Poly[bis-(piperazine-1,4-diium) [(μ4-cyclo-hexa-phosphato)dilithium] tetra-hydrate].

In the title compound, {(C4H12N2)2[Li2(P6O18)]·4H2O} n , the phosphate ring anion, located around an inversion center, adopts a chair conformation. Adjacent P6O18 rings are linked via corner-sharing by LiO4 tetra-hedra, generating anionic porous {[Li2(P6O18)](4-)} n layers parallel to (101). The piperazine-1,4-diium cations occupy the pores and develop hydrogen bonds with the inorganic framework. An extensive network of N-H⋯O and O-H⋯O hydrogen-bonding inter-actions link the components into a three-dimensional network and additional stabilization is provided by weak C-H⋯O hydrogen bonds.

Related literature

For applications of compounds with open-framework structures, see: Assani et al. (2012 ▶); Mahesh et al. (2002 ▶); Natarajan (2000 ▶). For related structures with cyclo­hexa­phosphate rings, see: Abid et al. (2011 ▶), Amri et al. (2009 ▶); Marouani et al. (2010 ▶); For related structures with piperazine rings, see: Essid et al. (2010 ▶), Xu et al. (2007 ▶). For the synthesis of the precursor, see: Schülke & Kayser (1985 ▶).

Experimental

Crystal data

(C4H12N2)2[Li2(P6O18)]·4H2O

M = 736.08

Monoclinic,

a = 10.245 (3) Å

b = 12.966 (4) Å

c = 10.910 (4) Å

β = 111.00 (3)°

V = 1352.8 (7) Å3

Z = 2

Ag Kα radiation

λ = 0.56085 Å

μ = 0.26 mm−1

T = 293 K

0.50 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

7884 measured reflections

6469 independent reflections

3904 reflections with I > 2σ(I)

R int = 0.038

2 standard reflections every 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.128

S = 1.00

6469 reflections

202 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813011756/pk2476sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011756/pk2476Isup2.hkl

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

(C4H12N2)2[Li2(P6O18)]·4H2O	F(000) = 760
Mr = 736.08	Dx = 1.807 Mg m−3
Monoclinic, P21/c	Ag Kα radiation, λ = 0.56085 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.245 (3) Å	θ = 9.1–10.9°
b = 12.966 (4) Å	µ = 0.26 mm−1
c = 10.910 (4) Å	T = 293 K
β = 111.00 (3)°	Parallelepiped, colourless
V = 1352.8 (7) Å3	0.50 × 0.40 × 0.30 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	Rint = 0.038
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.0°
Graphite monochromator	h = −17→15
non–profiled ω–scans	k = −3→21
7884 measured reflections	l = 0→18
6469 independent reflections	2 standard reflections every 120 min
3904 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.059P)2] where P = (Fo2 + 2Fc2)/3
6469 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.57 e Å−3
6 restraints	Δρmin = −0.47 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
P1	0.67085 (5)	0.82511 (4)	0.10243 (4)	0.01597 (10)
P2	0.73450 (5)	0.99726 (4)	0.28486 (5)	0.01656 (10)
P3	0.60626 (5)	1.16305 (4)	0.09894 (5)	0.01660 (10)
O3	0.75517 (14)	0.92532 (11)	0.17300 (12)	0.0195 (3)
O6	0.61176 (15)	1.07330 (12)	0.20122 (14)	0.0232 (3)
O5	0.86457 (16)	1.05454 (13)	0.34765 (15)	0.0287 (3)
O2	0.6560 (2)	0.75209 (12)	0.19975 (15)	0.0325 (4)
O4	0.67240 (16)	0.93559 (11)	0.36583 (13)	0.0227 (3)
O1	0.73374 (16)	0.78864 (13)	0.00746 (14)	0.0267 (3)
O8	0.73427 (15)	1.16386 (13)	0.06704 (14)	0.0251 (3)
O7	0.56459 (15)	1.26004 (11)	0.14913 (14)	0.0232 (3)
O9	0.52184 (15)	0.87728 (12)	0.02453 (14)	0.0265 (3)
N1	0.7657 (2)	1.11939 (14)	−0.17128 (17)	0.0267 (4)
H2A	0.7908	1.1407	−0.0875	0.032*
H2B	0.7086	1.1673	−0.2230	0.032*
C1	0.6902 (3)	1.01996 (18)	−0.1870 (2)	0.0304 (5)
H1A	0.6079	1.0284	−0.1637	0.036*
H1B	0.7501	0.9687	−0.1291	0.036*
C4	0.8925 (2)	1.1093 (2)	−0.2064 (2)	0.0354 (5)
H1C	0.9576	1.0617	−0.1464	0.042*
H1D	0.9381	1.1758	−0.1984	0.042*
C3	0.8530 (3)	1.0702 (2)	−0.3449 (2)	0.0335 (5)
H4A	0.7966	1.1217	−0.4054	0.040*
H4B	0.9370	1.0592	−0.3647	0.040*
N2	0.7735 (2)	0.97230 (15)	−0.36309 (18)	0.0290 (4)
H3A	0.8288	0.9229	−0.3127	0.035*
H3B	0.7476	0.9522	−0.4474	0.035*
Li1	0.6251 (4)	0.7890 (3)	0.3536 (3)	0.0246 (7)
C2	0.6474 (3)	0.98435 (18)	−0.3276 (2)	0.0307 (5)
H2C	0.5984	0.9190	−0.3383	0.037*
H2D	0.5846	1.0344	−0.3853	0.037*
O10	1.0185 (2)	1.28956 (19)	0.0074 (2)	0.0502 (6)
O11	0.9729 (2)	0.8504 (2)	−0.1959 (3)	0.0704 (9)
H110	1.094 (3)	1.281 (4)	−0.006 (4)	0.106*
H210	0.967 (4)	1.330 (3)	−0.047 (4)	0.106*
H111	1.058 (2)	0.863 (4)	−0.179 (4)	0.106*
H211	0.969 (5)	0.802 (3)	−0.144 (4)	0.106*

	U11	U22	U33	U12	U13	U23
P1	0.0187 (2)	0.0152 (2)	0.01382 (18)	0.00116 (17)	0.00556 (15)	−0.00189 (16)
P2	0.0190 (2)	0.0153 (2)	0.01505 (19)	−0.00225 (17)	0.00565 (15)	−0.00241 (16)
P3	0.0162 (2)	0.0158 (2)	0.01738 (19)	0.00004 (17)	0.00551 (15)	−0.00147 (16)
O3	0.0212 (6)	0.0209 (6)	0.0181 (6)	−0.0030 (5)	0.0091 (5)	−0.0058 (5)
O6	0.0217 (7)	0.0207 (7)	0.0302 (7)	0.0029 (5)	0.0128 (6)	0.0062 (6)
O5	0.0250 (7)	0.0285 (8)	0.0271 (7)	−0.0091 (6)	0.0027 (6)	−0.0082 (6)
O2	0.0594 (12)	0.0183 (7)	0.0234 (7)	−0.0060 (7)	0.0191 (7)	−0.0004 (6)
O4	0.0337 (8)	0.0192 (6)	0.0185 (6)	−0.0016 (6)	0.0137 (6)	0.0005 (5)
O1	0.0254 (7)	0.0347 (8)	0.0224 (6)	0.0018 (6)	0.0114 (6)	−0.0110 (6)
O8	0.0205 (6)	0.0345 (8)	0.0224 (6)	−0.0001 (6)	0.0103 (5)	0.0014 (6)
O7	0.0242 (7)	0.0161 (6)	0.0275 (7)	0.0000 (5)	0.0071 (6)	−0.0063 (5)
O9	0.0196 (7)	0.0258 (7)	0.0267 (7)	0.0058 (6)	−0.0007 (5)	−0.0122 (6)
N1	0.0352 (10)	0.0237 (9)	0.0192 (7)	0.0056 (7)	0.0076 (7)	−0.0028 (6)
C1	0.0372 (12)	0.0262 (10)	0.0362 (11)	0.0027 (9)	0.0235 (10)	0.0068 (9)
C4	0.0259 (11)	0.0373 (13)	0.0395 (12)	−0.0065 (10)	0.0075 (9)	−0.0058 (10)
C3	0.0349 (12)	0.0400 (13)	0.0333 (11)	0.0017 (10)	0.0215 (10)	0.0040 (10)
N2	0.0398 (11)	0.0255 (9)	0.0213 (8)	0.0097 (8)	0.0104 (7)	−0.0012 (7)
Li1	0.0339 (19)	0.0211 (17)	0.0196 (15)	−0.0037 (15)	0.0106 (14)	0.0038 (13)
C2	0.0304 (11)	0.0208 (10)	0.0384 (12)	−0.0015 (8)	0.0091 (9)	−0.0031 (9)
O10	0.0547 (13)	0.0556 (13)	0.0526 (12)	0.0314 (11)	0.0343 (11)	0.0273 (10)
O11	0.0229 (9)	0.0848 (19)	0.1003 (19)	0.0123 (11)	0.0183 (11)	0.0638 (16)

P1—O2	1.4707 (16)	N1—H2B	0.9000
P1—O1	1.4801 (15)	C1—C2	1.509 (3)
P1—O3	1.5970 (15)	C1—H1A	0.9700
P1—O9	1.6063 (16)	C1—H1B	0.9700
P1—Li1	2.978 (4)	C4—C3	1.505 (3)
P1—Li1i	2.978 (4)	C4—H1C	0.9700
P2—O5	1.4636 (16)	C4—H1D	0.9700
P2—O4	1.4925 (15)	C3—N2	1.483 (3)
P2—O6	1.6011 (16)	C3—H4A	0.9700
P2—O3	1.6091 (14)	C3—H4B	0.9700
P2—Li1	3.117 (4)	N2—C2	1.483 (3)
P3—O8	1.4725 (15)	N2—H3A	0.9000
P3—O7	1.4937 (15)	N2—H3B	0.9000
P3—O9ii	1.5945 (16)	Li1—O1iv	1.931 (4)
P3—O6	1.5991 (15)	Li1—O7v	1.969 (4)
P3—Li1iii	3.071 (4)	Li1—P1iv	2.978 (4)
O2—Li1	1.877 (4)	Li1—P3v	3.071 (4)
O4—Li1	1.954 (4)	C2—H2C	0.9700
O1—Li1i	1.931 (4)	C2—H2D	0.9700
O7—Li1iii	1.969 (4)	O10—H110	0.846 (18)
O9—P3ii	1.5945 (16)	O10—H210	0.822 (18)
N1—C1	1.482 (3)	O11—H111	0.840 (18)
N1—C4	1.485 (3)	O11—H211	0.851 (18)
N1—H2A	0.9000
O2—P1—O1	118.91 (10)	N1—C4—H1C	109.6
O2—P1—O3	110.72 (9)	C3—C4—H1C	109.6
O1—P1—O3	107.54 (9)	N1—C4—H1D	109.6
O2—P1—O9	109.16 (11)	C3—C4—H1D	109.6
O1—P1—O9	109.50 (9)	H1C—C4—H1D	108.2
O3—P1—O9	99.19 (8)	N2—C3—C4	111.03 (19)
O1—P1—Li1	147.71 (11)	N2—C3—H4A	109.4
O3—P1—Li1	85.45 (9)	C4—C3—H4A	109.4
O9—P1—Li1	96.89 (10)	N2—C3—H4B	109.4
O2—P1—Li1i	108.38 (10)	C4—C3—H4B	109.4
O1—P1—Li1i	33.78 (10)	H4A—C3—H4B	108.0
O3—P1—Li1i	136.45 (9)	C3—N2—C2	111.29 (17)
O9—P1—Li1i	85.28 (10)	C3—N2—H3A	109.4
Li1—P1—Li1i	137.36 (7)	C2—N2—H3A	109.4
O5—P2—O4	120.31 (9)	C3—N2—H3B	109.4
O5—P2—O6	110.58 (10)	C2—N2—H3B	109.4
O4—P2—O6	104.65 (8)	H3A—N2—H3B	108.0
O5—P2—O3	107.69 (9)	O2—Li1—O1iv	114.5 (2)
O4—P2—O3	109.77 (9)	O2—Li1—O4	101.07 (17)
O6—P2—O3	102.40 (8)	O1iv—Li1—O4	113.3 (2)
O5—P2—Li1	132.28 (10)	O2—Li1—O7v	114.8 (2)
O4—P2—Li1	29.20 (9)	O1iv—Li1—O7v	99.89 (17)
O6—P2—Li1	113.21 (9)	O4—Li1—O7v	113.9 (2)
O3—P2—Li1	80.59 (9)	O2—Li1—P1	23.82 (7)
O8—P3—O7	118.45 (10)	O1iv—Li1—P1	130.56 (19)
O8—P3—O9ii	109.62 (9)	O4—Li1—P1	78.06 (12)
O7—P3—O9ii	109.20 (8)	O7v—Li1—P1	119.75 (16)
O8—P3—O6	111.01 (9)	O2—Li1—P1iv	131.81 (19)
O7—P3—O6	107.46 (9)	O1iv—Li1—P1iv	25.22 (7)
O9ii—P3—O6	99.40 (9)	O4—Li1—P1iv	117.81 (16)
O8—P3—Li1iii	147.42 (10)	O7v—Li1—P1iv	75.57 (12)
O7—P3—Li1iii	31.94 (9)	P1—Li1—P1iv	153.12 (15)
O9ii—P3—Li1iii	82.27 (9)	O2—Li1—P3v	113.75 (17)
O6—P3—Li1iii	96.05 (9)	O1iv—Li1—P3v	79.37 (12)
P1—O3—P2	129.92 (9)	O4—Li1—P3v	133.85 (18)
P3—O6—P2	132.05 (9)	O7v—Li1—P3v	23.66 (7)
P1—O2—Li1	125.14 (15)	P1—Li1—P3v	128.64 (13)
P2—O4—Li1	128.93 (14)	P1iv—Li1—P3v	57.37 (7)
P1—O1—Li1i	121.01 (15)	O2—Li1—P2	79.37 (12)
P3—O7—Li1iii	124.41 (14)	O1iv—Li1—P2	121.05 (17)
P3ii—O9—P1	130.33 (10)	O4—Li1—P2	21.87 (6)
C1—N1—C4	111.21 (18)	O7v—Li1—P2	126.83 (17)
C1—N1—H2A	109.4	P1—Li1—P2	56.88 (6)
C4—N1—H2A	109.4	P1iv—Li1—P2	134.19 (13)
C1—N1—H2B	109.4	P3v—Li1—P2	150.11 (14)
C4—N1—H2B	109.4	N2—C2—C1	109.55 (19)
H2A—N1—H2B	108.0	N2—C2—H2C	109.8
N1—C1—C2	109.47 (17)	C1—C2—H2C	109.8
N1—C1—H1A	109.8	N2—C2—H2D	109.8
C2—C1—H1A	109.8	C1—C2—H2D	109.8
N1—C1—H1B	109.8	H2C—C2—H2D	108.2
C2—C1—H1B	109.8	H110—O10—H210	111 (3)
H1A—C1—H1B	108.2	H111—O11—H211	107 (3)
N1—C4—C3	110.11 (19)
O2—P1—O3—P2	−48.29 (15)	O3—P1—Li1—O1iv	−91.0 (2)
O1—P1—O3—P2	−179.72 (12)	O9—P1—Li1—O1iv	170.3 (2)
O9—P1—O3—P2	66.34 (13)	Li1i—P1—Li1—O1iv	79.8 (4)
Li1—P1—O3—P2	−29.92 (13)	O2—P1—Li1—O4	164.8 (3)
Li1i—P1—O3—P2	159.16 (13)	O1—P1—Li1—O4	135.73 (16)
O5—P2—O3—P1	160.31 (12)	O3—P1—Li1—O4	19.62 (12)
O4—P2—O3—P1	27.66 (14)	O9—P1—Li1—O4	−79.12 (13)
O6—P2—O3—P1	−83.09 (13)	Li1i—P1—Li1—O4	−169.63 (10)
Li1—P2—O3—P1	28.79 (13)	O2—P1—Li1—O7v	−84.4 (2)
O8—P3—O6—P2	8.74 (17)	O1—P1—Li1—O7v	−113.4 (2)
O7—P3—O6—P2	−122.24 (13)	O3—P1—Li1—O7v	130.49 (19)
O9ii—P3—O6—P2	124.08 (14)	O9—P1—Li1—O7v	31.8 (2)
Li1iii—P3—O6—P2	−152.78 (14)	Li1i—P1—Li1—O7v	−58.8 (3)
O5—P2—O6—P3	46.37 (16)	O2—P1—Li1—P1iv	35.2 (3)
O4—P2—O6—P3	177.31 (12)	O1—P1—Li1—P1iv	6.1 (4)
O3—P2—O6—P3	−68.15 (15)	O3—P1—Li1—P1iv	−110.0 (3)
Li1—P2—O6—P3	−153.10 (13)	O9—P1—Li1—P1iv	151.3 (3)
O1—P1—O2—Li1	162.77 (19)	Li1i—P1—Li1—P1iv	60.8 (5)
O3—P1—O2—Li1	37.5 (2)	O2—P1—Li1—P3v	−57.7 (2)
O9—P1—O2—Li1	−70.7 (2)	O1—P1—Li1—P3v	−86.8 (2)
Li1i—P1—O2—Li1	−162.0 (2)	O3—P1—Li1—P3v	157.13 (17)
O5—P2—O4—Li1	−123.45 (19)	O9—P1—Li1—P3v	58.39 (17)
O6—P2—O4—Li1	111.54 (19)	Li1i—P1—Li1—P3v	−32.1 (3)
O3—P2—O4—Li1	2.3 (2)	O2—P1—Li1—P2	158.8 (2)
O2—P1—O1—Li1i	79.75 (19)	O1—P1—Li1—P2	129.75 (16)
O3—P1—O1—Li1i	−153.48 (16)	O3—P1—Li1—P2	13.64 (6)
O9—P1—O1—Li1i	−46.64 (19)	O9—P1—Li1—P2	−85.09 (7)
Li1—P1—O1—Li1i	96.36 (17)	Li1i—P1—Li1—P2	−175.60 (15)
O8—P3—O7—Li1iii	160.49 (16)	O5—P2—Li1—O2	−110.53 (15)
O9ii—P3—O7—Li1iii	34.12 (19)	O4—P2—Li1—O2	172.7 (3)
O6—P3—O7—Li1iii	−72.80 (18)	O6—P2—Li1—O2	94.41 (14)
O2—P1—O9—P3ii	−83.58 (15)	O3—P2—Li1—O2	−5.13 (12)
O1—P1—O9—P3ii	48.19 (17)	O5—P2—Li1—O1iv	1.8 (3)
O3—P1—O9—P3ii	160.59 (13)	O4—P2—Li1—O1iv	−75.0 (2)
Li1—P1—O9—P3ii	−112.92 (15)	O6—P2—Li1—O1iv	−153.24 (17)
Li1i—P1—O9—P3ii	24.26 (15)	O3—P2—Li1—O1iv	107.2 (2)
C4—N1—C1—C2	−59.4 (2)	O5—P2—Li1—O4	76.8 (2)
C1—N1—C4—C3	57.2 (3)	O6—P2—Li1—O4	−78.3 (2)
N1—C4—C3—N2	−55.0 (3)	O3—P2—Li1—O4	−177.8 (2)
C4—C3—N2—C2	56.3 (3)	O5—P2—Li1—O7v	136.35 (18)
P1—O2—Li1—O1iv	−137.38 (19)	O4—P2—Li1—O7v	59.6 (2)
P1—O2—Li1—O4	−15.2 (3)	O6—P2—Li1—O7v	−18.7 (2)
P1—O2—Li1—O7v	107.9 (2)	O3—P2—Li1—O7v	−118.2 (2)
P1—O2—Li1—P1iv	−159.56 (17)	O5—P2—Li1—P1	−119.08 (11)
P1—O2—Li1—P3v	133.82 (15)	O4—P2—Li1—P1	164.1 (2)
P1—O2—Li1—P2	−17.96 (18)	O6—P2—Li1—P1	85.86 (9)
P2—O4—Li1—O2	−7.3 (3)	O3—P2—Li1—P1	−13.68 (6)
P2—O4—Li1—O1iv	115.71 (19)	O5—P2—Li1—P1iv	29.2 (3)
P2—O4—Li1—O7v	−130.98 (17)	O4—P2—Li1—P1iv	−47.53 (18)
P2—O4—Li1—P1	−13.53 (18)	O6—P2—Li1—P1iv	−125.81 (18)
P2—O4—Li1—P1iv	143.28 (13)	O3—P2—Li1—P1iv	134.6 (2)
P2—O4—Li1—P3v	−146.51 (15)	O5—P2—Li1—P3v	129.8 (2)
O1—P1—Li1—O2	−29.0 (3)	O4—P2—Li1—P3v	53.0 (2)
O3—P1—Li1—O2	−145.1 (2)	O6—P2—Li1—P3v	−25.3 (3)
O9—P1—Li1—O2	116.1 (2)	O3—P2—Li1—P3v	−124.8 (3)
Li1i—P1—Li1—O2	25.6 (3)	C3—N2—C2—C1	−58.0 (2)
O2—P1—Li1—O1iv	54.2 (2)	N1—C1—C2—N2	59.0 (2)
O1—P1—Li1—O1iv	25.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2A···O8	0.90	1.99	2.792 (3)	147
N1—H2B···O7vi	0.90	1.88	2.763 (3)	166
N2—H3A···O11	0.90	1.83	2.707 (4)	165
N2—H3B···O4vii	0.90	1.91	2.802 (2)	168
O10—H110···O1viii	0.84 (4)	1.99 (4)	2.792 (4)	159 (5)
O11—H111···O5viii	0.84 (3)	2.49 (4)	3.001 (3)	120 (3)
O11—H111···O8viii	0.84 (3)	2.07 (3)	2.826 (3)	150 (4)
O10—H210···O5vi	0.82 (4)	1.95 (4)	2.764 (3)	170 (4)
O11—H211···O10viii	0.86 (4)	1.87 (4)	2.720 (4)	170 (4)
C1—H1A···O6ii	0.97	2.51	3.273 (4)	135
C4—H1D···O10	0.97	2.56	3.227 (4)	126
C2—H2C···O2i	0.97	2.29	3.078 (3)	137
C3—H4B···O5viii	0.97	2.46	3.324 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2A⋯O8	0.90	1.99	2.792 (3)	147
N1—H2B⋯O7i	0.90	1.88	2.763 (3)	166
N2—H3A⋯O11	0.90	1.83	2.707 (4)	165
N2—H3B⋯O4ii	0.90	1.91	2.802 (2)	168
O10—H110⋯O1iii	0.84 (4)	1.99 (4)	2.792 (4)	159 (5)
O11—H111⋯O5iii	0.84 (3)	2.49 (4)	3.001 (3)	120 (3)
O11—H111⋯O8iii	0.84 (3)	2.07 (3)	2.826 (3)	150 (4)
O10—H210⋯O5i	0.82 (4)	1.95 (4)	2.764 (3)	170 (4)
O11—H211⋯O10iii	0.86 (4)	1.87 (4)	2.720 (4)	170 (4)
C1—H1A⋯O6iv	0.97	2.51	3.273 (4)	135
C4—H1D⋯O10	0.97	2.56	3.227 (4)	126
C2—H2C⋯O2v	0.97	2.29	3.078 (3)	137
C3—H4B⋯O5iii	0.97	2.46	3.324 (4)	148

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