Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703406X/wn2169sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680703406X/wn2169Isup2.hkl |
CCDC reference: 657773
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (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
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).
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.
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.
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).
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.
C14H12O3 | F(000) = 960 |
Mr = 228.24 | Dx = 1.303 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 14.303 (1) Å | θ = 4.7–21.7° |
b = 6.4799 (7) Å | µ = 0.75 mm−1 |
c = 25.113 (2) Å | T = 299 K |
V = 2327.5 (4) Å3 | Prism, colourless |
Z = 8 | 0.60 × 0.50 × 0.43 mm |
Enraf–Nonius CAD-4 diffractometer | 1876 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 66.9°, θmin = 3.5° |
ω/2θ scans | h = −17→0 |
Absorption correction: ψ scan (North et al., 1968) | k = −7→0 |
Tmin = 0.648, Tmax = 0.727 | l = −19→29 |
3699 measured reflections | 3 standard reflections every 120 min |
2067 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | Only 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 reflections | Δρmax = 0.14 e Å−3 |
191 parameters | Δρmin = −0.11 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0102 (5) |
C14H12O3 | V = 2327.5 (4) Å3 |
Mr = 228.24 | Z = 8 |
Orthorhombic, Pbca | Cu Kα radiation |
a = 14.303 (1) Å | µ = 0.75 mm−1 |
b = 6.4799 (7) Å | T = 299 K |
c = 25.113 (2) Å | 0.60 × 0.50 × 0.43 mm |
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 = 0.727 | 3 standard reflections every 120 min |
3699 measured reflections | intensity decay: none |
2067 independent reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.095 | Only H-atom coordinates refined |
S = 1.06 | Δρmax = 0.14 e Å−3 |
2067 reflections | Δρmin = −0.11 e Å−3 |
191 parameters |
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 | 0.12046 (8) | −0.07468 (18) | 0.77616 (5) | 0.0468 (3) | |
C2 | 0.16769 (8) | 0.10896 (19) | 0.77077 (5) | 0.0514 (3) | |
H2 | 0.1991 (10) | 0.164 (2) | 0.8005 (6) | 0.062* | |
C3 | 0.16764 (8) | 0.21005 (19) | 0.72225 (5) | 0.0503 (3) | |
H3 | 0.2002 (10) | 0.342 (2) | 0.7183 (5) | 0.060* | |
C4 | 0.12047 (8) | 0.12494 (18) | 0.67947 (4) | 0.0455 (3) | |
C5 | 0.07270 (8) | −0.06046 (18) | 0.68560 (5) | 0.0493 (3) | |
H5 | 0.0400 (10) | −0.118 (2) | 0.6556 (5) | 0.059* | |
C6 | 0.07288 (8) | −0.16024 (19) | 0.73398 (5) | 0.0494 (3) | |
H6 | 0.0408 (10) | −0.290 (2) | 0.7388 (5) | 0.059* | |
C7 | 0.09183 (8) | −0.11004 (19) | 0.86903 (5) | 0.0501 (3) | |
C8 | 0.10711 (8) | −0.24883 (19) | 0.91488 (5) | 0.0492 (3) | |
C9 | 0.14336 (10) | −0.4464 (2) | 0.90924 (6) | 0.0584 (3) | |
H9 | 0.1586 (11) | −0.496 (2) | 0.8733 (6) | 0.070* | |
C10 | 0.15736 (11) | −0.5668 (3) | 0.95396 (7) | 0.0716 (4) | |
H10 | 0.1801 (12) | −0.702 (3) | 0.9493 (7) | 0.086* | |
C11 | 0.13484 (12) | −0.4930 (3) | 1.00365 (7) | 0.0790 (5) | |
H11 | 0.1452 (12) | −0.582 (3) | 1.0353 (8) | 0.095* | |
C12 | 0.09794 (14) | −0.2973 (3) | 1.00923 (6) | 0.0800 (5) | |
H12 | 0.0753 (12) | −0.247 (3) | 1.0449 (7) | 0.096* | |
C13 | 0.08494 (11) | −0.1753 (2) | 0.96511 (5) | 0.0649 (4) | |
H13 | 0.0600 (11) | −0.038 (3) | 0.9686 (6) | 0.078* | |
C14 | 0.16889 (14) | 0.3934 (3) | 0.62070 (7) | 0.0706 (4) | |
H14A | 0.2357 (14) | 0.377 (3) | 0.6281 (6) | 0.085* | |
H14B | 0.1605 (12) | 0.420 (3) | 0.5825 (7) | 0.085* | |
H14C | 0.1478 (12) | 0.500 (3) | 0.6441 (7) | 0.085* | |
O1 | 0.12642 (6) | −0.19084 (13) | 0.82345 (3) | 0.0558 (3) | |
O2 | 0.05426 (8) | 0.05500 (15) | 0.87100 (4) | 0.0733 (3) | |
O3 | 0.11796 (7) | 0.20889 (14) | 0.62955 (3) | 0.0607 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0468 (6) | 0.0470 (6) | 0.0467 (6) | 0.0065 (5) | 0.0050 (5) | 0.0006 (5) |
C2 | 0.0504 (6) | 0.0552 (7) | 0.0485 (6) | −0.0045 (5) | −0.0054 (5) | −0.0059 (5) |
C3 | 0.0504 (6) | 0.0470 (6) | 0.0536 (7) | −0.0091 (5) | −0.0024 (5) | −0.0029 (5) |
C4 | 0.0450 (6) | 0.0466 (6) | 0.0450 (6) | 0.0004 (5) | 0.0003 (4) | −0.0030 (5) |
C5 | 0.0485 (6) | 0.0491 (6) | 0.0502 (6) | −0.0050 (5) | −0.0025 (5) | −0.0084 (5) |
C6 | 0.0475 (6) | 0.0432 (6) | 0.0574 (7) | −0.0041 (5) | 0.0058 (5) | −0.0040 (5) |
C7 | 0.0483 (6) | 0.0499 (7) | 0.0521 (7) | 0.0042 (5) | 0.0041 (5) | −0.0026 (5) |
C8 | 0.0464 (6) | 0.0516 (6) | 0.0496 (6) | −0.0012 (5) | 0.0013 (5) | −0.0001 (5) |
C9 | 0.0626 (8) | 0.0550 (7) | 0.0577 (7) | 0.0047 (6) | 0.0021 (6) | 0.0028 (6) |
C10 | 0.0758 (9) | 0.0622 (9) | 0.0769 (10) | 0.0045 (7) | −0.0038 (8) | 0.0158 (7) |
C11 | 0.0899 (11) | 0.0854 (11) | 0.0616 (9) | −0.0134 (9) | −0.0111 (8) | 0.0216 (8) |
C12 | 0.1012 (12) | 0.0885 (12) | 0.0504 (8) | −0.0148 (10) | 0.0035 (8) | 0.0003 (8) |
C13 | 0.0774 (9) | 0.0632 (8) | 0.0542 (7) | −0.0018 (7) | 0.0088 (6) | −0.0033 (6) |
C14 | 0.0887 (11) | 0.0603 (8) | 0.0629 (9) | −0.0134 (8) | −0.0013 (8) | 0.0120 (7) |
O1 | 0.0679 (5) | 0.0518 (5) | 0.0477 (5) | 0.0130 (4) | 0.0081 (4) | 0.0031 (4) |
O2 | 0.0954 (8) | 0.0579 (6) | 0.0666 (6) | 0.0280 (5) | 0.0150 (5) | 0.0029 (4) |
O3 | 0.0765 (6) | 0.0567 (5) | 0.0489 (5) | −0.0113 (4) | −0.0083 (4) | 0.0042 (4) |
C1—C2 | 1.3751 (17) | C8—C13 | 1.3852 (18) |
C1—C6 | 1.3756 (17) | C8—C9 | 1.3886 (18) |
C1—O1 | 1.4086 (14) | C9—C10 | 1.382 (2) |
C2—C3 | 1.3832 (17) | C9—H9 | 0.983 (15) |
C2—H2 | 0.943 (14) | C10—C11 | 1.375 (2) |
C3—C4 | 1.3833 (16) | C10—H10 | 0.942 (18) |
C3—H3 | 0.979 (14) | C11—C12 | 1.381 (3) |
C4—O3 | 1.3671 (14) | C11—H11 | 0.992 (19) |
C4—C5 | 1.3906 (16) | C12—C13 | 1.374 (2) |
C5—C6 | 1.3764 (17) | C12—H12 | 1.007 (18) |
C5—H5 | 0.963 (14) | C13—H13 | 0.961 (17) |
C6—H6 | 0.964 (15) | C14—O3 | 1.4176 (17) |
C7—O2 | 1.1978 (15) | C14—H14A | 0.98 (2) |
C7—O1 | 1.3524 (14) | C14—H14B | 0.982 (18) |
C7—C8 | 1.4774 (17) | C14—H14C | 0.956 (19) |
C2—C1—C6 | 121.06 (11) | C10—C9—C8 | 119.45 (14) |
C2—C1—O1 | 121.05 (11) | C10—C9—H9 | 122.0 (9) |
C6—C1—O1 | 117.63 (11) | C8—C9—H9 | 118.5 (9) |
C1—C2—C3 | 119.76 (11) | C11—C10—C9 | 120.48 (15) |
C1—C2—H2 | 118.9 (8) | C11—C10—H10 | 121.1 (11) |
C3—C2—H2 | 121.3 (8) | C9—C10—H10 | 118.4 (11) |
C4—C3—C2 | 119.70 (11) | C10—C11—C12 | 120.08 (15) |
C4—C3—H3 | 120.2 (8) | C10—C11—H11 | 119.3 (11) |
C2—C3—H3 | 120.1 (8) | C12—C11—H11 | 120.7 (11) |
O3—C4—C3 | 124.50 (11) | C13—C12—C11 | 119.90 (15) |
O3—C4—C5 | 115.61 (10) | C13—C12—H12 | 119.2 (11) |
C3—C4—C5 | 119.87 (11) | C11—C12—H12 | 120.7 (11) |
C6—C5—C4 | 120.17 (11) | C12—C13—C8 | 120.36 (15) |
C6—C5—H5 | 120.6 (8) | C12—C13—H13 | 120.5 (10) |
C4—C5—H5 | 119.2 (8) | C8—C13—H13 | 119.1 (10) |
C1—C6—C5 | 119.43 (11) | O3—C14—H14A | 112.3 (11) |
C1—C6—H6 | 119.3 (8) | O3—C14—H14B | 103.8 (10) |
C5—C6—H6 | 121.3 (8) | H14A—C14—H14B | 108.9 (14) |
O2—C7—O1 | 123.00 (11) | O3—C14—H14C | 110.6 (11) |
O2—C7—C8 | 125.29 (11) | H14A—C14—H14C | 105.6 (14) |
O1—C7—C8 | 111.71 (10) | H14B—C14—H14C | 115.8 (15) |
C13—C8—C9 | 119.71 (12) | C7—O1—C1 | 118.98 (9) |
C13—C8—C7 | 117.80 (12) | C4—O3—C14 | 117.76 (10) |
C9—C8—C7 | 122.48 (11) | ||
C6—C1—C2—C3 | 0.00 (18) | C13—C8—C9—C10 | −0.4 (2) |
O1—C1—C2—C3 | 173.98 (10) | C7—C8—C9—C10 | 178.90 (13) |
C1—C2—C3—C4 | −0.36 (18) | C8—C9—C10—C11 | 0.6 (2) |
C2—C3—C4—O3 | −178.21 (11) | C9—C10—C11—C12 | 0.0 (3) |
C2—C3—C4—C5 | 0.62 (18) | C10—C11—C12—C13 | −0.9 (3) |
O3—C4—C5—C6 | 178.39 (11) | C11—C12—C13—C8 | 1.1 (3) |
C3—C4—C5—C6 | −0.54 (17) | C9—C8—C13—C12 | −0.5 (2) |
C2—C1—C6—C5 | 0.08 (17) | C7—C8—C13—C12 | −179.82 (14) |
O1—C1—C6—C5 | −174.10 (10) | O2—C7—O1—C1 | 1.65 (19) |
C4—C5—C6—C1 | 0.18 (17) | C8—C7—O1—C1 | −177.86 (10) |
O2—C7—C8—C13 | −6.8 (2) | C2—C1—O1—C7 | 64.57 (15) |
O1—C7—C8—C13 | 172.67 (12) | C6—C1—O1—C7 | −121.25 (12) |
O2—C7—C8—C9 | 173.90 (14) | C3—C4—O3—C14 | 1.48 (19) |
O1—C7—C8—C9 | −6.61 (17) | C5—C4—O3—C14 | −177.40 (12) |
Experimental details
Crystal data | |
Chemical formula | C14H12O3 |
Mr | 228.24 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 299 |
a, b, c (Å) | 14.303 (1), 6.4799 (7), 25.113 (2) |
V (Å3) | 2327.5 (4) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.75 |
Crystal size (mm) | 0.60 × 0.50 × 0.43 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.648, 0.727 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3699, 2067, 1876 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.095, 1.06 |
No. of reflections | 2067 |
No. of parameters | 191 |
H-atom treatment | Only H-atom coordinates refined |
Δρmax, Δρmin (e Å−3) | 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.
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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).