(3Z)-1,1,1-Trifluoro-4-phenyl-4-[(2-{[(1Z)-4,4,4-trifluoro-3-oxo-1-phenyl-but-1-en-1-yl]amino}-eth-yl)amino]-but-3-en-2-one.

In the title compound, C(22)H(18)F(6)N(2)O(2), the five atoms comprising each O=C-C=C-N fragment are almost coplanar (the r.m.s. deviation for the fitted atoms being 0.008 and 0.002 Å) and form a dihedral angle of 47.70 (12)°. The phenyl ring attached to each of the O=C-C=C-N fragments is twisted out of the respective plane with dihedral angles of 64.46 (11) and 61.82 (10)°, respectively. An almost orthogonal relationship for the phenyl rings is indicated by the dihedral angle between them of 78.19 (14)°. The conformation about each ethyl-ene bond is Z, which allows for the formation of intra-molecular N-H⋯O hydrogen bonds which close S(6) loops. The most prominent feature of the crystal packing are N-H⋯O hydrogen bonds that result in supra-molecular chains along the a axis. The F atoms of one -CF(3) groups are disordered over three sets of sites with site-occupation factors of 0.318 (4), 0.360 (10) and 0.322 (9).

Related literature

For the structure of the compound in which the CF3 substituents of the title compound are replaced by 2-thienyl groups, see: Asiri et al. (2011 ▶).

Experimental

Crystal data

C22H18F6N2O2

M = 456.38

Monoclinic,

a = 13.0411 (9) Å

b = 15.897 (1) Å

c = 10.9417 (9) Å

β = 112.306 (9)°

V = 2098.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.35 × 0.15 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.538, T max = 1.000

10523 measured reflections

4845 independent reflections

3146 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.165

S = 1.02

4845 reflections

309 parameters

19 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028875/bt5954sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028875/bt5954Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028875/bt5954Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H18F6N2O2	F(000) = 936
Mr = 456.38	Dx = 1.444 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2319 reflections
a = 13.0411 (9) Å	θ = 2.4–27.5°
b = 15.897 (1) Å	µ = 0.13 mm−1
c = 10.9417 (9) Å	T = 100 K
β = 112.306 (9)°	Prism, colourless
V = 2098.6 (3) Å3	0.35 × 0.15 × 0.15 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	4845 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3146 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.041
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.4°
ω scan	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −15→20
Tmin = 0.538, Tmax = 1.000	l = −10→14
10523 measured reflections

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0641P)2 + 1.085P] where P = (Fo2 + 2Fc2)/3
4845 reflections	(Δ/σ)max = 0.002
309 parameters	Δρmax = 0.51 e Å−3
19 restraints	Δρmin = −0.50 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.01821 (13)	0.40373 (11)	0.50828 (17)	0.0287 (4)
O2	0.44440 (13)	0.44780 (12)	0.37678 (17)	0.0304 (4)
N2	0.63608 (17)	0.52490 (14)	0.3995 (2)	0.0276 (5)
N1	0.86126 (16)	0.46861 (13)	0.5887 (2)	0.0253 (5)
F1	1.0661 (7)	0.2668 (4)	0.3981 (6)	0.0556 (19)*	0.318 (4)
F2	1.1419 (5)	0.2588 (4)	0.6132 (6)	0.0514 (19)*	0.318 (4)
F3	0.9898 (5)	0.1853 (4)	0.4922 (7)	0.041 (2)*	0.318 (4)
F1'	1.0158 (7)	0.2543 (4)	0.3630 (4)	0.0332 (16)*	0.360 (10)
F2'	1.1461 (3)	0.2603 (3)	0.5612 (7)	0.0142 (13)*	0.360 (10)
F3'	1.0020 (5)	0.1831 (3)	0.5290 (9)	0.0150 (14)*	0.360 (10)
F1"	0.9793 (7)	0.2360 (5)	0.3631 (5)	0.055 (2)*	0.322 (9)
F2"	1.1364 (4)	0.2625 (3)	0.5098 (9)	0.0290 (17)*	0.322 (9)
F3"	1.0224 (6)	0.1860 (4)	0.5657 (8)	0.038 (2)*	0.322 (9)
F4	0.35986 (14)	0.28737 (11)	0.28834 (17)	0.0491 (5)
F5	0.37037 (12)	0.31466 (10)	0.10070 (16)	0.0394 (4)
F6	0.26345 (11)	0.38801 (10)	0.16715 (15)	0.0382 (4)
C1	1.0361 (2)	0.25715 (17)	0.4985 (3)	0.0370 (7)
C2	0.98029 (19)	0.33504 (16)	0.5274 (2)	0.0260 (6)
C3	0.8934 (2)	0.32256 (17)	0.5709 (3)	0.0284 (6)
H3	0.8712	0.2666	0.5791	0.034*
C4	0.83811 (19)	0.38913 (16)	0.6026 (2)	0.0252 (5)
C5	0.75063 (19)	0.36831 (17)	0.6547 (3)	0.0277 (6)
C6	0.6563 (2)	0.32548 (17)	0.5745 (3)	0.0314 (6)
H6	0.6480	0.3097	0.4875	0.038*
C7	0.5742 (2)	0.30574 (19)	0.6215 (3)	0.0379 (7)
H7	0.5091	0.2773	0.5660	0.045*
C8	0.5872 (2)	0.3275 (2)	0.7495 (3)	0.0409 (7)
H8	0.5310	0.3138	0.7815	0.049*
C9	0.6812 (2)	0.3689 (2)	0.8300 (3)	0.0413 (7)
H9	0.6902	0.3832	0.9178	0.050*
C10	0.7632 (2)	0.38983 (19)	0.7832 (3)	0.0347 (7)
H10	0.8278	0.4188	0.8388	0.042*
C11	0.80105 (19)	0.54221 (16)	0.6068 (3)	0.0274 (6)
H11A	0.8550	0.5849	0.6595	0.033*
H11B	0.7551	0.5255	0.6569	0.033*
C12	0.72688 (19)	0.58088 (16)	0.4758 (3)	0.0279 (6)
H12A	0.6956	0.6343	0.4930	0.033*
H12B	0.7720	0.5941	0.4232	0.033*
C13	0.62859 (19)	0.47929 (17)	0.2947 (2)	0.0265 (6)
C14	0.71669 (19)	0.48676 (17)	0.2393 (2)	0.0271 (6)
C15	0.7362 (2)	0.56297 (19)	0.1885 (3)	0.0369 (7)
H15	0.6925	0.6110	0.1874	0.044*
C16	0.8199 (2)	0.5682 (2)	0.1397 (3)	0.0437 (8)
H16	0.8335	0.6201	0.1053	0.052*
C17	0.8833 (2)	0.4990 (2)	0.1406 (3)	0.0440 (8)
H17	0.9409	0.5034	0.1079	0.053*
C18	0.8634 (2)	0.4231 (2)	0.1890 (3)	0.0396 (7)
H18	0.9074	0.3754	0.1896	0.047*
C19	0.7791 (2)	0.41635 (19)	0.2368 (3)	0.0315 (6)
H19	0.7642	0.3637	0.2678	0.038*
C20	0.54108 (19)	0.42385 (16)	0.2348 (2)	0.0267 (6)
H20	0.5397	0.3925	0.1603	0.032*
C21	0.45487 (19)	0.41255 (16)	0.2804 (2)	0.0263 (6)
C22	0.3625 (2)	0.35051 (17)	0.2078 (3)	0.0302 (6)
H1	0.918 (3)	0.479 (2)	0.562 (3)	0.054 (10)*
H2	0.583 (3)	0.5189 (19)	0.430 (3)	0.046 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0229 (9)	0.0269 (10)	0.0412 (10)	−0.0004 (8)	0.0176 (8)	0.0006 (8)
O2	0.0222 (8)	0.0362 (11)	0.0367 (10)	−0.0024 (8)	0.0155 (8)	−0.0076 (9)
N2	0.0201 (10)	0.0286 (12)	0.0379 (12)	−0.0047 (9)	0.0155 (9)	−0.0050 (10)
N1	0.0197 (10)	0.0252 (12)	0.0355 (11)	−0.0005 (9)	0.0156 (9)	−0.0017 (10)
F4	0.0464 (10)	0.0404 (10)	0.0557 (11)	−0.0172 (9)	0.0140 (9)	0.0040 (9)
F5	0.0262 (8)	0.0437 (10)	0.0501 (9)	−0.0018 (7)	0.0167 (7)	−0.0203 (8)
F6	0.0196 (7)	0.0469 (10)	0.0478 (9)	0.0001 (7)	0.0125 (7)	−0.0173 (8)
C1	0.0284 (14)	0.0281 (15)	0.0609 (19)	−0.0017 (12)	0.0241 (14)	0.0029 (14)
C2	0.0188 (11)	0.0237 (14)	0.0340 (13)	0.0021 (10)	0.0085 (10)	0.0008 (11)
C3	0.0231 (12)	0.0240 (14)	0.0407 (14)	−0.0012 (11)	0.0148 (11)	0.0035 (12)
C4	0.0172 (11)	0.0297 (14)	0.0278 (12)	−0.0022 (11)	0.0075 (10)	0.0006 (11)
C5	0.0204 (11)	0.0289 (14)	0.0366 (13)	0.0010 (11)	0.0139 (11)	0.0059 (12)
C6	0.0244 (12)	0.0327 (15)	0.0378 (14)	−0.0052 (12)	0.0126 (11)	0.0031 (12)
C7	0.0247 (13)	0.0413 (17)	0.0482 (16)	−0.0053 (13)	0.0144 (12)	0.0106 (14)
C8	0.0283 (14)	0.0485 (19)	0.0539 (18)	0.0021 (14)	0.0245 (14)	0.0166 (15)
C9	0.0376 (15)	0.056 (2)	0.0385 (15)	−0.0001 (15)	0.0235 (13)	0.0081 (15)
C10	0.0254 (13)	0.0469 (18)	0.0321 (14)	−0.0035 (13)	0.0114 (11)	0.0032 (13)
C11	0.0224 (12)	0.0255 (14)	0.0392 (14)	−0.0042 (11)	0.0170 (11)	−0.0078 (12)
C12	0.0230 (12)	0.0236 (13)	0.0419 (14)	−0.0031 (11)	0.0178 (11)	−0.0036 (12)
C13	0.0218 (12)	0.0253 (14)	0.0340 (13)	0.0052 (11)	0.0123 (11)	0.0027 (11)
C14	0.0214 (12)	0.0322 (14)	0.0287 (13)	−0.0039 (11)	0.0105 (10)	−0.0007 (11)
C15	0.0333 (14)	0.0386 (17)	0.0404 (15)	−0.0017 (13)	0.0159 (13)	0.0055 (13)
C16	0.0382 (16)	0.058 (2)	0.0377 (15)	−0.0148 (16)	0.0173 (13)	0.0064 (15)
C17	0.0307 (14)	0.071 (2)	0.0371 (16)	−0.0130 (16)	0.0208 (13)	−0.0074 (16)
C18	0.0277 (14)	0.057 (2)	0.0376 (15)	0.0010 (14)	0.0161 (12)	−0.0115 (14)
C19	0.0263 (13)	0.0392 (16)	0.0314 (13)	−0.0011 (12)	0.0136 (11)	−0.0063 (12)
C20	0.0213 (12)	0.0282 (14)	0.0313 (13)	−0.0007 (11)	0.0109 (10)	−0.0032 (11)
C21	0.0206 (12)	0.0248 (13)	0.0333 (13)	0.0002 (11)	0.0099 (11)	−0.0011 (11)
C22	0.0226 (12)	0.0306 (15)	0.0385 (14)	−0.0002 (11)	0.0129 (11)	−0.0045 (12)

O1—C2	1.249 (3)	C7—C8	1.389 (4)
O2—C21	1.247 (3)	C7—H7	0.9500
N2—C13	1.328 (3)	C8—C9	1.376 (4)
N2—C12	1.463 (3)	C8—H8	0.9500
N2—H2	0.88 (3)	C9—C10	1.390 (4)
N1—C4	1.321 (3)	C9—H9	0.9500
N1—C11	1.464 (3)	C10—H10	0.9500
N1—H1	0.91 (3)	C11—C12	1.521 (4)
F1—C1	1.308 (5)	C11—H11A	0.9900
F2—C1	1.471 (5)	C11—H11B	0.9900
F3—C1	1.282 (6)	C12—H12A	0.9900
F1'—C1	1.405 (5)	C12—H12B	0.9900
F2'—C1	1.335 (4)	C13—C20	1.393 (4)
F3'—C1	1.345 (5)	C13—C14	1.493 (3)
F1"—C1	1.422 (6)	C14—C19	1.390 (4)
F2"—C1	1.269 (5)	C14—C15	1.396 (4)
F3"—C1	1.397 (5)	C15—C16	1.388 (4)
F4—C22	1.344 (3)	C15—H15	0.9500
F5—C22	1.342 (3)	C16—C17	1.374 (4)
F6—C22	1.336 (3)	C16—H16	0.9500
C1—C2	1.529 (4)	C17—C18	1.382 (4)
C2—C3	1.400 (3)	C17—H17	0.9500
C3—C4	1.397 (4)	C18—C19	1.389 (4)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.493 (3)	C19—H19	0.9500
C5—C6	1.388 (4)	C20—C21	1.404 (3)
C5—C10	1.395 (4)	C20—H20	0.9500
C6—C7	1.388 (4)	C21—C22	1.526 (4)
C6—H6	0.9500
C13—N2—C12	127.1 (2)	C9—C10—C5	120.0 (3)
C13—N2—H2	117 (2)	C9—C10—H10	120.0
C12—N2—H2	116 (2)	C5—C10—H10	120.0
C4—N1—C11	126.2 (2)	N1—C11—C12	112.2 (2)
C4—N1—H1	118 (2)	N1—C11—H11A	109.2
C11—N1—H1	116 (2)	C12—C11—H11A	109.2
F3—C1—F1	110.2 (4)	N1—C11—H11B	109.2
F2'—C1—F3'	107.3 (4)	C12—C11—H11B	109.2
F2"—C1—F3"	109.6 (4)	H11A—C11—H11B	107.9
F2'—C1—F1'	106.2 (3)	N2—C12—C11	112.3 (2)
F3'—C1—F1'	106.6 (4)	N2—C12—H12A	109.1
F2"—C1—F1"	103.1 (4)	C11—C12—H12A	109.1
F3"—C1—F1"	103.7 (4)	N2—C12—H12B	109.1
F3—C1—F2	109.4 (4)	C11—C12—H12B	109.1
F1—C1—F2	103.4 (4)	H12A—C12—H12B	107.9
F2"—C1—C2	118.6 (3)	N2—C13—C20	122.0 (2)
F3—C1—C2	118.8 (4)	N2—C13—C14	119.4 (2)
F1—C1—C2	113.3 (4)	C20—C13—C14	118.6 (2)
F2'—C1—C2	111.5 (3)	C19—C14—C15	119.6 (2)
F3'—C1—C2	115.5 (3)	C19—C14—C13	119.4 (2)
F3"—C1—C2	112.4 (3)	C15—C14—C13	121.0 (2)
F1'—C1—C2	109.3 (3)	C16—C15—C14	119.7 (3)
F1"—C1—C2	107.8 (3)	C16—C15—H15	120.2
F2—C1—C2	100.1 (3)	C14—C15—H15	120.2
O1—C2—C3	127.2 (2)	C17—C16—C15	120.5 (3)
O1—C2—C1	115.1 (2)	C17—C16—H16	119.8
C3—C2—C1	117.7 (2)	C15—C16—H16	119.8
C4—C3—C2	122.6 (2)	C16—C17—C18	120.2 (3)
C4—C3—H3	118.7	C16—C17—H17	119.9
C2—C3—H3	118.7	C18—C17—H17	119.9
N1—C4—C3	122.3 (2)	C17—C18—C19	120.2 (3)
N1—C4—C5	119.8 (2)	C17—C18—H18	119.9
C3—C4—C5	117.9 (2)	C19—C18—H18	119.9
C6—C5—C10	119.6 (2)	C14—C19—C18	119.9 (3)
C6—C5—C4	119.3 (2)	C14—C19—H19	120.1
C10—C5—C4	121.1 (2)	C18—C19—H19	120.1
C7—C6—C5	120.0 (3)	C13—C20—C21	122.5 (2)
C7—C6—H6	120.0	C13—C20—H20	118.7
C5—C6—H6	120.0	C21—C20—H20	118.7
C6—C7—C8	120.1 (3)	O2—C21—C20	127.1 (2)
C6—C7—H7	120.0	O2—C21—C22	114.4 (2)
C8—C7—H7	120.0	C20—C21—C22	118.6 (2)
C9—C8—C7	120.2 (2)	F6—C22—F5	106.5 (2)
C9—C8—H8	119.9	F6—C22—F4	106.8 (2)
C7—C8—H8	119.9	F5—C22—F4	106.5 (2)
C8—C9—C10	120.1 (3)	F6—C22—C21	110.9 (2)
C8—C9—H9	119.9	F5—C22—C21	114.9 (2)
C10—C9—H9	119.9	F4—C22—C21	110.7 (2)
F2"—C1—C2—O1	27.6 (6)	C7—C8—C9—C10	0.6 (5)
F3—C1—C2—O1	−167.4 (4)	C8—C9—C10—C5	−0.5 (5)
F1—C1—C2—O1	−35.7 (5)	C6—C5—C10—C9	−0.4 (4)
F2'—C1—C2—O1	52.0 (4)	C4—C5—C10—C9	−179.2 (3)
F3'—C1—C2—O1	174.8 (5)	C4—N1—C11—C12	−104.0 (3)
F3"—C1—C2—O1	157.3 (4)	C13—N2—C12—C11	−103.8 (3)
F1'—C1—C2—O1	−65.0 (5)	N1—C11—C12—N2	66.1 (3)
F1"—C1—C2—O1	−89.0 (5)	C12—N2—C13—C20	175.8 (2)
F2—C1—C2—O1	73.7 (4)	C12—N2—C13—C14	−3.7 (4)
F2"—C1—C2—C3	−152.8 (5)	N2—C13—C14—C19	118.6 (3)
F3—C1—C2—C3	12.2 (5)	C20—C13—C14—C19	−60.9 (3)
F1—C1—C2—C3	144.0 (4)	N2—C13—C14—C15	−62.2 (3)
F2'—C1—C2—C3	−128.3 (4)	C20—C13—C14—C15	118.2 (3)
F3'—C1—C2—C3	−5.5 (5)	C19—C14—C15—C16	−1.9 (4)
F3"—C1—C2—C3	−23.1 (5)	C13—C14—C15—C16	179.0 (2)
F1'—C1—C2—C3	114.7 (5)	C14—C15—C16—C17	0.2 (4)
F1"—C1—C2—C3	90.7 (5)	C15—C16—C17—C18	0.7 (4)
F2—C1—C2—C3	−106.6 (4)	C16—C17—C18—C19	0.1 (4)
O1—C2—C3—C4	−1.7 (4)	C15—C14—C19—C18	2.7 (4)
C1—C2—C3—C4	178.7 (2)	C13—C14—C19—C18	−178.2 (2)
C11—N1—C4—C3	173.6 (2)	C17—C18—C19—C14	−1.8 (4)
C11—N1—C4—C5	−6.8 (4)	N2—C13—C20—C21	0.3 (4)
C2—C3—C4—N1	2.8 (4)	C14—C13—C20—C21	179.8 (2)
C2—C3—C4—C5	−176.9 (2)	C13—C20—C21—O2	−0.7 (4)
N1—C4—C5—C6	116.6 (3)	C13—C20—C21—C22	179.8 (2)
C3—C4—C5—C6	−63.7 (3)	O2—C21—C22—F6	56.6 (3)
N1—C4—C5—C10	−64.5 (3)	C20—C21—C22—F6	−123.8 (3)
C3—C4—C5—C10	115.1 (3)	O2—C21—C22—F5	177.4 (2)
C10—C5—C6—C7	1.2 (4)	C20—C21—C22—F5	−3.0 (4)
C4—C5—C6—C7	−179.9 (2)	O2—C21—C22—F4	−61.8 (3)
C5—C6—C7—C8	−1.1 (4)	C20—C21—C22—F4	117.7 (3)
C6—C7—C8—C9	0.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.91 (3)	2.02 (3)	2.719 (3)	133 (3)
N1—H1···O1i	0.91 (3)	2.28 (3)	2.997 (3)	135 (3)
N2—H2···O2	0.88 (3)	2.02 (3)	2.709 (3)	134 (3)
N2—H2···O2ii	0.88 (3)	2.33 (3)	3.039 (3)	137 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.91 (3)	2.02 (3)	2.719 (3)	133 (3)
N1—H1⋯O1i	0.91 (3)	2.28 (3)	2.997 (3)	135 (3)
N2—H2⋯O2	0.88 (3)	2.02 (3)	2.709 (3)	134 (3)
N2—H2⋯O2ii	0.88 (3)	2.33 (3)	3.039 (3)	137 (3)

Symmetry codes: (i) ; (ii) .