Home Physical Sciences Crystal structure of triethylammonium 2′-carboxy-[1,1′-biphenyl]-2-carboxylate, C20H25NO4
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Crystal structure of triethylammonium 2′-carboxy-[1,1′-biphenyl]-2-carboxylate, C20H25NO4

  • Yimin Hou EMAIL logo , Huahui Zeng and Xiangxiang Wu
Published/Copyright: February 25, 2016

Abstract

C20H25NO4, triclinic, P1̅ (no. 2), a = 8.3727(6) Å, b = 9.7374(7) Å, c = 12.3559(8) Å, α = 80.826(4)°, β = 73.432(4)°, γ = 75.425(4)°, V = 930.28(11) Å3, Z = 2, Rgt(F) = 0.0454, wRref(F2) = 0.1374, T = 296(2) K.

CCDC no.:: 1447822

Table 1

Data collection and handling.

Crystal:Colorless, block, size 0.12×0.25×0.51 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.85 cm−1
Diffractometer, scan mode:CCD area detector, φ and ω scans
2θmax:57°
N(hkl)measured, N(hkl)unique:9327, 4574
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3468
N(param)refined:262
Programs:BRUKER [5], SHELX [6]
Table 2

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

AtomSitexyzUiso
H(1)2i0.205(2)0.733(1)0.317(2)0.077
H(1N)2i0.054(2)0.206(2)0.268(1)0.065
H(3A)2i0.61620.64590.41920.058
H(4A)2i0.79320.80570.36500.068
H(5A)2i0.79560.95380.19910.070
H(6A)2i0.62890.93740.08460.061
H(10A)2i0.05970.88870.02860.057
H(11A)2i0.20170.7440−0.11550.065
H(12A)2i0.47850.6212−0.12640.070
H(13A)2i0.61220.63860.00840.062
H(15A)b2i0.04380.48060.30710.076
H(15B)b2i0.20690.38690.23380.076
H(15C)c2i−0.07280.48500.32320.079
H(15D)c2i−0.18020.40430.28090.079
H(16A)a2i0.05790.54380.11780.122
H(16B)a2i−0.10410.48000.17430.122
H(16C)a2i0.06000.38720.10070.122
H(16D)a2i−0.04820.54840.12960.122
H(16E)a2i0.02440.38840.10510.122
H(16F)a2i0.13160.46950.14740.122
H(17A)b2i−0.18980.36400.43230.063
H(17B)b2i−0.21920.35610.31390.063
H(17C)c2i−0.09650.27660.48240.080
H(17D)c2i0.00940.12500.44990.080
H(18A)a2i−0.34880.19610.44750.106
H(18B)a2i−0.17330.12020.47360.106
H(18C)a2i−0.20290.11240.35520.106
H(18D)a2i−0.28360.13010.48820.106
H(18E)a2i−0.19730.10390.36060.106
H(18F)a2i−0.30320.25570.39300.106
H(19A)b2i0.07210.13680.45620.076
H(19B)b2i0.10770.28680.45860.076
H(19C)c2i0.26050.33060.25500.092
H(19D)c2i0.18310.35570.38330.092
H(20A)a2i0.36820.11920.41930.111
H(20B)a2i0.36280.23160.31360.111
H(20C)a2i0.32750.08120.31280.111
H(20D)a2i0.41850.17460.36280.111
H(20E)a2i0.33570.09050.30340.111
H(20F)a2i0.25760.11530.43190.111

aoccupancy factor: 0.500; boccupancy factor: 0.782; coccupancy factor: 0.214.

Table 3

Atomic displacement parameters (Å2).

AtomSitexyzU11U22U33U12U13U23
C(1)2i0.5141(2)0.7853(1)0.1840(1)0.0313(6)0.0388(6)0.0386(6)−0.0047(5)−0.0072(5)−0.0053(5)
O(1)2i0.2347(1)0.6399(1)0.33584(9)0.0500(6)0.0457(5)0.0608(6)−0.0198(5)−0.0131(5)0.0034(5)
N(1)2i0.0291(2)0.2742(1)0.3195(1)0.0468(6)0.0399(6)0.0467(6)−0.0080(5)−0.0151(5)−0.0072(5)
C(2)2i0.5107(2)0.6981(1)0.2860(1)0.0367(6)0.0356(6)0.0401(6)−0.0036(5)−0.0092(5)−0.0057(5)
O(2)2i0.4557(2)0.4686(1)0.3533(1)0.0843(9)0.0383(6)0.104(1)−0.0129(6)−0.0390(8)0.0131(6)
C(3)2i0.6169(2)0.7055(2)0.3524(1)0.0466(7)0.0514(8)0.0463(7)−0.0055(6)−0.0176(6)−0.0028(6)
O(3)2i0.1368(1)0.9015(1)0.29988(8)0.0504(5)0.0484(6)0.0448(5)−0.0019(4)−0.0085(4)−0.0097(4)
C(4)2i0.7233(2)0.8008(2)0.3199(1)0.0471(8)0.071(1)0.0619(9)−0.0155(7)−0.0249(7)−0.0093(8)
O(4)2i0.0994(1)1.0776(1)0.16533(9)0.0655(7)0.0390(5)0.0619(6)0.0044(5)−0.0253(5)−0.0107(4)
C(5)2i0.7255(2)0.8885(2)0.2204(1)0.0458(8)0.071(1)0.0665(9)−0.0274(7)−0.0148(7)−0.0024(8)
C(6)2i0.6241(2)0.8796(2)0.1526(1)0.0449(7)0.0589(9)0.0492(8)−0.0204(7)−0.0109(6)0.0055(6)
C(7)2i0.3978(2)0.5921(1)0.3270(1)0.0542(8)0.0366(7)0.0430(7)−0.0113(6)−0.0161(6)−0.0007(5)
C(8)2i0.4166(2)0.7737(1)0.1025(1)0.0400(6)0.0353(6)0.0351(6)−0.0085(5)−0.0085(5)−0.0023(5)
C(9)2i0.2499(2)0.8511(1)0.1068(1)0.0409(6)0.0317(6)0.0398(6)−0.0088(5)−0.0128(5)−0.0018(5)
C(10)2i0.1711(2)0.8384(2)0.0250(1)0.0543(8)0.0423(7)0.0523(8)−0.0100(6)−0.0257(7)−0.0013(6)
C(11)2i0.2560(2)0.7521(2)−0.0616(1)0.079(1)0.0510(8)0.0449(7)−0.0219(8)−0.0282(7)−0.0034(6)
C(12)2i0.4205(2)0.6784(2)−0.0676(1)0.077(1)0.0568(9)0.0415(7)−0.0137(8)−0.0093(7)−0.0168(6)
C(13)2i0.5005(2)0.6889(2)0.0134(1)0.0501(8)0.0534(8)0.0459(7)−0.0027(6)−0.0063(6)−0.0127(6)
C(14)2i0.1552(2)0.9512(1)0.1969(1)0.0358(6)0.0387(7)0.0499(7)−0.0056(5)−0.0160(5)−0.0088(5)
C(15)b2i0.0831(3)0.4058(2)0.2562(2)0.068(2)0.047(1)0.083(2)−0.024(1)−0.025(1)−0.001(1)
C(15')c2i−0.065(1)0.4122(8)0.2756(7)0.079(6)0.046(4)0.062(5)0.001(4)−0.011(4)−0.006(3)
C(16)a2i0.0184(3)0.4589(2)0.1531(2)0.089(1)0.070(1)0.080(1)−0.026(1)−0.025(1)0.025(1)
C(16')a2i0.0184(3)0.4589(2)0.1531(2)0.089(1)0.070(1)0.080(1)−0.026(1)−0.025(1)0.025(1)
C(17)b2i−0.1620(2)0.3040(2)0.3710(2)0.046(1)0.053(1)0.053(1)0.0004(8)−0.0099(8)−0.0113(8)
C(17')c2i−0.065(1)0.2105(9)0.4250(6)0.081(6)0.060(5)0.049(4)−0.011(4)−0.002(4)−0.005(3)
C(18)a2i−0.2276(2)0.1714(2)0.4158(2)0.0541(9)0.071(1)0.078(1)−0.0169(8)−0.0007(8)−0.0032(9)
C(18')a2i−0.2276(2)0.1714(2)0.4158(2)0.0541(9)0.071(1)0.078(1)−0.0169(8)−0.0007(8)−0.0032(9)
C(19)b2i0.1218(3)0.2134(3)0.4099(2)0.062(1)0.072(2)0.058(1)−0.003(1)−0.030(1)−0.008(1)
C(19')c2i0.202(1)0.289(1)0.328(1)0.071(5)0.061(5)0.112(8)−0.021(4)−0.037(5)−0.011(5)
C(20)a2i0.3130(2)0.1560(2)0.3592(2)0.059(1)0.071(1)0.105(1)−0.0142(9)−0.041(1)−0.005(1)
C(20')a2i0.3130(2)0.1560(2)0.3592(2)0.059(1)0.071(1)0.105(1)−0.0142(9)−0.041(1)−0.005(1)

aoccupancy factor: 0.500; boccupancy factor: 0.782; coccupancy factor: 0.214.

The crystal structure is shown in the figure. Tables 13 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Source of material

2,2′-Dithiosalicyclic acid, 2,2′-biphenyldicarboxylic acid and triethylamine were dissolved in small quantities of water/ethanol according to the molar ratio of 1:2:2. The mixture was stirred for about 2 h, then stand aside to yield colorless block-shaped crystals of the title compound after about 7 days. But 2,2′-dithiosalicyclic acid is not present in the crystal structure.

Experimental details

All H atoms bonded to C were introduced in idealized dispositions. The H atoms bonded to O and N atoms were located in the difference maps. Additionally, triethylammonium is disordered.

Discussion

[1,1′-Biphenyl]-2,2′-dicarboxylic acid, which is an important medical intermediate, is widely used in MOF chemistry to explore different properties such as magnetism [1], fluorescent probe [2] and so on [3, 4]. In the aforementioned reaction triethylamine is monoprotonated by the dicarboxylic acid. The N—H group interacts with one O atom of the carboxylate group of the anion (N—H⋯O).

In the asymmetric unit of the title compound, there is one independent 2′-carboxy-[1,1′-biphenyl]-2-carboxylate anion and one triethylammonium cation. In the anion, the phenyl rings show a torsion angle of 94.8°, which indicates the two rings are almost perpendicular to each other. And the torsion angles of the carboxyl and the carboxy group with respect to the related rings are 53.3° and 55.9°. To further stabilize the configuration of the anion, there also exists one intramolecular O—H⋯O hydrogen bond.


Corresponding author: Yimin Hou, Pharmacy College, Henan University of Traditional Chinese Medicine, Zhengzhou, 450046, China, e-mail:

Acknowledgements:

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

References

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2. Guo, F.; Wang, F.; Yang, H.; Zhang, X.; Zhang, J.: Tuning structural topologies of three photoluminescent metal–organic frameworks via isomeric biphenyldicarboxylates. Inorg. Chem. 51 (2012) 9677–9682.10.1021/ic3008969Search in Google Scholar PubMed

3. Jeong, K. S.; Go, Y. B.; Shin, S. M.; Lee, S. J.; Kim, J.; Yaghib, O. M.; Jeong, N.: Asymmetric catalytic reactions by NbO-type chiral metal–organic frameworks. Chem. Sci. 2 (2011) 877–882.10.1039/c0sc00582gSearch in Google Scholar

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Received: 2015-11-19
Accepted: 2016-1-18
Published Online: 2016-2-25
Published in Print: 2016-6-1

©2016 Yimin Hou et al., published by De Gruyter.

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

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  58. Crystal structure of 2-amino-4-(3,5-difluoro-phenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H12F2N2O2
  59. Crystal structure of tris(N-nitroso-N-oxyanilino-κ2O, O′) oxidoniobium(V), C18H15N6O7Nb
  60. Crystal structure of 1-(5-benzoyl-4-methyl-2-(phenylamino)thiophen-3-yl)ethan-1-one, a structure with Z′ = 6, C20H17NO2S
  61. Crystal structure of diethyl-3-methyl-4-phenylthieno[2,3-b]thiophene-2,5-dicarboxylate, C19H18O4S2
  62. Crystal structure of 3,5-dicarboxybenzoate — benzene-1,3,5-tricarboxylic acid (1/1), C24H22N2O12
  63. The crystal structure of 2-chloro-1,3-bis(2,4,6-trimethylphenyl)-4,4-dimethyl-1,3,2λ3,4-diazaphosphasiletidine
  64. Crystal structure of hexaquamanganese(II) bis(hexaborato-κ3O,O′,O′′)manganese(II) dihydrate, B12H28Mn2O34
  65. Crystal structure of 1-propyl-3-methylimidazolium pentaborate, [C7H13N2][B5O6(OH)4]
  66. Crystal structure of 13-(4-fluorophenyl)-11,13-dihydro-1H-benzo[h]indazolo[6,7-b] [1, 6]naphthyridin-12(6H)-one — dimethylformamide — water (1/2/1), C29H31FN6O4
  67. Crystal structure of 1-(2-chlorophenyl)-2-(2-nitrophenyl)ethan-1-ol, C14H12ClNO3
  68. Crystal structure of (Z)-2-((2-bromo-1-phenylvinyl)oxy)benzonitrile, C15H10BrNO
  69. Crystal structure of tetrachlorido(1E,1′E)-N,N′-((1,4-phenylenebis(propane-2,2-diyl))bis(4,1-phenylene))bis(1-(pyridin-2-yl-κN)methanimine-κN)dizinc(II), C36H34N4Zn2Cl4
  70. Crystal structure of 2,6-bis(3-methylpyridinyl)hexahydro-4,8-ethenopyrrolo-[3,4-f]isoindole-1,3,5,7(2H,6H)-tetrone, C24H20N4O4
  71. Crystal structure of trans-bis(2-methylmaleato-κ2O,O′) bis(piperazinium-κN) cobalt(II) trihydrate, C18H36CoN4O11
  72. Crystal structure of (E)-4-chloro-N′-(4-(diethylamino)benzylidene)benzohydrazide, C18H20ClN3O
  73. Crystal structure of 3,6-di(1H-imidazol-1-yl)-9H-carbazole, C18H13N5
  74. Crystal structure of 4-(4-pyridinyl)-1-naphthoic acid, C16H11NO2
  75. Crystal structure of 1,1′-diformyl-4,4′-(6H,12H-5,11-methano-dibenzo[b,f][11,5]diazocine-2,8-diyl)dibenzene, C29H22N2O2
  76. Crystal structure of N′-(adamantan-2-ylidene)pyridine-3-carbohydrazide, C16H19N3O
  77. Crystal structure of 1,1′-(butane-1,4-diyl)bis(5-methyl-1H-pyrazole-3-carbaldehyde), C14H18N4O2
  78. Crystal structure of methyl 8-hydroxy-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,8,10a,10b-decahydrocyclohepta[e]indene-3a(1H)-carboxylate, C21H34O3
  79. Crystal structure of 6-oxo-4-propyl-2-(propylthio)-1,6-dihydropyrimidine-5-carbonitrile, C11H15N3OS
  80. Crystal structure of poly[diacetato(μ2-1,4-bis(1H-imidazol-1-yl)benzene-κ2N:N′)nickel(II)], C26H22N8NiO4
  81. Crystal structure of bis(2,4-dibromo-6-{(E)[(4-fluorobenzyl)imino]methyl}phenolato-κ2N,O) copper(II), C28H18Br4F2N2O2Cu
  82. Crystal structure of 1-(adamantan-1-yl)-3-phenylthiourea, C17H22N2S
  83. Crystal structure of 3-(6-(5-amino-1-phenyl-1H-pyrazol-3-yl)pyridin-2-yl)-1-phenyl-1H-pyrazol-5-amine – dioxan (2/1), C25H23N7O
  84. Crystal structure of 5-ethyl-6-[(3-methylphenyl)sulfanyl]pyrimidine-2,4(1H,3H)-dione, C13H14N2O2S
  85. Crystal structure of (((1E,1′E)-(cyclohexane-1,2-diylbis(azanylylidene-κ2N,N′))bis(methanylylidene))bis(2,1-phenylene))bis((2,6-diisopropylphenyl)amide-κ2N′′,N′′′)manganese(II), C44H54N4Mn
  86. Crystal structure of prop-2-en-1-yl 2-oxo-2H-1-benzopyran-3-carboxylate, C13H10O4
  87. Crystal structure of bis(μ2-2-((3-methylphenyl)imino)methylphenolato-κ2N,O:O)hexacarbonyldimanganese(I), C34H24Mn2N2O8
  88. Crystal structure of (Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxybut-2-en-1-one C9H12N2O2
  89. Crystal structure of 2,2′-[pentane-1,5-diylbis(oxy)]dibenzaldehyde, C19H20O4
  90. Crystal structure of 2-phenyl-5,6,7,8-tetrahydro-4H-benzo[4,5]thieno[2,3-d][1,3]oxazin-4-one, C16H13NO2S
  91. Crystal structure of (E)-1-(2-chlorophenyl)-N-(4-chlorophenyl)methanimine, C13H9Cl2N
  92. Crystal structure of ethyl 2-amino-5-bromothiazole-4-carboxylate, C6H7BrN2O2S
  93. Crystal structure of 2-benzylisothiouronium tetraphenylborate, C32H31BN2S
  94. Crystal structure of poly[(μ2-biphenyl-2,2′-dicarboxylato-κ4O,O′:O′′,O′′′)(μ2-4,4′-bipyridine-κ2N:N′)copper(II)], C24H16CuN2O4
  95. Crystal structure of (η5-pentamethylcyclopentadienyl)titanium(III)dichloride (THF), C14H23Cl2OTi
  96. Crystal structure of 3-ferrocenylsulfonyl-2-(4-methoxyphenyl)-3H-imidazo[4,5-b]pyridine, C23H19FeN3O3S
  97. Crystal structure of 2-benzoyl-3-(4-fluorophenyl)cyclopropane-1,1-dicarbonitrile, C18H11FN2O
  98. Crystal structure of 1,6-ditosyl-1,6-diazecane, C22H30N2O4S2
  99. Crystal structure of N-phenyl-2-(pyridin-4-ylcarbonyl)hydrazinecarboxamide with Z′ = 4, C13H12N4O2
  100. Crystal structure of N,N-bis(diphenylphosphanyl)cyclohexylamine, C30H31NP2
  101. Crystal structure of 3-(4-hydroxy-3-methoxyphenyl)-N-phenylpropanamide, C16H17NO3
  102. Crystal structure of 6-(2-fluorophenyl)-3-phenyl-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazole, C15H9FN4S
  103. Crystal structure of catena-poly[aqua(dicyanoazanido-2κN-μ2-dicyanoazanido-1κN:2κN′)(μ2-2-methoxy-6-(((2-((3-methoxy-2-oxidobenzylidene)amino)ethyl)imino)methyl)phenolato-1κ2N,N′,2κ2O,O′,1κ2O′′,O′′′:2κ2O′′,O′′′)cadmium(II)copper(II)], C22H20CdCuN8O5
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