Bis(2-amino-4-methyl-pyridinium) terephthalate tetra-hydrate.

In the crystal structure of the title salt, 2C(6)H(9)N(2) (+)·C(8)H(4)O(4) (2-)·4H(2)O, the terephthalate carboxyl-ate groups inter-acts with the 2-amino-4-methyl-pyridinium cations via a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. The water mol-ecules form an R(6) (6)(12) ring motif through O-H⋯O hydrogen bonds and these motifs are fused, forming a supra-molecular chain along the c axis. The R(2) (2)(8) and R(6) (6)(12) ring motifs are connected via O-H⋯O hydrogen bonds. In addition, π-π stacking inter-actions are observed between the pyridinium rings [centroid-centroid distance = 3.522 (12) Å].

Related literature

For details of non-covalent inter­actions, see: Desiraju (2007 ▶); Corna et al. (2004 ▶); Aakeröy & Seddon (1993 ▶). For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997 ▶); Katritzky et al. (1996 ▶). For the applications of terephthalic acid, see: Serre et al. (2007 ▶); Mukherjee et al. (2004 ▶); Sun et al. (2000 ▶); Lynch & Jones (2004 ▶); Spencer et al. (2004 ▶); Devi & Muthiah (2007 ▶). For details of hydrogen bonding, see: Jeffrey & Saenger (1991 ▶); Jeffrey (1997 ▶); Scheiner (1997 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

2C6H9N2 +·C8H4O4 2−·4H2O

M = 454.48

Monoclinic,

a = 17.6290 (16) Å

b = 13.8091 (13) Å

c = 9.2518 (9) Å

β = 93.940 (2)°

V = 2246.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.45 × 0.27 × 0.07 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.955, T max = 0.992

12651 measured reflections

3275 independent reflections

3004 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.06

3275 reflections

347 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025651/ci5123sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025651/ci5123Isup2.hkl

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

2C6H9N2+·C8H4O42−·4H2O	F(000) = 968
Mr = 454.48	Dx = 1.343 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 4430 reflections
a = 17.6290 (16) Å	θ = 2.3–30.0°
b = 13.8091 (13) Å	µ = 0.11 mm−1
c = 9.2518 (9) Å	T = 100 K
β = 93.940 (2)°	Plate, colourless
V = 2246.9 (4) Å3	0.45 × 0.27 × 0.07 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	3275 independent reflections
Radiation source: fine-focus sealed tube	3004 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 30.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→24
Tmin = 0.955, Tmax = 0.992	k = −19→13
12651 measured reflections	l = −13→13

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0657P)2 + 0.2622P] where P = (Fo2 + 2Fc2)/3
3275 reflections	(Δ/σ)max = 0.001
347 parameters	Δρmax = 0.46 e Å−3
2 restraints	Δρmin = −0.20 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1A	0.73749 (9)	0.27051 (12)	0.16796 (17)	0.0163 (3)
N2A	0.75478 (10)	0.43694 (12)	0.17137 (18)	0.0204 (3)
C1A	0.73275 (10)	0.35697 (14)	0.09938 (19)	0.0163 (4)
C2A	0.70424 (11)	0.35868 (15)	−0.0481 (2)	0.0187 (4)
H2AA	0.7016	0.4170	−0.0983	0.022*
C3A	0.68056 (10)	0.27471 (14)	−0.11685 (19)	0.0173 (4)
C4A	0.68604 (11)	0.18620 (14)	−0.0396 (2)	0.0188 (4)
H4AA	0.6702	0.1286	−0.0841	0.023*
C5A	0.71489 (11)	0.18657 (15)	0.1009 (2)	0.0202 (4)
H5AA	0.7192	0.1285	0.1518	0.024*
C6A	0.64919 (12)	0.27652 (16)	−0.2720 (2)	0.0230 (4)
H6AA	0.6584	0.3389	−0.3133	0.034*
H6AB	0.5954	0.2645	−0.2762	0.034*
H6AC	0.6736	0.2274	−0.3257	0.034*
N1B	0.48583 (10)	0.31843 (13)	−0.04463 (18)	0.0195 (3)
N2B	0.49724 (10)	0.15247 (12)	−0.02353 (17)	0.0184 (3)
C1B	0.50869 (11)	0.23962 (14)	0.03428 (19)	0.0169 (4)
C2B	0.54266 (11)	0.25447 (16)	0.1759 (2)	0.0183 (4)
H2BA	0.5582	0.2015	0.2326	0.022*
C3B	0.55264 (11)	0.34599 (15)	0.2296 (2)	0.0200 (4)
C4B	0.52752 (12)	0.42658 (16)	0.1435 (2)	0.0230 (4)
H4BA	0.5336	0.4894	0.1788	0.028*
C5B	0.49433 (12)	0.41005 (15)	0.0082 (2)	0.0220 (4)
H5BA	0.4773	0.4622	−0.0487	0.026*
C6B	0.58818 (13)	0.36063 (18)	0.3806 (2)	0.0271 (5)
H6BA	0.6173	0.3043	0.4099	0.041*
H6BB	0.5490	0.3707	0.4461	0.041*
H6BC	0.6210	0.4162	0.3822	0.041*
O1	0.79418 (8)	0.41120 (10)	0.47912 (14)	0.0196 (3)
O2	0.80222 (9)	0.25260 (10)	0.43950 (15)	0.0196 (3)
O3	0.95157 (10)	0.35431 (12)	1.18466 (16)	0.0258 (3)
O4	0.93553 (9)	0.19471 (11)	1.17111 (15)	0.0227 (3)
C7	0.87740 (10)	0.39144 (13)	0.75006 (19)	0.0156 (3)
H7A	0.8791	0.4520	0.7063	0.019*
C8	0.90527 (10)	0.37998 (14)	0.89289 (19)	0.0158 (3)
H8A	0.9248	0.4331	0.9447	0.019*
C9	0.90425 (10)	0.28948 (14)	0.95947 (18)	0.0148 (3)
C10	0.87640 (10)	0.20985 (14)	0.87956 (19)	0.0153 (3)
H10A	0.8771	0.1488	0.9219	0.018*
C11	0.84752 (11)	0.22144 (13)	0.73637 (19)	0.0156 (3)
H11A	0.8286	0.1681	0.6840	0.019*
C12	0.84683 (10)	0.31250 (13)	0.67150 (18)	0.0138 (3)
C13	0.81214 (10)	0.32704 (14)	0.51865 (18)	0.0147 (3)
C14	0.93282 (10)	0.27846 (14)	1.11620 (19)	0.0165 (4)
O1W	0.63068 (10)	0.06139 (12)	0.38459 (17)	0.0271 (3)
O2W	0.85423 (10)	0.02585 (12)	0.18024 (18)	0.0268 (3)
O3W	0.56061 (10)	0.01269 (12)	0.63491 (16)	0.0242 (3)
O4W	0.78771 (9)	0.05874 (11)	0.43863 (16)	0.0224 (3)
H1NA	0.7560 (17)	0.265 (2)	0.267 (3)	0.024 (7)*
H2NA	0.7743 (15)	0.432 (2)	0.255 (3)	0.022 (6)*
H3NA	0.7636 (14)	0.489 (2)	0.115 (3)	0.019 (6)*
H1NB	0.463 (3)	0.307 (3)	−0.147 (5)	0.077 (14)*
H2NB	0.4765 (19)	0.150 (2)	−0.115 (4)	0.038 (8)*
H3NB	0.5148 (17)	0.100 (2)	0.032 (3)	0.033 (8)*
H1W1	0.6143 (17)	0.050 (2)	0.456 (4)	0.025 (7)*
H2W1	0.680 (2)	0.051 (2)	0.404 (4)	0.040 (9)*
H1W2	0.8800 (16)	0.080 (2)	0.172 (3)	0.025 (7)*
H2W2	0.8348 (16)	0.035 (2)	0.264 (3)	0.025 (7)*
H1W3	0.529 (2)	0.049 (3)	0.649 (4)	0.059 (12)*
H2W3	0.5807 (17)	−0.003 (2)	0.719 (4)	0.034 (8)*
H1W4	0.7949 (18)	0.123 (3)	0.461 (3)	0.035 (8)*
H2W4	0.8036 (18)	0.029 (2)	0.508 (4)	0.031 (7)*

	U11	U22	U33	U12	U13	U23
N1A	0.0186 (7)	0.0172 (7)	0.0128 (7)	−0.0016 (6)	−0.0011 (6)	0.0010 (5)
N2A	0.0271 (8)	0.0185 (7)	0.0147 (7)	−0.0044 (6)	−0.0042 (6)	0.0014 (6)
C1A	0.0166 (8)	0.0170 (8)	0.0151 (8)	−0.0016 (7)	−0.0005 (6)	0.0016 (6)
C2A	0.0203 (9)	0.0220 (9)	0.0136 (7)	−0.0013 (7)	−0.0008 (6)	0.0026 (6)
C3A	0.0146 (8)	0.0234 (9)	0.0140 (8)	0.0014 (7)	0.0007 (6)	0.0006 (7)
C4A	0.0200 (9)	0.0182 (8)	0.0182 (8)	−0.0020 (7)	0.0015 (7)	−0.0031 (7)
C5A	0.0209 (9)	0.0184 (9)	0.0215 (9)	0.0021 (7)	0.0024 (7)	0.0027 (7)
C6A	0.0234 (10)	0.0321 (11)	0.0125 (8)	−0.0007 (8)	−0.0051 (7)	−0.0014 (7)
N1B	0.0219 (8)	0.0207 (8)	0.0153 (7)	−0.0009 (6)	−0.0021 (6)	0.0001 (6)
N2B	0.0225 (8)	0.0195 (8)	0.0127 (7)	−0.0017 (6)	−0.0024 (6)	−0.0006 (6)
C1B	0.0162 (8)	0.0211 (9)	0.0135 (8)	−0.0020 (6)	0.0013 (6)	0.0009 (6)
C2B	0.0172 (8)	0.0240 (9)	0.0137 (8)	−0.0006 (7)	0.0002 (6)	0.0005 (6)
C3B	0.0174 (9)	0.0295 (10)	0.0133 (8)	−0.0029 (7)	0.0020 (6)	−0.0019 (7)
C4B	0.0250 (10)	0.0221 (9)	0.0217 (9)	−0.0004 (8)	−0.0004 (7)	−0.0039 (7)
C5B	0.0232 (9)	0.0227 (9)	0.0198 (9)	0.0027 (7)	−0.0003 (7)	−0.0001 (7)
C6B	0.0282 (11)	0.0370 (12)	0.0151 (9)	0.0003 (9)	−0.0048 (8)	−0.0064 (8)
O1	0.0276 (7)	0.0164 (6)	0.0140 (6)	0.0043 (5)	−0.0034 (5)	0.0006 (5)
O2	0.0293 (7)	0.0149 (6)	0.0138 (6)	0.0008 (5)	−0.0032 (5)	−0.0006 (5)
O3	0.0373 (8)	0.0238 (7)	0.0151 (6)	−0.0085 (6)	−0.0064 (6)	0.0005 (5)
O4	0.0309 (8)	0.0196 (7)	0.0165 (6)	−0.0048 (6)	−0.0053 (5)	0.0033 (5)
C7	0.0165 (8)	0.0154 (8)	0.0146 (8)	0.0003 (6)	−0.0007 (6)	0.0007 (6)
C8	0.0160 (8)	0.0173 (8)	0.0138 (7)	−0.0027 (6)	−0.0014 (6)	−0.0012 (6)
C9	0.0143 (8)	0.0198 (8)	0.0103 (7)	0.0005 (6)	−0.0001 (6)	0.0015 (6)
C10	0.0183 (8)	0.0152 (8)	0.0124 (8)	0.0010 (7)	0.0002 (6)	0.0017 (6)
C11	0.0180 (8)	0.0161 (8)	0.0126 (8)	0.0004 (7)	−0.0006 (6)	−0.0006 (6)
C12	0.0136 (8)	0.0166 (8)	0.0112 (7)	0.0015 (6)	0.0010 (6)	0.0009 (6)
C13	0.0163 (8)	0.0177 (8)	0.0099 (7)	−0.0002 (6)	−0.0003 (6)	0.0006 (6)
C14	0.0177 (8)	0.0203 (9)	0.0109 (7)	−0.0035 (7)	−0.0028 (6)	0.0009 (6)
O1W	0.0280 (8)	0.0343 (9)	0.0189 (7)	−0.0029 (7)	−0.0002 (6)	0.0039 (6)
O2W	0.0357 (9)	0.0214 (7)	0.0236 (7)	−0.0049 (6)	0.0044 (6)	−0.0045 (6)
O3W	0.0289 (8)	0.0237 (7)	0.0197 (7)	0.0027 (6)	0.0002 (6)	−0.0012 (5)
O4W	0.0306 (8)	0.0169 (7)	0.0194 (7)	−0.0007 (6)	−0.0007 (6)	0.0001 (5)

N1A—C1A	1.352 (2)	C4B—H4BA	0.93
N1A—C5A	1.361 (3)	C5B—H5BA	0.93
N1A—H1NA	0.95 (3)	C6B—H6BA	0.96
N2A—C1A	1.334 (2)	C6B—H6BB	0.96
N2A—H2NA	0.83 (3)	C6B—H6BC	0.96
N2A—H3NA	0.91 (3)	O1—C13	1.253 (2)
C1A—C2A	1.421 (2)	O2—C13	1.267 (2)
C2A—C3A	1.374 (3)	O3—C14	1.256 (2)
C2A—H2AA	0.93	O4—C14	1.263 (2)
C3A—C4A	1.416 (3)	C7—C8	1.387 (2)
C3A—C6A	1.503 (2)	C7—C12	1.398 (2)
C4A—C5A	1.363 (3)	C7—H7A	0.93
C4A—H4AA	0.93	C8—C9	1.394 (3)
C5A—H5AA	0.93	C8—H8A	0.93
C6A—H6AA	0.96	C9—C10	1.395 (2)
C6A—H6AB	0.96	C9—C14	1.510 (2)
C6A—H6AC	0.96	C10—C11	1.395 (2)
N1B—C1B	1.356 (2)	C10—H10A	0.93
N1B—C5B	1.361 (3)	C11—C12	1.393 (2)
N1B—H1NB	1.01 (5)	C11—H11A	0.93
N2B—C1B	1.327 (3)	C12—C13	1.515 (2)
N2B—H2NB	0.90 (3)	O1W—H1W1	0.75 (3)
N2B—H3NB	0.93 (3)	O1W—H2W1	0.89 (3)
C1B—C2B	1.418 (2)	O2W—H1W2	0.88 (3)
C2B—C3B	1.365 (3)	O2W—H2W2	0.88 (3)
C2B—H2BA	0.93	O3W—H1W3	0.76 (5)
C3B—C4B	1.421 (3)	O3W—H2W3	0.86 (3)
C3B—C6B	1.505 (3)	O4W—H1W4	0.92 (3)
C4B—C5B	1.364 (3)	O4W—H2W4	0.79 (3)
C1A—N1A—C5A	122.10 (16)	C4B—C3B—C6B	120.57 (19)
C1A—N1A—H1NA	121.5 (17)	C5B—C4B—C3B	118.71 (19)
C5A—N1A—H1NA	116.4 (17)	C5B—C4B—H4BA	120.6
C1A—N2A—H2NA	118.8 (19)	C3B—C4B—H4BA	120.6
C1A—N2A—H3NA	115.1 (16)	N1B—C5B—C4B	121.01 (18)
H2NA—N2A—H3NA	122 (2)	N1B—C5B—H5BA	119.5
N2A—C1A—N1A	119.37 (16)	C4B—C5B—H5BA	119.5
N2A—C1A—C2A	122.50 (17)	C3B—C6B—H6BA	109.5
N1A—C1A—C2A	118.13 (16)	C3B—C6B—H6BB	109.5
C3A—C2A—C1A	120.45 (18)	H6BA—C6B—H6BB	109.5
C3A—C2A—H2AA	119.8	C3B—C6B—H6BC	109.5
C1A—C2A—H2AA	119.8	H6BA—C6B—H6BC	109.5
C2A—C3A—C4A	119.13 (16)	H6BB—C6B—H6BC	109.5
C2A—C3A—C6A	120.58 (18)	C8—C7—C12	120.35 (17)
C4A—C3A—C6A	120.29 (18)	C8—C7—H7A	119.8
C5A—C4A—C3A	119.09 (17)	C12—C7—H7A	119.8
C5A—C4A—H4AA	120.5	C7—C8—C9	120.59 (16)
C3A—C4A—H4AA	120.5	C7—C8—H8A	119.7
N1A—C5A—C4A	121.08 (18)	C9—C8—H8A	119.7
N1A—C5A—H5AA	119.5	C8—C9—C10	119.16 (15)
C4A—C5A—H5AA	119.5	C8—C9—C14	120.08 (15)
C3A—C6A—H6AA	109.5	C10—C9—C14	120.77 (16)
C3A—C6A—H6AB	109.5	C11—C10—C9	120.31 (16)
H6AA—C6A—H6AB	109.5	C11—C10—H10A	119.8
C3A—C6A—H6AC	109.5	C9—C10—H10A	119.8
H6AA—C6A—H6AC	109.5	C12—C11—C10	120.29 (16)
H6AB—C6A—H6AC	109.5	C12—C11—H11A	119.9
C1B—N1B—C5B	122.09 (16)	C10—C11—H11A	119.9
C1B—N1B—H1NB	118 (3)	C11—C12—C7	119.24 (15)
C5B—N1B—H1NB	120 (3)	C11—C12—C13	120.85 (15)
C1B—N2B—H2NB	117 (2)	C7—C12—C13	119.90 (16)
C1B—N2B—H3NB	116.5 (19)	O1—C13—O2	124.18 (16)
H2NB—N2B—H3NB	126 (3)	O1—C13—C12	118.25 (16)
N2B—C1B—N1B	118.66 (16)	O2—C13—C12	117.57 (16)
N2B—C1B—C2B	123.14 (18)	O3—C14—O4	124.01 (16)
N1B—C1B—C2B	118.19 (18)	O3—C14—C9	117.32 (16)
C3B—C2B—C1B	120.39 (19)	O4—C14—C9	118.66 (16)
C3B—C2B—H2BA	119.8	H1W1—O1W—H2W1	103 (3)
C1B—C2B—H2BA	119.8	H1W2—O2W—H2W2	101 (3)
C2B—C3B—C4B	119.60 (17)	H1W3—O3W—H2W3	106 (4)
C2B—C3B—C6B	119.81 (19)	H1W4—O4W—H2W4	106 (3)
C5A—N1A—C1A—N2A	179.05 (18)	C3B—C4B—C5B—N1B	−0.6 (3)
C5A—N1A—C1A—C2A	−1.0 (3)	C12—C7—C8—C9	0.9 (3)
N2A—C1A—C2A—C3A	−178.48 (19)	C7—C8—C9—C10	1.5 (3)
N1A—C1A—C2A—C3A	1.6 (3)	C7—C8—C9—C14	−178.37 (18)
C1A—C2A—C3A—C4A	−1.0 (3)	C8—C9—C10—C11	−2.2 (3)
C1A—C2A—C3A—C6A	178.99 (18)	C14—C9—C10—C11	177.62 (17)
C2A—C3A—C4A—C5A	−0.2 (3)	C9—C10—C11—C12	0.5 (3)
C6A—C3A—C4A—C5A	179.84 (18)	C10—C11—C12—C7	1.9 (3)
C1A—N1A—C5A—C4A	−0.2 (3)	C10—C11—C12—C13	−176.98 (17)
C3A—C4A—C5A—N1A	0.8 (3)	C8—C7—C12—C11	−2.6 (3)
C5B—N1B—C1B—N2B	178.77 (19)	C8—C7—C12—C13	176.24 (17)
C5B—N1B—C1B—C2B	−0.2 (3)	C11—C12—C13—O1	161.04 (18)
N2B—C1B—C2B—C3B	−179.74 (19)	C7—C12—C13—O1	−17.8 (3)
N1B—C1B—C2B—C3B	−0.8 (3)	C11—C12—C13—O2	−18.0 (3)
C1B—C2B—C3B—C4B	1.1 (3)	C7—C12—C13—O2	163.16 (17)
C1B—C2B—C3B—C6B	179.48 (19)	C8—C9—C14—O3	5.2 (3)
C2B—C3B—C4B—C5B	−0.4 (3)	C10—C9—C14—O3	−174.63 (18)
C6B—C3B—C4B—C5B	−178.8 (2)	C8—C9—C14—O4	−175.75 (19)
C1B—N1B—C5B—C4B	0.9 (3)	C10—C9—C14—O4	4.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O2	0.95 (3)	1.75 (3)	2.698 (2)	172 (3)
N2A—H2NA···O1	0.83 (3)	2.10 (3)	2.906 (2)	165 (3)
N2A—H3NA···O1i	0.91 (3)	1.97 (3)	2.866 (2)	171 (2)
N1B—H1NB···O4ii	1.02 (5)	1.72 (5)	2.723 (2)	169 (3)
N2B—H2NB···O3ii	0.90 (4)	1.88 (4)	2.765 (2)	170 (3)
N2B—H3NB···O3Wiii	0.93 (3)	1.97 (3)	2.894 (2)	174 (3)
O1W—H1W1···O3W	0.76 (4)	2.03 (3)	2.781 (2)	174 (4)
O1W—H2W1···O4W	0.89 (4)	1.91 (4)	2.779 (2)	167 (3)
O2W—H1W2···O4iv	0.88 (3)	1.86 (3)	2.741 (2)	175 (3)
O2W—H2W2···O4W	0.88 (3)	1.90 (3)	2.772 (2)	176 (3)
O3W—H1W3···O3v	0.77 (4)	1.95 (4)	2.721 (2)	178 (5)
O3W—H2W3···O1Wvi	0.86 (4)	1.89 (3)	2.742 (2)	168 (3)
O4W—H1W4···O2	0.92 (4)	1.81 (4)	2.689 (2)	161 (3)
O4W—H2W4···O2Wvi	0.80 (3)	1.93 (3)	2.716 (2)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O2	0.95 (3)	1.75 (3)	2.698 (2)	172 (3)
N2A—H2NA⋯O1	0.83 (3)	2.10 (3)	2.906 (2)	165 (3)
N2A—H3NA⋯O1i	0.91 (3)	1.97 (3)	2.866 (2)	171 (2)
N1B—H1NB⋯O4ii	1.02 (5)	1.72 (5)	2.723 (2)	169 (3)
N2B—H2NB⋯O3ii	0.90 (4)	1.88 (4)	2.765 (2)	170 (3)
N2B—H3NB⋯O3Wiii	0.93 (3)	1.97 (3)	2.894 (2)	174 (3)
O1W—H1W1⋯O3W	0.76 (4)	2.03 (3)	2.781 (2)	174 (4)
O1W—H2W1⋯O4W	0.89 (4)	1.91 (4)	2.779 (2)	167 (3)
O2W—H1W2⋯O4iv	0.88 (3)	1.86 (3)	2.741 (2)	175 (3)
O2W—H2W2⋯O4W	0.88 (3)	1.90 (3)	2.772 (2)	176 (3)
O3W—H1W3⋯O3v	0.77 (4)	1.95 (4)	2.721 (2)	178 (5)
O3W—H2W3⋯O1Wvi	0.86 (4)	1.89 (3)	2.742 (2)	168 (3)
O4W—H1W4⋯O2	0.92 (4)	1.81 (4)	2.689 (2)	161 (3)
O4W—H2W4⋯O2Wvi	0.80 (3)	1.93 (3)	2.716 (2)	171 (3)

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