1-{(Z)-[2-Meth­oxy-5-(trifluoro­meth­yl)anilino]methyl­idene}naphthalen-2(1H)-one

Kargılı, H.; Alaman Ağar, A.; Alpaslan, G.; Büyükgüngör, O.; Erdönmez, A.

doi:10.1107/S1600536812051410

1-{(Z)-[2-Methoxy-5-(trifluoromethyl)anilino]methylidene}naphthalen-2(1H)-one

H. Kargılı, A. Alaman Ağar, G. Alpaslan, O. Büyükgüngör and A. Erdönmez

The title compound, C₁₉H₁₄F₃NO₂, crystallizes in the keto–amine tautomeric form, with a strong intramolecular N—H

O hydrogen bond. The molecule is almost planar; the dihedral angle between the naphthalene ring system and the benzene ring is 4.60 (7)°. In the crystal, molecules are linked into chains along the c axis by C—H

O hydrogen bonds. The F atoms of the trifluoromethyl group are disordered over two positions with refined site occupancies of 0.668 (9) and 0.332 (9).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812051410/fy2084sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812051410/fy2084Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536812051410/fy2084Isup3.cml Supplementary material

CCDC reference: 925128

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R factor = 0.048
wR factor = 0.097
Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     36.124
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      6.166
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.920
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          7
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites ....          6
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................         12 Perc.
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C1     -C10           1.42 Ang.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         72

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   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
   6 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Schiff bases often exhibit various biological activities and in many cases were shown to have antibacterial, anticancer, anti-inflammatory and antitoxic properties (Lozier et al., 1975). Schiff bases have also been used as versatile ligands in coordination chemistry (Kargar et al., 2009; Yeap et al., 2009). There are two types of intramolecular hydrogen bonds in Schiff bases, namely N—H···O in keto (NH) (Hökelek et al., 2000) and N···H—O in enol (OH) (Odabaşoǧlu et al., 2005) tautomeric forms. The present X-ray investigation shows that the title compound is a Schiff base and exists in the keto-amine form in the solid state. An ORTEP-3 (Farrugia, 2012) plot of the molecule of (I) is shown in Fig. 1. The C2—O1 bond length of 1.272 (3) Å indicates double-bond character while the N1—C11 bond length of 1.322 (3) Å indicates single-bond character. These bond distances are comparable with those of compounds previously reported as keto–amine (Özek et al., 2004; Temel et al., 2010). The dihedral angle between the naphthalene ring system and the benzene ring is 4.60 (7)°. In the crystal, molecules are linked into chains (Fig. 2) along the c axis by intermolecular C-H···O hydrogen bonds (Table 1).

Related literature top

For the biological properties of Schiff bases, see: Lozier et al. (1975). For the coordination chemistry of Schiff bases, see: Kargar et al. (2009); Yeap et al. (2009). For Schiff base tautomerism, see: Hökelek et al. (2000); Odabaşoǧlu et al. (2005). For related strucures, see: Özek et al. (2004); Temel et al. (2010).

Experimental top

(Z)-1-[(2-Methoxy-5-(trifluoromethyl)phenylamino)methylene]naphthalen-2(1H)-one was prepared by refluxing a mixture of a solution containing 2-hydroxy-1-naphthaldehyde (17.22 mg, 0.1 mmol) in ethanol (20 ml) and a solution containing 2-methoxy-5-(trifluoromethyl)aniline (19.12 mg, 0.1 mmol) in ethanol (20 ml). The reaction mixture was stirred for 5 h under reflux. Single crystals of the title compound for X-ray analysis were obtained by slow evaporation of an ethanol solution (Yield 84%; m.p. 472–475 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound; dashed lines indicate intermolecular hydrogen bonds.

1-{(Z)-[2-Methoxy-5-(trifluoromethyl)anilino]methylidene}naphthalen- 2(1H)-one top

Crystal data top

C₁₉H₁₄F₃NO₂	F(000) = 712
M_r = 345.31	D_x = 1.435 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15281 reflections
a = 16.3922 (10) Å	θ = 1.5–28.0°
b = 5.7201 (2) Å	µ = 0.12 mm⁻¹
c = 17.7632 (10) Å	T = 296 K
β = 106.284 (5)°	Prism, brown
V = 1598.75 (14) Å³	0.58 × 0.35 × 0.13 mm
Z = 4

Data collection top

Stoe IPDSII diffractometer	3129 independent reflections
Radiation source: fine-focus sealed tube	1722 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.4°
ω scans	h = −20→20
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −7→7
T_min = 0.949, T_max = 0.984	l = −21→21
19794 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0399P)²] where P = (F_o² + 2F_c²)/3
3129 reflections	(Δ/σ)_max < 0.001
258 parameters	Δρ_max = 0.15 e Å⁻³
72 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₉H₁₄F₃NO₂	V = 1598.75 (14) Å³
M_r = 345.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.3922 (10) Å	µ = 0.12 mm⁻¹
b = 5.7201 (2) Å	T = 296 K
c = 17.7632 (10) Å	0.58 × 0.35 × 0.13 mm
β = 106.284 (5)°

Data collection top

Stoe IPDSII diffractometer	3129 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1722 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.984	R_int = 0.057
19794 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	72 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.15 e Å⁻³
3129 reflections	Δρ_min = −0.17 e Å⁻³
258 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
C1	0.17645 (13)	0.2354 (4)	0.18859 (12)	0.0443 (6)
C2	0.15233 (15)	0.1866 (5)	0.10590 (13)	0.0527 (6)
C3	0.10170 (16)	−0.0181 (5)	0.07934 (13)	0.0589 (7)
H3	0.0853	−0.0530	0.0261	0.071*
C4	0.07736 (15)	−0.1601 (5)	0.12881 (13)	0.0573 (7)
H4	0.0450	−0.2913	0.1088	0.069*
C5	0.09943 (13)	−0.1173 (4)	0.21140 (13)	0.0459 (6)
C6	0.07423 (15)	−0.2706 (4)	0.26206 (14)	0.0568 (6)
H6	0.0436	−0.4041	0.2417	0.068*
C7	0.09358 (16)	−0.2288 (5)	0.34056 (14)	0.0625 (7)
H7	0.0765	−0.3326	0.3735	0.075*
C8	0.13909 (17)	−0.0297 (5)	0.37078 (13)	0.0611 (7)
H8	0.1519	0.0010	0.4242	0.073*
C9	0.16550 (15)	0.1225 (4)	0.32305 (12)	0.0543 (6)
H9	0.1960	0.2550	0.3447	0.065*
C10	0.14750 (13)	0.0831 (4)	0.24208 (12)	0.0424 (5)
C11	0.22965 (14)	0.4238 (4)	0.21675 (13)	0.0466 (6)
H11	0.2449	0.4530	0.2704	0.056*
C12	0.31391 (14)	0.7553 (4)	0.19682 (13)	0.0470 (6)
C13	0.33425 (15)	0.8888 (4)	0.13842 (13)	0.0518 (6)
C14	0.38600 (16)	1.0818 (5)	0.15828 (15)	0.0611 (7)
H14	0.3995	1.1696	0.1194	0.073*
C15	0.41778 (15)	1.1448 (5)	0.23597 (16)	0.0616 (7)
H15	0.4525	1.2757	0.2492	0.074*
C16	0.39861 (15)	1.0159 (4)	0.29414 (14)	0.0526 (6)
C17	0.34681 (14)	0.8209 (4)	0.27413 (13)	0.0531 (6)
H17	0.3341	0.7330	0.3134	0.064*
C18	0.43282 (19)	1.0816 (6)	0.37746 (17)	0.0706 (8)
C19	0.3127 (2)	0.9460 (5)	0.00083 (15)	0.0800 (9)
H19A	0.2853	0.8708	−0.0480	0.120*
H19B	0.3725	0.9578	0.0066	0.120*
H19C	0.2893	1.0997	0.0014	0.120*
F1A	0.3844 (4)	1.0304 (15)	0.4230 (2)	0.112 (2)	0.668 (9)
F2A	0.5162 (2)	1.0948 (14)	0.3989 (3)	0.1156 (18)	0.668 (9)
F3A	0.4413 (6)	1.3154 (9)	0.3887 (3)	0.139 (2)	0.668 (9)
F1B	0.4342 (10)	0.897 (2)	0.4242 (4)	0.108 (4)	0.332 (9)
F2B	0.4937 (8)	0.945 (3)	0.4172 (5)	0.113 (4)	0.332 (9)
F3B	0.3934 (8)	1.252 (3)	0.3936 (6)	0.126 (5)	0.332 (9)
N1	0.25997 (12)	0.5641 (3)	0.17194 (11)	0.0489 (5)
O1	0.17545 (12)	0.3149 (3)	0.05715 (9)	0.0707 (5)
O2	0.29915 (11)	0.8115 (3)	0.06414 (9)	0.0651 (5)
H1	0.2375 (18)	0.521 (5)	0.1153 (17)	0.100 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0468 (13)	0.0434 (15)	0.0421 (12)	0.0046 (11)	0.0116 (10)	0.0010 (11)
C2	0.0547 (14)	0.0570 (16)	0.0451 (13)	0.0073 (13)	0.0120 (11)	0.0037 (13)
C3	0.0589 (16)	0.0727 (19)	0.0403 (12)	0.0039 (14)	0.0064 (11)	−0.0073 (13)
C4	0.0540 (15)	0.0602 (17)	0.0557 (15)	−0.0027 (13)	0.0117 (12)	−0.0125 (13)
C5	0.0426 (13)	0.0439 (14)	0.0516 (13)	0.0045 (11)	0.0141 (10)	−0.0030 (11)
C6	0.0534 (15)	0.0492 (16)	0.0699 (16)	−0.0039 (12)	0.0207 (13)	−0.0024 (13)
C7	0.0706 (17)	0.0593 (18)	0.0631 (16)	−0.0044 (15)	0.0281 (13)	0.0099 (14)
C8	0.0710 (17)	0.0699 (19)	0.0436 (13)	−0.0054 (15)	0.0179 (12)	0.0046 (13)
C9	0.0596 (15)	0.0574 (17)	0.0458 (13)	−0.0090 (13)	0.0144 (11)	−0.0018 (12)
C10	0.0391 (12)	0.0447 (14)	0.0431 (12)	0.0036 (11)	0.0113 (9)	0.0015 (11)
C11	0.0485 (13)	0.0489 (15)	0.0447 (12)	0.0066 (12)	0.0167 (11)	0.0070 (12)
C12	0.0470 (13)	0.0420 (14)	0.0551 (14)	0.0081 (12)	0.0195 (11)	0.0077 (12)
C13	0.0521 (14)	0.0543 (17)	0.0534 (15)	0.0044 (12)	0.0221 (12)	0.0049 (12)
C14	0.0652 (16)	0.0610 (18)	0.0643 (17)	−0.0004 (15)	0.0298 (13)	0.0125 (14)
C15	0.0542 (16)	0.0566 (17)	0.0786 (18)	−0.0081 (13)	0.0259 (14)	0.0024 (15)
C16	0.0476 (14)	0.0523 (16)	0.0598 (15)	−0.0011 (12)	0.0180 (11)	0.0005 (13)
C17	0.0549 (14)	0.0540 (16)	0.0538 (14)	0.0009 (13)	0.0206 (12)	0.0088 (12)
C18	0.065 (2)	0.070 (2)	0.077 (2)	−0.0131 (18)	0.0216 (16)	−0.0105 (18)
C19	0.099 (2)	0.090 (2)	0.0601 (16)	−0.0002 (18)	0.0382 (15)	0.0151 (16)
F1A	0.114 (3)	0.164 (5)	0.0654 (19)	−0.055 (3)	0.036 (2)	−0.023 (2)
F2A	0.072 (2)	0.171 (5)	0.091 (2)	−0.037 (3)	0.0024 (16)	−0.023 (3)
F3A	0.222 (6)	0.094 (3)	0.104 (3)	−0.050 (4)	0.048 (4)	−0.029 (2)
F1B	0.144 (8)	0.118 (6)	0.058 (3)	−0.058 (6)	0.024 (5)	0.008 (4)
F2B	0.086 (6)	0.154 (8)	0.080 (5)	0.052 (6)	−0.006 (4)	−0.029 (5)
F3B	0.129 (7)	0.140 (9)	0.100 (5)	0.047 (6)	0.018 (5)	−0.061 (6)
N1	0.0534 (12)	0.0474 (13)	0.0470 (11)	0.0008 (10)	0.0156 (9)	0.0033 (10)
O1	0.0933 (14)	0.0756 (13)	0.0442 (9)	−0.0021 (11)	0.0208 (9)	0.0103 (9)
O2	0.0776 (12)	0.0706 (13)	0.0525 (10)	−0.0053 (10)	0.0273 (9)	0.0083 (9)

Geometric parameters (Å, º) top

C1—C11	1.388 (3)	C12—C13	1.402 (3)
C1—C2	1.437 (3)	C13—O2	1.357 (3)
C1—C10	1.463 (3)	C13—C14	1.377 (3)
C2—O1	1.272 (3)	C14—C15	1.379 (3)
C2—C3	1.436 (3)	C14—H14	0.9300
C3—C4	1.337 (3)	C15—C16	1.376 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.430 (3)	C16—C17	1.387 (3)
C4—H4	0.9300	C16—C18	1.477 (4)
C5—C6	1.399 (3)	C17—H17	0.9300
C5—C10	1.411 (3)	C18—F3B	1.248 (8)
C6—C7	1.362 (3)	C18—F2B	1.308 (8)
C6—H6	0.9300	C18—F1A	1.315 (4)
C7—C8	1.385 (3)	C18—F2A	1.315 (4)
C7—H7	0.9300	C18—F1B	1.339 (8)
C8—C9	1.367 (3)	C18—F3A	1.354 (5)
C8—H8	0.9300	C19—O2	1.430 (3)
C9—C10	1.403 (3)	C19—H19A	0.9600
C9—H9	0.9300	C19—H19B	0.9600
C11—N1	1.322 (3)	C19—H19C	0.9600
C11—H11	0.9300	F2A—F3A	1.735 (10)
C12—C17	1.379 (3)	F1B—F2B	1.05 (2)
C12—N1	1.398 (3)	N1—H1	1.00 (3)

C11—C1—C2	119.0 (2)	C13—C14—C15	119.9 (2)
C11—C1—C10	120.90 (19)	C13—C14—H14	120.0
C2—C1—C10	120.1 (2)	C15—C14—H14	120.0
O1—C2—C3	120.1 (2)	C16—C15—C14	120.7 (2)
O1—C2—C1	122.3 (2)	C16—C15—H15	119.7
C3—C2—C1	117.5 (2)	C14—C15—H15	119.7
C4—C3—C2	122.1 (2)	C15—C16—C17	119.4 (2)
C4—C3—H3	119.0	C15—C16—C18	120.9 (3)
C2—C3—H3	119.0	C17—C16—C18	119.7 (2)
C3—C4—C5	122.3 (2)	C12—C17—C16	121.0 (2)
C3—C4—H4	118.9	C12—C17—H17	119.5
C5—C4—H4	118.9	C16—C17—H17	119.5
C6—C5—C10	119.6 (2)	F3B—C18—F2B	135.2 (6)
C6—C5—C4	121.1 (2)	F1A—C18—F2A	126.4 (4)
C10—C5—C4	119.2 (2)	F3B—C18—F1B	113.3 (7)
C7—C6—C5	121.5 (2)	F2B—C18—F1B	46.8 (11)
C7—C6—H6	119.3	F1A—C18—F3A	100.6 (4)
C5—C6—H6	119.3	F2A—C18—F3A	81.1 (6)
C6—C7—C8	119.1 (2)	F3B—C18—C16	110.7 (5)
C6—C7—H7	120.4	F2B—C18—C16	114.0 (4)
C8—C7—H7	120.4	F1A—C18—C16	115.8 (3)
C9—C8—C7	120.9 (2)	F2A—C18—C16	112.1 (3)
C9—C8—H8	119.6	F1B—C18—C16	110.9 (4)
C7—C8—H8	119.6	F3A—C18—C16	113.2 (4)
C8—C9—C10	121.4 (2)	O2—C19—H19A	109.5
C8—C9—H9	119.3	O2—C19—H19B	109.5
C10—C9—H9	119.3	H19A—C19—H19B	109.5
C9—C10—C5	117.4 (2)	O2—C19—H19C	109.5
C9—C10—C1	123.9 (2)	H19A—C19—H19C	109.5
C5—C10—C1	118.73 (19)	H19B—C19—H19C	109.5
N1—C11—C1	124.0 (2)	C18—F2A—F3A	50.4 (3)
N1—C11—H11	118.0	C18—F3A—F2A	48.5 (3)
C1—C11—H11	118.0	F2B—F1B—C18	65.0 (8)
C17—C12—N1	124.3 (2)	F1B—F2B—C18	68.1 (8)
C17—C12—C13	118.8 (2)	C11—N1—C12	126.6 (2)
N1—C12—C13	116.9 (2)	C11—N1—H1	111.3 (17)
O2—C13—C14	125.0 (2)	C12—N1—H1	122.1 (17)
O2—C13—C12	114.7 (2)	C13—O2—C19	118.2 (2)
C14—C13—C12	120.3 (2)

C11—C1—C2—O1	−2.7 (3)	C18—C16—C17—C12	180.0 (2)
C10—C1—C2—O1	179.5 (2)	C15—C16—C18—F3B	76.5 (10)
C11—C1—C2—C3	176.1 (2)	C17—C16—C18—F3B	−103.8 (10)
C10—C1—C2—C3	−1.7 (3)	C15—C16—C18—F2B	−106.0 (11)
O1—C2—C3—C4	178.8 (2)	C17—C16—C18—F2B	73.6 (11)
C1—C2—C3—C4	−0.1 (3)	C15—C16—C18—F1A	149.0 (5)
C2—C3—C4—C5	0.5 (4)	C17—C16—C18—F1A	−31.4 (6)
C3—C4—C5—C6	−179.0 (2)	C15—C16—C18—F2A	−55.9 (5)
C3—C4—C5—C10	0.9 (3)	C17—C16—C18—F2A	123.7 (5)
C10—C5—C6—C7	1.3 (3)	C15—C16—C18—F1B	−156.9 (9)
C4—C5—C6—C7	−178.7 (2)	C17—C16—C18—F1B	22.8 (10)
C5—C6—C7—C8	0.1 (4)	C15—C16—C18—F3A	33.6 (6)
C6—C7—C8—C9	−0.8 (4)	C17—C16—C18—F3A	−146.8 (5)
C7—C8—C9—C10	0.1 (4)	F3B—C18—F2A—F3A	−17.8 (9)
C8—C9—C10—C5	1.3 (3)	F2B—C18—F2A—F3A	−145.9 (6)
C8—C9—C10—C1	−177.9 (2)	F1A—C18—F2A—F3A	−96.6 (6)
C6—C5—C10—C9	−2.0 (3)	F1B—C18—F2A—F3A	−135.1 (6)
C4—C5—C10—C9	178.0 (2)	C16—C18—F2A—F3A	111.5 (4)
C6—C5—C10—C1	177.3 (2)	F3B—C18—F3A—F2A	154.8 (11)
C4—C5—C10—C1	−2.7 (3)	F2B—C18—F3A—F2A	27.3 (7)
C11—C1—C10—C9	4.5 (3)	F1A—C18—F3A—F2A	125.6 (4)
C2—C1—C10—C9	−177.7 (2)	F1B—C18—F3A—F2A	83.5 (10)
C11—C1—C10—C5	−174.70 (19)	C16—C18—F3A—F2A	−110.3 (4)
C2—C1—C10—C5	3.1 (3)	F3B—C18—F1B—F2B	−131.0 (8)
C2—C1—C11—N1	0.2 (3)	F1A—C18—F1B—F2B	−149.5 (8)
C10—C1—C11—N1	178.1 (2)	F2A—C18—F1B—F2B	−10.6 (7)
C17—C12—C13—O2	180.0 (2)	F3A—C18—F1B—F2B	−89.7 (11)
N1—C12—C13—O2	−0.8 (3)	C16—C18—F1B—F2B	103.9 (6)
C17—C12—C13—C14	−0.1 (3)	F3B—C18—F2B—F1B	79.9 (17)
N1—C12—C13—C14	179.0 (2)	F1A—C18—F2B—F1B	22.7 (7)
O2—C13—C14—C15	179.6 (2)	F2A—C18—F2B—F1B	165.1 (10)
C12—C13—C14—C15	−0.2 (4)	F3A—C18—F2B—F1B	126.0 (8)
C13—C14—C15—C16	0.3 (4)	C16—C18—F2B—F1B	−96.7 (8)
C14—C15—C16—C17	0.0 (4)	C1—C11—N1—C12	−179.7 (2)
C14—C15—C16—C18	179.6 (2)	C17—C12—N1—C11	2.8 (3)
N1—C12—C17—C16	−178.7 (2)	C13—C12—N1—C11	−176.3 (2)
C13—C12—C17—C16	0.4 (3)	C14—C13—O2—C19	−3.5 (3)
C15—C16—C17—C12	−0.4 (3)	C12—C13—O2—C19	176.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.93	2.51	3.423 (3)	166
N1—H1···O1	1.00 (3)	1.70 (3)	2.554 (3)	140 (2)

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄F₃NO₂
M_r	345.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.3922 (10), 5.7201 (2), 17.7632 (10)
β (°)	106.284 (5)
V (Å³)	1598.75 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.58 × 0.35 × 0.13

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.949, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	19794, 3129, 1722
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.097, 0.95
No. of reflections	3129
No. of parameters	258
No. of restraints	72
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).