Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038937/hb2481sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038937/hb2481Isup2.hkl |
CCDC reference: 660284
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.061
- wR factor = 0.165
- Data-to-parameter ratio = 19.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.22 Sigma PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 2000 Deg. PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5B PLAT301_ALERT_3_C Main Residue Disorder ......................... 13.00 Perc.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C4A = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C4B = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Allen (2002); Bruno et al. (2004); Desiraju (1995); Etter (1990); Ferguson et al. (1992); Khokhar & Lumetta (1989); Kuroda & Mason (1977); Ramasubramanian et al. (2007); Roy et al. (2005).
For related literature, see: Bu˘car et al. (2007).
Stoichiometric quantities of adipic acid and meso-1,2-diphenylethylene diamine were separately dissolved in methanol. These solutions were warmed to 343 K and slowly mixed in a 1:1 molar ratio of acid to amine. The resulting mixture was kept at room temperature for slow evaporation of the solvent. Colourless crystals of (I) appeared after two days and were washed with water and dried in vacuo.
The H atoms were placed in idealized positions (C—H = 0.95–1.00 Å, N—H = 0.91 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(N). In the disordered central portion of the cation, the populations of the two conformers [0.613 (8):0.387 (8)] were contrained to sum to unity.
From the viewpoint of crystal engineering (Desiraju, 1995), adipic acid is a useful species for constructing crystalline architectures because of its proton donating capability to generate hydrogen bonding accepting sites (Roy et al., 2005, Bu˘car et al., 2007), leading to a solid state array with defined dimensionality.
The survey of Khokhar & Lumetta (1989) suggests that meso-1,2-diphenylethylenediamine might be useful as a chemotherapeutic agent. This species and its organic and inorganic salts or complexes can develop supramolecular structures by self assembly of components which contain two hydrogen bonding donor sites (Ferguson et al., 1992; Kuroda & Mason, 1977).
As part of our ongoing studies of this species (Ramasubramanian et al.,2007), we now report the synthesis and structure of the title compound, (I), (Fig. 1). Double proton transfer from acid to amine has occurred. Both anion and cation are generated by inversion and there is a 61:39 disorder in the central fragment of the cation.
The C—O bond lengths in the adipate moiety indicate delocalization of charge [C—O = 1.244 (1) Å and 1.283 (1) Å] as they are intermediate between single and double bond lengths (Bruno et al., 2004; Allen, 2002).
The species interact by way of N—H···O and C—H···O interactions (Table 1, Fig. 2) such that each cation forms a R22(9) ring (Etter, 1990) with its neighbouring adipate anion. Several other hydrogen-bonded rings are apparent in the crystal packing and they are designated as R44(28), R23(10) R24(12), and R21(6). The R44(28) ring forms an infinite ladder in the crystal by N—H···O interactions (Fig. 3).
For related literature, see: Allen (2002); Bruno et al. (2004); Desiraju (1995); Etter (1990); Ferguson et al. (1992); Khokhar & Lumetta (1989); Kuroda & Mason (1977); Ramasubramanian et al. (2007); Roy et al. (2005).
For related literature, see: Bu˘car et al. (2007).
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C14H18N22+·C6H8O42− | Z = 1 |
Mr = 358.43 | F(000) = 192 |
Triclinic, P1 | Dx = 1.310 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.361 (3) Å | Cell parameters from 2369 reflections |
b = 6.931 (3) Å | θ = 2.5–30.0° |
c = 11.820 (5) Å | µ = 0.09 mm−1 |
α = 105.35 (2)° | T = 100 K |
β = 92.05 (2)° | Shard, colourless |
γ = 113.64 (2)° | 0.18 × 0.17 × 0.15 mm |
V = 454.4 (4) Å3 |
Nonius KappaCCD diffractometer | 1727 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 30.1°, θmin = 3.3° |
ω scans with κ offsets | h = −8→8 |
8038 measured reflections | k = −9→9 |
2643 independent reflections | l = −16→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.061 | H-atom parameters constrained |
wR(F2) = 0.165 | w = 1/[σ2(Fo2) + (0.0671P)2 + 0.226P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2643 reflections | Δρmax = 0.32 e Å−3 |
138 parameters | Δρmin = −0.35 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.029 (9) |
C14H18N22+·C6H8O42− | γ = 113.64 (2)° |
Mr = 358.43 | V = 454.4 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 6.361 (3) Å | Mo Kα radiation |
b = 6.931 (3) Å | µ = 0.09 mm−1 |
c = 11.820 (5) Å | T = 100 K |
α = 105.35 (2)° | 0.18 × 0.17 × 0.15 mm |
β = 92.05 (2)° |
Nonius KappaCCD diffractometer | 1727 reflections with I > 2σ(I) |
8038 measured reflections | Rint = 0.040 |
2643 independent reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.32 e Å−3 |
2643 reflections | Δρmin = −0.35 e Å−3 |
138 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 | Occ. (<1) | |
O1 | 0.2968 (2) | 0.6691 (2) | 0.29572 (11) | 0.0219 (3) | |
O2 | 0.0766 (2) | 0.8389 (2) | 0.37116 (10) | 0.0222 (3) | |
C1 | 0.1389 (3) | 0.7285 (3) | 0.28460 (15) | 0.0172 (4) | |
C2 | 0.0067 (3) | 0.6698 (3) | 0.16156 (15) | 0.0189 (4) | |
H2A | 0.0321 | 0.8088 | 0.1441 | 0.023* | |
H2B | −0.1614 | 0.5914 | 0.1631 | 0.023* | |
C3 | 0.0716 (3) | 0.5271 (3) | 0.06021 (14) | 0.0204 (4) | |
H3A | 0.0472 | 0.3874 | 0.0767 | 0.024* | |
H3B | 0.2387 | 0.6055 | 0.0564 | 0.024* | |
N1 | 0.3377 (3) | 0.2390 (2) | 0.54090 (14) | 0.0210 (4) | |
H1N | 0.2729 | 0.3005 | 0.5989 | 0.031* | 0.613 (8) |
H2N | 0.4619 | 0.2284 | 0.5746 | 0.031* | 0.613 (8) |
H3N | 0.2306 | 0.1017 | 0.4977 | 0.031* | 0.613 (8) |
H4N | 0.3499 | 0.1461 | 0.4735 | 0.031* | 0.387 (8) |
H5N | 0.1921 | 0.1784 | 0.5588 | 0.031* | 0.387 (8) |
H6N | 0.4440 | 0.2603 | 0.6019 | 0.031* | 0.387 (8) |
C4A | 0.4175 (5) | 0.3837 (5) | 0.4595 (3) | 0.0162 (9) | 0.613 (8) |
H4A | 0.2786 | 0.3923 | 0.4229 | 0.019* | 0.613 (8) |
C5A | 0.5268 (8) | 0.2904 (7) | 0.3605 (3) | 0.0156 (8) | 0.613 (8) |
C4B | 0.3833 (8) | 0.4618 (8) | 0.5214 (5) | 0.0158 (14) | 0.387 (8) |
H4B | 0.2628 | 0.4322 | 0.4545 | 0.019* | 0.387 (8) |
C5B | 0.6303 (13) | 0.3637 (10) | 0.3729 (4) | 0.0150 (12) | 0.387 (8) |
C6 | 0.7312 (4) | 0.2447 (3) | 0.38574 (18) | 0.0350 (5) | |
H6 | 0.8136 | 0.2963 | 0.4642 | 0.042* | |
C7 | 0.7970 (3) | 0.1269 (3) | 0.29318 (16) | 0.0222 (4) | |
H7 | 0.9117 | 0.0774 | 0.3076 | 0.027* | |
C8 | 0.6942 (4) | 0.0812 (4) | 0.17879 (18) | 0.0352 (5) | |
H8 | 0.7372 | −0.0020 | 0.1139 | 0.042* | |
C9 | 0.5293 (4) | 0.1554 (3) | 0.15777 (18) | 0.0303 (5) | |
H9 | 0.4608 | 0.1242 | 0.0785 | 0.036* | |
C10 | 0.4644 (4) | 0.2733 (4) | 0.25008 (18) | 0.0314 (5) | |
H10 | 0.3718 | 0.3446 | 0.2340 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0225 (7) | 0.0251 (7) | 0.0179 (6) | 0.0129 (6) | 0.0003 (5) | 0.0023 (5) |
O2 | 0.0251 (7) | 0.0265 (7) | 0.0134 (6) | 0.0137 (6) | 0.0021 (5) | −0.0004 (5) |
C1 | 0.0178 (8) | 0.0164 (8) | 0.0152 (8) | 0.0056 (7) | 0.0028 (6) | 0.0042 (6) |
C2 | 0.0194 (9) | 0.0215 (8) | 0.0144 (8) | 0.0099 (7) | 0.0013 (6) | 0.0014 (6) |
C3 | 0.0211 (9) | 0.0246 (9) | 0.0140 (8) | 0.0109 (8) | 0.0014 (7) | 0.0020 (7) |
N1 | 0.0176 (7) | 0.0203 (7) | 0.0240 (8) | 0.0060 (6) | 0.0016 (6) | 0.0089 (6) |
C4A | 0.0167 (14) | 0.0177 (14) | 0.0126 (17) | 0.0073 (12) | 0.0018 (11) | 0.0022 (12) |
C5A | 0.0159 (19) | 0.0112 (16) | 0.0156 (15) | 0.0046 (14) | 0.0025 (14) | −0.0004 (12) |
C4B | 0.018 (2) | 0.019 (2) | 0.014 (3) | 0.0102 (19) | 0.0033 (17) | 0.006 (2) |
C5B | 0.019 (3) | 0.012 (3) | 0.008 (2) | 0.004 (2) | 0.002 (2) | −0.0007 (19) |
C6 | 0.0673 (16) | 0.0301 (10) | 0.0156 (9) | 0.0320 (11) | −0.0003 (9) | 0.0026 (8) |
C7 | 0.0203 (9) | 0.0239 (9) | 0.0235 (9) | 0.0101 (8) | 0.0059 (7) | 0.0074 (7) |
C8 | 0.0468 (14) | 0.0465 (13) | 0.0190 (10) | 0.0334 (12) | 0.0045 (9) | −0.0013 (9) |
C9 | 0.0374 (12) | 0.0315 (11) | 0.0199 (9) | 0.0199 (10) | −0.0031 (8) | −0.0029 (8) |
C10 | 0.0459 (13) | 0.0395 (11) | 0.0295 (11) | 0.0319 (11) | 0.0193 (9) | 0.0196 (9) |
O1—C1 | 1.244 (2) | C4A—H4A | 1.0000 |
O2—C1 | 1.283 (2) | C5A—C10 | 1.311 (4) |
C1—C2 | 1.521 (2) | C5A—C6 | 1.494 (4) |
C2—C3 | 1.523 (2) | C4B—C4Bii | 1.518 (9) |
C2—H2A | 0.9900 | C4B—C5Bii | 1.524 (8) |
C2—H2B | 0.9900 | C4B—H4B | 1.0000 |
C3—C3i | 1.532 (3) | C5B—C6 | 1.264 (6) |
C3—H3A | 0.9900 | C5B—C4Bii | 1.524 (8) |
C3—H3B | 0.9900 | C5B—C10 | 1.579 (6) |
N1—C4A | 1.525 (3) | C6—C7 | 1.368 (3) |
N1—C4B | 1.535 (5) | C6—H6 | 0.9500 |
N1—H1N | 0.9100 | C7—C8 | 1.378 (3) |
N1—H2N | 0.9100 | C7—H7 | 0.9500 |
N1—H3N | 0.9100 | C8—C9 | 1.382 (3) |
N1—H4N | 0.9100 | C8—H8 | 0.9500 |
N1—H5N | 0.9100 | C9—C10 | 1.364 (3) |
N1—H6N | 0.9100 | C9—H9 | 0.9500 |
C4A—C5A | 1.513 (5) | C10—H10 | 0.9500 |
C4A—C4Aii | 1.540 (6) | ||
O1—C1—O2 | 124.40 (16) | C4Aii—C4A—H4A | 108.3 |
O1—C1—C2 | 119.49 (15) | C10—C5A—C6 | 117.1 (3) |
O2—C1—C2 | 116.11 (15) | C10—C5A—C4A | 120.7 (3) |
C1—C2—C3 | 115.80 (15) | C6—C5A—C4A | 121.6 (3) |
C1—C2—H2A | 108.3 | C4Bii—C4B—C5Bii | 112.9 (6) |
C3—C2—H2A | 108.3 | C4Bii—C4B—N1 | 106.0 (5) |
C1—C2—H2B | 108.3 | C5Bii—C4B—N1 | 115.8 (4) |
C3—C2—H2B | 108.3 | C4Bii—C4B—H4B | 107.2 |
H2A—C2—H2B | 107.4 | C5Bii—C4B—H4B | 107.2 |
C2—C3—C3i | 112.47 (18) | N1—C4B—H4B | 107.2 |
C2—C3—H3A | 109.1 | C6—C5B—C4Bii | 121.6 (4) |
C3i—C3—H3A | 109.1 | C6—C5B—C10 | 114.3 (4) |
C2—C3—H3B | 109.1 | C4Bii—C5B—C10 | 122.0 (4) |
C3i—C3—H3B | 109.1 | C5B—C6—C7 | 123.0 (3) |
H3A—C3—H3B | 107.8 | C7—C6—C5A | 118.5 (2) |
C4A—N1—H1N | 109.5 | C5B—C6—H6 | 110.9 |
C4A—N1—H2N | 109.5 | C7—C6—H6 | 120.8 |
H1N—N1—H2N | 109.5 | C5A—C6—H6 | 120.8 |
C4A—N1—H3N | 109.5 | C6—C7—C8 | 119.01 (18) |
H1N—N1—H3N | 109.5 | C6—C7—H7 | 120.5 |
H2N—N1—H3N | 109.5 | C8—C7—H7 | 120.5 |
C4B—N1—H4N | 109.5 | C7—C8—C9 | 120.51 (18) |
C4B—N1—H5N | 109.5 | C7—C8—H8 | 119.7 |
H4N—N1—H5N | 109.5 | C9—C8—H8 | 119.7 |
C4B—N1—H6N | 109.5 | C10—C9—C8 | 120.41 (19) |
H4N—N1—H6N | 109.5 | C10—C9—H9 | 119.8 |
H5N—N1—H6N | 109.5 | C8—C9—H9 | 119.8 |
C5A—C4A—N1 | 112.2 (2) | C5A—C10—C9 | 121.5 (2) |
C5A—C4A—C4Aii | 113.4 (4) | C9—C10—C5B | 114.8 (3) |
N1—C4A—C4Aii | 106.2 (3) | C5A—C10—H10 | 119.3 |
C5A—C4A—H4A | 108.3 | C9—C10—H10 | 119.3 |
N1—C4A—H4A | 108.3 | C5B—C10—H10 | 120.9 |
O1—C1—C2—C3 | 3.6 (2) | C10—C5A—C6—C7 | −19.3 (5) |
O2—C1—C2—C3 | −176.46 (15) | C4A—C5A—C6—C7 | 169.2 (3) |
C1—C2—C3—C3i | 179.22 (19) | C5B—C6—C7—C8 | −19.5 (5) |
C4B—N1—C4A—C5A | 168.8 (5) | C5A—C6—C7—C8 | 8.8 (4) |
C4B—N1—C4A—C4Aii | 44.4 (4) | C6—C7—C8—C9 | 0.8 (3) |
N1—C4A—C5A—C10 | 131.7 (3) | C7—C8—C9—C10 | −0.6 (4) |
C4Aii—C4A—C5A—C10 | −108.0 (4) | C6—C5A—C10—C9 | 20.1 (5) |
N1—C4A—C5A—C6 | −57.1 (4) | C4A—C5A—C10—C9 | −168.3 (3) |
C4Aii—C4A—C5A—C6 | 63.2 (5) | C6—C5A—C10—C5B | −59.2 (7) |
C4A—N1—C4B—C4Bii | −45.1 (4) | C4A—C5A—C10—C5B | 112.4 (8) |
C4A—N1—C4B—C5Bii | −171.2 (6) | C8—C9—C10—C5A | −10.8 (4) |
C4Bii—C5B—C6—C7 | −163.5 (4) | C8—C9—C10—C5B | 14.2 (4) |
C10—C5B—C6—C7 | 32.9 (7) | C6—C5B—C10—C5A | 82.6 (8) |
C4Bii—C5B—C6—C5A | 109.4 (10) | C4Bii—C5B—C10—C5A | −80.8 (8) |
C10—C5B—C6—C5A | −54.1 (6) | C6—C5B—C10—C9 | −30.0 (6) |
C10—C5A—C6—C5B | 88.3 (8) | C4Bii—C5B—C10—C9 | 166.5 (4) |
C4A—C5A—C6—C5B | −83.2 (7) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H5N···O2iii | 0.91 | 1.90 | 2.769 (2) | 159 |
N1—H6N···O1ii | 0.91 | 1.82 | 2.717 (2) | 167 |
N1—H3N···O2iv | 0.91 | 1.88 | 2.756 (2) | 161 |
C6—H6···O2ii | 0.95 | 2.56 | 3.359 (3) | 142 |
C7—H7···O2v | 0.95 | 2.53 | 3.421 (3) | 157 |
C10—H10···O1 | 0.95 | 2.42 | 3.249 (3) | 146 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) x, y−1, z; (v) x+1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C14H18N22+·C6H8O42− |
Mr | 358.43 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 6.361 (3), 6.931 (3), 11.820 (5) |
α, β, γ (°) | 105.35 (2), 92.05 (2), 113.64 (2) |
V (Å3) | 454.4 (4) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.18 × 0.17 × 0.15 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8038, 2643, 1727 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.706 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.165, 1.03 |
No. of reflections | 2643 |
No. of parameters | 138 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.35 |
Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H5N···O2i | 0.91 | 1.90 | 2.769 (2) | 159 |
N1—H6N···O1ii | 0.91 | 1.82 | 2.717 (2) | 167 |
N1—H3N···O2iii | 0.91 | 1.88 | 2.756 (2) | 161 |
C6—H6···O2ii | 0.95 | 2.56 | 3.359 (3) | 142 |
C7—H7···O2iv | 0.95 | 2.53 | 3.421 (3) | 157 |
C10—H10···O1 | 0.95 | 2.42 | 3.249 (3) | 146 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z; (iv) x+1, y−1, z. |
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From the viewpoint of crystal engineering (Desiraju, 1995), adipic acid is a useful species for constructing crystalline architectures because of its proton donating capability to generate hydrogen bonding accepting sites (Roy et al., 2005, Bu˘car et al., 2007), leading to a solid state array with defined dimensionality.
The survey of Khokhar & Lumetta (1989) suggests that meso-1,2-diphenylethylenediamine might be useful as a chemotherapeutic agent. This species and its organic and inorganic salts or complexes can develop supramolecular structures by self assembly of components which contain two hydrogen bonding donor sites (Ferguson et al., 1992; Kuroda & Mason, 1977).
As part of our ongoing studies of this species (Ramasubramanian et al.,2007), we now report the synthesis and structure of the title compound, (I), (Fig. 1). Double proton transfer from acid to amine has occurred. Both anion and cation are generated by inversion and there is a 61:39 disorder in the central fragment of the cation.
The C—O bond lengths in the adipate moiety indicate delocalization of charge [C—O = 1.244 (1) Å and 1.283 (1) Å] as they are intermediate between single and double bond lengths (Bruno et al., 2004; Allen, 2002).
The species interact by way of N—H···O and C—H···O interactions (Table 1, Fig. 2) such that each cation forms a R22(9) ring (Etter, 1990) with its neighbouring adipate anion. Several other hydrogen-bonded rings are apparent in the crystal packing and they are designated as R44(28), R23(10) R24(12), and R21(6). The R44(28) ring forms an infinite ladder in the crystal by N—H···O interactions (Fig. 3).