N-(3-Chloro-4-fluoro-phen-yl)-2,2-diphenyl-acetamide.

In the title compound, C(20)H(15)ClFNO, the dihedral angles between the mean planes of the acetamide group and the chloro-fluoro-substituted benzene ring and the two phenyl rings are 10.8 (8), 81.9 (7) and 85.8 (5)°, respectively. The crystal packing is stabilized by N-H⋯O hydrogen bonds and weak C-H⋯O inter-molecular inter-actions, forming infinite chains along the c axis.

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 their coordination abilities, see: Wu et al. (2008 ▶, 2010 ▶). For related structures, see: Davis & Healy (2010 ▶); Li et al. (2010 ▶); Li & Wu (2010 ▶); Wang et al. (2010 ▶); Xiao et al. (2010 ▶).

Experimental

Crystal data

C20H15ClFNO

M = 339.78

Monoclinic,

a = 9.3665 (17) Å

b = 10.2069 (12) Å

c = 9.7774 (16) Å

β = 114.42 (2)°

V = 851.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 173 K

0.35 × 0.12 × 0.12 mm

Data collection

Oxford Diffractio Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.921, T max = 0.972

7456 measured reflections

3794 independent reflections

3265 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.109

S = 1.01

3794 reflections

220 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1668 Friedel pairs

Flack parameter: −0.06 (6)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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) I. DOI: 10.1107/S1600536811036075/ya2145sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036075/ya2145Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036075/ya2145Isup3.cml

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

C20H15ClFNO	F(000) = 352
Mr = 339.78	Dx = 1.326 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 3667 reflections
a = 9.3665 (17) Å	θ = 3.0–32.4°
b = 10.2069 (12) Å	µ = 0.24 mm−1
c = 9.7774 (16) Å	T = 173 K
β = 114.42 (2)°	Block, colorless
V = 851.1 (2) Å3	0.35 × 0.12 × 0.12 mm
Z = 2

Oxford Diffractio Xcalibur Eos Gemini diffractometer	3794 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3265 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 16.1500 pixels mm-1	θmax = 28.3°, θmin = 3.0°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −13→13
Tmin = 0.921, Tmax = 0.972	l = −12→13
7456 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0597P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3794 reflections	Δρmax = 0.17 e Å−3
220 parameters	Δρmin = −0.17 e Å−3
3 restraints	Absolute structure: Flack (1983), 1668 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.06 (6)

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.

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	0.25355 (8)	0.11734 (7)	0.82272 (8)	0.0727 (2)
F1	0.15076 (18)	0.07394 (14)	0.50254 (19)	0.0658 (4)
O1	0.6516 (2)	0.52072 (16)	0.54006 (16)	0.0550 (4)
N1	0.6367 (2)	0.42807 (16)	0.74325 (18)	0.0431 (4)
H1N	0.665 (3)	0.433 (2)	0.837 (2)	0.052*
C1	0.4496 (3)	0.28097 (19)	0.7678 (2)	0.0446 (4)
H1A	0.4915	0.3022	0.8716	0.053*
C2	0.3294 (3)	0.19290 (18)	0.7097 (3)	0.0454 (5)
C3	0.2684 (2)	0.16238 (19)	0.5588 (3)	0.0461 (5)
C4	0.3265 (3)	0.2195 (2)	0.4665 (3)	0.0543 (5)
H4A	0.2836	0.1976	0.3628	0.065*
C5	0.4470 (3)	0.3086 (2)	0.5227 (2)	0.0506 (5)
H5A	0.4865	0.3489	0.4579	0.061*
C6	0.5107 (2)	0.33973 (18)	0.6746 (2)	0.0387 (4)
C7	0.6985 (2)	0.51195 (18)	0.6763 (2)	0.0390 (4)
C8	0.8312 (2)	0.59755 (18)	0.7841 (2)	0.0393 (4)
H8A	0.8897	0.5446	0.8765	0.047*
C9	0.7663 (3)	0.71731 (18)	0.8311 (2)	0.0433 (4)
C10	0.8448 (3)	0.7672 (2)	0.9741 (3)	0.0582 (6)
H10A	0.9365	0.7245	1.0431	0.070*
C11	0.7909 (4)	0.8791 (3)	1.0177 (4)	0.0751 (8)
H11A	0.8460	0.9124	1.1165	0.090*
C12	0.6600 (4)	0.9418 (3)	0.9208 (4)	0.0796 (9)
H12A	0.6245	1.0189	0.9515	0.096*
C13	0.5799 (4)	0.8935 (3)	0.7795 (4)	0.0767 (8)
H13A	0.4882	0.9370	0.7117	0.092*
C14	0.6317 (3)	0.7811 (3)	0.7341 (3)	0.0628 (6)
H14A	0.5745	0.7476	0.6357	0.075*
C15	0.9445 (2)	0.62793 (18)	0.7125 (2)	0.0416 (4)
C16	1.0589 (3)	0.5378 (2)	0.7245 (3)	0.0532 (5)
H16A	1.0688	0.4600	0.7810	0.064*
C17	1.1594 (3)	0.5589 (3)	0.6554 (3)	0.0649 (6)
H17A	1.2372	0.4956	0.6645	0.078*
C18	1.1470 (3)	0.6703 (3)	0.5742 (3)	0.0662 (7)
H18A	1.2167	0.6854	0.5277	0.079*
C19	1.0328 (3)	0.7606 (3)	0.5601 (3)	0.0662 (7)
H19A	1.0229	0.8377	0.5024	0.079*
C20	0.9324 (3)	0.7403 (2)	0.6290 (3)	0.0570 (6)
H20A	0.8545	0.8038	0.6191	0.068*

	U11	U22	U33	U12	U13	U23
Cl1	0.0985 (5)	0.0717 (4)	0.0713 (4)	−0.0219 (4)	0.0586 (4)	−0.0035 (3)
F1	0.0645 (8)	0.0659 (8)	0.0738 (10)	−0.0204 (7)	0.0356 (7)	−0.0198 (7)
O1	0.0727 (10)	0.0649 (9)	0.0269 (7)	−0.0149 (8)	0.0200 (7)	0.0038 (6)
N1	0.0602 (10)	0.0470 (8)	0.0244 (7)	−0.0089 (8)	0.0197 (8)	−0.0019 (7)
C1	0.0650 (12)	0.0413 (9)	0.0328 (10)	−0.0007 (9)	0.0257 (9)	0.0003 (7)
C2	0.0594 (12)	0.0392 (9)	0.0494 (12)	0.0018 (9)	0.0342 (10)	0.0011 (8)
C3	0.0482 (11)	0.0405 (9)	0.0520 (13)	−0.0027 (8)	0.0232 (10)	−0.0059 (9)
C4	0.0603 (13)	0.0646 (13)	0.0345 (10)	−0.0093 (10)	0.0161 (10)	−0.0079 (9)
C5	0.0651 (13)	0.0580 (11)	0.0328 (10)	−0.0110 (10)	0.0242 (10)	−0.0025 (9)
C6	0.0514 (10)	0.0391 (8)	0.0298 (9)	0.0015 (8)	0.0208 (8)	0.0004 (7)
C7	0.0512 (10)	0.0387 (9)	0.0299 (9)	0.0038 (7)	0.0196 (8)	0.0012 (7)
C8	0.0477 (10)	0.0413 (9)	0.0305 (9)	0.0021 (8)	0.0177 (8)	0.0030 (7)
C9	0.0516 (10)	0.0440 (9)	0.0401 (10)	−0.0048 (9)	0.0248 (9)	−0.0031 (8)
C10	0.0589 (14)	0.0617 (13)	0.0506 (13)	−0.0039 (11)	0.0193 (11)	−0.0142 (11)
C11	0.0766 (17)	0.0792 (17)	0.0691 (19)	−0.0120 (15)	0.0299 (15)	−0.0369 (14)
C12	0.088 (2)	0.0621 (14)	0.101 (3)	0.0039 (15)	0.0507 (19)	−0.0263 (16)
C13	0.0832 (18)	0.0728 (17)	0.076 (2)	0.0251 (15)	0.0355 (16)	−0.0065 (15)
C14	0.0691 (15)	0.0664 (13)	0.0487 (13)	0.0169 (12)	0.0202 (12)	−0.0032 (11)
C15	0.0491 (10)	0.0435 (10)	0.0333 (10)	−0.0019 (8)	0.0181 (8)	0.0004 (7)
C16	0.0645 (13)	0.0484 (11)	0.0518 (13)	0.0084 (10)	0.0293 (11)	0.0037 (9)
C17	0.0640 (14)	0.0715 (15)	0.0666 (17)	0.0085 (12)	0.0344 (13)	−0.0051 (13)
C18	0.0688 (15)	0.0879 (18)	0.0563 (16)	−0.0157 (14)	0.0403 (14)	−0.0130 (13)
C19	0.0809 (17)	0.0669 (14)	0.0597 (16)	−0.0054 (13)	0.0381 (14)	0.0155 (12)
C20	0.0653 (14)	0.0548 (12)	0.0586 (15)	0.0061 (11)	0.0332 (12)	0.0135 (10)

Cl1—C2	1.723 (2)	C10—C11	1.385 (4)
F1—C3	1.353 (3)	C10—H10A	0.9500
O1—C7	1.221 (2)	C11—C12	1.360 (5)
N1—C7	1.346 (3)	C11—H11A	0.9500
N1—C6	1.414 (3)	C12—C13	1.363 (5)
N1—H1N	0.847 (17)	C12—H12A	0.9500
C1—C2	1.367 (3)	C13—C14	1.388 (4)
C1—C6	1.396 (3)	C13—H13A	0.9500
C1—H1A	0.9500	C14—H14A	0.9500
C2—C3	1.379 (3)	C15—C16	1.380 (3)
C3—C4	1.363 (3)	C15—C20	1.385 (3)
C4—C5	1.374 (3)	C16—C17	1.384 (4)
C4—H4A	0.9500	C16—H16A	0.9500
C5—C6	1.389 (3)	C17—C18	1.364 (4)
C5—H5A	0.9500	C17—H17A	0.9500
C7—C8	1.528 (3)	C18—C19	1.375 (4)
C8—C9	1.519 (3)	C18—H18A	0.9500
C8—C15	1.526 (3)	C19—C20	1.380 (4)
C8—H8A	1.0000	C19—H19A	0.9500
C9—C10	1.380 (3)	C20—H20A	0.9500
C9—C14	1.387 (3)
C7—N1—C6	128.12 (17)	C9—C10—C11	120.4 (3)
C7—N1—H1N	118.9 (18)	C9—C10—H10A	119.8
C6—N1—H1N	112.4 (18)	C11—C10—H10A	119.8
C2—C1—C6	120.06 (19)	C12—C11—C10	120.8 (3)
C2—C1—H1A	120.0	C12—C11—H11A	119.6
C6—C1—H1A	120.0	C10—C11—H11A	119.6
C1—C2—C3	119.92 (19)	C11—C12—C13	119.7 (3)
C1—C2—Cl1	120.96 (17)	C11—C12—H12A	120.1
C3—C2—Cl1	119.12 (17)	C13—C12—H12A	120.1
F1—C3—C4	119.8 (2)	C12—C13—C14	120.3 (3)
F1—C3—C2	119.5 (2)	C12—C13—H13A	119.9
C4—C3—C2	120.61 (19)	C14—C13—H13A	119.9
C3—C4—C5	120.3 (2)	C9—C14—C13	120.6 (3)
C3—C4—H4A	119.8	C9—C14—H14A	119.7
C5—C4—H4A	119.8	C13—C14—H14A	119.7
C4—C5—C6	119.8 (2)	C16—C15—C20	118.3 (2)
C4—C5—H5A	120.1	C16—C15—C8	119.25 (18)
C6—C5—H5A	120.1	C20—C15—C8	122.37 (19)
C5—C6—C1	119.23 (19)	C15—C16—C17	121.1 (2)
C5—C6—N1	123.94 (18)	C15—C16—H16A	119.5
C1—C6—N1	116.83 (17)	C17—C16—H16A	119.5
O1—C7—N1	122.95 (18)	C18—C17—C16	120.2 (2)
O1—C7—C8	122.26 (17)	C18—C17—H17A	119.9
N1—C7—C8	114.79 (17)	C16—C17—H17A	119.9
C9—C8—C15	114.64 (16)	C17—C18—C19	119.5 (3)
C9—C8—C7	110.86 (16)	C17—C18—H18A	120.2
C15—C8—C7	108.75 (16)	C19—C18—H18A	120.2
C9—C8—H8A	107.4	C18—C19—C20	120.6 (2)
C15—C8—H8A	107.4	C18—C19—H19A	119.7
C7—C8—H8A	107.4	C20—C19—H19A	119.7
C10—C9—C14	118.2 (2)	C19—C20—C15	120.4 (2)
C10—C9—C8	119.4 (2)	C19—C20—H20A	119.8
C14—C9—C8	122.4 (2)	C15—C20—H20A	119.8
C6—C1—C2—C3	−0.1 (3)	C15—C8—C9—C14	88.2 (3)
C6—C1—C2—Cl1	179.12 (15)	C7—C8—C9—C14	−35.4 (3)
C1—C2—C3—F1	179.20 (19)	C14—C9—C10—C11	−0.9 (4)
Cl1—C2—C3—F1	−0.1 (3)	C8—C9—C10—C11	177.7 (3)
C1—C2—C3—C4	−0.2 (3)	C9—C10—C11—C12	0.0 (5)
Cl1—C2—C3—C4	−179.44 (18)	C10—C11—C12—C13	0.6 (5)
F1—C3—C4—C5	−179.4 (2)	C11—C12—C13—C14	−0.2 (6)
C2—C3—C4—C5	−0.1 (3)	C10—C9—C14—C13	1.2 (4)
C3—C4—C5—C6	0.6 (4)	C8—C9—C14—C13	−177.3 (3)
C4—C5—C6—C1	−0.9 (3)	C12—C13—C14—C9	−0.7 (5)
C4—C5—C6—N1	178.7 (2)	C9—C8—C15—C16	152.1 (2)
C2—C1—C6—C5	0.7 (3)	C7—C8—C15—C16	−83.2 (2)
C2—C1—C6—N1	−178.94 (18)	C9—C8—C15—C20	−31.1 (3)
C7—N1—C6—C5	12.1 (3)	C7—C8—C15—C20	93.6 (2)
C7—N1—C6—C1	−168.3 (2)	C20—C15—C16—C17	0.2 (3)
C6—N1—C7—O1	−1.1 (3)	C8—C15—C16—C17	177.0 (2)
C6—N1—C7—C8	177.97 (18)	C15—C16—C17—C18	0.2 (4)
O1—C7—C8—C9	95.3 (2)	C16—C17—C18—C19	−0.8 (4)
N1—C7—C8—C9	−83.8 (2)	C17—C18—C19—C20	0.9 (4)
O1—C7—C8—C15	−31.6 (2)	C18—C19—C20—C15	−0.5 (4)
N1—C7—C8—C15	149.28 (17)	C16—C15—C20—C19	0.0 (4)
C15—C8—C9—C10	−90.3 (3)	C8—C15—C20—C19	−176.8 (2)
C7—C8—C9—C10	146.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1i	0.95	2.49	3.256 (3)	138.
N1—H1N···O1i	0.85 (2)	2.09 (2)	2.895 (2)	158 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1i	0.95	2.49	3.256 (3)	138
N1—H1N⋯O1i	0.85 (2)	2.09 (2)	2.895 (2)	158 (2)

Symmetry code: (i) .