4,4'-Bipyridine-2,2'-(1,2-phenylene-dioxy)diacetic acid-water (1/1/1).

In the title 1:1:1 adduct, C(10)H(8)N(2)·C(10)H(10)O(6)·H(2)O, the dihedral angle between the rings of the 4,4-bipyridine molecule is 10.981 (8)°. In the crystal, O-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules into a zigzag chain structure.

Related literature

For the synthesis of 1,2-phenyl­enedi(oxyacetic acid), see: Mirci (1990 ▶). For related structures, see: Soleimannejad et al. (2009 ▶); Yu et al. (2006 ▶). For hydrogen-bonding motifs, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H8N2·C10H10O6·H2O

M = 400.38

Monoclinic,

a = 11.566 (5) Å

b = 9.712 (5) Å

c = 16.810 (7) Å

β = 90.81 (2)°

V = 1888.2 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 291 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.979, T max = 0.987

18105 measured reflections

4306 independent reflections

2654 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.113

S = 0.97

4306 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013905/dn2556sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013905/dn2556Isup2.hkl

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

C10H8N2·C10H10O6·H2O	F(000) = 840
Mr = 400.38	Dx = 1.408 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11161 reflections
a = 11.566 (5) Å	θ = 3.0–27.5°
b = 9.712 (5) Å	µ = 0.11 mm−1
c = 16.810 (7) Å	T = 291 K
β = 90.81 (2)°	Rod, colorless
V = 1888.2 (15) Å3	0.20 × 0.18 × 0.12 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	4306 independent reflections
Radiation source: fine-focus sealed tube	2654 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scan	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −15→14
Tmin = 0.979, Tmax = 0.987	k = −12→12
18105 measured reflections	l = −21→21

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0647P)2] where P = (Fo2 + 2Fc2)/3
4306 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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 > 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
N1	0.60888 (10)	0.06435 (13)	0.44070 (7)	0.0574 (3)
C1	0.59235 (13)	−0.04189 (17)	0.39244 (9)	0.0616 (4)
H1	0.5467	−0.0293	0.3470	0.074*
C2	0.63933 (12)	−0.16976 (16)	0.40627 (8)	0.0588 (4)
H2	0.6265	−0.2406	0.3700	0.071*
C3	0.70588 (11)	−0.19349 (14)	0.47429 (8)	0.0462 (3)
C4	0.72238 (12)	−0.08127 (15)	0.52468 (9)	0.0574 (4)
H4	0.7662	−0.0910	0.5712	0.069*
C5	0.67402 (13)	0.04364 (16)	0.50574 (9)	0.0613 (4)
H5	0.6873	0.1175	0.5399	0.074*
C6	0.75714 (11)	−0.33068 (14)	0.49263 (8)	0.0460 (3)
C7	0.72463 (14)	−0.44768 (16)	0.45093 (9)	0.0662 (4)
H7	0.6697	−0.4416	0.4101	0.079*
C8	0.77316 (14)	−0.57246 (17)	0.46966 (10)	0.0672 (4)
H8	0.7498	−0.6493	0.4406	0.081*
C9	0.88302 (13)	−0.47824 (16)	0.56821 (9)	0.0609 (4)
H9	0.9375	−0.4879	0.6091	0.073*
C10	0.83819 (12)	−0.34962 (15)	0.55282 (9)	0.0579 (4)
H10	0.8626	−0.2748	0.5832	0.069*
C11	0.27722 (11)	0.59624 (14)	0.26783 (7)	0.0458 (3)
C12	0.32396 (13)	0.71838 (15)	0.29545 (8)	0.0554 (4)
H12	0.3895	0.7167	0.3282	0.066*
C13	0.27396 (13)	0.84376 (16)	0.27477 (9)	0.0597 (4)
H13	0.3061	0.9256	0.2935	0.072*
C14	0.17787 (14)	0.84657 (15)	0.22704 (9)	0.0594 (4)
H14	0.1442	0.9305	0.2135	0.071*
C15	0.12991 (12)	0.72505 (14)	0.19859 (9)	0.0561 (4)
H15	0.0644	0.7282	0.1659	0.067*
C16	0.17855 (11)	0.59898 (13)	0.21839 (8)	0.0460 (3)
C17	0.04541 (11)	0.47710 (14)	0.13642 (8)	0.0495 (3)
H17A	0.0694	0.5276	0.0897	0.059*
H17B	−0.0208	0.5239	0.1587	0.059*
C18	0.01249 (11)	0.33352 (14)	0.11347 (8)	0.0479 (3)
C19	0.41863 (12)	0.46231 (15)	0.33609 (8)	0.0542 (4)
H19A	0.4001	0.5044	0.3867	0.065*
H19B	0.4818	0.5135	0.3130	0.065*
C20	0.45447 (12)	0.31491 (16)	0.34906 (9)	0.0548 (4)
N2	0.85154 (10)	−0.58951 (13)	0.52696 (7)	0.0564 (3)
O1	0.13736 (8)	0.47386 (9)	0.19334 (6)	0.0545 (3)
O2	0.05129 (9)	0.23016 (10)	0.14397 (6)	0.0597 (3)
O3	−0.06491 (9)	0.33379 (10)	0.05595 (6)	0.0651 (3)
H23	−0.0867	0.2512	0.0481	0.098*
O4	0.32100 (8)	0.46709 (9)	0.28462 (6)	0.0531 (3)
O5	0.42135 (9)	0.21927 (11)	0.30849 (7)	0.0710 (3)
O6	0.52702 (9)	0.30628 (11)	0.40864 (6)	0.0709 (3)
H24	0.5506	0.2251	0.4185	0.106*
O7	0.17765 (9)	0.17334 (11)	0.28219 (6)	0.0712 (3)
H21	0.2472	0.2012	0.2804	0.107*
H22	0.1466	0.2093	0.2410	0.107*

	U11	U22	U33	U12	U13	U23
N1	0.0485 (7)	0.0614 (8)	0.0619 (7)	0.0020 (6)	−0.0057 (6)	0.0183 (6)
C1	0.0563 (9)	0.0752 (11)	0.0530 (9)	0.0049 (8)	−0.0126 (7)	0.0131 (8)
C2	0.0600 (9)	0.0681 (10)	0.0477 (8)	0.0021 (7)	−0.0126 (7)	0.0027 (7)
C3	0.0390 (7)	0.0545 (8)	0.0450 (7)	−0.0045 (6)	−0.0039 (6)	0.0072 (6)
C4	0.0596 (9)	0.0545 (9)	0.0576 (9)	−0.0024 (7)	−0.0206 (7)	0.0064 (7)
C5	0.0631 (9)	0.0544 (9)	0.0659 (10)	−0.0012 (7)	−0.0148 (8)	0.0071 (7)
C6	0.0416 (7)	0.0524 (8)	0.0438 (7)	−0.0029 (6)	−0.0028 (6)	0.0038 (6)
C7	0.0703 (10)	0.0606 (10)	0.0669 (10)	0.0008 (8)	−0.0296 (8)	−0.0013 (7)
C8	0.0746 (11)	0.0555 (9)	0.0707 (10)	−0.0005 (8)	−0.0216 (9)	−0.0062 (8)
C9	0.0601 (9)	0.0614 (10)	0.0605 (9)	0.0063 (7)	−0.0208 (7)	−0.0002 (7)
C10	0.0591 (8)	0.0562 (9)	0.0578 (9)	0.0015 (7)	−0.0184 (7)	−0.0038 (7)
C11	0.0460 (7)	0.0424 (7)	0.0491 (8)	0.0020 (6)	−0.0019 (6)	0.0038 (6)
C12	0.0569 (8)	0.0524 (8)	0.0564 (9)	−0.0040 (7)	−0.0123 (7)	−0.0008 (7)
C13	0.0711 (10)	0.0460 (8)	0.0619 (9)	−0.0055 (7)	−0.0024 (8)	−0.0063 (7)
C14	0.0701 (9)	0.0429 (8)	0.0653 (9)	0.0085 (7)	−0.0010 (8)	−0.0015 (7)
C15	0.0536 (8)	0.0473 (8)	0.0673 (9)	0.0062 (6)	−0.0098 (7)	−0.0008 (7)
C16	0.0434 (7)	0.0412 (7)	0.0532 (8)	0.0010 (6)	−0.0036 (6)	−0.0006 (6)
C17	0.0436 (7)	0.0486 (8)	0.0559 (8)	0.0043 (6)	−0.0107 (6)	0.0010 (6)
C18	0.0419 (7)	0.0512 (8)	0.0504 (8)	0.0016 (6)	−0.0037 (6)	0.0006 (6)
C19	0.0486 (8)	0.0563 (9)	0.0572 (8)	−0.0028 (6)	−0.0138 (7)	0.0076 (7)
C20	0.0420 (7)	0.0605 (9)	0.0615 (9)	−0.0020 (7)	−0.0072 (7)	0.0113 (7)
N2	0.0542 (7)	0.0556 (7)	0.0592 (7)	0.0048 (6)	−0.0051 (6)	0.0036 (6)
O1	0.0508 (5)	0.0404 (5)	0.0718 (6)	0.0025 (4)	−0.0210 (5)	−0.0003 (4)
O2	0.0639 (6)	0.0475 (6)	0.0672 (7)	0.0036 (5)	−0.0183 (5)	0.0005 (5)
O3	0.0661 (6)	0.0540 (6)	0.0743 (7)	−0.0046 (5)	−0.0293 (6)	0.0030 (5)
O4	0.0492 (5)	0.0462 (6)	0.0635 (6)	0.0002 (4)	−0.0167 (4)	0.0052 (4)
O5	0.0635 (7)	0.0599 (7)	0.0888 (8)	0.0060 (5)	−0.0230 (6)	−0.0003 (6)
O6	0.0665 (7)	0.0639 (7)	0.0812 (8)	0.0023 (5)	−0.0319 (6)	0.0154 (6)
O7	0.0797 (7)	0.0581 (7)	0.0750 (7)	−0.0155 (5)	−0.0260 (6)	0.0135 (5)

N1—C1	1.325 (2)	C12—H12	0.9300
N1—C5	1.3342 (18)	C13—C14	1.362 (2)
C1—C2	1.374 (2)	C13—H13	0.9300
C1—H1	0.9300	C14—C15	1.386 (2)
C2—C3	1.3885 (18)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.3861 (19)
C3—C4	1.392 (2)	C15—H15	0.9300
C3—C6	1.489 (2)	C16—O1	1.3695 (16)
C4—C5	1.371 (2)	C17—O1	1.4208 (15)
C4—H4	0.9300	C17—C18	1.495 (2)
C5—H5	0.9300	C17—H17A	0.9700
C6—C10	1.3818 (18)	C17—H17B	0.9700
C6—C7	1.384 (2)	C18—O2	1.2105 (16)
C7—C8	1.370 (2)	C18—O3	1.3083 (16)
C7—H7	0.9300	C19—O4	1.4136 (15)
C8—N2	1.3237 (18)	C19—C20	1.505 (2)
C8—H8	0.9300	C19—H19A	0.9700
C9—N2	1.3320 (19)	C19—H19B	0.9700
C9—C10	1.376 (2)	C20—O5	1.2113 (18)
C9—H9	0.9300	C20—O6	1.3002 (16)
C10—H10	0.9300	O3—H23	0.8499
C11—O4	1.3803 (17)	O6—H24	0.8500
C11—C12	1.3812 (19)	O7—H21	0.8499
C11—C16	1.4025 (18)	O7—H22	0.8501
C12—C13	1.390 (2)
C1—N1—C5	117.34 (13)	C14—C13—C12	119.87 (13)
N1—C1—C2	123.17 (12)	C14—C13—H13	120.1
N1—C1—H1	118.4	C12—C13—H13	120.1
C2—C1—H1	118.4	C13—C14—C15	120.36 (13)
C1—C2—C3	120.17 (14)	C13—C14—H14	119.8
C1—C2—H2	119.9	C15—C14—H14	119.8
C3—C2—H2	119.9	C16—C15—C14	120.67 (13)
C2—C3—C4	116.16 (13)	C16—C15—H15	119.7
C2—C3—C6	122.24 (13)	C14—C15—H15	119.7
C4—C3—C6	121.60 (11)	O1—C16—C15	124.87 (11)
C5—C4—C3	119.96 (12)	O1—C16—C11	116.23 (11)
C5—C4—H4	120.0	C15—C16—C11	118.90 (12)
C3—C4—H4	120.0	O1—C17—C18	109.80 (10)
N1—C5—C4	123.18 (14)	O1—C17—H17A	109.7
N1—C5—H5	118.4	C18—C17—H17A	109.7
C4—C5—H5	118.4	O1—C17—H17B	109.7
C10—C6—C7	115.98 (13)	C18—C17—H17B	109.7
C10—C6—C3	122.33 (12)	H17A—C17—H17B	108.2
C7—C6—C3	121.68 (12)	O2—C18—O3	124.09 (13)
C8—C7—C6	120.14 (13)	O2—C18—C17	124.94 (12)
C8—C7—H7	119.9	O3—C18—C17	110.98 (11)
C6—C7—H7	119.9	O4—C19—C20	109.62 (11)
N2—C8—C7	123.49 (14)	O4—C19—H19A	109.7
N2—C8—H8	118.3	C20—C19—H19A	109.7
C7—C8—H8	118.3	O4—C19—H19B	109.7
N2—C9—C10	122.64 (12)	C20—C19—H19B	109.7
N2—C9—H9	118.7	H19A—C19—H19B	108.2
C10—C9—H9	118.7	O5—C20—O6	125.43 (14)
C9—C10—C6	120.57 (13)	O5—C20—C19	124.30 (12)
C9—C10—H10	119.7	O6—C20—C19	110.26 (13)
C6—C10—H10	119.7	C8—N2—C9	117.18 (13)
O4—C11—C12	124.82 (11)	C16—O1—C17	116.18 (10)
O4—C11—C16	115.56 (11)	C18—O3—H23	108.1
C12—C11—C16	119.61 (11)	C11—O4—C19	116.26 (10)
C11—C12—C13	120.59 (12)	C20—O6—H24	114.3
C11—C12—H12	119.7	H21—O7—H22	103.2
C13—C12—H12	119.7

D—H···A	D—H	H···A	D···A	D—H···A
O3—H23···N2i	0.85	1.76	2.6051 (19)	173
O6—H24···N1	0.85	1.74	2.5871 (19)	176
O7—H21···O5	0.85	2.07	2.8817 (19)	160
O7—H22···O2	0.85	1.97	2.7826 (17)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H23⋯N2i	0.85	1.76	2.6051 (19)	173
O6—H24⋯N1	0.85	1.74	2.5871 (19)	176
O7—H21⋯O5	0.85	2.07	2.8817 (19)	160
O7—H22⋯O2	0.85	1.97	2.7826 (17)	161

Symmetry code: (i) .