supplementary materials


hb6541 scheme

Acta Cryst. (2012). E68, o146    [ doi:10.1107/S1600536811051865 ]

3-Carboxymethyl-1H-indole-4-carboxylic acid

S. Mao

Abstract top

In the title compound, C11H9NO4, the carboxyl group bonded to the six-membered ring lies close to the plane of the 1H-indole ring system [dihedral angle = 13.13 (9)°], whereas the carboxylic acid group linked to the five-membered ring by a methylene bridge is close to perpendicular [78.85 (9)°]. In the crystal, O-H...O and N-H...O hydrogen bonds link the molecules, generating (110) sheets.

Related literature top

For background to indoles as pharmaceuticals, see: Lang et al. (2011).

Experimental top

To a solution of the title compound (0.2 g) in methanol (20 ml) by stirred at room temperature and then placed in a dark place. Yellow single crystals were obtained by slow evaporation of the solution over a period of 5 days.

Refinement top

Positional parameters of all the H atoms were calculated geometrically and refined using a riding model,, with C—H = 0.94Å and Uiso(H) =1.2Ueq(C) respectively.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I) with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram.
3-Carboxymethyl-1H-indole-4-carboxylic acid top
Crystal data top
C11H9NO4V = 498.3 (2) Å3
Mr = 219.19Z = 2
Triclinic, P1F(000) = 228
Hall symbol: -P 1Dx = 1.461 Mg m3
a = 5.4573 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.823 (2) Åθ = 3.4–27.4°
c = 9.940 (2) ŵ = 0.11 mm1
α = 73.90 (3)°T = 293 K
β = 78.57 (3)°Prism, yellow
γ = 80.40 (3)°0.30 × 0.23 × 0.20 mm
Data collection top
Rigaku SCXmini CCD
diffractometer
2263 independent reflections
Radiation source: fine-focus sealed tube1786 reflections with I > 2σ(I)
graphiteRint = 0.028
Detector resolution: 13.6612 pixels mm-1θmax = 27.4°, θmin = 3.4°
CCD_Profile_fitting scansh = 67
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1212
Tmin = 0.977, Tmax = 0.984l = 1212
5115 measured reflections
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0712P)2 + 0.1712P]
where P = (Fo2 + 2Fc2)/3
2239 reflections(Δ/σ)max = 0.015
147 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C11H9NO4γ = 80.40 (3)°
Mr = 219.19V = 498.3 (2) Å3
Triclinic, P1Z = 2
a = 5.4573 (11) ÅMo Kα radiation
b = 9.823 (2) ŵ = 0.11 mm1
c = 9.940 (2) ÅT = 293 K
α = 73.90 (3)°0.30 × 0.23 × 0.20 mm
β = 78.57 (3)°
Data collection top
Rigaku SCXmini CCD
diffractometer
2263 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
1786 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.984Rint = 0.028
5115 measured reflectionsθmax = 27.4°
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.132Δρmax = 0.30 e Å3
S = 0.95Δρmin = 0.21 e Å3
2239 reflectionsAbsolute structure: ?
147 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
O30.1544 (2)0.84288 (12)0.97213 (13)0.0443 (3)
O20.1686 (3)0.91438 (13)0.62549 (15)0.0579 (4)
O10.0340 (3)0.82135 (14)0.47736 (16)0.0648 (5)
H10.03200.90360.45200.097*
O40.2593 (3)1.06204 (12)0.86103 (17)0.0588 (4)
H40.12551.08560.90790.088*
N10.7240 (3)0.48127 (14)0.87277 (16)0.0423 (4)
H1B0.81030.40470.91340.051*
C30.4527 (3)0.63513 (15)0.73814 (15)0.0300 (3)
C110.2985 (3)0.92105 (16)0.88625 (17)0.0357 (4)
C90.1571 (3)0.81052 (17)0.58232 (17)0.0375 (4)
C40.2738 (3)0.66441 (16)0.64359 (16)0.0337 (4)
C20.5741 (3)0.71447 (16)0.80476 (17)0.0330 (3)
C80.5522 (3)0.48888 (16)0.78546 (17)0.0347 (4)
C70.4775 (3)0.37626 (17)0.74825 (19)0.0416 (4)
H70.54670.28260.78200.050*
C50.2020 (4)0.55078 (18)0.60716 (19)0.0440 (4)
H50.08570.57030.54540.053*
C10.7343 (3)0.61564 (19)0.8840 (2)0.0423 (4)
H1A0.83620.63740.93800.051*
C100.5422 (3)0.87055 (16)0.80186 (19)0.0375 (4)
H10A0.55090.92600.70400.045*
H10B0.68160.88940.83850.045*
C60.2990 (4)0.40813 (18)0.6605 (2)0.0463 (4)
H60.24240.33520.63630.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0485 (7)0.0270 (6)0.0508 (7)0.0021 (5)0.0007 (6)0.0082 (5)
O20.0848 (10)0.0310 (6)0.0679 (9)0.0111 (6)0.0480 (8)0.0141 (6)
O10.1008 (12)0.0354 (7)0.0696 (9)0.0118 (7)0.0576 (9)0.0129 (6)
O40.0616 (9)0.0258 (6)0.0804 (10)0.0021 (6)0.0096 (7)0.0159 (6)
N10.0411 (8)0.0319 (7)0.0511 (8)0.0107 (6)0.0162 (7)0.0083 (6)
C30.0320 (7)0.0255 (7)0.0294 (7)0.0008 (6)0.0016 (6)0.0068 (5)
C110.0407 (9)0.0251 (7)0.0438 (9)0.0001 (6)0.0134 (7)0.0106 (6)
C90.0443 (9)0.0319 (8)0.0362 (8)0.0010 (7)0.0138 (7)0.0064 (6)
C40.0388 (8)0.0274 (7)0.0333 (8)0.0005 (6)0.0069 (6)0.0061 (6)
C20.0302 (7)0.0313 (8)0.0372 (8)0.0007 (6)0.0056 (6)0.0105 (6)
C80.0355 (8)0.0286 (8)0.0354 (8)0.0043 (6)0.0041 (6)0.0063 (6)
C70.0517 (10)0.0234 (7)0.0452 (9)0.0025 (7)0.0043 (8)0.0076 (6)
C50.0546 (10)0.0338 (8)0.0481 (10)0.0030 (7)0.0194 (8)0.0112 (7)
C10.0378 (9)0.0411 (9)0.0494 (10)0.0038 (7)0.0144 (7)0.0138 (7)
C100.0366 (8)0.0313 (8)0.0470 (9)0.0034 (6)0.0101 (7)0.0122 (7)
C60.0628 (12)0.0300 (8)0.0498 (10)0.0063 (8)0.0128 (9)0.0128 (7)
Geometric parameters (Å, °) top
O3—C111.228 (2)C9—C41.483 (2)
O2—C91.226 (2)C4—C51.399 (2)
O1—C91.321 (2)C2—C11.376 (2)
O1—H10.8200C2—C101.507 (2)
O4—C111.3255 (19)C8—C71.401 (2)
O4—H40.8200C7—C61.375 (3)
N1—C11.366 (2)C7—H70.9300
N1—C81.379 (2)C5—C61.406 (2)
N1—H1B0.8600C5—H50.9300
C3—C41.428 (2)C1—H1A0.9300
C3—C81.430 (2)C10—H10A0.9700
C3—C21.455 (2)C10—H10B0.9700
C11—C101.512 (2)C6—H60.9300
C9—O1—H1109.5N1—C8—C3108.27 (14)
C11—O4—H4109.5C7—C8—C3123.86 (15)
C1—N1—C8108.65 (13)C6—C7—C8118.15 (15)
C1—N1—H1B125.7C6—C7—H7120.9
C8—N1—H1B125.7C8—C7—H7120.9
C4—C3—C8116.31 (14)C4—C5—C6122.44 (16)
C4—C3—C2137.91 (14)C4—C5—H5118.8
C8—C3—C2105.78 (13)C6—C5—H5118.8
O3—C11—O4122.70 (15)N1—C1—C2111.03 (15)
O3—C11—C10125.15 (14)N1—C1—H1A124.5
O4—C11—C10112.12 (14)C2—C1—H1A124.5
O2—C9—O1121.54 (15)C2—C10—C11114.51 (14)
O2—C9—C4123.59 (15)C2—C10—H10A108.6
O1—C9—C4114.86 (14)C11—C10—H10A108.6
C5—C4—C3119.06 (14)C2—C10—H10B108.6
C5—C4—C9117.85 (15)C11—C10—H10B108.6
C3—C4—C9123.09 (14)H10A—C10—H10B107.6
C1—C2—C3106.26 (14)C7—C6—C5120.11 (16)
C1—C2—C10122.09 (15)C7—C6—H6119.9
C3—C2—C10131.61 (14)C5—C6—H6119.9
N1—C8—C7127.86 (15)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.832.6504 (19)174
O4—H4···O3ii0.821.912.719 (2)171
N1—H1B···O3iii0.862.383.152 (2)150
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+2, −z+2; (iii) −x+1, −y+1, −z+2.
Table 1
Hydrogen-bond geometry (Å, °)
top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.832.6504 (19)174
O4—H4···O3ii0.821.912.719 (2)171
N1—H1B···O3iii0.862.383.152 (2)150
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+2, −z+2; (iii) −x+1, −y+1, −z+2.
references
References top

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.

Lang, L., Wu, J.-L., Shi, L.-J., Xia, C.-G. & Li, F.-W. (2011). Chem. Commun. 47, 12553–12555.

Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.