2,9-Dimethyl-1,10-phenanthrolin-1-ium 2,4,5-tri-carb-oxy-benzoate monohydrate.

In the preparation of the title hydrated salt, C14H13N2 (+)·C10H5O8 (-)·H2O, a proton has been transfered to the 2,9-dimethyl-1,10-phenanthrolinium cation, forming a 2,4,5-tri-carb-oxy-benzoate anion. In the anion, the mean planes of the protonated carboxyl-ate groups form dihedral angles of 11.0 (5), 4.4 (5) and 80.3 (4)° with the benzene ring to which they are attached. The mean plane of the deprotonated carboxyl-ate group forms a dihedral angle of 10.6 (5)° with the benzene ring. In the crystal, the anions are involved in carb-oxy-lic acid O-H⋯Ocarbox-yl hydrogen bonds, generating a two-dimensional network parallel to (001) containing R 4 (4)(28) and R 4 (4)(32) motifs. The 2,9-dimethyl-1,10-phenanthrolinium cations and water mol-ecules reside between the anion layers and are connected to the anions via N-H⋯Owater and Owater-H⋯Ocarbox-yl hydrogen bonds. An intra-molecular O-H⋯O hydrogen bond is also observed in the anion.

Related literature

For related structures, see: Adams & Ramdas (1978 ▶); Mrvos-Sermek et al. (1996) ▶; Sun et al. (2002a ▶,b ▶); Zhu et al. (2002 ▶); Li et al. (2003 ▶; 2006 ▶); Oscar et al. (2008 ▶). For background to mol­ecular recognition and supra­molecular chemistry, see: Batten & Robson (1998 ▶); Juan et al. (2002 ▶); Qiu et al. (2008 ▶). For hydrogen-bond graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H13N2 +·C10H5O8 −·H2O

M = 480.42

Orthorhombic,

a = 7.1135 (8) Å

b = 19.4512 (11) Å

c = 30.800 (2) Å

V = 4261.7 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 223 K

0.35 × 0.20 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.468, T max = 1.000

19580 measured reflections

4346 independent reflections

2278 reflections with I > 2σ(I)

R int = 0.173

Refinement

R[F 2 > 2σ(F 2)] = 0.088

wR(F 2) = 0.272

S = 1.00

4346 reflections

316 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); 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 ▶), PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813030857/lh5664sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030857/lh5664Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813030857/lh5664Isup3.cml

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

C14H13N2+·C10H5O8−·H2O	F(000) = 2000
Mr = 480.42	Dx = 1.498 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2016 reflections
a = 7.1135 (8) Å	θ = 3.4–26.0°
b = 19.4512 (11) Å	µ = 0.12 mm−1
c = 30.800 (2) Å	T = 223 K
V = 4261.7 (6) Å3	Block, colourless
Z = 8	0.35 × 0.20 × 0.15 mm

Rigaku Mercury CCD diffractometer	4346 independent reflections
Radiation source: fine-focus sealed tube	2278 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.173
Detector resolution: 28.5714 pixels mm-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −8→7
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −24→23
Tmin = 0.468, Tmax = 1.000	l = −38→30
19580 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)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.272	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1341P)2] where P = (Fo2 + 2Fc2)/3
4346 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.37 e Å−3
3 restraints	Δρmin = −0.40 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
O1	0.2749 (5)	0.08753 (12)	0.04898 (9)	0.0620 (10)
O1W	0.9045 (6)	0.17263 (15)	0.15048 (10)	0.0773 (11)
H1WA	0.8321	0.1863	0.1316	0.116*
H1WB	0.9732	0.2039	0.1586	0.116*
O2	0.1964 (5)	0.09431 (13)	−0.01923 (9)	0.0687 (11)
H2	0.1669	0.1239	−0.0369	0.103*
O3	0.1453 (4)	0.18081 (12)	−0.07332 (9)	0.0514 (8)
O4	0.1828 (5)	0.29265 (13)	−0.08131 (10)	0.0607 (9)
O5	0.1946 (5)	0.45577 (12)	0.02561 (9)	0.0710 (11)
H5	0.1941	0.4958	0.0340	0.106*
O6	0.1961 (6)	0.43455 (14)	0.09547 (10)	0.0814 (12)
O7	0.1129 (5)	0.29909 (14)	0.15299 (9)	0.0570 (9)
O8	0.4094 (5)	0.32175 (13)	0.13965 (9)	0.0526 (8)
H8	0.4812	0.3203	0.1189	0.079*
N1	0.3348 (5)	0.04067 (14)	0.32309 (11)	0.0418 (8)
H1A	0.3756	0.0820	0.3261	0.050*
N2	0.4269 (5)	0.12165 (13)	0.25335 (10)	0.0387 (8)
C1	0.2968 (6)	0.0044 (2)	0.35906 (14)	0.0505 (11)
C2	0.2298 (6)	−0.0628 (2)	0.35368 (16)	0.0565 (12)
H2B	0.2018	−0.0892	0.3780	0.068*
C3	0.2051 (6)	−0.0901 (2)	0.31345 (16)	0.0540 (12)
H3A	0.1608	−0.1348	0.3107	0.065*
C4	0.2457 (6)	−0.05151 (18)	0.27592 (15)	0.0464 (10)
C5	0.2205 (6)	−0.07699 (19)	0.23280 (16)	0.0510 (11)
H5A	0.1792	−0.1218	0.2285	0.061*
C6	0.2559 (6)	−0.0366 (2)	0.19861 (16)	0.0498 (11)
H6A	0.2354	−0.0539	0.1709	0.060*
C7	0.3240 (6)	0.03194 (17)	0.20314 (13)	0.0403 (9)
C8	0.3644 (6)	0.0762 (2)	0.16851 (14)	0.0488 (10)
H8A	0.3421	0.0621	0.1401	0.059*
C9	0.4360 (6)	0.13951 (19)	0.17649 (13)	0.0473 (10)
H9A	0.4648	0.1686	0.1535	0.057*
C10	0.4672 (6)	0.16161 (16)	0.21950 (12)	0.0416 (10)
C11	0.3565 (5)	0.05828 (17)	0.24523 (12)	0.0382 (9)
C12	0.3122 (5)	0.01557 (17)	0.28188 (13)	0.0397 (10)
C13	0.3258 (8)	0.0376 (2)	0.40228 (16)	0.0716 (15)
H13A	0.3728	0.0834	0.3982	0.107*
H13B	0.4149	0.0113	0.4188	0.107*
H13C	0.2084	0.0394	0.4176	0.107*
C14	0.5500 (6)	0.23092 (17)	0.22864 (14)	0.0505 (11)
H14A	0.5598	0.2375	0.2595	0.076*
H14B	0.4706	0.2659	0.2165	0.076*
H14C	0.6728	0.2338	0.2158	0.076*
C28	0.2079 (5)	0.20013 (15)	0.02367 (12)	0.0357 (9)
C29	0.1912 (5)	0.25062 (16)	−0.00893 (13)	0.0350 (9)
C30	0.1867 (5)	0.31977 (17)	0.00395 (12)	0.0378 (9)
H30A	0.1756	0.3535	−0.0173	0.045*
C31	0.1979 (5)	0.33993 (16)	0.04710 (12)	0.0376 (9)
C32	0.2144 (6)	0.28974 (16)	0.07952 (12)	0.0389 (10)
C33	0.2186 (6)	0.22157 (17)	0.06673 (12)	0.0394 (9)
H33A	0.2291	0.1881	0.0881	0.047*
C34	0.2288 (7)	0.12280 (18)	0.01805 (14)	0.0471 (11)
C35	0.1756 (6)	0.24134 (18)	−0.05812 (13)	0.0411 (10)
C36	0.1967 (6)	0.41454 (17)	0.05910 (13)	0.0457 (11)
C37	0.2376 (7)	0.30587 (16)	0.12675 (13)	0.0428 (10)

	U11	U22	U33	U12	U13	U23
O1	0.119 (3)	0.0212 (13)	0.0460 (18)	0.0077 (14)	−0.0028 (17)	−0.0004 (12)
O1W	0.107 (3)	0.066 (2)	0.058 (2)	−0.0367 (18)	−0.023 (2)	0.0200 (15)
O2	0.131 (3)	0.0301 (14)	0.0452 (18)	0.0046 (16)	−0.0161 (18)	−0.0095 (13)
O3	0.077 (2)	0.0359 (14)	0.0416 (17)	0.0044 (13)	−0.0108 (15)	−0.0086 (12)
O4	0.095 (3)	0.0408 (16)	0.0464 (18)	−0.0027 (14)	−0.0044 (17)	0.0012 (14)
O5	0.149 (4)	0.0180 (13)	0.0458 (19)	−0.0050 (15)	−0.0022 (19)	0.0033 (12)
O6	0.171 (4)	0.0306 (15)	0.0427 (19)	0.0046 (17)	0.000 (2)	−0.0069 (14)
O7	0.075 (2)	0.0492 (17)	0.0465 (18)	−0.0069 (14)	0.0186 (17)	−0.0076 (13)
O8	0.072 (2)	0.0489 (15)	0.0371 (16)	−0.0054 (14)	−0.0002 (15)	−0.0068 (12)
N1	0.054 (2)	0.0278 (15)	0.044 (2)	0.0022 (14)	0.0008 (16)	0.0035 (14)
N2	0.048 (2)	0.0261 (14)	0.0421 (19)	0.0036 (13)	−0.0007 (16)	0.0003 (13)
C1	0.057 (3)	0.042 (2)	0.053 (3)	0.0034 (19)	−0.001 (2)	0.0130 (19)
C2	0.059 (3)	0.040 (2)	0.071 (3)	0.005 (2)	0.006 (3)	0.022 (2)
C3	0.052 (3)	0.033 (2)	0.078 (3)	0.0028 (18)	0.009 (2)	0.009 (2)
C4	0.043 (2)	0.0283 (18)	0.068 (3)	0.0023 (16)	0.001 (2)	0.0029 (19)
C5	0.046 (3)	0.030 (2)	0.077 (3)	−0.0055 (17)	−0.003 (2)	−0.014 (2)
C6	0.051 (3)	0.043 (2)	0.056 (3)	0.0024 (19)	−0.001 (2)	−0.016 (2)
C7	0.045 (2)	0.0305 (19)	0.045 (2)	0.0050 (15)	−0.0001 (19)	−0.0067 (17)
C8	0.054 (3)	0.053 (2)	0.039 (2)	0.008 (2)	−0.002 (2)	−0.0088 (19)
C9	0.056 (3)	0.043 (2)	0.044 (2)	0.0074 (19)	0.005 (2)	0.0094 (18)
C10	0.049 (3)	0.0318 (17)	0.044 (2)	0.0032 (16)	−0.0029 (19)	0.0021 (16)
C11	0.042 (2)	0.0335 (18)	0.039 (2)	0.0060 (16)	0.0018 (18)	−0.0017 (16)
C12	0.040 (2)	0.0285 (18)	0.051 (3)	0.0043 (15)	−0.0003 (19)	−0.0022 (17)
C13	0.109 (5)	0.058 (3)	0.048 (3)	0.000 (3)	−0.002 (3)	0.015 (2)
C14	0.066 (3)	0.034 (2)	0.052 (3)	−0.0008 (19)	0.004 (2)	0.0064 (18)
C28	0.047 (2)	0.0222 (17)	0.038 (2)	−0.0023 (14)	−0.0021 (17)	−0.0018 (15)
C29	0.041 (2)	0.0259 (17)	0.038 (2)	−0.0004 (15)	0.0001 (17)	−0.0025 (15)
C30	0.051 (3)	0.0236 (17)	0.039 (2)	−0.0029 (16)	−0.0039 (18)	0.0019 (15)
C31	0.051 (3)	0.0217 (16)	0.040 (2)	0.0003 (15)	0.0012 (18)	−0.0030 (15)
C32	0.057 (3)	0.0230 (17)	0.037 (2)	−0.0001 (15)	0.0026 (18)	−0.0014 (15)
C33	0.056 (3)	0.0260 (17)	0.036 (2)	−0.0019 (16)	0.0024 (19)	0.0029 (15)
C34	0.071 (3)	0.0235 (18)	0.047 (2)	−0.0011 (17)	0.007 (2)	−0.0012 (18)
C35	0.050 (3)	0.033 (2)	0.040 (2)	0.0016 (16)	−0.0026 (19)	−0.0037 (17)
C36	0.074 (3)	0.0215 (18)	0.041 (2)	0.0029 (17)	0.005 (2)	−0.0009 (17)
C37	0.070 (3)	0.0175 (16)	0.041 (2)	−0.0042 (17)	−0.002 (2)	−0.0005 (16)

O1—C34	1.219 (5)	C6—C7	1.426 (5)
O1W—H1WA	0.8199	C6—H6A	0.9300
O1W—H1WB	0.8200	C7—C8	1.400 (6)
O2—C34	1.296 (5)	C7—C11	1.413 (5)
O2—H2	0.8200	C8—C9	1.356 (5)
O3—C35	1.285 (4)	C8—H8A	0.9300
O4—C35	1.228 (5)	C9—C10	1.410 (5)
O5—C36	1.307 (5)	C9—H9A	0.9300
O5—H5	0.8200	C10—C14	1.498 (5)
O6—C36	1.186 (5)	C11—C12	1.436 (5)
O7—C37	1.208 (5)	C13—H13A	0.9600
O8—C37	1.321 (5)	C13—H13B	0.9600
O8—H8	0.8200	C13—H13C	0.9600
N1—C1	1.341 (5)	C14—H14A	0.9600
N1—C12	1.369 (5)	C14—H14B	0.9600
N1—H1A	0.8600	C14—H14C	0.9600
N2—C10	1.331 (4)	C28—C33	1.392 (5)
N2—C11	1.354 (5)	C28—C29	1.409 (5)
C1—C2	1.401 (6)	C28—C34	1.521 (5)
C1—C13	1.494 (6)	C29—C30	1.403 (5)
C2—C3	1.359 (6)	C29—C35	1.530 (6)
C2—H2B	0.9300	C30—C31	1.388 (5)
C3—C4	1.408 (6)	C30—H30A	0.9300
C3—H3A	0.9300	C31—C32	1.402 (5)
C4—C12	1.400 (5)	C31—C36	1.498 (5)
C4—C5	1.429 (6)	C32—C33	1.384 (5)
C5—C6	1.337 (6)	C32—C37	1.497 (5)
C5—H5A	0.9300	C33—H33A	0.9300
H1WA—O1W—H1WB	110.5	C4—C12—C11	120.7 (4)
C34—O2—H2	109.5	C1—C13—H13A	109.5
C36—O5—H5	109.5	C1—C13—H13B	109.5
C37—O8—H8	109.5	H13A—C13—H13B	109.5
C1—N1—C12	123.7 (3)	C1—C13—H13C	109.5
C1—N1—H1A	118.2	H13A—C13—H13C	109.5
C12—N1—H1A	118.2	H13B—C13—H13C	109.5
C10—N2—C11	117.8 (3)	C10—C14—H14A	109.5
N1—C1—C2	117.5 (4)	C10—C14—H14B	109.5
N1—C1—C13	118.7 (4)	H14A—C14—H14B	109.5
C2—C1—C13	123.8 (4)	C10—C14—H14C	109.5
C3—C2—C1	121.0 (4)	H14A—C14—H14C	109.5
C3—C2—H2B	119.5	H14B—C14—H14C	109.5
C1—C2—H2B	119.5	C33—C28—C29	118.3 (3)
C2—C3—C4	121.0 (4)	C33—C28—C34	113.5 (3)
C2—C3—H3A	119.5	C29—C28—C34	128.0 (3)
C4—C3—H3A	119.5	C30—C29—C28	118.0 (3)
C12—C4—C3	117.3 (4)	C30—C29—C35	113.0 (3)
C12—C4—C5	119.2 (4)	C28—C29—C35	129.0 (3)
C3—C4—C5	123.6 (4)	C31—C30—C29	122.7 (3)
C6—C5—C4	120.3 (3)	C31—C30—H30A	118.6
C6—C5—H5A	119.8	C29—C30—H30A	118.6
C4—C5—H5A	119.8	C30—C31—C32	119.4 (3)
C5—C6—C7	122.4 (4)	C30—C31—C36	120.7 (3)
C5—C6—H6A	118.8	C32—C31—C36	120.0 (3)
C7—C6—H6A	118.8	C33—C32—C31	117.8 (3)
C8—C7—C11	116.3 (3)	C33—C32—C37	118.4 (3)
C8—C7—C6	124.7 (4)	C31—C32—C37	123.7 (3)
C11—C7—C6	119.0 (4)	C32—C33—C28	123.9 (3)
C9—C8—C7	119.8 (4)	C32—C33—H33A	118.1
C9—C8—H8A	120.1	C28—C33—H33A	118.1
C7—C8—H8A	120.1	O1—C34—O2	120.0 (3)
C8—C9—C10	120.4 (4)	O1—C34—C28	119.6 (3)
C8—C9—H9A	119.8	O2—C34—C28	120.4 (3)
C10—C9—H9A	119.8	O4—C35—O3	122.7 (4)
N2—C10—C9	121.6 (3)	O4—C35—C29	118.5 (3)
N2—C10—C14	117.6 (3)	O3—C35—C29	118.7 (3)
C9—C10—C14	120.8 (3)	O6—C36—O5	123.0 (3)
N2—C11—C7	124.1 (3)	O6—C36—C31	123.4 (3)
N2—C11—C12	117.6 (3)	O5—C36—C31	113.6 (3)
C7—C11—C12	118.4 (3)	O7—C37—O8	120.2 (4)
N1—C12—C4	119.6 (3)	O7—C37—C32	123.1 (4)
N1—C12—C11	119.8 (3)	O8—C37—C32	116.3 (4)
C12—N1—C1—C2	−0.2 (6)	C7—C11—C12—C4	2.5 (6)
C12—N1—C1—C13	−179.6 (4)	C33—C28—C29—C30	0.1 (6)
N1—C1—C2—C3	0.2 (7)	C34—C28—C29—C30	−175.6 (4)
C13—C1—C2—C3	179.6 (4)	C33—C28—C29—C35	−179.5 (4)
C1—C2—C3—C4	−0.2 (7)	C34—C28—C29—C35	4.8 (7)
C2—C3—C4—C12	0.1 (6)	C28—C29—C30—C31	0.0 (6)
C2—C3—C4—C5	−179.2 (4)	C35—C29—C30—C31	179.7 (4)
C12—C4—C5—C6	−1.6 (6)	C29—C30—C31—C32	0.0 (6)
C3—C4—C5—C6	177.7 (4)	C29—C30—C31—C36	178.6 (4)
C4—C5—C6—C7	1.7 (7)	C30—C31—C32—C33	−0.1 (6)
C5—C6—C7—C8	179.6 (4)	C36—C31—C32—C33	−178.7 (4)
C5—C6—C7—C11	0.4 (6)	C30—C31—C32—C37	176.7 (4)
C11—C7—C8—C9	1.9 (6)	C36—C31—C32—C37	−2.0 (6)
C6—C7—C8—C9	−177.3 (4)	C31—C32—C33—C28	0.2 (6)
C7—C8—C9—C10	−1.1 (6)	C37—C32—C33—C28	−176.7 (4)
C11—N2—C10—C9	0.7 (6)	C29—C28—C33—C32	−0.2 (6)
C11—N2—C10—C14	−178.3 (3)	C34—C28—C33—C32	176.1 (4)
C8—C9—C10—N2	−0.3 (6)	C33—C28—C34—O1	−8.9 (6)
C8—C9—C10—C14	178.7 (4)	C29—C28—C34—O1	167.0 (4)
C10—N2—C11—C7	0.3 (6)	C33—C28—C34—O2	170.5 (4)
C10—N2—C11—C12	−179.6 (3)	C29—C28—C34—O2	−13.6 (7)
C8—C7—C11—N2	−1.6 (6)	C30—C29—C35—O4	8.2 (5)
C6—C7—C11—N2	177.7 (3)	C28—C29—C35—O4	−172.2 (4)
C8—C7—C11—C12	178.3 (3)	C30—C29—C35—O3	−168.0 (3)
C6—C7—C11—C12	−2.5 (6)	C28—C29—C35—O3	11.6 (6)
C1—N1—C12—C4	0.1 (6)	C30—C31—C36—O6	175.9 (5)
C1—N1—C12—C11	180.0 (3)	C32—C31—C36—O6	−5.4 (7)
C3—C4—C12—N1	−0.1 (6)	C30—C31—C36—O5	−3.5 (6)
C5—C4—C12—N1	179.3 (4)	C32—C31—C36—O5	175.2 (4)
C3—C4—C12—C11	−179.9 (4)	C33—C32—C37—O7	−77.6 (5)
C5—C4—C12—C11	−0.6 (6)	C31—C32—C37—O7	105.7 (5)
N2—C11—C12—N1	2.6 (5)	C33—C32—C37—O8	95.8 (4)
C7—C11—C12—N1	−177.3 (3)	C31—C32—C37—O8	−81.0 (5)
N2—C11—C12—C4	−177.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.58	2.395 (4)	171
O5—H5···O1i	0.82	1.86	2.671 (3)	172
O8—H8···O3ii	0.82	1.82	2.645 (4)	178
N1—H1A···O1Wiii	0.86	1.92	2.738 (4)	160
O1W—H1WA···O4ii	0.82	1.92	2.735 (4)	171
O1W—H1WB···O7iv	0.82	2.11	2.873 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	1.58	2.395 (4)	171
O5—H5⋯O1i	0.82	1.86	2.671 (3)	172
O8—H8⋯O3ii	0.82	1.82	2.645 (4)	178
N1—H1A⋯O1W iii	0.86	1.92	2.738 (4)	160
O1W—H1WA⋯O4ii	0.82	1.92	2.735 (4)	171
O1W—H1WB⋯O7iv	0.82	2.11	2.873 (4)	155

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