Home Physical Sciences Crystal structure of guanidinium tetrapropylammonium bis(hydrogencarbonate) dihydrate, C15H40N4O8
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Crystal structure of guanidinium tetrapropylammonium bis(hydrogencarbonate) dihydrate, C15H40N4O8

  • Huahui Zeng , Qianjin Shen and Xiangxiang Wu EMAIL logo
Published/Copyright: September 8, 2018
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 233 Issue 6

Abstract

C15H40N4O8, monoclinic, Cc (no. 9), a = 25.986(3) Å, b = 8.3450(6) Å, c = 21.1358(15) Å, β = 90.877(6)°, V = 4582.9(6) Å3, Z = 8, Rgt(F) = 0.0357, wRref(F2) = 0.0916, T = 296(2) K.

CCDC no.: 1862438

The asymmetric unit of the title crystal structure is shown in the figure. 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:Colorless plate
Size:0.38 × 0.16 × 0.05 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:APEX2, φ and ω
θmax, completeness:23.7°, >99%
N(hkl)measured, N(hkl)unique, Rint:8322, 4217, 0.019
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3517
N(param)refined:523
Programs:SHELX [1, 2] , Bruker [3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.26820(10)−0.0439(3)0.09179(12)0.0720(7)
H10.2891(15)−0.095(5)0.117(2)0.108*
O1W0.17440(12)0.6009(3)0.20479(13)0.0707(7)
H1WA0.1627(19)0.612(5)0.2425(11)0.106*
H1WB0.1867(18)0.693(3)0.195(2)0.106*
N10.04595(11)0.7994(3)0.01959(13)0.0502(7)
C1−0.00372(14)0.7119(4)0.03113(18)0.0567(9)
H1A−0.01240.6506−0.00650.068*
H1B0.00210.63610.06530.068*
O20.19009(10)0.0554(3)0.09360(11)0.0655(7)
O2W0.13140(11)0.6658(5)−0.36468(18)0.0973(10)
H2WA0.1478(18)0.744(4)−0.380(3)0.146*
H2WB0.1520(16)0.593(5)−0.352(3)0.146*
N2−0.19118(11)1.1797(3)0.77811(13)0.0471(6)
C2−0.04944(17)0.8138(5)0.0475(2)0.0770(12)
H2A−0.05490.89430.01500.092*
H2B−0.04290.86850.08740.092*
O30.21937(10)−0.0886(3)0.17489(12)0.0702(7)
C3−0.09696(17)0.7109(7)0.0529(2)0.0890(14)
H3A−0.12580.77700.06340.133*
H3B−0.10360.65800.01330.133*
H3C−0.09160.63220.08550.133*
O3W0.37202(12)0.1012(5)−0.11960(14)0.0940(10)
H3WA0.372(2)0.145(6)−0.1563(14)0.141*
H3WB0.3970(15)0.035(5)−0.116(2)0.141*
N30.28407(13)0.0776(4)−0.04013(16)0.0777(10)
H3D0.28330.0383−0.00250.093*
H3E0.31180.0721−0.06160.093*
C40.06118(15)0.8990(4)0.07693(16)0.0558(9)
H4A0.09230.95760.06720.067*
H4B0.03430.97720.08420.067*
O4W0.06654(13)0.6502(5)−0.25316(18)0.1129(12)
H4WA0.0948(15)0.667(7)−0.273(3)0.169*
H4WB0.061(2)0.549(3)−0.259(3)0.169*
N40.24370(13)0.2051(4)−0.12278(15)0.0691(9)
H4C0.21670.2488−0.13920.083*
H4D0.27150.1994−0.14420.083*
O40.15079(12)0.3434(4)−0.17025(13)0.0825(8)
C50.07044(16)0.8069(4)0.13744(17)0.0639(10)
H5A0.10010.73760.13280.077*
H5B0.04080.74010.14610.077*
N50.20037(13)0.1544(4)−0.03166(15)0.0693(9)
H5C0.17310.1979−0.04760.083*
H5D0.20000.11600.00610.083*
O50.06988(13)0.4249(5)−0.16358(16)0.1065(12)
C60.07965(18)0.9213(5)0.19207(18)0.0758(12)
H6A0.08550.86120.23030.114*
H6B0.10930.98630.18370.114*
H6C0.05010.98880.19690.114*
N60.01729(12)0.6958(3)−0.40152(15)0.0626(8)
H6D0.04550.6882−0.37990.075*
H6E0.01780.6902−0.44210.075*
O60.10500(11)0.2749(4)−0.08837(13)0.0765(8)
H60.0760(11)0.291(6)−0.071(2)0.115*
C70.08630(14)0.6728(4)0.00641(18)0.0552(9)
H7A0.08730.59810.04160.066*
H7B0.07570.6134−0.03100.066*
N7−0.06954(12)0.7299(4)−0.40657(17)0.0736(9)
H7C−0.09840.7448−0.38820.088*
H7D−0.06850.7242−0.44720.088*
O70.01666(10)0.3090(3)−0.03477(12)0.0679(7)
C80.13982(16)0.7357(6)−0.0035(2)0.0802(12)
H8A0.13950.8089−0.03920.096*
H8B0.15090.79510.03370.096*
N8−0.02793(12)0.7246(4)−0.31044(15)0.0693(8)
H8C0.00010.7171−0.28850.083*
H8D−0.05680.7378−0.29180.083*
O8−0.02207(11)0.4235(4)−0.11735(14)0.0883(9)
H80.0089(10)0.427(7)−0.131(3)0.132*
C90.17736(18)0.6027(6)−0.0157(2)0.0919(14)
H9A0.21100.6470−0.02180.138*
H9B0.17830.53110.01990.138*
H9C0.16680.5449−0.05290.138*
O9−0.06723(12)0.3627(4)−0.03617(14)0.0941(10)
C100.04008(17)0.9141(4)−0.03604(17)0.0626(10)
H10A0.01580.9972−0.02460.075*
H10B0.07300.9655−0.04290.075*
O10−0.12304(10)0.2705(3)0.25737(12)0.0686(7)
C110.0222(2)0.8402(5)−0.09755(18)0.0844(13)
H11A0.04780.7645−0.11190.101*
H11B−0.00960.7820−0.09090.101*
O11−0.15950(10)0.3275(4)0.16466(13)0.0773(8)
C120.0135(3)0.9648(6)−0.1470(2)0.122(2)
H12A0.00220.9146−0.18560.183*
H12B−0.01221.0388−0.13310.183*
H12C0.04511.0214−0.15410.183*
O12−0.20531(9)0.3268(3)0.25178(11)0.0579(6)
H12−0.2299(12)0.353(5)0.2252(17)0.087*
C13−0.20440(14)1.0742(4)0.72163(15)0.0531(8)
H13A−0.17501.00650.71300.064*
H13B−0.23271.00460.73300.064*
C14−0.21912(16)1.1622(4)0.66153(16)0.0618(10)
H14A−0.25141.21820.66730.074*
H14B−0.19291.24100.65190.074*
C15−0.2245(2)1.0455(5)0.60743(19)0.0838(12)
H15A−0.23381.10240.56950.126*
H15B−0.19240.99120.60150.126*
H15C−0.25070.96840.61690.126*
C16−0.23471(14)1.2950(4)0.79196(17)0.0522(9)
H16A−0.22461.35990.82810.063*
H16B−0.23881.36650.75610.063*
C17−0.28614(15)1.2209(5)0.8053(2)0.0705(11)
H17A−0.28321.15150.84200.085*
H17B−0.29721.15620.76950.085*
C18−0.32542(18)1.3491(6)0.8174(2)0.0919(14)
H18A−0.35801.30030.82590.138*
H18B−0.31471.41210.85320.138*
H18C−0.32861.41680.78080.138*
C19−0.18125(16)1.0690(4)0.83360(16)0.0586(9)
H19A−0.21211.00640.84040.070*
H19B−0.15420.99480.82220.070*
C20−0.1660(2)1.1481(5)0.89538(19)0.0788(12)
H20A−0.13481.20980.88960.095*
H20B−0.19301.22120.90800.095*
C21−0.1572(2)1.0264(6)0.9462(2)0.1031(16)
H21A−0.14761.07950.98490.155*
H21B−0.18830.96640.95230.155*
H21C−0.13020.95500.93400.155*
C22−0.14388(14)1.2812(4)0.76450(18)0.0553(9)
H22A−0.15191.34930.72850.066*
H22B−0.13761.35070.80060.066*
C23−0.09506(16)1.1932(6)0.7510(3)0.0903(14)
H23A−0.10061.12080.71570.108*
H23B−0.08501.12980.78770.108*
C24−0.05293(18)1.3086(7)0.7357(2)0.0986(15)
H24A−0.02191.25030.72720.148*
H24B−0.06271.37020.69910.148*
H24C−0.04711.37910.77100.148*
C250.22351(14)−0.0254(4)0.12147(16)0.0519(8)
C260.10875(18)0.3516(5)−0.14343(19)0.0690(11)
C27−0.02480(17)0.3602(5)−0.05995(19)0.0620(10)
C28−0.16055(15)0.3076(4)0.22337(18)0.0542(9)
C290.24250(16)0.1467(4)−0.06488(18)0.0574(9)
C30−0.02670(14)0.7160(4)−0.37248(18)0.0544(9)

Source of material

1,2,4,5-tetrakis(4-carboxyphenyl)benzene and tetrapropylammonium hydroxide (30% aqueous solution) were dissolved in small amount of water/ethanol (v/v, 1:2) to yield clean solution with the participation of guanidine hydrochloride (A. R.). After vigorous stirring for an hour, the solution was set aside to generate colorless plate crystals of the title compound after about 2 weeks. The aromatic acid was not present in the obtained crystalline phase. It can be concluded that bicarbonate should be derived from carbon dioxide during the stirring process.

Experimental details

Hydrogen atoms cound to carbon and nitrogen atoms are introduced by a riding model. The coordinates of the hydrogen atoms at water molecules are refined freely. Uiso parameters are fixed for all hydrogen atoms.

Comment

A guanidinium cation is a perfect triangular potentially hydrogen-bonded motif due to its planar configuration and multiple –NH2 groups. Obviously, if another hydrogen-bond acceptor can be provided to cooperate with guanidine/guanidinium, it can generate interesting hydrogen bonding schemes. The bicarbonate is clearly a good choice to interact with guanidine/guanidinium, because it can be regarded as excellent hydrogen bond donor and acceptor. In the related crystal structures involving aromatic acids and tetraalkylammonium ions [4], [5], [6], [7], it can be found these two ions were often used to construct hydrogen-bonded frameworks, but the title compound and its structure has not been reported before.

In the asymmetric unit of the title compound, there are four independent bicarbonate ions, four water molecules, two guanidine ions and two tetrapropylammonium cations. Observing the structure, it can be found that each two bicarbonate ions firstly connect with each other to form the dimer by the intermolecular O—H⋯O interactions, then the dimers link with two guanidine ions and four water molecules to yield the three-dimensional framework with cavities by different O—H⋯O and N—H⋯O contacts. To obtain the stable crystal structure, those cavities are filled with tetrapropylammonium cations to form the close-packed structure. Apparently, although guanidine and bicarbonate are very simple molecules, they still can construct complicated hydrogen-bonded network with the suitable conditions. Bond lengths and angles in the ions are all in the expected ranges [8].

Acknowledgements

This work was financially supported by Natural Science Foundation of China (21601053, U1604185) and Scientific and Technological Brainstorm Project of Henan Province (182102410012).

References

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Received: 2018-04-09
Accepted: 2018-08-16
Published Online: 2018-09-08
Published in Print: 2018-11-27

©2018 Huahui Zeng et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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https://doi.org/10.1515/ncrs-2018-0142
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of di-μ2-aqua-tetraaqua-bis(4-(1H-1,2,4-triazol-1-yl)benzoato-κN)disodium(I) C18H24N6Na2O10
  3. Crystal structure of diaqua-bis(2-bromo-4-chloro-6-formylphenolato-κ2O,O′)cobalt(II), C16H16Cl2CrN3O7
  4. Crystal structure of catena-poly[(μ2-1-(4-(1H-pyrazol-1-yl)phenyl)ethan-1-one-κ2N:O)-bis(1,1,1-trifluoro-4-oxo-4-(thiophen-2-yl)but-2-en-2-olato-κ2O,O′)copper(II)], C27H18CuF6N2O5S2
  5. Crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C18H15F2NO5
  6. Crystal structure of 5,5′-dimethoxy-2,2′-[1,1′-(ethylenedioxydinitrilo)diethylidyne]diphenol, C20H24N2O6
  7. Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H14Cl2N2O2
  8. Crystal structure of 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine - trichloromethane (1/2), C98H84Cl6N8O8
  9. Crystal structure of methyl 2-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate, C24H21N3O5
  10. Crystal structure of catena-poly[(μ2-3,3′-thiodipropionato-κ2O:O′)-(bipyridine-κ2N,N′)copper(II)] C16H16CuN2O4S
  11. Crystal structure of [4-chloro-2-(((2-((3-ethoxy-2-oxidobenzylidene)amino)phenyl)imino)(phenyl)methyl)phenolato-κ4N,N′,O,O′}nickel(II) - ethyl acetate (1/1), C32H29ClN2NiO5
  12. Crystal structure of (4-(4-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C29H52Cl2N4NiO9
  13. Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C20H21NO5
  14. Structure and photochromism of 1,2-bis[2-methyl-5-(3-quinolyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C33H20F6N2S2
  15. Crystal structure of catena-poly[diaqua-bis(μ2-3,5-di(1H-1,2,4-triazol-1-yl)benzoate-κ2N:N′)cobalt(II))] 2.5 hydrate, C22H23CoN12O8.50
  16. The crystal structure of dichlorido(1,3-dimesityl-1H-3λ4-imidazol-2-yl)(morpholine-κN)palladium(IV), C25H33Cl2N3OPd
  17. Crystal structure of catena-poly[bis(4,4′-dipyridylaminium-kN)-(μ2-germanowolframato-κ2O:O′)-(2,2′-bipyridine-κ2N,N′)copper(II)] with a Keggin-type heteropolyoxoanion, [Cu(C10H8N2)(C10H10N3)2][GeW12O40] ⋅ H2O
  18. Crystal structure of diaqua-(N-(1-(pyrazin-2-yl)ethylidene)pyridin-1-ium-4-carbohydrazonate-κ3N,N′,O)-tris[nitrato-κ2O,O′)lanthanum(III), C12H15N8O12La
  19. The crystal structure of 2-hydroxy-4-((2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy)-3,6-dimethylbenzoic acid–methanol (1/1), C20H24O8
  20. Crystal structure of guanidinium tetrapropylammonium bis(hydrogencarbonate) dihydrate, C15H40N4O8
  21. Crystal structure of (Z)-2-bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-phenylprop-2-en-1-one, C23H27BrO2
  22. Crystal structure of 2-(4-(4H-1,2,4-triazol-4-yl)phenyl)acetic acid, C10H9N3O4
  23. Crystal structure of 4,4′-(1,4-phenylene)bis(1H-imidazol-3-ium)bis(2-carboxybenzoate), C30H26N4O8
  24. Crystal structure of 4,4′-(4,10-diphenyl-4,10-dihydropyreno[4,5-d:9,10-d′]diimidazole-5,11-diyl)bis(N,N-diphenylaniline), C66H44N6
  25. Crystal structure of catena-poly[diaqua-bis(μ2-5-(3-(1H-imidazol-5-yl)phenyl)tetrazol-2-ido-κ2N:N′)cobalt(II)], C20H18CoN12O2
  26. Crystal structure of 1,3-dimethyl-2-(p-tolyl)-1H-perimidin-3-ium iodide 1.5 hydrate, C20H22IN2O1.5
  27. Crystal structure of 2-(4-methoxyphenyl)chromane, C16H16O2
  28. Crystal structure of poly[(μ2-2-carboxy-5-nitroisophthalato-κ2O:O′)-(μ2-4-((1H-imidazol-1-yl)methyl)pyridine-κ2N:N′)zinc(II)], C18H12N4O8Zn
  29. Crystal structure of bis(1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)tetraiodidodicadmium(II), [Cd2(C13H15N5)2I4]
  30. Crystal structure of tetramethylammonium bis(acetato-κ1O)-tetrakis(μ3-3-((hydroxyimino)methyl)-5-methoxy-2-oxidobenzoate-κ5O,O′:O′,N:O′′)tetrazinc(II) — N,N′-dimethylformamide — water (1/2/2), C62H96Zn4N10O28
  31. Crystal structure of poly[(μ4-5-tert-butylisophthalato-κ4O:O′:O′′:O′′′)-(1,3-dimethyl-2-imidazolidinone-κO)zinc(II)] C17H22N2O5Zn
  32. Crystal structure of [tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′]-[(pyridine-2,6-dicarboxylato-κ2O,N)]cadmium(II)–methanol (1:3) C34H36CdN8O7
  33. The crystal structure of bis(1H-benzo[d]imidazol-2-amine-κN)-diiodidocadmium(II), C14H14CdI2N6
  34. Crystal structure of tetrakis(1H-benzimidazol-2-amine)-κN)-bis(μ2-sulfonato-κ2O:O′)dizinc(II) - methanol (1/1), C30H36N12O10S2Zn2
  35. Crystal structure of 3β-methoxy-20α-dimethylamino-pregn-5-ene, C24H41NO
  36. Crystal structure of dimethyl 4,4′-oxydibenzoate, C16H14O5
  37. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-3-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)zinc(II)], C17H16I2N4OZn
  38. Crystal structure of 4-((E)-((E)-5-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-4-oxopiperidin-3-ylidene)methyl)benzonitrile, C26H18F2N2O3S
  39. Crystal structure of bis(acetato-κ1O)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)zinc(II), C18H22N4O6Zn
  40. The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br
  41. Crystal stucture of 2-(tert-butyl)-6-(hydroxymethyl)-4-methylphenol, C12H18O2
  42. Crystal structure of catena-poly[(2-(5-chloroquinolin-8-yloxy)-1-(pyrrolidin-1-yl)ethan-1-one-κ3N,O,O′)-(dinitrato-κ2O,O′)mercury(II)], C15H15N4O8ClHg
  43. Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
  44. The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4
  45. Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
  46. The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
  47. Crystal structure of 5-bromo-7-chloro-3,3a-dihydrocyclopenta[b]chromen-1(2H)-one, C12H8BrClO2
  48. Crystal structure of 2-(bis(4-fluorophenyl)methylene)hydrazine-1-carbothioamide, C14H11F2N3S
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