Redetermination of 4-hydroxy-benzaldehyde.

This is a redetermination of the structure of the title compound, C(7)H(6)O(2), which was first reported by Iwasaki [Acta Cryst. (1977 ▶), B33, 1646-1648]. The results are obtained with greater precision in the present study. Crystal packing is stabilized by inter-molecular O-H⋯O inter-actions between the hydroxyl and aldehyde groups which link the mol-ecules into chains in a zigzag pattern along the [110] plane of the unit cell.

Related literature

For the previous structure determination, see: Iwasaki (1977 ▶). Forrelated structures, see: Matos Beja et al. (1997 ▶, 2000 ▶); Paixão et al. (2000 ▶); Silva et al. (2004 ▶). For related literature, see: Antonucci (1978 ▶); Bigi et al. (1999 ▶); Dean (1963 ▶); Samal et al. (1999 ▶).

Experimental

Crystal data

C7H6O2

M = 122.12

Monoclinic,

a = 6.6992 (8) Å

b = 13.5550 (12) Å

c = 7.1441 (11) Å

β = 112.871 (16)°

V = 597.74 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 (2) K

0.49 × 0.37 × 0.24 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.949, T max = 0.970

3559 measured reflections

1170 independent reflections

841 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.117

S = 1.06

1170 reflections

86 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlisPro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2000 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063659/lx2042sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063659/lx2042Isup2.hkl

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

C7H6O2	F000 = 256
Mr = 122.12	Dx = 1.357 Mg m−3
Monoclinic, P21/c	Melting point = 385–387 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 6.6992 (8) Å	Cell parameters from 1669 reflections
b = 13.5550 (12) Å	θ = 5.3–29.0º
c = 7.1441 (11) Å	µ = 0.10 mm−1
β = 112.871 (16)º	T = 296 (2) K
V = 597.74 (15) Å3	Chunk, colourless
Z = 4	0.49 × 0.37 × 0.24 mm

Oxford Diffraction Gemini R CCD diffractometer	1170 independent reflections
Radiation source: fine-focus sealed tube	841 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
Detector resolution: 10.5081 pixels mm-1	θmax = 26.0º
T = 296(2) K	θmin = 5.5º
φ and ω scans	h = −8→8
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	k = −15→16
Tmin = 0.949, Tmax = 0.970	l = −8→8
3559 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.068P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1170 reflections	Δρmax = 0.13 e Å−3
86 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.1345 (2)	0.72809 (8)	0.1335 (2)	0.0652 (4)
H1	0.016 (4)	0.7359 (17)	0.140 (3)	0.092 (8)*
O2	0.2691 (2)	0.26982 (8)	0.3786 (2)	0.0633 (4)
C1	0.1834 (2)	0.63218 (11)	0.1834 (2)	0.0458 (4)
C2	0.3718 (2)	0.59530 (11)	0.1700 (2)	0.0499 (4)
H2	0.4587	0.6359	0.1284	0.060*
C3	0.4277 (2)	0.49829 (11)	0.2187 (2)	0.0465 (4)
H3	0.5542	0.4740	0.2112	0.056*
C4	0.2990 (2)	0.43542 (11)	0.2793 (2)	0.0417 (4)
C5	0.1100 (2)	0.47379 (11)	0.2921 (2)	0.0452 (4)
H5	0.0218	0.4330	0.3317	0.054*
C6	0.0543 (2)	0.57089 (11)	0.2467 (2)	0.0470 (4)
H6	−0.0698	0.5959	0.2581	0.056*
C7	0.3667 (3)	0.33405 (12)	0.3294 (2)	0.0509 (4)
H7	0.4981	0.3161	0.3235	0.061*

	U11	U22	U33	U12	U13	U23
O1	0.0635 (8)	0.0422 (7)	0.1018 (10)	0.0034 (6)	0.0451 (7)	0.0091 (6)
O2	0.0586 (7)	0.0434 (7)	0.0917 (9)	−0.0019 (5)	0.0332 (7)	0.0049 (6)
C1	0.0463 (8)	0.0385 (8)	0.0547 (9)	−0.0030 (6)	0.0219 (7)	−0.0039 (7)
C2	0.0472 (9)	0.0463 (9)	0.0636 (10)	−0.0078 (7)	0.0297 (8)	−0.0039 (7)
C3	0.0372 (7)	0.0483 (9)	0.0582 (9)	−0.0026 (6)	0.0231 (7)	−0.0089 (7)
C4	0.0396 (8)	0.0404 (8)	0.0447 (8)	−0.0013 (6)	0.0157 (6)	−0.0058 (6)
C5	0.0417 (8)	0.0450 (9)	0.0536 (9)	−0.0050 (7)	0.0235 (7)	−0.0012 (7)
C6	0.0404 (8)	0.0466 (9)	0.0593 (9)	0.0020 (7)	0.0252 (7)	−0.0018 (7)
C7	0.0430 (8)	0.0455 (9)	0.0648 (10)	−0.0012 (7)	0.0217 (8)	−0.0055 (7)

O1—C1	1.354 (2)	C3—H3	0.9300
O1—H1	0.82 (3)	C4—C5	1.404 (2)
O2—C7	1.219 (2)	C4—C7	1.448 (2)
C1—C2	1.395 (2)	C5—C6	1.372 (2)
C1—C6	1.395 (2)	C5—H5	0.9300
C2—C3	1.374 (2)	C6—H6	0.9300
C2—H2	0.9300	C7—H7	0.9300
C3—C4	1.395 (2)
C1—O1—H1	104.4 (16)	C3—C4—C7	118.98 (13)
O1—C1—C2	117.30 (14)	C5—C4—C7	122.62 (13)
O1—C1—C6	122.68 (14)	C6—C5—C4	120.61 (13)
C2—C1—C6	120.02 (14)	C6—C5—H5	119.7
C3—C2—C1	119.35 (14)	C4—C5—H5	119.7
C3—C2—H2	120.3	C5—C6—C1	120.12 (14)
C1—C2—H2	120.3	C5—C6—H6	119.9
C2—C3—C4	121.50 (14)	C1—C6—H6	119.9
C2—C3—H3	119.3	O2—C7—C4	126.70 (15)
C4—C3—H3	119.3	O2—C7—H7	116.7
C3—C4—C5	118.39 (13)	C4—C7—H7	116.7
O1—C1—C2—C3	−179.85 (14)	C7—C4—C5—C6	178.77 (14)
C6—C1—C2—C3	0.3 (2)	C4—C5—C6—C1	1.2 (2)
C1—C2—C3—C4	0.7 (2)	O1—C1—C6—C5	178.90 (14)
C2—C3—C4—C5	−0.8 (2)	C2—C1—C6—C5	−1.2 (2)
C2—C3—C4—C7	−179.78 (14)	C3—C4—C7—O2	−177.67 (15)
C3—C4—C5—C6	−0.2 (2)	C5—C4—C7—O2	3.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82 (3)	1.92 (3)	2.731 (2)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82 (3)	1.92 (3)	2.731 (2)	171 (2)

Symmetry code: (i) .