3'-[(1H-Indol-3-yl)carbon-yl]-1'-methyl-2-oxo-4'-(thio-phen-2-yl)-spiro-[indoline-3,2'-pyrrolidine]-3'-carbo-nitrile.

In the title compound, C26H20N4O2S, the central pyrrolidine ring adopts a twist conformation on the C-C bond involving the spiro C atom. Its mean plane makes dihedral angles of 78.83 (14), 65.91 (15) and 44.49 (18)° with the mean planes of the adjacent oxindole ring system, the indole system and the thio-phene ring, respectively. The indole and indoline units are essentially planar, with maximum deviations of 0.019 (3) and 0.090 (3) Å, respectively. In the oxindole fused-ring system, the pyrrole ring adopts an envelope conformation with the spiro C atom as the flap. In the crystal, pairs of N-H⋯O hydrogen bonds link the mol-ecules, forming inversion dimers with an R (2) 2(8) ring motif. The dimers are linked by further N-H⋯O hydrogen bonds, forming a two-dimensional network lying parallel to (100).

Related literature

For background to indole derivatives and their biological activity, see: Srivastava 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

C26H20N4O2S

M = 452.52

Monoclinic,

a = 11.6215 (6) Å

b = 17.1050 (11) Å

c = 12.3381 (8) Å

β = 114.431 (2)°

V = 2233.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker APEXII2 CCD difractometer diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.941, T max = 0.957

16319 measured reflections

5279 independent reflections

3636 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.252

S = 1.07

5279 reflections

306 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.15 e Å−3

Δρmin = −0.98 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: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813025890/su2642sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025890/su2642Isup2.hkl

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

C26H20N4O2S	F(000) = 944
Mr = 452.52	Dx = 1.346 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5279 reflections
a = 11.6215 (6) Å	θ = 2.2–27.9°
b = 17.1050 (11) Å	µ = 0.18 mm−1
c = 12.3381 (8) Å	T = 293 K
β = 114.431 (2)°	Block, colourless
V = 2233.0 (2) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker APEXII2 CCD difractometer diffractometer	5279 independent reflections
Radiation source: fine-focus sealed tube	3636 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scan	θmax = 27.9°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→8
Tmin = 0.941, Tmax = 0.957	k = −21→22
16319 measured reflections	l = −14→16

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.252	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.1409P)2 + 1.6573P] where P = (Fo2 + 2Fc2)/3
5279 reflections	(Δ/σ)max = 0.003
306 parameters	Δρmax = 1.15 e Å−3
5 restraints	Δρmin = −0.98 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
C5	0.9175 (3)	0.04509 (16)	0.1198 (3)	0.0313 (6)
H5	0.8526	0.0371	0.0390	0.038*
C6	0.9536 (3)	−0.03507 (18)	0.1780 (3)	0.0403 (7)
H6A	0.9204	−0.0760	0.1188	0.048*
H6B	1.0448	−0.0403	0.2170	0.048*
C7	0.8686 (3)	−0.12000 (19)	0.2877 (4)	0.0502 (8)
H7A	0.9413	−0.1529	0.3064	0.075*
H7B	0.7999	−0.1397	0.2180	0.075*
H7C	0.8446	−0.1197	0.3534	0.075*
C8	0.7970 (2)	0.01482 (16)	0.2360 (2)	0.0289 (6)
C9	0.8532 (2)	0.08688 (16)	0.1927 (2)	0.0277 (6)
C10	0.7470 (2)	0.14477 (16)	0.1152 (2)	0.0303 (6)
C11	0.6903 (3)	0.19866 (17)	0.1672 (2)	0.0323 (6)
C12	0.5730 (2)	0.24011 (16)	0.1035 (2)	0.0311 (6)
C13	0.4806 (3)	0.24014 (19)	−0.0133 (3)	0.0394 (7)
H13	0.4882	0.2079	−0.0706	0.047*
C14	0.3773 (3)	0.2892 (2)	−0.0420 (3)	0.0474 (8)
H14	0.3153	0.2895	−0.1196	0.057*
C15	0.3641 (3)	0.3378 (2)	0.0420 (3)	0.0479 (8)
H15	0.2946	0.3710	0.0192	0.058*
C16	0.4511 (3)	0.33779 (19)	0.1576 (3)	0.0446 (8)
H16	0.4413	0.3694	0.2145	0.054*
C17	0.5550 (3)	0.28865 (18)	0.1871 (3)	0.0361 (6)
C18	0.7336 (3)	0.22322 (19)	0.2844 (3)	0.0419 (7)
H18	0.8071	0.2055	0.3463	0.050*
C19	0.7534 (2)	0.03331 (17)	0.3323 (2)	0.0313 (6)
C20	0.8205 (3)	0.0492 (2)	0.4520 (3)	0.0405 (7)
H20	0.9083	0.0468	0.4870	0.049*
C21	0.7536 (4)	0.0689 (2)	0.5186 (3)	0.0520 (9)
H21	0.7974	0.0807	0.5989	0.062*
C22	0.6227 (3)	0.0714 (2)	0.4675 (3)	0.0519 (9)
H22	0.5799	0.0856	0.5136	0.062*
C23	0.5554 (3)	0.0530 (2)	0.3496 (3)	0.0461 (8)
H23	0.4676	0.0533	0.3156	0.055*
C24	0.6223 (3)	0.03431 (18)	0.2832 (3)	0.0344 (6)
C25	0.6696 (2)	−0.00651 (17)	0.1305 (2)	0.0320 (6)
C26	0.9511 (3)	0.12412 (17)	0.2976 (3)	0.0338 (6)
N1	0.8989 (2)	−0.04069 (14)	0.2652 (2)	0.0314 (5)
N2	1.0305 (3)	0.1513 (2)	0.3775 (3)	0.0536 (8)
N3	0.5757 (2)	0.01076 (17)	0.1639 (2)	0.0384 (6)
N4	0.6549 (3)	0.27593 (17)	0.2955 (2)	0.0432 (6)
O1	0.7082 (2)	0.13787 (13)	0.00656 (18)	0.0420 (5)
O2	0.65774 (19)	−0.03273 (14)	0.03448 (19)	0.0431 (6)
C3	1.1633 (3)	0.07184 (19)	0.1643 (3)	0.0387 (7)
H3	1.2042	0.0288	0.2100	0.046*
C1	1.1410 (4)	0.1943 (2)	0.0621 (4)	0.0541 (9)
H1	1.1683	0.2385	0.0356	0.065*
C2	1.2182 (3)	0.1393 (2)	0.1252 (3)	0.0540 (9)
H2	1.3045	0.1423	0.1450	0.065*
C4	1.0225 (3)	0.09175 (19)	0.1099 (3)	0.0369 (6)
S1	0.98893 (10)	0.17802 (6)	0.03333 (12)	0.0667 (4)
H3A	0.4965 (19)	0.008 (4)	0.130 (5)	0.110 (19)*
H4A	0.669 (4)	0.303 (2)	0.357 (3)	0.066 (13)*

	U11	U22	U33	U12	U13	U23
C5	0.0313 (13)	0.0332 (14)	0.0297 (14)	0.0053 (11)	0.0129 (11)	−0.0025 (12)
C6	0.0417 (15)	0.0360 (16)	0.0468 (18)	0.0096 (12)	0.0220 (14)	0.0045 (14)
C7	0.0495 (18)	0.0358 (17)	0.066 (2)	0.0044 (14)	0.0248 (17)	0.0119 (16)
C8	0.0236 (11)	0.0356 (14)	0.0229 (12)	0.0021 (10)	0.0048 (10)	0.0001 (11)
C9	0.0257 (11)	0.0327 (13)	0.0229 (12)	0.0042 (10)	0.0084 (10)	0.0002 (11)
C10	0.0318 (12)	0.0323 (14)	0.0248 (13)	0.0061 (11)	0.0095 (11)	0.0021 (11)
C11	0.0337 (13)	0.0346 (14)	0.0265 (13)	0.0070 (11)	0.0103 (11)	0.0001 (11)
C12	0.0318 (13)	0.0314 (14)	0.0314 (14)	0.0035 (11)	0.0142 (11)	0.0020 (11)
C13	0.0350 (14)	0.0453 (17)	0.0357 (16)	0.0043 (12)	0.0123 (13)	0.0011 (14)
C14	0.0303 (14)	0.055 (2)	0.0478 (19)	0.0043 (13)	0.0066 (13)	0.0085 (16)
C15	0.0341 (15)	0.0502 (19)	0.062 (2)	0.0124 (13)	0.0223 (15)	0.0099 (17)
C16	0.0448 (16)	0.0409 (17)	0.056 (2)	0.0098 (14)	0.0284 (16)	0.0002 (15)
C17	0.0386 (14)	0.0352 (15)	0.0368 (16)	0.0033 (12)	0.0180 (13)	−0.0011 (13)
C18	0.0439 (16)	0.0426 (17)	0.0344 (16)	0.0111 (13)	0.0114 (13)	−0.0040 (13)
C19	0.0306 (13)	0.0366 (15)	0.0249 (13)	0.0020 (11)	0.0096 (11)	0.0030 (11)
C20	0.0363 (14)	0.0528 (19)	0.0269 (14)	0.0078 (13)	0.0076 (12)	0.0031 (13)
C21	0.058 (2)	0.070 (2)	0.0266 (15)	0.0113 (18)	0.0167 (15)	0.0025 (16)
C22	0.056 (2)	0.068 (2)	0.0418 (19)	0.0141 (17)	0.0301 (17)	0.0036 (17)
C23	0.0346 (15)	0.060 (2)	0.0468 (19)	0.0058 (14)	0.0197 (14)	0.0023 (16)
C24	0.0307 (13)	0.0400 (15)	0.0305 (14)	0.0023 (11)	0.0106 (11)	0.0029 (12)
C25	0.0271 (12)	0.0350 (14)	0.0280 (14)	0.0000 (11)	0.0056 (11)	−0.0010 (12)
C26	0.0300 (13)	0.0369 (15)	0.0329 (15)	0.0036 (11)	0.0114 (12)	−0.0023 (12)
N1	0.0288 (11)	0.0308 (12)	0.0310 (12)	0.0057 (9)	0.0088 (10)	0.0044 (10)
N2	0.0381 (14)	0.065 (2)	0.0456 (16)	−0.0050 (13)	0.0052 (13)	−0.0178 (15)
N3	0.0242 (11)	0.0548 (16)	0.0309 (13)	0.0000 (11)	0.0061 (10)	−0.0052 (12)
N4	0.0483 (15)	0.0466 (15)	0.0318 (14)	0.0116 (12)	0.0135 (12)	−0.0089 (12)
O1	0.0500 (12)	0.0498 (13)	0.0247 (10)	0.0188 (10)	0.0139 (9)	0.0043 (9)
O2	0.0329 (10)	0.0571 (14)	0.0322 (11)	0.0007 (9)	0.0064 (9)	−0.0134 (10)
C3	0.0327 (11)	0.0462 (16)	0.0462 (17)	−0.0091 (12)	0.0255 (12)	−0.0036 (14)
C1	0.057 (2)	0.0451 (19)	0.069 (2)	−0.0063 (16)	0.0351 (19)	−0.0027 (18)
C2	0.0441 (18)	0.057 (2)	0.066 (2)	−0.0071 (15)	0.0274 (17)	0.0100 (18)
C4	0.0348 (11)	0.0456 (14)	0.0338 (15)	0.0016 (12)	0.0177 (11)	−0.0060 (10)
S1	0.0605 (6)	0.0559 (6)	0.0906 (9)	0.0067 (4)	0.0380 (6)	0.0152 (5)

C5—C4	1.505 (4)	C16—C17	1.390 (4)
C5—C6	1.524 (4)	C16—H16	0.9300
C5—C9	1.560 (4)	C17—N4	1.379 (4)
C5—H5	0.9800	C18—N4	1.331 (4)
C6—N1	1.462 (4)	C18—H18	0.9300
C6—H6A	0.9700	C19—C20	1.382 (4)
C6—H6B	0.9700	C19—C24	1.388 (4)
C7—N1	1.457 (4)	C20—C21	1.385 (5)
C7—H7A	0.9600	C20—H20	0.9300
C7—H7B	0.9600	C21—C22	1.386 (5)
C7—H7C	0.9600	C21—H21	0.9300
C8—N1	1.442 (3)	C22—C23	1.372 (5)
C8—C19	1.506 (4)	C22—H22	0.9300
C8—C25	1.557 (3)	C23—C24	1.379 (4)
C8—C9	1.587 (4)	C23—H23	0.9300
C9—C26	1.469 (4)	C24—N3	1.401 (4)
C9—C10	1.562 (4)	C25—O2	1.220 (3)
C10—O1	1.231 (3)	C25—N3	1.349 (4)
C10—C11	1.430 (4)	C26—N2	1.135 (4)
C11—C18	1.385 (4)	N3—H3A	0.84 (2)
C11—C12	1.446 (4)	N4—H4A	0.844 (19)
C12—C13	1.396 (4)	C3—C2	1.492 (4)
C12—C17	1.405 (4)	C3—C4	1.528 (4)
C13—C14	1.385 (4)	C3—H3	0.9300
C13—H13	0.9300	C1—C2	1.310 (5)
C14—C15	1.386 (5)	C1—S1	1.676 (4)
C14—H14	0.9300	C1—H1	0.9300
C15—C16	1.365 (5)	C2—H2	0.9300
C15—H15	0.9300	C4—S1	1.708 (3)
C4—C5—C6	116.2 (2)	N4—C17—C16	129.9 (3)
C4—C5—C9	113.7 (2)	N4—C17—C12	107.3 (2)
C6—C5—C9	104.2 (2)	C16—C17—C12	122.8 (3)
C4—C5—H5	107.5	N4—C18—C11	110.1 (3)
C6—C5—H5	107.5	N4—C18—H18	124.9
C9—C5—H5	107.5	C11—C18—H18	124.9
N1—C6—C5	106.7 (2)	C20—C19—C24	119.8 (3)
N1—C6—H6A	110.4	C20—C19—C8	131.2 (3)
C5—C6—H6A	110.4	C24—C19—C8	109.0 (2)
N1—C6—H6B	110.4	C19—C20—C21	118.3 (3)
C5—C6—H6B	110.4	C19—C20—H20	120.8
H6A—C6—H6B	108.6	C21—C20—H20	120.8
N1—C7—H7A	109.5	C20—C21—C22	121.2 (3)
N1—C7—H7B	109.5	C20—C21—H21	119.4
H7A—C7—H7B	109.5	C22—C21—H21	119.4
N1—C7—H7C	109.5	C23—C22—C21	120.8 (3)
H7A—C7—H7C	109.5	C23—C22—H22	119.6
H7B—C7—H7C	109.5	C21—C22—H22	119.6
N1—C8—C19	116.8 (2)	C22—C23—C24	118.0 (3)
N1—C8—C25	116.9 (2)	C22—C23—H23	121.0
C19—C8—C25	101.2 (2)	C24—C23—H23	121.0
N1—C8—C9	100.7 (2)	C23—C24—C19	122.0 (3)
C19—C8—C9	115.0 (2)	C23—C24—N3	128.6 (3)
C25—C8—C9	106.4 (2)	C19—C24—N3	109.4 (2)
C26—C9—C5	109.0 (2)	O2—C25—N3	126.6 (3)
C26—C9—C10	113.1 (2)	O2—C25—C8	125.8 (2)
C5—C9—C10	112.5 (2)	N3—C25—C8	107.6 (2)
C26—C9—C8	108.5 (2)	N2—C26—C9	177.1 (3)
C5—C9—C8	101.5 (2)	C8—N1—C7	115.0 (2)
C10—C9—C8	111.6 (2)	C8—N1—C6	109.6 (2)
O1—C10—C11	121.4 (2)	C7—N1—C6	114.5 (3)
O1—C10—C9	116.5 (2)	C25—N3—C24	112.0 (2)
C11—C10—C9	121.9 (2)	C25—N3—H3A	134 (4)
C18—C11—C10	128.8 (3)	C24—N3—H3A	114 (4)
C18—C11—C12	105.8 (2)	C18—N4—C17	110.3 (3)
C10—C11—C12	125.3 (2)	C18—N4—H4A	125 (3)
C13—C12—C17	118.2 (3)	C17—N4—H4A	124 (3)
C13—C12—C11	135.3 (3)	C2—C3—C4	102.1 (3)
C17—C12—C11	106.5 (2)	C2—C3—H3	129.0
C14—C13—C12	118.7 (3)	C4—C3—H3	129.0
C14—C13—H13	120.7	C2—C1—S1	114.2 (3)
C12—C13—H13	120.7	C2—C1—H1	122.9
C13—C14—C15	121.6 (3)	S1—C1—H1	122.9
C13—C14—H14	119.2	C1—C2—C3	117.9 (3)
C15—C14—H14	119.2	C1—C2—H2	121.1
C16—C15—C14	121.2 (3)	C3—C2—H2	121.1
C16—C15—H15	119.4	C5—C4—C3	127.1 (3)
C14—C15—H15	119.4	C5—C4—S1	119.7 (2)
C15—C16—C17	117.5 (3)	C3—C4—S1	113.2 (2)
C15—C16—H16	121.3	C1—S1—C4	92.66 (17)
C17—C16—H16	121.3
C4—C5—C6—N1	132.7 (3)	N1—C8—C19—C24	−136.3 (3)
C9—C5—C6—N1	6.8 (3)	C25—C8—C19—C24	−8.2 (3)
C4—C5—C9—C26	−41.6 (3)	C9—C8—C19—C24	106.0 (3)
C6—C5—C9—C26	85.8 (3)	C24—C19—C20—C21	−2.6 (5)
C4—C5—C9—C10	84.7 (3)	C8—C19—C20—C21	176.3 (3)
C6—C5—C9—C10	−147.9 (2)	C19—C20—C21—C22	1.1 (6)
C4—C5—C9—C8	−155.9 (2)	C20—C21—C22—C23	1.1 (6)
C6—C5—C9—C8	−28.5 (3)	C21—C22—C23—C24	−1.8 (6)
N1—C8—C9—C26	−74.4 (3)	C22—C23—C24—C19	0.3 (5)
C19—C8—C9—C26	52.0 (3)	C22—C23—C24—N3	177.2 (3)
C25—C8—C9—C26	163.2 (2)	C20—C19—C24—C23	1.9 (5)
N1—C8—C9—C5	40.3 (2)	C8—C19—C24—C23	−177.1 (3)
C19—C8—C9—C5	166.8 (2)	C20—C19—C24—N3	−175.5 (3)
C25—C8—C9—C5	−82.1 (2)	C8—C19—C24—N3	5.4 (3)
N1—C8—C9—C10	160.4 (2)	N1—C8—C25—O2	−44.9 (4)
C19—C8—C9—C10	−73.2 (3)	C19—C8—C25—O2	−172.9 (3)
C25—C8—C9—C10	38.0 (3)	C9—C8—C25—O2	66.6 (4)
C26—C9—C10—O1	139.7 (3)	N1—C8—C25—N3	136.3 (3)
C5—C9—C10—O1	15.6 (4)	C19—C8—C25—N3	8.3 (3)
C8—C9—C10—O1	−97.7 (3)	C9—C8—C25—N3	−112.1 (3)
C26—C9—C10—C11	−45.4 (4)	C19—C8—N1—C7	65.8 (3)
C5—C9—C10—C11	−169.4 (3)	C25—C8—N1—C7	−54.3 (3)
C8—C9—C10—C11	77.2 (3)	C9—C8—N1—C7	−169.0 (2)
O1—C10—C11—C18	−168.2 (3)	C19—C8—N1—C6	−163.6 (2)
C9—C10—C11—C18	17.1 (5)	C25—C8—N1—C6	76.3 (3)
O1—C10—C11—C12	10.7 (5)	C9—C8—N1—C6	−38.4 (3)
C9—C10—C11—C12	−164.0 (3)	C5—C6—N1—C8	20.8 (3)
C18—C11—C12—C13	−176.8 (3)	C5—C6—N1—C7	151.7 (3)
C10—C11—C12—C13	4.1 (5)	O2—C25—N3—C24	175.5 (3)
C18—C11—C12—C17	1.3 (3)	C8—C25—N3—C24	−5.7 (3)
C10—C11—C12—C17	−177.8 (3)	C23—C24—N3—C25	−176.9 (3)
C17—C12—C13—C14	1.5 (4)	C19—C24—N3—C25	0.3 (4)
C11—C12—C13—C14	179.5 (3)	C11—C18—N4—C17	0.5 (4)
C12—C13—C14—C15	0.0 (5)	C16—C17—N4—C18	179.4 (3)
C13—C14—C15—C16	−1.7 (5)	C12—C17—N4—C18	0.3 (4)
C14—C15—C16—C17	1.6 (5)	S1—C1—C2—C3	−1.0 (5)
C15—C16—C17—N4	−178.9 (3)	C4—C3—C2—C1	1.1 (4)
C15—C16—C17—C12	0.1 (5)	C6—C5—C4—C3	−7.7 (4)
C13—C12—C17—N4	177.5 (3)	C9—C5—C4—C3	113.2 (3)
C11—C12—C17—N4	−1.0 (3)	C6—C5—C4—S1	173.7 (2)
C13—C12—C17—C16	−1.6 (5)	C9—C5—C4—S1	−65.4 (3)
C11—C12—C17—C16	179.8 (3)	C2—C3—C4—C5	−179.4 (3)
C10—C11—C18—N4	177.9 (3)	C2—C3—C4—S1	−0.7 (3)
C12—C11—C18—N4	−1.1 (4)	C2—C1—S1—C4	0.5 (3)
N1—C8—C19—C20	44.8 (4)	C5—C4—S1—C1	179.0 (3)
C25—C8—C19—C20	172.9 (3)	C3—C4—S1—C1	0.2 (3)
C9—C8—C19—C20	−72.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2i	0.84 (4)	2.12 (5)	2.828 (3)	142 (5)
N4—H4A···O1ii	0.85 (3)	1.99 (3)	2.829 (3)	177 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2i	0.84 (4)	2.12 (5)	2.828 (3)	142 (5)
N4—H4A⋯O1ii	0.85 (3)	1.99 (3)	2.829 (3)	177 (3)

Symmetry codes: (i) ; (ii) .