N-[4-Cyano-3-(trifluoro-meth-yl)phen-yl]-2-eth-oxy-benzamide.

In the title compound, C(17)H(13)F(3)N(2)O(2), the two aromatic rings are essentially coplanar, forming a dihedral angle of 2.78 (12)°. The non-H atoms of the eth-oxy group are coplanar with the attached ring [maximum deviation = 0.271 (3) Å]. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal structure, mol-ecules are linked by inter-molecular C-H⋯N and C-H⋯F hydrogen bonds.

Related literature

For background to the biological activity of ethoxy­benzamides, see: Mantelingu et al. (2007 ▶). For related structures, see: Ma et al. (2009 ▶); Saeed et al. (2010 ▶).

Experimental

Crystal data

C17H13F3N2O2

M = 334.29

Monoclinic,

a = 10.5010 (13) Å

b = 12.8830 (16) Å

c = 11.6130 (14) Å

β = 101.653 (6)°

V = 1538.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.32 × 0.30 × 0.27 mm

Data collection

MacScience DIPLabo 32001 diffractometer

5043 measured reflections

2704 independent reflections

1896 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.176

S = 1.02

2704 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810019811/wn2389sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019811/wn2389Isup2.hkl

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

C17H13F3N2O2	Z = 4
Mr = 334.29	F(000) = 688
Monoclinic, P21/n	Dx = 1.443 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.5010 (13) Å	µ = 0.12 mm−1
b = 12.8830 (16) Å	T = 293 K
c = 11.6130 (14) Å	Block, colorless
β = 101.653 (6)°	0.32 × 0.30 × 0.27 mm
V = 1538.7 (3) Å3

MacScience DIPLabo 32001 diffractometer	1896 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
graphite	θmax = 25.0°, θmin = 2.4°
Detector resolution: 10.0 pixels mm-1	h = −12→12
ω scan	k = −15→15
5043 measured reflections	l = −13→13
2704 independent 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1179P)2] where P = (Fo2 + 2Fc2)/3
2704 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.19 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
N7	0.87506 (17)	0.12966 (13)	0.60529 (15)	0.0493 (5)
H1	0.8991	0.0685	0.6519	0.059*
O24	0.7968 (2)	0.17185 (12)	0.41408 (15)	0.0740 (6)
O15	0.89269 (17)	−0.07252 (11)	0.65288 (15)	0.0610 (5)
F21	0.75451 (17)	0.57018 (11)	0.62234 (16)	0.0844 (5)
F22	0.79874 (19)	0.49654 (12)	0.47046 (14)	0.0996 (7)
C6	0.9373 (2)	0.23273 (17)	0.7779 (2)	0.0566 (6)
H6	0.9602	0.1701	0.8220	0.068*
C14	0.8480 (2)	−0.09241 (16)	0.5358 (2)	0.0513 (6)
C5	0.8896 (2)	0.22760 (15)	0.6581 (2)	0.0474 (5)
C9	0.8176 (2)	−0.00775 (16)	0.45831 (19)	0.0489 (5)
C2	0.9212 (2)	0.41873 (16)	0.7744 (2)	0.0537 (6)
C8	0.8285 (2)	0.10574 (17)	0.4903 (2)	0.0501 (6)
F23	0.94844 (17)	0.57372 (11)	0.59172 (17)	0.0881 (6)
C10	0.7724 (2)	−0.0286 (2)	0.3392 (2)	0.0608 (6)
H13	0.7506	0.0277	0.2847	0.073*
C4	0.8589 (2)	0.31994 (16)	0.5946 (2)	0.0516 (6)
H14	0.8274	0.3167	0.5111	0.062*
C18	0.9345 (2)	0.51680 (19)	0.8361 (2)	0.0638 (6)
C1	0.9528 (2)	0.32671 (18)	0.8361 (2)	0.0602 (6)
H16	0.9846	0.3279	0.9196	0.072*
C3	0.8748 (2)	0.41397 (16)	0.6531 (2)	0.0519 (6)
C13	0.8323 (3)	−0.19283 (18)	0.4910 (2)	0.0645 (7)
H18	0.8507	−0.2510	0.5433	0.077*
N19	0.9424 (3)	0.59476 (17)	0.8833 (2)	0.0817 (7)
C20	0.8439 (3)	0.51243 (18)	0.5837 (2)	0.0641 (7)
C16	0.9363 (3)	−0.15806 (18)	0.7317 (2)	0.0650 (7)
H21A	0.8635	−0.2019	0.7358	0.078*
H21B	1.0002	−0.1970	0.7014	0.078*
C11	0.7590 (3)	−0.1291 (2)	0.2959 (2)	0.0684 (7)
H22	0.7290	−0.1410	0.2133	0.082*
C12	0.7889 (3)	−0.2104 (2)	0.3733 (3)	0.0699 (7)
H23	0.7802	−0.2804	0.3444	0.084*
C17	0.9919 (3)	−0.1132 (2)	0.8500 (2)	0.0771 (8)
H24A	1.0226	−0.1674	0.9054	0.092*
H24B	0.9264	−0.0736	0.8771	0.092*
H24C	1.0631	−0.0686	0.8426	0.092*

	U11	U22	U33	U12	U13	U23
N7	0.0650 (11)	0.0285 (9)	0.0529 (11)	0.0026 (8)	0.0082 (8)	0.0020 (7)
O24	0.1173 (15)	0.0391 (9)	0.0591 (11)	0.0047 (9)	0.0021 (10)	0.0044 (8)
O15	0.0839 (11)	0.0346 (8)	0.0620 (11)	0.0028 (8)	0.0085 (8)	0.0058 (7)
F21	0.0949 (11)	0.0477 (9)	0.1143 (14)	0.0226 (8)	0.0300 (10)	0.0033 (8)
F22	0.1628 (18)	0.0520 (9)	0.0731 (11)	0.0248 (10)	−0.0023 (10)	0.0071 (8)
C6	0.0748 (15)	0.0384 (12)	0.0545 (14)	0.0010 (11)	0.0080 (11)	0.0026 (10)
C14	0.0574 (13)	0.0365 (11)	0.0605 (14)	−0.0025 (9)	0.0134 (10)	−0.0019 (9)
C5	0.0554 (12)	0.0329 (10)	0.0547 (13)	−0.0006 (9)	0.0129 (9)	−0.0007 (9)
C9	0.0533 (12)	0.0353 (11)	0.0585 (14)	0.0004 (9)	0.0118 (10)	−0.0014 (10)
C2	0.0624 (13)	0.0408 (12)	0.0594 (15)	−0.0033 (10)	0.0159 (11)	−0.0071 (10)
C8	0.0585 (13)	0.0361 (11)	0.0557 (14)	0.0011 (9)	0.0117 (10)	0.0022 (10)
F23	0.1009 (12)	0.0474 (8)	0.1229 (15)	−0.0056 (8)	0.0386 (10)	0.0167 (8)
C10	0.0701 (15)	0.0484 (13)	0.0618 (15)	−0.0015 (11)	0.0080 (11)	−0.0035 (11)
C4	0.0682 (14)	0.0342 (11)	0.0521 (13)	0.0048 (10)	0.0116 (10)	−0.0004 (9)
C18	0.0779 (16)	0.0476 (14)	0.0669 (15)	−0.0019 (12)	0.0174 (12)	−0.0099 (12)
C1	0.0761 (16)	0.0492 (13)	0.0534 (13)	−0.0027 (11)	0.0084 (11)	−0.0021 (11)
C3	0.0587 (13)	0.0338 (11)	0.0657 (15)	0.0021 (9)	0.0187 (11)	0.0008 (10)
C13	0.0798 (16)	0.0325 (11)	0.0818 (18)	−0.0040 (11)	0.0178 (13)	−0.0010 (11)
N19	0.110 (2)	0.0529 (13)	0.0824 (17)	−0.0022 (12)	0.0193 (14)	−0.0211 (12)
C20	0.0848 (17)	0.0377 (12)	0.0706 (17)	0.0092 (12)	0.0173 (13)	−0.0013 (11)
C16	0.0742 (15)	0.0465 (13)	0.0750 (17)	0.0069 (12)	0.0167 (13)	0.0178 (12)
C11	0.0798 (17)	0.0554 (15)	0.0681 (16)	−0.0080 (13)	0.0105 (13)	−0.0169 (13)
C12	0.0812 (17)	0.0438 (13)	0.086 (2)	−0.0117 (12)	0.0192 (14)	−0.0166 (13)
C17	0.0840 (18)	0.0718 (18)	0.0721 (18)	0.0127 (15)	0.0080 (14)	0.0129 (14)

N7—C8	1.362 (3)	F23—C20	1.340 (3)
N7—C5	1.398 (3)	C10—C11	1.386 (3)
N7—H1	0.9600	C10—H13	0.9600
O24—C8	1.225 (3)	C4—C3	1.382 (3)
O15—C14	1.370 (3)	C4—H14	0.9598
O15—C16	1.447 (3)	C18—N19	1.139 (3)
F21—C20	1.344 (3)	C1—H16	0.9599
F22—C20	1.321 (3)	C3—C20	1.503 (3)
C6—C1	1.380 (3)	C13—C12	1.370 (4)
C6—C5	1.381 (3)	C13—H18	0.9600
C6—H6	0.9600	C16—C17	1.496 (4)
C14—C13	1.392 (3)	C16—H21A	0.9600
C14—C9	1.409 (3)	C16—H21B	0.9599
C5—C4	1.403 (3)	C11—C12	1.374 (4)
C9—C10	1.395 (3)	C11—H22	0.9600
C9—C8	1.507 (3)	C12—H23	0.9601
C2—C1	1.390 (3)	C17—H24A	0.9600
C2—C3	1.395 (3)	C17—H24B	0.9600
C2—C18	1.445 (3)	C17—H24C	0.9600
C8—N7—C5	128.36 (18)	C2—C1—H16	120.3
C8—N7—H1	111.7	C4—C3—C2	121.2 (2)
C5—N7—H1	120.0	C4—C3—C20	119.0 (2)
C14—O15—C16	119.14 (18)	C2—C3—C20	119.9 (2)
C1—C6—C5	121.2 (2)	C12—C13—C14	121.1 (2)
C1—C6—H6	118.9	C12—C13—H18	119.2
C5—C6—H6	119.9	C14—C13—H18	119.7
O15—C14—C13	122.4 (2)	F22—C20—F23	106.6 (2)
O15—C14—C9	118.49 (19)	F22—C20—F21	106.5 (2)
C13—C14—C9	119.1 (2)	F23—C20—F21	105.6 (2)
C6—C5—N7	118.07 (19)	F22—C20—C3	113.5 (2)
C6—C5—C4	119.1 (2)	F23—C20—C3	112.1 (2)
N7—C5—C4	122.8 (2)	F21—C20—C3	112.2 (2)
C10—C9—C14	118.1 (2)	O15—C16—C17	107.6 (2)
C10—C9—C8	115.14 (19)	O15—C16—H21A	109.1
C14—C9—C8	126.7 (2)	C17—C16—H21A	110.4
C1—C2—C3	118.8 (2)	O15—C16—H21B	108.7
C1—C2—C18	120.0 (2)	C17—C16—H21B	111.5
C3—C2—C18	121.2 (2)	H21A—C16—H21B	109.5
O24—C8—N7	122.9 (2)	C12—C11—C10	118.8 (2)
O24—C8—C9	120.1 (2)	C12—C11—H22	121.2
N7—C8—C9	117.08 (18)	C10—C11—H22	120.1
C11—C10—C9	122.0 (2)	C13—C12—C11	120.9 (2)
C11—C10—H13	118.2	C13—C12—H23	119.5
C9—C10—H13	119.8	C11—C12—H23	119.7
C3—C4—C5	119.5 (2)	C16—C17—H24A	110.5
C3—C4—H14	121.1	C16—C17—H24B	109.5
C5—C4—H14	119.4	H24A—C17—H24B	109.5
N19—C18—C2	178.5 (3)	C16—C17—H24C	108.4
C6—C1—C2	120.2 (2)	H24A—C17—H24C	109.5
C6—C1—H16	119.4	H24B—C17—H24C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N7—H1···O15i	0.96	1.82	2.661 (2)	145
C1—H16···N19i	0.96	2.47	3.377 (3)	157
C13—H18···F23ii	0.96	2.50	3.365 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H1⋯O15	0.96	1.82	2.661 (2)	145
C1—H16⋯N19i	0.96	2.47	3.377 (3)	157
C13—H18⋯F23ii	0.96	2.50	3.365 (3)	150

Symmetry codes: (i) ; (ii) .