Bis(5-amino-3-carb-oxy-1H-1,2,4-triazol-4-ium) dihydrogenphosphate nitrate 5-amino-1H-1,2,4-triazol-4-ium-3-carboxyl-ate.

In the title compound, 2C(3)H(5)N(4)O(2) (+)·H(2)PO(4) (-)·NO(3) (-)·C(3)H(4)N(4)O(2), three independent 5-amino-1H-1,2,4-triazol-3-carb-oxy-lic acid moieties are observed. Two are in the form of cations, while the third is in the zwitterionic form. The triazole rings in the two cations are almost coplanar, making an angle of 4.11 (7)°. Layers parallel to the (20-1) plane, resulting from hydrogen bonding of the organic mol-ecules and the nitrate anions, are linked via H(2)PO(4) (-) infinite zigzag chains running parallel to the c axis. The crystal studied was an inversion twin, with refined components of 0.33 (7) and 0.67 (7).

Related literature

For structural studies of related compounds, see: Berrah et al. (2011 ▶, 2012 ▶); Fernandes et al. (2011 ▶); Ouakkaf et al. (2011 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Grell et al. (1999 ▶).

Experimental

Crystal data

2C3H5N4O2 +·NO3 −·H2PO4 −·C3H4N4O2

M = 545.32

Monoclinic,

a = 19.2249 (13) Å

b = 13.2036 (7) Å

c = 7.7468 (5) Å

β = 101.079 (7)°

V = 1929.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 180 K

0.45 × 0.43 × 0.16 mm

Data collection

Agilent Xcalibur Sapphire1 long-nozzle diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.832, T max = 1.000

10050 measured reflections

3836 independent reflections

3735 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.067

S = 1.05

3836 reflections

330 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 1858 Friedel pairs

Flack parameter: 0.33 (7)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812014481/fj2538sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014481/fj2538Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014481/fj2538Isup3.cml

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

2C3H5N4O2+·NO3−·H2PO4−·C3H4N4O2	F(000) = 1120
Mr = 545.32	Dx = 1.877 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 19.2249 (13) Å	Cell parameters from 8428 reflections
b = 13.2036 (7) Å	θ = 3.1–28.3°
c = 7.7468 (5) Å	µ = 0.25 mm−1
β = 101.079 (7)°	T = 180 K
V = 1929.8 (2) Å3	Box, colourless
Z = 4	0.45 × 0.43 × 0.16 mm

Agilent Xcalibur Sapphire1 long-nozzle diffractometer	3836 independent reflections
Radiation source: fine-focus sealed tube	3735 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.2632 pixels mm-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −24→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→16
Tmin = 0.832, Tmax = 1.000	l = −9→9
10050 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027	H-atom parameters constrained
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.0378P)2 + 0.9492P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.008
3836 reflections	Δρmax = 0.23 e Å−3
330 parameters	Δρmin = −0.27 e Å−3
2 restraints	Absolute structure: Flack (1983), 1858 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.33 (7)

Experimental. Absorption correction: empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlisPro (Agilent Technologies, 2011)

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
O6	0.41566 (8)	1.31611 (10)	0.5894 (2)	0.0222 (3)
N3C	0.18588 (9)	1.43700 (13)	0.1472 (2)	0.0236 (4)
O1C	0.30311 (8)	1.62763 (11)	0.3449 (2)	0.0272 (3)
N1B	0.58554 (9)	1.25858 (12)	0.9762 (2)	0.0217 (4)
H5B	0.6216	1.2555	1.061	0.026*
H3B	0.5677	1.3164	0.9405	0.026*
N4C	0.28426 (9)	1.41292 (12)	0.3399 (2)	0.0201 (4)
H4C	0.3233	1.4265	0.4111	0.024*
N1	0.43355 (9)	1.40196 (12)	0.6489 (2)	0.0184 (3)
C3C	0.25660 (10)	1.32115 (15)	0.3022 (3)	0.0187 (4)
O2C	0.19992 (9)	1.64211 (12)	0.1575 (2)	0.0349 (4)
N2C	0.19719 (9)	1.33628 (12)	0.1833 (2)	0.0219 (4)
H2C	0.1695	1.2886	0.1356	0.026*
O7	0.48583 (8)	1.41235 (11)	0.7696 (2)	0.0276 (3)
C1C	0.24818 (11)	1.59375 (15)	0.2508 (3)	0.0215 (4)
O5	0.39976 (9)	1.47811 (11)	0.5845 (2)	0.0313 (4)
N1C	0.28090 (10)	1.23307 (13)	0.3647 (2)	0.0266 (4)
H5C	0.3198	1.2297	0.4408	0.032*
H3C	0.2579	1.1786	0.3296	0.032*
C2C	0.23928 (11)	1.48136 (15)	0.2447 (3)	0.0202 (4)
P1	0.27249 (3)	0.89899 (3)	0.30351 (6)	0.01592 (11)
O2B	0.43278 (7)	0.92432 (10)	0.59606 (18)	0.0210 (3)
N2B	0.57956 (9)	1.08016 (13)	0.9423 (2)	0.0198 (3)
H2B	0.6152	1.0654	1.0238	0.024*
N4B	0.50067 (9)	1.16518 (12)	0.7706 (2)	0.0167 (3)
H4B	0.475	1.2135	0.7182	0.02*
N3B	0.53912 (9)	1.01015 (12)	0.8405 (2)	0.0194 (3)
C2B	0.49164 (10)	1.06425 (14)	0.7377 (2)	0.0167 (4)
C3B	0.55750 (10)	1.17458 (15)	0.9007 (2)	0.0159 (4)
O3	0.30722 (7)	0.99921 (10)	0.27601 (17)	0.0198 (3)
C3A	0.47957 (10)	1.70083 (15)	0.7432 (3)	0.0186 (4)
O2	0.32459 (7)	0.81370 (10)	0.2805 (2)	0.0247 (3)
H2	0.309	0.7593	0.3072	0.037*
O1	0.20396 (9)	0.88190 (12)	0.1753 (3)	0.0359 (4)
N3A	0.56813 (9)	1.75022 (12)	0.9580 (2)	0.0189 (3)
N2A	0.51436 (9)	1.78030 (13)	0.8257 (2)	0.0202 (3)
H2A	0.5042	1.8425	0.7988	0.024*
O2A	0.65270 (7)	1.62929 (11)	1.20239 (19)	0.0233 (3)
N1A	0.42476 (10)	1.70396 (14)	0.6126 (2)	0.0266 (4)
H5A	0.4079	1.7614	0.572	0.032*
H3A	0.4058	1.6486	0.5677	0.032*
C1B	0.43737 (10)	1.01611 (14)	0.6006 (3)	0.0164 (4)
N4A	0.51196 (9)	1.61845 (12)	0.8229 (2)	0.0181 (3)
H4A	0.5014	1.5563	0.7966	0.022*
O1B	0.40060 (7)	1.08030 (10)	0.49496 (18)	0.0185 (3)
H1B	0.3709	1.05	0.4234	0.028*
O4	0.25679 (10)	0.89062 (14)	0.4902 (2)	0.0431 (5)
H4	0.2766	0.9369	0.551	0.065*
O1A	0.60814 (8)	1.49336 (11)	1.0444 (2)	0.0267 (3)
H1A	0.6426	1.4631	1.0994	0.04*
C1A	0.61377 (10)	1.58682 (15)	1.0807 (3)	0.0180 (4)
C2A	0.56512 (10)	1.65246 (15)	0.9543 (3)	0.0174 (4)

	U11	U22	U33	U12	U13	U23
O6	0.0208 (7)	0.0113 (6)	0.0303 (7)	−0.0030 (5)	−0.0055 (6)	−0.0021 (6)
N3C	0.0210 (9)	0.0151 (8)	0.0305 (10)	−0.0020 (7)	−0.0057 (8)	0.0017 (7)
O1C	0.0224 (8)	0.0126 (7)	0.0398 (9)	−0.0015 (6)	−0.0109 (7)	0.0016 (6)
N1B	0.0206 (9)	0.0172 (8)	0.0232 (8)	−0.0014 (7)	−0.0061 (7)	0.0008 (7)
N4C	0.0175 (9)	0.0147 (8)	0.0243 (9)	−0.0010 (6)	−0.0059 (7)	0.0012 (6)
N1	0.0166 (8)	0.0133 (8)	0.0235 (8)	0.0012 (6)	−0.0006 (7)	0.0016 (6)
C3C	0.0191 (10)	0.0172 (9)	0.0193 (9)	−0.0020 (7)	0.0020 (8)	−0.0008 (7)
O2C	0.0277 (8)	0.0176 (8)	0.0494 (10)	0.0007 (7)	−0.0172 (7)	0.0056 (7)
N2C	0.0192 (9)	0.0122 (8)	0.0302 (9)	−0.0038 (6)	−0.0056 (7)	−0.0013 (7)
O7	0.0244 (8)	0.0181 (7)	0.0326 (8)	0.0005 (6)	−0.0138 (7)	−0.0017 (6)
C1C	0.0196 (10)	0.0153 (10)	0.0273 (11)	0.0014 (8)	−0.0012 (8)	0.0028 (8)
O5	0.0286 (8)	0.0129 (7)	0.0439 (9)	0.0020 (6)	−0.0145 (7)	0.0045 (6)
N1C	0.0271 (10)	0.0136 (8)	0.0333 (10)	−0.0019 (7)	−0.0091 (8)	0.0001 (7)
C2C	0.0171 (9)	0.0180 (10)	0.0230 (10)	−0.0005 (8)	−0.0024 (8)	0.0012 (8)
P1	0.0149 (2)	0.0125 (2)	0.0184 (2)	−0.0002 (2)	−0.00181 (17)	−0.00174 (19)
O2B	0.0221 (7)	0.0141 (7)	0.0247 (7)	−0.0016 (5)	−0.0009 (6)	−0.0013 (6)
N2B	0.0176 (8)	0.0166 (8)	0.0211 (8)	0.0007 (6)	−0.0062 (7)	0.0024 (6)
N4B	0.0166 (8)	0.0137 (8)	0.0174 (8)	0.0017 (6)	−0.0024 (6)	0.0021 (6)
N3B	0.0182 (8)	0.0160 (8)	0.0216 (8)	0.0006 (7)	−0.0019 (7)	0.0008 (6)
C2B	0.0171 (9)	0.0157 (9)	0.0169 (9)	0.0012 (7)	0.0027 (8)	0.0018 (7)
C3B	0.0124 (8)	0.0189 (9)	0.0155 (9)	−0.0011 (7)	0.0007 (7)	0.0011 (7)
O3	0.0214 (7)	0.0151 (6)	0.0197 (7)	−0.0021 (5)	−0.0041 (6)	0.0010 (5)
C3A	0.0188 (9)	0.0161 (10)	0.0199 (10)	0.0015 (7)	0.0014 (8)	−0.0001 (7)
O2	0.0193 (7)	0.0136 (6)	0.0412 (9)	0.0006 (5)	0.0063 (6)	0.0013 (6)
O1	0.0266 (8)	0.0177 (8)	0.0519 (10)	0.0006 (6)	−0.0217 (8)	−0.0017 (7)
N3A	0.0194 (8)	0.0145 (8)	0.0215 (8)	0.0002 (6)	0.0006 (7)	−0.0010 (6)
N2A	0.0226 (9)	0.0121 (7)	0.0239 (8)	0.0019 (6)	−0.0006 (7)	0.0013 (6)
O2A	0.0202 (7)	0.0217 (7)	0.0249 (7)	−0.0009 (6)	−0.0033 (6)	−0.0024 (6)
N1A	0.0279 (10)	0.0158 (9)	0.0311 (10)	0.0014 (7)	−0.0072 (8)	0.0009 (7)
C1B	0.0161 (9)	0.0146 (9)	0.0191 (9)	0.0012 (7)	0.0047 (7)	−0.0001 (7)
N4A	0.0184 (9)	0.0107 (8)	0.0232 (8)	0.0004 (6)	−0.0009 (7)	−0.0019 (6)
O1B	0.0181 (7)	0.0147 (6)	0.0194 (7)	−0.0009 (5)	−0.0042 (5)	0.0000 (5)
O4	0.0594 (12)	0.0425 (11)	0.0327 (9)	−0.0305 (9)	0.0219 (9)	−0.0148 (7)
O1A	0.0214 (7)	0.0154 (7)	0.0358 (8)	0.0041 (6)	−0.0132 (7)	−0.0001 (6)
C1A	0.0134 (9)	0.0166 (9)	0.0228 (10)	−0.0001 (7)	0.0003 (8)	−0.0010 (7)
C2A	0.0149 (9)	0.0168 (9)	0.0201 (9)	−0.0003 (7)	0.0020 (7)	−0.0022 (7)

O6—N1	1.247 (2)	N2B—N3B	1.358 (2)
N3C—C2C	1.292 (3)	N2B—H2B	0.86
N3C—N2C	1.368 (2)	N4B—C3B	1.342 (3)
O1C—C1C	1.245 (3)	N4B—C2B	1.362 (3)
N1B—C3B	1.320 (3)	N4B—H4B	0.86
N1B—H5B	0.86	N3B—C2B	1.303 (3)
N1B—H3B	0.86	C2B—C1B	1.482 (3)
N4C—C3C	1.333 (3)	C3A—N1A	1.314 (3)
N4C—C2C	1.365 (3)	C3A—N2A	1.339 (3)
N4C—H4C	0.86	C3A—N4A	1.343 (2)
N1—O7	1.241 (2)	O2—H2	0.82
N1—O5	1.248 (2)	N3A—C2A	1.292 (3)
C3C—N1C	1.311 (3)	N3A—N2A	1.367 (2)
C3C—N2C	1.337 (3)	N2A—H2A	0.86
O2C—C1C	1.238 (3)	O2A—C1A	1.222 (2)
N2C—H2C	0.86	N1A—H5A	0.86
C1C—C2C	1.493 (3)	N1A—H3A	0.86
N1C—H5C	0.86	C1B—O1B	1.290 (2)
N1C—H3C	0.86	N4A—C2A	1.372 (3)
P1—O1	1.5068 (16)	N4A—H4A	0.86
P1—O3	1.5156 (14)	O1B—H1B	0.82
P1—O4	1.5371 (16)	O4—H4	0.82
P1—O2	1.5402 (14)	O1A—C1A	1.266 (2)
O2B—C1B	1.215 (2)	O1A—H1A	0.82
N2B—C3B	1.336 (3)	C1A—C2A	1.494 (3)
C2C—N3C—N2C	104.11 (16)	C3B—N4B—H4B	126.7
C3B—N1B—H5B	120	C2B—N4B—H4B	126.7
C3B—N1B—H3B	120	C2B—N3B—N2B	103.72 (16)
H5B—N1B—H3B	120	N3B—C2B—N4B	111.91 (17)
C3C—N4C—C2C	107.38 (17)	N3B—C2B—C1B	121.13 (17)
C3C—N4C—H4C	126.3	N4B—C2B—C1B	126.94 (17)
C2C—N4C—H4C	126.3	N1B—C3B—N2B	126.42 (18)
O7—N1—O6	120.32 (16)	N1B—C3B—N4B	127.92 (18)
O7—N1—O5	119.72 (16)	N2B—C3B—N4B	105.64 (17)
O6—N1—O5	119.94 (18)	N1A—C3A—N2A	126.59 (19)
N1C—C3C—N4C	128.80 (19)	N1A—C3A—N4A	127.73 (19)
N1C—C3C—N2C	125.70 (18)	N2A—C3A—N4A	105.69 (17)
N4C—C3C—N2C	105.49 (17)	P1—O2—H2	109.5
C3C—N2C—N3C	111.56 (16)	C2A—N3A—N2A	104.42 (16)
C3C—N2C—H2C	124.2	C3A—N2A—N3A	111.50 (16)
N3C—N2C—H2C	124.2	C3A—N2A—H2A	124.3
O2C—C1C—O1C	127.77 (19)	N3A—N2A—H2A	124.3
O2C—C1C—C2C	115.2 (2)	C3A—N1A—H5A	120
O1C—C1C—C2C	117.04 (18)	C3A—N1A—H3A	120
C3C—N1C—H5C	120	H5A—N1A—H3A	120
C3C—N1C—H3C	120	O2B—C1B—O1B	127.51 (19)
H5C—N1C—H3C	120	O2B—C1B—C2B	119.06 (18)
N3C—C2C—N4C	111.43 (17)	O1B—C1B—C2B	113.41 (16)
N3C—C2C—C1C	122.84 (19)	C3A—N4A—C2A	106.82 (16)
N4C—C2C—C1C	125.72 (19)	C3A—N4A—H4A	126.6
O1—P1—O3	113.02 (9)	C2A—N4A—H4A	126.6
O1—P1—O4	107.73 (11)	C1B—O1B—H1B	109.5
O3—P1—O4	111.50 (8)	P1—O4—H4	109.5
O1—P1—O2	108.65 (9)	C1A—O1A—H1A	109.5
O3—P1—O2	107.95 (8)	O2A—C1A—O1A	129.23 (19)
O4—P1—O2	107.83 (10)	O2A—C1A—C2A	116.94 (17)
C3B—N2B—N3B	112.03 (16)	O1A—C1A—C2A	113.83 (17)
C3B—N2B—H2B	124	N3A—C2A—N4A	111.56 (18)
N3B—N2B—H2B	124	N3A—C2A—C1A	123.02 (18)
C3B—N4B—C2B	106.68 (16)	N4A—C2A—C1A	125.42 (17)
C2C—N4C—C3C—N1C	−178.8 (2)	C2B—N4B—C3B—N1B	−179.47 (19)
C2C—N4C—C3C—N2C	1.5 (2)	C2B—N4B—C3B—N2B	−0.86 (19)
N1C—C3C—N2C—N3C	179.1 (2)	N1A—C3A—N2A—N3A	178.89 (19)
N4C—C3C—N2C—N3C	−1.2 (2)	N4A—C3A—N2A—N3A	−0.6 (2)
C2C—N3C—N2C—C3C	0.4 (2)	C2A—N3A—N2A—C3A	−0.1 (2)
N2C—N3C—C2C—N4C	0.6 (2)	N3B—C2B—C1B—O2B	7.5 (3)
N2C—N3C—C2C—C1C	−178.60 (19)	N4B—C2B—C1B—O2B	−174.60 (18)
C3C—N4C—C2C—N3C	−1.3 (2)	N3B—C2B—C1B—O1B	−171.11 (17)
C3C—N4C—C2C—C1C	177.8 (2)	N4B—C2B—C1B—O1B	6.8 (3)
O2C—C1C—C2C—N3C	1.2 (3)	N1A—C3A—N4A—C2A	−178.5 (2)
O1C—C1C—C2C—N3C	−177.4 (2)	N2A—C3A—N4A—C2A	1.0 (2)
O2C—C1C—C2C—N4C	−177.9 (2)	N2A—N3A—C2A—N4A	0.8 (2)
O1C—C1C—C2C—N4C	3.5 (3)	N2A—N3A—C2A—C1A	−178.54 (16)
C3B—N2B—N3B—C2B	−0.7 (2)	C3A—N4A—C2A—N3A	−1.1 (2)
N2B—N3B—C2B—N4B	0.1 (2)	C3A—N4A—C2A—C1A	178.15 (18)
N2B—N3B—C2B—C1B	178.28 (17)	O2A—C1A—C2A—N3A	7.6 (3)
C3B—N4B—C2B—N3B	0.5 (2)	O1A—C1A—C2A—N3A	−172.49 (19)
C3B—N4B—C2B—C1B	−177.57 (19)	O2A—C1A—C2A—N4A	−171.63 (18)
N3B—N2B—C3B—N1B	179.60 (19)	O1A—C1A—C2A—N4A	8.3 (3)
N3B—N2B—C3B—N4B	1.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H5B···O2Ci	0.86	2.15	2.826 (2)	135
N1B—H5B···O1ii	0.86	2.35	2.977 (2)	130
N1B—H3B···O7	0.86	2.24	3.030 (2)	152
N1B—H3B···O1A	0.86	2.54	3.161 (2)	129
N4C—H4C···O5	0.86	1.92	2.765 (2)	169
N4C—H4C···O6	0.86	2.5	3.142 (2)	132
N4C—H4C···N1	0.86	2.55	3.369 (2)	160
N2C—H2C···O2Aiii	0.86	2.21	2.876 (2)	135
N2C—H2C···N3Aiii	0.86	2.22	2.971 (2)	146
N1C—H5C···O6	0.86	2.28	3.035 (2)	146
N1C—H5C···O1B	0.86	2.5	3.081 (2)	126
N1C—H3C···O2Aiii	0.86	2.17	2.888 (2)	140
N1C—H3C···O3	0.86	2.61	3.224 (2)	129
N2B—H2B···O2Ci	0.86	2.03	2.706 (2)	135
N2B—H2B···N3Ci	0.86	2.27	3.004 (2)	144
N4B—H4B···O6	0.86	1.92	2.780 (2)	177
N4B—H4B···O7	0.86	2.66	3.276 (2)	130
N4B—H4B···N1	0.86	2.64	3.444 (2)	157
O2—H2···O1Civ	0.82	1.77	2.5563 (19)	160
N2A—H2A···O2Bv	0.86	2.17	2.858 (2)	137
N2A—H2A···N3Bv	0.86	2.32	3.071 (2)	146
N1A—H5A···O2Bv	0.86	2.2	2.918 (2)	140
N1A—H5A···O2v	0.86	2.6	3.244 (2)	133
N1A—H3A···O5	0.86	2.26	3.022 (2)	148
N1A—H3A···O1C	0.86	2.38	2.987 (2)	129
N4A—H4A···O7	0.86	1.93	2.784 (2)	172
N4A—H4A···O5	0.86	2.52	3.157 (2)	132
N4A—H4A···N1	0.86	2.57	3.388 (2)	160
O1B—H1B···O3	0.82	1.65	2.4648 (19)	175
O4—H4···O3vi	0.82	1.92	2.671 (2)	151
O1A—H1A···O1ii	0.82	1.62	2.423 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H3B⋯O7	0.86	2.24	3.030 (2)	152
N4C—H4C⋯O5	0.86	1.92	2.765 (2)	169
N4B—H4B⋯O6	0.86	1.92	2.780 (2)	177
O2—H2⋯O1Ci	0.82	1.77	2.5563 (19)	160
N4A—H4A⋯O7	0.86	1.93	2.784 (2)	172
O1B—H1B⋯O3	0.82	1.65	2.4648 (19)	175
O4—H4⋯O3ii	0.82	1.92	2.671 (2)	151
O1A—H1A⋯O1iii	0.82	1.62	2.423 (2)	166

Symmetry codes: (i) ; (ii) ; (iii) .