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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1610.
Published online 2008 July 26. doi:  10.1107/S1600536808022514
PMCID: PMC2962222

N-Benzyl-2-(2,6-dichloro­phen­oxy)­acetamide

Abstract

The structure determination of the title compound, C15H13Cl2NO2, was undertaken as part of a project on the inter­action of small mol­ecules with proteins. In the crystal structure, the dihedral angle between the two aryl rings is 40.71 (11)°. The mol­ecules are connected via N—H(...)O hydrogen bonding into chains, which extend in the direction of the b axis.

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Object name is e-64-o1610-scheme1.jpg

Experimental

Crystal data

  • C15H13Cl2NO2
  • M r = 310.16
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1610-efi1.jpg
  • a = 14.8886 (10) Å
  • b = 8.6579 (6) Å
  • c = 22.9867 (14) Å
  • V = 2963.1 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.44 mm−1
  • T = 298 (2) K
  • 0.20 × 0.20 × 0.10 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.918, T max = 0.958
  • 16445 measured reflections
  • 3412 independent reflections
  • 2103 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.131
  • S = 1.02
  • 3412 reflections
  • 181 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: APEX2; 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, global. DOI: 10.1107/S1600536808022514/nc2111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022514/nc2111Isup2.hkl

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

Acknowledgments

This study was supported by the Key Program Projects of the Municipal Natural Science Foundation of Chongqing, China (grant No. CSTC, 2007AC1042).

supplementary crystallographic information

Experimental

A solution of 2,6-dichlorophenol (1.0 mmol), N-benzyl-2-chloroacetamide (1.1 mmol), K2CO3 (1.1 mmol) in CH3CN (20 ml) was refluxed for 3 h and afterwards cooled down to room temperature. The solvent was removed under reduced pressure and the residue was poured into water and adjusted to pH 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 obtained by column chromatography on silica gel using ethyl acetate as eluent. (yield 90%). Crystals suitable for X-ray diffraction were obtained by slow cooling of a solution of the solid in ethyl acetate/hexane at room temperature for 4 d.

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.

Figures

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

Crystal data

C15H13Cl2NO2Dx = 1.391 Mg m3
Mr = 310.16Mo Kα radiation λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 2733 reflections
a = 14.8886 (10) Åθ = 2.2–21.8º
b = 8.6579 (6) ŵ = 0.44 mm1
c = 22.9867 (14) ÅT = 298 (2) K
V = 2963.1 (3) Å3Block, colorless
Z = 80.20 × 0.20 × 0.10 mm
F000 = 1280

Data collection

Bruker SMART CCD area-detector diffractometer3412 independent reflections
Radiation source: fine-focus sealed tube2103 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.040
T = 298(2) Kθmax = 27.5º
[var phi] and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −19→18
Tmin = 0.918, Tmax = 0.958k = −10→11
16445 measured reflectionsl = −20→29

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.131  w = 1/[σ2(Fo2) + (0.0631P)2 + 0.3666P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3412 reflectionsΔρmax = 0.20 e Å3
181 parametersΔρmin = −0.34 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

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

xyzUiso*/Ueq
N10.74097 (11)0.0194 (2)0.64026 (7)0.0521 (4)
H1A0.70040.07340.62300.063*
Cl10.74730 (5)0.13003 (7)0.41952 (3)0.0787 (2)
Cl20.55214 (5)−0.24316 (9)0.55609 (4)0.0985 (3)
O10.68835 (9)−0.00499 (15)0.53078 (6)0.0526 (4)
O20.84330 (10)−0.17088 (18)0.62980 (6)0.0591 (4)
C10.65927 (14)0.0023 (2)0.42821 (9)0.0515 (5)
C20.60907 (17)−0.0417 (3)0.38036 (11)0.0679 (7)
H2A0.6217−0.00140.34380.081*
C30.54023 (18)−0.1457 (3)0.38759 (14)0.0802 (8)
H3A0.5057−0.17460.35570.096*
C40.52178 (17)−0.2071 (3)0.44101 (13)0.0761 (8)
H4A0.4755−0.27830.44540.091*
C50.57263 (15)−0.1625 (3)0.48853 (11)0.0603 (6)
C60.64111 (13)−0.0555 (2)0.48288 (9)0.0466 (5)
C70.76294 (14)−0.1008 (3)0.54620 (9)0.0522 (5)
H7A0.8148−0.07170.52310.063*
H7B0.7487−0.20760.53750.063*
C80.78542 (13)−0.0856 (2)0.60971 (9)0.0433 (5)
C90.75781 (14)0.0471 (3)0.70161 (9)0.0597 (6)
H9A0.78480.14840.70600.072*
H9B0.8007−0.02860.71550.072*
C100.67475 (13)0.0393 (2)0.73885 (8)0.0471 (5)
C110.67143 (16)0.1244 (3)0.78942 (9)0.0586 (6)
H11A0.71900.18940.79880.070*
C120.59859 (17)0.1148 (3)0.82645 (10)0.0696 (7)
H12A0.59790.17180.86070.084*
C130.52742 (17)0.0216 (3)0.81283 (11)0.0693 (7)
H13A0.47800.01650.83750.083*
C140.52928 (16)−0.0638 (3)0.76294 (11)0.0697 (7)
H14A0.4814−0.12830.75380.084*
C150.60248 (15)−0.0545 (3)0.72586 (10)0.0609 (6)
H15A0.6029−0.11230.69180.073*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0540 (10)0.0620 (11)0.0404 (9)0.0117 (8)0.0022 (8)−0.0039 (8)
Cl10.0982 (5)0.0733 (4)0.0644 (4)−0.0303 (4)−0.0038 (3)0.0045 (3)
Cl20.0904 (5)0.1033 (6)0.1019 (6)−0.0081 (4)0.0394 (4)0.0184 (4)
O10.0594 (9)0.0521 (8)0.0463 (8)0.0140 (7)−0.0084 (7)−0.0094 (6)
O20.0484 (8)0.0657 (9)0.0633 (10)0.0121 (7)−0.0112 (7)−0.0085 (7)
C10.0582 (12)0.0460 (12)0.0503 (12)0.0008 (10)−0.0087 (10)−0.0080 (9)
C20.0867 (18)0.0606 (14)0.0565 (14)0.0067 (13)−0.0203 (12)−0.0093 (11)
C30.0734 (18)0.0740 (18)0.093 (2)0.0044 (14)−0.0355 (16)−0.0234 (15)
C40.0485 (13)0.0675 (17)0.112 (2)−0.0034 (12)−0.0089 (14)−0.0132 (15)
C50.0466 (12)0.0599 (13)0.0745 (16)0.0051 (11)0.0084 (11)−0.0035 (11)
C60.0443 (11)0.0458 (11)0.0497 (12)0.0084 (9)−0.0027 (9)−0.0087 (9)
C70.0507 (12)0.0603 (13)0.0456 (12)0.0127 (10)0.0006 (9)−0.0098 (9)
C80.0362 (10)0.0448 (11)0.0488 (12)−0.0023 (9)0.0028 (9)−0.0019 (9)
C90.0522 (12)0.0828 (17)0.0441 (12)−0.0021 (11)0.0004 (10)−0.0138 (11)
C100.0481 (11)0.0523 (12)0.0409 (11)0.0042 (9)−0.0021 (9)0.0014 (9)
C110.0599 (13)0.0665 (15)0.0495 (12)−0.0068 (11)0.0043 (11)−0.0085 (10)
C120.0749 (16)0.0836 (17)0.0503 (13)−0.0039 (14)0.0138 (12)−0.0113 (12)
C130.0610 (14)0.0832 (18)0.0636 (16)−0.0015 (13)0.0164 (12)0.0084 (13)
C140.0580 (14)0.0770 (16)0.0740 (17)−0.0139 (13)0.0017 (12)0.0038 (13)
C150.0621 (14)0.0654 (14)0.0552 (14)−0.0045 (12)−0.0020 (11)−0.0112 (11)

Geometric parameters (Å, °)

N1—C81.326 (2)C7—C81.504 (3)
N1—C91.452 (3)C7—H7A0.9700
N1—H1A0.8600C7—H7B0.9700
Cl1—C11.726 (2)C9—C101.506 (3)
Cl2—C51.730 (3)C9—H9A0.9700
O1—C61.378 (2)C9—H9B0.9700
O1—C71.431 (2)C10—C111.378 (3)
O2—C81.225 (2)C10—C151.381 (3)
C1—C61.379 (3)C11—C121.381 (3)
C1—C21.383 (3)C11—H11A0.9300
C2—C31.374 (4)C12—C131.368 (3)
C2—H2A0.9300C12—H12A0.9300
C3—C41.366 (4)C13—C141.365 (3)
C3—H3A0.9300C13—H13A0.9300
C4—C51.384 (3)C14—C151.386 (3)
C4—H4A0.9300C14—H14A0.9300
C5—C61.384 (3)C15—H15A0.9300
C8—N1—C9122.78 (18)O2—C8—N1124.39 (19)
C8—N1—H1A118.6O2—C8—C7118.03 (18)
C9—N1—H1A118.6N1—C8—C7117.58 (17)
C6—O1—C7114.23 (14)N1—C9—C10113.75 (17)
C6—C1—C2121.2 (2)N1—C9—H9A108.8
C6—C1—Cl1119.12 (15)C10—C9—H9A108.8
C2—C1—Cl1119.65 (18)N1—C9—H9B108.8
C3—C2—C1119.2 (2)C10—C9—H9B108.8
C3—C2—H2A120.4H9A—C9—H9B107.7
C1—C2—H2A120.4C11—C10—C15118.0 (2)
C4—C3—C2120.9 (2)C11—C10—C9119.02 (19)
C4—C3—H3A119.5C15—C10—C9122.96 (19)
C2—C3—H3A119.5C10—C11—C12121.1 (2)
C3—C4—C5119.4 (2)C10—C11—H11A119.5
C3—C4—H4A120.3C12—C11—H11A119.5
C5—C4—H4A120.3C13—C12—C11120.2 (2)
C6—C5—C4121.0 (2)C13—C12—H12A119.9
C6—C5—Cl2118.98 (18)C11—C12—H12A119.9
C4—C5—Cl2120.0 (2)C14—C13—C12119.7 (2)
O1—C6—C1120.84 (19)C14—C13—H13A120.1
O1—C6—C5120.90 (19)C12—C13—H13A120.1
C1—C6—C5118.23 (19)C13—C14—C15120.1 (2)
O1—C7—C8111.28 (15)C13—C14—H14A120.0
O1—C7—H7A109.4C15—C14—H14A120.0
C8—C7—H7A109.4C10—C15—C14120.9 (2)
O1—C7—H7B109.4C10—C15—H15A119.5
C8—C7—H7B109.4C14—C15—H15A119.5
H7A—C7—H7B108.0
C6—C1—C2—C3−0.4 (3)C6—O1—C7—C8−154.72 (17)
Cl1—C1—C2—C3178.76 (18)C9—N1—C8—O21.3 (3)
C1—C2—C3—C4−0.9 (4)C9—N1—C8—C7−178.76 (19)
C2—C3—C4—C50.7 (4)O1—C7—C8—O2174.13 (18)
C3—C4—C5—C60.7 (4)O1—C7—C8—N1−5.8 (3)
C3—C4—C5—Cl2−178.2 (2)C8—N1—C9—C10−126.9 (2)
C7—O1—C6—C1−95.4 (2)N1—C9—C10—C11−151.9 (2)
C7—O1—C6—C586.3 (2)N1—C9—C10—C1530.6 (3)
C2—C1—C6—O1−176.57 (18)C15—C10—C11—C120.9 (3)
Cl1—C1—C6—O14.3 (3)C9—C10—C11—C12−176.7 (2)
C2—C1—C6—C51.7 (3)C10—C11—C12—C13−1.1 (4)
Cl1—C1—C6—C5−177.41 (15)C11—C12—C13—C141.1 (4)
C4—C5—C6—O1176.40 (19)C12—C13—C14—C15−0.9 (4)
Cl2—C5—C6—O1−4.6 (3)C11—C10—C15—C14−0.7 (3)
C4—C5—C6—C1−1.9 (3)C9—C10—C15—C14176.8 (2)
Cl2—C5—C6—C1177.05 (16)C13—C14—C15—C100.7 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.862.232.644 (2)109
N1—H1A···O2i0.862.312.970 (2)133

Symmetry codes: (i) −x+3/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2111).

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.
  • 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