7-Fluoro-2-(prop-2-en-1-ylsulfan-yl)-3-(1H-1,2,4-triazol-1-yl)-4H-thio-chromen-4-one.

The asymmetric unit of the title compound, C(14)H(10)FN(3)OS(2), contains two independent mol-ecules which differ in the relative orientations of the triazole and allyl-sulfanyl groups with respect to the planar thio-chromen-4-one frameworks. The N-N-C-C torsion angles are 128.2 (5) and -120.9 (5)°, while the C-S-C-S torsion angles are -17.4 (4) and 16.4 (4)°. In the crystal, inter-molecular C-H⋯O and C-H⋯N hydrogen bonds link the mol-ecules in a stacked arrangement along the a axis.

Related literature

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

Experimental

Crystal data

C14H10FN3OS2

M = 319.39

Triclinic,

a = 8.1730 (16) Å

b = 11.646 (2) Å

c = 15.124 (3) Å

α = 82.43 (3)°

β = 83.98 (3)°

γ = 80.14 (3)°

V = 1400.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.926, T max = 0.962

5541 measured reflections

5149 independent reflections

3087 reflections with I > 2σ(I)

R int = 0.037

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.176

S = 1.01

5149 reflections

379 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985) ▶; cell refinement: CAD-4 Software ▶; 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 datablock(s) I, global. DOI: 10.1107/S1600536811022665/zq2103sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022665/zq2103Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022665/zq2103Isup3.cml

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

C14H10FN3OS2	Z = 4
Mr = 319.39	F(000) = 656
Triclinic, P1	Dx = 1.514 Mg m−3
Hall symbol: -P 1	Melting point: 385 K
a = 8.1730 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.646 (2) Å	Cell parameters from 25 reflections
c = 15.124 (3) Å	θ = 9–12°
α = 82.43 (3)°	µ = 0.39 mm−1
β = 83.98 (3)°	T = 293 K
γ = 80.14 (3)°	Block, yellow
V = 1400.9 (5) Å3	0.20 × 0.10 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	3087 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
graphite	θmax = 25.5°, θmin = 1.4°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −13→14
Tmin = 0.926, Tmax = 0.962	l = −18→18
5541 measured reflections	3 standard reflections every 200 reflections
5149 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.080P)2 + 1.P] where P = (Fo2 + 2Fc2)/3
5149 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.52 e Å−3
1 restraint	Δρmin = −0.40 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	0.44048 (18)	0.30108 (12)	0.42901 (7)	0.0563 (4)
O1	0.3291 (5)	0.4374 (3)	0.69021 (19)	0.0718 (11)
F1	0.0540 (4)	0.6601 (3)	0.3288 (2)	0.0787 (10)
N1	0.5146 (5)	0.2210 (3)	0.6888 (2)	0.0472 (10)
C1	0.2380 (6)	0.4976 (4)	0.3820 (3)	0.0511 (12)
H1A	0.2597	0.4748	0.3247	0.061*
S2	0.64594 (19)	0.10674 (12)	0.52776 (8)	0.0604 (4)
N2	0.6087 (6)	0.1689 (4)	0.8194 (3)	0.0640 (12)
C2	0.1322 (7)	0.5970 (5)	0.3969 (3)	0.0538 (13)
C3	0.1006 (6)	0.6363 (4)	0.4802 (3)	0.0552 (13)
H3A	0.0285	0.7057	0.4886	0.066*
N3	0.4931 (6)	0.1073 (4)	0.7111 (2)	0.0610 (12)
C4	0.1774 (6)	0.5709 (4)	0.5491 (3)	0.0526 (13)
H4A	0.1579	0.5967	0.6054	0.063*
C5	0.2847 (6)	0.4662 (4)	0.5386 (3)	0.0414 (11)
C6	0.3135 (6)	0.4303 (4)	0.4532 (3)	0.0419 (11)
C7	0.3553 (6)	0.3979 (4)	0.6171 (3)	0.0495 (12)
C8	0.4592 (6)	0.2856 (4)	0.6084 (3)	0.0428 (11)
C9	0.5093 (6)	0.2390 (4)	0.5298 (3)	0.0457 (11)
C10	0.5830 (7)	0.2549 (5)	0.7553 (3)	0.0563 (14)
H10A	0.6088	0.3295	0.7559	0.068*
C11	0.5504 (8)	0.0820 (5)	0.7890 (3)	0.0659 (16)
H11A	0.5510	0.0085	0.8218	0.079*
C12	0.7155 (8)	0.1027 (5)	0.4101 (3)	0.0734 (18)
H12A	0.6357	0.0727	0.3799	0.088*
H12B	0.7267	0.1810	0.3817	0.088*
C13	0.8773 (11)	0.0255 (7)	0.4051 (4)	0.108 (3)
H13A	0.9647	0.0519	0.4269	0.129*
C14	0.9121 (11)	−0.0722 (6)	0.3748 (4)	0.112 (3)
H14A	0.8299	−0.1031	0.3520	0.134*
H14B	1.0201	−0.1134	0.3751	0.134*
S3	0.24689 (18)	0.41381 (11)	0.89646 (7)	0.0544 (4)
S4	0.1326 (2)	0.20977 (13)	1.00091 (8)	0.0656 (4)
F2	0.4001 (4)	0.8034 (3)	0.78292 (18)	0.0770 (10)
N4	0.1606 (5)	0.3240 (3)	1.1599 (2)	0.0478 (10)
N5	0.0575 (6)	0.2723 (4)	1.2953 (3)	0.0605 (12)
N6	0.2392 (6)	0.2129 (4)	1.1815 (3)	0.0635 (13)
O2	0.2657 (5)	0.5303 (3)	1.15925 (19)	0.0618 (10)
C15	0.3312 (6)	0.6232 (4)	0.8431 (3)	0.0516 (13)
H15A	0.3294	0.6027	0.7859	0.062*
C16	0.3687 (7)	0.7272 (5)	0.8545 (3)	0.0553 (13)
C17	0.3756 (7)	0.7615 (5)	0.9382 (3)	0.0568 (13)
H17A	0.4038	0.8339	0.9444	0.068*
C18	0.3395 (6)	0.6851 (4)	1.0112 (3)	0.0518 (13)
H18A	0.3440	0.7063	1.0680	0.062*
C19	0.2964 (6)	0.5765 (4)	1.0038 (3)	0.0417 (11)
C20	0.2946 (6)	0.5460 (4)	0.9182 (3)	0.0431 (11)
C21	0.2567 (6)	0.4993 (4)	1.0857 (3)	0.0428 (11)
C22	0.2014 (6)	0.3908 (4)	1.0784 (3)	0.0416 (11)
C23	0.1920 (6)	0.3458 (4)	1.0007 (3)	0.0463 (12)
C24	0.0550 (6)	0.3569 (5)	1.2292 (3)	0.0528 (13)
H24A	−0.0114	0.4301	1.2301	0.063*
C25	0.1744 (8)	0.1885 (5)	1.2630 (3)	0.0685 (16)
H25A	0.2072	0.1171	1.2969	0.082*
C26	0.0874 (8)	0.2065 (5)	0.8870 (3)	0.0665 (16)
H26A	0.0070	0.2745	0.8682	0.080*
H26B	0.1882	0.2071	0.8470	0.080*
C27	0.0185 (10)	0.0971 (6)	0.8850 (4)	0.094 (2)
H27A	−0.0860	0.0931	0.9150	0.113*
C28	0.0857 (11)	0.0102 (6)	0.8476 (4)	0.105 (3)
H28C	0.1904	0.0097	0.8166	0.126*
H28A	0.0315	−0.0543	0.8504	0.126*

	U11	U22	U33	U12	U13	U23
S1	0.0737 (10)	0.0671 (9)	0.0274 (6)	0.0032 (7)	−0.0070 (5)	−0.0204 (5)
O1	0.108 (3)	0.080 (3)	0.0250 (16)	0.005 (2)	−0.0030 (17)	−0.0291 (16)
F1	0.091 (3)	0.081 (2)	0.0559 (18)	0.0140 (19)	−0.0192 (17)	−0.0051 (16)
N1	0.067 (3)	0.052 (2)	0.0259 (18)	−0.015 (2)	−0.0017 (17)	−0.0117 (16)
C1	0.056 (3)	0.068 (3)	0.033 (2)	−0.012 (3)	−0.004 (2)	−0.014 (2)
S2	0.0812 (10)	0.0641 (9)	0.0325 (6)	0.0045 (7)	−0.0051 (6)	−0.0139 (6)
N2	0.086 (4)	0.068 (3)	0.040 (2)	−0.010 (3)	−0.017 (2)	−0.007 (2)
C2	0.060 (3)	0.059 (3)	0.042 (3)	−0.009 (3)	−0.007 (2)	−0.003 (2)
C3	0.054 (3)	0.055 (3)	0.054 (3)	−0.002 (3)	0.001 (2)	−0.013 (2)
N3	0.095 (4)	0.059 (3)	0.034 (2)	−0.022 (2)	−0.005 (2)	−0.0076 (18)
C4	0.060 (3)	0.063 (3)	0.035 (2)	−0.009 (3)	0.005 (2)	−0.015 (2)
C5	0.043 (3)	0.054 (3)	0.030 (2)	−0.012 (2)	0.0027 (19)	−0.0129 (19)
C6	0.047 (3)	0.054 (3)	0.028 (2)	−0.012 (2)	−0.0005 (19)	−0.0150 (19)
C7	0.056 (3)	0.068 (3)	0.029 (2)	−0.017 (3)	0.003 (2)	−0.018 (2)
C8	0.055 (3)	0.052 (3)	0.025 (2)	−0.017 (2)	−0.0035 (19)	−0.0091 (19)
C9	0.051 (3)	0.058 (3)	0.033 (2)	−0.016 (2)	−0.002 (2)	−0.014 (2)
C10	0.079 (4)	0.056 (3)	0.038 (3)	−0.011 (3)	−0.014 (2)	−0.016 (2)
C11	0.099 (5)	0.066 (4)	0.034 (3)	−0.019 (3)	−0.003 (3)	−0.006 (2)
C12	0.089 (4)	0.084 (4)	0.034 (3)	0.028 (3)	−0.001 (3)	−0.018 (3)
C13	0.143 (7)	0.116 (6)	0.047 (4)	0.031 (5)	−0.007 (4)	−0.013 (4)
C14	0.152 (8)	0.096 (6)	0.077 (5)	0.025 (5)	−0.022 (5)	−0.018 (4)
S3	0.0840 (10)	0.0579 (8)	0.0237 (5)	−0.0125 (7)	−0.0015 (5)	−0.0138 (5)
S4	0.0998 (12)	0.0617 (9)	0.0420 (7)	−0.0247 (8)	−0.0080 (7)	−0.0136 (6)
F2	0.113 (3)	0.081 (2)	0.0412 (16)	−0.039 (2)	−0.0052 (16)	0.0077 (15)
N4	0.062 (3)	0.057 (3)	0.0225 (18)	−0.005 (2)	−0.0003 (17)	−0.0076 (16)
N5	0.076 (3)	0.064 (3)	0.039 (2)	−0.014 (2)	0.013 (2)	−0.008 (2)
N6	0.089 (4)	0.056 (3)	0.036 (2)	0.001 (2)	0.010 (2)	−0.0021 (18)
O2	0.098 (3)	0.071 (2)	0.0242 (16)	−0.025 (2)	−0.0040 (16)	−0.0166 (15)
C15	0.065 (3)	0.061 (3)	0.031 (2)	−0.013 (3)	−0.006 (2)	−0.006 (2)
C16	0.064 (4)	0.065 (3)	0.036 (3)	−0.016 (3)	0.000 (2)	0.001 (2)
C17	0.075 (4)	0.059 (3)	0.041 (3)	−0.020 (3)	−0.005 (2)	−0.008 (2)
C18	0.065 (3)	0.060 (3)	0.033 (2)	−0.011 (3)	−0.008 (2)	−0.011 (2)
C19	0.045 (3)	0.051 (3)	0.028 (2)	0.000 (2)	−0.0042 (18)	−0.0087 (19)
C20	0.044 (3)	0.052 (3)	0.033 (2)	−0.004 (2)	−0.0044 (19)	−0.0087 (19)
C21	0.047 (3)	0.056 (3)	0.025 (2)	−0.004 (2)	−0.0011 (18)	−0.0099 (19)
C22	0.046 (3)	0.049 (3)	0.029 (2)	−0.005 (2)	−0.0012 (19)	−0.0078 (19)
C23	0.056 (3)	0.052 (3)	0.030 (2)	−0.002 (2)	−0.002 (2)	−0.012 (2)
C24	0.062 (3)	0.061 (3)	0.037 (3)	−0.013 (3)	0.008 (2)	−0.015 (2)
C25	0.098 (5)	0.064 (4)	0.036 (3)	−0.004 (3)	0.004 (3)	0.002 (2)
C26	0.098 (5)	0.057 (3)	0.048 (3)	−0.011 (3)	−0.011 (3)	−0.018 (2)
C27	0.131 (6)	0.103 (6)	0.060 (4)	−0.042 (5)	−0.009 (4)	−0.028 (4)
C28	0.166 (8)	0.092 (5)	0.066 (4)	−0.037 (5)	0.001 (4)	−0.032 (4)

S1—C9	1.706 (5)	S3—C23	1.720 (4)
S1—C6	1.734 (5)	S3—C20	1.731 (5)
O1—C7	1.237 (5)	S4—C23	1.734 (5)
F1—C2	1.337 (5)	S4—C26	1.806 (5)
N1—C10	1.334 (5)	F2—C16	1.339 (5)
N1—N3	1.359 (5)	N4—C24	1.339 (5)
N1—C8	1.416 (5)	N4—N6	1.357 (5)
C1—C2	1.350 (7)	N4—C22	1.409 (5)
C1—C6	1.380 (6)	N5—C24	1.307 (6)
C1—H1A	0.9300	N5—C25	1.347 (6)
S2—C9	1.743 (5)	N6—C25	1.305 (6)
S2—C12	1.814 (5)	O2—C21	1.227 (5)
N2—C10	1.305 (6)	C15—C16	1.335 (7)
N2—C11	1.340 (7)	C15—C20	1.393 (6)
C2—C3	1.381 (6)	C15—H15A	0.9300
C3—C4	1.350 (7)	C16—C17	1.387 (6)
C3—H3A	0.9300	C17—C18	1.364 (6)
N3—C11	1.293 (6)	C17—H17A	0.9300
C4—C5	1.392 (6)	C18—C19	1.391 (6)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.393 (5)	C19—C20	1.389 (6)
C5—C7	1.454 (6)	C19—C21	1.473 (6)
C7—C8	1.446 (7)	C21—C22	1.435 (6)
C8—C9	1.367 (6)	C22—C23	1.362 (6)
C10—H10A	0.9300	C24—H24A	0.9300
C11—H11A	0.9300	C25—H25A	0.9300
C12—C13	1.467 (9)	C26—C27	1.484 (8)
C12—H12A	0.9700	C26—H26A	0.9700
C12—H12B	0.9700	C26—H26B	0.9700
C13—C14	1.259 (7)	C27—C28	1.241 (9)
C13—H13A	0.9300	C27—H27A	0.9300
C14—H14A	0.9300	C28—H28C	0.9300
C14—H14B	0.9300	C28—H28A	0.9300
C9—S1—C6	104.0 (2)	C23—S3—C20	103.9 (2)
C10—N1—N3	108.5 (4)	C23—S4—C26	104.5 (2)
C10—N1—C8	130.2 (4)	C24—N4—N6	109.1 (4)
N3—N1—C8	121.2 (4)	C24—N4—C22	128.8 (4)
C2—C1—C6	118.9 (4)	N6—N4—C22	121.9 (4)
C2—C1—H1A	120.5	C24—N5—C25	101.9 (4)
C6—C1—H1A	120.5	C25—N6—N4	101.7 (4)
C9—S2—C12	103.8 (2)	C16—C15—C20	119.0 (4)
C10—N2—C11	102.7 (4)	C16—C15—H15A	120.5
F1—C2—C1	119.2 (4)	C20—C15—H15A	120.5
F1—C2—C3	118.3 (5)	C15—C16—F2	119.7 (4)
C1—C2—C3	122.5 (5)	C15—C16—C17	122.9 (5)
C4—C3—C2	118.0 (5)	F2—C16—C17	117.5 (5)
C4—C3—H3A	121.0	C18—C17—C16	117.5 (5)
C2—C3—H3A	121.0	C18—C17—H17A	121.2
C11—N3—N1	102.7 (4)	C16—C17—H17A	121.2
C3—C4—C5	122.2 (4)	C17—C18—C19	122.4 (4)
C3—C4—H4A	118.9	C17—C18—H18A	118.8
C5—C4—H4A	118.9	C19—C18—H18A	118.8
C4—C5—C6	117.8 (4)	C20—C19—C18	117.6 (4)
C4—C5—C7	118.7 (4)	C20—C19—C21	123.2 (4)
C6—C5—C7	123.5 (4)	C18—C19—C21	119.3 (4)
C1—C6—C5	120.5 (4)	C19—C20—C15	120.7 (4)
C1—C6—S1	115.9 (3)	C19—C20—S3	123.8 (4)
C5—C6—S1	123.6 (4)	C15—C20—S3	115.5 (3)
O1—C7—C8	120.6 (4)	O2—C21—C22	120.8 (4)
O1—C7—C5	119.9 (5)	O2—C21—C19	119.8 (4)
C8—C7—C5	119.5 (4)	C22—C21—C19	119.4 (4)
C9—C8—N1	118.4 (4)	C23—C22—N4	118.3 (4)
C9—C8—C7	125.4 (4)	C23—C22—C21	125.8 (4)
N1—C8—C7	116.2 (4)	N4—C22—C21	115.8 (4)
C8—C9—S1	123.7 (4)	C22—C23—S3	123.6 (4)
C8—C9—S2	120.8 (4)	C22—C23—S4	121.4 (4)
S1—C9—S2	115.5 (2)	S3—C23—S4	114.9 (2)
N2—C10—N1	110.6 (5)	N5—C24—N4	111.0 (5)
N2—C10—H10A	124.7	N5—C24—H24A	124.5
N1—C10—H10A	124.7	N4—C24—H24A	124.5
N3—C11—N2	115.5 (5)	N6—C25—N5	116.2 (5)
N3—C11—H11A	122.3	N6—C25—H25A	121.9
N2—C11—H11A	122.3	N5—C25—H25A	121.9
C13—C12—S2	107.3 (4)	C27—C26—S4	107.0 (4)
C13—C12—H12A	110.3	C27—C26—H26A	110.3
S2—C12—H12A	110.3	S4—C26—H26A	110.3
C13—C12—H12B	110.3	C27—C26—H26B	110.3
S2—C12—H12B	110.3	S4—C26—H26B	110.3
H12A—C12—H12B	108.5	H26A—C26—H26B	108.6
C14—C13—C12	127.8 (9)	C28—C27—C26	126.9 (8)
C14—C13—H13A	116.1	C28—C27—H27A	116.6
C12—C13—H13A	116.1	C26—C27—H27A	116.6
C13—C14—H14A	120.0	C27—C28—H28C	120.0
C13—C14—H14B	120.0	C27—C28—H28A	120.0
H14A—C14—H14B	120.0	H28C—C28—H28A	120.0
C6—C1—C2—F1	−177.5 (4)	C24—N4—N6—C25	−0.5 (6)
C6—C1—C2—C3	2.2 (8)	C22—N4—N6—C25	175.2 (5)
F1—C2—C3—C4	178.7 (5)	C20—C15—C16—F2	−178.4 (4)
C1—C2—C3—C4	−1.0 (8)	C20—C15—C16—C17	1.0 (8)
C10—N1—N3—C11	−0.1 (6)	C15—C16—C17—C18	−1.0 (8)
C8—N1—N3—C11	−176.8 (5)	F2—C16—C17—C18	178.4 (5)
C2—C3—C4—C5	−0.5 (8)	C16—C17—C18—C19	−0.3 (8)
C3—C4—C5—C6	0.9 (7)	C17—C18—C19—C20	1.5 (7)
C3—C4—C5—C7	−176.7 (5)	C17—C18—C19—C21	−179.1 (5)
C2—C1—C6—C5	−1.9 (7)	C18—C19—C20—C15	−1.5 (7)
C2—C1—C6—S1	177.3 (4)	C21—C19—C20—C15	179.1 (4)
C4—C5—C6—C1	0.4 (7)	C18—C19—C20—S3	179.1 (4)
C7—C5—C6—C1	177.8 (4)	C21—C19—C20—S3	−0.3 (7)
C4—C5—C6—S1	−178.8 (4)	C16—C15—C20—C19	0.3 (7)
C7—C5—C6—S1	−1.3 (7)	C16—C15—C20—S3	179.8 (4)
C9—S1—C6—C1	−178.8 (4)	C23—S3—C20—C19	4.4 (5)
C9—S1—C6—C5	0.4 (5)	C23—S3—C20—C15	−175.1 (4)
C4—C5—C7—O1	−5.2 (7)	C20—C19—C21—O2	177.7 (4)
C6—C5—C7—O1	177.4 (5)	C18—C19—C21—O2	−1.7 (7)
C4—C5—C7—C8	176.4 (4)	C20—C19—C21—C22	−4.7 (7)
C6—C5—C7—C8	−1.0 (7)	C18—C19—C21—C22	175.9 (4)
C10—N1—C8—C9	131.2 (5)	C24—N4—C22—C23	−128.9 (5)
N3—N1—C8—C9	−52.9 (6)	N6—N4—C22—C23	56.5 (6)
C10—N1—C8—C7	−47.7 (7)	C24—N4—C22—C21	53.8 (7)
N3—N1—C8—C7	128.2 (5)	N6—N4—C22—C21	−120.9 (5)
O1—C7—C8—C9	−173.4 (5)	O2—C21—C22—C23	−177.6 (5)
C5—C7—C8—C9	5.1 (7)	C19—C21—C22—C23	4.9 (7)
O1—C7—C8—N1	5.5 (7)	O2—C21—C22—N4	−0.5 (7)
C5—C7—C8—N1	−176.1 (4)	C19—C21—C22—N4	−178.0 (4)
N1—C8—C9—S1	174.9 (3)	N4—C22—C23—S3	−176.9 (3)
C7—C8—C9—S1	−6.3 (7)	C21—C22—C23—S3	0.1 (7)
N1—C8—C9—S2	−3.1 (6)	N4—C22—C23—S4	−0.3 (6)
C7—C8—C9—S2	175.8 (4)	C21—C22—C23—S4	176.8 (4)
C6—S1—C9—C8	3.3 (5)	C20—S3—C23—C22	−4.3 (5)
C6—S1—C9—S2	−178.7 (3)	C20—S3—C23—S4	178.8 (3)
C12—S2—C9—C8	−165.5 (4)	C26—S4—C23—C22	165.7 (4)
C12—S2—C9—S1	16.4 (4)	C26—S4—C23—S3	−17.4 (4)
C11—N2—C10—N1	−0.9 (6)	C25—N5—C24—N4	2.0 (6)
N3—N1—C10—N2	0.6 (6)	N6—N4—C24—N5	−1.1 (6)
C8—N1—C10—N2	176.9 (5)	C22—N4—C24—N5	−176.3 (4)
N1—N3—C11—N2	−0.5 (7)	N4—N6—C25—N5	1.9 (7)
C10—N2—C11—N3	0.9 (7)	C24—N5—C25—N6	−2.5 (7)
C9—S2—C12—C13	156.2 (5)	C23—S4—C26—C27	−174.1 (5)
S2—C12—C13—C14	113.6 (7)	S4—C26—C27—C28	−111.7 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2i	0.93	2.50	3.328 (5)	149
C4—H4A···N5ii	0.93	2.61	3.397 (7)	143
C15—H15A···O1	0.93	2.56	3.372 (6)	147
C18—H18A···N2iii	0.93	2.48	3.355 (7)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2i	0.93	2.50	3.328 (5)	149
C4—H4A⋯N5ii	0.93	2.61	3.397 (7)	143
C15—H15A⋯O1	0.93	2.56	3.372 (6)	147
C18—H18A⋯N2iii	0.93	2.48	3.355 (7)	157

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