Bis(2,6-diamino-pyridinium)-adipate-adipic acid-water (2/1/1/2).

The crystal structure of the title compound, 2C(5)H(8)N(3) (+)·C(6)H(8)O(4) (2-)·C(6)H(10)O(4)·2H(2)O, consists of amino-pyridinium cations, adipate dianions, adipic acid mol-ecules and disordered solvent water mol-ecules [occupancies 0.50 (4) and 0.50 (4)]. Both the adipate and adipic acid are located across inversion centres. Eight-membered hydrogen-bonded rings exist involving amino-pyridinium and adipate ions. Adipic acid mol-ecules and adipate anions are linked into zigzag supra-molecular chains by O-H⋯O hydrogen bonds.

Related literature

For general background, see: Lah et al. (2001 ▶); Yang et al. (1995 ▶); Goswami & Ghosh (1997 ▶); Lehn (1990 ▶). For related structures, see: Büyükgüngör & Odabaşoğlu (2002 ▶, 2006 ▶); Odabaşoğlu & Büyükgüngör (2006 ▶); Shanmuga Sundara Raj et al., (2000 ▶). For synthesis, see: Odabaşoğlu & Büyükgüngör (2006 ▶).

Experimental

Crystal data

2C5H8N3 +·C6H8O4 2−·C6H10O4·2H2O

M = 546.58

Triclinic,

a = 5.0645 (7) Å

b = 7.6261 (11) Å

c = 17.702 (3) Å

α = 87.861 (11)°

β = 85.169 (11)°

γ = 73.323 (11)°

V = 652.55 (18) Å3

Z = 1

Mo Kα radiation

μ = 0.11 mm−1

T = 296 (2) K

0.60 × 0.48 × 0.08 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.949, T max = 0.993

7575 measured reflections

2996 independent reflections

2261 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.118

S = 1.05

2996 reflections

192 parameters

17 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807055602/xu2332sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807055602/xu2332Isup2.hkl

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

2C5H8N3+·C6H8O42–·C6H10O4·2H2O	Z = 1
Mr = 546.58	F000 = 292
Triclinic, P1	Dx = 1.391 Mg m−3
Hall symbol: -P 1	Melting point = 428–429 K
a = 5.0645 (7) Å	Mo Kα radiation λ = 0.71073 Å
b = 7.6261 (11) Å	Cell parameters from 8371 reflections
c = 17.702 (3) Å	θ = 2.3–27.9º
α = 87.861 (11)º	µ = 0.11 mm−1
β = 85.169 (11)º	T = 296 (2) K
γ = 73.323 (11)º	Plate, colourless
V = 652.55 (18) Å3	0.60 × 0.48 × 0.08 mm

Stoe IPDS 2 diffractometer	2996 independent reflections
Radiation source: fine-focus sealed tube	2261 reflections with I > 2σ(I)
Monochromator: plane graphite	Rint = 0.043
T = 296(2) K	θmax = 27.5º
ω scans	θmin = 2.3º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	h = −6→6
Tmin = 0.949, Tmax = 0.993	k = −9→9
7575 measured reflections	l = −20→22

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0653P)2 + 0.039P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2996 reflections	Δρmax = 0.21 e Å−3
192 parameters	Δρmin = −0.18 e Å−3
17 restraints	Extinction correction: SHELXL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (10)

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)
O3	1.2490 (2)	0.92346 (16)	0.72447 (6)	0.0543 (3)
O4	1.5316 (2)	0.79673 (16)	0.62672 (5)	0.0512 (3)
C6	1.3110 (3)	0.89651 (18)	0.65252 (7)	0.0374 (3)
N3	1.1687 (3)	0.4528 (2)	0.91704 (7)	0.0546 (4)
H3A	1.0050	0.5265	0.9243	0.066*
H3B	1.2601	0.4051	0.9552	0.066*
C2	1.5414 (3)	0.2937 (2)	0.82983 (8)	0.0460 (3)
H2	1.6516	0.2374	0.8683	0.055*
C7	1.0880 (3)	1.00201 (19)	0.60401 (7)	0.0418 (3)
H7A	1.0818	1.1303	0.6047	0.050*
H7B	0.9120	0.9916	0.6267	0.050*
C1	1.2800 (3)	0.41269 (18)	0.84710 (7)	0.0378 (3)
C11	0.1384 (3)	0.92888 (18)	0.99095 (7)	0.0382 (3)
H11A	0.1273	0.8107	1.0108	0.046*
H11B	0.2798	0.9613	1.0164	0.046*
O2	0.6439 (2)	0.69564 (16)	0.93768 (6)	0.0543 (3)
C3	1.6345 (3)	0.2603 (2)	0.75544 (9)	0.0501 (4)
H3	1.8095	0.1809	0.7438	0.060*
C8	1.1183 (3)	0.94351 (18)	0.52225 (7)	0.0388 (3)
H8A	1.1244	0.8154	0.5207	0.047*
H8B	1.2916	0.9562	0.4985	0.047*
C9	0.5041 (3)	0.77673 (18)	0.88646 (7)	0.0364 (3)
C10	0.2239 (3)	0.91266 (19)	0.90622 (7)	0.0388 (3)
H10A	0.0849	0.8764	0.8812	0.047*
H10B	0.2273	1.0322	0.8862	0.047*
N1	1.1255 (2)	0.49227 (15)	0.78902 (6)	0.0370 (3)
H1	0.9640	0.5662	0.7997	0.044*
C4	1.4745 (3)	0.3419 (2)	0.69719 (8)	0.0498 (4)
H4	1.5402	0.3177	0.6469	0.060*
O1	0.58652 (19)	0.75241 (14)	0.81637 (5)	0.0438 (3)
C5	1.2154 (3)	0.45998 (19)	0.71505 (7)	0.0396 (3)
N2	1.0457 (3)	0.5462 (2)	0.66285 (7)	0.0553 (4)
H2A	0.8862	0.6189	0.6767	0.066*
H2B	1.0960	0.5289	0.6154	0.066*
O5	1.2848 (3)	0.4164 (2)	0.50152 (7)	0.0631 (4)
H4A	1.373 (4)	0.865 (3)	0.7510 (13)	0.094 (8)*
H5A	1.335 (4)	0.338 (3)	0.4684 (11)	0.076 (6)*
H5B	1.114 (4)	0.448 (7)	0.506 (3)	0.089 (15)*	0.50 (4)
H5C	1.416 (7)	0.457 (6)	0.507 (3)	0.083 (15)*	0.50 (4)

	U11	U22	U33	U12	U13	U23
O3	0.0458 (6)	0.0706 (7)	0.0278 (5)	0.0149 (5)	−0.0071 (4)	−0.0044 (5)
O4	0.0367 (5)	0.0684 (7)	0.0338 (5)	0.0096 (4)	−0.0053 (4)	−0.0049 (4)
C6	0.0346 (6)	0.0427 (7)	0.0292 (6)	−0.0012 (5)	−0.0052 (5)	−0.0017 (5)
N3	0.0456 (7)	0.0723 (8)	0.0295 (6)	0.0086 (6)	−0.0002 (5)	0.0004 (5)
C2	0.0378 (7)	0.0526 (8)	0.0361 (7)	0.0061 (6)	−0.0075 (5)	0.0038 (6)
C7	0.0372 (7)	0.0470 (7)	0.0322 (6)	0.0043 (5)	−0.0076 (5)	−0.0020 (5)
C1	0.0358 (6)	0.0415 (7)	0.0310 (6)	−0.0029 (5)	−0.0029 (5)	0.0011 (5)
C11	0.0341 (6)	0.0455 (7)	0.0288 (6)	−0.0018 (5)	−0.0010 (5)	−0.0020 (5)
O2	0.0410 (5)	0.0729 (7)	0.0315 (5)	0.0124 (5)	−0.0062 (4)	0.0011 (5)
C3	0.0370 (7)	0.0570 (8)	0.0419 (7)	0.0092 (6)	−0.0005 (6)	−0.0042 (6)
C8	0.0343 (6)	0.0441 (7)	0.0309 (6)	0.0016 (5)	−0.0079 (5)	0.0001 (5)
C9	0.0322 (6)	0.0426 (6)	0.0292 (6)	−0.0021 (5)	−0.0027 (5)	−0.0017 (5)
C10	0.0335 (6)	0.0443 (7)	0.0311 (6)	0.0006 (5)	−0.0013 (5)	−0.0006 (5)
N1	0.0298 (5)	0.0424 (6)	0.0312 (5)	0.0016 (4)	−0.0012 (4)	−0.0001 (4)
C4	0.0418 (7)	0.0618 (9)	0.0324 (7)	0.0056 (6)	0.0021 (6)	−0.0043 (6)
O1	0.0373 (5)	0.0547 (6)	0.0274 (5)	0.0052 (4)	0.0000 (4)	−0.0023 (4)
C5	0.0366 (6)	0.0456 (7)	0.0311 (6)	−0.0032 (5)	−0.0031 (5)	0.0016 (5)
N2	0.0421 (7)	0.0760 (9)	0.0331 (6)	0.0073 (6)	−0.0075 (5)	0.0038 (6)
O5	0.0483 (7)	0.0801 (9)	0.0503 (7)	0.0009 (6)	−0.0029 (6)	−0.0218 (6)

O3—C6	1.2955 (15)	C3—C4	1.382 (2)
O3—H4A	0.829 (17)	C3—H3	0.9300
O4—C6	1.2196 (16)	C8—C8ii	1.521 (2)
C6—C7	1.5001 (18)	C8—H8A	0.9700
N3—C1	1.3252 (17)	C8—H8B	0.9700
N3—H3A	0.8600	C9—O1	1.2781 (15)
N3—H3B	0.8600	C9—C10	1.5199 (16)
C2—C3	1.369 (2)	C10—H10A	0.9700
C2—C1	1.3901 (18)	C10—H10B	0.9700
C2—H2	0.9300	N1—C5	1.3572 (16)
C7—C8	1.5129 (17)	N1—H1	0.8600
C7—H7A	0.9700	C4—C5	1.3806 (18)
C7—H7B	0.9700	C4—H4	0.9300
C1—N1	1.3617 (17)	C5—N2	1.3375 (17)
C11—C11i	1.524 (2)	N2—H2A	0.8600
C11—C10	1.5253 (17)	N2—H2B	0.8600
C11—H11A	0.9700	O5—H5A	0.824 (16)
C11—H11B	0.9700	O5—H5B	0.824 (19)
O2—C9	1.2332 (16)	O5—H5C	0.823 (19)
C6—O3—H4A	113.2 (17)	C7—C8—H8A	109.2
O4—C6—O3	123.06 (12)	C8ii—C8—H8A	109.2
O4—C6—C7	123.27 (11)	C7—C8—H8B	109.2
O3—C6—C7	113.66 (11)	C8ii—C8—H8B	109.2
C1—N3—H3A	120.0	H8A—C8—H8B	107.9
C1—N3—H3B	120.0	O2—C9—O1	122.48 (11)
H3A—N3—H3B	120.0	O2—C9—C10	119.63 (11)
C3—C2—C1	119.16 (13)	O1—C9—C10	117.89 (11)
C3—C2—H2	120.4	C9—C10—C11	114.35 (11)
C1—C2—H2	120.4	C9—C10—H10A	108.7
C6—C7—C8	115.81 (10)	C11—C10—H10A	108.7
C6—C7—H7A	108.3	C9—C10—H10B	108.7
C8—C7—H7A	108.3	C11—C10—H10B	108.7
C6—C7—H7B	108.3	H10A—C10—H10B	107.6
C8—C7—H7B	108.3	C5—N1—C1	122.82 (11)
H7A—C7—H7B	107.4	C5—N1—H1	118.6
N3—C1—N1	117.35 (12)	C1—N1—H1	118.6
N3—C1—C2	124.09 (13)	C5—C4—C3	118.80 (13)
N1—C1—C2	118.55 (12)	C5—C4—H4	120.6
C11i—C11—C10	113.06 (13)	C3—C4—H4	120.6
C11i—C11—H11A	109.0	N2—C5—N1	117.53 (12)
C10—C11—H11A	109.0	N2—C5—C4	123.31 (12)
C11i—C11—H11B	109.0	N1—C5—C4	119.16 (12)
C10—C11—H11B	109.0	C5—N2—H2A	120.0
H11A—C11—H11B	107.8	C5—N2—H2B	120.0
C2—C3—C4	121.51 (13)	H2A—N2—H2B	120.0
C2—C3—H3	119.2	H5A—O5—H5B	108 (4)
C4—C3—H3	119.2	H5A—O5—H5C	107 (4)
C7—C8—C8ii	112.10 (13)	H5B—O5—H5C	140 (5)
O4—C6—C7—C8	14.8 (2)	C11i—C11—C10—C9	177.91 (14)
O3—C6—C7—C8	−166.16 (13)	N3—C1—N1—C5	−179.08 (13)
C3—C2—C1—N3	179.15 (16)	C2—C1—N1—C5	0.2 (2)
C3—C2—C1—N1	−0.1 (2)	C2—C3—C4—C5	0.2 (3)
C1—C2—C3—C4	−0.1 (3)	C1—N1—C5—N2	−179.90 (13)
C6—C7—C8—C8ii	179.37 (15)	C1—N1—C5—C4	−0.1 (2)
O2—C9—C10—C11	−2.29 (19)	C3—C4—C5—N2	179.70 (16)
O1—C9—C10—C11	178.28 (12)	C3—C4—C5—N1	−0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.03	2.8917 (14)	175
N2—H2A···O4iii	0.86	2.15	2.8589 (16)	139
N2—H2B···O5	0.86	2.25	3.0892 (18)	166
N3—H3A···O2	0.86	1.91	2.7729 (16)	178
N3—H3B···O2iv	0.86	2.06	2.8936 (17)	162
O3—H4A···O1v	0.829 (17)	1.688 (17)	2.5099 (15)	171 (3)
O5—H5A···O4vi	0.824 (16)	1.972 (17)	2.7773 (15)	165 (2)
O5—H5B···O5vii	0.824 (19)	2.00 (2)	2.804 (3)	164 (5)
O5—H5C···O5vi	0.823 (19)	2.01 (2)	2.819 (3)	168 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	2.03	2.8917 (14)	175
N2—H2A⋯O4i	0.86	2.15	2.8589 (16)	139
N2—H2B⋯O5	0.86	2.25	3.0892 (18)	166
N3—H3A⋯O2	0.86	1.91	2.7729 (16)	178
N3—H3B⋯O2ii	0.86	2.06	2.8936 (17)	162
O3—H4A⋯O1iii	0.829 (17)	1.688 (17)	2.5099 (15)	171 (3)
O5—H5A⋯O4iv	0.824 (16)	1.972 (17)	2.7773 (15)	165 (2)
O5—H5B⋯O5v	0.824 (19)	2.00 (2)	2.804 (3)	164 (5)
O5—H5C⋯O5iv	0.823 (19)	2.01 (2)	2.819 (3)	168 (5)

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