N,N′-Bis(2-ammonio­ethyl)propane-1,3-diaminium tris­(perchlorate) chloride

The crystal structure of the title compound, C₇H₂₄N₄⁴⁺·3ClO₄⁻·Cl⁻, is mainly determined by electrostatic inter­actions between the charged species and a number of relatively weak N—H...O and N—H...Cl⁻ hydrogen bonds. The rich structure of such hydrogen bonds creates infinite layers of ions extending along the [001] direction. The tetra­cation has the gttttttg conformation, similar to the single previously known example of such a cation. The presence of two different anions can be connected with the undecided competition between them, and some of the packing advantages of such a situation are found in the crystal structure.

S1. Comment

Condensation reactions of carbonyl compounds and primary amines lead to the formation of the azomethine bond (see, for example, Ibrahim & Sharif, 2007), which is a characteristic structural feature of Schiff bases and therefore may be applied in analytical determination. The importance of these compounds is mainly due to their resemblance to natural biological substances (de Hoog et al., 2004; Mukherjee et al., 2005), and their relatively simple preparation procedures and synthetic flexibility, which make the introduction of suitable structural properties relatively easy. Unfortunately, the serious drawback of the majority of Schiff bases is their chemical instability, which concerns equilibrium lability, i.e. hydrolysis, tautomeric interconversions or ionized species formation (Galic et al., 1997). In the course of our studies of the synthesis of a macrocyclic Schiff base with the ytterbium ion that has already been reported (Patroniak et al., 2004), we obtained, quite unexpectedly, the title salt, (I), of the quadruply protonated N,N'-bis(2-aminoethyl)propane-1,3-diamine with one chloride and three perchlorate anions.

In the Cambridge Structural Database (CSD, Version 5.30 of November 2008; Allen, 2002) there are only two structures of uncomplexed N,N'-bis(2-aminoethyl)propane-1,3-diamine, one a tetracation (benzene-1,2,4,5-tetracarboxylate; Su et al., 2002) and one an uncommon trication (tris-trifluoromethanesulfonate; Patroniak et al., 2008). Their conformations differ substantially: while the tetracation is gttttttg (g denotes gauche and t trans), in the trication the intramolecular N—H···N hydrogen bond enforces a more complicated gttggggt conformation. The conformation of (I) is similar to that found earlier in the tetracation (Su et al., 2002); the torsion angles along the chain are -71.9 (3), 176.8 (2), 179.7 (2), -160.9 (2), 178.8 (2), -167.1 (2), -167.1 (2) and -94.5 (3)°. The mean length of the Csp³—Csp³ bond is 1.519 (8) Å and that of the Nsp³—Csp³ bond is 1.491 (5) Å. The perchlorate anions are close to a tetrahedral geometry, with a mean Cl—O distance of 1.445 (8) Å.

The crystal packing of (I) is determined by the electrostatic interactions between the charged species and by an extensive network of hydrogen bonds. Probably due to the great number of hydrogen-bond donors and acceptors, the resulting interactions are relatively weak (see Table 1). In the crystal structure these hydrogen bonds create a complicated network of rings and chains.

The presence of both perchlorate and chloride anions in the structure is not particularly rare. There are 160 examples in the CSD (most of which, 149, are organometallics) including one similar structure, of diethylenetriammonium chloride diperchlorate (Mazus et al., 1987). Such a situation might be regarded as an example of undecided competition between the anions (see, for example, Warden et al., 2004). In every case one should find the packing advantages of such a composition of the `supramolecule'. In the case of (I) it might be noted that the terminal hydrogen-bond donor groups (atoms N1 and N11) interact mainly with the perchlorate anions, while the `internal' ones (atoms N4 and N8) interact mainly with the chlorides. This can be connected with the tendency to form centrosymmetric `face-to-face' dimers by means of N—H···Cl···H—N hydrogen-bond networks, and the small Cl<sup>-</sup> anions, accessible from all directions, are well suited for this. Indeed, such dimers can be seen in the crystal structure of (I). Pairs of cations at (x, y, z) and (1 - x, 1 - y, -z) are connected into a hydrogen-bonded dimer involving both N4—H groups as acceptors, and two Cl4 anions (Fig. 2, top). The graph set (Etter et al., 1990; Bernstein et al., 1995) connected with this dimer is R<sup>4</sup><sub>2</sub>(8). Additional N1—H1C···Cl4 hydrogen bonds [R<sup>2</sup><sub>1</sub>(7) ring motif] add to the formation of this dimer. Another dimer is created by a pair of cations at (x, y, z) and (-x, 1 - y, -z). While the first dimer displays a kind of shift between the constituent long molecules, this one is almost exactly in a head-to-tail disposition (Fig. 2, bottom), with the ends closed by hydrogen bonds between terminal amine groups and perchlorate anions. The hydrogen-bond motifs in this dimer can be described by graph symbols R<sup>4</sup><sub>2</sub>(16) (the `inner' ring) and R⁴₄(32) (the `outer' ring). Together, these two dimeric structures form a ribbon of cations extending approximately along the [110] direction (Fig. 2c [There is no part (c) - please clarify]). N—H···O hydrogen bonds with perchlorate anions connect these ribbons into infinite tapes one unit-cell parameter wide, extending along the [001] direction (Fig. 3). Only weak interactions are observed between these tapes. Some relatively short and directional C—H···O contacts are also present in the structure, but they are probably `secondary' interactions, a consequence of the geometry of the molecules.

The Cl^- anion accepts four hydrogen bonds, with the donor N atoms forming a distorted tetrahedron. Such an arrangement is less common than a three-coordinated one, with the Cl atom on top of a more or less flattened tripodal coordination pyramid (Warden et al., 2004). There are 492 organic structures (N···Cl distances shorter than 3.25 Å) with three N—H donor groups in the CSD, while only 65 have four such groups.

S2. Experimental

To a mixture of ytterbium chloride hexahydrate (0.096 mg, 0.247 mmol) and 2,6-diacetylpyridyne [-pyridine?] (61.7 mg, 0.38 mmol) in methanol (15 ml), ytterbium perchlorate hexahydrate (72 mg,0.12 mmol) was added and N,N'-bis(2-aminoethyl)-1,3-propanediamine (60.1 mg,0.38 mmol) was added dropwise with stirring. The reaction mixture was stirred for 24 h at 341 K. Red crystals of (I) were obtained by slow diffusion of toluene into the acetonitrile solution.

S3. Refinement

The positions of the NH₃ h atoms were found geometrically and these atoms were treated as a rigid group with one common N—H distance refined. All other H atoms were found in a difference Fourier map and their positions were freely refined [Please give ranges of refined C—H and N—H distances]. U_iso(H) = 1.2 (1.4 for NH₃ groups) times U_eq(parent).

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. The ionic components of (I), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are drawn as dashed lines.
	Fig. 2. The two dimeric hydrogen-bonded motifs (see text). Hydrogen bonds are drawn as dashed lines. Symmetry codes as in Table 1. [Part (c) is missing]
	Fig. 3. The packing of the ionic species, viewed along the c direction. Hydrogen bonds are depicted as dashed lines.

N,N'-Bis(2-ammonioethyl)propane-1,3-diaminium tris(perchlorate) chloride

Crystal data

C7H24N4^4+·3ClO4^−·Cl^−	Z = 2
Mr = 498.10	F(000) = 516
Triclinic, P1	Dx = 1.731 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9755 (9) Å	Cell parameters from 2192 reflections
b = 11.2619 (15) Å	θ = 3–24°
c = 11.4848 (16) Å	µ = 0.69 mm^−1
α = 77.358 (11)°	T = 100 K
β = 78.991 (10)°	Block, colourless
γ = 73.488 (11)°	0.15 × 0.1 × 0.1 mm
V = 955.9 (2) Å^3

Data collection

Kuma KM-4 CCD area-detector diffractometer	4148 independent reflections
Radiation source: fine-focus sealed tube	2461 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
ω scans	θmax = 28.0°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2009)	h = −10→9
Tmin = 0.901, Tmax = 0.936	k = −14→14
9313 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.061	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ^2(Fo^2) + (0.01P)^2] where P = (Fo^2 + 2Fc^2)/3
4148 reflections	(Δ/σ)max < 0.001
302 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.45 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.4399 (3)	0.5522 (2)	0.3040 (2)	0.0189 (7)
H1A	0.339	0.5898	0.3552	0.026*
H1B	0.5336	0.5098	0.3503	0.026*
H1C	0.411	0.4935	0.2678	0.026*
C2	0.4961 (4)	0.6517 (3)	0.2081 (3)	0.0185 (8)
H2A	0.587 (4)	0.606 (2)	0.155 (3)	0.022*
H2B	0.554 (3)	0.696 (3)	0.252 (3)	0.022*
C3	0.3472 (4)	0.7430 (3)	0.1482 (3)	0.0129 (7)
H3A	0.261 (4)	0.774 (2)	0.203 (3)	0.016*
H3B	0.392 (3)	0.812 (2)	0.098 (2)	0.016*
N4	0.2758 (3)	0.6895 (2)	0.0667 (2)	0.0111 (6)
H4A	0.240 (3)	0.621 (2)	0.110 (3)	0.013*
H4B	0.360 (3)	0.667 (2)	0.003 (3)	0.013*
C5	0.1211 (4)	0.7806 (3)	0.0128 (3)	0.0130 (8)
H5A	0.164 (3)	0.853 (2)	−0.028 (2)	0.016*
H5B	0.035 (3)	0.800 (2)	0.078 (3)	0.016*
C6	0.0519 (4)	0.7231 (3)	−0.0699 (3)	0.0125 (7)
H6A	−0.016 (3)	0.669 (2)	−0.024 (2)	0.015*
H6B	0.149 (3)	0.679 (2)	−0.121 (3)	0.015*
C7	−0.0577 (4)	0.8288 (3)	−0.1520 (3)	0.0122 (7)
H7A	−0.156 (3)	0.883 (2)	−0.108 (3)	0.015*
H7B	0.016 (3)	0.888 (2)	−0.206 (2)	0.015*
N8	−0.1284 (3)	0.7804 (2)	−0.2385 (2)	0.0108 (6)
H8A	−0.214 (3)	0.737 (2)	−0.194 (2)	0.013*
H8B	−0.041 (3)	0.720 (2)	−0.271 (3)	0.013*
C9	−0.1999 (4)	0.8834 (3)	−0.3370 (3)	0.0122 (7)
H9A	−0.091 (3)	0.917 (2)	−0.389 (2)	0.015*
H9B	−0.271 (3)	0.951 (2)	−0.299 (3)	0.015*
C10	−0.3098 (4)	0.8439 (3)	−0.4091 (3)	0.0123 (7)
H10A	−0.351 (3)	0.776 (3)	−0.364 (2)	0.015*
H10B	−0.407 (3)	0.916 (3)	−0.434 (2)	0.015*
N11	−0.2077 (3)	0.7980 (2)	−0.5209 (2)	0.0152 (7)
H11A	−0.182	0.8639	−0.5759	0.021*
H11B	−0.2733	0.7616	−0.5519	0.021*
H11C	−0.1060	0.7407	−0.5030	0.021*
Cl4	0.39415 (9)	0.39015 (7)	0.12660 (7)	0.0167 (2)
Cl2	0.29209 (9)	0.76166 (7)	−0.46282 (7)	0.01362 (19)
O21	0.1861 (2)	0.7561 (2)	−0.55049 (19)	0.0229 (6)
O22	0.2812 (2)	0.89031 (18)	−0.4603 (2)	0.0217 (6)
O23	0.2285 (2)	0.70112 (19)	−0.34518 (18)	0.0194 (5)
O24	0.4732 (2)	0.69349 (18)	−0.49555 (19)	0.0175 (5)
Cl1	−0.33868 (10)	0.95303 (8)	−0.80726 (7)	0.0196 (2)
O11	−0.4324 (3)	1.0810 (2)	−0.8461 (2)	0.0430 (8)
O12	−0.3068 (3)	0.8828 (2)	−0.9031 (2)	0.0345 (7)
O13	−0.1720 (3)	0.94997 (19)	−0.77252 (19)	0.0222 (6)
O14	−0.4433 (2)	0.89698 (18)	−0.70434 (18)	0.0181 (5)
Cl3	0.95147 (10)	0.53687 (7)	0.31430 (7)	0.01299 (18)
O31	0.7812 (2)	0.56698 (19)	0.38721 (19)	0.0189 (5)
O32	1.0338 (3)	0.63899 (18)	0.29900 (19)	0.0215 (6)
O33	0.9303 (3)	0.51784 (19)	0.19863 (19)	0.0203 (5)
O34	1.0636 (2)	0.42402 (18)	0.37423 (18)	0.0163 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0215 (16)	0.0177 (15)	0.0187 (17)	0.0009 (12)	−0.0132 (13)	−0.0044 (13)
C2	0.015 (2)	0.023 (2)	0.019 (2)	−0.0050 (16)	−0.0056 (16)	−0.0036 (16)
C3	0.0139 (19)	0.0149 (19)	0.012 (2)	−0.0037 (15)	−0.0044 (15)	−0.0034 (15)
N4	0.0088 (14)	0.0138 (15)	0.0108 (17)	−0.0021 (12)	0.0006 (12)	−0.0053 (12)
C5	0.0126 (18)	0.0108 (17)	0.015 (2)	0.0003 (15)	−0.0068 (15)	−0.0015 (15)
C6	0.0141 (18)	0.0125 (18)	0.0101 (19)	−0.0033 (14)	−0.0030 (15)	0.0008 (14)
C7	0.0134 (18)	0.0182 (18)	0.0075 (18)	−0.0057 (15)	−0.0014 (14)	−0.0051 (14)
N8	0.0112 (15)	0.0134 (15)	0.0088 (16)	−0.0036 (12)	−0.0009 (12)	−0.0042 (12)
C9	0.0124 (18)	0.0105 (18)	0.013 (2)	0.0007 (14)	−0.0067 (15)	−0.0005 (14)
C10	0.0124 (18)	0.0126 (18)	0.012 (2)	−0.0020 (14)	−0.0044 (15)	−0.0025 (15)
N11	0.0146 (15)	0.0209 (15)	0.0128 (16)	−0.0062 (12)	−0.0062 (12)	−0.0027 (13)
Cl4	0.0172 (4)	0.0142 (4)	0.0190 (5)	−0.0063 (3)	0.0027 (4)	−0.0045 (4)
Cl2	0.0098 (4)	0.0195 (4)	0.0129 (5)	−0.0054 (3)	−0.0020 (3)	−0.0031 (4)
O21	0.0128 (12)	0.0440 (15)	0.0169 (14)	−0.0088 (11)	−0.0072 (10)	−0.0088 (12)
O22	0.0211 (13)	0.0136 (12)	0.0297 (15)	−0.0006 (10)	−0.0059 (11)	−0.0051 (11)
O23	0.0179 (12)	0.0292 (13)	0.0109 (13)	−0.0108 (10)	0.0029 (10)	−0.0011 (11)
O24	0.0059 (11)	0.0246 (13)	0.0198 (14)	0.0005 (10)	0.0003 (9)	−0.0068 (11)
Cl1	0.0182 (5)	0.0210 (5)	0.0152 (5)	−0.0022 (4)	0.0007 (4)	−0.0005 (4)
O11	0.0332 (15)	0.0245 (14)	0.0463 (19)	0.0067 (12)	0.0037 (13)	0.0195 (13)
O12	0.0235 (14)	0.0669 (18)	0.0179 (15)	−0.0116 (13)	0.0031 (11)	−0.0224 (14)
O13	0.0222 (13)	0.0238 (13)	0.0243 (15)	−0.0125 (10)	−0.0024 (11)	−0.0036 (11)
O14	0.0159 (12)	0.0193 (12)	0.0150 (13)	−0.0047 (10)	0.0034 (10)	0.0010 (10)
Cl3	0.0117 (4)	0.0136 (4)	0.0143 (5)	−0.0019 (3)	−0.0033 (3)	−0.0039 (3)
O31	0.0080 (11)	0.0280 (13)	0.0212 (14)	−0.0008 (10)	0.0033 (10)	−0.0145 (11)
O32	0.0238 (13)	0.0140 (12)	0.0283 (15)	−0.0085 (10)	−0.0029 (11)	−0.0026 (11)
O33	0.0221 (13)	0.0282 (13)	0.0119 (13)	−0.0018 (10)	−0.0065 (10)	−0.0084 (11)
O34	0.0145 (12)	0.0150 (12)	0.0164 (13)	0.0019 (10)	−0.0066 (10)	0.0001 (10)

Geometric parameters (Å, º)

N1—C2	1.492 (4)	N8—H8A	0.96 (3)
N1—H1A	0.9523	N8—H8B	0.91 (3)
N1—H1B	0.9523	C9—C10	1.521 (4)
N1—H1C	0.9523	C9—H9A	1.07 (3)
C2—C3	1.500 (4)	C9—H9B	0.95 (3)
C2—H2A	0.96 (3)	C10—N11	1.494 (4)
C2—H2B	1.02 (3)	C10—H10A	0.93 (3)
C3—N4	1.486 (4)	C10—H10B	0.98 (2)
C3—H3A	0.89 (3)	N11—H11A	0.9083
C3—H3B	0.98 (3)	N11—H11B	0.9083
N4—C5	1.501 (4)	N11—H11C	0.9083
N4—H4A	0.91 (3)	Cl2—O22	1.433 (2)
N4—H4B	0.92 (3)	Cl2—O23	1.442 (2)
C5—C6	1.515 (4)	Cl2—O24	1.4509 (19)
C5—H5A	0.97 (3)	Cl2—O21	1.454 (2)
C5—H5B	0.93 (3)	Cl1—O12	1.435 (2)
C6—C7	1.517 (4)	Cl1—O11	1.438 (2)
C6—H6A	0.94 (3)	Cl1—O14	1.445 (2)
C6—H6B	0.96 (3)	Cl1—O13	1.449 (2)
C7—N8	1.493 (4)	Cl3—O33	1.439 (2)
C7—H7A	0.97 (3)	Cl3—O32	1.443 (2)
C7—H7B	1.04 (3)	Cl3—O31	1.445 (2)
N8—C9	1.499 (4)	Cl3—O34	1.4474 (18)
C2—N1—H1A	109.5	C7—N8—C9	111.7 (2)
C2—N1—H1B	109.5	C7—N8—H8A	108.3 (17)
H1A—N1—H1B	109.5	C9—N8—H8A	112.8 (16)
C2—N1—H1C	109.5	C7—N8—H8B	109.2 (18)
H1A—N1—H1C	109.5	C9—N8—H8B	109.9 (18)
H1B—N1—H1C	109.5	H8A—N8—H8B	105 (2)
N1—C2—C3	113.9 (3)	N8—C9—C10	112.8 (3)
N1—C2—H2A	104.4 (17)	N8—C9—H9A	107.3 (14)
C3—C2—H2A	114.6 (17)	C10—C9—H9A	114.9 (15)
N1—C2—H2B	104.3 (16)	N8—C9—H9B	106.1 (17)
C3—C2—H2B	110.8 (15)	C10—C9—H9B	109.6 (17)
H2A—C2—H2B	108 (2)	H9A—C9—H9B	106 (2)
N4—C3—C2	114.0 (3)	N11—C10—C9	113.6 (3)
N4—C3—H3A	109.9 (19)	N11—C10—H10A	104.9 (17)
C2—C3—H3A	110.4 (18)	C9—C10—H10A	109.6 (18)
N4—C3—H3B	106.0 (17)	N11—C10—H10B	107.3 (16)
C2—C3—H3B	108.0 (15)	C9—C10—H10B	109.3 (16)
H3A—C3—H3B	108 (2)	H10A—C10—H10B	112 (2)
C3—N4—C5	112.9 (2)	C10—N11—H11A	109.5
C3—N4—H4A	108.7 (18)	C10—N11—H11B	109.5
C5—N4—H4A	108.0 (17)	H11A—N11—H11B	109.5
C3—N4—H4B	110.8 (17)	C10—N11—H11C	109.5
C5—N4—H4B	106.2 (17)	H11A—N11—H11C	109.5
H4A—N4—H4B	110 (2)	H11B—N11—H11C	109.5
N4—C5—C6	111.5 (2)	O22—Cl2—O23	109.73 (13)
N4—C5—H5A	104.9 (15)	O22—Cl2—O24	111.00 (12)
C6—C5—H5A	113.3 (17)	O23—Cl2—O24	108.04 (12)
N4—C5—H5B	105.6 (17)	O22—Cl2—O21	109.65 (13)
C6—C5—H5B	109.9 (18)	O23—Cl2—O21	109.66 (13)
H5A—C5—H5B	111 (2)	O24—Cl2—O21	108.73 (13)
C5—C6—C7	108.4 (2)	O12—Cl1—O11	109.87 (15)
C5—C6—H6A	109.7 (18)	O12—Cl1—O14	109.47 (14)
C7—C6—H6A	111.1 (16)	O11—Cl1—O14	109.22 (13)
C5—C6—H6B	109.8 (17)	O12—Cl1—O13	109.56 (13)
C7—C6—H6B	106.8 (17)	O11—Cl1—O13	109.93 (14)
H6A—C6—H6B	111 (2)	O14—Cl1—O13	108.78 (13)
N8—C7—C6	112.0 (2)	O33—Cl3—O32	109.89 (13)
N8—C7—H7A	108.9 (17)	O33—Cl3—O31	109.95 (13)
C6—C7—H7A	113.0 (17)	O32—Cl3—O31	109.06 (12)
N8—C7—H7B	104.8 (16)	O33—Cl3—O34	109.60 (12)
C6—C7—H7B	112.1 (14)	O32—Cl3—O34	108.47 (12)
H7A—C7—H7B	106 (2)	O31—Cl3—O34	109.83 (12)
N1—C2—C3—N4	−72.2 (4)	C5—C6—C7—N8	178.8 (3)
C2—C3—N4—C5	177.1 (3)	C6—C7—N8—C9	−166.8 (2)
C3—N4—C5—C6	179.9 (3)	C7—N8—C9—C10	−166.7 (3)
N4—C5—C6—C7	−161.0 (2)	N8—C9—C10—N11	−94.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O21^i	0.95	2.29	3.147 (3)	149
N1—H1A···O32^ii	0.95	2.52	3.114 (3)	121
N1—H1B···O31	0.95	2.38	3.110 (3)	133
N1—H1B···O23^iii	0.95	2.59	3.110 (3)	133
N1—H1B···O24^iii	0.95	2.53	3.131 (3)	121
N1—H1C···Cl4	0.95	2.24	3.147 (3)	160
C2—H2B···O14^iv	1.02 (3)	2.43 (3)	3.321 (4)	146 (2)
N4—H4A···O32^ii	0.91 (3)	2.47 (3)	3.026 (3)	120 (2)
N4—H4A···Cl4	0.91 (3)	2.52 (3)	3.187 (3)	130 (2)
N4—H4B···Cl4^iii	0.92 (3)	2.25 (3)	3.156 (3)	168 (2)
C5—H5A···O11^v	0.97 (3)	2.54 (3)	3.367 (4)	143 (2)
C6—H6B···O23	0.96 (3)	2.51 (3)	3.238 (4)	133 (2)
C7—H7A···O12^i	0.97 (3)	2.43 (3)	3.224 (4)	138 (2)
C7—H7B···O13^v	1.04 (3)	2.43 (3)	3.370 (4)	150 (2)
N8—H8A···Cl4^vi	0.96 (3)	2.23 (3)	3.167 (3)	166 (2)
N8—H8B···O23	0.91 (3)	2.12 (3)	2.846 (3)	135 (2)
N8—H8B···O33^iii	0.91 (3)	2.57 (3)	3.252 (3)	132 (2)
N8—H8B···O34^iii	0.91 (3)	2.27 (3)	2.930 (3)	129 (2)
N11—H11A···O13	0.91	2.25	3.026 (3)	143
N11—H11B···O31^vii	0.91	2.34	3.043 (3)	134
N11—H11B···O24^ii	0.91	2.29	3.037 (3)	139
N11—H11B···O14	0.91	2.41	2.916 (3)	116
N11—H11B···O31^vii	0.91	2.34	3.043 (3)	134
N11—H11C···O34^iii	0.91	2.09	2.770 (3)	131
N11—H11C···O21	0.91	2.34	3.004 (3)	130

Symmetry codes: (i) x, y, z+1; (ii) x−1, y, z; (iii) −x+1, −y+1, −z; (iv) x+1, y, z+1; (v) −x, −y+2, −z−1; (vi) −x, −y+1, −z; (vii) x−1, y, z−1.