4,4′-Imino­dipyridinium 5-hydroxy­isophthalate trihydrate

In the title hydrated salt, C₁₀H₁₁N₂⁺·C₈H₄O₅⁻·3H₂O, doubly protonated 4,4′-dipyridylamine mol­ecules engage in N—H...O hydrogen bonding with 5-hydroxy­isophthalate dianions to form undulating one-dimensional chains, which aggregate into three dimensions by O—H...O and N—H...O hydrogen-bonding patterns mediated by water mol­ecules of crystallization.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.119
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.

Author Response: CCD detector used

Alert level B
PLAT410_ALERT_2_B Short Intra H...H Contact  H2     ..  H9      ..       1.83 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.15
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C18 H21 N3 O8
            Atom count from _chemical_formula_moiety:C18 H21 N2 O8
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         13

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Co-crystals of carboxylic acids and amines or imines have been the focus of recent studies in part because of potentially useful physical properties such as ferroelectricity (Horiuchi et al., 2005). Also, the stability of pharmaceutically important formulations can be increased by co-crystal formation (Trask et al., 2005). Proton transfer between carboxylic acid and pyridine components has been observed in several co-crystals, with the resulting charge-separated hydrogen bonding interactions exerting strong structure directing effects (Bhogala & Nangia, 2003).

The hydrated title salt was obtained during an attempt to synthesize a zinc-based coordination polymer containing 4,4'-dipyridylamine (dpa) and 5-hydroxyisophthalate (hip). The asymmetric unit consists of a doubly protonated [H₂dpa]²⁺ dication, a doubly deprotonated [hip]^2- anion, and three water molecules of crystallization (Fig. 1). The similar C—O bond lengths at the carboxylate termini reflect the presence of delocalized π bonds (Table 1).

Adjacent [H₂dpa]²⁺ and [hip]^2- moieties interact via N—H···O hydrogen bonding to construct undulating one-dimensional chains that course parallel to the b crystal direction. These in turn interact through O—H···O and N—H···O supramolecular interactions mediated by the amine functional group of [H₂dpa]²⁺, the hydroxy group within [hip]^2- and water molecules of crystallization to form two-dimensional layer motifs coincident with the [101] crystal planes (Fig. 2). The [H₂dpa]²⁺ cations exhibit a slight inter-ring torsion of ~0.8° in order to maximize the supramolecular contacts. The {[H₂dpa][hip]^.3H₂O} layers subsequently stack along the (101) crystal direction through O—H···O hydrogen bonding patterns between water molecules of type O2W and O3W to create the three-dimensional structure of (I) (Fig. 3). Interlayer connectivity is enhanced by π-π stacking mechanisms and non-classical C—H···O interactions. Metrical parameters for the classical hydrogen bonding interactions are given in the table.

Related literature

A salt containing monoprotonated 4,4'-dipyridylamine and singly deprotonated isophthalic acid has been previously reported (Amoore & Kepert, 2005 or??2006). In contrast to the title compound, no water molecules of crystallization were observed.

For related literature, see: Bhogala & Nangia (2003); Horiuchi et al. (2005); Trask et al. (2005); Zapf et al. (1998).

S2. Experimental

Zinc nitrate hexahydrate and 5-hydroxyisophthalic acid were obtained commercially. 4,4'-dipyridylamine was prepared via a published procedure (GET, et al., GET). A mixture of zinc nitrate hexahydrate (110 mg, 0.37 mmol), 5-hydroxyisophthalic acid (67 mg, 0.37 mmol), 4,4'-dipyridylamine (127 mg, 0.74 mmol) and 10.0 g water (550 mmol) was placed into a 23 ml Teflon-lined Parr Acid Digestion bomb, which was then heated under autogenous pressure at 393 K for 72 h. Large white rhombs of the title compound were isolated after cooling, along with an amorphous white solid.

S3. Refinement

All H atoms bound to C atoms were placed in calculated positions, with C—H = 0.95 Å and refined in riding mode with U_iso = 1.2U_eq(C). All H atoms bound to O atoms were placed in calculated positions. The H atoms bound to N and O were found via Fourier difference map, restrained with N—H = 0.85 (2) Å or O—H = 0.89 (2) Å, and refined with U_iso = 1.2U_eq(O,N).

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalMaker (CrystalMaker, 2005); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Asymmetric unit of the title compound, showing 50% probability ellipsoids and atom numbering scheme. Most hydrogen atoms have been omitted for clarity.
	Fig. 2. A layer in the title compund. Color codes: light-blue N, red O within organic moieties, orange O within water molecules, black C, pink H. Hydrogen bonding is shown as dashed lines.
	Fig. 3. Packing diagram illustrating the stacking of layers to form the 3-D crystal structure of the title compound. Hydrogen bonding is shown as dashed lines.

4,4'-Iminodipyridinium 5-hydroxyisophthalate trihydrate

Crystal data

C10H11N2^+·C8H4O5^−·3H2O	F(000) = 856
Mr = 407.38	Dx = 1.447 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 18586 reflections
a = 7.266 (3) Å	θ = 2.5–28.2°
b = 32.701 (12) Å	µ = 0.12 mm^−1
c = 8.373 (3) Å	T = 293 K
β = 109.971 (6)°	Rhomb, colourless
V = 1869.7 (12) Å^3	0.70 × 0.25 × 0.25 mm
Z = 4

Data collection

Bruker SMART 1K diffractometer	4299 independent reflections
Radiation source: fine-focus sealed tube	3383 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scans	θmax = 28.2°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.844, Tmax = 0.970	k = −43→42
18586 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0567P)^2 + 0.5827P] where P = (Fo^2 + 2Fc^2)/3
4299 reflections	(Δ/σ)max < 0.001
292 parameters	Δρmax = 0.21 e Å^−3
13 restraints	Δρmin = −0.23 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.17693 (18)	0.21437 (3)	0.25784 (15)	0.0438 (3)
O1W	0.1022 (2)	−0.07026 (4)	0.21597 (15)	0.0478 (3)
H1WA	0.141 (3)	−0.0644 (6)	0.130 (2)	0.057*
H1WB	0.056 (3)	−0.0470 (5)	0.238 (3)	0.057*
O2	−0.08396 (17)	0.18913 (3)	0.05970 (14)	0.0421 (3)
O2W	0.3655 (2)	0.26570 (5)	0.52078 (19)	0.0629 (4)
H2WA	0.303 (3)	0.2478 (7)	0.447 (3)	0.075*
H2WB	0.299 (3)	0.2692 (7)	0.588 (3)	0.075*
O3	−0.19225 (18)	0.03830 (3)	0.05520 (14)	0.0434 (3)
O3W	0.5209 (2)	0.33012 (5)	0.3846 (2)	0.0749 (5)
H3WA	0.463 (4)	0.3108 (7)	0.418 (3)	0.090*
H3WB	0.643 (2)	0.3273 (8)	0.431 (3)	0.090*
O4	−0.0280 (2)	0.00170 (3)	0.28294 (16)	0.0501 (3)
O5	0.3678 (2)	0.10164 (4)	0.70746 (15)	0.0517 (4)
H5O	0.410 (3)	0.1259 (5)	0.750 (3)	0.062*
N1	0.3734 (2)	0.47531 (4)	0.61321 (16)	0.0352 (3)
H1N	0.301 (2)	0.4950 (5)	0.537 (2)	0.042*
N2	0.69030 (18)	0.39251 (4)	0.97808 (15)	0.0296 (3)
H2N	0.754 (2)	0.4053 (5)	1.0786 (18)	0.035*
N3	0.8395 (2)	0.27018 (4)	1.02502 (17)	0.0379 (3)
H3N	0.872 (3)	0.2428 (5)	1.039 (2)	0.045*
C1	0.3611 (2)	0.43590 (5)	0.5722 (2)	0.0403 (4)
H1	0.2815	0.4280	0.4639	0.048*
C2	0.4631 (2)	0.40653 (5)	0.6854 (2)	0.0376 (4)
H2	0.4528	0.3791	0.6535	0.045*
C3	0.5821 (2)	0.41810 (4)	0.84837 (18)	0.0274 (3)
C4	0.5959 (2)	0.45988 (5)	0.88553 (19)	0.0368 (4)
H4	0.6770	0.4690	0.9914	0.044*
C5	0.4905 (3)	0.48740 (5)	0.7667 (2)	0.0398 (4)
H5	0.5005	0.5151	0.7932	0.048*
C6	0.9166 (3)	0.29658 (5)	1.1534 (2)	0.0434 (4)
H6	1.0078	0.2873	1.2546	0.052*
C7	0.8632 (3)	0.33660 (5)	1.1376 (2)	0.0387 (4)
H7	0.9159	0.3543	1.2287	0.046*
C8	0.7285 (2)	0.35143 (4)	0.98427 (18)	0.0272 (3)
C9	0.6495 (3)	0.32274 (5)	0.8556 (2)	0.0418 (4)
H9	0.5574	0.3308	0.7528	0.050*
C10	0.7077 (3)	0.28279 (5)	0.8809 (2)	0.0429 (4)
H10	0.6533	0.2639	0.7944	0.052*
C11	0.0241 (2)	0.07331 (4)	0.29357 (18)	0.0270 (3)
C12	−0.0087 (2)	0.11074 (4)	0.20894 (17)	0.0268 (3)
H12	−0.0965	0.1125	0.0983	0.032*
C13	0.0899 (2)	0.14548 (4)	0.28976 (17)	0.0260 (3)
C14	0.2193 (2)	0.14313 (5)	0.45664 (18)	0.0298 (3)
H14	0.2876	0.1662	0.5098	0.036*
C15	0.2460 (2)	0.10607 (5)	0.54350 (18)	0.0324 (3)
C16	0.1486 (2)	0.07122 (4)	0.46149 (18)	0.0312 (3)
H16	0.1670	0.0464	0.5193	0.037*
C17	0.0591 (2)	0.18573 (4)	0.19650 (18)	0.0295 (3)
C18	−0.0714 (2)	0.03461 (4)	0.20551 (19)	0.0316 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0534 (7)	0.0261 (6)	0.0406 (6)	−0.0103 (5)	0.0013 (5)	0.0009 (5)
O1W	0.0707 (9)	0.0344 (6)	0.0330 (6)	0.0092 (6)	0.0108 (6)	0.0052 (5)
O2	0.0473 (7)	0.0253 (6)	0.0385 (6)	0.0005 (5)	−0.0051 (5)	0.0047 (5)
O2W	0.0617 (9)	0.0714 (10)	0.0543 (9)	−0.0202 (8)	0.0182 (7)	−0.0257 (7)
O3	0.0573 (7)	0.0304 (6)	0.0346 (6)	−0.0140 (5)	0.0055 (5)	−0.0067 (4)
O3W	0.0541 (9)	0.0675 (11)	0.0819 (12)	0.0072 (8)	−0.0040 (8)	0.0278 (9)
O4	0.0779 (9)	0.0212 (6)	0.0485 (7)	−0.0009 (6)	0.0183 (6)	0.0022 (5)
O5	0.0616 (8)	0.0461 (8)	0.0292 (6)	−0.0090 (6)	−0.0081 (5)	0.0076 (5)
N1	0.0388 (7)	0.0313 (7)	0.0320 (7)	0.0102 (6)	0.0075 (5)	0.0083 (5)
N2	0.0344 (7)	0.0240 (6)	0.0253 (6)	0.0024 (5)	0.0038 (5)	0.0012 (5)
N3	0.0455 (8)	0.0231 (6)	0.0403 (7)	0.0057 (6)	0.0086 (6)	0.0056 (5)
C1	0.0429 (9)	0.0384 (9)	0.0299 (8)	0.0056 (7)	−0.0003 (7)	0.0015 (6)
C2	0.0444 (9)	0.0250 (8)	0.0339 (8)	0.0045 (6)	0.0012 (7)	−0.0003 (6)
C3	0.0278 (7)	0.0260 (7)	0.0282 (7)	0.0037 (5)	0.0090 (6)	0.0036 (5)
C4	0.0458 (9)	0.0286 (8)	0.0281 (7)	0.0037 (7)	0.0024 (6)	−0.0005 (6)
C5	0.0495 (10)	0.0264 (8)	0.0377 (9)	0.0071 (7)	0.0075 (7)	0.0015 (6)
C6	0.0527 (10)	0.0334 (9)	0.0333 (8)	0.0094 (7)	0.0007 (7)	0.0079 (6)
C7	0.0495 (10)	0.0298 (8)	0.0282 (8)	0.0035 (7)	0.0020 (7)	0.0009 (6)
C8	0.0274 (7)	0.0248 (7)	0.0290 (7)	0.0018 (5)	0.0092 (6)	0.0040 (5)
C9	0.0475 (10)	0.0300 (8)	0.0334 (8)	0.0060 (7)	−0.0049 (7)	0.0007 (6)
C10	0.0495 (10)	0.0282 (8)	0.0400 (9)	0.0024 (7)	0.0009 (7)	−0.0035 (7)
C11	0.0299 (7)	0.0219 (7)	0.0288 (7)	0.0007 (5)	0.0098 (6)	−0.0007 (5)
C12	0.0285 (7)	0.0235 (7)	0.0243 (7)	0.0012 (5)	0.0037 (5)	−0.0009 (5)
C13	0.0278 (7)	0.0223 (7)	0.0272 (7)	0.0018 (5)	0.0084 (6)	−0.0008 (5)
C14	0.0303 (7)	0.0269 (7)	0.0291 (7)	−0.0034 (6)	0.0062 (6)	−0.0046 (5)
C15	0.0324 (8)	0.0349 (8)	0.0249 (7)	−0.0001 (6)	0.0034 (6)	0.0025 (6)
C16	0.0357 (8)	0.0246 (7)	0.0312 (8)	0.0027 (6)	0.0086 (6)	0.0059 (6)
C17	0.0357 (8)	0.0211 (7)	0.0286 (7)	0.0009 (6)	0.0070 (6)	−0.0016 (5)
C18	0.0398 (8)	0.0243 (7)	0.0329 (8)	−0.0027 (6)	0.0150 (6)	−0.0032 (6)

Geometric parameters (Å, º)

O1—C17	1.2546 (18)	C2—H2	0.9300
O1W—H1WA	0.878 (15)	C3—C4	1.397 (2)
O1W—H1WB	0.872 (15)	C4—C5	1.366 (2)
O2—C17	1.2614 (18)	C4—H4	0.9300
O2W—H2WA	0.861 (16)	C5—H5	0.9300
O2W—H2WB	0.871 (16)	C6—C7	1.358 (2)
O3—C18	1.2706 (19)	C6—H6	0.9300
O3W—H3WA	0.855 (16)	C7—C8	1.408 (2)
O3W—H3WB	0.841 (17)	C7—H7	0.9300
O4—C18	1.2402 (19)	C8—C9	1.396 (2)
O5—C15	1.3632 (18)	C9—C10	1.367 (2)
O5—H5O	0.882 (15)	C9—H9	0.9300
N1—C1	1.329 (2)	C10—H10	0.9300
N1—C5	1.336 (2)	C11—C16	1.390 (2)
N1—H1N	0.934 (14)	C11—C12	1.393 (2)
N2—C8	1.3691 (19)	C11—C18	1.509 (2)
N2—C3	1.3836 (18)	C12—C13	1.3895 (19)
N2—H2N	0.912 (14)	C12—H12	0.9300
N3—C10	1.325 (2)	C13—C14	1.395 (2)
N3—C6	1.343 (2)	C13—C17	1.507 (2)
N3—H3N	0.922 (14)	C14—C15	1.392 (2)
C1—C2	1.375 (2)	C14—H14	0.9300
C1—H1	0.9300	C15—C16	1.393 (2)
C2—C3	1.396 (2)	C16—H16	0.9300
H1WA—O1W—H1WB	103.5 (18)	N2—C8—C9	127.28 (13)
H2WA—O2W—H2WB	107 (2)	N2—C8—C7	116.18 (13)
H3WA—O3W—H3WB	109 (2)	C9—C8—C7	116.53 (14)
C15—O5—H5O	109.3 (14)	C10—C9—C8	119.94 (14)
C1—N1—C5	120.00 (14)	C10—C9—H9	120.0
C1—N1—H1N	121.3 (11)	C8—C9—H9	120.0
C5—N1—H1N	118.7 (11)	N3—C10—C9	121.84 (15)
C8—N2—C3	132.57 (13)	N3—C10—H10	119.1
C8—N2—H2N	112.5 (11)	C9—C10—H10	119.1
C3—N2—H2N	114.8 (11)	C16—C11—C12	119.78 (13)
C10—N3—C6	120.21 (14)	C16—C11—C18	119.01 (13)
C10—N3—H3N	119.6 (12)	C12—C11—C18	121.20 (13)
C6—N3—H3N	120.1 (12)	C13—C12—C11	120.04 (13)
N1—C1—C2	121.76 (15)	C13—C12—H12	120.0
N1—C1—H1	119.1	C11—C12—H12	120.0
C2—C1—H1	119.1	C12—C13—C14	120.11 (13)
C1—C2—C3	119.54 (15)	C12—C13—C17	120.06 (13)
C1—C2—H2	120.2	C14—C13—C17	119.82 (13)
C3—C2—H2	120.2	C15—C14—C13	119.83 (13)
N2—C3—C2	126.87 (14)	C15—C14—H14	120.1
N2—C3—C4	115.99 (13)	C13—C14—H14	120.1
C2—C3—C4	117.14 (13)	O5—C15—C14	123.04 (14)
C5—C4—C3	120.15 (14)	O5—C15—C16	117.08 (14)
C5—C4—H4	119.9	C14—C15—C16	119.87 (13)
C3—C4—H4	119.9	C11—C16—C15	120.28 (13)
N1—C5—C4	121.35 (15)	C11—C16—H16	119.9
N1—C5—H5	119.3	C15—C16—H16	119.9
C4—C5—H5	119.3	O1—C17—O2	122.78 (13)
N3—C6—C7	120.96 (15)	O1—C17—C13	118.67 (13)
N3—C6—H6	119.5	O2—C17—C13	118.55 (13)
C7—C6—H6	119.5	O4—C18—O3	124.50 (14)
C6—C7—C8	120.46 (15)	O4—C18—C11	118.68 (14)
C6—C7—H7	119.8	O3—C18—C11	116.82 (13)
C8—C7—H7	119.8
C5—N1—C1—C2	1.5 (3)	C16—C11—C12—C13	2.9 (2)
N1—C1—C2—C3	0.4 (3)	C18—C11—C12—C13	−176.23 (13)
C8—N2—C3—C2	6.9 (3)	C11—C12—C13—C14	−1.1 (2)
C8—N2—C3—C4	−172.55 (15)	C11—C12—C13—C17	178.20 (13)
C1—C2—C3—N2	178.42 (15)	C12—C13—C14—C15	−1.5 (2)
C1—C2—C3—C4	−2.2 (2)	C17—C13—C14—C15	179.22 (13)
N2—C3—C4—C5	−178.40 (15)	C13—C14—C15—O5	−179.00 (14)
C2—C3—C4—C5	2.1 (2)	C13—C14—C15—C16	2.2 (2)
C1—N1—C5—C4	−1.6 (3)	C12—C11—C16—C15	−2.3 (2)
C3—C4—C5—N1	−0.3 (3)	C18—C11—C16—C15	176.95 (14)
C10—N3—C6—C7	−0.8 (3)	O5—C15—C16—C11	−179.19 (14)
N3—C6—C7—C8	−1.4 (3)	C14—C15—C16—C11	−0.3 (2)
C3—N2—C8—C9	−5.9 (3)	C12—C13—C17—O1	−165.67 (14)
C3—N2—C8—C7	173.86 (15)	C14—C13—C17—O1	13.6 (2)
C6—C7—C8—N2	−177.25 (16)	C12—C13—C17—O2	14.1 (2)
C6—C7—C8—C9	2.5 (2)	C14—C13—C17—O2	−166.62 (14)
N2—C8—C9—C10	178.13 (16)	C16—C11—C18—O4	−3.7 (2)
C7—C8—C9—C10	−1.6 (2)	C12—C11—C18—O4	175.53 (14)
C6—N3—C10—C9	1.7 (3)	C16—C11—C18—O3	176.31 (14)
C8—C9—C10—N3	−0.5 (3)	C12—C11—C18—O3	−4.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3^i	0.88 (2)	1.92 (2)	2.7732 (19)	165 (2)
O1W—H1WB···O4	0.87 (2)	1.79 (2)	2.6661 (19)	178 (2)
O2W—H2WA···O1	0.86 (2)	1.88 (2)	2.7351 (18)	170 (2)
O2W—H2WB···O1^ii	0.87 (2)	1.99 (2)	2.846 (2)	170 (2)
O3W—H3WA···O2W	0.86 (2)	1.96 (2)	2.809 (2)	172 (3)
O3W—H3WB···O2^iii	0.84 (2)	1.98 (2)	2.813 (2)	169 (3)
O5—H5O···O3W^ii	0.88 (2)	1.83 (2)	2.700 (2)	167 (2)
N1—H1N···O3^iv	0.93 (1)	1.67 (2)	2.5876 (17)	165 (2)
N2—H2N···O1W^v	0.91 (1)	1.86 (1)	2.7712 (19)	177 (2)
N3—H3N···O2^vi	0.92 (1)	1.78 (2)	2.7034 (19)	176 (2)

Symmetry codes: (i) −x, −y, −z; (ii) x, −y+1/2, z+1/2; (iii) x+1, −y+1/2, z+1/2; (iv) −x, y+1/2, −z+1/2; (v) −x+1, y+1/2, −z+3/2; (vi) x+1, y, z+1.