Bis(2-hy-droxy-ethanaminium) biphenyl-4,4'-dicarboxyl-ate.

In the title compound, 2C(2)H(8)NO(+)·C(14)H(8)O(4) (2-), the dihedral angle between the benzene rings of the dianion is 9.95 (12)°. In the crystal, the cations and anions are linked via inter-molecular 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 n class="Chemical">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+·C14H8O4 2−

M = 364.39

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.173

S = 1.08

3380 reflections

267 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.18 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013523/lh5226sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

2C2H8NO+·C14H8O42−	F(000) = 1552
Mr = 364.39	Dx = 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

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

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(Fo2) + (0.0845P)2 + 1.5997P] where P = (Fo2 + 2Fc2)/3
3380 reflections	(Δ/σ)max < 0.001
267 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···O1iv	0.95 (4)	1.91 (4)	2.866 (3)	174 (4)

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⋯O1iv	0.95 (4)	1.91 (4)	2.866 (3)	174 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .