2-Hy-droxy-3-meth-oxy-methyl-5-methyl-benzaldehyde.

In the title mol-ecule, C(10)H(12)O(3), all non-H atoms lie in a common plane (r.m.s deviation = 0.010 Å). The mol-ecular conformation is stabilized by an intra-molecular O-H⋯O hydrogen bond.

Related literature

For the biological activity of methyl­benzene derivatives, see: Anbarasan et al. (2011 ▶); Chan & Daniels (2007 ▶). For related structures see: Wang et al. (2011 ▶); Kılıç et al. (2009 ▶); For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H12O3

M = 180.20

Monoclinic,

a = 13.899 (3) Å

b = 8.9184 (19) Å

c = 7.5043 (16) Å

β = 94.098 (6)°

V = 927.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.30 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.981

10089 measured reflections

2329 independent reflections

1213 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.181

S = 1.03

2329 reflections

121 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813002845/bt6886sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002845/bt6886Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002845/bt6886Isup3.cml

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

C10H12O3	F(000) = 384
Mr = 180.20	Dx = 1.290 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3221 reflections
a = 13.899 (3) Å	θ = 2.7–24.8°
b = 8.9184 (19) Å	µ = 0.10 mm−1
c = 7.5043 (16) Å	T = 295 K
β = 94.098 (6)°	Block, yellow
V = 927.8 (3) Å3	0.30 × 0.24 × 0.20 mm
Z = 4

Bruker Kappa APEXII diffractometer	2329 independent reflections
Radiation source: fine-focus sealed tube	1213 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ω and φ scans	θmax = 28.7°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.972, Tmax = 0.981	k = −11→12
10089 measured reflections	l = −9→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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0625P)2 + 0.4641P] where P = (Fo2 + 2Fc2)/3
2329 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

	x	y	z	Uiso*/Ueq
C8	0.92734 (18)	1.0908 (3)	0.1482 (4)	0.0617 (7)
H8	0.9842	1.1345	0.1959	0.074*
C1	0.85176 (16)	1.1898 (2)	0.0792 (3)	0.0459 (6)
C6	0.86550 (16)	1.3446 (3)	0.0868 (3)	0.0497 (6)
H6	0.9241	1.3825	0.1349	0.060*
C5	0.79476 (17)	1.4420 (2)	0.0250 (3)	0.0479 (6)
C4	0.70806 (16)	1.3801 (2)	−0.0467 (3)	0.0457 (6)
H4	0.6595	1.4449	−0.0906	0.055*
C3	0.69089 (16)	1.2288 (2)	−0.0558 (3)	0.0426 (5)
C2	0.76424 (16)	1.1324 (2)	0.0081 (3)	0.0438 (5)
C9	0.59741 (17)	1.1631 (3)	−0.1290 (3)	0.0536 (6)
H9A	0.6088	1.0965	−0.2275	0.064*
H9B	0.5690	1.1049	−0.0370	0.064*
C10	0.4451 (2)	1.2195 (3)	−0.2637 (4)	0.0741 (9)
H10A	0.4569	1.1579	−0.3648	0.111*
H10B	0.4030	1.3006	−0.3012	0.111*
H10C	0.4155	1.1602	−0.1759	0.111*
C7	0.8079 (2)	1.6091 (3)	0.0330 (4)	0.0687 (8)
H7A	0.7929	1.6451	0.1483	0.103*
H7B	0.7657	1.6556	−0.0576	0.103*
H7C	0.8736	1.6336	0.0132	0.103*
O1	0.92264 (14)	0.9535 (2)	0.1490 (3)	0.0772 (6)
O2	0.74664 (13)	0.98329 (17)	0.0006 (3)	0.0618 (5)
H2	0.7946	0.9376	0.0410	0.093*
O3	0.53348 (12)	1.27783 (19)	−0.1888 (3)	0.0638 (5)

	U11	U22	U33	U12	U13	U23
C8	0.0507 (15)	0.0628 (17)	0.0718 (19)	0.0088 (12)	0.0061 (12)	0.0047 (13)
C1	0.0469 (13)	0.0412 (12)	0.0500 (14)	0.0053 (10)	0.0060 (10)	0.0027 (9)
C6	0.0463 (13)	0.0475 (14)	0.0549 (15)	−0.0047 (10)	0.0020 (10)	−0.0034 (11)
C5	0.0530 (14)	0.0374 (11)	0.0532 (14)	−0.0033 (10)	0.0039 (10)	−0.0027 (10)
C4	0.0475 (13)	0.0361 (11)	0.0535 (14)	0.0042 (9)	0.0028 (10)	0.0029 (10)
C3	0.0475 (12)	0.0357 (11)	0.0449 (13)	−0.0051 (9)	0.0059 (9)	0.0007 (9)
C2	0.0515 (13)	0.0319 (11)	0.0487 (13)	−0.0005 (9)	0.0086 (10)	0.0017 (9)
C9	0.0560 (14)	0.0406 (12)	0.0638 (16)	−0.0052 (11)	0.0027 (12)	0.0040 (11)
C10	0.0586 (17)	0.0758 (19)	0.085 (2)	−0.0147 (14)	−0.0139 (14)	0.0095 (16)
C7	0.0728 (18)	0.0374 (13)	0.095 (2)	−0.0071 (12)	−0.0003 (15)	−0.0078 (13)
O1	0.0704 (13)	0.0538 (12)	0.1080 (18)	0.0216 (9)	0.0109 (11)	0.0142 (11)
O2	0.0665 (12)	0.0333 (9)	0.0858 (14)	0.0009 (7)	0.0063 (10)	0.0045 (8)
O3	0.0500 (10)	0.0528 (10)	0.0858 (13)	−0.0075 (8)	−0.0136 (9)	0.0087 (9)

C8—O1	1.227 (3)	C2—O2	1.352 (2)
C8—C1	1.440 (3)	C9—O3	1.407 (3)
C8—H8	0.9300	C9—H9A	0.9700
C1—C2	1.391 (3)	C9—H9B	0.9700
C1—C6	1.394 (3)	C10—O3	1.413 (3)
C6—C5	1.368 (3)	C10—H10A	0.9600
C6—H6	0.9300	C10—H10B	0.9600
C5—C4	1.398 (3)	C10—H10C	0.9600
C5—C7	1.503 (3)	C7—H7A	0.9600
C4—C3	1.372 (3)	C7—H7B	0.9600
C4—H4	0.9300	C7—H7C	0.9600
C3—C2	1.392 (3)	O2—H2	0.8200
C3—C9	1.494 (3)
O1—C8—C1	125.2 (3)	O3—C9—C3	110.18 (18)
O1—C8—H8	117.4	O3—C9—H9A	109.6
C1—C8—H8	117.4	C3—C9—H9A	109.6
C2—C1—C6	119.6 (2)	O3—C9—H9B	109.6
C2—C1—C8	120.5 (2)	C3—C9—H9B	109.6
C6—C1—C8	119.9 (2)	H9A—C9—H9B	108.1
C5—C6—C1	121.5 (2)	O3—C10—H10A	109.5
C5—C6—H6	119.3	O3—C10—H10B	109.5
C1—C6—H6	119.3	H10A—C10—H10B	109.5
C6—C5—C4	117.3 (2)	O3—C10—H10C	109.5
C6—C5—C7	122.3 (2)	H10A—C10—H10C	109.5
C4—C5—C7	120.4 (2)	H10B—C10—H10C	109.5
C3—C4—C5	123.3 (2)	C5—C7—H7A	109.5
C3—C4—H4	118.3	C5—C7—H7B	109.5
C5—C4—H4	118.3	H7A—C7—H7B	109.5
C4—C3—C2	118.0 (2)	C5—C7—H7C	109.5
C4—C3—C9	123.2 (2)	H7A—C7—H7C	109.5
C2—C3—C9	118.74 (19)	H7B—C7—H7C	109.5
O2—C2—C1	121.9 (2)	C2—O2—H2	109.5
O2—C2—C3	117.8 (2)	C9—O3—C10	111.7 (2)
C1—C2—C3	120.25 (19)
O1—C8—C1—C2	0.9 (4)	C8—C1—C2—O2	−0.1 (3)
O1—C8—C1—C6	179.6 (2)	C6—C1—C2—C3	0.2 (3)
C2—C1—C6—C5	−0.3 (3)	C8—C1—C2—C3	179.0 (2)
C8—C1—C6—C5	−179.0 (2)	C4—C3—C2—O2	179.3 (2)
C1—C6—C5—C4	−0.2 (3)	C9—C3—C2—O2	−0.1 (3)
C1—C6—C5—C7	179.6 (2)	C4—C3—C2—C1	0.2 (3)
C6—C5—C4—C3	0.7 (3)	C9—C3—C2—C1	−179.2 (2)
C7—C5—C4—C3	−179.1 (2)	C4—C3—C9—O3	1.4 (3)
C5—C4—C3—C2	−0.8 (3)	C2—C3—C9—O3	−179.2 (2)
C5—C4—C3—C9	178.7 (2)	C3—C9—O3—C10	178.3 (2)
C6—C1—C2—O2	−178.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.91	2.628 (3)	146
C4—H4···O3	0.93	2.38	2.736 (3)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.91	2.628 (3)	146