N-{3-[2-(4-Fluoro-phen-oxy)eth-yl]-2,4-dioxo-1,3-diaza-spiro-[4.5]decan-7-yl}-4-methyl-benzamide.

In the title compound, C(24)H(26)FN(3)O(4), the two aromatic rings form a dihedral angle of 88.81 (15)°. The cyclo-hexane ring adopts a chair conformation and the five-membered ring is essentially planar, with a maximum deviation from planarity of 0.041 (2) Å. The crystal structure displays inter-molecular C-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For the biological activity of related compounds, see: Cartwright et al. (2007 ▶); Collins (2000 ▶); Warshakoon et al. (2006 ▶). For the pharmaceutical activity of related compounds, see: Kiselyov et al. (2006 ▶); Sakthivel & Cook (2005 ▶); Eldrup et al. (2004 ▶); Bamford et al. (2005 ▶); Puerstinger et al. (2006 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H26FN3O4

M = 439.48

Triclinic,

a = 9.1436 (17) Å

b = 10.103 (2) Å

c = 13.939 (2) Å

α = 99.239 (15)°

β = 106.550 (14)°

γ = 107.417 (18)°

V = 1134.5 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.22 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010 ▶) T min = 0.770, T max = 1.000

7145 measured reflections

3967 independent reflections

2163 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.135

S = 0.90

3967 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017946/wn2425sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017946/wn2425Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017946/wn2425Isup3.cml

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

C24H26FN3O4	Z = 2
Mr = 439.48	F(000) = 464
Triclinic, P1	Dx = 1.287 Mg m−3
Hall symbol: -P 1	Melting point: 419 K
a = 9.1436 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.103 (2) Å	Cell parameters from 3967 reflections
c = 13.939 (2) Å	θ = 2.7–25.0°
α = 99.239 (15)°	µ = 0.09 mm−1
β = 106.550 (14)°	T = 293 K
γ = 107.417 (18)°	Prism, colourless
V = 1134.5 (4) Å3	0.22 × 0.15 × 0.12 mm

Oxford Diffraction Xcalibur diffractometer	3967 independent reflections
Radiation source: fine-focus sealed tube	2163 reflections with I > 2σ(I)
graphite	Rint = 0.045
Detector resolution: 15.9821 pixels mm-1	θmax = 25.0°, θmin = 2.7°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)	k = −12→12
Tmin = 0.770, Tmax = 1.000	l = −16→16
7145 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 0.90	w = 1/[σ2(Fo2) + (0.0758P)2] where P = (Fo2 + 2Fc2)/3
3967 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05–01–2010 CrysAlis171. NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.1H NMR 400 MHz, DMSO-d6:δ 9.00 (s, 1H), 8.18 (d, J = 8.12 Hz, 1H), 7.72 (d, J = 8.16 Hz, 2H), 6.87–7.25 (m, 6H), 4.12 (q, J = 5.76 Hz, 3H), 3.71 (t, J = 5.84 Hz, 2H), 2.49–2.51 (m, 1H), 2.34 (s, 3H), 1.13–1.85 (m, 7H); MS:m/z 439.5 (M+), 440.5 (M+1); Anal.calcd for C24H26FN3O4: C, 65.59; H, 5.96; N, 9.56%; Found: C, 65.54; H, 5.92; N, 9.53%.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
F1	−0.5189 (2)	1.1248 (2)	−0.66068 (14)	0.1221 (8)
O2	−0.0604 (2)	1.1356 (2)	−0.30513 (13)	0.0641 (5)
O3	−0.1769 (2)	0.91403 (17)	−0.11175 (13)	0.0591 (5)
O4	0.32910 (19)	1.06151 (17)	−0.14001 (13)	0.0621 (5)
O5	0.18882 (18)	0.46876 (16)	0.09178 (12)	0.0594 (5)
N6	0.0690 (2)	1.01919 (18)	−0.13490 (14)	0.0458 (5)
N7	−0.0049 (2)	0.79320 (18)	−0.12864 (13)	0.0459 (5)
H7	−0.0661	0.7084	−0.1313	0.055*
N8	0.3607 (2)	0.67071 (18)	0.07755 (14)	0.0447 (5)
H8	0.4547	0.7397	0.1050	0.054*
C9	−0.4037 (4)	1.1332 (3)	−0.5707 (3)	0.0780 (10)
C10	−0.4070 (4)	1.1951 (3)	−0.4784 (3)	0.0768 (9)
H10	−0.4858	1.2350	−0.4762	0.092*
C11	−0.2930 (3)	1.1989 (3)	−0.3869 (2)	0.0626 (7)
H11	−0.2940	1.2426	−0.3231	0.075*
C12	−0.1786 (3)	1.1383 (3)	−0.39054 (19)	0.0532 (7)
C13	−0.1785 (3)	1.0763 (3)	−0.4859 (2)	0.0733 (8)
H13	−0.1014	1.0347	−0.4891	0.088*
C14	−0.2902 (4)	1.0748 (4)	−0.5763 (2)	0.0835 (10)
H14	−0.2879	1.0343	−0.6404	0.100*
C15	−0.0734 (3)	1.1746 (3)	−0.20599 (18)	0.0560 (7)
H15A	−0.1757	1.1104	−0.2052	0.067*
H15B	−0.0723	1.2721	−0.1916	0.067*
C16	0.0680 (3)	1.1645 (2)	−0.12513 (19)	0.0585 (7)
H16A	0.1691	1.2258	−0.1293	0.070*
H16B	0.0656	1.2010	−0.0571	0.070*
C17	−0.0530 (3)	0.9055 (2)	−0.12341 (17)	0.0447 (6)
C18	0.2006 (3)	0.9841 (2)	−0.13550 (16)	0.0458 (6)
C19	0.1618 (2)	0.8280 (2)	−0.12944 (16)	0.0393 (5)
C20	0.2797 (3)	0.8245 (2)	−0.02788 (16)	0.0402 (6)
H20A	0.3916	0.8675	−0.0249	0.048*
H20B	0.2671	0.8808	0.0304	0.048*
C21	0.2468 (3)	0.6706 (2)	−0.01947 (16)	0.0411 (6)
H21	0.1354	0.6307	−0.0189	0.049*
C22	0.2571 (3)	0.5788 (3)	−0.11345 (19)	0.0598 (7)
H22A	0.3678	0.6149	−0.1138	0.072*
H22B	0.2324	0.4805	−0.1083	0.072*
C23	0.1382 (3)	0.5806 (3)	−0.21441 (19)	0.0645 (8)
H23A	0.0267	0.5373	−0.2168	0.077*
H23B	0.1504	0.5240	−0.2727	0.077*
C24	0.1700 (3)	0.7340 (3)	−0.22326 (18)	0.0571 (7)
H24A	0.0890	0.7334	−0.2860	0.069*
H24B	0.2773	0.7738	−0.2282	0.069*
C25	0.3252 (3)	0.5671 (2)	0.12644 (17)	0.0408 (6)
C26	0.4538 (2)	0.5767 (2)	0.22404 (17)	0.0391 (5)
C27	0.6002 (3)	0.6884 (3)	0.27164 (19)	0.0662 (8)
H27	0.6238	0.7647	0.2420	0.079*
C28	0.7148 (3)	0.6921 (3)	0.3625 (2)	0.0723 (9)
H28	0.8133	0.7705	0.3921	0.087*
C29	0.6874 (3)	0.5846 (3)	0.40928 (19)	0.0638 (8)
C30	0.5429 (4)	0.4727 (4)	0.3620 (3)	0.1180 (16)
H30	0.5198	0.3969	0.3922	0.142*
C31	0.4285 (3)	0.4671 (3)	0.2704 (3)	0.1025 (13)
H31	0.3321	0.3868	0.2397	0.123*
C32	0.8132 (4)	0.5897 (4)	0.5090 (2)	0.1124 (14)
H32A	0.7719	0.5052	0.5309	0.169*
H32B	0.8347	0.6739	0.5619	0.169*
H32C	0.9127	0.5933	0.4975	0.169*

	U11	U22	U33	U12	U13	U23
F1	0.1175 (15)	0.1150 (16)	0.0906 (13)	0.0165 (13)	−0.0120 (12)	0.0524 (12)
O2	0.0677 (11)	0.0840 (14)	0.0567 (11)	0.0419 (10)	0.0252 (9)	0.0281 (10)
O3	0.0558 (11)	0.0495 (10)	0.0745 (12)	0.0177 (9)	0.0234 (10)	0.0255 (9)
O4	0.0522 (10)	0.0471 (10)	0.0820 (12)	0.0029 (8)	0.0205 (9)	0.0392 (9)
O5	0.0469 (10)	0.0457 (10)	0.0702 (11)	−0.0024 (8)	0.0085 (9)	0.0339 (9)
N6	0.0492 (11)	0.0292 (10)	0.0504 (11)	0.0061 (9)	0.0094 (10)	0.0186 (9)
N7	0.0410 (10)	0.0278 (10)	0.0575 (12)	0.0006 (8)	0.0088 (9)	0.0200 (9)
N8	0.0381 (10)	0.0322 (10)	0.0571 (11)	0.0031 (8)	0.0111 (9)	0.0236 (9)
C9	0.078 (2)	0.071 (2)	0.067 (2)	0.0094 (17)	0.0062 (18)	0.0400 (18)
C10	0.077 (2)	0.075 (2)	0.091 (2)	0.0356 (17)	0.0264 (19)	0.0465 (19)
C11	0.0764 (19)	0.0647 (18)	0.0670 (17)	0.0395 (16)	0.0321 (16)	0.0322 (15)
C12	0.0574 (15)	0.0552 (15)	0.0560 (16)	0.0213 (13)	0.0253 (14)	0.0277 (13)
C13	0.0655 (18)	0.088 (2)	0.067 (2)	0.0270 (17)	0.0276 (16)	0.0163 (17)
C14	0.094 (2)	0.084 (2)	0.0567 (19)	0.011 (2)	0.0255 (19)	0.0180 (17)
C15	0.0770 (18)	0.0440 (14)	0.0574 (16)	0.0267 (13)	0.0279 (14)	0.0244 (13)
C16	0.0807 (18)	0.0293 (12)	0.0588 (15)	0.0152 (12)	0.0164 (14)	0.0185 (12)
C17	0.0451 (14)	0.0358 (13)	0.0418 (13)	0.0047 (11)	0.0057 (11)	0.0175 (11)
C18	0.0488 (14)	0.0351 (12)	0.0381 (12)	0.0004 (12)	0.0041 (11)	0.0182 (11)
C19	0.0408 (12)	0.0308 (11)	0.0415 (13)	0.0054 (10)	0.0116 (10)	0.0168 (10)
C20	0.0437 (12)	0.0306 (12)	0.0428 (12)	0.0062 (10)	0.0149 (11)	0.0155 (10)
C21	0.0406 (12)	0.0327 (12)	0.0490 (13)	0.0083 (10)	0.0150 (11)	0.0196 (11)
C22	0.0767 (18)	0.0399 (14)	0.0686 (17)	0.0234 (13)	0.0290 (15)	0.0192 (13)
C23	0.089 (2)	0.0459 (15)	0.0531 (15)	0.0195 (14)	0.0259 (15)	0.0058 (13)
C24	0.0681 (17)	0.0527 (15)	0.0434 (14)	0.0113 (13)	0.0174 (13)	0.0190 (13)
C25	0.0421 (12)	0.0301 (12)	0.0529 (13)	0.0106 (10)	0.0192 (11)	0.0191 (11)
C26	0.0404 (12)	0.0315 (12)	0.0490 (13)	0.0121 (10)	0.0186 (11)	0.0175 (10)
C27	0.0681 (17)	0.0468 (15)	0.0579 (15)	−0.0049 (13)	0.0059 (14)	0.0257 (13)
C28	0.0620 (17)	0.0583 (18)	0.0632 (17)	−0.0048 (14)	−0.0006 (14)	0.0215 (15)
C29	0.0542 (15)	0.0684 (18)	0.0593 (16)	0.0170 (14)	0.0058 (13)	0.0281 (14)
C30	0.078 (2)	0.092 (2)	0.133 (3)	−0.0113 (19)	−0.023 (2)	0.086 (2)
C31	0.0685 (19)	0.070 (2)	0.117 (3)	−0.0167 (16)	−0.0207 (18)	0.067 (2)
C32	0.082 (2)	0.121 (3)	0.092 (2)	0.010 (2)	−0.0166 (19)	0.055 (2)

F1—C9	1.360 (3)	C19—C24	1.522 (3)
O2—C12	1.372 (3)	C19—C20	1.529 (3)
O2—C15	1.423 (3)	C20—C21	1.523 (3)
O3—C17	1.216 (3)	C20—H20A	0.9700
O4—C18	1.226 (2)	C20—H20B	0.9700
O5—C25	1.239 (2)	C21—C22	1.522 (3)
N6—C18	1.355 (3)	C21—H21	0.9800
N6—C17	1.408 (3)	C22—C23	1.520 (3)
N6—C16	1.455 (3)	C22—H22A	0.9700
N7—C17	1.332 (3)	C22—H22B	0.9700
N7—C19	1.462 (3)	C23—C24	1.521 (3)
N7—H7	0.8600	C23—H23A	0.9700
N8—C25	1.348 (2)	C23—H23B	0.9700
N8—C21	1.453 (3)	C24—H24A	0.9700
N8—H8	0.8600	C24—H24B	0.9700
C9—C10	1.350 (4)	C25—C26	1.490 (3)
C9—C14	1.353 (4)	C26—C27	1.362 (3)
C10—C11	1.385 (4)	C26—C31	1.364 (3)
C10—H10	0.9300	C27—C28	1.381 (3)
C11—C12	1.369 (3)	C27—H27	0.9300
C11—H11	0.9300	C28—C29	1.351 (3)
C12—C13	1.377 (4)	C28—H28	0.9300
C13—C14	1.372 (4)	C29—C30	1.352 (4)
C13—H13	0.9300	C29—C32	1.513 (4)
C14—H14	0.9300	C30—C31	1.381 (4)
C15—C16	1.496 (3)	C30—H30	0.9300
C15—H15A	0.9700	C31—H31	0.9300
C15—H15B	0.9700	C32—H32A	0.9600
C16—H16A	0.9700	C32—H32B	0.9600
C16—H16B	0.9700	C32—H32C	0.9600
C18—C19	1.531 (3)
C12—O2—C15	118.2 (2)	C21—C20—H20B	109.4
C18—N6—C17	111.22 (18)	C19—C20—H20B	109.4
C18—N6—C16	123.88 (18)	H20A—C20—H20B	108.0
C17—N6—C16	123.7 (2)	N8—C21—C22	112.08 (19)
C17—N7—C19	113.54 (17)	N8—C21—C20	109.75 (17)
C17—N7—H7	123.2	C22—C21—C20	110.07 (16)
C19—N7—H7	123.2	N8—C21—H21	108.3
C25—N8—C21	122.74 (17)	C22—C21—H21	108.3
C25—N8—H8	118.6	C20—C21—H21	108.3
C21—N8—H8	118.6	C23—C22—C21	111.5 (2)
C10—C9—C14	121.4 (3)	C23—C22—H22A	109.3
C10—C9—F1	120.1 (4)	C21—C22—H22A	109.3
C14—C9—F1	118.5 (4)	C23—C22—H22B	109.3
C9—C10—C11	119.9 (3)	C21—C22—H22B	109.3
C9—C10—H10	120.0	H22A—C22—H22B	108.0
C11—C10—H10	120.0	C22—C23—C24	110.7 (2)
C12—C11—C10	119.8 (3)	C22—C23—H23A	109.5
C12—C11—H11	120.1	C24—C23—H23A	109.5
C10—C11—H11	120.1	C22—C23—H23B	109.5
C11—C12—O2	124.8 (2)	C24—C23—H23B	109.5
C11—C12—C13	118.9 (3)	H23A—C23—H23B	108.1
O2—C12—C13	116.3 (3)	C23—C24—C19	110.85 (17)
C14—C13—C12	121.1 (3)	C23—C24—H24A	109.5
C14—C13—H13	119.5	C19—C24—H24A	109.5
C12—C13—H13	119.5	C23—C24—H24B	109.5
C9—C14—C13	118.9 (3)	C19—C24—H24B	109.5
C9—C14—H14	120.5	H24A—C24—H24B	108.1
C13—C14—H14	120.5	O5—C25—N8	120.7 (2)
O2—C15—C16	108.8 (2)	O5—C25—C26	121.51 (17)
O2—C15—H15A	109.9	N8—C25—C26	117.78 (18)
C16—C15—H15A	109.9	C27—C26—C31	115.8 (2)
O2—C15—H15B	109.9	C27—C26—C25	124.64 (18)
C16—C15—H15B	109.9	C31—C26—C25	119.5 (2)
H15A—C15—H15B	108.3	C26—C27—C28	122.2 (2)
N6—C16—C15	114.0 (2)	C26—C27—H27	118.9
N6—C16—H16A	108.7	C28—C27—H27	118.9
C15—C16—H16A	108.7	C29—C28—C27	121.6 (2)
N6—C16—H16B	108.7	C29—C28—H28	119.2
C15—C16—H16B	108.7	C27—C28—H28	119.2
H16A—C16—H16B	107.6	C28—C29—C30	116.6 (2)
O3—C17—N7	128.92 (19)	C28—C29—C32	121.3 (2)
O3—C17—N6	124.1 (2)	C30—C29—C32	122.1 (2)
N7—C17—N6	106.9 (2)	C29—C30—C31	122.2 (2)
O4—C18—N6	127.1 (2)	C29—C30—H30	118.9
O4—C18—C19	125.1 (2)	C31—C30—H30	118.9
N6—C18—C19	107.82 (17)	C26—C31—C30	121.5 (2)
N7—C19—C24	112.72 (18)	C26—C31—H31	119.2
N7—C19—C20	111.68 (16)	C30—C31—H31	119.2
C24—C19—C20	111.41 (19)	C29—C32—H32A	109.5
N7—C19—C18	99.91 (19)	C29—C32—H32B	109.5
C24—C19—C18	111.22 (16)	H32A—C32—H32B	109.5
C20—C19—C18	109.34 (17)	C29—C32—H32C	109.5
C21—C20—C19	111.03 (17)	H32A—C32—H32C	109.5
C21—C20—H20A	109.4	H32B—C32—H32C	109.5
C19—C20—H20A	109.4
C14—C9—C10—C11	−0.4 (4)	O4—C18—C19—C20	64.1 (3)
F1—C9—C10—C11	177.8 (2)	N6—C18—C19—C20	−115.9 (2)
C9—C10—C11—C12	−0.8 (4)	N7—C19—C20—C21	71.2 (2)
C10—C11—C12—O2	−179.9 (2)	C24—C19—C20—C21	−55.8 (2)
C10—C11—C12—C13	0.9 (4)	C18—C19—C20—C21	−179.18 (19)
C15—O2—C12—C11	11.8 (3)	C25—N8—C21—C22	−84.7 (2)
C15—O2—C12—C13	−168.9 (2)	C25—N8—C21—C20	152.6 (2)
C11—C12—C13—C14	0.1 (4)	C19—C20—C21—N8	179.89 (18)
O2—C12—C13—C14	−179.2 (2)	C19—C20—C21—C22	56.1 (2)
C10—C9—C14—C13	1.4 (4)	N8—C21—C22—C23	−179.60 (16)
F1—C9—C14—C13	−176.8 (2)	C20—C21—C22—C23	−57.2 (2)
C12—C13—C14—C9	−1.2 (4)	C21—C22—C23—C24	57.2 (3)
C12—O2—C15—C16	−179.74 (19)	C22—C23—C24—C19	−55.8 (3)
C18—N6—C16—C15	129.5 (2)	N7—C19—C24—C23	−71.1 (2)
C17—N6—C16—C15	−64.1 (3)	C20—C19—C24—C23	55.4 (3)
O2—C15—C16—N6	−64.6 (2)	C18—C19—C24—C23	177.7 (2)
C19—N7—C17—O3	−172.4 (2)	C21—N8—C25—O5	−2.8 (3)
C19—N7—C17—N6	8.0 (2)	C21—N8—C25—C26	178.4 (2)
C18—N6—C17—O3	173.5 (2)	O5—C25—C26—C27	−173.7 (2)
C16—N6—C17—O3	5.6 (3)	N8—C25—C26—C27	5.1 (3)
C18—N6—C17—N7	−6.9 (2)	O5—C25—C26—C31	7.3 (4)
C16—N6—C17—N7	−174.82 (19)	N8—C25—C26—C31	−173.8 (3)
C17—N6—C18—O4	−176.8 (2)	C31—C26—C27—C28	−1.3 (4)
C16—N6—C18—O4	−8.9 (4)	C25—C26—C27—C28	179.7 (3)
C17—N6—C18—C19	3.2 (2)	C26—C27—C28—C29	−0.2 (5)
C16—N6—C18—C19	171.07 (18)	C27—C28—C29—C30	0.7 (5)
C17—N7—C19—C24	−124.0 (2)	C27—C28—C29—C32	−179.7 (3)
C17—N7—C19—C20	109.7 (2)	C28—C29—C30—C31	0.2 (6)
C17—N7—C19—C18	−5.9 (2)	C32—C29—C30—C31	−179.4 (4)
O4—C18—C19—N7	−178.6 (2)	C27—C26—C31—C30	2.2 (5)
N6—C18—C19—N7	1.4 (2)	C25—C26—C31—C30	−178.7 (3)
O4—C18—C19—C24	−59.4 (3)	C29—C30—C31—C26	−1.7 (6)
N6—C18—C19—C24	120.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O5i	0.86	2.06	2.892 (3)	163
N8—H8···O4ii	0.86	2.22	3.060 (3)	165
C27—H27···O4ii	0.93	2.45	3.370 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O5i	0.86	2.06	2.892 (3)	163
N8—H8⋯O4ii	0.86	2.22	3.060 (3)	165
C27—H27⋯O4ii	0.93	2.45	3.370 (3)	172

Symmetry codes: (i) ; (ii) .