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The title compound, C7H6O2, forms infinite chains where the mol­ecules are hydrogen bonded via the hydroxyl and aldehyde groups, with an O...O distance of 2.719 (3) Å. Interchain interactions are weak. The geometry of the ring differs from the ideal form due to the effect of the substituents. Ab initio (Hartree–Fock self-consistent field–molecular orbital and density functional theory) calculations for the free mol­ecule reproduce well the observed small distortions of the ring. In the crystal, the geometry deviates from the ideal Cs symmetry of the free mol­ecule, as given by the ab initio calculations. The aldehyde and hydroxyl groups are twisted around the single bonds which join them to the ring as a result of the intermolecular hydrogen-bond interactions. These are also responsible for an elongation of the hydroxy C—OH bond compared with that calculated for the free mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010441/gd1106sup1.cif
Contains datablocks I, default, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010441/gd1106Isup2.hkl
Contains datablock I

CCDC reference: 153898

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

m-hydroxybenzaldehyde top
Crystal data top
C7H6O2F(000) = 256
Mr = 122.12Dx = 1.359 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 25 reflections
a = 18.858 (7) Åθ = 5.9–18.4°
b = 3.864 (1) ŵ = 0.10 mm1
c = 8.190 (7) ÅT = 293 K
V = 596.8 (6) Å3Prism, colourless
Z = 40.55 × 0.30 × 0.25 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.037
Radiation source: fine-focus sealed tubeθmax = 29.9°, θmin = 5.4°
Graphite monochromatorh = 2624
profile data from ω–2θ scansk = 55
5064 measured reflectionsl = 1010
768 independent reflections3 standard reflections every 180 min
591 reflections with I > 2σ(I) intensity decay: 1.8%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0415P)2 + 0.0908P]
where P = (Fo2 + 2Fc2)/3
768 reflections(Δ/σ)max < 0.001
88 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.14 e Å3
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
xyzUiso*/Ueq
O10.11479 (11)0.0907 (7)0.0379 (2)0.0663 (6)
O20.05694 (10)0.2467 (6)0.6671 (2)0.0579 (5)
H20.082 (2)0.174 (9)0.753 (6)0.087*
C10.11486 (11)0.1137 (6)0.2506 (3)0.0361 (5)
C20.07385 (13)0.2065 (6)0.3839 (3)0.0387 (5)
H2A0.02950.30660.36840.046*
C30.09917 (12)0.1496 (6)0.5402 (3)0.0389 (5)
C40.16498 (12)0.0014 (6)0.5614 (3)0.0429 (5)
H40.18200.04250.66620.051*
C50.20532 (12)0.0911 (6)0.4279 (3)0.0466 (6)
H50.24980.19010.44360.056*
C60.18096 (11)0.0367 (6)0.2716 (3)0.0420 (5)
H60.20830.09960.18190.050*
C70.08598 (13)0.1771 (7)0.0875 (3)0.0459 (6)
H70.0389 (15)0.293 (7)0.086 (4)0.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0658 (12)0.1042 (18)0.0289 (8)0.0082 (11)0.0020 (8)0.0015 (10)
O20.0553 (10)0.0896 (14)0.0287 (8)0.0158 (11)0.0032 (8)0.0002 (9)
C10.0373 (10)0.0432 (10)0.0278 (10)0.0023 (9)0.0004 (9)0.0014 (10)
C20.0339 (9)0.0496 (12)0.0326 (11)0.0034 (10)0.0024 (9)0.0028 (10)
C30.0402 (11)0.0476 (13)0.0291 (10)0.0013 (10)0.0035 (9)0.0003 (10)
C40.0427 (10)0.0527 (13)0.0334 (12)0.0011 (11)0.0071 (9)0.0033 (10)
C50.0354 (10)0.0559 (14)0.0486 (14)0.0063 (10)0.0031 (10)0.0048 (12)
C60.0398 (10)0.0493 (13)0.0368 (12)0.0029 (9)0.0060 (9)0.0004 (10)
C70.0434 (11)0.0618 (16)0.0326 (11)0.0000 (11)0.0028 (10)0.0044 (12)
Geometric parameters (Å, º) top
O1—C71.209 (3)C3—C41.382 (3)
O2—C31.362 (3)C4—C51.376 (3)
O2—H20.89 (4)C4—H40.9300
C1—C21.385 (3)C5—C61.376 (4)
C1—C61.386 (3)C5—H50.9300
C1—C71.463 (3)C6—H60.9300
C2—C31.384 (4)C7—H70.99 (3)
C2—H2A0.9300
C3—O2—H2102 (3)C5—C4—H4119.9
C2—C1—C6120.8 (2)C3—C4—H4119.9
C2—C1—C7117.93 (19)C6—C5—C4121.1 (2)
C6—C1—C7121.2 (2)C6—C5—H5119.5
C3—C2—C1119.7 (2)C4—C5—H5119.5
C3—C2—H2A120.2C5—C6—C1118.7 (2)
C1—C2—H2A120.2C5—C6—H6120.7
O2—C3—C4123.0 (2)C1—C6—H6120.7
O2—C3—C2117.4 (2)O1—C7—C1124.2 (2)
C4—C3—C2119.6 (2)O1—C7—H7121.2 (18)
C5—C4—C3120.2 (2)C1—C7—H7114.5 (18)
C6—C1—C2—C30.2 (3)C3—C4—C5—C60.7 (4)
C7—C1—C2—C3179.8 (2)C4—C5—C6—C10.5 (4)
C1—C2—C3—O2179.7 (2)C2—C1—C6—C50.3 (3)
C1—C2—C3—C40.4 (3)C7—C1—C6—C5179.8 (2)
O2—C3—C4—C5179.5 (2)C2—C1—C7—O1175.8 (3)
C2—C3—C4—C50.7 (3)C6—C1—C7—O13.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.89 (4)1.85 (5)2.719 (3)164 (4)
Symmetry code: (i) x, y, z+1.
 

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