organic compounds
Bis(2-hydroxyethanaminium) biphenyl-4,4′-dicarboxylate
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
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
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Refinement
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Data collection: SMART (Bruker, 1998); cell 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
10.1107/S1600536811013523/lh5226sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811013523/lh5226Isup2.hkl
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%).
H atoms bonded to C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 - 0.97Å and Uiso(H) = 1.2Ueq(C). H atoms bonded to N and O atoms were refined independently with isotropic displacement parameters.
Data collection: SMART (Bruker, 1998); cell
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).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). |
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 monochromator | 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 |
2C2H8NO+·C14H8O42− | V = 3468.5 (6) Å3 |
Mr = 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 |
Bruker SMART CCD diffractometer | 3380 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2606 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.981 | Rint = 0.044 |
14999 measured reflections |
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 | Δρmax = 0.47 e Å−3 |
3380 reflections | Δρmin = −0.18 e Å−3 |
267 parameters |
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) |
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− |
Mr | 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) |
Tmin, Tmax | 0.969, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14999, 3380, 2606 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.47, −0.18 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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) −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
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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 BDB2- 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 BDB2- 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).