6-(2-Fluorobenzylidene)-2-[1-(2-fluoro-4-biphenyl)ethyl]thiazolo[3,2-b][1,2,4]triazol-5(6H)-one

The title compound, C₂₅H₁₇F₂N₃OS, was synthesized from 6-(benzyl­idene)­thia­zolo­[3,2-b][1,2,4]triazol-5(6H)-one. The fused thia­zolo­[3,2-b][1,2,4]triazole system is essentially planar, and bifurcated C—H...O, C—H...N and C—H...F interactions are present between mol­ecules.

S1. Comment

Since 6-benzylidenethiazolo[3,2-b]-1,2,4-triazole-5(6H)-one is structurally related to 5-(3,5-di-tert-butyl-4-hydroxy benzylidene)thiazol-4-one, which forms the nucleus of a number of compounds with anti-inflammatory activity, our interest has focused recently on the synthesis and chemistry of this type of compound (Song et al., 1999). In earlier studies, we synthesized new derivatives by combining condensed triazole with ibuprofen and S-naproxen, which belong to the class of 2-arylpropionic acid derivatives of non-steroidal anti-inflammatory drugs, to improve its effectiveness, and these were evaluated for their anti-inflammatory activity. In a continuation of our research programme on the synthesis of novel heterocyclic systems which have analgesic or anti-inflammatory activity, we have prepared some new 6-benzylidenethiazolo[3,2-b]-1,2,4-triazole-5(6H)-ones starting from Flurbiprofen and have determined their anti-inflammatory activity. In order to clarify the structure of this type of compounds, an X-ray structure determination of the title compound, (I), which gave a single-crystal of suitable quality, has been carried out and the results are presented here. \sch

In compound (I), the fused thiazolo[3,2-b]-1,2,4-triazole system is essentially planar. The maximum deviations from the plane of the eight-membered thiazolo-triazole system are 0.031 (6) and −0.040 (4) Å for atoms C9 and N1, respectively. The puckering parameters (Cremer & Pople, 1975) of this system are q₂ 0.045 (5)° and ϕ 260 (5)°. Atoms C10 and N1 are on opposite sides of the plane passing through atoms S1, C8 and C9, at distances of 0.081 (5) and 0.106 (4) Å, respectively. The thiazolo-triazole system makes dihedral angles of 34.54 (17)° with the C1—C6 ring and 86.83 (11)° with the C14—C19 ring. Rings C1—C6 and C14—C19 are almost perpendicular to each other, with a dihedral angle of 85.37 (16)°.

The C7—C8 bond is a double bond, while C1—C7 and C11—C12 are single bonds. A similar lengthening of the S1—C8 bond relative to the S1—C10 bond has been seen in the structure of a similar compound (Özbey et al., 1999).

Compound (I) is stabilized by C—H···O, C—H···N and C—H···F intermolecular contacts. The C4—H4 bond in fact forms a bifurcated contact to two acceptors, namely atoms N3 and O1 [C4—H4···O1ⁱ and C4—H4···N3ⁱ; symmetry code: (i) x − 5/4, y − 1/4, 1/4 − z] (Table 2). The bifurcated nature of the contact explains the relatively large H···A distance and relatively small D—H···A angles. Other important intermolecular contacts are C15—H15···F2ⁱⁱ and C23—H23···F2ⁱⁱⁱ (Table 2), where atom F2 accepts hydrogen bonds from C—H donors [symmetry codes: (ii) x + 1/4, y + 1/4, 1/4 − z; (iii) x − 3/4, 3/4 − y, z − 1/4].

S2. Experimental

The synthesis of (I) was carried out simply by heating equimolar amounts of 3-{1-[(3-fluoro-4-phenyl)phenyl]ethyl}-5-mercapto-1,2,4-triazole, chloroacetic acid and 2-fluorobenzaldehyde dissolved in acetic acid and acetic anhydride in the presence of anhydrous sodium acetate. The starting compound, 3-{1-[(3-fluoro-4-phenyl)phenyl]ethyl}-5-mercapto-1,2,4-triazole, was prepared by employing the previously reported procedure (Tozkoparan et al., 2000; Berk et al., 2001). Compound (I) was crystallized from acetone/su (su is? Ratio?) (yield 67.8%, m.p. 432–433 K). Spectroscopic analysis: IR (ν, cm⁻¹): 3087, 3032 (aromatic C—H), 2970, 2932 (aliphatic C—H), 1744 (lactam C═O), 1616 (C═N); ¹H NMR (CDCl₃, δ, p.p.m.): 1.75 (d, 3H,CH₃), 4.30 (q, 1H, CH), 7.10–7.60 (m, 12H, aromatic H), 8.30 (s, 1H, CH).

S3. Refinement

H atoms were located geometrically and refined using a riding model, fixing the aromatic C—H distance at 0.93 Å, the C—H₂ distance at 0.97 Å and the C—H₃ distance at 0.96 Å. The intensity data collected for (I) were generally weak, so the least-squares goodness-of-fit parameter lies outside the range (goodness-of-fit given 0.627). 1421 Friedel-related reflections were merged in the final refinement because of the meaninglessness of the absolute structure parameter value.

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

Figures

	Fig. 1. A view of the molecule of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A crystal-packing diagram for (I), viewed along the a axis. Please check added text.

2-[1-[(3-fluoro-4-phenyl]ethyl]-6-(2-fluorobenzylidene)thiazolo[3,2-b]- 1,2,4-triazol-5(6H)-one

Crystal data

C25H17F2N3OS	Dx = 1.391 Mg m^−3
Mr = 445.48	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 8331 reflections
a = 24.059 (3) Å	θ = 1.5–24.9°
b = 54.213 (5) Å	µ = 0.19 mm^−1
c = 6.5223 (5) Å	T = 293 K
V = 8507.3 (15) Å^3	Prism, yellow
Z = 16	0.40 × 0.23 × 0.13 mm
F(000) = 3680

Data collection

Stoe IPDS-2 diffractometer	813 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.065
Graphite monochromator	θmax = 25.5°, θmin = 1.9°
Detector resolution: 6.67 pixels mm^-1	h = −28→28
ω scans	k = −52→64
10401 measured reflections	l = −6→7
2135 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0269P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.069	(Δ/σ)max < 0.001
S = 0.67	Δρmax = 0.24 e Å^−3
2135 reflections	Δρmin = −0.12 e Å^−3
291 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.00023 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (14)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.07714 (6)	0.17418 (3)	0.6643 (7)	0.0940 (5)
N1	0.01094 (17)	0.17434 (8)	0.3538 (7)	0.0721 (13)
C16	−0.1676 (2)	0.24505 (9)	0.6269 (9)	0.0774 (16)
H16	−0.1969	0.2366	0.6883	0.093*
C14	−0.0880 (2)	0.24472 (10)	0.3935 (9)	0.0689 (15)
C11	−0.0236 (2)	0.20917 (11)	0.3207 (10)	0.0742 (17)
F1	−0.10176 (11)	0.30505 (6)	0.6125 (6)	0.1113 (12)
C17	−0.1577 (2)	0.26982 (11)	0.6725 (9)	0.0671 (15)
C19	−0.0778 (2)	0.26911 (9)	0.4342 (9)	0.0721 (15)
H19	−0.0484	0.2775	0.3737	0.087*
N2	0.00902 (17)	0.21042 (9)	0.4935 (8)	0.0838 (15)
N3	−0.02406 (16)	0.18772 (9)	0.2268 (8)	0.0792 (13)
C10	0.0291 (2)	0.18827 (11)	0.5010 (10)	0.0764 (17)
C18	−0.1137 (2)	0.28048 (9)	0.5698 (9)	0.0708 (16)
C20	−0.1909 (2)	0.28429 (10)	0.8210 (9)	0.0682 (15)
C12	−0.0502 (2)	0.23210 (10)	0.2327 (9)	0.0784 (17)
H12	−0.0202	0.2437	0.1999	0.094*
O1	0.02261 (17)	0.13589 (7)	0.2060 (8)	0.1104 (16)
C2	0.1233 (2)	0.09494 (13)	0.8111 (12)	0.104 (2)
C25	−0.2119 (2)	0.30721 (11)	0.7762 (11)	0.103 (2)
H25	−0.2047	0.3143	0.6492	0.123*
C15	−0.1324 (2)	0.23315 (9)	0.4856 (10)	0.0776 (18)
H15	−0.1395	0.2167	0.4531	0.093*
C8	0.0705 (2)	0.14711 (9)	0.5165 (9)	0.0748 (17)
C6	0.1627 (3)	0.13439 (12)	0.8337 (12)	0.110 (3)
H6	0.1673	0.1505	0.7885	0.133*
C3	0.1514 (3)	0.08637 (12)	0.9763 (12)	0.115 (3)
H3	0.1473	0.0702	1.0215	0.138*
C1	0.1268 (2)	0.11855 (10)	0.7323 (10)	0.0758 (17)
C9	0.0327 (2)	0.15059 (11)	0.3371 (10)	0.085 (2)
C13	−0.0803 (2)	0.22664 (11)	0.0374 (9)	0.093 (2)
H13C	−0.1107	0.2156	0.0647	0.111*
H13B	−0.0553	0.2191	−0.0584	0.111*
H13A	−0.0945	0.2417	−0.0196	0.111*
C22	−0.2337 (2)	0.28721 (14)	1.1543 (12)	0.108 (2)
H22	−0.2412	0.2805	1.2827	0.130*
C21	−0.2016 (2)	0.27401 (11)	1.0111 (10)	0.0835 (19)
H21	−0.1877	0.2585	1.0439	0.100*
C4	0.1854 (3)	0.10215 (15)	1.0715 (11)	0.111 (2)
H4	0.2053	0.0969	1.1859	0.133*
C23	−0.2537 (3)	0.30999 (13)	1.1019 (15)	0.119 (3)
H23	−0.2748	0.3188	1.1962	0.143*
C5	0.1916 (3)	0.12579 (13)	1.0041 (13)	0.120 (3)
H5	0.2156	0.1364	1.0733	0.144*
C7	0.0932 (2)	0.12531 (9)	0.5593 (9)	0.0808 (18)
H7	0.0864	0.1128	0.4647	0.097*
C24	−0.2435 (3)	0.31973 (12)	0.9183 (14)	0.115 (2)
H24	−0.2578	0.3352	0.8856	0.138*
F2	0.08862 (16)	0.07911 (6)	0.7174 (7)	0.164 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.1255 (12)	0.0651 (9)	0.0913 (13)	0.0232 (9)	−0.0458 (10)	−0.0145 (11)
N1	0.092 (3)	0.048 (3)	0.077 (4)	0.017 (2)	−0.030 (3)	−0.009 (3)
C16	0.110 (4)	0.052 (4)	0.071 (4)	0.026 (3)	−0.020 (4)	−0.007 (4)
C14	0.089 (4)	0.059 (4)	0.058 (4)	0.021 (3)	−0.019 (3)	−0.003 (4)
C11	0.086 (4)	0.061 (4)	0.076 (5)	0.024 (3)	−0.020 (4)	−0.010 (4)
F1	0.135 (3)	0.080 (2)	0.120 (3)	−0.0026 (17)	0.031 (2)	−0.006 (2)
C17	0.061 (3)	0.074 (4)	0.067 (4)	0.009 (3)	0.004 (3)	0.008 (4)
C19	0.089 (4)	0.060 (4)	0.067 (5)	0.017 (3)	−0.002 (3)	0.005 (4)
N2	0.106 (4)	0.071 (4)	0.074 (4)	0.033 (3)	−0.027 (3)	−0.024 (3)
N3	0.100 (3)	0.064 (3)	0.074 (4)	0.018 (3)	−0.018 (3)	0.011 (3)
C10	0.089 (4)	0.060 (4)	0.081 (5)	0.021 (3)	−0.028 (4)	0.005 (4)
C18	0.100 (4)	0.038 (3)	0.073 (5)	0.012 (3)	−0.010 (4)	−0.002 (3)
C20	0.082 (4)	0.061 (4)	0.062 (5)	0.007 (3)	0.010 (3)	−0.004 (4)
C12	0.094 (4)	0.059 (4)	0.082 (5)	0.022 (3)	−0.006 (4)	0.001 (4)
O1	0.161 (3)	0.060 (3)	0.110 (4)	0.031 (2)	−0.067 (3)	−0.021 (3)
C2	0.117 (5)	0.079 (5)	0.116 (8)	−0.003 (4)	−0.046 (5)	0.002 (5)
C25	0.124 (5)	0.082 (5)	0.102 (6)	0.041 (4)	0.025 (4)	0.007 (5)
C15	0.090 (4)	0.045 (3)	0.097 (6)	0.001 (3)	−0.023 (4)	−0.003 (4)
C8	0.100 (4)	0.048 (4)	0.076 (5)	0.006 (3)	−0.029 (3)	−0.007 (3)
C6	0.116 (5)	0.074 (4)	0.141 (8)	0.007 (4)	−0.061 (5)	−0.005 (5)
C3	0.152 (6)	0.083 (5)	0.109 (7)	0.000 (4)	−0.060 (5)	0.017 (5)
C1	0.093 (4)	0.057 (4)	0.077 (5)	0.015 (3)	−0.026 (4)	0.001 (4)
C9	0.119 (5)	0.054 (4)	0.083 (6)	0.011 (3)	−0.033 (4)	0.006 (4)
C13	0.125 (5)	0.091 (5)	0.062 (5)	0.037 (4)	−0.019 (4)	−0.001 (4)
C22	0.120 (6)	0.104 (6)	0.100 (6)	−0.003 (4)	0.031 (5)	0.008 (6)
C21	0.080 (4)	0.084 (5)	0.086 (5)	0.009 (3)	0.023 (4)	0.003 (4)
C4	0.141 (6)	0.099 (6)	0.093 (6)	0.044 (5)	−0.044 (4)	0.013 (5)
C23	0.152 (6)	0.081 (5)	0.124 (8)	0.010 (5)	0.060 (6)	−0.016 (6)
C5	0.133 (5)	0.089 (6)	0.136 (8)	0.020 (4)	−0.077 (5)	−0.033 (5)
C7	0.102 (4)	0.053 (4)	0.088 (5)	0.003 (3)	−0.029 (3)	−0.007 (4)
C24	0.146 (7)	0.084 (5)	0.114 (7)	0.038 (4)	0.028 (5)	0.002 (6)
F2	0.217 (4)	0.069 (2)	0.207 (6)	−0.012 (3)	−0.137 (4)	0.028 (3)

Geometric parameters (Å, º)

S1—C10	1.747 (6)	C2—C1	1.382 (7)
S1—C8	1.763 (6)	C25—C24	1.377 (8)
N1—C10	1.299 (6)	C25—H25	0.9300
N1—N3	1.386 (5)	C15—H15	0.9300
N1—C9	1.394 (7)	C8—C7	1.331 (6)
C16—C17	1.396 (7)	C8—C9	1.494 (7)
C16—C15	1.408 (7)	C6—C1	1.385 (7)
C16—H16	0.9300	C6—C5	1.392 (9)
C14—C19	1.371 (6)	C6—H6	0.9300
C14—C15	1.377 (7)	C3—C4	1.337 (8)
C14—C12	1.548 (7)	C3—H3	0.9300
C11—N3	1.314 (6)	C1—C7	1.435 (7)
C11—N2	1.376 (6)	C13—H13C	0.9600
C11—C12	1.511 (7)	C13—H13B	0.9600
F1—C18	1.391 (5)	C13—H13A	0.9600
C17—C18	1.380 (7)	C22—C23	1.369 (8)
C17—C20	1.481 (7)	C22—C21	1.407 (8)
C19—C18	1.381 (7)	C22—H22	0.9300
C19—H19	0.9300	C21—H21	0.9300
N2—C10	1.296 (6)	C4—C5	1.363 (8)
C20—C25	1.372 (7)	C4—H4	0.9300
C20—C21	1.384 (7)	C23—C24	1.332 (9)
C12—C13	1.496 (7)	C23—H23	0.9300
C12—H12	0.9800	C5—H5	0.9300
O1—C9	1.193 (6)	C7—H7	0.9300
C2—F2	1.345 (6)	C24—H24	0.9300
C2—C3	1.354 (8)
C10—S1—C8	88.3 (3)	C16—C15—H15	118.5
C10—N1—N3	110.0 (4)	C7—C8—C9	121.7 (5)
C10—N1—C9	117.9 (5)	C7—C8—S1	125.9 (4)
N3—N1—C9	131.7 (5)	C9—C8—S1	112.2 (4)
C17—C16—C15	118.5 (5)	C1—C6—C5	119.0 (7)
C17—C16—H16	120.8	C1—C6—H6	120.5
C15—C16—H16	120.8	C5—C6—H6	120.5
C19—C14—C15	119.6 (5)	C4—C3—C2	117.1 (7)
C19—C14—C12	116.9 (5)	C4—C3—H3	121.4
C15—C14—C12	123.4 (5)	C2—C3—H3	121.4
N3—C11—N2	115.5 (5)	C2—C1—C6	115.7 (6)
N3—C11—C12	123.2 (5)	C2—C1—C7	119.7 (6)
N2—C11—C12	120.8 (6)	C6—C1—C7	124.6 (6)
C18—C17—C16	115.5 (5)	O1—C9—N1	126.6 (5)
C18—C17—C20	120.6 (5)	O1—C9—C8	126.9 (5)
C16—C17—C20	123.8 (5)	N1—C9—C8	106.5 (5)
C14—C19—C18	116.3 (5)	C12—C13—H13C	109.5
C14—C19—H19	121.9	C12—C13—H13B	109.5
C18—C19—H19	121.9	H13C—C13—H13B	109.5
C10—N2—C11	101.4 (5)	C12—C13—H13A	109.5
C11—N3—N1	100.4 (4)	H13C—C13—H13A	109.5
N1—C10—N2	112.7 (5)	H13B—C13—H13A	109.5
N1—C10—S1	114.8 (4)	C23—C22—C21	119.1 (7)
N2—C10—S1	132.5 (5)	C23—C22—H22	120.5
C19—C18—C17	127.1 (5)	C21—C22—H22	120.5
C19—C18—F1	115.3 (5)	C20—C21—C22	119.5 (6)
C17—C18—F1	117.5 (5)	C20—C21—H21	120.3
C25—C20—C21	119.1 (6)	C22—C21—H21	120.3
C25—C20—C17	122.6 (6)	C3—C4—C5	121.2 (6)
C21—C20—C17	118.2 (6)	C3—C4—H4	119.4
C13—C12—C11	111.5 (5)	C5—C4—H4	119.4
C13—C12—C14	112.3 (5)	C24—C23—C22	121.1 (7)
C11—C12—C14	110.8 (5)	C24—C23—H23	119.4
C13—C12—H12	107.3	C22—C23—H23	119.4
C11—C12—H12	107.3	C4—C5—C6	121.2 (6)
C14—C12—H12	107.3	C4—C5—H5	119.4
F2—C2—C3	116.9 (7)	C6—C5—H5	119.4
F2—C2—C1	117.4 (6)	C8—C7—C1	128.5 (5)
C3—C2—C1	125.7 (7)	C8—C7—H7	115.8
C20—C25—C24	120.4 (7)	C1—C7—H7	115.8
C20—C25—H25	119.8	C23—C24—C25	120.8 (7)
C24—C25—H25	119.8	C23—C24—H24	119.6
C14—C15—C16	122.9 (5)	C25—C24—H24	119.6
C14—C15—H15	118.5
C15—C16—C17—C18	0.9 (7)	C21—C20—C25—C24	−0.4 (9)
C15—C16—C17—C20	−178.8 (5)	C17—C20—C25—C24	178.7 (6)
C15—C14—C19—C18	0.6 (8)	C19—C14—C15—C16	−2.0 (9)
C12—C14—C19—C18	176.7 (5)	C12—C14—C15—C16	−177.9 (5)
N3—C11—N2—C10	0.2 (7)	C17—C16—C15—C14	1.2 (8)
C12—C11—N2—C10	−171.8 (5)	C10—S1—C8—C7	−173.7 (5)
N2—C11—N3—N1	0.7 (7)	C10—S1—C8—C9	2.8 (5)
C12—C11—N3—N1	172.5 (5)	F2—C2—C3—C4	−179.1 (7)
C10—N1—N3—C11	−1.3 (6)	C1—C2—C3—C4	0.1 (12)
C9—N1—N3—C11	−174.1 (5)	F2—C2—C1—C6	179.5 (6)
N3—N1—C10—N2	1.6 (7)	C3—C2—C1—C6	0.3 (10)
C9—N1—C10—N2	175.5 (5)	F2—C2—C1—C7	1.1 (9)
N3—N1—C10—S1	−176.4 (4)	C3—C2—C1—C7	−178.1 (6)
C9—N1—C10—S1	−2.4 (7)	C5—C6—C1—C2	−0.5 (9)
C11—N2—C10—N1	−1.1 (7)	C5—C6—C1—C7	177.8 (5)
C11—N2—C10—S1	176.4 (5)	C10—N1—C9—O1	−176.2 (6)
C8—S1—C10—N1	−0.4 (5)	N3—N1—C9—O1	−3.8 (10)
C8—S1—C10—N2	−177.9 (7)	C10—N1—C9—C8	4.4 (7)
C14—C19—C18—C17	1.7 (8)	N3—N1—C9—C8	176.7 (5)
C14—C19—C18—F1	178.5 (5)	C7—C8—C9—O1	−7.2 (11)
C16—C17—C18—C19	−2.4 (8)	S1—C8—C9—O1	176.1 (6)
C20—C17—C18—C19	177.2 (5)	C7—C8—C9—N1	172.2 (5)
C16—C17—C18—F1	−179.2 (4)	S1—C8—C9—N1	−4.4 (6)
C20—C17—C18—F1	0.5 (7)	C25—C20—C21—C22	0.0 (9)
C18—C17—C20—C25	49.0 (8)	C17—C20—C21—C22	−179.2 (5)
C16—C17—C20—C25	−131.3 (6)	C23—C22—C21—C20	0.1 (10)
C18—C17—C20—C21	−131.8 (5)	C2—C3—C4—C5	−0.3 (12)
C16—C17—C20—C21	47.8 (8)	C21—C22—C23—C24	0.2 (11)
N3—C11—C12—C13	4.6 (8)	C3—C4—C5—C6	0.1 (12)
N2—C11—C12—C13	176.0 (5)	C1—C6—C5—C4	0.4 (11)
N3—C11—C12—C14	130.5 (6)	C9—C8—C7—C1	−175.0 (5)
N2—C11—C12—C14	−58.2 (7)	S1—C8—C7—C1	1.1 (9)
C19—C14—C12—C13	−109.1 (6)	C2—C1—C7—C8	146.5 (6)
C15—C14—C12—C13	66.8 (7)	C6—C1—C7—C8	−31.8 (9)
C19—C14—C12—C11	125.5 (5)	C22—C23—C24—C25	−0.7 (12)
C15—C14—C12—C11	−58.5 (7)	C20—C25—C24—C23	0.8 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1^i	0.93	2.57	3.333 (8)	140
C4—H4···N3^i	0.93	2.71	3.551 (8)	150
C15—H15···F2^ii	0.93	2.54	3.448 (6)	165
C23—H23···F2^iii	0.93	2.41	3.307 (8)	162

Symmetry codes: (i) x+1/4, −y+1/4, z+5/4; (ii) x−1/4, −y+1/4, z−1/4; (iii) −x−1/4, y+1/4, z+3/4.