Bis(2-phenyl-biguanidium) adipate tetra-hydrate.

In the title salt, 2C(8)H(12)N(5) (+)·C(6)H(8)O(4) (2-)·4H(2)O, the anion is located on a centre of symmetry. The observed supra-molecular network of the crystal structure is produced by ten different hydrogen bonds of the N-H⋯N, N-H⋯O and O-H⋯O types. One additional O-H group is not connected to an acceptor site.

Related literature

For uses of biguanide complexes in medicine, see: Sirtori & Pasik (1994 ▶); Clement & Girreser (1999 ▶); Thompson et al. (1999 ▶); Ross et al. (2004 ▶); Woo et al. (1999 ▶); Watkins et al. (1987 ▶); Morain et al. (1994 ▶); Marchi et al. (1999 ▶); Shapiro et al. (1959a ▶,b ▶). The salts of biguanidium (1+) or (2+) cations have been tested for non-linear optical properties, see: Matulková et al. (2008 ▶, 2010 ▶); Martin et al. (1996 ▶); Martin & Pinkerton (1996 ▶); Pinkerton et al. (1978 ▶).

Experimental

Crystal data

2C8H12N5 +·C6H8O4 2−·4H2O

M = 572.64

Triclinic,

a = 7.1560 (1) Å

b = 10.8670 (2) Å

c = 11.1410 (2) Å

α = 61.5590 (9)°

β = 88.682 (1)°

γ = 71.702 (1)°

V = 714.93 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 150 K

0.4 × 0.4 × 0.3 mm

Data collection

Nonius KappaCCD area-detector diffractometer

20455 measured reflections

3260 independent reflections

2953 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.06

3260 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶) and DENZO (Otwinowski & Minor, 1997 ▶); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810049925/im2248sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049925/im2248Isup2.hkl

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

2C8H12N5+·C6H8O42−·4H2O	Z = 1
Mr = 572.64	F(000) = 306
Triclinic, P1	Dx = 1.330 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1560 (1) Å	Cell parameters from 3257 reflections
b = 10.8670 (2) Å	θ = 1.0–27.5°
c = 11.1410 (2) Å	µ = 0.10 mm−1
α = 61.5590 (9)°	T = 150 K
β = 88.682 (1)°	Prism, colourless
γ = 71.702 (1)°	0.4 × 0.4 × 0.3 mm
V = 714.93 (2) Å3

Nonius KappaCCD area-detector diffractometer	2953 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 27.4°, θmin = 2.1°
Detector resolution: 9.091 pixels mm-1	h = −9→9
ω and π scans to fill the Ewald sphere	k = −14→14
20455 measured reflections	l = −14→14
3260 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.0427P)2 + 0.2629P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.093	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.25 e Å−3
3260 reflections	Δρmin = −0.25 e Å−3
181 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
C1	1.08265 (15)	0.19532 (11)	0.51868 (10)	0.0166 (2)
C2	1.02860 (14)	0.43683 (11)	0.33714 (10)	0.0157 (2)
N1	1.01068 (14)	0.10880 (10)	0.62783 (9)	0.0198 (2)
H1	0.9966	0.3356	0.2376	0.024*
N2	1.23411 (14)	0.12406 (10)	0.47705 (10)	0.0211 (2)
H2A	1.2927	0.0211	0.5352	0.025*
H2B	1.3012	0.1750	0.4191	0.025*
N3	1.00775 (13)	0.34344 (10)	0.46586 (9)	0.01745 (19)
N4	1.03596 (14)	0.56792 (10)	0.31118 (9)	0.0205 (2)
H4A	1.0268	0.5929	0.3779	0.025*
H4B	1.0357	0.6423	0.2236	0.025*
N5	1.03464 (14)	0.40864 (10)	0.23239 (9)	0.01899 (19)
H5A	1.0784	0.0048	0.6749	0.023*
H5B	1.0304	0.4875	0.1479	0.023*
C3	0.83808 (15)	0.16121 (11)	0.67987 (11)	0.0170 (2)
C4	0.85199 (17)	0.11060 (13)	0.82069 (11)	0.0232 (2)
H4	0.9739	0.0489	0.8776	0.028*
C5	0.68398 (18)	0.15191 (14)	0.87700 (12)	0.0262 (2)
H5	0.6938	0.1175	0.9715	0.031*
C6	0.50251 (17)	0.24393 (13)	0.79302 (13)	0.0246 (2)
H6	0.3900	0.2708	0.8308	0.030*
C7	0.48929 (17)	0.29590 (14)	0.65196 (13)	0.0289 (3)
H7	0.3678	0.3591	0.5950	0.035*
C8	0.65620 (17)	0.25428 (14)	0.59510 (12)	0.0251 (2)
H8	0.6461	0.2886	0.5006	0.030*
C9	0.65021 (15)	0.26120 (11)	0.25517 (10)	0.0159 (2)
C10	0.55128 (16)	0.42815 (11)	0.19755 (11)	0.0185 (2)
H10A	0.6186	0.4595	0.2467	0.022*
H10B	0.4142	0.4488	0.2143	0.022*
C11	0.55403 (16)	0.51991 (11)	0.04279 (10)	0.0180 (2)
H11A	0.4914	0.6250	0.0133	0.022*
H11B	0.6910	0.5030	0.0260	0.022*
O1	0.82344 (11)	0.21203 (8)	0.23165 (8)	0.02091 (18)
O2	0.55463 (12)	0.17812 (8)	0.32638 (8)	0.02243 (18)
O1W	0.98182 (13)	0.70284 (10)	0.00316 (8)	0.0287 (2)
H11	1.0494	0.7325	−0.0619	0.034*
H12	0.8552	0.7580	−0.0462	0.034*
O2W	0.40159 (15)	0.11820 (11)	0.13910 (10)	0.0353 (2)
H21	0.4200	0.0216	0.1821	0.042*
H22	0.4504	0.1220	0.2138	0.042*

	U11	U22	U33	U12	U13	U23
C1	0.0182 (5)	0.0161 (5)	0.0150 (5)	−0.0064 (4)	0.0028 (4)	−0.0069 (4)
C2	0.0126 (4)	0.0157 (5)	0.0168 (5)	−0.0042 (4)	0.0033 (4)	−0.0070 (4)
N1	0.0214 (4)	0.0130 (4)	0.0193 (4)	−0.0042 (3)	0.0081 (4)	−0.0049 (3)
N2	0.0208 (5)	0.0142 (4)	0.0214 (4)	−0.0042 (3)	0.0091 (4)	−0.0050 (4)
N3	0.0211 (4)	0.0142 (4)	0.0158 (4)	−0.0063 (3)	0.0057 (3)	−0.0065 (3)
N4	0.0296 (5)	0.0158 (4)	0.0166 (4)	−0.0101 (4)	0.0067 (4)	−0.0071 (4)
N5	0.0246 (5)	0.0182 (4)	0.0151 (4)	−0.0103 (4)	0.0043 (3)	−0.0073 (3)
C3	0.0197 (5)	0.0140 (5)	0.0186 (5)	−0.0077 (4)	0.0064 (4)	−0.0080 (4)
C4	0.0222 (5)	0.0234 (5)	0.0182 (5)	−0.0051 (4)	0.0024 (4)	−0.0075 (4)
C5	0.0303 (6)	0.0293 (6)	0.0185 (5)	−0.0092 (5)	0.0081 (4)	−0.0124 (5)
C6	0.0229 (5)	0.0248 (6)	0.0299 (6)	−0.0083 (4)	0.0110 (5)	−0.0166 (5)
C7	0.0195 (6)	0.0327 (6)	0.0277 (6)	−0.0031 (5)	0.0016 (5)	−0.0133 (5)
C8	0.0236 (6)	0.0303 (6)	0.0171 (5)	−0.0069 (5)	0.0026 (4)	−0.0099 (5)
C9	0.0177 (5)	0.0159 (5)	0.0121 (4)	−0.0055 (4)	0.0011 (4)	−0.0055 (4)
C10	0.0194 (5)	0.0152 (5)	0.0176 (5)	−0.0041 (4)	0.0027 (4)	−0.0068 (4)
C11	0.0199 (5)	0.0132 (5)	0.0171 (5)	−0.0053 (4)	0.0013 (4)	−0.0047 (4)
O1	0.0181 (4)	0.0159 (4)	0.0228 (4)	−0.0045 (3)	0.0060 (3)	−0.0061 (3)
O2	0.0218 (4)	0.0176 (4)	0.0228 (4)	−0.0080 (3)	0.0078 (3)	−0.0056 (3)
O1W	0.0340 (5)	0.0277 (4)	0.0182 (4)	−0.0116 (4)	0.0084 (3)	−0.0063 (3)
O2W	0.0436 (5)	0.0304 (5)	0.0366 (5)	−0.0187 (4)	0.0049 (4)	−0.0164 (4)

C1—N2	1.3347 (13)	C5—H5	0.9300
C1—N3	1.3397 (13)	C6—C7	1.3877 (17)
C1—N1	1.3469 (13)	C6—H6	0.9300
C2—N4	1.3303 (13)	C7—C8	1.3897 (16)
C2—N5	1.3370 (13)	C7—H7	0.9300
C2—N3	1.3445 (13)	C8—H8	0.9300
N1—C3	1.4233 (13)	C9—O2	1.2622 (13)
N1—H5A	0.9432	C9—O1	1.2623 (13)
N2—H2A	0.9353	C9—C10	1.5198 (14)
N2—H2B	0.8755	C10—C11	1.5299 (14)
N4—H4A	0.8999	C10—H10A	0.9700
N4—H4B	0.9233	C10—H10B	0.9700
N5—H1	0.8934	C11—C11i	1.527 (2)
N5—H5B	0.9158	C11—H11A	0.9700
C3—C4	1.3874 (15)	C11—H11B	0.9700
C3—C8	1.3888 (15)	O1W—H11	0.8499
C4—C5	1.3911 (16)	O1W—H12	0.9225
C4—H4	0.9300	O2W—H21	0.8864
C5—C6	1.3824 (17)	O2W—H22	0.9334
N2—C1—N3	124.93 (9)	C4—C5—H5	119.9
N2—C1—N1	116.20 (9)	C5—C6—C7	119.57 (10)
N3—C1—N1	118.73 (9)	C5—C6—H6	120.2
N4—C2—N5	117.95 (9)	C7—C6—H6	120.2
N4—C2—N3	117.89 (9)	C6—C7—C8	120.50 (11)
N5—C2—N3	124.12 (9)	C6—C7—H7	119.8
C1—N1—C3	125.27 (9)	C8—C7—H7	119.8
C1—N1—H5A	118.6	C3—C8—C7	119.77 (10)
C3—N1—H5A	116.1	C3—C8—H8	120.1
C1—N2—H2A	116.5	C7—C8—H8	120.1
C1—N2—H2B	118.5	O2—C9—O1	123.20 (9)
H2A—N2—H2B	120.5	O2—C9—C10	117.75 (9)
C1—N3—C2	121.23 (9)	O1—C9—C10	119.03 (9)
C2—N4—H4A	120.7	C9—C10—C11	113.44 (8)
C2—N4—H4B	123.1	C9—C10—H10A	108.9
H4A—N4—H4B	115.8	C11—C10—H10A	108.9
C2—N5—H1	121.2	C9—C10—H10B	108.9
C2—N5—H5B	114.6	C11—C10—H10B	108.9
H1—N5—H5B	119.8	H10A—C10—H10B	107.7
C4—C3—C8	119.78 (10)	C11i—C11—C10	112.27 (11)
C4—C3—N1	118.26 (10)	C11i—C11—H11A	109.2
C8—C3—N1	121.87 (10)	C10—C11—H11A	109.2
C3—C4—C5	120.12 (11)	C11i—C11—H11B	109.2
C3—C4—H4	119.9	C10—C11—H11B	109.2
C5—C4—H4	119.9	H11A—C11—H11B	107.9
C6—C5—C4	120.25 (11)	H11—O1W—H12	99.6
C6—C5—H5	119.9	H21—O2W—H22	97.8

D—H···A	D—H	H···A	D···A	D—H···A
N5—H1···O1	0.89	2.12	2.982 (1)	163
N2—H2A···O2ii	0.94	1.92	2.837 (1)	168
N2—H2B···O2iii	0.88	2.07	2.855 (1)	149
N4—H4A···N3iv	0.90	2.14	3.041 (1)	178
N4—H4B···O1W	0.92	2.23	2.998 (1)	141
N1—H5A···O1ii	0.94	1.95	2.882 (1)	171
N5—H5B···O1W	0.92	2.03	2.897 (1)	158
O1W—H11···O1v	0.85	1.99	2.825 (1)	168
O1W—H12···O2Wi	0.92	1.86	2.781 (1)	174
O2W—H22···O2	0.93	1.89	2.797 (1)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H1⋯O1	0.89	2.12	2.982 (1)	163
N2—H2A⋯O2i	0.94	1.92	2.837 (1)	168
N2—H2B⋯O2ii	0.88	2.07	2.855 (1)	149
N4—H4A⋯N3iii	0.90	2.14	3.041 (1)	178
N4—H4B⋯O1W	0.92	2.23	2.998 (1)	141
N1—H5A⋯O1i	0.94	1.95	2.882 (1)	171
N5—H5B⋯O1W	0.92	2.03	2.897 (1)	158
O1W—H11⋯O1iv	0.85	1.99	2.825 (1)	168
O1W—H12⋯O2Wv	0.92	1.86	2.781 (1)	174
O2W—H22⋯O2	0.93	1.89	2.797 (1)	165

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