Bis[tris(propane-1,3-diamine-κ(2) N,N')-nickel(II)] di-aqua-bis(propane-1,3-di-amine-κ(2) N,N')nickel(II) hexa-bromide dihydrate.

In the title compound, [Ni(C3H10N2)3]2[Ni(C3H10N2)2(H2O)2]Br6·2H2O, one Ni(2+) cation, located on an inversion centre, is coordinated by four N atoms from two ligands and by two water O atoms. The other Ni(2+) cation, located in a general position, is coordinated by six N atoms from three ligands. In both cases, the Ni(2+) cation has an octa-hedral coordination environment. The overall structural cohesion is ensured by three types of hydrogen bonds, N-H⋯Br, O-H⋯Br and O-H⋯O, which connect the two types of complex cations, the bromide counter-anions and the lattice water molecules into a three-dimensional network.

Related literature

For the multiple coordination modes of amine derivatives as ligands to metal ions, see: Manzur et al. (2007 ▶); Ismayilov et al. (2007 ▶); Austria et al. (2007 ▶). For control of the aggregation of mol­ecules or ions in the solid state in crystal engineering, see: Burrows (2004 ▶). For hydrogen bonding in bifunctional ligands, see: Simard et al. (1991 ▶); Zerkowski & Whitesides (1994 ▶).

Experimental

Crystal data

[Ni(C3H10N2)3]2[Ni(C3H10N2)2(H2O)2]Br6·2H2O

M = 1320.57

Triclinic,

a = 8.760 (5) Å

b = 13.327 (5) Å

c = 13.387 (5) Å

α = 107.774 (5)°

β = 109.045 (5)°

γ = 99.504 (5)°

V = 1344.6 (11) Å3

Z = 1

Mo Kα radiation

μ = 5.54 mm−1

T = 296 K

0.36 × 0.30 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: analytical (de Meulenaer & Tompa, 1965 ▶) T min = 0.215, T max = 0.330

17594 measured reflections

8674 independent reflections

5022 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.084

S = 1.00

8674 reflections

257 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.90 e Å−3

Δρmin = −0.74 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: HKL (Otwinowski & Minor 1997 ▶); data reduction: HKL (Otwinowski & Minor 1997 ▶) and HKL ; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814011052/rk2424sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814011052/rk2424Isup2.hkl

CCDC reference: 1002808

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Ni(C3H10N2)3]2[Ni(C3H10N2)2(H2O)2]Br6·2H2O	Z = 1
Mr = 1320.57	F(000) = 670
Triclinic, P1	Dx = 1.631 Mg m−3
a = 8.760 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.327 (5) Å	Cell parameters from 17594 reflections
c = 13.387 (5) Å	θ = 1.7–31.2°
α = 107.774 (5)°	µ = 5.54 mm−1
β = 109.045 (5)°	T = 296 K
γ = 99.504 (5)°	Pellets, purple
V = 1344.6 (11) Å3	0.36 × 0.30 × 0.16 mm

Nonius KappaCCD diffractometer	8674 independent reflections
Radiation source: fine–focus sealed tube	5022 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.028
Detector resolution: 9 pixels mm-1	θmax = 31.2°, θmin = 1.7°
rotation images, thick slices scans	h = −12→12
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	k = −19→18
Tmin = 0.215, Tmax = 0.330	l = −19→18
17594 measured 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) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0337P)2 + 0.1194P] where P = (Fo2 + 2Fc2)/3
8674 reflections	(Δ/σ)max = 0.001
257 parameters	Δρmax = 0.90 e Å−3
6 restraints	Δρmin = −0.74 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Br1	0.69831 (4)	0.50049 (3)	0.37689 (3)	0.05784 (10)
Br3	0.38496 (5)	1.04327 (3)	0.31879 (3)	0.07285 (12)
Ni1	0.0000	0.0000	0.0000	0.03393 (11)
Ni2	0.24711 (4)	0.65812 (2)	0.34338 (3)	0.03374 (9)
N3	0.1826 (3)	0.80148 (18)	0.3275 (2)	0.0479 (6)
H3A	0.2872	0.8609	0.3623	0.057*
H3B	0.1356	0.7875	0.2464	0.057*
N4	0.2454 (3)	0.71517 (19)	0.51262 (19)	0.0465 (6)
H4A	0.2339	0.6523	0.5346	0.056*
H4B	0.3555	0.7668	0.5650	0.056*
N5	−0.0146 (3)	0.56993 (17)	0.26203 (19)	0.0424 (5)
H5A	−0.0588	0.5801	0.3209	0.051*
H5B	−0.0703	0.6044	0.2122	0.051*
N6	0.3057 (3)	0.51614 (18)	0.3677 (2)	0.0491 (6)
H6A	0.4190	0.5213	0.3709	0.059*
H6B	0.3108	0.5223	0.4429	0.059*
N7	0.2549 (3)	0.6107 (2)	0.1765 (2)	0.0487 (6)
H7A	0.2807	0.5409	0.1602	0.058*
H7B	0.1415	0.5965	0.1215	0.058*
N8	0.5159 (3)	0.7397 (2)	0.4153 (2)	0.0527 (6)
H8A	0.5440	0.7955	0.4901	0.063*
H8B	0.5733	0.6855	0.4278	0.063*
C9	0.1995 (5)	0.4044 (2)	0.2877 (3)	0.0694 (10)
H9A	0.2356	0.3520	0.3198	0.083*
H9B	0.2153	0.3886	0.2167	0.083*
O2	0.4632 (4)	0.2799 (2)	0.1212 (3)	0.0724 (7)
C7	−0.0660 (4)	0.4506 (3)	0.1937 (3)	0.0608 (9)
H7C	−0.0349	0.4388	0.1287	0.073*
H7D	−0.1878	0.4215	0.1644	0.073*
C8	0.0148 (5)	0.3893 (3)	0.2623 (3)	0.0762 (11)
H8C	−0.0453	0.3114	0.2213	0.091*
H8D	0.0017	0.4128	0.3343	0.091*
C12	0.3715 (4)	0.6846 (3)	0.1526 (3)	0.0668 (10)
H12A	0.3364	0.7505	0.1559	0.080*
H12B	0.3629	0.6478	0.0754	0.080*
C10	0.5908 (4)	0.7931 (3)	0.3539 (3)	0.0670 (10)
H10A	0.7124	0.8206	0.3962	0.080*
H10B	0.5493	0.8558	0.3514	0.080*
C11	0.5517 (4)	0.7177 (3)	0.2342 (3)	0.0700 (10)
H11A	0.6220	0.7537	0.2047	0.084*
H11B	0.5825	0.6515	0.2365	0.084*
C6	0.1161 (4)	0.7689 (3)	0.5323 (3)	0.0581 (8)
H6C	0.1345	0.7911	0.6124	0.070*
H6D	0.0048	0.7160	0.4872	0.070*
C5	0.1219 (4)	0.8689 (2)	0.5008 (3)	0.0602 (9)
H5C	0.0513	0.9085	0.5289	0.072*
H5D	0.2369	0.9174	0.5397	0.072*
C4	0.0649 (4)	0.8433 (3)	0.3750 (3)	0.0561 (8)
H4C	−0.0453	0.7888	0.3348	0.067*
H4D	0.0530	0.9097	0.3614	0.067*
O1	0.2016 (3)	0.13735 (17)	0.13311 (19)	0.0517 (5)
N1	−0.0659 (3)	−0.03912 (19)	0.1248 (2)	0.0458 (6)
H1A	−0.0704	−0.1156	0.1105	0.055*
H1B	0.0263	0.0048	0.1986	0.055*
C2	−0.2457 (4)	0.0852 (2)	0.1389 (3)	0.0557 (8)
H2A	−0.1409	0.1416	0.1933	0.067*
H2B	−0.3326	0.0984	0.1668	0.067*
C1	−0.2248 (4)	−0.0249 (2)	0.1366 (3)	0.0566 (8)
H1C	−0.2239	−0.0320	0.2068	0.068*
H1D	−0.3203	−0.0828	0.0731	0.068*
C3	−0.2917 (4)	0.0979 (3)	0.0259 (3)	0.0570 (8)
H3C	−0.3864	0.0353	−0.0318	0.068*
H3D	−0.3278	0.1637	0.0321	0.068*
N2	−0.1514 (3)	0.10575 (18)	−0.0122 (2)	0.0446 (6)
H2C	−0.0768	0.1806	0.0304	0.053*
H2D	−0.1994	0.0965	−0.0919	0.053*
Br2	0.12791 (4)	0.32662 (3)	−0.04291 (3)	0.05752 (10)
H2	0.261 (4)	0.119 (3)	0.184 (2)	0.070 (12)*
H1	0.270 (4)	0.185 (3)	0.128 (3)	0.108 (17)*
H3	0.521 (4)	0.330 (2)	0.1855 (18)	0.084 (14)*
H4	0.405 (5)	0.307 (3)	0.079 (3)	0.111 (19)*

	U11	U22	U33	U12	U13	U23
Br1	0.0568 (2)	0.0720 (2)	0.0668 (2)	0.02667 (17)	0.03530 (17)	0.04018 (18)
Br3	0.0733 (2)	0.04978 (19)	0.0567 (2)	−0.00541 (16)	−0.01077 (18)	0.02214 (16)
Ni1	0.0335 (2)	0.0323 (2)	0.0336 (3)	0.00772 (19)	0.0118 (2)	0.01223 (19)
Ni2	0.03470 (18)	0.03048 (17)	0.03582 (19)	0.00762 (13)	0.01576 (15)	0.01176 (14)
N3	0.0499 (14)	0.0408 (13)	0.0612 (16)	0.0171 (11)	0.0269 (13)	0.0235 (12)
N4	0.0570 (15)	0.0414 (13)	0.0385 (13)	0.0122 (11)	0.0188 (12)	0.0137 (10)
N5	0.0420 (13)	0.0409 (12)	0.0389 (13)	0.0028 (10)	0.0187 (11)	0.0106 (10)
N6	0.0630 (16)	0.0460 (14)	0.0553 (16)	0.0250 (12)	0.0345 (14)	0.0252 (12)
N7	0.0516 (15)	0.0519 (14)	0.0452 (14)	0.0109 (12)	0.0265 (12)	0.0169 (12)
N8	0.0403 (14)	0.0534 (15)	0.0570 (16)	0.0084 (12)	0.0165 (12)	0.0178 (12)
C9	0.108 (3)	0.0420 (18)	0.074 (2)	0.0338 (19)	0.049 (2)	0.0228 (17)
O2	0.0647 (17)	0.0603 (16)	0.081 (2)	0.0147 (14)	0.0234 (15)	0.0215 (16)
C7	0.059 (2)	0.0519 (18)	0.051 (2)	−0.0073 (16)	0.0266 (17)	0.0003 (15)
C8	0.099 (3)	0.0324 (16)	0.087 (3)	−0.0027 (18)	0.047 (2)	0.0101 (17)
C12	0.063 (2)	0.089 (3)	0.071 (2)	0.022 (2)	0.039 (2)	0.048 (2)
C10	0.0399 (17)	0.068 (2)	0.095 (3)	0.0065 (16)	0.0271 (19)	0.039 (2)
C11	0.059 (2)	0.093 (3)	0.091 (3)	0.028 (2)	0.049 (2)	0.055 (2)
C6	0.064 (2)	0.064 (2)	0.0399 (17)	0.0155 (17)	0.0264 (16)	0.0068 (15)
C5	0.060 (2)	0.0494 (18)	0.057 (2)	0.0242 (16)	0.0199 (17)	0.0008 (15)
C4	0.0552 (19)	0.0573 (19)	0.066 (2)	0.0295 (16)	0.0289 (17)	0.0248 (16)
O1	0.0493 (13)	0.0416 (12)	0.0456 (13)	0.0006 (10)	0.0058 (11)	0.0136 (10)
N1	0.0493 (14)	0.0446 (13)	0.0431 (14)	0.0090 (11)	0.0194 (12)	0.0181 (11)
C2	0.0550 (19)	0.0469 (17)	0.063 (2)	0.0095 (15)	0.0342 (17)	0.0097 (15)
C1	0.059 (2)	0.0500 (18)	0.061 (2)	0.0045 (15)	0.0353 (17)	0.0156 (15)
C3	0.0442 (17)	0.0560 (19)	0.068 (2)	0.0177 (15)	0.0221 (16)	0.0183 (16)
N2	0.0412 (13)	0.0419 (13)	0.0522 (15)	0.0136 (11)	0.0179 (12)	0.0204 (11)
Br2	0.0688 (2)	0.05470 (19)	0.04544 (18)	0.01940 (16)	0.01714 (16)	0.02018 (14)

Ni1—N2i	2.095 (2)	C7—H7C	0.9700
Ni1—N2	2.095 (2)	C7—H7D	0.9700
Ni1—N1i	2.112 (2)	C8—H8C	0.9700
Ni1—N1	2.112 (2)	C8—H8D	0.9700
Ni1—O1i	2.129 (2)	C12—C11	1.493 (5)
Ni1—O1	2.129 (2)	C12—H12A	0.9700
Ni2—N5	2.127 (2)	C12—H12B	0.9700
Ni2—N6	2.130 (2)	C10—C11	1.497 (5)
Ni2—N3	2.131 (2)	C10—H10A	0.9700
Ni2—N7	2.155 (2)	C10—H10B	0.9700
Ni2—N4	2.165 (2)	C11—H11A	0.9700
Ni2—N8	2.166 (3)	C11—H11B	0.9700
N3—C4	1.476 (4)	C6—C5	1.513 (4)
N3—H3A	0.9700	C6—H6C	0.9700
N3—H3B	0.9700	C6—H6D	0.9700
N4—C6	1.487 (4)	C5—C4	1.499 (4)
N4—H4A	0.9700	C5—H5C	0.9700
N4—H4B	0.9700	C5—H5D	0.9700
N5—C7	1.475 (4)	C4—H4C	0.9700
N5—H5A	0.9700	C4—H4D	0.9700
N5—H5B	0.9700	O1—H2	0.843 (17)
N6—C9	1.465 (4)	O1—H1	0.839 (18)
N6—H6A	0.9700	N1—C1	1.486 (4)
N6—H6B	0.9700	N1—H1A	0.9700
N7—C12	1.481 (4)	N1—H1B	0.9700
N7—H7A	0.9700	C2—C1	1.501 (4)
N7—H7B	0.9700	C2—C3	1.504 (5)
N8—C10	1.472 (4)	C2—H2A	0.9700
N8—H8A	0.9700	C2—H2B	0.9700
N8—H8B	0.9700	C1—H1C	0.9700
C9—C8	1.505 (5)	C1—H1D	0.9700
C9—H9A	0.9700	C3—N2	1.476 (4)
C9—H9B	0.9700	C3—H3C	0.9700
O2—H3	0.834 (17)	C3—H3D	0.9700
O2—H4	0.841 (17)	N2—H2C	0.9700
C7—C8	1.495 (5)	N2—H2D	0.9700
N2i—Ni1—N2	180.0	C8—C7—H7D	109.2
N2i—Ni1—N1i	93.54 (9)	H7C—C7—H7D	107.9
N2—Ni1—N1i	86.46 (9)	C7—C8—C9	115.0 (3)
N2i—Ni1—N1	86.46 (9)	C7—C8—H8C	108.5
N2—Ni1—N1	93.54 (9)	C9—C8—H8C	108.5
N1i—Ni1—N1	180.0	C7—C8—H8D	108.5
N2i—Ni1—O1i	88.38 (10)	C9—C8—H8D	108.5
N2—Ni1—O1i	91.62 (10)	H8C—C8—H8D	107.5
N1i—Ni1—O1i	89.33 (10)	N7—C12—C11	113.5 (3)
N1—Ni1—O1i	90.67 (10)	N7—C12—H12A	108.9
N2i—Ni1—O1	91.62 (10)	C11—C12—H12A	108.9
N2—Ni1—O1	88.38 (10)	N7—C12—H12B	108.9
N1i—Ni1—O1	90.67 (10)	C11—C12—H12B	108.9
N1—Ni1—O1	89.33 (10)	H12A—C12—H12B	107.7
O1i—Ni1—O1	180.0	N8—C10—C11	113.4 (3)
N5—Ni2—N6	90.12 (10)	N8—C10—H10A	108.9
N5—Ni2—N3	88.80 (10)	C11—C10—H10A	108.9
N6—Ni2—N3	176.31 (9)	N8—C10—H10B	108.9
N5—Ni2—N7	88.31 (9)	C11—C10—H10B	108.9
N6—Ni2—N7	93.53 (9)	H10A—C10—H10B	107.7
N3—Ni2—N7	89.98 (10)	C12—C11—C10	115.1 (3)
N5—Ni2—N4	93.56 (9)	C12—C11—H11A	108.5
N6—Ni2—N4	89.02 (9)	C10—C11—H11A	108.5
N3—Ni2—N4	87.51 (9)	C12—C11—H11B	108.5
N7—Ni2—N4	176.84 (9)	C10—C11—H11B	108.5
N5—Ni2—N8	175.67 (9)	H11A—C11—H11B	107.5
N6—Ni2—N8	88.21 (10)	N4—C6—C5	112.3 (3)
N3—Ni2—N8	93.10 (10)	N4—C6—H6C	109.1
N7—Ni2—N8	87.80 (10)	C5—C6—H6C	109.1
N4—Ni2—N8	90.41 (10)	N4—C6—H6D	109.1
C4—N3—Ni2	120.60 (19)	C5—C6—H6D	109.1
C4—N3—H3A	107.2	H6C—C6—H6D	107.9
Ni2—N3—H3A	107.2	C4—C5—C6	114.6 (2)
C4—N3—H3B	107.2	C4—C5—H5C	108.6
Ni2—N3—H3B	107.2	C6—C5—H5C	108.6
H3A—N3—H3B	106.8	C4—C5—H5D	108.6
C6—N4—Ni2	119.51 (19)	C6—C5—H5D	108.6
C6—N4—H4A	107.4	H5C—C5—H5D	107.6
Ni2—N4—H4A	107.4	N3—C4—C5	113.1 (3)
C6—N4—H4B	107.4	N3—C4—H4C	109.0
Ni2—N4—H4B	107.4	C5—C4—H4C	109.0
H4A—N4—H4B	107.0	N3—C4—H4D	109.0
C7—N5—Ni2	118.69 (19)	C5—C4—H4D	109.0
C7—N5—H5A	107.6	H4C—C4—H4D	107.8
Ni2—N5—H5A	107.6	Ni1—O1—H2	112 (2)
C7—N5—H5B	107.6	Ni1—O1—H1	129 (3)
Ni2—N5—H5B	107.6	H2—O1—H1	105 (2)
H5A—N5—H5B	107.1	C1—N1—Ni1	120.33 (19)
C9—N6—Ni2	121.6 (2)	C1—N1—H1A	107.2
C9—N6—H6A	106.9	Ni1—N1—H1A	107.2
Ni2—N6—H6A	106.9	C1—N1—H1B	107.2
C9—N6—H6B	106.9	Ni1—N1—H1B	107.2
Ni2—N6—H6B	106.9	H1A—N1—H1B	106.9
H6A—N6—H6B	106.7	C1—C2—C3	115.4 (3)
C12—N7—Ni2	120.5 (2)	C1—C2—H2A	108.4
C12—N7—H7A	107.2	C3—C2—H2A	108.4
Ni2—N7—H7A	107.2	C1—C2—H2B	108.4
C12—N7—H7B	107.2	C3—C2—H2B	108.4
Ni2—N7—H7B	107.2	H2A—C2—H2B	107.5
H7A—N7—H7B	106.8	N1—C1—C2	111.9 (2)
C10—N8—Ni2	120.6 (2)	N1—C1—H1C	109.2
C10—N8—H8A	107.2	C2—C1—H1C	109.2
Ni2—N8—H8A	107.2	N1—C1—H1D	109.2
C10—N8—H8B	107.2	C2—C1—H1D	109.2
Ni2—N8—H8B	107.2	H1C—C1—H1D	107.9
H8A—N8—H8B	106.8	N2—C3—C2	113.4 (3)
N6—C9—C8	112.7 (3)	N2—C3—H3C	108.9
N6—C9—H9A	109.1	C2—C3—H3C	108.9
C8—C9—H9A	109.1	N2—C3—H3D	108.9
N6—C9—H9B	109.1	C2—C3—H3D	108.9
C8—C9—H9B	109.1	H3C—C3—H3D	107.7
H9A—C9—H9B	107.8	C3—N2—Ni1	120.99 (18)
H3—O2—H4	109 (3)	C3—N2—H2C	107.1
N5—C7—C8	112.1 (3)	Ni1—N2—H2C	107.1
N5—C7—H7C	109.2	C3—N2—H2D	107.1
C8—C7—H7C	109.2	Ni1—N2—H2D	107.1
N5—C7—H7D	109.2	H2C—N2—H2D	106.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84 (2)	1.98 (2)	2.805 (4)	169 (4)
O1—H2···Br3ii	0.84 (2)	2.37 (2)	3.208 (3)	170 (3)
O2—H4···Br2	0.84 (2)	2.55 (2)	3.327 (3)	154 (4)
O2—H3···Br1	0.83 (2)	2.61 (2)	3.443 (3)	174 (3)
N1—H1A···Br2i	0.97	2.58	3.541 (3)	170
N1—H1B···Br3ii	0.97	2.90	3.699 (3)	141
N2—H2D···Br3iii	0.97	2.77	3.630 (3)	149
N2—H2C···Br2	0.97	3.02	3.720 (3)	130
N3—H3A···Br3	0.97	2.73	3.467 (3)	133
N3—H3B···Br2iii	0.97	2.70	3.544 (3)	146
N4—H4A···Br1iv	0.97	2.70	3.644 (3)	163
N4—H4B···Br3v	0.97	2.72	3.646 (3)	161
N5—H5A···Br1vi	0.97	2.64	3.488 (2)	146
N5—H5B···Br2iii	0.97	2.63	3.537 (3)	156
N6—H6A···Br1	0.97	2.49	3.445 (3)	170
N6—H6B···Br1iv	0.97	2.55	3.504 (3)	169
N7—H7B···Br2iii	0.97	2.75	3.615 (3)	149
N7—H7A···Br2	0.97	2.99	3.726 (3)	133
N8—H8A···Br3v	0.97	2.59	3.558 (3)	175
N8—H8B···Br1	0.97	2.85	3.768 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84 (2)	1.98 (2)	2.805 (4)	169 (4)
O1—H2⋯Br3i	0.84 (2)	2.37 (2)	3.208 (3)	170 (3)
O2—H4⋯Br2	0.84 (2)	2.55 (2)	3.327 (3)	154 (4)
O2—H3⋯Br1	0.83 (2)	2.61 (2)	3.443 (3)	174 (3)
N1—H1A⋯Br2ii	0.97	2.58	3.541 (3)	170
N1—H1B⋯Br3i	0.97	2.90	3.699 (3)	141
N2—H2D⋯Br3iii	0.97	2.77	3.630 (3)	149
N2—H2C⋯Br2	0.97	3.02	3.720 (3)	130
N3—H3A⋯Br3	0.97	2.73	3.467 (3)	133
N3—H3B⋯Br2iii	0.97	2.70	3.544 (3)	146
N4—H4A⋯Br1iv	0.97	2.70	3.644 (3)	163
N4—H4B⋯Br3v	0.97	2.72	3.646 (3)	161
N5—H5A⋯Br1vi	0.97	2.64	3.488 (2)	146
N5—H5B⋯Br2iii	0.97	2.63	3.537 (3)	156
N6—H6A⋯Br1	0.97	2.49	3.445 (3)	170
N6—H6B⋯Br1iv	0.97	2.55	3.504 (3)	169
N7—H7B⋯Br2iii	0.97	2.75	3.615 (3)	149
N7—H7A⋯Br2	0.97	2.99	3.726 (3)	133
N8—H8A⋯Br3v	0.97	2.59	3.558 (3)	175
N8—H8B⋯Br1	0.97	2.85	3.768 (3)	159

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