1-(3-Carboxyl-atophen-yl)-4,4'-bipyridin-1-ium dihydrate.

In the crystal structure of the title compound, C17H12N2O2·2H2O, the carboxyl-ate group is linked via O-H⋯O hydrogen bonds to two water mol-ecules. The crystal packing is best described as parallel layers (viewed along the a axis) of viologen and water mol-ecules associated via O-H⋯O hydrogen bonds and π-π inter-actions, with a centroid-centroid separation of 3.8276 (9) Å.

Related literature

For background to the applications of viologen complexes, see: Strutt et al. (2012 ▶). For related structures, see: Coe et al. (1998 ▶); Leblanc et al. (2010 ▶); Xu et al. (2007 ▶).

Experimental

Crystal data

C17H12N2O2·2H2O

M = 312.32

Triclinic,

a = 7.8700 (16) Å

b = 10.090 (2) Å

c = 10.250 (2) Å

α = 81.36 (3)°

β = 73.13 (3)°

γ = 74.64 (3)°

V = 748.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.13 × 0.12 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.971, T max = 0.993

6136 measured reflections

2741 independent reflections

2120 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.172

S = 1.18

2741 reflections

221 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813024197/fj2640sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024197/fj2640Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024197/fj2640Isup3.cml

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

C17H12N2O2·2H2O	Z = 2
Mr = 312.32	F(000) = 328
Triclinic, P1	Dx = 1.385 Mg m−3
a = 7.8700 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.090 (2) Å	Cell parameters from 6136 reflections
c = 10.250 (2) Å	θ = 3.0–25.4°
α = 81.36 (3)°	µ = 0.10 mm−1
β = 73.13 (3)°	T = 298 K
γ = 74.64 (3)°	Block, yellow
V = 748.7 (3) Å3	0.13 × 0.12 × 0.12 mm

Bruker SMART CCD diffractometer	2120 reflections with I > 2σ(I)
Radiation source: fine-focus tube	Rint = 0.014
ω scans	θmax = 25.4°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.971, Tmax = 0.993	k = −12→12
6136 measured reflections	l = −12→12
2741 independent reflections

Refinement on F2	4 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.172	w = 1/[σ2(Fo2) + (0.1108P)2 + 0.0207P] where P = (Fo2 + 2Fc2)/3
S = 1.18	(Δ/σ)max < 0.001
2741 reflections	Δρmax = 0.26 e Å−3
221 parameters	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	−0.30377 (18)	0.27817 (16)	0.65560 (13)	0.0580 (4)
O2	−0.32509 (18)	0.40158 (14)	0.82326 (13)	0.0604 (4)
O3	−0.2973 (2)	0.5061 (2)	1.05692 (18)	0.0752 (5)
H1	−0.297 (4)	0.472 (3)	0.980 (2)	0.113*
H2	−0.411 (3)	0.549 (3)	1.091 (3)	0.113*
O4	−0.2512 (2)	0.16627 (17)	0.41923 (14)	0.0644 (4)
H3	−0.255 (4)	0.213 (3)	0.487 (2)	0.087*
H4	−0.177 (4)	0.192 (3)	0.348 (2)	0.113 (11)*
N1	0.9650 (2)	−0.16420 (18)	−0.16937 (16)	0.0582 (5)
N2	0.35792 (18)	0.20963 (14)	0.37683 (13)	0.0390 (4)
C1	0.8954 (3)	−0.2281 (2)	−0.0513 (2)	0.0700 (7)
H1A	0.9321	−0.3238	−0.0414	0.084*
C2	0.7715 (3)	−0.1613 (2)	0.0583 (2)	0.0640 (6)
H2A	0.7263	−0.2118	0.1387	0.077*
C3	0.9079 (3)	−0.0286 (2)	−0.1783 (2)	0.0677 (6)
H3A	0.9535	0.0193	−0.2605	0.081*
C4	0.7868 (3)	0.0465 (2)	−0.0755 (2)	0.0635 (6)
H4A	0.7529	0.1421	−0.0888	0.076*
C5	0.7152 (2)	−0.01950 (17)	0.04765 (16)	0.0402 (4)
C6	0.5871 (2)	0.05920 (17)	0.16200 (16)	0.0392 (4)
C7	0.4871 (2)	−0.00366 (18)	0.27897 (17)	0.0442 (4)
H7A	0.4963	−0.0981	0.2854	0.053*
C8	0.3756 (2)	0.07283 (18)	0.38421 (17)	0.0440 (4)
H8A	0.3111	0.0294	0.4621	0.053*
C9	0.5631 (3)	0.20167 (19)	0.15781 (18)	0.0501 (5)
H9A	0.6250	0.2481	0.0809	0.060*
C10	0.4506 (3)	0.27350 (18)	0.26465 (18)	0.0484 (5)
H10A	0.4375	0.3683	0.2602	0.058*
C11	0.2450 (2)	0.28855 (17)	0.49151 (16)	0.0388 (4)
C12	0.3181 (2)	0.37361 (19)	0.54246 (18)	0.0469 (5)
H12A	0.4384	0.3802	0.5042	0.056*
C13	0.2094 (3)	0.4484 (2)	0.65104 (19)	0.0516 (5)
H13A	0.2568	0.5055	0.6871	0.062*
C14	0.0297 (3)	0.43901 (19)	0.70679 (18)	0.0469 (4)
H14A	−0.0429	0.4906	0.7795	0.056*
C15	0.0660 (2)	0.27777 (17)	0.54661 (16)	0.0393 (4)
H15A	0.0194	0.2200	0.5108	0.047*
C16	−0.0432 (2)	0.35330 (17)	0.65519 (15)	0.0388 (4)
C17	−0.2405 (2)	0.34373 (17)	0.71527 (16)	0.0413 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0458 (8)	0.0799 (10)	0.0496 (7)	−0.0242 (7)	0.0005 (6)	−0.0184 (7)
O2	0.0515 (8)	0.0625 (9)	0.0572 (8)	−0.0111 (7)	0.0101 (6)	−0.0272 (7)
O3	0.0608 (10)	0.0918 (13)	0.0733 (10)	−0.0222 (9)	−0.0073 (8)	−0.0201 (9)
O4	0.0642 (10)	0.0820 (11)	0.0501 (8)	−0.0358 (8)	0.0032 (7)	−0.0173 (7)
N1	0.0570 (10)	0.0578 (10)	0.0506 (9)	−0.0097 (8)	0.0010 (7)	−0.0132 (8)
N2	0.0331 (7)	0.0408 (8)	0.0408 (7)	−0.0077 (6)	−0.0065 (6)	−0.0044 (6)
C1	0.0842 (16)	0.0437 (11)	0.0632 (13)	−0.0089 (10)	0.0087 (11)	−0.0138 (10)
C2	0.0801 (15)	0.0448 (11)	0.0489 (11)	−0.0109 (10)	0.0079 (10)	−0.0045 (9)
C3	0.0795 (15)	0.0595 (13)	0.0436 (10)	−0.0115 (11)	0.0092 (10)	−0.0007 (9)
C4	0.0781 (14)	0.0440 (10)	0.0470 (11)	−0.0038 (9)	0.0059 (9)	−0.0017 (9)
C5	0.0384 (9)	0.0431 (9)	0.0388 (9)	−0.0099 (7)	−0.0086 (7)	−0.0042 (7)
C6	0.0371 (9)	0.0402 (9)	0.0388 (9)	−0.0085 (7)	−0.0085 (7)	−0.0023 (7)
C7	0.0495 (10)	0.0378 (9)	0.0420 (9)	−0.0125 (7)	−0.0041 (7)	−0.0041 (7)
C8	0.0431 (9)	0.0430 (9)	0.0417 (9)	−0.0132 (7)	−0.0028 (7)	−0.0013 (7)
C9	0.0538 (11)	0.0420 (10)	0.0438 (9)	−0.0116 (8)	0.0016 (8)	0.0008 (8)
C10	0.0528 (11)	0.0362 (9)	0.0472 (10)	−0.0093 (8)	−0.0011 (8)	−0.0024 (8)
C11	0.0347 (9)	0.0409 (9)	0.0379 (8)	−0.0050 (7)	−0.0074 (7)	−0.0054 (7)
C12	0.0367 (9)	0.0502 (10)	0.0546 (10)	−0.0110 (8)	−0.0101 (8)	−0.0090 (8)
C13	0.0538 (11)	0.0529 (11)	0.0551 (10)	−0.0166 (9)	−0.0162 (8)	−0.0145 (9)
C14	0.0494 (10)	0.0452 (10)	0.0434 (9)	−0.0077 (8)	−0.0076 (7)	−0.0109 (8)
C15	0.0375 (9)	0.0410 (9)	0.0396 (9)	−0.0085 (7)	−0.0087 (7)	−0.0076 (7)
C16	0.0389 (9)	0.0378 (8)	0.0361 (8)	−0.0048 (7)	−0.0077 (7)	−0.0036 (7)
C17	0.0420 (9)	0.0383 (9)	0.0379 (8)	−0.0058 (7)	−0.0035 (7)	−0.0061 (7)

O1—C17	1.238 (2)	C8—H8A	0.9300
O2—C17	1.253 (2)	C9—C10	1.358 (3)
N1—C3	1.320 (3)	C9—H9A	0.9300
N1—C1	1.322 (3)	C10—H10A	0.9300
N2—C8	1.343 (2)	C11—C12	1.383 (3)
N2—C10	1.345 (2)	C11—C15	1.384 (2)
N2—C11	1.451 (2)	C12—C13	1.378 (3)
C1—C2	1.382 (3)	C12—H12A	0.9300
C1—H1A	0.9300	C13—C14	1.386 (3)
C2—C5	1.379 (3)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C16	1.390 (3)
C3—C4	1.367 (3)	C14—H14A	0.9300
C3—H3A	0.9300	C15—C16	1.382 (2)
C4—C5	1.374 (3)	C15—H15A	0.9300
C4—H4A	0.9300	C16—C17	1.519 (2)
C5—C6	1.480 (2)	O4—H3	0.891 (17)
C6—C9	1.395 (2)	O4—H4	0.847 (17)
C6—C7	1.396 (2)	O3—H2	0.880 (18)
C7—C8	1.368 (2)	O3—H1	0.904 (18)
C7—H7A	0.9300
C3—N1—C1	115.64 (17)	C10—C9—H9A	119.6
C8—N2—C10	119.98 (15)	C6—C9—H9A	119.6
C8—N2—C11	120.41 (14)	N2—C10—C9	121.01 (16)
C10—N2—C11	119.57 (14)	N2—C10—H10A	119.5
N1—C1—C2	123.91 (19)	C9—C10—H10A	119.5
N1—C1—H1A	118.0	C12—C11—C15	121.54 (16)
C2—C1—H1A	118.0	C12—C11—N2	119.25 (15)
C5—C2—C1	119.65 (17)	C15—C11—N2	119.20 (15)
C5—C2—H2A	120.2	C13—C12—C11	118.75 (16)
C1—C2—H2A	120.2	C13—C12—H12A	120.6
N1—C3—C4	124.66 (18)	C11—C12—H12A	120.6
N1—C3—H3A	117.7	C12—C13—C14	120.29 (17)
C4—C3—H3A	117.7	C12—C13—H13A	119.9
C3—C4—C5	119.83 (18)	C14—C13—H13A	119.9
C3—C4—H4A	120.1	C13—C14—C16	120.73 (17)
C5—C4—H4A	120.1	C13—C14—H14A	119.6
C4—C5—C2	116.29 (17)	C16—C14—H14A	119.6
C4—C5—C6	121.07 (16)	C16—C15—C11	119.65 (16)
C2—C5—C6	122.63 (15)	C16—C15—H15A	120.2
C9—C6—C7	116.72 (16)	C11—C15—H15A	120.2
C9—C6—C5	120.71 (15)	C15—C16—C14	119.05 (16)
C7—C6—C5	122.56 (15)	C15—C16—C17	120.11 (15)
C8—C7—C6	120.38 (16)	C14—C16—C17	120.83 (16)
C8—C7—H7A	119.8	O1—C17—O2	125.33 (17)
C6—C7—H7A	119.8	O1—C17—C16	117.90 (15)
N2—C8—C7	121.04 (15)	O2—C17—C16	116.75 (16)
N2—C8—H8A	119.5	H3—O4—H4	108 (3)
C7—C8—H8A	119.5	H2—O3—H1	105 (3)
C10—C9—C6	120.85 (16)
C3—N1—C1—C2	−0.3 (4)	C11—N2—C10—C9	177.37 (16)
N1—C1—C2—C5	−0.5 (4)	C6—C9—C10—N2	−0.7 (3)
C1—N1—C3—C4	0.7 (4)	C8—N2—C11—C12	127.44 (17)
N1—C3—C4—C5	−0.2 (4)	C10—N2—C11—C12	−50.1 (2)
C3—C4—C5—C2	−0.6 (3)	C8—N2—C11—C15	−53.1 (2)
C3—C4—C5—C6	178.5 (2)	C10—N2—C11—C15	129.41 (17)
C1—C2—C5—C4	0.9 (3)	C15—C11—C12—C13	0.3 (3)
C1—C2—C5—C6	−178.2 (2)	N2—C11—C12—C13	179.77 (15)
C4—C5—C6—C9	−12.6 (3)	C11—C12—C13—C14	−0.6 (3)
C2—C5—C6—C9	166.49 (19)	C12—C13—C14—C16	0.6 (3)
C4—C5—C6—C7	168.32 (19)	C12—C11—C15—C16	−0.1 (2)
C2—C5—C6—C7	−12.6 (3)	N2—C11—C15—C16	−179.52 (13)
C9—C6—C7—C8	−1.6 (3)	C11—C15—C16—C14	0.1 (2)
C5—C6—C7—C8	177.51 (15)	C11—C15—C16—C17	179.20 (14)
C10—N2—C8—C7	0.0 (3)	C13—C14—C16—C15	−0.4 (3)
C11—N2—C8—C7	−177.48 (15)	C13—C14—C16—C17	−179.46 (15)
C6—C7—C8—N2	0.9 (3)	C15—C16—C17—O1	−7.1 (2)
C7—C6—C9—C10	1.5 (3)	C14—C16—C17—O1	171.97 (16)
C5—C6—C9—C10	−177.65 (16)	C15—C16—C17—O2	171.73 (14)
C8—N2—C10—C9	−0.1 (3)	C14—C16—C17—O2	−9.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H3···O1	0.89 (3)	1.84 (2)	2.703 (2)	164 (1)
O3—H1···O2	0.91 (2)	1.94 (2)	2.843 (3)	174 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H3⋯O1	0.89 (3)	1.84 (2)	2.703 (2)	164 (1)
O3—H1⋯O2	0.91 (2)	1.94 (2)	2.843 (3)	174 (1)