3-Methyl-1-phenyl-4-{phen­yl[4-(tri­fluoro­meth­yl)anilino]methyl­ene}-1H-pyrazol-5(4H)-one

Sun, Y.-F.; Wang, X.-L.; Ma, S.-Y.; Wang, Z.-Y.

doi:10.1107/S1600536807037993

3-Methyl-1-phenyl-4-{phenyl[4-(trifluoromethyl)anilino]methylene}-1H-pyrazol-5(4H)-one

Y.-F. Sun, X.-L. Wang, S.-Y. Ma and Z.-Y. Wang

In the title compound, C₂₄H₁₈F₃N₃O, the molecule exists in the enamine–keto tautomeric form. The pyrazolone ring makes dihedral angles of 31.8 (2), 45.4 (2) and 71.2 (2)° with the 1-phenyl, aniline and methylene-bound phenyl rings, respectively. An intramolecular N—H

O hydrogen bond helps to stabilize the molecular conformation.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037993/hb2502sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037993/hb2502Isup2.hkl Contains datablock I

CCDC reference: 660223

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.004 Å
R factor = 0.055
wR factor = 0.163
Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C18

Author Response: The F atoms of the -CF~3~ group show substantial motion, possibly relating to disorder, although this was not modelled.



Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.705
            Test value =      0.675
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.70 e/A   
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.

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

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

Comment top

The title compound, (I), was synthesized as part of a continuing project involving the structures of pyrazolone derivatives. Pyrazolone derivatives are well known for their potential applications in the areas of pharmaceuticals, agrochemicals, dyes, and pigments, and also as chelating agents and extracting agents. Moreover, they are capable of prototropic tautomerism (Akama & Tong, 1996; Eller & Holzer, 2004).

The molecule of (I) exists in enamine-keto tautomeric form in the crystal instead of the imine form (Fig. 1), as in 4-[(Z)-(benzylamino) phenylmethylene]-5-methyl-2-phenyl-2H-pyrazol-3-one (Jiang et al., 2004). The central pyrazolone (C1–C3/N1/N2) ring is essentially planar, with an r.m.s. deviation of 0.0116 Å for the fitted atoms. This ring makes dihedral angles of 31.8 (2), 45.4 (2) and 71.2 (2)° with the C5–C10, C12–C17 and C19–C24 phenyl rings, respectively. Similar tautomerism has also been observed in related pyrazolone analogues reported by us previously (Sun et al., 2006, 2007). In addition, the present compound also features an intramolecular hydrogen bond between the N3 and O1 atoms (Table 1), leading to the fact that atoms O1 and N3 are on the same side of the C2–C11 bond, which will be the potential bidentate N,O-chelate positions after deprotonation to form functional complexes as candidates with catalytic applications (Lu et al., 2006).

Related literature top

For related structures, see: Sun et al. (2006, 2007). For background literature, see: Akama & Tong (1996); Eller & Holzer (2004); Jiang et al. (2004); Lu et al.(2006).

Experimental top

A mixture of 1-phenyl-3-methyl-4-benzoyl-pyrazolone-5 (1 mmol) and 4-trifluoromethylaniline (1 mmol) in anhydrous ethanol (30 ml) was refluxed for 3 hr, and then cooled to room temperature. The precipitate was filtered and dried. The crude product was recrystallized from ethanol. Yellow crystals were thus obtained in 83% yield. A single-crystal of (I) suitable for an X-ray structural analysis was obtained by slowly evaporating a ethanolic solution at room temperature.

Structure description top

For related structures, see: Sun et al. (2006, 2007). For background literature, see: Akama & Tong (1996); Eller & Holzer (2004); Jiang et al. (2004); Lu et al.(2006).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. View of the molecular structure of (I) showing displacement ellipsoids at the 50% probability level. H atoms are shown as spheres of arbitrary radius. The dashed line indicates hydrogen bond.

3-Methyl-1-phenyl-4-{phenyl[4-(trifluoromethyl)anilino]methylene}-1H-pyrazol-5(4H)-one top

Crystal data top

C₂₄H₁₈F₃N₃O	Z = 2
M_r = 421.41	F(000) = 436
Triclinic, P1	D_x = 1.382 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6059 (9) Å	Cell parameters from 3675 reflections
b = 10.9913 (12) Å	θ = 2.1–28.2°
c = 13.8057 (15) Å	µ = 0.11 mm⁻¹
α = 108.448 (2)°	T = 273 K
β = 100.227 (2)°	Block, yellow
γ = 105.178 (2)°	0.35 × 0.26 × 0.18 mm
V = 1013.0 (2) Å³

Data collection top

Bruker SMART CCD diffractometer	3527 independent reflections
Radiation source: fine-focus sealed tube	3079 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.964, T_max = 0.981	k = −12→13
5150 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.163	w = 1/[σ²(F_o²) + (0.088P)² + 0.5882P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3527 reflections	Δρ_max = 0.71 e Å⁻³
282 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (5)

Crystal data top

C₂₄H₁₈F₃N₃O	γ = 105.178 (2)°
M_r = 421.41	V = 1013.0 (2) Å³
Triclinic, P1	Z = 2
a = 7.6059 (9) Å	Mo Kα radiation
b = 10.9913 (12) Å	µ = 0.11 mm⁻¹
c = 13.8057 (15) Å	T = 273 K
α = 108.448 (2)°	0.35 × 0.26 × 0.18 mm
β = 100.227 (2)°

Data collection top

Bruker SMART CCD diffractometer	3527 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3079 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.981	R_int = 0.011
5150 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.00	Δρ_max = 0.71 e Å⁻³
3527 reflections	Δρ_min = −0.40 e Å⁻³
282 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
F1	1.2873 (3)	0.7703 (4)	0.52098 (18)	0.1651 (15)
F2	1.1537 (3)	0.7329 (3)	0.6340 (3)	0.1570 (13)
F3	1.2712 (3)	0.9287 (2)	0.64567 (18)	0.1190 (8)
O1	0.2518 (2)	0.89023 (15)	0.26159 (13)	0.0553 (4)
N1	−0.0459 (2)	0.74140 (17)	0.14646 (14)	0.0452 (4)
N2	−0.1474 (3)	0.60170 (17)	0.10526 (14)	0.0481 (5)
N3	0.4577 (2)	0.74680 (18)	0.32255 (14)	0.0489 (5)
H3	0.4386	0.8219	0.3269	0.059*
C1	0.1347 (3)	0.7735 (2)	0.20940 (17)	0.0433 (5)
C2	0.1515 (3)	0.6428 (2)	0.20245 (16)	0.0418 (5)
C3	−0.0321 (3)	0.5436 (2)	0.13746 (17)	0.0445 (5)
C4	−0.1047 (4)	0.3929 (2)	0.1069 (2)	0.0617 (7)
H4A	−0.2385	0.3579	0.0713	0.093*
H4B	−0.0832	0.3724	0.1697	0.093*
H4C	−0.0393	0.3514	0.0599	0.093*
C5	−0.1398 (3)	0.8326 (2)	0.13113 (16)	0.0446 (5)
C6	−0.3329 (3)	0.7998 (3)	0.11965 (19)	0.0545 (6)
H6	−0.4027	0.7169	0.1203	0.065*
C7	−0.4214 (4)	0.8914 (3)	0.1072 (2)	0.0634 (7)
H7	−0.5509	0.8701	0.0998	0.076*
C8	−0.3185 (4)	1.0139 (3)	0.1055 (2)	0.0668 (7)
H8	−0.3780	1.0756	0.0978	0.080*
C9	−0.1283 (4)	1.0441 (3)	0.1152 (2)	0.0692 (7)
H9	−0.0592	1.1263	0.1133	0.083*
C10	−0.0376 (4)	0.9544 (2)	0.1279 (2)	0.0583 (6)
H10	0.0917	0.9759	0.1342	0.070*
C11	0.3135 (3)	0.6321 (2)	0.25890 (16)	0.0418 (5)
C12	0.6381 (3)	0.7604 (2)	0.38376 (17)	0.0454 (5)
C13	0.7166 (3)	0.8622 (2)	0.48522 (18)	0.0504 (5)
H13	0.6512	0.9199	0.5115	0.061*
C14	0.8908 (3)	0.8778 (2)	0.54689 (18)	0.0551 (6)
H14	0.9428	0.9462	0.6147	0.066*
C15	0.9884 (3)	0.7923 (3)	0.50833 (18)	0.0523 (6)
C16	0.9117 (3)	0.6922 (3)	0.40642 (18)	0.0566 (6)
H16	0.9775	0.6347	0.3802	0.068*
C17	0.7391 (3)	0.6772 (3)	0.34380 (18)	0.0552 (6)
H17	0.6902	0.6115	0.2748	0.066*
C18	1.1727 (4)	0.8038 (3)	0.5758 (2)	0.0710 (8)
C19	0.3297 (3)	0.4991 (2)	0.25615 (16)	0.0433 (5)
C20	0.3411 (3)	0.4054 (2)	0.16447 (18)	0.0525 (6)
H20	0.3318	0.4228	0.1024	0.063*
C21	0.3666 (4)	0.2856 (2)	0.1664 (2)	0.0650 (7)
H21	0.3753	0.2228	0.1054	0.078*
C22	0.3792 (4)	0.2590 (3)	0.2577 (2)	0.0694 (8)
H22	0.3982	0.1791	0.2586	0.083*
C23	0.3637 (4)	0.3507 (3)	0.3479 (2)	0.0670 (7)
H23	0.3692	0.3317	0.4091	0.080*
C24	0.3399 (3)	0.4708 (2)	0.34747 (19)	0.0540 (6)
H24	0.3307	0.5329	0.4086	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0721 (13)	0.299 (4)	0.0878 (15)	0.0989 (19)	0.0070 (11)	0.0061 (19)
F2	0.0921 (16)	0.199 (3)	0.202 (3)	0.0332 (17)	−0.0128 (16)	0.148 (3)
F3	0.0832 (13)	0.1226 (17)	0.0949 (14)	0.0156 (12)	−0.0288 (11)	0.0146 (13)
O1	0.0488 (9)	0.0386 (8)	0.0681 (10)	0.0136 (7)	0.0022 (7)	0.0158 (7)
N1	0.0427 (9)	0.0382 (9)	0.0524 (10)	0.0155 (7)	0.0047 (8)	0.0179 (8)
N2	0.0468 (10)	0.0396 (9)	0.0520 (10)	0.0136 (8)	0.0049 (8)	0.0159 (8)
N3	0.0460 (10)	0.0439 (10)	0.0538 (11)	0.0185 (8)	0.0044 (8)	0.0175 (8)
C1	0.0419 (11)	0.0416 (11)	0.0464 (11)	0.0161 (9)	0.0095 (9)	0.0170 (9)
C2	0.0450 (11)	0.0394 (10)	0.0426 (10)	0.0177 (9)	0.0102 (9)	0.0161 (8)
C3	0.0460 (11)	0.0412 (11)	0.0455 (11)	0.0162 (9)	0.0088 (9)	0.0167 (9)
C4	0.0560 (14)	0.0396 (12)	0.0779 (17)	0.0128 (10)	0.0039 (12)	0.0184 (11)
C5	0.0494 (12)	0.0447 (11)	0.0410 (11)	0.0221 (9)	0.0074 (9)	0.0163 (9)
C6	0.0501 (13)	0.0626 (14)	0.0567 (13)	0.0241 (11)	0.0124 (10)	0.0277 (11)
C7	0.0550 (14)	0.0838 (18)	0.0582 (14)	0.0401 (14)	0.0110 (11)	0.0251 (13)
C8	0.0799 (18)	0.0612 (15)	0.0594 (15)	0.0437 (14)	0.0031 (13)	0.0162 (12)
C9	0.0738 (17)	0.0480 (13)	0.0828 (18)	0.0259 (12)	0.0036 (14)	0.0273 (13)
C10	0.0531 (13)	0.0477 (13)	0.0747 (16)	0.0195 (10)	0.0091 (11)	0.0273 (12)
C11	0.0463 (11)	0.0435 (11)	0.0386 (10)	0.0189 (9)	0.0130 (9)	0.0162 (8)
C12	0.0420 (11)	0.0480 (11)	0.0476 (11)	0.0156 (9)	0.0101 (9)	0.0215 (9)
C13	0.0486 (12)	0.0439 (11)	0.0547 (13)	0.0155 (9)	0.0128 (10)	0.0147 (10)
C14	0.0493 (12)	0.0561 (13)	0.0465 (12)	0.0113 (10)	0.0078 (10)	0.0111 (10)
C15	0.0418 (11)	0.0667 (14)	0.0468 (12)	0.0154 (10)	0.0123 (9)	0.0220 (11)
C16	0.0479 (12)	0.0717 (16)	0.0513 (13)	0.0291 (11)	0.0153 (10)	0.0172 (11)
C17	0.0477 (12)	0.0669 (15)	0.0427 (11)	0.0225 (11)	0.0092 (9)	0.0099 (10)
C18	0.0534 (15)	0.095 (2)	0.0564 (15)	0.0266 (14)	0.0080 (12)	0.0216 (15)
C19	0.0410 (11)	0.0446 (11)	0.0462 (11)	0.0188 (9)	0.0080 (8)	0.0188 (9)
C20	0.0580 (13)	0.0514 (13)	0.0474 (12)	0.0253 (11)	0.0082 (10)	0.0162 (10)
C21	0.0654 (15)	0.0501 (13)	0.0686 (16)	0.0292 (12)	0.0031 (12)	0.0096 (12)
C22	0.0652 (16)	0.0463 (13)	0.087 (2)	0.0205 (12)	−0.0063 (14)	0.0266 (13)
C23	0.0690 (16)	0.0641 (16)	0.0682 (16)	0.0160 (13)	0.0025 (13)	0.0403 (14)
C24	0.0594 (14)	0.0561 (13)	0.0494 (12)	0.0209 (11)	0.0129 (10)	0.0243 (10)

Geometric parameters (Å, º) top

F1—C18	1.301 (3)	C9—C10	1.379 (3)
F2—C18	1.286 (4)	C9—H9	0.9300
F3—C18	1.321 (4)	C10—H10	0.9300
O1—C1	1.244 (3)	C11—C19	1.488 (3)
N1—C1	1.377 (3)	C12—C17	1.389 (3)
N1—N2	1.396 (2)	C12—C13	1.390 (3)
N1—C5	1.419 (3)	C13—C14	1.378 (3)
N2—C3	1.307 (3)	C13—H13	0.9300
N3—C11	1.340 (3)	C14—C15	1.381 (3)
N3—C12	1.421 (3)	C14—H14	0.9300
N3—H3	0.8600	C15—C16	1.387 (3)
C1—C2	1.451 (3)	C15—C18	1.489 (3)
C2—C11	1.390 (3)	C16—C17	1.375 (3)
C2—C3	1.442 (3)	C16—H16	0.9300
C3—C4	1.491 (3)	C17—H17	0.9300
C4—H4A	0.9600	C19—C24	1.385 (3)
C4—H4B	0.9600	C19—C20	1.390 (3)
C4—H4C	0.9600	C20—C21	1.388 (3)
C5—C10	1.380 (3)	C20—H20	0.9300
C5—C6	1.385 (3)	C21—C22	1.375 (4)
C6—C7	1.385 (3)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.379 (4)
C7—C8	1.379 (4)	C22—H22	0.9300
C7—H7	0.9300	C23—C24	1.380 (3)
C8—C9	1.368 (4)	C23—H23	0.9300
C8—H8	0.9300	C24—H24	0.9300

C1—N1—N2	112.32 (16)	C17—C12—C13	119.5 (2)
C1—N1—C5	127.73 (17)	C17—C12—N3	121.8 (2)
N2—N1—C5	119.51 (17)	C13—C12—N3	118.66 (19)
C3—N2—N1	106.70 (17)	C14—C13—C12	120.2 (2)
C11—N3—C12	128.37 (18)	C14—C13—H13	119.9
C11—N3—H3	115.8	C12—C13—H13	119.9
C12—N3—H3	115.8	C13—C14—C15	120.2 (2)
O1—C1—N1	126.24 (19)	C13—C14—H14	119.9
O1—C1—C2	129.26 (19)	C15—C14—H14	119.9
N1—C1—C2	104.48 (17)	C14—C15—C16	119.7 (2)
C11—C2—C3	132.65 (19)	C14—C15—C18	120.9 (2)
C11—C2—C1	122.13 (19)	C16—C15—C18	119.4 (2)
C3—C2—C1	104.96 (17)	C17—C16—C15	120.5 (2)
N2—C3—C2	111.44 (18)	C17—C16—H16	119.8
N2—C3—C4	118.50 (19)	C15—C16—H16	119.8
C2—C3—C4	130.03 (19)	C16—C17—C12	119.9 (2)
C3—C4—H4A	109.5	C16—C17—H17	120.1
C3—C4—H4B	109.5	C12—C17—H17	120.1
H4A—C4—H4B	109.5	F2—C18—F1	108.1 (3)
C3—C4—H4C	109.5	F2—C18—F3	103.3 (3)
H4A—C4—H4C	109.5	F1—C18—F3	104.5 (3)
H4B—C4—H4C	109.5	F2—C18—C15	113.4 (2)
C10—C5—C6	120.1 (2)	F1—C18—C15	113.1 (2)
C10—C5—N1	119.7 (2)	F3—C18—C15	113.5 (3)
C6—C5—N1	120.2 (2)	C24—C19—C20	119.8 (2)
C5—C6—C7	119.4 (2)	C24—C19—C11	119.31 (19)
C5—C6—H6	120.3	C20—C19—C11	120.87 (19)
C7—C6—H6	120.3	C21—C20—C19	119.4 (2)
C8—C7—C6	120.4 (2)	C21—C20—H20	120.3
C8—C7—H7	119.8	C19—C20—H20	120.3
C6—C7—H7	119.8	C22—C21—C20	120.5 (2)
C9—C8—C7	119.5 (2)	C22—C21—H21	119.8
C9—C8—H8	120.3	C20—C21—H21	119.8
C7—C8—H8	120.3	C21—C22—C23	120.0 (2)
C8—C9—C10	121.0 (3)	C21—C22—H22	120.0
C8—C9—H9	119.5	C23—C22—H22	120.0
C10—C9—H9	119.5	C22—C23—C24	120.1 (2)
C9—C10—C5	119.6 (2)	C22—C23—H23	119.9
C9—C10—H10	120.2	C24—C23—H23	119.9
C5—C10—H10	120.2	C23—C24—C19	120.2 (2)
N3—C11—C2	118.67 (18)	C23—C24—H24	119.9
N3—C11—C19	118.50 (18)	C19—C24—H24	119.9
C2—C11—C19	122.75 (18)

C1—N1—N2—C3	−2.4 (2)	C3—C2—C11—C19	4.0 (4)
C5—N1—N2—C3	−175.31 (18)	C1—C2—C11—C19	177.36 (19)
N2—N1—C1—O1	−175.1 (2)	C11—N3—C12—C17	41.3 (3)
C5—N1—C1—O1	−3.0 (4)	C11—N3—C12—C13	−140.4 (2)
N2—N1—C1—C2	3.3 (2)	C17—C12—C13—C14	−1.9 (3)
C5—N1—C1—C2	175.43 (19)	N3—C12—C13—C14	179.7 (2)
O1—C1—C2—C11	0.6 (4)	C12—C13—C14—C15	−0.1 (4)
N1—C1—C2—C11	−177.68 (19)	C13—C14—C15—C16	1.2 (4)
O1—C1—C2—C3	175.5 (2)	C13—C14—C15—C18	−177.2 (2)
N1—C1—C2—C3	−2.8 (2)	C14—C15—C16—C17	−0.2 (4)
N1—N2—C3—C2	0.5 (2)	C18—C15—C16—C17	178.2 (2)
N1—N2—C3—C4	178.7 (2)	C15—C16—C17—C12	−1.8 (4)
C11—C2—C3—N2	175.6 (2)	C13—C12—C17—C16	2.9 (4)
C1—C2—C3—N2	1.5 (2)	N3—C12—C17—C16	−178.8 (2)
C11—C2—C3—C4	−2.4 (4)	C14—C15—C18—F2	87.5 (4)
C1—C2—C3—C4	−176.5 (2)	C16—C15—C18—F2	−90.9 (3)
C1—N1—C5—C10	36.3 (3)	C14—C15—C18—F1	−148.9 (3)
N2—N1—C5—C10	−152.0 (2)	C16—C15—C18—F1	32.7 (4)
C1—N1—C5—C6	−143.6 (2)	C14—C15—C18—F3	−30.0 (4)
N2—N1—C5—C6	28.1 (3)	C16—C15—C18—F3	151.6 (3)
C10—C5—C6—C7	−1.3 (3)	N3—C11—C19—C24	64.0 (3)
N1—C5—C6—C7	178.6 (2)	C2—C11—C19—C24	−112.7 (2)
C5—C6—C7—C8	0.4 (4)	N3—C11—C19—C20	−113.8 (2)
C6—C7—C8—C9	0.6 (4)	C2—C11—C19—C20	69.5 (3)
C7—C8—C9—C10	−0.7 (4)	C24—C19—C20—C21	−1.3 (3)
C8—C9—C10—C5	−0.2 (4)	C11—C19—C20—C21	176.5 (2)
C6—C5—C10—C9	1.2 (4)	C19—C20—C21—C22	0.5 (4)
N1—C5—C10—C9	−178.6 (2)	C20—C21—C22—C23	1.0 (4)
C12—N3—C11—C2	−177.2 (2)	C21—C22—C23—C24	−1.5 (4)
C12—N3—C11—C19	6.0 (3)	C22—C23—C24—C19	0.6 (4)
C3—C2—C11—N3	−172.6 (2)	C20—C19—C24—C23	0.8 (4)
C1—C2—C11—N3	0.7 (3)	C11—C19—C24—C23	−177.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.86	1.98	2.704 (2)	141

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈F₃N₃O
M_r	421.41
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.6059 (9), 10.9913 (12), 13.8057 (15)
α, β, γ (°)	108.448 (2), 100.227 (2), 105.178 (2)
V (Å³)	1013.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.35 × 0.26 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.964, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	5150, 3527, 3079
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.163, 1.00
No. of reflections	3527
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.40

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.