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The title compound, C
7H
6O
2, 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
CCDC reference: 153898
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
C7H6O2 | F(000) = 256 |
Mr = 122.12 | Dx = 1.359 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 25 reflections |
a = 18.858 (7) Å | θ = 5.9–18.4° |
b = 3.864 (1) Å | µ = 0.10 mm−1 |
c = 8.190 (7) Å | T = 293 K |
V = 596.8 (6) Å3 | Prism, colourless |
Z = 4 | 0.55 × 0.30 × 0.25 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.037 |
Radiation source: fine-focus sealed tube | θmax = 29.9°, θmin = 5.4° |
Graphite monochromator | h = −26→24 |
profile data from ω–2θ scans | k = −5→5 |
5064 measured reflections | l = −10→10 |
768 independent reflections | 3 standard reflections every 180 min |
591 reflections with I > 2σ(I) | intensity decay: 1.8% |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-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 parameters | Δρmax = 0.15 e Å−3 |
1 restraint | Δρmin = −0.14 e Å−3 |
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 | Uiso*/Ueq | |
O1 | 0.11479 (11) | 0.0907 (7) | −0.0379 (2) | 0.0663 (6) | |
O2 | 0.05694 (10) | 0.2467 (6) | 0.6671 (2) | 0.0579 (5) | |
H2 | 0.082 (2) | 0.174 (9) | 0.753 (6) | 0.087* | |
C1 | 0.11486 (11) | 0.1137 (6) | 0.2506 (3) | 0.0361 (5) | |
C2 | 0.07385 (13) | 0.2065 (6) | 0.3839 (3) | 0.0387 (5) | |
H2A | 0.0295 | 0.3066 | 0.3684 | 0.046* | |
C3 | 0.09917 (12) | 0.1496 (6) | 0.5402 (3) | 0.0389 (5) | |
C4 | 0.16498 (12) | −0.0014 (6) | 0.5614 (3) | 0.0429 (5) | |
H4 | 0.1820 | −0.0425 | 0.6662 | 0.051* | |
C5 | 0.20532 (12) | −0.0911 (6) | 0.4279 (3) | 0.0466 (6) | |
H5 | 0.2498 | −0.1901 | 0.4436 | 0.056* | |
C6 | 0.18096 (11) | −0.0367 (6) | 0.2716 (3) | 0.0420 (5) | |
H6 | 0.2083 | −0.0996 | 0.1819 | 0.050* | |
C7 | 0.08598 (13) | 0.1771 (7) | 0.0875 (3) | 0.0459 (6) | |
H7 | 0.0389 (15) | 0.293 (7) | 0.086 (4) | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0658 (12) | 0.1042 (18) | 0.0289 (8) | 0.0082 (11) | 0.0020 (8) | −0.0015 (10) |
O2 | 0.0553 (10) | 0.0896 (14) | 0.0287 (8) | 0.0158 (11) | 0.0032 (8) | −0.0002 (9) |
C1 | 0.0373 (10) | 0.0432 (10) | 0.0278 (10) | −0.0023 (9) | −0.0004 (9) | 0.0014 (10) |
C2 | 0.0339 (9) | 0.0496 (12) | 0.0326 (11) | 0.0034 (10) | −0.0024 (9) | 0.0028 (10) |
C3 | 0.0402 (11) | 0.0476 (13) | 0.0291 (10) | −0.0013 (10) | 0.0035 (9) | −0.0003 (10) |
C4 | 0.0427 (10) | 0.0527 (13) | 0.0334 (12) | −0.0011 (11) | −0.0071 (9) | 0.0033 (10) |
C5 | 0.0354 (10) | 0.0559 (14) | 0.0486 (14) | 0.0063 (10) | −0.0031 (10) | 0.0048 (12) |
C6 | 0.0398 (10) | 0.0493 (13) | 0.0368 (12) | 0.0029 (9) | 0.0060 (9) | 0.0004 (10) |
C7 | 0.0434 (11) | 0.0618 (16) | 0.0326 (11) | 0.0000 (11) | −0.0028 (10) | 0.0044 (12) |
Geometric parameters (Å, º) top
O1—C7 | 1.209 (3) | C3—C4 | 1.382 (3) |
O2—C3 | 1.362 (3) | C4—C5 | 1.376 (3) |
O2—H2 | 0.89 (4) | C4—H4 | 0.9300 |
C1—C2 | 1.385 (3) | C5—C6 | 1.376 (4) |
C1—C6 | 1.386 (3) | C5—H5 | 0.9300 |
C1—C7 | 1.463 (3) | C6—H6 | 0.9300 |
C2—C3 | 1.384 (4) | C7—H7 | 0.99 (3) |
C2—H2A | 0.9300 | | |
| | | |
C3—O2—H2 | 102 (3) | C5—C4—H4 | 119.9 |
C2—C1—C6 | 120.8 (2) | C3—C4—H4 | 119.9 |
C2—C1—C7 | 117.93 (19) | C6—C5—C4 | 121.1 (2) |
C6—C1—C7 | 121.2 (2) | C6—C5—H5 | 119.5 |
C3—C2—C1 | 119.7 (2) | C4—C5—H5 | 119.5 |
C3—C2—H2A | 120.2 | C5—C6—C1 | 118.7 (2) |
C1—C2—H2A | 120.2 | C5—C6—H6 | 120.7 |
O2—C3—C4 | 123.0 (2) | C1—C6—H6 | 120.7 |
O2—C3—C2 | 117.4 (2) | O1—C7—C1 | 124.2 (2) |
C4—C3—C2 | 119.6 (2) | O1—C7—H7 | 121.2 (18) |
C5—C4—C3 | 120.2 (2) | C1—C7—H7 | 114.5 (18) |
| | | |
C6—C1—C2—C3 | 0.2 (3) | C3—C4—C5—C6 | −0.7 (4) |
C7—C1—C2—C3 | 179.8 (2) | C4—C5—C6—C1 | 0.5 (4) |
C1—C2—C3—O2 | 179.7 (2) | C2—C1—C6—C5 | −0.3 (3) |
C1—C2—C3—C4 | −0.4 (3) | C7—C1—C6—C5 | −179.8 (2) |
O2—C3—C4—C5 | −179.5 (2) | C2—C1—C7—O1 | −175.8 (3) |
C2—C3—C4—C5 | 0.7 (3) | C6—C1—C7—O1 | 3.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.89 (4) | 1.85 (5) | 2.719 (3) | 164 (4) |
Symmetry code: (i) x, y, z+1. |
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