Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The structure of the title compound (4MPBA), C14H12O3, resembles that of phenyl benzoate (PBA), with similar geometric parameters. The dihedral angle between the phenyl and benzene rings in 4MPBA is 56.42 (3)°, compared with 55.7° observed for PBA. The mol­ecules in the title compound pack in layers parallel to the ac plane and in columns parallel to the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703406X/wn2169sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680703406X/wn2169Isup2.hkl
Contains datablock I

CCDC reference: 657773

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.095
  • Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

As part of a study of substituent effects on the solid state structures of chemically and biologically significant compounds (Gowda, Foro & Fuess, 2007; Gowda, Kozisek, Svoboda & Fuess, 2007; Gowda, Kozisek et al., 2007a, b; Gowda, Nayak et al., 2007; Gowda, Svoboda & Fuess, 2007) the structure of 4-methoxyphenyl benzoate (4MPBA) has been determined. The structure of 4MPBA (Fig. 1) resembles that of phenyl benzoate (PBA) (Adams & Morsi, 1976). The bond parameters in 4MPBA are similar to those in PBA and other benzoates. The molecules in the title compound pack in layers parallel to the ac plane and columns parallel to the c axis (Fig. 2).

Related literature top

For related literature, see: Adams & Morsi (1976); Gowda, Kozisek, Tokarcik et al. (2007a, 2007b); Gowda, Foro & Fuess (2007); Gowda, Kozisek, Svoboda et al. (2007); Gowda, Nayak et al. (2007); Gowda, Svoboda et al. (2007); Nayak & Gowda (2007).

Experimental top

The title compound was prepared according to a literature method (Nayak & Gowda, 2007). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Nayak & Gowda, 2007). Single crystals of the title compound were obtained by slow evaporation of an ethanolic solution and used for X-ray diffraction studies at room temperature.

Refinement top

The H atoms were located in difference map and their positions refined, with Uiso(H) = 1.2Ueq(parent atom). The range of refined C—H distances was 0.94 (1) - 1.01 (2) Å.

Structure description top

As part of a study of substituent effects on the solid state structures of chemically and biologically significant compounds (Gowda, Foro & Fuess, 2007; Gowda, Kozisek, Svoboda & Fuess, 2007; Gowda, Kozisek et al., 2007a, b; Gowda, Nayak et al., 2007; Gowda, Svoboda & Fuess, 2007) the structure of 4-methoxyphenyl benzoate (4MPBA) has been determined. The structure of 4MPBA (Fig. 1) resembles that of phenyl benzoate (PBA) (Adams & Morsi, 1976). The bond parameters in 4MPBA are similar to those in PBA and other benzoates. The molecules in the title compound pack in layers parallel to the ac plane and columns parallel to the c axis (Fig. 2).

For related literature, see: Adams & Morsi (1976); Gowda, Kozisek, Tokarcik et al. (2007a, 2007b); Gowda, Foro & Fuess (2007); Gowda, Kozisek, Svoboda et al. (2007); Gowda, Nayak et al. (2007); Gowda, Svoboda et al. (2007); Nayak & Gowda (2007).

Computing details top

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. Packing diagram of the title compound, as viewed perpendicular to the ac plane.
4-Methoxyphenyl benzoate top
Crystal data top
C14H12O3F(000) = 960
Mr = 228.24Dx = 1.303 Mg m3
Orthorhombic, PbcaCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 14.303 (1) Åθ = 4.7–21.7°
b = 6.4799 (7) ŵ = 0.75 mm1
c = 25.113 (2) ÅT = 299 K
V = 2327.5 (4) Å3Prism, colourless
Z = 80.60 × 0.50 × 0.43 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1876 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 66.9°, θmin = 3.5°
ω/2θ scansh = 170
Absorption correction: ψ scan
(North et al., 1968)
k = 70
Tmin = 0.648, Tmax = 0.727l = 1929
3699 measured reflections3 standard reflections every 120 min
2067 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033Only H-atom coordinates refined
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0479P)2 + 0.3393P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.005
2067 reflectionsΔρmax = 0.14 e Å3
191 parametersΔρmin = 0.11 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0102 (5)
Crystal data top
C14H12O3V = 2327.5 (4) Å3
Mr = 228.24Z = 8
Orthorhombic, PbcaCu Kα radiation
a = 14.303 (1) ŵ = 0.75 mm1
b = 6.4799 (7) ÅT = 299 K
c = 25.113 (2) Å0.60 × 0.50 × 0.43 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1876 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.017
Tmin = 0.648, Tmax = 0.7273 standard reflections every 120 min
3699 measured reflections intensity decay: none
2067 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.095Only H-atom coordinates refined
S = 1.06Δρmax = 0.14 e Å3
2067 reflectionsΔρmin = 0.11 e Å3
191 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
C10.12046 (8)0.07468 (18)0.77616 (5)0.0468 (3)
C20.16769 (8)0.10896 (19)0.77077 (5)0.0514 (3)
H20.1991 (10)0.164 (2)0.8005 (6)0.062*
C30.16764 (8)0.21005 (19)0.72225 (5)0.0503 (3)
H30.2002 (10)0.342 (2)0.7183 (5)0.060*
C40.12047 (8)0.12494 (18)0.67947 (4)0.0455 (3)
C50.07270 (8)0.06046 (18)0.68560 (5)0.0493 (3)
H50.0400 (10)0.118 (2)0.6556 (5)0.059*
C60.07288 (8)0.16024 (19)0.73398 (5)0.0494 (3)
H60.0408 (10)0.290 (2)0.7388 (5)0.059*
C70.09183 (8)0.11004 (19)0.86903 (5)0.0501 (3)
C80.10711 (8)0.24883 (19)0.91488 (5)0.0492 (3)
C90.14336 (10)0.4464 (2)0.90924 (6)0.0584 (3)
H90.1586 (11)0.496 (2)0.8733 (6)0.070*
C100.15736 (11)0.5668 (3)0.95396 (7)0.0716 (4)
H100.1801 (12)0.702 (3)0.9493 (7)0.086*
C110.13484 (12)0.4930 (3)1.00365 (7)0.0790 (5)
H110.1452 (12)0.582 (3)1.0353 (8)0.095*
C120.09794 (14)0.2973 (3)1.00923 (6)0.0800 (5)
H120.0753 (12)0.247 (3)1.0449 (7)0.096*
C130.08494 (11)0.1753 (2)0.96511 (5)0.0649 (4)
H130.0600 (11)0.038 (3)0.9686 (6)0.078*
C140.16889 (14)0.3934 (3)0.62070 (7)0.0706 (4)
H14A0.2357 (14)0.377 (3)0.6281 (6)0.085*
H14B0.1605 (12)0.420 (3)0.5825 (7)0.085*
H14C0.1478 (12)0.500 (3)0.6441 (7)0.085*
O10.12642 (6)0.19084 (13)0.82345 (3)0.0558 (3)
O20.05426 (8)0.05500 (15)0.87100 (4)0.0733 (3)
O30.11796 (7)0.20889 (14)0.62955 (3)0.0607 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0468 (6)0.0470 (6)0.0467 (6)0.0065 (5)0.0050 (5)0.0006 (5)
C20.0504 (6)0.0552 (7)0.0485 (6)0.0045 (5)0.0054 (5)0.0059 (5)
C30.0504 (6)0.0470 (6)0.0536 (7)0.0091 (5)0.0024 (5)0.0029 (5)
C40.0450 (6)0.0466 (6)0.0450 (6)0.0004 (5)0.0003 (4)0.0030 (5)
C50.0485 (6)0.0491 (6)0.0502 (6)0.0050 (5)0.0025 (5)0.0084 (5)
C60.0475 (6)0.0432 (6)0.0574 (7)0.0041 (5)0.0058 (5)0.0040 (5)
C70.0483 (6)0.0499 (7)0.0521 (7)0.0042 (5)0.0041 (5)0.0026 (5)
C80.0464 (6)0.0516 (6)0.0496 (6)0.0012 (5)0.0013 (5)0.0001 (5)
C90.0626 (8)0.0550 (7)0.0577 (7)0.0047 (6)0.0021 (6)0.0028 (6)
C100.0758 (9)0.0622 (9)0.0769 (10)0.0045 (7)0.0038 (8)0.0158 (7)
C110.0899 (11)0.0854 (11)0.0616 (9)0.0134 (9)0.0111 (8)0.0216 (8)
C120.1012 (12)0.0885 (12)0.0504 (8)0.0148 (10)0.0035 (8)0.0003 (8)
C130.0774 (9)0.0632 (8)0.0542 (7)0.0018 (7)0.0088 (6)0.0033 (6)
C140.0887 (11)0.0603 (8)0.0629 (9)0.0134 (8)0.0013 (8)0.0120 (7)
O10.0679 (5)0.0518 (5)0.0477 (5)0.0130 (4)0.0081 (4)0.0031 (4)
O20.0954 (8)0.0579 (6)0.0666 (6)0.0280 (5)0.0150 (5)0.0029 (4)
O30.0765 (6)0.0567 (5)0.0489 (5)0.0113 (4)0.0083 (4)0.0042 (4)
Geometric parameters (Å, º) top
C1—C21.3751 (17)C8—C131.3852 (18)
C1—C61.3756 (17)C8—C91.3886 (18)
C1—O11.4086 (14)C9—C101.382 (2)
C2—C31.3832 (17)C9—H90.983 (15)
C2—H20.943 (14)C10—C111.375 (2)
C3—C41.3833 (16)C10—H100.942 (18)
C3—H30.979 (14)C11—C121.381 (3)
C4—O31.3671 (14)C11—H110.992 (19)
C4—C51.3906 (16)C12—C131.374 (2)
C5—C61.3764 (17)C12—H121.007 (18)
C5—H50.963 (14)C13—H130.961 (17)
C6—H60.964 (15)C14—O31.4176 (17)
C7—O21.1978 (15)C14—H14A0.98 (2)
C7—O11.3524 (14)C14—H14B0.982 (18)
C7—C81.4774 (17)C14—H14C0.956 (19)
C2—C1—C6121.06 (11)C10—C9—C8119.45 (14)
C2—C1—O1121.05 (11)C10—C9—H9122.0 (9)
C6—C1—O1117.63 (11)C8—C9—H9118.5 (9)
C1—C2—C3119.76 (11)C11—C10—C9120.48 (15)
C1—C2—H2118.9 (8)C11—C10—H10121.1 (11)
C3—C2—H2121.3 (8)C9—C10—H10118.4 (11)
C4—C3—C2119.70 (11)C10—C11—C12120.08 (15)
C4—C3—H3120.2 (8)C10—C11—H11119.3 (11)
C2—C3—H3120.1 (8)C12—C11—H11120.7 (11)
O3—C4—C3124.50 (11)C13—C12—C11119.90 (15)
O3—C4—C5115.61 (10)C13—C12—H12119.2 (11)
C3—C4—C5119.87 (11)C11—C12—H12120.7 (11)
C6—C5—C4120.17 (11)C12—C13—C8120.36 (15)
C6—C5—H5120.6 (8)C12—C13—H13120.5 (10)
C4—C5—H5119.2 (8)C8—C13—H13119.1 (10)
C1—C6—C5119.43 (11)O3—C14—H14A112.3 (11)
C1—C6—H6119.3 (8)O3—C14—H14B103.8 (10)
C5—C6—H6121.3 (8)H14A—C14—H14B108.9 (14)
O2—C7—O1123.00 (11)O3—C14—H14C110.6 (11)
O2—C7—C8125.29 (11)H14A—C14—H14C105.6 (14)
O1—C7—C8111.71 (10)H14B—C14—H14C115.8 (15)
C13—C8—C9119.71 (12)C7—O1—C1118.98 (9)
C13—C8—C7117.80 (12)C4—O3—C14117.76 (10)
C9—C8—C7122.48 (11)
C6—C1—C2—C30.00 (18)C13—C8—C9—C100.4 (2)
O1—C1—C2—C3173.98 (10)C7—C8—C9—C10178.90 (13)
C1—C2—C3—C40.36 (18)C8—C9—C10—C110.6 (2)
C2—C3—C4—O3178.21 (11)C9—C10—C11—C120.0 (3)
C2—C3—C4—C50.62 (18)C10—C11—C12—C130.9 (3)
O3—C4—C5—C6178.39 (11)C11—C12—C13—C81.1 (3)
C3—C4—C5—C60.54 (17)C9—C8—C13—C120.5 (2)
C2—C1—C6—C50.08 (17)C7—C8—C13—C12179.82 (14)
O1—C1—C6—C5174.10 (10)O2—C7—O1—C11.65 (19)
C4—C5—C6—C10.18 (17)C8—C7—O1—C1177.86 (10)
O2—C7—C8—C136.8 (2)C2—C1—O1—C764.57 (15)
O1—C7—C8—C13172.67 (12)C6—C1—O1—C7121.25 (12)
O2—C7—C8—C9173.90 (14)C3—C4—O3—C141.48 (19)
O1—C7—C8—C96.61 (17)C5—C4—O3—C14177.40 (12)

Experimental details

Crystal data
Chemical formulaC14H12O3
Mr228.24
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)299
a, b, c (Å)14.303 (1), 6.4799 (7), 25.113 (2)
V3)2327.5 (4)
Z8
Radiation typeCu Kα
µ (mm1)0.75
Crystal size (mm)0.60 × 0.50 × 0.43
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.648, 0.727
No. of measured, independent and
observed [I > 2σ(I)] reflections
3699, 2067, 1876
Rint0.017
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.095, 1.06
No. of reflections2067
No. of parameters191
H-atom treatmentOnly H-atom coordinates refined
Δρmax, Δρmin (e Å3)0.14, 0.11

Computer programs: CAD-4-PC Software (Enraf–Nonius, 1996), CAD-4-PC Software, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds