2-Amino-5-methyl-pyridinium 1H-pyrazole-3,5-dicarboxyl-ate trihydrate.

In the title compound, 2C(6)H(9)N(2) (+)·C(5)H(2)N(2)O(4) (2-)·3H(2)O, the 1H-pyrazole-3,5-dicarboxyl-ate anion is close to planar [maximum deviation = 0.208 (1) Å]. The two distinct 2-amino-5-methyl-pyridinium cations are also almost planar, with maximum deviations of 0.018 (2) and 0.014 (2) Å. In the crystal, pairs of inter-molecular N-H⋯O and O-H⋯O hydrogen bonds connect neighbouring mol-ecules into dimers, generating R(2) (2)(8) and R(2) (4)(8) ring motifs, respectively. Further inter-molecular N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997 ▶); Katritzky et al. (1996 ▶). 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 related structures, see; Xia et al. (2007 ▶); King et al. (2004 ▶). For details and applications of pyrazole-3,5-dicarb­oxy­lic acid, see: Lee et al. (1989 ▶); Chambers et al. (1985 ▶); Pan et al. (2000 ▶); Pan, Ching et al. (2001 ▶); Pan, Frydel et al. (2001 ▶).

Experimental

Crystal data

2C6H9N2 +·C5H2N2O4 2−·3H2O

M = 426.44

Triclinic,

a = 7.8985 (1) Å

b = 9.2195 (1) Å

c = 15.3922 (2) Å

α = 101.942 (1)°

β = 93.883 (1)°

γ = 104.648 (1)°

V = 1052.40 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.47 × 0.24 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.952, T max = 0.978

26056 measured reflections

6103 independent reflections

5085 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.113

S = 1.07

6103 reflections

325 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.24 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/S1600536810041644/hb5681sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041644/hb5681Isup2.hkl

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

2C6H9N2+·C5H2N2O42−·3H2O	Z = 2
Mr = 426.44	F(000) = 452
Triclinic, P1	Dx = 1.346 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8985 (1) Å	Cell parameters from 9892 reflections
b = 9.2195 (1) Å	θ = 2.4–35.1°
c = 15.3922 (2) Å	µ = 0.11 mm−1
α = 101.942 (1)°	T = 100 K
β = 93.883 (1)°	Block, colourless
γ = 104.648 (1)°	0.47 × 0.24 × 0.21 mm
V = 1052.40 (2) Å3

Bruker SMART APEXII CCD diffractometer	6103 independent reflections
Radiation source: fine-focus sealed tube	5085 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 30.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.952, Tmax = 0.978	k = −12→12
26056 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.2775P] where P = (Fo2 + 2Fc2)/3
6103 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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

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.

	x	y	z	Uiso*/Ueq
O1	0.68720 (11)	0.64094 (9)	0.43780 (5)	0.02004 (16)
O2	0.63845 (11)	0.84955 (9)	0.40067 (5)	0.02212 (17)
O3	0.70719 (11)	0.24170 (9)	0.10667 (5)	0.02152 (17)
O4	0.58424 (10)	0.33899 (9)	0.00540 (5)	0.01827 (16)
N1	0.56503 (12)	0.68973 (10)	0.21937 (6)	0.01756 (18)
N2	0.56444 (12)	0.58634 (10)	0.14333 (6)	0.01631 (17)
C1	0.65092 (14)	0.71292 (12)	0.38074 (7)	0.01627 (19)
C2	0.62433 (13)	0.63055 (11)	0.28462 (6)	0.01510 (19)
C3	0.66147 (13)	0.49037 (11)	0.24972 (6)	0.01555 (19)
H3A	0.7032	0.4279	0.2812	0.019*
C4	0.62226 (13)	0.46589 (11)	0.15823 (6)	0.01420 (18)
C5	0.63753 (13)	0.33966 (11)	0.08394 (6)	0.01463 (18)
N3A	0.80196 (12)	0.03401 (11)	0.55694 (6)	0.01923 (18)
N4A	0.90801 (14)	−0.15177 (12)	0.60538 (7)	0.0248 (2)
C6A	0.89063 (14)	−0.00860 (13)	0.62071 (7)	0.0192 (2)
C7A	0.96163 (15)	0.10318 (14)	0.70158 (7)	0.0226 (2)
H7AA	1.0235	0.0786	0.7475	0.027*
C8A	0.93848 (15)	0.24717 (14)	0.71159 (8)	0.0239 (2)
H8AA	0.9838	0.3193	0.7653	0.029*
C9A	0.84776 (15)	0.29051 (13)	0.64303 (8)	0.0224 (2)
C10	0.78076 (15)	0.17873 (13)	0.56658 (7)	0.0212 (2)
H10A	0.7192	0.2017	0.5199	0.025*
C11A	0.82578 (18)	0.45015 (14)	0.65337 (10)	0.0324 (3)
H11A	0.7779	0.4614	0.5969	0.049*
H11B	0.9384	0.5245	0.6729	0.049*
H11C	0.7470	0.4665	0.6969	0.049*
N3B	0.26714 (12)	0.00202 (10)	0.01212 (6)	0.01689 (17)
N4B	0.37262 (14)	−0.08155 (12)	0.13095 (7)	0.02199 (19)
C6B	0.30472 (14)	0.02005 (12)	0.10101 (7)	0.01719 (19)
C7B	0.26600 (15)	0.14651 (13)	0.15793 (7)	0.0213 (2)
H7BA	0.2909	0.1642	0.2197	0.026*
C8B	0.19158 (15)	0.24211 (12)	0.12087 (8)	0.0214 (2)
H8BA	0.1650	0.3240	0.1585	0.026*
C9B	0.15376 (14)	0.22026 (12)	0.02713 (8)	0.0197 (2)
C10B	0.19410 (14)	0.09771 (12)	−0.02480 (7)	0.0184 (2)
H10B	0.1712	0.0791	−0.0868	0.022*
C11B	0.07429 (16)	0.32759 (14)	−0.01255 (9)	0.0264 (2)
H11D	0.0564	0.2936	−0.0766	0.040*
H11E	0.1526	0.4299	0.0046	0.040*
H11F	−0.0369	0.3278	0.0090	0.040*
O3W	0.52828 (12)	1.04505 (10)	0.31330 (5)	0.02258 (17)
O2W	0.54335 (13)	0.32242 (10)	0.43022 (6)	0.02698 (19)
O1W	0.84767 (12)	0.15951 (12)	0.25161 (6)	0.0291 (2)
H1N2	0.523 (2)	0.6047 (18)	0.0897 (11)	0.027 (4)*
H3NA	0.968 (2)	−0.176 (2)	0.6462 (12)	0.040 (5)*
H1NB	0.286 (2)	−0.080 (2)	−0.0250 (11)	0.033 (4)*
H2NB	0.393 (2)	−0.162 (2)	0.0913 (12)	0.039 (4)*
H3NB	0.409 (2)	−0.063 (2)	0.1891 (12)	0.038 (4)*
H1NA	0.749 (2)	−0.037 (2)	0.5028 (12)	0.040 (4)*
H2NA	0.853 (2)	−0.220 (2)	0.5538 (12)	0.039 (4)*
H1W1	0.820 (2)	0.200 (2)	0.2082 (13)	0.045 (5)*
H2W1	0.751 (3)	0.123 (2)	0.2703 (14)	0.053 (6)*
H1W2	0.591 (2)	0.414 (2)	0.4263 (12)	0.043 (5)*
H2W2	0.470 (2)	0.330 (2)	0.4684 (13)	0.044 (5)*
H1W3	0.558 (2)	0.9771 (19)	0.3403 (11)	0.034 (4)*
H2W3	0.529 (2)	1.128 (2)	0.3540 (12)	0.043 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0295 (4)	0.0177 (4)	0.0135 (3)	0.0084 (3)	0.0007 (3)	0.0032 (3)
O2	0.0349 (4)	0.0168 (4)	0.0150 (3)	0.0118 (3)	−0.0016 (3)	0.0001 (3)
O3	0.0337 (4)	0.0199 (4)	0.0145 (3)	0.0152 (3)	0.0010 (3)	0.0026 (3)
O4	0.0249 (4)	0.0174 (4)	0.0129 (3)	0.0083 (3)	−0.0006 (3)	0.0022 (3)
N1	0.0240 (4)	0.0158 (4)	0.0130 (4)	0.0078 (3)	0.0007 (3)	0.0013 (3)
N2	0.0224 (4)	0.0151 (4)	0.0120 (4)	0.0080 (3)	0.0004 (3)	0.0014 (3)
C1	0.0186 (5)	0.0164 (4)	0.0130 (4)	0.0051 (4)	0.0010 (3)	0.0015 (3)
C2	0.0181 (4)	0.0143 (4)	0.0124 (4)	0.0047 (4)	0.0010 (3)	0.0020 (3)
C3	0.0188 (5)	0.0148 (4)	0.0135 (4)	0.0055 (4)	0.0011 (3)	0.0034 (3)
C4	0.0157 (4)	0.0129 (4)	0.0138 (4)	0.0046 (3)	0.0010 (3)	0.0022 (3)
C5	0.0167 (4)	0.0140 (4)	0.0128 (4)	0.0039 (3)	0.0020 (3)	0.0027 (3)
N3A	0.0224 (4)	0.0195 (4)	0.0143 (4)	0.0057 (3)	−0.0004 (3)	0.0016 (3)
N4A	0.0293 (5)	0.0217 (5)	0.0213 (5)	0.0068 (4)	−0.0069 (4)	0.0037 (4)
C6A	0.0182 (5)	0.0214 (5)	0.0164 (5)	0.0025 (4)	0.0006 (4)	0.0047 (4)
C7A	0.0210 (5)	0.0264 (5)	0.0158 (5)	0.0009 (4)	−0.0030 (4)	0.0037 (4)
C8A	0.0203 (5)	0.0256 (6)	0.0189 (5)	−0.0002 (4)	−0.0002 (4)	−0.0015 (4)
C9A	0.0206 (5)	0.0207 (5)	0.0228 (5)	0.0042 (4)	0.0021 (4)	0.0002 (4)
C10	0.0223 (5)	0.0212 (5)	0.0199 (5)	0.0074 (4)	0.0008 (4)	0.0033 (4)
C11A	0.0317 (6)	0.0207 (6)	0.0391 (7)	0.0074 (5)	−0.0022 (5)	−0.0039 (5)
N3B	0.0194 (4)	0.0146 (4)	0.0160 (4)	0.0062 (3)	0.0015 (3)	0.0005 (3)
N4B	0.0294 (5)	0.0216 (5)	0.0152 (4)	0.0108 (4)	−0.0015 (4)	0.0013 (3)
C6B	0.0168 (4)	0.0158 (5)	0.0168 (5)	0.0028 (4)	0.0016 (3)	0.0012 (4)
C7B	0.0238 (5)	0.0187 (5)	0.0184 (5)	0.0050 (4)	0.0034 (4)	−0.0009 (4)
C8B	0.0209 (5)	0.0152 (5)	0.0260 (5)	0.0047 (4)	0.0065 (4)	−0.0009 (4)
C9B	0.0168 (5)	0.0154 (5)	0.0272 (5)	0.0046 (4)	0.0049 (4)	0.0049 (4)
C10B	0.0184 (5)	0.0174 (5)	0.0194 (5)	0.0048 (4)	0.0021 (4)	0.0048 (4)
C11B	0.0260 (6)	0.0207 (5)	0.0370 (6)	0.0100 (4)	0.0063 (5)	0.0112 (5)
O3W	0.0336 (5)	0.0189 (4)	0.0159 (4)	0.0100 (3)	−0.0003 (3)	0.0032 (3)
O2W	0.0402 (5)	0.0185 (4)	0.0252 (4)	0.0108 (4)	0.0132 (4)	0.0052 (3)
O1W	0.0251 (4)	0.0407 (5)	0.0259 (4)	0.0095 (4)	−0.0003 (3)	0.0182 (4)

O1—C1	1.2637 (12)	C11A—H11A	0.9600
O2—C1	1.2640 (13)	C11A—H11B	0.9600
O3—C5	1.2637 (12)	C11A—H11C	0.9600
O4—C5	1.2511 (12)	N3B—C6B	1.3468 (13)
N1—N2	1.3467 (12)	N3B—C10B	1.3618 (13)
N1—C2	1.3483 (13)	N3B—H1NB	0.897 (17)
N2—C4	1.3572 (12)	N4B—C6B	1.3329 (14)
N2—H1N2	0.929 (16)	N4B—H2NB	0.910 (18)
C1—C2	1.4907 (14)	N4B—H3NB	0.890 (18)
C2—C3	1.4038 (14)	C6B—C7B	1.4193 (14)
C3—C4	1.3798 (13)	C7B—C8B	1.3683 (16)
C3—H3A	0.9300	C7B—H7BA	0.9300
C4—C5	1.4884 (13)	C8B—C9B	1.4153 (16)
N3A—C6A	1.3468 (14)	C8B—H8BA	0.9300
N3A—C10	1.3656 (14)	C9B—C10B	1.3638 (15)
N3A—H1NA	0.943 (18)	C9B—C11B	1.5027 (15)
N4A—C6A	1.3356 (15)	C10B—H10B	0.9300
N4A—H3NA	0.863 (18)	C11B—H11D	0.9600
N4A—H2NA	0.909 (18)	C11B—H11E	0.9600
C6A—C7A	1.4171 (15)	C11B—H11F	0.9600
C7A—C8A	1.3643 (17)	O3W—H1W3	0.889 (18)
C7A—H7AA	0.9300	O3W—H2W3	0.879 (19)
C8A—C9A	1.4155 (17)	O2W—H1W2	0.85 (2)
C8A—H8AA	0.9300	O2W—H2W2	0.86 (2)
C9A—C10	1.3656 (15)	O1W—H1W1	0.87 (2)
C9A—C11A	1.5026 (17)	O1W—H2W1	0.85 (2)
C10—H10A	0.9300
N2—N1—C2	104.08 (8)	N3A—C10—H10A	119.2
N1—N2—C4	112.83 (8)	C9A—C10—H10A	119.2
N1—N2—H1N2	117.6 (9)	C9A—C11A—H11A	109.5
C4—N2—H1N2	129.5 (9)	C9A—C11A—H11B	109.5
O1—C1—O2	123.84 (9)	H11A—C11A—H11B	109.5
O1—C1—C2	117.16 (9)	C9A—C11A—H11C	109.5
O2—C1—C2	119.00 (9)	H11A—C11A—H11C	109.5
N1—C2—C3	111.76 (9)	H11B—C11A—H11C	109.5
N1—C2—C1	121.73 (9)	C6B—N3B—C10B	123.39 (9)
C3—C2—C1	126.47 (9)	C6B—N3B—H1NB	118.8 (11)
C4—C3—C2	104.59 (9)	C10B—N3B—H1NB	117.7 (11)
C4—C3—H3A	127.7	C6B—N4B—H2NB	119.7 (11)
C2—C3—H3A	127.7	C6B—N4B—H3NB	118.8 (11)
N2—C4—C3	106.73 (9)	H2NB—N4B—H3NB	121.1 (16)
N2—C4—C5	122.30 (9)	N4B—C6B—N3B	119.07 (10)
C3—C4—C5	130.96 (9)	N4B—C6B—C7B	123.59 (10)
O4—C5—O3	125.34 (9)	N3B—C6B—C7B	117.33 (10)
O4—C5—C4	118.90 (9)	C8B—C7B—C6B	119.29 (10)
O3—C5—C4	115.76 (9)	C8B—C7B—H7BA	120.4
C6A—N3A—C10	123.07 (10)	C6B—C7B—H7BA	120.4
C6A—N3A—H1NA	120.5 (11)	C7B—C8B—C9B	122.07 (10)
C10—N3A—H1NA	116.5 (11)	C7B—C8B—H8BA	119.0
C6A—N4A—H3NA	118.1 (12)	C9B—C8B—H8BA	119.0
C6A—N4A—H2NA	119.0 (11)	C10B—C9B—C8B	116.49 (10)
H3NA—N4A—H2NA	122.8 (16)	C10B—C9B—C11B	122.09 (10)
N4A—C6A—N3A	119.34 (10)	C8B—C9B—C11B	121.41 (10)
N4A—C6A—C7A	123.26 (10)	N3B—C10B—C9B	121.42 (10)
N3A—C6A—C7A	117.41 (10)	N3B—C10B—H10B	119.3
C8A—C7A—C6A	119.48 (10)	C9B—C10B—H10B	119.3
C8A—C7A—H7AA	120.3	C9B—C11B—H11D	109.5
C6A—C7A—H7AA	120.3	C9B—C11B—H11E	109.5
C7A—C8A—C9A	122.21 (10)	H11D—C11B—H11E	109.5
C7A—C8A—H8AA	118.9	C9B—C11B—H11F	109.5
C9A—C8A—H8AA	118.9	H11D—C11B—H11F	109.5
C10—C9A—C8A	116.20 (10)	H11E—C11B—H11F	109.5
C10—C9A—C11A	121.63 (11)	H1W3—O3W—H2W3	109.1 (15)
C8A—C9A—C11A	122.17 (11)	H1W2—O2W—H2W2	105.7 (17)
N3A—C10—C9A	121.62 (10)	H1W1—O1W—H2W1	105.7 (18)
C2—N1—N2—C4	−0.55 (11)	N4A—C6A—C7A—C8A	179.69 (11)
N2—N1—C2—C3	0.16 (11)	N3A—C6A—C7A—C8A	−0.19 (16)
N2—N1—C2—C1	177.98 (9)	C6A—C7A—C8A—C9A	−1.06 (17)
O1—C1—C2—N1	172.05 (10)	C7A—C8A—C9A—C10	1.43 (17)
O2—C1—C2—N1	−8.81 (15)	C7A—C8A—C9A—C11A	−178.63 (11)
O1—C1—C2—C3	−10.46 (16)	C6A—N3A—C10—C9A	−0.66 (17)
O2—C1—C2—C3	168.68 (10)	C8A—C9A—C10—N3A	−0.58 (16)
N1—C2—C3—C4	0.25 (12)	C11A—C9A—C10—N3A	179.48 (11)
C1—C2—C3—C4	−177.44 (10)	C10B—N3B—C6B—N4B	178.55 (10)
N1—N2—C4—C3	0.72 (12)	C10B—N3B—C6B—C7B	−0.34 (15)
N1—N2—C4—C5	−178.32 (9)	N4B—C6B—C7B—C8B	−178.10 (11)
C2—C3—C4—N2	−0.56 (11)	N3B—C6B—C7B—C8B	0.74 (15)
C2—C3—C4—C5	178.37 (10)	C6B—C7B—C8B—C9B	−0.84 (17)
N2—C4—C5—O4	−4.89 (15)	C7B—C8B—C9B—C10B	0.50 (16)
C3—C4—C5—O4	176.33 (10)	C7B—C8B—C9B—C11B	−179.15 (10)
N2—C4—C5—O3	174.18 (9)	C6B—N3B—C10B—C9B	0.02 (16)
C3—C4—C5—O3	−4.60 (16)	C8B—C9B—C10B—N3B	−0.08 (15)
C10—N3A—C6A—N4A	−178.84 (10)	C11B—C9B—C10B—N3B	179.57 (10)
C10—N3A—C6A—C7A	1.05 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O4i	0.931 (16)	1.871 (16)	2.7912 (12)	169.7 (15)
N4A—H3NA···O1Wii	0.861 (18)	2.024 (17)	2.8520 (14)	161.2 (17)
N3B—H1NB···O3iii	0.900 (17)	1.755 (17)	2.6483 (12)	171.4 (16)
N4B—H2NB···O4iii	0.914 (18)	2.022 (18)	2.9323 (13)	173.8 (16)
N4B—H3NB···O3Wiv	0.889 (18)	2.007 (18)	2.8641 (13)	161.6 (17)
N3A—H1NA···O2iv	0.942 (18)	1.732 (18)	2.6686 (12)	172.8 (17)
N4A—H2NA···O1iv	0.907 (18)	2.106 (18)	3.0021 (13)	169.4 (15)
O1W—H1W1···O3	0.871 (19)	1.902 (19)	2.7517 (12)	164.8 (17)
O1W—H2W1···O3Wiv	0.85 (2)	1.94 (2)	2.7878 (14)	178 (2)
O2W—H1W2···O1	0.850 (18)	2.003 (18)	2.8427 (12)	169.8 (17)
O2W—H2W2···O1v	0.858 (18)	1.987 (18)	2.8434 (13)	176.1 (15)
O3W—H1W3···O2	0.888 (17)	1.844 (17)	2.7299 (12)	174.8 (15)
O3W—H2W3···O2Wvi	0.881 (18)	1.900 (18)	2.7758 (13)	172.1 (17)
C10—H10A···O2W	0.93	2.50	3.3986 (15)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O4i	0.931 (16)	1.871 (16)	2.7912 (12)	169.7 (15)
N4A—H3NA⋯O1Wii	0.861 (18)	2.024 (17)	2.8520 (14)	161.2 (17)
N3B—H1NB⋯O3iii	0.900 (17)	1.755 (17)	2.6483 (12)	171.4 (16)
N4B—H2NB⋯O4iii	0.914 (18)	2.022 (18)	2.9323 (13)	173.8 (16)
N4B—H3NB⋯O3Wiv	0.889 (18)	2.007 (18)	2.8641 (13)	161.6 (17)
N3A—H1NA⋯O2iv	0.942 (18)	1.732 (18)	2.6686 (12)	172.8 (17)
N4A—H2NA⋯O1iv	0.907 (18)	2.106 (18)	3.0021 (13)	169.4 (15)
O1W—H1W1⋯O3	0.871 (19)	1.902 (19)	2.7517 (12)	164.8 (17)
O1W—H2W1⋯O3Wiv	0.85 (2)	1.94 (2)	2.7878 (14)	178 (2)
O2W—H1W2⋯O1	0.850 (18)	2.003 (18)	2.8427 (12)	169.8 (17)
O2W—H2W2⋯O1v	0.858 (18)	1.987 (18)	2.8434 (13)	176.1 (15)
O3W—H1W3⋯O2	0.888 (17)	1.844 (17)	2.7299 (12)	174.8 (15)
O3W—H2W3⋯O2Wvi	0.881 (18)	1.900 (18)	2.7758 (13)	172.1 (17)
C10—H10A⋯O2W	0.93	2.50	3.3986 (15)	164

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