −0.0013 (8) 0.0128 (8) 0.0000 (8) C8 0.0378 (10) 0.0302 (9) 0.0468 (10) −0.0020 (8) 0.0109 (8) 0.0014 (8) C9 0.0428 (10) 0.0386 (10) 0.0558 (12) 0.0021 (8) 0.0224 (9) 0.0027 (8) C10 0.0456 (11) 0.0372 (10) 0.0537 (12) −0.0036 (9) 0.0209 (9) 0.0060 (8) C11 0.0398 (10) 0.0328 (9) 0.0395 (9) −0.0017 (8) 0.0136 (8) 0.0021 (7) C12 0.0443 (11) 0.0385 (10) 0.0589 (12) 0.0035 (8) 0.0253 (10) 0.0055 (9) C13 0.0438 (11) 0.0361 (10) 0.0603 (12) −0.0028 (8) 0.0236 (10) 0.0080 (8) C14 0.0477 (11) 0.0344 (9) 0.0431 (10) −0.0026 (8) 0.0151 (9) −0.0007 (8) C15 0.0664 (13) 0.0352 (10) 0.0630 (13) 0.0093 (10) 0.0219 (11) 0.0005 (9)

Geometric parameters (Å, º)

O1—C7 1.194 (2) C5—H5 0.9300

O2—C7 1.352 (2) C6—C7 1.478 (2)

O2—C8 1.401 (2) C8—C13 1.367 (2)

O3—C14 1.200 (2) C8—C9 1.375 (2)

O4—C14 1.335 (2) C9—C10 1.380 (2)

O4—C15 1.441 (2) C9—H9 0.9300

C1—C6 1.376 (2) C10—C11 1.383 (3)

C1—C2 1.386 (3) C10—H10 0.9300

C1—H1 0.9300 C11—C12 1.382 (2)

C2—C3 1.364 (3) C11—C14 1.482 (2)

C2—H2 0.9300 C12—C13 1.383 (2)

C3—C4 1.367 (3) C12—H12 0.9300

C3—H3 0.9300 C13—H13 0.9300

C4—C5 1.381 (3) C15—H15A 0.9600

C4—H4 0.9300 C15—H15B 0.9600

C5—C6 1.376 (2) C15—H15C 0.9600

C7—O2—C8 121.76 (13) C9—C8—O2 123.42 (16)

C14—O4—C15 116.49 (15) C8—C9—C10 118.51 (17)

C6—C1—C2 120.22 (18) C8—C9—H9 120.7

C6—C1—H1 119.9 C10—C9—H9 120.7

C2—C1—H1 119.9 C9—C10—C11 120.99 (17)

C3—C2—C1 119.91 (19) C9—C10—H10 119.5

C3—C2—H2 120.0 C11—C10—H10 119.5

C1—C2—H2 120.0 C12—C11—C10 119.20 (16)

C2—C3—C4 120.24 (19) C12—C11—C14 121.81 (17)

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C4—C3—H3 119.9 C11—C12—C13 120.24 (17)

C3—C4—C5 120.1 (2) C11—C12—H12 119.9

C3—C4—H4 119.9 C13—C12—H12 119.9

C5—C4—H4 119.9 C8—C13—C12 119.31 (17)

C6—C5—C4 120.16 (19) C8—C13—H13 120.3

C6—C5—H5 119.9 C12—C13—H13 120.3

C4—C5—H5 119.9 O3—C14—O4 123.15 (17)

C1—C6—C5 119.32 (16) O3—C14—C11 124.93 (18)

C1—C6—C7 122.55 (16) O4—C14—C11 111.90 (16)

C5—C6—C7 118.13 (16) O4—C15—H15A 109.5

O1—C7—O2 123.53 (15) O4—C15—H15B 109.5

O1—C7—C6 125.13 (16) H15A—C15—H15B 109.5

O2—C7—C6 111.33 (15) O4—C15—H15C 109.5

C13—C8—C9 121.72 (16) H15A—C15—H15C 109.5

C13—C8—O2 114.62 (15) H15B—C15—H15C 109.5

C6—C1—C2—C3 1.0 (3) C13—C8—C9—C10 −0.3 (3)

C1—C2—C3—C4 −0.1 (3) O2—C8—C9—C10 173.84 (16)

C2—C3—C4—C5 −0.9 (3) C8—C9—C10—C11 −1.1 (3)

C3—C4—C5—C6 1.1 (3) C9—C10—C11—C12 1.9 (3)

C2—C1—C6—C5 −0.9 (3) C9—C10—C11—C14 −175.79 (17)

C2—C1—C6—C7 179.50 (19) C10—C11—C12—C13 −1.3 (3)

C4—C5—C6—C1 −0.2 (3) C14—C11—C12—C13 176.33 (17)

C4—C5—C6—C7 179.49 (19) C9—C8—C13—C12 0.9 (3)

C8—O2—C7—O1 −1.1 (3) O2—C8—C13—C12 −173.73 (16)

C8—O2—C7—C6 177.84 (15) C11—C12—C13—C8 0.0 (3)

C1—C6—C7—O1 172.78 (18) C15—O4—C14—O3 0.8 (3)

C5—C6—C7—O1 −6.9 (3) C15—O4—C14—C11 −177.97 (15)

C1—C6—C7—O2 −6.1 (2) C12—C11—C14—O3 176.19 (19)

C5—C6—C7—O2 174.25 (15) C10—C11—C14—O3 −6.1 (3)

C7—O2—C8—C13 −138.14 (17) C12—C11—C14—O4 −5.1 (2)

C7—O2—C8—C9 47.4 (3) C10—C11—C14—O4 172.63 (16)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

C13—H13···O1i _0.93 _2.46 _{3.362 (2)} ₁₆₄

C15—H15A···O1ii _0.96 _2.57 _{3.443 (2)} ₁₅₂