4,4′-Bipyridinium bis(perchlorate)–4-aminobenzoic acid–4,4′-bipyridine–water (1/4/2/2)

Meng, Q.-H.; Han, L.; Hou, J.-D.; Luo, Y.-F.; Zeng, R.-H.

doi:10.1107/S1600536808042207

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages o132-o133

doi:10.1107/S1600536808042207

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4,4′-Bipyridinium bis(perchlorate)–4-aminobenzoic acid–4,4′-bipyridine–water (1/4/2/2)

Qun-Hui Meng,^a Lu Han,^a Jian-Dong Hou,^a Yi-Fan Luo ^a ^* and Rong-Hua Zeng ^a,^b

^aSchool of Chemistry and the Environment, South China Normal University, Guangzhou 510006, People's Republic of China, and ^bKey Laboratory of Technology on Electrochemical Energy Storage and Power Generation in Guangdong Universities, Guangzhou 510631, People's Republic of China
^*Correspondence e-mail: luoyf2004@yahoo.com.cn

(Received 21 November 2008; accepted 11 December 2008; online 17 December 2008)

In the structure of the title compound, C₁₀H₁₀N₂²⁺·2ClO₄⁻·4C₇H₇NO₂·2C₁₀H₈N₂·2H₂O, the 4,4′-bipyridinium cation has a crystallographically imposed centre of symmetry. The cation is linked by N—H⋯N hydrogen bonds to adjacent 4,4′-bipyridine molecules, which in turn interact via O—H⋯N hydrogen bonds with 4-aminobenzoic acid molecules, forming chains running parallel to [30 $[\overline{2}]$ ]. The chains are further connected into a three-dimensional network by N—H⋯O and O—H⋯O hydrogen-bonding interactions involving the perchlorate anion, the water molecules and the 4-aminobenzoic acid molecules. In addition, π–π stacking interactions with centroid–centroid distances ranging from 3.663 (6) to 3.695 (6) Å are present. The O atoms of the perchlorate anion are disordered over two sets of positions, with refined site occupancies of 0.724 (9) and 0.276 (9).

Related literature

For details of the hydrogen-bonding networks formed by 4-aminobenzoic acid and 4,4-bipyridine, see: Clemente & Marzotto (2004 ); Hu et al. (2003 ); Yang et al. (2004 ).

Experimental

Crystal data

C₁₀H₁₀N₂²⁺·2ClO₄⁻·4C₇H₇NO₂·2C₁₀H₈N₂·2H₂O
M_r = 1254.04
Triclinic, $[P \overline 1]$
a = 10.1007 (3) Å
b = 10.1105 (4) Å
c = 16.5830 (6) Å
α = 91.487 (2)°
β = 98.529 (3)°
γ = 118.500 (2)°
V = 1462.68 (10) Å³
Z = 1
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 (2) K
0.20 × 0.18 × 0.15 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: none
18132 measured reflections
5242 independent reflections
3142 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.198
S = 1.04
5242 reflections
455 parameters
74 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1C⋯N2ⁱ	0.89 (4)	1.78 (4)	2.673 (4)	174 (5)
O3—H3C⋯O5ⁱⁱ	0.90 (5)	1.72 (4)	2.609 (4)	168 (5)
O5—H5B⋯O4ⁱⁱⁱ	0.86 (4)	1.93 (4)	2.775 (4)	171 (4)
O5—H5A⋯O2^iv	0.852 (11)	1.903 (13)	2.739 (4)	167 (3)
N5—H5C⋯N1	0.90 (5)	1.78 (5)	2.680 (4)	175 (5)
N3—H3A⋯O6	0.86	2.24	3.079 (6)	166
N3—H3A⋯O7′	0.86	2.31	3.113 (15)	156
N3—H3B⋯O6^v	0.86	2.25	3.085 (8)	166
N3—H3B⋯O6′^v	0.86	2.09	2.917 (18)	162
N4—H4A⋯O8^vi	0.86	2.22	3.028 (10)	157
N4—H4A⋯O8′^vi	0.86	2.55	3.351 (19)	156
N4—H4B⋯O8	0.86	2.57	3.174 (13)	129
N4—H4B⋯O8′	0.86	2.57	3.25 (2)	136
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y+1, -z; (iii) x-1, y+1, z; (iv) x-1, y, z; (v) -x+1, -y+1, -z+1; (vi) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042207/rz2274sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808042207/rz2274Isup2.hkl

checkCIF report

Comment top

Hydrogen-bonding interactions between ligands are specific and directional. In this sense, 4-aminobenzoic acid and 4,4-bipyridine are the excellent candidates for the construction of three-dimensional network motifs, as they form regular hydrogen bonds functioning as both hydrogen-bond donors and acceptors (Clemente & Marzotto, 2004; Hu et al., 2003; Yang et al., 2004). Recently, we obtained the title compound under hydrothermal conditions and report its crystal structure herein.

In the title compound (Fig. 1), all bond lengths and angles are unexceptional. The 4,4'-bipyridinium cation, which is located on a centre of symmetry, acts as a N—H hydrogen bond donor on both sides to unprotonated 4,4'-bipyridine molecules, which in turn act as O—H hydrogen bond acceptors from one of the two independent 4-aminobenzoic acid molecules. Two 4-aminobenzoic acid molecules, two 4,4'-bipyridine molecules and the cation are thus connected by hydrogen bonding interactions to form a linear centrosymmetric chain running parallel to the [3 0 2] direction. These chains are further connected by O—H···O and N—H···O hydrogen bonds (Table 1) via the interstitial solvate water molecules, the perchlorate anions and the other 4-aminobenzoic acid molecules, forming a three-dimensional network (Fig. 2). The crystal packing is stabilized by π-π stacking interactions involving both pyridine rings of the unprotonated 4,4'-bipyridine molecule, the N5/C25-C29 pyridine ring of the cation and the C12-C17 benzene ring of one 4-aminobenzoic acid molecule: Cg1···Cg2ⁱ = 3.695 (6) Å; Cg1···Cg3 = 3.663 (6) Å; Cg3···Cg4ⁱⁱ = 3.674 (7) Å [Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/C1–C5, N2/C6–C10, C12–CC17 and N5/C25–C29 rings, respectively. Symmetry codes: (i) = 1-x, 1-y, -z; (ii) = 1-x, y, z].

Related literature top

For details of the hydrogen-bonding networks formed by 4-aminobenzoic acid and 4,4-bipyridine, see: Clemente & Marzotto (2004); Hu et al. (2003); Yang et al. (2004);

Experimental top

4-Aminobenzoic acid (1 mmol, 0.137 g,), 4,4-bipyridine (1 mmol, 0.156 g,) and sodium perchlorate (1 mmol, 0.123 g,) were dissolved in hot water with stirring. Colourless single crystals were obtained at room temperature by slow evaporation of the solvent over a period of several days.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure showing the atomic-numbering scheme. Displacement ellipsoids drawn at the 30% probability level. Symmetry codes: (i)-x, 1-y, 1-z.
	Fig. 2. Packing diagram of the title compound viewed along the a axis. Hydrogen bonds are shown as dashed lines.

4,4'-Bipyridinium bis(perchlorate)–4-aminobenzoic acid–4,4'-bipyridine–water (1/4/2/2) top

Crystal data top

C₁₀H₁₀N₂²⁺·2ClO₄⁻·4C₇H₇NO₂·2C₁₀H₈N₂·2H₂O	Z = 1
M_r = 1254.04	F(000) = 654
Triclinic, P1	D_x = 1.424 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1007 (3) Å	Cell parameters from 2787 reflections
b = 10.1105 (4) Å	θ = 2.4–21.0°
c = 16.5830 (6) Å	µ = 0.19 mm⁻¹
α = 91.487 (2)°	T = 296 K
β = 98.529 (3)°	Block, colourless
γ = 118.500 (2)°	0.20 × 0.18 × 0.15 mm
V = 1462.68 (10) Å³

Data collection top

Bruker APEXII area-detector diffractometer	3142 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.058
Graphite monochromator	θ_max = 25.2°, θ_min = 2.3°
ϕ and ω scans	h = −12→11
18132 measured reflections	k = −11→12
5242 independent reflections	l = −18→19

Refinement top

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) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0835P)² + 0.5543P] where P = (F_o² + 2F_c²)/3
5242 reflections	(Δ/σ)_max < 0.001
455 parameters	Δρ_max = 0.37 e Å⁻³
74 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₀H₁₀N₂²⁺·2ClO₄⁻·4C₇H₇NO₂·2C₁₀H₈N₂·2H₂O	γ = 118.500 (2)°
M_r = 1254.04	V = 1462.68 (10) Å³
Triclinic, P1	Z = 1
a = 10.1007 (3) Å	Mo Kα radiation
b = 10.1105 (4) Å	µ = 0.19 mm⁻¹
c = 16.5830 (6) Å	T = 296 K
α = 91.487 (2)°	0.20 × 0.18 × 0.15 mm
β = 98.529 (3)°

Data collection top

Bruker APEXII area-detector diffractometer	3142 reflections with I > 2σ(I)
18132 measured reflections	R_int = 0.058
5242 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	74 restraints
wR(F²) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.37 e Å⁻³
5242 reflections	Δρ_min = −0.41 e Å⁻³
455 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.4592 (5)	0.5702 (4)	0.2272 (2)	0.0780 (12)
H1	0.4688	0.6561	0.2552	0.094*
C2	0.5531 (5)	0.5894 (4)	0.1716 (2)	0.0718 (11)
H2	0.6235	0.6866	0.1627	0.086*
C3	0.5438 (3)	0.4659 (3)	0.12897 (17)	0.0445 (7)
C4	0.4368 (4)	0.3262 (4)	0.1468 (2)	0.0621 (9)
H4	0.4256	0.2382	0.1204	0.075*
C5	0.3468 (4)	0.3170 (4)	0.2035 (2)	0.0667 (10)
H5	0.2758	0.2216	0.2145	0.080*
C6	0.6445 (3)	0.4829 (3)	0.06907 (17)	0.0454 (7)
C7	0.7468 (4)	0.6237 (4)	0.0504 (2)	0.0640 (10)
H7	0.7552	0.7104	0.0767	0.077*
C8	0.8361 (4)	0.6363 (4)	−0.0067 (2)	0.0681 (10)
H8	0.9044	0.7329	−0.0176	0.082*
C9	0.7333 (5)	0.3836 (5)	−0.0301 (2)	0.0774 (12)
H9	0.7272	0.2990	−0.0576	0.093*
C10	0.6398 (5)	0.3613 (4)	0.0269 (2)	0.0716 (11)
H10	0.5731	0.2634	0.0368	0.086*
C11	1.0179 (4)	0.5687 (4)	0.1962 (2)	0.0570 (9)
C12	0.9160 (4)	0.5534 (4)	0.25473 (18)	0.0504 (8)
C13	0.8008 (4)	0.4134 (4)	0.26858 (19)	0.0529 (8)
H13	0.7875	0.3258	0.2406	0.064*
C14	0.7066 (4)	0.4019 (4)	0.32255 (19)	0.0556 (8)
H14	0.6304	0.3070	0.3307	0.067*
C15	0.7238 (4)	0.5309 (4)	0.3653 (2)	0.0566 (9)
C16	0.8404 (4)	0.6714 (4)	0.3531 (2)	0.0647 (10)
H16	0.8550	0.7588	0.3820	0.078*
C17	0.9340 (4)	0.6819 (4)	0.2984 (2)	0.0601 (9)
H17	1.0108	0.7767	0.2904	0.072*
C18	0.8014 (5)	0.0246 (4)	0.0816 (2)	0.0625 (9)
C19	0.7278 (4)	0.0094 (3)	0.1525 (2)	0.0573 (9)
C20	0.8008 (4)	0.0010 (4)	0.2290 (2)	0.0653 (10)
H20	0.8963	0.0066	0.2340	0.078*
C21	0.7339 (5)	−0.0152 (4)	0.2969 (2)	0.0713 (11)
H21	0.7847	−0.0200	0.3473	0.086*
C22	0.5911 (5)	−0.0244 (4)	0.2912 (3)	0.0735 (11)
C23	0.5181 (5)	−0.0161 (4)	0.2145 (3)	0.0747 (11)
H23	0.4226	−0.0216	0.2094	0.090*
C24	0.5850 (4)	0.0000 (4)	0.1471 (2)	0.0644 (10)
H24	0.5341	0.0047	0.0966	0.077*
C25	0.2424 (5)	0.5900 (5)	0.3916 (2)	0.0785 (12)
H25	0.3251	0.6733	0.3770	0.094*
C26	0.1654 (5)	0.6129 (4)	0.4471 (2)	0.0716 (11)
H26	0.1951	0.7107	0.4689	0.086*
C27	0.0433 (3)	0.4902 (4)	0.47059 (17)	0.0466 (7)
C28	0.0067 (4)	0.3484 (4)	0.4352 (2)	0.0657 (10)
H28	−0.0737	0.2620	0.4491	0.079*
C29	0.0886 (4)	0.3356 (5)	0.3799 (2)	0.0709 (11)
H29	0.0623	0.2396	0.3567	0.085*
N1	0.3567 (3)	0.4374 (3)	0.24310 (16)	0.0579 (7)
N2	0.8310 (3)	0.5191 (4)	−0.04737 (17)	0.0607 (8)
N3	0.6272 (4)	0.5201 (4)	0.41820 (18)	0.0758 (9)
H3A	0.5550	0.4328	0.4251	0.091*
H3B	0.6389	0.6007	0.4443	0.091*
N4	0.5226 (5)	−0.0444 (5)	0.3583 (2)	0.1091 (13)
H4A	0.5680	−0.0514	0.4049	0.131*
H4B	0.4342	−0.0499	0.3540	0.131*
N5	0.2031 (4)	0.4537 (4)	0.35815 (17)	0.0598 (8)
O1	0.9981 (3)	0.4406 (3)	0.16264 (16)	0.0718 (7)
O2	1.1150 (3)	0.6913 (3)	0.18048 (17)	0.0787 (8)
O3	0.7226 (3)	0.0324 (3)	0.01186 (18)	0.0793 (8)
O4	0.9250 (3)	0.0302 (3)	0.08352 (18)	0.0848 (8)
O5	0.1553 (3)	0.9533 (3)	0.11791 (17)	0.0720 (7)
H1C	1.058 (4)	0.451 (5)	0.126 (2)	0.119 (17)*
H3C	0.776 (5)	0.039 (6)	−0.028 (2)	0.122 (19)*
H5A	0.128 (4)	0.866 (2)	0.133 (2)	0.078 (13)*
H5B	0.079 (3)	0.970 (4)	0.111 (3)	0.12 (2)*
H5C	0.251 (5)	0.442 (6)	0.319 (2)	0.14 (2)*
O6	0.3808 (7)	0.2312 (5)	0.4742 (4)	0.153 (3)	0.724 (9)
O7	0.2540 (10)	0.0812 (8)	0.3516 (3)	0.158 (3)	0.724 (9)
O8	0.2998 (12)	−0.0234 (8)	0.4681 (6)	0.155 (4)	0.724 (9)
O9	0.1258 (8)	0.0621 (9)	0.4610 (6)	0.190 (4)	0.724 (9)
Cl1	0.26368 (13)	0.08898 (12)	0.43474 (8)	0.0877 (4)	0.724 (9)
O6'	0.265 (2)	0.1766 (19)	0.5022 (7)	0.158 (7)	0.276 (9)
O7'	0.3803 (16)	0.1791 (19)	0.3902 (11)	0.175 (8)	0.276 (9)
O8'	0.264 (2)	−0.0437 (14)	0.4533 (12)	0.109 (7)	0.276 (9)
O9'	0.1148 (13)	0.0416 (13)	0.3755 (9)	0.115 (6)	0.276 (9)
Cl1'	0.26368 (13)	0.08898 (12)	0.43474 (8)	0.0877 (4)	0.276 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.101 (3)	0.059 (2)	0.088 (3)	0.041 (2)	0.048 (2)	0.007 (2)
C2	0.087 (3)	0.048 (2)	0.086 (3)	0.029 (2)	0.045 (2)	0.0136 (19)
C3	0.0441 (17)	0.0503 (19)	0.0398 (16)	0.0236 (15)	0.0071 (13)	0.0044 (13)
C4	0.068 (2)	0.050 (2)	0.067 (2)	0.0218 (18)	0.0303 (18)	0.0017 (16)
C5	0.065 (2)	0.057 (2)	0.071 (2)	0.0190 (18)	0.0278 (18)	0.0058 (18)
C6	0.0450 (17)	0.0509 (19)	0.0415 (16)	0.0240 (15)	0.0085 (13)	0.0076 (14)
C7	0.062 (2)	0.051 (2)	0.070 (2)	0.0167 (17)	0.0244 (18)	0.0000 (17)
C8	0.057 (2)	0.062 (2)	0.068 (2)	0.0113 (18)	0.0246 (18)	0.0100 (19)
C9	0.099 (3)	0.066 (3)	0.084 (3)	0.043 (2)	0.051 (2)	0.014 (2)
C10	0.088 (3)	0.051 (2)	0.086 (3)	0.033 (2)	0.050 (2)	0.0181 (19)
C11	0.051 (2)	0.067 (2)	0.053 (2)	0.0286 (19)	0.0115 (16)	0.0133 (18)
C12	0.0505 (19)	0.058 (2)	0.0458 (17)	0.0287 (17)	0.0082 (14)	0.0096 (15)
C13	0.057 (2)	0.055 (2)	0.0496 (18)	0.0293 (17)	0.0115 (15)	0.0056 (15)
C14	0.054 (2)	0.059 (2)	0.0524 (19)	0.0248 (17)	0.0139 (15)	0.0097 (16)
C15	0.056 (2)	0.074 (2)	0.0492 (19)	0.0380 (19)	0.0113 (16)	0.0105 (17)
C16	0.073 (2)	0.063 (2)	0.066 (2)	0.039 (2)	0.0136 (19)	0.0012 (18)
C17	0.059 (2)	0.054 (2)	0.065 (2)	0.0247 (17)	0.0153 (17)	0.0110 (17)
C18	0.066 (2)	0.047 (2)	0.077 (3)	0.0274 (18)	0.018 (2)	0.0114 (17)
C19	0.056 (2)	0.0402 (18)	0.074 (2)	0.0217 (16)	0.0126 (17)	0.0086 (16)
C20	0.062 (2)	0.057 (2)	0.077 (3)	0.0304 (19)	0.0102 (19)	0.0050 (18)
C21	0.084 (3)	0.059 (2)	0.069 (2)	0.034 (2)	0.011 (2)	0.0068 (18)
C22	0.082 (3)	0.050 (2)	0.089 (3)	0.027 (2)	0.034 (2)	0.014 (2)
C23	0.061 (2)	0.064 (2)	0.103 (3)	0.031 (2)	0.023 (2)	0.019 (2)
C24	0.061 (2)	0.056 (2)	0.079 (3)	0.0292 (18)	0.0149 (19)	0.0149 (18)
C25	0.090 (3)	0.067 (3)	0.083 (3)	0.032 (2)	0.050 (2)	0.017 (2)
C26	0.088 (3)	0.053 (2)	0.083 (3)	0.033 (2)	0.047 (2)	0.0095 (18)
C27	0.0489 (18)	0.0546 (19)	0.0420 (16)	0.0294 (16)	0.0090 (13)	0.0066 (14)
C28	0.060 (2)	0.056 (2)	0.078 (2)	0.0229 (18)	0.0246 (18)	−0.0046 (18)
C29	0.066 (2)	0.063 (2)	0.077 (3)	0.026 (2)	0.021 (2)	−0.0122 (19)
N1	0.0571 (17)	0.067 (2)	0.0516 (16)	0.0300 (15)	0.0159 (13)	0.0041 (14)
N2	0.0552 (17)	0.074 (2)	0.0550 (17)	0.0302 (16)	0.0203 (13)	0.0093 (15)
N3	0.073 (2)	0.093 (2)	0.072 (2)	0.0439 (19)	0.0284 (17)	0.0050 (18)
N4	0.125 (3)	0.118 (3)	0.103 (3)	0.062 (3)	0.060 (3)	0.037 (3)
N5	0.0637 (19)	0.077 (2)	0.0497 (16)	0.0412 (18)	0.0156 (14)	0.0034 (15)
O1	0.0788 (18)	0.0675 (17)	0.0739 (17)	0.0323 (14)	0.0395 (14)	0.0093 (14)
O2	0.0747 (17)	0.0691 (17)	0.0948 (19)	0.0289 (15)	0.0418 (15)	0.0247 (15)
O3	0.0734 (18)	0.095 (2)	0.0739 (19)	0.0426 (16)	0.0169 (15)	0.0200 (15)
O4	0.0781 (19)	0.101 (2)	0.098 (2)	0.0563 (17)	0.0312 (16)	0.0246 (16)
O5	0.0724 (18)	0.0648 (18)	0.0782 (18)	0.0317 (15)	0.0163 (14)	0.0169 (14)
O6	0.165 (5)	0.067 (3)	0.187 (6)	0.018 (3)	0.060 (4)	−0.015 (3)
O7	0.213 (8)	0.156 (5)	0.086 (4)	0.072 (5)	0.043 (4)	0.021 (3)
O8	0.199 (8)	0.095 (5)	0.177 (7)	0.077 (5)	0.030 (6)	0.017 (4)
O9	0.148 (6)	0.210 (7)	0.237 (8)	0.084 (5)	0.114 (6)	0.047 (6)
Cl1	0.0960 (9)	0.0596 (7)	0.1150 (10)	0.0368 (6)	0.0438 (7)	0.0144 (6)
O6'	0.195 (12)	0.143 (10)	0.156 (10)	0.094 (9)	0.056 (8)	−0.036 (7)
O7'	0.172 (11)	0.162 (11)	0.170 (12)	0.048 (8)	0.082 (9)	0.058 (9)
O8'	0.115 (9)	0.063 (9)	0.145 (11)	0.045 (7)	−0.003 (7)	0.037 (7)
O9'	0.095 (8)	0.096 (8)	0.139 (10)	0.051 (6)	−0.030 (7)	−0.010 (6)
Cl1'	0.0960 (9)	0.0596 (7)	0.1150 (10)	0.0368 (6)	0.0438 (7)	0.0144 (6)

Geometric parameters (Å, º) top

C1—N1	1.310 (5)	C18—C19	1.456 (5)
C1—C2	1.371 (5)	C19—C24	1.388 (5)
C1—H1	0.9300	C19—C20	1.396 (5)
C2—C3	1.376 (5)	C20—C21	1.372 (5)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.382 (4)	C21—C22	1.388 (6)
C3—C6	1.481 (4)	C21—H21	0.9300
C4—C5	1.378 (5)	C22—N4	1.366 (5)
C4—H4	0.9300	C22—C23	1.397 (6)
C5—N1	1.321 (4)	C23—C24	1.365 (5)
C5—H5	0.9300	C23—H23	0.9300
C6—C10	1.375 (5)	C24—H24	0.9300
C6—C7	1.380 (4)	C25—N5	1.318 (5)
C7—C8	1.371 (5)	C25—C26	1.371 (5)
C7—H7	0.9300	C25—H25	0.9300
C8—N2	1.323 (5)	C26—C27	1.385 (5)
C8—H8	0.9300	C26—H26	0.9300
C9—N2	1.322 (5)	C27—C28	1.387 (5)
C9—C10	1.381 (5)	C27—C27ⁱ	1.472 (6)
C9—H9	0.9300	C28—C29	1.365 (5)
C10—H10	0.9300	C28—H28	0.9300
C11—O2	1.224 (4)	C29—N5	1.312 (5)
C11—O1	1.308 (4)	C29—H29	0.9300
C11—C12	1.475 (5)	N3—H3A	0.8600
C12—C17	1.390 (5)	N3—H3B	0.8600
C12—C13	1.391 (5)	N4—H4A	0.8600
C13—C14	1.368 (4)	N4—H4B	0.8600
C13—H13	0.9300	N5—H5C	0.90 (5)
C14—C15	1.390 (5)	O1—H1C	0.89 (4)
C14—H14	0.9300	O3—H3C	0.90 (5)
C15—N3	1.375 (4)	O5—H5A	0.852 (11)
C15—C16	1.391 (5)	O5—H5B	0.86 (4)
C16—C17	1.376 (5)	O6—Cl1	1.412 (4)
C16—H16	0.9300	O7—Cl1	1.365 (4)
C17—H17	0.9300	O8—Cl1	1.448 (5)
C18—O4	1.218 (4)	O9—Cl1	1.424 (5)
C18—O3	1.329 (4)

N1—C1—C2	123.6 (3)	C24—C19—C20	118.0 (3)
N1—C1—H1	118.2	C24—C19—C18	122.5 (3)
C2—C1—H1	118.2	C20—C19—C18	119.5 (3)
C1—C2—C3	120.4 (3)	C21—C20—C19	121.0 (4)
C1—C2—H2	119.8	C21—C20—H20	119.5
C3—C2—H2	119.8	C19—C20—H20	119.5
C2—C3—C4	115.7 (3)	C20—C21—C22	120.8 (4)
C2—C3—C6	121.7 (3)	C20—C21—H21	119.6
C4—C3—C6	122.6 (3)	C22—C21—H21	119.6
C5—C4—C3	120.2 (3)	N4—C22—C21	120.8 (4)
C5—C4—H4	119.9	N4—C22—C23	121.0 (4)
C3—C4—H4	119.9	C21—C22—C23	118.2 (4)
N1—C5—C4	123.0 (3)	C24—C23—C22	120.9 (4)
N1—C5—H5	118.5	C24—C23—H23	119.5
C4—C5—H5	118.5	C22—C23—H23	119.5
C10—C6—C7	115.7 (3)	C23—C24—C19	121.1 (4)
C10—C6—C3	122.9 (3)	C23—C24—H24	119.4
C7—C6—C3	121.4 (3)	C19—C24—H24	119.4
C8—C7—C6	120.3 (3)	N5—C25—C26	122.2 (4)
C8—C7—H7	119.8	N5—C25—H25	118.9
C6—C7—H7	119.8	C26—C25—H25	118.9
N2—C8—C7	123.9 (3)	C25—C26—C27	119.9 (3)
N2—C8—H8	118.1	C25—C26—H26	120.0
C7—C8—H8	118.1	C27—C26—H26	120.0
N2—C9—C10	123.3 (3)	C26—C27—C28	116.4 (3)
N2—C9—H9	118.4	C26—C27—C27ⁱ	121.7 (4)
C10—C9—H9	118.4	C28—C27—C27ⁱ	121.9 (4)
C6—C10—C9	120.5 (3)	C29—C28—C27	120.0 (3)
C6—C10—H10	119.8	C29—C28—H28	120.0
C9—C10—H10	119.8	C27—C28—H28	120.0
O2—C11—O1	122.0 (3)	N5—C29—C28	122.5 (4)
O2—C11—C12	123.2 (3)	N5—C29—H29	118.8
O1—C11—C12	114.8 (3)	C28—C29—H29	118.8
C17—C12—C13	117.9 (3)	C1—N1—C5	117.1 (3)
C17—C12—C11	119.8 (3)	C9—N2—C8	116.4 (3)
C13—C12—C11	122.3 (3)	C15—N3—H3A	120.0
C14—C13—C12	121.3 (3)	C15—N3—H3B	120.0
C14—C13—H13	119.3	H3A—N3—H3B	120.0
C12—C13—H13	119.3	C22—N4—H4A	120.0
C13—C14—C15	120.6 (3)	C22—N4—H4B	120.0
C13—C14—H14	119.7	H4A—N4—H4B	120.0
C15—C14—H14	119.7	C29—N5—C25	119.1 (3)
N3—C15—C14	120.8 (3)	C29—N5—H5C	120 (4)
N3—C15—C16	120.6 (3)	C25—N5—H5C	121 (4)
C14—C15—C16	118.6 (3)	C11—O1—H1C	114 (3)
C17—C16—C15	120.4 (3)	C18—O3—H3C	108 (3)
C17—C16—H16	119.8	H5A—O5—H5B	110 (4)
C15—C16—H16	119.8	O7—Cl1—O6	111.8 (4)
C16—C17—C12	121.2 (3)	O7—Cl1—O9	114.1 (5)
C16—C17—H17	119.4	O6—Cl1—O9	107.3 (4)
C12—C17—H17	119.4	O7—Cl1—O8	110.9 (4)
O4—C18—O3	120.9 (4)	O6—Cl1—O8	106.6 (5)
O4—C18—C19	124.5 (4)	O9—Cl1—O8	105.7 (5)
O3—C18—C19	114.6 (3)

N1—C1—C2—C3	−0.3 (7)	C13—C12—C17—C16	−0.5 (5)
C1—C2—C3—C4	−0.5 (6)	C11—C12—C17—C16	179.7 (3)
C1—C2—C3—C6	−179.4 (4)	O4—C18—C19—C24	−178.5 (3)
C2—C3—C4—C5	0.6 (5)	O3—C18—C19—C24	1.6 (5)
C6—C3—C4—C5	179.5 (3)	O4—C18—C19—C20	0.3 (5)
C3—C4—C5—N1	0.1 (6)	O3—C18—C19—C20	−179.6 (3)
C2—C3—C6—C10	178.6 (3)	C24—C19—C20—C21	−0.3 (5)
C4—C3—C6—C10	−0.3 (5)	C18—C19—C20—C21	−179.2 (3)
C2—C3—C6—C7	−3.3 (5)	C19—C20—C21—C22	0.3 (5)
C4—C3—C6—C7	177.8 (3)	C20—C21—C22—N4	178.3 (4)
C10—C6—C7—C8	−0.2 (5)	C20—C21—C22—C23	−0.3 (5)
C3—C6—C7—C8	−178.4 (3)	N4—C22—C23—C24	−178.3 (4)
C6—C7—C8—N2	0.4 (6)	C21—C22—C23—C24	0.3 (6)
C7—C6—C10—C9	−0.1 (6)	C22—C23—C24—C19	−0.4 (6)
C3—C6—C10—C9	178.1 (3)	C20—C19—C24—C23	0.4 (5)
N2—C9—C10—C6	0.1 (7)	C18—C19—C24—C23	179.2 (3)
O2—C11—C12—C17	−3.6 (5)	N5—C25—C26—C27	1.0 (7)
O1—C11—C12—C17	175.5 (3)	C25—C26—C27—C28	0.0 (6)
O2—C11—C12—C13	176.5 (3)	C25—C26—C27—C27ⁱ	−179.4 (4)
O1—C11—C12—C13	−4.3 (5)	C26—C27—C28—C29	−0.5 (5)
C17—C12—C13—C14	0.8 (5)	C27ⁱ—C27—C28—C29	178.9 (4)
C11—C12—C13—C14	−179.3 (3)	C27—C28—C29—N5	0.1 (6)
C12—C13—C14—C15	−0.1 (5)	C2—C1—N1—C5	1.0 (6)
C13—C14—C15—N3	178.5 (3)	C4—C5—N1—C1	−0.9 (6)
C13—C14—C15—C16	−1.1 (5)	C10—C9—N2—C8	0.0 (6)
N3—C15—C16—C17	−178.2 (3)	C7—C8—N2—C9	−0.3 (6)
C14—C15—C16—C17	1.4 (5)	C28—C29—N5—C25	0.9 (6)
C15—C16—C17—C12	−0.6 (5)	C26—C25—N5—C29	−1.5 (6)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···N2ⁱⁱ	0.89 (4)	1.78 (4)	2.673 (4)	174 (5)
O3—H3C···O5ⁱⁱⁱ	0.90 (5)	1.72 (4)	2.609 (4)	168 (5)
O5—H5B···O4^iv	0.86 (4)	1.93 (4)	2.775 (4)	171 (4)
O5—H5A···O2^v	0.85 (1)	1.90 (1)	2.739 (4)	167 (3)
N5—H5C···N1	0.90 (5)	1.78 (5)	2.680 (4)	175 (5)
N3—H3A···O6	0.86	2.24	3.079 (6)	166
N3—H3A···O7′	0.86	2.31	3.113 (15)	156
N3—H3B···O6^vi	0.86	2.25	3.085 (8)	166
N3—H3B···O6′^vi	0.86	2.09	2.917 (18)	162
N4—H4A···O8^vii	0.86	2.22	3.028 (10)	157
N4—H4A···O8′^vii	0.86	2.55	3.351 (19)	156
N4—H4B···O8	0.86	2.57	3.174 (13)	129
N4—H4B···O8′	0.86	2.57	3.25 (2)	136

Symmetry codes: (ii) −x+2, −y+1, −z; (iii) −x+1, −y+1, −z; (iv) x−1, y+1, z; (v) x−1, y, z; (vi) −x+1, −y+1, −z+1; (vii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₂²⁺·2ClO₄⁻·4C₇H₇NO₂·2C₁₀H₈N₂·2H₂O
M_r	1254.04
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.1007 (3), 10.1105 (4), 16.5830 (6)
α, β, γ (°)	91.487 (2), 98.529 (3), 118.500 (2)
V (Å³)	1462.68 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18132, 5242, 3142
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.198, 1.04
No. of reflections	5242
No. of parameters	455
No. of restraints	74
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.41

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···N2ⁱ	0.89 (4)	1.78 (4)	2.673 (4)	174 (5)
O3—H3C···O5ⁱⁱ	0.90 (5)	1.72 (4)	2.609 (4)	168 (5)
O5—H5B···O4ⁱⁱⁱ	0.86 (4)	1.93 (4)	2.775 (4)	171 (4)
O5—H5A···O2^iv	0.852 (11)	1.903 (13)	2.739 (4)	167 (3)
N5—H5C···N1	0.90 (5)	1.78 (5)	2.680 (4)	175 (5)
N3—H3A···O6	0.86	2.237	3.079 (6)	166
N3—H3A···O7'	0.86	2.308	3.113 (15)	156
N3—H3B···O6^v	0.86	2.245	3.085 (8)	166
N3—H3B···O6'^v	0.86	2.087	2.917 (18)	162
N4—H4A···O8^vi	0.86	2.216	3.028 (10)	157
N4—H4A···O8'^vi	0.86	2.545	3.351 (19)	156
N4—H4B···O8	0.86	2.565	3.174 (13)	129
N4—H4B···O8'	0.86	2.571	3.25 (2)	136

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z; (iii) x−1, y+1, z; (iv) x−1, y, z; (v) −x+1, −y+1, −z+1; (vi) −x+1, −y, −z+1.

Acknowledgements

The authors acknowledge South China Normal University for supporting this work.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Clemente, D. A. & Marzotto, A. (2004). Acta Cryst. B60, 287–292. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Hu, D. H., Huang, W., Gou, S. H., Fang, J. L. & Fun, H. K. (2003). Polyhedron, 22, 2661–2667. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, G. P., Wang, Z. Y. & Chen, J. T. (2004). J. Mol. Struct., 707, 223–229. Google Scholar

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Volume 65| Part 1| January 2009| Pages o132-o133

doi:10.1107/S1600536808042207

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4,4′-Bipyridinium bis­(perchlorate)–4-amino­benzoic acid–4,4′-bi­pyridine–water (1/4/2/2)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4,4′-Bipyridinium bis(perchlorate)–4-aminobenzoic acid–4,4′-bipyridine–water (1/4/2/2)