Raltegravir monohydrate.

THE HYDRATED TITLE COMPOUND [SYSTEMATIC NAME: N-(4-fluoro-benz-yl)-5-hy-droxy-1-methyl-2-{1-methyl-1-[(5-methyl-1,3,4-oxa-diazol-2-ylcarbon-yl)amino]-eth-yl}-6-oxo-1,6-di-hydro-pyrimidine-4-carb-oxamide monohydrate], C20H21FN6O5·H2O, is recognised as the first HIV integrase inhibitor. In the mol-ecule, the dihedral angles between the mean planes of the pyrimidine ring and the phenyl and oxa-diazole rings are 72.0 (1) and 61.8 (3)°, respectively. The mean plane of the oxa-diazole ring is twisted by 15.6 (3)° from that of the benzene ring, while the mean plane of amide group bound to the oxadiaole ring is twisted by 18.8 (3)° from its mean plane. Intra-molecular O-H⋯O and C-H⋯N hydrogen bonds are observed in the mol-ecule. The crystal packing features O-H⋯O hydrogen bonds, which include bifurcated O-H⋯(O,O) hydrogen bonds from one H atom of the water mol-ecule. In addition, N-H⋯O hydrogen bonds are observed involving the two amide groups. These inter-actions link the mol-ecules into chains along [010].

Related literature

For general background to and pharmacological properties of Raltegravir, see: Burger (2010 ▶); Cocohoba & Dong (2008 ▶); Croxtall & Keam (2009 ▶); Evering & Markowitz (2008 ▶); Hicks & Gulick (2009 ▶); Savarino (2006 ▶); Temesgen & Siraj (2008 ▶). For related structures, see: Fun et al. (2011 ▶); Shang et al. (2012 ▶); Shang, Ha et al. (2011 ▶); Shang, Qi et al. (2011 ▶); Thiruvalluvar et al. (2007 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H21FN6O5·H2O

M = 462.44

Triclinic,

a = 8.3860 (6) Å

b = 11.8610 (9) Å

c = 12.1102 (9) Å

α = 110.481 (7)°

β = 108.093 (7)°

γ = 92.329 (6)°

V = 1057.44 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 173 K

0.44 × 0.32 × 0.26 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.890, T max = 1.000

12734 measured reflections

7007 independent reflections

5042 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.206

S = 1.03

7007 reflections

306 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813029747/sj5363sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029747/sj5363Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813029747/sj5363Isup3.cml

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

C20H21FN6O5·H2O	Z = 2
Mr = 462.44	F(000) = 484
Triclinic, P1	Dx = 1.452 Mg m−3
a = 8.3860 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.8610 (9) Å	Cell parameters from 3215 reflections
c = 12.1102 (9) Å	θ = 3.0–32.9°
α = 110.481 (7)°	µ = 0.12 mm−1
β = 108.093 (7)°	T = 173 K
γ = 92.329 (6)°	Irregular, colourless
V = 1057.44 (15) Å3	0.44 × 0.32 × 0.26 mm

Agilent Xcalibur (Eos, Gemini) diffractometer	7007 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5042 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.025
ω scans	θmax = 33.0°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −12→12
Tmin = 0.890, Tmax = 1.000	k = −14→17
12734 measured reflections	l = −17→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.206	w = 1/[σ2(Fo2) + (0.0974P)2 + 0.6433P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
7007 reflections	Δρmax = 0.78 e Å−3
306 parameters	Δρmin = −0.39 e Å−3
0 restraints

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
F1	1.1554 (2)	0.33688 (15)	1.31637 (13)	0.0578 (4)
O1	0.7785 (2)	0.36533 (14)	0.09901 (14)	0.0412 (4)
O2	0.7121 (2)	0.44719 (13)	0.32679 (14)	0.0398 (4)
O3	0.50567 (19)	−0.13326 (13)	0.34626 (15)	0.0355 (3)
O4	0.76855 (19)	−0.16476 (12)	0.52110 (14)	0.0320 (3)
H4	0.8570	−0.1629	0.5789	0.048*
O5	1.04993 (19)	−0.05743 (13)	0.70762 (13)	0.0315 (3)
N1	0.7540 (2)	0.26143 (14)	0.33868 (14)	0.0273 (3)
H1	0.7661	0.1875	0.2950	0.033*
N2	0.62443 (18)	0.06543 (13)	0.40189 (13)	0.0221 (3)
N3	0.87875 (19)	0.15547 (13)	0.57317 (13)	0.0228 (3)
N4	1.1487 (2)	0.14234 (15)	0.76091 (14)	0.0282 (3)
H4A	1.1334	0.2069	0.7414	0.034*
N5	0.7269 (2)	0.17737 (16)	0.08576 (16)	0.0347 (4)
N6	0.7475 (3)	0.17321 (18)	−0.02828 (18)	0.0427 (5)
C1	0.7546 (2)	0.28635 (15)	0.46715 (16)	0.0238 (3)
C2	0.7531 (2)	0.16307 (15)	0.48264 (15)	0.0211 (3)
C3	0.6221 (2)	−0.04688 (16)	0.41474 (17)	0.0245 (3)
C4	0.7677 (2)	−0.05480 (15)	0.51363 (16)	0.0237 (3)
C5	0.8866 (2)	0.04642 (15)	0.58924 (15)	0.0222 (3)
C6	1.0360 (2)	0.04108 (16)	0.69173 (16)	0.0247 (3)
C7	1.2983 (3)	0.1521 (2)	0.86874 (18)	0.0331 (4)
H7A	1.3951	0.2062	0.8731	0.040*
H7B	1.3306	0.0705	0.8568	0.040*
C8	1.2642 (2)	0.20230 (17)	0.99030 (17)	0.0271 (4)
C9	1.1883 (3)	0.12534 (17)	1.02977 (18)	0.0304 (4)
H9	1.1619	0.0401	0.9810	0.036*
C10	1.1498 (3)	0.17008 (19)	1.13923 (19)	0.0333 (4)
H10	1.0959	0.1170	1.1652	0.040*
C11	1.1919 (3)	0.2928 (2)	1.20832 (18)	0.0370 (5)
C12	1.2710 (4)	0.3723 (2)	1.1741 (2)	0.0527 (7)
H12	1.3007	0.4570	1.2252	0.063*
C13	1.3067 (4)	0.3264 (2)	1.0637 (2)	0.0438 (5)
H13	1.3604	0.3800	1.0383	0.053*
C14	0.7364 (3)	0.34282 (17)	0.28320 (18)	0.0297 (4)
C15	0.7465 (3)	0.28953 (17)	0.15403 (18)	0.0312 (4)
C16	0.7766 (3)	0.2857 (2)	−0.0153 (2)	0.0388 (5)
C17	0.8092 (5)	0.3338 (3)	−0.1049 (3)	0.0595 (7)
H17A	0.7148	0.3741	−0.1349	0.089*
H17B	0.8190	0.2664	−0.1763	0.089*
H17C	0.9153	0.3928	−0.0628	0.089*
C18	0.6015 (3)	0.34431 (18)	0.4921 (2)	0.0330 (4)
H18A	0.6208	0.4311	0.5063	0.049*
H18B	0.5885	0.3358	0.5666	0.049*
H18C	0.4979	0.3029	0.4192	0.049*
C19	0.9184 (3)	0.37382 (17)	0.56034 (19)	0.0319 (4)
H19A	1.0168	0.3375	0.5464	0.048*
H19B	0.9234	0.3889	0.6464	0.048*
H19C	0.9198	0.4512	0.5480	0.048*
C20	0.4769 (2)	0.06994 (17)	0.29878 (17)	0.0276 (4)
H20A	0.3837	0.0935	0.3300	0.041*
H20B	0.4396	−0.0107	0.2302	0.041*
H20C	0.5098	0.1300	0.2677	0.041*
O1W	0.6377 (4)	0.63744 (18)	0.2332 (2)	0.0697 (7)
H1WA	0.6255	0.6900	0.2977	0.105*
H1WB	0.6630	0.5741	0.2478	0.105*

	U11	U22	U33	U12	U13	U23
F1	0.0781 (11)	0.0643 (10)	0.0310 (7)	0.0282 (8)	0.0259 (7)	0.0103 (7)
O1	0.0611 (10)	0.0302 (7)	0.0326 (7)	0.0038 (7)	0.0138 (7)	0.0148 (6)
O2	0.0591 (10)	0.0230 (7)	0.0362 (8)	0.0116 (6)	0.0114 (7)	0.0141 (6)
O3	0.0303 (7)	0.0291 (7)	0.0434 (8)	0.0000 (5)	0.0075 (6)	0.0146 (6)
O4	0.0379 (7)	0.0250 (6)	0.0390 (8)	0.0094 (5)	0.0142 (6)	0.0177 (6)
O5	0.0391 (7)	0.0331 (7)	0.0319 (7)	0.0168 (6)	0.0152 (6)	0.0199 (6)
N1	0.0373 (8)	0.0221 (7)	0.0258 (7)	0.0095 (6)	0.0117 (6)	0.0117 (6)
N2	0.0222 (6)	0.0234 (7)	0.0214 (6)	0.0066 (5)	0.0083 (5)	0.0087 (5)
N3	0.0263 (7)	0.0235 (7)	0.0208 (6)	0.0081 (5)	0.0089 (5)	0.0099 (5)
N4	0.0308 (8)	0.0335 (8)	0.0224 (7)	0.0104 (6)	0.0076 (6)	0.0139 (6)
N5	0.0431 (10)	0.0295 (8)	0.0276 (8)	0.0060 (7)	0.0050 (7)	0.0127 (6)
N6	0.0521 (11)	0.0388 (10)	0.0306 (9)	0.0076 (8)	0.0060 (8)	0.0128 (7)
C1	0.0277 (8)	0.0210 (7)	0.0231 (7)	0.0080 (6)	0.0076 (6)	0.0096 (6)
C2	0.0237 (7)	0.0206 (7)	0.0209 (7)	0.0070 (6)	0.0100 (6)	0.0078 (6)
C3	0.0261 (8)	0.0239 (8)	0.0275 (8)	0.0064 (6)	0.0133 (7)	0.0105 (6)
C4	0.0284 (8)	0.0235 (8)	0.0264 (8)	0.0099 (6)	0.0154 (7)	0.0123 (6)
C5	0.0267 (8)	0.0247 (8)	0.0201 (7)	0.0104 (6)	0.0115 (6)	0.0109 (6)
C6	0.0308 (8)	0.0305 (8)	0.0210 (7)	0.0140 (7)	0.0146 (7)	0.0133 (6)
C7	0.0287 (9)	0.0455 (11)	0.0261 (8)	0.0126 (8)	0.0067 (7)	0.0166 (8)
C8	0.0263 (8)	0.0295 (9)	0.0225 (8)	0.0076 (7)	0.0030 (6)	0.0109 (7)
C9	0.0356 (9)	0.0258 (8)	0.0255 (8)	0.0037 (7)	0.0072 (7)	0.0078 (7)
C10	0.0339 (10)	0.0377 (10)	0.0282 (9)	0.0043 (8)	0.0091 (8)	0.0139 (8)
C11	0.0439 (11)	0.0408 (11)	0.0233 (8)	0.0162 (9)	0.0095 (8)	0.0095 (8)
C12	0.086 (2)	0.0259 (10)	0.0368 (12)	0.0083 (11)	0.0186 (12)	0.0033 (9)
C13	0.0619 (15)	0.0297 (10)	0.0376 (11)	−0.0005 (10)	0.0146 (10)	0.0137 (9)
C14	0.0366 (9)	0.0243 (8)	0.0270 (8)	0.0046 (7)	0.0059 (7)	0.0129 (7)
C15	0.0365 (10)	0.0267 (9)	0.0292 (9)	0.0036 (7)	0.0054 (7)	0.0146 (7)
C16	0.0408 (11)	0.0407 (11)	0.0289 (9)	0.0022 (9)	0.0056 (8)	0.0126 (8)
C17	0.080 (2)	0.0575 (16)	0.0426 (13)	0.0024 (14)	0.0169 (13)	0.0253 (12)
C18	0.0334 (9)	0.0293 (9)	0.0374 (10)	0.0141 (7)	0.0147 (8)	0.0109 (8)
C19	0.0322 (9)	0.0241 (8)	0.0343 (9)	0.0027 (7)	0.0041 (8)	0.0118 (7)
C20	0.0241 (8)	0.0307 (9)	0.0265 (8)	0.0061 (7)	0.0060 (7)	0.0113 (7)
O1W	0.121 (2)	0.0388 (10)	0.0519 (11)	0.0309 (12)	0.0242 (13)	0.0241 (9)

F1—C11	1.364 (2)	C7—H7B	0.9900
O1—C15	1.355 (2)	C7—C8	1.505 (3)
O1—C16	1.371 (3)	C8—C9	1.384 (3)
O2—C14	1.217 (2)	C8—C13	1.389 (3)
O3—C3	1.229 (2)	C9—H9	0.9500
O4—H4	0.8400	C9—C10	1.389 (3)
O4—C4	1.339 (2)	C10—H10	0.9500
O5—C6	1.253 (2)	C10—C11	1.366 (3)
N1—H1	0.8800	C11—C12	1.376 (4)
N1—C1	1.477 (2)	C12—H12	0.9500
N1—C14	1.345 (2)	C12—C13	1.388 (4)
N2—C2	1.383 (2)	C13—H13	0.9500
N2—C3	1.394 (2)	C14—C15	1.500 (3)
N2—C20	1.478 (2)	C16—C17	1.476 (4)
N3—C2	1.296 (2)	C17—H17A	0.9800
N3—C5	1.375 (2)	C17—H17B	0.9800
N4—H4A	0.8800	C17—H17C	0.9800
N4—C6	1.323 (3)	C18—H18A	0.9800
N4—C7	1.469 (2)	C18—H18B	0.9800
N5—N6	1.429 (3)	C18—H18C	0.9800
N5—C15	1.268 (3)	C19—H19A	0.9800
N6—C16	1.291 (3)	C19—H19B	0.9800
C1—C2	1.538 (2)	C19—H19C	0.9800
C1—C18	1.542 (3)	C20—H20A	0.9800
C1—C19	1.529 (3)	C20—H20B	0.9800
C3—C4	1.454 (2)	C20—H20C	0.9800
C4—C5	1.357 (3)	O1W—H1WA	0.8500
C5—C6	1.487 (2)	O1W—H1WB	0.8504
C7—H7A	0.9900
C15—O1—C16	102.68 (16)	C9—C10—H10	121.1
C4—O4—H4	109.5	C11—C10—C9	117.9 (2)
C1—N1—H1	117.4	C11—C10—H10	121.1
C14—N1—H1	117.4	F1—C11—C10	118.0 (2)
C14—N1—C1	125.12 (15)	F1—C11—C12	119.3 (2)
C2—N2—C3	121.45 (14)	C10—C11—C12	122.7 (2)
C2—N2—C20	124.45 (14)	C11—C12—H12	120.6
C3—N2—C20	114.08 (14)	C11—C12—C13	118.7 (2)
C2—N3—C5	119.27 (15)	C13—C12—H12	120.6
C6—N4—H4A	118.4	C8—C13—H13	119.9
C6—N4—C7	123.12 (16)	C12—C13—C8	120.2 (2)
C7—N4—H4A	118.4	C12—C13—H13	119.9
C15—N5—N6	106.18 (17)	O2—C14—N1	126.78 (19)
C16—N6—N5	105.55 (18)	O2—C14—C15	121.48 (17)
N1—C1—C2	106.42 (13)	N1—C14—C15	111.74 (16)
N1—C1—C18	113.17 (14)	O1—C15—C14	119.28 (17)
N1—C1—C19	108.21 (15)	N5—C15—O1	113.46 (18)
C2—C1—C18	110.32 (15)	N5—C15—C14	127.26 (17)
C19—C1—C2	110.05 (14)	O1—C16—C17	119.6 (2)
C19—C1—C18	108.63 (15)	N6—C16—O1	112.1 (2)
N2—C2—C1	120.93 (14)	N6—C16—C17	128.3 (2)
N3—C2—N2	122.32 (15)	C16—C17—H17A	109.5
N3—C2—C1	116.75 (15)	C16—C17—H17B	109.5
O3—C3—N2	122.18 (16)	C16—C17—H17C	109.5
O3—C3—C4	122.56 (16)	H17A—C17—H17B	109.5
N2—C3—C4	115.25 (15)	H17A—C17—H17C	109.5
O4—C4—C3	114.82 (16)	H17B—C17—H17C	109.5
O4—C4—C5	126.23 (16)	C1—C18—H18A	109.5
C5—C4—C3	118.95 (15)	C1—C18—H18B	109.5
N3—C5—C6	117.28 (15)	C1—C18—H18C	109.5
C4—C5—N3	122.65 (15)	H18A—C18—H18B	109.5
C4—C5—C6	120.04 (15)	H18A—C18—H18C	109.5
O5—C6—N4	123.62 (16)	H18B—C18—H18C	109.5
O5—C6—C5	119.27 (17)	C1—C19—H19A	109.5
N4—C6—C5	117.11 (15)	C1—C19—H19B	109.5
N4—C7—H7A	109.3	C1—C19—H19C	109.5
N4—C7—H7B	109.3	H19A—C19—H19B	109.5
N4—C7—C8	111.60 (16)	H19A—C19—H19C	109.5
H7A—C7—H7B	108.0	H19B—C19—H19C	109.5
C8—C7—H7A	109.3	N2—C20—H20A	109.5
C8—C7—H7B	109.3	N2—C20—H20B	109.5
C9—C8—C7	120.34 (17)	N2—C20—H20C	109.5
C9—C8—C13	119.05 (19)	H20A—C20—H20B	109.5
C13—C8—C7	120.60 (19)	H20A—C20—H20C	109.5
C8—C9—H9	119.3	H20B—C20—H20C	109.5
C8—C9—C10	121.39 (18)	H1WA—O1W—H1WB	109.4
C10—C9—H9	119.3
F1—C11—C12—C13	−179.7 (2)	C4—C5—C6—N4	178.97 (16)
O2—C14—C15—O1	19.2 (3)	C5—N3—C2—N2	0.9 (2)
O2—C14—C15—N5	−160.2 (2)	C5—N3—C2—C1	−178.19 (14)
O3—C3—C4—O4	2.5 (3)	C6—N4—C7—C8	−94.3 (2)
O3—C3—C4—C5	−176.74 (17)	C7—N4—C6—O5	−3.5 (3)
O4—C4—C5—N3	178.19 (16)	C7—N4—C6—C5	177.18 (16)
O4—C4—C5—C6	0.3 (3)	C7—C8—C9—C10	−177.60 (18)
N1—C1—C2—N2	−57.7 (2)	C7—C8—C13—C12	178.4 (2)
N1—C1—C2—N3	121.37 (16)	C8—C9—C10—C11	−1.1 (3)
N1—C14—C15—O1	−161.84 (18)	C9—C8—C13—C12	−0.9 (4)
N1—C14—C15—N5	18.8 (3)	C9—C10—C11—F1	−179.51 (18)
N2—C3—C4—O4	−176.77 (15)	C9—C10—C11—C12	−0.4 (3)
N2—C3—C4—C5	4.0 (2)	C10—C11—C12—C13	1.2 (4)
N3—C5—C6—O5	−178.36 (15)	C11—C12—C13—C8	−0.5 (4)
N3—C5—C6—N4	1.0 (2)	C13—C8—C9—C10	1.8 (3)
N4—C7—C8—C9	85.1 (2)	C14—N1—C1—C2	172.40 (17)
N4—C7—C8—C13	−94.3 (2)	C14—N1—C1—C18	51.1 (2)
N5—N6—C16—O1	0.5 (3)	C14—N1—C1—C19	−69.4 (2)
N5—N6—C16—C17	179.3 (3)	C15—O1—C16—N6	−0.3 (3)
N6—N5—C15—O1	0.2 (2)	C15—O1—C16—C17	−179.2 (2)
N6—N5—C15—C14	179.65 (19)	C15—N5—N6—C16	−0.4 (2)
C1—N1—C14—O2	−2.9 (3)	C16—O1—C15—N5	0.1 (2)
C1—N1—C14—C15	178.28 (17)	C16—O1—C15—C14	−179.43 (18)
C2—N2—C3—O3	177.59 (16)	C18—C1—C2—N2	65.4 (2)
C2—N2—C3—C4	−3.1 (2)	C18—C1—C2—N3	−115.50 (17)
C2—N3—C5—C4	0.1 (2)	C19—C1—C2—N2	−174.73 (15)
C2—N3—C5—C6	178.05 (15)	C19—C1—C2—N3	4.3 (2)
C3—N2—C2—N3	0.8 (2)	C20—N2—C2—N3	178.83 (16)
C3—N2—C2—C1	179.79 (15)	C20—N2—C2—C1	−2.2 (2)
C3—C4—C5—N3	−2.7 (3)	C20—N2—C3—O3	−0.6 (2)
C3—C4—C5—C6	179.50 (15)	C20—N2—C3—C4	178.63 (15)
C4—C5—C6—O5	−0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5	0.84	1.88	2.593 (2)	143
O1W—H1WB···O2	0.85	2.04	2.869 (2)	164
C20—H20C···N1	0.98	2.25	2.982 (3)	130
N1—H1···O5i	0.88	2.23	2.970 (2)	142
N4—H4A···O1Wii	0.88	2.48	3.074 (3)	126
C7—H7A···O1Wii	0.99	2.58	3.240 (3)	124
C10—H10···O5iii	0.95	2.50	3.393 (3)	158
C20—H20A···O4iv	0.98	2.46	3.394 (2)	160
C20—H20B···N6v	0.98	2.50	3.422 (3)	158
O1W—H1WA···O4vi	0.85	2.51	3.249 (3)	146
O1W—H1WA···O3vi	0.85	2.33	3.013 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O5	0.84	1.88	2.593 (2)	143
C20—H20C⋯N1	0.98	2.25	2.982 (3)	130
N1—H1⋯O5i	0.88	2.23	2.970 (2)	142
N4—H4A⋯O1W ii	0.88	2.48	3.074 (3)	126
C7—H7A⋯O1W ii	0.99	2.58	3.240 (3)	124
C10—H10⋯O5iii	0.95	2.50	3.393 (3)	158
C20—H20A⋯O4iv	0.98	2.46	3.394 (2)	160
C20—H20B⋯N6v	0.98	2.50	3.422 (3)	158
O1W—H1WA⋯O4vi	0.85	2.51	3.249 (3)	146
O1W—H1WA⋯O3vi	0.85	2.33	3.013 (3)	138
O1W—H1WB⋯O2	0.85	2.04	2.869 (2)	164

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