Crystal structure of ethyl 5''-fluoro-2'',3-dioxo-6',7',8',8a'-tetra-hydro-2'H,3H,5'H-di-spiro-[benzo[b]thio-phene-2,1'-indol-izine-3',3''-indoline]-2'-carboxyl-ate.

In the title compound, C25H23FN2O4S, the fused piperidine ring of the octa-hydro-indolizine ring system adopts a chair conformation and the five-membered ring has a twisted conformation on the N-C(spiro) bond. The mean planes of the benzo-thio-phene and indoline ring systems are inclined to the mean plane of the pyrrolidine ring by 83.1 (1) and 84.9 (1)°, respectively, and to each other by 29.37 (17)°. In the crystal, mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. The dimers are linked via C-H⋯O hydrogen bonds, forming slabs lying parallel to (100). The packing between the slabs features a short [2.734 (2) Å] F⋯F contact.

Related literature

For the biological activity of indole derivatives, see: Barden (2011 ▸); Oudard et al. (2011 ▸); Beale (2011 ▸); Aanandhi et al. (2008 ▸); Muthukumar et al. (2008 ▸). For crystal structures of similar compounds, see: Savithri et al. (2014 ▸).

Experimental

Crystal data

C25H23FN2O4S

M = 466.51

Monoclinic,

a = 13.877 (2) Å

b = 11.8999 (19) Å

c = 15.426 (4) Å

β = 116.463 (4)°

V = 2280.5 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.30 × 0.30 × 0.30 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.947, T max = 0.955

32121 measured reflections

4784 independent reflections

3652 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.04

4784 reflections

303 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.24 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: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL2014 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015002121/su5063sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015002121/su5063Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015002121/su5063fig1.tif

The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015002121/su5063fig2.tif

A view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in these inter­actions have been omitted for clarity).

CCDC reference: 1046671

Additional supporting information: crystallographic information; 3D view; checkCIF report

C25H23FN2O4S	F(000) = 976
Mr = 466.51	Dx = 1.359 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.877 (2) Å	Cell parameters from 3238 reflections
b = 11.8999 (19) Å	θ = 1.6–25.0°
c = 15.426 (4) Å	µ = 0.19 mm−1
β = 116.463 (4)°	T = 293 K
V = 2280.5 (8) Å3	Block, colourless
Z = 4	0.30 × 0.30 × 0.30 mm

Bruker SMART APEXII area-detector diffractometer	4784 independent reflections
Radiation source: fine-focus sealed tube	3652 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scans	θmax = 26.6°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −17→17
Tmin = 0.947, Tmax = 0.955	k = −15→15
32121 measured reflections	l = −19→19

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0484P)2 + 1.3589P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
4784 reflections	Δρmax = 0.38 e Å−3
303 parameters	Δρmin = −0.24 e Å−3

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
S1	0.35506 (4)	0.59504 (4)	0.45922 (4)	0.04126 (16)
F1	0.07518 (12)	1.08370 (13)	0.02567 (10)	0.0707 (5)
O1	0.42901 (14)	0.75803 (15)	0.29676 (15)	0.0677 (5)
O2	0.32609 (12)	0.60522 (12)	0.24108 (12)	0.0484 (4)
O3	0.06507 (11)	0.61184 (12)	0.25149 (11)	0.0497 (4)
O4	0.42650 (12)	0.85900 (12)	0.48990 (10)	0.0464 (4)
N1	0.18102 (13)	0.86296 (13)	0.36986 (11)	0.0320 (4)
N2	0.39881 (14)	1.00547 (14)	0.38496 (13)	0.0413 (4)
H2	0.453 (2)	1.047 (2)	0.4226 (18)	0.055 (7)*
C1	0.3758 (4)	0.4290 (3)	0.2058 (4)	0.1166 (15)
H1A	0.4227	0.3898	0.1854	0.175*
H1B	0.3032	0.4248	0.1557	0.175*
H1C	0.3799	0.3950	0.2638	0.175*
C2	0.4091 (2)	0.5476 (2)	0.2250 (2)	0.0677 (8)
H2A	0.4781	0.5538	0.2817	0.081*
H2B	0.4155	0.5801	0.1701	0.081*
C3	0.34861 (16)	0.70724 (17)	0.27985 (16)	0.0401 (5)
C4	0.25734 (14)	0.74688 (15)	0.29925 (13)	0.0308 (4)
H4	0.1921	0.7407	0.2377	0.037*
C5	0.23753 (14)	0.67371 (15)	0.37302 (13)	0.0305 (4)
C6	0.10876 (18)	0.73457 (18)	0.44935 (17)	0.0459 (5)
H6A	0.1225	0.6662	0.4873	0.055*
H6B	0.0443	0.7236	0.3890	0.055*
C7	0.0934 (2)	0.8330 (2)	0.50504 (19)	0.0569 (6)
H7A	0.0297	0.8203	0.5146	0.068*
H7B	0.1548	0.8380	0.5683	0.068*
C8	0.0813 (2)	0.9427 (2)	0.45076 (19)	0.0553 (6)
H8A	0.0129	0.9426	0.3930	0.066*
H8B	0.0806	1.0046	0.4914	0.066*
C9	0.17105 (19)	0.96107 (17)	0.42185 (17)	0.0454 (5)
H9A	0.1557	1.0270	0.3809	0.054*
H9B	0.2383	0.9737	0.4792	0.054*
C10	0.20346 (16)	0.76111 (15)	0.42910 (14)	0.0336 (4)
H10	0.2660	0.7761	0.4912	0.040*
C11	0.26183 (14)	0.86879 (15)	0.33304 (13)	0.0298 (4)
C12	0.23884 (15)	0.95884 (15)	0.25758 (13)	0.0315 (4)
C13	0.15370 (16)	0.97322 (17)	0.16708 (14)	0.0381 (5)
H13	0.0970	0.9223	0.1421	0.046*
C14	0.15659 (17)	1.06670 (19)	0.11540 (15)	0.0443 (5)
C15	0.23724 (19)	1.14452 (19)	0.14926 (17)	0.0499 (6)
H15	0.2349	1.2064	0.1116	0.060*
C16	0.32277 (18)	1.13050 (18)	0.24034 (17)	0.0467 (5)
H16	0.3788	1.1822	0.2652	0.056*
C17	0.32165 (16)	1.03742 (16)	0.29245 (14)	0.0358 (4)
C18	0.37352 (15)	0.90668 (16)	0.41243 (14)	0.0346 (4)
C19	0.14945 (14)	0.58543 (15)	0.31808 (14)	0.0331 (4)
C20	0.18285 (15)	0.47195 (16)	0.35464 (14)	0.0344 (4)
C21	0.11991 (19)	0.37579 (17)	0.32308 (17)	0.0464 (5)
H21	0.0485	0.3808	0.2767	0.056*
C22	0.1637 (2)	0.27384 (19)	0.3607 (2)	0.0601 (7)
H22	0.1221	0.2090	0.3404	0.072*
C23	0.2707 (2)	0.26735 (18)	0.4297 (2)	0.0589 (7)
H23	0.3002	0.1973	0.4537	0.071*
C24	0.33419 (19)	0.36132 (18)	0.46330 (17)	0.0474 (5)
H24	0.4053	0.3556	0.5101	0.057*
C25	0.28901 (16)	0.46518 (16)	0.42540 (14)	0.0349 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0304 (2)	0.0319 (3)	0.0474 (3)	−0.0023 (2)	0.0046 (2)	0.0043 (2)
F1	0.0645 (9)	0.0798 (11)	0.0452 (8)	−0.0036 (8)	0.0042 (7)	0.0238 (7)
O1	0.0545 (10)	0.0552 (10)	0.1114 (15)	−0.0150 (8)	0.0533 (11)	−0.0126 (10)
O2	0.0471 (9)	0.0390 (8)	0.0651 (10)	0.0031 (7)	0.0304 (8)	−0.0106 (7)
O3	0.0325 (7)	0.0351 (8)	0.0596 (10)	−0.0030 (6)	0.0009 (7)	−0.0007 (7)
O4	0.0420 (8)	0.0379 (8)	0.0404 (8)	−0.0110 (6)	0.0013 (6)	0.0069 (6)
N1	0.0370 (8)	0.0234 (8)	0.0375 (9)	−0.0013 (6)	0.0184 (7)	−0.0005 (6)
N2	0.0395 (9)	0.0313 (9)	0.0403 (9)	−0.0136 (8)	0.0063 (8)	0.0003 (7)
C1	0.159 (4)	0.0526 (19)	0.188 (4)	0.030 (2)	0.123 (4)	−0.005 (2)
C2	0.0676 (17)	0.0603 (16)	0.094 (2)	0.0148 (14)	0.0527 (16)	−0.0084 (15)
C3	0.0392 (11)	0.0346 (11)	0.0480 (12)	−0.0025 (9)	0.0208 (9)	−0.0010 (9)
C4	0.0295 (9)	0.0270 (9)	0.0330 (10)	−0.0038 (7)	0.0112 (8)	−0.0033 (7)
C5	0.0257 (9)	0.0241 (9)	0.0365 (10)	−0.0021 (7)	0.0093 (8)	0.0006 (7)
C6	0.0538 (13)	0.0395 (12)	0.0549 (13)	−0.0007 (10)	0.0336 (11)	0.0064 (10)
C7	0.0713 (17)	0.0557 (15)	0.0614 (15)	0.0034 (13)	0.0456 (14)	0.0020 (12)
C8	0.0738 (17)	0.0443 (13)	0.0642 (15)	0.0102 (12)	0.0455 (14)	−0.0025 (12)
C9	0.0647 (14)	0.0286 (10)	0.0512 (13)	0.0016 (10)	0.0333 (11)	−0.0036 (9)
C10	0.0379 (10)	0.0264 (9)	0.0347 (10)	−0.0021 (8)	0.0145 (8)	0.0017 (8)
C11	0.0301 (9)	0.0252 (9)	0.0304 (9)	−0.0041 (7)	0.0101 (8)	−0.0010 (7)
C12	0.0343 (10)	0.0264 (9)	0.0348 (10)	−0.0018 (8)	0.0162 (8)	−0.0013 (8)
C13	0.0374 (10)	0.0397 (11)	0.0349 (10)	−0.0035 (9)	0.0141 (9)	0.0007 (9)
C14	0.0432 (12)	0.0489 (13)	0.0354 (11)	0.0049 (10)	0.0127 (9)	0.0086 (10)
C15	0.0589 (14)	0.0420 (12)	0.0505 (13)	0.0003 (11)	0.0259 (11)	0.0169 (10)
C16	0.0495 (13)	0.0345 (11)	0.0534 (13)	−0.0098 (9)	0.0205 (11)	0.0053 (10)
C17	0.0377 (10)	0.0298 (10)	0.0389 (11)	−0.0031 (8)	0.0161 (9)	0.0013 (8)
C18	0.0351 (10)	0.0275 (9)	0.0364 (10)	−0.0064 (8)	0.0117 (8)	−0.0015 (8)
C19	0.0280 (9)	0.0267 (9)	0.0414 (11)	−0.0035 (7)	0.0126 (8)	−0.0040 (8)
C20	0.0347 (10)	0.0266 (9)	0.0427 (11)	−0.0019 (8)	0.0180 (9)	−0.0011 (8)
C21	0.0468 (12)	0.0335 (11)	0.0554 (13)	−0.0079 (9)	0.0198 (11)	−0.0049 (10)
C22	0.0697 (17)	0.0259 (11)	0.0760 (17)	−0.0098 (11)	0.0246 (14)	−0.0020 (11)
C23	0.0758 (17)	0.0253 (11)	0.0736 (17)	0.0053 (11)	0.0313 (14)	0.0067 (11)
C24	0.0468 (12)	0.0377 (11)	0.0536 (13)	0.0078 (10)	0.0186 (11)	0.0079 (10)
C25	0.0374 (10)	0.0273 (9)	0.0416 (11)	0.0004 (8)	0.0191 (9)	0.0015 (8)

S1—C25	1.753 (2)	C7—H7A	0.9700
S1—C5	1.8362 (18)	C7—H7B	0.9700
F1—C14	1.356 (2)	C8—C9	1.515 (3)
O1—C3	1.191 (3)	C8—H8A	0.9700
O2—C3	1.328 (2)	C8—H8B	0.9700
O2—C2	1.454 (3)	C9—H9A	0.9700
O3—C19	1.205 (2)	C9—H9B	0.9700
O4—C18	1.228 (2)	C10—H10	0.9800
N1—C9	1.458 (2)	C11—C12	1.508 (3)
N1—C10	1.465 (2)	C11—C18	1.554 (2)
N1—C11	1.467 (2)	C12—C13	1.380 (3)
N2—C18	1.348 (2)	C12—C17	1.390 (3)
N2—C17	1.402 (3)	C13—C14	1.380 (3)
N2—H2	0.87 (3)	C13—H13	0.9300
C1—C2	1.474 (4)	C14—C15	1.365 (3)
C1—H1A	0.9600	C15—C16	1.387 (3)
C1—H1B	0.9600	C15—H15	0.9300
C1—H1C	0.9600	C16—C17	1.373 (3)
C2—H2A	0.9700	C16—H16	0.9300
C2—H2B	0.9700	C19—C20	1.457 (3)
C3—C4	1.501 (3)	C20—C21	1.389 (3)
C4—C11	1.533 (2)	C20—C25	1.391 (3)
C4—C5	1.552 (3)	C21—C22	1.365 (3)
C4—H4	0.9800	C21—H21	0.9300
C5—C19	1.547 (2)	C22—C23	1.391 (4)
C5—C10	1.555 (3)	C22—H22	0.9300
C6—C10	1.513 (3)	C23—C24	1.374 (3)
C6—C7	1.523 (3)	C23—H23	0.9300
C6—H6A	0.9700	C24—C25	1.391 (3)
C6—H6B	0.9700	C24—H24	0.9300
C7—C8	1.520 (3)
C25—S1—C5	93.21 (9)	C8—C9—H9B	109.7
C3—O2—C2	117.57 (19)	H9A—C9—H9B	108.2
C9—N1—C10	111.42 (15)	N1—C10—C6	109.79 (16)
C9—N1—C11	116.84 (15)	N1—C10—C5	103.83 (15)
C10—N1—C11	107.09 (14)	C6—C10—C5	118.85 (16)
C18—N2—C17	111.63 (16)	N1—C10—H10	108.0
C18—N2—H2	123.8 (16)	C6—C10—H10	108.0
C17—N2—H2	124.2 (16)	C5—C10—H10	108.0
C2—C1—H1A	109.5	N1—C11—C12	113.40 (15)
C2—C1—H1B	109.5	N1—C11—C4	99.47 (14)
H1A—C1—H1B	109.5	C12—C11—C4	116.58 (15)
C2—C1—H1C	109.5	N1—C11—C18	112.01 (15)
H1A—C1—H1C	109.5	C12—C11—C18	101.29 (14)
H1B—C1—H1C	109.5	C4—C11—C18	114.69 (15)
O2—C2—C1	106.6 (2)	C13—C12—C17	119.70 (18)
O2—C2—H2A	110.4	C13—C12—C11	131.32 (17)
C1—C2—H2A	110.4	C17—C12—C11	108.98 (16)
O2—C2—H2B	110.4	C14—C13—C12	116.89 (19)
C1—C2—H2B	110.4	C14—C13—H13	121.6
H2A—C2—H2B	108.6	C12—C13—H13	121.6
O1—C3—O2	124.9 (2)	F1—C14—C15	117.2 (2)
O1—C3—C4	126.0 (2)	F1—C14—C13	118.98 (19)
O2—C3—C4	109.08 (17)	C15—C14—C13	123.8 (2)
C3—C4—C11	117.05 (16)	C14—C15—C16	119.4 (2)
C3—C4—C5	114.26 (16)	C14—C15—H15	120.3
C11—C4—C5	105.98 (15)	C16—C15—H15	120.3
C3—C4—H4	106.3	C17—C16—C15	117.5 (2)
C11—C4—H4	106.3	C17—C16—H16	121.2
C5—C4—H4	106.3	C15—C16—H16	121.2
C19—C5—C4	109.53 (15)	C16—C17—C12	122.62 (19)
C19—C5—C10	113.40 (15)	C16—C17—N2	127.73 (19)
C4—C5—C10	103.29 (14)	C12—C17—N2	109.64 (17)
C19—C5—S1	106.29 (12)	O4—C18—N2	125.60 (18)
C4—C5—S1	115.26 (13)	O4—C18—C11	125.97 (17)
C10—C5—S1	109.29 (13)	N2—C18—C11	108.26 (16)
C10—C6—C7	108.01 (18)	O3—C19—C20	126.31 (17)
C10—C6—H6A	110.1	O3—C19—C5	121.35 (17)
C7—C6—H6A	110.1	C20—C19—C5	112.32 (15)
C10—C6—H6B	110.1	C21—C20—C25	120.52 (18)
C7—C6—H6B	110.1	C21—C20—C19	125.85 (18)
H6A—C6—H6B	108.4	C25—C20—C19	113.60 (16)
C8—C7—C6	111.02 (19)	C22—C21—C20	119.5 (2)
C8—C7—H7A	109.4	C22—C21—H21	120.3
C6—C7—H7A	109.4	C20—C21—H21	120.3
C8—C7—H7B	109.4	C21—C22—C23	119.7 (2)
C6—C7—H7B	109.4	C21—C22—H22	120.1
H7A—C7—H7B	108.0	C23—C22—H22	120.1
C9—C8—C7	112.5 (2)	C24—C23—C22	122.0 (2)
C9—C8—H8A	109.1	C24—C23—H23	119.0
C7—C8—H8A	109.1	C22—C23—H23	119.0
C9—C8—H8B	109.1	C23—C24—C25	118.1 (2)
C7—C8—H8B	109.1	C23—C24—H24	120.9
H8A—C8—H8B	107.8	C25—C24—H24	120.9
N1—C9—C8	109.79 (18)	C20—C25—C24	120.17 (18)
N1—C9—H9A	109.7	C20—C25—S1	114.38 (14)
C8—C9—H9A	109.7	C24—C25—S1	125.45 (16)
N1—C9—H9B	109.7
C3—O2—C2—C1	165.9 (3)	C4—C11—C12—C17	−128.26 (18)
C2—O2—C3—O1	5.0 (4)	C18—C11—C12—C17	−3.1 (2)
C2—O2—C3—C4	−174.5 (2)	C17—C12—C13—C14	0.4 (3)
O1—C3—C4—C11	7.5 (3)	C11—C12—C13—C14	179.6 (2)
O2—C3—C4—C11	−172.97 (16)	C12—C13—C14—F1	179.32 (19)
O1—C3—C4—C5	−117.2 (2)	C12—C13—C14—C15	−0.8 (3)
O2—C3—C4—C5	62.3 (2)	F1—C14—C15—C16	−179.5 (2)
C3—C4—C5—C19	−94.74 (18)	C13—C14—C15—C16	0.6 (4)
C11—C4—C5—C19	134.87 (15)	C14—C15—C16—C17	0.0 (4)
C3—C4—C5—C10	144.15 (16)	C15—C16—C17—C12	−0.3 (3)
C11—C4—C5—C10	13.77 (18)	C15—C16—C17—N2	179.6 (2)
C3—C4—C5—S1	25.0 (2)	C13—C12—C17—C16	0.1 (3)
C11—C4—C5—S1	−105.36 (15)	C11—C12—C17—C16	−179.2 (2)
C25—S1—C5—C19	−1.52 (14)	C13—C12—C17—N2	−179.83 (18)
C25—S1—C5—C4	−123.05 (14)	C11—C12—C17—N2	0.8 (2)
C25—S1—C5—C10	121.20 (13)	C18—N2—C17—C16	−177.7 (2)
C10—C6—C7—C8	54.8 (3)	C18—N2—C17—C12	2.3 (2)
C6—C7—C8—C9	−51.8 (3)	C17—N2—C18—O4	−179.8 (2)
C10—N1—C9—C8	−58.9 (2)	C17—N2—C18—C11	−4.3 (2)
C11—N1—C9—C8	177.59 (17)	N1—C11—C18—O4	58.7 (3)
C7—C8—C9—N1	52.5 (3)	C12—C11—C18—O4	179.9 (2)
C9—N1—C10—C6	64.7 (2)	C4—C11—C18—O4	−53.7 (3)
C11—N1—C10—C6	−166.38 (16)	N1—C11—C18—N2	−116.76 (18)
C9—N1—C10—C5	−167.21 (16)	C12—C11—C18—N2	4.4 (2)
C11—N1—C10—C5	−38.31 (17)	C4—C11—C18—N2	130.83 (18)
C7—C6—C10—N1	−61.1 (2)	C4—C5—C19—O3	−49.5 (3)
C7—C6—C10—C5	179.72 (18)	C10—C5—C19—O3	65.3 (2)
C19—C5—C10—N1	−104.87 (17)	S1—C5—C19—O3	−174.61 (17)
C4—C5—C10—N1	13.58 (17)	C4—C5—C19—C20	128.87 (17)
S1—C5—C10—N1	136.76 (13)	C10—C5—C19—C20	−116.35 (18)
C19—C5—C10—C6	17.4 (2)	S1—C5—C19—C20	3.7 (2)
C4—C5—C10—C6	135.84 (18)	O3—C19—C20—C21	−4.7 (4)
S1—C5—C10—C6	−100.99 (18)	C5—C19—C20—C21	177.0 (2)
C9—N1—C11—C12	−63.7 (2)	O3—C19—C20—C25	173.4 (2)
C10—N1—C11—C12	170.60 (15)	C5—C19—C20—C25	−4.8 (2)
C9—N1—C11—C4	171.82 (16)	C25—C20—C21—C22	−1.3 (3)
C10—N1—C11—C4	46.10 (17)	C19—C20—C21—C22	176.8 (2)
C9—N1—C11—C18	50.2 (2)	C20—C21—C22—C23	−0.4 (4)
C10—N1—C11—C18	−75.51 (17)	C21—C22—C23—C24	1.5 (4)
C3—C4—C11—N1	−164.31 (16)	C22—C23—C24—C25	−0.9 (4)
C5—C4—C11—N1	−35.55 (17)	C21—C20—C25—C24	1.9 (3)
C3—C4—C11—C12	73.4 (2)	C19—C20—C25—C24	−176.41 (19)
C5—C4—C11—C12	−157.80 (15)	C21—C20—C25—S1	−178.07 (17)
C3—C4—C11—C18	−44.7 (2)	C19—C20—C25—S1	3.6 (2)
C5—C4—C11—C18	84.10 (18)	C23—C24—C25—C20	−0.8 (3)
N1—C11—C12—C13	−62.1 (3)	C23—C24—C25—S1	179.14 (19)
C4—C11—C12—C13	52.5 (3)	C5—S1—C25—C20	−1.11 (17)
C18—C11—C12—C13	177.7 (2)	C5—S1—C25—C24	179.0 (2)
N1—C11—C12—C17	117.10 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4i	0.87 (3)	1.96 (3)	2.834 (2)	179 (2)
C1—H1A···O1ii	0.96	2.50	3.401 (4)	156

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N2H2O4i	0.87(3)	1.96(3)	2.834(2)	179(2)
C1H1AO1ii	0.96	2.50	3.401(4)	156

Symmetry codes: (i) ; (ii) .