Literature DB >> 23795146

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

A S Praveen¹, H S Yathirajan, Jerry P Jasinski, Amanda C Keeley, B Narayana, B K Sarojini.

Abstract

In the title compound, C14H10ClF2NO, the dihedral angle between the mean planes of the 4-chloro-phenyl and 3,4-di-fluoro-phenyl rings is 65.2 (1)°. These two planes are twisted by 83.5 (5) and 38.9 (9)°, respectively, from that of the acetamide group. In the crystal, N-H⋯O hydrogen bonds form infinite chains along [100]. Weak C-H⋯O and C-H⋯F inter-actions are also observed and stack mol-ecules along the b axis.

Entities: Chemical Disease Gene

Year: 2013 PMID： 23795146 PMCID： PMC3685127 DOI： 10.1107/S1600536813014165

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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

C14H10ClF2NO M = 281.68 Orthorhombic, a = 4.8935 (5) Å b = 5.8995 (6) Å c = 42.572 (4) Å V = 1229.0 (2) Å3 Z = 4 Cu Kα radiation μ = 2.92 mm−1 T = 173 K 0.36 × 0.18 × 0.08 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.608, T max = 1.000 7056 measured reflections 2358 independent reflections 2293 reflections with I > 2σ(I) R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.111 S = 1.14 2358 reflections 172 parameters H-atom parameters constrained Δρmax = 0.42 e Å−3 Δρmin = −0.28 e Å−3 Absolute structure: Flack x determined using 852 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons & Flack, 2004 ▶). Flack parameter: −0.003 (14) Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 (Dolomanov et al., 2009 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014165/sj5323sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014165/sj5323Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813014165/sj5323Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₀ClF₂NO	D_x = 1.523 Mg m⁻³
M_r = 281.68	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2751 reflections
a = 4.8935 (5) Å	θ = 4.2–71.8°
b = 5.8995 (6) Å	µ = 2.92 mm⁻¹
c = 42.572 (4) Å	T = 173 K
V = 1229.0 (2) Å³	Block, colourless
Z = 4	0.36 × 0.18 × 0.08 mm
F(000) = 576

Agilent Xcalibur (Eos, Gemini) diffractometer	2358 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2293 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 16.1500 pixels mm^-1	θ_max = 71.9°, θ_min = 4.2°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −5→7
T_min = 0.608, T_max = 1.000	l = −51→52
7056 measured reflections

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.0565P)² + 0.5753P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.111	(Δ/σ)_max = 0.001
S = 1.14	Δρ_max = 0.42 e Å⁻³
2358 reflections	Δρ_min = −0.28 e Å⁻³
172 parameters	Absolute structure: Flack x determined using 852 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004).
0 restraints	Flack parameter: −0.003 (14)
Primary atom site location: structure-invariant direct methods

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	U_iso*/U_eq
Cl1	0.07824 (18)	1.15259 (14)	0.52637 (2)	0.0318 (2)
F1	1.2311 (7)	−0.3034 (4)	0.69693 (6)	0.0598 (8)
F2	0.8308 (7)	−0.2387 (5)	0.73854 (6)	0.0667 (9)
O1	0.5599 (5)	0.4621 (4)	0.62977 (6)	0.0325 (6)
N1	0.9971 (6)	0.3740 (5)	0.64241 (6)	0.0278 (6)
H1	1.1690	0.4034	0.6379	0.033*
C1	0.8043 (7)	0.4794 (5)	0.62509 (7)	0.0235 (7)
C2	0.9212 (8)	0.6146 (6)	0.59751 (8)	0.0302 (7)
H2A	1.0618	0.7206	0.6055	0.036*
H2B	1.0118	0.5088	0.5828	0.036*
C3	0.7068 (7)	0.7477 (6)	0.57993 (7)	0.0256 (7)
C4	0.6153 (8)	0.9550 (6)	0.59132 (8)	0.0280 (7)
H4	0.6866	1.0118	0.6105	0.034*
C5	0.4220 (8)	1.0801 (5)	0.57515 (7)	0.0274 (7)
H5	0.3605	1.2217	0.5831	0.033*
C6	0.3201 (7)	0.9951 (6)	0.54724 (7)	0.0242 (7)
C7	0.4066 (8)	0.7886 (6)	0.53548 (7)	0.0276 (7)
H7	0.3341	0.7315	0.5164	0.033*
C8	0.5996 (7)	0.6671 (6)	0.55194 (7)	0.0281 (7)
H8	0.6604	0.5254	0.5440	0.034*
C9	0.9458 (7)	0.2196 (6)	0.66731 (7)	0.0268 (7)
C10	1.1106 (8)	0.0296 (6)	0.66937 (8)	0.0332 (8)
H10	1.2496	0.0031	0.6542	0.040*
C11	1.0702 (9)	−0.1211 (6)	0.69379 (9)	0.0388 (9)
C12	0.8660 (9)	−0.0846 (7)	0.71526 (9)	0.0414 (10)
C13	0.7041 (9)	0.1022 (8)	0.71351 (8)	0.0420 (10)
H13	0.5651	0.1263	0.7287	0.050*
C14	0.7420 (7)	0.2572 (7)	0.68951 (8)	0.0328 (8)
H14	0.6298	0.3882	0.6882	0.039*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0302 (4)	0.0333 (4)	0.0318 (4)	0.0079 (4)	−0.0016 (3)	0.0064 (3)
F1	0.071 (2)	0.0458 (15)	0.0624 (16)	0.0100 (14)	−0.0095 (14)	0.0118 (13)
F2	0.0690 (19)	0.079 (2)	0.0520 (14)	−0.0119 (17)	−0.0029 (13)	0.0405 (14)
O1	0.0169 (13)	0.0455 (14)	0.0351 (12)	−0.0013 (12)	0.0013 (10)	0.0068 (11)
N1	0.0156 (14)	0.0387 (16)	0.0292 (13)	−0.0024 (11)	0.0008 (10)	0.0070 (12)
C1	0.0190 (17)	0.0247 (16)	0.0267 (15)	−0.0005 (13)	0.0014 (12)	−0.0011 (12)
C2	0.0221 (17)	0.0332 (17)	0.0355 (17)	−0.0003 (17)	0.0047 (14)	0.0104 (14)
C3	0.0216 (16)	0.0264 (16)	0.0288 (16)	−0.0002 (14)	0.0052 (13)	0.0072 (13)
C4	0.0282 (19)	0.0296 (16)	0.0263 (15)	−0.0030 (15)	−0.0021 (13)	−0.0010 (13)
C5	0.0298 (18)	0.0225 (15)	0.0298 (15)	0.0022 (15)	0.0040 (14)	−0.0023 (12)
C6	0.0192 (16)	0.0259 (16)	0.0275 (15)	0.0004 (13)	0.0019 (12)	0.0065 (12)
C7	0.0285 (18)	0.0285 (16)	0.0259 (14)	0.0003 (15)	0.0006 (13)	−0.0021 (12)
C8	0.0290 (18)	0.0249 (15)	0.0303 (15)	0.0063 (15)	0.0045 (14)	−0.0014 (12)
C9	0.0210 (16)	0.0343 (18)	0.0251 (14)	−0.0050 (15)	−0.0043 (13)	0.0024 (12)
C10	0.029 (2)	0.0396 (19)	0.0315 (16)	−0.0003 (16)	−0.0016 (14)	0.0014 (14)
C11	0.039 (2)	0.0347 (19)	0.0425 (19)	−0.0027 (19)	−0.0121 (18)	0.0079 (16)
C12	0.036 (2)	0.053 (2)	0.0352 (18)	−0.0142 (18)	−0.0074 (16)	0.0164 (18)
C13	0.033 (2)	0.065 (3)	0.0282 (17)	−0.007 (2)	0.0036 (15)	0.0057 (18)
C14	0.0234 (19)	0.045 (2)	0.0301 (17)	0.0004 (16)	0.0002 (13)	0.0005 (16)

Cl1—C6	1.747 (3)	C5—H5	0.9500
F1—C11	1.339 (5)	C5—C6	1.383 (5)
F2—C12	1.356 (4)	C6—C7	1.383 (5)
O1—C1	1.217 (4)	C7—H7	0.9500
N1—H1	0.8800	C7—C8	1.377 (5)
N1—C1	1.349 (4)	C8—H8	0.9500
N1—C9	1.420 (4)	C9—C10	1.384 (5)
C1—C2	1.530 (4)	C9—C14	1.392 (5)
C2—H2A	0.9900	C10—H10	0.9500
C2—H2B	0.9900	C10—C11	1.382 (5)
C2—C3	1.509 (5)	C11—C12	1.371 (6)
C3—C4	1.390 (5)	C12—C13	1.359 (6)
C3—C8	1.386 (5)	C13—H13	0.9500
C4—H4	0.9500	C13—C14	1.383 (5)
C4—C5	1.383 (5)	C14—H14	0.9500

C1—N1—H1	117.3	C6—C7—H7	120.5
C1—N1—C9	125.5 (3)	C8—C7—C6	118.9 (3)
C9—N1—H1	117.3	C8—C7—H7	120.5
O1—C1—N1	124.0 (3)	C3—C8—H8	119.4
O1—C1—C2	122.5 (3)	C7—C8—C3	121.2 (3)
N1—C1—C2	113.5 (3)	C7—C8—H8	119.4
C1—C2—H2A	109.0	C10—C9—N1	117.7 (3)
C1—C2—H2B	109.0	C10—C9—C14	120.2 (3)
H2A—C2—H2B	107.8	C14—C9—N1	122.1 (3)
C3—C2—C1	113.1 (3)	C9—C10—H10	120.5
C3—C2—H2A	109.0	C11—C10—C9	119.0 (4)
C3—C2—H2B	109.0	C11—C10—H10	120.5
C4—C3—C2	120.6 (3)	F1—C11—C10	120.5 (4)
C8—C3—C2	120.7 (3)	F1—C11—C12	119.2 (3)
C8—C3—C4	118.7 (3)	C12—C11—C10	120.3 (4)
C3—C4—H4	119.5	F2—C12—C11	118.3 (4)
C5—C4—C3	121.1 (3)	F2—C12—C13	120.6 (4)
C5—C4—H4	119.5	C13—C12—C11	121.0 (3)
C4—C5—H5	120.6	C12—C13—H13	120.1
C4—C5—C6	118.7 (3)	C12—C13—C14	119.9 (4)
C6—C5—H5	120.6	C14—C13—H13	120.1
C5—C6—Cl1	119.2 (3)	C9—C14—H14	120.3
C5—C6—C7	121.3 (3)	C13—C14—C9	119.5 (4)
C7—C6—Cl1	119.4 (3)	C13—C14—H14	120.3

Cl1—C6—C7—C8	179.3 (3)	C4—C5—C6—Cl1	−179.4 (3)
F1—C11—C12—F2	−1.6 (6)	C4—C5—C6—C7	0.3 (5)
F1—C11—C12—C13	177.8 (4)	C5—C6—C7—C8	−0.5 (5)
F2—C12—C13—C14	−179.7 (4)	C6—C7—C8—C3	0.2 (5)
O1—C1—C2—C3	8.0 (5)	C8—C3—C4—C5	−0.3 (5)
N1—C1—C2—C3	−175.1 (3)	C9—N1—C1—O1	3.5 (6)
N1—C9—C10—C11	178.5 (3)	C9—N1—C1—C2	−173.4 (3)
N1—C9—C14—C13	−179.1 (3)	C9—C10—C11—F1	−178.2 (3)
C1—N1—C9—C10	139.2 (4)	C9—C10—C11—C12	1.3 (6)
C1—N1—C9—C14	−42.1 (5)	C10—C9—C14—C13	−0.5 (5)
C1—C2—C3—C4	80.6 (4)	C10—C11—C12—F2	178.9 (4)
C1—C2—C3—C8	−100.1 (4)	C10—C11—C12—C13	−1.6 (6)
C2—C3—C4—C5	179.0 (3)	C11—C12—C13—C14	0.9 (6)
C2—C3—C8—C7	−179.1 (3)	C12—C13—C14—C9	0.2 (6)
C3—C4—C5—C6	0.0 (5)	C14—C9—C10—C11	−0.2 (5)
C4—C3—C8—C7	0.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	1.97	2.854 (4)	177
C5—H5···O1ⁱⁱ	0.95	2.63	3.307 (4)	129
C14—H14···F1ⁱⁱⁱ	0.95	2.69	3.615 (5)	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	2.854 (4)	177
C5—H5⋯O1ⁱⁱ	0.95	2.63	3.307 (4)	129
C14—H14⋯F1ⁱⁱⁱ	0.95	2.69	3.615 (5)	164

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

6 in total

1 in total

1. Crystal structures of two C,N-disubstituted acetamides: 2-(4-chloro-phen-yl)-N-(2-iodo-phen-yl)acetamide and 2-(4-chloro-phen-yl)-N-(pyrazin-2-yl)acetamide.

Authors: Badiadka Narayana; Hemmige S Yathirajan; Ravindranath Rathore; Christopher Glidewell
Journal: Acta Crystallogr E Crystallogr Commun Date: 2016-08-09

1 in total

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

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

2. Aqua-[N-phenyl-2-(quinolin-8-yl-oxy)acetamide]dinitratozinc(II).

3. N-(3-Chloro-4-fluoro-phen-yl)-2-(naphthalen-1-yl)acetamide.

4. N-(4-Chloro-1,3-benzothia-zol-2-yl)-2-(3-methyl-phen-yl)acetamide monohydrate.

5. N-(4,6-Dimeth-oxy-pyrimidin-2-yl)-2-(3-methyl-phen-yl)acetamide.

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

1. Crystal structures of two C,N-disubstituted acetamides: 2-(4-chloro-phen-yl)-N-(2-iodo-phen-yl)acetamide and 2-(4-chloro-phen-yl)-N-(pyrazin-2-yl)acetamide.