Bis(2-hy­droxy­ethanaminium) biphenyl-4,4′-dicarboxyl­ate

Deng, B.; Yu, R.-J.

doi:10.1107/S1600536811013523

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1337

doi:10.1107/S1600536811013523

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Bis(2-hydroxyethanaminium) biphenyl-4,4′-dicarboxylate

Bin Deng ^a and Rui-Jin Yu ^b ^*

^aDepartment of Chemistry and Life Sciences, Xiangnan University, Chenzhou 423000, People's Republic of China, and ^bCollege of Science, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China
^*Correspondence e-mail: gzxian2010@yahoo.cn

(Received 25 March 2011; accepted 11 April 2011; online 7 May 2011)

In the title compound, 2C₂H₈NO⁺·C₁₄H₈O₄²⁻, the dihedral angle between the benzene rings of the dianion is 9.95 (12)°. In the crystal, the cations and anions are linked via intermolecular O—H⋯O and N—H⋯O hydrogen bonds, generating layers lying parallel to (001).

Related literature

For backround to organic salts, see: Holman et al. (2001 ); Plaut et al. (2000 ); Russell et al. (1997 ). For hydrogen-bond networks in related compounds, see; Ranganathan et al., (1999 ); Swift et al. (1998 ); Zhang & Chen (2005 ); Bhogala & Nangia (2003 ). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

2C₂H₈NO⁺·C₁₄H₈O₄²⁻
M_r = 364.39
Orthorhombic, P b c a
a = 7.3410 (7) Å
b = 12.4094 (13) Å
c = 38.074 (4) Å
V = 3468.5 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.30 × 0.27 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.969, T_max = 0.981
14999 measured reflections
3380 independent reflections
2606 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.173
S = 1.08
3380 reflections
267 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5O⋯O1	0.87 (4)	1.94 (4)	2.793 (3)	165 (4)
N1—H1A⋯O2	0.96 (4)	1.76 (4)	2.704 (3)	169 (3)
N1—H1B⋯O3ⁱ	0.94 (4)	1.87 (4)	2.807 (3)	180 (4)
N1—H1C⋯O1ⁱⁱ	0.90 (4)	2.09 (4)	2.892 (3)	149 (3)
O6—H6O⋯O4	0.92 (4)	1.89 (4)	2.778 (3)	164 (4)
N2—H2A⋯O3	0.95 (3)	1.82 (4)	2.759 (3)	170 (3)
N2—H2B⋯O4ⁱⁱⁱ	0.95 (4)	2.00 (4)	2.854 (3)	149 (3)
N2—H2C⋯O1^iv	0.95 (4)	1.91 (4)	2.866 (3)	174 (4)
Symmetry codes: (i) -x, -y, -z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); 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 I, global. DOI: 10.1107/S1600536811013523/lh5226sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013523/lh5226Isup2.hkl

checkCIF report

Comment top

Organic crystals built from acid-base complexes have received much attention in the predictable assembly of supramolecular architectures (Holman et al., 2001; Plaut et al., 2000; Russell et al., 1997). One of the most important applications, is the use of self-assembly of small molecules with O—H···O, N—H···O and other weaker intermolecular interactions to create one-, two- and three-dimensional networks (Ranganathan et al., 1999; Swift et al., 1998; Zhang et al., 2005). Aromatic acids have attracted our interest because of their importance in crystal engineering and they can form strong directional hydrogen bonds (Bhogala & Nangia, 2003). It is known that ethanolamine (ED) is a good organic base and has hydrogen-bond donor sites. Therefore, combinations of 4,4'-dicarboxyl-biphenyl(BDB) with ethanolamine molecules may be expected to display an interesting network. Herein, we report the crystal structure of the title organic salt (I).

The asymmetric unit of (I) is composed of two independent ED+ cations and one BDB^2- dianion (Fig. 1). The protons of two carboxyl groups from BDB are transferred to the amido groups of ED. The dihedral angle between the two benzene rings of the BDB^2- dianion is 9.95 (12) °. In the crystal, dianions and cations are linked via intermolecular O—H···O and N—H···O hydrogen bonds to form a two-dimensional network parallel to (001) which includes R²₂(9) rings (Bernstein et al., 1995).

Related literature top

For backround to organic salts, see: Holman et al. (2001); Plaut et al. (2000); Russell et al. (1997). For hydrogen-bond networks in related compounds, see; Ranganathan et al., (1999); Swift et al. (1998); Zhang & Chen (2005); Bhogala & Nangia (2003). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995).

Experimental top

BDB (0.024 g, 0.01 mmol) and ED (0.012 g, 0.02 mol) were dissolved in hot EtOH/H₂O (1:1) solution (20 mL). The solution was allowed to cool to room temperature and was evaporated in air for 4 days to give colorless crystals of the title compound (yield: 23%).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure showing a two-dimensional hydrogen-bonded (dashed lines) layer parallel to (001).

Bis(2-hydroxyethanaminium) biphenyl-4,4'-dicarboxylate top

Crystal data top

2C₂H₈NO⁺·C₁₄H₈O₄²⁻	F(000) = 1552
M_r = 364.39	D_x = 1.396 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3380 reflections
a = 7.3410 (7) Å	θ = 2.1–26.0°
b = 12.4094 (13) Å	µ = 0.11 mm⁻¹
c = 38.074 (4) Å	T = 293 K
V = 3468.5 (6) Å³	Block, colorless
Z = 8	0.30 × 0.27 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	3380 independent reflections
Radiation source: fine-focus sealed tube	2606 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
T_min = 0.969, T_max = 0.981	k = −15→14
14999 measured reflections	l = −27→46

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0845P)² + 1.5997P] where P = (F_o² + 2F_c²)/3
3380 reflections	(Δ/σ)_max < 0.001
267 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

2C₂H₈NO⁺·C₁₄H₈O₄²⁻	V = 3468.5 (6) Å³
M_r = 364.39	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.3410 (7) Å	µ = 0.11 mm⁻¹
b = 12.4094 (13) Å	T = 293 K
c = 38.074 (4) Å	0.30 × 0.27 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	3380 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2606 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.981	R_int = 0.044
14999 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.47 e Å⁻³
3380 reflections	Δρ_min = −0.18 e Å⁻³
267 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.0874 (3)	−0.00499 (14)	−0.14379 (4)	0.0385 (5)
O2	0.3194 (3)	−0.10392 (16)	−0.12492 (5)	0.0489 (6)
O3	0.0498 (3)	0.35559 (14)	0.13128 (5)	0.0377 (5)
O4	0.2920 (3)	0.25707 (14)	0.14555 (4)	0.0384 (5)
C1	0.1729 (3)	0.00670 (18)	−0.08337 (6)	0.0264 (5)
C2	0.2609 (4)	−0.0429 (2)	−0.05568 (6)	0.0319 (6)
H2	0.3272	−0.1056	−0.0597	0.038*
C3	0.2524 (3)	−0.0012 (2)	−0.02219 (6)	0.0310 (6)
H3	0.3124	−0.0365	−0.0040	0.037*
C4	0.1558 (3)	0.09265 (18)	−0.01495 (6)	0.0240 (5)
C5	0.0640 (4)	0.1404 (2)	−0.04283 (6)	0.0337 (6)
H5	−0.0037	0.2026	−0.0389	0.040*
C6	0.0711 (4)	0.0977 (2)	−0.07628 (6)	0.0339 (6)
H6	0.0063	0.1307	−0.0943	0.041*
C7	0.1556 (3)	0.14109 (18)	0.02092 (6)	0.0256 (5)
C8	0.2715 (4)	0.1027 (2)	0.04696 (6)	0.0329 (6)
H8	0.3465	0.0441	0.0421	0.039*
C9	0.2776 (4)	0.1497 (2)	0.07989 (6)	0.0324 (6)
H9	0.3594	0.1239	0.0965	0.039*
C10	0.1640 (3)	0.23463 (18)	0.08846 (6)	0.0263 (5)
C11	0.0479 (4)	0.2731 (2)	0.06293 (7)	0.0362 (6)
H11	−0.0299	0.3300	0.0681	0.043*
C12	0.0455 (4)	0.2282 (2)	0.02960 (7)	0.0374 (7)
H12	−0.0316	0.2571	0.0127	0.045*
C13	0.1935 (4)	−0.03813 (19)	−0.11985 (6)	0.0311 (6)
C14	0.1693 (3)	0.28548 (19)	0.12432 (6)	0.0290 (6)
O5	0.2304 (3)	−0.09198 (17)	−0.20556 (6)	0.0521 (6)
H5O	0.206 (5)	−0.066 (3)	−0.1849 (10)	0.081 (13)*
C15	0.1517 (5)	−0.1945 (2)	−0.21076 (8)	0.0503 (8)
H15A	0.1241	−0.2034	−0.2355	0.060*
H15B	0.0378	−0.1982	−0.1979	0.060*
C16	0.2713 (5)	−0.2841 (2)	−0.19924 (7)	0.0480 (8)
H16A	0.2242	−0.3515	−0.2084	0.058*
H16B	0.3923	−0.2735	−0.2089	0.058*
N1	0.2835 (4)	−0.2910 (2)	−0.16066 (6)	0.0386 (6)
H1A	0.310 (4)	−0.224 (3)	−0.1494 (9)	0.059 (10)*
H1B	0.172 (5)	−0.313 (3)	−0.1509 (9)	0.056 (10)*
H1C	0.362 (5)	−0.342 (3)	−0.1539 (9)	0.059 (10)*
O6	0.2281 (4)	0.34359 (17)	0.21172 (6)	0.0619 (7)
H6O	0.267 (6)	0.324 (3)	0.1898 (11)	0.092 (14)*
C17	0.3001 (5)	0.4453 (2)	0.21715 (8)	0.0549 (9)
H17A	0.4237	0.4461	0.2082	0.066*
H17B	0.3067	0.4580	0.2423	0.066*
C18	0.1995 (4)	0.5355 (2)	0.20099 (7)	0.0406 (7)
H18A	0.2489	0.6032	0.2095	0.049*
H18B	0.0726	0.5319	0.2080	0.049*
N2	0.2115 (4)	0.5327 (2)	0.16204 (6)	0.0379 (6)
H2A	0.145 (4)	0.473 (3)	0.1534 (8)	0.059 (9)*
H2B	0.168 (5)	0.600 (3)	0.1536 (9)	0.070 (11)*
H2C	0.336 (6)	0.527 (3)	0.1547 (10)	0.084 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0438 (11)	0.0429 (11)	0.0287 (10)	0.0014 (9)	−0.0091 (9)	−0.0037 (7)
O2	0.0548 (13)	0.0513 (12)	0.0405 (11)	0.0195 (11)	−0.0082 (10)	−0.0194 (9)
O3	0.0385 (11)	0.0364 (10)	0.0383 (10)	0.0059 (9)	0.0008 (8)	−0.0135 (8)
O4	0.0477 (12)	0.0380 (10)	0.0294 (9)	0.0072 (9)	−0.0068 (8)	−0.0062 (7)
C1	0.0265 (13)	0.0271 (12)	0.0257 (12)	−0.0037 (10)	−0.0016 (10)	−0.0020 (9)
C2	0.0346 (14)	0.0258 (12)	0.0353 (14)	0.0048 (11)	−0.0031 (11)	−0.0032 (10)
C3	0.0348 (14)	0.0314 (13)	0.0267 (12)	0.0051 (11)	−0.0069 (11)	0.0004 (10)
C4	0.0216 (12)	0.0245 (12)	0.0258 (12)	−0.0041 (10)	0.0017 (9)	−0.0005 (9)
C5	0.0357 (15)	0.0326 (13)	0.0329 (14)	0.0107 (12)	−0.0011 (11)	−0.0033 (10)
C6	0.0370 (15)	0.0385 (14)	0.0262 (13)	0.0105 (12)	−0.0057 (11)	0.0009 (10)
C7	0.0240 (13)	0.0253 (12)	0.0277 (13)	−0.0019 (10)	0.0008 (10)	−0.0018 (9)
C8	0.0359 (15)	0.0332 (14)	0.0295 (13)	0.0116 (12)	0.0010 (11)	−0.0027 (10)
C9	0.0363 (15)	0.0376 (14)	0.0234 (12)	0.0064 (12)	−0.0019 (11)	0.0001 (10)
C10	0.0268 (13)	0.0259 (12)	0.0263 (12)	−0.0035 (10)	0.0032 (10)	−0.0023 (9)
C11	0.0393 (16)	0.0327 (14)	0.0367 (14)	0.0104 (12)	−0.0026 (12)	−0.0099 (11)
C12	0.0406 (16)	0.0403 (15)	0.0312 (14)	0.0124 (13)	−0.0116 (12)	−0.0052 (11)
C13	0.0352 (15)	0.0264 (12)	0.0317 (13)	−0.0035 (11)	−0.0037 (11)	−0.0039 (10)
C14	0.0327 (14)	0.0250 (12)	0.0293 (13)	−0.0057 (11)	0.0042 (11)	−0.0024 (10)
O5	0.0747 (16)	0.0416 (12)	0.0399 (12)	−0.0011 (11)	0.0125 (11)	0.0027 (9)
C15	0.062 (2)	0.0510 (19)	0.0379 (16)	0.0007 (16)	−0.0091 (15)	−0.0050 (13)
C16	0.062 (2)	0.0407 (16)	0.0413 (16)	0.0055 (15)	0.0064 (15)	−0.0114 (12)
N1	0.0397 (15)	0.0317 (13)	0.0445 (14)	0.0062 (12)	0.0061 (12)	−0.0016 (11)
O6	0.108 (2)	0.0403 (12)	0.0376 (12)	−0.0153 (13)	0.0034 (13)	0.0029 (9)
C17	0.082 (3)	0.0512 (19)	0.0319 (15)	−0.0059 (18)	−0.0003 (16)	−0.0017 (13)
C18	0.0464 (18)	0.0347 (15)	0.0407 (15)	−0.0025 (13)	0.0095 (13)	−0.0067 (11)
N2	0.0474 (16)	0.0274 (12)	0.0389 (13)	0.0002 (11)	0.0018 (12)	0.0014 (10)

Geometric parameters (Å, º) top

O1—C13	1.268 (3)	C11—H11	0.9300
O2—C13	1.248 (3)	C12—H12	0.9300
O3—C14	1.264 (3)	O5—C15	1.411 (4)
O4—C14	1.261 (3)	O5—H5O	0.87 (4)
C1—C6	1.381 (3)	C15—C16	1.483 (4)
C1—C2	1.381 (3)	C15—H15A	0.9700
C1—C13	1.504 (3)	C15—H15B	0.9700
C2—C3	1.378 (3)	C16—N1	1.474 (4)
C2—H2	0.9300	C16—H16A	0.9700
C3—C4	1.391 (3)	C16—H16B	0.9700
C3—H3	0.9300	N1—H1A	0.96 (4)
C4—C5	1.390 (3)	N1—H1B	0.94 (4)
C4—C7	1.492 (3)	N1—H1C	0.90 (4)
C5—C6	1.381 (3)	O6—C17	1.384 (4)
C5—H5	0.9300	O6—H6O	0.92 (4)
C6—H6	0.9300	C17—C18	1.475 (4)
C7—C12	1.390 (3)	C17—H17A	0.9700
C7—C8	1.391 (3)	C17—H17B	0.9700
C8—C9	1.384 (3)	C18—N2	1.486 (4)
C8—H8	0.9300	C18—H18A	0.9700
C9—C10	1.383 (3)	C18—H18B	0.9700
C9—H9	0.9300	N2—H2A	0.95 (3)
C10—C11	1.378 (3)	N2—H2B	0.95 (4)
C10—C14	1.505 (3)	N2—H2C	0.95 (4)
C11—C12	1.386 (3)

C6—C1—C2	117.9 (2)	O4—C14—C10	118.9 (2)
C6—C1—C13	122.5 (2)	O3—C14—C10	117.5 (2)
C2—C1—C13	119.5 (2)	C15—O5—H5O	112 (3)
C3—C2—C1	121.2 (2)	O5—C15—C16	113.1 (3)
C3—C2—H2	119.4	O5—C15—H15A	109.0
C1—C2—H2	119.4	C16—C15—H15A	109.0
C2—C3—C4	121.4 (2)	O5—C15—H15B	109.0
C2—C3—H3	119.3	C16—C15—H15B	109.0
C4—C3—H3	119.3	H15A—C15—H15B	107.8
C5—C4—C3	116.9 (2)	N1—C16—C15	112.0 (2)
C5—C4—C7	121.8 (2)	N1—C16—H16A	109.2
C3—C4—C7	121.3 (2)	C15—C16—H16A	109.2
C6—C5—C4	121.5 (2)	N1—C16—H16B	109.2
C6—C5—H5	119.3	C15—C16—H16B	109.2
C4—C5—H5	119.3	H16A—C16—H16B	107.9
C1—C6—C5	121.0 (2)	C16—N1—H1A	114 (2)
C1—C6—H6	119.5	C16—N1—H1B	111 (2)
C5—C6—H6	119.5	H1A—N1—H1B	105 (3)
C12—C7—C8	116.9 (2)	C16—N1—H1C	111 (2)
C12—C7—C4	122.1 (2)	H1A—N1—H1C	111 (3)
C8—C7—C4	120.9 (2)	H1B—N1—H1C	104 (3)
C9—C8—C7	121.4 (2)	C17—O6—H6O	105 (3)
C9—C8—H8	119.3	O6—C17—C18	116.0 (3)
C7—C8—H8	119.3	O6—C17—H17A	108.3
C10—C9—C8	121.0 (2)	C18—C17—H17A	108.3
C10—C9—H9	119.5	O6—C17—H17B	108.3
C8—C9—H9	119.5	C18—C17—H17B	108.3
C11—C10—C9	118.1 (2)	H17A—C17—H17B	107.4
C11—C10—C14	120.7 (2)	C17—C18—N2	111.6 (2)
C9—C10—C14	121.2 (2)	C17—C18—H18A	109.3
C10—C11—C12	121.0 (2)	N2—C18—H18A	109.3
C10—C11—H11	119.5	C17—C18—H18B	109.3
C12—C11—H11	119.5	N2—C18—H18B	109.3
C11—C12—C7	121.5 (2)	H18A—C18—H18B	108.0
C11—C12—H12	119.2	C18—N2—H2A	109 (2)
C7—C12—H12	119.2	C18—N2—H2B	107 (2)
O2—C13—O1	123.8 (2)	H2A—N2—H2B	113 (3)
O2—C13—C1	117.3 (2)	C18—N2—H2C	110 (2)
O1—C13—C1	118.8 (2)	H2A—N2—H2C	109 (3)
O4—C14—O3	123.6 (2)	H2B—N2—H2C	107 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5O···O1	0.87 (4)	1.94 (4)	2.793 (3)	165 (4)
N1—H1A···O2	0.96 (4)	1.76 (4)	2.704 (3)	169 (3)
N1—H1B···O3ⁱ	0.94 (4)	1.87 (4)	2.807 (3)	180 (4)
N1—H1C···O1ⁱⁱ	0.90 (4)	2.09 (4)	2.892 (3)	149 (3)
O6—H6O···O4	0.92 (4)	1.89 (4)	2.778 (3)	164 (4)
N2—H2A···O3	0.95 (3)	1.82 (4)	2.759 (3)	170 (3)
N2—H2B···O4ⁱⁱⁱ	0.95 (4)	2.00 (4)	2.854 (3)	149 (3)
N2—H2C···O1^iv	0.95 (4)	1.91 (4)	2.866 (3)	174 (4)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1/2, y−1/2, z; (iii) −x+1/2, y+1/2, z; (iv) x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	2C₂H₈NO⁺·C₁₄H₈O₄²⁻
M_r	364.39
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	7.3410 (7), 12.4094 (13), 38.074 (4)
V (Å³)	3468.5 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.27 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.969, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	14999, 3380, 2606
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.173, 1.08
No. of reflections	3380
No. of parameters	267
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.18

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), 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
O5—H5O···O1	0.87 (4)	1.94 (4)	2.793 (3)	165 (4)
N1—H1A···O2	0.96 (4)	1.76 (4)	2.704 (3)	169 (3)
N1—H1B···O3ⁱ	0.94 (4)	1.87 (4)	2.807 (3)	180 (4)
N1—H1C···O1ⁱⁱ	0.90 (4)	2.09 (4)	2.892 (3)	149 (3)
O6—H6O···O4	0.92 (4)	1.89 (4)	2.778 (3)	164 (4)
N2—H2A···O3	0.95 (3)	1.82 (4)	2.759 (3)	170 (3)
N2—H2B···O4ⁱⁱⁱ	0.95 (4)	2.00 (4)	2.854 (3)	149 (3)
N2—H2C···O1^iv	0.95 (4)	1.91 (4)	2.866 (3)	174 (4)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1/2, y−1/2, z; (iii) −x+1/2, y+1/2, z; (iv) x+1/2, −y+1/2, −z.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573 CrossRef CAS Google Scholar
Bhogala, B. R. & Nangia, A. (2003). Cryst. Growth Des. 3, 547–554. Web of Science CSD CrossRef CAS Google Scholar
Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Holman, K. T., Martin, S. M., Parker, D. P. & Ward, M. D. (2001). J. Am. Chem. Soc. 123, 4421–4431. Web of Science CSD CrossRef PubMed CAS Google Scholar
Plaut, D. J., Lund, K. M. & Ward, M. D. (2000). Chem. Commun. pp. 769–770. Web of Science CSD CrossRef Google Scholar
Ranganathan, A., Pedireddi, V. R. & Rao, C. N. R. (1999). J. Am. Chem. Soc. 121, 1752–1753. Web of Science CSD CrossRef CAS Google Scholar
Russell, V. A., Evans, C. C., Li, W. J. & Ward, M. D. (1997). Science, 276, 575–579. CSD CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Swift, J. A., Pivovar, A. M., Reynolds, A. M. & Ward, M. D. (1998). J. Am. Chem. Soc. 120, 5887–5894. Web of Science CSD CrossRef CAS Google Scholar
Zhang, X.-L. & Chen, X.-M. (2005). Cryst. Growth Des. 5, 617–622. Web of Science CSD CrossRef CAS Google Scholar

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