2-Ethyl-sulfanyl-7-fluoro-3-(1H-1,2,4-triazol-1-yl)-4H-thio-chromen-4-one.

The asymmetric unit of the title compound, C(13)H(10)FN(3)OS(2), contains two independent mol-ecules, which differ slightly in the relative orientations of the triazole and ethyl-sulfanyl groups with respect to the planar thio-chromen-4-one frameworks. The dihedral angles between the mean planes of the triazole groups and the corresponding six-membered C(5)OS rings are 56.8 (1) and 52.9 (1)°, while the S-C-S-C dihedral angles are -11.7 (2) and -16.3 (2)°. In the crystal structure, inter-molecular C-H⋯O and C-H⋯N hydrogen bonds link the mol-ecules in a stacked arrangement along the a axis. A weak intramolecular C-H⋯·O interaction results in the formation of a non-planar five-membered ring.

Related literature

For related compounds containing the 4H-thio­chromen-4-one fragment, see: Adams et al. (1991 ▶); Nakazumi et al. (1992 ▶); Weiss et al. (2008 ▶); Li, Xiao, Liu & Yu (2010 ▶); Li, Xiao, Yu & Liu (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H10FN3OS2

M = 307.36

Triclinic,

a = 8.1060 (16) Å

b = 11.288 (2) Å

c = 15.163 (3) Å

α = 83.12 (3)°

β = 83.15 (3)°

γ = 79.36 (3)°

V = 1347.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.888, T max = 0.961

5271 measured reflections

4892 independent reflections

3725 reflections with I > 2σ(I)

R int = 0.020

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.135

S = 1.00

4892 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810030175/zq2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030175/zq2051Isup2.hkl

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

C13H10FN3OS2	Z = 4
Mr = 307.36	F(000) = 632
Triclinic, P1	Dx = 1.516 Mg m−3
Hall symbol: -P 1	Melting point: 432 K
a = 8.1060 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.288 (2) Å	Cell parameters from 25 reflections
c = 15.163 (3) Å	θ = 9–14°
α = 83.12 (3)°	µ = 0.41 mm−1
β = 83.15 (3)°	T = 293 K
γ = 79.36 (3)°	Block, yellow
V = 1347.0 (5) Å3	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	3725 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
graphite	θmax = 25.3°, θmin = 1.4°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −13→13
Tmin = 0.888, Tmax = 0.961	l = −18→18
5271 measured reflections	3 standard reflections every 200 reflections
4892 independent reflections	intensity decay: 1%

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.087P)2] where P = (Fo2 + 2Fc2)/3
4892 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.29 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	−0.15082 (10)	0.40138 (7)	−0.02746 (5)	0.0448 (2)
S2	0.05140 (10)	0.20004 (7)	0.07527 (4)	0.0415 (2)
F1	0.4481 (3)	−0.17048 (19)	0.17733 (13)	0.0733 (6)
O1	0.1829 (3)	0.05374 (19)	−0.18751 (13)	0.0564 (6)
N1	−0.0026 (3)	0.2800 (2)	−0.18726 (14)	0.0374 (5)
N2	0.0365 (4)	0.3935 (2)	−0.21190 (16)	0.0474 (6)
N3	−0.0921 (4)	0.3345 (2)	−0.31908 (16)	0.0505 (7)
C1	−0.3454 (5)	0.5338 (3)	0.0936 (2)	0.0671 (10)
H1A	−0.3849	0.5452	0.1547	0.101*
H1B	−0.4391	0.5298	0.0615	0.101*
H1C	−0.2920	0.6005	0.0671	0.101*
C2	−0.2196 (4)	0.4170 (3)	0.08944 (19)	0.0483 (8)
H2B	−0.2719	0.3488	0.1161	0.058*
H2C	−0.1242	0.4199	0.1216	0.058*
C3	−0.0111 (3)	0.2636 (2)	−0.02745 (17)	0.0346 (6)
C4	0.1860 (3)	0.0661 (2)	0.05066 (17)	0.0335 (6)
C5	0.2616 (4)	−0.0010 (3)	0.12351 (19)	0.0423 (7)
H5A	0.2386	0.0250	0.1803	0.051*
C6	0.3705 (4)	−0.1061 (3)	0.1084 (2)	0.0489 (8)
C7	0.4072 (4)	−0.1493 (3)	0.0251 (2)	0.0476 (7)
H7A	0.4816	−0.2214	0.0173	0.057*
C8	0.3312 (4)	−0.0832 (3)	−0.04493 (19)	0.0419 (7)
H8A	0.3534	−0.1116	−0.1010	0.050*
C9	0.2199 (3)	0.0267 (2)	−0.03439 (17)	0.0335 (6)
C10	0.1509 (4)	0.0959 (2)	−0.11443 (17)	0.0369 (6)
C11	0.0459 (3)	0.2127 (2)	−0.10583 (17)	0.0340 (6)
C12	−0.0763 (4)	0.2477 (3)	−0.25322 (19)	0.0460 (7)
H12A	−0.1115	0.1737	−0.2524	0.055*
C13	−0.0206 (4)	0.4192 (3)	−0.29026 (19)	0.0485 (8)
H13A	−0.0122	0.4924	−0.3244	0.058*
S3	−0.37421 (11)	−0.30227 (7)	0.49425 (5)	0.0502 (2)
S4	−0.26104 (10)	−0.08916 (6)	0.39414 (4)	0.0418 (2)
F2	−0.1135 (3)	0.31666 (19)	0.28874 (13)	0.0754 (7)
O2	−0.2316 (3)	0.0220 (2)	0.66100 (13)	0.0554 (6)
N4	−0.3399 (3)	−0.1897 (2)	0.65791 (14)	0.0391 (5)
N5	−0.2627 (4)	−0.3070 (2)	0.67609 (17)	0.0596 (8)
N6	−0.4426 (4)	−0.2446 (2)	0.79373 (16)	0.0547 (7)
C14	−0.4777 (5)	−0.4194 (3)	0.3729 (3)	0.0699 (11)
H14A	−0.5044	−0.4217	0.3133	0.105*
H14B	−0.5756	−0.4267	0.4141	0.105*
H14C	−0.3883	−0.4852	0.3869	0.105*
C15	−0.4220 (4)	−0.3008 (3)	0.3800 (2)	0.0519 (8)
H15A	−0.5110	−0.2335	0.3658	0.062*
H15B	−0.3227	−0.2924	0.3388	0.062*
C16	−0.3121 (3)	−0.1627 (2)	0.49766 (17)	0.0367 (6)
C17	−0.2133 (3)	0.0464 (2)	0.41911 (17)	0.0355 (6)
C18	−0.1784 (4)	0.1276 (3)	0.34501 (19)	0.0441 (7)
H18A	−0.1813	0.1085	0.2873	0.053*
C19	−0.1398 (4)	0.2359 (3)	0.3600 (2)	0.0487 (8)
C20	−0.1302 (4)	0.2667 (3)	0.4445 (2)	0.0492 (8)
H20A	−0.1024	0.3408	0.4524	0.059*
C21	−0.1624 (4)	0.1861 (3)	0.51620 (19)	0.0427 (7)
H21A	−0.1550	0.2054	0.5734	0.051*
C22	−0.2065 (3)	0.0748 (2)	0.50541 (17)	0.0359 (6)
C23	−0.2438 (4)	−0.0071 (3)	0.58617 (17)	0.0383 (6)
C24	−0.2987 (3)	−0.1197 (2)	0.57607 (17)	0.0359 (6)
C25	−0.4443 (4)	−0.1566 (3)	0.72971 (19)	0.0439 (7)
H25A	−0.5098	−0.0801	0.7333	0.053*
C26	−0.3311 (5)	−0.3339 (3)	0.7569 (2)	0.0652 (10)
H26A	−0.3043	−0.4105	0.7873	0.078*

	U11	U22	U33	U12	U13	U23
S1	0.0554 (5)	0.0408 (4)	0.0355 (4)	0.0018 (3)	−0.0064 (3)	−0.0074 (3)
S2	0.0526 (5)	0.0448 (4)	0.0255 (3)	0.0000 (3)	−0.0058 (3)	−0.0078 (3)
F1	0.0731 (14)	0.0811 (14)	0.0548 (12)	0.0135 (11)	−0.0248 (11)	0.0130 (10)
O1	0.0879 (17)	0.0500 (12)	0.0260 (10)	0.0068 (12)	−0.0063 (11)	−0.0105 (9)
N1	0.0508 (14)	0.0344 (12)	0.0284 (11)	−0.0104 (11)	−0.0063 (10)	−0.0021 (9)
N2	0.0697 (18)	0.0384 (13)	0.0372 (13)	−0.0180 (12)	−0.0082 (12)	0.0000 (10)
N3	0.0672 (18)	0.0487 (15)	0.0369 (13)	−0.0085 (13)	−0.0183 (13)	0.0007 (11)
C1	0.062 (2)	0.067 (2)	0.070 (2)	0.0081 (19)	−0.0055 (19)	−0.0280 (19)
C2	0.0549 (19)	0.0489 (17)	0.0391 (16)	−0.0026 (15)	0.0006 (14)	−0.0117 (13)
C3	0.0408 (15)	0.0357 (14)	0.0293 (13)	−0.0092 (12)	−0.0068 (12)	−0.0049 (11)
C4	0.0333 (14)	0.0389 (15)	0.0297 (13)	−0.0108 (12)	−0.0036 (11)	−0.0016 (11)
C5	0.0457 (17)	0.0504 (17)	0.0317 (15)	−0.0112 (14)	−0.0054 (13)	−0.0013 (13)
C6	0.0417 (17)	0.0577 (19)	0.0442 (18)	−0.0061 (15)	−0.0110 (14)	0.0104 (15)
C7	0.0420 (17)	0.0426 (17)	0.0541 (19)	−0.0012 (14)	−0.0004 (15)	−0.0018 (14)
C8	0.0465 (17)	0.0412 (16)	0.0366 (15)	−0.0066 (13)	0.0025 (13)	−0.0058 (12)
C9	0.0340 (14)	0.0377 (14)	0.0294 (13)	−0.0090 (12)	−0.0005 (11)	−0.0039 (11)
C10	0.0431 (16)	0.0393 (15)	0.0287 (14)	−0.0089 (13)	−0.0013 (12)	−0.0044 (11)
C11	0.0430 (16)	0.0354 (14)	0.0256 (13)	−0.0106 (12)	−0.0048 (11)	−0.0031 (11)
C12	0.060 (2)	0.0435 (16)	0.0386 (16)	−0.0134 (15)	−0.0140 (14)	−0.0045 (13)
C13	0.067 (2)	0.0403 (16)	0.0354 (16)	−0.0082 (15)	−0.0043 (15)	0.0032 (13)
S3	0.0691 (6)	0.0424 (4)	0.0421 (4)	−0.0165 (4)	−0.0088 (4)	−0.0015 (3)
S4	0.0586 (5)	0.0421 (4)	0.0258 (4)	−0.0112 (3)	−0.0035 (3)	−0.0048 (3)
F2	0.1168 (19)	0.0736 (14)	0.0465 (11)	−0.0540 (13)	−0.0166 (11)	0.0177 (10)
O2	0.0827 (17)	0.0599 (14)	0.0287 (11)	−0.0237 (12)	−0.0071 (11)	−0.0062 (9)
N4	0.0420 (14)	0.0436 (13)	0.0289 (12)	−0.0032 (11)	−0.0011 (10)	−0.0009 (10)
N5	0.073 (2)	0.0467 (15)	0.0439 (15)	0.0110 (14)	0.0090 (14)	0.0074 (12)
N6	0.0624 (18)	0.0575 (17)	0.0366 (14)	−0.0042 (14)	0.0075 (13)	0.0038 (12)
C14	0.087 (3)	0.064 (2)	0.068 (2)	−0.023 (2)	−0.015 (2)	−0.0210 (19)
C15	0.061 (2)	0.0527 (19)	0.0441 (18)	−0.0092 (16)	−0.0056 (16)	−0.0123 (15)
C16	0.0371 (15)	0.0382 (15)	0.0328 (14)	−0.0022 (12)	−0.0023 (12)	−0.0028 (11)
C17	0.0354 (15)	0.0426 (15)	0.0276 (13)	−0.0050 (12)	−0.0030 (11)	−0.0028 (11)
C18	0.0482 (18)	0.0550 (18)	0.0309 (15)	−0.0136 (15)	−0.0058 (13)	−0.0023 (13)
C19	0.0531 (19)	0.0575 (19)	0.0384 (16)	−0.0210 (16)	−0.0079 (14)	0.0052 (14)
C20	0.054 (2)	0.0489 (18)	0.0495 (18)	−0.0194 (15)	−0.0093 (15)	−0.0039 (14)
C21	0.0459 (17)	0.0492 (17)	0.0353 (15)	−0.0101 (14)	−0.0077 (13)	−0.0073 (13)
C22	0.0338 (15)	0.0408 (15)	0.0332 (14)	−0.0049 (12)	−0.0063 (12)	−0.0031 (12)
C23	0.0423 (16)	0.0433 (16)	0.0277 (14)	−0.0027 (13)	−0.0038 (12)	−0.0036 (12)
C24	0.0356 (15)	0.0418 (15)	0.0270 (13)	−0.0002 (12)	−0.0012 (11)	−0.0018 (11)
C25	0.0454 (17)	0.0479 (17)	0.0356 (15)	−0.0048 (14)	0.0039 (13)	−0.0060 (13)
C26	0.083 (3)	0.053 (2)	0.0447 (19)	0.0065 (19)	0.0102 (18)	0.0120 (15)

S1—C3	1.747 (3)	S3—C16	1.749 (3)
S1—C2	1.813 (3)	S3—C15	1.817 (3)
S2—C3	1.727 (3)	S4—C16	1.727 (3)
S2—C4	1.745 (3)	S4—C17	1.740 (3)
F1—C6	1.350 (3)	F2—C19	1.351 (3)
O1—C10	1.238 (3)	O2—C23	1.238 (3)
N1—C12	1.342 (3)	N4—C25	1.343 (4)
N1—N2	1.375 (3)	N4—N5	1.367 (3)
N1—C11	1.427 (3)	N4—C24	1.428 (3)
N2—C13	1.308 (4)	N5—C26	1.308 (4)
N3—C12	1.313 (4)	N6—C25	1.303 (4)
N3—C13	1.344 (4)	N6—C26	1.350 (4)
C1—C2	1.513 (4)	C14—C15	1.509 (4)
C1—H1A	0.9600	C14—H14A	0.9600
C1—H1B	0.9600	C14—H14B	0.9600
C1—H1C	0.9600	C14—H14C	0.9600
C2—H2B	0.9700	C15—H15A	0.9700
C2—H2C	0.9700	C15—H15B	0.9700
C3—C11	1.375 (4)	C16—C24	1.360 (4)
C4—C9	1.394 (4)	C17—C22	1.393 (4)
C4—C5	1.400 (4)	C17—C18	1.398 (4)
C5—C6	1.367 (4)	C18—C19	1.368 (4)
C5—H5A	0.9300	C18—H18A	0.9300
C6—C7	1.387 (4)	C19—C20	1.381 (4)
C7—C8	1.364 (4)	C20—C21	1.364 (4)
C7—H7A	0.9300	C20—H20A	0.9300
C8—C9	1.407 (4)	C21—C22	1.401 (4)
C8—H8A	0.9300	C21—H21A	0.9300
C9—C10	1.472 (4)	C22—C23	1.479 (4)
C10—C11	1.443 (4)	C23—C24	1.452 (4)
C12—H12A	0.9300	C25—H25A	0.9300
C13—H13A	0.9300	C26—H26A	0.9300
C3—S1—C2	104.62 (14)	C16—S3—C15	104.65 (14)
C3—S2—C4	103.44 (13)	C16—S4—C17	103.64 (13)
C12—N1—N2	108.8 (2)	C25—N4—N5	108.5 (2)
C12—N1—C11	130.1 (2)	C25—N4—C24	129.6 (2)
N2—N1—C11	120.9 (2)	N5—N4—C24	121.8 (2)
C13—N2—N1	101.4 (2)	C26—N5—N4	101.7 (3)
C12—N3—C13	102.1 (2)	C25—N6—C26	101.7 (3)
C2—C1—H1A	109.5	C15—C14—H14A	109.5
C2—C1—H1B	109.5	C15—C14—H14B	109.5
H1A—C1—H1B	109.5	H14A—C14—H14B	109.5
C2—C1—H1C	109.5	C15—C14—H14C	109.5
H1A—C1—H1C	109.5	H14A—C14—H14C	109.5
H1B—C1—H1C	109.5	H14B—C14—H14C	109.5
C1—C2—S1	107.1 (2)	C14—C15—S3	107.2 (2)
C1—C2—H2B	110.3	C14—C15—H15A	110.3
S1—C2—H2B	110.3	S3—C15—H15A	110.3
C1—C2—H2C	110.3	C14—C15—H15B	110.3
S1—C2—H2C	110.3	S3—C15—H15B	110.3
H2B—C2—H2C	108.6	H15A—C15—H15B	108.5
C11—C3—S2	123.5 (2)	C24—C16—S4	123.6 (2)
C11—C3—S1	120.6 (2)	C24—C16—S3	121.9 (2)
S2—C3—S1	115.83 (15)	S4—C16—S3	114.44 (15)
C9—C4—C5	121.1 (3)	C22—C17—C18	120.8 (3)
C9—C4—S2	124.0 (2)	C22—C17—S4	124.2 (2)
C5—C4—S2	114.9 (2)	C18—C17—S4	115.0 (2)
C6—C5—C4	117.8 (3)	C19—C18—C17	117.9 (3)
C6—C5—H5A	121.1	C19—C18—H18A	121.0
C4—C5—H5A	121.1	C17—C18—H18A	121.0
F1—C6—C5	118.7 (3)	F2—C19—C18	118.0 (3)
F1—C6—C7	118.2 (3)	F2—C19—C20	119.1 (3)
C5—C6—C7	123.2 (3)	C18—C19—C20	122.9 (3)
C8—C7—C6	118.2 (3)	C21—C20—C19	118.6 (3)
C8—C7—H7A	120.9	C21—C20—H20A	120.7
C6—C7—H7A	120.9	C19—C20—H20A	120.7
C7—C8—C9	121.6 (3)	C20—C21—C22	121.3 (3)
C7—C8—H8A	119.2	C20—C21—H21A	119.4
C9—C8—H8A	119.2	C22—C21—H21A	119.4
C4—C9—C8	118.1 (3)	C17—C22—C21	118.4 (3)
C4—C9—C10	123.7 (2)	C17—C22—C23	123.1 (3)
C8—C9—C10	118.1 (2)	C21—C22—C23	118.5 (2)
O1—C10—C11	121.0 (2)	O2—C23—C24	121.0 (3)
O1—C10—C9	120.2 (2)	O2—C23—C22	120.0 (3)
C11—C10—C9	118.8 (2)	C24—C23—C22	118.9 (2)
C3—C11—N1	118.0 (2)	C16—C24—N4	118.9 (3)
C3—C11—C10	126.2 (2)	C16—C24—C23	126.2 (3)
N1—C11—C10	115.8 (2)	N4—C24—C23	114.9 (2)
N3—C12—N1	111.0 (3)	N6—C25—N4	111.7 (3)
N3—C12—H12A	124.5	N6—C25—H25A	124.2
N1—C12—H12A	124.5	N4—C25—H25A	124.2
N2—C13—N3	116.7 (3)	N5—C26—N6	116.4 (3)
N2—C13—H13A	121.7	N5—C26—H26A	121.8
N3—C13—H13A	121.7	N6—C26—H26A	121.8
C12—N1—N2—C13	1.0 (3)	C25—N4—N5—C26	1.2 (4)
C11—N1—N2—C13	176.8 (3)	C24—N4—N5—C26	177.5 (3)
C3—S1—C2—C1	−178.5 (2)	C16—S3—C15—C14	−179.7 (2)
C4—S2—C3—C11	−1.7 (3)	C17—S4—C16—C24	−4.9 (3)
C4—S2—C3—S1	179.60 (15)	C17—S4—C16—S3	177.84 (15)
C2—S1—C3—C11	169.6 (2)	C15—S3—C16—C24	166.5 (2)
C2—S1—C3—S2	−11.7 (2)	C15—S3—C16—S4	−16.2 (2)
C3—S2—C4—C9	−2.3 (3)	C16—S4—C17—C22	5.2 (3)
C3—S2—C4—C5	177.1 (2)	C16—S4—C17—C18	−175.8 (2)
C9—C4—C5—C6	0.4 (4)	C22—C17—C18—C19	−0.9 (4)
S2—C4—C5—C6	−179.1 (2)	S4—C17—C18—C19	−180.0 (2)
C4—C5—C6—F1	178.3 (3)	C17—C18—C19—F2	−177.1 (3)
C4—C5—C6—C7	−0.9 (5)	C17—C18—C19—C20	1.5 (5)
F1—C6—C7—C8	−178.9 (3)	F2—C19—C20—C21	177.9 (3)
C5—C6—C7—C8	0.3 (5)	C18—C19—C20—C21	−0.7 (5)
C6—C7—C8—C9	0.8 (5)	C19—C20—C21—C22	−0.8 (5)
C5—C4—C9—C8	0.6 (4)	C18—C17—C22—C21	−0.5 (4)
S2—C4—C9—C8	180.0 (2)	S4—C17—C22—C21	178.5 (2)
C5—C4—C9—C10	−177.0 (3)	C18—C17—C22—C23	179.4 (3)
S2—C4—C9—C10	2.4 (4)	S4—C17—C22—C23	−1.6 (4)
C7—C8—C9—C4	−1.2 (4)	C20—C21—C22—C17	1.4 (4)
C7—C8—C9—C10	176.5 (3)	C20—C21—C22—C23	−178.5 (3)
C4—C9—C10—O1	−178.1 (3)	C17—C22—C23—O2	178.3 (3)
C8—C9—C10—O1	4.3 (4)	C21—C22—C23—O2	−1.8 (4)
C4—C9—C10—C11	1.8 (4)	C17—C22—C23—C24	−3.3 (4)
C8—C9—C10—C11	−175.8 (2)	C21—C22—C23—C24	176.6 (2)
S2—C3—C11—N1	−174.04 (19)	S4—C16—C24—N4	−178.25 (19)
S1—C3—C11—N1	4.6 (4)	S3—C16—C24—N4	−1.2 (4)
S2—C3—C11—C10	6.3 (4)	S4—C16—C24—C23	1.1 (4)
S1—C3—C11—C10	−175.1 (2)	S3—C16—C24—C23	178.1 (2)
C12—N1—C11—C3	−126.8 (3)	C25—N4—C24—C16	−128.4 (3)
N2—N1—C11—C3	58.4 (4)	N5—N4—C24—C16	56.1 (4)
C12—N1—C11—C10	52.9 (4)	C25—N4—C24—C23	52.2 (4)
N2—N1—C11—C10	−121.8 (3)	N5—N4—C24—C23	−123.3 (3)
O1—C10—C11—C3	173.5 (3)	O2—C23—C24—C16	−177.9 (3)
C9—C10—C11—C3	−6.4 (4)	C22—C23—C24—C16	3.7 (4)
O1—C10—C11—N1	−6.2 (4)	O2—C23—C24—N4	1.4 (4)
C9—C10—C11—N1	173.9 (2)	C22—C23—C24—N4	−177.0 (2)
C13—N3—C12—N1	1.4 (4)	C26—N6—C25—N4	−0.1 (4)
N2—N1—C12—N3	−1.6 (4)	N5—N4—C25—N6	−0.7 (4)
C11—N1—C12—N3	−176.8 (3)	C24—N4—C25—N6	−176.7 (3)
N1—N2—C13—N3	−0.1 (4)	N4—N5—C26—N6	−1.4 (5)
C12—N3—C13—N2	−0.8 (4)	C25—N6—C26—N5	1.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O2i	0.93	2.40	3.231 (4)	149.
C8—H8A···O1	0.93	2.45	2.764 (4)	100.
C8—H8A···N6ii	0.93	2.56	3.381 (4)	147.
C18—H18A···O1iii	0.93	2.51	3.334 (4)	147.
C21—H21A···O2	0.93	2.46	2.772 (4)	100.
C21—H21A···N3iv	0.93	2.47	3.326 (4)	154.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O2i	0.93	2.40	3.231 (4)	149
C8—H8A⋯O1	0.93	2.45	2.764 (4)	100
C8—H8A⋯N6ii	0.93	2.56	3.381 (4)	147
C18—H18A⋯O1iii	0.93	2.51	3.334 (4)	147
C21—H21A⋯O2	0.93	2.46	2.772 (4)	100
C21—H21A⋯N3iv	0.93	2.47	3.326 (4)	154

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