2,6-Di-fluoro-N-(prop-2-yn-yl)benzamide.

In the mol-ecule of the title di-fluoro-benzamide derivative, C10H7F2NO, the angle formed by the least-squares mean line through the prop-2-ynyl group [maximum deviation = 0.011 (3) Å] and the normal to the benzene ring is 59.03 (7)°. In the crystal, mol-ecules are linked via N-H⋯O and C-H⋯F hydrogen bonds into layers parallel to the ac plane.

Related literature

For the biological activity of di­fluoro­benzamide derivatives, see: Chang et al. (2002 ▶); Kees et al. (1989 ▶); Ragavan et al. (2010 ▶); Carmellino et al. (1994 ▶); Rauko et al. (2001 ▶). For the crystal structure of a related compound, see: Fun et al. (2010 ▶).

Experimental

Crystal data

C10H7F2NO

M = 195.17

Monoclinic,

a = 5.0479 (8) Å

b = 19.738 (3) Å

c = 9.2428 (15) Å

β = 91.432 (4)°

V = 920.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 273 K

0.38 × 0.17 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

5388 measured reflections

1669 independent reflections

1283 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.099

S = 1.03

1669 reflections

135 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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 datablock(s) global, I. DOI: 10.1107/S1600536813021120/rz5082sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021120/rz5082Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813021120/rz5082Isup3.cml

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

C10H7F2NO	F(000) = 400
Mr = 195.17	Dx = 1.408 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1280 reflections
a = 5.0479 (8) Å	θ = 2.4–22.9°
b = 19.738 (3) Å	µ = 0.12 mm−1
c = 9.2428 (15) Å	T = 273 K
β = 91.432 (4)°	Block, colourless
V = 920.6 (3) Å3	0.38 × 0.17 × 0.10 mm
Z = 4

Bruker SMART APEX CCD diffractometer	1283 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 25.5°, θmin = 2.1°
phi and ω scans	h = −6→6
5388 measured reflections	k = −23→22
1669 independent reflections	l = −10→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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0397P)2 + 0.172P] where P = (Fo2 + 2Fc2)/3
1669 reflections	(Δ/σ)max < 0.001
135 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.15 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
F1	0.4706 (2)	0.66642 (6)	0.01184 (13)	0.0784 (4)
F2	1.1590 (2)	0.68247 (6)	−0.31627 (13)	0.0808 (4)
O1	1.0617 (2)	0.56728 (6)	−0.15774 (16)	0.0689 (4)
N1	0.6219 (3)	0.55850 (7)	−0.17077 (17)	0.0520 (4)
C1	0.6337 (3)	0.70378 (9)	−0.06950 (19)	0.0533 (5)
C2	0.6133 (4)	0.77291 (10)	−0.0635 (2)	0.0670 (6)
H2A	0.4884	0.7934	−0.0055	0.080*
C3	0.7807 (4)	0.81150 (10)	−0.1445 (2)	0.0690 (6)
H3A	0.7685	0.8585	−0.1419	0.083*
C4	0.9655 (4)	0.78117 (10)	−0.2290 (2)	0.0664 (5)
H4A	1.0802	0.8071	−0.2835	0.080*
C5	0.9778 (3)	0.71209 (9)	−0.2314 (2)	0.0546 (5)
C6	0.8147 (3)	0.66992 (8)	−0.15372 (17)	0.0453 (4)
C7	0.8430 (3)	0.59431 (9)	−0.16021 (17)	0.0475 (4)
C8	0.6276 (4)	0.48497 (9)	−0.1809 (2)	0.0607 (5)
H8A	0.4535	0.4673	−0.1599	0.073*
H8B	0.7519	0.4674	−0.1085	0.073*
C9	0.7041 (4)	0.46128 (9)	−0.3233 (2)	0.0621 (5)
C10	0.7642 (5)	0.44382 (12)	−0.4380 (3)	0.0880 (7)
H1	0.475 (4)	0.5775 (9)	−0.1715 (19)	0.061 (6)*
H2	0.817 (5)	0.4327 (13)	−0.524 (3)	0.120 (10)*

	U11	U22	U33	U12	U13	U23
F1	0.0691 (7)	0.0792 (8)	0.0889 (9)	−0.0091 (6)	0.0395 (6)	−0.0161 (6)
F2	0.0727 (7)	0.0810 (8)	0.0907 (9)	−0.0041 (6)	0.0418 (7)	−0.0052 (6)
O1	0.0315 (6)	0.0655 (8)	0.1096 (11)	0.0057 (5)	0.0013 (6)	−0.0028 (7)
N1	0.0316 (7)	0.0521 (9)	0.0726 (11)	0.0022 (6)	0.0071 (7)	−0.0047 (7)
C1	0.0412 (9)	0.0628 (11)	0.0559 (11)	−0.0019 (8)	0.0054 (8)	−0.0104 (9)
C2	0.0543 (10)	0.0674 (13)	0.0794 (14)	0.0088 (9)	0.0033 (10)	−0.0230 (10)
C3	0.0648 (12)	0.0532 (11)	0.0885 (16)	0.0037 (9)	−0.0073 (11)	−0.0048 (10)
C4	0.0604 (11)	0.0634 (12)	0.0753 (14)	−0.0065 (9)	0.0039 (10)	0.0069 (10)
C5	0.0432 (9)	0.0629 (11)	0.0579 (11)	−0.0003 (8)	0.0070 (8)	−0.0048 (9)
C6	0.0320 (8)	0.0553 (10)	0.0484 (10)	0.0000 (7)	−0.0021 (7)	−0.0053 (8)
C7	0.0328 (8)	0.0571 (10)	0.0527 (10)	0.0014 (7)	0.0052 (7)	−0.0023 (8)
C8	0.0503 (10)	0.0529 (11)	0.0794 (14)	−0.0025 (8)	0.0094 (9)	0.0042 (9)
C9	0.0579 (11)	0.0451 (10)	0.0835 (16)	0.0055 (8)	0.0048 (11)	−0.0031 (10)
C10	0.1032 (19)	0.0689 (15)	0.092 (2)	0.0121 (12)	0.0132 (16)	−0.0128 (14)

F1—C1	1.3482 (19)	C3—H3A	0.9300
F2—C5	1.3530 (18)	C4—C5	1.365 (3)
O1—C7	1.2256 (17)	C4—H4A	0.9300
N1—C7	1.323 (2)	C5—C6	1.384 (2)
N1—C8	1.455 (2)	C6—C7	1.501 (2)
N1—H1	0.830 (19)	C8—C9	1.458 (3)
C1—C2	1.370 (3)	C8—H8A	0.9700
C1—C6	1.387 (2)	C8—H8B	0.9700
C2—C3	1.374 (3)	C9—C10	1.162 (3)
C2—H2A	0.9300	C10—H2	0.87 (3)
C3—C4	1.369 (3)
C7—N1—C8	121.31 (15)	F2—C5—C6	117.42 (16)
C7—N1—H1	120.7 (13)	C4—C5—C6	124.38 (16)
C8—N1—H1	118.0 (13)	C5—C6—C1	114.22 (16)
F1—C1—C2	118.34 (15)	C5—C6—C7	121.27 (14)
F1—C1—C6	118.01 (16)	C1—C6—C7	124.49 (15)
C2—C1—C6	123.65 (17)	O1—C7—N1	121.78 (16)
C1—C2—C3	118.85 (17)	O1—C7—C6	121.24 (14)
C1—C2—H2A	120.6	N1—C7—C6	116.97 (13)
C3—C2—H2A	120.6	N1—C8—C9	112.60 (15)
C4—C3—C2	120.37 (18)	N1—C8—H8A	109.1
C4—C3—H3A	119.8	C9—C8—H8A	109.1
C2—C3—H3A	119.8	N1—C8—H8B	109.1
C5—C4—C3	118.53 (18)	C9—C8—H8B	109.1
C5—C4—H4A	120.7	H8A—C8—H8B	107.8
C3—C4—H4A	120.7	C10—C9—C8	178.5 (2)
F2—C5—C4	118.19 (16)	C9—C10—H2	176.4 (19)
F1—C1—C2—C3	179.19 (17)	C2—C1—C6—C5	0.6 (3)
C6—C1—C2—C3	−0.2 (3)	F1—C1—C6—C7	−0.3 (2)
C1—C2—C3—C4	−0.4 (3)	C2—C1—C6—C7	179.05 (18)
C2—C3—C4—C5	0.4 (3)	C8—N1—C7—O1	−0.4 (3)
C3—C4—C5—F2	179.33 (17)	C8—N1—C7—C6	178.68 (15)
C3—C4—C5—C6	0.1 (3)	C5—C6—C7—O1	41.8 (2)
F2—C5—C6—C1	−179.83 (15)	C1—C6—C7—O1	−136.53 (18)
C4—C5—C6—C1	−0.6 (3)	C5—C6—C7—N1	−137.26 (17)
F2—C5—C6—C7	1.7 (2)	C1—C6—C7—N1	44.4 (2)
C4—C5—C6—C7	−179.07 (18)	C7—N1—C8—C9	−75.0 (2)
F1—C1—C6—C5	−178.74 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.83 (2)	2.10 (2)	2.8387 (19)	147.4 (17)
C2—H2A···F2ii	0.93	2.49	3.394 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.83 (2)	2.10 (2)	2.8387 (19)	147.4 (17)
C2—H2A⋯F2ii	0.93	2.49	3.394 (2)	164

Symmetry codes: (i) ; (ii) .