4'-(1H-Imidazol-2-yl)-3'-[(1H-indol-3-yl)carbon-yl]-1'-methyl-2-oxo-spiro-[indoline-3,2'-pyrrolidine]-3'-carbo-nitrile 0.15-hydrate.

In the title compound, C25H20N6O2·0.15H2O, the dihedral angles between the least-squares planes of the indole and pyrrolidine rings and between the oxindole and imidazole rings are 77.66 (7) and 45.31 (7)°, respectively. The pyrrolidine ring and the fused five-membered pyrrolidine ring of the oxindole moiety exhibit twisted conformations. The amide N atom is involved in both intra- and inter-molecular hydrogen bonding, having a bifurcated character. The mol-ecular structure is characterized by an intra-molecular N-H⋯O hydrogen bond, which generates an S(7) ring motif while an inter-molecular N-H⋯O hydrogen bond links the organic and solvent water mol-ecules. In the crystal, N-H⋯N hydrogen bonds generate a zigzag chain running parallel to c-axis direction. The H atoms of the solvent water mol-ecule were not located.

Related literature

For background to indole derivatives and their biological activity, see: Rudrangi et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For a related structure, see: Inglebert et al. (2013 ▶).

Experimental

Crystal data

C25H20N6O2·0.15H2O

M = 439.17

Monoclinic,

a = 8.650 (5) Å

b = 16.952 (5) Å

c = 14.438 (5) Å

β = 97.161 (5)°

V = 2100.6 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.968, T max = 0.977

22198 measured reflections

4819 independent reflections

3757 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.03

4819 reflections

320 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813023246/rk2411sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023246/rk2411Isup2.hkl

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

C25H20N6O2·0.15H2O	F(000) = 916.8
Mr = 439.17	Dx = 1.389 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4819 reflections
a = 8.650 (5) Å	θ = 2.4–27.5°
b = 16.952 (5) Å	µ = 0.09 mm−1
c = 14.438 (5) Å	T = 295 K
β = 97.161 (5)°	Block, colourless
V = 2100.6 (15) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4819 independent reflections
Radiation source: fine–focus sealed tube	3757 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω and φ scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→10
Tmin = 0.968, Tmax = 0.977	k = −21→22
22198 measured reflections	l = −18→18

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0524P)2 + 0.5356P] where P = (Fo2 + 2Fc2)/3
4819 reflections	(Δ/σ)max < 0.001
320 parameters	Δρmax = 0.21 e Å−3
3 restraints	Δρmin = −0.18 e Å−3

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 > 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	Occ. (<1)
O1	0.37937 (14)	0.07447 (6)	0.49050 (7)	0.0487 (3)
O2	0.60471 (12)	0.18182 (6)	0.64371 (8)	0.0489 (3)
N3	0.33938 (14)	0.30031 (7)	0.63558 (8)	0.0366 (3)
N2	0.66582 (14)	0.25656 (8)	0.52028 (9)	0.0406 (3)
N1	0.38442 (14)	0.21594 (7)	0.22422 (8)	0.0380 (3)
C15	0.40978 (15)	0.26985 (7)	0.55702 (9)	0.0315 (3)
C10	0.28828 (14)	0.20355 (7)	0.52052 (9)	0.0292 (3)
N6	0.12101 (15)	0.03867 (7)	0.61150 (9)	0.0432 (3)
N5	−0.02773 (15)	0.14222 (8)	0.61946 (11)	0.0508 (3)
C1	0.42119 (15)	0.09829 (8)	0.29638 (9)	0.0318 (3)
C16	0.44630 (15)	0.33152 (8)	0.48826 (9)	0.0340 (3)
C11	0.25875 (15)	0.16641 (8)	0.61571 (9)	0.0326 (3)
H11	0.3466	0.1309	0.6343	0.039*
C6	0.43006 (16)	0.13884 (8)	0.21219 (9)	0.0352 (3)
C9	0.34886 (14)	0.13897 (8)	0.45599 (9)	0.0313 (3)
C8	0.36716 (15)	0.15545 (8)	0.36003 (9)	0.0316 (3)
C12	0.27540 (17)	0.23523 (8)	0.68508 (10)	0.0399 (3)
H12A	0.1749	0.2494	0.7034	0.048*
H12B	0.3452	0.2213	0.7406	0.048*
C7	0.34692 (16)	0.22545 (8)	0.31089 (9)	0.0359 (3)
H7	0.3123	0.2724	0.3345	0.043*
C21	0.59667 (16)	0.31921 (8)	0.46655 (10)	0.0368 (3)
C2	0.46065 (17)	0.01848 (8)	0.30176 (10)	0.0386 (3)
H2	0.4569	−0.0096	0.3568	0.046*
C22	0.57128 (15)	0.22878 (8)	0.58113 (10)	0.0359 (3)
C13	0.14541 (16)	0.24026 (8)	0.47441 (9)	0.0361 (3)
C3	0.50525 (19)	−0.01783 (9)	0.22397 (11)	0.0478 (4)
H3	0.5299	−0.0712	0.2266	0.057*
C23	0.11522 (16)	0.11799 (8)	0.61483 (9)	0.0351 (3)
C19	0.5689 (2)	0.42550 (10)	0.36056 (12)	0.0552 (4)
H19	0.6079	0.4569	0.3160	0.066*
N4	0.03167 (16)	0.26634 (9)	0.43965 (10)	0.0581 (4)
C5	0.47677 (19)	0.10239 (10)	0.13400 (10)	0.0467 (4)
H5	0.4824	0.1302	0.0790	0.056*
C20	0.66026 (19)	0.36546 (10)	0.40259 (11)	0.0476 (4)
H20	0.7607	0.3566	0.3883	0.057*
C4	0.5143 (2)	0.02372 (10)	0.14131 (11)	0.0512 (4)
H4	0.5462	−0.0023	0.0903	0.061*
C17	0.35815 (18)	0.39336 (8)	0.44843 (11)	0.0424 (3)
H17	0.2594	0.4036	0.4648	0.051*
C18	0.4207 (2)	0.44015 (9)	0.38310 (12)	0.0524 (4)
H18	0.3625	0.4815	0.3544	0.063*
C25	−0.1158 (2)	0.07419 (10)	0.61833 (14)	0.0584 (5)
H25	−0.2227	0.0728	0.6207	0.070*
C14	0.4324 (2)	0.35557 (10)	0.69609 (12)	0.0555 (4)
H14A	0.5180	0.3281	0.7306	0.083*
H14B	0.3690	0.3790	0.7387	0.083*
H14C	0.4718	0.3961	0.6589	0.083*
C24	−0.0261 (2)	0.01074 (10)	0.61340 (12)	0.0513 (4)
H24	−0.0576	−0.0418	0.6116	0.062*
O1W	0.2610 (10)	−0.0987 (6)	0.5729 (7)	0.082 (3)	0.15
H2A	0.7632 (12)	0.2407 (9)	0.5205 (12)	0.052 (5)*
H1A	0.393 (2)	0.2564 (8)	0.1861 (11)	0.061 (5)*
H6A	0.2060 (17)	0.0112 (11)	0.6021 (15)	0.075 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0721 (8)	0.0369 (6)	0.0403 (5)	0.0139 (5)	0.0190 (5)	0.0060 (4)
O2	0.0363 (6)	0.0479 (6)	0.0605 (7)	0.0013 (5)	−0.0018 (5)	0.0177 (5)
N3	0.0386 (6)	0.0330 (6)	0.0384 (6)	−0.0033 (5)	0.0063 (5)	−0.0054 (5)
N2	0.0267 (6)	0.0464 (7)	0.0486 (7)	0.0010 (5)	0.0047 (5)	0.0038 (5)
N1	0.0448 (7)	0.0351 (6)	0.0344 (6)	0.0017 (5)	0.0053 (5)	0.0064 (5)
C15	0.0275 (6)	0.0294 (6)	0.0374 (6)	−0.0001 (5)	0.0035 (5)	0.0001 (5)
C10	0.0257 (6)	0.0300 (6)	0.0324 (6)	0.0002 (5)	0.0053 (5)	0.0000 (5)
N6	0.0462 (8)	0.0346 (7)	0.0494 (7)	−0.0044 (6)	0.0088 (6)	−0.0035 (5)
N5	0.0386 (7)	0.0406 (7)	0.0776 (9)	−0.0088 (6)	0.0247 (6)	−0.0085 (6)
C1	0.0292 (6)	0.0354 (7)	0.0315 (6)	−0.0020 (5)	0.0064 (5)	0.0007 (5)
C16	0.0333 (7)	0.0297 (7)	0.0389 (7)	−0.0044 (5)	0.0041 (5)	−0.0004 (5)
C11	0.0324 (7)	0.0348 (7)	0.0316 (6)	−0.0025 (5)	0.0077 (5)	−0.0014 (5)
C6	0.0350 (7)	0.0360 (7)	0.0350 (7)	−0.0007 (6)	0.0059 (5)	0.0028 (5)
C9	0.0294 (6)	0.0312 (7)	0.0339 (6)	0.0005 (5)	0.0060 (5)	0.0006 (5)
C8	0.0295 (6)	0.0323 (7)	0.0334 (6)	−0.0004 (5)	0.0059 (5)	0.0003 (5)
C12	0.0425 (8)	0.0419 (8)	0.0364 (7)	−0.0086 (6)	0.0098 (6)	−0.0073 (6)
C7	0.0355 (7)	0.0358 (7)	0.0361 (7)	0.0022 (6)	0.0027 (5)	−0.0003 (5)
C21	0.0346 (7)	0.0364 (7)	0.0393 (7)	−0.0054 (6)	0.0043 (5)	−0.0027 (6)
C2	0.0435 (8)	0.0353 (7)	0.0384 (7)	0.0014 (6)	0.0103 (6)	0.0040 (6)
C22	0.0288 (7)	0.0349 (7)	0.0428 (7)	−0.0029 (5)	−0.0006 (5)	0.0002 (6)
C13	0.0313 (7)	0.0401 (8)	0.0371 (7)	0.0006 (6)	0.0054 (5)	−0.0046 (6)
C3	0.0597 (10)	0.0378 (8)	0.0474 (8)	0.0095 (7)	0.0127 (7)	−0.0012 (6)
C23	0.0393 (8)	0.0335 (7)	0.0343 (6)	−0.0058 (6)	0.0117 (5)	−0.0038 (5)
C19	0.0660 (11)	0.0504 (10)	0.0516 (9)	−0.0112 (8)	0.0166 (8)	0.0112 (7)
N4	0.0386 (7)	0.0737 (10)	0.0595 (8)	0.0149 (7)	−0.0037 (6)	−0.0056 (7)
C5	0.0568 (9)	0.0520 (9)	0.0331 (7)	0.0037 (7)	0.0129 (6)	0.0051 (6)
C20	0.0454 (9)	0.0515 (9)	0.0480 (8)	−0.0071 (7)	0.0141 (7)	0.0021 (7)
C4	0.0645 (11)	0.0526 (10)	0.0391 (8)	0.0101 (8)	0.0165 (7)	−0.0054 (7)
C17	0.0436 (8)	0.0324 (7)	0.0513 (8)	0.0022 (6)	0.0066 (6)	0.0023 (6)
C18	0.0642 (11)	0.0359 (8)	0.0564 (9)	0.0003 (7)	0.0048 (8)	0.0115 (7)
C25	0.0441 (9)	0.0502 (10)	0.0849 (13)	−0.0177 (8)	0.0239 (8)	−0.0101 (9)
C14	0.0714 (11)	0.0435 (9)	0.0515 (9)	−0.0174 (8)	0.0078 (8)	−0.0134 (7)
C24	0.0586 (10)	0.0394 (8)	0.0569 (9)	−0.0187 (8)	0.0116 (7)	−0.0048 (7)
O1W	0.063 (5)	0.070 (6)	0.102 (7)	0.036 (5)	−0.028 (5)	−0.039 (5)

O1—C9	1.2168 (16)	C11—H11	0.9800
O2—C22	1.2119 (17)	C6—C5	1.390 (2)
N3—C15	1.4478 (17)	C9—C8	1.4413 (18)
N3—C14	1.4538 (19)	C8—C7	1.3826 (19)
N3—C12	1.4604 (18)	C12—H12A	0.9700
N2—C22	1.3570 (19)	C12—H12B	0.9700
N2—C21	1.4043 (19)	C7—H7	0.9300
N2—H2A	0.884 (9)	C21—C20	1.377 (2)
N1—C7	1.3410 (18)	C2—C3	1.377 (2)
N1—C6	1.3825 (19)	C2—H2	0.9300
N1—H1A	0.888 (9)	C13—N4	1.1367 (19)
C15—C16	1.5022 (18)	C3—C4	1.396 (2)
C15—C22	1.561 (2)	C3—H3	0.9300
C15—C10	1.5835 (18)	C19—C20	1.382 (2)
C10—C13	1.4671 (19)	C19—C18	1.383 (3)
C10—C11	1.5615 (18)	C19—H19	0.9300
C10—C9	1.5693 (18)	C5—C4	1.373 (2)
N6—C23	1.3467 (19)	C5—H5	0.9300
N6—C24	1.361 (2)	C20—H20	0.9300
N6—H6A	0.895 (9)	C4—H4	0.9300
N5—C23	1.313 (2)	C17—C18	1.393 (2)
N5—C25	1.381 (2)	C17—H17	0.9300
C1—C2	1.395 (2)	C18—H18	0.9300
C1—C6	1.4068 (18)	C25—C24	1.333 (2)
C1—C8	1.4522 (18)	C25—H25	0.9300
C16—C17	1.3790 (19)	C14—H14A	0.9600
C16—C21	1.391 (2)	C14—H14B	0.9600
C11—C23	1.4871 (19)	C14—H14C	0.9600
C11—C12	1.5325 (19)	C24—H24	0.9300
C15—N3—C14	116.43 (12)	H12A—C12—H12B	108.8
C15—N3—C12	109.63 (11)	N1—C7—C8	110.23 (12)
C14—N3—C12	114.08 (12)	N1—C7—H7	124.9
C22—N2—C21	111.75 (12)	C8—C7—H7	124.9
C22—N2—H2A	122.9 (11)	C20—C21—C16	121.90 (14)
C21—N2—H2A	124.9 (11)	C20—C21—N2	128.52 (14)
C7—N1—C6	109.69 (11)	C16—C21—N2	109.56 (12)
C7—N1—H1A	122.3 (12)	C3—C2—C1	118.65 (13)
C6—N1—H1A	127.3 (12)	C3—C2—H2	120.7
N3—C15—C16	114.40 (11)	C1—C2—H2	120.7
N3—C15—C22	115.88 (11)	O2—C22—N2	127.13 (13)
C16—C15—C22	101.64 (10)	O2—C22—C15	125.67 (13)
N3—C15—C10	100.80 (10)	N2—C22—C15	107.20 (12)
C16—C15—C10	117.35 (11)	N4—C13—C10	177.44 (16)
C22—C15—C10	107.23 (10)	C2—C3—C4	121.51 (14)
C13—C10—C11	110.45 (11)	C2—C3—H3	119.2
C13—C10—C9	110.56 (10)	C4—C3—H3	119.2
C11—C10—C9	110.16 (10)	N5—C23—N6	110.71 (12)
C13—C10—C15	109.67 (11)	N5—C23—C11	128.15 (13)
C11—C10—C15	99.66 (10)	N6—C23—C11	121.11 (13)
C9—C10—C15	115.84 (10)	C20—C19—C18	121.66 (15)
C23—N6—C24	107.91 (13)	C20—C19—H19	119.2
C23—N6—H6A	124.1 (14)	C18—C19—H19	119.2
C24—N6—H6A	127.6 (14)	C4—C5—C6	117.31 (13)
C23—N5—C25	105.06 (14)	C4—C5—H5	121.3
C2—C1—C6	118.86 (12)	C6—C5—H5	121.3
C2—C1—C8	135.04 (12)	C21—C20—C19	117.34 (15)
C6—C1—C8	106.10 (12)	C21—C20—H20	121.3
C17—C16—C21	120.26 (13)	C19—C20—H20	121.3
C17—C16—C15	130.83 (13)	C5—C4—C3	121.18 (14)
C21—C16—C15	108.91 (12)	C5—C4—H4	119.4
C23—C11—C12	115.86 (11)	C3—C4—H4	119.4
C23—C11—C10	116.30 (11)	C16—C17—C18	118.30 (15)
C12—C11—C10	104.83 (11)	C16—C17—H17	120.9
C23—C11—H11	106.4	C18—C17—H17	120.9
C12—C11—H11	106.4	C19—C18—C17	120.45 (15)
C10—C11—H11	106.4	C19—C18—H18	119.8
N1—C6—C5	129.68 (13)	C17—C18—H18	119.8
N1—C6—C1	107.83 (12)	C24—C25—N5	110.53 (15)
C5—C6—C1	122.49 (13)	C24—C25—H25	124.7
O1—C9—C8	121.56 (12)	N5—C25—H25	124.7
O1—C9—C10	117.08 (11)	N3—C14—H14A	109.5
C8—C9—C10	121.35 (11)	N3—C14—H14B	109.5
C7—C8—C9	129.61 (12)	H14A—C14—H14B	109.5
C7—C8—C1	106.14 (11)	N3—C14—H14C	109.5
C9—C8—C1	124.17 (12)	H14A—C14—H14C	109.5
N3—C12—C11	105.41 (11)	H14B—C14—H14C	109.5
N3—C12—H12A	110.7	C25—C24—N6	105.79 (14)
C11—C12—H12A	110.7	C25—C24—H24	127.1
N3—C12—H12B	110.7	N6—C24—H24	127.1
C11—C12—H12B	110.7
C14—N3—C15—C16	−62.11 (16)	C15—N3—C12—C11	−19.05 (14)
C12—N3—C15—C16	166.52 (11)	C14—N3—C12—C11	−151.66 (13)
C14—N3—C15—C22	55.69 (16)	C23—C11—C12—N3	−139.92 (12)
C12—N3—C15—C22	−75.69 (14)	C10—C11—C12—N3	−10.31 (14)
C14—N3—C15—C10	171.01 (12)	C6—N1—C7—C8	0.44 (16)
C12—N3—C15—C10	39.64 (13)	C9—C8—C7—N1	176.60 (13)
N3—C15—C10—C13	72.92 (12)	C1—C8—C7—N1	−0.36 (15)
C16—C15—C10—C13	−51.98 (14)	C17—C16—C21—C20	−2.7 (2)
C22—C15—C10—C13	−165.45 (11)	C15—C16—C21—C20	177.84 (13)
N3—C15—C10—C11	−43.01 (11)	C17—C16—C21—N2	175.99 (12)
C16—C15—C10—C11	−167.91 (11)	C15—C16—C21—N2	−3.47 (15)
C22—C15—C10—C11	78.62 (12)	C22—N2—C21—C20	175.24 (14)
N3—C15—C10—C9	−161.10 (10)	C22—N2—C21—C16	−3.34 (16)
C16—C15—C10—C9	74.00 (14)	C6—C1—C2—C3	−0.7 (2)
C22—C15—C10—C9	−39.47 (14)	C8—C1—C2—C3	178.51 (15)
N3—C15—C16—C17	−45.93 (19)	C21—N2—C22—O2	−170.64 (14)
C22—C15—C16—C17	−171.58 (14)	C21—N2—C22—C15	8.35 (15)
C10—C15—C16—C17	71.86 (19)	N3—C15—C22—O2	44.68 (19)
N3—C15—C16—C21	133.45 (12)	C16—C15—C22—O2	169.35 (14)
C22—C15—C16—C21	7.80 (14)	C10—C15—C22—O2	−66.94 (17)
C10—C15—C16—C21	−108.75 (13)	N3—C15—C22—N2	−134.34 (12)
C13—C10—C11—C23	46.36 (16)	C16—C15—C22—N2	−9.67 (13)
C9—C10—C11—C23	−76.07 (14)	C10—C15—C22—N2	114.04 (12)
C15—C10—C11—C23	161.69 (11)	C1—C2—C3—C4	1.2 (2)
C13—C10—C11—C12	−82.99 (13)	C25—N5—C23—N6	−0.39 (18)
C9—C10—C11—C12	154.58 (11)	C25—N5—C23—C11	−178.58 (14)
C15—C10—C11—C12	32.35 (12)	C24—N6—C23—N5	0.46 (17)
C7—N1—C6—C5	179.16 (15)	C24—N6—C23—C11	178.79 (12)
C7—N1—C6—C1	−0.33 (16)	C12—C11—C23—N5	41.7 (2)
C2—C1—C6—N1	179.51 (12)	C10—C11—C23—N5	−82.13 (18)
C8—C1—C6—N1	0.10 (15)	C12—C11—C23—N6	−136.32 (14)
C2—C1—C6—C5	0.0 (2)	C10—C11—C23—N6	99.85 (15)
C8—C1—C6—C5	−179.43 (13)	N1—C6—C5—C4	−179.14 (15)
C13—C10—C9—O1	−129.88 (13)	C1—C6—C5—C4	0.3 (2)
C11—C10—C9—O1	−7.51 (16)	C16—C21—C20—C19	0.3 (2)
C15—C10—C9—O1	104.60 (14)	N2—C21—C20—C19	−178.08 (15)
C13—C10—C9—C8	50.01 (16)	C18—C19—C20—C21	1.5 (3)
C11—C10—C9—C8	172.37 (11)	C6—C5—C4—C3	0.2 (3)
C15—C10—C9—C8	−75.52 (15)	C2—C3—C4—C5	−0.9 (3)
O1—C9—C8—C7	−176.01 (14)	C21—C16—C17—C18	3.1 (2)
C10—C9—C8—C7	4.1 (2)	C15—C16—C17—C18	−177.58 (14)
O1—C9—C8—C1	0.5 (2)	C20—C19—C18—C17	−1.1 (3)
C10—C9—C8—C1	−179.41 (11)	C16—C17—C18—C19	−1.3 (2)
C2—C1—C8—C7	−179.12 (15)	C23—N5—C25—C24	0.2 (2)
C6—C1—C8—C7	0.15 (14)	N5—C25—C24—N6	0.1 (2)
C2—C1—C8—C9	3.7 (2)	C23—N6—C24—C25	−0.32 (19)
C6—C1—C8—C9	−177.02 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N5i	0.89 (1)	2.13 (1)	2.9889 (19)	164 (2)
N6—H6A···O1W	0.90 (1)	1.98 (2)	2.714 (8)	138 (2)
N6—H6A···O1	0.90 (1)	2.57 (2)	3.064 (2)	116 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N5i	0.89 (1)	2.13 (1)	2.9889 (19)	164 (2)
N6—H6A⋯O1W	0.90 (1)	1.98 (2)	2.714 (8)	138 (2)
N6—H6A⋯O1	0.90 (1)	2.57 (2)	3.064 (2)	116 (2)

Symmetry code: (i) .