supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2008). E64, o1968    [ doi:10.1107/S1600536808029371 ]

N-Benzyl-2-(2,4-dichlorophenoxy)acetamide

M.-J. Chen, Y.-W. Fu, W.-L. Dong, Z.-B. Li and H. Zuo

Abstract top

In the title compound, C15H13Cl2NO2, the dihedral angle between the aromatic rings is 27.17 (11)°. In the crystal the molecules are linked by N-H...O hydrogen bonds.

Comment top

The structure determination was performed as a part of a project on the interactions of small molecules with proteins. The single-crystal characterization should be valuable to understand such interactions. In our previous papers we reported single crystal structures of N-benzyl-2-(2-chloro-4-methylphenoxy)acetamide (Li et al., 2008a) and N-benzyl-2-(2,6-dichlorophenoxy)acetamide (Li et al., 2008b). In the title compound, C15H13Cl2NO2, all bond lengths and angles are normal. The dihedral angle between the two aryl rings is 27.17 (11)o. The molecules are connected via N-H···O hydrogen bonding into chains.

Related literature top

For related literature, see: Li et al. (2008a, 2008b).

Experimental top

The solution of 2,4-dichlorophenol (1.0 mmol), N-benzyl-2-chloroacetamide (1.1 mmol), K2CO3 (1.1 mmol) and CH3CN (20 ml) was refluxed for 3 h. After completion of the reaction, the solution was cooled; solvent was evaporated under reduced pressure. The residue was poured into water and adjusted the pH to 6–7 with dilute hydrochloric acid (10%) and extracted with ethyl acetate, washed with brine and dried over anhydrous MgSO4 to obtain the corresponding crude product. The product was purified by column chromatography on silica gel using ethyl acetate as eluent (yield 87%). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid dissolved in ethyl acetate/hexane at room temperatures for 4 days.

Refinement top

All H atoms were placed in geometrically calculated positions and refined using a riding model with C—H = 0.97 Å (for CH2 groups) and 0.96 Å (for CH3 groups), their isotropic displacement parameters were set to 1.2 times (1.5 times for CH3 groups) the equivalent displacement parameter of their parent atoms, except the N-H one which was freely refined.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WINGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing displacement ellipsoids drawn at 50% probability level.
N-benzyl-2-(2,4-dichlorophenoxy)acetamide top
Crystal data top
C15H13Cl2NO2F(000) = 640
Mr = 310.16Dx = 1.421 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2023 reflections
a = 4.7447 (6) Åθ = 2.4–24.3°
b = 26.821 (3) ŵ = 0.45 mm−1
c = 11.3962 (15) ÅT = 298 K
β = 90.402 (2)°Prism, colourless
V = 1450.2 (3) Å30.30 × 0.10 × 0.05 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		3254 independent reflections
Radiation source: fine-focus sealed tube2233 reflections with I > 2σ(I)
graphiteRint = 0.027
phi and ω scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan
(PROGRAM? REFERENCE?)		h = −6→6
Tmin = 0.878, Tmax = 0.978k = −26→34
8418 measured reflectionsl = −14→14
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0422P)2 + 0.2337P]
where P = (Fo2 + 2Fc2)/3
3254 reflections(Δ/σ)max = 0.001
185 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C15H13Cl2NO2V = 1450.2 (3) Å3
Mr = 310.16Z = 4
Monoclinic, P21/cMo Kα radiation
a = 4.7447 (6) ŵ = 0.45 mm−1
b = 26.821 (3) ÅT = 298 K
c = 11.3962 (15) Å0.30 × 0.10 × 0.05 mm
β = 90.402 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3254 independent reflections
Absorption correction: multi-scan
(PROGRAM? REFERENCE?)		2233 reflections with I > 2σ(I)
Tmin = 0.878, Tmax = 0.978Rint = 0.027
8418 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103Δρmax = 0.19 e Å−3
S = 1.03Δρmin = −0.24 e Å−3
3254 reflectionsAbsolute structure: ?
185 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N−0.5859 (3)0.13972 (6)1.13239 (14)0.0432 (4)
H0A−0.757 (4)0.1456 (7)1.1390 (16)0.045 (6)*
Cl1−0.01187 (15)0.32457 (2)1.38966 (5)0.0718 (2)
Cl20.22803 (14)0.39046 (2)0.95534 (5)0.0711 (2)
O1−0.3722 (3)0.25520 (5)1.27258 (11)0.0467 (3)
O2−0.1562 (3)0.17031 (5)1.18000 (13)0.0533 (4)
C1−0.0568 (4)0.32072 (6)1.23900 (15)0.0419 (4)
C20.0880 (4)0.35291 (7)1.16733 (16)0.0470 (5)
H2A0.20870.37671.19910.056*
C30.0511 (4)0.34928 (7)1.04765 (16)0.0462 (5)
C4−0.1215 (4)0.31367 (7)0.99970 (17)0.0496 (5)
H4A−0.14150.31120.91870.059*
C5−0.2659 (4)0.28142 (7)1.07243 (16)0.0468 (5)
H5A−0.38340.25731.03980.056*
C6−0.2379 (4)0.28461 (6)1.19306 (15)0.0386 (4)
C7−0.5631 (4)0.21854 (7)1.23010 (18)0.0468 (5)
H7A−0.68420.23341.17070.056*
H7B−0.68160.20751.29410.056*
C8−0.4137 (4)0.17379 (6)1.17797 (15)0.0370 (4)
C9−0.4894 (4)0.09348 (7)1.08006 (17)0.0507 (5)
H9A−0.29100.09661.06150.061*
H9B−0.59120.08801.00710.061*
C10−0.5293 (4)0.04881 (7)1.15846 (17)0.0459 (5)
C11−0.7149 (5)0.01174 (9)1.1278 (2)0.0726 (7)
H11A−0.81460.01401.05740.087*
C12−0.7554 (7)−0.02898 (10)1.2005 (3)0.0908 (9)
H12A−0.8836−0.05361.17880.109*
C13−0.6107 (7)−0.03343 (10)1.3027 (3)0.0872 (9)
H13A−0.6395−0.06081.35140.105*
C14−0.4209 (6)0.00298 (11)1.3337 (2)0.0822 (8)
H14A−0.31900.00011.40340.099*
C15−0.3801 (5)0.04402 (9)1.2619 (2)0.0640 (6)
H15A−0.25120.06851.28380.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0327 (9)0.0426 (9)0.0543 (10)0.0032 (7)0.0025 (7)−0.0059 (7)
Cl10.1088 (5)0.0673 (4)0.0393 (3)−0.0261 (3)−0.0006 (3)−0.0106 (2)
Cl20.0869 (5)0.0663 (4)0.0604 (3)−0.0168 (3)0.0117 (3)0.0131 (3)
O10.0517 (8)0.0405 (7)0.0479 (7)−0.0087 (6)0.0045 (6)−0.0019 (6)
O20.0307 (7)0.0527 (8)0.0764 (10)0.0030 (6)0.0010 (6)−0.0051 (7)
C10.0511 (11)0.0370 (10)0.0376 (9)−0.0001 (8)0.0002 (8)−0.0071 (8)
C20.0539 (12)0.0377 (10)0.0492 (11)−0.0072 (9)0.0011 (9)−0.0065 (8)
C30.0506 (11)0.0407 (10)0.0475 (11)0.0004 (9)0.0053 (9)0.0029 (9)
C40.0584 (13)0.0515 (12)0.0388 (10)0.0030 (10)−0.0048 (9)0.0002 (9)
C50.0488 (11)0.0439 (11)0.0478 (11)−0.0042 (9)−0.0083 (9)−0.0046 (9)
C60.0394 (10)0.0320 (9)0.0445 (10)0.0029 (8)0.0014 (8)−0.0020 (8)
C70.0377 (10)0.0403 (10)0.0626 (12)−0.0041 (8)0.0075 (9)−0.0021 (9)
C80.0329 (10)0.0354 (9)0.0428 (10)0.0010 (7)0.0025 (7)0.0057 (7)
C90.0542 (13)0.0478 (12)0.0501 (11)0.0018 (9)0.0049 (9)−0.0093 (9)
C100.0456 (11)0.0404 (10)0.0519 (11)0.0043 (9)0.0101 (9)−0.0087 (9)
C110.0747 (17)0.0613 (15)0.0816 (17)−0.0152 (13)−0.0013 (13)−0.0055 (13)
C120.098 (2)0.0560 (16)0.119 (3)−0.0247 (15)0.020 (2)−0.0025 (16)
C130.103 (2)0.0540 (16)0.105 (2)0.0148 (16)0.0368 (19)0.0151 (15)
C140.096 (2)0.0809 (19)0.0693 (17)0.0239 (17)0.0031 (14)0.0134 (15)
C150.0697 (15)0.0590 (14)0.0632 (14)0.0012 (11)−0.0021 (12)−0.0024 (11)
Geometric parameters (Å, °) top
N—C81.329 (2)C7—C81.517 (2)
N—C91.451 (2)C7—H7A0.9700
N—H0A0.83 (2)C7—H7B0.9700
Cl1—C11.7318 (18)C9—C101.507 (3)
Cl2—C31.7448 (19)C9—H9A0.9700
O1—C61.363 (2)C9—H9B0.9700
O1—C71.420 (2)C10—C111.372 (3)
O2—C81.225 (2)C10—C151.377 (3)
C1—C21.376 (3)C11—C121.385 (4)
C1—C61.394 (2)C11—H11A0.9300
C2—C31.377 (3)C12—C131.353 (4)
C2—H2A0.9300C12—H12A0.9300
C3—C41.369 (3)C13—C141.373 (4)
C4—C51.383 (3)C13—H13A0.9300
C4—H4A0.9300C14—C151.386 (3)
C5—C61.383 (2)C14—H14A0.9300
C5—H5A0.9300C15—H15A0.9300
C8—N—C9123.59 (16)O2—C8—N124.41 (16)
C8—N—H0A115.6 (14)O2—C8—C7121.43 (16)
C9—N—H0A120.7 (14)N—C8—C7114.16 (15)
C6—O1—C7118.32 (14)N—C9—C10113.22 (16)
C2—C1—C6121.47 (17)N—C9—H9A108.9
C2—C1—Cl1119.52 (14)C10—C9—H9A108.9
C6—C1—Cl1119.00 (14)N—C9—H9B108.9
C1—C2—C3118.88 (17)C10—C9—H9B108.9
C1—C2—H2A120.6H9A—C9—H9B107.7
C3—C2—H2A120.6C11—C10—C15118.4 (2)
C4—C3—C2121.07 (18)C11—C10—C9120.5 (2)
C4—C3—Cl2119.33 (15)C15—C10—C9121.05 (19)
C2—C3—Cl2119.60 (15)C10—C11—C12120.7 (3)
C3—C4—C5119.63 (18)C10—C11—H11A119.7
C3—C4—H4A120.2C12—C11—H11A119.7
C5—C4—H4A120.2C13—C12—C11120.9 (3)
C6—C5—C4120.84 (18)C13—C12—H12A119.6
C6—C5—H5A119.6C11—C12—H12A119.6
C4—C5—H5A119.6C12—C13—C14119.1 (3)
O1—C6—C5125.67 (16)C12—C13—H13A120.5
O1—C6—C1116.25 (15)C14—C13—H13A120.5
C5—C6—C1118.09 (17)C13—C14—C15120.5 (3)
O1—C7—C8112.50 (14)C13—C14—H14A119.8
O1—C7—H7A109.1C15—C14—H14A119.8
C8—C7—H7A109.1C10—C15—C14120.4 (2)
O1—C7—H7B109.1C10—C15—H15A119.8
C8—C7—H7B109.1C14—C15—H15A119.8
H7A—C7—H7B107.8
C6—C1—C2—C30.3 (3)C9—N—C8—O20.7 (3)
Cl1—C1—C2—C3179.74 (15)C9—N—C8—C7−178.70 (16)
C1—C2—C3—C4−1.4 (3)O1—C7—C8—O23.5 (3)
C1—C2—C3—Cl2178.90 (14)O1—C7—C8—N−177.05 (15)
C2—C3—C4—C51.3 (3)C8—N—C9—C10103.3 (2)
Cl2—C3—C4—C5−178.97 (15)N—C9—C10—C11113.8 (2)
C3—C4—C5—C6−0.1 (3)N—C9—C10—C15−66.5 (3)
C7—O1—C6—C5−1.4 (2)C15—C10—C11—C121.4 (3)
C7—O1—C6—C1178.78 (15)C9—C10—C11—C12−179.0 (2)
C4—C5—C6—O1179.23 (17)C10—C11—C12—C13−0.8 (4)
C4—C5—C6—C1−1.0 (3)C11—C12—C13—C14−0.3 (4)
C2—C1—C6—O1−179.29 (16)C12—C13—C14—C150.7 (4)
Cl1—C1—C6—O11.3 (2)C11—C10—C15—C14−0.9 (3)
C2—C1—C6—C50.9 (3)C9—C10—C15—C14179.4 (2)
Cl1—C1—C6—C5−178.57 (14)C13—C14—C15—C10−0.1 (4)
C6—O1—C7—C875.3 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N—H0A···O2i0.83 (2)2.06 (2)2.883 (2)169 (2)
Symmetry codes: (i) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N—H0A···O2i0.83 (2)2.06 (2)2.883 (2)169 (2)
Symmetry codes: (i) x−1, y, z.
Acknowledgements top

This study was supported by the Science and Technology Key Project of Chongqing Science and Technology Commission, China (grant No. CSTC, 2008 A A1001)

references
References top

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Li, Z.-B., Luo, Y.-H., Dong, W.-L., Li, J. & Zuo, H. (2008a). Acta Cryst. E64, o1610.

Li, Z.-B., Zuo, H., Dong, W.-L., He, X.-Y. & Chen, Z.-B. (2008b). Acta Cryst. E64, o1609.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.