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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1968.
Published online 2008 September 20. doi:  10.1107/S1600536808029371
PMCID: PMC2959228

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

Abstract

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.

Related literature

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

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Object name is e-64-o1968-scheme1.jpg

Experimental

Crystal data

  • C15H13Cl2NO2
  • M r = 310.16
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1968-efi1.jpg
  • a = 4.7447 (6) Å
  • b = 26.821 (3) Å
  • c = 11.3962 (15) Å
  • β = 90.402 (2)°
  • V = 1450.2 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.45 mm−1
  • T = 298 (2) K
  • 0.30 × 0.10 × 0.05 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle])T min = 0.877, T max = 0.978
  • 8418 measured reflections
  • 3254 independent reflections
  • 2233 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.103
  • S = 1.03
  • 3254 reflections
  • 185 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.24 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808029371/cs2090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029371/cs2090Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

Fig. 1.
The molecular structure of the title compound showing displacement ellipsoids drawn at 50% probability level.

Crystal data

C15H13Cl2NO2F(000) = 640
Mr = 310.16Dx = 1.421 Mg m3
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 mm1
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

Bruker SMART CCD area-detector diffractometer3254 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

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 = 1.03w = 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 Å3
0 restraintsΔρmin = −0.24 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2090).

References

  • 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). SADABS and 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. [PMC free article] [PubMed]
  • Li, Z.-B., Zuo, H., Dong, W.-L., He, X.-Y. & Chen, Z.-B. (2008b). Acta Cryst. E64, o1609. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography