3-[(E)-4-(2-Nitro­phen­yl)vin­yl]-1-(tri­fluoro­meth­yl)-1,2,4-triazolo[4,3-a]quinoxaline

Thiruvalluvar, A.; Subramanyam, M.; Butcher, R.J.; Wagle, S.; Adhikari, A.V.

doi:10.1107/S1600536807060783

3-[(E)-4-(2-Nitrophenyl)vinyl]-1-(trifluoromethyl)-1,2,4-triazolo[4,3-a]quinoxaline

A. Thiruvalluvar, M. Subramanyam, R. J. Butcher, S. Wagle and A. V. Adhikari

In the title molecule, C₁₈H₁₀F₃N₅O₂, the 1,2,4-triazolo[4,3-a]quinoxaline unit is nearly planar. The central pyrazine ring makes dihedral angles of 1.67 (6) and 2.44 (5)° with the 1,2,4-triazole and fused benzene ring, respectively. The nitrophenyl ring makes dihedral angles of 2.82 (6), 3.15 (6) and 3.63 (6)° with the triazole, pyrazine and benzene rings, respectively. The nitro group is slightly twisted away from the plane of the attached benzene ring. C—H

O and C—H

F hydrogen bonds are found in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060783/cs2062sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060783/cs2062Isup2.hkl Contains datablock I

CCDC reference: 673059

checkCIF report

Key indicators

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R factor = 0.043
wR factor = 0.125
Data-to-parameter ratio = 21.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT230_ALERT_2_C Hirshfeld Test Diff for    F1     -   C51     ..       5.82 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N5     -   C12     ..       6.28 su
PLAT431_ALERT_2_C Short Inter HL..A Contact  F2     ..  N5      ..       2.98 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C5      ..       3.01 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.972
            Tmax scaled      0.972 Tmin scaled      0.874

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In addition to purines and pteridines, many other fused heterocyclic ring systems are known. Of these the most important is that containing ring junction nitrogen, in which the nitrogen is common to two rings. The vast majority of these systems do not occur naturally, they have been the subject of many studies from the theoretical viewpoint and for the preparation of biologically active analogues. Earlier studies revealed that most of the compounds derived from 1,2,4-triazoles have been shown to display a wide spectrum of biological activities. Moreover, a few fused triazoles of different heterocycles have been found to be significant anticonvulsant and tranquillizing agents. Also, 1,2,4-triazolo quinoxalines have been reported as antidepressant, cardiotonics and antifatigue agents (Ali et al., 2004; Bicking, 1959; Chimirri et al., 2002; Dawood et al., 2006; Ilkay et al., 2004; Potts, 1961; Trivedi, 1988; Xie et al., 2005).

In the title molecule, C₁₈H₁₀F₃N₅O₂, Fig.1, the [1,2,4]triazolo[4,3-a]quinoxaline unit is nearly planar. The central pyrazine ring makes a dihedral angle of 1.67 (6)° and 2.44 (5)° with that of the 1,2,4-triazole and the fused benzene ring respectively. The nitro phenyl ring makes a dihedral angle of 2.82 (6)°, 3.15 (6)°, and 3.63 (6)° with that of triazole, pyrazine and benzene rings respectively. The nitro group is slightly twisted away from the plane of the attached phenyl ring. C—H···O and C—H···F hydrogen bonds are found in the crystal structure; see Fig. 2., and the hydrogen bond table.

Related literature top

For the uses of [1,2,4]triazoloquinoxalines, see Ali et al. (2004); Bicking (1959); Chimirri et al. (2002); Dawood et al. (2006); Ilkay et al. (2004); Potts (1961); Trivedi (1988); Xie et al. (2005).

Experimental top

To a mixture of compounds 4-methyl-1-(trifluoromethyl)[1,2,4]triazolo[4,3-a]quinoxaline (5.0 g, 0.0198 mol), and 2-nitrobenzaldehyde (3.14 g, 0.0208 mol) in methanol (20 ml) added catalytic amount (0.2 ml) of conc. sulfuric acid. The reaction mass was refluxed (338 K) for 8 h. The reaction mass was cooled to room temperature, and kept overnight. The separated solid was filtered, washed with methanol (5 ml) to obtain the title compound. The compound was further recrystalized from ethanol to give pale yellow crystals 4.0 g, 52.6%.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

3-[(E)-4-(2-Nitrophenyl)vinyl]-1-(trifluoromethyl)- 1,2,4-triazolo[4,3-a]quinoxaline top

Crystal data top

C₁₈H₁₀F₃N₅O₂	F(000) = 784
M_r = 385.31	D_x = 1.575 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 472(1) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.0065 (2) Å	Cell parameters from 6025 reflections
b = 16.9010 (4) Å	θ = 4.8–32.5°
c = 12.0204 (3) Å	µ = 0.13 mm⁻¹
β = 92.633 (2)°	T = 200 K
V = 1624.86 (7) Å³	Prism, pale yellow
Z = 4	0.37 × 0.35 × 0.22 mm

Data collection top

Oxford Diffraction Gemini diffractometer	5345 independent reflections
Radiation source: fine-focus sealed tube	3157 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 10.5081 pixels mm^-1	θ_max = 32.6°, θ_min = 4.8°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −25→25
T_min = 0.899, T_max = 1.000	l = −17→17
15678 measured reflections

Refinement top

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0729P)²] where P = (F_o² + 2F_c²)/3
5345 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₈H₁₀F₃N₅O₂	V = 1624.86 (7) Å³
M_r = 385.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0065 (2) Å	µ = 0.13 mm⁻¹
b = 16.9010 (4) Å	T = 200 K
c = 12.0204 (3) Å	0.37 × 0.35 × 0.22 mm
β = 92.633 (2)°

Data collection top

Oxford Diffraction Gemini diffractometer	5345 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	3157 reflections with I > 2σ(I)
T_min = 0.899, T_max = 1.000	R_int = 0.023
15678 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 0.98	Δρ_max = 0.35 e Å⁻³
5345 reflections	Δρ_min = −0.28 e Å⁻³
253 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.33806 (11)	0.79608 (5)	0.83090 (7)	0.0536 (3)
F2	0.56207 (10)	0.81556 (5)	0.74471 (7)	0.0473 (3)
F3	0.33485 (13)	0.87452 (5)	0.69060 (8)	0.0638 (4)
O1	0.30844 (12)	0.28804 (5)	0.43450 (8)	0.0420 (3)
O2	0.12053 (14)	0.20138 (6)	0.38762 (11)	0.0588 (4)
N1	0.26886 (14)	0.75604 (6)	0.55632 (9)	0.0381 (3)
N2	0.23975 (14)	0.68574 (6)	0.50247 (9)	0.0359 (3)
N4	0.37684 (11)	0.66121 (6)	0.66443 (7)	0.0253 (3)
N4A	0.37242 (12)	0.49810 (6)	0.62414 (8)	0.0293 (3)
N5	0.17977 (14)	0.26776 (6)	0.38229 (9)	0.0367 (3)
C1	0.22162 (15)	0.51486 (7)	0.44843 (10)	0.0302 (3)
C2	0.17674 (14)	0.43913 (7)	0.43653 (9)	0.0290 (3)
C3	0.30453 (14)	0.63014 (7)	0.56780 (9)	0.0268 (3)
C3A	0.30274 (14)	0.54560 (7)	0.55073 (9)	0.0274 (3)
C4A	0.45134 (14)	0.52974 (7)	0.71888 (9)	0.0266 (3)
C5	0.34938 (15)	0.74113 (7)	0.65139 (10)	0.0305 (3)
C5A	0.53147 (15)	0.47701 (7)	0.79337 (10)	0.0329 (3)
C6	0.61637 (17)	0.50386 (8)	0.88796 (11)	0.0384 (4)
C7	0.62241 (16)	0.58451 (8)	0.91106 (10)	0.0373 (4)
C8	0.54455 (15)	0.63835 (7)	0.84044 (10)	0.0314 (3)
C8A	0.45896 (14)	0.61160 (7)	0.74388 (9)	0.0254 (3)
C11	0.09609 (14)	0.40639 (7)	0.33468 (9)	0.0283 (3)
C12	0.09491 (15)	0.32572 (7)	0.30827 (10)	0.0298 (3)
C13	0.01979 (17)	0.29588 (8)	0.21091 (12)	0.0400 (4)
C14	−0.05853 (17)	0.34677 (9)	0.13569 (11)	0.0447 (5)
C15	−0.06427 (16)	0.42677 (9)	0.16040 (11)	0.0416 (4)
C16	0.01072 (16)	0.45550 (8)	0.25819 (10)	0.0342 (4)
C51	0.39666 (17)	0.80652 (7)	0.72976 (12)	0.0389 (4)
H1	0.19990	0.55012	0.38794	0.0362*
H2	0.19835	0.40442	0.49767	0.0348*
H5	0.52718	0.42184	0.77840	0.0395*
H6	0.67091	0.46736	0.93754	0.0460*
H7	0.68122	0.60262	0.97662	0.0448*
H8	0.54894	0.69326	0.85719	0.0377*
H13	0.02229	0.24068	0.19614	0.0479*
H14	−0.10796	0.32725	0.06776	0.0536*
H15	−0.12013	0.46215	0.10981	0.0499*
H16	0.00385	0.51049	0.27373	0.0410*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0648 (5)	0.0496 (5)	0.0472 (5)	−0.0069 (4)	0.0121 (4)	−0.0219 (4)
F2	0.0486 (5)	0.0391 (4)	0.0534 (5)	−0.0125 (4)	−0.0049 (4)	−0.0113 (4)
F3	0.0897 (7)	0.0208 (4)	0.0781 (7)	0.0094 (4)	−0.0264 (5)	−0.0086 (4)
O1	0.0420 (5)	0.0355 (5)	0.0478 (5)	0.0043 (4)	−0.0047 (4)	0.0018 (4)
O2	0.0655 (7)	0.0227 (5)	0.0879 (9)	−0.0070 (5)	0.0008 (6)	0.0064 (5)
N1	0.0484 (6)	0.0241 (5)	0.0409 (6)	−0.0006 (5)	−0.0084 (5)	0.0002 (5)
N2	0.0488 (6)	0.0237 (5)	0.0341 (6)	−0.0012 (5)	−0.0103 (5)	0.0006 (4)
N4	0.0307 (5)	0.0203 (4)	0.0247 (5)	−0.0019 (4)	−0.0022 (4)	−0.0026 (4)
N4A	0.0371 (5)	0.0229 (5)	0.0274 (5)	−0.0029 (4)	−0.0027 (4)	−0.0029 (4)
N5	0.0404 (6)	0.0237 (5)	0.0463 (6)	0.0003 (5)	0.0047 (5)	−0.0019 (5)
C1	0.0384 (6)	0.0245 (6)	0.0271 (6)	−0.0013 (5)	−0.0054 (5)	−0.0024 (5)
C2	0.0333 (6)	0.0246 (6)	0.0286 (6)	0.0011 (5)	−0.0041 (5)	−0.0025 (5)
C3	0.0325 (6)	0.0231 (5)	0.0245 (5)	−0.0032 (4)	−0.0025 (4)	−0.0025 (4)
C3A	0.0336 (6)	0.0229 (5)	0.0254 (5)	−0.0038 (5)	−0.0008 (4)	−0.0032 (5)
C4A	0.0302 (6)	0.0232 (5)	0.0262 (5)	−0.0029 (4)	−0.0012 (4)	−0.0018 (5)
C5	0.0371 (6)	0.0191 (5)	0.0350 (6)	−0.0008 (5)	−0.0021 (5)	−0.0028 (5)
C5A	0.0407 (7)	0.0224 (5)	0.0352 (6)	−0.0005 (5)	−0.0039 (5)	0.0015 (5)
C6	0.0456 (7)	0.0337 (7)	0.0348 (7)	−0.0012 (6)	−0.0089 (5)	0.0066 (6)
C7	0.0450 (7)	0.0357 (7)	0.0303 (6)	−0.0068 (6)	−0.0088 (5)	−0.0007 (6)
C8	0.0406 (6)	0.0258 (6)	0.0274 (6)	−0.0054 (5)	−0.0026 (5)	−0.0033 (5)
C8A	0.0282 (5)	0.0225 (5)	0.0254 (5)	−0.0011 (4)	−0.0008 (4)	0.0007 (4)
C11	0.0308 (5)	0.0238 (5)	0.0298 (6)	−0.0033 (5)	−0.0031 (4)	−0.0040 (5)
C12	0.0294 (5)	0.0249 (5)	0.0348 (6)	−0.0022 (5)	0.0000 (5)	−0.0037 (5)
C13	0.0411 (7)	0.0326 (7)	0.0461 (8)	−0.0078 (6)	0.0007 (6)	−0.0147 (6)
C14	0.0470 (8)	0.0505 (9)	0.0356 (7)	−0.0107 (7)	−0.0093 (6)	−0.0149 (7)
C15	0.0406 (7)	0.0480 (8)	0.0350 (7)	−0.0018 (6)	−0.0114 (5)	−0.0014 (6)
C16	0.0386 (7)	0.0266 (6)	0.0364 (6)	−0.0002 (5)	−0.0094 (5)	−0.0015 (5)
C51	0.0478 (8)	0.0216 (6)	0.0465 (8)	−0.0012 (5)	−0.0051 (6)	−0.0048 (6)

Geometric parameters (Å, º) top

F1—C51	1.3348 (17)	C5A—C6	1.3747 (18)
F2—C51	1.3370 (16)	C6—C7	1.3915 (19)
F3—C51	1.3289 (15)	C7—C8	1.3743 (18)
O1—N5	1.2301 (15)	C8—C8A	1.3958 (16)
O2—N5	1.2209 (15)	C11—C12	1.3998 (17)
N1—N2	1.3679 (15)	C11—C16	1.3942 (17)
N1—C5	1.3105 (16)	C12—C13	1.3860 (19)
N2—C3	1.3158 (16)	C13—C14	1.378 (2)
N4—C3	1.3778 (14)	C14—C15	1.386 (2)
N4—C5	1.3763 (16)	C15—C16	1.3832 (18)
N4—C8A	1.4106 (14)	C1—H1	0.9500
N4A—C3A	1.2997 (15)	C2—H2	0.9500
N4A—C4A	1.3842 (15)	C5A—H5	0.9500
N5—C12	1.4688 (16)	C6—H6	0.9500
C1—C2	1.3353 (17)	C7—H7	0.9500
C1—C3A	1.4596 (16)	C8—H8	0.9500
C2—C11	1.4661 (16)	C13—H13	0.9500
C3—C3A	1.4435 (17)	C14—H14	0.9500
C4A—C5A	1.3981 (16)	C15—H15	0.9500
C4A—C8A	1.4165 (17)	C16—H16	0.9500
C5—C51	1.4898 (18)

F1···N4	3.0583 (13)	C3A···C16ⁱ	3.4791 (17)
F1···C8	3.1362 (15)	C4A···C1ⁱⁱⁱ	3.4573 (16)
F1···C13ⁱ	3.2779 (16)	C4A···C15ⁱ	3.5586 (17)
F1···O1ⁱⁱ	3.1065 (13)	C5···O1ⁱⁱⁱ	3.0124 (15)
F1···C14ⁱ	3.3289 (17)	C5···C13ⁱ	3.5096 (18)
F2···O2ⁱⁱⁱ	3.0727 (14)	C5A···O2^viii	3.2875 (16)
F2···C8	3.2139 (15)	C5A···C1ⁱⁱⁱ	3.5921 (17)
F2···N4	3.1312 (13)	C6···C16ⁱⁱⁱ	3.5992 (19)
F2···N5ⁱⁱⁱ	2.9792 (14)	C6···C6^ix	3.3475 (19)
F2···O1ⁱⁱⁱ	2.9977 (12)	C6···C7^ix	3.4852 (18)
F3···C16^iv	3.2850 (16)	C7···C6^ix	3.4852 (18)
F3···N1	2.6107 (14)	C7···N1^iv	3.3909 (17)
F1···H8	2.4300	C8···F1	3.1362 (15)
F1···H2ⁱⁱ	2.7800	C8···C51	3.3325 (17)
F2···H8	2.4700	C8···C12ⁱⁱⁱ	3.5173 (17)
F3···H7^v	2.8300	C8···F2	3.2139 (15)
F3···H16^iv	2.5500	C8A···C15ⁱ	3.4734 (17)
O1···C2	2.7633 (15)	C8A···O1ⁱⁱⁱ	3.3630 (15)
O1···N4ⁱⁱⁱ	2.9622 (13)	C11···C3ⁱ	3.5198 (16)
O1···F1^vi	3.1065 (13)	C12···C8ⁱⁱⁱ	3.5173 (17)
O1···F2ⁱⁱⁱ	2.9977 (12)	C13···C5ⁱ	3.5096 (18)
O1···C8Aⁱⁱⁱ	3.3630 (15)	C13···F1ⁱ	3.2779 (16)
O1···C3ⁱⁱⁱ	3.3946 (15)	C14···F1ⁱ	3.3289 (17)
O1···C5ⁱⁱⁱ	3.0124 (15)	C15···C8Aⁱ	3.4734 (17)
O2···F2ⁱⁱⁱ	3.0727 (14)	C15···C4Aⁱ	3.5586 (17)
O2···C5A^vii	3.2875 (16)	C16···C3Aⁱ	3.4791 (17)
O1···H2	2.3000	C16···C6ⁱⁱⁱ	3.5992 (19)
O1···H14^viii	2.5900	C16···F3^v	3.2850 (16)
O2···H13	2.4900	C51···C8	3.3325 (17)
O2···H5^vii	2.5600	C1···H16	2.6700
N1···F3	2.6107 (14)	C5···H8	2.9900
N1···N4	2.2140 (14)	C16···H1	2.6600
N1···C7^v	3.3909 (17)	C51···H8	2.7100
N2···N4	2.2295 (14)	H1···N2	2.6900
N4···O1ⁱⁱⁱ	2.9622 (13)	H1···C16	2.6600
N4···N1	2.2140 (14)	H1···H16	2.1400
N4···F1	3.0583 (13)	H2···O1	2.3000
N4···F2	3.1312 (13)	H2···N4A	2.5600
N4···N4A	2.7989 (14)	H2···N5	2.6900
N4A···N4	2.7989 (14)	H2···F1^vi	2.7800
N4A···C1ⁱⁱⁱ	3.4109 (15)	H5···O2^viii	2.5600
N5···F2ⁱⁱⁱ	2.9792 (14)	H7···F3^iv	2.8300
N1···H7^v	2.6600	H7···N1^iv	2.6600
N2···H1	2.6900	H8···F1	2.4300
N4A···H2	2.5600	H8···F2	2.4700
N5···H2	2.6900	H8···C5	2.9900
C1···C5Aⁱⁱⁱ	3.5921 (17)	H8···C51	2.7100
C1···N4Aⁱⁱⁱ	3.4109 (15)	H13···O2	2.4900
C1···C4Aⁱⁱⁱ	3.4573 (16)	H14···O1^vii	2.5900
C2···O1	2.7633 (15)	H16···C1	2.6700
C3···C11ⁱ	3.5198 (16)	H16···H1	2.1400
C3···O1ⁱⁱⁱ	3.3946 (15)	H16···F3^v	2.5500

N2—N1—C5	108.18 (10)	N5—C12—C11	120.94 (10)
N1—N2—C3	106.50 (10)	N5—C12—C13	116.07 (11)
C3—N4—C5	102.67 (9)	C11—C12—C13	122.96 (11)
C3—N4—C8A	120.60 (10)	C12—C13—C14	119.59 (12)
C5—N4—C8A	136.68 (10)	C13—C14—C15	119.15 (13)
C3A—N4A—C4A	119.04 (10)	C14—C15—C16	120.49 (13)
O1—N5—O2	123.20 (11)	C11—C16—C15	122.14 (12)
O1—N5—C12	118.46 (10)	F1—C51—F2	106.27 (11)
O2—N5—C12	118.34 (11)	F1—C51—F3	107.23 (11)
C2—C1—C3A	122.59 (11)	F1—C51—C5	112.84 (10)
C1—C2—C11	123.87 (11)	F2—C51—F3	107.41 (10)
N2—C3—N4	111.70 (10)	F2—C51—C5	113.02 (11)
N2—C3—C3A	128.39 (10)	F3—C51—C5	109.75 (11)
N4—C3—C3A	119.88 (10)	C2—C1—H1	119.00
N4A—C3A—C1	120.84 (11)	C3A—C1—H1	119.00
N4A—C3A—C3	120.92 (10)	C1—C2—H2	118.00
C1—C3A—C3	118.24 (10)	C11—C2—H2	118.00
N4A—C4A—C5A	117.35 (10)	C4A—C5A—H5	120.00
N4A—C4A—C8A	124.43 (10)	C6—C5A—H5	120.00
C5A—C4A—C8A	118.21 (10)	C5A—C6—H6	120.00
N1—C5—N4	110.96 (10)	C7—C6—H6	120.00
N1—C5—C51	120.62 (11)	C6—C7—H7	120.00
N4—C5—C51	128.42 (11)	C8—C7—H7	120.00
C4A—C5A—C6	120.94 (11)	C7—C8—H8	120.00
C5A—C6—C7	119.98 (12)	C8A—C8—H8	120.00
C6—C7—C8	120.98 (12)	C12—C13—H13	120.00
C7—C8—C8A	119.38 (11)	C14—C13—H13	120.00
N4—C8A—C4A	115.01 (10)	C13—C14—H14	120.00
N4—C8A—C8	124.49 (11)	C15—C14—H14	120.00
C4A—C8A—C8	120.50 (10)	C14—C15—H15	120.00
C2—C11—C12	123.72 (10)	C16—C15—H15	120.00
C2—C11—C16	120.65 (11)	C11—C16—H16	119.00
C12—C11—C16	115.61 (11)	C15—C16—H16	119.00

C5—N1—N2—C3	0.00 (15)	N2—C3—C3A—C1	0.73 (18)
N2—N1—C5—N4	0.03 (14)	N4—C3—C3A—N4A	−1.80 (17)
N2—N1—C5—C51	−179.10 (11)	N4—C3—C3A—C1	178.63 (10)
N1—N2—C3—N4	−0.06 (14)	N4A—C4A—C5A—C6	178.31 (11)
N1—N2—C3—C3A	177.98 (11)	C8A—C4A—C5A—C6	−0.44 (18)
C5—N4—C3—N2	0.08 (13)	N4A—C4A—C8A—N4	0.71 (16)
C5—N4—C3—C3A	−178.15 (10)	N4A—C4A—C8A—C8	−178.61 (11)
C8A—N4—C3—N2	−177.62 (10)	C5A—C4A—C8A—N4	179.36 (10)
C8A—N4—C3—C3A	4.16 (15)	C5A—C4A—C8A—C8	0.04 (17)
C3—N4—C5—N1	−0.07 (13)	N1—C5—C51—F1	123.92 (13)
C3—N4—C5—C51	178.98 (12)	N1—C5—C51—F2	−115.47 (13)
C8A—N4—C5—N1	177.04 (12)	N1—C5—C51—F3	4.40 (17)
C8A—N4—C5—C51	−3.9 (2)	N4—C5—C51—F1	−55.05 (17)
C3—N4—C8A—C4A	−3.52 (15)	N4—C5—C51—F2	65.57 (17)
C3—N4—C8A—C8	175.77 (11)	N4—C5—C51—F3	−174.56 (11)
C5—N4—C8A—C4A	179.76 (12)	C4A—C5A—C6—C7	0.45 (19)
C5—N4—C8A—C8	−1.0 (2)	C5A—C6—C7—C8	−0.1 (2)
C4A—N4A—C3A—C1	178.55 (10)	C6—C7—C8—C8A	−0.33 (19)
C4A—N4A—C3A—C3	−1.01 (16)	C7—C8—C8A—N4	−178.92 (11)
C3A—N4A—C4A—C5A	−177.11 (11)	C7—C8—C8A—C4A	0.34 (17)
C3A—N4A—C4A—C8A	1.56 (17)	C2—C11—C12—N5	−1.24 (18)
O1—N5—C12—C11	−33.51 (17)	C2—C11—C12—C13	−179.18 (12)
O1—N5—C12—C13	144.57 (12)	C16—C11—C12—N5	−179.76 (11)
O2—N5—C12—C11	147.64 (12)	C16—C11—C12—C13	2.30 (18)
O2—N5—C12—C13	−34.28 (17)	C2—C11—C16—C15	178.86 (11)
C3A—C1—C2—C11	−179.60 (11)	C12—C11—C16—C15	−2.57 (18)
C2—C1—C3A—N4A	17.38 (18)	N5—C12—C13—C14	−178.28 (12)
C2—C1—C3A—C3	−163.05 (11)	C11—C12—C13—C14	−0.2 (2)
C1—C2—C11—C12	159.64 (12)	C12—C13—C14—C15	−1.7 (2)
C1—C2—C11—C16	−21.91 (18)	C13—C14—C15—C16	1.4 (2)
N2—C3—C3A—N4A	−179.70 (12)	C14—C15—C16—C11	0.8 (2)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+1; (iv) x+1/2, −y+3/2, z+1/2; (v) x−1/2, −y+3/2, z−1/2; (vi) −x+1/2, y−1/2, −z+3/2; (vii) x−1/2, −y+1/2, z−1/2; (viii) x+1/2, −y+1/2, z+1/2; (ix) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.95	2.30	2.7633 (15)	109
C5A—H5···O2^viii	0.95	2.56	3.2875 (16)	134
C8—H8···F1	0.95	2.43	3.1362 (15)	131
C8—H8···F2	0.95	2.47	3.2139 (15)	135
C14—H14···O1^vii	0.95	2.59	3.4551 (17)	151
C16—H16···F3^v	0.95	2.55	3.2850 (16)	135

Symmetry codes: (v) x−1/2, −y+3/2, z−1/2; (vii) x−1/2, −y+1/2, z−1/2; (viii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₀F₃N₅O₂
M_r	385.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	8.0065 (2), 16.9010 (4), 12.0204 (3)
β (°)	92.633 (2)
V (Å³)	1624.86 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.37 × 0.35 × 0.22

Data collection
Diffractometer	Oxford Diffraction Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.899, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15678, 5345, 3157
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.757

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.125, 0.98
No. of reflections	5345
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.28

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).