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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 Oct 28;65(Pt 11):o2860. doi: 10.1107/S1600536809043463

2-(Carbazol-9-yl)acetic acid

Min-Hao Xie a, Pei Zou a, Yong-Jun He a, Ya-Ling Liu a, Biao Huang a,*
PMCID: PMC2971217  PMID: 21578447

Abstract

In the title compound, C14H11NO2, the tricyclic aromatic ring system is essentially planar [maximum deviation = 0.025 (2) Å]. The dihedral angle between the two benzene rings is 2.8 (5)°, while the carboxyl group forms a dihedral angle of 88.5 (1)° with the pyrrole ring. Inter­molecular O—H⋯O hydrogen bonds may contribute to the overall stabilization of the crystal structure.

Related literature

For the use of the title compound in high-performance liquid chromatography, see: Jinmao et al. (2001). For synthesis: Xie et al. (2006).graphic file with name e-65-o2860-scheme1.jpg

Experimental

Crystal data

  • C14H11NO2

  • M r = 225.24

  • Monoclinic, Inline graphic

  • a = 32.067 (19) Å

  • b = 5.340 (3) Å

  • c = 13.134 (7) Å

  • β = 97.756 (8)°

  • V = 2229 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 93 K

  • 0.40 × 0.30 × 0.08 mm

Data collection

  • Rigaku SPIDER diffractometer

  • Absorption correction: none

  • 8360 measured reflections

  • 2534 independent reflections

  • 1749 reflections with I > 2σ(I)

  • R int = 0.067

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048

  • wR(F 2) = 0.093

  • S = 1.00

  • 2534 reflections

  • 159 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.25 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043463/cs2123sup1.cif

e-65-o2860-sup1.cif (15.9KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043463/cs2123Isup2.hkl

e-65-o2860-Isup2.hkl (124.6KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2O⋯O1i 0.95 (3) 1.70 (3) 2.645 (2) 171 (2)

Symmetry code: (i) Inline graphic.

Acknowledgments

The Key Laboratory of Nuclear Medicine of the Ministry Health of China is thanked for supporting this work.

supplementary crystallographic information

Comment

Carbazoles are ubiquitous structural subunits of numerous naturally occurring compounds as well as synthetic materials. The title molecule (Fig. 1), is useful as an important agent for determination of alcohols by high-performance liquid chromatography with fluorimetric detection after pre-column derivatization (Jinmao et al., 2001; Xie et al., 2006). The crystal structure shows that the tricyclic aromatic ring system is coplanar. The dihedral angle between the two benzene rings is 2.8 (5)°. The pyrrole ring makes dihedral angles of 1.5 (5)° and 1.3 (5)° with the benzene rings, respectively. The pyrrole ring and the carboxylic acid group (O1/C14/O2) are twisted to each other by a torsion angles of 88.5 (1)°. The crystal structure may be stabilized by intermolecular O2–H2O···O1i [i= 1-x, 1-y, 1-z] hydrogen bonds.

Experimental

The title compound was prepared by a method reported earlier (Xie et al., 2006). The pure product (0.1 g) obtained was dissolved in 50% ethanol (10 ml). The solution was evaporated in air affording colourless platelet crystals suitable for X-ray analysis (yield: 67.2%).

Refinement

Positional parameters of all the H atoms bonded to C atoms were calculated geometrically and were allowed to ride on the C atoms to which they are bonded,with C—H=0.95 and 0.99 Å for aromatic and methylene and with Uiso(H) = 1.2Ueq(aromatic,methylene) parent atoms. The carboxylic H atom was taken from a differnce density map and refined.

Figures

Fig. 1.

Fig. 1.

A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.

Crystal data

C14H11NO2 F(000) = 944
Mr = 225.24 Dx = 1.343 Mg m3
Monoclinic, C2/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc Cell parameters from 2975 reflections
a = 32.067 (19) Å θ = 3.1–27.5°
b = 5.340 (3) Å µ = 0.09 mm1
c = 13.134 (7) Å T = 93 K
β = 97.756 (8)° Platelet, colorless
V = 2229 (2) Å3 0.40 × 0.30 × 0.08 mm
Z = 8

Data collection

Rigaku SPIDER diffractometer 1749 reflections with I > 2σ(I)
Radiation source: Rotating Anode Rint = 0.067
graphite θmax = 27.5°, θmin = 3.1°
ω scans h = −41→41
8360 measured reflections k = −6→6
2534 independent reflections l = −17→17

Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.0136P)2 + 0.660P] where P = (Fo2 + 2Fc2)/3
S = 1.00 (Δ/σ)max < 0.001
2534 reflections Δρmax = 0.22 e Å3
159 parameters Δρmin = −0.25 e Å3
0 restraints Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods Extinction coefficient: 0.0006 (2)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.45527 (4) 0.3887 (2) 0.43806 (10) 0.0305 (3)
O2 0.48708 (4) 0.7517 (2) 0.40940 (10) 0.0322 (4)
N1 0.38917 (5) 0.4955 (3) 0.28479 (11) 0.0248 (4)
C1 0.39216 (6) 0.3113 (3) 0.21154 (13) 0.0240 (4)
C2 0.42431 (6) 0.2678 (3) 0.15246 (14) 0.0285 (5)
H2 0.4486 0.3715 0.1582 0.034*
C3 0.41955 (6) 0.0674 (3) 0.08487 (14) 0.0309 (5)
H3 0.4411 0.0330 0.0438 0.037*
C4 0.38388 (6) −0.0852 (4) 0.07555 (14) 0.0303 (5)
H4 0.3814 −0.2204 0.0281 0.036*
C5 0.35211 (6) −0.0411 (3) 0.13498 (14) 0.0281 (5)
H5 0.3279 −0.1456 0.1287 0.034*
C6 0.35604 (6) 0.1578 (3) 0.20388 (13) 0.0235 (4)
C7 0.33048 (6) 0.2527 (3) 0.27875 (13) 0.0245 (4)
C8 0.29237 (6) 0.1775 (4) 0.30960 (14) 0.0291 (5)
H8 0.2775 0.0374 0.2785 0.035*
C9 0.27678 (6) 0.3113 (4) 0.38653 (15) 0.0338 (5)
H9 0.2510 0.2615 0.4086 0.041*
C10 0.29835 (6) 0.5181 (4) 0.43219 (15) 0.0344 (5)
H10 0.2867 0.6077 0.4841 0.041*
C11 0.33618 (6) 0.5962 (4) 0.40406 (14) 0.0303 (5)
H11 0.3509 0.7360 0.4360 0.036*
C12 0.35197 (6) 0.4611 (3) 0.32662 (14) 0.0255 (4)
C13 0.42069 (6) 0.6818 (3) 0.31517 (14) 0.0277 (5)
H13A 0.4072 0.8275 0.3440 0.033*
H13B 0.4326 0.7395 0.2535 0.033*
C14 0.45600 (6) 0.5897 (4) 0.39346 (14) 0.0257 (4)
H2O 0.5081 (8) 0.687 (4) 0.4603 (19) 0.088 (9)*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0316 (8) 0.0297 (8) 0.0293 (8) −0.0020 (6) 0.0000 (6) 0.0064 (6)
O2 0.0290 (8) 0.0318 (8) 0.0337 (8) −0.0065 (7) −0.0034 (6) 0.0074 (7)
N1 0.0252 (9) 0.0249 (9) 0.0238 (9) −0.0024 (7) 0.0011 (7) 0.0003 (7)
C1 0.0286 (10) 0.0238 (11) 0.0187 (9) 0.0017 (8) 0.0001 (7) 0.0037 (8)
C2 0.0285 (11) 0.0308 (11) 0.0262 (10) 0.0003 (9) 0.0038 (8) 0.0068 (9)
C3 0.0373 (12) 0.0344 (12) 0.0214 (10) 0.0081 (9) 0.0057 (9) 0.0053 (9)
C4 0.0405 (12) 0.0283 (11) 0.0211 (10) 0.0068 (9) 0.0004 (9) 0.0011 (8)
C5 0.0330 (11) 0.0264 (11) 0.0235 (10) 0.0003 (9) −0.0009 (8) 0.0019 (8)
C6 0.0262 (10) 0.0241 (11) 0.0190 (9) 0.0030 (8) −0.0018 (7) 0.0031 (8)
C7 0.0252 (10) 0.0259 (10) 0.0210 (10) 0.0022 (8) −0.0015 (7) 0.0040 (8)
C8 0.0261 (11) 0.0326 (12) 0.0274 (11) −0.0014 (9) −0.0004 (8) 0.0034 (9)
C9 0.0287 (11) 0.0460 (14) 0.0270 (11) 0.0019 (10) 0.0047 (8) 0.0056 (10)
C10 0.0354 (12) 0.0405 (13) 0.0275 (11) 0.0080 (10) 0.0043 (9) −0.0007 (10)
C11 0.0356 (12) 0.0298 (11) 0.0240 (11) 0.0038 (9) −0.0009 (8) −0.0005 (9)
C12 0.0266 (10) 0.0269 (11) 0.0220 (10) 0.0015 (8) −0.0001 (8) 0.0054 (8)
C13 0.0281 (10) 0.0275 (11) 0.0264 (10) −0.0021 (8) −0.0005 (8) 0.0033 (8)
C14 0.0282 (11) 0.0273 (11) 0.0221 (10) −0.0015 (8) 0.0048 (8) −0.0015 (8)

Geometric parameters (Å, °)

O1—C14 1.224 (2) C5—H5 0.9500
O2—C14 1.315 (2) C6—C7 1.454 (2)
O2—H2O 0.95 (3) C7—C8 1.397 (2)
N1—C1 1.388 (2) C7—C12 1.411 (2)
N1—C12 1.391 (2) C8—C9 1.385 (3)
N1—C13 1.436 (2) C8—H8 0.9500
C1—C2 1.391 (2) C9—C10 1.395 (3)
C1—C6 1.412 (2) C9—H9 0.9500
C2—C3 1.386 (2) C10—C11 1.379 (3)
C2—H2 0.9500 C10—H10 0.9500
C3—C4 1.397 (3) C11—C12 1.397 (2)
C3—H3 0.9500 C11—H11 0.9500
C4—C5 1.385 (3) C13—C14 1.506 (2)
C4—H4 0.9500 C13—H13A 0.9900
C5—C6 1.390 (2) C13—H13B 0.9900
C14—O2—H2O 109.0 (14) C9—C8—C7 118.62 (18)
C1—N1—C12 108.85 (15) C9—C8—H8 120.7
C1—N1—C13 124.87 (16) C7—C8—H8 120.7
C12—N1—C13 126.21 (16) C8—C9—C10 121.03 (19)
N1—C1—C2 129.09 (17) C8—C9—H9 119.5
N1—C1—C6 109.17 (16) C10—C9—H9 119.5
C2—C1—C6 121.74 (17) C11—C10—C9 121.81 (19)
C3—C2—C1 117.42 (18) C11—C10—H10 119.1
C3—C2—H2 121.3 C9—C10—H10 119.1
C1—C2—H2 121.3 C10—C11—C12 117.21 (18)
C2—C3—C4 121.67 (18) C10—C11—H11 121.4
C2—C3—H3 119.2 C12—C11—H11 121.4
C4—C3—H3 119.2 N1—C12—C11 129.33 (18)
C5—C4—C3 120.51 (18) N1—C12—C7 108.75 (17)
C5—C4—H4 119.7 C11—C12—C7 121.91 (18)
C3—C4—H4 119.7 N1—C13—C14 113.56 (15)
C4—C5—C6 119.20 (18) N1—C13—H13A 108.9
C4—C5—H5 120.4 C14—C13—H13A 108.9
C6—C5—H5 120.4 N1—C13—H13B 108.9
C5—C6—C1 119.46 (17) C14—C13—H13B 108.9
C5—C6—C7 134.18 (18) H13A—C13—H13B 107.7
C1—C6—C7 106.34 (16) O1—C14—O2 124.31 (18)
C8—C7—C12 119.41 (18) O1—C14—C13 123.49 (17)
C8—C7—C6 133.70 (18) O2—C14—C13 112.19 (16)
C12—C7—C6 106.88 (16)
C12—N1—C1—C2 −177.99 (18) C12—C7—C8—C9 0.2 (3)
C13—N1—C1—C2 −0.9 (3) C6—C7—C8—C9 178.84 (18)
C12—N1—C1—C6 1.23 (19) C7—C8—C9—C10 0.4 (3)
C13—N1—C1—C6 178.30 (15) C8—C9—C10—C11 −0.9 (3)
N1—C1—C2—C3 179.41 (16) C9—C10—C11—C12 0.8 (3)
C6—C1—C2—C3 0.3 (3) C1—N1—C12—C11 178.33 (18)
C1—C2—C3—C4 0.3 (3) C13—N1—C12—C11 1.3 (3)
C2—C3—C4—C5 −0.6 (3) C1—N1—C12—C7 −0.6 (2)
C3—C4—C5—C6 0.3 (3) C13—N1—C12—C7 −177.59 (15)
C4—C5—C6—C1 0.3 (3) C10—C11—C12—N1 −178.94 (17)
C4—C5—C6—C7 −177.68 (18) C10—C11—C12—C7 −0.2 (3)
N1—C1—C6—C5 −179.87 (15) C8—C7—C12—N1 178.71 (15)
C2—C1—C6—C5 −0.6 (3) C6—C7—C12—N1 −0.3 (2)
N1—C1—C6—C7 −1.38 (19) C8—C7—C12—C11 −0.3 (3)
C2—C1—C6—C7 177.91 (16) C6—C7—C12—C11 −179.28 (16)
C5—C6—C7—C8 0.4 (4) C1—N1—C13—C14 −82.2 (2)
C1—C6—C7—C8 −177.79 (19) C12—N1—C13—C14 94.4 (2)
C5—C6—C7—C12 179.19 (19) N1—C13—C14—O1 −9.8 (3)
C1—C6—C7—C12 1.01 (19) N1—C13—C14—O2 171.34 (15)

Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O2—H2O···O1i 0.95 (3) 1.70 (3) 2.645 (2) 171 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2123).

References

  1. Jinmao, Y., Bo, Zh. & Weibing, Zh. (2001). J. Chromatogr. A, 909, 171–182.
  2. Rigaku (2004). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  3. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  4. Xie, M. H., Qiu, A. Y., He, Y. J., Wu, J., Zhou, X. Q., Zou, P., Liu, Y. L. & Luo, S. N. (2006). Chin. J. Anal. Chem.34, S131–134.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043463/cs2123sup1.cif

e-65-o2860-sup1.cif (15.9KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043463/cs2123Isup2.hkl

e-65-o2860-Isup2.hkl (124.6KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report


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