1-{5-Methyl-1-[8-(trifluoro­meth­yl)quinolin-4-yl]-1H-1,2,3-triazol-4-yl}ethanone

Thiruvalluvar, A.; Subramanyam, M.; Butcher, R.J.; Mahalinga, M.

doi:10.1107/S1600536807059193

1-{5-Methyl-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-1,2,3-triazol-4-yl}ethanone

A. Thiruvalluvar, M. Subramanyam, R. J. Butcher and M. Mahalinga

In the title molecule, C₁₅H₁₁F₃N₄O, the quinoline unit is nearly planar. The dihedral angle between the pyridine ring and the fused benzene ring is 2.45 (6)°. The triazole ring makes dihedral angles of 63.7 (1) and 64.7 (1)° with the pyridine and benzene rings, respectively. The ethanone group is coplanar with the attached triazole ring, except for the methyl H atoms. C—H

O, C—H

N and C—H

F hydrogen bonds are found in the crystal structure.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059193/im2045sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059193/im2045Isup2.hkl Contains datablock I

CCDC reference: 673019

checkCIF report

Key indicators

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R factor = 0.043
wR factor = 0.126
Data-to-parameter ratio = 22.0

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    C4     -   C5      ..       6.87 su
PLAT432_ALERT_2_C Short Inter X...Y Contact  C12    ..  C12     ..       3.12 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      0.935

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   2 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

1,2,3-Triazoles and their benzoderivatives have attracted considerable attention because of their theoretical interest and synthetic value. They also find numerous applications in industry and agriculture due to their extensive biological activities and successful application as fluorescent whiteners, light stabilizers and optical brightening agents (Sanghvi, et al., 1990). Many 1,2,3-triazoles are found to be potent antimicrobial (Chen, et al., 2000; Sherement, et al., 2004), analgesic (Kreutzberger & Stratmann, 1980), anti- inflammatory, local anesthetic (Banu, et al., 1999), anticonvulsant (Peter & Roger, 2004), antineoplastic (Passannanti, et al., 1998), antimalarial (Jilino & Stevens, 1998) and antiviral agents (Safonova, et al., 2003). Some of them also exhibited antiproliferative (Manfredini, et al., 2000) and anticancer activity (Melo, et al., 2003). A good number of derivatives of 1,2,3-triazoles are used as DNA cleaving agents and potassium channel activators (Biagi, et al., 2004).

In the title molecule, C₁₅H₁₁F₃N₄O, Fig.1., the quinoline unit is nearly planar. The dihedral angle between the pyridine ring and the fused benzene ring is 2.45 (6)°. The triazole ring makes a dihedral angle of 63.7 (1)° and 64.7 (1)°, with that of pyridine and benzene rings respectively. The ethanone group is coplanar with the attached triazole ring, except the methyl H atoms. C—H···O, C—H···N and C—H···F hydrogen bonds are found in the crystal structure; see Fig.2 and hydrogen bond table. Furthermore, there is a short intermolecular C12···C12 contact which is caused by an intermolecular hydrogen bond H12 is involved in as well as by π-stacking effects.

Related literature top

For the uses of 1,2,3-triazoles and their benzo derivatives, see Banu et al. (1999); Biagi et al. (2004); Chen et al. (2000); Jilino & Stevens (1998); Kreutzberger & Stratmann (1980); Manfredini et al. (2000); Melo et al. (2003); Passannanti et al. (1988); Peter & Roger (2004); Safonova et al. (2003); Sanghvi et al. (1990); Sherement et al. (2004).

Experimental top

4-Azido-8-trifluoromethyl quinoline (15 g, 0.06 mol) was treated with acetylacetone (6.4 g, 0.06 mol) in methanol (75 ml) and the mixture was cooled to 273 K. Sodium methoxide (3.5 g, 0.06 mol) was added under nitrogen atmosphere to the above mixture and then stirred at ambient temperature for 6–8 h. Progress of the reaction was monitored by TLC (ethylacetate:n-hexane: 2:3, v/v). The reaction mass was poured into ice cold water, precipitated solid was filtered and washed with water. The crude product was recrystallized from methanol. Yield 13.5 g (65%).

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 c axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

1-{5-Methyl-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-1,2,3-triazol- 4-yl}ethanone top

Crystal data top

C₁₅H₁₁F₃N₄O	F(000) = 656
M_r = 320.28	D_x = 1.544 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 459(1) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.7974 (4) Å	Cell parameters from 5005 reflections
b = 8.2946 (2) Å	θ = 4.6–32.5°
c = 14.6706 (4) Å	µ = 0.13 mm⁻¹
β = 106.273 (3)°	T = 200 K
V = 1378.07 (7) Å³	Plate, colourless
Z = 4	0.44 × 0.37 × 0.22 mm

Data collection top

Oxford Diffraction Gemini diffractometer	4615 independent reflections
Radiation source: fine-focus sealed tube	2511 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 10.5081 pixels mm^-1	θ_max = 32.6°, θ_min = 4.6°
ϕ and ω scans	h = −17→17
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −12→11
T_min = 0.962, T_max = 1.000	l = −22→20
13863 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) = 0.126	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0712P)²] where P = (F_o² + 2F_c²)/3
4615 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₁F₃N₄O	V = 1378.07 (7) Å³
M_r = 320.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.7974 (4) Å	µ = 0.13 mm⁻¹
b = 8.2946 (2) Å	T = 200 K
c = 14.6706 (4) Å	0.44 × 0.37 × 0.22 mm
β = 106.273 (3)°

Data collection top

Oxford Diffraction Gemini diffractometer	4615 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2511 reflections with I > 2σ(I)
T_min = 0.962, T_max = 1.000	R_int = 0.027
13863 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 0.96	Δρ_max = 0.30 e Å⁻³
4615 reflections	Δρ_min = −0.24 e Å⁻³
210 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.65453 (7)	0.13558 (11)	0.67581 (5)	0.0531 (3)
F2	0.73949 (7)	−0.09155 (11)	0.67264 (5)	0.0470 (3)
F3	0.83628 (7)	0.12893 (9)	0.67695 (5)	0.0445 (3)
O41	0.87328 (10)	0.13080 (14)	−0.00685 (7)	0.0567 (4)
N1	0.77553 (9)	−0.04634 (13)	0.22873 (7)	0.0309 (3)
N2	0.67283 (10)	−0.11480 (14)	0.17371 (7)	0.0410 (4)
N3	0.66767 (9)	−0.08334 (14)	0.08593 (7)	0.0380 (3)
N11	0.86194 (9)	−0.09327 (13)	0.52759 (7)	0.0303 (3)
C4	0.76499 (10)	0.00397 (14)	0.08307 (8)	0.0296 (3)
C5	0.83557 (10)	0.02833 (14)	0.17441 (8)	0.0281 (3)
C6	0.95054 (10)	0.11275 (16)	0.21160 (9)	0.0343 (4)
C12	0.92664 (11)	−0.15856 (14)	0.47733 (8)	0.0308 (3)
C13	0.90248 (10)	−0.14431 (15)	0.37815 (8)	0.0317 (4)
C14	0.80417 (10)	−0.06296 (15)	0.32991 (8)	0.0279 (3)
C14A	0.72793 (10)	0.00695 (14)	0.37893 (8)	0.0268 (3)
C15	0.62311 (11)	0.09220 (15)	0.33425 (9)	0.0321 (4)
C16	0.55839 (11)	0.16221 (16)	0.38699 (9)	0.0359 (4)
C17	0.59412 (11)	0.15093 (15)	0.48661 (9)	0.0342 (4)
C18	0.69379 (10)	0.06727 (15)	0.53191 (8)	0.0289 (4)
C18A	0.76407 (10)	−0.00955 (14)	0.47940 (8)	0.0267 (3)
C19	0.73096 (11)	0.05847 (17)	0.63863 (9)	0.0350 (4)
C41	0.78389 (12)	0.05745 (16)	−0.00728 (9)	0.0370 (4)
C42	0.69031 (14)	0.0203 (2)	−0.09740 (9)	0.0514 (5)
H6A	0.97595	0.10527	0.28105	0.0515*
H6B	1.00988	0.06222	0.18563	0.0515*
H6C	0.94153	0.22637	0.19263	0.0515*
H12	0.99402	−0.21921	0.51019	0.0370*
H13	0.95383	−0.19059	0.34570	0.0380*
H15	0.59782	0.10056	0.26699	0.0385*
H16	0.48832	0.21932	0.35621	0.0431*
H17	0.54873	0.20176	0.52263	0.0410*
H42A	0.69885	0.09280	−0.14779	0.0771*
H42B	0.69863	−0.09168	−0.11590	0.0771*
H42C	0.61224	0.03535	−0.08746	0.0771*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0538 (5)	0.0722 (7)	0.0382 (4)	0.0185 (4)	0.0211 (4)	−0.0015 (4)
F2	0.0608 (5)	0.0461 (5)	0.0365 (4)	0.0014 (4)	0.0178 (4)	0.0109 (3)
F3	0.0427 (4)	0.0504 (5)	0.0361 (4)	−0.0019 (4)	0.0042 (3)	−0.0039 (3)
O41	0.0561 (7)	0.0696 (8)	0.0486 (6)	−0.0104 (6)	0.0216 (5)	0.0131 (5)
N1	0.0315 (5)	0.0346 (6)	0.0267 (5)	−0.0062 (4)	0.0083 (4)	−0.0024 (4)
N2	0.0389 (6)	0.0516 (8)	0.0316 (6)	−0.0177 (5)	0.0082 (5)	−0.0046 (5)
N3	0.0402 (6)	0.0415 (7)	0.0313 (5)	−0.0097 (5)	0.0084 (5)	−0.0037 (5)
N11	0.0289 (5)	0.0302 (6)	0.0310 (5)	0.0015 (4)	0.0072 (4)	0.0024 (4)
C4	0.0316 (6)	0.0274 (6)	0.0294 (6)	−0.0006 (5)	0.0079 (5)	−0.0011 (5)
C5	0.0300 (6)	0.0243 (6)	0.0326 (6)	0.0015 (5)	0.0130 (5)	0.0004 (5)
C6	0.0290 (6)	0.0344 (7)	0.0406 (7)	−0.0041 (5)	0.0115 (5)	−0.0005 (5)
C12	0.0267 (6)	0.0285 (6)	0.0343 (6)	0.0011 (5)	0.0037 (5)	0.0000 (5)
C13	0.0292 (6)	0.0337 (7)	0.0333 (6)	−0.0029 (5)	0.0107 (5)	−0.0065 (5)
C14	0.0296 (6)	0.0290 (7)	0.0249 (5)	−0.0078 (5)	0.0071 (5)	−0.0020 (5)
C14A	0.0282 (6)	0.0259 (6)	0.0258 (6)	−0.0053 (5)	0.0066 (5)	0.0014 (5)
C15	0.0310 (6)	0.0334 (7)	0.0287 (6)	−0.0007 (5)	0.0033 (5)	0.0072 (5)
C16	0.0288 (6)	0.0369 (7)	0.0393 (7)	0.0044 (5)	0.0051 (5)	0.0088 (6)
C17	0.0309 (6)	0.0344 (7)	0.0389 (7)	0.0014 (5)	0.0126 (5)	0.0020 (5)
C18	0.0286 (6)	0.0299 (7)	0.0288 (6)	−0.0023 (5)	0.0091 (5)	0.0014 (5)
C18A	0.0261 (6)	0.0244 (6)	0.0293 (6)	−0.0019 (5)	0.0072 (5)	0.0032 (5)
C19	0.0351 (7)	0.0401 (8)	0.0314 (6)	0.0052 (6)	0.0119 (5)	0.0020 (6)
C41	0.0464 (8)	0.0334 (7)	0.0332 (7)	0.0026 (6)	0.0145 (6)	0.0018 (6)
C42	0.0752 (11)	0.0481 (9)	0.0289 (7)	−0.0060 (8)	0.0115 (7)	−0.0021 (6)

Geometric parameters (Å, º) top

F1—C19	1.3399 (16)	C14A—C18A	1.4216 (16)
F2—C19	1.3339 (17)	C15—C16	1.3601 (19)
F3—C19	1.3454 (16)	C16—C17	1.4061 (18)
O41—C41	1.2160 (19)	C17—C18	1.3667 (18)
N1—N2	1.3762 (16)	C18—C18A	1.4300 (17)
N1—C5	1.3553 (16)	C18—C19	1.5047 (17)
N1—C14	1.4337 (15)	C41—C42	1.4979 (19)
N2—N3	1.2986 (14)	C6—H6A	0.9800
N3—C4	1.3680 (16)	C6—H6B	0.9800
N11—C12	1.3172 (16)	C6—H6C	0.9800
N11—C18A	1.3630 (16)	C12—H12	0.9500
C4—C5	1.3800 (16)	C13—H13	0.9500
C4—C41	1.4728 (17)	C15—H15	0.9500
C5—C6	1.4876 (17)	C16—H16	0.9500
C12—C13	1.4071 (16)	C17—H17	0.9500
C13—C14	1.3570 (17)	C42—H42A	0.9800
C14—C14A	1.4230 (17)	C42—H42B	0.9800
C14A—C15	1.4158 (18)	C42—H42C	0.9800

F1···C6ⁱ	3.3366 (15)	C12···C13ⁱⁱ	3.5320 (17)
F2···N11	2.8876 (13)	C13···N11ⁱⁱ	3.3713 (16)
F3···N11	2.9431 (13)	C13···C6	3.4080 (18)
F3···C6ⁱⁱ	3.2730 (15)	C13···C12ⁱⁱ	3.5320 (17)
F1···H42Aⁱⁱⁱ	2.5200	C15···N2^vi	3.4457 (18)
F1···H6Cⁱ	2.8300	C15···N1^vi	3.4485 (17)
F1···H17	2.3100	C15···N2	3.1005 (17)
F2···H42A^iv	2.7700	C16···C4^vi	3.4724 (18)
F2···H16^v	2.8100	C16···C5^vi	3.4972 (18)
F3···H42B^vi	2.4800	C17···O41ⁱ	3.1961 (18)
F3···H6Bⁱⁱ	2.8000	C17···C17^v	3.4415 (18)
F3···H13ⁱⁱ	2.6400	C41···N11^vi	3.3399 (17)
O41···C6	3.0801 (16)	C41···C12^vi	3.5387 (19)
O41···C17^vii	3.1961 (18)	C5···H13	3.1000
O41···H6B	2.8900	C13···H15^iv	3.0000
O41···H6C	2.9200	C13···H6A	2.7900
O41···H17^vii	2.4300	C14···H6A	2.7200
N1···C15^iv	3.4485 (17)	C14A···H6C^iv	3.0600
N2···C15	3.1005 (17)	C19···H42B^vi	3.0600
N2···C6^iv	3.3807 (17)	H6A···C13	2.7900
N2···C15^iv	3.4457 (18)	H6A···C14	2.7200
N11···C41^iv	3.3399 (17)	H6A···N11ⁱⁱ	2.9200
N11···F3	2.9431 (13)	H6B···O41	2.8900
N11···C13ⁱⁱ	3.3713 (16)	H6B···F3ⁱⁱ	2.8000
N11···F2	2.8876 (13)	H6C···O41	2.9200
N11···C12ⁱⁱ	3.2696 (17)	H6C···C14A^vi	3.0600
N1···H15	2.6200	H6C···F1^vii	2.8300
N2···H15	2.5500	H12···N3^ix	2.6100
N3···H12^viii	2.6100	H13···C5	3.1000
N3···H42C	2.6300	H13···H15^iv	2.3500
N11···H6Aⁱⁱ	2.9200	H13···F3ⁱⁱ	2.6400
C4···C12^vi	3.5509 (17)	H15···N1	2.6200
C4···C16^iv	3.4724 (18)	H15···N2	2.5500
C5···C16^iv	3.4972 (18)	H15···C13^vi	3.0000
C6···C13	3.4080 (18)	H15···H13^vi	2.3500
C6···O41	3.0801 (16)	H16···F2^v	2.8100
C6···F1^vii	3.3366 (15)	H17···F1	2.3100
C6···N2^vi	3.3807 (17)	H17···O41ⁱ	2.4300
C6···F3ⁱⁱ	3.2730 (15)	H42A···F1^x	2.5200
C12···C4^iv	3.5509 (17)	H42A···F2^vi	2.7700
C12···C12ⁱⁱ	3.1164 (17)	H42B···F3^iv	2.4800
C12···C41^iv	3.5387 (19)	H42B···C19^iv	3.0600
C12···N11ⁱⁱ	3.2696 (17)	H42C···N3	2.6300

N2—N1—C5	111.28 (9)	F1—C19—F3	105.70 (10)
N2—N1—C14	118.75 (10)	F1—C19—C18	111.55 (11)
C5—N1—C14	129.97 (11)	F2—C19—F3	106.55 (10)
N1—N2—N3	106.72 (10)	F2—C19—C18	113.82 (11)
N2—N3—C4	109.29 (10)	F3—C19—C18	112.30 (11)
C12—N11—C18A	117.30 (10)	O41—C41—C4	119.73 (12)
N3—C4—C5	109.33 (10)	O41—C41—C42	122.08 (12)
N3—C4—C41	121.81 (11)	C4—C41—C42	118.19 (12)
C5—C4—C41	128.87 (11)	C5—C6—H6A	109.00
N1—C5—C4	103.39 (10)	C5—C6—H6B	109.00
N1—C5—C6	124.93 (10)	C5—C6—H6C	109.00
C4—C5—C6	131.69 (11)	H6A—C6—H6B	109.00
N11—C12—C13	124.27 (11)	H6A—C6—H6C	109.00
C12—C13—C14	118.49 (11)	H6B—C6—H6C	109.00
N1—C14—C13	120.45 (11)	N11—C12—H12	118.00
N1—C14—C14A	119.02 (10)	C13—C12—H12	118.00
C13—C14—C14A	120.53 (11)	C12—C13—H13	121.00
C14—C14A—C15	124.28 (11)	C14—C13—H13	121.00
C14—C14A—C18A	115.87 (11)	C14A—C15—H15	120.00
C15—C14A—C18A	119.83 (11)	C16—C15—H15	120.00
C14A—C15—C16	120.44 (12)	C15—C16—H16	120.00
C15—C16—C17	120.68 (12)	C17—C16—H16	120.00
C16—C17—C18	120.38 (12)	C16—C17—H17	120.00
C17—C18—C18A	120.93 (11)	C18—C17—H17	120.00
C17—C18—C19	119.39 (11)	C41—C42—H42A	109.00
C18A—C18—C19	119.67 (11)	C41—C42—H42B	109.00
N11—C18A—C14A	123.45 (11)	C41—C42—H42C	109.00
N11—C18A—C18	118.84 (10)	H42A—C42—H42B	109.00
C14A—C18A—C18	117.71 (11)	H42A—C42—H42C	109.00
F1—C19—F2	106.37 (10)	H42B—C42—H42C	109.00

C5—N1—N2—N3	−0.27 (14)	C12—C13—C14—C14A	0.38 (18)
C14—N1—N2—N3	−179.85 (11)	N1—C14—C14A—C15	0.63 (18)
N2—N1—C5—C4	0.37 (13)	N1—C14—C14A—C18A	−177.90 (11)
N2—N1—C5—C6	−179.34 (11)	C13—C14—C14A—C15	−179.30 (12)
C14—N1—C5—C4	179.89 (12)	C13—C14—C14A—C18A	2.17 (17)
C14—N1—C5—C6	0.2 (2)	C14—C14A—C15—C16	−176.69 (12)
N2—N1—C14—C13	116.76 (13)	C18A—C14A—C15—C16	1.79 (19)
N2—N1—C14—C14A	−63.17 (15)	C14—C14A—C18A—N11	−3.21 (17)
C5—N1—C14—C13	−62.72 (18)	C14—C14A—C18A—C18	176.32 (11)
C5—N1—C14—C14A	117.34 (14)	C15—C14A—C18A—N11	178.19 (11)
N1—N2—N3—C4	0.04 (13)	C15—C14A—C18A—C18	−2.28 (17)
N2—N3—C4—C5	0.19 (14)	C14A—C15—C16—C17	−0.2 (2)
N2—N3—C4—C41	179.89 (12)	C15—C16—C17—C18	−0.9 (2)
C18A—N11—C12—C13	1.42 (18)	C16—C17—C18—C18A	0.36 (19)
C12—N11—C18A—C14A	1.48 (18)	C16—C17—C18—C19	179.32 (12)
C12—N11—C18A—C18	−178.05 (11)	C17—C18—C18A—N11	−179.22 (12)
N3—C4—C5—N1	−0.34 (13)	C17—C18—C18A—C14A	1.23 (18)
N3—C4—C5—C6	179.35 (12)	C19—C18—C18A—N11	1.82 (17)
C41—C4—C5—N1	179.97 (12)	C19—C18—C18A—C14A	−177.73 (11)
C41—C4—C5—C6	−0.3 (2)	C17—C18—C19—F1	1.58 (17)
N3—C4—C41—O41	−177.86 (13)	C17—C18—C19—F2	121.95 (13)
N3—C4—C41—C42	2.76 (19)	C17—C18—C19—F3	−116.87 (13)
C5—C4—C41—O41	1.8 (2)	C18A—C18—C19—F1	−179.45 (11)
C5—C4—C41—C42	−177.60 (13)	C18A—C18—C19—F2	−59.08 (16)
N11—C12—C13—C14	−2.36 (19)	C18A—C18—C19—F3	62.10 (16)
C12—C13—C14—N1	−179.56 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N3^ix	0.95	2.61	3.559 (2)	173.00
C15—H15···N2	0.95	2.55	3.101 (2)	117.00
C17—H17···F1	0.95	2.31	2.668 (2)	102.00
C17—H17···O41ⁱ	0.95	2.43	3.196 (2)	138.00
C42—H42A···F1^x	0.98	2.52	3.373 (2)	146.00
C42—H42B···F3^iv	0.98	2.48	3.434 (2)	165.00

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (iv) −x+3/2, y−1/2, −z+1/2; (ix) x+1/2, −y−1/2, z+1/2; (x) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁F₃N₄O
M_r	320.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	11.7974 (4), 8.2946 (2), 14.6706 (4)
β (°)	106.273 (3)
V (Å³)	1378.07 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.44 × 0.37 × 0.22

Data collection
Diffractometer	Oxford Diffraction Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.962, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13863, 4615, 2511
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.126, 0.96
No. of reflections	4615
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.24

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).