(2E)-2-[2-(4-Chloro­phen­yl)hydrazin-1-yl­idene]-4,4,4-trifluoro-3-oxobutanal

Huo, Y.-P.; Zhou, L.-H.

doi:10.1107/S1600536810021835

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1654

doi:10.1107/S1600536810021835

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(2E)-2-[2-(4-Chlorophenyl)hydrazin-1-ylidene]-4,4,4-trifluoro-3-oxobutanal

Yan-Ping Huo ^a ^* and Li-Hua Zhou ^a

^aFaculty of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: tigerhuo1974@yahoo.com.cn

(Received 9 April 2010; accepted 8 June 2010; online 16 June 2010)

The title compound, C₁₀H₆ClF₃N₂O₂, was synthesized by coupling 4-dimethylamino-1,1,1-trifluorobut-3-en-2-one with 4-chlorobenzenediazonium chloride. It crystallizes with two molecules in the asymmetric unit, which form two similar centrosymmetric dimers via hydrogen bonds. Extensive electron delocalization and intramolecular N—H⋯O hydrogen bonds are responsible for a planar conformation of the molecules (maximum deviations = 0.010 and −0.015 Å for the two molecules). In addition to hydrogen bonds, π–π stacking interactions with centroid–centroid distances of 3.604 (2) and 3.583 (2) Å contribute to the stability of the crystal structure.

Related literature

For the crystal structure of the isostructural iodo derivative, see: Jiang & Zhu (2008 ).

Experimental

Crystal data

C₁₀H₆ClF₃N₂O₂
M_r = 278.62
Triclinic, $[P \overline 1]$
a = 7.6440 (4) Å
b = 7.7139 (4) Å
c = 19.4221 (10) Å
α = 86.134 (1)°
β = 81.706 (1)°
γ = 88.999 (1)°
V = 1130.63 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 173 K
0.44 × 0.38 × 0.35 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.853, T_max = 0.880
8820 measured reflections
4387 independent reflections
3577 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.111
S = 1.05
4387 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11⋯O8	0.88	2.01	2.6746 (18)	131
N29—H29⋯O26	0.88	2.03	2.679 (2)	130
N29—H29⋯O26ⁱ	0.88	2.42	3.2159 (19)	150
C27—H27⋯O6ⁱⁱ	0.95	2.59	3.491 (2)	158
C36—H36⋯O26ⁱ	0.95	2.52	3.323 (3)	143
Symmetry codes: (i) -x, -y, -z+2; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003 ); data reduction: SAINT-Plus; 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, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021835/gk2268sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021835/gk2268Isup2.hkl

checkCIF report

Comment top

Herein, we report the crystal structure of (2E)-2-[2-(4-chlorophenyl)]hydrazinylidene]-4,4,4-trifluoro-3-oxobutanal, which was prepared via a reaction of 4-(dimethylamino)-1,1,1-trifluorobut-3-en-2-one with diazonium salt according to the procedure reported by Zhu et al. (2008). The title compound, 3, has been characterized by ESI-MS, NMR, FTIR spectroscopy and elemental analysis. Here we report the crystal structure of 3. It crystallizes with two almost identical molecules in the asymmetric unit. The molecule is almost planar except for the –CF₃ group F atoms. There are some supramolecular interactions in the compound 3. The intramolecular N—H···O hydrogen bonds are N11—H11···O8 and N29—H29···O26 (Table 1) together with strong π-π stacking interactions [centroid-to-centroid distance = 3.604 (2) Å; 3.583 (2) Å] that contribute to the stability of the structure.

Related literature top

For the crystal structure of the isostructural iodo derivative, see: Jiang & Zhu (2008).

Experimental top

The title compound was prepared via the reaction of 4-(dimethylamino)-1,1,1-trifluorobut-3-en-2-one with diazonium salt according to the procedure reported by Zhu et al. (2008). A solution of the p-chloroaniline 2 (1.28 g, 10 mmol) in a solution of 3 M HCl (5 ml) was diazotized at 0 °C by slow addition of a solution of NaNO₂ (0.7 g, 10 mmol) in 5 ml H₂O. The solution of aniline diazonium salt was added dropwise to a mixture of compound 1 (see scheme) (1.67 g, 10 mmol) with NaOH (1.6 g, 40 mmol) and ethanol (50 ml) in ice-salt bath. The reaction mixture was stirred for 1 h at the same temperature, then TLC analysis showed that the reaction had finished. The resulting precipitate was filtered off. Purification by column chromatography on silica gel (hexane:AcOEt = 30:1) gave red solid 3 in 75% yield. mp 418-420 K. ¹H NMR (CDCl₃, 300 MHz) δ14.87 (1H, s, NH), 10.03 (1H, s, CHO), 7.45 (4H, s, Ph), ¹⁹F NMR (CDCl₃): -71.50 (3 F, s, CF₃). IR (KBr, cm^-1): 2924, 1699, 1526, 1308, 1187, 1157, 897; ESI-MS m/z: 279.9 ([M+H]⁺); Elemental analysis: found C: 43.13, H: 2.29, N: 10.07; calculated for (C₁₀H₆ClF₃N₂O₂) C: 43.11 H: 2.17 N: 10.05 (%). 20 mg of compound 3 was dissolved in 10 ml (EtOAc:pPetroleum ether = 1:8) and the solution was kept at room temperature for 6 d, natural evaporation gave red single crystals of compound 3 suitable for X-ray analysis.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); 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, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The synthesis of (E)-2-(2-(4-Chlophenyl)hydrazono)-4,4,4-trifluoro-3-oxobutanal
	Fig. 2. View of the asymmetric unit in the title compound.

(2E)-2-[2-(4-Chlorophenyl)hydrazin-1-ylidene]-4,4,4-trifluoro- 3-oxobutanal top

Crystal data top

C₁₀H₆ClF₃N₂O₂	Z = 4
M_r = 278.62	F(000) = 560
Triclinic, P1	D_x = 1.637 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6440 (4) Å	Cell parameters from 8820 reflections
b = 7.7139 (4) Å	θ = 1.1–26.0°
c = 19.4221 (10) Å	µ = 0.37 mm⁻¹
α = 86.134 (1)°	T = 173 K
β = 81.706 (1)°	Block, yellow
γ = 88.999 (1)°	0.44 × 0.38 × 0.35 mm
V = 1130.63 (10) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	4387 independent reflections
Radiation source: fine-focus sealed tube	3577 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 26.0°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.853, T_max = 0.880	k = −9→9
8820 measured reflections	l = −23→23

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0688P)² + 0.2643P] where P = (F_o² + 2F_c²)/3
4387 reflections	(Δ/σ)_max = 0.001
325 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₀H₆ClF₃N₂O₂	γ = 88.999 (1)°
M_r = 278.62	V = 1130.63 (10) Å³
Triclinic, P1	Z = 4
a = 7.6440 (4) Å	Mo Kα radiation
b = 7.7139 (4) Å	µ = 0.37 mm⁻¹
c = 19.4221 (10) Å	T = 173 K
α = 86.134 (1)°	0.44 × 0.38 × 0.35 mm
β = 81.706 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	4387 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3577 reflections with I > 2σ(I)
T_min = 0.853, T_max = 0.880	R_int = 0.017
8820 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.05	Δρ_max = 0.29 e Å⁻³
4387 reflections	Δρ_min = −0.23 e Å⁻³
325 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
F1	0.41928 (17)	−0.14617 (18)	0.81983 (6)	0.0571 (4)
F2	0.43024 (15)	0.08932 (15)	0.75482 (6)	0.0461 (3)
F3	0.36230 (15)	−0.15031 (16)	0.71485 (6)	0.0464 (3)
C4	0.4666 (3)	−0.0800 (3)	0.75480 (10)	0.0373 (4)
C5	0.6660 (2)	−0.1153 (2)	0.73104 (9)	0.0312 (4)
O6	0.7481 (2)	−0.19276 (19)	0.77259 (7)	0.0478 (4)
C7	0.7407 (2)	−0.0528 (2)	0.66091 (9)	0.0271 (4)
O8	0.99555 (16)	−0.04137 (17)	0.57727 (7)	0.0362 (3)
C9	0.9266 (2)	−0.0873 (2)	0.63594 (10)	0.0315 (4)
H9	0.9963	−0.1478	0.6666	0.038*
N10	0.62895 (18)	0.03374 (17)	0.62508 (7)	0.0258 (3)
N11	0.67864 (18)	0.09586 (17)	0.56194 (7)	0.0255 (3)
H11	0.7879	0.0804	0.5417	0.031*
C12	0.5552 (2)	0.18901 (19)	0.52582 (8)	0.0244 (3)
C13	0.3785 (2)	0.2002 (2)	0.55450 (9)	0.0287 (4)
H13	0.3384	0.1459	0.5992	0.034*
C14	0.2614 (2)	0.2914 (2)	0.51727 (10)	0.0316 (4)
H14	0.1398	0.2989	0.5359	0.038*
C15	0.3231 (2)	0.3710 (2)	0.45304 (9)	0.0290 (4)
Cl16	0.17686 (7)	0.48727 (6)	0.40584 (3)	0.04196 (15)
C17	0.4984 (2)	0.3604 (2)	0.42417 (9)	0.0296 (4)
H17	0.5382	0.4158	0.3796	0.036*
C18	0.6156 (2)	0.2678 (2)	0.46094 (9)	0.0287 (4)
H18	0.7367	0.2585	0.4417	0.034*
F19	0.14628 (17)	0.47780 (18)	0.67586 (6)	0.0541 (3)
F20	0.32094 (14)	0.45871 (15)	0.75272 (6)	0.0422 (3)
F21	0.06433 (17)	0.57720 (15)	0.77605 (7)	0.0525 (3)
C22	0.1519 (2)	0.4478 (3)	0.74380 (10)	0.0368 (4)
C23	0.0728 (2)	0.2668 (2)	0.76964 (10)	0.0344 (4)
O24	0.0173 (2)	0.1827 (2)	0.72714 (8)	0.0522 (4)
C25	0.0720 (2)	0.2110 (2)	0.84266 (9)	0.0302 (4)
O26	0.0099 (2)	−0.01845 (17)	0.92755 (7)	0.0438 (3)
C27	0.0109 (2)	0.0371 (2)	0.86723 (10)	0.0367 (4)
H27	−0.0294	−0.0355	0.8353	0.044*
N28	0.13267 (18)	0.32559 (19)	0.88092 (7)	0.0287 (3)
N29	0.13874 (19)	0.29289 (19)	0.94648 (7)	0.0295 (3)
H29	0.1023	0.1924	0.9673	0.035*
C30	0.2050 (2)	0.4213 (2)	0.98458 (9)	0.0287 (4)
C31	0.2464 (2)	0.5856 (2)	0.95348 (10)	0.0346 (4)
H31	0.2305	0.6132	0.9064	0.042*
C32	0.3108 (3)	0.7084 (3)	0.99149 (11)	0.0391 (4)
H32	0.3400	0.8212	0.9707	0.047*
C33	0.3327 (2)	0.6661 (3)	1.06009 (10)	0.0367 (4)
Cl34	0.41607 (7)	0.82172 (8)	1.10737 (3)	0.05462 (18)
C35	0.2909 (3)	0.5042 (3)	1.09141 (10)	0.0397 (4)
H35	0.3058	0.4773	1.1387	0.048*
C36	0.2265 (2)	0.3804 (3)	1.05305 (10)	0.0355 (4)
H36	0.1974	0.2677	1.0739	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0558 (8)	0.0763 (9)	0.0332 (7)	−0.0031 (7)	0.0083 (6)	0.0094 (6)
F2	0.0472 (7)	0.0443 (7)	0.0457 (7)	0.0121 (5)	−0.0005 (5)	−0.0122 (5)
F3	0.0399 (6)	0.0555 (7)	0.0441 (7)	−0.0124 (5)	−0.0044 (5)	−0.0055 (5)
C4	0.0405 (11)	0.0413 (10)	0.0281 (9)	−0.0002 (8)	0.0008 (8)	−0.0012 (8)
C5	0.0361 (9)	0.0271 (8)	0.0306 (9)	0.0005 (7)	−0.0056 (8)	−0.0019 (7)
O6	0.0513 (9)	0.0526 (9)	0.0378 (8)	0.0088 (7)	−0.0084 (7)	0.0115 (7)
C7	0.0293 (8)	0.0254 (8)	0.0274 (9)	0.0005 (7)	−0.0058 (7)	−0.0031 (6)
O8	0.0294 (7)	0.0437 (7)	0.0344 (7)	0.0009 (6)	−0.0017 (5)	−0.0011 (6)
C9	0.0299 (9)	0.0311 (9)	0.0344 (10)	0.0017 (7)	−0.0068 (8)	−0.0031 (7)
N10	0.0293 (7)	0.0225 (7)	0.0262 (7)	−0.0011 (6)	−0.0056 (6)	−0.0028 (5)
N11	0.0238 (7)	0.0257 (7)	0.0267 (7)	−0.0001 (5)	−0.0031 (6)	−0.0007 (6)
C12	0.0289 (8)	0.0188 (7)	0.0266 (8)	0.0002 (6)	−0.0071 (7)	−0.0035 (6)
C13	0.0307 (9)	0.0256 (8)	0.0290 (9)	−0.0008 (7)	−0.0018 (7)	−0.0008 (7)
C14	0.0269 (9)	0.0285 (9)	0.0398 (10)	0.0013 (7)	−0.0044 (7)	−0.0050 (7)
C15	0.0344 (9)	0.0235 (8)	0.0318 (9)	0.0047 (7)	−0.0129 (7)	−0.0052 (7)
Cl16	0.0452 (3)	0.0363 (3)	0.0482 (3)	0.0099 (2)	−0.0215 (2)	−0.0017 (2)
C17	0.0369 (9)	0.0266 (8)	0.0255 (9)	0.0000 (7)	−0.0056 (7)	−0.0012 (7)
C18	0.0282 (8)	0.0281 (8)	0.0294 (9)	0.0005 (7)	−0.0020 (7)	−0.0028 (7)
F19	0.0567 (8)	0.0720 (9)	0.0322 (6)	−0.0073 (6)	−0.0087 (5)	0.0149 (6)
F20	0.0355 (6)	0.0476 (6)	0.0424 (6)	−0.0043 (5)	−0.0058 (5)	0.0071 (5)
F21	0.0563 (8)	0.0395 (6)	0.0557 (8)	0.0145 (6)	0.0049 (6)	0.0082 (6)
C22	0.0339 (10)	0.0426 (11)	0.0326 (10)	0.0036 (8)	−0.0030 (8)	0.0024 (8)
C23	0.0291 (9)	0.0417 (10)	0.0321 (10)	0.0027 (8)	−0.0039 (7)	−0.0026 (8)
O24	0.0641 (10)	0.0588 (9)	0.0367 (8)	−0.0119 (8)	−0.0154 (7)	−0.0049 (7)
C25	0.0281 (9)	0.0313 (9)	0.0302 (9)	0.0021 (7)	−0.0015 (7)	−0.0020 (7)
O26	0.0559 (9)	0.0368 (7)	0.0379 (8)	−0.0070 (6)	−0.0066 (6)	0.0050 (6)
C27	0.0389 (10)	0.0337 (10)	0.0374 (11)	−0.0014 (8)	−0.0037 (8)	−0.0041 (8)
N28	0.0245 (7)	0.0328 (8)	0.0277 (8)	0.0039 (6)	−0.0008 (6)	−0.0002 (6)
N29	0.0295 (7)	0.0310 (8)	0.0268 (8)	−0.0002 (6)	−0.0011 (6)	0.0006 (6)
C30	0.0215 (8)	0.0346 (9)	0.0291 (9)	0.0017 (7)	−0.0002 (7)	−0.0030 (7)
C31	0.0340 (9)	0.0383 (10)	0.0303 (9)	−0.0017 (8)	−0.0014 (8)	0.0003 (8)
C32	0.0363 (10)	0.0373 (10)	0.0424 (11)	−0.0042 (8)	−0.0012 (8)	−0.0028 (8)
C33	0.0253 (9)	0.0460 (11)	0.0396 (11)	−0.0003 (8)	−0.0028 (8)	−0.0137 (8)
Cl34	0.0433 (3)	0.0645 (4)	0.0607 (4)	−0.0052 (3)	−0.0112 (3)	−0.0283 (3)
C35	0.0346 (10)	0.0545 (12)	0.0308 (10)	0.0021 (9)	−0.0076 (8)	−0.0049 (9)
C36	0.0354 (10)	0.0397 (10)	0.0307 (10)	0.0005 (8)	−0.0051 (8)	0.0023 (8)

Geometric parameters (Å, º) top

F1—C4	1.332 (2)	F19—C22	1.331 (2)
F2—C4	1.331 (2)	F20—C22	1.333 (2)
F3—C4	1.335 (2)	F21—C22	1.333 (2)
C4—C5	1.553 (3)	C22—C23	1.553 (3)
C5—O6	1.213 (2)	C23—O24	1.210 (2)
C5—C7	1.453 (2)	C23—C25	1.453 (3)
C7—N10	1.322 (2)	C25—N28	1.324 (2)
C7—C9	1.459 (2)	C25—C27	1.455 (2)
O8—C9	1.217 (2)	O26—C27	1.219 (2)
C9—H9	0.9500	C27—H27	0.9500
N10—N11	1.2924 (19)	N28—N29	1.289 (2)
N11—C12	1.414 (2)	N29—C30	1.418 (2)
N11—H11	0.8800	N29—H29	0.8800
C12—C18	1.382 (2)	C30—C36	1.378 (3)
C12—C13	1.388 (2)	C30—C31	1.388 (3)
C13—C14	1.384 (2)	C31—C32	1.378 (3)
C13—H13	0.9500	C31—H31	0.9500
C14—C15	1.376 (3)	C32—C33	1.383 (3)
C14—H14	0.9500	C32—H32	0.9500
C15—C17	1.380 (3)	C33—C35	1.374 (3)
C15—Cl16	1.7444 (17)	C33—Cl34	1.7418 (19)
C17—C18	1.384 (2)	C35—C36	1.388 (3)
C17—H17	0.9500	C35—H35	0.9500
C18—H18	0.9500	C36—H36	0.9500

F2—C4—F1	106.75 (15)	F19—C22—F20	106.75 (15)
F2—C4—F3	107.72 (16)	F19—C22—F21	107.22 (15)
F1—C4—F3	107.31 (15)	F20—C22—F21	107.53 (16)
F2—C4—C5	111.72 (15)	F19—C22—C23	110.29 (16)
F1—C4—C5	110.14 (16)	F20—C22—C23	112.13 (15)
F3—C4—C5	112.91 (15)	F21—C22—C23	112.62 (15)
O6—C5—C7	124.78 (17)	O24—C23—C25	124.99 (18)
O6—C5—C4	117.46 (17)	O24—C23—C22	117.30 (17)
C7—C5—C4	117.76 (15)	C25—C23—C22	117.70 (16)
N10—C7—C5	114.86 (15)	N28—C25—C23	115.36 (16)
N10—C7—C9	125.69 (16)	N28—C25—C27	125.67 (17)
C5—C7—C9	119.46 (15)	C23—C25—C27	118.95 (16)
O8—C9—C7	122.43 (16)	O26—C27—C25	122.08 (18)
O8—C9—H9	118.8	O26—C27—H27	119.0
C7—C9—H9	118.8	C25—C27—H27	119.0
N11—N10—C7	121.04 (14)	N29—N28—C25	121.73 (15)
N10—N11—C12	119.13 (14)	N28—N29—C30	118.97 (14)
N10—N11—H11	120.4	N28—N29—H29	120.5
C12—N11—H11	120.4	C30—N29—H29	120.5
C18—C12—C13	121.04 (15)	C36—C30—C31	120.69 (17)
C18—C12—N11	117.95 (15)	C36—C30—N29	118.84 (16)
C13—C12—N11	121.01 (15)	C31—C30—N29	120.47 (16)
C14—C13—C12	119.29 (16)	C32—C31—C30	119.47 (18)
C14—C13—H13	120.4	C32—C31—H31	120.3
C12—C13—H13	120.4	C30—C31—H31	120.3
C15—C14—C13	119.29 (16)	C31—C32—C33	119.50 (18)
C15—C14—H14	120.4	C31—C32—H32	120.2
C13—C14—H14	120.4	C33—C32—H32	120.2
C14—C15—C17	121.74 (16)	C35—C33—C32	121.38 (18)
C14—C15—Cl16	119.69 (14)	C35—C33—Cl34	119.53 (16)
C17—C15—Cl16	118.57 (14)	C32—C33—Cl34	119.09 (16)
C15—C17—C18	119.14 (16)	C33—C35—C36	119.10 (18)
C15—C17—H17	120.4	C33—C35—H35	120.4
C18—C17—H17	120.4	C36—C35—H35	120.4
C12—C18—C17	119.49 (16)	C30—C36—C35	119.85 (18)
C12—C18—H18	120.3	C30—C36—H36	120.1
C17—C18—H18	120.3	C35—C36—H36	120.1

F2—C4—C5—O6	117.94 (19)	F19—C22—C23—O24	−0.9 (2)
F1—C4—C5—O6	−0.5 (2)	F20—C22—C23—O24	−119.74 (19)
F3—C4—C5—O6	−120.46 (19)	F21—C22—C23—O24	118.8 (2)
F2—C4—C5—C7	−61.9 (2)	F19—C22—C23—C25	178.66 (15)
F1—C4—C5—C7	179.66 (15)	F20—C22—C23—C25	59.8 (2)
F3—C4—C5—C7	59.7 (2)	F21—C22—C23—C25	−61.6 (2)
O6—C5—C7—N10	−177.83 (17)	O24—C23—C25—N28	−177.47 (18)
C4—C5—C7—N10	2.0 (2)	C22—C23—C25—N28	3.0 (2)
O6—C5—C7—C9	1.8 (3)	O24—C23—C25—C27	4.1 (3)
C4—C5—C7—C9	−178.39 (15)	C22—C23—C25—C27	−175.47 (16)
N10—C7—C9—O8	−2.0 (3)	N28—C25—C27—O26	0.5 (3)
C5—C7—C9—O8	178.45 (16)	C23—C25—C27—O26	178.74 (17)
C5—C7—N10—N11	−179.81 (14)	C23—C25—N28—N29	179.78 (15)
C9—C7—N10—N11	0.6 (2)	C27—C25—N28—N29	−1.9 (3)
C7—N10—N11—C12	−179.37 (14)	C25—N28—N29—C30	−179.92 (14)
N10—N11—C12—C18	174.08 (14)	N28—N29—C30—C36	−174.13 (15)
N10—N11—C12—C13	−6.2 (2)	N28—N29—C30—C31	6.3 (2)
C18—C12—C13—C14	0.2 (2)	C36—C30—C31—C32	0.5 (3)
N11—C12—C13—C14	−179.47 (15)	N29—C30—C31—C32	−179.94 (16)
C12—C13—C14—C15	−0.9 (2)	C30—C31—C32—C33	−0.2 (3)
C13—C14—C15—C17	1.0 (3)	C31—C32—C33—C35	−0.3 (3)
C13—C14—C15—Cl16	−179.66 (13)	C31—C32—C33—Cl34	179.43 (14)
C14—C15—C17—C18	−0.3 (3)	C32—C33—C35—C36	0.5 (3)
Cl16—C15—C17—C18	−179.69 (13)	Cl34—C33—C35—C36	−179.23 (14)
C13—C12—C18—C17	0.4 (2)	C31—C30—C36—C35	−0.3 (3)
N11—C12—C18—C17	−179.87 (14)	N29—C30—C36—C35	−179.87 (15)
C15—C17—C18—C12	−0.4 (2)	C33—C35—C36—C30	−0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O8	0.88	2.01	2.6746 (18)	131
N29—H29···O26	0.88	2.03	2.679 (2)	130
N29—H29···O26ⁱ	0.88	2.42	3.2159 (19)	150
C27—H27···O6ⁱⁱ	0.95	2.59	3.491 (2)	158
C36—H36···O26ⁱ	0.95	2.52	3.323 (3)	143

Symmetry codes: (i) −x, −y, −z+2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₆ClF₃N₂O₂
M_r	278.62
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.6440 (4), 7.7139 (4), 19.4221 (10)
α, β, γ (°)	86.134 (1), 81.706 (1), 88.999 (1)
V (Å³)	1130.63 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.44 × 0.38 × 0.35

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.853, 0.880
No. of measured, independent and observed [I > 2σ(I)] reflections	8820, 4387, 3577
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.111, 1.05
No. of reflections	4387
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.23

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O8	0.88	2.01	2.6746 (18)	131
N29—H29···O26	0.88	2.03	2.679 (2)	130
N29—H29···O26ⁱ	0.88	2.42	3.2159 (19)	150
C27—H27···O6ⁱⁱ	0.95	2.59	3.491 (2)	158
C36—H36···O26ⁱ	0.95	2.52	3.323 (3)	143

Symmetry codes: (i) −x, −y, −z+2; (ii) x−1, y, z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20802010), the Natural Science Foundation of Guangdong Province (No.07300884) and the 211 project of Guangdong Province.

References

Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Jiang, H. & Zhu, S. (2008). J. Fluorine Chem. 129, 40–44. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar