Methyl phenyl terephthalate

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.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.117
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

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Computing details

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.

Methyl phenyl terephthalate

Crystal data

C15H12O4	Dx = 1.384 Mg m^−3
Mr = 256.25	Melting point: 405 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.1654 (13) Å	Cell parameters from 2124 reflections
b = 29.374 (6) Å	θ = 2.8–25.8°
c = 7.2827 (16) Å	µ = 0.10 mm^−1
β = 111.188 (4)°	T = 294 K
V = 1229.8 (5) Å^3	Block, colourless
Z = 4	0.30 × 0.28 × 0.20 mm
F(000) = 536

Data collection

Bruker SMART CCD area-detector diffractometer	2526 independent reflections
Radiation source: fine-focus sealed tube	1623 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 26.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −3→7
Tmin = 0.967, Tmax = 0.980	k = −36→36
6896 measured reflections	l = −9→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0459P)^2 + 0.2662P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
2526 reflections	Δρmax = 0.16 e Å^−3
174 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (2)

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0409 (8)	0.0420 (8)	0.0757 (10)	−0.0064 (6)	0.0090 (7)	0.0002 (7)
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)
C2—C3—H3	119.9	C10—C11—C14	118.95 (16)
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···O1^i	0.93	2.46	3.362 (2)	164
C15—H15A···O1^ii	0.96	2.57	3.443 (2)	152

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+2.