Home The crystal structure of 2-(2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)phenoxy)acetate, C19H18N2O3
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The crystal structure of 2-(2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)phenoxy)acetate, C19H18N2O3

  • Wang Li-Hua and Tai Xi-Shi ORCID logo EMAIL logo
Published/Copyright: July 22, 2020

Abstract

C19H18N2O3, monoclinic, P21/c (no. 14), a = 12.6187(7) Å, b = 9.4445(5) Å, c = 13.7424(8) Å, β = 99.248(5)°, V = 1616.49(16) Å3, Z = 4, Rgt(F) = 0.0793, wRref(F2) = 0.2220, T = 100(10) K.

CCDC no.: 2015520

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.13 × 0.12 × 0.09 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:0.74 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax, completeness:73.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:3187, 3187,
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2800
N(param)refined:218
Programs:Bruker [1], Olex2 [2], SHELX [3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
O10.5085(2)0.1878(3)0.3942(2)0.0192(7)
O20.5907(2)0.2430(3)0.2318(2)0.0189(6)
O30.4614(2)0.1269(3)0.1337(2)0.0204(7)
N10.7459(3)0.4256(4)0.6624(3)0.0179(8)
H10.7052400.3745430.6928480.021*
N20.6697(3)0.4037(4)0.3903(3)0.0156(7)
H2A0.6360550.3428720.3464390.019*
H2B0.6348040.4858230.3819100.019*
C10.9546(3)0.6802(5)0.6557(4)0.0217(9)
H1A0.9864530.7246830.6074100.026*
C20.9873(4)0.7112(5)0.7543(4)0.0269(11)
H21.0412960.7776400.7720510.032*
C30.9406(4)0.6444(5)0.8277(3)0.0246(10)
H30.9655230.6657760.8934960.029*
C40.8582(4)0.5471(5)0.8049(3)0.0226(10)
H40.8266410.5033440.8536660.027*
C50.8249(3)0.5180(5)0.7055(3)0.0172(9)
C60.8723(3)0.5801(5)0.6298(3)0.0175(9)
C70.8202(3)0.5205(4)0.5382(3)0.0165(9)
C80.7441(3)0.4299(4)0.5619(3)0.0159(8)
C90.6636(3)0.3492(4)0.4924(3)0.0156(8)
H90.5921640.3715030.5075740.019*
C100.8363(3)0.5439(5)0.4334(3)0.0188(9)
H10A0.9123430.5443600.4294400.023*
H10B0.8062510.6345360.4099790.023*
C110.7805(3)0.4249(5)0.3698(3)0.0197(9)
H11A0.7781310.4479980.3007060.024*
H11B0.8211060.3379030.3833050.024*
C120.6766(3)0.1898(4)0.4944(3)0.0166(9)
C130.7628(4)0.1195(5)0.5491(3)0.0209(9)
H130.8173280.1717510.5862500.025*
C140.7691(4)−0.0271(5)0.5496(3)0.0231(10)
H140.827093−0.0728820.5869090.028*
C150.6877(4)−0.1045(5)0.4938(3)0.0245(10)
H150.691570−0.2028520.4938810.029*
C160.6005(4)−0.0379(5)0.4378(3)0.0214(9)
H160.546887−0.0908090.4000160.026*
C170.5946(3)0.1094(5)0.4391(3)0.0165(8)
C180.4487(3)0.1378(5)0.3038(3)0.0220(10)
H18A0.3780250.1810050.2937690.026*
H18B0.4393350.0360970.3078900.026*
C190.5042(3)0.1715(4)0.2164(3)0.0176(9)

Source of material

0.0901 g (2-Formylphenoxy)acetic acid (0.5 mmol), 0.0801 g tryptamin (0.5 mmol) and 0.020 g NaOH (0.5 mmol) were added to the solution of water-ethanol (v:v = 1:1) and the solution was heated up to 70 °C with stirring. After 1 h, 0.1098 g zinc(II) acetate dihydrate (0.5 mmol) was added. The mixture continued stirring for 4 hours at 70 °C. After cooled to room temperature, the mixture was filtered. The colorless crystals of 2-(2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)phenoxy)acetate were received through slow evaporation after 30 days.

Experimental details

Coordinates of hydrogen atoms were refined without any constraints or restraints. The hydrogen atoms were positioned geometrically (C—H = 0.93–0.97 Å and N—H = 0.86–0.89 Å). Their Uiso values were set to 1.2Ueq of the parent atoms.

Comment

Many ylide compounds show widespread applications in organic chemistry [5], [6], [7], [8]. In this paper, we report the synthesis of the side-product of the reaction of (2-formylphenoxy)acetic acid, tryptamin and Zn(II)ion. The new three-membered ring ylide compound, 2-(2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)phenoxy)acetate, has been obtained. In the title compound, the C—N bond distances are 1.378(5) Å (N1—C8), 1.384(5) Å (N1—C5), 1.508(5) Å (N2—C9) and 1.484(5) Å (N2—C11), respectively. The C—O bond distances are 1.376(5) Å (O1—C17), 1.427(5) Å (O1—C18), 1.272(5) Å (O2—C19) and 1.250(5) Å (O3—C19), respectively. The dihedral angles of ring 1 (C1—C2—C3—C4—C5—C6) and ring 2 (C5—C6—C7—C8—N1), ring 1 (C1—C2—C3—C4—C5—C6) and ring 3 (C7—C8—C9—N2—C11—C10), ring 2 (C7—C8—C9—N2—C11—C10) and ring 3 (C7—C8—C9—N2—C11—C10) are 1.4°, 5.8° and 4.4°, respectively, indicating that these rings are almost coplanar. However, the dihedral angles of ring 4 (C12—C13—C14—C15—C16—C17) with ring 1, ring 2 and ring 3 are 69.6°, 71.0° and 75.1°, respectively (see the figure). Geometric parameters are all in the expected ranges [9].

References

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Received: 2020-05-18
Accepted: 2020-07-10
Published Online: 2020-07-22
Published in Print: 2020-10-27

©2020 Wang Li-Hua et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  72. Crystal structure of 4-[(3-methoxyphenyl)carbamoyl]butanoic acid, C12H15NO4
  73. Crystal structure of dichlorido-bis(tri-4-tolylphosphane oxide-κO)-di(4-chlorophenyl-κC)tin(IV), C54H50Cl4O2P2Sn
  74. Crystal structure of dichloridodimethylbis(tri-4-tolylphosphane oxide-κO)-tin(IV), C44H48Cl2O2P2Sn
  75. Crystal structure of chlorido(2-methylquinolin-8-olato-κ2N,O)-bis(4-tolyl-κC)tin(IV), C24H22ClNOSn
  76. Crystal structure of (E)-dichloro(1-chloro-3-methoxyprop-1-en-2-yl)(4-methoxyphenyl)-λ4-tellane, C11H13Cl3O2Te
  77. Crystal structure of bis{N-methyl-N′-[3-(4-methoxyphenyl)-1-methylpropane-1-ylidene]carbamohydrazonothioato}zinc(II), C26H36N6O2S2Zn
  78. Crystal structure of (2-carboxy-4-(3-carboxy-5-carboxylatophenoxy)benzoato-κ2O,O′)bis(1,10-phenantroline-κ2N,N′)cobalt(II), C40H24N4O9Co
  79. The crystal structure of (3S,8R,10R,14R)-17-((2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)-4,4,8,10,14-pentamethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate, C32H52O5
  80. Crystal structure of (μ2-1,1′-bis(diphenylphosphino)ferrocene-κ2P,P′)-bis[(Z)N-(3-fluorophenyl)-O-methylthiocarbamato-S]digold(I) chloroform solvate, C50H42Au2F2FeN2O2P2S2, CHCl3
  81. Crystal structure of poly[bis(μ2-1,4-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(μ2-tetraoxidomolybdato(VI)-κ2O:O′)cobalt(II)], C24H20N8O4MoCo
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