2-Methoxy­naphthalene-1-carbaldehyde

Tang, C.

doi:10.1107/S1600536809014287

organic compounds

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Volume 65| Part 5| May 2009| Page o1088

doi:10.1107/S1600536809014287

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2-Methoxynaphthalene-1-carbaldehyde

Chunbao Tang ^a ^*

^aDepartment of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China
^*Correspondence e-mail: chunbao_tang@126.com

(Received 15 April 2009; accepted 16 April 2009; online 22 April 2009)

In the title compound, C₁₂H₁₀O₂, the aldehyde and methoxy groups are slightly twisted around the single bonds that join them to the naphthalene ring system. In the crystal structure, molecules are linked through intermolecular C—H⋯O hydrogen bonds, forming chains running along the c axis.

Related literature

For crystal structures of Schiff bases, see: Yehye et al. (2008 ); Tabatabaee et al. (2007 ); Zhang & Li (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₁₀O₂
M_r = 186.20
Monoclinic, P 2₁ /c
a = 8.689 (3) Å
b = 14.155 (4) Å
c = 7.667 (2) Å
β = 94.805 (4)°
V = 939.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.982, T_max = 0.984
5187 measured reflections
2046 independent reflections
1477 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.124
S = 1.03
2046 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12C⋯O1ⁱ	0.96	2.46	3.362 (4)	156 (6)
Symmetry code: (i) x, y, z+1.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536809014287/ci2783sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014287/ci2783Isup2.hkl

checkCIF report

Comment top

A large number of aldehydes were chosen as starting materials for the synthesis of Schiff base derivatives (Yehye et al., 2008; Tabatabaee et al., 2007; Zhang & Li, 2007). We report here the crystal structure of the title compound.

In the title molecule (Fig. 1), the bond lengths are within normal ranges (Allen et al., 1987). The carbonyl oxygen atom O1 deviates from the plane of the naphthalene ring system by 0.027 (2) Å. The aldehyde and methoxy groups are slightly twisted away from the naphthalene ring system [C10—C1—C11—O1 10.6 (3)° and C12—O2—C2—C3 = 8.4 (2)°].

In the crystal structure, molecules are linked through intermolecular C–H···O hydrogen bonds (Table 1), forming chains running along the c axis (Fig. 2).

Related literature top

For crystal structures of Schiff bases, see: Yehye et al. (2008); Tabatabaee et al. (2007); Zhang & Li (2007). For bond-length values, see: Allen et al. (1987).

Experimental top

The title compound was obtained commercially (Lancaster). Single crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution of the compound.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
	Fig. 2. The molecular packing of the title compound, viewed along the b axis. Intermolecular C–H···O hydrogen bonds are shown as dashed lines.

2-Methoxynaphthalene-1-carbaldehyde top

Crystal data top

C₁₂H₁₀O₂	F(000) = 392
M_r = 186.20	D_x = 1.316 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1550 reflections
a = 8.689 (3) Å	θ = 2.3–25.3°
b = 14.155 (4) Å	µ = 0.09 mm⁻¹
c = 7.667 (2) Å	T = 298 K
β = 94.805 (4)°	Block, colourless
V = 939.7 (5) Å³	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2046 independent reflections
Radiation source: fine-focus sealed tube	1477 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→11
T_min = 0.982, T_max = 0.984	k = −17→18
5187 measured reflections	l = −8→9

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0588P)² + 0.1007P] where P = (F_o² + 2F_c²)/3
2046 reflections	(Δ/σ)_max = 0.001
128 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₂H₁₀O₂	V = 939.7 (5) Å³
M_r = 186.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.689 (3) Å	µ = 0.09 mm⁻¹
b = 14.155 (4) Å	T = 298 K
c = 7.667 (2) Å	0.20 × 0.20 × 0.18 mm
β = 94.805 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2046 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1477 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.984	R_int = 0.018
5187 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	Δρ_max = 0.12 e Å⁻³
2046 reflections	Δρ_min = −0.17 e Å⁻³
128 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	0.28487 (13)	0.04582 (12)	−0.30026 (16)	0.0951 (5)
O2	0.37442 (12)	0.12897 (9)	0.17417 (14)	0.0716 (4)
C1	0.17514 (14)	0.10308 (9)	−0.04428 (17)	0.0445 (3)
C2	0.22015 (16)	0.13172 (9)	0.12545 (18)	0.0493 (3)
C3	0.11126 (18)	0.16328 (10)	0.23780 (19)	0.0570 (4)
H3	0.1427	0.1806	0.3523	0.068*
C4	−0.03974 (18)	0.16829 (10)	0.17843 (19)	0.0561 (4)
H4	−0.1109	0.1892	0.2539	0.067*
C5	−0.09270 (15)	0.14282 (9)	0.00617 (18)	0.0467 (3)
C6	−0.25038 (17)	0.15016 (10)	−0.0548 (2)	0.0596 (4)
H6	−0.3211	0.1723	0.0200	0.072*
C7	−0.29984 (17)	0.12527 (11)	−0.2210 (2)	0.0644 (4)
H7	−0.4038	0.1305	−0.2597	0.077*
C8	−0.19430 (18)	0.09191 (11)	−0.3336 (2)	0.0617 (4)
H8	−0.2289	0.0748	−0.4473	0.074*
C9	−0.04112 (16)	0.08386 (10)	−0.28015 (18)	0.0527 (4)
H9	0.0269	0.0613	−0.3578	0.063*
C10	0.01568 (14)	0.10936 (8)	−0.10843 (17)	0.0426 (3)
C11	0.29521 (17)	0.06484 (12)	−0.1473 (2)	0.0618 (4)
H11	0.3909	0.0540	−0.0870	0.074*
C12	0.4284 (2)	0.14661 (15)	0.3509 (2)	0.0850 (6)
H12A	0.4022	0.2100	0.3816	0.128*
H12B	0.5385	0.1389	0.3649	0.128*
H12C	0.3809	0.1029	0.4257	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0651 (8)	0.1637 (14)	0.0584 (8)	0.0113 (7)	0.0161 (6)	−0.0216 (8)
O2	0.0509 (6)	0.1051 (9)	0.0568 (7)	−0.0042 (6)	−0.0083 (5)	−0.0022 (6)
C1	0.0433 (7)	0.0458 (7)	0.0447 (8)	−0.0016 (5)	0.0056 (5)	0.0043 (5)
C2	0.0471 (8)	0.0500 (8)	0.0498 (8)	−0.0030 (6)	−0.0009 (6)	0.0033 (6)
C3	0.0680 (10)	0.0567 (8)	0.0457 (8)	0.0016 (7)	0.0013 (7)	−0.0087 (6)
C4	0.0613 (9)	0.0534 (8)	0.0555 (9)	0.0088 (6)	0.0156 (7)	−0.0047 (6)
C5	0.0475 (7)	0.0399 (7)	0.0533 (8)	0.0015 (5)	0.0082 (6)	0.0027 (6)
C6	0.0469 (8)	0.0604 (9)	0.0727 (11)	0.0051 (6)	0.0122 (7)	0.0066 (7)
C7	0.0431 (8)	0.0705 (10)	0.0782 (12)	−0.0019 (7)	−0.0039 (7)	0.0090 (8)
C8	0.0575 (9)	0.0658 (9)	0.0595 (10)	−0.0065 (7)	−0.0090 (7)	−0.0017 (7)
C9	0.0523 (8)	0.0546 (8)	0.0508 (8)	−0.0024 (6)	0.0028 (6)	−0.0024 (6)
C10	0.0453 (7)	0.0372 (6)	0.0456 (8)	−0.0018 (5)	0.0045 (5)	0.0035 (5)
C11	0.0463 (8)	0.0847 (11)	0.0552 (9)	0.0004 (7)	0.0089 (6)	0.0020 (8)
C12	0.0713 (11)	0.1163 (16)	0.0632 (11)	−0.0073 (10)	−0.0195 (9)	−0.0018 (10)

Geometric parameters (Å, º) top

O1—C11	1.1991 (18)	C6—C7	1.357 (2)
O2—C2	1.3615 (16)	C6—H6	0.93
O2—C12	1.4180 (19)	C7—C8	1.393 (2)
C1—C2	1.3877 (19)	C7—H7	0.93
C1—C10	1.4336 (18)	C8—C9	1.364 (2)
C1—C11	1.4641 (19)	C8—H8	0.93
C2—C3	1.405 (2)	C9—C10	1.4137 (19)
C3—C4	1.354 (2)	C9—H9	0.93
C3—H3	0.93	C11—H11	0.93
C4—C5	1.409 (2)	C12—H12A	0.96
C4—H4	0.93	C12—H12B	0.96
C5—C6	1.414 (2)	C12—H12C	0.96
C5—C10	1.4219 (19)

C2—O2—C12	119.74 (13)	C6—C7—H7	120.1
C2—C1—C10	119.47 (12)	C8—C7—H7	120.1
C2—C1—C11	117.16 (12)	C9—C8—C7	121.22 (14)
C10—C1—C11	123.34 (12)	C9—C8—H8	119.4
O2—C2—C1	116.27 (12)	C7—C8—H8	119.4
O2—C2—C3	122.61 (13)	C8—C9—C10	120.94 (14)
C1—C2—C3	121.11 (13)	C8—C9—H9	119.5
C4—C3—C2	119.60 (13)	C10—C9—H9	119.5
C4—C3—H3	120.2	C9—C10—C5	117.58 (12)
C2—C3—H3	120.2	C9—C10—C1	123.75 (12)
C3—C4—C5	122.21 (13)	C5—C10—C1	118.67 (12)
C3—C4—H4	118.9	O1—C11—C1	127.75 (15)
C5—C4—H4	118.9	O1—C11—H11	116.1
C4—C5—C6	121.50 (13)	C1—C11—H11	116.1
C4—C5—C10	118.91 (13)	O2—C12—H12A	109.5
C6—C5—C10	119.59 (13)	O2—C12—H12B	109.5
C7—C6—C5	120.87 (14)	H12A—C12—H12B	109.5
C7—C6—H6	119.6	O2—C12—H12C	109.5
C5—C6—H6	119.6	H12A—C12—H12C	109.5
C6—C7—C8	119.79 (14)	H12B—C12—H12C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···O1ⁱ	0.96	2.46	3.362 (4)	156 (6)

Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀O₂
M_r	186.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.689 (3), 14.155 (4), 7.667 (2)
β (°)	94.805 (4)
V (Å³)	939.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.982, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	5187, 2046, 1477
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.124, 1.03
No. of reflections	2046
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.17

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···O1ⁱ	0.96	2.46	3.362 (4)	156 (6)

Symmetry code: (i) x, y, z+1.

Acknowledgements

Financial support from the Jiaying University Research Fund is gratefully acknowledged.

References

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