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Hydrogen bonds link planar molecules of 2,3-dihydroxy­benzaldehyde, C7H6O3, into ribbons.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019719/bt6686sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019719/bt6686Isup2.hkl
Contains datablock I

CCDC reference: 277215

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.111
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.794 0.980 Tmin' and Tmax expected: 0.962 0.980 RR' = 0.826 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

2,3-Dihydroxybenzaldehyde top
Crystal data top
C7H6O3F(000) = 288
Mr = 138.12Dx = 1.518 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4742 reflections
a = 12.409 (3) Åθ = 3.2–27.5°
b = 3.768 (2) ŵ = 0.12 mm1
c = 13.349 (3) ÅT = 295 K
β = 104.42 (3)°Block, colorless
V = 604.5 (4) Å30.32 × 0.24 × 0.17 mm
Z = 4
Data collection top
Rigaki RAXIS-RAPID IP
diffractometer
1372 independent reflections
Radiation source: fine-focus sealed tube1193 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1616
Tmin = 0.794, Tmax = 0.980k = 44
5427 measured reflectionsl = 1716
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111All H-atom parameters refined
S = 1.09 w = 1/[σ2(Fo2) + (0.0714P)2 + 0.0682P]
where P = (Fo2 + 2Fc2)/3
1372 reflections(Δ/σ)max = 0.001
115 parametersΔρmax = 0.33 e Å3
6 restraintsΔρmin = 0.14 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.29265 (7)0.6809 (3)0.66748 (6)0.0400 (3)
O20.40512 (6)0.8004 (2)0.86410 (6)0.0376 (3)
O30.72895 (7)0.5865 (3)0.97454 (7)0.0467 (3)
C10.4021 (1)0.5806 (3)0.6955 (1)0.0302 (3)
C20.4581 (1)0.6467 (3)0.7986 (1)0.0275 (3)
C30.5703 (1)0.5558 (3)0.8335 (1)0.0278 (3)
C40.6253 (1)0.3978 (3)0.7652 (1)0.0325 (3)
C50.5696 (1)0.3336 (3)0.6641 (1)0.0377 (3)
C60.4575 (1)0.4244 (3)0.6296 (1)0.0365 (3)
C70.6302 (1)0.6445 (3)0.9386 (1)0.0328 (3)
H1o0.277 (2)0.755 (5)0.605 (1)0.070 (5)*
H2o0.340 (1)0.856 (4)0.833 (1)0.055 (4)*
H40.701 (1)0.333 (4)0.789 (1)0.044 (4)*
H50.608 (1)0.228 (4)0.618 (1)0.048 (4)*
H60.417 (1)0.381 (4)0.560 (1)0.049 (4)*
H70.587 (1)0.754 (4)0.980 (1)0.044 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0245 (4)0.0622 (6)0.0296 (4)0.0025 (3)0.0000 (3)0.0062 (4)
O20.0244 (4)0.0576 (5)0.0297 (4)0.0066 (3)0.0048 (3)0.0037 (3)
O30.0268 (4)0.0733 (6)0.0354 (4)0.0023 (4)0.0009 (3)0.0057 (4)
C10.0246 (5)0.0367 (5)0.0272 (5)0.0053 (4)0.0022 (4)0.0039 (4)
C20.0243 (5)0.0319 (5)0.0256 (5)0.0030 (4)0.0050 (4)0.0021 (4)
C30.0244 (5)0.0303 (5)0.0275 (5)0.0022 (4)0.0044 (4)0.0021 (4)
C40.0277 (5)0.0341 (5)0.0361 (6)0.0010 (4)0.0084 (4)0.0013 (4)
C50.0419 (7)0.0405 (6)0.0337 (6)0.0003 (5)0.0151 (5)0.0034 (5)
C60.0391 (6)0.0431 (6)0.0255 (5)0.0062 (5)0.0046 (4)0.0024 (4)
C70.0253 (5)0.0417 (6)0.0295 (5)0.0003 (4)0.0032 (4)0.0004 (4)
Geometric parameters (Å, º) top
O1—C11.369 (1)C4—C51.375 (2)
O2—C21.348 (1)C5—C61.394 (2)
O3—C71.219 (1)O1—H1o0.86 (1)
C1—C61.376 (2)O2—H2o0.84 (1)
C1—C21.402 (2)C7—H70.95 (1)
C2—C31.397 (2)C4—H40.95 (1)
C3—C41.400 (2)C5—H50.95 (1)
C3—C71.454 (2)C6—H60.95 (1)
O3—C7—C3124.1 (1)C1—C6—C5120.7 (1)
O1—C1—C6124.3 (1)C1—O1—H1o109 (1)
O1—C1—C2115.7 (1)C2—O2—H2o111 (1)
C6—C1—C2120.0 (1)O3—C7—H7120 (1)
O2—C2—C3119.7 (1)C5—C4—H4120 (1)
O2—C2—C1120.8 (1)C3—C4—H4120 (1)
C3—C2—C1119.5 (1)C3—C7—H7116 (1)
C2—C3—C4119.6 (1)C4—C5—H5120 (1)
C2—C3—C7119.5 (1)C6—C5—H5120 (1)
C4—C3—C7120.8 (1)C1—C6—H6118 (1)
C5—C4—C3120.4 (1)C5—C6—H6121 (1)
C4—C5—C6119.8 (1)
O1—C1—C2—O20.1 (2)O3—C7—C3—C2177.4 (1)
C6—C1—C2—O2179.8 (1)O3—C7—C3—C40.9 (2)
O1—C1—C2—C3179.4 (1)C2—C3—C4—C50.3 (2)
C6—C1—C2—C30.6 (2)C7—C3—C4—C5176.2 (1)
O2—C2—C3—C4179.7 (1)C3—C4—C5—C60.4 (2)
C1—C2—C3—C40.4 (2)O1—C1—C6—C5179.3 (1)
O2—C2—C3—C73.1 (2)C2—C1—C6—C50.6 (2)
C1—C2—C3—C7176.2 (1)C4—C5—C6—C10.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O3i0.86 (1)1.80 (1)2.648 (1)174 (2)
O2—H2o···O1ii0.84 (1)2.05 (1)2.782 (1)145 (2)
Symmetry codes: (i) x1/2, y+3/2, z1/2; (ii) x+1/2, y+1/2, z+3/2.
 

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