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The crystal structure of indole-3-carboxyl­ic acid, C9H7NO2, shows the presence of centrosymmetric hydrogen-bonded cyclic carboxyl­ic acid dimers [O...O = 2.649 (2) Å]. These dimers are linked into a sheet structure through peripheral intermolecular hydrogen bonds between the carboxyl­ic acid groups and the hetero-amine group of the n-glide-related indole ring [O...N = 3.013 (2) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803022670/ww6128sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803022670/ww6128Isup2.hkl
Contains datablock I

CCDC reference: 227000

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.152
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: TEXSAN for Windows (Molecular Structure Corporation, 1999); data reduction: TEXSAN for Windows; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: PLATON for Windows.

1H-indole-3-carboxylic acid top
Crystal data top
C9H7NO2F(000) = 336
Mr = 161.16Dx = 1.415 Mg m3
Monoclinic, P21/nMelting point = 483–484 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71069 Å
a = 16.048 (3) ÅCell parameters from 25 reflections
b = 10.611 (3) Åθ = 12.5–17.4°
c = 4.4588 (16) ŵ = 0.10 mm1
β = 94.95 (2)°T = 295 K
V = 756.5 (4) Å3Block, colourless
Z = 40.40 × 0.35 × 0.15 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.054
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.6°
Graphite monochromatorh = 2020
ω–2θ scansk = 013
2023 measured reflectionsl = 52
1723 independent reflections3 standard reflections every 150 reflections
1148 reflections with I > 2σ(I) intensity decay: 1.0%
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 0.93 w = 1/[σ2(Fo2) + (0.1P)2 + 0.2856P]
where P = (Fo2 + 2Fc2)/3
1723 reflections(Δ/σ)max = 0.004
118 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O310.95392 (8)0.63915 (14)0.1747 (4)0.0617 (6)
O320.90078 (8)0.47819 (13)0.0703 (3)0.0494 (5)
N10.71411 (11)0.77920 (16)0.2844 (4)0.0440 (5)
C20.79524 (12)0.74662 (18)0.2885 (4)0.0420 (6)
C30.81204 (11)0.64470 (16)0.1034 (4)0.0369 (5)
C40.71154 (12)0.52017 (17)0.2253 (4)0.0418 (6)
C50.62999 (14)0.5186 (2)0.2969 (5)0.0513 (7)
C60.57115 (13)0.6065 (2)0.1756 (5)0.0538 (7)
C70.59325 (12)0.6977 (2)0.0201 (5)0.0496 (7)
C80.67524 (12)0.69927 (17)0.0952 (4)0.0389 (6)
C90.73551 (11)0.61164 (16)0.0239 (4)0.0355 (5)
C310.89139 (11)0.58096 (18)0.0611 (4)0.0390 (5)
H10.6893 (14)0.842 (2)0.386 (5)0.054 (6)*
H20.8351000.7880000.4037000.0480*
H40.7508000.4596000.3107000.0470*
H50.6129000.4564000.4339000.0600*
H60.5146000.6015000.2299000.0620*
H70.5539000.7605000.1007000.0570*
H311.0030 (14)0.586 (2)0.137 (5)0.0380*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O310.0321 (7)0.0524 (9)0.1008 (13)0.0004 (6)0.0067 (8)0.0273 (8)
O320.0304 (7)0.0400 (8)0.0766 (10)0.0011 (5)0.0022 (6)0.0133 (7)
N10.0427 (9)0.0381 (9)0.0501 (9)0.0092 (7)0.0030 (7)0.0022 (7)
C20.0391 (10)0.0363 (10)0.0499 (11)0.0001 (8)0.0002 (8)0.0011 (8)
C30.0319 (9)0.0335 (9)0.0441 (9)0.0010 (7)0.0034 (7)0.0032 (7)
C40.0420 (10)0.0397 (10)0.0431 (10)0.0007 (8)0.0006 (8)0.0037 (8)
C50.0507 (12)0.0534 (13)0.0512 (11)0.0038 (9)0.0133 (10)0.0030 (10)
C60.0369 (10)0.0674 (14)0.0581 (12)0.0007 (9)0.0096 (9)0.0116 (11)
C70.0372 (10)0.0586 (13)0.0518 (11)0.0135 (9)0.0022 (9)0.0126 (10)
C80.0382 (10)0.0384 (10)0.0390 (9)0.0067 (7)0.0034 (7)0.0085 (8)
C90.0324 (9)0.0347 (9)0.0384 (9)0.0007 (7)0.0033 (7)0.0080 (7)
C310.0288 (8)0.0360 (9)0.0509 (10)0.0042 (7)0.0033 (7)0.0008 (8)
Geometric parameters (Å, º) top
O31—C311.316 (2)C4—C51.374 (3)
O32—C311.241 (2)C5—C61.402 (3)
O31—H310.97 (2)C6—C71.370 (3)
N1—C21.349 (3)C7—C81.386 (3)
N1—C81.382 (3)C8—C91.412 (3)
N1—H10.88 (2)C2—H20.9605
C2—C31.373 (3)C4—H40.9558
C3—C91.440 (3)C5—H50.9554
C3—C311.440 (3)C6—H60.9607
C4—C91.399 (3)C7—H70.9658
C31—O31—H31107.1 (13)C3—C9—C4135.50 (17)
C2—N1—C8109.75 (16)C3—C9—C8105.73 (15)
C2—N1—H1125.5 (15)O31—C31—O32121.90 (17)
C8—N1—H1124.7 (15)O31—C31—C3115.10 (16)
N1—C2—C3109.48 (17)O32—C31—C3123.00 (16)
C2—C3—C9107.39 (16)N1—C2—H2125.33
C9—C3—C31127.49 (16)C3—C2—H2125.19
C2—C3—C31125.05 (17)C5—C4—H4120.51
C5—C4—C9118.55 (18)C9—C4—H4120.93
C4—C5—C6121.7 (2)C4—C5—H5119.26
C5—C6—C7120.9 (2)C6—C5—H5119.03
C6—C7—C8117.76 (19)C5—C6—H6119.04
N1—C8—C7130.00 (18)C7—C6—H6120.11
N1—C8—C9107.64 (16)C6—C7—H7121.83
C7—C8—C9122.36 (17)C8—C7—H7120.39
C4—C9—C8118.76 (17)
C2—N1—C8—C7179.4 (2)C9—C3—C31—O328.2 (3)
C8—N1—C2—C30.1 (2)C5—C4—C9—C80.6 (3)
C2—N1—C8—C90.3 (2)C9—C4—C5—C60.6 (3)
N1—C2—C3—C90.17 (19)C5—C4—C9—C3179.5 (2)
N1—C2—C3—C31177.40 (17)C4—C5—C6—C70.0 (3)
C2—C3—C9—C4179.4 (2)C5—C6—C7—C80.5 (3)
C2—C3—C9—C80.3 (2)C6—C7—C8—N1179.9 (2)
C31—C3—C9—C43.5 (3)C6—C7—C8—C90.4 (3)
C31—C3—C9—C8177.49 (18)N1—C8—C9—C30.4 (2)
C9—C3—C31—O31172.38 (18)N1—C8—C9—C4179.61 (16)
C2—C3—C31—O3111.0 (3)C7—C8—C9—C3179.34 (18)
C2—C3—C31—O32168.49 (18)C7—C8—C9—C40.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O32i0.88 (2)2.16 (2)3.013 (2)164 (2)
O31—H31···O32ii0.97 (2)1.69 (2)2.649 (2)168 (2)
Symmetry codes: (i) x+3/2, y+1/2, z1/2; (ii) x+2, y+1, z.
 

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