1-Ethyl-6-fluoro-7-(4-methyl-piperazin-4-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate hexa-hydrate.

In the title compound, C(17)H(20)FN(3)O(3)·6H(2)O, the pefloxacin (pef) neutral zwitterion is accompanied by six water mol-ecules of hydration. An extensive network of O-H⋯O and N-H⋯O hydrogen bonds help to establish the crystal packing.

Related literature

For metal complexes of the pef anion, see: Baenziger et al. (1986 ▶); An, Huang & Qi (2007 ▶); An, Qi & Huang (2007 ▶). For background on the medicinal uses of Hpef, see: Mizuki et al. (1996 ▶).

Experimental

Crystal data

C17H20FN3O3·6H2O

M = 441.46

Monoclinic,

a = 8.0925 (15) Å

b = 24.075 (5) Å

c = 10.8006 (19) Å

β = 92.064 (3)°

V = 2102.9 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 (2) K

0.34 × 0.26 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.960, T max = 0.978

10920 measured reflections

3743 independent reflections

2239 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.134

S = 1.02

3743 reflections

312 parameters

19 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Bruker, 1998 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000421/hb2680sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000421/hb2680Isup2.hkl

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

C17H20FN3O3·6H2O	F000 = 944
Mr = 441.46	Dx = 1.394 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10069 reflections
a = 8.0925 (15) Å	θ = 2.1–25.1º
b = 24.075 (5) Å	µ = 0.12 mm−1
c = 10.8006 (19) Å	T = 296 (2) K
β = 92.064 (3)º	Prism, colorless
V = 2102.9 (7) Å3	0.34 × 0.26 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	3743 independent reflections
Radiation source: fine-focus sealed tube	2239 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.051
T = 295(2) K	θmax = 25.1º
ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 1998)	h = −9→9
Tmin = 0.960, Tmax = 0.978	k = −25→28
10920 measured reflections	l = −8→12

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.0315P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3743 reflections	Δρmax = 0.22 e Å−3
312 parameters	Δρmin = −0.20 e Å−3
19 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
F1	0.4982 (2)	0.12293 (6)	0.56081 (13)	0.0524 (5)
O1	0.9475 (3)	−0.18675 (8)	0.62111 (17)	0.0512 (5)
O2	0.9816 (3)	−0.13364 (8)	0.78658 (17)	0.0548 (6)
O3	0.7598 (2)	−0.04158 (7)	0.76314 (16)	0.0436 (5)
O1W	1.0319 (4)	−0.28815 (9)	0.7094 (2)	0.0761 (7)
H1W1	1.010 (5)	−0.2538 (6)	0.695 (3)	0.114*
H1W2	1.104 (4)	−0.2906 (13)	0.768 (3)	0.114*
O2W	1.0567 (3)	−0.19330 (10)	0.9952 (2)	0.0687 (7)
H2W1	1.042 (4)	−0.1772 (13)	0.9256 (17)	0.103*
H2W2	1.121 (4)	−0.1734 (12)	1.042 (2)	0.103*
O3W	1.2764 (3)	−0.26876 (9)	0.92250 (17)	0.0558 (6)
H3W2	1.318 (4)	−0.2872 (11)	0.9835 (19)	0.084*
H3W1	1.204 (3)	−0.2460 (12)	0.950 (2)	0.084*
O4W	0.6261 (3)	0.02774 (10)	0.9339 (2)	0.0637 (6)
O5W	1.0677 (3)	−0.04707 (12)	0.9484 (2)	0.0817 (8)
H5W1	1.022 (4)	−0.0705 (13)	0.899 (3)	0.123*
H5W2	0.997 (3)	−0.0308 (15)	0.990 (4)	0.123*
O6W	1.2719 (3)	−0.13973 (11)	1.1601 (3)	0.0914 (9)
H6W1	1.360 (3)	−0.1585 (13)	1.176 (4)	0.137*
H6W2	1.298 (5)	−0.1066 (7)	1.143 (4)	0.137*
N1	0.8676 (2)	−0.05154 (8)	0.39571 (18)	0.0325 (5)
N2	0.5711 (3)	0.12232 (8)	0.31502 (18)	0.0351 (5)
N3	0.4587 (3)	0.20866 (9)	0.1516 (2)	0.0399 (6)
H3N	0.552 (2)	0.2224 (11)	0.119 (2)	0.060*
C1	0.9405 (3)	−0.14034 (11)	0.6754 (3)	0.0361 (6)
C2	0.8807 (3)	−0.09193 (10)	0.6006 (2)	0.0318 (6)
C3	0.7935 (3)	−0.04596 (10)	0.6512 (2)	0.0320 (6)
C4	0.7415 (3)	−0.00337 (10)	0.5619 (2)	0.0303 (6)
C5	0.6494 (3)	0.04228 (10)	0.6011 (2)	0.0350 (6)
H5	0.6234	0.0454	0.6840	0.042*
C6	0.5981 (3)	0.08168 (11)	0.5202 (2)	0.0354 (6)
C7	0.6356 (3)	0.08101 (11)	0.3938 (2)	0.0327 (6)
C8	0.7274 (3)	0.03613 (10)	0.3540 (2)	0.0318 (6)
H8	0.7556	0.0341	0.2714	0.038*
C9	0.7785 (3)	−0.00614 (10)	0.4361 (2)	0.0294 (6)
C10	0.9112 (3)	−0.09195 (10)	0.4773 (2)	0.0337 (6)
H10	0.9671	−0.1225	0.4467	0.040*
C11	0.6038 (3)	0.18058 (10)	0.3458 (2)	0.0404 (7)
H11B	0.7100	0.1916	0.3149	0.048*
H11A	0.6076	0.1853	0.4351	0.048*
C12	0.4696 (4)	0.21632 (11)	0.2885 (2)	0.0422 (7)
H12B	0.3646	0.2067	0.3233	0.051*
H12A	0.4924	0.2550	0.3076	0.051*
C13	0.4413 (3)	0.14871 (11)	0.1185 (2)	0.0390 (7)
H13B	0.4475	0.1445	0.0295	0.047*
H13A	0.3338	0.1355	0.1424	0.047*
C14	0.5745 (3)	0.11382 (11)	0.1818 (2)	0.0391 (7)
H14B	0.5560	0.0749	0.1627	0.047*
H14A	0.6818	0.1243	0.1522	0.047*
C15	0.3210 (4)	0.24236 (14)	0.0946 (3)	0.0607 (9)
H15A	0.3180	0.2374	0.0064	0.091*
H15B	0.3387	0.2809	0.1138	0.091*
H15C	0.2179	0.2305	0.1270	0.091*
C16	0.9107 (3)	−0.05917 (12)	0.2649 (2)	0.0390 (7)
H16B	1.0083	−0.0824	0.2617	0.047*
H16A	0.9375	−0.0233	0.2299	0.047*
C17	0.7735 (4)	−0.08525 (15)	0.1874 (3)	0.0642 (10)
H17A	0.7489	−0.1213	0.2198	0.096*
H17B	0.8072	−0.0888	0.1035	0.096*
H17C	0.6766	−0.0623	0.1895	0.096*
H4W1	0.657 (4)	0.0071 (13)	0.874 (2)	0.096*
H4W2	0.709 (3)	0.0325 (14)	0.984 (2)	0.096*

	U11	U22	U33	U12	U13	U23
F1	0.0657 (11)	0.0498 (11)	0.0420 (10)	0.0227 (9)	0.0072 (8)	−0.0003 (7)
O1	0.0692 (14)	0.0320 (12)	0.0515 (13)	0.0057 (10)	−0.0116 (10)	0.0010 (9)
O2	0.0748 (15)	0.0505 (13)	0.0380 (13)	0.0082 (11)	−0.0155 (10)	0.0037 (9)
O3	0.0604 (13)	0.0411 (12)	0.0293 (11)	0.0039 (10)	0.0017 (9)	0.0017 (8)
O1W	0.097 (2)	0.0451 (14)	0.0843 (19)	−0.0009 (14)	−0.0253 (14)	0.0077 (12)
O2W	0.0744 (18)	0.0650 (16)	0.0660 (16)	0.0009 (13)	−0.0099 (13)	0.0230 (12)
O3W	0.0567 (15)	0.0574 (15)	0.0531 (14)	−0.0038 (11)	−0.0015 (10)	0.0151 (10)
O4W	0.0667 (15)	0.0719 (17)	0.0519 (15)	0.0112 (13)	−0.0060 (11)	−0.0213 (11)
O5W	0.091 (2)	0.081 (2)	0.0720 (19)	−0.0046 (16)	−0.0108 (14)	−0.0229 (12)
O6W	0.107 (2)	0.0690 (18)	0.096 (2)	0.0147 (16)	−0.0310 (17)	−0.0081 (16)
N1	0.0363 (13)	0.0324 (12)	0.0290 (12)	0.0011 (10)	0.0018 (9)	−0.0018 (10)
N2	0.0484 (14)	0.0282 (12)	0.0280 (12)	−0.0011 (11)	−0.0074 (10)	−0.0007 (9)
N3	0.0408 (15)	0.0389 (14)	0.0400 (14)	0.0036 (11)	0.0015 (11)	0.0076 (10)
C1	0.0346 (16)	0.0341 (16)	0.0395 (17)	−0.0036 (13)	−0.0005 (12)	0.0017 (13)
C2	0.0330 (15)	0.0322 (15)	0.0298 (15)	−0.0020 (12)	−0.0040 (11)	0.0008 (11)
C3	0.0324 (15)	0.0327 (15)	0.0305 (15)	−0.0051 (12)	−0.0031 (11)	−0.0002 (12)
C4	0.0325 (15)	0.0285 (14)	0.0295 (14)	−0.0049 (12)	−0.0025 (11)	−0.0001 (11)
C5	0.0409 (16)	0.0380 (16)	0.0258 (14)	0.0016 (13)	−0.0013 (11)	−0.0029 (12)
C6	0.0377 (16)	0.0359 (16)	0.0325 (15)	0.0056 (13)	−0.0003 (12)	−0.0046 (12)
C7	0.0316 (14)	0.0332 (15)	0.0327 (15)	−0.0062 (12)	−0.0045 (11)	0.0026 (12)
C8	0.0338 (15)	0.0317 (15)	0.0299 (14)	−0.0024 (12)	0.0026 (11)	0.0000 (11)
C9	0.0278 (14)	0.0304 (14)	0.0299 (14)	−0.0053 (12)	0.0009 (11)	−0.0011 (11)
C10	0.0340 (15)	0.0266 (14)	0.0405 (16)	0.0019 (12)	−0.0015 (12)	−0.0020 (12)
C11	0.0492 (18)	0.0333 (16)	0.0378 (16)	−0.0046 (14)	−0.0090 (12)	−0.0014 (12)
C12	0.0522 (19)	0.0367 (16)	0.0379 (17)	0.0030 (14)	0.0035 (13)	−0.0014 (12)
C13	0.0450 (17)	0.0415 (17)	0.0304 (15)	−0.0026 (14)	−0.0021 (12)	0.0020 (12)
C14	0.0504 (17)	0.0338 (16)	0.0329 (16)	0.0014 (13)	−0.0010 (12)	0.0005 (12)
C15	0.053 (2)	0.061 (2)	0.068 (2)	0.0162 (17)	−0.0062 (16)	0.0190 (16)
C16	0.0476 (17)	0.0404 (16)	0.0294 (15)	0.0017 (13)	0.0086 (12)	−0.0007 (12)
C17	0.073 (2)	0.077 (2)	0.0430 (19)	−0.019 (2)	0.0019 (16)	−0.0111 (16)

F1—C6	1.363 (3)	C3—C4	1.459 (3)
C1—O1	1.264 (3)	C4—C5	1.402 (3)
C1—O2	1.245 (3)	C4—C9	1.404 (3)
C3—O3	1.253 (3)	C5—C6	1.345 (3)
O1W—H1W1	0.857 (10)	C5—H5	0.9300
O1W—H1W2	0.85 (3)	C6—C7	1.409 (3)
O2W—H2W1	0.851 (10)	C7—C8	1.388 (3)
O2W—H2W2	0.86 (3)	C8—C9	1.402 (3)
O3W—H3W2	0.852 (10)	C8—H8	0.9300
O3W—H3W1	0.86 (3)	C10—H10	0.9300
O4W—H4W1	0.86 (3)	C11—C12	1.501 (4)
O4W—H4W2	0.851 (10)	C11—H11B	0.9700
O5W—H5W1	0.85 (3)	C11—H11A	0.9700
O5W—H5W2	0.84 (3)	C12—H12B	0.9700
O6W—H6W1	0.86 (3)	C12—H12A	0.9700
O6W—H6W2	0.847 (10)	C13—C14	1.510 (4)
N1—C10	1.351 (3)	C13—H13B	0.9700
N1—C9	1.388 (3)	C13—H13A	0.9700
N1—C16	1.479 (3)	C14—H14B	0.9700
N2—C7	1.397 (3)	C14—H14A	0.9700
N2—C14	1.454 (3)	C15—H15A	0.9600
N2—C11	1.463 (3)	C15—H15B	0.9600
N3—C12	1.490 (3)	C15—H15C	0.9600
N3—C13	1.492 (3)	C16—C17	1.504 (4)
N3—C15	1.493 (3)	C16—H16B	0.9700
N3—H3N	0.910 (10)	C16—H16A	0.9700
C1—C2	1.489 (4)	C17—H17A	0.9600
C2—C10	1.363 (3)	C17—H17B	0.9600
C2—C3	1.431 (3)	C17—H17C	0.9600
H1W1—O1W—H1W2	109.3 (17)	N1—C10—C2	125.8 (2)
H2W1—O2W—H2W2	109.4 (16)	N1—C10—H10	117.1
H3W2—O3W—H3W1	108.6 (16)	C2—C10—H10	117.1
H4W1—O4W—H4W2	108.2 (16)	N2—C11—C12	109.5 (2)
H5W1—O5W—H5W2	110.9 (18)	N2—C11—H11B	109.8
H6W1—O6W—H6W2	109.4 (17)	C12—C11—H11B	109.8
C10—N1—C9	119.2 (2)	N2—C11—H11A	109.8
C10—N1—C16	118.0 (2)	C12—C11—H11A	109.8
C9—N1—C16	122.7 (2)	H11B—C11—H11A	108.2
C7—N2—C14	118.8 (2)	N3—C12—C11	110.8 (2)
C7—N2—C11	118.89 (19)	N3—C12—H12B	109.5
C14—N2—C11	110.49 (19)	C11—C12—H12B	109.5
C12—N3—C13	111.04 (19)	N3—C12—H12A	109.5
C12—N3—C15	111.0 (2)	C11—C12—H12A	109.5
C13—N3—C15	111.4 (2)	H12B—C12—H12A	108.1
C12—N3—H3N	108.4 (19)	N3—C13—C14	111.7 (2)
C13—N3—H3N	109.5 (19)	N3—C13—H13B	109.3
C15—N3—H3N	105.3 (19)	C14—C13—H13B	109.3
O2—C1—O1	123.2 (2)	N3—C13—H13A	109.3
O2—C1—C2	119.5 (2)	C14—C13—H13A	109.3
O1—C1—C2	117.3 (2)	H13B—C13—H13A	107.9
C10—C2—C3	118.9 (2)	N2—C14—C13	109.3 (2)
C10—C2—C1	117.6 (2)	N2—C14—H14B	109.8
C3—C2—C1	123.6 (2)	C13—C14—H14B	109.8
O3—C3—C2	124.1 (2)	N2—C14—H14A	109.8
O3—C3—C4	120.7 (2)	C13—C14—H14A	109.8
C2—C3—C4	115.2 (2)	H14B—C14—H14A	108.3
C5—C4—C9	117.6 (2)	N3—C15—H15A	109.5
C5—C4—C3	119.7 (2)	N3—C15—H15B	109.5
C9—C4—C3	122.7 (2)	H15A—C15—H15B	109.5
C6—C5—C4	120.8 (2)	N3—C15—H15C	109.5
C6—C5—H5	119.6	H15A—C15—H15C	109.5
C4—C5—H5	119.6	H15B—C15—H15C	109.5
C5—C6—F1	118.5 (2)	N1—C16—C17	112.9 (2)
C5—C6—C7	123.3 (2)	N1—C16—H16B	109.0
F1—C6—C7	118.1 (2)	C17—C16—H16B	109.0
C8—C7—N2	123.9 (2)	N1—C16—H16A	109.0
C8—C7—C6	116.4 (2)	C17—C16—H16A	109.0
N2—C7—C6	119.5 (2)	H16B—C16—H16A	107.8
C7—C8—C9	121.2 (2)	C16—C17—H17A	109.5
C7—C8—H8	119.4	C16—C17—H17B	109.5
C9—C8—H8	119.4	H17A—C17—H17B	109.5
N1—C9—C8	121.2 (2)	C16—C17—H17C	109.5
N1—C9—C4	118.2 (2)	H17A—C17—H17C	109.5
C8—C9—C4	120.6 (2)	H17B—C17—H17C	109.5
O2—C1—C2—C10	149.2 (3)	C10—N1—C9—C8	−178.5 (2)
O1—C1—C2—C10	−30.5 (3)	C16—N1—C9—C8	−1.6 (3)
O2—C1—C2—C3	−30.8 (4)	C10—N1—C9—C4	1.9 (3)
O1—C1—C2—C3	149.5 (2)	C16—N1—C9—C4	178.8 (2)
C10—C2—C3—O3	−179.6 (2)	C7—C8—C9—N1	178.8 (2)
C1—C2—C3—O3	0.5 (4)	C7—C8—C9—C4	−1.7 (3)
C10—C2—C3—C4	1.5 (3)	C5—C4—C9—N1	−179.1 (2)
C1—C2—C3—C4	−178.4 (2)	C3—C4—C9—N1	0.3 (3)
O3—C3—C4—C5	−1.5 (3)	C5—C4—C9—C8	1.3 (3)
C2—C3—C4—C5	177.4 (2)	C3—C4—C9—C8	−179.3 (2)
O3—C3—C4—C9	179.1 (2)	C9—N1—C10—C2	−2.5 (4)
C2—C3—C4—C9	−2.0 (3)	C16—N1—C10—C2	−179.6 (2)
C9—C4—C5—C6	0.3 (4)	C3—C2—C10—N1	0.6 (4)
C3—C4—C5—C6	−179.1 (2)	C1—C2—C10—N1	−179.4 (2)
C4—C5—C6—F1	175.0 (2)	C7—N2—C11—C12	−154.7 (2)
C4—C5—C6—C7	−1.7 (4)	C14—N2—C11—C12	62.7 (3)
C14—N2—C7—C8	11.0 (4)	C13—N3—C12—C11	53.2 (3)
C11—N2—C7—C8	−128.5 (3)	C15—N3—C12—C11	177.7 (2)
C14—N2—C7—C6	−164.6 (2)	N2—C11—C12—N3	−58.1 (3)
C11—N2—C7—C6	56.0 (3)	C12—N3—C13—C14	−52.3 (3)
C5—C6—C7—C8	1.3 (4)	C15—N3—C13—C14	−176.6 (2)
F1—C6—C7—C8	−175.4 (2)	C7—N2—C14—C13	156.2 (2)
C5—C6—C7—N2	177.2 (2)	C11—N2—C14—C13	−61.2 (3)
F1—C6—C7—N2	0.4 (3)	N3—C13—C14—N2	56.0 (3)
N2—C7—C8—C9	−175.3 (2)	C10—N1—C16—C17	93.5 (3)
C6—C7—C8—C9	0.4 (3)	C9—N1—C16—C17	−83.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1	0.857 (10)	1.866 (12)	2.700 (3)	164 (3)
O1W—H1W2···O3W	0.85 (3)	2.201 (16)	3.017 (3)	162 (3)
O2W—H2W1···O2	0.851 (10)	1.881 (13)	2.722 (3)	170 (4)
O2W—H2W2···O6W	0.86 (3)	1.91 (3)	2.765 (3)	171 (3)
O3W—H3W2···O1i	0.852 (10)	1.896 (13)	2.730 (3)	166 (3)
O3W—H3W1···O2W	0.86 (3)	1.82 (3)	2.679 (3)	175 (3)
O6W—H6W1···O1Wi	0.86 (3)	1.92 (3)	2.765 (4)	170 (4)
O6W—H6W2···O4Wii	0.847 (10)	2.17 (3)	3.007 (4)	170 (4)
N3—H3N···O3Wiii	0.910 (10)	1.847 (13)	2.730 (3)	163 (3)
O4W—H4W1···O3	0.86 (3)	1.89 (3)	2.739 (3)	169 (3)
O4W—H4W2···O5Wii	0.85 (3)	1.959 (15)	2.783 (3)	163 (3)
O5W—H5W1···O2	0.85 (3)	1.97 (3)	2.792 (3)	164 (4)
O5W—H5W1···O3	0.85 (3)	2.63 (4)	3.142 (3)	120 (3)
O5W—H5W2···O5Wii	0.84 (3)	2.06 (2)	2.769 (5)	142 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O1	0.857 (10)	1.866 (12)	2.700 (3)	164 (3)
O1W—H1W2⋯O3W	0.85 (3)	2.201 (16)	3.017 (3)	162 (3)
O2W—H2W1⋯O2	0.851 (10)	1.881 (13)	2.722 (3)	170 (4)
O2W—H2W2⋯O6W	0.86 (3)	1.91 (3)	2.765 (3)	171 (3)
O3W—H3W2⋯O1i	0.852 (10)	1.896 (13)	2.730 (3)	166 (3)
O3W—H3W1⋯O2W	0.86 (3)	1.82 (3)	2.679 (3)	175 (3)
O6W—H6W1⋯O1Wi	0.86 (3)	1.92 (3)	2.765 (4)	170 (4)
O6W—H6W2⋯O4Wii	0.847 (10)	2.17 (3)	3.007 (4)	170 (4)
N3—H3N⋯O3Wiii	0.910 (10)	1.847 (13)	2.730 (3)	163 (3)
O4W—H4W1⋯O3	0.86 (3)	1.89 (3)	2.739 (3)	169 (3)
O4W—H4W2⋯O5Wii	0.85 (3)	1.959 (15)	2.783 (3)	163 (3)
O5W—H5W1⋯O2	0.85 (3)	1.97 (3)	2.792 (3)	164 (4)
O5W—H5W1⋯O3	0.85 (3)	2.63 (4)	3.142 (3)	120 (3)
O5W—H5W2⋯O5Wii	0.84 (3)	2.06 (2)	2.769 (5)	142 (3)

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