7-Benzyl-3-(4-fluoro-phen-yl)-2-(pyrrol-idin-1-yl)-5,6,7,8-tetra-hydro-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4(3H)-one.

In the title compound, C(26)H(25)FN(4)OS, the thienopyrimidine fused-ring system is close to planar (r.m.s. deviation = 0.066 Å), with a maximum deviation of 0.1243 (17) Å for the N atom adjacent to the carbonyl group. This ring system forms dihedral angles of 67.5 (1) and 88.9 (1) ° with the adjacent six-membered rings. Inter-molecular C-H⋯O hydrogen bonding and C-H⋯π inter-actions help to stabilize the crystal structure.

Related literature

For the biological and pharmaceutical properties of compounds containing the fused thienopyrimidine system, see: Amr et al. (2010 ▶); Huang et al. (2009 ▶); Jennings et al. (2005 ▶); Kikuchi et al. (2006 ▶); Mavrova et al. (2010 ▶); Santagati et al. (2002 ▶). For related structures, see: Hu et al. (2007 ▶); Xie et al. (2008 ▶).

Experimental

Crystal data

C26H25FN4OS

M = 460.56

Triclinic,

a = 8.132 (10) Å

b = 9.736 (11) Å

c = 15.540 (18) Å

α = 99.742 (16)°

β = 99.636 (11)°

γ = 105.551 (14)°

V = 1139 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 296 K

0.23 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.960, T max = 0.974

12210 measured reflections

5233 independent reflections

4018 reflections with I > 2σ(I)

R int = 0.154

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.180

S = 1.05

5233 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811030625/zq2114sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030625/zq2114Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030625/zq2114Isup3.cml

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

C26H25FN4OS	Z = 2
Mr = 460.56	F(000) = 484
Triclinic, P1	Dx = 1.343 Mg m−3
Hall symbol: -P 1	Melting point: 485 K
a = 8.132 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.736 (11) Å	Cell parameters from 2106 reflections
c = 15.540 (18) Å	θ = 2.7–27.5°
α = 99.742 (16)°	µ = 0.18 mm−1
β = 99.636 (11)°	T = 296 K
γ = 105.551 (14)°	Block, colourless
V = 1139 (2) Å3	0.23 × 0.20 × 0.15 mm

Bruker SMART CCD diffractometer	5233 independent reflections
Radiation source: fine-focus sealed tube	4018 reflections with I > 2σ(I)
graphite	Rint = 0.154
CCD Profile fitting scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.960, Tmax = 0.974	k = −12→12
12210 measured reflections	l = −20→20

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0691P)2] where P = (Fo2 + 2Fc2)/3
5233 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.38 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
S1	0.44564 (6)	0.17251 (6)	0.31146 (3)	0.04008 (18)
N2	0.3853 (2)	0.28656 (17)	0.47059 (11)	0.0354 (4)
O1	0.7783 (2)	0.16116 (16)	0.60615 (10)	0.0477 (4)
N3	0.57983 (19)	0.29116 (16)	0.60532 (10)	0.0318 (3)
N4	0.3472 (2)	0.39607 (17)	0.60525 (11)	0.0349 (4)
C13	0.6094 (2)	0.16139 (18)	0.46627 (13)	0.0322 (4)
C15	0.4366 (2)	0.32359 (19)	0.55846 (13)	0.0315 (4)
C17	0.6746 (2)	0.3752 (2)	0.69460 (12)	0.0335 (4)
C14	0.6647 (2)	0.19681 (19)	0.56157 (13)	0.0328 (4)
C16	0.4790 (2)	0.21316 (19)	0.42757 (13)	0.0332 (4)
N1	0.7929 (2)	−0.04640 (17)	0.25491 (12)	0.0401 (4)
C10	0.6883 (2)	0.09292 (18)	0.40137 (13)	0.0329 (4)
C23	0.3336 (3)	0.4011 (2)	0.69915 (14)	0.0403 (4)
H23A	0.4258	0.4826	0.7396	0.048*
H23B	0.3403	0.3110	0.7161	0.048*
C11	0.6146 (3)	0.0929 (2)	0.31656 (13)	0.0351 (4)
C22	0.7449 (3)	0.5255 (2)	0.70756 (14)	0.0393 (4)
H22	0.7291	0.5706	0.6600	0.047*
C26	0.2043 (2)	0.4368 (2)	0.55417 (15)	0.0402 (5)
H26A	0.1182	0.3514	0.5136	0.048*
H26B	0.2495	0.5072	0.5200	0.048*
C9	0.8400 (3)	0.0331 (2)	0.41996 (14)	0.0381 (4)
H9A	0.7991	−0.0636	0.4318	0.046*
H9B	0.9257	0.0961	0.4726	0.046*
C12	0.6811 (3)	0.0451 (2)	0.23597 (14)	0.0399 (5)
H12A	0.5828	−0.0095	0.1865	0.048*
H12B	0.7473	0.1305	0.2184	0.048*
C18	0.7011 (3)	0.3054 (2)	0.76407 (14)	0.0452 (5)
H18	0.6543	0.2044	0.7545	0.054*
C8	0.9246 (3)	0.0243 (2)	0.33961 (15)	0.0435 (5)
H8A	0.9891	0.1222	0.3367	0.052*
H8B	1.0071	−0.0308	0.3473	0.052*
F1	0.9572 (3)	0.6188 (2)	0.94182 (12)	0.1047 (7)
C4	0.7603 (3)	−0.1314 (3)	0.09123 (16)	0.0513 (6)
C21	0.8389 (3)	0.6084 (3)	0.79164 (17)	0.0530 (6)
H21	0.8838	0.7097	0.8019	0.064*
C19	0.7981 (3)	0.3875 (3)	0.84799 (16)	0.0596 (6)
H19	0.8183	0.3429	0.8954	0.072*
C24	0.1546 (3)	0.4208 (3)	0.70031 (16)	0.0516 (6)
H24A	0.1543	0.4772	0.7580	0.062*
H24B	0.0648	0.3269	0.6874	0.062*
C25	0.1256 (3)	0.5036 (2)	0.62624 (17)	0.0504 (5)
H25A	0.0018	0.4885	0.6040	0.061*
H25B	0.1850	0.6077	0.6478	0.061*
C7	0.8822 (3)	−0.0742 (3)	0.18182 (17)	0.0520 (6)
H7A	0.9434	−0.1444	0.1933	0.062*
H7B	0.9690	0.0161	0.1816	0.062*
C20	0.8637 (3)	0.5372 (3)	0.85920 (16)	0.0621 (7)
C3	0.6252 (4)	−0.2613 (3)	0.0722 (2)	0.0719 (8)
H3	0.6104	−0.3154	0.1158	0.086*
C5	0.7773 (4)	−0.0546 (3)	0.0246 (2)	0.0709 (8)
H5	0.8661	0.0339	0.0366	0.085*
C6	0.6658 (5)	−0.1054 (4)	−0.0599 (2)	0.0875 (10)
H6	0.6812	−0.0521	−0.1039	0.105*
C2	0.5115 (5)	−0.3116 (4)	−0.0117 (2)	0.0837 (9)
H2	0.4197	−0.3982	−0.0237	0.100*
C1	0.5346 (6)	−0.2330 (4)	−0.0777 (2)	0.0861 (10)
H1	0.4599	−0.2680	−0.1342	0.103*

	U11	U22	U33	U12	U13	U23
S1	0.0408 (3)	0.0565 (3)	0.0278 (3)	0.0268 (2)	0.0029 (2)	0.0076 (2)
N2	0.0305 (8)	0.0460 (9)	0.0319 (8)	0.0176 (7)	0.0042 (6)	0.0075 (7)
O1	0.0476 (9)	0.0631 (9)	0.0363 (8)	0.0338 (7)	−0.0036 (6)	0.0069 (7)
N3	0.0275 (7)	0.0394 (8)	0.0274 (8)	0.0124 (6)	0.0015 (6)	0.0056 (7)
N4	0.0297 (8)	0.0465 (8)	0.0312 (8)	0.0171 (7)	0.0059 (6)	0.0080 (7)
C13	0.0308 (9)	0.0346 (9)	0.0324 (10)	0.0131 (7)	0.0039 (7)	0.0082 (8)
C15	0.0261 (8)	0.0378 (9)	0.0307 (9)	0.0104 (7)	0.0040 (7)	0.0092 (8)
C17	0.0274 (8)	0.0467 (10)	0.0265 (9)	0.0141 (8)	0.0035 (7)	0.0062 (8)
C14	0.0301 (9)	0.0346 (9)	0.0326 (10)	0.0120 (7)	0.0015 (7)	0.0065 (8)
C16	0.0301 (9)	0.0403 (9)	0.0284 (9)	0.0140 (7)	0.0015 (7)	0.0058 (8)
N1	0.0432 (9)	0.0462 (9)	0.0363 (9)	0.0233 (8)	0.0103 (7)	0.0063 (8)
C10	0.0313 (9)	0.0341 (8)	0.0330 (10)	0.0128 (7)	0.0027 (7)	0.0065 (8)
C23	0.0353 (10)	0.0537 (11)	0.0334 (10)	0.0143 (9)	0.0110 (8)	0.0093 (9)
C11	0.0377 (10)	0.0399 (9)	0.0307 (10)	0.0183 (8)	0.0056 (8)	0.0076 (8)
C22	0.0326 (9)	0.0475 (10)	0.0375 (11)	0.0147 (8)	0.0062 (8)	0.0064 (9)
C26	0.0283 (9)	0.0514 (11)	0.0429 (12)	0.0166 (8)	0.0051 (8)	0.0119 (9)
C9	0.0352 (10)	0.0406 (9)	0.0371 (10)	0.0169 (8)	0.0003 (8)	0.0041 (8)
C12	0.0457 (11)	0.0466 (10)	0.0332 (10)	0.0233 (9)	0.0094 (9)	0.0090 (9)
C18	0.0461 (12)	0.0581 (12)	0.0318 (11)	0.0178 (10)	0.0051 (9)	0.0117 (10)
C8	0.0380 (11)	0.0500 (11)	0.0460 (12)	0.0208 (9)	0.0074 (9)	0.0097 (10)
F1	0.1166 (17)	0.1151 (14)	0.0450 (10)	0.0321 (12)	−0.0342 (10)	−0.0244 (10)
C4	0.0655 (15)	0.0610 (13)	0.0401 (12)	0.0356 (12)	0.0211 (11)	0.0099 (11)
C21	0.0433 (12)	0.0515 (12)	0.0502 (14)	0.0117 (10)	−0.0017 (10)	−0.0087 (11)
C19	0.0610 (15)	0.0860 (18)	0.0301 (11)	0.0277 (13)	−0.0020 (10)	0.0119 (12)
C24	0.0349 (11)	0.0754 (15)	0.0473 (13)	0.0192 (10)	0.0149 (9)	0.0119 (12)
C25	0.0361 (11)	0.0599 (13)	0.0606 (15)	0.0225 (10)	0.0135 (10)	0.0123 (12)
C7	0.0541 (13)	0.0638 (13)	0.0486 (14)	0.0317 (11)	0.0187 (11)	0.0111 (11)
C20	0.0575 (15)	0.0801 (17)	0.0335 (12)	0.0234 (13)	−0.0117 (10)	−0.0104 (12)
C3	0.102 (2)	0.0659 (16)	0.0445 (15)	0.0245 (16)	0.0109 (14)	0.0097 (13)
C5	0.0764 (19)	0.0890 (19)	0.0595 (18)	0.0321 (16)	0.0261 (15)	0.0278 (16)
C6	0.111 (3)	0.109 (3)	0.056 (2)	0.043 (2)	0.0215 (19)	0.037 (2)
C2	0.108 (3)	0.0735 (18)	0.0561 (19)	0.0235 (17)	0.0034 (16)	−0.0004 (16)
C1	0.121 (3)	0.100 (2)	0.0404 (15)	0.053 (2)	0.0078 (17)	0.0041 (16)

S1—C16	1.739 (3)	C9—H9B	0.9700
S1—C11	1.747 (2)	C12—H12A	0.9700
N2—C15	1.316 (3)	C12—H12B	0.9700
N2—C16	1.357 (3)	C18—C19	1.388 (3)
O1—C14	1.222 (2)	C18—H18	0.9300
N3—C15	1.406 (2)	C8—H8A	0.9700
N3—C14	1.438 (3)	C8—H8B	0.9700
N3—C17	1.452 (3)	F1—C20	1.364 (3)
N4—C15	1.354 (3)	C4—C5	1.380 (4)
N4—C23	1.475 (3)	C4—C3	1.383 (4)
N4—C26	1.478 (3)	C4—C7	1.499 (4)
C13—C16	1.384 (3)	C21—C20	1.369 (4)
C13—C14	1.427 (3)	C21—H21	0.9300
C13—C10	1.446 (3)	C19—C20	1.380 (4)
C17—C22	1.387 (3)	C19—H19	0.9300
C17—C18	1.386 (3)	C24—C25	1.535 (3)
N1—C12	1.463 (3)	C24—H24A	0.9700
N1—C7	1.473 (3)	C24—H24B	0.9700
N1—C8	1.476 (3)	C25—H25A	0.9700
C10—C11	1.353 (3)	C25—H25B	0.9700
C10—C9	1.506 (3)	C7—H7A	0.9700
C23—C24	1.521 (3)	C7—H7B	0.9700
C23—H23A	0.9700	C3—C2	1.391 (4)
C23—H23B	0.9700	C3—H3	0.9300
C11—C12	1.497 (3)	C5—C6	1.390 (5)
C22—C21	1.386 (3)	C5—H5	0.9300
C22—H22	0.9300	C6—C1	1.354 (5)
C26—C25	1.518 (3)	C6—H6	0.9300
C26—H26A	0.9700	C2—C1	1.387 (5)
C26—H26B	0.9700	C2—H2	0.9300
C9—C8	1.524 (3)	C1—H1	0.9300
C9—H9A	0.9700
C16—S1—C11	91.27 (9)	C11—C12—H12B	109.5
C15—N2—C16	115.47 (16)	H12A—C12—H12B	108.1
C15—N3—C14	121.92 (17)	C19—C18—C17	119.4 (2)
C15—N3—C17	121.57 (16)	C19—C18—H18	120.3
C14—N3—C17	115.13 (15)	C17—C18—H18	120.3
C15—N4—C23	127.56 (16)	N1—C8—C9	111.67 (19)
C15—N4—C26	117.88 (18)	N1—C8—H8A	109.3
C23—N4—C26	111.67 (16)	C9—C8—H8A	109.3
C16—C13—C14	118.39 (17)	N1—C8—H8B	109.3
C16—C13—C10	112.99 (18)	C9—C8—H8B	109.3
C14—C13—C10	128.06 (17)	H8A—C8—H8B	107.9
N2—C15—N4	118.25 (17)	C5—C4—C3	117.9 (3)
N2—C15—N3	122.75 (17)	C5—C4—C7	120.9 (3)
N4—C15—N3	118.99 (18)	C3—C4—C7	121.2 (2)
C22—C17—C18	120.97 (19)	C20—C21—C22	118.2 (2)
C22—C17—N3	118.44 (17)	C20—C21—H21	120.9
C18—C17—N3	120.52 (18)	C22—C21—H21	120.9
O1—C14—C13	126.76 (18)	C20—C19—C18	118.2 (2)
O1—C14—N3	119.67 (19)	C20—C19—H19	120.9
C13—C14—N3	113.47 (15)	C18—C19—H19	120.9
N2—C16—C13	127.03 (19)	C23—C24—C25	103.86 (17)
N2—C16—S1	121.94 (14)	C23—C24—H24A	111.0
C13—C16—S1	111.04 (14)	C25—C24—H24A	111.0
C12—N1—C7	111.41 (18)	C23—C24—H24B	111.0
C12—N1—C8	110.24 (16)	C25—C24—H24B	111.0
C7—N1—C8	109.4 (2)	H24A—C24—H24B	109.0
C11—C10—C13	111.91 (18)	C26—C25—C24	103.37 (18)
C11—C10—C9	120.74 (18)	C26—C25—H25A	111.1
C13—C10—C9	127.28 (18)	C24—C25—H25A	111.1
N4—C23—C24	103.68 (16)	C26—C25—H25B	111.1
N4—C23—H23A	111.0	C24—C25—H25B	111.1
C24—C23—H23A	111.0	H25A—C25—H25B	109.1
N4—C23—H23B	111.0	N1—C7—C4	113.4 (2)
C24—C23—H23B	111.0	N1—C7—H7A	108.9
H23A—C23—H23B	109.0	C4—C7—H7A	108.9
C10—C11—C12	124.32 (19)	N1—C7—H7B	108.9
C10—C11—S1	112.73 (15)	C4—C7—H7B	108.9
C12—C11—S1	122.64 (15)	H7A—C7—H7B	107.7
C21—C22—C17	119.8 (2)	F1—C20—C21	118.2 (3)
C21—C22—H22	120.1	F1—C20—C19	118.5 (3)
C17—C22—H22	120.1	C21—C20—C19	123.3 (2)
N4—C26—C25	103.64 (19)	C4—C3—C2	120.4 (3)
N4—C26—H26A	111.0	C4—C3—H3	119.8
C25—C26—H26A	111.0	C2—C3—H3	119.8
N4—C26—H26B	111.0	C4—C5—C6	122.0 (3)
C25—C26—H26B	111.0	C4—C5—H5	119.0
H26A—C26—H26B	109.0	C6—C5—H5	119.0
C10—C9—C8	109.86 (18)	C1—C6—C5	119.5 (3)
C10—C9—H9A	109.7	C1—C6—H6	120.3
C8—C9—H9A	109.7	C5—C6—H6	120.3
C10—C9—H9B	109.7	C1—C2—C3	120.2 (4)
C8—C9—H9B	109.7	C1—C2—H2	119.9
H9A—C9—H9B	108.2	C3—C2—H2	119.9
N1—C12—C11	110.81 (17)	C6—C1—C2	120.1 (3)
N1—C12—H12A	109.5	C6—C1—H1	120.0
C11—C12—H12A	109.5	C2—C1—H1	120.0
N1—C12—H12B	109.5
C16—N2—C15—N4	−179.48 (15)	C9—C10—C11—S1	−178.14 (13)
C16—N2—C15—N3	0.6 (3)	C16—S1—C11—C10	1.92 (16)
C23—N4—C15—N2	155.38 (18)	C16—S1—C11—C12	−172.02 (17)
C26—N4—C15—N2	−3.6 (2)	C18—C17—C22—C21	−1.9 (3)
C23—N4—C15—N3	−24.7 (3)	N3—C17—C22—C21	−178.84 (18)
C26—N4—C15—N3	176.30 (15)	C15—N4—C26—C25	175.64 (16)
C14—N3—C15—N2	−9.2 (3)	C23—N4—C26—C25	13.4 (2)
C17—N3—C15—N2	156.74 (18)	C11—C10—C9—C8	18.0 (2)
C14—N3—C15—N4	170.88 (16)	C13—C10—C9—C8	−158.70 (18)
C17—N3—C15—N4	−23.2 (2)	C7—N1—C12—C11	−170.65 (17)
C15—N3—C17—C22	−55.7 (2)	C8—N1—C12—C11	−49.0 (2)
C14—N3—C17—C22	111.1 (2)	C10—C11—C12—N1	19.6 (3)
C15—N3—C17—C18	127.3 (2)	S1—C11—C12—N1	−167.21 (13)
C14—N3—C17—C18	−65.8 (2)	C22—C17—C18—C19	0.6 (3)
C16—C13—C14—O1	−179.38 (18)	N3—C17—C18—C19	177.5 (2)
C10—C13—C14—O1	−8.6 (3)	C12—N1—C8—C9	66.5 (2)
C16—C13—C14—N3	−3.1 (2)	C7—N1—C8—C9	−170.69 (17)
C10—C13—C14—N3	167.70 (16)	C10—C9—C8—N1	−48.3 (2)
C15—N3—C14—O1	−173.49 (17)	C17—C22—C21—C20	2.0 (3)
C17—N3—C14—O1	19.7 (2)	C17—C18—C19—C20	0.5 (4)
C15—N3—C14—C13	9.9 (2)	N4—C23—C24—C25	−29.0 (2)
C17—N3—C14—C13	−156.85 (16)	N4—C26—C25—C24	−31.0 (2)
C15—N2—C16—C13	6.9 (3)	C23—C24—C25—C26	37.6 (2)
C15—N2—C16—S1	−173.02 (14)	C12—N1—C7—C4	−51.8 (3)
C14—C13—C16—N2	−5.5 (3)	C8—N1—C7—C4	−173.91 (18)
C10—C13—C16—N2	−177.61 (17)	C5—C4—C7—N1	118.8 (3)
C14—C13—C16—S1	174.45 (14)	C3—C4—C7—N1	−60.0 (3)
C10—C13—C16—S1	2.31 (19)	C22—C21—C20—F1	179.6 (2)
C11—S1—C16—N2	177.55 (16)	C22—C21—C20—C19	−0.8 (4)
C11—S1—C16—C13	−2.38 (14)	C18—C19—C20—F1	179.2 (2)
C16—C13—C10—C11	−0.9 (2)	C18—C19—C20—C21	−0.4 (4)
C14—C13—C10—C11	−172.11 (18)	C5—C4—C3—C2	0.1 (4)
C16—C13—C10—C9	176.07 (17)	C7—C4—C3—C2	178.9 (3)
C14—C13—C10—C9	4.9 (3)	C3—C4—C5—C6	−1.2 (4)
C15—N4—C23—C24	−150.15 (19)	C7—C4—C5—C6	180.0 (3)
C26—N4—C23—C24	9.9 (2)	C4—C5—C6—C1	0.9 (5)
C13—C10—C11—C12	172.87 (17)	C4—C3—C2—C1	1.2 (5)
C9—C10—C11—C12	−4.3 (3)	C5—C6—C1—C2	0.4 (5)
C13—C10—C11—S1	−0.9 (2)	C3—C2—C1—C6	−1.4 (5)

Cg1 and Cg2 are the centroids of the S1-C11-C10-C13-C16 and N2-C15-N3-C14-C13-C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O1i	0.97	2.50	3.461 (5)	171
C24—H24B···O1ii	0.97	2.44	3.316 (5)	151
C25—H25B···Cg1iii	0.97	2.86	3.693 (5)	144
C26—H26B···Cg2iii	0.97	2.80	3.717 (5)	158

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S1-C11-C10-C13-C16 and N2-C15-N3-C14-C13-C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O1i	0.97	2.50	3.461 (5)	171
C24—H24B⋯O1ii	0.97	2.44	3.316 (5)	151
C25—H25B⋯Cg1iii	0.97	2.86	3.693 (5)	144
C26—H26B⋯Cg2iii	0.97	2.80	3.717 (5)	158

Symmetry codes: (i) ; (ii) ; (iii) .