Bis{1-[(1H-benzimidazol-1-yl)meth-yl]-1H-imidazole-κN (3)}bis-(3,5-dicarb-oxy-benzoato-κ(2) O (1),O (1'))nickel(II) octa-hydrate.

In the title complex, [Ni(C9H5O6)2(C11H10N4)2]·8H2O, the Ni(II) ion exhibits site symmetry 2. It has a distorted octa-hedral coordination defined by two N atoms from two symmetry-related 1-[(1H-benzimidazol-1-yl)meth-yl]-1H-imidazole ligands and four O atoms from two symmetry-related 3,5-dicarb-oxy-benzoate anions. In the crystal, the complex mol-ecules and solvent water mol-ecules are linked via O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds, forming a three-dimensional structure. There are also a number of C-H⋯O inter-actions present.

Related literature

For background information to NiII complexes constructed from both aromatic carboxyl­ates and N-heterocyclic ligands, see: Hu et al. (2011 ▶); Xu et al. (2010 ▶).

Experimental

Crystal data

[Ni(C9H5O6)2(C11H10N4)2]·8H2O

M = 1017.56

Monoclinic,

a = 20.623 (4) Å

b = 14.626 (3) Å

c = 15.471 (3) Å

β = 104.03 (3)°

V = 4527.2 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.52 mm−1

T = 293 K

0.19 × 0.17 × 0.12 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004 ▶) T min = 0.908, T max = 0.940

16185 measured reflections

4215 independent reflections

3719 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.172

S = 1.13

4215 reflections

314 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813003322/su2557sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003322/su2557Isup2.hkl

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

[Ni(C9H5O6)2(C11H10N4)2]·8H2O	F(000) = 2120
Mr = 1017.56	Dx = 1.493 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.623 (4) Å	Cell parameters from 5823 reflections
b = 14.626 (3) Å	θ = 1.7–27.9°
c = 15.471 (3) Å	µ = 0.52 mm−1
β = 104.03 (3)°	T = 293 K
V = 4527.2 (16) Å3	Prism, green
Z = 4	0.19 × 0.17 × 0.12 mm

Rigaku Saturn diffractometer	4215 independent reflections
Radiation source: fine-focus sealed tube	3719 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 28.5714 pixels mm-1	θmax = 25.5°, θmin = 2.0°
ω scans	h = −24→24
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	k = −14→17
Tmin = 0.908, Tmax = 0.940	l = −18→15
16185 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0894P)2 + 4.146P] where P = (Fo2 + 2Fc2)/3
4215 reflections	(Δ/σ)max < 0.001
314 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
Ni1	0.50000	0.05398 (4)	0.25000	0.0263 (2)
O1	0.44973 (11)	0.17115 (16)	0.15907 (16)	0.0365 (8)
O2	0.40111 (11)	0.07735 (16)	0.23391 (16)	0.0338 (8)
O3	0.15958 (15)	0.0697 (2)	0.1857 (2)	0.0608 (13)
O4	0.09844 (14)	0.1905 (2)	0.1294 (3)	0.0686 (13)
O5	0.20784 (14)	0.46292 (18)	0.0447 (2)	0.0522 (10)
O6	0.31803 (15)	0.46684 (19)	0.0667 (2)	0.0568 (10)
N1	0.51386 (13)	−0.03683 (19)	0.35162 (18)	0.0300 (9)
N2	0.54931 (13)	−0.09621 (19)	0.48450 (18)	0.0293 (8)
N3	0.65040 (14)	−0.2528 (2)	0.61442 (19)	0.0340 (9)
N4	0.70616 (14)	−0.13469 (19)	0.58371 (19)	0.0327 (9)
C1	0.55815 (16)	−0.0300 (2)	0.4289 (2)	0.0277 (10)
C2	0.47484 (17)	−0.1117 (2)	0.3587 (2)	0.0377 (11)
C3	0.49601 (18)	−0.1488 (3)	0.4409 (2)	0.0390 (12)
C4	0.58605 (17)	−0.1066 (2)	0.5776 (2)	0.0335 (11)
C5	0.64692 (16)	−0.1648 (2)	0.5901 (2)	0.0292 (10)
C6	0.75139 (17)	−0.2070 (2)	0.6066 (2)	0.0326 (10)
C7	0.81932 (18)	−0.2116 (3)	0.6135 (2)	0.0413 (11)
C8	0.8498 (2)	−0.2936 (3)	0.6411 (3)	0.0488 (14)
C9	0.8142 (2)	−0.3693 (3)	0.6597 (3)	0.0491 (14)
C10	0.7470 (2)	−0.3652 (3)	0.6525 (3)	0.0473 (14)
C11	0.71606 (17)	−0.2822 (2)	0.6260 (2)	0.0329 (11)
C12	0.39819 (16)	0.1458 (2)	0.1831 (2)	0.0305 (10)
C13	0.33326 (16)	0.1947 (2)	0.1540 (2)	0.0298 (10)
C14	0.27601 (17)	0.1527 (2)	0.1660 (2)	0.0338 (11)
C15	0.21442 (16)	0.1966 (2)	0.1419 (2)	0.0330 (11)
C16	0.21099 (17)	0.2849 (2)	0.1080 (2)	0.0352 (11)
C17	0.26850 (17)	0.3292 (2)	0.0971 (2)	0.0331 (11)
C18	0.32924 (17)	0.2827 (2)	0.1189 (2)	0.0325 (10)
C19	0.15416 (19)	0.1473 (3)	0.1539 (3)	0.0441 (14)
C20	0.26497 (19)	0.4268 (2)	0.0666 (3)	0.0403 (11)
O7	−0.07964 (17)	−0.0247 (2)	0.2232 (2)	0.0719 (11)
O8	−0.03597 (17)	−0.1763 (2)	0.3458 (3)	0.0795 (14)
O9	0.5992 (2)	0.5579 (3)	0.5235 (3)	0.107 (2)
O10	−0.0070 (3)	0.0946 (5)	0.1264 (4)	0.183 (3)
H1A	0.59100	0.01480	0.44280	0.0330*
H2A	0.43950	−0.13330	0.31400	0.0450*
H3	0.12890	0.06020	0.20980	0.0730*
H3A	0.47820	−0.19940	0.46330	0.0470*
H3B	0.61750	−0.28560	0.62170	0.0410*
H4A	0.55640	−0.13310	0.61090	0.0400*
H4B	0.59910	−0.04650	0.60230	0.0400*
H5	0.21090	0.51760	0.05690	0.0630*
H7A	0.84320	−0.16180	0.60010	0.0500*
H8A	0.89570	−0.29890	0.64760	0.0580*
H9A	0.83670	−0.42380	0.67730	0.0590*
H10A	0.72310	−0.41550	0.66490	0.0570*
H14A	0.27870	0.09430	0.19040	0.0410*
H16A	0.17000	0.31480	0.09230	0.0420*
H18A	0.36750	0.31080	0.11000	0.0390*
H1W	−0.06060	0.01530	0.19800	0.0860*
H2W	−0.11320	−0.02630	0.17870	0.0860*
H3W	−0.00440	−0.21200	0.34160	0.0950*
H4W	−0.04180	−0.14410	0.29870	0.0950*
H5W	0.61540	0.52330	0.56760	0.1280*
H6W	0.63240	0.55220	0.50050	0.1280*
H7W	0.02720	0.12840	0.13100	0.2200*
H8W	−0.03660	0.09890	0.07760	0.2200*

	U11	U22	U33	U12	U13	U23
Ni1	0.0205 (3)	0.0263 (4)	0.0307 (4)	0.0000	0.0033 (2)	0.0000
O1	0.0243 (12)	0.0331 (14)	0.0513 (15)	0.0031 (10)	0.0077 (11)	0.0034 (11)
O2	0.0270 (12)	0.0347 (14)	0.0377 (13)	0.0067 (10)	0.0042 (10)	0.0067 (11)
O3	0.0446 (18)	0.0437 (18)	0.102 (3)	0.0041 (13)	0.0330 (17)	0.0223 (16)
O4	0.0281 (15)	0.0512 (19)	0.124 (3)	0.0069 (13)	0.0135 (16)	0.0257 (18)
O5	0.0395 (16)	0.0236 (13)	0.087 (2)	0.0071 (11)	0.0026 (14)	0.0013 (14)
O6	0.0411 (17)	0.0366 (16)	0.091 (2)	−0.0024 (13)	0.0129 (15)	0.0155 (15)
N1	0.0242 (14)	0.0300 (15)	0.0347 (16)	0.0026 (11)	0.0048 (12)	0.0012 (12)
N2	0.0243 (14)	0.0289 (15)	0.0332 (15)	0.0024 (11)	0.0039 (11)	0.0034 (12)
N3	0.0287 (15)	0.0293 (16)	0.0445 (17)	−0.0005 (12)	0.0101 (13)	0.0083 (13)
N4	0.0280 (15)	0.0285 (15)	0.0395 (16)	0.0000 (12)	0.0044 (12)	0.0006 (12)
C1	0.0224 (15)	0.0256 (17)	0.0349 (18)	0.0017 (13)	0.0067 (13)	0.0007 (13)
C2	0.0286 (18)	0.037 (2)	0.043 (2)	−0.0081 (15)	0.0002 (15)	0.0003 (16)
C3	0.036 (2)	0.032 (2)	0.047 (2)	−0.0066 (15)	0.0064 (16)	0.0048 (16)
C4	0.0305 (18)	0.037 (2)	0.0316 (18)	0.0079 (15)	0.0049 (14)	0.0020 (15)
C5	0.0297 (17)	0.0279 (18)	0.0280 (17)	0.0025 (13)	0.0029 (13)	0.0005 (13)
C6	0.0335 (18)	0.0285 (18)	0.0341 (18)	0.0037 (14)	0.0048 (14)	−0.0005 (14)
C7	0.0310 (19)	0.045 (2)	0.047 (2)	0.0018 (16)	0.0079 (16)	−0.0029 (17)
C8	0.034 (2)	0.056 (3)	0.055 (2)	0.0137 (18)	0.0083 (17)	−0.003 (2)
C9	0.044 (2)	0.040 (2)	0.060 (3)	0.0183 (18)	0.0065 (19)	0.0026 (19)
C10	0.045 (2)	0.035 (2)	0.061 (3)	0.0074 (17)	0.0112 (19)	0.0092 (19)
C11	0.0298 (18)	0.0283 (18)	0.0387 (19)	0.0059 (14)	0.0044 (14)	0.0016 (14)
C12	0.0264 (17)	0.0296 (18)	0.0324 (18)	0.0049 (14)	0.0012 (13)	−0.0053 (14)
C13	0.0272 (17)	0.0275 (18)	0.0325 (18)	0.0050 (13)	0.0030 (13)	−0.0008 (14)
C14	0.0286 (17)	0.0263 (18)	0.045 (2)	0.0036 (14)	0.0061 (15)	0.0034 (15)
C15	0.0262 (17)	0.0280 (18)	0.044 (2)	0.0009 (14)	0.0067 (15)	0.0008 (15)
C16	0.0262 (17)	0.0310 (19)	0.047 (2)	0.0073 (14)	0.0062 (15)	0.0017 (15)
C17	0.0269 (17)	0.0274 (18)	0.042 (2)	0.0052 (13)	0.0023 (14)	−0.0004 (14)
C18	0.0278 (17)	0.0298 (18)	0.0400 (19)	0.0018 (13)	0.0082 (14)	−0.0026 (15)
C19	0.034 (2)	0.036 (2)	0.061 (3)	0.0022 (16)	0.0092 (17)	0.0035 (18)
C20	0.038 (2)	0.0285 (19)	0.053 (2)	0.0036 (15)	0.0081 (17)	0.0001 (16)
O7	0.0484 (19)	0.075 (2)	0.090 (2)	−0.0035 (17)	0.0122 (17)	−0.0016 (19)
O8	0.074 (2)	0.059 (2)	0.125 (3)	0.0071 (18)	0.062 (2)	0.008 (2)
O9	0.114 (4)	0.104 (4)	0.106 (3)	0.019 (3)	0.034 (3)	0.002 (3)
O10	0.087 (4)	0.270 (8)	0.165 (5)	−0.095 (5)	−0.024 (4)	0.106 (5)

Ni1—O1	2.299 (2)	N3—H3B	0.8600
Ni1—O2	2.023 (2)	C2—C3	1.354 (4)
Ni1—N1	2.025 (3)	C4—C5	1.490 (5)
Ni1—O1i	2.299 (2)	C6—C11	1.392 (4)
Ni1—O2i	2.023 (2)	C6—C7	1.381 (5)
Ni1—N1i	2.025 (3)	C7—C8	1.373 (6)
O1—C12	1.264 (4)	C8—C9	1.397 (6)
O2—C12	1.265 (4)	C9—C10	1.365 (6)
O3—C19	1.231 (5)	C10—C11	1.386 (5)
O4—C19	1.285 (5)	C12—C13	1.488 (5)
O5—C20	1.260 (5)	C13—C18	1.392 (4)
O6—C20	1.241 (5)	C13—C14	1.383 (5)
O3—H3	0.8200	C14—C15	1.391 (5)
O5—H5	0.8200	C15—C16	1.389 (4)
O7—H1W	0.8500	C15—C19	1.487 (5)
O7—H2W	0.8500	C16—C17	1.397 (5)
O8—H3W	0.8500	C17—C18	1.393 (5)
O8—H4W	0.8500	C17—C20	1.500 (4)
O9—H5W	0.8500	C1—H1A	0.9300
O9—H6W	0.8500	C2—H2A	0.9300
O10—H8W	0.8500	C3—H3A	0.9300
O10—H7W	0.8500	C4—H4A	0.9700
N1—C1	1.321 (4)	C4—H4B	0.9700
N1—C2	1.379 (4)	C7—H7A	0.9300
N2—C4	1.464 (4)	C8—H8A	0.9300
N2—C3	1.377 (5)	C9—H9A	0.9300
N2—C1	1.337 (4)	C10—H10A	0.9300
N3—C5	1.338 (4)	C14—H14A	0.9300
N3—C11	1.390 (5)	C16—H16A	0.9300
N4—C6	1.398 (4)	C18—H18A	0.9300
N4—C5	1.325 (4)
O1—Ni1—O2	60.46 (9)	C6—C11—C10	121.9 (3)
O1—Ni1—N1	157.24 (10)	N3—C11—C10	132.3 (3)
O1—Ni1—O1i	83.59 (9)	O1—C12—O2	119.9 (3)
O1—Ni1—O2i	103.95 (10)	O1—C12—C13	122.0 (3)
O1—Ni1—N1i	93.21 (10)	O2—C12—C13	118.2 (3)
O2—Ni1—N1	98.90 (11)	C12—C13—C14	118.7 (3)
O1i—Ni1—O2	103.95 (10)	C14—C13—C18	119.4 (3)
O2—Ni1—O2i	160.54 (10)	C12—C13—C18	121.8 (3)
O2—Ni1—N1i	93.84 (11)	C13—C14—C15	120.9 (3)
O1i—Ni1—N1	93.21 (10)	C14—C15—C19	118.6 (3)
O2i—Ni1—N1	93.84 (11)	C16—C15—C19	122.0 (3)
N1—Ni1—N1i	98.01 (12)	C14—C15—C16	119.3 (3)
O1i—Ni1—O2i	60.46 (9)	C15—C16—C17	120.6 (3)
O1i—Ni1—N1i	157.24 (10)	C16—C17—C20	120.1 (3)
O2i—Ni1—N1i	98.90 (11)	C16—C17—C18	119.0 (3)
Ni1—O1—C12	83.57 (18)	C18—C17—C20	120.9 (3)
Ni1—O2—C12	96.0 (2)	C13—C18—C17	120.7 (3)
C19—O3—H3	109.00	O3—C19—O4	124.0 (4)
C20—O5—H5	109.00	O3—C19—C15	120.0 (4)
H1W—O7—H2W	91.00	O4—C19—C15	116.1 (4)
H3W—O8—H4W	103.00	O6—C20—C17	118.3 (3)
H5W—O9—H6W	94.00	O5—C20—O6	124.7 (3)
H7W—O10—H8W	116.00	O5—C20—C17	117.0 (3)
Ni1—N1—C2	127.4 (2)	N2—C1—H1A	125.00
Ni1—N1—C1	126.1 (2)	N1—C1—H1A	125.00
C1—N1—C2	106.1 (3)	N1—C2—H2A	125.00
C1—N2—C4	126.1 (3)	C3—C2—H2A	125.00
C1—N2—C3	107.9 (3)	N2—C3—H3A	127.00
C3—N2—C4	125.8 (3)	C2—C3—H3A	127.00
C5—N3—C11	108.5 (3)	N2—C4—H4B	109.00
C5—N4—C6	107.5 (3)	C5—C4—H4A	109.00
C11—N3—H3B	126.00	C5—C4—H4B	109.00
C5—N3—H3B	126.00	N2—C4—H4A	109.00
N1—C1—N2	110.8 (3)	H4A—C4—H4B	108.00
N1—C2—C3	109.4 (3)	C8—C7—H7A	122.00
N2—C3—C2	105.9 (3)	C6—C7—H7A	122.00
N2—C4—C5	113.9 (3)	C9—C8—H8A	119.00
N3—C5—N4	110.7 (3)	C7—C8—H8A	119.00
N3—C5—C4	124.9 (3)	C10—C9—H9A	119.00
N4—C5—C4	124.3 (3)	C8—C9—H9A	119.00
N4—C6—C7	131.2 (3)	C9—C10—H10A	122.00
C7—C6—C11	121.3 (3)	C11—C10—H10A	122.00
N4—C6—C11	107.5 (3)	C13—C14—H14A	120.00
C6—C7—C8	116.5 (4)	C15—C14—H14A	120.00
C7—C8—C9	122.2 (4)	C17—C16—H16A	120.00
C8—C9—C10	121.5 (4)	C15—C16—H16A	120.00
C9—C10—C11	116.6 (4)	C13—C18—H18A	120.00
N3—C11—C6	105.8 (3)	C17—C18—H18A	120.00
O2—Ni1—O1—C12	1.55 (17)	C5—N4—C6—C11	0.7 (3)
N1—Ni1—O1—C12	−25.5 (3)	N1—C2—C3—N2	−0.6 (4)
O1i—Ni1—O1—C12	−108.47 (18)	N2—C4—C5—N3	−99.5 (4)
O2i—Ni1—O1—C12	−165.85 (18)	N2—C4—C5—N4	84.7 (4)
N1i—Ni1—O1—C12	94.15 (19)	N4—C6—C7—C8	177.7 (4)
O1—Ni1—O2—C12	−1.55 (17)	C11—C6—C7—C8	−0.6 (5)
N1—Ni1—O2—C12	168.19 (19)	N4—C6—C11—N3	−0.2 (3)
O1i—Ni1—O2—C12	72.61 (19)	N4—C6—C11—C10	−179.1 (3)
N1i—Ni1—O2—C12	−93.1 (2)	C7—C6—C11—N3	178.5 (3)
O1—Ni1—N1—C1	−101.9 (3)	C7—C6—C11—C10	−0.4 (5)
O1—Ni1—N1—C2	70.1 (4)	C6—C7—C8—C9	1.2 (6)
O2—Ni1—N1—C1	−125.5 (3)	C7—C8—C9—C10	−0.9 (7)
O2—Ni1—N1—C2	46.5 (3)	C8—C9—C10—C11	−0.1 (6)
O1i—Ni1—N1—C1	−20.8 (3)	C9—C10—C11—N3	−177.8 (4)
O1i—Ni1—N1—C2	151.2 (3)	C9—C10—C11—C6	0.8 (6)
O2i—Ni1—N1—C1	39.8 (3)	O1—C12—C13—C14	166.0 (3)
O2i—Ni1—N1—C2	−148.3 (3)	O1—C12—C13—C18	−16.9 (5)
N1i—Ni1—N1—C1	139.4 (3)	O2—C12—C13—C14	−14.5 (4)
N1i—Ni1—N1—C2	−48.7 (3)	O2—C12—C13—C18	162.6 (3)
Ni1—O1—C12—O2	−2.5 (3)	C12—C13—C14—C15	178.4 (3)
Ni1—O1—C12—C13	177.0 (3)	C18—C13—C14—C15	1.2 (5)
Ni1—O2—C12—O1	2.8 (3)	C12—C13—C18—C17	−176.1 (3)
Ni1—O2—C12—C13	−176.7 (2)	C14—C13—C18—C17	1.0 (5)
Ni1—N1—C1—N2	173.3 (2)	C13—C14—C15—C16	−2.1 (5)
C2—N1—C1—N2	−0.1 (4)	C13—C14—C15—C19	178.3 (3)
Ni1—N1—C2—C3	−172.8 (2)	C14—C15—C16—C17	0.7 (5)
C1—N1—C2—C3	0.4 (4)	C19—C15—C16—C17	−179.7 (3)
C3—N2—C1—N1	−0.3 (4)	C14—C15—C19—O3	0.9 (6)
C4—N2—C1—N1	−175.6 (3)	C14—C15—C19—O4	−179.1 (4)
C1—N2—C3—C2	0.5 (4)	C16—C15—C19—O3	−178.7 (4)
C4—N2—C3—C2	175.9 (3)	C16—C15—C19—O4	1.3 (6)
C1—N2—C4—C5	−91.3 (4)	C15—C16—C17—C18	1.4 (4)
C3—N2—C4—C5	94.2 (4)	C15—C16—C17—C20	−175.7 (3)
C11—N3—C5—N4	0.9 (4)	C16—C17—C18—C13	−2.3 (4)
C11—N3—C5—C4	−175.4 (3)	C20—C17—C18—C13	174.8 (3)
C5—N3—C11—C6	−0.4 (3)	C16—C17—C20—O5	−5.8 (5)
C5—N3—C11—C10	178.3 (4)	C16—C17—C20—O6	172.5 (3)
C6—N4—C5—N3	−1.0 (4)	C18—C17—C20—O5	177.2 (3)
C6—N4—C5—C4	175.3 (3)	C18—C17—C20—O6	−4.5 (5)
C5—N4—C6—C7	−177.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H1W···O10	0.85	2.09	2.936 (7)	170
O7—H2W···O6ii	0.85	1.96	2.802 (4)	172
O3—H3···O7iii	0.82	2.04	2.782 (5)	150
N3—H3B···O8iv	0.86	1.95	2.780 (5)	162
O8—H3W···O1v	0.85	2.05	2.866 (4)	161
O8—H4W···O7	0.85	2.14	2.915 (5)	151
O5—H5···N4vi	0.82	1.77	2.586 (4)	172
O9—H5W···O3vii	0.85	2.28	3.133 (5)	180
O9—H6W···O6i	0.85	2.05	2.791 (5)	146
O10—H7W···O4	0.85	1.73	2.579 (7)	173
C1—H1A···O5vii	0.93	2.56	3.320 (4)	139
C3—H3A···O4v	0.93	2.46	3.078 (5)	124
C4—H4A···O2viii	0.97	2.49	2.895 (4)	105
C4—H4A···O1ix	0.97	2.55	3.479 (4)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H1W⋯O10	0.85	2.09	2.936 (7)	170
O7—H2W⋯O6ii	0.85	1.96	2.802 (4)	172
O3—H3⋯O7iii	0.82	2.04	2.782 (5)	150
N3—H3B⋯O8iv	0.86	1.95	2.780 (5)	162
O8—H3W⋯O1v	0.85	2.05	2.866 (4)	161
O8—H4W⋯O7	0.85	2.14	2.915 (5)	151
O5—H5⋯N4vi	0.82	1.77	2.586 (4)	172
O9—H5W⋯O3vii	0.85	2.28	3.133 (5)	180
O9—H6W⋯O6i	0.85	2.05	2.791 (5)	146
O10—H7W⋯O4	0.85	1.73	2.579 (7)	173
C1—H1A⋯O5vii	0.93	2.56	3.320 (4)	139
C3—H3A⋯O4v	0.93	2.46	3.078 (5)	124
C4—H4A⋯O1viii	0.97	2.55	3.479 (4)	160

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