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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page o446
https://doi.org/10.1107/S1600536810002163

1-Methyl-1,2,3,4-tetra­hydro­carbolin-2-ium-3-carboxyl­ate

Cheng-Tao Lu,a Lin-lin Jing,a Hai-Bo Wang,a Hai-Feng Tangb* and Xiao-Li Suna*

aDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032 Xi-An, People's Republic of China, and bDepartment of Pharmacy, Xijing Hospital, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032 Xi-An, People's Republic of China
*Correspondence e-mail: tanghaifeng71@163.com, xiaoli_sun@yahoo.cn

(Received 23 November 2009; accepted 18 January 2010; online 27 January 2010)

The title compound, C13H14N2O2, is a natural product isolated from Cicer arietinum L. (chickpea). The benzene ring and pyrrole rings display planar conformations and the piperidine ring has a half-chair conformation. Inter­molecular C—H⋯π inter­actions between a methyl H atom and the pyrrole ring of an adjacent mol­ecule are present in the crystal structure.

Related literature

For the isolation of the title compound as a natural product, see: Kicha et al. (2003[Kicha, A. A., Ivanchina, N. V., Kalinovsky, A. I., Dmitrenok, P. S. & Stonik, V. A. (2003). Tetrahedron Lett. 44, 1935-1937.]). For the bioactivity of the title compound, see: Adachi et al. (1991[Adachi, J., Mizoi, Y., Naito, T., Ogawa, Y., Uetani, Y. & Ninomiya, I. (1991). J. Nutr. 121, 646-652.]); Ogawa & Adachi (1993[Ogawa, Y. & Adachi, J. (1993). Arch. Toxicol. 67, 290-293.]).

[Scheme 1]

Experimental

Crystal data

  • C13H14N2O2

  • Mr = 230.26

  • Orthorhombic, P 21 21 21

  • a = 4.9772 (8) Å

  • b = 14.520 (2) Å

  • c = 15.307 (2) Å

  • V = 1106.3 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.32 × 0.23 × 0.13 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.971, Tmax = 0.988

  • 5528 measured reflections

  • 1166 independent reflections

  • 880 reflections with I > 2σ(I)

  • Rint = 0.053
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.117

  • S = 1.00

  • 1166 reflections

  • 156 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C1/C6/C7/C11/N1 pyrrole ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C10—H10⋯Cg1i 0.98 2.69 3.644 (3) 165
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2000[Bruker (2000). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]) and ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810002163/pb2017sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002163/pb2017Isup2.hkl

checkCIF report


Comment top

The title compound is isolated from Cicer arietinum L. (Chickpea), It is a precursor of mutagenic N-nitroso compounds, which show direct-acting mutagenicity on Salmonlla typhimurium TA 100 (Adachi et al., 1991) and may cause eosinophilia-myalgia syndrome (EMS) associated with ingestion of L-tryptophan (Ogawa, 1993).

The benzene ring and pyrrole ring display a planar conformation, and the piperidine ring has a half chair conformation. The molecular packing is stabilized by an intermolecular C–H···π interactions between methyl H atom of piperidine ring pyrrole ring of an adjacent molecule, with a C10–H10···Cg1 separation of 2.69 Å (Table 1, Cg1 is the centroid of C1—C6—C7—C11—N1 pyrrole ring).

Related literature top

For the isolation of the title compound as a natural product, see: Kicha et al. (2003). For the bioactivity of the title compound, see: Adachi et al. (1991); Ogawa et al. (1993).

Experimental top

6 kg of the dried chickpea seeds were crushed and refluxed with 70% ethanol. After condensation in a rotary evaporator, 0.6 L of a syrupy residue was obtained. The residue was suspended in water and extracted by successive partitioning with petroleum ether, EtOAc, and n-butanol saturated with H2O, respectively. The n-butanol portion (60 g) was fractionated over silica gel column eluted with a continuous gradient of CHCl3/MeOH/H2O (15:1:0–6:4:0.8) mixtures of increasing polarity. Fraction eluted with CHCl3/MeOH/H2O (7:3:0.5) was combined and afforded crude title compound (1.13 g). Suitable crystal for determining the X-ray stucture was obtained with a further purification by re-crystallization in MeOH/H2O (1:1). [α] D= 86° (MeOH, 1/4). Spectroscopic analysis: 1H NMR(CD3OD, 500 MHz): δH 4.71 (1H, q, J=7 Hz), 3.96 (1H, dd, J=12, 5.0 Hz), 3.03 (1H, m), 3.45 (1H, m), 7.47 (1H, d, J=8.0 Hz), 7.05 (1H, m), 7.13 (1H, m), 7.34 (1H, d, J=8.0 Hz), 1.75 (3H, d, J=7.0 Hz); 13C NMR (CD3OD, 125 MHz): δc 51.2 (C-10), 59.8 (C-9), 24.3 (C-8), 107.8 (C-7), 127.5 (C-6), 119.2 (C-5), 120.6 (C-4), 123.3 (C-3), 112.3 (C-2), 138.6 (C-1), 131.3 (C-11), 17.1 (C-12), 173.6(C-13).

Refinement top

All H atoms were positioned geometrically and treated as riding with aromatic C—H = 0.93 Å, methine C—H = 0.98 Å, methylene C—H = 0.97Å & methyl C—H = 0.96 Å. The H atom isotropic displacement parameters were fixed; Uiso(aromatic H, methine H) = 1.2 times Ueq of the parent atom; Uiso(methylene H, methyl H) = 1.5 times Ueq of the parent atom. Friedel pairs were merged.

Structure description top

The title compound is isolated from Cicer arietinum L. (Chickpea), It is a precursor of mutagenic N-nitroso compounds, which show direct-acting mutagenicity on Salmonlla typhimurium TA 100 (Adachi et al., 1991) and may cause eosinophilia-myalgia syndrome (EMS) associated with ingestion of L-tryptophan (Ogawa, 1993).

The benzene ring and pyrrole ring display a planar conformation, and the piperidine ring has a half chair conformation. The molecular packing is stabilized by an intermolecular C–H···π interactions between methyl H atom of piperidine ring pyrrole ring of an adjacent molecule, with a C10–H10···Cg1 separation of 2.69 Å (Table 1, Cg1 is the centroid of C1—C6—C7—C11—N1 pyrrole ring).

For the isolation of the title compound as a natural product, see: Kicha et al. (2003). For the bioactivity of the title compound, see: Adachi et al. (1991); Ogawa et al. (1993).

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound (I), showing the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
1-Methyl-1,2,3,4-tetrahydrocarbolin-2-ium-3-carboxylate top
Crystal data top
C13H14N2O2F(000) = 488
Mr = 230.26Dx = 1.383 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 666 reflections
a = 4.9772 (8) Åθ = 2.7–18.0°
b = 14.520 (2) ŵ = 0.10 mm−1
c = 15.307 (2) ÅT = 296 K
V = 1106.3 (3) Å3Needle, colorless
Z = 40.32 × 0.23 × 0.13 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		1166 independent reflections
Radiation source: fine-focus sealed tube880 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
phi and ω scansθmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −5→5
Tmin = 0.971, Tmax = 0.988k = −17→15
5528 measured reflectionsl = −16→18
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.074P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
1166 reflectionsΔρmax = 0.22 e Å−3
156 parametersΔρmin = −0.17 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (6)
Crystal data top
C13H14N2O2V = 1106.3 (3) Å3
Mr = 230.26Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.9772 (8) ŵ = 0.10 mm−1
b = 14.520 (2) ÅT = 296 K
c = 15.307 (2) Å0.32 × 0.23 × 0.13 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		1166 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		880 reflections with I > 2σ(I)
Tmin = 0.971, Tmax = 0.988Rint = 0.053
5528 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.00Δρmax = 0.22 e Å−3
1166 reflectionsΔρmin = −0.17 e Å−3
156 parameters
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
N10.3184 (7)0.56276 (18)0.71317 (15)0.0402 (7)
H10.28780.50450.71040.048*
N2−0.0123 (6)0.67564 (14)0.90152 (14)0.0319 (6)
H2A−0.14860.66680.93930.038*
H2B0.14210.67290.93200.038*
O2−0.0135 (5)0.82385 (13)1.00915 (13)0.0390 (6)
O1−0.2002 (7)0.91384 (15)0.90704 (15)0.0581 (8)
C10.4997 (7)0.6110 (2)0.66226 (19)0.0382 (8)
C20.6786 (8)0.5800 (3)0.59940 (19)0.0476 (9)
H20.68260.51830.58300.057*
C30.8495 (8)0.6429 (3)0.5621 (2)0.0539 (11)
H30.97450.62320.52090.065*
C40.8388 (8)0.7364 (3)0.5849 (2)0.0503 (9)
H40.95230.77820.55740.060*
C50.6633 (8)0.7669 (3)0.6473 (2)0.0441 (9)
H50.65730.82900.66220.053*
C60.4939 (7)0.7043 (2)0.68836 (19)0.0348 (7)
C70.2982 (7)0.7105 (2)0.75634 (17)0.0343 (8)
C80.2132 (7)0.7924 (2)0.8087 (2)0.0369 (8)
H8A0.17590.84370.76990.044*
H8B0.35740.81050.84770.044*
C9−0.0383 (7)0.7696 (2)0.86201 (19)0.0325 (8)
H9−0.19240.76900.82220.039*
C10−0.0145 (7)0.59951 (19)0.83517 (18)0.0345 (8)
H10−0.19020.59890.80620.041*
C110.1945 (8)0.6245 (2)0.76945 (19)0.0348 (8)
C120.0263 (10)0.5078 (2)0.8807 (2)0.0550 (11)
H12A0.19710.50780.90980.082*
H12B0.02190.45910.83830.082*
H12C−0.11420.49860.92280.082*
C13−0.0897 (7)0.8423 (2)0.9318 (2)0.0355 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0454 (19)0.0379 (14)0.0374 (15)−0.0017 (15)0.0046 (15)−0.0056 (11)
N20.0258 (15)0.0372 (13)0.0326 (13)−0.0020 (13)−0.0009 (14)−0.0002 (10)
O20.0340 (14)0.0448 (13)0.0381 (12)0.0015 (11)0.0012 (12)−0.0039 (10)
O10.076 (2)0.0457 (14)0.0523 (14)0.0215 (15)0.0009 (15)0.0018 (12)
C10.035 (2)0.0501 (19)0.0292 (16)0.0034 (19)−0.0021 (17)−0.0026 (13)
C20.048 (2)0.061 (2)0.0336 (17)0.011 (2)0.0031 (19)−0.0081 (17)
C30.038 (2)0.087 (3)0.037 (2)0.005 (2)0.0069 (19)−0.0038 (19)
C40.034 (2)0.079 (3)0.0377 (18)−0.009 (2)0.0057 (19)0.0038 (18)
C50.038 (2)0.056 (2)0.0382 (17)−0.0014 (19)0.0014 (18)0.0012 (15)
C60.0291 (18)0.0470 (18)0.0283 (14)0.0000 (17)−0.0003 (16)−0.0008 (13)
C70.032 (2)0.0406 (17)0.0303 (16)−0.0006 (15)−0.0002 (16)−0.0013 (12)
C80.033 (2)0.0390 (17)0.0383 (16)−0.0018 (15)0.0021 (16)0.0035 (13)
C90.026 (2)0.0388 (17)0.0324 (15)0.0009 (14)0.0005 (15)0.0017 (13)
C100.0354 (19)0.0374 (17)0.0306 (16)−0.0050 (17)0.0013 (17)−0.0018 (12)
C110.0312 (19)0.0412 (18)0.0319 (15)0.0003 (15)−0.0038 (15)−0.0034 (13)
C120.073 (3)0.041 (2)0.051 (2)−0.001 (2)0.009 (2)0.0002 (15)
C130.0307 (19)0.0395 (18)0.0363 (18)−0.0005 (15)0.0043 (15)0.0011 (14)
Geometric parameters (Å, º) top
N1—C11.383 (4)C5—C61.390 (5)
N1—C111.388 (4)C5—H50.9300
N1—H10.8600C6—C71.428 (5)
N2—C91.498 (4)C7—C111.367 (4)
N2—C101.501 (3)C7—C81.495 (4)
N2—H2A0.9000C8—C91.530 (5)
N2—H2B0.9000C8—H8A0.9700
O2—C131.272 (4)C8—H8B0.9700
O1—C131.234 (4)C9—C131.523 (4)
C1—C21.386 (5)C9—H90.9800
C1—C61.412 (4)C10—C111.492 (4)
C2—C31.373 (5)C10—C121.516 (4)
C2—H20.9300C10—H100.9800
C3—C41.404 (5)C12—H12A0.9600
C3—H30.9300C12—H12B0.9600
C4—C51.368 (5)C12—H12C0.9600
C4—H40.9300
C1—N1—C11108.2 (3)C7—C8—C9110.2 (3)
C1—N1—H1125.9C7—C8—H8A109.6
C11—N1—H1125.9C9—C8—H8A109.6
C9—N2—C10113.4 (2)C7—C8—H8B109.6
C9—N2—H2A108.9C9—C8—H8B109.6
C10—N2—H2A108.9H8A—C8—H8B108.1
C9—N2—H2B108.9N2—C9—C13111.3 (2)
C10—N2—H2B108.9N2—C9—C8110.0 (3)
H2A—N2—H2B107.7C13—C9—C8111.2 (3)
N1—C1—C2130.2 (3)N2—C9—H9108.1
N1—C1—C6108.2 (3)C13—C9—H9108.1
C2—C1—C6121.4 (3)C8—C9—H9108.1
C3—C2—C1118.1 (3)C11—C10—N2105.8 (2)
C3—C2—H2121.0C11—C10—C12115.5 (3)
C1—C2—H2121.0N2—C10—C12109.5 (2)
C2—C3—C4121.1 (3)C11—C10—H10108.6
C2—C3—H3119.5N2—C10—H10108.6
C4—C3—H3119.5C12—C10—H10108.6
C5—C4—C3120.8 (4)C7—C11—N1109.4 (3)
C5—C4—H4119.6C7—C11—C10125.8 (3)
C3—C4—H4119.6N1—C11—C10124.9 (3)
C4—C5—C6119.4 (3)C10—C12—H12A109.5
C4—C5—H5120.3C10—C12—H12B109.5
C6—C5—H5120.3H12A—C12—H12B109.5
C5—C6—C1119.1 (3)C10—C12—H12C109.5
C5—C6—C7134.5 (3)H12A—C12—H12C109.5
C1—C6—C7106.3 (3)H12B—C12—H12C109.5
C11—C7—C6107.8 (3)O1—C13—O2126.5 (3)
C11—C7—C8122.8 (3)O1—C13—C9116.3 (3)
C6—C7—C8129.4 (3)O2—C13—C9117.2 (3)
C11—N1—C1—C2177.1 (3)C10—N2—C9—C8−67.4 (3)
C11—N1—C1—C61.3 (4)C7—C8—C9—N242.5 (3)
N1—C1—C2—C3−176.0 (3)C7—C8—C9—C13166.2 (3)
C6—C1—C2—C3−0.7 (5)C9—N2—C10—C1152.2 (3)
C1—C2—C3—C4−1.8 (5)C9—N2—C10—C12177.2 (3)
C2—C3—C4—C52.2 (6)C6—C7—C11—N10.7 (4)
C3—C4—C5—C60.0 (6)C8—C7—C11—N1−178.1 (3)
C4—C5—C6—C1−2.4 (5)C6—C7—C11—C10179.4 (3)
C4—C5—C6—C7177.5 (4)C8—C7—C11—C100.6 (5)
N1—C1—C6—C5179.0 (3)C1—N1—C11—C7−1.3 (4)
C2—C1—C6—C52.8 (5)C1—N1—C11—C10−180.0 (3)
N1—C1—C6—C7−0.9 (3)N2—C10—C11—C7−19.6 (4)
C2—C1—C6—C7−177.1 (3)C12—C10—C11—C7−140.9 (4)
C5—C6—C7—C11−179.8 (4)N2—C10—C11—N1158.9 (3)
C1—C6—C7—C110.1 (4)C12—C10—C11—N137.6 (4)
C5—C6—C7—C8−1.1 (6)N2—C9—C13—O1−156.8 (3)
C1—C6—C7—C8178.8 (3)C8—C9—C13—O180.3 (4)
C11—C7—C8—C9−12.0 (4)N2—C9—C13—O223.7 (4)
C6—C7—C8—C9169.5 (3)C8—C9—C13—O2−99.2 (3)
C10—N2—C9—C13168.9 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of C1/C6/C7/C11/N1 pyrrole ring.
D—H···AD—HH···AD···AD—H···A
C10—H10···Cg1i0.982.693.644 (3)165
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC13H14N2O2
Mr230.26
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)4.9772 (8), 14.520 (2), 15.307 (2)
V (Å3)1106.3 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.32 × 0.23 × 0.13
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.971, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections		5528, 1166, 880
Rint0.053
(sin θ/λ)max (Å−1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.117, 1.00
No. of reflections1166
No. of parameters156
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.22, −0.17

Computer programs: APEX2 (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of C1/C6/C7/C11/N1 pyrrole ring.
D—H···AD—HH···AD···AD—H···A
C10—H10···Cg1i0.982.693.644 (3)165
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

We thank the Natural Science Foundation of China (grant No. 20802092) for financial support.

References

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ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page o446
https://doi.org/10.1107/S1600536810002163
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