2-Amino-3-carb-oxy-pyrazin-1-ium perchlorate bis-(2-amino-pyrazin-1-ium-3-carboxyl-ate) monohydrate.

The asymmetric unit of the title compound, C(5)H(6)N(3)O(2) (+)·ClO(4) (-)·2C(5)H(5)N(3)O(2)·H(2)O, comprises two symmetry-independent zwitterions, one cation, one perchlorate anion and one water mol-ecule. In the crystal, the three different types of organic entities are linked by N-H⋯O and N-H⋯N hydrogen bonds, forming undulating sheets parallel to (1-10). These sheets are in turn connected by O-H⋯N and O-H⋯O hydrogen bonds involving perchlorate anions and water mol-ecules, forming a three-dimensional network. Intra-molecular N-H⋯O and weak inter-molecular C-H⋯O hydrogen bonds are also present.

Related literature

For crystal structures of hybrid compounds obtained from 3-amino-pyrazine 2-carb­oxy­lic acid, see: Berrah et al. (2011a ▶,b ▶,c ▶). For related perchlorate compounds, see: Bendjeddou et al. (2003 ▶); Berrah et al. (2012 ▶); Toumi Akriche et al.(2010 ▶).

Experimental

Crystal data

C5H6N3O2 +·ClO4 −·2C5H5N3O2·H2O

M = 535.83

Triclinic,

a = 8.1332 (14) Å

b = 11.816 (2) Å

c = 11.850 (2) Å

α = 95.696 (9)°

β = 108.148 (8)°

γ = 102.416 (8)°

V = 1039.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 150 K

0.46 × 0.27 × 0.17 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.855, T max = 0.955

15575 measured reflections

4705 independent reflections

4165 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.1

S = 1.04

4705 reflections

332 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al. 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021071/lh5470sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021071/lh5470Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021071/lh5470Isup3.cml

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

C5H6N3O2+·ClO4−·2C5H5N3O2·H2O	Z = 2
Mr = 535.83	F(000) = 552
Triclinic, P1	Dx = 1.712 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1332 (14) Å	Cell parameters from 7298 reflections
b = 11.816 (2) Å	θ = 2.7–27.4°
c = 11.850 (2) Å	µ = 0.27 mm−1
α = 95.696 (9)°	T = 150 K
β = 108.148 (8)°	Prism, colourless
γ = 102.416 (8)°	0.46 × 0.27 × 0.17 mm
V = 1039.8 (3) Å3

Bruker APEXII diffractometer	4165 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −10→10
Tmin = 0.855, Tmax = 0.955	k = −15→15
15575 measured reflections	l = −14→15
4705 independent reflections

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) = 0.1	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0379P)2 + 0.495P] where P = (Fo2 + 2Fc2)/3
4705 reflections	(Δ/σ)max = 0.001
332 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.48 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.

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
Cl1	0.69001 (5)	0.36663 (3)	−0.00929 (3)	0.01747 (11)
O3	0.68759 (17)	0.43096 (11)	0.09976 (11)	0.0282 (3)
C2A	0.07122 (19)	−0.13735 (13)	0.05029 (13)	0.0142 (3)
O2	0.62112 (16)	0.24144 (10)	−0.01437 (11)	0.0248 (3)
O1A	0.32377 (15)	0.00920 (10)	0.18281 (10)	0.0214 (3)
H1A	0.4049	0.0661	0.1869	0.032*
O1W	0.55592 (16)	0.19617 (10)	0.19895 (12)	0.0222 (3)
H1W	0.663 (3)	0.2094 (19)	0.254 (2)	0.033*
H2W	0.566 (3)	0.205 (2)	0.132 (2)	0.033*
O2C	0.40678 (15)	0.39784 (9)	0.29630 (10)	0.0185 (2)
N2C	0.88489 (17)	0.53957 (11)	0.58581 (12)	0.0170 (3)
H2C	0.9651	0.6013	0.588	0.02*
O1	0.57705 (18)	0.40133 (11)	−0.11220 (11)	0.0298 (3)
N3C	0.63598 (17)	0.34284 (12)	0.58168 (12)	0.0176 (3)
O1B	0.11825 (16)	−0.26089 (10)	0.61036 (11)	0.0235 (3)
C5B	0.3196 (2)	0.08607 (14)	0.75159 (14)	0.0183 (3)
H5B	0.3426	0.1123	0.833	0.022*
C5C	0.7831 (2)	0.38892 (15)	0.68069 (15)	0.0197 (3)
H5C	0.7998	0.3523	0.7478	0.024*
O4	0.86893 (17)	0.38880 (12)	−0.01070 (14)	0.0359 (3)
N1A	−0.01642 (18)	−0.16806 (12)	−0.17083 (12)	0.0212 (3)
H11A	−0.0909	−0.2062	−0.2398	0.025*
H12A	0.0748	−0.1132	−0.1671	0.025*
N2B	0.34558 (17)	0.12346 (11)	0.56691 (12)	0.0176 (3)
H2B	0.3852	0.1715	0.5257	0.021*
C1C	0.4396 (2)	0.34074 (13)	0.38055 (14)	0.0156 (3)
C4B	0.3817 (2)	0.16113 (14)	0.68530 (14)	0.0186 (3)
H4B	0.4485	0.2378	0.7214	0.022*
C2C	0.61173 (19)	0.39387 (13)	0.48635 (14)	0.0147 (3)
C3C	0.7406 (2)	0.49782 (13)	0.48389 (14)	0.0150 (3)
O2B	−0.00600 (16)	−0.22021 (10)	0.42749 (10)	0.0239 (3)
O1C	0.34056 (15)	0.24560 (10)	0.38619 (10)	0.0219 (3)
C3A	−0.04216 (19)	−0.19367 (13)	−0.07064 (14)	0.0150 (3)
N2A	−0.18714 (16)	−0.28048 (11)	−0.08043 (11)	0.0152 (3)
H2A	−0.2602	−0.3146	−0.1513	0.018*
N1C	0.72791 (18)	0.55293 (12)	0.39109 (12)	0.0199 (3)
H11C	0.8106	0.6143	0.3961	0.024*
H12C	0.6369	0.5274	0.3257	0.024*
C5A	−0.1068 (2)	−0.26064 (14)	0.12868 (14)	0.0178 (3)
H5A	−0.1291	−0.2857	0.1957	0.021*
N3B	0.22488 (17)	−0.02635 (12)	0.70059 (12)	0.0173 (3)
C1B	0.0919 (2)	−0.19231 (14)	0.53518 (14)	0.0172 (3)
O2A	0.25539 (16)	0.00695 (10)	−0.01483 (10)	0.0239 (3)
C2B	0.1914 (2)	−0.06368 (13)	0.58521 (14)	0.0156 (3)
N3A	0.03789 (17)	−0.17121 (11)	0.14528 (12)	0.0164 (3)
C1A	0.2274 (2)	−0.03376 (13)	0.06933 (14)	0.0154 (3)
C4C	0.9077 (2)	0.48821 (15)	0.68396 (15)	0.0200 (3)
H4C	1.0073	0.52	0.7532	0.024*
N1B	0.2181 (2)	−0.01866 (13)	0.39418 (13)	0.0263 (3)
H11B	0.2591	0.0311	0.3549	0.032*
H12B	0.1569	−0.0888	0.3577	0.032*
C3B	0.2491 (2)	0.01272 (14)	0.51060 (14)	0.0170 (3)
C4A	−0.2213 (2)	−0.31536 (13)	0.01601 (14)	0.0168 (3)
H4A	−0.3216	−0.376	0.0063	0.02*

	U11	U22	U33	U12	U13	U23
Cl1	0.01646 (19)	0.01438 (19)	0.0198 (2)	0.00210 (14)	0.00545 (15)	0.00173 (14)
O3	0.0371 (7)	0.0237 (6)	0.0195 (6)	0.0060 (5)	0.0069 (5)	−0.0027 (5)
C2A	0.0137 (7)	0.0142 (7)	0.0136 (7)	0.0036 (6)	0.0033 (6)	0.0016 (6)
O2	0.0290 (6)	0.0143 (6)	0.0267 (7)	−0.0020 (5)	0.0092 (5)	0.0016 (5)
O1A	0.0193 (6)	0.0231 (6)	0.0145 (6)	−0.0055 (4)	0.0039 (4)	0.0011 (5)
O1W	0.0196 (6)	0.0226 (6)	0.0202 (6)	−0.0005 (5)	0.0047 (5)	0.0046 (5)
O2C	0.0207 (6)	0.0158 (5)	0.0141 (5)	0.0003 (4)	0.0019 (4)	0.0031 (4)
N2C	0.0142 (6)	0.0147 (6)	0.0187 (7)	−0.0012 (5)	0.0050 (5)	0.0012 (5)
O1	0.0366 (7)	0.0292 (7)	0.0208 (6)	0.0125 (6)	0.0033 (5)	0.0057 (5)
N3C	0.0171 (6)	0.0169 (7)	0.0171 (7)	0.0018 (5)	0.0052 (5)	0.0038 (5)
O1B	0.0256 (6)	0.0160 (6)	0.0206 (6)	−0.0040 (5)	0.0023 (5)	0.0050 (5)
C5B	0.0214 (8)	0.0167 (8)	0.0134 (7)	0.0013 (6)	0.0044 (6)	0.0004 (6)
C5C	0.0184 (8)	0.0233 (8)	0.0156 (8)	0.0037 (6)	0.0036 (6)	0.0062 (6)
O4	0.0208 (6)	0.0277 (7)	0.0630 (10)	0.0046 (5)	0.0204 (7)	0.0096 (7)
N1A	0.0205 (7)	0.0232 (7)	0.0126 (7)	−0.0041 (5)	0.0026 (5)	0.0016 (5)
N2B	0.0201 (7)	0.0144 (6)	0.0180 (7)	−0.0002 (5)	0.0084 (5)	0.0058 (5)
C1C	0.0167 (7)	0.0146 (7)	0.0137 (7)	0.0004 (6)	0.0057 (6)	0.0006 (6)
C4B	0.0206 (8)	0.0136 (7)	0.0171 (8)	−0.0005 (6)	0.0045 (6)	−0.0011 (6)
C2C	0.0151 (7)	0.0126 (7)	0.0154 (7)	0.0011 (6)	0.0058 (6)	0.0015 (6)
C3C	0.0156 (7)	0.0131 (7)	0.0155 (7)	0.0017 (6)	0.0063 (6)	0.0003 (6)
O2B	0.0263 (6)	0.0210 (6)	0.0156 (6)	−0.0051 (5)	0.0031 (5)	0.0006 (5)
O1C	0.0221 (6)	0.0186 (6)	0.0165 (6)	−0.0066 (4)	0.0029 (5)	0.0036 (4)
C3A	0.0148 (7)	0.0153 (7)	0.0147 (7)	0.0046 (6)	0.0043 (6)	0.0022 (6)
N2A	0.0139 (6)	0.0154 (6)	0.0127 (6)	0.0018 (5)	0.0016 (5)	0.0007 (5)
N1C	0.0192 (7)	0.0173 (7)	0.0176 (7)	−0.0042 (5)	0.0040 (5)	0.0051 (5)
C5A	0.0190 (7)	0.0193 (8)	0.0152 (8)	0.0019 (6)	0.0080 (6)	0.0035 (6)
N3B	0.0182 (6)	0.0166 (7)	0.0153 (7)	0.0011 (5)	0.0053 (5)	0.0034 (5)
C1B	0.0157 (7)	0.0164 (8)	0.0172 (8)	−0.0014 (6)	0.0070 (6)	0.0009 (6)
O2A	0.0270 (6)	0.0226 (6)	0.0164 (6)	−0.0036 (5)	0.0056 (5)	0.0055 (5)
C2B	0.0148 (7)	0.0155 (7)	0.0142 (7)	0.0002 (6)	0.0043 (6)	0.0020 (6)
N3A	0.0170 (6)	0.0171 (7)	0.0142 (6)	0.0032 (5)	0.0053 (5)	0.0022 (5)
C1A	0.0152 (7)	0.0150 (7)	0.0143 (7)	0.0035 (6)	0.0036 (6)	0.0003 (6)
C4C	0.0173 (7)	0.0226 (8)	0.0161 (8)	0.0035 (6)	0.0025 (6)	0.0002 (6)
N1B	0.0368 (8)	0.0218 (7)	0.0159 (7)	−0.0043 (6)	0.0116 (6)	0.0017 (6)
C3B	0.0166 (7)	0.0163 (8)	0.0157 (8)	0.0008 (6)	0.0048 (6)	0.0027 (6)
C4A	0.0150 (7)	0.0149 (7)	0.0202 (8)	0.0016 (6)	0.0072 (6)	0.0029 (6)

Cl1—O4	1.4279 (13)	N2B—C4B	1.347 (2)
Cl1—O1	1.4362 (13)	N2B—C3B	1.354 (2)
Cl1—O3	1.4406 (13)	N2B—H2B	0.86
Cl1—O2	1.4528 (12)	C1C—O1C	1.2553 (19)
C2A—N3A	1.317 (2)	C1C—C2C	1.516 (2)
C2A—C3A	1.439 (2)	C4B—H4B	0.93
C2A—C1A	1.504 (2)	C2C—C3C	1.442 (2)
O1A—C1A	1.3103 (18)	C3C—N1C	1.321 (2)
O1A—H1A	0.82	O2B—C1B	1.2418 (19)
O1W—H1W	0.88 (2)	C3A—N2A	1.352 (2)
O1W—H2W	0.84 (2)	N2A—C4A	1.340 (2)
O2C—C1C	1.2524 (19)	N2A—H2A	0.86
N2C—C4C	1.345 (2)	N1C—H11C	0.86
N2C—C3C	1.353 (2)	N1C—H12C	0.86
N2C—H2C	0.86	C5A—N3A	1.349 (2)
N3C—C2C	1.314 (2)	C5A—C4A	1.365 (2)
N3C—C5C	1.350 (2)	C5A—H5A	0.93
O1B—C1B	1.2631 (19)	N3B—C2B	1.317 (2)
C5B—N3B	1.354 (2)	C1B—C2B	1.520 (2)
C5B—C4B	1.361 (2)	O2A—C1A	1.2112 (19)
C5B—H5B	0.93	C2B—C3B	1.432 (2)
C5C—C4C	1.364 (2)	C4C—H4C	0.93
C5C—H5C	0.93	N1B—C3B	1.321 (2)
N1A—C3A	1.321 (2)	N1B—H11B	0.86
N1A—H11A	0.86	N1B—H12B	0.86
N1A—H12A	0.86	C4A—H4A	0.93
O4—Cl1—O1	110.11 (9)	N1C—C3C—C2C	125.21 (14)
O4—Cl1—O3	110.07 (8)	N2C—C3C—C2C	115.84 (14)
O1—Cl1—O3	109.55 (8)	N1A—C3A—N2A	118.17 (14)
O4—Cl1—O2	109.26 (8)	N1A—C3A—C2A	125.89 (14)
O1—Cl1—O2	108.67 (8)	N2A—C3A—C2A	115.95 (13)
O3—Cl1—O2	109.15 (8)	C4A—N2A—C3A	122.52 (13)
N3A—C2A—C3A	121.68 (14)	C4A—N2A—H2A	118.7
N3A—C2A—C1A	118.80 (13)	C3A—N2A—H2A	118.7
C3A—C2A—C1A	119.47 (13)	C3C—N1C—H11C	120
C1A—O1A—H1A	109.5	C3C—N1C—H12C	120
H1W—O1W—H2W	110 (2)	H11C—N1C—H12C	120
C4C—N2C—C3C	122.50 (14)	N3A—C5A—C4A	121.69 (14)
C4C—N2C—H2C	118.8	N3A—C5A—H5A	119.2
C3C—N2C—H2C	118.8	C4A—C5A—H5A	119.2
C2C—N3C—C5C	119.78 (14)	C2B—N3B—C5B	119.75 (14)
N3B—C5B—C4B	120.86 (15)	O2B—C1B—O1B	126.42 (15)
N3B—C5B—H5B	119.6	O2B—C1B—C2B	118.62 (14)
C4B—C5B—H5B	119.6	O1B—C1B—C2B	114.96 (13)
N3C—C5C—C4C	121.16 (15)	N3B—C2B—C3B	121.61 (14)
N3C—C5C—H5C	119.4	N3B—C2B—C1B	117.00 (14)
C4C—C5C—H5C	119.4	C3B—C2B—C1B	121.38 (14)
C3A—N1A—H11A	120	C2A—N3A—C5A	119.10 (13)
C3A—N1A—H12A	120	O2A—C1A—O1A	124.13 (14)
H11A—N1A—H12A	120	O2A—C1A—C2A	121.45 (14)
C4B—N2B—C3B	122.34 (14)	O1A—C1A—C2A	114.38 (13)
C4B—N2B—H2B	118.8	N2C—C4C—C5C	119.23 (14)
C3B—N2B—H2B	118.8	N2C—C4C—H4C	120.4
O2C—C1C—O1C	125.77 (14)	C5C—C4C—H4C	120.4
O2C—C1C—C2C	116.62 (13)	C3B—N1B—H11B	120
O1C—C1C—C2C	117.59 (13)	C3B—N1B—H12B	120
N2B—C4B—C5B	119.43 (14)	H11B—N1B—H12B	120
N2B—C4B—H4B	120.3	N1B—C3B—N2B	119.36 (14)
C5B—C4B—H4B	120.3	N1B—C3B—C2B	124.66 (15)
N3C—C2C—C3C	121.48 (14)	N2B—C3B—C2B	115.96 (14)
N3C—C2C—C1C	116.98 (13)	N2A—C4A—C5A	119.01 (14)
C3C—C2C—C1C	121.52 (13)	N2A—C4A—H4A	120.5
N1C—C3C—N2C	118.95 (14)	C5A—C4A—H4A	120.5
C2C—N3C—C5C—C4C	0.2 (2)	C5B—N3B—C2B—C1B	177.24 (13)
C3B—N2B—C4B—C5B	−0.1 (2)	O2B—C1B—C2B—N3B	150.06 (15)
N3B—C5B—C4B—N2B	1.2 (2)	O1B—C1B—C2B—N3B	−29.6 (2)
C5C—N3C—C2C—C3C	0.9 (2)	O2B—C1B—C2B—C3B	−31.1 (2)
C5C—N3C—C2C—C1C	−177.26 (14)	O1B—C1B—C2B—C3B	149.24 (15)
O2C—C1C—C2C—N3C	171.42 (14)	C3A—C2A—N3A—C5A	−0.3 (2)
O1C—C1C—C2C—N3C	−6.8 (2)	C1A—C2A—N3A—C5A	177.01 (13)
O2C—C1C—C2C—C3C	−6.8 (2)	C4A—C5A—N3A—C2A	−1.3 (2)
O1C—C1C—C2C—C3C	175.03 (14)	N3A—C2A—C1A—O2A	−173.93 (14)
C4C—N2C—C3C—N1C	−179.80 (14)	C3A—C2A—C1A—O2A	3.5 (2)
C4C—N2C—C3C—C2C	−0.2 (2)	N3A—C2A—C1A—O1A	3.9 (2)
N3C—C2C—C3C—N1C	178.63 (15)	C3A—C2A—C1A—O1A	−178.67 (13)
C1C—C2C—C3C—N1C	−3.3 (2)	C3C—N2C—C4C—C5C	1.3 (2)
N3C—C2C—C3C—N2C	−0.9 (2)	N3C—C5C—C4C—N2C	−1.3 (2)
C1C—C2C—C3C—N2C	177.19 (13)	C4B—N2B—C3B—N1B	179.88 (15)
N3A—C2A—C3A—N1A	−177.91 (14)	C4B—N2B—C3B—C2B	−1.7 (2)
C1A—C2A—C3A—N1A	4.8 (2)	N3B—C2B—C3B—N1B	−179.13 (16)
N3A—C2A—C3A—N2A	2.0 (2)	C1B—C2B—C3B—N1B	2.1 (2)
C1A—C2A—C3A—N2A	−175.33 (12)	N3B—C2B—C3B—N2B	2.5 (2)
N1A—C3A—N2A—C4A	177.75 (14)	C1B—C2B—C3B—N2B	−176.22 (13)
C2A—C3A—N2A—C4A	−2.1 (2)	C3A—N2A—C4A—C5A	0.7 (2)
C4B—C5B—N3B—C2B	−0.3 (2)	N3A—C5A—C4A—N2A	1.1 (2)
C5B—N3B—C2B—C3B	−1.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1W	0.82	1.71	2.5258 (18)	172
O1W—H1W···O1Bi	0.88 (2)	1.92 (2)	2.7873 (19)	169 (2)
O1W—H2W···O2	0.84 (2)	1.99 (2)	2.8176 (19)	172 (2)
O1W—H1W···N3Bi	0.88 (2)	2.56 (2)	3.052 (2)	115.8 (17)
N2B—H2B···O1C	0.86	1.92	2.6935 (18)	149
N1C—H11C···O2Bii	0.86	2.11	2.958 (2)	170
N2C—H2C···O1Bii	0.86	1.76	2.6156 (19)	171
N2A—H2A···O2Ciii	0.86	1.80	2.6536 (17)	175
N1A—H11A···O1Ciii	0.86	2.14	2.9340 (19)	153
N1B—H11B···O1A	0.86	2.26	2.916 (2)	133
N1B—H11B···O1C	0.86	2.44	3.087 (2)	133
N1B—H12B···O2B	0.86	2.21	2.814 (2)	127
N1A—H12A···O2A	0.86	2.09	2.7038 (19)	128
N1C—H12C···O2C	0.86	2.06	2.6734 (19)	128
N2B—H2B···N3C	0.86	2.41	3.058 (2)	132
N1B—H12B···N3A	0.86	2.41	3.035 (2)	130
N1A—H12A···N3Biv	0.86	2.44	3.152 (2)	140
C4B—H4B···O1v	0.93	2.41	3.267 (2)	153
C4C—H4C···O3vi	0.93	2.45	3.350 (2)	162
C5A—H5A···O2B	0.93	2.58	3.336 (2)	138
C5B—H5B···O2v	0.93	2.48	3.145 (2)	129
C5B—H5B···O2Av	0.93	2.48	3.164 (2)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O1W	0.82	1.71	2.5258 (18)	172
O1W—H1W⋯O1Bi	0.88 (2)	1.92 (2)	2.7873 (19)	169 (2)
O1W—H2W⋯O2	0.84 (2)	1.99 (2)	2.8176 (19)	172 (2)
O1W—H1W⋯N3Bi	0.88 (2)	2.56 (2)	3.052 (2)	115.8 (17)
N2B—H2B⋯O1C	0.86	1.92	2.6935 (18)	149
N1C—H11C⋯O2Bii	0.86	2.11	2.958 (2)	170
N2C—H2C⋯O1Bii	0.86	1.76	2.6156 (19)	171
N2A—H2A⋯O2Ciii	0.86	1.80	2.6536 (17)	175
N1A—H11A⋯O1Ciii	0.86	2.14	2.9340 (19)	153
N1B—H11B⋯O1A	0.86	2.26	2.916 (2)	133
N1B—H11B⋯O1C	0.86	2.44	3.087 (2)	133
N1B—H12B⋯O2B	0.86	2.21	2.814 (2)	127
N1A—H12A⋯O2A	0.86	2.09	2.7038 (19)	128
N1C—H12C⋯O2C	0.86	2.06	2.6734 (19)	128
N2B—H2B⋯N3C	0.86	2.41	3.058 (2)	132
N1B—H12B⋯N3A	0.86	2.41	3.035 (2)	130
N1A—H12A⋯N3Biv	0.86	2.44	3.152 (2)	140
C4B—H4B⋯O1v	0.93	2.41	3.267 (2)	153
C4C—H4C⋯O3vi	0.93	2.45	3.350 (2)	162
C5A—H5A⋯O2B	0.93	2.58	3.336 (2)	138
C5B—H5B⋯O2v	0.93	2.48	3.145 (2)	129
C5B—H5B⋯O2Av	0.93	2.48	3.164 (2)	130

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