2-(4-Bromo-phen-yl)-N-(3,4-di-fluoro-phen-yl)acetamide.

In the title compound, C14H10BrF2NO, the dihedral angle between the mean planes of the 4-bromo-phenyl and 3,4-di-fluoro-phenyl rings is 66.4 (1)°. These two planes are twisted by 40.0 (5) and 86.3 (2)°, respectively, from that of the acetamide group. In the crystal, N-H⋯O hydrogen bonds and weak C-H⋯O and C-H⋯F inter-actions form infinite chains along [100].

Related literature

For the structural similarity of N-substituted 2-aryl­acetamides to the lateral chain of natural benzyl­penicillin, see: Mijin & Marinkovic (2006 ▶); Mijin et al. (2008 ▶). For the coordination abilities of amides, see: Wu et al. (2008 ▶, 2010 ▶). For related structures, see: Praveen et al. (2011a ▶,b ▶,c ▶, 2012 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H10BrF2NO

M = 326.14

Orthorhombic,

a = 4.9136 (3) Å

b = 6.0218 (4) Å

c = 42.514 (2) Å

V = 1257.96 (13) Å3

Z = 4

Cu Kα radiation

μ = 4.62 mm−1

T = 173 K

0.48 × 0.32 × 0.16 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.257, T max = 1.000

6592 measured reflections

2402 independent reflections

2388 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.106

S = 1.15

2402 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.87 e Å−3

Δρmin = −0.59 e Å−3

Absolute structure: Flack x determined using 915 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons & Flack, 2004 ▶)

Flack parameter: −0.01 (2)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012865/hg5313sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012865/hg5313Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012865/hg5313Isup3.cml

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

C14H10BrF2NO	Dx = 1.722 Mg m−3
Mr = 326.14	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 3482 reflections
a = 4.9136 (3) Å	θ = 3.1–71.3°
b = 6.0218 (4) Å	µ = 4.62 mm−1
c = 42.514 (2) Å	T = 173 K
V = 1257.96 (13) Å3	Block, colorless
Z = 4	0.48 × 0.32 × 0.16 mm
F(000) = 648

Agilent Xcalibur (Eos, Gemini) diffractometer	2402 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2388 reflections with I > 2σ(I)
Detector resolution: 16.1500 pixels mm-1	Rint = 0.036
ω scans	θmax = 71.4°, θmin = 4.2°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −5→4
Tmin = 0.257, Tmax = 1.000	k = −7→7
6592 measured reflections	l = −51→52

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0518P)2 + 2.6477P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.041	(Δ/σ)max = 0.001
wR(F2) = 0.106	Δρmax = 0.87 e Å−3
S = 1.15	Δρmin = −0.59 e Å−3
2402 reflections	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
173 parameters	Extinction coefficient: 0.0034 (5)
0 restraints	Absolute structure: Flack x determined using 915 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
Hydrogen site location: inferred from neighbouring sites	Flack parameter: −0.01 (2)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
Br1	0.05444 (13)	1.14849 (10)	0.52705 (2)	0.0255 (2)
F1	0.8291 (12)	−0.2536 (11)	0.73852 (13)	0.0682 (16)
F2	1.2315 (12)	−0.3056 (8)	0.69684 (13)	0.0577 (14)
O1	0.5535 (9)	0.4454 (8)	0.63179 (10)	0.0308 (9)
N1	0.9924 (9)	0.3661 (9)	0.64466 (11)	0.0243 (11)
H1	1.1630	0.3988	0.6404	0.029*
C1	0.7964 (12)	0.4695 (10)	0.62744 (13)	0.0203 (12)
C2	0.9134 (13)	0.6097 (10)	0.60058 (15)	0.0283 (13)
H2A	1.0489	0.7148	0.6093	0.034*
H2B	1.0088	0.5109	0.5856	0.034*
C3	0.6979 (12)	0.7387 (11)	0.58317 (14)	0.0222 (12)
C4	0.5905 (13)	0.6561 (11)	0.55519 (14)	0.0274 (12)
H4	0.6491	0.5161	0.5474	0.033*
C5	0.3960 (12)	0.7791 (10)	0.53850 (14)	0.0231 (13)
H5	0.3216	0.7238	0.5194	0.028*
C6	0.3155 (12)	0.9796 (10)	0.55018 (13)	0.0206 (11)
C7	0.4148 (13)	1.0645 (10)	0.57804 (14)	0.0235 (12)
H7	0.3531	1.2035	0.5858	0.028*
C8	0.6072 (12)	0.9412 (11)	0.59439 (13)	0.0255 (13)
H8	0.6779	0.9970	0.6136	0.031*
C9	0.9424 (13)	0.2099 (10)	0.66883 (13)	0.0247 (12)
C10	1.1086 (13)	0.0238 (12)	0.67050 (15)	0.0300 (14)
H10	1.2496	0.0018	0.6555	0.036*
C11	1.0656 (16)	−0.1289 (11)	0.69426 (16)	0.0365 (15)
C12	0.8674 (15)	−0.0986 (14)	0.71582 (17)	0.0427 (19)
C13	0.7024 (15)	0.0831 (15)	0.71475 (16)	0.0415 (19)
H13	0.5641	0.1022	0.7301	0.050*
C14	0.7366 (14)	0.2408 (13)	0.69109 (15)	0.0305 (14)
H14	0.6217	0.3675	0.6901	0.037*

	U11	U22	U33	U12	U13	U23
Br1	0.0229 (3)	0.0270 (3)	0.0266 (3)	0.0051 (2)	0.0000 (2)	0.0054 (2)
F1	0.062 (3)	0.089 (4)	0.054 (3)	−0.020 (3)	−0.005 (3)	0.045 (3)
F2	0.063 (3)	0.045 (3)	0.065 (3)	0.010 (2)	−0.009 (3)	0.009 (2)
O1	0.015 (2)	0.045 (2)	0.032 (2)	0.003 (2)	0.0007 (18)	0.0076 (19)
N1	0.007 (2)	0.037 (3)	0.029 (2)	−0.001 (2)	0.0003 (16)	0.006 (2)
C1	0.011 (3)	0.025 (3)	0.025 (3)	0.001 (2)	0.000 (2)	−0.002 (2)
C2	0.016 (3)	0.031 (3)	0.038 (3)	−0.005 (3)	0.005 (2)	0.009 (2)
C3	0.012 (3)	0.030 (3)	0.024 (3)	0.002 (2)	0.004 (2)	0.006 (2)
C4	0.026 (3)	0.024 (3)	0.032 (3)	0.009 (3)	0.005 (2)	−0.002 (2)
C5	0.023 (3)	0.022 (3)	0.024 (3)	0.004 (2)	0.000 (2)	−0.002 (2)
C6	0.013 (3)	0.024 (3)	0.024 (3)	0.002 (2)	−0.003 (2)	0.007 (2)
C7	0.021 (3)	0.023 (3)	0.027 (3)	0.006 (3)	0.002 (2)	−0.005 (2)
C8	0.024 (3)	0.030 (3)	0.022 (3)	−0.003 (3)	0.001 (2)	−0.002 (2)
C9	0.017 (3)	0.033 (3)	0.024 (3)	−0.010 (3)	−0.006 (2)	0.003 (2)
C10	0.022 (3)	0.040 (4)	0.027 (3)	0.003 (3)	0.000 (2)	0.003 (3)
C11	0.038 (4)	0.031 (3)	0.041 (3)	−0.006 (4)	−0.013 (3)	0.006 (3)
C12	0.036 (4)	0.057 (5)	0.035 (3)	−0.016 (3)	−0.012 (3)	0.020 (3)
C13	0.025 (4)	0.069 (6)	0.029 (3)	−0.009 (4)	0.001 (3)	0.007 (3)
C14	0.024 (3)	0.042 (4)	0.025 (3)	0.002 (3)	0.001 (2)	0.003 (3)

Br1—C6	1.909 (6)	C5—C6	1.364 (9)
F1—C12	1.356 (8)	C5—H5	0.9500
F2—C11	1.345 (9)	C6—C7	1.379 (8)
O1—C1	1.217 (8)	C7—C8	1.389 (9)
N1—C1	1.360 (7)	C7—H7	0.9500
N1—C9	1.414 (8)	C8—H8	0.9500
N1—H1	0.8800	C9—C10	1.388 (10)
C1—C2	1.532 (8)	C9—C14	1.398 (9)
C2—C3	1.508 (8)	C10—C11	1.382 (9)
C2—H2A	0.9900	C10—H10	0.9500
C2—H2B	0.9900	C11—C12	1.350 (11)
C3—C8	1.383 (9)	C12—C13	1.362 (12)
C3—C4	1.393 (9)	C13—C14	1.394 (10)
C4—C5	1.402 (8)	C13—H13	0.9500
C4—H4	0.9500	C14—H14	0.9500
C1—N1—C9	124.9 (5)	C6—C7—C8	118.2 (5)
C1—N1—H1	117.5	C6—C7—H7	120.9
C9—N1—H1	117.5	C8—C7—H7	120.9
O1—C1—N1	123.9 (6)	C3—C8—C7	121.2 (6)
O1—C1—C2	123.2 (6)	C3—C8—H8	119.4
N1—C1—C2	112.8 (5)	C7—C8—H8	119.4
C3—C2—C1	112.7 (5)	C10—C9—C14	119.9 (6)
C3—C2—H2A	109.0	C10—C9—N1	118.2 (6)
C1—C2—H2A	109.0	C14—C9—N1	122.0 (6)
C3—C2—H2B	109.0	C11—C10—C9	119.0 (6)
C1—C2—H2B	109.0	C11—C10—H10	120.5
H2A—C2—H2B	107.8	C9—C10—H10	120.5
C8—C3—C4	119.2 (6)	F2—C11—C12	119.3 (6)
C8—C3—C2	120.7 (6)	F2—C11—C10	119.6 (7)
C4—C3—C2	120.1 (6)	C12—C11—C10	121.1 (7)
C3—C4—C5	120.1 (6)	C11—C12—F1	119.4 (8)
C3—C4—H4	119.9	C11—C12—C13	121.0 (7)
C5—C4—H4	119.9	F1—C12—C13	119.6 (8)
C6—C5—C4	118.8 (6)	C12—C13—C14	120.0 (7)
C6—C5—H5	120.6	C12—C13—H13	120.0
C4—C5—H5	120.6	C14—C13—H13	120.0
C5—C6—C7	122.5 (6)	C13—C14—C9	119.0 (7)
C5—C6—Br1	118.6 (4)	C13—C14—H14	120.5
C7—C6—Br1	118.9 (5)	C9—C14—H14	120.5
C9—N1—C1—O1	3.0 (10)	C1—N1—C9—C10	138.7 (6)
C9—N1—C1—C2	−173.6 (5)	C1—N1—C9—C14	−42.7 (9)
O1—C1—C2—C3	8.0 (9)	C14—C9—C10—C11	0.3 (9)
N1—C1—C2—C3	−175.4 (5)	N1—C9—C10—C11	179.0 (6)
C1—C2—C3—C8	83.5 (7)	C9—C10—C11—F2	−177.5 (6)
C1—C2—C3—C4	−97.5 (7)	C9—C10—C11—C12	−0.6 (10)
C8—C3—C4—C5	0.9 (9)	F2—C11—C12—F1	−3.9 (11)
C2—C3—C4—C5	−178.1 (5)	C10—C11—C12—F1	179.1 (6)
C3—C4—C5—C6	0.1 (9)	F2—C11—C12—C13	177.3 (7)
C4—C5—C6—C7	−1.1 (9)	C10—C11—C12—C13	0.3 (11)
C4—C5—C6—Br1	179.1 (5)	C11—C12—C13—C14	0.1 (11)
C5—C6—C7—C8	1.1 (9)	F1—C12—C13—C14	−178.6 (7)
Br1—C6—C7—C8	−179.1 (5)	C12—C13—C14—C9	−0.4 (11)
C4—C3—C8—C7	−1.0 (9)	C10—C9—C14—C13	0.1 (10)
C2—C3—C8—C7	178.0 (6)	N1—C9—C14—C13	−178.5 (6)
C6—C7—C8—C3	0.0 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	1.97	2.851 (7)	175
C7—H7···O1ii	0.95	2.63	3.309 (8)	129
C13—H13···F1iii	0.95	2.50	3.426 (9)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	1.97	2.851 (7)	175
C7—H7⋯O1ii	0.95	2.63	3.309 (8)	129
C13—H13⋯F1iii	0.95	2.50	3.426 (9)	164

Symmetry codes: (i) ; (ii) ; (iii) .