Bis[dieth­yl(hy­droxy)ammonium] benzene-1,4-dicarboxyl­ate

Xie, D.-M.; Chen, C.-X.; Chen, H.-X.; Wang, H.-B.

doi:10.1107/S1600536810027868

organic compounds

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Volume 66| Part 8| August 2010| Page o2074

https://doi.org/10.1107/S1600536810027868

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Bis[diethyl(hydroxy)ammonium] benzene-1,4-dicarboxylate

De-Ming Xie,^a Chun-Xiao Chen,^a Hai-Xiang Chen ^b ^* and Hai-Bin Wang ^c

^aResearch Institute of Materials and Surface Engineering, School of Mechnical Engineering, Zhejiang University of Technology, Hangzhou 310032, People's Republic of China, ^bAnalytical Center, Zhejiang Sci-Tech University, Hangzhou 310018, People's Republic of China, and ^cCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310018, People's Republic of China
^*Correspondence e-mail: cchhyy@sina.cn

(Received 18 March 2010; accepted 13 July 2010; online 21 July 2010)

In the centrosymmetric title compound, 2C₄H₁₂NO⁺·C₈H₄O₄²⁻, two N,N-diethyl(hydroxy)ammonium cations are linked to a benzene-1,4-dicarboxylate dianion by a combination of O—H⋯O and N—H⋯O hydrogen bonds, which can be described in graph-set terminology as R₂²(7). The crystal structure is further stabilized by C—H⋯O hydrogen bonds, leading to the fomation of a ribbon-like network.

Related literature

For similar supamolecular structures involving benzenedicarboxylic acids, see: Chatterjee et al. (2000 ); Herbstein & Kapon (1978 ); Karpova et al. (2004 ); Mak & Xue (2000 ); Yuge et al. (2006 ); Zhao et al. (2007 ). For graph-set theory, see: Bernstein et al. (1995 ).

Experimental

Crystal data

2C₄H₁₂NO⁺·C₈H₄O₄²⁻
M_r = 344.40
Monoclinic, P 2₁ /c
a = 6.507 (2) Å
b = 11.478 (4) Å
c = 12.649 (5) Å
β = 97.380 (7)°
V = 936.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 273 K
0.37 × 0.31 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.954, T_max = 0.969
4737 measured reflections
1653 independent reflections
1460 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.087
wR(F²) = 0.220
S = 1.13
1653 reflections
112 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.78	2.576 (5)	164
N1—H1⋯O1	0.91	1.72	2.605 (5)	164
C7—H7b⋯O2ⁱ	0.97	2.42	3.327 (5)	156
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810027868/su2169sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027868/su2169Isup2.hkl

checkCIF report

Comment top

Supramolecular aggregate design is an active field of research and in a series of papers various supramolecular structures comprising benzene-dicarboxylic acids have been elucidated (Herbstein et al., 1978; Chatterjee et al., 2000; Karpova et al., 2004; Zhao et al., 2007). Some cases have been reported where the use of terephthalic acid has lead to the fomation of supramolecular architectures through hydrogen bonding (Mak et al., 2000; Yuge et al., 2006). The title compound was synthesized by the reaction of terephthalic acid with N,N-diethylhydroxylammine.

As shown in Fig. 1 two N,N-diethylhydroxylammonium (DTHA) cations are linked to the benzene-1,4-dicarboxylate anion (BDL), which is situated about an inversion center, by a special combination of O—H···O and N—H···O hydrogen bonds (Table 1), N1—H1···O1 and O3—H3···O2, which can be described by graph-set R²₂(7) [Bernstein, et al., 1995].

In the BDL anion the dihedral angle between phenyl ring and carboxylate group is 11.3 (3)/%. In general the BDLanion is almost coplanar with the mean plane through the C and N-atoms in the DTHA cations. The carboxylate groups are nearly perpendicular with the mean plane through the C and N-atoms of DTHA [dihedral angle of 81.0 (3)/%].

In the crystal structure a ribbon-like structure (Fig. 2 and Table 1), is fomed via C7—H7···O2ⁱ interactions [symmetry code (i) = 1 + x, y, z] .

Related literature top

For similar supamolecular structures involving benzenedicarboxylic acids, see: Chatterjee et al. (2000); Herbstein & Kapon (1978); Karpova et al. (2004); Mak & Xue (2000); Yuge et al. (2006); Zhao et al. (2007). For graph-set theory, see: Bernstein et al. (1995).

Experimental top

N,N-diethylhydroxylammine and terephthalic acid, in a molar ratio of 2:1, were mixed and dissolved in sufficient ethanol that by heating to 353 K a clear solution was obtained. The reaction system was then cooled slowly to RT, and crystals of the title compound were formed. They were collected and washed with ethanol.

Structure description top

In the crystal structure a ribbon-like structure (Fig. 2 and Table 1), is fomed via C7—H7···O2ⁱ interactions [symmetry code (i) = 1 + x, y, z] .

For similar supamolecular structures involving benzenedicarboxylic acids, see: Chatterjee et al. (2000); Herbstein & Kapon (1978); Karpova et al. (2004); Mak & Xue (2000); Yuge et al. (2006); Zhao et al. (2007). For graph-set theory, see: Bernstein et al. (1995).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of the title compound [The O—H···O and N—H···O hydrogen bonds are illustrated by dotted lines].
	Fig. 2. A perspective view, along the c-axis, of the crystal packing of the title compound [The O—H···O and N—H···O hydrogen bonds nd the C-H···O interactions are illustrated by dotted lines; the symmetry code for the atom labeled O2^' is = x+1, y, z].

Bis[diethyl(hydroxy)ammonium] benzene-1,4-dicarboxylate top

Crystal data top

2C₄H₁₂NO⁺·C₈H₄O₄²⁻	F(000) = 372.0
M_r = 344.40	D_x = 1.221 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2185 reflections
a = 6.507 (2) Å	θ = 2.1–25.0°
b = 11.478 (4) Å	µ = 0.09 mm⁻¹
c = 12.649 (5) Å	T = 273 K
β = 97.380 (7)°	Block, colorless
V = 936.9 (6) Å³	0.37 × 0.31 × 0.27 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	1653 independent reflections
Radiation source: fine-focus sealed tube	1460 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
phi and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −7→7
T_min = 0.954, T_max = 0.969	k = −10→13
4737 measured reflections	l = −14→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.220	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0871P)² + 0.9891P] where P = (F_o² + 2F_c²)/3
1653 reflections	(Δ/σ)_max < 0.001
112 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

2C₄H₁₂NO⁺·C₈H₄O₄²⁻	V = 936.9 (6) Å³
M_r = 344.40	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.507 (2) Å	µ = 0.09 mm⁻¹
b = 11.478 (4) Å	T = 273 K
c = 12.649 (5) Å	0.37 × 0.31 × 0.27 mm
β = 97.380 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1653 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1460 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.969	R_int = 0.023
4737 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.087	0 restraints
wR(F²) = 0.220	H-atom parameters constrained
S = 1.13	Δρ_max = 0.66 e Å⁻³
1653 reflections	Δρ_min = −0.27 e Å⁻³
112 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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

	x	y	z	U_iso*/U_eq
O1	0.4427 (3)	0.3065 (2)	0.0657 (2)	0.0636 (8)
O2	0.1752 (4)	0.2241 (2)	0.1261 (2)	0.0682 (8)
C1	0.2564 (5)	0.3044 (3)	0.0788 (3)	0.0482 (8)
C2	0.1228 (4)	0.4052 (3)	0.0370 (2)	0.0423 (8)
C3	−0.0744 (5)	0.4198 (3)	0.0657 (3)	0.0476 (8)
H3A	−0.1258	0.3653	0.1100	0.057*
C4	0.1945 (5)	0.4869 (3)	−0.0298 (3)	0.0469 (8)
H4	0.3257	0.4784	−0.0505	0.056*
O3	0.4471 (5)	0.0641 (2)	0.1778 (3)	0.0851 (10)
H3	0.3444	0.1052	0.1629	0.128*
N1	0.6262 (5)	0.1284 (3)	0.1645 (2)	0.0573 (8)
H1	0.5847	0.1967	0.1320	0.069*
C5	0.6600 (11)	0.2447 (5)	0.3266 (4)	0.110 (2)
H5A	0.6382	0.3143	0.2846	0.164*
H5B	0.7486	0.2617	0.3914	0.164*
H5C	0.5292	0.2162	0.3433	0.164*
C6	0.7561 (8)	0.1574 (4)	0.2672 (3)	0.0784 (13)
H6A	0.7786	0.0874	0.3101	0.094*
H6B	0.8901	0.1855	0.2525	0.094*
C7	0.7465 (6)	0.0633 (4)	0.0917 (3)	0.0660 (11)
H7A	0.6599	0.0520	0.0241	0.079*
H7B	0.8644	0.1102	0.0783	0.079*
C8	0.8225 (8)	−0.0519 (4)	0.1328 (4)	0.0938 (16)
H8A	0.9352	−0.0411	0.1888	0.141*
H8B	0.8694	−0.0961	0.0761	0.141*
H8C	0.7121	−0.0930	0.1601	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0377 (13)	0.0655 (17)	0.0879 (19)	0.0015 (11)	0.0087 (12)	0.0270 (14)
O2	0.0510 (15)	0.0536 (15)	0.103 (2)	−0.0012 (12)	0.0227 (14)	0.0214 (15)
C1	0.0434 (19)	0.0489 (19)	0.0519 (19)	−0.0079 (15)	0.0049 (14)	−0.0012 (15)
C2	0.0377 (16)	0.0466 (18)	0.0418 (16)	−0.0111 (13)	0.0013 (13)	−0.0047 (14)
C3	0.0415 (17)	0.053 (2)	0.0490 (18)	−0.0096 (15)	0.0093 (14)	0.0067 (15)
C4	0.0342 (16)	0.058 (2)	0.0500 (18)	−0.0045 (14)	0.0094 (13)	0.0012 (16)
O3	0.0704 (18)	0.0558 (17)	0.137 (3)	0.0022 (14)	0.0415 (19)	0.0251 (18)
N1	0.0621 (18)	0.0444 (16)	0.0636 (19)	−0.0028 (14)	0.0010 (15)	0.0095 (14)
C5	0.167 (6)	0.094 (4)	0.070 (3)	0.034 (4)	0.024 (3)	−0.002 (3)
C6	0.100 (3)	0.071 (3)	0.062 (2)	0.019 (2)	0.004 (2)	0.010 (2)
C7	0.058 (2)	0.072 (3)	0.066 (2)	−0.0090 (19)	0.0050 (18)	0.002 (2)
C8	0.100 (4)	0.073 (3)	0.111 (4)	0.015 (3)	0.020 (3)	−0.006 (3)

Geometric parameters (Å, º) top

O1—C1	1.245 (4)	N1—H1	0.9100
O2—C1	1.252 (4)	C5—C6	1.442 (6)
C1—C2	1.502 (5)	C5—H5A	0.9600
C2—C4	1.384 (4)	C5—H5B	0.9600
C2—C3	1.388 (4)	C5—H5C	0.9600
C3—C4ⁱ	1.368 (5)	C6—H6A	0.9700
C3—H3A	0.9300	C6—H6B	0.9700
C4—C3ⁱ	1.368 (5)	C7—C8	1.481 (6)
C4—H4	0.9300	C7—H7A	0.9700
O3—N1	1.408 (4)	C7—H7B	0.9700
O3—H3	0.8200	C8—H8A	0.9600
N1—C7	1.484 (5)	C8—H8B	0.9600
N1—C6	1.494 (5)	C8—H8C	0.9600

O1—C1—O2	123.8 (3)	C6—C5—H5C	109.5
O1—C1—C2	117.9 (3)	H5A—C5—H5C	109.5
O2—C1—C2	118.3 (3)	H5B—C5—H5C	109.5
C4—C2—C3	118.3 (3)	C5—C6—N1	111.9 (4)
C4—C2—C1	120.8 (3)	C5—C6—H6A	109.2
C3—C2—C1	120.9 (3)	N1—C6—H6A	109.2
C4ⁱ—C3—C2	121.0 (3)	C5—C6—H6B	109.2
C4ⁱ—C3—H3A	119.5	N1—C6—H6B	109.2
C2—C3—H3A	119.5	H6A—C6—H6B	107.9
C3ⁱ—C4—C2	120.7 (3)	C8—C7—N1	114.3 (4)
C3ⁱ—C4—H4	119.7	C8—C7—H7A	108.7
C2—C4—H4	119.7	N1—C7—H7A	108.7
N1—O3—H3	109.5	C8—C7—H7B	108.7
O3—N1—C7	108.7 (3)	N1—C7—H7B	108.7
O3—N1—C6	113.4 (3)	H7A—C7—H7B	107.6
C7—N1—C6	111.6 (3)	C7—C8—H8A	109.5
O3—N1—H1	107.7	C7—C8—H8B	109.5
C7—N1—H1	107.7	H8A—C8—H8B	109.5
C6—N1—H1	107.7	C7—C8—H8C	109.5
C6—C5—H5A	109.5	H8A—C8—H8C	109.5
C6—C5—H5B	109.5	H8B—C8—H8C	109.5
H5A—C5—H5B	109.5

O1—C1—C2—C4	11.2 (5)	C3—C2—C4—C3ⁱ	0.6 (5)
O2—C1—C2—C4	−169.9 (3)	C1—C2—C4—C3ⁱ	−178.4 (3)
O1—C1—C2—C3	−167.8 (3)	O3—N1—C6—C5	−71.7 (5)
O2—C1—C2—C3	11.1 (5)	C7—N1—C6—C5	165.2 (4)
C4—C2—C3—C4ⁱ	−0.6 (5)	O3—N1—C7—C8	−62.6 (4)
C1—C2—C3—C4ⁱ	178.4 (3)	C6—N1—C7—C8	63.1 (5)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.78	2.576 (5)	164
N1—H1···O1	0.91	1.72	2.605 (5)	164
C7—H7b···O2ⁱⁱ	0.97	2.42	3.327 (5)	156

Symmetry code: (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	2C₄H₁₂NO⁺·C₈H₄O₄²⁻
M_r	344.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	6.507 (2), 11.478 (4), 12.649 (5)
β (°)	97.380 (7)
V (Å³)	936.9 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.37 × 0.31 × 0.27

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.954, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	4737, 1653, 1460
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.087, 0.220, 1.13
No. of reflections	1653
No. of parameters	112
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.27

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.78	2.576 (5)	164
N1—H1···O1	0.91	1.72	2.605 (5)	164
C7—H7b···O2ⁱ	0.97	2.42	3.327 (5)	156

Symmetry code: (i) x+1, y, z.

References

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2074

https://doi.org/10.1107/S1600536810027868

Open

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