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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 71| Part 12| December 2015| Page o1021
https://doi.org/10.1107/S2056989015022707

Crystal structure of 4-(4-meth­­oxy­phen­­oxy)benzaldehyde

Andreas Schäfer,a Ljuba Iovkova-Berends,a Stefan Gilke,a Paul Kossmann,a Hans Preuta* and Martin Hiersemanna

aFakultät Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany
*Correspondence e-mail: hans.preut@tu-dortmund.de

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 25 November 2015; accepted 26 November 2015; online 6 December 2015)

The title compound, C14H12O3, was synthesized via the nucleophilic addition of 4-meth­oxy­phenol to 4-fluoro­benzaldehyde. The dihedral angle between the least-squares planes of the benzene rings is 71.52 (3)° and the C—O—C angle at the central O atom is 118.82 (8)°. In the crystal, weak C—H⋯O hydrogen bonds link the molecules to generate supra­molecular layers in the bc plane. The layers are linked by weak C—H⋯π inter­actions.

CCDC reference: 1439095

Similar articles

1. Related literature

For the synthesis of 4-(4-meth­oxy­phen­oxy)benzaldehyde in an undergraduate laboratory course, see: Taber & Brannick (2015[Taber, D. F. & Brannick, S. J. (2015). J. Chem. Educ. 92, 1261-1262.]). For the synthesis of 4-aryl­oxybenzaldehydes and aceto­phenones, see: Yeager & Schissel (1991[Yeager, G. W. & Schissel, D. N. (1991). Synthesis, pp. 63-68.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C14H12O3

  • Mr = 228.24

  • Monoclinic, P 21 /c

  • a = 12.1297 (7) Å

  • b = 7.6581 (4) Å

  • c = 12.3577 (7) Å

  • β = 103.769 (6)°

  • V = 1114.92 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 173 K

  • 0.56 × 0.40 × 0.30 mm

2.2. Data collection

  • Oxford Diffraction Xcalibur2 CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Yarnton, England.]) Tmin = 0.808, Tmax = 1.000

  • 10049 measured reflections

  • 2967 independent reflections

  • 2551 reflections with I > 2σ(I)

  • Rint = 0.023

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.112

  • S = 1.04

  • 2967 reflections

  • 155 parameters

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C13—H13A⋯O1i 0.95 2.58 3.5129 (14) 167
C7—H7A⋯O1ii 0.95 2.56 3.2500 (14) 130
C1—H1A⋯Cg1iii 0.95 2.73 3.5453 (12) 145
C10—H10A⋯Cg2iv 0.95 2.88 3.7465 (12) 152
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [-x+1, y+{\script{1\over 2}}, -z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: SHELXP2014 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL2013 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 1439095

Crystal structure: contains datablocks I, 3352b. DOI: https://doi.org/10.1107/S2056989015022707/tk5411sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015022707/tk5411Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015022707/tk5411Isup3.cml

checkCIF report


Comment top

As part of an evaluation of single step experiments for an undergraduate laboratory course, we came across a literature protocol that describes the preparation of crystalline 4-aryloxybenzaldehyde by nucleophilic aromatic substitution (Taber & Brannick, 2015). The reaction of 4-fluorobenzaldehyde (II) with 4-methoxyphenol (III) in the presence of potassium carbonate in dimethyl sulfoxide provided 4-(4-methoxyphenoxy)benzaldehyde (I) as large pale yellow crystals. The recrystallization of a small amount of (I) from n-heptane provided clear colourless crystals, suitable for X-ray analysis. In our hands, the literature protocol failed to deliver precipitated crude product upon dilution of the reaction mixture with water and subsequent drying on filter paper. Our modified protocol is characterized by a general aqueous work-up procedure, including extraction with brine for removal of dimethyl sulfoxide.

Related literature top

For the synthesis of 4-(4-methoxyphenoxy)benzaldehyde in an undergraduate laboratory course, see: Taber & Brannick (2015). For the synthesis of 4-aryloxybenzaldehydes and acetophenones, see: Yeager & Schissel (1991).

Experimental top

In a glass test tube (160x16 mm) 4-fluorobenzaldehyde (II) (C7H5FO, M =124.11 g/mol, 250 mg, 2.01 mmol, 1 eq), 4-methoxyphenol (III) (C7H8O2, M = 124.14 g/mol, 250 mg, 2.01 mmol, 1 eq) and potassium carbonate (K2CO3, M = 138.20 g/mol, 550 mg, 3.98 mmol, 2 eq) were suspended in dimethyl sulfoxide (2 ml, 1 ml/mmol). The reaction mixture was heated to 413 K and stirred at this temperature for 45 min. After consumption of the starting materials, the oil bath was removed and the suspension was cooled to room temperature. The reaction mixture was diluted with water (6 ml, 3 ml/mmol) and stirred at ambient temperature for 30 min. The resulting suspension was tranferred into a separatory funnel with water and then extracted with ethyl acetate (3x). The combined organic phases were extracted with saturated aqueous sodium chloride solution (5x) and dried over MgSO4. After removal of the solvents under reduced pressure, the light brown viscous oil was dissolved in dichloromethane (2 ml) and transferred into a wide-necked flask. The solution was diluted with n-heptane (1 ml) and the solvent was allowed to evaporate over three days. Crystals slowly form and grow, coating the sides of the flask. The large pale yellow crystals were washed with n-heptane (1 ml) and dried in vacuo to deliver 4-(4-methoxyphenoxy)benzaldehyde (I) (C14H12O3, M = 228.25 g/mol, 440 mg, 1.93 mmol, 96%). Recrystallization of a small amount of (I) from n-heptane by slow evaporation over one week provided clear colourless crystals. Rf 0.48 (cyclohexane/ethyl acetate 5/1); m.p. 323–325 K (n-heptane) [m.p. 332.5–333.5 K (n-hexane) (Yeager & Schissel, 1991)]; 1H NMR (CDCl3, 500 MHz) δ 3.83 (s, 3H), 6.92–6.95 (m, 2H), 6.99–7.05 (m, 4H), 7.81–7.83 (m, 2H), 9.90 (s, 1H); 13C NMR (CDCl3, 126 MHz) δ 55.8 (CH3), 115.3 (CH), 116.9 (CH), 122.0 (CH), 131.0 (C), 132.1 (CH), 148.3 (C), 157.0 (C), 164.2 (C), 190.9 (CH); IR ν 3005 (w), 2965 (w), 2835 (w), 2745 (w), 1680 (s), 1595 (m), 1575 (s), 1495 (s), 1440 (m), 1230 (s), 1195 (s), 1150 (s), 1100 (m), 1085 (s), 875 (m), 845 (m), 830 (s), 785 (s), 745 (m), 565 (m), 525 (m), 510 (s).

Refinement top

H-atoms attached to C, except those in CH3, were placed in calculated positions (C—H = 0.95 Å and Uiso(H) = 1.2 Ueq(C)). CH3 hydrogen atoms, which were taken from a Fourier map, were allowed to rotate but not to tip (C—H = 0.98 Å and Uiso(H) = 1.5 Ueq(C)).

Structure description top

As part of an evaluation of single step experiments for an undergraduate laboratory course, we came across a literature protocol that describes the preparation of crystalline 4-aryloxybenzaldehyde by nucleophilic aromatic substitution (Taber & Brannick, 2015). The reaction of 4-fluorobenzaldehyde (II) with 4-methoxyphenol (III) in the presence of potassium carbonate in dimethyl sulfoxide provided 4-(4-methoxyphenoxy)benzaldehyde (I) as large pale yellow crystals. The recrystallization of a small amount of (I) from n-heptane provided clear colourless crystals, suitable for X-ray analysis. In our hands, the literature protocol failed to deliver precipitated crude product upon dilution of the reaction mixture with water and subsequent drying on filter paper. Our modified protocol is characterized by a general aqueous work-up procedure, including extraction with brine for removal of dimethyl sulfoxide.

For the synthesis of 4-(4-methoxyphenoxy)benzaldehyde in an undergraduate laboratory course, see: Taber & Brannick (2015). For the synthesis of 4-aryloxybenzaldehydes and acetophenones, see: Yeager & Schissel (1991).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2008); cell refinement: CrysAlis PRO (Oxford Diffraction, 2008); data reduction: CrysAlis PRO (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXP2014 (Sheldrick, 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the labelling of all non-H atoms. Displacement ellipsoids are shown at the 50% probability level.
4-(4-Methoxyphenoxy)benzaldehyde top
Crystal data top
C14H12O3Dx = 1.360 Mg m−3
Mr = 228.24Melting point = 323–325 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.1297 (7) ÅCell parameters from 10396 reflections
b = 7.6581 (4) Åθ = 3.2–31.0°
c = 12.3577 (7) ŵ = 0.10 mm−1
β = 103.769 (6)°T = 173 K
V = 1114.92 (11) Å3Block, colourless
Z = 40.56 × 0.40 × 0.30 mm
F(000) = 480
Data collection top
Oxford Diffraction Xcalibur2 CCD
diffractometer		2967 independent reflections
Radiation source: fine-focus sealed tube2551 reflections with I > 2σ(I)
Detector resolution: 16.0560 pixels mm-1Rint = 0.023
ω und ψ scanθmax = 29.0°, θmin = 3.2°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)		h = −16→16
Tmin = 0.808, Tmax = 1.000k = −10→10
10049 measured reflectionsl = −16→14
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0604P)2 + 0.2707P]
where P = (Fo2 + 2Fc2)/3
2967 reflections(Δ/σ)max < 0.001
155 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C14H12O3V = 1114.92 (11) Å3
Mr = 228.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.1297 (7) ŵ = 0.10 mm−1
b = 7.6581 (4) ÅT = 173 K
c = 12.3577 (7) Å0.56 × 0.40 × 0.30 mm
β = 103.769 (6)°
Data collection top
Oxford Diffraction Xcalibur2 CCD
diffractometer		2967 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)		2551 reflections with I > 2σ(I)
Tmin = 0.808, Tmax = 1.000Rint = 0.023
10049 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.04Δρmax = 0.28 e Å−3
2967 reflectionsΔρmin = −0.22 e Å−3
155 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O11.04659 (7)0.20198 (13)0.46684 (7)0.0345 (2)
C11.03112 (9)0.22947 (15)0.36759 (9)0.0254 (2)
H1A1.08800.29330.34350.030*
O20.65559 (6)0.00429 (11)0.03836 (6)0.02476 (19)
C20.93213 (9)0.17254 (14)0.28176 (8)0.0207 (2)
O30.60491 (7)0.07872 (11)−0.41611 (6)0.02479 (19)
C30.84285 (9)0.07946 (14)0.30868 (8)0.0207 (2)
H3A0.84530.05240.38420.025*
C40.75139 (9)0.02708 (14)0.22570 (8)0.0204 (2)
H4A0.6902−0.03430.24400.025*
C50.74924 (8)0.06494 (13)0.11433 (8)0.0191 (2)
C60.83733 (9)0.15660 (14)0.08603 (8)0.0225 (2)
H6A0.83540.18170.01030.027*
C70.92811 (9)0.21065 (14)0.17041 (9)0.0233 (2)
H7A0.98840.27450.15220.028*
C80.65010 (9)0.02527 (14)−0.07551 (8)0.0210 (2)
C90.56903 (9)0.13878 (14)−0.13564 (9)0.0221 (2)
H9A0.52280.2056−0.09900.026*
C100.55637 (9)0.15361 (14)−0.24972 (9)0.0221 (2)
H10A0.50120.2310−0.29160.027*
C110.62441 (8)0.05530 (13)−0.30341 (8)0.0198 (2)
C120.70607 (9)−0.05710 (14)−0.24197 (9)0.0228 (2)
H12A0.7531−0.1232−0.27810.027*
C130.71864 (9)−0.07229 (14)−0.12726 (9)0.0239 (2)
H13A0.7739−0.1491−0.08490.029*
C140.66492 (10)−0.03182 (16)−0.47516 (9)0.0280 (2)
H14A0.7466−0.0111−0.44880.042*
H14B0.6412−0.0062−0.55500.042*
H14C0.6482−0.1542−0.46220.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0325 (4)0.0469 (5)0.0221 (4)−0.0060 (4)0.0023 (3)−0.0031 (4)
C10.0219 (5)0.0302 (6)0.0241 (5)−0.0030 (4)0.0057 (4)−0.0041 (4)
O20.0225 (4)0.0336 (4)0.0178 (4)−0.0075 (3)0.0041 (3)0.0004 (3)
C20.0216 (5)0.0215 (5)0.0194 (5)0.0002 (4)0.0058 (4)−0.0017 (4)
O30.0275 (4)0.0287 (4)0.0177 (4)0.0030 (3)0.0047 (3)−0.0011 (3)
C30.0238 (5)0.0228 (5)0.0168 (4)0.0009 (4)0.0073 (4)0.0002 (4)
C40.0205 (5)0.0217 (5)0.0211 (5)−0.0012 (4)0.0088 (4)0.0007 (4)
C50.0194 (5)0.0192 (5)0.0187 (5)0.0004 (3)0.0042 (4)−0.0005 (4)
C60.0256 (5)0.0241 (5)0.0185 (5)−0.0027 (4)0.0067 (4)0.0034 (4)
C70.0236 (5)0.0254 (5)0.0222 (5)−0.0046 (4)0.0079 (4)0.0013 (4)
C80.0209 (5)0.0241 (5)0.0175 (4)−0.0053 (4)0.0037 (4)−0.0010 (4)
C90.0195 (5)0.0233 (5)0.0238 (5)−0.0010 (4)0.0061 (4)−0.0044 (4)
C100.0192 (5)0.0229 (5)0.0227 (5)0.0013 (4)0.0020 (4)−0.0011 (4)
C110.0205 (5)0.0203 (5)0.0183 (4)−0.0035 (4)0.0040 (4)−0.0016 (4)
C120.0228 (5)0.0234 (5)0.0233 (5)0.0023 (4)0.0074 (4)−0.0010 (4)
C130.0224 (5)0.0249 (5)0.0235 (5)0.0023 (4)0.0036 (4)0.0033 (4)
C140.0323 (6)0.0309 (6)0.0232 (5)0.0002 (5)0.0115 (4)−0.0027 (4)
Geometric parameters (Å, º) top
O1—C11.2142 (14)C6—H6A0.9500
C1—C21.4664 (14)C7—H7A0.9500
C1—H1A0.9500C8—C131.3826 (15)
O2—C51.3711 (12)C8—C91.3881 (15)
O2—C81.4021 (12)C9—C101.3861 (14)
C2—C71.3962 (14)C9—H9A0.9500
C2—C31.4010 (14)C10—C111.3959 (14)
O3—C111.3678 (12)C10—H10A0.9500
O3—C141.4254 (13)C11—C121.3931 (14)
C3—C41.3791 (14)C12—C131.3940 (14)
C3—H3A0.9500C12—H12A0.9500
C4—C51.4006 (13)C13—H13A0.9500
C4—H4A0.9500C14—H14A0.9800
C5—C61.3909 (14)C14—H14B0.9800
C6—C71.3873 (14)C14—H14C0.9800
O1—C1—C2125.60 (10)C13—C8—O2120.81 (9)
O1—C1—H1A117.2C9—C8—O2117.86 (9)
C2—C1—H1A117.2C10—C9—C8119.25 (10)
C5—O2—C8118.82 (8)C10—C9—H9A120.4
C7—C2—C3119.52 (9)C8—C9—H9A120.4
C7—C2—C1118.77 (10)C9—C10—C11120.29 (9)
C3—C2—C1121.71 (9)C9—C10—H10A119.9
C11—O3—C14117.25 (8)C11—C10—H10A119.9
C4—C3—C2120.13 (9)O3—C11—C12124.34 (9)
C4—C3—H3A119.9O3—C11—C10115.76 (9)
C2—C3—H3A119.9C12—C11—C10119.89 (9)
C3—C4—C5119.60 (9)C11—C12—C13119.82 (10)
C3—C4—H4A120.2C11—C12—H12A120.1
C5—C4—H4A120.2C13—C12—H12A120.1
O2—C5—C6124.03 (9)C8—C13—C12119.54 (9)
O2—C5—C4114.91 (9)C8—C13—H13A120.2
C6—C5—C4121.05 (9)C12—C13—H13A120.2
C7—C6—C5118.78 (9)O3—C14—H14A109.5
C7—C6—H6A120.6O3—C14—H14B109.5
C5—C6—H6A120.6H14A—C14—H14B109.5
C6—C7—C2120.91 (10)O3—C14—H14C109.5
C6—C7—H7A119.5H14A—C14—H14C109.5
C2—C7—H7A119.5H14B—C14—H14C109.5
C13—C8—C9121.21 (9)
O1—C1—C2—C7−178.37 (11)C5—O2—C8—C1371.52 (13)
O1—C1—C2—C30.79 (18)C5—O2—C8—C9−112.38 (11)
C7—C2—C3—C4−0.45 (16)C13—C8—C9—C100.34 (15)
C1—C2—C3—C4−179.60 (10)O2—C8—C9—C10−175.74 (9)
C2—C3—C4—C51.06 (16)C8—C9—C10—C110.04 (15)
C8—O2—C5—C64.13 (15)C14—O3—C11—C126.25 (15)
C8—O2—C5—C4−175.51 (9)C14—O3—C11—C10−174.01 (9)
C3—C4—C5—O2178.84 (9)C9—C10—C11—O3179.69 (9)
C3—C4—C5—C6−0.82 (16)C9—C10—C11—C12−0.56 (15)
O2—C5—C6—C7−179.68 (10)O3—C11—C12—C13−179.58 (9)
C4—C5—C6—C7−0.06 (16)C10—C11—C12—C130.69 (15)
C5—C6—C7—C20.69 (16)C9—C8—C13—C12−0.21 (16)
C3—C2—C7—C6−0.44 (16)O2—C8—C13—C12175.76 (9)
C1—C2—C7—C6178.74 (10)C11—C12—C13—C8−0.31 (16)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C13—H13A···O1i0.952.583.5129 (14)167
C7—H7A···O1ii0.952.563.2500 (14)130
C1—H1A···Cg1iii0.952.733.5453 (12)145
C10—H10A···Cg2iv0.952.883.7465 (12)152
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, y+1/2, −z+1/2; (iv) −x+1, y+1/2, −z−1/2.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C13—H13A···O1i0.952.583.5129 (14)167
C7—H7A···O1ii0.952.563.2500 (14)130
C1—H1A···Cg1iii0.952.733.5453 (12)145
C10—H10A···Cg2iv0.952.883.7465 (12)152
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, y+1/2, −z+1/2; (iv) −x+1, y+1/2, −z−1/2.
 

Acknowledgements

The TU Dortmund is greatefully acknowledged for financial support.

References

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 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 71| Part 12| December 2015| Page o1021
https://doi.org/10.1107/S2056989015022707
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