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

In the title compound, C(20)H(15)F(2)NO, the mean plane of the acetamide group makes dihedral angles of 88.26 (6), 78.30 (7) and 9.83 (6)° with the two terminal benzene rings and difluoro-substituted benzene ring, respectively. One F atom is disordered over two orientations rotated by 180°, with a site-occupancy ratio of 0.557 (2):0.443 (2). An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds into chains along the c axis. The crystal structure is further consolidated by C-H⋯π inter-actions.

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 hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Praveen et al. (2011a ▶,b ▶,c ▶); Fun et al. (2011a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H15F2NO

M = 323.33

Monoclinic,

a = 9.9756 (2) Å

b = 18.0181 (3) Å

c = 9.8107 (2) Å

β = 117.064 (1)°

V = 1570.29 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.54 × 0.41 × 0.37 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.947, T max = 0.964

30289 measured reflections

6276 independent reflections

4829 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.130

S = 1.03

6276 reflections

231 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812014675/rz2732sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014675/rz2732Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014675/rz2732Isup3.cml

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

C20H15F2NO	F(000) = 672
Mr = 323.33	Dx = 1.368 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9889 reflections
a = 9.9756 (2) Å	θ = 2.3–33.5°
b = 18.0181 (3) Å	µ = 0.10 mm−1
c = 9.8107 (2) Å	T = 100 K
β = 117.064 (1)°	Block, colourless
V = 1570.29 (5) Å3	0.54 × 0.41 × 0.37 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6276 independent reflections
Radiation source: fine-focus sealed tube	4829 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 33.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.947, Tmax = 0.964	k = −21→28
30289 measured reflections	l = −15→15

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0529P)2 + 0.484P] where P = (Fo2 + 2Fc2)/3
6276 reflections	(Δ/σ)max = 0.001
231 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	Occ. (<1)
F1	0.47032 (19)	0.52149 (9)	0.89774 (16)	0.0561 (5)	0.557 (2)
F1X	0.56321 (18)	0.57786 (10)	0.4987 (2)	0.0389 (5)	0.443 (2)
F2	0.63567 (10)	0.50352 (5)	0.75745 (11)	0.0597 (3)
O1	0.13830 (10)	0.74131 (4)	0.30771 (8)	0.03033 (18)
N1	0.16602 (10)	0.70449 (5)	0.54187 (9)	0.02392 (17)
C1	−0.28769 (13)	0.78053 (6)	0.36744 (13)	0.0319 (2)
H1A	−0.2742	0.8252	0.4238	0.038*
C2	−0.42202 (15)	0.74209 (7)	0.31632 (16)	0.0392 (3)
H2A	−0.4989	0.7598	0.3397	0.047*
C3	−0.44453 (15)	0.67783 (8)	0.23120 (16)	0.0412 (3)
H3A	−0.5370	0.6516	0.1954	0.049*
C4	−0.33179 (16)	0.65211 (7)	0.19871 (15)	0.0409 (3)
H4A	−0.3472	0.6082	0.1397	0.049*
C5	−0.19550 (14)	0.69013 (7)	0.25202 (13)	0.0334 (2)
H5A	−0.1183	0.6718	0.2298	0.040*
C6	−0.17167 (12)	0.75480 (6)	0.33758 (11)	0.02586 (19)
C7	−0.02249 (12)	0.79671 (6)	0.40525 (10)	0.02398 (18)
H7A	0.0016	0.8095	0.5132	0.029*
C8	−0.02398 (12)	0.86899 (5)	0.32524 (11)	0.02398 (18)
C9	0.06364 (13)	0.92810 (6)	0.41162 (12)	0.0299 (2)
H9A	0.1219	0.9227	0.5192	0.036*
C10	0.06666 (15)	0.99493 (6)	0.34203 (14)	0.0344 (2)
H10A	0.1272	1.0348	0.4020	0.041*
C11	−0.01879 (15)	1.00341 (6)	0.18504 (14)	0.0335 (2)
H11A	−0.0178	1.0492	0.1374	0.040*
C12	−0.10549 (13)	0.94485 (6)	0.09827 (13)	0.0315 (2)
H12A	−0.1634	0.9505	−0.0093	0.038*
C13	−0.10860 (12)	0.87771 (6)	0.16718 (11)	0.02652 (19)
H13A	−0.1683	0.8378	0.1066	0.032*
C14	0.10303 (12)	0.74572 (5)	0.41253 (10)	0.02300 (18)
C15	0.28155 (11)	0.65108 (5)	0.58492 (10)	0.02453 (19)
C16	0.31134 (13)	0.61006 (6)	0.71693 (11)	0.0316 (2)
H16A	0.2508	0.6162	0.7679	0.038*
C17	0.43000 (15)	0.56061 (7)	0.77189 (13)	0.0407 (3)
H17A	0.4512	0.5327	0.8616	0.049*	0.443 (2)
C18	0.51753 (15)	0.55115 (7)	0.69909 (15)	0.0426 (3)
C19	0.48590 (14)	0.58994 (7)	0.56743 (14)	0.0370 (3)
H19A	0.5457	0.5822	0.5160	0.044*	0.557 (2)
C20	0.36784 (12)	0.64020 (6)	0.50857 (12)	0.0284 (2)
H20A	0.3463	0.6668	0.4173	0.034*
H1N1	0.1318 (17)	0.7138 (8)	0.6086 (17)	0.038 (4)*

	U11	U22	U33	U12	U13	U23
F1	0.0638 (10)	0.0395 (8)	0.0371 (7)	−0.0028 (7)	−0.0014 (7)	0.0203 (6)
F1X	0.0291 (8)	0.0390 (9)	0.0512 (10)	0.0090 (7)	0.0206 (7)	0.0087 (7)
F2	0.0463 (5)	0.0449 (5)	0.0598 (5)	0.0190 (4)	−0.0003 (4)	0.0138 (4)
O1	0.0440 (4)	0.0325 (4)	0.0208 (3)	0.0134 (3)	0.0203 (3)	0.0071 (3)
N1	0.0304 (4)	0.0267 (4)	0.0160 (3)	0.0008 (3)	0.0118 (3)	0.0027 (3)
C1	0.0358 (6)	0.0282 (5)	0.0345 (5)	0.0092 (4)	0.0184 (4)	0.0082 (4)
C2	0.0332 (6)	0.0376 (6)	0.0483 (7)	0.0096 (5)	0.0198 (5)	0.0154 (5)
C3	0.0347 (6)	0.0402 (7)	0.0429 (6)	−0.0029 (5)	0.0126 (5)	0.0131 (5)
C4	0.0485 (7)	0.0336 (6)	0.0398 (6)	−0.0085 (5)	0.0195 (6)	−0.0023 (5)
C5	0.0405 (6)	0.0308 (5)	0.0332 (5)	−0.0027 (5)	0.0205 (5)	−0.0032 (4)
C6	0.0326 (5)	0.0244 (4)	0.0223 (4)	0.0032 (4)	0.0140 (4)	0.0047 (3)
C7	0.0324 (5)	0.0243 (4)	0.0185 (4)	0.0036 (4)	0.0144 (3)	−0.0003 (3)
C8	0.0311 (5)	0.0225 (4)	0.0228 (4)	0.0043 (4)	0.0161 (4)	−0.0008 (3)
C9	0.0409 (6)	0.0266 (5)	0.0263 (4)	−0.0002 (4)	0.0189 (4)	−0.0054 (4)
C10	0.0471 (7)	0.0241 (5)	0.0403 (6)	−0.0028 (5)	0.0271 (5)	−0.0073 (4)
C11	0.0433 (6)	0.0236 (5)	0.0432 (6)	0.0061 (4)	0.0280 (5)	0.0052 (4)
C12	0.0350 (5)	0.0312 (5)	0.0304 (5)	0.0059 (4)	0.0167 (4)	0.0077 (4)
C13	0.0312 (5)	0.0257 (5)	0.0241 (4)	0.0030 (4)	0.0139 (4)	0.0016 (3)
C14	0.0307 (5)	0.0227 (4)	0.0169 (3)	0.0018 (4)	0.0120 (3)	0.0009 (3)
C15	0.0281 (5)	0.0220 (4)	0.0182 (3)	−0.0023 (4)	0.0059 (3)	0.0023 (3)
C16	0.0382 (6)	0.0274 (5)	0.0215 (4)	−0.0067 (4)	0.0069 (4)	0.0051 (4)
C17	0.0451 (7)	0.0289 (6)	0.0278 (5)	−0.0035 (5)	−0.0010 (5)	0.0100 (4)
C18	0.0370 (6)	0.0289 (6)	0.0396 (6)	0.0062 (5)	−0.0020 (5)	0.0058 (5)
C19	0.0332 (6)	0.0319 (6)	0.0374 (6)	0.0046 (5)	0.0086 (5)	0.0013 (4)
C20	0.0304 (5)	0.0270 (5)	0.0244 (4)	0.0035 (4)	0.0094 (4)	0.0035 (3)

F1—C17	1.3157 (17)	C8—C9	1.3938 (15)
F1X—C19	1.253 (2)	C8—C13	1.3967 (13)
F2—C18	1.3561 (14)	C9—C10	1.3913 (16)
O1—C14	1.2316 (11)	C9—H9A	0.9500
N1—C14	1.3533 (12)	C10—C11	1.3883 (18)
N1—C15	1.4107 (14)	C10—H10A	0.9500
N1—H1N1	0.881 (15)	C11—C12	1.3843 (17)
C1—C2	1.3839 (18)	C11—H11A	0.9500
C1—C6	1.3960 (15)	C12—C13	1.3931 (15)
C1—H1A	0.9500	C12—H12A	0.9500
C2—C3	1.385 (2)	C13—H13A	0.9500
C2—H2A	0.9500	C15—C20	1.3882 (15)
C3—C4	1.381 (2)	C15—C16	1.4006 (13)
C3—H3A	0.9500	C16—C17	1.3802 (18)
C4—C5	1.3944 (18)	C16—H16A	0.9500
C4—H4A	0.9500	C17—C18	1.367 (2)
C5—C6	1.3918 (15)	C17—H17A	0.9500
C5—H5A	0.9500	C18—C19	1.3733 (18)
C6—C7	1.5253 (15)	C19—C20	1.3863 (16)
C7—C8	1.5172 (14)	C19—H19A	0.9500
C7—C14	1.5283 (14)	C20—H20A	0.9500
C7—H7A	1.0000
C14—N1—C15	128.51 (8)	C9—C10—H10A	120.0
C14—N1—H1N1	114.9 (10)	C12—C11—C10	119.66 (10)
C15—N1—H1N1	116.6 (10)	C12—C11—H11A	120.2
C2—C1—C6	121.09 (11)	C10—C11—H11A	120.2
C2—C1—H1A	119.5	C11—C12—C13	120.60 (10)
C6—C1—H1A	119.5	C11—C12—H12A	119.7
C1—C2—C3	120.10 (12)	C13—C12—H12A	119.7
C1—C2—H2A	120.0	C12—C13—C8	120.06 (10)
C3—C2—H2A	120.0	C12—C13—H13A	120.0
C4—C3—C2	119.61 (12)	C8—C13—H13A	120.0
C4—C3—H3A	120.2	O1—C14—N1	124.08 (9)
C2—C3—H3A	120.2	O1—C14—C7	122.62 (8)
C3—C4—C5	120.39 (12)	N1—C14—C7	113.25 (8)
C3—C4—H4A	119.8	C20—C15—C16	120.11 (10)
C5—C4—H4A	119.8	C20—C15—N1	123.88 (8)
C6—C5—C4	120.49 (11)	C16—C15—N1	115.95 (9)
C6—C5—H5A	119.8	C17—C16—C15	119.03 (11)
C4—C5—H5A	119.8	C17—C16—H16A	120.5
C5—C6—C1	118.30 (11)	C15—C16—H16A	120.5
C5—C6—C7	122.82 (10)	F1—C17—C18	115.35 (14)
C1—C6—C7	118.83 (9)	F1—C17—C16	123.65 (15)
C8—C7—C6	114.95 (8)	C18—C17—C16	120.96 (11)
C8—C7—C14	110.80 (8)	C18—C17—H17A	119.5
C6—C7—C14	109.82 (8)	C16—C17—H17A	119.5
C8—C7—H7A	107.0	F2—C18—C17	119.82 (12)
C6—C7—H7A	107.0	F2—C18—C19	120.18 (14)
C14—C7—H7A	107.0	C17—C18—C19	120.00 (11)
C9—C8—C13	118.95 (9)	F1X—C19—C18	118.92 (13)
C9—C8—C7	119.05 (9)	F1X—C19—C20	120.23 (13)
C13—C8—C7	121.99 (9)	C18—C19—C20	120.82 (12)
C10—C9—C8	120.71 (10)	C18—C19—H19A	119.6
C10—C9—H9A	119.6	C20—C19—H19A	119.6
C8—C9—H9A	119.6	C19—C20—C15	119.03 (10)
C11—C10—C9	120.01 (11)	C19—C20—H20A	120.5
C11—C10—H10A	120.0	C15—C20—H20A	120.5
C6—C1—C2—C3	−1.41 (17)	C15—N1—C14—O1	1.15 (17)
C1—C2—C3—C4	0.48 (18)	C15—N1—C14—C7	178.67 (9)
C2—C3—C4—C5	0.48 (19)	C8—C7—C14—O1	−37.01 (13)
C3—C4—C5—C6	−0.52 (19)	C6—C7—C14—O1	91.06 (11)
C4—C5—C6—C1	−0.38 (16)	C8—C7—C14—N1	145.43 (9)
C4—C5—C6—C7	177.03 (10)	C6—C7—C14—N1	−86.51 (10)
C2—C1—C6—C5	1.35 (16)	C14—N1—C15—C20	10.68 (16)
C2—C1—C6—C7	−176.17 (10)	C14—N1—C15—C16	−172.12 (10)
C5—C6—C7—C8	106.72 (11)	C20—C15—C16—C17	1.90 (16)
C1—C6—C7—C8	−75.88 (11)	N1—C15—C16—C17	−175.41 (10)
C5—C6—C7—C14	−19.02 (12)	C15—C16—C17—F1	177.53 (13)
C1—C6—C7—C14	158.38 (9)	C15—C16—C17—C18	−0.26 (18)
C6—C7—C8—C9	145.85 (9)	F1—C17—C18—F2	0.46 (19)
C14—C7—C8—C9	−88.93 (10)	C16—C17—C18—F2	178.43 (11)
C6—C7—C8—C13	−35.24 (13)	F1—C17—C18—C19	−179.40 (13)
C14—C7—C8—C13	89.99 (11)	C16—C17—C18—C19	−1.44 (19)
C13—C8—C9—C10	0.23 (16)	F2—C18—C19—F1X	3.4 (2)
C7—C8—C9—C10	179.18 (10)	C17—C18—C19—F1X	−176.70 (14)
C8—C9—C10—C11	0.33 (17)	F2—C18—C19—C20	−178.36 (11)
C9—C10—C11—C12	−0.68 (17)	C17—C18—C19—C20	1.50 (19)
C10—C11—C12—C13	0.46 (17)	F1X—C19—C20—C15	178.32 (14)
C11—C12—C13—C8	0.11 (16)	C18—C19—C20—C15	0.14 (18)
C9—C8—C13—C12	−0.45 (15)	C16—C15—C20—C19	−1.84 (16)
C7—C8—C13—C12	−179.37 (9)	N1—C15—C20—C19	175.24 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.881 (15)	2.088 (16)	2.9134 (11)	155.7 (14)
C13—H13A···Cg1ii	0.95	2.98	3.7633 (11)	140
C16—H16A···Cg2iii	0.95	2.82	3.5998 (15)	140
C20—H20A···O1	0.95	2.29	2.8878 (14)	120

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.881 (15)	2.088 (16)	2.9134 (11)	155.7 (14)
C13—H13A⋯Cg1ii	0.95	2.98	3.7633 (11)	140
C16—H16A⋯Cg2iii	0.95	2.82	3.5998 (15)	140
C20—H20A⋯O1	0.95	2.29	2.8878 (14)	120

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