2-Methoxy-naphthalene-1-carbaldehyde.

In the title compound, C(12)H(10)O(2), the aldehyde and meth-oxy groups are slightly twisted around the single bonds that join them to the naphthalene ring system. In the crystal structure, mol-ecules are linked through inter-molecular 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 = 186.20

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.124

S = 1.03

2046 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.17 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014287/ci2783sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H10O2	F(000) = 392
Mr = 186.20	Dx = 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

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

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(Fo2) + (0.0588P)2 + 0.1007P] where P = (Fo2 + 2Fc2)/3
2046 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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	0.28487 (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*

	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)

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

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

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) .