4-Meth­oxy-3-(meth­oxy­meth­yl)benzalde­hyde

Zhang, J.-C.; Sun, J.; Zhang, J.; Liu, G.-L.; Guo, C.

doi:10.1107/S1600536812050350

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o112

https://doi.org/10.1107/S1600536812050350

Open

access

4-Methoxy-3-(methoxymethyl)benzaldehyde

Jing-Chao Zhang,^a Jun Sun,^a Juan Zhang,^a Guang-Lin Liu ^a and Cheng Guo ^a ^*

^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

(Received 7 December 2012; accepted 11 December 2012; online 19 December 2012)

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

C₁₀H₁₂O₃
M_r = 180.20
Monoclinic, P 2₁ /c
a = 7.8100 (16) Å
b = 8.3970 (17) Å
c = 14.510 (3) Å
β = 98.01 (3)°
V = 942.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.973, T_max = 0.991
1860 measured reflections
1729 independent reflections
860 reflections with I > 2σ(I)
R_int = 0.099
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.165
S = 1.01
1729 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812050350/hb7010sup1.cif

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

checkCIF report

Related literature top

For the synthesis and applications of the title compound see: Jonali et al. (2003).

Experimental top

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.

Structure description top

For the synthesis and applications of the title compound see: Jonali et al. (2003).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: 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).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I).

4-Methoxy-3-(methoxymethyl)benzaldehyde top

Crystal data top

C₁₀H₁₂O₃	F(000) = 384
M_r = 180.20	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	860 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.099
Graphite monochromator	θ_max = 25.4°, θ_min = 2.6°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
T_min = 0.973, T_max = 0.991	l = −17→17
1860 measured reflections	3 standard reflections every 200 reflections
1729 independent reflections	intensity decay: 1%

Refinement top

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(F_o²) + (0.070P)²] where P = (F_o² + 2F_c²)/3
1729 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₀H₁₂O₃	V = 942.3 (3) Å³
M_r = 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)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	860 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.099
T_min = 0.973, T_max = 0.991	3 standard reflections every 200 reflections
1860 measured reflections	intensity decay: 1%
1729 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.165	H-atom parameters constrained
S = 1.01	Δρ_max = 0.19 e Å⁻³
1729 reflections	Δρ_min = −0.18 e Å⁻³
118 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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.973, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	1860, 1729, 860
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o112

https://doi.org/10.1107/S1600536812050350

Open

access