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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1609.
Published online 2008 July 26. doi:  10.1107/S1600536808022526
PMCID: PMC2962221

N-Benzyl-2-(2-chloro-4-methyl­phen­oxy)acetamide

Abstract

The structure determination of the title compound, C16H16ClNO2, was performed as part of a project on the inter­actions between small organic mol­ecules and proteins. In the crystal structure, the dihedral angle between the two aromatic rings is 16.14 (12)°. 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-o1609-scheme1.jpg

Experimental

Crystal data

  • C16H16ClNO2
  • M r = 289.75
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1609-efi1.jpg
  • a = 11.9900 (18) Å
  • b = 9.2986 (14) Å
  • c = 25.868 (4) Å
  • V = 2884.1 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 273 (2) K
  • 0.15 × 0.10 × 0.10 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: none
  • 15831 measured reflections
  • 3286 independent reflections
  • 1964 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.133
  • S = 0.96
  • 3286 reflections
  • 185 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.22 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/S1600536808022526/nc2110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022526/nc2110Isup2.hkl

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

Acknowledgments

This study was supported by the Key Project of the Municipal Natural Science Foundation of Chongqing, China (grant No. CSTC, 2008 A A1001).

supplementary crystallographic information

Experimental

A solution of 2-chloro-4-methylphenol (1.0 mmol), N-benzyl-2-chloroacetamide (1.1 mmol), K2CO3 (1.1 mmol) in CH3CN (20 ml) was refluxed for 3 h. Afterwards the mixture has cooled down to room temperature the solvent was evaporated under reduced pressure. The residue was poured into water and adjusted the pH 6–7. The aqueous phase was extracted with ethyl acetate, washed with brine and dried over anhydrous MgSO4. Finally the product was purified by column chromatography on silica gel. Crystals of (I) suitable for X-ray diffraction were obtained by cooling of a solution of the title compound in a mixture of ethylacetate and hexane.

Refinement

All C-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. The N-H H atom was freely refined.

Figures

Fig. 1.
The molecular structure of (I) with labelling and displacement ellipsoids drawn at the 50% probability level.

Crystal data

C16H16ClNO2Dx = 1.335 Mg m3
Mr = 289.75Mo Kα radiation λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 2043 reflections
a = 11.9900 (18) Åθ = 2.9–22.9º
b = 9.2986 (14) ŵ = 0.27 mm1
c = 25.868 (4) ÅT = 273 (2) K
V = 2884.1 (7) Å3Block, colorless
Z = 80.15 × 0.10 × 0.10 mm
F000 = 1216

Data collection

Bruker SMART CCD area-detector diffractometer1964 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.051
Monochromator: graphiteθmax = 27.5º
T = 273(2) Kθmin = 1.6º
[var phi] and ω scansh = −15→15
Absorption correction: nonek = −12→11
15831 measured reflectionsl = −25→33
3286 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133  w = 1/[σ2(Fo2) + (0.06P)2 + 0.774P] where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
3286 reflectionsΔρmax = 0.21 e Å3
185 parametersΔρmin = −0.22 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
N0.25818 (17)0.4733 (2)0.38688 (7)0.0475 (5)
H0.2699 (18)0.557 (3)0.3929 (9)0.049 (7)*
Cl10.03007 (5)0.17559 (7)0.57574 (3)0.0657 (2)
O10.12962 (13)0.38711 (16)0.50994 (6)0.0518 (4)
O20.19800 (14)0.26379 (16)0.42037 (6)0.0557 (4)
C10.17217 (18)0.2116 (2)0.57204 (8)0.0449 (5)
C20.24535 (19)0.1359 (2)0.60276 (8)0.0479 (5)
H20.21780.06750.62570.057*
C30.35942 (19)0.1599 (2)0.60016 (9)0.0484 (5)
C40.4390 (2)0.0750 (3)0.63326 (10)0.0669 (7)
H4A0.51400.10530.62630.100*
H4B0.4315−0.02550.62550.100*
H4C0.42210.09110.66910.100*
C50.3965 (2)0.2623 (3)0.56529 (9)0.0518 (6)
H50.47260.28030.56260.062*
C60.32366 (19)0.3384 (2)0.53445 (9)0.0498 (6)
H60.35140.40620.51130.060*
C70.20977 (18)0.3153 (2)0.53747 (8)0.0431 (5)
C80.1658 (2)0.4792 (2)0.46959 (8)0.0510 (6)
H8A0.22390.54220.48250.061*
H8B0.10380.53870.45840.061*
C90.21020 (18)0.3948 (2)0.42362 (8)0.0428 (5)
C100.2954 (2)0.4080 (2)0.33864 (8)0.0510 (6)
H10A0.23650.34730.32500.061*
H10B0.35970.34770.34540.061*
C110.32561 (18)0.5196 (2)0.29900 (8)0.0441 (5)
C120.2495 (2)0.5609 (2)0.26193 (9)0.0547 (6)
H120.17870.52010.26190.066*
C130.2765 (2)0.6617 (3)0.22488 (10)0.0653 (7)
H130.22410.68800.20010.078*
C140.3801 (2)0.7230 (3)0.22441 (10)0.0655 (7)
H140.39850.79010.19910.079*
C150.4562 (2)0.6855 (3)0.26101 (12)0.0686 (7)
H150.52630.72820.26110.082*
C160.4294 (2)0.5832 (3)0.29846 (10)0.0608 (7)
H160.48200.55770.32320.073*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N0.0699 (13)0.0305 (10)0.0421 (10)−0.0025 (9)0.0022 (9)−0.0059 (8)
Cl10.0507 (4)0.0739 (5)0.0724 (5)−0.0075 (3)0.0088 (3)0.0085 (3)
O10.0589 (10)0.0498 (9)0.0468 (9)0.0051 (8)0.0059 (7)0.0039 (7)
O20.0827 (12)0.0299 (8)0.0546 (10)0.0008 (8)0.0042 (8)−0.0021 (7)
C10.0479 (12)0.0466 (12)0.0403 (12)−0.0045 (10)0.0084 (10)−0.0056 (10)
C20.0601 (14)0.0441 (12)0.0393 (11)−0.0043 (11)0.0071 (11)−0.0013 (10)
C30.0573 (14)0.0465 (13)0.0413 (12)0.0001 (11)0.0005 (10)−0.0075 (10)
C40.0665 (16)0.0714 (17)0.0627 (16)0.0036 (14)−0.0056 (13)0.0011 (14)
C50.0480 (13)0.0502 (14)0.0572 (14)−0.0033 (11)0.0017 (11)−0.0088 (11)
C60.0588 (14)0.0441 (12)0.0465 (13)−0.0063 (11)0.0104 (11)−0.0021 (10)
C70.0525 (13)0.0409 (11)0.0360 (11)−0.0006 (10)0.0058 (9)−0.0072 (9)
C80.0690 (15)0.0373 (11)0.0468 (13)0.0048 (11)0.0035 (11)0.0006 (10)
C90.0546 (13)0.0341 (11)0.0397 (12)0.0046 (9)−0.0050 (10)0.0012 (9)
C100.0690 (15)0.0424 (12)0.0414 (12)0.0060 (11)−0.0006 (11)−0.0038 (10)
C110.0501 (13)0.0410 (11)0.0410 (12)0.0054 (10)0.0032 (10)−0.0050 (9)
C120.0540 (14)0.0569 (14)0.0531 (14)−0.0011 (12)−0.0045 (11)0.0017 (11)
C130.0795 (19)0.0671 (16)0.0494 (14)0.0046 (14)−0.0054 (13)0.0077 (13)
C140.084 (2)0.0584 (16)0.0541 (16)0.0035 (14)0.0201 (15)0.0046 (12)
C150.0574 (16)0.0654 (17)0.083 (2)−0.0106 (13)0.0191 (14)−0.0030 (15)
C160.0523 (14)0.0636 (16)0.0665 (17)0.0048 (12)−0.0075 (12)−0.0037 (13)

Geometric parameters (Å, °)

N—C91.329 (3)C6—H60.9300
N—C101.458 (3)C8—C91.521 (3)
N—H0.80 (2)C8—H8A0.9700
Cl1—C11.739 (2)C8—H8B0.9700
O1—C71.370 (3)C10—C111.503 (3)
O1—C81.418 (3)C10—H10A0.9700
O2—C91.230 (2)C10—H10B0.9700
C1—C21.377 (3)C11—C161.378 (3)
C1—C71.390 (3)C11—C121.378 (3)
C2—C31.387 (3)C12—C131.380 (3)
C2—H20.9300C12—H120.9300
C3—C51.385 (3)C13—C141.366 (4)
C3—C41.505 (3)C13—H130.9300
C4—H4A0.9600C14—C151.361 (4)
C4—H4B0.9600C14—H140.9300
C4—H4C0.9600C15—C161.395 (4)
C5—C61.378 (3)C15—H150.9300
C5—H50.9300C16—H160.9300
C6—C71.385 (3)
C9—N—C10121.07 (19)O1—C8—H8B109.3
C9—N—H117.9 (16)C9—C8—H8B109.3
C10—N—H120.9 (16)H8A—C8—H8B107.9
C7—O1—C8117.56 (17)O2—C9—N123.1 (2)
C2—C1—C7121.3 (2)O2—C9—C8121.51 (19)
C2—C1—Cl1119.61 (17)N—C9—C8115.30 (18)
C7—C1—Cl1119.12 (17)N—C10—C11111.74 (17)
C1—C2—C3121.2 (2)N—C10—H10A109.3
C1—C2—H2119.4C11—C10—H10A109.3
C3—C2—H2119.4N—C10—H10B109.3
C2—C3—C5117.3 (2)C11—C10—H10B109.3
C2—C3—C4120.9 (2)H10A—C10—H10B107.9
C5—C3—C4121.8 (2)C16—C11—C12118.1 (2)
C3—C4—H4A109.5C16—C11—C10121.4 (2)
C3—C4—H4B109.5C12—C11—C10120.5 (2)
H4A—C4—H4B109.5C11—C12—C13121.1 (2)
C3—C4—H4C109.5C11—C12—H12119.4
H4A—C4—H4C109.5C13—C12—H12119.4
H4B—C4—H4C109.5C14—C13—C12120.2 (3)
C6—C5—C3121.8 (2)C14—C13—H13119.9
C6—C5—H5119.1C12—C13—H13119.9
C3—C5—H5119.1C15—C14—C13119.8 (2)
C5—C6—C7120.8 (2)C15—C14—H14120.1
C5—C6—H6119.6C13—C14—H14120.1
C7—C6—H6119.6C14—C15—C16120.2 (2)
O1—C7—C6125.9 (2)C14—C15—H15119.9
O1—C7—C1116.42 (19)C16—C15—H15119.9
C6—C7—C1117.6 (2)C11—C16—C15120.5 (2)
O1—C8—C9111.79 (17)C11—C16—H16119.8
O1—C8—H8A109.3C15—C16—H16119.8
C9—C8—H8A109.3
C7—C1—C2—C3−0.3 (3)C10—N—C9—O22.8 (3)
Cl1—C1—C2—C3178.82 (16)C10—N—C9—C8−174.4 (2)
C1—C2—C3—C5−0.3 (3)O1—C8—C9—O210.6 (3)
C1—C2—C3—C4−179.0 (2)O1—C8—C9—N−172.11 (19)
C2—C3—C5—C60.3 (3)C9—N—C10—C11168.6 (2)
C4—C3—C5—C6179.0 (2)N—C10—C11—C1683.7 (3)
C3—C5—C6—C70.3 (3)N—C10—C11—C12−96.4 (2)
C8—O1—C7—C69.4 (3)C16—C11—C12—C130.8 (3)
C8—O1—C7—C1−171.68 (17)C10—C11—C12—C13−179.1 (2)
C5—C6—C7—O1178.02 (19)C11—C12—C13—C14−0.1 (4)
C5—C6—C7—C1−0.9 (3)C12—C13—C14—C15−0.8 (4)
C2—C1—C7—O1−178.11 (18)C13—C14—C15—C161.0 (4)
Cl1—C1—C7—O12.7 (2)C12—C11—C16—C15−0.5 (3)
C2—C1—C7—C60.9 (3)C10—C11—C16—C15179.4 (2)
Cl1—C1—C7—C6−178.22 (16)C14—C15—C16—C11−0.4 (4)
C7—O1—C8—C971.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N—H···O2i0.80 (2)2.09 (3)2.885 (2)169 (2)

Symmetry codes: (i) −x+1/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2110).

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). 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