N-(3,4-Difluoro-phen-yl)-2-(3,4-dimethoxy-phen-yl)acetamide.

In the title amide, C(16)H(15)F(2)NO(3), the dihedral angle between the benzene rings is 53.7 (1)°. Mol-ecules are linked in the crystal structure by an inter-molecular N-H⋯O hydrogen bond involving N-H and C=O functionalities of the amide group. A one-dimensional network is thus formed along the [001] direction. No significant inter-chain contacts are observed.

Related literature

For general background, see: Maeda et al. (1991 ▶); Dawley et al. (1993 ▶); Nerya et al. (2003 ▶); Lee et al. (2007 ▶); Ha et al. (2007 ▶); Hong et al. (2008 ▶); Yan et al. (2007 ▶).

Experimental

Crystal data

C16H15F2NO3

M = 307.29

Monoclinic,

a = 8.6440 (11) Å

b = 18.867 (6) Å

c = 9.4827 (13) Å

β = 111.019 (11)°

V = 1443.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 295 (2) K

0.26 × 0.26 × 0.23 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2855 measured reflections

2689 independent reflections

1089 reflections with I > 2σ(I)

R int = 0.050

3 standard reflections every 400 reflections intensity decay: 3%

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.161

S = 0.99

2689 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003590/bh2160sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003590/bh2160Isup2.hkl

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

C16H15F2NO3	F000 = 640
Mr = 307.29	Dx = 1.414 Mg m−3
Monoclinic, P21/c	Melting point: 393 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 8.6440 (11) Å	Cell parameters from 25 reflections
b = 18.867 (6) Å	θ = 10.0–13.5º
c = 9.4827 (13) Å	µ = 0.12 mm−1
β = 111.019 (11)º	T = 295 (2) K
V = 1443.6 (5) Å3	Block, colourless
Z = 4	0.26 × 0.26 × 0.23 mm

Enraf–Nonius CAD-4 diffractometer	θmin = 2.2º
non–profiled ω/2θ scans	h = −10→9
Absorption correction: none	k = 0→22
2855 measured reflections	l = 0→11
2689 independent reflections	3 standard reflections
1089 reflections with I > 2σ(I)	every 400 reflections
Rint = 0.050	intensity decay: 3%
θmax = 25.5º

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0403P)2] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.076	(Δ/σ)max < 0.001
wR(F2) = 0.161	Δρmax = 0.19 e Å−3
S = 1.00	Δρmin = −0.19 e Å−3
2689 reflections	Extinction correction: none
203 parameters

	x	y	z	Uiso*/Ueq
C1	0.1632 (6)	0.6519 (2)	−0.2444 (5)	0.0423 (12)
C2	0.0544 (6)	0.6516 (3)	−0.3939 (5)	0.0492 (13)
H2	0.0578	0.6871	−0.4606	0.059*
C3	−0.0570 (7)	0.5976 (3)	−0.4396 (6)	0.0581 (15)
C4	−0.0637 (7)	0.5447 (3)	−0.3452 (6)	0.0593 (15)
C5	0.0438 (7)	0.5443 (3)	−0.1995 (6)	0.0671 (17)
H5	0.0407	0.5079	−0.1346	0.081*
C6	0.1575 (6)	0.5985 (3)	−0.1487 (5)	0.0531 (14)
H6	0.2306	0.5988	−0.0489	0.064*
F1	−0.1663 (4)	0.59760 (17)	−0.5842 (3)	0.0941 (12)
F2	−0.1777 (4)	0.49215 (17)	−0.3968 (4)	0.0917 (12)
N7	0.2760 (5)	0.7098 (2)	−0.2001 (4)	0.0446 (11)
H7	0.304 (6)	0.729 (3)	−0.273 (5)	0.08 (2)*
C8	0.3307 (6)	0.7408 (3)	−0.0639 (5)	0.0418 (12)
O9	0.2978 (4)	0.71902 (17)	0.0431 (3)	0.0608 (11)
C10	0.4341 (6)	0.8066 (3)	−0.0549 (5)	0.0566 (15)
H10A	0.5055	0.7986	−0.1122	0.068*
H10B	0.3607	0.8457	−0.1019	0.068*
C11	0.5399 (6)	0.8276 (3)	0.1044 (5)	0.0464 (13)
C12	0.5239 (6)	0.8935 (3)	0.1612 (5)	0.0502 (14)
H12	0.4463	0.9254	0.1007	0.06*
C13	0.6219 (6)	0.9127 (3)	0.3069 (5)	0.0490 (14)
C14	0.7395 (6)	0.8654 (3)	0.3968 (5)	0.0498 (13)
C15	0.7552 (6)	0.8002 (3)	0.3398 (5)	0.0611 (16)
H15	0.8334	0.7682	0.3993	0.073*
C16	0.6557 (6)	0.7815 (3)	0.1945 (6)	0.0599 (15)
H16	0.6677	0.737	0.1575	0.072*
O17	0.6123 (4)	0.97621 (19)	0.3725 (4)	0.0741 (12)
C18	0.4880 (7)	1.0251 (3)	0.2884 (6)	0.0797 (19)
H18A	0.4946	1.0671	0.3474	0.12*
H18B	0.3807	1.0039	0.2643	0.12*
H18C	0.505	1.0373	0.1968	0.12*
O19	0.8299 (4)	0.88921 (18)	0.5388 (4)	0.0679 (11)
C20	0.9656 (6)	0.8464 (3)	0.6292 (5)	0.0686 (17)
H20A	1.0195	0.869	0.7251	0.103*
H20B	1.0431	0.8408	0.5786	0.103*
H20C	0.9252	0.8008	0.6446	0.103*

	U11	U22	U33	U12	U13	U23
C1	0.047 (3)	0.043 (3)	0.037 (3)	0.001 (3)	0.015 (2)	−0.006 (2)
C2	0.054 (3)	0.045 (3)	0.039 (3)	0.000 (3)	0.006 (3)	0.006 (2)
C3	0.060 (4)	0.062 (4)	0.040 (3)	0.001 (3)	0.004 (3)	−0.013 (3)
C4	0.061 (4)	0.053 (4)	0.060 (4)	−0.007 (3)	0.018 (3)	−0.010 (3)
C5	0.092 (5)	0.043 (4)	0.066 (4)	−0.010 (3)	0.028 (4)	0.001 (3)
C6	0.067 (4)	0.047 (3)	0.040 (3)	0.002 (3)	0.012 (3)	0.006 (3)
F1	0.087 (3)	0.103 (3)	0.062 (2)	−0.025 (2)	−0.0110 (18)	−0.010 (2)
F2	0.093 (3)	0.073 (2)	0.103 (3)	−0.036 (2)	0.028 (2)	−0.024 (2)
N7	0.047 (3)	0.053 (3)	0.030 (2)	−0.004 (2)	0.010 (2)	−0.003 (2)
C8	0.041 (3)	0.053 (3)	0.029 (3)	−0.002 (3)	0.010 (2)	−0.003 (3)
O9	0.078 (3)	0.073 (3)	0.0360 (19)	−0.027 (2)	0.0258 (18)	−0.0142 (18)
C10	0.056 (3)	0.066 (4)	0.045 (3)	−0.009 (3)	0.015 (3)	−0.003 (3)
C11	0.045 (3)	0.051 (3)	0.041 (3)	−0.004 (3)	0.012 (2)	−0.003 (3)
C12	0.044 (3)	0.056 (4)	0.044 (3)	−0.001 (3)	0.009 (3)	0.004 (3)
C13	0.050 (3)	0.049 (3)	0.041 (3)	0.000 (3)	0.007 (3)	−0.011 (3)
C14	0.041 (3)	0.058 (4)	0.041 (3)	−0.001 (3)	0.004 (2)	−0.006 (3)
C15	0.056 (3)	0.057 (4)	0.054 (3)	0.011 (3)	0.000 (3)	−0.014 (3)
C16	0.060 (4)	0.059 (4)	0.057 (3)	0.000 (3)	0.018 (3)	−0.009 (3)
O17	0.069 (3)	0.062 (3)	0.062 (2)	0.020 (2)	−0.012 (2)	−0.008 (2)
C18	0.074 (4)	0.059 (4)	0.083 (4)	0.016 (3)	0.000 (3)	−0.006 (3)
O19	0.062 (2)	0.070 (3)	0.048 (2)	0.019 (2)	−0.0085 (19)	−0.0103 (19)
C20	0.054 (3)	0.078 (4)	0.051 (3)	0.010 (3)	−0.009 (3)	0.000 (3)

C1—C6	1.368 (6)	C11—C16	1.369 (6)
C1—C2	1.392 (6)	C11—C12	1.381 (6)
C1—N7	1.423 (6)	C12—C13	1.386 (6)
C2—C3	1.362 (6)	C12—H12	0.93
C2—H2	0.93	C13—O17	1.367 (5)
C3—C4	1.356 (7)	C13—C14	1.390 (6)
C3—F1	1.357 (5)	C14—O19	1.368 (5)
C4—F2	1.359 (5)	C14—C15	1.370 (6)
C4—C5	1.361 (6)	C15—C16	1.383 (6)
C5—C6	1.380 (6)	C15—H15	0.93
C5—H5	0.93	C16—H16	0.93
C6—H6	0.93	O17—C18	1.423 (5)
N7—C8	1.340 (5)	C18—H18A	0.96
N7—H7	0.89 (5)	C18—H18B	0.96
C8—O9	1.219 (5)	C18—H18C	0.96
C8—C10	1.515 (6)	O19—C20	1.428 (5)
C10—C11	1.511 (6)	C20—H20A	0.96
C10—H10A	0.97	C20—H20B	0.96
C10—H10B	0.97	C20—H20C	0.96
C6—C1—C2	120.0 (5)	C16—C11—C10	120.2 (5)
C6—C1—N7	123.6 (4)	C12—C11—C10	121.0 (4)
C2—C1—N7	116.4 (4)	C11—C12—C13	120.9 (5)
C3—C2—C1	118.0 (5)	C11—C12—H12	119.6
C3—C2—H2	121	C13—C12—H12	119.6
C1—C2—H2	121	O17—C13—C12	124.6 (4)
C4—C3—F1	119.2 (5)	O17—C13—C14	115.7 (4)
C4—C3—C2	122.2 (5)	C12—C13—C14	119.7 (5)
F1—C3—C2	118.5 (5)	O19—C14—C15	125.5 (4)
C3—C4—F2	119.8 (5)	O19—C14—C13	115.3 (4)
C3—C4—C5	119.9 (5)	C15—C14—C13	119.2 (4)
F2—C4—C5	120.4 (5)	C14—C15—C16	120.5 (5)
C4—C5—C6	119.5 (5)	C14—C15—H15	119.7
C4—C5—H5	120.2	C16—C15—H15	119.7
C6—C5—H5	120.2	C11—C16—C15	120.9 (5)
C1—C6—C5	120.3 (5)	C11—C16—H16	119.5
C1—C6—H6	119.9	C15—C16—H16	119.5
C5—C6—H6	119.9	C13—O17—C18	118.1 (4)
C8—N7—C1	125.9 (4)	O17—C18—H18A	109.5
C8—N7—H7	118 (3)	O17—C18—H18B	109.5
C1—N7—H7	116 (3)	H18A—C18—H18B	109.5
O9—C8—N7	123.3 (5)	O17—C18—H18C	109.5
O9—C8—C10	122.6 (4)	H18A—C18—H18C	109.5
N7—C8—C10	114.1 (4)	H18B—C18—H18C	109.5
C11—C10—C8	113.8 (4)	C14—O19—C20	117.5 (4)
C11—C10—H10A	108.8	O19—C20—H20A	109.5
C8—C10—H10A	108.8	O19—C20—H20B	109.5
C11—C10—H10B	108.8	H20A—C20—H20B	109.5
C8—C10—H10B	108.8	O19—C20—H20C	109.5
H10A—C10—H10B	107.7	H20A—C20—H20C	109.5
C16—C11—C12	118.8 (4)	H20B—C20—H20C	109.5
C6—C1—C2—C3	0.8 (7)	C8—C10—C11—C16	59.3 (6)
N7—C1—C2—C3	−178.9 (4)	C8—C10—C11—C12	−121.7 (5)
C1—C2—C3—C4	−0.6 (8)	C16—C11—C12—C13	−0.6 (7)
C1—C2—C3—F1	178.5 (4)	C10—C11—C12—C13	−179.5 (4)
F1—C3—C4—F2	0.8 (8)	C11—C12—C13—O17	−178.9 (5)
C2—C3—C4—F2	179.9 (5)	C11—C12—C13—C14	0.8 (7)
F1—C3—C4—C5	−179.3 (5)	O17—C13—C14—O19	−0.2 (7)
C2—C3—C4—C5	−0.2 (9)	C12—C13—C14—O19	−180.0 (4)
C3—C4—C5—C6	0.8 (8)	O17—C13—C14—C15	179.1 (5)
F2—C4—C5—C6	−179.3 (5)	C12—C13—C14—C15	−0.6 (8)
C2—C1—C6—C5	−0.2 (7)	O19—C14—C15—C16	179.4 (5)
N7—C1—C6—C5	179.5 (5)	C13—C14—C15—C16	0.2 (8)
C4—C5—C6—C1	−0.6 (8)	C12—C11—C16—C15	0.1 (8)
C6—C1—N7—C8	−34.1 (7)	C10—C11—C16—C15	179.1 (5)
C2—C1—N7—C8	145.6 (5)	C14—C15—C16—C11	0.1 (8)
C1—N7—C8—O9	5.3 (8)	C12—C13—O17—C18	3.0 (7)
C1—N7—C8—C10	−173.2 (4)	C14—C13—O17—C18	−176.8 (5)
O9—C8—C10—C11	20.3 (7)	C15—C14—O19—C20	8.1 (8)
N7—C8—C10—C11	−161.2 (4)	C13—C14—O19—C20	−172.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O9i	0.89 (5)	1.98 (5)	2.846 (5)	163 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O9i	0.89 (5)	1.98 (5)	2.846 (5)	163 (5)

Symmetry code: (i) .