Home Crystal structure of tripropylammonium 2′-carboxy-[1,1′-biphenyl]-2-carboxylate – [1,1′-biphenyl]-2,2′-dicarboxylic acid (2/1), C60H72N2O12
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Crystal structure of tripropylammonium 2′-carboxy-[1,1′-biphenyl]-2-carboxylate – [1,1′-biphenyl]-2,2′-dicarboxylic acid (2/1), C60H72N2O12

  • Xiangxiang Wu EMAIL logo and Yanbing Zai
Published/Copyright: November 12, 2016

Abstract

C60H72N2O12, triclinic, P1 (no. 1), a = 9.6569(4) Å, b = 10.9361(4) Å, c = 13.8551(6) Å, α = 113.198(3)°, β = 95.632(4)°, γ = 91.114(3)°, V = 1335.72(9) Å3, Z = 1, Rgt(F) = 0.0512, wRref(F2) = 0.1380, T = 150(2) K.

CCDC no.:: 1510401

The asymmetric unit of the title crystal structure is shown in the figure (hydrogen atoms are omitted for clarity). Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Yellow block
Size:0.26 × 0.16 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.9 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:50°, >99%
N(hkl)measured, N(hkl)unique, Rint:9438, 7449, 0.023
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 6838
N(param)refined:685
Programs:Bruker programs [4], SHELX [5]
Table 2

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

AtomxyzUiso*/Ueq
N10.9301(3)0.3645(3)0.6838(3)0.0363(7)
H11.0229(18)0.343(5)0.683(4)0.054*
C10.1031(3)0.9018(3)0.9611(3)0.0293(7)
O10.1222(3)1.0297(3)0.81658(19)0.0375(6)
H1A0.127(5)1.073(4)0.777(3)0.056*
N20.4457(3)0.6138(3)0.1896(3)0.0353(7)
H20.3531(19)0.580(4)0.176(4)0.053*
C2−0.0040(3)0.9684(3)0.9306(3)0.0284(7)
O2−0.0821(3)1.1129(4)0.8510(3)0.0668(10)
O30.2223(3)1.1652(2)1.06002(19)0.0364(6)
H30.216(5)1.2468(18)1.103(3)0.055*
C3−0.1343(4)0.9670(4)0.9641(3)0.0360(8)
H3A−0.20621.01230.94280.043*
C4−0.1622(4)0.9009(4)1.0278(3)0.0394(9)
H4A−0.25220.90091.05010.047*
O40.4331(3)1.2140(3)1.0317(4)0.0820(13)
O51.2268(3)0.3222(3)0.65534(19)0.0379(6)
C5−0.0576(4)0.8353(4)1.0586(3)0.0416(9)
H5A−0.07560.78921.10200.050*
O61.1329(3)0.1754(3)0.7062(2)0.0445(6)
C60.0726(4)0.8362(4)1.0266(3)0.0373(8)
H6A0.14380.79151.04940.045*
O71.4457(3)0.4005(2)0.59524(19)0.0360(6)
H71.374(3)0.379(5)0.619(4)0.054*
C70.0088(3)1.0437(3)0.8610(3)0.0317(8)
O81.5544(3)0.3667(2)0.4545(2)0.0435(7)
C80.2457(4)0.8869(3)0.9261(3)0.0291(7)
C90.3516(3)0.9882(3)0.9543(3)0.0296(7)
O90.2186(3)0.4265(3)0.1603(2)0.0446(7)
C100.4815(4)0.9550(4)0.9196(3)0.0354(8)
H10A0.55391.02340.94000.042*
O100.1261(3)0.6217(2)0.22056(19)0.0389(6)
C110.5092(4)0.8259(4)0.8563(3)0.0429(9)
H11A0.59810.80610.83210.051*
O11−0.0903(3)0.7472(2)0.28426(19)0.0359(6)
H11−0.009(2)0.716(5)0.273(4)0.054*
C120.4045(4)0.7270(4)0.8294(3)0.0423(9)
H12A0.42090.63750.78630.051*
O12−0.1907(3)0.8537(3)0.4288(2)0.0413(6)
C130.2767(4)0.7574(4)0.8646(3)0.0379(8)
H13A0.20660.68740.84640.045*
C140.3399(3)1.1327(4)1.0204(3)0.0349(8)
C151.4168(3)0.1068(3)0.5566(3)0.0269(7)
C161.3631(4)0.1457(3)0.6550(3)0.0304(7)
C171.4394(4)0.1222(4)0.7365(3)0.0393(9)
H17A1.40140.14210.80130.047*
C181.5672(4)0.0712(4)0.7246(3)0.0405(9)
H18A1.61990.06120.78240.049*
C191.6208(4)0.0335(4)0.6281(3)0.0358(8)
H19A1.7091−0.00370.61920.043*
C201.5442(3)0.0509(3)0.5453(3)0.0301(7)
H20A1.58000.02380.47900.036*
C211.2323(4)0.2175(4)0.6742(3)0.0352(8)
C221.3319(3)0.1182(3)0.4644(2)0.0276(7)
C231.3566(4)0.2211(3)0.4317(3)0.0281(7)
C241.2826(4)0.2203(4)0.3391(3)0.0352(8)
H24A1.30210.28910.31580.042*
C251.1813(4)0.1199(4)0.2815(3)0.0370(8)
H25A1.12940.12100.22000.044*
C261.1560(4)0.0175(4)0.3141(3)0.0359(8)
H26A1.0867−0.05190.27480.043*
C271.2317(4)0.0168(3)0.4034(3)0.0309(7)
H27A1.2150−0.05490.42410.037*
C281.4608(4)0.3349(3)0.4944(3)0.0325(8)
C29−0.0607(3)0.4890(3)0.3132(3)0.0268(7)
C30−0.0103(4)0.4362(3)0.2148(3)0.0327(8)
C31−0.0864(4)0.3345(4)0.1318(3)0.0413(9)
H31A−0.05030.29720.06560.050*
C32−0.2144(4)0.2855(4)0.1427(3)0.0421(9)
H32A−0.26690.21640.08450.051*
C33−0.2650(4)0.3396(3)0.2410(3)0.0374(8)
H33A−0.35300.30760.24970.045*
C34−0.1884(4)0.4388(3)0.3250(3)0.0326(8)
H34A−0.22310.47350.39180.039*
C350.1205(4)0.4974(4)0.1973(3)0.0347(8)
C360.0240(3)0.5920(3)0.4092(3)0.0269(7)
C370.0011(4)0.7274(3)0.4456(3)0.0285(7)
C380.0752(4)0.8170(3)0.5392(3)0.0346(8)
H38A0.05760.90890.56490.041*
C390.1746(4)0.7722(4)0.5949(3)0.0387(8)
H39A0.22640.83380.65780.046*
C400.1983(4)0.6387(4)0.5593(3)0.0361(8)
H40A0.26630.60830.59750.043*
C410.1227(4)0.5488(3)0.4676(3)0.0320(8)
H41A0.13820.45660.44400.038*
C42−0.1015(4)0.7826(3)0.3874(3)0.0302(7)
C430.8673(5)0.3564(4)0.7749(3)0.0467(10)
H43A0.87740.26550.77280.056*
H43B0.76620.36850.76560.056*
C440.9272(5)0.4558(5)0.8837(3)0.0547(11)
H44A0.91180.54700.88800.066*
H44B0.87550.44200.93720.066*
C451.0802(6)0.4467(6)0.9111(4)0.0683(13)
H45A1.11100.51440.98180.102*
H45B1.13280.46170.85930.102*
H45C1.09640.35790.90980.102*
C460.9376(4)0.5030(3)0.6862(3)0.0363(8)
H46A0.98870.50220.62740.044*
H46B0.99260.56260.75310.044*
C470.7978(4)0.5614(4)0.6774(3)0.0411(9)
H47A0.74080.50270.61120.049*
H47B0.74700.56720.73760.049*
C480.8199(5)0.6989(4)0.6777(3)0.0484(10)
H48A0.72930.73590.67200.073*
H48B0.86920.69270.61750.073*
H48C0.87550.75700.74360.073*
C490.8572(4)0.2621(4)0.5823(3)0.0367(8)
H49A0.85860.17400.58670.044*
H49B0.75840.28340.57580.044*
C500.9181(4)0.2517(4)0.4839(3)0.0389(8)
H50A1.01660.22890.48840.047*
H50B0.91580.33860.47730.047*
C510.8360(4)0.1455(4)0.3878(3)0.0423(9)
H51A0.87640.13940.32400.063*
H51B0.73880.16880.38300.063*
H51C0.83940.05940.39410.063*
C520.5143(4)0.6182(4)0.2925(3)0.0368(8)
H52A0.61170.65500.30270.044*
H52B0.51780.52580.28820.044*
C530.4443(4)0.6999(4)0.3890(3)0.0391(8)
H53A0.34650.66480.38030.047*
H53B0.44340.79380.39660.047*
C540.5231(5)0.6932(4)0.4880(3)0.0455(9)
H54A0.47710.74570.55000.068*
H54B0.61940.72950.49710.068*
H54C0.52330.60030.48040.068*
C550.4227(4)0.7497(4)0.1895(3)0.0366(8)
H55A0.36810.79910.24820.044*
H55B0.36640.73860.12260.044*
C560.5554(4)0.8320(4)0.2011(3)0.0415(9)
H56A0.61000.78510.14180.050*
H56B0.61270.84440.26790.050*
C570.5205(5)0.9665(4)0.2013(3)0.0471(10)
H57A0.60691.01980.20940.071*
H57B0.46671.01280.26020.071*
H57C0.46530.95390.13450.071*
C580.5257(4)0.5284(4)0.1007(3)0.0440(9)
H58A0.53500.44040.10460.053*
H58B0.62080.57070.11180.053*
C590.4600(5)0.5068(5)−0.0091(3)0.0539(11)
H59A0.37310.4492−0.02630.065*
H59B0.43500.5937−0.01010.065*
C600.5555(7)0.4435(7)−0.0918(5)0.0852(17)
H60A0.50890.4317−0.16130.128*
H60B0.57890.3565−0.09230.128*
H60C0.64100.5010−0.07590.128*

Source of material

Biphenyl-2,2′-dicarboxylic acid and tripropylamine, which were purchased from Aladdin Corporation, were mixed with a molar ratio of 1:4 and dissolved in the water/ethanol solvent (1:2 v/v). The mixture was vigorously stirred for 1 h at room temperature to get a yellow solution. After setting aside for 1 week at room temperature, yellow block crystals of the title compound were obtained.

Experimental details

In the crystal structure, non-hydrogen atoms were refined with anisotropic displacement parameters, and all H atoms bonded to C atoms were positioned at calculated positions, riding on the parent atom. The H atoms bonded to O and N atoms were located in difference maps and refined with the riding model of the fixed O—H distance of 0.86 ± 0.01 Å and N—H of 0.93 ± 0.01 Å.

Discussion

As an aromatic acid with two carboxyl groups, biphenyl-2,2′-dicarboxylic acid can be used to interact with different compounds to obtain various crystal structures [1], [2], [3]. However, the crystal structure of biphenyl-2,2′-dicarboxylic acid and tripropylamine has not been reported till now. Herein we report the related title crystal structure, which can help to understand the crystallography of biphenyl-2,2′-dicarboxylic acid and the deprotonated anions under basic conditions. Due to its two carboxyl groups, biphenyl-2,2′-dicarboxylic acid tends to form the related anions [2, 3].

In the asymmetric unit of the title compound, there are one molecule of biphenyl-2,2′-dicarboxylic acid, two biphenyl-2,2′-dicarboxylate monoanions and two tripropyl-ammonium cations. The two anions display very similar configurations with the similar interplanar angles of 81.7° and 83.5° and the torsion angles of 51.7° and 56.0° between the carboxyl groups and the related benzene rings. The neutral molecule shows a smaller interplanar angle of 65.5° and the carboxyl groups are almost coplanar with the adjacent ring with angles of 6.1° and 10.2° between the planes. Obviously, the deprotonation of biphenyl-2,2′-dicarboxylic acid result in very different configurations between the neutral molecule and the related anions. It can be observed that the neutral molecule mentioned above can link two related anions with intermolecular O—H⋯O hydrogen bonding to yield a butterfly-like motif, in which the molecule can be regarded as the ‘body’ of the ‘butterfly’ and the two anions are just like two ‘wings’. Furthermore, there exist intramolecular O—H⋯O hydrogen bonds in these two anions to stabilize their spacial configurations. Then the two counterions of tripropylazanium interact with the two anions to generate the final structure with strong N—H⋯O hydrogen bonds, in which the cations are just like two ‘streamers’ decorated on the two ‘wings’. Undoubtedly, various O—H⋯O and N—H⋯O hydrogen bonding are crucial factors in forming the crystal structure of the title compound.

Acknowledgements

We thank for the support from Henan University of Traditional Chinese Medicine.

References

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2 Imai, Y.; Sato, T.; Kuroda, R.: Efficient optical resolution of secondary alkyl alcohols by chiral supramolecular hosts. Chem. Commun. 26 (2005) 3289–3291.10.1039/b504164cSearch in Google Scholar PubMed

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Received: 2016-6-1
Accepted: 2016-10-18
Published Online: 2016-11-12
Published in Print: 2017-1-1

©2016 Xiangxiang Wu et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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  52. Crystal structure of (E)-3-((naphthalen-1-ylimino)methyl)-4-nitrophenol, C17H12N2O3
  53. Crystal structure of 2-dichloromethyl-2-p-nitrophenyl-1,3-dioxolane, C10H9Cl2NO4
  54. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanopalladate(II), C14H24N8Pd2
  55. Crystal structure of 2-(4-oxo-2-thioxothiazolidin-3-yl)acetic acid monohydrate, C5H7NO4S2
  56. Crystal structure of a P4-bridged (η5-pentamethyl-cyclopentadienyl)(η5-adamantylcyclopentadienyl) titanium(III)complex, C50H66P4Ti2
  57. Crystal structure of cis-bis(2,2′-bipyrimidine-κ2N,N′)bis(thiocyanato-κN)nickel(II), C18H12N10NiS2
  58. Crystal structure of cis-bis(2,2′-bipyridine-κ2N,N′)dibromidomanganese(II), C20H16Br2MnN4
  59. Crystal structure of cis-bis(2,2′-bipyridine-κ2N,N′)bis(thiocyanato-κN)nickel(II), C22H16N6NiS2
  60. Crystal structure of trans-dibromido(1,4,8,11-tetraazacyclotetradecane)nickel(II), C10H24Br2N4Ni
  61. Crystal structure of cis-tetrabromidobis(pyridine-κN)platinum(IV), C10H10Br4N2Pt
  62. Crystal structure of (E)-5-((4-chlorophenyl)diazenyl)-2-(5-(4-fluorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole, C23H17ClFN5S2
  63. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridocobaltate(II) monohydrate, C10H18Cl4CoN2O
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