N-Acetyl-N-{2-[(Z)-2-chloro-3,3,3-tri-fluoro-prop-1-en-yl]phen-yl}acetamide.

The title compound, C(13)H(11)ClF(3)NO(2), adopts a Z conformation. Halogen⋯oxygen inter-actions [Cl⋯O = 2.967 (3) Å] in the crystal packing lead to the formation of a dimer joined by two Cl⋯O bonds.

Related literature

The title compound is an important medical inter­mediate, see: Zhou et al. (2009 ▶). For the van der Waals radii of chlorine and oxygen, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C13H11ClF3NO2

M = 305.68

Triclinic,

a = 8.4408 (19) Å

b = 9.385 (2) Å

c = 9.455 (2) Å

α = 64.599 (3)°

β = 80.727 (4)°

γ = 89.756 (3)°

V = 666.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.13 × 0.13 × 0.07 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.958, T max = 0.978

3747 measured reflections

2562 independent reflections

2155 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.136

S = 1.03

2562 reflections

177 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014779/kj2121sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014779/kj2121Isup2.hkl

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

C13H11ClF3NO2	Z = 2
Mr = 305.68	F(000) = 312
Triclinic, P1	Dx = 1.524 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4408 (19) Å	Cell parameters from 1359 reflections
b = 9.385 (2) Å	θ = 2.3–24.8°
c = 9.455 (2) Å	µ = 0.32 mm−1
α = 64.599 (3)°	T = 293 K
β = 80.727 (4)°	Block, colorless
γ = 89.756 (3)°	0.13 × 0.13 × 0.07 mm
V = 666.0 (3) Å3

Bruker APEX CCD area-detector diffractometer	2562 independent reflections
Radiation source: fine-focus sealed tube	2155 reflections with I > 2σ(I)
graphite	Rint = 0.010
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SAINT-Plus; Bruker, 2003)	h = −10→7
Tmin = 0.958, Tmax = 0.978	k = −11→10
3747 measured reflections	l = −11→11

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.06P)2 + 0.4882P] where P = (Fo2 + 2Fc2)/3
2562 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.38 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
Cl1	0.34597 (9)	0.48032 (9)	1.17904 (9)	0.0624 (3)
F1	0.1487 (3)	0.0570 (2)	1.3535 (2)	0.0876 (7)
F2	0.3488 (2)	0.1468 (2)	1.4086 (2)	0.0839 (6)
F3	0.1179 (3)	0.2263 (3)	1.4482 (2)	0.0849 (6)
N1	0.2505 (2)	0.2173 (2)	0.8013 (2)	0.0395 (5)
O1	0.1014 (3)	−0.0027 (2)	0.8367 (3)	0.0615 (5)
O2	0.5147 (2)	0.2397 (3)	0.8026 (3)	0.0669 (6)
C1	−0.0380 (4)	0.2291 (4)	0.7833 (4)	0.0625 (6)
H1A	−0.1288	0.1624	0.7927	0.094*
H1B	−0.0184	0.3158	0.6790	0.094*
H1C	−0.0600	0.2692	0.8617	0.094*
C2	0.1066 (3)	0.1358 (3)	0.8087 (3)	0.0439 (6)
C3	0.4252 (4)	−0.0064 (4)	0.8221 (4)	0.0625 (6)
H3A	0.5363	−0.0280	0.8237	0.094*
H3B	0.3932	−0.0141	0.7325	0.094*
H3C	0.3602	−0.0820	0.9185	0.094*
C4	0.4031 (3)	0.1564 (3)	0.8091 (3)	0.0462 (6)
C5	0.2485 (3)	0.3838 (3)	0.7692 (3)	0.0387 (5)
C6	0.2754 (3)	0.4964 (3)	0.6127 (3)	0.0501 (6)
H6	0.2997	0.4655	0.5310	0.060*
C7	0.2665 (4)	0.6545 (3)	0.5773 (3)	0.0585 (7)
H7	0.2850	0.7301	0.4720	0.070*
C8	0.2300 (4)	0.6998 (3)	0.6988 (4)	0.0564 (7)
H8	0.2196	0.8059	0.6753	0.068*
C9	0.2089 (3)	0.5884 (3)	0.8548 (3)	0.0483 (6)
H9	0.1863	0.6208	0.9356	0.058*
C10	0.2205 (3)	0.4277 (3)	0.8945 (3)	0.0376 (5)
C11	0.2003 (3)	0.3065 (3)	1.0601 (3)	0.0401 (5)
H11	0.1495	0.2099	1.0813	0.048*
C12	0.2460 (3)	0.3182 (3)	1.1831 (3)	0.0419 (5)
C13	0.2142 (4)	0.1867 (4)	1.3472 (3)	0.0559 (7)

	U11	U22	U33	U12	U13	U23
Cl1	0.0723 (5)	0.0633 (5)	0.0603 (5)	−0.0114 (3)	−0.0172 (3)	−0.0328 (4)
F1	0.1321 (18)	0.0637 (11)	0.0503 (10)	−0.0312 (11)	−0.0168 (11)	−0.0086 (9)
F2	0.0850 (13)	0.0953 (15)	0.0632 (12)	0.0159 (11)	−0.0323 (10)	−0.0202 (11)
F3	0.0907 (14)	0.1127 (16)	0.0463 (10)	0.0056 (12)	0.0090 (9)	−0.0369 (10)
N1	0.0450 (11)	0.0410 (10)	0.0386 (11)	0.0010 (8)	−0.0083 (8)	−0.0226 (9)
O1	0.0679 (12)	0.0511 (11)	0.0724 (14)	−0.0081 (9)	−0.0115 (10)	−0.0334 (10)
O2	0.0480 (11)	0.0663 (13)	0.0952 (17)	0.0048 (9)	−0.0180 (11)	−0.0414 (12)
C1	0.0555 (12)	0.0646 (13)	0.0786 (15)	0.0087 (10)	−0.0172 (10)	−0.0398 (12)
C2	0.0502 (14)	0.0494 (14)	0.0369 (13)	−0.0043 (11)	−0.0062 (10)	−0.0235 (11)
C3	0.0555 (12)	0.0646 (13)	0.0786 (15)	0.0087 (10)	−0.0172 (10)	−0.0398 (12)
C4	0.0487 (14)	0.0510 (14)	0.0452 (14)	0.0062 (11)	−0.0096 (11)	−0.0263 (12)
C5	0.0398 (12)	0.0399 (12)	0.0389 (12)	0.0010 (9)	−0.0073 (10)	−0.0193 (10)
C6	0.0584 (16)	0.0553 (15)	0.0371 (13)	0.0008 (12)	−0.0074 (11)	−0.0208 (12)
C7	0.0726 (19)	0.0469 (15)	0.0438 (15)	−0.0042 (13)	−0.0144 (13)	−0.0067 (12)
C8	0.0687 (18)	0.0388 (14)	0.0620 (18)	0.0044 (12)	−0.0221 (14)	−0.0184 (13)
C9	0.0547 (15)	0.0457 (14)	0.0532 (15)	0.0074 (11)	−0.0149 (12)	−0.0277 (12)
C10	0.0375 (12)	0.0399 (12)	0.0391 (12)	0.0006 (9)	−0.0080 (9)	−0.0202 (10)
C11	0.0433 (12)	0.0404 (12)	0.0404 (13)	−0.0009 (10)	−0.0045 (10)	−0.0219 (11)
C12	0.0416 (12)	0.0485 (13)	0.0402 (13)	0.0009 (10)	−0.0040 (10)	−0.0247 (11)
C13	0.0649 (17)	0.0642 (18)	0.0407 (14)	−0.0006 (14)	−0.0095 (13)	−0.0246 (13)

Cl1—C12	1.726 (2)	C3—H3C	0.9600
F1—C13	1.312 (3)	C5—C6	1.382 (3)
F2—C13	1.338 (3)	C5—C10	1.399 (3)
F3—C13	1.328 (3)	C6—C7	1.378 (4)
N1—C4	1.407 (3)	C6—H6	0.9300
N1—C2	1.414 (3)	C7—C8	1.378 (4)
N1—C5	1.458 (3)	C7—H7	0.9300
O1—C2	1.209 (3)	C8—C9	1.377 (4)
O2—C4	1.204 (3)	C8—H8	0.9300
C1—C2	1.489 (4)	C9—C10	1.396 (3)
C1—H1A	0.9600	C9—H9	0.9300
C1—H1B	0.9600	C10—C11	1.471 (3)
C1—H1C	0.9600	C11—C12	1.329 (3)
C3—C4	1.493 (4)	C11—H11	0.9300
C3—H3A	0.9600	C12—C13	1.493 (4)
C3—H3B	0.9600
C4—N1—C2	125.8 (2)	C5—C6—H6	119.9
C4—N1—C5	115.01 (19)	C8—C7—C6	119.7 (3)
C2—N1—C5	119.0 (2)	C8—C7—H7	120.2
C2—C1—H1A	109.5	C6—C7—H7	120.2
C2—C1—H1B	109.5	C9—C8—C7	120.1 (2)
H1A—C1—H1B	109.5	C9—C8—H8	119.9
C2—C1—H1C	109.5	C7—C8—H8	119.9
H1A—C1—H1C	109.5	C8—C9—C10	121.5 (2)
H1B—C1—H1C	109.5	C8—C9—H9	119.3
O1—C2—N1	121.5 (2)	C10—C9—H9	119.3
O1—C2—C1	122.1 (2)	C9—C10—C5	117.2 (2)
N1—C2—C1	116.3 (2)	C9—C10—C11	122.6 (2)
C4—C3—H3A	109.5	C5—C10—C11	120.2 (2)
C4—C3—H3B	109.5	C12—C11—C10	127.9 (2)
H3A—C3—H3B	109.5	C12—C11—H11	116.1
C4—C3—H3C	109.5	C10—C11—H11	116.1
H3A—C3—H3C	109.5	C11—C12—C13	122.5 (2)
H3B—C3—H3C	109.5	C11—C12—Cl1	126.5 (2)
O2—C4—N1	118.3 (2)	C13—C12—Cl1	111.00 (18)
O2—C4—C3	121.3 (2)	F1—C13—F3	107.5 (2)
N1—C4—C3	120.4 (2)	F1—C13—F2	106.4 (3)
C6—C5—C10	121.0 (2)	F3—C13—F2	105.2 (2)
C6—C5—N1	118.5 (2)	F1—C13—C12	113.0 (2)
C10—C5—N1	120.5 (2)	F3—C13—C12	112.0 (2)
C7—C6—C5	120.3 (2)	F2—C13—C12	112.2 (2)
C7—C6—H6	119.9