organic compounds
4-Methoxy-3-(methoxymethyl)benzaldehyde
aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 211816, People's Republic of China
*Correspondence e-mail: guocheng@njut.edu.cn
In the title compound, C10H12O3, the dihedral angle between the benzene ring and the methoxymethyl side chain is 9.7 (2)°. The O atom of the aldehyde group and the C atom of the methoxy group deviate from the plane of the ring by 0.039 (3) and 0.338 (4) Å, respectively. The only intermolecular interactions are very weak C—H⋯π interactions.
Related literature
For the synthesis and applications of the title compound see: Jonali et al. (2003).
Experimental
Crystal data
|
Refinement
|
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536812050350/hb7010sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050350/hb7010Isup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812050350/hb7010Isup3.cml
The title compound, (I) was prepared by the literature method (Jonali et al. 2003). Colourless blocks were obtained by dissolving (I) (0.18 g, 1.0 mmol) in acetone (25 ml) and evaporating the solvent slowly at room temperature for about 7 d.
H atoms were positioned geometrically and refined as riding groups with Uiso(H) = xUeq(C), where x = 1.2 for aromatic H, and x = 1.5 for other H.
For the synthesis and applications of the title compound see: Jonali et al. (2003).
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell
CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. A packing diagram of (I). |
C10H12O3 | F(000) = 384 |
Mr = 180.20 | Dx = 1.270 Mg m−3 |
Monoclinic, P21/c | Melting point: 341 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8100 (16) Å | Cell parameters from 25 reflections |
b = 8.3970 (17) Å | θ = 9–13° |
c = 14.510 (3) Å | µ = 0.09 mm−1 |
β = 98.01 (3)° | T = 293 K |
V = 942.3 (3) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.20 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 860 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.099 |
Graphite monochromator | θmax = 25.4°, θmin = 2.6° |
ω/2θ scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→10 |
Tmin = 0.973, Tmax = 0.991 | l = −17→17 |
1860 measured reflections | 3 standard reflections every 200 reflections |
1729 independent reflections | intensity decay: 1% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.070P)2] where P = (Fo2 + 2Fc2)/3 |
1729 reflections | (Δ/σ)max < 0.001 |
118 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C10H12O3 | V = 942.3 (3) Å3 |
Mr = 180.20 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.8100 (16) Å | µ = 0.09 mm−1 |
b = 8.3970 (17) Å | T = 293 K |
c = 14.510 (3) Å | 0.30 × 0.20 × 0.10 mm |
β = 98.01 (3)° |
Enraf–Nonius CAD-4 diffractometer | 860 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.099 |
Tmin = 0.973, Tmax = 0.991 | 3 standard reflections every 200 reflections |
1860 measured reflections | intensity decay: 1% |
1729 independent reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.19 e Å−3 |
1729 reflections | Δρmin = −0.18 e Å−3 |
118 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 | ||
O1 | 0.3742 (3) | −0.2060 (2) | 0.10208 (17) | 0.0606 (7) | |
C1 | 0.4323 (4) | 0.0653 (3) | 0.1125 (2) | 0.0449 (8) | |
O2 | 0.2282 (3) | 0.2507 (3) | 0.03860 (18) | 0.0736 (8) | |
C2 | 0.5453 (4) | 0.1885 (4) | 0.1380 (2) | 0.0512 (9) | |
H2A | 0.5092 | 0.2927 | 0.1250 | 0.061* | |
O3 | 0.8048 (3) | 0.4313 (3) | 0.1968 (2) | 0.0838 (10) | |
C3 | 0.7125 (5) | 0.1612 (4) | 0.1829 (2) | 0.0531 (9) | |
C4 | 0.7648 (4) | 0.0059 (4) | 0.2027 (3) | 0.0608 (10) | |
H4A | 0.8752 | −0.0133 | 0.2339 | 0.073* | |
C5 | 0.6561 (5) | −0.1209 (4) | 0.1772 (3) | 0.0579 (10) | |
H5A | 0.6928 | −0.2248 | 0.1904 | 0.070* | |
C6 | 0.4919 (4) | −0.0912 (3) | 0.1318 (2) | 0.0494 (9) | |
C7 | 0.4335 (5) | −0.3667 (4) | 0.1007 (3) | 0.0688 (12) | |
H7A | 0.3380 | −0.4353 | 0.0791 | 0.103* | |
H7B | 0.4826 | −0.3978 | 0.1624 | 0.103* | |
H7C | 0.5196 | −0.3749 | 0.0598 | 0.103* | |
C8 | 0.2523 (4) | 0.0900 (3) | 0.0654 (2) | 0.0547 (9) | |
H8A | 0.2307 | 0.0221 | 0.0110 | 0.066* | |
H8B | 0.1709 | 0.0614 | 0.1075 | 0.066* | |
C9 | 0.0623 (5) | 0.2781 (4) | −0.0121 (3) | 0.0835 (13) | |
H9A | 0.0509 | 0.3887 | −0.0286 | 0.125* | |
H9B | −0.0248 | 0.2497 | 0.0256 | 0.125* | |
H9C | 0.0485 | 0.2145 | −0.0676 | 0.125* | |
C10 | 0.8314 (5) | 0.2919 (5) | 0.2107 (3) | 0.0680 (11) | |
H10A | 0.9390 | 0.2644 | 0.2425 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0666 (16) | 0.0309 (13) | 0.0856 (18) | −0.0025 (11) | 0.0151 (13) | −0.0033 (11) |
C1 | 0.050 (2) | 0.0358 (18) | 0.052 (2) | −0.0002 (16) | 0.0158 (16) | −0.0018 (14) |
O2 | 0.0662 (17) | 0.0371 (14) | 0.112 (2) | 0.0032 (13) | −0.0070 (15) | 0.0046 (13) |
C2 | 0.058 (2) | 0.0342 (17) | 0.063 (2) | 0.0024 (16) | 0.0133 (18) | 0.0005 (15) |
O3 | 0.082 (2) | 0.0481 (16) | 0.118 (3) | −0.0127 (14) | 0.0024 (17) | −0.0007 (16) |
C3 | 0.058 (2) | 0.0404 (19) | 0.062 (2) | 0.0006 (18) | 0.0120 (18) | −0.0036 (17) |
C4 | 0.055 (2) | 0.053 (2) | 0.075 (3) | 0.0049 (19) | 0.0107 (19) | −0.0041 (19) |
C5 | 0.064 (2) | 0.040 (2) | 0.073 (3) | 0.0082 (18) | 0.019 (2) | 0.0009 (18) |
C6 | 0.057 (2) | 0.0321 (18) | 0.061 (2) | −0.0024 (16) | 0.0157 (19) | −0.0034 (15) |
C7 | 0.084 (3) | 0.0297 (18) | 0.097 (3) | 0.0005 (18) | 0.029 (2) | −0.0046 (18) |
C8 | 0.060 (2) | 0.0332 (18) | 0.072 (3) | −0.0042 (16) | 0.0143 (19) | 0.0049 (16) |
C9 | 0.066 (3) | 0.062 (3) | 0.119 (4) | 0.016 (2) | 0.000 (3) | 0.004 (2) |
C10 | 0.060 (2) | 0.058 (2) | 0.084 (3) | −0.007 (2) | 0.006 (2) | −0.003 (2) |
O1—C6 | 1.360 (4) | C4—H4A | 0.9300 |
O1—C7 | 1.427 (3) | C5—C6 | 1.380 (4) |
C1—C2 | 1.376 (4) | C5—H5A | 0.9300 |
C1—C6 | 1.409 (4) | C7—H7A | 0.9600 |
C1—C8 | 1.490 (4) | C7—H7B | 0.9600 |
O2—C8 | 1.410 (3) | C7—H7C | 0.9600 |
O2—C9 | 1.416 (4) | C8—H8A | 0.9700 |
C2—C3 | 1.395 (5) | C8—H8B | 0.9700 |
C2—H2A | 0.9300 | C9—H9A | 0.9600 |
O3—C10 | 1.201 (4) | C9—H9B | 0.9600 |
C3—C4 | 1.385 (4) | C9—H9C | 0.9600 |
C3—C10 | 1.457 (5) | C10—H10A | 0.9300 |
C4—C5 | 1.380 (4) | ||
C6—O1—C7 | 118.0 (3) | O1—C7—H7B | 109.5 |
C2—C1—C6 | 117.8 (3) | H7A—C7—H7B | 109.5 |
C2—C1—C8 | 123.2 (3) | O1—C7—H7C | 109.5 |
C6—C1—C8 | 119.0 (3) | H7A—C7—H7C | 109.5 |
C8—O2—C9 | 112.1 (3) | H7B—C7—H7C | 109.5 |
C1—C2—C3 | 121.7 (3) | O2—C8—C1 | 109.9 (3) |
C1—C2—H2A | 119.2 | O2—C8—H8A | 109.7 |
C3—C2—H2A | 119.2 | C1—C8—H8A | 109.7 |
C4—C3—C2 | 118.8 (3) | O2—C8—H8B | 109.7 |
C4—C3—C10 | 119.6 (3) | C1—C8—H8B | 109.7 |
C2—C3—C10 | 121.6 (3) | H8A—C8—H8B | 108.2 |
C5—C4—C3 | 121.2 (3) | O2—C9—H9A | 109.5 |
C5—C4—H4A | 119.4 | O2—C9—H9B | 109.5 |
C3—C4—H4A | 119.4 | H9A—C9—H9B | 109.5 |
C4—C5—C6 | 119.0 (3) | O2—C9—H9C | 109.5 |
C4—C5—H5A | 120.5 | H9A—C9—H9C | 109.5 |
C6—C5—H5A | 120.5 | H9B—C9—H9C | 109.5 |
O1—C6—C5 | 124.4 (3) | O3—C10—C3 | 126.8 (4) |
O1—C6—C1 | 114.1 (3) | O3—C10—H10A | 116.6 |
C5—C6—C1 | 121.5 (3) | C3—C10—H10A | 116.6 |
O1—C7—H7A | 109.5 | ||
C6—C1—C2—C3 | −1.0 (5) | C4—C5—C6—C1 | −1.0 (5) |
C8—C1—C2—C3 | 179.3 (3) | C2—C1—C6—O1 | −178.2 (3) |
C1—C2—C3—C4 | −0.6 (5) | C8—C1—C6—O1 | 1.5 (4) |
C1—C2—C3—C10 | −179.4 (3) | C2—C1—C6—C5 | 1.8 (5) |
C2—C3—C4—C5 | 1.4 (5) | C8—C1—C6—C5 | −178.4 (3) |
C10—C3—C4—C5 | −179.8 (3) | C9—O2—C8—C1 | 176.0 (3) |
C3—C4—C5—C6 | −0.6 (5) | C2—C1—C8—O2 | 9.5 (4) |
C7—O1—C6—C5 | −13.0 (5) | C6—C1—C8—O2 | −170.2 (3) |
C7—O1—C6—C1 | 167.1 (3) | C4—C3—C10—O3 | 178.7 (4) |
C4—C5—C6—O1 | 179.0 (3) | C2—C3—C10—O3 | −2.5 (6) |
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7B···Cg1i | 0.96 | 2.84 | 3.650 (5) | 143 |
C8—H8A···Cg1ii | 0.97 | 2.97 | 3.731 (3) | 136 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C10H12O3 |
Mr | 180.20 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 7.8100 (16), 8.3970 (17), 14.510 (3) |
β (°) | 98.01 (3) |
V (Å3) | 942.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.973, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1860, 1729, 860 |
Rint | 0.099 |
(sin θ/λ)max (Å−1) | 0.604 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.165, 1.01 |
No. of reflections | 1729 |
No. of parameters | 118 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.18 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7B···Cg1i | 0.96 | 2.84 | 3.650 (5) | 143 |
C8—H8A···Cg1ii | 0.97 | 2.97 | 3.731 (3) | 136 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y, −z. |
Acknowledgements
The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.
References
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Jonali, G., Naleen, B. & Amrit, G. (2003). J. Chem. Res. S, 200–203. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.