5-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetra-hydropyrimidin-5-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrim-idine-2,4(3H,5H)-dione 3.5-hydrate.

The title compound, C19H19N5O5·3.5H2O, crystallizes with 3.5 mol-ecules of water in the asymmetric unit, one of which lies on a mirror plane. One of the water mol-ecules links the mol-ecules, forming centrosymmetric dimers. These dimers are then linked through further N-H⋯O and O-H⋯O hydrogen bonding, leading to the observed three-dimensional structure.

Related literature

Many chromene derivatives occur in natural products, see: Hatakeyama et al. (1988 ▶). For the biological activity of functionalized chromenes, see: Brooks (1998 ▶); Valenti et al. (1993 ▶); Tang et al. (2007 ▶). For the use of 6-amino-uracil derivatives as precursors in the synthesis of biologically significant fused uracils, see: Shaw (1996 ▶). The fusion of a chromene unit to the uracil ring is found to increase the biological activity, see: Sabry et al. (2011 ▶).

Experimental

Crystal data

C19H19N5O5·3.5H2O

M = 460.45

Monoclinic,

a = 29.993 (4) Å

b = 7.9105 (6) Å

c = 21.458 (3) Å

β = 119.860 (16)°

V = 4415.3 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.32 × 0.12 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.93, T max = 1.00

9327 measured reflections

4554 independent reflections

2538 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.137

S = 0.98

4554 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: OLEX.SOLVE (Bourhis et al., 2013 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013986/go2089sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013986/go2089Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013986/go2089Isup3.cdx

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

C19H19N5O5·3.5H2O	Z = 8
Mr = 460.45	F(000) = 1944
Monoclinic, C2/c	Dx = 1.385 Mg m−3
a = 29.993 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.9105 (6) Å	µ = 0.11 mm−1
c = 21.458 (3) Å	T = 298 K
β = 119.860 (16)°	Block, clear colourless
V = 4415.3 (10) Å3	0.32 × 0.12 × 0.06 mm

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer	4554 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2538 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 16.1511 pixels mm-1	θmax = 26.5°, θmin = 2.8°
ω scans	h = −37→36
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −9→5
Tmin = 0.93, Tmax = 1.00	l = −26→26
9327 measured reflections

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.037P)2] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.060	(Δ/σ)max = 0.001
wR(F2) = 0.137	Δρmax = 0.24 e Å−3
S = 0.98	Δρmin = −0.25 e Å−3
4554 reflections	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
308 parameters	Extinction coefficient: 0.0029 (2)
0 restraints

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
O1	0.20391 (8)	1.0426 (2)	0.41093 (10)	0.0553 (6)
O2	0.36262 (7)	0.8244 (2)	0.56168 (9)	0.0444 (5)
O3	0.51160 (8)	0.8412 (3)	0.44642 (10)	0.0579 (6)
O4	0.34405 (7)	0.6704 (2)	0.34016 (8)	0.0442 (5)
O5	0.24740 (6)	0.5527 (2)	0.34356 (8)	0.0378 (5)
N1	0.28226 (8)	0.9305 (3)	0.48757 (10)	0.0350 (5)
N2	0.22732 (8)	0.8001 (3)	0.37727 (10)	0.0374 (6)
N3	0.42861 (9)	0.7489 (3)	0.39256 (11)	0.0399 (6)
N4	0.48358 (8)	0.7140 (3)	0.51612 (10)	0.0359 (6)
N6	0.45814 (8)	0.5830 (3)	0.58939 (10)	0.0469 (7)
H6A	0.4358	0.5337	0.5972	0.056*
H6B	0.4891	0.5975	0.6240	0.056*
C1	0.23592 (11)	0.9317 (4)	0.42411 (14)	0.0398 (7)
C2	0.26390 (10)	0.6756 (3)	0.39378 (12)	0.0316 (6)
C3	0.31020 (9)	0.6787 (3)	0.45432 (12)	0.0289 (6)
C4	0.32143 (10)	0.8121 (3)	0.50451 (12)	0.0323 (6)
C5	0.47635 (11)	0.7709 (3)	0.45087 (14)	0.0394 (7)
C6	0.44477 (10)	0.6371 (3)	0.52362 (12)	0.0307 (6)
C7	0.39607 (9)	0.6201 (3)	0.46424 (11)	0.0284 (6)
C8	0.38635 (11)	0.6784 (3)	0.39612 (12)	0.0338 (6)
C9	0.35107 (9)	0.5470 (3)	0.46939 (11)	0.0297 (6)
H9	0.3645	0.5081	0.5189	0.036*
C10	0.32640 (10)	0.3965 (3)	0.42059 (12)	0.0294 (6)
C11	0.27754 (10)	0.4047 (3)	0.36074 (12)	0.0307 (6)
C12	0.25456 (11)	0.2707 (3)	0.31460 (13)	0.0418 (7)
H12	0.2217	0.2811	0.2751	0.050*
C13	0.28154 (13)	0.1200 (4)	0.32827 (14)	0.0484 (8)
H13	0.2669	0.0284	0.2975	0.058*
C14	0.33003 (12)	0.1059 (4)	0.38743 (15)	0.0466 (8)
H14	0.3480	0.0047	0.3966	0.056*
C15	0.35207 (11)	0.2422 (3)	0.43328 (13)	0.0384 (7)
H15	0.3846	0.2306	0.4733	0.046*
C16	0.17779 (11)	0.7988 (4)	0.30914 (13)	0.0573 (9)
H16A	0.1795	0.7193	0.2766	0.086*
H16B	0.1709	0.9096	0.2881	0.086*
H16C	0.1508	0.7667	0.3184	0.086*
C17	0.29347 (11)	1.0725 (3)	0.53773 (14)	0.0498 (8)
H17A	0.3180	1.0370	0.5856	0.075*
H17B	0.2623	1.1077	0.5363	0.075*
H17C	0.3074	1.1651	0.5240	0.075*
C18	0.53408 (11)	0.7462 (4)	0.57937 (14)	0.0517 (8)
H18A	0.5296	0.8003	0.6159	0.078*
H18B	0.5538	0.8184	0.5662	0.078*
H18C	0.5519	0.6410	0.5974	0.078*
C19	0.41982 (13)	0.8013 (4)	0.32181 (13)	0.0627 (10)
H19A	0.3910	0.7404	0.2851	0.094*
H19B	0.4499	0.7775	0.3183	0.094*
H19C	0.4128	0.9204	0.3157	0.094*
O6W	0.40247 (8)	1.3900 (3)	0.65089 (12)	0.0588 (6)
H6WA	0.3707	1.3937	0.6386	0.088*
H6WB	0.4104	1.2891	0.6470	0.088*
O7W	0.43622 (9)	1.0753 (3)	0.62611 (10)	0.0552 (6)
H7WA	0.4531	1.1006	0.6055	0.083*
H7WB	0.4155	0.9949	0.6036	0.083*
O8W	0.54970 (10)	0.6130 (4)	0.72984 (11)	0.0811 (8)
H8WA	0.5350	0.6963	0.7373	0.122*
H8WB	0.5579	0.5401	0.7631	0.122*
O9W	0.5000	0.8957 (5)	0.7500	0.1228 (18)
H9W	0.4827	0.9612	0.7146	0.184*

	U11	U22	U33	U12	U13	U23
O1	0.0445 (13)	0.0462 (12)	0.0788 (14)	0.0148 (11)	0.0333 (12)	0.0016 (11)
O2	0.0366 (12)	0.0490 (12)	0.0398 (10)	−0.0016 (10)	0.0131 (9)	−0.0123 (9)
O3	0.0455 (14)	0.0749 (15)	0.0645 (13)	−0.0121 (12)	0.0357 (11)	0.0036 (11)
O4	0.0348 (12)	0.0556 (12)	0.0329 (9)	−0.0022 (10)	0.0098 (9)	0.0056 (9)
O5	0.0291 (10)	0.0419 (11)	0.0321 (9)	−0.0001 (9)	0.0075 (8)	−0.0069 (8)
N1	0.0314 (13)	0.0298 (12)	0.0480 (12)	0.0017 (11)	0.0229 (11)	−0.0050 (10)
N2	0.0227 (12)	0.0441 (14)	0.0399 (12)	0.0061 (11)	0.0114 (10)	−0.0007 (11)
N3	0.0388 (15)	0.0482 (14)	0.0377 (12)	−0.0051 (12)	0.0229 (11)	0.0031 (11)
N4	0.0251 (13)	0.0444 (13)	0.0371 (11)	0.0000 (11)	0.0146 (10)	0.0003 (10)
N6	0.0248 (13)	0.0726 (17)	0.0309 (11)	−0.0112 (13)	0.0044 (10)	0.0060 (11)
C1	0.0354 (16)	0.0398 (16)	0.0509 (16)	0.0040 (14)	0.0266 (14)	0.0040 (14)
C2	0.0241 (14)	0.0342 (14)	0.0349 (13)	−0.0023 (12)	0.0134 (12)	−0.0023 (11)
C3	0.0232 (14)	0.0298 (14)	0.0326 (12)	−0.0032 (11)	0.0131 (11)	−0.0041 (11)
C4	0.0302 (15)	0.0366 (15)	0.0333 (13)	−0.0059 (13)	0.0181 (12)	−0.0033 (11)
C5	0.0329 (17)	0.0404 (16)	0.0521 (17)	0.0039 (14)	0.0268 (14)	0.0025 (14)
C6	0.0263 (14)	0.0345 (14)	0.0327 (13)	0.0023 (12)	0.0158 (11)	−0.0005 (12)
C7	0.0222 (14)	0.0303 (14)	0.0312 (12)	0.0054 (11)	0.0121 (11)	0.0025 (11)
C8	0.0340 (16)	0.0348 (15)	0.0313 (13)	0.0019 (13)	0.0153 (12)	−0.0010 (11)
C9	0.0246 (14)	0.0342 (14)	0.0260 (12)	−0.0001 (12)	0.0094 (11)	−0.0015 (11)
C10	0.0302 (15)	0.0307 (14)	0.0333 (13)	−0.0038 (12)	0.0204 (12)	−0.0032 (11)
C11	0.0312 (15)	0.0337 (14)	0.0284 (12)	0.0008 (12)	0.0157 (11)	−0.0024 (11)
C12	0.0442 (18)	0.0456 (17)	0.0338 (14)	−0.0154 (15)	0.0182 (13)	−0.0104 (13)
C13	0.065 (2)	0.0394 (17)	0.0512 (17)	−0.0101 (17)	0.0370 (17)	−0.0134 (14)
C14	0.060 (2)	0.0339 (16)	0.0600 (18)	−0.0009 (15)	0.0404 (17)	−0.0045 (14)
C15	0.0395 (17)	0.0361 (15)	0.0443 (15)	0.0054 (14)	0.0243 (13)	0.0037 (13)
C16	0.0357 (19)	0.069 (2)	0.0505 (17)	0.0128 (17)	0.0093 (15)	−0.0031 (16)
C17	0.057 (2)	0.0424 (17)	0.0625 (18)	−0.0016 (16)	0.0394 (17)	−0.0147 (15)
C18	0.0275 (16)	0.069 (2)	0.0514 (17)	−0.0142 (16)	0.0140 (14)	−0.0073 (16)
C19	0.073 (3)	0.080 (2)	0.0452 (16)	−0.018 (2)	0.0366 (17)	0.0045 (17)
O6W	0.0444 (14)	0.0660 (15)	0.0617 (13)	−0.0016 (12)	0.0231 (12)	−0.0009 (12)
O7W	0.0469 (15)	0.0627 (15)	0.0571 (12)	−0.0127 (12)	0.0267 (11)	−0.0025 (11)
O8W	0.0576 (17)	0.114 (2)	0.0506 (13)	0.0053 (16)	0.0110 (12)	0.0133 (14)
O9W	0.157 (4)	0.076 (3)	0.060 (2)	0.000	−0.002 (2)	0.000

O1—C1	1.225 (3)	C10—C11	1.388 (3)
O2—C4	1.238 (3)	C10—C15	1.396 (3)
O3—C5	1.240 (3)	C11—C12	1.378 (3)
O4—C8	1.240 (3)	C12—H12	0.9300
O5—C2	1.349 (3)	C12—C13	1.388 (4)
O5—C11	1.411 (3)	C13—H13	0.9300
N1—C1	1.379 (3)	C13—C14	1.379 (4)
N1—C4	1.401 (3)	C14—H14	0.9300
N1—C17	1.474 (3)	C14—C15	1.385 (3)
N2—C1	1.379 (3)	C15—H15	0.9300
N2—C2	1.383 (3)	C16—H16A	0.9600
N2—C16	1.477 (3)	C16—H16B	0.9600
N3—C5	1.365 (3)	C16—H16C	0.9600
N3—C8	1.421 (3)	C17—H17A	0.9600
N3—C19	1.465 (3)	C17—H17B	0.9600
N4—C5	1.381 (3)	C17—H17C	0.9600
N4—C6	1.392 (3)	C18—H18A	0.9600
N4—C18	1.468 (3)	C18—H18B	0.9600
N6—H6A	0.8600	C18—H18C	0.9600
N6—H6B	0.8600	C19—H19A	0.9600
N6—C6	1.331 (3)	C19—H19B	0.9600
C2—C3	1.349 (3)	C19—H19C	0.9600
C3—C4	1.424 (3)	O6W—H6WA	0.8524
C3—C9	1.516 (3)	O6W—H6WB	0.8486
C6—C7	1.386 (3)	O7W—H7WA	0.8449
C7—C8	1.418 (3)	O7W—H7WB	0.8516
C7—C9	1.522 (3)	O8W—H8WA	0.8524
C9—H9	0.9800	O8W—H8WB	0.8519
C9—C10	1.513 (3)	O9W—H9W	0.8500
C2—O5—C11	117.17 (18)	C11—C10—C9	122.1 (2)
C1—N1—C4	124.3 (2)	C11—C10—C15	116.6 (2)
C1—N1—C17	117.8 (2)	C15—C10—C9	121.4 (2)
C4—N1—C17	117.6 (2)	C10—C11—O5	121.6 (2)
C1—N2—C2	121.0 (2)	C12—C11—O5	115.1 (2)
C1—N2—C16	117.2 (2)	C12—C11—C10	123.3 (2)
C2—N2—C16	121.8 (2)	C11—C12—H12	120.7
C5—N3—C8	123.9 (2)	C11—C12—C13	118.6 (3)
C5—N3—C19	118.6 (2)	C13—C12—H12	120.7
C8—N3—C19	117.5 (2)	C12—C13—H13	120.0
C5—N4—C6	122.8 (2)	C14—C13—C12	120.0 (3)
C5—N4—C18	116.7 (2)	C14—C13—H13	120.0
C6—N4—C18	120.4 (2)	C13—C14—H14	119.9
H6A—N6—H6B	120.0	C13—C14—C15	120.2 (3)
C6—N6—H6A	120.0	C15—C14—H14	119.9
C6—N6—H6B	120.0	C10—C15—H15	119.3
O1—C1—N1	121.4 (3)	C14—C15—C10	121.3 (3)
O1—C1—N2	122.1 (3)	C14—C15—H15	119.3
N1—C1—N2	116.4 (2)	N2—C16—H16A	109.5
O5—C2—N2	112.3 (2)	N2—C16—H16B	109.5
O5—C2—C3	125.1 (2)	N2—C16—H16C	109.5
C3—C2—N2	122.6 (2)	H16A—C16—H16B	109.5
C2—C3—C4	119.0 (2)	H16A—C16—H16C	109.5
C2—C3—C9	121.9 (2)	H16B—C16—H16C	109.5
C4—C3—C9	119.1 (2)	N1—C17—H17A	109.5
O2—C4—N1	119.9 (2)	N1—C17—H17B	109.5
O2—C4—C3	123.5 (2)	N1—C17—H17C	109.5
N1—C4—C3	116.6 (2)	H17A—C17—H17B	109.5
O3—C5—N3	122.2 (2)	H17A—C17—H17C	109.5
O3—C5—N4	121.0 (3)	H17B—C17—H17C	109.5
N3—C5—N4	116.8 (2)	N4—C18—H18A	109.5
N6—C6—N4	115.8 (2)	N4—C18—H18B	109.5
N6—C6—C7	124.5 (2)	N4—C18—H18C	109.5
C7—C6—N4	119.7 (2)	H18A—C18—H18B	109.5
C6—C7—C8	119.9 (2)	H18A—C18—H18C	109.5
C6—C7—C9	122.5 (2)	H18B—C18—H18C	109.5
C8—C7—C9	117.6 (2)	N3—C19—H19A	109.5
O4—C8—N3	118.5 (2)	N3—C19—H19B	109.5
O4—C8—C7	124.6 (3)	N3—C19—H19C	109.5
C7—C8—N3	116.9 (2)	H19A—C19—H19B	109.5
C3—C9—C7	112.1 (2)	H19A—C19—H19C	109.5
C3—C9—H9	107.4	H19B—C19—H19C	109.5
C7—C9—H9	107.4	H6WA—O6W—H6WB	109.1
C10—C9—C3	109.15 (19)	H7WA—O7W—H7WB	109.8
C10—C9—C7	113.24 (19)	H8WA—O8W—H8WB	109.1
C10—C9—H9	107.4
O5—C2—C3—C4	−176.7 (2)	C7—C9—C10—C15	68.9 (3)
O5—C2—C3—C9	5.0 (4)	C8—N3—C5—O3	−176.0 (2)
O5—C11—C12—C13	−179.4 (2)	C8—N3—C5—N4	2.7 (4)
N2—C2—C3—C4	2.1 (4)	C8—C7—C9—C3	−65.0 (3)
N2—C2—C3—C9	−176.2 (2)	C8—C7—C9—C10	59.0 (3)
N4—C6—C7—C8	1.1 (4)	C9—C3—C4—O2	−2.4 (4)
N4—C6—C7—C9	−176.3 (2)	C9—C3—C4—N1	179.7 (2)
N6—C6—C7—C8	−178.3 (2)	C9—C7—C8—O4	−1.7 (4)
N6—C6—C7—C9	4.3 (4)	C9—C7—C8—N3	179.0 (2)
C1—N1—C4—O2	177.3 (2)	C9—C10—C11—O5	−2.3 (4)
C1—N1—C4—C3	−4.7 (4)	C9—C10—C11—C12	178.7 (2)
C1—N2—C2—O5	176.3 (2)	C9—C10—C15—C14	−178.2 (2)
C1—N2—C2—C3	−2.6 (4)	C10—C11—C12—C13	−0.2 (4)
C2—O5—C11—C10	−11.2 (3)	C11—O5—C2—N2	−168.9 (2)
C2—O5—C11—C12	167.9 (2)	C11—O5—C2—C3	10.0 (4)
C2—N2—C1—O1	−179.3 (2)	C11—C10—C15—C14	1.2 (4)
C2—N2—C1—N1	−0.5 (4)	C11—C12—C13—C14	0.7 (4)
C2—C3—C4—O2	179.3 (2)	C12—C13—C14—C15	−0.2 (4)
C2—C3—C4—N1	1.4 (4)	C13—C14—C15—C10	−0.8 (4)
C2—C3—C9—C7	109.6 (3)	C15—C10—C11—O5	178.3 (2)
C2—C3—C9—C10	−16.7 (3)	C15—C10—C11—C12	−0.7 (4)
C3—C9—C10—C11	15.2 (3)	C16—N2—C1—O1	0.9 (4)
C3—C9—C10—C15	−165.5 (2)	C16—N2—C1—N1	179.7 (2)
C4—N1—C1—O1	−176.9 (2)	C16—N2—C2—O5	−4.0 (3)
C4—N1—C1—N2	4.3 (4)	C16—N2—C2—C3	177.1 (2)
C4—C3—C9—C7	−68.7 (3)	C17—N1—C1—O1	−3.3 (4)
C4—C3—C9—C10	165.0 (2)	C17—N1—C1—N2	177.9 (2)
C5—N3—C8—O4	177.1 (2)	C17—N1—C4—O2	3.7 (4)
C5—N3—C8—C7	−3.5 (4)	C17—N1—C4—C3	−178.4 (2)
C5—N4—C6—N6	177.5 (2)	C18—N4—C5—O3	2.0 (4)
C5—N4—C6—C7	−2.0 (4)	C18—N4—C5—N3	−176.7 (2)
C6—N4—C5—O3	178.9 (3)	C18—N4—C6—N6	−5.8 (4)
C6—N4—C5—N3	0.1 (4)	C18—N4—C6—C7	174.7 (2)
C6—C7—C8—O4	−179.2 (2)	C19—N3—C5—O3	3.7 (4)
C6—C7—C8—N3	1.5 (3)	C19—N3—C5—N4	−177.6 (2)
C6—C7—C9—C3	112.4 (3)	C19—N3—C8—O4	−2.5 (4)
C6—C7—C9—C10	−123.6 (2)	C19—N3—C8—C7	176.8 (2)
C7—C9—C10—C11	−110.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O6Wi	0.86	2.18	3.009 (3)	161
N6—H6B···O8W	0.86	2.09	2.905 (3)	158
O6W—H6WA···O1ii	0.85	2.01	2.830 (3)	162
O6W—H6WB···O7W	0.85	2.00	2.835 (3)	167
O7W—H7WA···O3iii	0.84	1.94	2.781 (3)	177
O7W—H7WB···O2	0.85	1.93	2.773 (3)	170
O8W—H8WA···O9W	0.85	1.99	2.838 (4)	177
O8W—H8WB···O6Wiv	0.85	2.01	2.840 (3)	164
O9W—H9W···O7W	0.85	1.93	2.772 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯O6W i	0.86	2.18	3.009 (3)	161
N6—H6B⋯O8W	0.86	2.09	2.905 (3)	158
O6W—H6WA⋯O1ii	0.85	2.01	2.830 (3)	162
O6W—H6WB⋯O7W	0.85	2.00	2.835 (3)	167
O7W—H7WA⋯O3iii	0.84	1.94	2.781 (3)	177
O7W—H7WB⋯O2	0.85	1.93	2.773 (3)	170
O8W—H8WA⋯O9W	0.85	1.99	2.838 (4)	177
O8W—H8WB⋯O6W iv	0.85	2.01	2.840 (3)	164
O9W—H9W⋯O7W	0.85	1.93	2.772 (3)	170

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